Dictionary

of
Terpenoids
VOLUME 1

Mono- and Sesquiterpenoids

Dictionary
of
Terpenoids
VOLUME 1

Mono- and Sesquiterpenoids

J. D. Connolly and R. A. Hill

University of Glasgow, UK

I~ Ill SPRINGER-SCIENCE+BUSINESS MEDIA, B.V.

Dictionary
of
Terpenoids
VOLUME 2

Di- and higher Terpenoids

J. D . Connolly and R. A. Hill

University of Glasgow, UK

I~I'I SPRlNGER-SCIENCE+BUSINESS MEDIA, B.V.

Dictionary
of
Terpenoids
INDEXES

J. D. Connolly and R. A. Hill

University of Glasgow, UK

~ 1]I
I SPRINGER-SCIENCE+BUSINESS MEDIA, B. V.
First edition 1991

© Springer Science+Business Media Dordrecht 1991

Originally published by Chapman & Hall in 1991
Softcover reprint of the hardcover 1st edition 1991

ISBN 978-0-412-25770-4 ISBN 978-1-4899-4513-6 (eBook)

DOI 10.1007/978-1-4899-4513-6

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Contents

In Volume 1

Preface pageix

Introduction XI

Description of Main Terpenoid Types XIV

Hemiterpenoids (Entries Hm-0000 1 to Hm-000 18) 1

Monoterpenoids (Entries Mo-00001 to Mo-00843) 7

Sesquiterpenoids (Entries Sq-00001 to Sq-02835) 153

In Volume 2

Diterpenoids (Entries Di-00001 to Di-02494) page 655

Sesterterpenoids (Entries St-00001 to St-00117) 1097

Triterpenoids (Entries Tr-00001 to Tr-01508) 1119
Tetraterpenoids (Entries Te-00001 to Te-00249) 1417
Polyterpenoids (Entries Py-00001 to Py-00013) 1457

In Volume 3

Name Index page 1

Molecular Formula Index 177

CAS Registry Number Index 325
Species Index 447
Corrigenda

Owing to coding errors, a small number of entries in the Dictionary inadvertently appear in the wrong
sections. This does not affect in any way the content of the individual entries. A list of the entries affected is
as follows:

Entry No. Name Correct Section

Sq-01228 9-Eremophilene-11, 12-diol Simple Eremophilanes
Sq-01275 Alhanol 12,6-Eudesmanolides
Sq-01290 Douglaninine 12,6-Eudesmanolides
Sq-01388 Furanoeremophilan-14,6-olide 12,8-Eremophilanolides and
furanoeremophilanes
Sq-01400 3-Hydroxyfuranoeremphilane 12,8-Eremophilanolides and
furanoeremophilanes
Sq-01601 3,4-Dihydro-6-hydroxy-4, 7-dimethyl-2H-1-benzopyran Nor- and secocadinanes
Sq-01665 5,5a,6, 7-Tetrahydro-1 ,5-dimethylnaphtho[2, 1-b]furan- Nor- and secocadinanes
8(4H)-one
Sq-01761 Echinaxanthol Carabranes
Sq-01769 3-Chloro-2-oxo-1(1 0),3, 7(11 )-guaiatetraen-12,6-olide 12,6-Guaianolides
Sq-01783 Furopelargone Secoguaianes
Sq-01956 3-Hydroxyambrosin damsinate Pseudoguaianes
Sq-02142 Hymenoratin D 12,8-Guaianolides
Sq-02211 Zierone Secoaromadendranes
Di-00486 Bacchulatifolin Labdanes
Di-00500 12,15-Epoxy-8(17), 12,14-labdatrien-16-ol Labdanes
Di-00507 Haplomitrenolide A Labdanes
Di-00575 Cardiophyllidin Secoclerodanes
Di-00653 14,15-Dinor-2,4(18)-clerodadien-13-one Norclerodanes
Di-00654 14,15-Dinor-3, 11-clerodadien-13-one Norclerodanes
Di-00655 Eeniolide Secoclerodanes
Di-00770 17-Hydroxy-12,17-epoxystrictic acid Secoclerodanes
Di-00777 Isoteuflin Norclerodanes
Di-00790 Secoeeniolide Secoclerodanes
Di-01042 8,11,13-Abietatriene-12,20-diol Abietanes
Di-01061 12,16-Epoxy-11, 14-dihydroxy-5,8, 11, 13-abietatetraen-7- Abietanes
one
Di-01068 11-Hydroxy-5, 7,9(11 ), 13-abietatetraen-12-one Abietanes
Di-01071 Turbinatone Abietanes
Di-01085 Gnidiglaucin Daphnanes
Di-01304 4,17-Dihydroxy-19-nor-8(14), 15-isopimaradien-7-one Norpimaranes and
norisopimaranes
Di-01308 Icacenone Norpimaranes and
norisopimaranes
Di-01311 18-Nor-8(14), 15-pimaradien-4-o1 Norpimaranes and
norisopimaranes
Di-01898 Coralloidolide C Rearranged cembranes
St-00061 Coralloidolide D Cembranes
Tr-00162 Nigranoic Aid Cycloartanes
Tr-00473 Skimmiarepin A Apotirucallanes
Tr-01082 Walsurenol Multiftoranes
Tr-01154 lguesterin Nor- and secofriedelanes
Tr-01494 Xestolide Miscellaneous monocyclic
diterpenoids
 Caution
Treat all organic compounds as if they have dangerous properties.
The publisher makes no representation, express or implied, with regard to the
accuracy of the information contained in this Dictionary, and cannot accept any legal
responsibility or liability for any errors or omissions that may be made.
The specific information in this publication on the hazardous and toxic properties of
certain compounds is included to alert the reader to possible dangers associated with
the use of those compounds. The absence of such information should not however be
taken as an indication of safety in use or misuse.
Preface
Terpenoids are the largest and most widespread class of secondary metabolite. A
few have been known for centuries but in recent decades the level of research
activity in isolating and studying new substances has shown no sign of abating; the
discovery of completely new carbon skeletons among the naturally occurring plant
and animal terpenoids is a frequent occurrence. The wide variety of biochemical
activity shown by terpenoids, our knowledge of which is being continually
augmented as new substances are investigated, underlines their practical
importance.
With this proliferation of information it is not surprising that there is no current
authoritative documentary source on terpenoid structures and properties, and this
Dictionary has been assembled to remedy that situation. Its compulation would
have been impossible in the timescale which we have achieved were it not for our
continued involvement with the Fifth Edition of the Dictionary of Organic
Compounds (1982) and its supplements (1983 onwards), the terpenoid contents of
which have been classified, checked, rearranged and considerably augumented.
This process was made possible by the database design which made it relatively
easy to expand, replace or rearrange entries as necessary.
The resulting Dictionary contains over 22,000 terpenoids logically arranged.
The coverage, whilst very extensive, is not completely comprehensive because of the
size and diversity of the group, but work will continue to update and augment the
data set for publication in print and/or electronic form. We would be pleased to
hear from users concerning any significant omissions noted.
A fairly small proportion of the entries were originally compiled for DOC Main
Work in 1980-1982 by other contributors at Glasgow and elsewhere.
J.D.C. R.A.H.
Introduction
1. Using the Dictionary
The Dictionary is arranged in eight main sections,
which are: Hemiterpenoids (Hm), Monoterpenoids
(Mo), Sesquiterpenoids (Sq), Diterpenoids (Di),
Sesterterpenoids (St), Triterpenoids (Tr), Tetra-
terpenoids (Te) and Polyterpenoids (Py). Within
each main section the terpenoid classes are arranged
into structural classes broadly in order of increasing
structural and biogenetic complexity and following
the order laid down in the descriptive classification
section which follows. An individual entry may
contain data on several (or in some cases, a large
number) of individual terpenoids. The location of an
individual terpenoid in the smaller categories should
be almost immediate, but in the case of terpenoids
having the common skeletal types, it is preferable to
use the Name Index in Volume 3.
The guidelines which have been followed as far as
possible in combining related terpenoids within one
entry are as follows:
(1) In the case of the common structural types, e.g.
guaianes, kauranes, oleananes and others, natural
products which have the same oxygenation pattern
are normally collected in the same entry. For example
under x,y-Oleananediol will normally be found
x-Hydroxy-y-oleananone, y-Hydroxy-x-oleananone
and x, y-Oleananedione.
(2) Simple acylated derivatives such as angelates,
tiglates and many others, and glycosides, are
normally collected under the parent compound.
(3) In the case of the rarer terpenoids having
complex skeletons, more extensive structural
variations are often collected within the same entry
whenever this can be done without any ambiguity.
This has the advantage not only of saving space but
of reducing the possibility that minor errors or
inconsistencies in drawing complex structures will
make closely related natural products appear
different.
Indexes
There are four printed indexes which are located in
the separate Index Volume. These are:
Name Index. This lists every name given throughout
the Dictionary, whether it refers to an entry, stereo-
isomer or derivative, and including some names
embedded in the text of entries.
xi
Molecular Formula Index. This lists all molecular
formulae given in the Dictionary in Hill convention
order. Molecular formulae are reported for all
natural terpenoids but not normally for character-
isation derivatives.
CAS Registry Number Index. Lists all CAS (Chemical
Abstracts Service) Registry numbers given through-
out the Dictionary.
Species Index. This index lists in alphabetical order all
species names given throughout the Dictionary, with
an accompanying list of all terpenoids recorded in the
Dictionary as occurring in that species. Where the
Dictionary cites only the generic name a generic entry
will appear.
It is important to note that some common
terpenoids are so widespread that, in the context of
this Dictionary, only a general indication of their
occurrence may be given (e.g. 'widespread in the
Compositae'). Such a general statement of
occurrence will generate no entries in the Species
Index, which must therefore be used with caution and
is best suited to the tracing of rarer terpenoids.
2. Chemical names and synonyms
A fuller treatment of nomenclature and nomen-
clature policy is given in the following section.
Names corresponding to those used by CAS during
the 8th and 9th Collective Index Periods (1967-1971
and 1972-1976 respectively) are labelled with the
suffixes SCI, 9CI. Names first introduced since 1976
are referred to as 9CI as there have been no sub-
stantial changes of CA nomenclature affecting
organic compounds since that date.
If a compound cannot be located immediately in
the main body of the entries, it is important to use the
indexes.
3. Bibliographic references and literature coverage
The selection of references is made with the aim of
facilitating entry into the literature for the user who
wishes to locate more detailed information about a
particular compound. Reference contents are
indicated using suffixes.
Journal abbreviations generally follow the practice
of the Chemical Abstracts Service Source Index
(CASSI).
Introduction

In compiling this Dictionary the primary literature many cases have been checked against Gozmany [5].
has been surveyed to early 1991 and extensive Microbiological names are as reported in the primary
reference has been made to reviews available at literature.
that time.
The authoritative reference source for all plant
isolations made before 1966 is Karrer [1], and entries 6. Hazard information
for many common terpenoids carry a citation to this
Some terpenoids are toxic. Information on their
source.
toxicity is highlighted by the use of the symbol I>,
which also appears in the indexes (except the
species index). Whilst every effort has been made to
4. Coverage
alert the user to potential hazards associated with
This Dictionary is intended to report all naturally particular substances, the absence of such information
occurring terpenoids. A considerable amount of cannot be taken as a guarantee of safety in use or
effort has been expended to ensure that this aim has misuse.
been achieved as fully as possible, although it is
certain that there have been inadvertent omissions.
Terpenoids have been less thoroughly reviewed than 8. Principal abbreviations
some other classes of natural product such as
alkaloids and flavonoids, and the use of Chemical [a] specific rotation
Abstracts to find omissions is much easier for some absconfig absolute configuration
groups than for others. In general the coverage is Ac Acetyl
considered to be close to 100% for the smaller AcOH Acetic acid
terpenoid groups and somewhat lower, whilst still Ac2 0 Acetic anhydride
extensive, for the large groups. amorph amorphous
Extensive documentation of semisynthetic anal analytical applications, analysis
terpenoids would be outside the scope of the or detection
Dictionary; for example, many semisynthetic aq. aqueous
monoterpenes are known as they have played a B base
leading role in mechanistic and stereochemical bibl. bibliography
studies ever since the 19th century. However, the biosynth biosynthesis
most common and significant semisynthetics have Bp boiling point
been included. BAN British Approved N arne
In general, terpenoids of unknown structure are c concentration
not covered. ca. (circa) about
This Dictionary does not in general cover steroids, cd circular dichroism
and the reader is referred to the companion chromatog chromatography
cmr 13 C nuc1ear magnetic
· resonance
Dictionary of Steroids [2] for an extensive
documentation of these. However, naturally col colour, coloration
occurring lanostanes, cycloartanes and other groups cone concentrated
on the borderline between terpenes and steroids are config configuration
given in the triterpenoid section. Similarly, the only constit constituent
alkaloids included in this Dictionary are a restricted compd compound
range which are nitrogenous esters of a nitrogen-free cryst struct X-ray crystal structure
terpenoid moiety such as the nicotinoyl esters found determination
in the ,8-agarofuran eudesmane group; terpene d density
alkaloids proper in which the N atom is part of the dec decomposes, decomposition
terpenoid framework are covered by the Dictionary degradn degradation
of Alkaloids [3]. deriv(s) derivatives
descr described
detn detection
dil dilute, dilution
5. Taxonomic classification
dimorph dimorphic
The botanical names for higher plants given through- esr electron spin resonance
out the Dictionary are based on Willis [4]. Zoological Et Ethyl
names are derived from the primary literature but in EtOAc Ethyl acetate

Xll
 Introduction

fluor fluoresces, fluorescence resoln resolution

glc gas liquid chromatography rev review
Glc P-n-Glucopyranosyl r.t. room temperature
haz hazard sl slightly
hydrol hydrolyses, hydrolysed, hydrolysis sol soluble
INN International Nonproprietary soln solution
Name solv solvent
ir infra-red spectrum subl sublimation, sublimes
isol isolation synth synthesis
isom isomerises, isomers tautom tautomerism
JAN Japanese Accepted N arne tic thin layer chromatography
LD lethal dose: LD 50 , a dose which is tox toxicity, toxicology
lethal to 50% of the animals unsatd unsaturated
tested USAN United States Adopted Name
M molecular weight (formula weight) uv ultraviolet spectrum
max maximum v very
Me Methyl vol volume
metab metabolism, metabolite t indicates a (trivial) name which is
mise miscible duplicated in the literature
mixt mixture (not necessarily by another
mod moderately terpenoid)
Mp melting point
ms mass spectrum
n index of refraction (e.g. n~0 for
20° and sodium light) References
obt obtained 1. Konstitution und Vorkommen der Organischen
occur occurrence Pflanzenstoffe, 2nd Ed. and 2 supplements, Ed.
ord optical rotatory dispersion W. Karrer, E. Hurlimann and W. Cherbuliez,
pet. ether petroleum ether (light petroleum) Birkhaiiser Verlag, Basel, 1972-1985.
Ph phenyl (C6 H 5 ) 2. Dictionary of Steroids, Ed. R.A. Hill, D.N. Kirk,
H.L.J. Makin and G.M. Murphy, Chapman and Hall,
pharmacal pharmacology
1991.
pmr proton CH) nuclear magnetic 3. Dictionary of Alkaloids, Ed. I.W. Southon and
resonance J. Buckingham, Chapman and Hall, 1989.
props properties 4. A Dictionary of the Flowering Plants and Ferns, J.C.
purifn purification Willis, 8th Ed., Cambridge, 1988.
Py Pyridine 5. Seven Language Thesaurus of European Animals,
ref reference L. Gozmany, Chapman and Hall, 1990.

xiii
 Description of
Main Terpenoid Types
Classification of terpenoids skeleton (e.g. seco- nor- and cyclo-); such additional
categories are not specifically referred to here.
The immense variety of structural types found in the
Generally, acyclic skeletons precede monocyclic
terpenoids was rationalised by the isoprene rule of
which precede bicyclic etc. Only carbon rings are
Ruzicka [1, 2]. However, the number of exceptions
considered, heterocyclic systems being regarded as
to the regular arrangement of isoprene units led to the
open carbon chains.
biogenetic isoprene rule [3] which encompassed the
A large number of terpenoids have a skeleton
possibility of rearrangements during biosynthesis.
which can be related formally to the steroid carbon
Terpenoids are thus seen as being formed from linear
skeleton. (Note that steroids are not included in this
arrangements of isoprene units followed by various
Dictionary; see The Dictionary of Steroids [60]). The
cyclisations and rearrangements of the carbon
widely used numbering system of the ring carbons of
skeleton. They can also be biosynthetically modified
steroids has been adopted in part in many terpenoid
by the loss or addition of carbon atoms. It is useful
skeletons.
to classify terpenoids according to the number of
isoprene units from which they are biogenetically
derived, even though some carbons may have been
added or lost. (This sometimes causes some
uncertainty if it is believed that more than five
carbons have been lost; only a biosynthetic study can Basic steroid structure
resolve this issue. For example the irones (C 15 ) are
derived biosynthetically from the iridial group (C31) ).
In this Dictionary the entries are grouped into Nomenclature
sections as follows, according to the number of
isoprene units from which they are biogenetically The systems used for the nomenclature of terpenoids
derived: have evolved over a long period. For many terpenoid
classes more than one name has been proposed for
Number of Abbreviations the carbon skeleton and in a large number of cases
carbons several numbering systems are in use. (It is not un-
Volume] precedented for the same authors to use different
Hemiterpenoids 5 Hm numbering schemes in different papers!) This
Monoterpenoids 10 Mo Dictionary has used the most accepted numbering
Sesquiterpenoids 15 Sq system for most skeletal types. In cases for which no
Volume2 numbering system has been proposed or where
Diterpenoids 20 Di several are in use, preference has been given to the
Sesterterpenoids 25 St biogenetic system. Specialists in particular fields have
Triterpenoids 30 Tr been consulted where appropriate.
Tetraterpenoids 40 Te In general, IUPAC principles are followed in the
Polyterpenoids 5n(n>8) Py Dictionary when naming compounds based upon
these terpenoid skeletons, although there are
Within each section the entries are collected together numerous breaches in the terpene literature. Names
into groups having the same carbon skeleton. Within used by authors which are gross violations of good
the group entries are arranged alphabetically. IUPAC practice (e.g. where the substituents are
Wherever possible biogenetic relationships have ordered non-alphabetically) are not reported but
been used to place groups of related skeletons near have been corrected.
to each other. Thus, for example, lanostanes are There however is one common class of compounds
followed by cycloartanes (9,19-cyclolanostanes). which is commonly named in a way breaching the
Many of the larger categories are immediately fundamental IUPAC principle that each compound
followed by categories containing variants of the shall have only one principal functional group. In

xiv

the case of certain lactones this principle is almost
universally broken in the literature because of the
difficulty of naming them according to good IUPAC
practice, and this system is employed in the
Dictionary. Lactones are named using the 'olide'
suffix together with two locants, the first being the
locant for the carbonyl carbon, and this system is used
even when a high-priority substituent (usually
COOH) is also present, necessitating the appearance
of two principal suffixes.
~
0 terpenoids will not be indexed under the skeletal
p-Menthan-9,3-olid-7-oic acid
Chemical Abstracts nomenclature
Chemical Abstracts uses stereoparents as a basis for
the nomenclature of some classes of terpenoids (see
Appendix IV in the current Chemical Abstracts Index
Guide) whereas for other classes a systematic name
has precedence. Caution should be used when using
Chemical Abstracts stereoparents as the numbering
systems are sometimes different from those
commonly accepted, particularly when dealing with
gem-dimethyl substituents. Thus in CA a 29-
hydroxylanostane is described as a (4P)-28-hydroxy-
lanostane.
The systematic nomenclature system used in CA
from the Ninth Collective Index period onwards
(9CI nomenclature), and which has evolved to assist
the rigid classification of structural types, whether
terpenoid or not, is largely incompatible with the
terpenoid chemist's scheme used in this Dictionary
(the superseded nomenclature in SCI and earlier
was much closer). For this reason, and because of
their frequent length, 9CI synonyms are given in
Dictionary entries only for some structurally simple
terpenoids and not for the majority. The following
examples illustrate how terpenoids may be widely
separated in CA.
~H,OH
p-Menthan-7-ol = p-Menthane-8,9-diol =
Cyclohexanemethanol 1,2-Propanediol,
4-(1-methylethyl), 9CI 2-(4-methylcyclohexyl), 9CI
XV
Chemical Abstracts nomenclature
HO
0
Janerin = 2-Propenoic acid, 2-(hydroxymethyl)-,
decahydro-8-hydroxy-3,6-bis(methylene)-2-oxospiro-
[azuleno[4,5-b ]furan-9(2H), 2' -oxiran ]-4-yl ester, 9CI
The CA names of most of the parent carbon skeleton
are given in these notes, and a combination of this
with the extensive range of CAS registry numbers
given in the Dictionary should allow the location of
most terpenes in CA. It should be borne in mind
however that the CA names of the majority of actual
name but will depend on the oxygenation pattern
(presence of additional heterocyclic rings, esterifying
acyl groups which take priority, etc). However the
information given below should be of considerable
assistance.
Configurations and the ent-system
The ring systems of terpenoids are represented in
the conventional way with substituents below the
plane of the ring drawn with a dashed bond and
designated as having the a-configuration, and
substituents above the ring drawn with a wedge bond
and designated as having the P-configuration. In
many common ring systems the a-hydrogen atoms
found at ring junctions are omitted for clarity if they
have the natural configurations. For example the
hydrogen atoms at C-5 and C-9 are omitted from the
isopimarane skeleton. However P-hydrogen atoms
are always shown.
~-_#
HOJXV
15-Isopimaren-3fl-ol ent-15- Isopimaren-3fl-ol
5aH, 9otH implied
Some skeletal classes of terpenoids occur naturally
in two enantiomeric series. The configuration of the
'unnatural' series is indicated by the prefix ent- before
the complete name of the compound. The prefix ent-
changes the configuration of all centres in the
compound so that, for example, 15-isopimaren-3P-ol
and ent-15-isopimaren-3P-ol are enantiomers. The
ent-P-configuration is below the plane of the ring and
the ent-a-configuration above.
For acyclic carbon atoms the Cahn-lngold-Prelog
sequence rule descriptors (R or S) are used [4, 5]. The
Description of Main Terpenoid Types
ent-prefix necessitates a reversal of all configurations
thus, for example ent-8(17),14-labdadien-13R-ol has
w
the 13S-configuration.
ent-8(17), 14-labdadien-13R-ol
Structure diagrams given throughout the
Dictionary are believed to represent the correct
absolute configurations where known, but in a few
groups these are uncertain and it may be necessary to
consult the primary iterature to determine how
secure the absolute configuration assignment is, or
whether only relative configurations appear to be
known.
Abeo-, nor-, seco- and friedo- preftxes
Prefixes are used to indicate changes to the normal
terpenoid skeleton.
The abeo-prefix indicates that a bond has
migrated. Thus 5(4~ 3)-abeolupane is a lupane
in which the 5,4-bond has been replaced by a
5,3-bond.
The nor-prefix is used to indicate loss of carbons
from a skeleton. The highest available locant is
always eliminated when one of a set of equivalent
carbons is lost.
The seco-prefix is used to indicate cleavage of a
bond, with the locants for both ends of the broken
bond given, e.g. 3,4-secoeudesmane.
The friedo-prefix is used to indicate that carbon
atoms such as angular methyls and hydrogens have
migrated from their normal positions.
For more information see the current Chemical
Abstracts Index Guide. CA uses these prefixes
extensively for some classes oftriterpenes, e.g. D: C-
Friedoursane for Bauerane. In this Dictionary these
four prefixes are not italicised and form an in-
separable part of the indexable name, following CA
practice.
The main terpenoid classes
The purpose of this section is to provide basic
information about the various terpenoid classes
together with some biosynthetic information and
the numbering system adopted in this Dictionary.
Particular problems of nomenclature or numbering
are highlighted where appropriate. The order of
terpenoid groups discussed here is the same as in the
main body of the Dictionary. Within each skeletal
group the entries are arranged alphabetically in the
main Dictionary, but in order to locate a particular
terpenoid rapidly, use the Name Index first.
XVI
Hemiterpenoids Hm-00001-Hm-00018
The biogenetic isoprene rule implies the involvement
of a branched five carbon unit in the biosynthesis of
terpenoids. Isoprene, although a natural product [6],
is not a precursor of the terpenoids. The biosynthetic
origin of this five carbon unit is well established [7].
The pathway involves mevalonic acid which is
converted into isopentenyl pyrophosphate, the five-
carbon precursor of the terpenoids.
Isoprene Mevalonic acid
0 0
II II
CH 0-P-O-p-OH
?" 2 I I
OH OH
Isopentenyl pyrophosphate
There are relatively few naturally-occurring
branched C5 compounds. There are many natural
compounds having a terpenoid substituent such as an
isoprenyl group attached to a non-terpenoid nucleus,
e.g. a coumarin or flavonoid, and these are not
covered by this Dictionary.
Monoterpenoids Mo-00001-Mo-000843
Monoterpenoids have been isolated from the fragrant
oils of many plants and are important in the
perfumery and flavour industries. Monoterpenoids
are also found in many marine organisms, where they
are generally halogenated, and as insect pheremones
and defence secretions. The biosynthetic pathways of
the main classes of monoterpenes have been well
studied [8, 9].
Acyclic monoterpenoids Mo-00001-Mo-00097
In this section are grouped the regular linear mono-
terpenoids, that is those formed by a head to tail
arrangement of the isoprene units. They are
principally found in plants and in insect exudates. No
semi-systematic name has been ascribed to this
carbon skeleton probably because the systematic
2,6-dimethyloctane naming is straightforward. (Note
numbering however).
9 10
~1
8 6 4 2
Regular acyclic monoterpenoid skeleton
2,6-Dimethyloctane, 9CI, SCI
 The monoterpenoids

Irregular acyclic monoterpenoids Cyclopropane monoterpenoids and Cyclobutane

~o-00098-~o-00123
Some acyclic monoterpenoids arise from other
arrangements of the isoprene units. These may arise
by alternative linkages ofthe units, e.g. head to head,
by rearrangement of regular acyclic monoterpenoids
or by cleavage of cyclic monoterpenoids.
monoterpenoids ~o-00209-~o-00225
These groups include the pyrethrin terpenoids such as
chrysamthemic acid, and grandisol the pheromone of
the male boll weevil.
lridoids, 10-Alkyliridoids and Secoiridoids
~o-00226-~o-00412

The iridoids and secoiridoids form a large group of

Irregular acyclic monoterpenoid skeletons
Halogenated dimethyloctanes ~o-00124-~o-00171
This group is obtained principally from marine
organisms [10]. They are all regular acyclic mono-
terpenoids and the numbering system follows the
plant constituents that are found usually, but not
invariably, as glucosides [11, 12]. Their biosynthesis
has been well established [13]. The nitrogen-
containing iridoids and the large and important group
of alkaloids derived from secologanin are not
included in this Dictionary (see the Dictionary of
Alkaloids [61]).
11

accepted pattern.

10

Ochtodanes ~o-00172-~o-00190 Iridoid skeleton Secoiridoid skeleton

4,7-Dimethylcyclopenta-
The ochtodanes are also principally from marine [c]pyran, 9CI
organisms particularly Octodes spp. [10] and
presumably arise by cyclisation of myrcene.

Y
Other cyclopentane monoterpenoids
~o-00413-~o-00447
2
1

7
8 This is a large group containing several carbon
skeletons that probably arise biogenetically by
9 10
cleavage of bicyclic monoterpenoids. Also included
Myrcene Octodane
in this section are some synthetic compounds of
3-Ethyl-1, 1-dimethylcyclohexane, 9CI
historical importance in the determination of mono-
terpenoid structures.

1-Ethyl-1,3-dimethylcyclohexanes and
1-Ethyl-2,4-dimethylcyclohexanes
~o-00191-~o-00208

These two terpenoid skeletons are only found in

marine organisms [10] and presumably arise by Some cyclopentane monoterpenoid skeletons
cyclisation of a regular acyclic monoterpene skeleton
and cyclisation followed by an ethyl migration,
respectively. The numbering systems reflect their
probable biogenetic relationship. Menthanes ~o-00448-~o-00678
The menthane group comprises three isomeric types,
10v
9
7
o-, m- and p-menthanes. The p-menthanes are the
8
5 1
4 2
most widespread and arise by a cyclisation of a
3
regular acyclic monoterpenoid. The o- and m-
1-Ethyl-1,3-dimethyl- 1-Ethyl-2,4-dimethyl- menthanes are much rarer, and presumably arise by
cyclohexane cyclohexane alkyl migration of p-menthanes. The numbering

xvii
Description of Main Terpenoid Types

systems of the menthanes reflect their biogenetic by various rearrangements. They easily undergo a
relationship. Since p-menthane has a plane of wide variety of skeletal rearrangements [14) and
symmetry the numbering of ring substituents is many may be artefacts produced during isolation
chosen to give the lowest numbers and the use of procedures. The numbering systems given below are
compound locants for double bonds avoided if those most commonly used, although particularly in
possible. the older literature several numbering systems have
7 been used, e.g. for the pinanes.
Camphane has a plane of symmetry which is
2
destroyed by suitable substitution, leading to a
9
8 complex stereochemical literature, particularly in
view of the many rearrangements which occur.

2
,10
o-Menthane m-Menthane However the large number of known bicyclic mono-
terpenoids known synthetically and which have been
7
used in mechanistic studies lie outside the scope of
2
this Dictionary.
3

~
10 9

p-Menthane, SCI

~~
1-Methyl-4-(1-methylethyl)cyclohexane, 9CI
9

Camphane Fenchane
1,7, 7-Trimethylbicyclo- 1,3 ,3-Trimethylbicyclo-
Other cydobexane monoterpenoids [2.2.1)heptane, 9CI [2.2.1)heptane, 9CI
Mo-00679-Mo-00704
Cyclohexane skeletons that are not included in
previous groups are collected here. They probably
arise by cleavage of bicyclic monoterpenoids.

Pinane
2,6,6-Trimethylbicyclo[3.1.1 ]heptane, 9CI
Other cyclohexane monoterpenoid skeletons

Cydobeptane monoterpenoids Mo-00705-Mo-00723

This small group of compounds may arise by ring
expansion of the p-menthane skeleton.

q_
Carane Thujane
3,7, 7-TrimethylbicyclQ- 4-Methyl-1-(1-methylethyl)-
[4.1.0)heptane, 9CI bicyclo[3.1.0)hexane, 9CI

Cycloheptane monoterpenoid skeletons

Bicyclic monoterpe11oids Mo-00724--Mo-00836

The bicyclic monoterpenoids arise biogenetically by
further cyclisation of monocyclic terpenoids followed Miscellaneous bicyclic monoterpenoids

XVlll
 The sesquiterpenoids

Tricyclic monoterpenoids Mo-00837-Mo-00843 rearrangement of a regular acyclic precursor or by

cleavage of a cyclic terpenoid structure.
Tricyclene and isocyclene are two examples of this
small group of natural compounds.

Some irregular acyclic sesquiterpenoid skeletons

Tricyclene
1,7, 7-Trimethyltricyclo-
[2.2.1.02'6]heptane, 9CI
Isocyclene
3 ,3,4-Trimethyltricyclo-
Cyclopentane sesquiterpenoids Sq-00116-Sq-00136
[2.2.1.02'6]heptane, 9CI
This group contains a variety of miscellaneous cyclo-
pentane sesquiterpenoids.

Sesquiterpenoids Sq-00001-Sq-02835
The sesquiterpenoids are C15 compounds formed by
the assembly of three isoprenoid units. They are
found in many living systems but particularly in
Some miscellaneous cyclopentane sesquiterpenoid skeletons
higher plants [15, 16]. There is a vast number of
sesquiterpenoid carbon skeletons, which all however
arise from the common precursor, farnesyl
pyrophosphate, by various modes of cyclisations Cyclofarnesanes and rearranged cyclofarnesanes
followed, in many cases, by skeletal rearrangement Sq-00137-Sq-00170
[7, 17, 18, 19].
Cyclofarnesanes arise by formation of a six-
membered ring between carbons 6 and 11 of
farnesane. They include abscisic acid whose accepted
Simple farnesane sesquiterpenoids numbering system is 'non-farnesane'. Methyl group
Sq-00001-Sq-00066 migration gives the rearranged cyclofarnesane
There is no semi-systematic name for this carbon skeleton
skeleton, the systematic trimethyldodecane naming 12 13 15

being used instead. However there is an accepted 11 13~12 1 .

2
farnesane numbering system which is used as a
biogenetic numbering system for many 14

sesquiterpenoid skeletons. Cyclofarnesane Rearranged cyclofarnesane

1,1 ,3-Trimethyl-2-(3-methyl- skeleton
13 14 15 pentyl)cyclohexane 1,2,4-Trimethyl-3-(3-methyl-
12~
w
1 8 6 4 2
pentyl)cyclohexane

Famesane
2,6,10-Trimethyldodecane, 9CI
Furanoid farnesanes Sq-00067-Sq-00107
Although many numbering systems have been used
for furanoid farnesanes, such as ngaione, it is logical
to use the farnesane numbering system for this group.
Bisabolanes Sq-00171-Sq-00291
The bisabolanes are a fairly large group mainly found
as constituents of higher plants. The numbering
system used for bisabolanes is the same as the
farnesane system. Since the cyclohexane ring has a
plane of symmetry, substitutents in this ring should be
numbered where possible avoiding the compound
locant, 1(6), for a double bond.

Irregular acyclic sesquiterpenoids

8~
1
9
: 0
6
1
5
2
4
3
15
Sq-00108--Sq-00115
13 11 li!
The various skeletons that are not clearly head to tail Bisabolane
arrangements of isoprenoid units may arise by 1-(1 ,5-Dimethylhexyl)-4-methylcyclohexane, 9CI

XIX
Description of Main Terpenoid Types

Cyclobisabolanes Sq-00329-Sq-00331 substituents at carbons drawn as reentrant angles

[20]. Wherever possible germacranes should be
This section includes th~ sesquicarane and
drawn without substituents at reentrant centres as in
sesquisabinane carbon skeletons numbered in
this Dictionary, and care should be exercised when
accordance with bisabolane.
reading the literature. All such configurations in this
14
Dictionary have been checked and there should be
few errors.
The large germacrane group is divided into simple
5 15 germacranes, that is those without a lactone or
furan ring, 12,6-germacranolides, 12,8-germacran-
Sesquicarane
olides and furanogermacranes, nor- and homo-
Sesquisabinane
3,7-Dimethyl-7-(4-methyl- 1-(1 ,5-Dimethylhexyl)- germacranes, secogermacranes and cyclo-
3-pentenyl)bicyclo- 4-methylbicyclo[3.1.0)- germacranes.
[4.1.0)heptane, 9CI hexane,9CI

12
Elemanes Sq-00332-Sq-00389
15 13
Elemanes are numbered consistently with Germacrane Furanogermacrane
eudesmanes and germacranes (see below). They are 1,7-Dimethyl-4-(1-methyl- 4,5,6,7,8,9,10,11-0ctahydro-
rapidly formed in vitro by Cope rearrangement of ethyl)cyclodecane, 9CI 3 ,6, 10-trimethylcyclodeca[b ]- .
furan,9CI
the corresponding 1(10),4-germacradienes and it is
possible that they are artefacts produced during the
isolation procedures [16, 20, 21]. Some elemanes are
oxidatively modified, e.g. vemolepin which Lepidozanes and bicyclogermacranes
presumably is not formed by a Cope rearrangement Sq-00721-Sq-00732
during isolation.
Bicyclogermacranes, found in higher plants, have a
14
cis-fused cyclopropane ring junction whereas the
stereoisomeric lepidozanes from liverworts have a
trans-fused ring junction.
15 13

Elemane 1(10), 4-Germacradiene

1-Ethyl-1-methyl-2,4-bis-
( 1-methylethyl)cyclo-
hexane,9CI
15 12
13
Bicyclogermacrane
3,7,11,11-Tetramethylbicyclo[8.1.0)undecane, 9CI

Germacranes Sq-00390-Sq-00720
The numbering of the germacrane skeleton poses a
problem since there is a plane of symmetry through
carbons 2 and 7 [18]. Germacranes are normally
drawn in a conventional way as shown below with
H-7 in the a-configuration. Care should be taken with
the small number of germacranes with a double bond
at C-7 as the ring can be numbered in either direction.
Germacranes frequently have double bonds in the
1(10) and 4 positions. There have been proposals
to give different names to the skeletons with
(1(10)Z,4E) (melampolides) and (1(10)E,4Z)
(heliangolides) configurations. However this is
confusing and in this Dictionary all compounds are
Humulanes Sq-00733-Sq-00760
At least three numbering systems are in use for the
humulane skeleton. In this Dictionary the famesane
numbering system has been chosen rather than those
based on germacrane numbering since the
biosynthetic pathway to humulane does not involve
germacrane.
12
15 13

named as germacranes. A further problem with the Humulane

representation of germacranes arises from 1,1 ,4,8-Tetramethylcycloundecane, 9CI

XX
 The sesquiterpenoids

Caryophillanes Sq-00761-Sq-00787 Herbertanes Sq-00813-Sq-00818

Further cyclisation of the humulane skeleton
between carbons 2 and 10 produces the caryophillane
skeleton. Several numbering systems are in use for
caryophillanes; the one chosen for this Dictionary is
that based on famesane.
Herbertanes are a small group of compounds isolated
from liverworts and fungi. As the biosynthesis of this
skeleton is not known the numbering system
proposed in the literature is used.

13
14
14 15
12

Herbertane
(Mostly named as substituted benzenes in 9CI)
Caryophillane
2,6, 10,10-Tetramethylbicyclo[7 .2.0]undecane, 9CI

Lauranes Sq-00819-Sq-00829
Bicyclohumulanes Sq-00788-Sq-00789 Lauranes are found in marine organisms, particularly
Laurencia sp.
A small group of 7 ,9-cyclohumulanes is named as
bicyclohumulanes.
15 12

13

15
Bicyclohumulane
1 ,5,8,8-Tetramethylbicyclo[8.1.0]undecane, 9CI
Cuparanes Sq-00790--Sq-00810
Cuparane is formed by cyclisation between carbons 6
and 11 of the bisabolane skeleton [17, 18] and the
numbering system used here takes account of this
fact. Cuparanes are found in liverworts, higher plants
and marine organisms.
Laurane
(Mostly named as substituted benzenes in 9CI)
Trichothecanes Sq-00830--Sq-00884
The biologically active trichothecanes are produced
by various species of imperfect fungi [22]. Probably
their most important biological activity is their
cytostatic action. Most trichothecanes contain a
12,13-epoxide grouping (Scirpane) and for
convenience many trichothecanes are grouped under
the parent Scirpane in the Dictionary.

16

15

12 13

Cuparane
Trichothecane, 9CI
(Most have an aromatic ring and are named in CA
as substituted benzenes)

Cyclolauranes Sq-00811-Sq-00812
Cyclolauranes found in marine organisms may be
considered as cyclocuparanes but as they co-occur
with lauranes, the numbering system has been chosen
to agree with the accepted laurane system.
15
13
Cyclolaurane
1 ,2-Dimethyl-2-( 4-methylcyclohexyl)bicyclo[3.1.0]hexane, 9CI
Eudesmanes Sq-00885-Sq-01317
Eudesmanes are called selinanes in the older
literature. The eudesmanes found in higher plants
[20] generally have the stereochemistry shown below.
ent-eudesmanes are found in some species of liver-
worts. As with the germacrane group, the
eudesmanes are divided into groups containing
simple eudesmanes, eudesman-12,6-olides,
eudesman-12,8-olides and furanoeudesmanes, seco-
eudesmanes, and noreudesmanes. There is also a
large group of esters based on the dihydro-p-agaro-
furan skeleton which are grouped separately. Within

XXl
Description of Main Terpenoid Types

the eudesmane group there is some confusion EremophDanes Sq-01355-Sq-01497

concerning the numbering of carbons 14 and 15. The
The eremophilanes have been shown to be derived
numbering given here should be adopted.
from eudesmanes by migration of the methyl group at
14
C-10 to C-5 [23]. There is confusion in the literature
about the numbering of carbons 14 and 15; the bio-
genetic numbering given below should be used. The
normal stereochemistry is shown, although there are
13 several exceptions to this. As with the other larger
Eudesmane Dihydro-p-agarofuran
Decahydro-1 ,4a-dimethyl- 2,2,5 ,9-Tetramethyl-
categories, the eremophilanes are separated into
7-(1-methylethyl)- 2H-3,9a-methano- simple eremophilanes, 12,8-eremophilanolides and
naphthalene, 9CI 1-benzoxepin, 9CI furanoeremophilanes, seco- and abeoeremophilanes
and noreremophilanes.
Emmotin group Sq-01318-Sq-01327 H H
The emmotin group are abeoeudesmanes which have
an aromatic ring A and the methyl at C-10 migrated
to C-1. CD{"
sX\
13

Eremophilane Furanoeremophilane
Decahydro-1 ,8a-dimethyl-7- 4,4a,5,6,7 ,8,8a,9-0ctahydro-
(1-methylethyl)- 3,4a,5-trimethylnaphtho-
naphthalene, 9CI [2,3-b]furan, 9CI
IS

Emmotin skeleton

Oppositanes Sq-01328-Sq-01332
The oppositanes are 8(7 ~ 6)-abeoeudesmanes and
are found in higher plants and marine organisms.
14
Chiloscyphanes Sq-01498-Sq-01499
The chiloscyphanes, a small group isolated from
liverworts, are 8(7 ~ 6)-abeoeremophilanes.

13
13
Oppositane Chiloscyphane
Octahydro-3a, 7-dimethyl-1-(2-methylpropyl)-1H-indene, 9CI Octahydro-7, 7a-dimethyl-1-(2-methylpropyl)-1H-indene, 9CI

Cycloeudesmanes Sq-01335-Sq-01352
Aristolanes Sq-01500-Sq-01509
Various cycloeudesmanes are included in this The aristolanes, isolated inter alia from Aristolochia
section. spp., are 6,11-cycloeremophilanes.

12
Gorgonanes Sq-01353-Sq-01354 13
Aristolane
The gorgonanes are derived from eudesmanes by Decahydro-1 ,1, 7, 7a-tetramethyl-1H-cyclopropa-
isopropyl group migration to C-6. (a]naphthalene, 9CI

Gorgonane
Decahydro-1 ,4a-dimethyl-8-
(1-methylethyi)naphthalene, 9CI
Nardosinanes Sq-01510-Sq-01518
The nardosinanes, isolated from marine organisms,
are eremophilanes in which the isopropyl group has
migrated to carbon 6.

xxii
 The sesquiterpenoids

~ 15

Nardosinane
Decahydro-1 ,Sa-dimethyl-5-(1-methylethyl)naphthalene

CadinBlle group Sq-01546-Sq-01687

BrasilBlles Sq-01519-Sq-01521 The nomenclature, numbering and absolute stereo-
chemistry of this group is somewhat confused [24].
No biosynthetic scheme has been proposed for this
Biogenetic (germacrane) numbering is used here, but
skeleton.
many other numbering systems have been used in the
literature. The names of the skeletons depend on the
13 relative stereochemistries at carbons 1, 6 and 7 as
indicated. Moreover, the aromatised skeletons are
given different names, calamenene and cadalene, and
these are often given different numbering systems.
Brasilane Nor- and seco-cadinanes are grouped separately.
Octahydro-1 ,6,6-trimethyl-4-(1-methylethyl)-1H-indene

14

Cacalol group Sq-01522-Sq-01534

The cacalol sesquiterpenoids occur, inter alia, in 15

Cacalia spp. and are also eremophilanes, typically

with an aromatic ring B, in which carbon-14 has Cadinane Muurolane
further migrated to C-6. Decahydro-1 ,6-dimethyl-
4-(1-methylethyl)-
naphthalene, 9CI

& ;j)
14 13

Cacalol skeleton

H• H·
Valenmes Sq-01535-Sq-01538 A A
Bulgarane Amorphane
The valeranes (also called jatamansanes), mainly
from Valeriana spp., are eudesmanes where the
methyl group at C-4 has migrated to C-5. There is
normally a carbonyl group at C-4.

12

Calamenene Cadalene
13
Valerane
Decahydro-4a,8a-dimethyl-2-(1-methylethyl)naphthalene

MisceiJSlleous rearranged eudesmBlles
Sq-01539-Sq-01545
Various methyl-migrated eudesmanes are grouped
together here. The methyl groups should retain their
numbering on migration.
Alliacanes Sq-01688-Sq-01690
The alliacanes from Marasmius alliacus and the
aromatic primnatrienes from a Primnoeides sp. have
unfortunately been assigned different numbering
systems. The biosynthesis of this skeleton has not
been established.

xxiii
Description of Main Terpenoid Types

10 Coloranes Sq-01749-sq-01757

15 The coloranes, few in number, are related to the

14 drimanes. A methyl migration from C-4 to C-3 has
occurred.

11
Aliiacane Primnatriene
Octahydro-2,2,4-trimethyl-
7-(1-methylethyl)-
1H-indene, 9CI
14

13
Colorane
Decahydro-1 ,2,4a,5 ,6-pentamethylnaphthalene
Oplopanes Sq-01691-sq-01703
Oplopanes, from higher plants, are 3(4~ 5)-
abeocadinanes and the numbering system used here XIUlthiUles Sq-01758-sq-01765
is biogenetic. The xanthanes, originally isolated from Xanthium
spp., are 4,5-secoguaianes [18, 19].

15

Oplopane
13
1-Ethyloctahydro-4-methyl-7-(1-methylethyl)-1H-indene
Xanthane
1-Butyl-2-methyl-5-(1-methylethyl)cycloheptane

MutisiiUlthol group Sq-01704-sq-01705

CarabriUles Sq-01766-sq-01767
This is a small group of 6(7 ~ 8)-abeocadinanes from
Jungia and Mutisia spp. Again the numbering system The carabranes are a small group of 5,10-cyclo-
is biogenetic. xanthanes.
14
14

15

13
Carabrane
Mutisianthol group skeleton 7-Butyl-1-methyl-4-(1-methylethyl)bicyclo[4.1.0 )heptane
Octahydro-1 ,5-dimethyl-3-(2-methylpropyl)-1H-indene

GuaiiUles Sq-01768--Sq-02110
DrimiUles Sq-01706-sq-01748
This large group is divided into simple guaianes,
The drimanes, from fungi and higher plants, arise by 12,6-guaianolides, 12,8-guaianolides, guaiane
direct cyclisation of a farnesane derivative [18]. The dimers, and seco-, cyclo- and abeo-guaianes [20, 21].
accepted numbering system is shown.
14

11

12

12
,
t3 14
13

Drimane Guaiane
Decahydro-1, 1,4a,5 ,6-pentamethylnaphthalene Decahydro-1 ,4-dimethyl-7-(1-methylethyl)azulene, 9CI

xxiv
 The sesquiterpeooids

Pseudoguaianes Sq-02111-Sq-02180 14 14 14

The migration of a methyl group. of the guaiane

skeleton from C-4 to C-5 produces the pseudoguaiane
skeleton [20, 21]. There is often an oxygen function 15 15 15

at C-4. Patchoulane Rearranged patchoulanes

14

Valerenanes Sq-02248-Sq-02251
Valerenanes are 8(7 ~ 6)-abeoguaianes. Only a few
13 representatives have been reported. They are not to
Pseudoguaiane be confused with the valeranes (see above).
Decahydro-4,8a-dimethyl-7-(1-methylethyl)azulene

Aromadendranes Sq-02181-Sq-02227 12

The aromadendranes are 6,11-cycloguaianes. The

smaller groups of 5, 10-cycloaromadendranes and Valerenane
seco-aromadendranes, including the plagiochilins Octahydro-1 ,4-dimethyl-7-(2-methylpropyl)-1H-indene
which are 2,3-seco-aromadendranes, have been given
separate sections.
14

Mricananes Sq-02252-Sq-02256
The famesane numbering system is used for the
africanane skeleton although the biosynthesis has not
13 12 been established conclusively.
Aromadrendrane 14
Decahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene, 9CI
9

1
15
Cubebanes and JyaxiJJaranes Sq-02228-Sq-02237 13
12

Africanane
The small groups of cubebanes and ivaxillaranes are Decahydro-3,3 ,5, 7b-tetramethyl-1H-cycloprop[e]azulene
1,6- and 8,10-cycloguaianes respectively.
14 14

Himachalanes Sq-02257-Sq-02270
Many numbering systems have been used for the
13 himachalane skeleton. The famesane system has
13 12
been used here.
Cubebane Ivaxillarane
14
Octahydro-3,7-dimethyl-
4-(1-methylethyl)-
1H-cyclopenta[1 ,3]- 15
cyclopropa(1,2]benzene, 9CI

Patchoulanes and rearranged patchoulanes
Sq-02238-Sq-02247
Patchoulanes are 1,11-cycloguaianes. Various
rearranged patchoulanes are also found, in for
example patchouli oil. Biogenetic numbering has
been used here.
XXV
12
Himachalane
Decahydro-2,5 ,9 ,9-tetramethyl-1H-benzocycloheptene, 9CI
Longipinanes Sq-02271-Sq-02280
Longipinanes are 2,7-cyclohimachalanes. Several
numbering systems have been used for this skeleton;
Description of Main Terpenoid Types

the famesane system being used for consistency here. Thapsanes and Fukinanes Sq-02303-Sq-02311
The absolute configuration of this group is in some
The thapsanes occur in Thapsia spp. while fukinanes
doubt.
are found in Petasites japonicus. Both types are
14 relatively uncommon. One group of workers has
defined the thapsane skeleton as including an oxygen
15
bridge, but that is not followed here.
12

13
15
Longipinane
2,6,6,9-Tetramethyltricyclo(5.4.0.!f·8 ]undecane, 9CI
15
Thapsane Fukinane
Octahydro-1,2,3a,7,7,7a- Octahydro-2,3a,4-trimethyl-
hexamethyl-1H-indene 2-(1-methylethyl)-1H-indene
Longifolanes Sq-02281-Sq-02285
Several numbering systems have been used in the Picrotoxanes Sq-02312-Sq-02330
older literature but as the biosynthesis has been
established [25], the biogenetic farnesane system is The picrotoxanes are bitter, toxic constituents of
used here. the Orchidaceae [20, 21]. They are generally highly
oxygenated. The numbering system in general use
12 13
seems to be based on the menthane system and is
inconsistent with the majority of other schemes.

Longifolane
Decahydro-4,8,8,9-tetramethyl-1 ,4-methanoazulene, 9CI
~· 15
Picrotoxane
10

Octahydro-1 ,4, 7a-trimethyl-5-(1-methylethyl)-1H-indene

Longibornanes Sq-0228frSq-02287 Daucanes Sq-02331-Sq-02359

Longibornanes are 3, 7-cyclohimachalanes.
Many numbering systems have been used for the
daucanes; that chosen here is related to the guaiane
system. Daucanes are also called carotanes but this
name is not recommended because of possible
confusion with the carotenoids.
15

Longibornane
Decahydro-1 ,5 ,5 ,Sa-tetramethyl-1 ,4-methanoazulene, 9CI 14
12

13
Daucane
Pinguisanes Sq-02288-Sq-02302 Decahydro-3a,6-dimethyl-1-(1-methylethyl)azulene

The structures of several pinguisanes from liverworts

have recently been revised. Many of the trivial names lsodaucanes Sq-023@-Sq-02364
in this group are confusing. The commonly used The isodaucanes (also called salviolanes) are clearly
numbering system is given here. related to daucanes. The numbering system used here
is again related to the guaiane system.
IS 15
10
11

12

Pinguisane lsodaucane
5-Ethyloctahydro-1 ,3a,4, 7a-tetramethyl-1H-indene Decahydro-3a, 7-dimethyl-1-(1-methylethyl)azulene

xxvi
 The sesquiterpenoids

Perfonmes and pacifigorgianes Sq-02365-Sq-02368 14

The performances form a small group found in 12

Laurencia spp. Pacifigorgianes are found in
liverworts, higher plants and marine organisms. 15

Sterpurane
Decahydro-2a,5,5,7-trimethyl-1H-cyclobut(flindene, 9CI
15

12

14

13
15
llludalanes Sq-02398-Sq-02414
13 14 12

Perforane Pacifigorgiane The illudalanes are 4,6-secoilludanes and include the

Decahydro-1,4,7 ,9a-tetra- Octahydro-1 ,5-dimethyl-4- pterosins from bracken [26].
methyl-1H-benzocyclo- (2-methylpropyl)-1H-indene
heptene

13
12

Asteriscanes Sq-02369-Sq-02370
15
The asteriscanes form a small group isolated from Illudalane
Asteriscus spp. The farnesane numbering system is 5-Ethyloctahydro-2,2,4,6-tetramethyl-1H-indene, 9CI
used here.

14
Isolactaranes, Lactaranes and Marasmananes
Sq-02415-Sq-02449
These three groups are biogenetically related to the
15
illudanes and the numbering system used here
Asteriscane reflects this fact. Numbering systems in the literature
Decahydro-2,2,4,8-tetramethyl-lH-cyclopentacyclooctene, 9CI are similar but care should be exercised with the
numbering of the methyl groups.

llludanes and ProtoHludanes Sq-02371-Sq-02390 14

14

12 12
Although historically different numbering systems 13 13
have been proposed for the illudane skeleton and the
related groups, we use the biogenetic farnesane 15 15

numbering shown here. Isolactarane Lactarane

14
14
13
13
12
12

15 15

llludane Protoilludane Marasmanane

Decahydro-2' ,2' ,4' ,6' -tetra- Decahydro-3,6,6,7b-tetra-
methylspiro[cyclopropane- methyl-1H-cyclobut[e]-
1,5' -(5H]indene], 9CI indene,9CI

Furodysin and furodysinin groups

Sterpuranes Sq-02391-Sq-02397 Sq-02450-Sq-02454
Sterpuranes are biogenetically related to the A farnesane numbering system is used for the
illudanes. The farnesane numbering system is used in furodysin and the rearranged furodysinin groups
preference to others. from Dysidea spp.

xxvii
Description of Main Terpenoid Types

12 13
Furodysin skeleton
3-Ethyldecahydro-
1,1 ,6-trimethylnaphthalene
14
Chamigranes Sq-02491-Sq-02539
The chamigranes form a large group of mainly marine
natural products, mostly from Laurencia and Aplysia
12 13 spp. The numbering system is based on famesane.
Furodysinin skeleton
2-Ethyldecahydro- 12
1, 1,6-trimethylnaphthalene

15

14

Botrydial group Sq-02455-Sq-02460 Chamigrane

1,1,5,9-Tetramethylspiro[5.5]undecane, 9CI
The non-biogenetic numbering system has been
adopted for the botrydial group from Botrytus spp.

11 MisceDaneous spirosesquiterpenoids
Sq-02540-Sq-02554
Some miscellaneous spirosesquiterpenoid skeletons
Botrydial skeleton
are collected in this section.
Octahydro-1, 1,3,3,4,5-hexamethyl-1H-indene

Spirovetivanes Sq-02461-Sq-02474
Spirovetivanes (also known as vetispiranes) are 1,2,5 ,9-Tetramethylspiro- 1,6-Dimethyl-8-(1-methyl-
found in vetiver oil and also occur as phytoalexins in [5.5]undecane ethyl)spiro[4. 5]decane
infected potatoes. The numbering system reflects
their eudesmane derivation [27).

Cedranes and Isocedranes Sq-02555-Sq-02583

The cedranes occur in wood oils and lac resins.
Several numbering systems have been used. The
13 famesane system is used here. Isocedranes are
rearranged cedranes; a related numbering system is
Spirovetivane
6,10-Dimethyl-2-(1-methylethyl)spiro[4.5]decane, 9CI in use.

Acoranes Sq-02475-Sq-02490 13

The acoranes and the enantiomeric alaskanes have

a symmetrical six-membered ring. It has been Cedrane lsocedrane
Octahydro-3,6,8,8-tetra- Octahydro-3,4,8,8-tetra-
suggested [24) that C-2 should be chosen to be syn methyl-1H-3a, 7-methano- methyl-1H-3a, 7-methano-
to C-14. azulene azulene

14

Zizaanes and Prezizaanes Sq-02584-Sq-02598

13

Acorane The zizaanes and prezizaanes are found in wood oils

1,8-Dimethyl-4-(1-methylethyl)spiro[4.5]decane, 9CI including vetiver oil.

xxviii
 The sesquiterpenoids

13 PeDtaleDanes Sq-02620-Sq-02626
15
The pentalenanes are antibiotics from Streptomyces
spp. Also included in this section are the rearranged
and seco-pentalenanes.
Zizaane Prezizaane 14
Octahydro-3,7 ,8,8-tetra- Octahydro-3,7,7,8-tetra-
methyl-1H-3a,6-methano- methyl-1H-3a,6-methano- 14
13 15 13
azulene, 9CI azulene 15

Pentalenane Rearranged pentalenane

Clovanes Sq-02599-Sq-02601 Decahydro-1,4,7,7-tetra- Decahydro-1,4,6,7-tetra-
Only one clovane is natural and it is possibly an methylcyclopenta[c]- methylcyclopenta[c]-
pentalene pentalene
artefact from the acid catalysed rearrangement of
a caryophyllene.

SHphiDanes, SHpbiperfolianes and

PresHpbiperfolianes Sq-02627-Sq-02641
13

These three groups are related biogenetically. The

absolute configurations have not been established
Clovane unambiguously.
Decahydro-1,1,7-trimethyl-3a,7-methano-
3aH-cyclopentacyclooctene, 9CI
15

14
13
PrecapDelJanes and CapDeHanes Sq-02602-Sq-02611 13

12 12
Precapnellanes and capnellanes are of marine origin. Silphinane Silphiperfoliane
Capnellanes are 4, 11-cycloprecapnellanes. Decahydro-1 ,4,4,5a-tetra- Decahydro-1 ,4,5 ,5b-tetra-
methylcyclopenta[ c]- methylcyclopenta[c)
pentalene pentalene

15
14 13

Precapnellane Capnellane 14

Decahydro-1 ,5 ,8,8-tetra- Decahydro-3,3,4,7a-tetra- 13

methyl-1H-cyclopenta- methyl-1H-cyclopenta[a]- 12
cyclooctene pentalene, 9CI
Presilphiperfoliane

Hirsutsmes and rearranged hirsutsmes

Sq-02612-Sq-02619
lsocomanes Sq-02642-Sq-02649
The hirsutanes are antibiotics from various fungi.
Several numbering systems have been used for this
Methyl migrated analogues are also found.
skeleton, including four from one author. The
originally proposed system is used here.

12

15 13

Hirsutane Rearranged hirsutane

12
Decahydro-2,2,3b,4-tetra- Decahydro-2,3,3b ,4-tetra-
methyl-1H-cyclopenta[a]- methyl-1H-cyclopenta[a]- Isocomane
pentalene pentalene Decahydro-1 ,3a,4,5-tetramethylcyclopenta[c)pentalene

xxix
Description of Main Terpenoid Types

Pamlsinsanes Sq-02650-Sq-02652 1-2 12

The panasinsanes from Panax ginseng are 2,7-cyclo-

caryophyllanes. The farnesane numbering system is
used here.
Campherenane a-Santalane
1,7-Dimethyl-7-(4-methyl- 2,3-Dimethyl-2-(4-methyl-
13
pentyl)bicyclo[2.2.1]- pentyl)tricyclo[2.2.1.02·6]-
heptane, 9CI heptane

Panasinsane
Decahydro-2,2,4a,8-tetramethylcyclobut[c]indene, 9CI

P-Santalane
2,3-Dimethyl-2-(4-methylpentyl)bicyclo[2.2.1]heptane

Modhephanes Sq-02653-Sq-02655
The modhephanes form a small group of bridged
tricyclic sesquiterpenes from Isocoma wrightii. The
Sativanes and Helmillthosporanes
numbering system originally proposed is used here.
Sq-02673-Sq-02677
The sativanes and their 13,14-seco-derivatives, the
helminthosporanes, are fungal metabolites from
Helminthosporum sativum.
12

Modhephane
Tetrahydro-1 ,1 ,3,4-tetramethyl-1H,4H-propanopentalene

15 15

13

12 12

Sativane Helminthosporane
Quadranes Sq-0265fr-Sq-02657 1,6,7 ,8-Tetramethyl-4-
Octahydro-4,8-dimethyl-7-
The quadranes are antibiotics from Aspergillus (1-methylethyl)1 ,4-methano- (1-methylethyl )bicyclo-
1H-indene [3.2.1]octane
terreus.
14 15

Copacamphanes and Sillularanes Sq-02678-Sq-02683

Copacamphanes and cyclocopacamphanes have
Quadrane regular farnesane skeletons and a farnesane
numbering system has been used. Sinularanes and
cyclocopacamphanes are rearrangement products.

13
Campherenanes, a-Santalanes and P-Santalanes 13

Sq-02659-Sq-02672
15
The campherenanes from Cinnamomum camphora Copacamphane Cyclocopacamphane
and the a- and {J-santalanes from sandalwood oil Octahydro-4,8-dimethyl-7- Octahydro-1, 7a-dimethyl-5·
(Santalum album) are biogenetically related. The (1-methylethyl)-1 ,4-methano- (1-methylethyl)-1,2,4-
farnesane numbering system is used. 1H-indene, 9CI metheno-1H-indene, 9CI

XXX
 The diterpenoids

Tbujopsanes Sq-02697-sq-02702
13 13
Thujopsanes are found in higher plants whilst ent-
thujopsanes are found in liverworts. The biogenetic
farnesane numbering system is used.
15 15

Sinularane Cyclosinularane 14
Octahydro-7a,8-dimethyl-5- Octahydro-1 ,4-dimethyl-7-
(1-methylethyl)-1 ,4-methano- (1-methylethyl)-1 ,2,4-
1H-indene, 9CI metheno-1H-indene, 9CI 15

12 13

Thujopsane
Decahydro-2,4a,8,8-tetramethylcyclopropa[d]naphthalene, 9CI

CopaiUles Sq-02684-Sq-02688
Copaanes can either be considered as 5,10-cyclo-
cadinanes or 1,6-cycloeudesmanes. BourboniUles Sq-02703-sq-02706
Bourbonanes are 6,10-cycloguaianes. A guaiane
14
numbering system is used.

14

15

Copaane
1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02 ' 7]decane, 9CI
Bourbonane
Decahydro-3a,6-dimethyl-1-(1-methylethyl)cyclobuta[1 ,3 : 3,4]-
dicyclopentene, 9CI

lsbwaranes Sq-02689-Sq-02693
The ishwaranes form a small group of 10,12-cyclo- GymnomitriUles Sq-02707-sq-02712
eremophilanes from Aristolochia spp. 7,11- And
Gymnomitranes are biogenetically related to
8,11-seco derivatives are known and are included in
this group. cuparanes. A farnesane numbering system is used
here.
15 12

15 14 13

Ishwarane Gymnomitrane
Decahydro-1 ,6,6a-trimethyl-1 ,2a-methano- Decahydro-3a,4, 7 ,Sa-tetramethyl-4,8-methanoazulene, 9CI
2aH-cyclopropa[b]naphthalene, 9CI

MisceiiiUleous sesquiterpenoids Sq-02713-Sq-02835

RotundiUles Sq-02694-Sq-02696 Sesquiterpenoid skeletons that do not fit easily into
The rotundanes are 10,12-cycloguaianes. the above categories are collected here. They are
divided into bicyclic, tricyclic and tetracyclic
14
sesquiterpenoids.

15
Diterpenoids Di-00001-Di-02494
Rotundane The diterpenoids constitute a large group of
Decahydro-1 ,4,6-trimethyl-4,7-ethanoazulene, 9CI compounds derived from geranylgeranyl pyro-

xxxi
Description of Main Terpenoid Types

phosphate [7, 28, 29, 30]. They are found in higher

plants, fungi, insects and marine organisms. 15

Phytanes Di-00001-Di-00084
Labdane Halimane
Phytanes are regular acyclic diterpenoids. The Decahydro-1 ,1 ,4a,6-tetra- Decahydro-1,1,5,6-tetra-
phytane numbering system is shown here. methyl-5-(3-methyl- methyl-5-(3-methyl-
pentyl)naphthalene, 9CI pentyl)naphthalene
17 18 20

11 4 3 12 14
16 12 10 6
15

Phytane
2,6,10,14-Tetramethylhexadecane

Prenylbisabolanes and 10,15-Cydophytanes
Di-00112-Di-00144
The prenylbisabolanes arise by cyclisation between
carbons 1 and 6 of the phytane skeleton. They retain
their phytane numbering system. The 10,15-
cyclophytanes are important compounds including
the retinal group. Since 10,15-cyclophytanes
resemble carotenoids, a carotenoid-like numbering
system has usually been adopted. It is possible to view
10,15-cyclophytanes as 9,10-secolabdanes and some
are named as such in the literature.
19 18 17
Gnaphalane
Colensane6 and Clerodanes Di-00568-Di-00877
Colensanes are a small group of 4(3 ~ 2)abeo-
labdanes. Clerodanes arise from labdanes by two
methyl migrations. They are abundant and are found
particularly in Teucrium spp. where they are highly
oxygenated [31]. In the past ent-clerodanes have been
named as neoclerodanes and kolavanes but these
names are not widely used.
12
15
15

15 16
3

19 ',
18 18
Prenylbisabolane
Colensane ent-Clerodane
1-Methyl-4-(1 ,5,9-trimethyldecyl)cyclohexane
Octahydro-1,1,2,3a,5- Decahydro-1 ,2,4a,5-
pentamethyl-4-(3-methyl- tetramethyl-1-(3-methyl-
pentyl)-1H-indene pentyl)naphthalene, 9CI

15
14 Abietanes Di-00878-Di-01071
Abietanes may arise from pimaranes by migration of
10,15-Cyclophytane the methyl group at C-13. This large group is divided
1 ,1 ,3-Trimethyl-2-(3, 7-dimethylnonyl)cyclohexane into sections including furanoabietanes, seco-
abietanes and secofriedoabietanes, nor- and homo-
abietanes, abeoabietanes and abietane dimers.
16

Labdanes and Halimanes Di-00145-Di-00567

Labdanes form a large group and occur in both
enantiomeric series. The halimanes are derived from
labdanes by migration of the methyl group C-10 to Abietane
C-9. Nor-, seco- and rearranged labdanes, including Tetradecahydro-1 ,4,4a-trimethyl-7-(1-methylethyl)-
the gnaphalanes, are presented in separate sections. phenanthrene, 9CI

xxxii
 The diterpenoids

13,16-Cydoabietlmes 1111d 17(15-16)-A.beoabietsnes
Di-01072-Di-01113
These groups include the coleons, lanugones and
plectranthones from Coleus and Plectranthus spp.
Included in each group are the corresponding
19(4-3)-abeo derivatives.
the isopimaranes they are anti. Both pimaranes and
isopimaranes occur in both enantiomeric series.
Rosanes arise by migration of the C-10 methyl group
of pimaranes to C-9. 13-epi-Rosanes, e.g. Rimuene
arise in a similar manner from isopimaranes.
Erythoxylanes, parguaranes and devadaranes
represent a further degree of rearrangement of

Q?.J
16 16
pimaranes and isopimaranes.
17
17

19

18

13,16-Cycloabietane 19(4.- 3)-Abeo-13,16-cyclo-

abietane Pimarane Isopimarane
7-Ethyltetradecahydro-
1S 17
1S
1,1,4a,7-tetramethyl-
phenanthrene

p 16

19

18

17(15.-16)-Abeoabietane 17(15.-16), 19(4.-3)-

Tetradecahydro-1,1,4a- Bisabeoabietane
18
trimethyl-7-propyl- Tetradecahydro-1 ,2,4a-
phenanthrene trimethyl-7-propyl- Rosane Erythroxylane
phenanthrene 7-Ethyltetradecahydro- 7-Ethyltetradecahydro-
1,1,4b,7-tetramethyl- 1,4b,7 ,10a-tetra-
phenanthrene methylphenanthrene

Totaranes 1111d the Nagilactone group

Di-01114-Di-01148
The totaranes may arise from abietanes by migration
of the isopropyl group from C-13 to C-14. They
normally have an aromatic ring C and are found in Paraguarane Devadarane
several species of higher plants. The nagilactone 5-Ethyltetradecahydro- 8-Ethyltetradecahydro-
group are seco, nor-totaranes that are found in 1a,5,7b-trimethyl-1H- 3a,8,10a-trimethyl-
Podocarpus spp. cyclopropa[a]phenanthrene cyclopropa[j]phenanthrene

16 Cassanes 1111d Vouacapanes Di-01321-Di-01355

Totarane
Tetradecahydro-1 ,4,4a-
trimethyl-8-(1-methyl-
ethyl)phenanthrene
The cassanes presumably arise by methyl migration in
the pimarane skeleton from C-13 to C-14. The
Erythrophleum alkaloids are simple derivatives of
Nagilactone skeleton
cassanes and they are included in this section.
Furanocassanes are called vouacapanes.

16

Pimaranes, Rosanes, Erythroxyl1111es, Paraguaranes,

Devadaranes and lsopimaranes Di-01149-Di-01320
The pimaranes and isopimaranes (formerly called
Cassane Vouacapane skeleton
sandaracopimaranes) arise by further cyclisation of 7-Ethyltetradecahydro-
the labdane skeleton. Pimaranes have the ethyl group 1 ,1 ,4a,8-tetramethyl-
at C-13 syn- to the methyl group at C-10 whereas in phenanthrene

xxxiii
Description of Main Terpenoid Types

Cleistsntbanes and Isocleistantbanes

Di-01356-Di-01373 17 17

The cleistanthane skeleton arises from pimaranes or

isopimaranes by the migration of the ethyl group
from C-13 to C-14. Isocleistanthane is a 2(4-3)-
abeocleistanthane. ent-Kaurane Phyllocladane
==Kaurane, 9CI =:5a,9a,lOP-Kaurane, 9CI

Beyeranes Di-01710-Di-01746
Beyeranes are formed by cyclisation of a pimarane
19
18 cation intermediate without rearrangement. Most
Cleistanthane lsocleistanthane skeleton beyeranes belong to the ent-series. ent-Beyerane is
8-Ethyltetradecahydro- also known as stachane. Chemical Abstracts names
1,4,4a,7-tetramethyl- ent-beyeranes as 13-methyl-17-norkauranes.
phenanthrene

lsocopalanes and Spongianes Di-01374-Di-01423

Isocopalanes and spongianes are of marine origin and
both have the same carbon skeleton. A spongiane or
spongian is a 15,16-epoxyisocoplane. ent-Beyerane

Villanovanes, Atisanes, Trachylobanes and

Helrifulvanes Di-01747-Di-01795
Rearrangement of the beyerane cation intermediate
produces the villanovane and atisane skeletons.
lsocopalane Spongiane skeleton
Tetradecahydro-l,l,4a,7,8,8a- Rearrangement of the beyerane cation intermediate
hexamethylphenanthrene followed by cyclisation leads to the trachylobane and
helvifulvane skeletons. These skeletons are mostly
found in the ent-series. ent-Atisane and ent-
Podocarpanes Di-01424-Di-01441 trachylobane are trivially named in CA as a tisane and
trachylobane (see remarks under kaurane, above).
Miscellaneous podocarpane derivatives that cannot
be easily classified are collected in this section. 17

4 4

Kauranes and PhyHocladanes Di-01442-Di-01709 1s ·.H

19
H
18 '.
19
ent-Villanovane ent-Atisane
The kauranes arise by further cyclisation of pimarane Tetradecahydro-4,4,8,llb- ==Atisane, 9CI
cation
r
intermediate followed by rearrangement (30). tetramethyl-9 ,lla-methano-
Most kauranes occur in the ent-series. The less llaH-cyclohepta(a]-
common phyllocladanes have the methylene bridge naphthalene, 9CI
on the opposite side from the methyl at C-10. Nor-,
12
seco- and rearranged kauranes are placed in separate
sections. The seco-kaurane group includes the
Rabdosia constituents, e.g. Enmein [32). Care should
be taken when using Chemical Abstracts for this
skeleton as ent-kaurane is taken as the stereoparent
and is named kaurane; 19-substituted ent-kauranes
are named as having a (4a )-18-substituent and phyllo- ent-Trachylobane ent-Helvifulvane
==Trachylobane, 9CI Tetradecahydro-4,4,7a,9b-
cladanes are named as (5a,9a,10P)-kauranes. CA tetramethyl-8,8a-methano-
also uses Enmein as a basis for naming some of the 9aH-cyclopropa(b]-
seco-kauranes. phenanthrene, 9CI

xxxiv

Aphidocolanes Di-01796-Di-01798
This small group includes the biologically active
aphidicolin and the stemodin type from Stemodia
maritima. The methano-bridge stereochemistry is
opposite in aphidicolin and stemodin.
17
Aphidicolane
4,4,17-Trirnethyl-9 ,15-cyclo-C, 18-dinor-14, 15-secoandrostane
Gibberellins Di-01799-Di-01836
The gibberellins, important plant hormones, are
based on the ent-gibberellane skeleton. They are
produced by higher plants and the rice plant infecting
fungus Gibberella fujikuroi. They have also been
isolated from red and green algae [33, 34, 35]. The
biosynthesis of the gibberellins has been well studied
and it is clear that they are derived from ent-kaurene.
The biosynthesis and bibliography of this class have
been recently reviewed [36]. In CA they are named as
derivatives of the stereoparent gibbane, which is a
C15 skeleton and has a completely different
numbering scheme. Many of the natural gibberellins
are c19 norditerpenes.
17
ent-Gibberellane Gibbane, 9CI
The Leucothol group and the Grayanotoxanes
Di-01837-Di-01858
The leucothol group and the grayanotoxins are also
rearrangement products of the ent-kaurane skeleton.
Leucothol skeleton Grayanotoxane, 9CI
XXXV
The diterpenoids
Cembranes Di-01859-Di-01960
The cembranes form a large group of diterpenoids
found in higher plants (e.g. tobacco and conifers),
insects and marine organisms. The cembrane nucleus
has a plane of symmetry and is conventionally drawn
with C-7 at the top as defined by the C-1, C-8 axis, C-7
being chosen as bearing a double bond or equivalent
[37]. The numbering system shown is generally
accepted. Many polycyclic diterpenoids can be
regarded as formally arising by cyclisation of the
cembrane skeleton (or the related casbane skeleton-
see below). As with germacranes, care is necessary in
interpreting published configurations at centres
involving reentrant angles.
18
20
Cembrane
1,7,11-Trirnethyl-4-(1-methylethyl)cyclotetradecane
Rearranged cembranes Di-01961-Di-01996
This group contains assorted, unusual macrocyclic
diterpenoids including a basmanc derivative which is
formally a cyclised (2,12: 7,11) cembrane.
18
19
17
Basmane
Eunicellanes and Asbestinanes
Di-01997-Di-02007
These are marine natural products. The eunicellane
(cladiellane) skeleton is formally a 5,14-cyclo-
cembrane and the cembrane numbering system is
preferred. The closely related asbestinane group has
been ascribed a different numbering system.
19
20
Eunicellane Asbestinane
Description of Main Terpenoid Types

Sphaeranes Di-02008-Di-02014 used. The modified dolastane group contains 8,9-

secodolastanes and a chromophycane, a new skeletal
The bromosphaerol group of marine natural products
type related to dolastane by migration of the methyl
contains an unusual carbon skeleton. The numbering
C-20 to C-13.
system is as shown. Bicyclic (lacking the 1,10-bond) 18
and tetracyclic (with a 2,17-bond) derivatives are 19

known. (N.B. Sphaeranes are not to be confused with

sphaeroanes, see above).

15
Dolastane
Tetradecahydro-3a ,5 ,8a-trimethyl-1-(1-methylethyl)-
benz(flazulene, 9CI

Sphaerane
Tetradecahydro-5 ,Sa, lOa-trimethyl-1-(1-methylethyl)-
phenanthrene Cyathanes Di-02099-Di-02109
The cyathanes are fungal metabolites. The
Briaranes Di-02015-Di-02045 biosynthesis of this unusual skeleton has been studied
[38]. The accepted numbering system is as shown.
The briaranes are marine diterpenoids with the 17

numbering system as shown. The carbon skeleton is

formerly a 3,8-cyclocembrane.
15
16
19

15

Cyathane
18 Tetradecahydro-3a,5a,8-trimethyl-1-(1-methylethyl)-
Briarane cyclohept(e]indene

DolabeHanes and modified dolabeHanes

Sphaeroanes Di-02110-Di-02113
Di-02046-Di-02074
The sphaeroanes are marine algal products with a
Dolabellanes are found in marine organism and in
skeleton which is formally a 2,7-cyclodolabellane
liverworts. Several numbering systems have been
though the numbering system is different from that of
used in the literature. We have used the one shown.
The modified dolabellane group includes the neo- dolabellanes.
20
dolabellanes in which a methyl has migrated from C-1 19

to C-11. A rare 3,9-cyclodolabellane is also included

in this group. 16

20 20
19 19

15

Sphaeroane
Dodecahydro-3a,6,9-trimethyl-3-(1-methylethyl)-
16 16
benz[e]azulene, 9CI
Dolabellane Neodolabellane

Dolastanes and modified dolastanes Verrucosanes and modified yerrucosanes

Di-02075-Di-02098
The name clavularane was originally used for this
group of marine natural products but now dolastane
appears to be widely accepted. Dolastane is a 3,8-
cyclodolabellane but a different numbering system is
Di-02114-Di-02121
Verrucosanes and their modifications, including neo-
verrucosanes, are liverwort natural products. The
tetracyclic verrucosane skeleton is formally related to
dolabellane by 4,10- and 6,8-bond formation. A

xxxvi
 The diterpenoids

different numbering system from that of dolabellane
is used. The isomeric neoverrucosane has the
cyclopropane bridging C-2 and C-3.
17
formally a 6,10-cyclocasbane. There is some
confusion in the literature over the configuration of
the methyl group attached to C-13. Reentrant angles
should be avoided if possible.
20

4
16

1,9

Verrucosane Lathyrane
Tetradecahydro-3a,5a, 7a-trimethyl-1-(1-methylethyl)- Tetradecahydro-1, 1 ,3,6,9-pentamethyl-1H-cyclopenta[a1-
cyclopent[a1cyclopropa[g1naphthalene, 9CI cyclopropa[flcycloundecene

Casbanes Di-02123-Di-02127
Rhamnofolanes and Daphnanes Di-02149-Di-02164
The casbane skeleton is closely related to cembrane
The rhamnofolane and daphnane skeletons are
and it seems logical to use the cembrane numbering
closely related, being formally derived from casbane
system although many others have been used in the
by two cyclisations (6,10 and 5,14) followed by
literature. Casbane, like cembrane, is the formal
cleavage of the 1,15 (daphnane) or 2,15 (rhamno-
parent of several important groups of diterpenoids
folane) cyclopropane bonds. For a review see (39].
especially from the Euphorbiaceae and Thymelae-
16
ceae [39]. Berdimerane has a rearranged casbane
skeleton. 17

18

19 19
19

20 20

Rhamnofolane Daphnane
20 (N .B. in CA, Daphnane is an
Casbane alkaloidal stereoparent.
3,7,11,15,15-Pentamethylbicyclo[12.1.01pentadecane, 9CI Terpenoid daphnane
derivatives are named as
derivatives ofDaphnetoxin)

Jatrophanes and Cyclojatrophanes

Di-02128-Di-02136
Jatrophane is the parent skeleton of a group of
macrocyclic diterpenoids from Euphorbia species
[39]. Formally it can be derived from casbene by 6,10-
cyclisation and opening of the cyclopropane. The
numbering system shown is used fairly consistently in
all the related diterpenoids of this series. Two
examples of the 9,13-cyclojatrophane skeleton have
been isolated.
20
Tiglianes and Ingenanes Di-02165-Di-02171
The tigliane nucleus is formerly derived from casbene
by 6,10- and 5,14-cyclisations. This is the carbon
framework of phorbol whose derivatives occur widely
in the Euphorbiaceae and are renowned for their
tumour promoting and irritant activity (39]. The
ingenane skeleton is derived by rearrangement of
tigliane. Ingenane esters have irritant properties.

16
18

19 19
Jatrophane
20
20
Tigliane Ingenane
Tetradecahydro-1,1,3,6,8- Dodecahydro-1 ,4, 7,9-
Lathyranes Di-02137-Di-02148 pentamethyl-1H-cyclo- pentamethyl-1H-2,8a-
propa[3 .41benz[1 ,2-e1- methanocyclopenta[a1-
Derivatives of the lathyrane skeleton occur M.dely in azulene, 9CI cyclopropa[e1cyclo-
the Euphorbiaceae as mixed esters [39]. Lathyrane is decene,9CI

xxxvn
Description of Main Terpenoid Types

JatrophoiBBes BBd crotofolues Di-02178-Di-02182 numbering system is used. Only a few members of
this group have been reported.
Jatropholanes arise by 5,13- and 6,10-cyclisation of
casbane. Subsequent cleavage of the 2,15- 18
cyclopropane bond affords crotofolane. Only a few
examples of these skeletons have been reported [39).

16
Verticillane
4,8, 12, 15, 15-Pentamethylbicyclo[9 .3 .1 )pentadecane, 9CI

Jatropholane
Hexadecahydro-1, 1,2,5, 7-
pentamethyl-6H-cyclo-
propa[3,4)cyclohept-
[1,2-e)indene
FusicoccBBes Di-02183-Di-02205
Crotofolane
Tetradecahydro-2,5, 10- TaxBBes Di-02232-Di-02250
trimethyl-6-(1-methyl-
ethyl)cyclohept[e]- The taxanes form an important group of biologically
indene,9CI active diterpenoids and alkaloids from Taxus spp.
The skeleton is related to verticillane by a further
cyclisation. The accepted numbering system is as
shown.

Fusicoccanes occur in fungi and liverworts.

Biosynthetic evidence [38) favours the involvement
of a dolabellane-like precursor. The accepted
numberi~g system differs from that of dolabellane.
20
19
20 Taxane
Tetradecahydro-4,9,12a,13,13-pentamethyl-
6,10-methanobenzocyclodecene, 9CI

16 Trinervitanes BBd Kempanes Di-02251-Di-02266

Fusicoccane
Tetradecahydro-1 ,4,9a-trimethyl-7-(1-methylethyl)- The trinervitanes, 7 ,16-secotrinervitanes, 17-methyl-
dicyclopenta[a,d)cyclooctene, 9CI trinervitanes and kempanes are constituents of the
defence secretions of termites. Kempanes are 11,15-
cyclotrinervitanes. The numbering system of these
unusual diterpenoids is as shown.
Spatanes Di-02206-Di-02227
19
The spatane skeleton is formally derived from a 19

prenylgermacrane by 1,5- and 6,10-cyclisation. The

numbering system unfortunately does not reflect this 20

derivation. Spatanes and the related 4,10-

secospatanes are marine natural products. 14

12
Trinervitane Kern pane
Hexadecahydro-1 ,4,8,12- Hexadecahydro-2a,7 ,10,10c-
tetramethyl-1 ,11-ethano- tetramethylnapth[2, 1 ,8-cde]-
cyclopentacycloundecane, 9CI azulene, 9CI
20

Spatane
Decahydro-3a,6-dimethyl-1-(1 ,5-dimethylhexyl)cyclobuta-
[1,2: 3,4)dicyclopentene, 9CI
VerticiiiBBes Di-02228-Di-02231
The verticillane group is formally derivable from
cembrane by an 11,15-cyclisation. A non-cembrane
AmphHectanes, CycloamphHectanes BBd AdociBBes
Di-02267-Di-02277
The amphilectanes (including the pseudopterosins),
the cycloamphilectanes and adocianes are marine
products. They are found with serrulatane derivatives
from which amphilectanes are presumably derived by
cyclisation. Cycloamphilectanes represent a further

xxxviii
 The diterpenoids

cyc11sat1on and adocianes have undergone a methyl Eremanes Di-02333-Di-02335

migration. Eremanes have an unusual carbon skeleton. They are
16
isolated from Eremophila spp.
17

20

19
19

Amphilectane Cycloamphilectane
Dodecahydro-1,4,7-trimethyl- Hexadecahydro-1,4,7 ,7- 12
3-(2-methylpropyi)-1H- tettamettiylpyrene Eremane
phenalene, 9CI Decahydro-1 ,5,5-trimethyl-4-(4-methylpentyl)-
3a,6-ethano-3aH-indene
16

17
Prenyleudesmanes, Prenylgermacranes and
Prenylbicyclogermacranes Di-02336-Di-02348
19
These three groups of 'extended' sesquiterpenoid
Adociane
skeletons are largely of marine origin.
Hexadecahydro-1 ,2,5,8-tetramethylpyrene, 9CI 19

Xenicanes and XeniapbyDanes Di-02278--Di-02330 16 16

Xenicanes and xeniaphyllanes are marine natural 20 18 17 17

products. Various nor-, seco- and cyclo-xenicanes Prenyleudesmane Prenylgermacrane

Decahydro-7-(1 ,5-dimethyl- 4-(1,5-Dimethylhexyl)1,7-
are placed in a separate section. Xeniaphyllanes hexyl)-1 ,4a-dimethyl- dimethylcyclodecane
are the diterpenoid equivalent of the caryophyllane naphthalene
skeleton. Xenicanes are cleaved xeniaphyllanes.
16
17

15
16
17

20 20 Prenylbicyclogermacrarie
3,7,11-Trimethyl-11-(4-methylpentyl)bicyclo[8.1.0)undecane

19 19

Xenicane Xeniaphyllane Lobanes Di-02349-Di-02355

1 ,2,6-Trimethyl-3- 2,6,10-Trimethyl-10-
(1 ,5-dimethylhexyl)- (4-methylpentyl)- Lobanes are of marine origin and are 'extended'
cyclononane bicyclo[7 .2.0Jundecane elemanes. A most unusual non-standard system is
used in the literature.
Viscidanes Di-02331-Di-02332
Viscidanes, from Eremophila spp., are the 11 20
diterpenoid equivalents of the acoranes.
12 14
19
Lobane
4-(1 ,5-Dimethylhexyl)-1-ethyl-1-methyl-2-
20
(1-methylethyl)cyclohexane

12

Prenylguaines and Prenylaromadendranes

Di-02356-Di-02376
16

Viscidane These two groups are also 'extended' sesquiter-

1,8-Dimethyl-4-(1 ,5-dimethylhexyl)spiro[4.5)decane penoids. The prenylguaianes, including the dictyols,

xxxix
Description of Main Terpenoid Types

are of marine origin and the prenylaromadendranes 11

are found in leaves of Cneorum ·tricoccon. 12

18 14

16

20 19 18 20
19 20
Sacculatane
Prenylguaiane Prenylaromadendrane Decahydro-1 ,4a,5 ,6-tetramethyl-1-( 4-methylpentyl)naphthalene
Decahydro-7-(1 ,5-dimethyl- Decahydro-1,4,7-trimethyl-1-
hexyl)-1 ,4-dimethyl- (4-methylpentyl)-1H-
azulene cycloprop[e)azulene Obtusanes Di-02400-Di-02401
The obtusanes, from Laurencia obtusa, are bicyclic
Serrulatanes and binoranes Di-02379-Di-02392 phytanes. The numbering system is almost the same
The serrulatane skeleton is found in marine as for phytane. (Note that the terpenoid Obtusane
organisms, insects and Eremophila spp. The skeleton itself is a chamigrane).
is an 'extended' cadinane. The serrulatane name is 16

given to the aromatic derivative. Unfortunately

different numbering systems have been given to
serrulatanes and bifloranes. 19 20 17
Obtusane
20 19
1 ,1 ,3-Trimethyl-2-[3-(4-methylcyclohexyl)butyl)-
cyclohexane

19 20
The ireol group Di-02402-Di-02407
The ireol group from Laurencia spp. represents an
unusual diterpenoid skeleton.
18

Serrulatane Biflorane
Decahydro-4-(1 ,5-dimethyl-
hexyl)-1 ,6-dimethyl-
naphthalene

Decipianes Di-02393-Di-02394 Ireol skeleton

Octahydro-1-[ (3 ,3-dimethylcyclohexyl)methyl]-
Decipianes from Eremophila spp. are cyclised 3a, 7-dimethyl-1H-indene
bifloranes. Yet another numbering system is used for
this skeleton.
20
Sphenolobanes Di-02408-Di-02416
The sphenolobane skeleton is an 'extended' daucane
19 skeleton.
20

11

Decipiane
12
Decahydro-1 ,2,5-trimethyl-1-(4-methylpentyl)-
Sphenolobane
1H-cyclobuta[de)naphthalene, 9CI
Decahydro-1-(1 ,5-dimethylhexyl)-3a,6-dimethylazulene

Sacculatanes Di-02395-Di-02399 Miscellaneous diterpenoids Di-02417-Di-02494

Sacculatanes are 'extended' drimanes and are found Diterpenoids that do not easily fit into the other
in liverworts. categories are collected here. Mono-, bi-, tri- and

xl
 The sesterterpenoids

tetra-cyclic diterpenoids are placed in separate 24 25

sections.

Sesterterpenoids St-00001-St-00117 16 18

Sesterterpenoids are a small group of natural Cericerane

1-(1 ,5-Dimethylhexyl)-4 ,8, 12-trimethylcyclotetradecane
products that arise from five isoprene units [40, 41].
Although sesterterpenoids strictly have 25 carbons,
there are many nor- and alkylated members. Also
included here are the C21 acyclic terpenoids although
their biosynthetic relationship with the sesterpenoids
Bicyclic sesterterpenoids St-00046-St-00056
has not been established [42]. Sesterterpenoids are
found in fungi, higher plants, insects and marine Various bicyclic sesterterpenoids are known. Some
organisms. are prenylated analogues of diterpene skeletons and
the numbering systems are related to the
corresponding diterpenoid systems. Others have
Acyclic and noracyclic sesterterpenoids biogenetic numbering systems.
St-00001-St-00033 12 14 16 18
19
The acyclic sesterterpenoids arise by a head to tail 15

fusion of isoprene units. The accepted numbering 20

system is used here. The noracyclic sesterterpenoids

are numbered in a similar way; however, a problem
arises with the symmetry of the c21 compounds as
they may be numbered from either end. The acyclic
19
sesterterpenoids frequently contain furanoid rings.
21 22 23 24 25
13
11
20 18 16 14 12 10
24
Acyclic sesterterpenoid skeleton
2,6,10,14,18-Pentamethylicosane 24

14

c21 sesterterpenoid skeleton

3, 7,11,15-Tetramethylheptadecane
21

25
Cyclohexane sesterterpenoids St-00034-St-00039
Most of the cyclohexane sesterterpenoids arise by
cyclisation of the acyclic skeleton between carbons 14
and 19.
20

12 10 6 4
11 Some bicyclic sesterterpenoid skeletons
21 20 23 24 25

Cericeranes St-00040-St-00045
CheHanthanes and Ophiobolanes St-00057-St-00073
Cericeranes arise by cyclisation between carbons 1
and 14 of the acyclic skeleton, retaining the The accepted numbering systems for the cheil-
numbering system. The symmetry of the cyclo- anthanes and ophiobolanes are shown here.
tetradecane ring leads to some ambiguity of Chemical Abstracts uses ophiobolane as a stereo-
numbering. parent (see Appendix IV in the current Chemical

xli
Description of Main Terpenoid Types

Abstracts Index Guide); however it uses a different 2,3-epoxide adopts when the initial cyclisation takes
numbering system for the non-ring carbons. place determines the stereochemistry of the ring
12
junctions in the triterpenoid produced. Thus
cyclisation of the chair-boat-chair-boat conformation
9
gives the protostane cation and cyclisation of the
chair-chair-chair-boat conformation leads to the
dammarane cation. The initially formed cation
21 20 intermediate may undergo a series of 1,2-hydride and
Cheilanthane methyl migrations, commonly called backbone re-
4,4,8-Trimethyl-D(15) ,24- arrangements, to give a variety of skeletal types.
dinor-13,17-secocholane, 9CI

25

Squalene

20
Ophiobolane

21

Squalene 2,3-epoxide

24
Ophiobolane, CA numbering

Scalaranes St-00074-St-00101 Cation intermediate

The scalarane numbering system is shown here.

Carbons 12, 24 and 25 are generally oxygenated in
this skeleton. A few methyl and dimethyl scalaranes
are found in marine organisms.
25
24
Scalarane
4,4,8,17, 17a-Pentamethyl-D-homoandrostane, 9CI
Triterpenoids Tr-00001-Tr-01508
The triterpenoids constitute a large diverse group of
natural products derived from squalene [43, 44].
They are best classified biogenetically [2] and the
discussion that follows is based on such
considerations. In general triterpenoids arise by
cyclisation of squalene or, in the case of 3P-hydroxy-
triterpenoids, the 3S- isomer of squalene 2,3-
epoxide. The conformation that all-trans-squalene
Backbone rearrangement of the protostane cation
below gives the lanostane skeleton; lanosterol is the
biogenetic precursor of the steroids. The methyl
groups at carbons 4 and 14 are removed during
steroid biosynthesis. The steroid numbering system is
adopted for lanostane and related tetracyclic
triterpenoids. The three methyl groups that were
removed during the biosynthesis of steroids are
currently numbered as 28, 29 and 30 as shown.
However, older literature uses the numbers 31, 30
and 32, respectively. This was based on the
assignment of carbon numbers 28 and 29 to the
stigmastane ethyl group, even though most lanostanes
do not have such an ethyl group. The numbering in
this Dictionary follows the currently accepted
convention.
24
27
Lanostane numbering Steroid numbering

xlii
 Nomenclature of tetracyclic triterpenoids in Chemical Abstracts

The main tetracyclic triterpenoid skeletons have the »ouycoccenes Tr-00016-Tr-00025

steroid numbering for the skeleton including the side
The alga Botryococcus braunii produces a series of
chain and only the methyl groups will be numbered in
branched alkylated isoprenoid hydrocarbons based
the structures that follow. As a general rule the
on botryococcane. The names of individual
methyls which migrate during terpenoid biosynthesis
compounds indicate the number of carbons, e.g. C34
retain their numbering.
botryococcene. Of the several numbering systems
that have been used, the one below is preferred.
23 24

Nomenclature of tetracyclic triterpenoids in 22

Chemical Abstracts
28 29 30

CA uses stereoparents as a basis for the nomenclature C30- Botryococcane

of steroids (see Appendix IV in the current Chemical 10-Ethyl-2,6,10,13,17,21-hexamethyldocosane
Abstracts Index Guide). This has the advantage that
compounds with the same carbon skeleton are listed
together in CA but has the disadvantage that some
tetracyclic triterpenoids are assigned different names Protostanes and fusidanes Tr-00026-Tr-00039
from those commonly used. The CA names for some The protostanes, e.g. protosterol, form a small group
common skeletons are listed below. that arise from cyclisation of squalene or its 2,3-
epoxide without backbone rearrangement. The
Chemical Abstracts name fusidanes form a small but important group of anti-
Protostane Dammarane, (8a, 9{J, 13a, 14{3)- biotics, e.g. fusidic acid, which lack one of the methyl
Fusidane 29-Nordammarane, (4a, Sa, 13a, 14{3)- groups at carbon 4. The numbering and stereo-
Cycloartane 9, 19-Cyclolanostane chemistry of these skeletons is indicated below.
Cucurbitane 19-Norlanostane, 9-methyl-, (9{J, lOa)-
Euphane Lanostane, (13a, 14{3, 17a)- ~·y
Tirucallane Lanostane, (13a, 14{3, 17a, 20S)- I;I:
I
Apotirucallane Cholestane, 4,4,8-trimethyl-,
(13a, 17a, 20S)

The CA nomenclature of some other triterpenoids is

2s
idiosyncratic, e.g. Malabaricanes. 29

Protostane Fusidane

Linear triterpenoids Tr-00001-Tr-00015 Lanostanes Tr-00040-Tr-00202

This group contains simple derivatives of squalene.
The preferred numbering system is shown and is used
for the related polyether derivatives found in marine
algae, e.g. Laurencia spp. Also included are C30
polyprenols, and some homo- and nor-squalenes.
Squalene is formed biosynthetically from famesyl
pyrophosphate via presqualene pyrophosphate [45].
25 26 27
Backbone rearrangement of the protostane cation
leads to the lanostanes, a large group. They are
uncommon in plants but some fungi are a prolific
source. Some rearranged lanostanes are also included
in this section.

24
0

28 29 30

Squalane Lanostane
2,6,10,15,19,24-Hexamethyltetracosane, 9CI

011 011 ~--~

K, · """1 . """r
I
Cycloartanes Tr-00203-Tr-00313
HO-~-O-r-OH2C ---~
OH ow H Backbone rearrangement of the protostane cation
Presqualene pyrophosphate including cyclisation to form a 9,19 bond produces the

xliii
Description of Main Terpenoid Types
cycloartane skeleton. Plants use cycloartenol and not
lanosterol for the biosynthesis of phytosterols.
Cycloartane
Cucurbitanes Tr-00314-Tr-00347
More extensive backbone rearrangement of the
protostane cation affords the cucurbitane skeleton:
The cucurbitacins, e.g. cucurbitacin A are found in
the Cucurbitaceae and are of interest bacause of their
biological activity [46). Many occur as glycosides.
Cucurbitane
IJsmmlmmes Tr-00348-Tr-00428
Collapse of the dammarane cation without backbone
rearrangement leads to the dammarane skeleton (a
stereoisomer of protostane). Dammaranes often
occur as glycosides and are commonly found among
the saponins of ginseng [47].
Dammarane
Euphanes and tirucallanes Tr-00429-Tr-00482
Backbone rearrangement of the dammarane cation
(analogous to the protostane-lanostane rearrange-
ment) yields the euphane skeleton and its 20-epimer,
the tirucallane skeleton. There is frequent confusion
in the· literature about the stereochemistry at
carbon-20 in these compounds.
xliv
Euphane Tirucallane
Apotirucallanes Tr-00483-Tr-00495
Further rearrangement of the tirucallane skeleton,
the apo-rearrangement, affords the apotirucallane
skeleton. Apotirucallanes are the notional parents
of the tetranortriterpenoids (limonoids) and the
quassinoids.
wo
18~
29 '
28
Apotirucallane
Nortriterpenoids Tr-00496-Tr-00676
The tetranortriterpenoids (limonoids) [48] are
formed by loss of four terminal carbons of the apo-
tirucallane skeleton. The side chain is typically a
,8-substituted furan although other oxidation levels
are found to a lesser extent. A series of ring-cleavages
and rearrangements can lead to a wide range of
structures. For example cleavage of rings B and C
may be followed by cyclisation to form a bicyclo-
[3.3.1]nonanolide system. These compounds are
presented in three groups - tetranortriterpenoids,
ring cleaved derivatives and rearranged derivatives.
The last group contains the bitter principles of the
Cneoraceae, e.g. Cneorin C [49].
() ()
#
29 :is
Tetranortriterpenoid A tetranortriterpenoid with
skeleton rings B and D cleaved
 Nomenclature of tetracyclic triterpenoids in Chemical Abstracts

like numbering system is used. This cyclisation of

squalene provides an entry into the pentacyclic
triperpenoids.
7
MeOOC
l 0

0
A bicyclo[3.3.1 ]nonanolide tetranortriterpenoid
Baccharane
D: B-Friedo-18,19-secolupane, 9CI

Quassinoids Tr-00677-Tr-00729
The quassinoids are found in the Simaroubaceae
family [50] and are closely related to the tetra-
nortriterpenoids. This relationship is emphasised by
Lupanes Tr-00733-Tr-00809
the presence of several c25 precursors (e.g.
simarolide) which lose a further five carbon atoms to Formation of a five membered ring E from the
give the C20 picrasane skeleton. C18 and C19 baccharane precursor affords the lupane skeleton
quassinoids are also known but are less common. The whose numbering system is as shown. 3(2~ 1)-Abeo-
quassinoids have attracted much synthetic effort lupanes and assorted nor-, friedo- and seco-lupanes
because of their cytotoxic activity. Chemical are included in separate groups.
Abstracts uses the picrasane skeleton as a stereo-
parent, however the numbering system used by
Chemical Abstracts differs from the accepted system;
the oxygen atom is numbered.

23

Lupane, 9CI
28
is C2s Quassinoid Picrasane (C2 0 )-
(23/24 substituents specified in CA as (4a)23- and
(4P)23- respectively)
skeleton usual numbering

0/eananes Tr-00810-Tr-01082
Forination of a six-membered ring E from the
18 baccharane precursor leads to the oleanane group.
Picrasane, CA-numbering Oleananes form the largest group of triterpenoids
and occur widely in the plant kingdom often as
glycosides [51, 52].

Baccharanes Tr-00730-Tr-00732
Cyclisation of squalene or squalene 2,3-epoxide in
the chair-chair-chair-boat conformation leads
initially to the baccharane skeleton. Backbone re-
arr~gement of this skeleton leads to the
lemnaphyllane and shionane skeletons (included in
24 '23
the miscellaneous triterpenoid group). Chemical
Oleanane, 9CI
Abstracts treats this group as 18,19-secolupanes. The (23124 substituents specified inCA as (4a)23- and
numbering system parallels that of lupane apart from (4P)23 respectively; and 29/30 substituents as (20a)29
the carbon atoms of ring D. Occasionally a steroid- and (20p)29 respectively)

xlv
Description of Main Terpenoid Types

Taraxeranes, MultiOoranes, Glutinanes

and Friedelanes Tr-01083--Tr-01169
These triterpenoids [53] arise by increasing degrees of
backbone rearrangement of the oleanane skeleton.

Taraxastene Ursane,9CI

Taraxerane Multiflorane
D-Friedoleanane, 9CI D: C-Friedooleanane, 9CI

Bauerane
D: CcFriedoursane, 9CI

Hopanes Tr-01308--Tr-01374
23 Cyclisation of squalene in the chair-chair-chair-chair-
Glutinane Friedelane
chair conformation affords the hopane skeleton and
D: B-Friedooleanane, 9CI D: A-Friedooleanane, 9CI following a ring E expansion step, the gammacerane
skeleton (see below). Degraded and extended
hopanes occur widely in natural sediments. 21aH-
Hopanes (moretanes) arise by cyclisation of squalene
in the chair-chair-chair-chair-boat conformation.
Pachysananes Tr-01170-Tr-01172
The pachysananes are friedelane derivatives which
have the C-28 methyl group attached to C-16.

Hopane
A'-Neogammacerane, 9CI

Neohopanes, Fernanes, Adiananes and Filicanes

Pachysanane
16-Methyl-D: A-friedo-28-noroleanane, 9CI
Tr-01375-Tr-01413
Backbone rearrangement of the moretane skeleton
leads in turn to the neohopanes (neomotianes),
fernanes, adiananes and filicanes.

Taraxastanes, Ursanes and Baueranes

Tr-01173--Tr-01307
Methyl migration in ring E of the oleanane precursor
leads to the taraxastane skeleton (following proton
loss) or to the ursane skeleton (following a series of
hydride shifts). These two systems are often confused Neohopane Fernane
in the literature. The bauerane skeleton is related to B' :A'-Neogammacerane, 9CI D: C-Friedo-B' :A'-
ursane by backbone rearrangement. neogammacerane, 9CI

xlvi
 Nomenclature of tetracyclic triterpenoids in Chemical Abstracts

Serratanes and Onoceranes Tr-01426-Tr-01454

Cyclisation of squalene, or more likely, its
bisepoxide, from both ends affords the onocerane
skeleton. Further cyclisation leads to the serratane
skeleton.

Adianane Filicane
D: B-Friedo-B' ,A'- D :A-Friedo-B' ,A'-
neogammacerane, 9CI neogammacerane, 9CI

Serratane Onocerane
C(14a)-Homo-27- 8,4-Secogammacerane, 9CI
norgammacerane, 9CI
Arborinanes and Stictanes Tr-01414-Tr-01419
Cyclisation of squalene, or its 2,3-epoxide, in the
chair-boat-chair-chair-boat conformation followed Malabaricanes Tr-01455-Tr-01461
by ring expansion of ring E yields the stictane Partial cyclisation of squalene 2,5-epoxide from one
skeleton. Members of this group occur in lichens, e.g. end leads to the malabaricane group. The most
Sticta spp. Backbone rearrangement of this initial common numbering system in use is that based on
cyclisation product gives the arborinane skeleton. lanostane. The isomalabaricane skeleton (8,9-
Two variants to this series (see Miscellaneous diepimer of malabaricane) has recently emerged.
Triterpenoids), Boehmerol and Boehemerone have
undergone partal backbone rearrangement.
26

Malabaricane
15-Methyl-D-homo-C,30-dinor-13,17a-secodammarane, 9CI

Arborinane Stictane Miscellaneous triterpenoids Tr-01462-Tr-01494

D: C-Friedo-B': A'- 21,21-Dimetbyl-29,30-
neogammacerane, 9CI dinorgammacerane, 9CI This group contains assorted triterpenoid skeletons
which are less easily classified. It includes intriguing
compounds such as sipholenone C from the sponge
Siphochalina siphonella.

Gammaceranes Tr-01420-Tr-01425
The gammacerane skeleton arises from the same
cyclisation as hopane. The most notable
gammacerane derivative is tetrahymenol, a
metabolite of the protozoon Tetrahymena pyriformis,
whose hydroxyl function is derived from water and
not from squalene oxide.
The iridal group Tr-01495-Tr-01508
The iridals are constituents of Iris spp. which serve as
the precursors of the important perfumery chemicals,
the irones [53, 54]. The numbering system of iridal is
based on that of squalene. The irones are also
included in this section. The numbering system of the
irone skeleton is based on the carotenoids.

25

Gammacerane, 9CI Iridal

xlvii
 Description of Main Terpenoid Types

Abstracts Index Guide). The following examples

14
10
illustrate this point.

IUPACname Chemical Abstracts name

lrone 5,6-Dihydro-p,p- 5,6-Dihydro-P ,p-
caroten-3-ol caroten-3-ol
5,6-Dihydro-p,p- 5,6-Dihydro-6-hydroxy-
caroten-6-ol p,p-carotene
Tetraterpenoids Te-00001-Te-00249
The tetraterpenes arise by head to head coupling of Megastigmanes Te-00156--Te-00190
two geranylgeranylpyrophosphate molecules [55). This is a large group of c13 compounds generally
thought to be degraded carotenoids [58) or
catabolites of abscisic acid [59).
Carotenoids Te-00001-Te-00155 11 12

These include the hydrocarbons (carotenes) and their 10

oxygenated derivatives (xanthophylls) [56).
Carotenoid nomenclature is based on a stem name,
carotene and two Greek letters as prefixes to define Megastigmane
2-Butyl-1 ,1 ,3-trimethylcyclohexane
the two end groups [57). The numbering system and
end groups are given below.
17 18 19 20
1 3 5 7 15 14' 12· 1o· 8' 6' 4' 2· 16. Apocarotenoids Te-00191-Te-00249
16 ~2 4 '\ ~8 9~o1~21~4 ~5' ~3' ~1' ~9' '\. ~,
20' 19' 18' 17' Apocarotenoids are carotenoids in which the carbon
1J1,1ji-Carotene skeleton has been shortened by the formal removal of
fragments from one or both ends. A locant is used to
indicate that all the molecule beyond the carbon with
17

~\
18
Y0 that locant has been removed [57). It is not necessary
to give a Greek-letter end group designation if the
16 4 6 ~18 apo-locant is greater than 5.
/1 y

&.
16 Polyterpenoids Py-00001-Py-00013
This section includes the higher carotenoids and
polyprenols with more than 40 carbons.
E

References
16

17
1. Ruzicka, L. eta/., Helv. Chim. Acta, 1921, 4, 505
2. Ruzicka, L., Proc. Chern. Soc., 1959, 341
3. Ruzicka, L. eta/., Experientia, 1953,9,357
18
4. Cahn, R.S. eta/. ,J. Chern. Soc., 1951, 612; Experientia,
X
1956, 12, 81; Angew. Chern. Internat. Ed., 1966, 5, 385
Carotenoid end-groups 5. Prelog, V. eta/., Angew. Chern. Internal. Ed., 1982,
21,567
IUPAC treats the 'hydro' prefix as non-detachable. 6. Loomis, W.D. eta/., Recent Adv. Phytochem., 1973,
6,147
This Dictionary follows IUPAC recommendations
7. Hanson, J .R. in Comprehensive Organic Chemistry,
for nomenclature except that the 'hydro' prefix is Ed. Barton, D.H.R. eta/., Pergamon, Oxford, 1979,
treated as detachable and is placed alphabetically Vol. 5, p. 989
with the other prefixes. CA also uses a detachable 8. Banthorpe, D.V. eta/., Chern. Rev., 1972,72,115
'hydro' prefix but it does not use hypothetical parents 9. Croteau, R. in Biosynthesis of Isoprenoid Compounds,
such as P-caroten-6-ols which are incapable of Ed. Porter,J.W. eta/., 1981, Wiley, New York, Vol.1,
existence (see current Chemical Abstracts Index p. 225

xlviii
 Nomenclature of tetracyclic triterpenoids in Chemical Abstracts
10. Naylor, S. et al., Prog. Chem. Org. Nat. Prod., 1983,
44,189
11. El-Naggar, L.J. eta/., J. Nat. Prod., 1980, 43, 649
12. Boros, C.A. et al., J. Nat. Prod., 1990, 53, 1055
13. Inouye, H. et al., Prog. Chem. Org. Nat. Prod., 1986,
50,169
14. Pelter, A. et al., Rodd's Chemistry of Carbon
Compounds, 2nd Ed., 1969, IIC, 136.
15. Bryant, R., Rodd's Chemistry of Carbon Compounds,
2nd Ed., 1969, IIC, 256
16. Roberts, J .S. in Chemistry ofTerpenes and Terpenoids,
Ed. Newman, A.A., Academic Press, London, 1972,
p. 88
17. Parker, W. et al., Quart. Rev. Chem. Soc., 1967, 21,
331
18. Cordell, G.A., Chem. Rev., 1976,76,425
19. Cane, D .E., in Biosynthesis ofIsoprenoid Compounds,
Ed. Porter, J.W. eta/., 1981, Wiley, New York, Vol.1~
p.283
20. Fischer, N.H. et al., Prog. Chem. Org. Nat. Prod.,
1979,38,47
21. Fischer, N.H., Recent Adv. Phytochem., 1990, 24, 161
22. McDougal, P.G. eta/., Prog. Chem. Org. Nat. Prod.,
1985,47,153
23. Pinder, A.R., Prog. Chem. Org. Nat. Prod., 1977,
34,82
24. Bordoloi, M. et al., Phytochemistry, 1989, 28, 2007
25. Dev, S., Ace. Chem. Res., 1981,14, 82; Prog. Chem.
Org. Nat. Prod., 1981, 40, 49
26. Murakami, T. eta/., Prog. Chem. Org. Nat. Prod.,
1988,50,1
27. Marshall, J.A. eta/., Prog. Chem. Org. Nat. Prod.,
1974,31,283
28. Hanson, J.R., Prog. Chem. Org. Nat. Prod., 1971,
29,395
29. Hanson, J.R. in Chemistry of Terpenes and
Terpenoids, Ed. Newman, A.A., Academic Press,
London,1972,p. 155
30. West, C.A. in Biosynthesis of Isoprenoid Compounds,
Ed. Porter, J.W. et al., 1981, Wiley, New York,
Vol. 1, p. 375
31. Piozzi, F. eta/., Heterocycles, 1987,25,807
32. Fujita, E. et a/., Prog. Chem. Org. Nat. Prod., 1984,
46, 77
33. Lang, A. et al., Annu. Rev. Plant Physiol., 1970, 21,
537
34. MacMillan, J. et al., Aspects Terpenoid Chem.
Biochem., Proc. Phytochem. Soc. Symp., 2nd,
1970,153
35. Bearder, J .R. et al., Biochem. Soc. Trans., 1977,5, 569
36. Phinney, B.O. eta/., Recent Adv. Phytochem., 1990,
24,203
37. Weinheimer, A.J. eta/., Prog. Chem. Org. Nat. Prod.,
1979,36,285
38. Turner, W.B. et al., Fungal Metabolites II, Academic
Press, London, 1983
39. Evans, F.J. eta/., Prog. Chem. Org. Nat. Prod., 1983,
44,1
40. Crews, P. eta/., Prog. Chem. Org. Nat. Prod., 1985,
48,203
41. Cordell, G.A., Phytochemistry, 1974, 13, 2343
42. Gonzalez, A. G. et al., J. Nat. Prod., 1983, 46, 256
43. Connolly, J.D., et al., in Chemistry of Terpenes and
Terpenoids, Ed. Newman, A.A., Academic Press,
London,1972,p.207
44. Goodwin, T.W. in Biosynthesis of Isoprenoid
Compounds, Ed. Porter, J.W. et al., 1981, Wiley,
New York, Vol. 1, p. 443
. 45. Poulter, C.D. et al., in Biosynthesis of Isoprenoid
Compounds, Ed. Porter, J.W. eta/., 1981, Wiley,
New York, Vol. 1, p. 413
46. Lavie, D. et al., Prog. Chem. Org. Nat. Prod., 1971,
29,307
47. Tanaka, 0. eta/., Prog. Chem. Org. Nat. Prod., 1984,
46,1
48. Taylor, D.A.H., Prog. Chem. Org. Nat. Prod., 1984,
45,1
49. Mondon, A. eta/., Prog. Chem. Org. Nat. Prod., 1983,
44,101
50. Polonsky, J., Prog. Chem. Org. Nat. Prod., 1973,30,
101;1985,47,221
51. Tschesche, R. et a/., Prog. Chem. Org. Nat. Prod.,
1973,30,461
52. Mahato, S.B. eta/., Phytochemistry, 1988,27,3037
53. Chandler, R.F., eta/., Phytochemistry, 1979,18,711
54. Jaenicke, L. eta/., Prog. Chem. Org. Nat. Prod., 1986,
50, 1; Pure Appl. Chem., 1990,62, 1365
55. Spurgeon, S.L. et al., in Biosynthesis of Isoprenoid
Compounds, Ed. Porter, J.W. et al., 1981, Wiley,
New York, Vol. 2, p. 1
56. Ramage, R. in Chemistry ofTerpenes and Terpenoids,
Ed. Newman, A.A., Academic Press, London, 1972,
p.288
57. IUPAC, PureAppl. Chem., 1975,41,407
58. Izoe, S. et al., Tetrahedron Lett., 1969, 279
59. Powell, R.G. eta/., J. Org. Chem., 1986, 51, 1074
60. Dictionary of Steroids, Ed. Hill, R.A. eta/., Chapman
and Hall, London, 1991
61. Dictionary of Alkaloids, Ed. Southon, I.W. and
Buckingham, J., Chapman and Hall, London, 1988.
xlix
Hemiterpenoids
3,5-Dihydroxy-3-methylpentanoic ... - 2-Methyl-1,3-butadiene Hm-00001 - Hm-00004

Homomevalonolactone Hm-00002
4-Ethyltetrahydro-4-hydroxy-2H-pyran-2-one
Hemiterpenoids
60
-----. OH

(R)-form

3,5-Dihydroxy-3-methylpentanoic acid Hm-00001 C7H 120 3 M 144.170

Mevalonic acid. Hiochic acid (R)-form
[150-97-0] Probable intermed. in insect juvenile hormone biosynth.
<(H2 COOH Lee, E. eta/, J. Chern. Soc., Chern. Commun., 1983, 268 (synth)
(R)-form
H3C-C•OH Absolute
• configuration 3-Hydroxy-3-methylpentanedioic acid, 9CI Hm-00003
CH2 CH2 0H 3-Hydroxy-3-methylglutaric acid, 8CI. Dicrotalic acid.
Meglutol, USAN, INN. Medroglutaric acid. Lipoglutaren.
C6H 120 4 M 148.158 Lipomen. Mevalon. CB 337. HMG
(R)-form [17817-88-8] [503-49-1]
Intermed. in biosynth. of terpenoids and steroids. Oil.
l5-Lactone: [19115-49-2]. Mevalonolactone. Divalonic acid H3C,CCH2 COOH
C6HI003 M 130.143
In equilibrium with mevalonic acid, well incorporated H<f "cH2 COOH
into terpenes and steroids. Cryst. Mp 28°. Bp0 _005 100-
1080. [oc]~ -23° (c, 6 in EtOH). C6H 1o0 5 M 162.142
Occurs free in Crotalaria dura and C. globifera and bound
5-Phosphate: 5-Phosphomevalonic acid in Dicrotaline. Biosynth. precursor of isoprenoids.
C6H 130 7P M 228.138 Antihyperlipoproteinaemic agent. Cryst. (Et20jpet.
Isol. from various plants and microorganisms. Active ether). Mp 109°.
form of mevalonic acid. Mp 152-154° (as tris-
cyclohexylammonium salt). t> MA3753000.
5-Pyrophosphate: Anhydride, Ac:
C6H 140 1oP2 M 308.118 C8H 1o0 5 M 186.164
Intermed. in terpene biosynth. Oil. Prisms (EtzO). Mp 85°.
5-Pyrophosphate, dibrucine salt: Cryst. + 6Hz0 (Me 2CO Amide-nitrile: [72060-90-3].
aq.). Mp 173-175°. C6H 10N 20 2 M 142.157
Cryst. (EtzO). Mp 72-73°.
(S)-form
Oil. Diamide: [72060-91-4].
C6H 12 N 20 3 M 160.172
l5-Lactone: [19022-60-7]. Mp 134-135°.
Cryst. Mp 28°. [oc]i,6 + 22.8° (c, 10 in EtOH).
Adams, R. eta/, J. Am. Chern. Soc., 1953, 75, 2377.
(±)-form Savoie, L.L. eta/, Arzneim.-Forsch., 1975, 25, 1284 (tox)
Lactone: [674-26-0]. Savoie, L.L. eta/, Can. J. Physio/. Pharmacal., 1975, 53, 638
Mp 27-28°. Bp0 _1 110°. (metab)
Yousufzai, S.Y.K. eta/, Experientia, 1976, 32, 1033 (props)
Eberle, M. eta/, Helv. Chim. Acta, 1960, 43, 1508 (abs config)
Lupien, P.J. eta/, J. Clin. Pharmacal., 1979, 19, 120 (props)
Cornforth, J.W. eta/, Biochem. Soc. Symp., 1970, 5 (rev)
Yavrouian, A.H. eta/, Synthesis, 1981, 791 (synth, bib[)
Hanson, J.R., Adv. Steroid Biochem. Pharmacal., 1971, 1, 51
Sax, N.l., Dangerous Properties of Industrial Materials, 6th Ed.,
(biosynth)
Van Nostrand-Reinhold, 1984, 1580.
Johnson, R.N. et a/, Aust. J. Chern., 1971, 24, 1659 (pmr)
Cornforth, J.W., Chern. Soc. Rev., 1973, 2, 1 (rev)
Ellison, R.A. eta/, Synthesis, 1974, 719 (synth) 2-Methyl-1,3-butadiene, 9CI Hm-00004
Huang, F. eta/, J. Am. Chern. Soc., 1975, 97, 4144 (synth) Isoprene
Hanson, J.R., Compr. Org. Chern., 1979, 5, 989 (rev)
Lewer, P. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 1417 (synth) [78-79-5]
Takano, S. et a/, J. Chern. Soc., Chern. Commun., 1984, 82 (synth)
Bardshiri, E. eta/, J. Chern. Soc., Perkin Trans. I, 1984, 1765
H 2C=C(CH 3)CH=CH 2
(synth) C5H11 M68.118
Bonadies, F. et a/, Tetrahedron Lett., 1984, 25, 5431 (synth) Used in manuf. of synthetic and butyl rubbers, copolymer
Frye, S.V. eta/, J. Org. Chern., 1985, 50, 3402 (synth)
Mori, K. et a/, Tetrahedron, 1985, 41, 557 (synth)
for synthetic rubbers. d~g 0.681. Fp -147°. Bp 34.5-
Schneider, J.A. eta/, J. Org. Chern., 1986, 51, 1077 (synth) 35.00. n~ 1.4216. Readily polymerises.
Ferraboschi, P. eta/, J. Chern. Soc., Perkin Trans. I, 1987, 2301 t> Mod. irritant. Extremely flammable, flash p. -53°. Forms
(synth, pmr) explosive peroxide in air. NT4037000.
Sargsyan, M.S. eta/, Khim. Prir. Soedin., 1990, 26, 31; Chern. Nat.
Gallant, R.W., Hydrocarbon Process., 1967, 46, 155 (props)
Compd. (Engl. Trans/.), 24 (synth)
Fowler, R. et a/, Chern. Eng. (London), 1971, 253, 322 (rev)
Tai, J.C. eta/, J. Am. Chern. Soc., 1976, 98, 7928 (conformn,
struct)
Kirk-Othmer Encycl. Chern. Techno/., 3rd Ed., Wiley, N.Y., 1978-
1984, 13, 819 (rev)
Bretherick, L., Handbook of Reactive Chemical Hazards, 2nd Ed.,
Butterworths, London and Boston, 1979, 530.

3
3-Methylbutanal - 3-Methylbutanoic acid Hm-00005 - Hm-00008

Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed., Org. Synth., 1946, 26, 54 (synth)
Van Nostrand-Reinhold, 1979, 753. Rossi, R. et al, Gazz. Chim. /tal., 1968, 98, 1391 (synth)
Hazards in the Chemical Laboratory, (Bretherick, L., Ed.), 3rd Ed., Schouwstra, Y., Acta Crystal/ogr., Sect. B, 1973, 29, 1636 (cryst
Royal Society of Chemistry, London, 1981, 371. struct)
Freeman, J.P. et al, J. Org. Chern., 1975, 40, 3402 (synth)
Craig, J.C. et al, Tetrahedron, 1977, 33, 183 (conformn. abs conjig)
3-Methylbutanal, 9CI Hm-00005 Achiwa, K., Chern. Lett., 1978, 561, 567 (synth)
lsovaleraldehyde. 3-Methylbutyraldehyde Achiwa, K., Tetrahedron Lett., 1978, 1475 (synth)
[590-86-3]
(H 3C) 2CHCH 2CHO 2-Methylbutanoic acid, 9CI Hm-00007
Ethylmethylacetic acid. Butane-2-carboxylic acid
C5H 100 M 86.133 [116-53-0]
Occurs in orange, bergamot, lemon, sandalwood,
citronella, peppermint, eucalyptus and other oils. Also COOH (R)-form
I
in cider and foodstuffs. Used in manuf. of flavours and Absolute
perfumes. Alarm pheromone in honeybees. Liq. with H-cI .... cH3
configuration
pungent, apple-like odour. Misc. EtOH, Etp, spar. sol. CH2CH3
Hp. Fp -51°. Bp 92.5".
C5H 100 2 M 102.133
~ ES3450000.
(R)-form [32231-50-8]
Oxime: [626-90-4]. Degradn. prod. of many natural products. Bp 176-177°.
C5H 11NO M 101.148
Cryst. Mp 48.5°. Bp 164-165°. Me ester: [55449-44-0].
C6 H 120 2 M 116.160
2,4-Dinitrophenylhydrazone: [2256-0 1-1]. Bp 115-1 W. [a]:.,S -19.42° (H20).
Cryst. Mp 122-123°.
(S)-form [1730-91-2]
Di-Me acetal: [57094-35-6]. 1,1-Dimethoxy-3-methylbutane lsol. from many essential oils and other bioi. sources.
C7H 160 2 M 132.202 Bp 177°, Bp 15 76-78°.
Liq. Bp 128°.
Me ester: [10307-60-5].
Sabatier, P. et al, Compt. Rend. Hebd. Seances Acad. Sci., 1913, Bp 115.5-116". [a] 0 +16.56° (Hp).
156, 1730; 1914, 158, 985 (synth)
Meyers, A.l. et al, J. Org. Chern., 1973, 38, 36 (synth) Chloride: [27763-54-8].
Larcheveque, M. et al, Tetrahedron Lett., 1975, 3851 (synth) C5H 9Cl0 M 120.578
Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed., Bp 119-120°. [aJi1 + 19.2° (H 20).
Van Nostrand-Reinhold, 1979, 758. Amide: [13133-74-9].
C5H 11NO M 101.148
2-Methylbutanedioic acid, 9CI Hm-00006 Cryst. Mp lW. [aJi1 +22.4°.
Methylsuccinic acid, 8CI. Pyrotartaric acid. Propane-1,2- Nitrile: [25570-03-0]. 2-Cyanobutane
dicarboxylic acid C5H 9N M 83.133
[498-21-5] Bp 125-126°.
(±)-form [600-07-7]
COOH
I
(R)-form df~ 0.938. Bp 177°, Bp 21 84°. n0 1.4047.
Absolute
H-cI ... cH3 Et ester: [7452-79-1].
configuration
C7 H 140 2 M 130.186
CH2COOH
Bp 133.5".
C5H 80 4 M 132.116 Chloride: [57526-28-0].
(R)-form [3641-51-8] Bp 115-116°.
Degradn. prod. of many terpenes etc. Cryst. Amide: [1113-57-1].
(C6H 6 jEtp). Mp 115°. [a]~ + 16.88° (c, 2.16 in EtOH). Cryst. (Et20). Mp 112°.
Di-Me ester: [22644-27-5]. Anhydride:
C7H 120 4 M 160.169 C 10H 180 3 M 186.250
BPom 93-94°. [gc]~· 9 +9.98°. Bp 17 103-104°.
(S)-form [2174-58-5] Nitrile: [18936-17-9].
Degradn. prod. of many natural prods. Cryst. Bp 125°.
(C 6H 6/Etp). Mp 115°. [a]~ -15.9° (EtOH). ~ EU0530000.
Di-Me ester: [63163-08-6]. Org. Synth., Col/. Vol., I, 1932, 353; 2nd Ed., 361 (synth)
Bp 12 140°. [a]g'· 4 + 9.94°. Freudenberg, K. et a/, Justus Liebigs Ann. Chern., 1955, 594, 76
(±)-form [636-60-2] (abs conjig)
Prisms. V. sol. Hp. Mp 111-113°. pK. 1 4.06, pK.2 3.64. Brechbiihler, S. et al, J. Org. Chern., 1967, 32, 2641 (ahs config)
Heat at 200° --+ anhydride. Korver, 0. et al, Tetrahedron, 1974, 30, 4041 (cd, conformn)
Bestmann, H.J. et al, Tetrahedron Lett., 1974, 1275 (synth)
Di-Me ester: [21307-96-0]. Eberson, L. et al, Acta Chern. Scand., Ser. B, 1976, 30, 186 (synth)
Oil. Fp -80° approx. Bp 197°, Bp22 101°. Meyers, A.l. eta/, J. Am. Chern. Soc., 1976, 98, 567 (svnth)
Diamide: [77928-77-9].
C5H 10NP 2 M 130.146 3-Methylbutanoic acid Hm-00008
Cryst. Mod. sol. Hp, insol. org. solvs. Mp 225°. Isovaleric acid. Viburnum acid. Buldrianic acid. Phocenic
acid. lsopropylacetic acid. /sopentanoic acid
[503-74-2]

4
3-Methyl-1-butanol - 2-Methyl-2-butenoic acid Hm-00009 - Hm-00013

C5H 100 2 M 102.133 3-Methyl-2-butenal, 9CI Hm-00010

Constit. of tobacco, hops, cheese etc. Simple esters are 3-Methylcrotonaldehyde, SCI. 3,3-Dimethylacrolein.
used in flavourings and perfumes. Oil with cheese Senecioaldehyde. Senecialdehyde
aroma. Mod. sol. Hp. dl8 0.933. Mp -37.6°. Bp [107-86-8]
176.7°. pK._ 4.8.
I> NY 1400000. (H 3C) 2C=CHCHO
Me ester: C5H80 M 84.118
C6H 120 2 M 116.160 d~0 0.872. Bp 132-133°. n~ 1.4526. Readily oxid.
Oil. Bp 116-117°. Semicarbazone: Cryst. (MeOH). Mp 221-222°.
Et ester: Phenylhydrazone: Reddish-violet cryst. Mp 161-162°.
C7H140 2 M 130.186
Oil. Mp -99.3°. Bp 134.7°. Di-Et acetal: [1740-74-5]. 4,4-Diethoxy-2-methyl-2-butene
C,H180 2 M 158.240
3-Methylbutyl ester: [659-70-1]. Isopentyl isopentanoate Bp 163-165°. Easily dec.
ctoH 180 2 M 170.251
Constit. of banana fruit and tomatoes. Bp 190.5°. Wittig, G. eta/, Tetrahedron, Suppl., No. 8, 1966, 347 (synth)
Meyers, A.l. et al, J. Am. Chern. Soc., 1969, 91, 764 (synth)
I> NY1508000. Pauling, H. et al, Helv. Chim. Acta, 1976, 59, 1233 (synth)
Chloride: Cainelli, G. et al, J. Am. Chern. Soc., 1976, 98, 6737 (synth)
C5H,Cl0 M 120.578 Cardillo, G. et al, Tetrahedron, 1976, 32, 107 (synth)
Liq. Bp771 114.5-115.5°. Erman, M.B. et al, Tetrahedron Lett., 1976, 2981 (synth)
Schuda, P.F. et al, J. Org. Chern., 1987, 52, 1972 (synth, pmr, ir)
Amide:
Klusener, P.A.A. et al, J. Org. Chern., 1987, 52, 5261 (synth, pmr)
C5H 11NO M 101.148 Sax, N.J., Dangerous Properties of Industrial Materials, 5th Ed.,
Mp 131°. Van Nostrand-Reinhold, 1979, 967.
Nitrile: 1-Cyano-2-methylpropane. Isobutyl cyanide
C5H 9N M 83.133 2-Methyl-2-butene, 9CI Hm-00011
Fp -101°. Bp 130.SO (126-128°). Isopentene 2. P-Isoamylene. Penta/
Gustak, E. et al, Ark. Kemi, 1952, 24, II; CA, 49, 163e (:.ynth) [513-35-9]
Schmeltz; I. et al, J. Assoc. Off. Agric. Chern.; 1963, 46, 779 (isol)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 689 (occur) C5H 10 M 70.134
Batchelor, J.G. eta/, J. Magn. Reson., 1975, 20, 19 (cmr) Produced by Puccinia graminis. d0 0.678. Fp -134°. Bp
38.4°. n:;
1.3908.
3-Methyl-1-butanol, 9CI Hm-00009 I> EM7650000.
Isopentyl alcohol, SCI. Isoamyl alcohol Applequist, D.E. et al, J. Org. Chern., 1962, 27, 288 (synth)
[123-51-3] Jacobs, T.L. et al, J. Am. Chern. Soc., 1964, 86, 2240 (synth)
Nussim, M. eta/, J. Org. Chern., 1964, 29, 1120 (synth)
(H 3C) 2CHCH 2CHpH Roach, L.C. eta/, J. Chern. Soc., Chern. Commun., 1970, 606
(synth)
C5H 120 M 88.149 Abruscato, G.J. et al, J. Chern. Soc., Chern. Commun., 1972, 988
Major component of fusel oil and com!. amyl alcohol. (cmr)
Also a common constit. of plant oils, freeand as esters.
Solvent for fats, resins etc. Spar. sol. Hp. dl5 0.813. Bp
132°. n~ 1.4075.
3-Methyl-2-butene-1-thiol, 9CI Hm-00012
Dime thy/ally/mercaptan
I> Mod. toxic. An exp. carcinogen. EL5425000.
[5287 -45-6]
Ac: Isopentyl acetate. Isoamyl acetate
C7H 140 2 M 130.186 (H 3ChC=CHCH 2SH
dl5 0.876. Bp 142°. n~ 1.3999.
C5 H 10S M 102.200
3,5-Dinitrobenzoyl: Mp 60-62°. Substance responsible for "sun-struck" flavour of beer.
1-Naphthylurethane: Mp 76°. Liq. with leek-like aroma. Bp 125.5-127°.
Me ether: [626-91-5]. 1-Methoxy-3-methylbutane, 9CI Kuroiwa, Y. et al, Agric. Bioi. Chern., 1961, 25, 257 (isol)
C6H 1P M 102.176 Obota, Y. et al, Nature (London), 1961, 190, 635 (isol, synth)
dl 1 0.687. Bp 91°. Moore, C.G. et a/, Tetrahedron, 1962, 18, 205 (synth)
Et ether: [628-04-6]. 1-Ethoxy-3-methylbutane, 9CI. Ethyl 3- Lui, K.-C. et al, Arch. Pharm. (Weinheim, Ger.), 1976, 309, 1019
methylbutyl ether. Ethyl isopentyl ether (synth)
C7H 160 M 116.203
Liq. d 18 0.764. Bp 112°. 2-Methyl-2-butenoic acid Hm-00013
Peter, A.H., Ber., 1899, 32, 1419 (deriv) [13201-46-2]
Cerchez, V., Bull. Soc. Chim. Fr., 1928, 43, 766 (deriv)
Brown, H.C. eta/, J. Am. Chern. Soc., 1960, 82, 1504 (synth) H COOH
\ I
Blackburn, T.F. et a/, Tetrahedron Lett., 1975, 3041 (synth) C=C
Debal, A. eta/, Synthesis, 1976, 391 (synth) (E)-form
Bieber, H., Encycl. Chern. Process. Des., 1977, 3, 278 (rev) H3c( 'cHJ
Sharman, P.D. et a/, Kirk-Othmer Encycl. Chern. Techno/., 3rd
Ed., Wiley, N.Y., 1978-1984, 2, 570 (rev) C5H80 2 M 100.117
Sax, N.J., Dangerous Properties of Industrial Materials, 5th Ed., (E)-form [80-59-1] Tiglic acid
Van Nostrand-Reinhold, 1979, 748. Occurs as esters in many oils including Roman cumis oil
(Artemis nobilis). Cryst. (H20). Mp 63.5-64.0°. Bp
198.SO, Bp 1 u 95-96°.

5
3-Methyl-2-butenoic acid - 3-Methyl-3-buten-2-ol Hm-00014- Hm-00018

I> GQ5430000. p-Nitrobenzoyl: Mp 115-115.5°.

Me ester: [6622-76-0]. Naves, Y.-R. eta/, Bull. Soc. Chim. Fr., 1971, 886 (isol)
C6H 100 2 M 114.144 Melendez, E. eta/, An. Quim., 1972, 68, 1283 (synth, pmr)
Oil. Bp766 139.4-139.6°. Olah, G.A. eta/, J. Am. Chern. Soc., 1975, 97, 1539 (cmr)
Amide: [6028-38-2].
C5f4NO M 99.132 3-Methyl-2-buten-1-ol Hm-00016
Constit. of Agaia spp. Cryst. Mp 73-74°. Prenol. /sopentenyl alcohol
(Z)-form [565-63-9] Angelic acid [556-82-l]
Constit. of Angelica archange/ica and as esters of many
alcohols. Monoclinic prisms with spicy odour (H 20). (H 3C)zC=CHCHzOH
Mp 45°. Bp 185°, Bp 10 88-89°. Steam-volatile. Isomerises C5H 100 M 86.133
to (E)-form at Bp. Constit. of ylang-ylang and hop oils. Oil. Bp 137-138°.
Me ester: [5953-76-4]. I> EM9472500.
Bp 128°.
Ac: [1191-16-8].
Amide: lsol. from fruit oil of Laserpitium hispidum. Mp C7 H 120 2 M 128.171
127-128°. Constit. of ylang-ylang oil. Perfumery ingredient. Oil.
Buckles, R.E. eta/, Chern. Rev., 1955, 55, 659 (rev) Bp 32 54-56°.
Leete, E. eta/, Tetrahedron Lett., 1967, 1727 (biosynth) I> EM9473700.
Myles, A. eta/, J. Med. Chern., 1968, 11, 143 (synth)
3,5-Dinitrobenzoyl: Mp 71°.
Johns, S.R. eta/, Aust. J. Chern., 1969, 22, 1315 (isol)
Vogeli, U. eta/, Org. Magn. Reson., 1975, 7, 617 (cmr) Naves, Y.-R. eta/, Bull. Soc. Chim. Fr., 1971, 886 (isol)
McGaw, B.A. et a/, Phytochemistry, 1979, 18, 1647 (biosynth) Crombie, L. eta/, J. Chern. Soc., Perkin Trans. 1, 1975, 913 (cmr)
Hill, R.K. et a/, J. Am. Chern. Soc., 1980, 102, 7344 (biosynth) Wenkert, E. eta/, Org. Magn. Reson., 1975, 7, 51 (cmr)
Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 1032.
3-Methyl-3-buten-1-ol Hm-00017
[763-32-6]
3-Methyl-2-butenoic acid, 9CI Hm-00014
3-Methylcrotonic acid, 8CI. 3,3-Dimethylacry/ic acid. H 2C=C(CH 3)CH 2CH 20H
Senecioic acid. Isopropylideneacetic acid
C5 H 100 M 86.133
[541-47-9] Constit. of ylang-ylang oil. Oil.
(H 3C) 2C=CHCOOH 3,5-Dinitrobenzoyl: Cryst. Mp 56-56.5°.
Naves, Y.-R., Bull. Soc. Chim. Fr., 1971, 886 (isol)
C5 H 80 2 M 100.117 Trost, B.M. eta/, J. Am. Chern. Soc., 1975, 97, 7152 (synth)
lsol. from some plants e.g. Peucedanum japonicum. Residue
present in some terpenes and pyrrolizidine alkaloids.
Prisms (HzO). Mp 70°. Bp 199°, Bp40 114°. Sublimes. 3-Methyl-3-buten-2-ol, 9CI Hm-00018
I> GQ5425000. /sopropenylmethylcarbinol. 3-Hydroxy-2-methyl-1-butene
Me ester: [924-50-5]. [10473-14-0]
c,H 100 2 M 114.144
yH3
Bp 135-138°.
Chloride: [3350-78-5]. H-c... oH
C
I

C5 H 7Cl0 M 118.562 (S)-form

Bp 145-150°. H3 C...-- ""'CH2
Amide: [4479-75-8]. C5H 100 M 86.133
C5H9 NO M 99.132 Constit. of orange, blackcurrant, grape and hops.
Mp 107-108°.
(S)-form [88376-46-9]
Nitrile: [4786-24-7]. Bp 130°. [oc]if -5.6° (c, 8 in CHC1 3).
C5H 7N M 81.117
(±)-form [60041-32-9]
Bp 140-142°.
Bp 116-117°, Bp60 54.6-56.8°.
Org. Synth., Col/. Vol., 3, 1955, 302 (synth, bib/)
Akahori, Y., Chern. Pharm. Bull., 1961, 9, 921,936 (isol) 3,5-Dinitrobenzoyl: Mp 110°.
Collin, P.J. eta/, Aust. J. Chern., 1966, 19, 317 (pmr) Phenylurethane: Cryst. (pet. ether). Mp 66-66.5°.
Edwards, J.D. eta/, J. Org. Chern., 1966, 31, 2282 (synth) Lauchenauer, A. eta/, Helv. Chim. Acta, 1951, 34, 1514 (synth)
Santi, R. eta/, J. Organomet. Chern., 1979, 182, 117 (synth) Green, M.B. eta/, J. Chern. Soc., 1957, 3262 (synth)
King, R.B. eta/, Tetrahedron, 1986, 41, 3235 (deriv, synth, pmr, Hart, H. eta/, J. Org. Chern., 1959, 24, 1261 (synth)
cmr, ir) Hartley, R.D. eta/, Chern. Ind. (London), 1967, 1601 (isol)
Crout, D.H.G. eta/, J. Chern. Soc., Perkin Trans. 1, 1983, 2435
2-Methyl-3-buten-2-ol Hm-00015 (synth, resoln)
/soprenyl alcohol
[ll5-l8-4]
(H 3C) 2C(OH)CH=CH 2
C5H 100 M 86.133
Constit. of ylang-ylang and Lavandula oils and hops.
Intermediate in the manuf. of terpene alcohols for
perfumery industry. Oil. Bp 98-99°.

6
Monoterpenoids
Batatic acid - 1,7-Dihydroxy-3,7-dimethyl-2,5-... Mo-00001 - Mo-00007

ciOHI6s4 M 264.500
Constit. of hops. Yellow oil.
Acyclic monoterpenoids Elvidge, J.A. et al, J. Chern. Soc., Perkin Trans. I, 1982, 1089.

4,7-Dihydro-5-(4-methyl-3-pentenyl)-1,2,3- Mo-00005
trithiepin, 9CI
5-(4-M ethyl-3-pentenyl)-1 ,2,3-trithia-5-cycloheptene
Batatic acid Mo-00001 [73188-26-8]
a-Methyl-!5-oxo-3-furanpentanoic acid
[496-07-1]
0
(S)-form
~c=H Absolute
configuration
0
C 10H 120 4 M 196.202 C 10H 16S3 M 232.434
Constit. of hops. Yellow oil.
(S)-form
Obtd. from sweet potato infected with Ceratostomella Elvidge, J.A. et al, J. Chern. Soc., Perkin Trans. I, 1982, 1089.
fimbriata. Mp 88.5-89.SO. [a]~ + 17.SO (EtOH).
2,4-Dinitrophenylhydrazone: Mp 154.5-155.SO. 6, 7-Dihydroxy-2,6-dimethyl-2,4- Mo-00006
(±)-form octadienoic acid
Mp 106-107°.
Kubota, T., Tetrahedron, 1958, 4, 68.
HOOC..-
1. -"-'-HO~ly ~
~ ~ (6R,7R)-form
~-Clause nan Mo-00002 OH
3-Methyl-2-(3-methyl-1 ,3-butadienyl1furan
CtoH 160 4 M 200.234
[62641-75-2] (6R,7R)-form

u{ Me ester: [94120-03-3]. Citreodiol

C11 H 180 4 M 214.261
Metab. of Penicillium citreo-viride B (IFO 6050). Oil.
1(0~ Occurs as mixt. with epicitreodiol.
Me ester, carbonate: Cryst. (EtOAcfhexane). Mp 89-90°.
CIOH120 M 148.204 [rxJ3& + 70° (c, 0.1 in MeOH).
Constit. of Clausena willdenovii. Oil. Bp 177-178°, Bp 50
102°. (6S,7S)-form
Rao, P.L.N., CA, 1948, 42, 5290 (isol) Me ester: Oil. [ali? +4.3° (c, 1.0 in CHC1 3).
Rao, G.S.R.S. et al, Phytochemistry, 1984, 23, 399 (struct) (6S,7R)-form
Me ester: [94136-10-4]. Epicitreodiol
Cleviolide Mo-00003 Metab. of P. citreo-viride B (IFO 6050). Oil. Occurs as
4-(4-Methyl-3-penten-l-ynyl)-2(5H)-furanone, 9CI mixt. with citreodiol.
[81 052-99-5] (6R,7S)-form
Me ester: Oil. [a]i] -7.1 o (c, 2.3 in CHC1 3).
Shizuri, Y. et al, Tetrahedron Lett., 1984, 25, 4771 (struct, synth)

1,7-Dihydroxy-3,7-dimethyl-2,5-octadien- Mo-00007
4-one

C10H 100 2 M 162.188

Constit. of Senecio clevelandii. Cryst. (pet. ether). Mp 64°.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 2425.
C10H 160 3 M 184.235
5,8-Dihydro-6-(4-methyl-3-pentenyl)- Mo-00004 (2E,5E)-form
1,2,3,4-tetrathiocin, 9CI Constit. of Artemisia aucheri. Oil.
6-(4-Methyl-3-pentenyl)-1 ,2,3,4-tetrathia-6-cyclooctene l-Ac: [111394-39-9]. l-Acetoxy-7-hydroxy-3,7-dimethyl-
[82203-03-0] 2E,5E-octadien-4-one
C 12 H 180 4 M 226.272
From A. aucheri. Oil.
7-Hydroperoxide: [111480-78-5]. 7-Hydroxy-l-hydroxy-3,7-
dimethyl-2E,5E-octadien-4-one
C 10H 160 4 M 200.234
From A. aucheri. Oil.
7-Hydroxyperoxy, l-Ac: [111394-41-3]. J-Acetoxy-7-
hydroperoxy-3,7-dimethyl-2E,5E-octadien-4-one

9
1,5-Dimethyl-6,8-dioxabicyclo[3.2.1] ... - 3,7-Dimethyl-2,4-octadiene Mo-00008 - Mo-00013

C 12H 180 5 M 242.271 C 10H 160 M 152.236

From A. aucheri. Oil. I> RG5075000.
Rustaiyan, A. et a/, Phytochemistry, 1987, 26, 2307. (E)-form {141-27-5] Geranial. Citra/ a
Occurs in lemon, orange and many other essential oils.
1,5-Dimethyl-6,8-dioxabicyclo(3.2.1)octane Mo-00008 Important in the food and perfume industry Bp 229°,
Fronta/in Bp20 119°.
I> RG5075100.
Semicarbazone: Cryst. Mp 164°.
(Z)-form [106-26-3] Neral. Citra/ b
(+)-form Occurs with Geranial. Bp 12 103°.
Semicarbazone: Cryst. Mp 171°.
C 8H 140 2 M 142.197 Org. Synth., 1943, 23, 78 (synth)
Attractant for Western Pine Beetle. Simonsen, J.L. et a/, The Terpenes, 2nd Ed., Cambridge Univ.
Press, 1947, 1, 83 (rev)
(+)-form [57917-96-1] Ohtsura, M. et a/, J. Chern. Soc. B, 1967, 1033 (pmr)
Pheromone from Dendroctonus frontalis and D. Kogami, K. et a/, Bull. Chern. Soc. Jpn., 1968, 41, 2508 (synth)
breviconis. Bp 121 100-103°. [a]i] +53.4° (Et20). Karrer, W. eta/, Konstitution und Vorkommen der Organischen
(-)-form [28401-39-0] Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 371 (occur)
Bp 120 99-100°. [a]i] -52.0° (Etp).
Vortkevich, S.A., Parfums, Cosmet. Savons Fr., 1972, 2, 407 (rev)
I> JG6825000. Akhila, A., Phytochemistry, 1985, 24, 2585 (biosynth)
(±)-form [60478-96-8] Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Bp!OO 92-93°. Van Nostrand-Reinhold, 1979, 507.
Kinzer, G.W. et a/, Nature (London), 1969, 221, 477 (isol)
Mori, K. et a/, Tetrahedron, 1975, 31, 1381 (synth, abs config) 2,6-Dimethyl-2,6-octadiene, 9CI Mo-00011
Ohrui, H. eta/, Agric. Bioi. Chern., 1976, 40, 2267 (synth) Dihydroocimene. Dihydromyrcene
Hicks, D.R. eta/, J. Chern. Soc., Chern. Commun., 1976, 869
(synth) [2792-39-4]
Gore, W.E. eta/, J. Org. Chern., 1976, 41, 607, 1926 (ms, pmr)
Magnus, P. eta/, J. Chern. Soc., Chern. Commun., 1978, 297
(synth) ~ (E)-form
Wilson, R.M. eta/, J. Am. Chern. Soc., 1981, 103, 207 (synth)
Jarosz, S. eta/, J. Org. Chern., 1982, 47, 935 (synth) CIOH18 M 138.252
Fuganti, C. et a/, J. Chern. Soc., Perkin Trans. I, 1983, 241 (synth) (E)-form [2609-23-6]
Meister, C. et a/, Justus Liebigs Ann. Chern., 1983, 913 (synth) Liq. Bp40 70°.
Naef, R. eta/, Justus Liebigs Ann. Chern., 1983, 913, 1930 (synth) (Z)-form [2492-22-0]
Utaka, M. eta/, Tetrahedron Lett., 1983, 24, 2567 (synth)
Liq.
Johnston, B.D. eta/, Can. J. Chern., 1984, 62, 2148 (synth)
Lee, A.W.M. eta/, J. Chern. Soc., Chern. Commun., 1984, 578 Suga, K. et a/, Bull. Chern. Soc. Jpn., 1967, 40, 1257 (synth,
(synth) spectra)
Kongathip, B. et a/, Chern. Lett., 1985, 1849 (synth) Imaizumi, F., Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1972,
Hagiwara, H. eta/, J. Chern. Soc., Perkin Trans. I, 1985, 283 1695 (synth)
(synth)
Trehan, I.R. eta/, Indian J. Chern., Sect. B, 1986, 25, 1243 (synth) 3,7-Dimethyl-1,6-octadiene
Whitesell, J.K. eta/, J. Org. Chern., 1986, 51, 5443 (synth)
Mo-00012
Trinh, M.-C. eta/, J. Chern. Soc., Chern. Commun., 1987, 615 P- Linalolene. Citronellene
(synth) [2436-90-0]

7,7-Dimethyl-6,8- Mo-00009 ~ (R)-form

dioxabicyclo(3.2.1)octane, 9CI
CIOH18 M 138.252
[16566-94-2]
I> RG5340000.
(R)-form
Degradn. prod. of Zingiberene. Oil. Bp 158-159°. [ali?
+8.7°.
(±)-form
d~ 8 0.761. Bp720 155-156°. n~ 1.4385.
Daniewski, W. eta/, Pol. J. Chern. (Rocz. Chern.), 1971, 45, 923
C8H 140 2 M 142.197 (synth)
Constit. of the essential oil of "Shinshu-wase" hops. Bp 12 Rienaecker, R., Chimia, 1973, 27, 97 (synth)
55°. Watanabe, S. et al, J. Appl. Chern. Biotechnol., 1974, 24, 639
Naya, Y. eta/, Tetrahedron Lett., 1967, 2459 (isol, synth) (synth)
Colonge, J. et al, Bull. Soc. Chim. Fr., 1969, 956 (synth)
3,7-Dimethyl-2,4-octadiene Mo-00013
3,7-Dimethyl-2,6-octadienal Mo-00010 [56523-26-3]
Citra/
[5392-40-5] I I (E,E)-form
~
~CHO (E)-form
CIOH18 M 138.252
(E,E)-form [6874-39-1]

10
2,6-Dimethyl-1,7-octadiene-3,6-diol - 3, 7 -Dimethyl-2,6-octadiene-1,4-diol Mo-00014 - Mo-00021

Liq. Bp 12 58°. 2,6-Dimethyl-5,7-octadiene-2,3-diol Mo-00017

(2E,4Z)-form 6,7-Dihydro-6,7-ocimenediol
Liq. Bp 164-167°. [87563-25-5]
Abe1mann, P., Ber., 1910, 43, 1588 (synth)

HO~
Pastureau, M. et a/, Bull. Soc. Chim. Fr., 1926, 39, 1436 (synth)

2,6-Dimethyl-1,7-octadiene-3,6-diol Mo-00014
[51276-33-6] OH
C 10H 180 2 M 170.251

Jy0C
OH
(Z)-form
Constit. of Aster bakeranus. Oil.
Tsankova, E. et a/, Phytochemistry, 1983, 22, 1285.
CIOHI802 M 170.251
Constit. of Cinnamomum camphora. Oil. 3,7-Dimethyl-1 ,5-octadiene-3,7-diol Mo-00018
Takaoka, D. et al, Phytochemistry, 1976, 15, 330. [13741-21-4]

2,6-Dimethyl-2,7-octadiene-1,6-diol Mo-00015 HO_/ \PH

~
3
9 OH
HOH 2 C~I
(2E,6S)-form
CIOHI802 M 170.251
Constit. of Cinnamomum camphora. Oil.
CIOHI802 M 170.251 3,4-Dihydro: 3,7-Dimethyl-1-octene-3,7-diol
C 10H 200 2 M 172.267
(2E,6S)-form [66957-95-7]
Constit. of Vitis vinifera. Cryst. Mp 51-52°.
Constit. of Nicotiana tabacum and of a Ferreyranthus sp.
Oil. [1X]n + 17.SO (c, 0.79 in MeOH). No rotn. given for Takoada, D. et a/, Phytochemistry, 1976, 15, 330 (isol, struct)
F. sp. sample. Williams, P.J. eta/, Phytochemistry, 1980, 19, 1137 (deriv)
(2E,6R)-form [61434-50-2]
Oil. [1X]i,S -12.8° (c, 1.08 in MeOH). 3,7-Dimethyl-1,6-octadiene-3,4-diol, 9CI Mo-00019
(2E,6f,)-form Cornusol
1-0-P-n-Glucoside: [64776-96-1]. Betulalbuside A [68042-45-5]
C 16H 280 7 M 332.393
Constit. of Betula alba and Chaenomeles japonica. Oil. l, /"-
'y_OH.&o
..--~y~
(2Z,6f,)-form
1-0-P-n-Glucoside: [64813-08-7]. Betulalbuside B OH
C 16H 28 0 7 M 332.393
CIOHI802 M 170.251
From B. alba and C. japonica. Oil. lsol. from the essential oil of Comus controversa. Bp3 75-
Suga, T. et al, Chern. Lett., 1976, 1245 (synth) no.
Tschesche, R. et al, Chern. Ber., 1977, 110, 3111 (Betulalbusides)
Behr, D. et al, Acta Chern. Scand., Ser. B, 1978, 32, 228 (isol, Kurihara, T. et a/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1978,
synth) 98, 969 (isol, ir, pmr)
Vig, O.P. et a[, Indian J. Chern., Sect. B, 1979, 17, 619 (synth)
Gray, N.A.B. et al, J. Org. Chern., 1981, 46, 703 (cmr) 3,7-Dimethyl-2,5-octadiene-1,7-diol Mo-00020
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1669 (isol)

2,6-Dimethyl-3,7-octadiene-2,6-diol, 9CI Mo-00016

HO~CH20H
c.oHI802 M 170.251
HO,/ \PH 1-Ac: [33766-42-6]. 8-Acetoxy-2,6-dimethyl-3,6-octadien-2-ol
~ C 12H 200 3 M 212.288
CIOHI802 M 170.251 Constit. of Jasonia montana. Oil.
Constit. of Achillea ligustica and Cinnamomum camphora. Ahmed, A.A. et a/, Phytochemistry, 1988, 27, 3875.
Detected in many fruits and aromatic oils and in wines.
Photooxidn. prod. of linalool. Oil. [1X]i;' + 3.6° (c, 0.38 in 3,7-Dimethyl-2,6-octadiene-1,4-diol Mo-00021
CHCI 3).
Rosiridol
[51276-34-7, 76540-50-6, 112420-84-5)
[101391-01-9]
Takaoka, D. et a/, Phytochemistry, 1976, 15, 330 (isol, pmr)
Bruno, M. eta/, Phytochemistry, 1988, 27, 1871 (isol)
~CH20H
OH
c.oHI802 M 170.251
Constit. of Rhodiola rosea. Oil. [IX]~ -7.7° (c, 1.3 in
Me 2CO).
8-0-P-n-Glucopyranoside: [100462-37-1]. Rosiridin

11
3,7-Dimethyl-2,7-octadiene-1,6-diol - 3,7-Dimethyl-1,6-octadien-3-ol Mo-00022 - Mo-00028

C 16H 28 0 7 M 332.393 Campbell, R.V.M. et at, J. Chern. Soc., Perkin Trans. 1, 1975, 897
From R. rosea. Oil. [ali? -32.7° (c, 1.1 in Me 2CO). (synth)
Fujita, Y., Chern. Lett., 1978, 533 (nitrile)
Kurkin, V.A. et at, Khim. Prir. Soedin., 1985, 21, 593.

3,7-Dimethyl-2,7-octadiene-1,6-diol Mo-00022
2,6-Dimethyl-2,6-octadien-4-ol Mo-00026

OH
~
~CH20H CIOH180 M 154.252
BPo.7 50o.
CIOH1802 M 170.251 [85676-86-4, 85676-97-7)
(E)-form Morrison, N.J., J. Chern. Soc., Perkin Trans. I, 1982, 3027 (synth,
Constit. of Jasonia montana. Oil. spectra)
Ahmed, A.A. et at, Phytochemistry, 1990, 29, 3658 (isot, pmr)
2,6-Dimethyl-4,7-octadien-2-ol Mo-00027
3,7-Dimethyl-2,6-octadiene-1-thiol, 9CI Mo-00023 Achillenol
Thiogeraniol
[3823 7-00-21 HO~I ! (R,E)-form
~ Absolute
~CH2 SH configuration
CIOH180 M 154.252
C 10H 18S M 170.318 (R,E)-form [33303-1 0-51
(E)-form [39067-80-61 Constit. of Achillea .filipendulina. Oil. Bp 20 83°. [al5& + 0
Flavouring ingredient. 20, -5.9, -12.9°.
Mantegani, A. et at, Chim. Ther., 1972, 7, 411 (synth) (R,Z)-form [33303-11-61
Ger. Pat., 2 221 626, (1972); CA, 78, 71402 (synth, use) Constit. of A . .filipendulina. Oil. Bp 20 83°. [ali~ + 71.2°.
Schulte-Elte, K.H. et at, Hetv. Chim. Acta, 1971, 54, 1095.
2,6-Dimethyl-3,6-octadiene-1,2,8-triol Mo-00024
3,7-Dimethyl-1,6-octadien-3-ol Mo-00028
HOH2 C~CHOH Linalool. Linalol. Linalyl alcohol
HO~I I 2
[78-70-61
CIOH1803 M 186.250
(3E,6E)-form I H~/ (R)-form
Constit. of Jasonia montana. Oil. ~ Absolute
Ahmed, A.A. et at, Phytochemistry, 1990, 29, 3658 (isot, pmr) configuration
CIOH180 M 154.252
3,7-Dimethyl-2,6-octadienoic acid Mo-00025 Used extensively in perfumery industry.
Geranic acid. Geranoic acid I> Mod. toxic. RG5775000.
(R)-form [126-91-0l
~COOH (E)-form Licareol
Constit. of many essential oils including rose. neroli and
CIOH1602 M 168.235 lavender. Major component of oil of Mentha arvensis.
Present in petitgrain, lemon grass and other essential oils, Oil. Bp756 197-200°. [ali? -17°.
(early samples without assignment of config.). (S)-form [126-90-91
(E)-form [4698-08-21 Coriandrol
Geranic acid a Constit. of coriander and other essential oils. Major
Constit. of Daphne flowers and Rodgersia podophylla. component of oil of Cryptocarya moschata and C.
Oil. aschersoniana. Oil. Bp 198-200°, Bp20 85-90°.
Me ester: 3-0-P-n-Glucopyranoside: [82928-12-91.
C11 H 180 2 M 182.262 C 16H 280 6 M 316.394
Oil. Bp0.35 63°. Constit. of fronds of Arachniodes maximowiczii. Oil. [ali;1
Nitrile: [5146-66-7]. Geranonitrile -160° (c, 4.0 in MeOH).
CIOH15N M 149.235 3-0-[p-L-Glucopyranosyl-(1-+6)-P-n-glucopyranosidel:
Lemon olfactant. Bp 10 110°. Bp refers to a mixt. of (E)- C22H 380 11 M 478.536
and (Z)-forms. Constit of fronds of A. maximowiczii. Syrup. [ali;1 -27°
(Z)-form [4613-38-1] (c, 2.0 in MeOH).
Geranic acid b. Nerolic acid Ohloff, G. et at, Tetrahedron, 1962, 18, 37 (abs config)
Oil. Naves, Y.R. et at, Hetv. Chim. Acta, 1963, 46, 1056, 2551 (isot, uv)
Me ester: Oil. Bp0.4 58°. Wilhalm, B. et at, Acta Chern. Scand., 1964, 18, 1573 lms)
Nair, G.V. eta/, Tetrahedron Lett., 1966, 5097 (synth)
Burrell, J.W.K. et at, J. Chern. Soc. C, 1966, 2144 (synth, ptnr) Suga, T. et at, Bull. Chern. Soc. Jpn., 1972, 45, 1480 (biosynth)
Albright, J.A. et at, Org. Prep. Proced. Int., 1972, 4, 215 (synth, Karrer, W. et at, Konstitution und Vorkommen der Organischen
derivs) Pjlanzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
Kabayashi, S. et at, Chern. Lett., 1974, 705 (synth) no. 120 (occur)
Bohlmann, F. et at, Org. Magn. Reson., 1975, 7, 426 (cmr)

12
3,7-Dimethyl-2,6-octadien-1-ol - 2,6-Dimethyloctane Mo-00029 - Mo-00034

Takabe, K. et al, Tetrahedron Lett., 1975, 3005 (synth) 3,7-Dimethyl-3,7-octad.ien-1-ol Mo-00031

Julia, M. et al, Bull. Soc. Chim. Fr., 1976, 513 (synth) /sogeraniol
Scarborough, R.M. et al, J. Org. Chern., 1979, 44, 1742 (synth)
Tange, K. et al, Bull. Chern. Soc. Jpn., 1981, 54, 2763 (biosynth) [19788-92-2]
Tanaka, N. et al, Chern. Pharm. Bull., 1986, 34, 1015 (derivs)
Ohwa, M. et al, J. Org. Chern., 1986, 51, 2599 (synth)
Howell, A.R. et al, J. Chern. Soc., Perkin Trans. I, 1990, 2715 ~CH2 0H
(synth)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed., C 10H 180 M 154.252
Van Nostrand-Reinhold, 1979, 772. (E)-form
Oil with rose odour. Bp9 102-103°.
3,7-Dimethyl-2,6-octad.ien-1-ol Mo-00029 Brady, S.F. eta/, J. Am. Chern. Soc., 1968, 90, 2882.

~~OH
(E)-form 2,6-Dimethyl-5,7-octad.ien-4-one Mo-00032
Tagetone
C 10H 180 M 154.252
(E)-form (106-24-1] Geraniol. Geranyl alcohol. Lemonol
Found in free state and as esters in many essential oils
including geranium oil. Extensively used in perfumery.
~(E)-form
Oil with sweet rose odour. Bp 230°. C10H 160 M 152.236
I> RG5830000. (E)-form [6752-80-3]
Formyl: [105-86-2]. Constit. of the essential oil of Tagetes glandulifera and
C 11H 180 1 M 182.262 other T. spp. Oil. Bp2 64-66°.
Constit. of geranium oil. Used in artificial rose oils. Oil (Z)-form [3588-18-9]
with rose odour. Bp 15 113-114°. Major constit. of the essential oil of T. glandulifera.
I> RG5925700. Unstable oil. Bp 205-210°.
Ac: [105-87-3]. Geranyl acetate Boehm, E.E. eta/, J. Chern. Soc., 1963, 2535 (synth, struct)
C 12H 200 2 M 196.289 Adams, D.R. et al, J. Chern. Soc., Perkin Trans. I, 1975, 1741
Constit. of citronella, orange and other oils. Used (synth)
extensively in perfumery. Oil with fragrant odour. Bp22 Guittet, E. eta/, Tetrahedron Lett., 1978, 1155 (synth)
130-132°.
I> RG5920000. 3,7-Dimethyl-2,6-octadienylamine Mo-00033
(Z)-form [106-25-2] Nero/. Neryl alcohol 1-Amino-3,7-dimethyl-2,6-octadiene
Constit. of many essential oils including neroli and
bergamot oils. Used extensively in perfumery. Oil. Bp
225-226°. ~CH2NH2
I> RG5840000.
CIOH19N M 153.267
Ac: [141-12-8]. Neryl acetate (E)-form [6246-48-6]
C 12H 200 2 M 196.289 Geranylamine
Used in perfumery. Oil. Bp 0 _25 49-52°.
Bates, R.B. et al, J. Org. Chern., 1963, 28, 1086 (struct) Phthalimido deriv.: Cryst. (MeOH). Mp 60-6l.SO.
Burrell, J.W.K. et al, J. Chern. Soc. C, 1966, 2144 (synth)
Karrer, W. et al, Konstitution und Vorkommen der Organischen (Z)-form [36615-19-7]
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, Nerylamine
nos. 118, 119 (occur) Oil. Bp0 _3 48-50°.
Casey, C.P. et al, Synth. Commun., 1973, 3, 321 (synth) Phthalimido deriv.: Cryst. (MeOH). Mp 59-60.SO.
Pitzele, B.S. et al, J. Org. Chern., 1975, 40, 269 (synth)
Banthorpe, D.V. et al, Phytochemistry, 1976, 15, 91 (biosynth) Bunton, C.A. eta/, J. Org. Chern., 1972, 37, 4036.
Derguini-Boumechal, F. eta/, Tetrahedron Lett., 1977, 1181
(synth) 2,6-Dimethyloctane Mo-00034
Mathew, K.K. eta/, Indian J. Chern., Sect. B, 1981, 20, 340 (synth)
Banthorpe, D.V. et al, Phytochemistry, 1983, 22, 2459 (biosynth) [2051-30-1]
Howell, A.R. eta/, J. Chern. Soc., Perkin Trans. I, 1990, 2715
(synth)

3,7-Dimethyl-2,7-octadien-1-ol Mo-00030 C 10Hn M 142.284

(+)-form
~CH20H Liq. Bp 160-161°. [cx]v +6.27°.
(±)-form
C 10H 180 M 154.252 Liq. Bp l60-l60.SO.
(E)-form [1117-82-4]
Propanoyl: Vavon, G., Ann. Chim. (Paris), 1914, 1, 169 (synth)
C 13Hn01 M 210.316 Escorrov, R., Bull. Soc. Chim. Fr., 1928, 43, 1101 (synth)
Component of the pheromone of the San Jose scale, Suga, K. et al, Bull. Chern. Soc. Jpn., 1967, 40, 1257 (synth,
Quadraspidiotus pernicious. spectra)
(Z)-form
Propanoyl: Component of pheromone of San Jose scale.
Alerdice, M. et al, Tetrahedron Lett., 1984, 25, 1643 (synth)

13
2,6-Dimethyloctanoic acid- 2,6-Dimethyl-1,4,7-octatriene Mo-00035 - Mo-00041

2,6-Dimethyloctanoic acid Mo-00035 4-Methy/benzenesu/fony/: Oil. Bp0 .05 58°. [cxln + 2.00° (c,
[7414-45-1] 4.00 in C 6H 6).
(S)-form
Sol. Et20. Bp 212-213°, Bp 15 109°.
H~ (±)-form [59204-02-3]
C10H 220 M 158.283
C1oH:zo0 2 M 172.267
Constit. of feather waxes of various birds. Bp 212-213°.
Bertlesen, 0., Ark. Kemi, 1970, 32, 17 (glc, ms)
Ac: [20780-49-8].
Jacob, J. eta/, Z. Naturforsch., B, 1970, 25, 1438 (glc, ms) Bp 12 109-110°.
t> RH0920000.
Jarolin, V. eta/, Collect. Czech. Chern. Commun., 1974, 39, 596
2,6-Dimethyl-2-octanol Mo-00036 (use)
[18479-57-7] Nagai, K. eta/, Bull. Chern. Soc. Jpn., 1976, 49, 265 (.1ynth)
Chan, K.-E. eta/, J. Org. Chern., 1976, 41, 3497 (synth, use)
HO~ Cohen, N. eta/, J. Org. Chern., 1976, 41, 3505 (syllth, use)
Schmidt, M. et a/, Helv. Chim. Acta, 1979, 62, 464 (synth, use)
Zell, R. eta/, Helv. Chim. Acta, 1979, 62, 474 (synth, use)
C10H 220 M 158.283 Fuganti, C. eta/, J. Chern. Soc., Chern. Commun., 1979, 995
(±)-form (synth, use)
Perfumery ingredient. Liq. Bp 10 80.5°.
Sutherland, M.D., J. Am. Chern. Soc., 1953, 75, 5944 (synth) 2,6-Dimethyl-1,3,5,7-octatetraene, 9CI Mo-00039
Cosmene
3,7-Dimethyl-3-octanol, 9CI Mo-00037 [460-01-5]
Tetrahydrolinalool. 2,6-Dirnethy/-6-octano/
[78-69-3]
~
C 10H 14 M 134.221
(R)-form Constit. of Cosmos bipinnatus and other compositae. Liq.
Mp -2° to -1°. Bp0 _3 30°. ni? 1.584.
C 10H 220 M 158.283
Naylor, P. et a/, J. Chern. Soc., 1954, 4006 (synth)
t> RH0905000. Sorensen, N.A. eta/, Acta Chern. Scand., 1954, 8, 280 (iso[)
(R)-form [56577-25-4]
Bp2 . 2 57°. [cxln +0.96° (c, 15.5 in hexane).
2,6-Dimethyl-1,3,7-octatriene, 9CI Mo-00040
4-Nitrobenzoy/: [39998-98-6]. cx-Hyrnentherene
[cxJn + 1.67° (C6H 6).
[6876-07-9]
(S)-form
Bp5 54-59.5°. [cx]n -0.63° (pentane). (S)-(E)-forrn
4-Nitrobenzoy/: [39999-20-7].
Mp 39.5-40°. [cx]~.s -0.93° (c, 26.5 in C6H 6). ~ Absolute
configuration
Ph ether: Bp4 140-145°. [cx]i;· 2 -5.53°. C10H 16 M 136.236
(±)-form (S)-(E)-form [33303-06-9]
Perfumery ingredient. Liq. Bp 715 185-186°. Oil. Bp 161°. [cx]i? + W.
Stevens, P.G. et a/, J. Am. Chern. Soc., 1939, 61, 1295 (corifig) (S)-(Z)-form [33303-07-0]
Corman, R.H. eta/, Aust. J. Chern., 1960, 29, 133 (synth, pmr) Oil. [cx]i? -7.8°.
Cornforth, R.H. eta/, Justus Liebigs Ann. Chern., 1960, 634, 197
Ogata, Y. eta/, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1942,
(abs con.fig) 63, 417, 419; CA, 41, 3039 (synth)
Verkade, P.E. eta/, Reel. Trav. Chim. Pays-Bas (J. R. Neth. Chern.
Klein, E. eta/, Chern. Ber., 1964, 97, 2700 (abs config)
Soc.), 1964, 83, 367 (config) Schulte-Elte, K.H. eta/, Helv. Chim. Acta, 1971, 54, 1095 (pmr, ir)
Mehta, G., Tetrahedron, 1973, 29, 1119 (synth)
Takahashi, K. eta/, Bull. Chern. Soc. Jpn., 1973, 46, 600 (synth)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)
Hiroshi, Y. et a/, Synthesis, 1977, 334 (synth)

3,7-Dimethyloctanol, 9CI Mo-00038 2,6-Dimethyl-1,4,7-octatriene Mo-00041

Dihydrocitronellol. Tetrahydrogeraniol Achillene
[106-21-8]

~CH20H (R)-form
(R,E)-form
C 10H 16 M 136.236
C 10H 220 M 158.283
(R,E)-form [33303-13-8]
t> RH0900000. Constit. of Achillea filipendulina. Oil. [cxln -3 8°.
(R)-form [1117-60-8] (R,Z)-form [33303-12-7]
Found in essential oil of geranium. Intermed. in terpene Constit. of A. filipendulina. Oil. [cx]i? + 64°.
synth., especially ex-tocopherol side chains. Also a
perfumery ingredient. Oil. Bp 212-213°, Bp 10 105-106°. Schu1te-Eite, K.H. et al, Helv. Chim. Acta, 1971, 54, 1095.
Ac:
C 12H 240 2 M 200.320
Found in essential oil of Mentha spp. Bp0. 3 60-62°.

14
2,6-Dimethyl-2,4,7-octatriene - 2,6-Dimethyl-7-octene-2,3,6-triol Mo-00042 - Mo-00049

2,6-Dimethyl-2,4,7-octatriene. Mo-00042 3,7-Dimethyl-2,4,6-octatrien-1-ol Mo-00046

~llyn~entherene

~CH20H
~ (R,E)-form C 10H 160 M 152.236
CtoH 16 M 136.236 (2Z,4E)-forn~ [50656-63-8] Dehydronerol
Hymentherene is a major constit. of the oil of Oil.
llymenantherum tenuifolium. 3-Methylbutanoyl: [49831-79-0]. Dehydroneryl isovalerate
(R,E)-forn~ CtsH240 2 M 236.353
Oil. [1X]i? -go. Constit. of Anthemis montana. Oil.
(R,Z)-forn~ [33403-67-7] Bohlmann, F. et al, Tetrahedron Lett., 1973, 2065 (isol)
Oil. [1X]i? + 16l.SO. Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1773 (synth)
Cardillo, G. et al, Tetrahedron, 1976, 32, 107 (synth)
Shulte-Eite, K.H. et a/, Helv. Chim. Acta, 1971, 54, 1095.

3,7-Dimethyl-1,3,6-octatriene, 9CI Mo-00043 3,7-Dimethyl-6-octenal Mo-00047

Alloocin~ene. P-Ocimene CitroneUal
[13877-91-3] [106-23-0]

~ (E)-form
~CHO (R)-form
C 10H 180 M 154.252
C10H 16 M 136.236
Monoterpene occurring in many essential oils, usually (R)-forn~ [2385-77-5]
accompanied by the !J.7 isomer. Oil with pleasant odour. Constit. of citronella oil. Also in oils of eucalyptus,
lavender, Ocimum gratissimum, Phlebalium nudum,
BP7o lOOo.
Citrus spp. and others. Bp 204-205°, Bp 14 90°.
(E)-forn~
(S)-forn~ [5949-05-3]
ni? 1.4893, A.max 232 nm (e 27 600) (EtOH).
Reported from oils of Backhousia citriodora and C.
(Z)-forn~
hystrix.
ni? 1.4877, A.max 237.5 nm (e 21 000) (EtOH).
Arigoni, D. eta/, Helv. Chim. Acta, 1954, 37, 881 (abs config)
Ryhage, R. eta/, Acta Chern. Scand., 1963, 17, 2025 (ms) O'Donnell, G.W. eta/, Aust. J. Chern., 1966, 19, 525.
Ohloff, G. eta/, Justus Liebigs Ann. Chern., 1964, 675, 83. Karrer, W. et al, Konstitution und Vorkommen der Organischen
Thieme, H. et al, Pharmazie, 1972, 27, 255 (rev) Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr) no. 366, 367 (occur)
Sokol'skii, D.V., Dokl. Akad. Nauk SSSR, 1978, 242, 1126 (synth)
3,7-Dimethyl-1,3,7-octatriene Mo-00044 Akhila, A., Phytochemistry, 1986, 25, 421 (biosynth)
Chimirri, A. et al, Heterocycles, 1987, 26, 2469.
rx.-Ocin~ene

3,7-Dimethyl-2-octene-1,8-diol Mo-00048
~ [33150-33-3]
C10H 16 M 136.236
(E)-forn~ [6874-10-8]
Constit. of Ocimum rubrum. Oil. HOH2~CH20H
(Z)-forn~ [6874-44-8] CtoH200 2 M 172.267
Constit. of 0. rubrum oil. Oil. Pheromone of the hair-pencil secretion of Danaus
Thieme, H. eta/, Pharmazie, 1972, 27, 255. chrysippus. Oil.
Meinwald, J. et al, Tetrahedron Lett., 1971, 3485 (synth)
3,7-Dimethyl-1,5,7-octatrien-3-ol Mo-00045 Morizur, J.P. eta/, Tetrahedron Lett., 1975, 4167 (synth)
Fujisawa, T. eta/, Tetrahedron Lett., 1982, 23, 3193 (synth)
[29957-43-5] Joshi, N.N. eta/, Indian J. Chern., Sect. B, 1984, 23, 238 (synth)

I H<l/
2,6-Dimethyl-7-octene-2,3,6-triol Mo-00049
~
[73815-21-1]
CtoHt,O M 152.236

HO~
(R,E)-forn~[20053-88-7] llotrienol
Constit. of Ho-leaf. Oil. Bp2 62°. [1X]i? -15.2°.
(S,E)-forn~
Constit. of tea flavour. Oil. [1X]n + 11.9°. OH
[38818-60-9, 53834-70-1, 83541-43·9] C10H 200 3 M 188.266
Nakatani, Y. et al, Agric. Bioi. Chern., 1969, 33, 967 (isol, abs Constit. of Vitis vinifera. Oil. Bp 1 126-128°.
config) Williams, P.J. eta/, Phytochemistry, 1980, 19, 1137.
Moiseenkov, A.M. et al, J. Chern. Soc., Chern. Commun., 1982,
109 (synth)

15
3,7-Dimethyl-6-octenoic acid - Eldanolide Mo-00050 - Mo-00055

3,7-Dimethyl-6-octenoic acid Mo-00050 McAndrew, B.A. et a/, J. Chern. Soc., Perkin Trans. I. 1972, 367
Citronellic acid. Rhodinic acid. Callitrol (synth)
LeBorgne, J.F. et al, Tetrahedron Lett., 1976, 1379 (synth)
[502-47-6]

I,_ f COOH
3,7-Dimethyl-6-octen-1-yn-3-ol, 9CI Mo-00053
~ (R)-form Dehydro-P-linalool
C,oH 180 2 M 170.251 [29171-20-8]
I> RH3230000.
(R)-form [18951-85-4]
Oil. Bp 257°, Bp 10 143°.
(S)-form [2111-53-7]
Constit. of Callitris glauca, C. intratropica, c,oH 160 M 152.236
Intermed. in manuf. of terpene alcohols for perfumery etc.
Chamaecyparis obtusa, Thujopsis dolabrata, Juniperus
Bp 13 89-90°.
spp. and other plants. Bp0 _6 118°. [cx]~4 -6.6°.
(±)-form
Ac: [29171-21-9].
Isol. from Camphor oil. Bp4 126°. C12H 180 2 M 194.273
BPo.os 56o.
Mori, K. et al, Tetrahedron, 1977, 33, 289 (stereochem)
Carlton, J.L et al, Can. J. Chern., 1980, 58, 458 (synth) U.K. Pat., 948 752, (1964); CA, 60, 13147 (synth)
Kulesza, J. eta/, Przem. Chern., 1966, 45, 149; CA, 65, 751 (synth)

3,7-Dimethyl-6-octen-1-ol Mo-00051
Citronellol. P-Rhodinol. P-Citronellol. Y acarol. Rhodinol
Egomaketone Mo-00054
1-(3-Furanyl)-4-methyl-3-penten-1-one, 9CI. 3-(4-Methyl-3-
[106-22-9] pentenoyl)furan
[59204-74-9]
~CH20H (R)-form 0

C10H 200 M 156.267
I> RH3400000.
(R)-form [1117-61-9]
Constit. of Nigella sativa seeds and Cymbopogon distans.
A common constit. of plant oils, esp. in the Rutaceae.
Also isol. from alligator secretions. Oil. Bp0 _5 68°. [cxln
+ 5.45° (neat).
I> JX2580000.
(S)-form [7540-51-4]
Constit. of geranium and citronella oils. Alcohol acetate
and other simple esters used in perfumery and flavour
industries. Oil. Bp0 _5 68-70°. [cxln -4.76°.
Burrell, J.W.K. et al, J. Chern. Soc. C, 1966, 2144 (synth) Eldanolide
Karrer, W. et al, Konstitution und Vorkommen tier Organischen
Pflanzenstoffe, 2nd Ed., Birkhauser Verlag, Basel, 1972-1985,
no. Ill (occur)
Suga, T. et al, Bull. Chern. Soc. Jpn., 1973, 46, 3545 (biosynth)
Wollmann, H. eta/, Pharmazie, 1973, 28, 56 (isol)
Shono, T. et al, Tetrahedron Lett., 1974, 1295 (synth)
Hidai, M. et al, J. Chern. Soc., Chern. Commun., 1975, 170 (synth)
Chan, K.-K. eta/, J. Org. Chern., 1976, 41, 3497 (synth)
Corey, E.J. et al, J. Org. Chern., 1976, 41, 380 (synth)
Lanza, E. et a/, Phytochemistry, 1977, 16, 1555 (biosynth)
Hiroma, M. eta/, J. Org. Chern., 1985, 50, 127 (synth)
Soai, K. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 415 (synth)
3,7-Dimethyl-1-octen-5-one Mo-00052
Dihydrotagetone
[1879-00-1]
(S)-form
C 10H, 80 M 154.252
(S)-form [51468-47-4]
Constit. of Tagetes glandulifera. Liq. Bp40 97-98°. [cxln
+ 1.50.
Semicarbazone: Cryst. (EtOH aq.). Mp 95-96°.
(±)-form
BPis 82o.
Jones, T.G.H. et al, J. Chern. Soc., 1925, 127, 2530.
Vig, O.P. eta/, Indian J. Chern., 1970, 8, 107 (synth)
~
0
C 10H 120 2 M 164.204
Constit. of Perilla frutescens. Cryst. Mp 17°. Bp 13 116-
1170.
Hoppmann, A. et al, Tetrahedron, 1978, 34, 1723 (synth)
Gosselin, P. eta/, J. Org. Chern., 1979, 44, 2807 (synth)
Mo-00055
Dihydro-4-methyl-5-(3-methyl-2-butenyl)-2(3H)-furanone,
9CI. 3,7-Dimethyl-6-octen-4-olide. 4-Methyl-5-prenyl-y-
butyrolactone
[84107-93-7]
Absolute
configuration
CIOH1602 M 168.235
Wing gland phereomone of the male African sugar-cane
borer Eldona saccharina. Oil. Bp2. 5 75°. [cx]i;' +51.5° (c,
1.15 in MeOH).
Kunesch, G. et al, Tetrahedron Lett., 1981, 22, 5271 (isol, struct)
Uematsu, T. et al, Agric. Bioi. Chern., 1983, 47, 597 (synth)
Yokoyama, Y. et al, Chern. Lett., 1983, 1245 (synth)
Chakraborty, T.K. et al, Tetrahedron Lett., 1984, 25, 2891 (synth)
Vigneron, J.P. et al, Tetrahedron, 1984, 40, 3521 (struct, synth, abs
conjig)
Davies, H.G. et al, J. Chern. Soc., Chern. Commun., 1985, 1166
(synth)
Suzuki, K. et al, Tetrahedron Lett., 1985, 26, 861 (synth)
Frauenrath, H. et al, Tetrahedron, 1986, 42, 1135 (synth)
Butt, S. et al, J. Chern. Soc., Perkin Trans. I, 1987, 903 (synth)
Ortuiio, R.M. et al, Tetrahedron, 1987, 43, 4497 (synth)

16
Elsholtzidiol - 8-Hydroxy-2,6-dimethyl-2,6-... Mo-00056 - Mo-00062

Elsholtzidiol Mo-00056 2,4-Dinitrophenylhydrazone: Red-orange needles (EtOH).

2-(2,3-Dihydroxy-3-methylbutyl)-3-methylfuran. 3-Methyl-1- Mp 149.5°.
(3-methyl-2-furanyl)-2,3-butanediol, 9CI Oxime: Needles (EtOH aq.). Mp 62-64°.
[28666-20-8] Kondo, K. eta/, Tetrahedron Lett., 1976, 4363 (synth)
Kitamura, T. eta/, Synth. Commun., 1977, 7, 521 (synth)

r( ?H . Abdu1la, R.F. eta/, J. Org. Chern., 1978, 43, 4248 (synth)

Inomata, K. et a/, Chern. Lett., 1979, 709 (synth)
Garst, J.E. eta/, J. Agric. Food Chern., 1984, 22, 1083 (synth)
"o~'~~~m Kaezuka, Y. et a/, Planta Med., 1985, 480 (iso/, props)

C 10H 160 3 M 184.235

Constit. of Elsholtzia densa. Cryst. (pet. ether). Mp 58-59°. Fusalanipyrone Mo-00060
3-Methyl-6-( 1-methyl-1-propenyl)-2H-pyran-2-one, 9CI
Vashist, V.N. eta/, Experientia, 1970, 26, 817.
[118169-29-2]
Elsholtzione Mo-00057
3-Methyl-1-(3-methyl-2-furanyl)-1-butanone, 9CI. 2-
/sobutyryl-3-methylfuran
[488-05-1]
CIOHI202 M 164.204
Metab. of Fusarium so/ani. Oil. Shown not to be of
terpenoid origin although is apparently a
monoterperoid.
Abraham, W.-R. eta/, Phytochemistry, 1988, 27, 3310; 1990, 29,
C 10H 140 2 M 166.219 2877 (isol, struct, biosynth) ·
Constit. of Elsholtzia cristata and other£. spp. Oil. Bp 2. 2
59.5-60°. 6-Hydroxy-2,6-dimethyl-2,7-octadienoic Mo-00061
Semicarbazone: Cryst. (MeOH). Mp 171-172°. acid
2',3'-Didehydro: [6138-88-1]. 3-Methyl-1-(3-methyl-1-
furanyl)-2-buten-1-one, 9CJ. Dehydroelshotzione. Naginata
ketone
I \PH_
H~ (R,E)-form
CIOHI202 M 164.204
Constit. of E. oldhami, E. ciliata and Perilla spp. Oil. d~0 CIOHI603 M 184.235
1.016. Bp2. 2 81°. ni? 1.5351. (R,E)-form
Naves, Y.-R. eta/, He/v. Chim. Acta, 1960, 43, 406 (isol) Oil.
Cazes, B. eta/, Synth. Commun., 1977, 7, 113 (synth) [(1-0-4-Hydroxyphenyl)-P-D-glucopyranosyl-6-y~ ester: see
Pi11ot, J.P. eta/, Tetrahedron Lett., 1980, 4717 (synth)
Liu, C. et a/, J. Heterocycl. Chern., 1984, 21, 129 (isol, purifn, ir, Phlebotrichin, Mo-00092
pmr) (S,E)-form
rx-L-Arabinopyranoside: [92751-87-6].
2,3-Epoxy-2,6-dimethyl-5,7-octadien-4-ol Mo-00058 C15H240 7 M 316.350
Constit. of fruits of'Gymnocladus chinensis. Needles
6, 7- Epoxy-5-hydroxyocimene
(MeOH). Mp 142-144°. [rx]i; +4.7° (c, 1.07 in MeOH).
[119308-ll-1]
[p-D-Glucopyranosyl-(1-+3)-4-0-(2-methylbutanoyl)-rx-L-
arabinopyranoside]: [92751-84-3].

~ 0
C26H 4z0 13 M 562.610
Constit. of G. chinensis. Powder (MeOHjEtzO). Mp
163-166°. [rx]i; +38.8° (c, 1.25 in MeOH).
C 10H 160 2 M 168.235 ((1-0-4-Hydroxyphenyl)-P-D-g/ucopyranosyl-6-y~ ester: see
Constit. of Cineraria britteniae. Oil. Phlebotrichin, Mo-00092
Lehmann, L. eta/, Phytochemistry, 1988, 27, 3307. Konoshima, T. eta/, Chern. Pharm. Bull., 1984, 32, 2617.

1-(3-Furanyl)-4-methyl-1-pentanone, 9CI, Mo-00059 8-Hydroxy-2,6-dimethyl-2,6-octadienoic Mo-00062

SCI acid
Perilla ketone 7
HOOC
[553-84-4] ~CH2 0H
0
C 10H 160 3 M 184.235

~(0
Constit. of Radermachia sinica. Oil.
Me ester:
C11 H 180 3 M 198.261
Isol. from Hoffmannia strigillosa. Oil.
C 10H 1P 2 M 166.219
lsol. from the essential oil of Perilla frutescens. Promotes Glucosyl ester:
intestinal propulsion in mice. Light-yellow liq. Bp 30 Ct6H 260 8 M 346.377
130°. Constit. of R. sinica. Oil. [rxln -II .SO (c, 0.47 in
I> SA8935000. MeOH).

17
1-Hydroxy-3,7-dimethyl-2,6-octadien-.•. - Isoegomaketone Mo-00063 - Mo-00069

6,7-Dihydro: 8-Hydroxy-2,6-dimetltyl-6-octelloic acid. 2,3- Constit. of Chondrococcus hornemannii. Oil. [~]n -17.9°
Dihydro-8-geranio/oic acid (c, 0.001 in CHC13).
C1JI110 3 M 186.250 Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1983 (isol, pmr, cmr)
lsol. from H. strigillosa (as Me ester). Oil (Me ester). Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (isol, pmr)
Iwagawa, T. eta/, Phytochemistry, 1990, 29, 1913 (isol, pmr, cmr)
Jaensch, M. eta/, Phytochemistry, 1990, 29, 3587 (isol, pmr, derivs)
6-Hydroxy-6-methyl-3,7-octadien-2-one Mo-00067
[88153-61-1]
l-Hydroxy-3,7-dimethyl-2,6-octadien-5- Mo-00063
one
~
? \PH
Y ) Y C H20H C9H 140 1 M 154.208
(E)-form [80368-34-9]
C1JI160 1 M 168.235 Constit. of Calea rotundifolia. Oil.
1-0-P-D-Giucopyranoside: [128502-89-6].
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1635.
C16H160 7 M 330.377
Constit. of Spiraea cantoniensis. Amorph. powder. [a]n
-19.6° (c, 1 in MeOH). 3-Hydroxy-2,2,6-trimethyl-6- Mo-00068
Takeda, Y. eta/, Phytochemistry, 1990, 29, 1591 (isol, pmr, cmr) vinyltetrahydropyran
6-Ethenyl-3,4,5,6-tetrahydro-2,2,6-trimethyi-2H-pyran-3-ol

(o+H
6-Hydroxy-2,6-dimethyl-2,7-octadien-4- Mo-00064 (14049-11-7]
one
(64661-54-7]

~ 2 3 C10H 180 1 M 170.251

Constit. of Tanacetum boreale and Ajania fastigiata, Citrus
C10H 160 1 M 168.235 spp. and others. Oil. Bp 10 97-98°. [a]i? + 15.8°. Earlier
Constit. of Citrus junos. Oil. Bp0 _7 69-70°. isolates contained Linalyl oxide, Mo-00072, which entry
2,3-Dihydro: [71547-63-2). 6-Hydroxy-2,6-dimethy/-7-octen- see for further synonyms and references.
4-one
Ac: [67674-42-4]. 3-Acetoxy-2,2,6-trimethy/-6-
C10H 180 1 M 170.251 viny/tetrahydropyran
Constit. of C.junos. Oil. Bp0 _7 60-61°.
CuH100 3 M 212.288
Kitahara, T. eta/, Agric. Bioi. Chern., 1980, 44, 897. From T. boreale and A. fastigiata. Oil. Bp 10 98-99°. [a]i?
+17.SO.
8-Hydroxy-2,6-dimethyl-2,5-octadien-4- Mo-00065 3-Ketone: (33933-72-1]. 3-0xo-2,2,6-trimethy/-6-
one viny/tetrahydropyran
C 10H 160 1 M 168.235
Y ' t y ' C H20H From T. boreale and A. fastigiata. Oil. [a]i? -· 9.3°.
(E)-form 3-Ketone, 2,4-Dinitropheny/hydrazone: Cryst. Mp lll-
C 1JI1,01 M 168.235 112.SO.
(E)-form Klein, E. eta/, Tetrahedron Lett., 1983, ll09 (synth)
Dembitskii, A.D. eta/, Khim. Prir. Soedin., 1985, 332 (isol)
0-P-D-Glucopyranoside: [128502-90-9].
C 16H 160 7 M 330.377
Constit. of Spiraea cantoniensis. Amorph. powder. [a]i;l lsoegomaketone Mo-00069
-13.0° (c, 1 in MeOH). 1-(3-Furanyl)-4-methy/-2-penten-1-one, 9CI
(Z)-form [128502-91-0] [34348-59-9]
0-P-D-Giucopyranoside: 0
C16H160 7 M 330.377
Constit. of S. cantoniensis. Amorph. powder. [a]i;l
-20.1° (c, 1.69 in MeOH).
Takeda, Y. et a/, Phytochemistry, 1990, 25, 1591 (isol, pmr, cmr)
~ 0
C10Hu01 M 164.204
3-Hydroxymethyl-7-methyl-2,7-octadiene- Mo-00066 Constit. of the seeds of Perilla frutescens. Oil. Bp 1 77-80°.
1,6-diol I> 883921000.
2,4-Dinitropheny/hydrazone: Red solid (MeOH). Mp 179-
1800.
Dihydro: see 1-(3-Furanyl)-4-methy/-1-pentanone, Mo-
. 00059
Ito, H., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1964, 84, ll23
(isol, struct)
C 10H 180 3 M 186.250 Massy-Westropp, R.A. eta/, Aust. J. Chern., 1966, 19, 891 (synth)
(Z)-form [125538-00-3] Abdulla, R.F. et al, J. Org. Chern., 1978, 43, 4248 (synth)
Pillot, J.-P. et a/, Tetrahedron Lett., 1980, 4717 (synth)
Watanabe, E. eta/, Bull. Chern. Soc. Jpn., 1982, 52, 3225 (synth)

18
Lepalone- 7-Methyl-3-methylene-1,6-octadiene Mo-00070 - Mo-00075

Lepalone Mo-00070 Felix, D. et al, Helv. Chim. Acta, 1963, 46, 1513 (synth)
Attaway, J.A. et al, Phytochemistry, 1966, S, 1273 (isol)
5-(3-Fury/)-2-methyl-1-penten-3-one
Rychnovsky, S.D. et al, J. Am. Chern. Soc., 1981, 103, 3963
[80445-58-5] (synth)
Utaka, M. eta/, Tetrahedron Lett., 1983, 24, 2567 (synth)
0

0
~ 3-Methyl-2-(3-methyl-2-butenyl)furan
Rosefuran. y-Clausenan
[15186-51-3]
Mo-00073

C10H 110 2 M 164.204

Constit. of Roman camomile oil (Anthemis nobilis). Oil.
3-Alcohol: [72075-28-6]. a.-(1-Methylethenyl)-3-
furanpropanol, 9CI. 5-(3-Fury/)-2-methyl-1-penten-3-ol.
Lepalol
CIOHI.Ol M 166.219
I sol. from essential oil of Ledum pa/ustre. Oil with
pleasant odour. Bp4 108-111°. nijll.4925. Opt. inactive.
Mikhailova, N.S. et al, Khim. Prir. Soedin., 1979, 322; Chern. Nat.
Compd. (Engl. Trans/.), 278 (Lepalol)
Thomas, A.F. eta/, Helv. Chim. Acta, 1981, 64, 2393 (Lepalone)
Lilac alcohol Mo-00071
5-Ethenyltetrahydro-P,5-dimethyl-2-furanmethanol, 9CI
CIOHI40 M 150.220
Constit. of the odour of rose oil and found in Clausena
willdenovii. Oil. Bp 1 39-40°.
Vig, O.P. et a/, J. Indian Chern. Soc., 1974, 51, 900 (synth)
Birch, A.J. eta/, Tetrahedron Lett., 1976, 2079 (synth)
Ly, N.D. eta/, Helv. Chim. Acta, 1977, 60, 2085 (synth)
Gedge, D.R. eta/, Tetrahedron Lett., 1977, 4443 (synth)
Ismail, Z.M. eta/, Angew. Chern., Int. Ed. Engl., 1983, 22, 719
(synth)
Takano, S. eta/, Chern. Lett., 1984, 1261 (synth)
Rao, G.S.R.S. eta/, Phytochemistry, 1984, 23, 399 (isol)
Tsukasa, H. eta/, Agric. Bioi. Chern., 1989, 53, 3091 (synth)

2-Methyl-6-methylene-1,7-octadiene, 9CI Mo-00074

C1gH 180 2 M 170.251 r~.-Myrcene
Opt. rotns. are those measured for natl. lilac alcohols, [1686-30-2]
which were obt. only in small amts. Somewhat different
values were obt. for synthetic material of both
enantiomeric series synth. from ( + )- and (- )-linalool.
(ftS,2S,5S)-form [33081-34-4]
Lilac alcohol a CIOHI6 M 136.236
Constit. of Syringa vulgaris. [a.]i_? + 12.2° (c, 4.1 in Found in many essential oils, usually a_§ a mixt. with P-
CHC1 3). myrcene. Intermed. in manuf. of terpene alcohols for
(ftR,2S,5S)-form [33081-35-5] perfumery etc. Oil. Bp 10 44°.
Lilac alcohol b 3-Hydroperoxy: 3-Hydroperoxy-7-methy/-6-methylene-1,7-
Constit. of S. vulgaris. [a.]i_? -6.6° (c, 3.6 in CHC1 3). octadiene. r~.-Myrcene hydroperoxide
(ftR,2R.SS)-form [33081-36-6] cloH1,02 M 168.235
Lilac alcohol c Constit. of Artemisia annua. Unstable oil.
Constit. of S. vulgaris. [a.]i_? -1.4° (c, 1.8 in CHC1 3). Wrolstad, R.E. et a/, J. Agric. Food Chern., 1964, 12, 507 (ir)
Ohloff, G. eta/, Justus Liebigs Ann. Chern., 1964, 675, 83 (synth,
(ftS,2R,5S)-form [33081-37-7]
spectra)
Lilac alcohol d Ryhage, R. eta/, Acta Chern. Scand., 1965, 17, 2025 (ms)
Constit. of S. vulgaris. [a.]i_? +4.3° (c, 1.7 in CHC1 3). Mitzner, B.M. eta/, J. Org. Chern., 1965, 30, 646 (synth, spectra)
Wakayama, S. et a/, Bull. Chern. Soc. Jpn., 1973, 46, 3183. Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhauser Verlag, Basel, 1972-1985,
no. 32 (occur)
Linalyl oxide Mo-00072 Rucker, G. eta/, J. Nat. Prod. (Lloydia), 1987, SO, 287
5-Ethenyltetrahydro-a.,a.,5-trimethyl-2-furanmethanol, 9CI. (hydroperoxide)
Tetrahydro-2-methy/-5-( 1-hydroxy-1-methy/ethyl)-2-
viny/furan. Linalool monoxide. Linaloo/ epoxide.
Epoxydihydrolinalool. Epoxylinalool
7-Methyl-3-methylene-1,6-octadiene Mo-00075
Myrcene. P-Myrcene
[60047-17-8]
[123-35-3]

'\. _£1_)/ (2R,5R)-form

H0/0~
CIOHI802 M 170.251 CIOHI6 M 136.236
Isol. from Citrus paradisi, Thea sinensis and other sources. Found in many essential oils, e.g. hop oil. Oil. Bp 116°,
Normally occurs with Mo-00068 to which it is closely Bp8.5 51-5l.SO.
related and to which the older synonyms also refer. I> RG5365000.
(2R,5R)-form Wrolstad, R.E. et a/, J. Agric. Food Chern., 1964, 12, 507 (ir)
Oil. [a.]~ +3.4°. Beckley, H.D. et a/, Org. Mass Spectrom., 1968, 1, 47 (ms)
(2R.SS)-form Waller, G.R. eta/, Phytochemistry, 1968, 7, 213 (biosynth)
Vig, O.P. et a/, Indian J. Chern., 1969, 7, 450; 1975, 13, 1244
Oil. [a.] 0 -12.1°. (synth)

19
2-Methyl-6-methylene-2,7-octadien-1-•.. - 7-Methyl-3-methylene-6-octen-1-ol Mo-00076 - Mo-00082

Karrer, W. et al, Konstitution und Vorkommen der Organischen Silverstein, R.M. et al, Tetrahedron, 1966, 22, 1929 (isol)
Pjlanzenstoffe, 2nd Ed., BirkhiiuseJ: Verlag, Basel, 1972-1985, v. Schantz, M. et al, Acta Chern. Scand., 1973, 27, 551 (isol, struct)
no. 32 (occur) Mori, K., Agric. Bioi. Chern., 1974, 38, 2045 (synth)
Harris, R.K. et al, Org. Magn. Reson., 1977, 9, 483 (pmr) Karlsen, S. et al, Acta Chem. Scand., Ser. B, 1976, 30, 664 (synth)
Riicker, G. et al, J. Nat. Prod. (Lloydia), 1987, 50, 287 (/J-Myrcene
hydroperoxide)
2-Methyl-6-methylene-2,7-octadien-1-ol, Mo-00076
9CI
8-Myrcenol
7-Methyl-3-methylene-1-octanol, 9CI Mo-00079
Bupleurol
[57072-58-9]
[57197-03-2]
yH20H I
~ ~CH2 0H
C1of1160 M 152.236 C10H200 M 156.267
(Z)-form [38228-40-9] Isol. from ethereal oil of Bupleurum fruticosum and from
Constit. of the essential oil of Thymus vulgaris. lsol. by B. linearifolium seed oils. Bp 209-210°.
glc. [1407-75-6]
Granger, R. et al, Phytochemistry, 1972, 11, 2301 (isol) Wolinsky, J. et al, J. Org. Chern., 1976, 41, 278 (synth, ir, pmr)
Vig, O.P. et al, J. Indian Chern. Soc., 1975, 52, 161 (synth) Ashraf, M. et al, Pak. J. Sci. Ind. Res., 1979, 22, 325; CA, 93,
245254j (isol)
2-Methyl-6-methylene-2,7-octadien-4-ol Mo-ooon
lpsdienol 2-Methyl-6-methylene-7-octene-2,3-diol, Mo-00080
9CI
I, ?H II 6,7-Dihydro-6,7-myrcenediol
~ (R)-form [24202-05-9)
C10H 160 M 152.236
A major component of the floral fragrance of several
species of orchids. Racemic ipsdienol attracts various
HO~
species of euglossine bees. OH
(R)-form [60894-97-5] C10H 180 2 M 170.251
Pheromone of the bark beetle, Ips confusus, that bores Constit. of roots of Bidens graveolens. Oil.
into Pinus ponderosa. Oil. [a]n -13.6° (c, 1 in MeOH).
[100664-21-9]
2,3-Dihydro: [35628-05-8]. 2-Methyl-6-methylene-7-octen-4-
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1281.
ol. /psenol
C10H 180 M 154.252
Pheromone of/. confusus and I. paraconfusus. Oil. Bp 15 2-Methyl-6-methylene-7-octen-2-ol, 9CI Mo-00081
86-88°. [a]n -17.5° (c, 1 in MeOH). Myrcenol
(S)-form [35628-00-3] [543-39-5]
Pheromone of I. paraconfusus. Oil. [a]i! + 11.9° (c, 0.26
in MeOH). HO_I II
Baekstrom, P. et al, Acta Chern. Scand., Ser. B, 1983, 37, I (synth, ~
bib[) C10H 180 M 154.252
Sakurai, H. et al, Tetrahedron, 1983, 39, 883 (synth) Perfumery ingredient. Liq. with lemon-like odour. Bp 15
Yamamoto, H. et al, J. Am. Chern. Soc., 1986, 108, 483 (synth)
Backstrom, P. et al, Acta Chern. Scand., Ser. B, 1987, 41, 442 105-106°, Bp5 78°.
(synth) I> RH3580000.
Klusener, P.A.A. et al, J. Org. Chern., 1987, 52, 5261 (synth) Ac: [1118-39-4]. 7-Acetoxy-7-methyl-3-methylene-1-octene.
Whitten, W.M. et al, Phytochemistry, 1988, 27, 2759 (isol) Myrcenyl acetate
Nomoto, T. et al, J. Chern. Soc., Chern. Commun., 1989, 295
(synth)
C12H 200 2 M 196.289
Oertle, K. et al, Helv. Chim. Acta, 1990, 73, 353 (synth) Perfumery ingredient. Liq. with woody cologne-like
Imai, T. et al, J. Org. Chern., 1990, 55, 4849 (synth) odour. Bp0.5 53°.
Brown, H.C. et al, Tetrahedron Lett., 1990, 31, 455 (synth) I> RH3585000.
Houlihan, W.J. et al, J. Am. Chern. Soc., 1959, 81, 4692 (struct, uv,
2-Methyl-6-methylene-3,7-octadien-2-ol Mo-00078 ir)
U.S. Pat., 3 176 022, (1965); CA, 62, 16316 (synth, uv, ir)
[22459-09-2] Freeman, S.K. et a/, Appl. Spectrosc., 1969, 23, 610 (ir)
Vig, O.P. et al, J. Indian Chem. Soc., 1972, 49, 163; 1973, SO, 329
HO_I II (synth)
~ Opdyke, D.L.J., Food Cosmet. Toxicol., 1976, 14, 617 (rev)

C10H 160 M 152.236

(E)-form [6994-89-4]
7-Methyl-3-methylene-6-octen-1-ol Mo-00082
Pheromone of the bark beetle, Ips confusus, which bores y-Geraniol
into Pinus ponderosa. Oil. Bp1. 4 55-57°. [13066-51-8)
2-Hydroperoxide: 2-Hydroperoxy-2-methyl-6-methylene-3,7-
octadiene. JJ-Myrcene hydroperoxide
C10H 160 2 M 168.235
~CH20H
Constit. of Artemisia annua. Unstable oil.

20
7-Methyl-3-methylene-7-octen-1-ol - Nectriapyrone Mo-00083 - Mo-00091

CIOHtsO M 154.252 2-(4-Methyl-3-pentenyl)-2-butene-1,4-diol Mo-00087

Oil. 3-Hydroxymethyl-7-methyl-2,6-octadien-1-ol
Mandai, T. et at, J. Org. Chern., 1984, 49, 3403 (synth)
~CH20H
7-Methyl-3-methylene-7-octen-1-ol Mo-00083 CHzOH
[73945-79-6] clOHJs01 M 170.251
(Z)-form [76480-92-7]
~CH2 0H Constit. of Chondrococcus hornemannii. Pale yellow oil.
Poulter, C.D. et at, J. Org. Chern., 1981, 46, 1532 (synth, pmr)
C 10H 180 M 154.252 Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1983 (isot, pmr, cmr)
Component of pheromone of San Jose scale.
Propanoyl: 3-(4-Methyl-3-pentenyl)furan Mo-00088
C13H 110 1 M 210.316 3-/sohexenylfuran. Perillene
Constit. of pheromone of San Jose scale.
[539-52-6]
Alerdice, M. et at, Tetrahedron Lett., 1984, 25, 1643.

3-Methyl-5-(2-methylpropyl)-2-
furancarboxaldehyde, 9CI
Mo-00084
0~
5-/sobutyl-3-methyl-2-furancarbaldehyde C10H 1P M 150.220
[90052-91-8] Constit. of oil from Perilla citriodora. Defence secretion
component from ants (Lasius fulginosus). Oil. Bp 185-
1860.

~CHO 0
Bemadi, R. et at, Tetrahedron Lett., 1967, 40, 3893 (isol)
Kaiser, R. eta/, Helv. Chim. Acta, 1976, 59, 1797 (isol)
Wiley, R.A. eta/, J. Org. Chern., 1983, 48, 1106 (synth, bib/)
C 10H 140 1 M 166.219 Takano, S. et at, Chern. Lett., 1984, 1261 (synth)
Constit. of essential oil of Tagetes glandulifera. Oil. Bp0 .2
80-90° (bath). 3-(4-Methyl-3-pentenyl)thiophene Mo-00089
Maurer, B. eta/, Tetrahedron Lett., 1984, 25, 1061 (struct, synth) [62469-65-2]

~
3-(4-Methyl-1,4-pentadienyl)furan Mo-00085
Lepalene. Lepalin

0
~ C 10H 14S M 166.287
s
C10H 110 M 148.204 Constit. of hops. Oil.
(E)-form [72057-12-6] Peppard, T.L. eta/, Chern. Ind. (London), 1979, 552 (isot, struct)
Constit. of Ledum palustre. Oil. Bp4 91-93°. Elvidge, J.A. et al, J. Chern. Soc., Perkin Trans. I, 1982, 1089 (isot,
synth)
Mikhailova, N.S. et at, Khim. Prir. Soedin., 1979, 322.

4-(4-Methyl-1,3-pentadienyl)-2(511)- Mo-00086
6- Methyl-2-vinyl-5-heptene-1,2-diol Mo-00090
3-Hydroxymethyl-7-methyl-] ,6-octadien-3-ol
furanone, 9CI
Scobinolide. Dihydrocleviolide [73510-11-9]

~0
HO CH 0H 2

C10H 180 1 M 170.251

Constit. of Chondrococcus hornemannii. Oil.
Ishida, T. et al, J. Pharm. Sci., 1981, 70, 406.
Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1983 (isol, pmr, cmr)
C10H 110 1 M 164.204
(E)-form [81053-16-9]
Metab. of fungus Psathyrella scobinacea. Also isol. from Nectriapyrone Mo-00091
Senecio clevelandii. Needles (EtzOjpet. ether). Mp 114- 4-M ethoxy-3-methyl-6-( 1-methyl-1-propenyl)-2H -pyran-2-
1150. one
(Z)-form [81053-17-0] [57685-79-7]
Cryst. (Et20jpet. ether). Mp 45°.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2425 (isol)
Gadir, S.A. eta/, J. Chern. Res. (S), 1986, 102 (isol, synth)

M 194.230

21
Phlebotrichin - Ursinanolide Mo-00092 - Mo-00097

Metab. of Gyrostroma missouriense. Cryst. Mp 100-102°. Tetrahydro-2,2-dimethyl-5-(1-methyl-1- Mo-00095

Nair, M.S.R. eta/, Tetrahedron Lett., 1975, 1655 (isol) propenyl)furan
Reffstrup, T. eta/, Tetrahedron Lett., 1976, 1903 (synth) [7416-35-5]

Phlebotricbin Mo-00092
[87392-63-0]
C10H 180 M 154.252
Isol. from oil of Citrus aurantifolia. Oil. d20 0.867. [ex]~+
0°. n~ 1.4662.
[56058-69-6, 56058-70-9)
Kovats, E. eta/, Helv. Chim. Acta, 1963, 46, 2705; 1966, 49, 2055
(is of)
Corbier, B. eta/, Recherches, 1974, 19, 235 (synth)

2,2,9-Trimethyl-1,6-dioxaspiro[4.4)non-3- Mo-00096
ene
C22H 300 9 M 438.474
Constit. of Viburnum phlebotrichurn. Powder
(EtOAcjhexane). Mp 141-143°. [cx]i7 -32.6° (c, 5 in
EtOH).
6-Epimer: [83905-61-7]. Phlebotricoside
CtoH 160 2 M 168.235
C 22H 300 9 M 438.474 (5R* ,9R*)-form [92356-04-2]
Constit. of V. phlebotrichum. Plates (MeOH/C 6H 6). Mp Constit. of Geranium oil. Oil.
140-142°. [cx] 0 -37.SO (c, 0.016 in EtOH). 3,4-Dihydro: [92356-10-0]. 2,2,9-Trimethyl-1,6-
Hase, T. et a/, Phytochemistry, 1982, 21, 1435 (Phlebotricoside) dioxaspiro[ 4.1]nonane
Takido, M. et a/, Phytochemistry, 1983, 22, 223 (Phlebotrichin) C 10H 180 2 M 170.251
From Geranium oil. Oil.
Rose oxide Mo-00093 (5R* ,9S*)-form [92356-08-6]
Tetrahydro-4-methyl-2-(2-methyl-1-propenyl)pyran, 9CI. 2- From Geranium oil. Oil.
/sobutenyl-4-methyltetrahydropyran 3,4-Dihydro: [92356-09-7].
[16409-43-1] From Geranium oil. Oil.
Kaiser, R., Helv. Chim. Acta, 1984, 67, 1198.

A (2R, 4R)-form Mo-00097

l 0 3t-A Ursinanolide
[83882-99-9]
C 10H 180 M 154.252
Constit. of essential oil of Pelargoniurn spp. and secretions
of Aromia moschata. Perfumery ingredient.
I> UQ1470000.
(2R,4R)-form [5258-11-7] C15H 1804 M 262.305
(-)-trans-form Constit. of Ursinia nana. Gum.
Oil. Bp1. 3 41-47°. [cx] 0 -18°. Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1309.
(2S,4R)-form [4610-11-1]
(-)-cis-form
Oil. Bpu 41-47°. [cx] 0 -15.3°.
Vidari, G. et a/, Tetrahedron Lett., 1973, 4065.
Snowden, R.L. eta/, Helv. Chim. Acta, 1987, 70, 1879 (synth)

3-(Tetrahydro-5,5-dimethyl-2-furanyl)-2- Mo-00094
buten-1-ol, 9CI

N y C H2 0H

C10H180 2 M 170.251
(E)-form [84184-43-0]
Constit. of peppermint oil. Oil with dry grassy hay
odour.
[84184-42-9)
Sakurai, K. et a/, Agric. Bioi. Chern., 1983, 47, 1249.

22
4,6-Dimethyl-4-octen-3-one - 4-Ethenyl-3-hydroxy-2-hydroxymethyl-... Mo-00098 - Mo-00105

Constit. of Artemisia arbuscula. Oil. [ocln +9.4° (c, 4.24 in

CHC13).
Irregular acyclic Epstein, W.W. eta/, Phytochemistry, 1984, 23, 2257.

monoterpenoids 2,5-Dimethyl-4-vinyl-2,3,5-hexanetriol
4-Ethenyl-2,5-dimethy/-2,3,5-hexanetrio/. 1-Santo/inene-
4,5,8-trio/
Mo-001 02

~
OH
4,6-Dimethyl-4-octen-3-one Mo-00098

OH
HO
C 10H 100 3 M 188.266
C 10H 180 M 154.252 Constit. of Achillea fragrantissima.
(S,E)-form [60132-36-7] Mflllicone Ahmed, A.A. et al, Phytochemistry, 1990, 29, 1322 (isol, pmr, ir)
Pheromone from the mandibular glands of the ants
Manica mutica, M. bradleyi and M. rubida. Oil. 2,5-Dimethyl-4-vinyl-5-hexene-2,3-diol Mo-001 03
Blanco, L. eta/, Tetrahedron Lett., 1981, 645 (isol, struct) 4-Etheny/-2,5-dimethyl-5-hexene-2,3-dio/. 4,5-Hydroxy-1,8-
Alexakis, A. eta/, Tetrahedron, 1984, 40, 715 (synth) santo/inadiene. 1,8-Santo/inadiene-4,5-dio/
Bestmann, H.J. et al, Angew. Chern., Int. Ed. Engl., 1987, 26, 784
(abs con.fig)
Yoneda, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 3163
(synth)

5-(1,1-Dimethyl-2-propenyl)-3-methyl- Mo-00099
2(4H)-furanone
C10H 180 1 M 170.251
(R)-form [98168-58-2]
lsol. from Achillea filipendulina and Artemisia herba-
alba. Oil. [ocln -11 o (c, 0.3 in CHC13). Abs. config. of
the A. herba-a/ba isolate inferred from its opt. rotn.
C 10H 140 1 M 166.219 (S)-form [98168-59-3]
Constit. of Pentzia calva. Oil. lsol. from Achillea fi/ipendulina. Oil.
Zdero, C. et al, Phytochemistry, 1990, 29, 189 (isol, pmr) Banarjee, S. et al, Planta Med., 1985, 51, 177 (isol, ir, ms, pmr)
Marco, J.A. et al, Phytochemistry, 1989, 28, 3121 (isol, pmr)
2,5-Dimethyl-3-vinyl-1,4-hexadiene Mo-001 00
3-Etheny/-2,5-dimethy/-1 ,4-hexadiene. Santolinatriene 1,2-Epoxy-2,5-dimethyl-3-vinyl-4-hexene Mo-001 04
[2153-66-4] 2-(1-Etheny/-3-methy/-2-butenyl)-2-methy/oxirane, 9CI
[66428-32-8]
y

CtoH16 M 136.236
(S)-form [70005-95-7]
JA
Constit. of Santo/ina chamaecyparissus. Oil. Bp 143°.
[ocln +64o. C 10H 160 M 152.236
.1AH

Constit. of Artemisia tridentata. Oil. Bp 18 65-70°. [ocln

Thomas, A.F. et al, Tetrahedron Lett., 1964, 3775 (isol) -37.2° (c, 0.8 in CHC1 3).
Bates, R.B. eta/, Tetrahedron Lett., 1965, 1453 (biosynth)
Sucrow, W., Angew. Chern., Int. Ed. Engl., 1968, 7, 629 (synth) Noble, T.A. et al, Tetrahedron Lett., 1977, 3933.
Thomas, A.F. et al, Helv. Chim. Acta, 1971, 54, 1822 (synth)
Poulter, C.D., J. Agric. Food Chern., 1974, 22, 167 (rev) 4-Ethenyl-3-hydroxy-2-hydroxymethyl- Mo-00105
Dembitskii, A.D. et a/, Izv. Akad. Nauk Kaz. SSR, Ser. Khim.,
1978, 28, 45 (isol) 2,5,5-trimethyltetrahydrofuran
Takano, S. et al, J. Org. Chern., 1985, SO, 931 (synth) 5,8-Epoxy-1-santo/inene-4,6-dio/

HO t=
2,5-Dimethyl-4-vinyl-1,5-hexadien-3-ol Mo-001 01 \ I

4-Etheny/-2,5-dimethy/-1 ,5-hexadien-3-o/, 9CI. lsolyratol

[96203-74-6] HOH2M
C 10H 180 3 M 186.250

~ OH
Constit. of Achillea fragrantissima.
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 1322 (isol, pmr, ir)

M 152.236

23
5-Ethylidene-5,6-dihydro-3,6,6-... - 5-Methyl-2-methylene-4-vinyl-5-... Mo-00106 - Mo-00112

S-Ethylidene-5,6-dihydro-3,6,6-trimethyl- Mo-001 06 d~0 0.977. Bp 12 143-144°. n~ 1.4560.

2-pyranone [20777-39-3]
4-Ethylidene-2,5-dimethy/-2-hexen-5-o/ide Schinz, H. eta/, Helv. Chim. Acta, 1947, 30, 1483 (synth)
[24449-37-4] Soucek, M. eta/, Collect. Czech. Chern. Commun., 1959, 24, 3802
(abs conjig)

lyy Baba, S.N. eta/, Tetrahedron, 1966, 22, 903 (synth, ret')
Banthorpe, D.V. eta/, Phytochemistry, 1977, 16, 85 (biosynth)
Bertrand, M. eta/, Tetrahedron Lett., 1977, 1785 (synth)
+o~o Kramer, A. et a/, Helv. Chim. Acta, 1982, 65, 293 (synth, ir, pmr,
bib[)
Takano, S. eta/, J. Org. Chern., 1985, SO, 931 (synth)
C 1.,H140 1 M 166.219 Celebuski, J. eta/, Tetrahedron, 1985, 41, 5741 (synth)
lsol. from Chrysanthemumfiosculosum. Cryst. Mp 64.5°.
Bohlmann, F. eta/, Tetrahedron Lett., 1969, 2413.
Lyratol Mo-00110
4-Etheny/-2,5-dimethy/-2,5-hexadien-1-o/. 2,5-Dimethy/-4-
S-Hydroxy-2,5-dimethyl-4-vinyl-2-hexen- Mo-001 07 viny/-2 ,5-hexadien-1-o/
1-al

HOH,CAXr
4-Ethenyl-5-hydroxy-2,5-dimethy/-2-hexen-1-a/. 8-Hydroxy-
1,4-santolinadien-6-a/ ~
[128571-52-8]

?*OH C 10H 160 M 152.236

(S)-form [19889-92-0]
Constit. of Cyathoc/ine lyrata essential oil. Oil. Bp 2 105°.
[1X]n +62.3° (c, 4.6 in CHC1 3).
]-Carboxylic acid: [17152-12-4]. 4-Etheny/-2,5-dimethy/-2,5-
CHO hexadienoic acid, 9CI. 2,5-Dimethy/-4-viny/-2,5-
C 10H 160 1 M 168.235 hexadienoic acid. Lyratic acid. Lyratoic acid
Constit. of Achillea fragrantissima. Oil. C 10H 140 1 M 166.219
Constit. of C. lyrata. Bp4 110°. The S-config. does not
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 1322 (isol, pmr, ir) appear to have been explicitly detd. but is assumed here.
No opt. rotn. reported.
4-Hydroxy-6-isopropyl-3,S-dimethyl-2H- Mo-00108 Deugan, O.N. eta/, Curr. Sci., 1967, 36, 205 (isol)
pyran-2-one Devgan, O.N. eta/, Tetrahedron, 1969, 25, 3217 (strucl)
4-Hydroxy-3,5-dimethyl-6-(1-methylethyi)-2H-pyran-2-one, Sucrow, W., Tetrahedron Lett., 1970, 4725 (synth)
9CJ Bamboria, B.K. eta/, Indian J. Chern., 1971, 9, 186 (isol)
[103771-79-5]
Marmelolactone Mo-00111

'' (2R,4S)-form

0~
Absolute
configuration

C 10H 140 3 M 182.219 CioH 140 1 M 166.219

Constit. of Helichrysum zeyheri. Oil. (2R,4S)-form [74133-35-0]
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 1133. Marmelolactone A
Constit. of Cydonia oblonga. Syrup. [IX]~ +93.6° (c, 0.09
Lavandulol Mo-00109 in MeOH).
5-Methyl-2-(1-methy/ethenyl)-4-hexen-J-o/, 9CI. 2- (2R,4R)-form [74183-60-1]
Isopropenyl-5-methy/-4-hexen-J-o/ Marmelolactone B
From C. ob/onga. Syrup. [IX]~ +21.8° (c, 0.11 in
MeOH).
(R)-form Tsuneya, T. eta/, Agric. Bioi. Chern., 1980, 44, 957 (isol)
Ishihara, M. eta/, Agric. Bioi. Chern., 1983, 47, 2121 (abs conjig)
Nishida, Y. eta/, Agric. Bioi. Chern., 1983, 47, 2123; 1986, SO, 191,
C 1.,H 180 M 154.252 813 (synth, cmr, cd)
Both the parent alcohol and its simple esters (esp. the
acetate) are used in perfumery. S-Methyl-2-methylene-4-vinyl-S-hexene- Mo-00112
(R)-form [498-16-8] 1,3-diol
Constit. of French lavender oil. Bp 13 94-95°. [IX]~ 7-Hydroxy-5,6-dehydro-4,5-dihydrolyratrol

yy
-10.7° (c, 1.01 in MeOH) (opt. pure).
(S)-form [50373-53-0] HOH2
[a]~ + 10.11° (pure substance) (opt. pure).
(±)-form [1845-51-8]
df 0.880. Bp6 100-101°. nJ11.4710. ~OH
Ac: [25905-14-0].
C 11H 100 1 M 196.289

24
5-Methyl-2-(1-methylethenyl)-3-... - Santolinolides Mo-00113 - Mo-00118

C10H 160 1 M 168.235 Pyrolysis prod. of Chrysanthemic acid, Mo-00211.

Constit. of Artemisia herba-a/ba. Oil. Shows insecticidal activity. Cryst. Mp 83.5-84.SO. [cxln
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 3661 (isol, pmr) +64° (c, 0.6 in EtOH).
(S)-form [29799-64-2]
Mo-00113 Cryst. Mp 84°. [cx]i;l -57.7° (EtOH).
5-Methyl-2-(1-methylethenyl)-3-hexene-
1,5-d.iol, 9CI (±)-form
2-Isopropenyl-5-methy/-3-hexene-1 ,5-diol
Mp 59-60°. Bp9 116-119°.
Takeda, A. et al, Bull. Chern. Soc. Jpn., 1977, SO, 1133.

Santolina alcohol Mo-00116

3-Etheny/-2,5-dimethyl-4-hexen-2-o/, 9Cl. 2,5-Dimethy/-3-
vinyl-4-hexen-2-o/
C10H 180 1 M 170.251 [35671-15-9]
(E)-form

~
l-Ac: [38237-37-5].
CuH100 3 M 212.288 Absolute
Constit. of Lavandin abrialis. Appears to be wrongly
configuration
named as (1-methylethylidene) in CA. H
Belstein, J.C. et al, Tetrahedron, 1972, 28, 3439. C 10H 180 M 154.252
(S)-form [21149-19-9]
Multistriatin Mo-00114 Cons tit. of the essential oil of Ormenis multicaulis. Oil.
5-Ethyl-2 ,4-dimethy/-6,8-dioxabicyclo(3.2 .J]octane [cx)i: + 13.SO.
Chretien-Bessiere, Y. et al, Bull. Soc. Chim. Fr., 1968, 2018 (isol,
struct)
Poulter, C.D. et al, Tetrahedron Lett., 1972, 71 (abs config)
(1S,2R,4S,5R)-form Moiseenkov, A.M. et al, J. Chern. Soc., Chern. Commun., 1982,
109 (synth)
C10H 180 1 M 170.251
(JS,2R,4S,5R)-form [59014-03-8] rr.-Muhistriatin Santolinic acid Mo-00117
Component of aggregation pheromone of North 3-Etheny/-2,5-dimethyl-4-hexenoic acid, 9CI. 2,5-Dimethyl-3-
American populations of the European elm bark beetle, viny/-4-hexenoic acid
Scolytus multistriatus. Oil. [cx]i;l -47° (hexane). [58191-71-2]
(1S,1S,4R,5R)-form [59014-05-0] P-Muhistriatin
Oil. [cx]i;l -73° (hexane). HOOC} I
(1S,2R,4R,5R)-form [54832-21-2] y-Muhistriatin
Oil. [cx]n - 21 ° (hexane). ~
(1S,2S,4S,5R)-form [54832-22-3] ~-Multistriatin H
Component of aggregation pheromone of European cJoH160 1 M 168.235
populations of S. multistriatus. Oil. [cx]i? -80° (hexane). Me ester: [57784-47-1].
Gore, W.E. et al, J. Org. Chern., 1976, 41, 1926 (pmr, conformn) C 11H 180 1 M 182.262
Pearce, G.T. et al, J. Org. Chern., 1976, 41, 2797 (synth, abs config) Constit. of Artemisia tridentada, isol. by glc. [cxln + 10.6°
Cernigliaro, G.J. et al, J. Org. Chern., 1977, 42, 3622 (synth) (c, 0.76 in MeOH).
Pearce, G.T. et al, J. Magn. Reson., 1977, 27, 297 (cmr)
Weiter, L., Can. J. Chern., 1978, 56, 2700 (synth) Shaw, J. et al, J. Chern. Soc., Chern. Commun., 1975, 590 (isol,
Bartlett, P.A. et al, J. Org. Chern., 1979, 44, 1625 (synth) struct)
Mori, K. et al, Tetrahedron, 1980, 36, 87 (syrllh) Boyd, J. et al, J. Chern. Soc., Chern. Commun., 1976, 380 (synth)
Hoffmann, R.W. eta/, Chern. Ber., 1981, 114, 2802 (synth)
Plaumann, D.E. et al, J. Org. Chern., 1982, 47, 941 (synth) Santolinolides Mo-00118
Sum, P.-E. et al, Can. J. Chern., 1982, 60, 327 (synth)
4-Ethenyldihydro-3-methyl-5-(J-methylethenyl)-2(3H)-
Helbig, W., Justus Liebigs Ann. Chern., 1984, 1165 (synth)
Mulzer, J. et al, Justus Liebigs Ann. Chern., 1986, 1152 (synth) furanone, 9CI. 5-Isopropenyl-3-methyl-4-vinyl-2(3H)-
Larcheveque, M. et al, Tetrahedron, 1987, 43, 2303 (synth) furanone
Mori, K. et al, Tetrahedron, 1988, 44, 1035 (synth) [72203-49-7]

Pyrocin
4,5-Dihydro-5,5-dimethyl-4-(2-methyl-2-propenyl)-2(3H)-
Mo-00115
~/ (2S,3S,4S)-form
furanone lrl{;~o
[473-50-7]
C 10H 140 2 M 166.219
Oil.

~0
(R)-form
Absolute (2S,3S,4S)-form [70898-17-8]
configuration Santolinolide A
Constit. of Artemisia tridentata. Oil. [cxln -9.4° (c, 1.69
in CHC1 3). Artifact of epimerisation.
CtoHt60 1 M 168.235
(2R,3S,4S)-form
(R)-form [17779-19-0]
Santolinolide B

25
Tetrahydro-4-methyl-2-(3-methyl-1,3-... - 3,3,6-Trimethyl-5-heptene-1,2,4-... Mo-00119 - Mo-00123

Main constit. of the Santolinolide fraction from A. Ruppert, J.F. et ai, J. Org. Chern., 1976, 41, 550 (synth)
tridentata. Oil. [1X]n +64° (c, 0.023 in CHC1 3). Grandi, R. et ai, Phytochemistry, 1976, 15, 1770 (isol)
Dale, P.C. et ai, J. Am. Chern. Soc., 1977, 99, 3816 (synth)
(2S,3S,4R)-form [70898-20-3] Poulter, C.D. et ai, J. Am. Chern. Soc., 1977, 99, 3816 (synth)
Santolinolide B' Segal, R. et ai, Phytochemistry, 1980, 19, 2761 (isoi, bihl)
Isol. from A. tridentata. Artifact of epimerisation, isol. Brown, H.C. et ai, Tetrahedron Lett., 1986, 25, 1215 (synth)
only as a rnixt. with lactone B.
(2R,3S,4R)-form [70898-19-0] 3,3,6-Trimethyl-1,5-heptadien-4-one Mo-00122
Santolinolide C Artemisia ketone
lsol. from A. tridentata. Solid. [1X]n -12.8° (c, 1.2 in
CHC1 3). Artifact of epimerisation. [546-49-6]
Epstein, W.W. et ai, J. Org. Chern., 1979, 44, 3113. 0

Tetrahydro-4-methyl-2-(3-methyl-1,3-
butadienyl)furan, 9CI
Mo-00119 ~
CIOH160 M 152.236
4-Methyl- 2-(3-methyl-1-butadienyl)oxolane Constit. of Santo/ina chamaecyparissus.

b.F<
5,6-Epoxide: [79507-83-8]. 5,6-Epoxy-3 ,3,6-trimethyl-1-
hepten-4-one. 1-(3,3-Dimethyloxiranyl)-2,2-dimethyl-3-
(2R,4S)-(E)-form
buten-1-one, 9Cl. Epoxyartemisia ketone
0 CIOH1602 M 168.235
CIOH160 M 152.236 Constit. of Artemisia vulgaris. Oil. Bp 10 75°.
(2R,4S,E)-form [89103-55-9] Zalkow, L.H. et a/, J. Org. Chern., 1964, 29, 2786 (isoi, struct)
M armelo oxide A Pillot, J.-P. et ai, Tetrahedron Lett., 1976, 1871 (synth)
Flavour component of quince fruit. Oil. [1X]n -33.4° (c, Banthorpe, D.V. et ai, Phytochemistry, 1977, 16, 1387 (biosynth)
0.18 in Et20). Michelot, D. eta/, Synth. Commun., 1977, 7, 95 (synth)
Risinger, G.E., Experientia, 1978, 34, 1121 (synth)
(2R,4R,E)-form [89103-56-0] Gosselin, P. et ai, Tetrahedron Lett., 1978, 2717 (synth)
Marmelo oxide B Naf-Miiller, R. et ai, Heiv. Chim. Acta, 1981, 64, 1424 (epoxide)
Flavour component of quince fruit. Oil. [oc]i;' + 23.SO (c, Fehr, C. eta/, Helv. Chim. Acta, 1987, 70, 1745 (synth)
0.15 in Et20).
Tsuneya, T. et ai, Agric. Bioi. Chern., 1980, 44, 957 (isoi, struct), 3,3,6-Trimethyl-5-heptene-1,2,4-triol, 9CI Mo-00123

fH
Nishida, Y. et ai, Agric. Bioi. Chern., 1983, 47, 2969 (synth, abs
config)
~H 1
Mo-00120 HOH2C'!(~"
2,5,5-Trimethyl-3,6-heptadien-2-ol
Yomogi alcohol A
C 10H 200 3 M 188.266
[26127 -98-0]
Tri-Ac: [83117-67-3]. 1,2,4-Triacetoxy-3,3,6-trimethyl-5-
~ ~ 1 heptene
Ct6H 260 6 M 314.378
~ x~b"H Constit. of Calea oxylepis. Oil.
C10H 180 M 154.252 Bohlmann, F. et ai, Phytochemistry, 1982, 21, 1164.
Constit. of the essential oil of Artemesia feddei. Oil. Bp 10
71-72°.
Thomas, A.F. et ai, Heiv. Chim. Acta, 1971, 54, 1822 (struct,
synth)
Poulter, C.D., J. Agric. Food Chern., 1974, 22, 167 (biosynth, rev)
Oshima, K. et ai, Bull. Chern. Soc. Jpn., 1975, 48, 1567 (synth)
Poulter, C.D. et ai, J. Am. Chern. Soc., 1977, 99, 3816 (synth)

3,3,6-Trimethyl-1,5-heptadien-4-ol Mo-00121
Artemisia alcohol

(R)-form

C 10H 180 M 154.252

(R)-form [77363-66-7]
Constit. of Artemisia herba-alba. Oil. [ali;' + 32.1° (neat).
(S)-form [29887-38-5]
Constit. of Achillea ageratum, Artemisia japonia and
Artemisia ludoviciana. Oil. Bp9 92-95°. [oc]i;' -32.12°
(neat).
Ac: [3465-88-1]. Artemisia alcohol acetate
C 12H 200 2 M 196.289
From A. spp. Oil. Bp6 74-76°. [IX]~ -33.9°.
Epstein, W.W. et al, Phytochemistry, 1973, 12, 737 (isol)

26
Aplysiapyranoid A - 8-Bromo-3,7-dichloro-2,6-dimethyl-... Mo-00124 - Mo-00132

C 10H 16Br2Cl2 M 366.950

Constit. of Chondrococcus hornemanni. Oil.
Halogenated Burreson, B.J. eta/, Chern. Lett., 1975, 1111.

dimethyloctanes 6-Bromo-3-bromomethyl-2,3,7-trichloro-7- Mo-00128

methyl-1-octene
[58086-84-3)

c~Br
Aplysiapyranoid A Mo-00124

b
[109927-30-2] Br Cl
C10H 15Br2Cl3 M 401.395
,.Br Constit. of Chondrococcus hornemanni. Oil.
R-
2 Burreson, B.J. eta/, Chern. Lett., 1975, 1111.
I 0
;==' 7-Bromo-3-bromomethyl-2,3,6-trichloro-7- Mo-00129
Cl
methyl-1-octene
R 1 = Br, R2 = H [58086-79-6)
C 10H 15Br2CIO M 346.489
Constit. of Aplysia kurodai. Oil. [1X) 0 +4.4° (c, 1 in B~Br
CHCI 3).
2-Epimer: [108212-12-0). Aplysiapyranoid B Cl Cl
C10H 15Br2CIO M 346.489
Constit. of A. kurodai. Cryst. (EtOH). Mp 46-49°. [1X) 0 C10H 15Br2Cl3 M 401.395
-27° (c, 0.91 in CHCI 3). Constit. of Chondrococcus hornemanni. Oil.
Burreson, B.J. eta/, Chern. Lett., 1975, 1111.
Kusumi, T. et a/, J. Org. Chern., 1987, 52, 4597.

Aplysiapyranoid C Mo-00125 3-Bromo-8-chloro-6-chloromethyl-2- Mo-00130

methyl-1,6-octadiene
[109927-31-3)
As Aplysiapyranoid A, Mo-00124 with
lH2 C~ ~
R1 = H, R2 = Cl CIH2C~ ............... Y"
CIOHI5BrCI20 M 302.037 Br
Constit. of Aplysia kurodai. Oil. [1X) 0 + 52° (c, 1 in CHC1 3).
C 10H 15BrCI2 M 286.038
2-Epimer: [109927-32-4). Aplysiapyranoid D
(Z)-form [125537-99-7]
C 10H 15BrC120 M 302.037
Constit. of Chondrococcus hornemannii. Oil. [1X) 0 -22.SO
From A. kurodai. Oil. [1X) 0 + 3.4° (c, 1.1 in CHC1 3).
.(c, 0.008 in CHCI 3).
Kusumi, T. eta/, J. Org. Chern., 1987, 52, 4597.
Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1983 (iso/, prnr, crnr)

6-Bromo-3-bromomethyl-3,7-dichloro-7- Mo-00126 2-(Bromochloromethyl)-1,5,6-trichloro-6- Mo-00131

methyl-1-octene methyl-1,3,7~octatriene, 9CI
[58086-83-2)
[89197-88-6)

c~r CHBrCI CI

Br
Cl
~ Cl
C 10H 16Br2Cl2 M 366.950
Isolated as an inseparable mixture with 7-Bromo-3- C10H 11 BrC14 M 352.912
bromomethyl-3,6-dichloro-7-methyl-1-octene, Mo- (3R*,4S* .SE,7E)-form
00127. Constit. of Chondrococcus hornemanni. Constit. of Plocamium cartilagineum. Oil.
Burreson, B.J. eta/, Chern. Lett., 1975, 1111 (isol) Crews, P. et a/, J. Org. Chern., 1984, 49, 1371 (isol, struct, crnr)

7-Bromo-3-bromomethyl-3,6-dichloro-7- Mo-00127 8-Bromo-3,7-dichloro-2,6-dimethyl-1,5- Mo-00132

methyl-1-octene octadiene
[58086-82-1]
~CH2Br
Cl Cl
C 10H 15BrC12 M 286.038
(E)-form [73328-38-8)

27
3-Bromomethyl-3-chloro-7-methyl-1,6-... - 1-Chloro-3-chloromethyl-7-methyl-... Mo-00133- Mo-00141

Constit. of Plocamium angustum. Oil. [IX]~ + 19° (c, 0.5 Constit. of Plocamium spp. Shows antifungal props. Oil.
in CHC1 3). [1X] 0 -48.8° (c, 0.86 in CHC1 3).
Dunlop, R.W. et a/, Aust. J. Chern., 1979, 32, 2735. Stierle, D.B. et al, Tetrahedron, 1979, 35, 2855.

3-Bromomethyl-3-chloro-7-methyl-1,6- Mo-00133 1-Bromo-4,6,8-trichloro-3,7-d.imethyl-3,7- Mo-00138

octad.iene octadien-2-ol
[60696-34-6] Costatol
[63023-57-4]
~Br OH
H 1 CH2 Br

C10H 16BrC1 M 251.593

Constit. of Chondrococcus hornemanni. Oil. [IX]~ -3.7° (c, -::7 # Absolute
15 in CH2Cl0.- Cl Cl Cl configuration
Woolard, F.X. et al, Phytochemistry, 1976, 15, 1069.
C10H 14BrC130 M 336.482
3-Bromomethyl-2,3-d.ichloro-7-methyl-1,6- Mo-00134 Constit. of Plocamium costatum. Cryst. (hexane). Mp 88-
890. [1X] 0 -103° (c, 1 in CHC1 3).
octadiene
Kazlauskas, R. et al, Tetrahedron Lett., 1976, 4451.
[58086-81-0]

L OVCH~Br 7-Bromo-4,6,8-trichloro-2,6-d.imethyl-1,4-
octadien-3-one
Mo-00139

~Cl
Plocamenone
[89353-92-4]
. C10H 15BrC12 M 286.038
Constit. of Chondrococcus hornemanni. Oil.
Burreson, B.J., Chern. Lett., 1975, 1111.
.JJ(f y 'y_Cl.
-::?' :CH Cl 2

0 H Br
3-Bromomethyl-2,3,6-trichloro-7-methyl- Mo-00135
1,6-octad.iene C10H 12BrC130 M 334.466
Constit. of the red alga Plocamium sp. Oil. [1X] 0 -17.3°
[58086-80-9]
(CHC1 3).
I> Shows mutagenic props.
~Br Stierle, D.B. et al, Tetrahedron Lett., 1984, 25, !53 (isol)
Naylor, S. et al, J. Nat. Prod. (Lloydia), 1985, 48, 72 (struct, cmr)
C1 C1
C 10H 14BrC13 M 320.483 Cartilagineal Mo-00140
Constit. of Chondrpcoccus hornemanni. Oil. 5,6-Dichloro-2-(chloromethylene)-6-methyl-3, 7-oc tadienal,
Burreson, B.J. et al, Chern. Lett., 1975, 1111. 9CI
[53915-35-8]
8-Bromo-1,3,4,7-tetrachloro-7- Mo-00136
CHO C1
chloromethyl-3-methyl-1,5-octadiene
ClH2 C CH2 Br Cl
Cl~
a
Cl~Cl C10H 11 Cl30 M 253.554
C1 Constit. of Plocamium cartilagineum. Viscous liq. Bp0 _1
C10H12BrC15 M 389.372 130°.
(JE,3R,4S,5E)-form [72719-90-5] Crews, P. et al, J. Org. Chern., 1974, 39, 3303.
Constit. of Plocamium spp. Antifungal agent. Oil. [1X] 0
-20.2° (c, l.l9 in CHC1 3). 1-Chloro-3-chloromethyl-7-methyl-2,6- Mo-00141
Stierle, D.B. et al, Tetrahedron, 1979, 35, 2855. octad.iene, 9CI
8-Bromo-1,3,4,7-tetrachloro-3,7-d.imethyl- Mo-00137 I ?H20
1,5-octad.iene ~CH2 Cl

C10H 16Cl2 M 207.142

VCH2 ~r ~p ~ (Z)-form [112642-61-2]
Cl/~Y~'Cl
Constit. of Chondrococcus hornemannii. Oil.
Cl Coli, J.C. et al, Aust. J. Chern., 1987, 40, 1893.
C10H 13BrC14 M 354.928
(JE,3R,4S,5E)-form [72719-89-2]

28
8-Chloro-6-chloromethyl-2-methyl-... - Costatone Mo-00142 - Mo-00149

8-Chloro-6-chloromethyl-2-methyl-1,6- Mo-00142 3-Chloromethyl-7-methyl-2,7-octadiene- Mo-00146

octadien-3-ol 1,6-diol

C1ofl16Cl20 M 223.141 C 10H 17Cl0 2 M 204.696

(Z)-form [125538-02-5] (Z)-form
Constit. of Chondrococcus hornemannii. Oil. [cx] 0 -12.3° Di-Me ether: [125538-05-8]. 6-Chloromethyl-3,8-dimethoxy-
(c, 0.002 in CHC1 3). 2-methyl-1 ,6-octadiene
3-Me ether: [125538-01-4]. 8-Chloro-6-chloromethyl-3- CuH21 Cl02 M 232.749

Cl
methoxy-2-methyl-1 ,6-octadiene
C 11H 18 20 M 237.168
Constit. of C. hornemannii. Oil. [cx] 0 -16.SO (c, 0.017 in
Constit. of Chondrococcus hornemannii. Oil. [cx] 0 -23.9°
(c, 0.004 in CHC1 3).
Coli, J.C. et a/, Aust. J. Chern., 1989, 42, 1983 (isol, prnr, crnr)
CHC1 3).
Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1983 (isol, prnr, crnr) 6-Chloromethyl-2-methyl-2,6-octadiene- Mo-00147
1,8-diol
8-Chloro-6-chloromethyl-2-methyl-2,6- Mo-00143
octadien-1-ol CH2Cl

CH2Cl HOH2C~CH20H
CIH2C~CH20H C 10H 17Cl02 M 204.696
(2E,6Z)-form
C1ofl 16Cl20 M 223.141
Di-Me ether: [125538-06-9]. 6-Chloromethyl-1 ,8-dimethoxy-
(2E,6Z)-form [125538-04-7] 2-methyl-2,6-octadiene
Constit. of Chondrococcus hornemannii. Oil. CuH21 Cl02 M 232.749
Me ether: [125538-03-8]. 1-Chloro-3~chloromethyl-8- Constit. of Chondrococcus hornemannii. Oil.
methoxy-7-methyl-2 ,6-octadiene Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1983 (isol, prnr, crnr)
C 11H 18Cl20 M 237.168
Constit. of C. hornemannii. Oil.
Costatolidet Mo-00148
Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1983 (isol, prnr, crnr)
[63023-58-5]
1-Chloro-3,7-dimethyl-2,6-octadiene Mo-00144
Cl!Y Absolute
~CH2Cl ~),oAo configuration

C1ofl 17Cl M 172.697

(E)-form [5389-87-7] C9H 10Cl20 2 M 221.082
Geranyl chloride Constit. of Plocamium costatum. Oil. [cx] 0 -152° (c, 0.87 in
Intermed. in manuf. of terperte alcohols used in CHCI 3).
perfumery etc. Oil. Bp0 _4 47-49°. Stierle, D.B. et a/, Tetrahedron Lett., 1976, 4455 (isol, struct)
Williard, P.G. et al, J. Org. Chern., 1983, 48, 1123 (synth)
Org. Synth., 1974, 54, 63.

6-Chloro-2,6-dimethyl-2,7-octadiene Mo-00145 Costatone Mo-00149

Linalyl chloride (63023-59-6]

L _ (tCH,lk
[471-10-3]
Absolute

~ "l OH
configuration

C 10H 17Cl M 172.697

In termed. in the manuf. of terpene alcohols. Bp6 79-80°.
(cx] 0 -4.7°.
Nitrosate: Cryst. (CHCI 3jpet. ether). Mp 109°.
Barnard, D. et al, J. Chern. Soc., 1950, 126 (synth)
Piguleoski, G.V. eta/, J. Gen. Chern. USSR (Engl. Trans/.), 1957,
27, 891 (synth)
Hori, T. et al, J. Org. Chern., 1979, 44, 4208 (synth, bib[)
C 10HuBr2Cl20 2 M 394.917
Constit. of Plocamium costatum. Cryst. (hexane). Mp 70°.
[cx] 0 -52.4° (c, I in CHCI 3).
Kazlauskas, R. eta/, Tetrahedron Lett., 1976, 4451 (isol, struct)
Stierle, D.B. et al, Tetrahedron Lett., 1976, 4455 (cryst struct)
Williard, P.G. et al, Tetrahedron Lett., 1984, 25, 5009 (synth)

29
4,6-Dibromo-1-chloro-3,7-dimethyl-... - 1,8-Dibromo-3,4,7-trichloro-3,7-... Mo-00150 - Mo-00158

4,6-Dibromo-1-chloro-3,7-dimethyl-2,7- Mo-00150 (JE,JZ)-form [96300-26-4]

octadiene Constit. of Plocamium cartilagineum. Oil.
[62743-07-1] Blunt, J.W. et al, Aust. J. Chern., 1985, 38, 319.

4,8-Dibromo-3,7-dichloro-3,7-dimethyl- Mo-00155
~CH2Cl 1,5-octadiene
Br Br [119903-44-5]
C 1.,H15Br1Cl M 330.489
Constit. of Plocamium violaceum. Oil. [cx]i? -35° (c, 1.43 in
CHC1 3).
Crews, P. et al, J. Org. Chern., 1977, 42, 2812.
C10H 14Br1Cl1 M 364.934
7,8-Dibromo-6-(chloromethylene)-2- Mo-00151 Constit. of Plocamium hamatum. Oil. [cxln -7° (c, 0.006 in
methyl-2-octene, 9CI CHCl 3).
[112642-60-1] Coli, J.C. et al, Aust. J. Chern., 1988, 41, 1743.

Cl
2-(Dibromomethyl)-1,5,6-trichloro-6- Mo-00156
~CH,Ik methyl-1,3,7-octatriene
[65207-96-7]
Br
CHBr2 Cl
C 10H 15Br1Cl M 330.489
Constit. of Chondrococcus hornemannii. Oil. [cx]n
O.Q15 in CHC1 3).
Coli, J.C. et al, Aust. J. Chern., 1987, 40, 1893.
+ 12.5° (c,
~
Cl C1
C 10H 11 Br1Cl3 M 397.363
4,6-Dibromo-3,7-dichloro-3,7-dimethyl- Mo-00152 Constit. of Aplysia limacina. Oil. [cx]n -9.7° (c, 0.4 in
CHCl3).
1,2-epoxyoctane
(2,4-Dibromo-1 ,5-dichloro-1 ,5-dimethylhexyl)oxirane, 9CI Imperato, F. et al, Experientia, 1977, 33, 1273 (isol)
Crews, P. et al, J. Org. Chern., 1984, 49, 1371 (crnr, struct)
[96300-29-7]
4,7-Dibromo-3,6,8-trichloro-3,7-dimethyl- Mo-00157

~Br Br 0
1,2-epoxyoctane
(2,5-Dibromo-1 ,4,6-trichloro-1 ,5-dimethylhexyl)oxirane, 9CI
[96300-30-0]
C 1.,H16Br1Cl10 M 382.949
Constit. of Plocamium cartilagineum. Oil. Br Cl
Blunt, J.W. et al, Aust. J. Chern., 1985, 38, 319. ClH2 C~
Cl Br O
4,7-Dibromo-3,6-dichloro-3,7-dimethyl- Mo-00153
C 10H 15Br2Cl30 M 417.394
1,2-epoxyoctane Constit. of Plocamium cartilagineum. Oil.
(2,5-Dibromo-1 ,4-dichloro-1 ,5-dimethylhexyl)oxirane, 9CI
Blunt, J.W. et al, Aust. J. Chern., 1985; 38, 319.
[96300-28-6]
1,8-Dibromo-3,4,7-trichloro-3,7-dimethyl- Mo-00158

~ Cl Br
1,5-octadiene
CH2 Br Cl

C 10H 16Br1Cl10 M 382.949 Cl~Br

Constit. of Plocamium cartilagineum. Cl
Blunt, J.W. eta/, Aust. J. Chern., 1985, 38, 319. C10H 13Br1Cl3 M 399.379
(JE,3R,4S,5E,7S)-form [73245-53-1]
1,6-Dibromo-2,7-dichloro-3,7-dimethyl- Mo-00154 Constit. of Plocamium spp. Shows antifungal props.
1,3-octadiene, 9CI Cryst. Mp 48.5-49°. [cx]n -46.3° (c, 1.03 in CHCl 3).
Stierle, D.B. et al, Tetrahedron, 1979, 35, 2855 (cryst struct, abs

~"'
config)

Br
M 364.934

30
1,7-Dibromo-2,6,8-trichloro-3,7-... - 1,8,8-Tribromo-3,4,7-trichloro-3,7-... Mo-00159 - Mo-00168

1,7-Dibromo-2,6,8-trichloro-3,7-dimethyl- Mo-00159 1,4,6-Tribromo-7-chloro-3,7-dimethyl-1- Mo-00164

3-octene octen-3-ol

VBr - j CH2 Br c~PH ,::r Br

CIH2 C-"Y~
C1 C1 r Br
C 10H 15Br2Cl3 M 401.395 C 10H 16Br3Cl0 M 427.400
(2R,3E,6R,7S)-form [96300-27-5] (JE,3R,4R,6R)-form [52194-66-8]
Constit. of Plocamium cartilagineum. Oil. Constit. of Aplysia californica and Plocamium
Blunt, J.W. eta/, Aust. J. Chern., 1985, 38, 319. cartilagineum. Oil. [cx]i? -64° (c, 2.25 in CHC1 3).
Faulkner, D.J. et al, Tetrahedron Lett., 1973, 1171 (isol)
Willcott, M.R. eta/, Tetrahedron Lett., 1973, 3967 (struct)
1,8-Dichloro-6-chloromethyl-2-methyl-2,6- Mo-00160 Mynderse, J.S. eta/, Tetrahedron, 1975, 31, 1963 (isol)
octadiene, 9CI
[112642-59-8] 1,4,8-Tribromo-3,7-dichloro-3,7-dimethyl- Mo-00165
I yH2Cl
1,5-octadiene
ClH2C~CH2 C1 Clj ~p .
CIOH15Cl3 M 241.587 Br~c~Br
Constit. of Chondrococcus hornemannii. Oil. Br
Coli, J.C. eta/, Aust. J. Chern., 1987, 40, 1893. C 10H 13Br3Cl2 M 443.830
(JE,3R,4S,5E)-form [75207-35-1]
3,8-Dichloro-6-chloromethyl-2-methyl-1,6- Mo-00161 Constit. of Aplysia californica. Cryst. (MeOH). Mp 20°.
octadiene, 9CI Ireland, C. eta/, J. Org. Chern., 1976, 41, 2461 (isol)
Stierle, D.B. eta/, Tetrahedron, 1979, 35, 2855 (struct)
[112642-62-3]

_J ~ 1~2Cl
~y~~CH2 Cl
1,4,6-Tribromo-3,7-dichloro-3,7-dimethyl-
2-octanol, 9CI
Mo-00166

[96300-32-2]
C1
C1 C1
C 10H 15C13 M 241.587
Constit. of Chondrococcus hornemannii. Oil. [cx]n -33.7° (c, ~CH2 Br
0.002 in CHC1 3).
Br Br OH
Coli, J.C. eta/, Aust. J. Chern., 1987, 40, 1893.
C10H 17Br3C120 M 463.861
Constit. of Plocamium cartilagineum. Oil.
2,6-Dichloro-7-niethyl-3-methylene-1,6- Mo-00162
Blunt, J.W. et a/, Aust. J. Chern., 1985, 38, 319.
octadiene
[57461-73-1]
1,4,7-Tribromo-3,6-dichloro-3,7-dimethyl- Mo-00167
2-octanol, 9CI

~Cl Cl
[96300-31-1]

Brj_ ~ 'xC1
C 10H 14Cl2 M 205.126
Constit. of Chondrococcus hornemanni. Oil.
_: l l JCH2Br

Burreson, B.J. eta/, Tetrahedron Lett., 1975, 2155. C1 Br OH

C 10H 17Br3Clz0 M 463.861
Kurodainol Mo-00163 Constit. of Plocamium cartilagineum.
I ,8-Dibromo-6-(bromomethylene)-2,7-dichloro-2-methyl-3- Blunt, J.W. et al, Aust. J. Chern., 1985, 38, 319.
octanol, 9CI
[81720-12-9] 1,8,8-Tribromo-3,4,7-trichloro-3,7- Mo-00168
dimethyl-1,5-octadiene
Br

BcH,~CH,Bc
C1 C1
Br~Br
OH C1 Br C1
C 10H 15Br3C120 M 461.845 C10H 12Br3Cl3 M 478.275
Constit. of Aplysia kurodai. Oil. [ex]~ -1.7° (c, 7.6 in (3R,4S,7S,E,E)-form [51212-86-3]
CC14). Constit. of Aplysia californica and Plocamium
Katayama, A. et a/, Agric. Bioi. Chern., 1982, 46, 859. cartilagineum. Cryst. (MeOH). Mp 54°. [cx]ii -50.2° (c,
1.0 in CHC1 3).

31
1,4, 7-Tribromo-3,6,8-trichloro-3,7-... - 6-Bromo-1,2,8-trichloro-3-ochtodene Mo-00169- Mo-00174

Faulkner, D.J. eta/, J. Am. Chern. Soc., 1973, 95, 3413 (cryst
struct, isol)
Mynderse, J.S. et a/, Tetrahedron, 1975, 31, 1963 (isol)
Ochtodanes
1,4,7-Tribromo-3,6,8-trichloro-3,7- Mo-00169
dimethyl-2-octanol, 9CI
[96300-33-3]
6-Bromo-1,4-epoxy-2-ochtoden-8-ol Mo-00172
Br Cl 6-Bromo-2,3,5,6,7,7a-hexahydro-5,5-dimethyl-4-
CIH2C C~Br benzofuranol, 9CI
H
C10H 16Br3Cl30 M 498.306
Constit. of Plocamium cartilagineum. Oil.
Blunt, J.W. eta/, Aust. J. Chern., 1985, 38, 319.

1,1,7-Tribromo-2,6,8-trichloro-3,7- Mo-00170 C 10 H 1 ~Br0 2 M 247.131

dimethyl-3-octene (4R* ,68* ,88*)-form [73872-78-3]
Constit. of Ochtodes crockeri. Oil. (ex]~ +30° (c, 2 in

CIH2C~CHBr2 CHCI 3).

Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401.
Cl Cl
C 10H 14Br3Cl3 M 480.291 6-Bromo-1,4-epoxy-3(8)-ochtoden-2-ol Mo-00173
6-Bromo-2,3,5,6,7,7a-hexahydro-5,5-dimethyl-3-

Q
(2R,3E,6R,7S)-form [72994-84-4]
benzofuranol, 9CI
Constit. of Plocamium cruciferum. Cryst. (EtOH). Mp
60.5-6l.SO. (ex]~ +99° (c, 0.0002 in cyclohexane).
Bates, P. eta/, Aust. J. Chern., 1979, 32, 2545.
-OH (2R*,4R•,6R*}form
1 Relative
1,5,7-Tribromo-2,6,8-trichloro-2,6- Mo-00171 Br configuration
dimethyl-3-octene
[119903-43-4] C 10 H 1 ~Br0 2 M 247.131
(2R* ,4R* ,68*)-form [73872-80-7]
Constit. of Ochtodes crockeri. Oil. [ex]~ -55° (c, 1 in
CHC1 3).
(28* ,4R* ,68*)-form [73872-79-4]
Constit. of 0. crockeri. Oil. [ex]~ -64.6° (c, 0.7 in
C 10H 14Br3Cl3 M 480.291 CHCI 3).
Constit. of Plocamium hamatum. Cryst. Mp 92.5-94°. [exln
-118° (c, 0.017 in CHC1 3). Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401.
Coli, J.C. eta/, Aust. J. Chern., 1988, 41, 1743 (iso/, cryst struct)
6-Bromo-1,2,8-trichloro-3-ochtodene Mo-00174
4-Bromo-6-chloro-J-(1,2-dichloroethyl)-5,5-
dimethy/cyc/ohexene, 9CI

4~
C 10H 14BrC13 M 320.483
Isol. from Chondrococcus hornemanni. Oil. Mixt. of 2-
epimers. Called 1,2-dichloro-3-ochtodene in reference.
[94450-32-5, 94450-33-6]
Crews, P. eta/, Phytochemistry, 1984, 23, 1449.

32
2-Chloro-1-hydroxy-3(8),5-ochtodien-... - 1,6-Dibromo-8-chloro-1,3-ochtodiene Mo-00175- Mo-00182

2-Chloro-1-hydroxy-3(8),5-ochtodien-4- Mo-00175 1-0xo: [68612-44-2]. Chondrocolactone. 6-Bromo-4-ch/oro-

one 5,6,7,7a-tetrahydro-5,5-dimethyi-2(4H)-benzofuranone,
2-(1-Ch/oro-2-hydroxyethyl)-4,4-dimethy/-2,5-cyc/ohexadien- 9CI. 6- B.romo-8-ch/oro-2,4-epoxy-2-ochtoden-1-one
1-one, 9CI C 10H 12BrC101 M 279.560
Constit. of C. hornemanni. Cryst. (CH 2Cl2/hexane). Mp
[97457-28-8] 107-108°. [ex]i;4 -48° (c, 0.6 in CH 2Cl2).

ifCH,OH
o a Burreson, B.J. et al, Tetrahedron Lett., 1975, 2155 (isol)
Woolard, F.X. et al, Tetrahedron Lett., 1978, 2367 (cmr, struct)

Chondrocole C Mo-00179
4,6-Dibromo-2,4,5',6,7,7a-hexahydro-5,5-dimethylbenzofuran,
9C/. 6,8-Dibromo-1 ,4-epoxy-2-ochtodene
C 10H 13Cl01 M 200.664
Constit. of red alga Desmia hornemanni. Pale-yellow oil. [58086-77-4]
[ex)i: -87.2° (c, 1.29 in CH 2Cl0. Unstable, As Chondrocole A, Mo-00 178 with
spontaneously transformed into 4,5-dimethylbenzofuran.
R = P-Br
Higa, T., Tetrahedron Lett., 1985, 26, 2335.
C 10H 14Br10 M 310.028
1-Chloro-2,4-ochtodien-6-ol Mo-00176 Constit. of Chondrococcus hornemanni.
4-(2-Ch/oroethylidene)-6,6-dimethy/-2-cyc/ohexen-1-o/ Burreson, B.J. et al, Chern. Lett., 1975, 1111.

1,6-Dibromo-2-chloro-3(8)-ochtoden-4-ol Mo-00180
5-Bromo-2-(2-bromo-1-ch/oroethyl)-4,4-dimethy/-2-
cyc/ohexen-1-o/, 9CI
[73872-77-2]
C 10H 15Cl0 M 186.681
(E)-form [73872-81-8]
Constit. of Ochtodes crockeri. Oil. [ex]~ + 5. 7° (c, 1 in
CHC1 3).
Paul, V.J. et al, J. Org. Chern., 1980, 45, 3401 (isol, struct)
Zegarsk:i, J. et al, Tetrahedron Lett., 1985, 26, 1363 (synth)
C10H 15Br1CIO M 346.489
2-Chloro-1,6,8-tribromo-3(8)-ochtodene Mo-00177 (4R*,6S*)-form
2,4-Dibromo-1-(2-bromo-1-ch/oroethyl)-3 ,3- Constit. of Ochtodes crockeri. Oil. [ex]~ -26.8° (c, 1 in
dimethy/cyc/ohexene, 9CI CHC1 3).
[92632-96-7) Paul, V.J. et al, J. Org. Chern., 1980, 45, 3401.

1,6-Dibrmno-8-chloro-2-ochtoden-4-ol Mo-00181
5-Bromo-2-(2-bromoethylidene)-3-chloro-4,4-
dimethy/cyc/ohexano/, 9C/
[89197 -89-7)
C 10H 14Br3Cl M 409.385
Metab. of Ochtodes secundiramea. Oil. [ex]n + 55° (c, 0.74
in CHC1 3).
Gerwick, W.H., Phytochemistry, 1984, 23, 1323.

Chondrocole A Mo-00178 C 10H 15Br1CIO M 346.489

6-Bromo-4-ch/oro-2,4,5,6,7,7a-hexahydro-5,5- Constit. of Ochtodes secundiramea. Oil.
dimethylbenzofuran, 9CI. 6-Bromo-8-ch/oro-4-epoxy-2-
Crews, P. et al, J. Org. Chern., 1984, 49, 1371 (isol, struct, cmr)
ochtodene
[57461-72-0]
1,6-Dibromo-8-chloro-1,3-ochtodiene Mo-00182
4-Bromo-1-(2-bromoethenyl)-6-ch/oro-5,5-
dimethy/cyc/ohexene, 9CI

R = cx-Cl
CIOH14BrC10 M 265.577
Constit. of Chondrococcus hornemanni. Oil. [ex]n -16° (c,
C 10H 13Br1Cl M 328.473
6.2 in CHCI 3).
(1E,6S*,8S*)-form [73872-74-9]
8-Epimer: [57496-04-5]. Chondrocole B
C 10H 14BrC10 M 265.577
Constit. of C. hornemanni. Oil.

33
1,8-Dibromo-2,6-dichloro-3-... - 2,4-0chtodiene-1,6-diol Mo-00183 - Mo-00189

Constit. of Ochtodes crockeri. Oil. [1X]i:' + 16.7° (c, 5.4 in Traas, P.C. et at, Reel. Trav. Chim. Pays-Bas (J. R. Neth. Chern.
CHC1 3). Soc.), 1976, 95, 308 (synth)
de Souza, J.P. eta/, J. Org. Chern., 1978, 43, 2068 (synth)
[89197-93-3]
Masaki, Y. eta/, Tetrahedron Lett., 1982, 23, 1481 (synth)
Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401.
Ochtodene Mo-00186
1,8-Dibromo-2,6-dichloro-3-ochtodene Mo-00183 1-Bromo-4-(2-bromoethylidene)-3,5-dichloro-2,2-
6-Bromo-1-(2-bromo-1-ch/oroethyl)-4-ch/oro-5 ,5- dimethy/cyc/ohexane, 9CI. 1,6-Dibromo-4,8-dich/oro-2-
dimethy/cyc/ohexene, 9CI ochtodene
[58086-86-5] [67237-02-9]

~=
CI~'Br
C 1.,H 14Br2CI2 M 364.934 C 10H 14Br2CI2 M 364.934
Constit. of Chondrococcus hornemanni. Oil. Constit. of Ochtodes secundiramea. Mp 60-62°. [1X]i; + 179°
(c, 12 in CHCI 3).
Burreson, B.J. eta/, Chern. Lett., 1975, 1111 (isol)
Crews, P. eta/, J. Org. Chern., 1984, 40, 1371 (crnr, struct) McConnell, O.J. eta/, J. Org. Chern., 1978, 43, 4238.

1,6-Dibromo-1,3(8)-ochtodien-4-ol Mo-00184 1,3(8)-0chtodiene-5,6-diol Mo-00187

5-Bromo-2-(2-bromoethenyl)-4,4-dimethy/-2-cyc/ohexen-1-o/ 5-Ethenyl-3,3-dimethy/-4-cyc/ohexene-1,2-diol, 9Cl. 3,3-
Dimethyl-5-viny/-4-cyc/ohexene-1 ,2-dio/
NBr
HOdl
~ I
Br~ ( IE,4R.,6S~form HO
C 10H 14Br20 M 310.028 C 10H 160 2 M 168.235
(1E,4R*,6S*)-form [73872-75-0] (5R* ,6R*)-form [73872-83-0]
Constit. of Ochtodes crockeri. Oil. [1X]i:' -45.4° (c, 2.5 in Constit. of Ochtodes crockeri. Oil. [1X]i:' + 0° (c, 1.2 in
CHCI 3). CHCI 3).
(JE,4S*,6S*)-form [73872-76-1] (5f.,6S*)-form [73872-84-1]
Constit. of 0. crockeri. Oil. [1X]i:' -71.2° (c, 3.2 in Constit. of 0. crockeri. Oil. [1X]i:'+ oo (c, 1 in CHCI 3).
CHC1 3). Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401 (isol, struct)
Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401. Zegarski, J. eta/, Tetrahedron Lett., 1985, 26, 1363 (synth)

2-0chtoden-1-al Mo-00185 1,4-0chtodiene-3,6-diol Mo-00188

(3,3-Dimethylcyc/ohexylidene)acetaldehyde, 9CI 1-Etheny/-5 ,5-dimethyl-2-cyc/ohexene-1 ,4-dio/, 9Cl. 5,5-

q
Dimethy/-1-vinyl-2-cyc/ohexene-1 ,4-diol
[73872-85-2)

~
OH
HO'
(E)-form
CIOH1602 M 168.235
C 1.,H160 M 152.236 Constit. of Ochtodes crockeri. Oil. [1X]i:' -14.8° (c, 0.5 in
(E)-form [26532-25-2] CHCI3).
Sex attractant of the male boll weevil. Oil. Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401 (isol, struct)
1-A/coho/: [30346-27-1]. 2-0chtoden-1-ol. 2-(3,3- Zegarski, J. et at, Tetrahedron Lett., 1985, 26, 1363 (synth)
Dimethy/cyc/ohexylidene)ethanol, 9Cl. 3-(2-
Hydroxyethy/idene)-1, 1-dimethylcyc/ohexane
2,4-0chtodiene-1,6-diol Mo-00189
C 10H 180 M 154.252
4-(2-Hydroxyethylidene)-6,6-dimethy/-2-cyc/ohexen-1-o/, 9CI
Sex attractant of the male boll weevil.
(Z)-form [26532-24-1]
Sex attractant of the male boll weevil.
1-Alcohol: [26532-23-0]. (E)-form
Sex attractant of the male boll weevil.
Tomlinson, J.H. et at, J. Org. Chern., 1971, 36, 2616 (isol) C 10H 160 2 M 168.235
Bedoukian, R.H. et at, J. Org. Chern., 1975, 40, 2154 (synth) (E)-form [73891-29-9]
Pelletier, S.W. et at, J. Org. Chern., 1976, 41, l069 (synth) Constit. of Ochtodes crockeri. Oil. [1X]i:' +4.3° (c, 2 in
CHCI 3).

34
Ochtodiol - Mertensene Mo-00190 - Mo-00197'

(Z)-form 2-Bromo-4-chloro-1-(2-chloroethenyl)-1- Mo-00193

Constit. of 0. crockeri. Oil. [oc]i?+ oo (c, 2 in CHC1 3). methyl-5-methylenecyclohexane, 9CI
Paul, V.J. eta/, J. Org. Chern., 1980, 45, 3401 (isol, struct) [119903-45-6]
Masaki, Y. et al, Tetrahedron Lett., 1982, 23, 1481 (synth)
Zegarski, J. et al, Tetrahedron Lett., 1985, 26, 1363 (synth)
~Cl
Ochtodiol
4-Bromo-oc-(chloromethyl)-6-hydroxy-3 ,3-dimethyl-1-
Mo-00190
Cl~r
cyclohexene-1-methanol, 9CI. 6-Bromo-1-chloro-3(8)- C 10H 13BrC12 M 284.022
ochtodene-2,4-diol Constit. of Plocamium hamatum. Oil. [oc] 0 -34° (c, 0.008
[67237-01-8] in CHC1 3).
Coli, J.C. eta/, Aust. J. Chern., 1988, 41, 1743.

4-Chloro-5-(2-chloroethenyl)-1- Mo-00194
chloromethyl-5-methylcyclohexane
[73191-61-4]

C 10H 16BrC10 2 M 283.592

Constit. of Ochtodes secundiramea.
Di-Ac: Oil. [oc]~ -37° (c, 0.3 in CHC1 3).
McConnell, O.J. et al, J. Org. Chern., 1978, 43, 4238. C 10H 13C13 M 239.571
Constit. of Plocamium cartilagineum. Antifungal agent. Oil.
[oc] 0 -110° (c, 0.91 in CHC1 3).
Stierle, D.B. eta/, Tetrahedron, 1979, 35, 1261 (iso/, abs config)

1-Ethyl-1,3- 2,4-Dibromo-1-chloro-5-(2-chloroethenyl)-
1,5-dimethylcyclohexane
Mo-00195

dimethylcyclohexanes [66328-04-9]

Cl~Cl
Br'~Br
2-Bromo-1-(2-bromoethenyl)-4,5-dichloro- Mo-00191 C 10H 14Br2Cl2 M 364.934
1,5-dimethylcyclohexane (1R,2S,4S,5S)-form
Constit. of Plocamium cartilagineum. Oil. [oc]i? +32.3°
C~l
I Br (c, 1.75 in CHC1 3).
- 5 I
Higgs, M.D. et al, Tetrahedron, 1977, 33, 2775 (iso/, pmr, ir, uv,
4 2
ms, cmr)
Cl Br
C 1Jl14Br2Cl 2 M 364.934 Gelidene Mo-00196
(JR* ,2R* ,4S* ,5R*)-form [68370-29-6] 1,2 ,4-Trichloro-5-(2-chloroethenyl)-1 ,5-dimethylcyclohexane,
Constit. of Plocamium cartilagineum. Cryst. (hexane). 9CI
Mp 72-73°. [oc] 0 + > 18° (CHC1 3). [123805-38-9]
Gonzalez, A.G. et a/, Phytochemistry, 1978, 17, 947.
Cl,~C1
4-Bromo-5-bromomethyl-2,5-dichloro-1- Mo-00192
chloroethenyl-1-methylcyclohexane C1~Cl
[66321-24-2] C10H 14C14 M 276.031
Metab. of Gelidium sesquipedale and Plocamium hamatum.
BrH2C Cryst. Mp 86-88° (82°). [oc] 0 +9.4° (c, O.Dl in CHC1 3).
CL~Cl 5 I [106621-87-8, 106621-88-9, 106621-89-0, 106621-90-3, 119945-08-3]
4 2
Coli, J.C. eta/, Aust. J. Chern., 1988, 41, 1743 (iso/, cryst struct)
Bi 'Cl Aazizi, M.A. eta/, J. Nat. Prod. (Lioydia), 1989, 52, 829 (iso/, pmr,
C 10H 13Br2Cl3 M 399.379 cmr)
Constit. of Plocamium cartilagineum. Antifungal agent. Mp
74-74.SO. [ocJi? -43.8° (c, 1.01 in CHCl 3), [oc] 0 -67.8°. Mertensene Mo-00197
Higgs, M.D. et a/, Tetrahedron, 1977, 33, 2775 (isol) 2-Bromo-4,5-dichloro-1-(2-chloroethenyl)-1 ,5-
Stierle, D.B. eta/, Tetrahedron, 1979, 35, 1261 (iso/, abs con.fig) dimethylcyclohexane
[66389-40-0]

Cl,~Cl

C1~r
35
Plocamene D- 4-Bromo-1,5-dichloro-2-... Mo-00198 - Mo-00204

C10H 14BrC13 M 320.483 Violacene Mo-00201

Constit. of Plocamium mertensii and P. hamatum. Needles 1-(Bromomethyl)-1 ,2,4-trichloro-5-(2-chloroethenyl)-5-
(hexane). Mp 105.5-106°. [1X]n +20° (c, 0.3 in CHC1 3). methylcyclohexane, 9CI
2-Epimer: [95044-70-5]. Coccinenet [54279-01-5]
C10H 14BrC13 M 320.483
Constit. of P. coccineum. Cryst. (hexane). Mp 65°. [1X]i;' BrH 2 C
-24° (c, 0.82 in CHC1 3). Cl-h/~Cl
Norton, R.S. et al, Tetrahedron Lett., 1977, 3905 (isol)
Capon, R.J. et al, Aust. J. Chern., 1984, 37, 537 (isol)
Castedo, L. eta/, J. Nat. Prod. (Lloydia), 1984, 47, 724 (isol,
crV-a
Coccinene) C 10H 13BrC14 M 354.928
Crews, P. et a/, J. Org. Chern., 1984, 49, 1371 (cmr, struct) Constit. of Plocamium violaceum and Microcladia spp.
Sardina, F.J. et al, Chern. Lett., 1985, 697 (struct) Cryst. Mp 71-71.5°.
Coli, J.C. et al, Aust. J. Chern., 1988, 41, 1743 (struct, cmr) Mynderse, J.S. et al, J. Am. Chern. Soc., 1974, 96, 6771 (isol)
Crews, P. et a/, J. Org. Chern., 1978, 43, 116 (struct)
Plocamene D Mo-00198 v. Engen, D., Tetrahedron Lett., 1978, 29 (cryst struct)
2,4-Dichloro-1-(2-chloroethenyl)-1-methyl-5-
methylenecyclohexane
[62560-51-4]

~/~/Cl 1-Ethyl-2,4-
ccV'sr
C10H 13Cl3 M 239.571 dimethylcyclohexanes
Constit. of Microcladia spp. Oil. [1X]i? -4.1° (c, 0.73 in
CHC1 3).
4-Epimer: [73191-60-3]. epi-Plocamene D
C 10H 13Cl3 M 239.571 5-Bromo-4-chloro-1-chloroethenyl-2,4- Mo-00202
Constit. of Plocamium violaceum and P. cartilagineum.
Shows antifungal props. Oil. [1X]n -63.3° (c, 0.98 in
dimethylcyclohexene
CHC1 3). [66321-22-0]
Crews, P. eta/, Phytochemistry, 1976, 15, 1707.
Crews, P. et al, J. Org. Chern., 1978, 43, 116; 1984, 49, 1371 (isol, Br~Cl
struct, pmr, cmr)
Stierle, D.B. eta/, Tetrahedron, 1979, 35, 1261 (epimer) Cl~ I

Plocamene D' Mo-00199 C10H 13BrC12 M 284.022

4-Bromo-2-chloro-1-(2-chloroethenyl)-1-methyl-5- Constit. of Plocamium cartilagineum. Mp 104-105°. [1X]it
methylenecyclohexane - 13.2° (c, 1.1 in CHC1 3).
[63883-43-2] Higgs, M.D. et a/, Tetrahedron, 1977, 33, 2775 (isol)
Norton, R.S. et al, Tetrahedron Lett., 1977, 3905 (isol. cmr)

Y"'i--~Cl Absolute 2-Bromo-1-chloro-4-(2-chloroethenyl)-1- Mo-00203

Br~'Cl configuration methyl-5-methylenecyclohexane
C 10H 13BrC12 M 284.022
Constit. of Plocamium cartilagineum and P. violaceum. Br~Cl
Antifungal agent. Oil. [1X]n +31.3° (c, 0.86 in CHC1 3).
Crews, P. et a/, J. Org. Chern., 1978, 43, 116. Cl~ I
Stierle, D.B. et al, Tetrahedron, 1979, 35, 1261 (isol, abs config)
C 10H 13BrC12 M 284.022
(1R,2S,4S,l' E)-form [66321-25-3]
Telfairine Mo-00200
Constit. of Plocamium mertensii and P. cartilagineum.
1-(2-Bromoethenyl)-2,4,5-trichloro-1,5-dimethylcyclohexane
Cryst. (MeOH aq.). Mp 46.5-47°. [1X]n -120° (c, 0.7 in
[120163-22-6] CHC1 3).
Higgs, M.D. et a/, Tetrahedron, 1977, 33, 2775.
CI_~Br Capon, R.J. eta/, Aust. J. Chern., 1984, 37, 537.

Cl~Cl 4-Bromo-1,5-dichloro-2-chloroethenyl-1,5- Mo-00204

C 10H 14BrCI3 M 320.483 dimethylcyclohexane
Constit. of Plocamium telfairiae. Amorph. powder [66389-42-2]
(hexane). Mp 62-63°. [1X]i;' -18° (c, 0.1 in MeOH).
Watanabe, K. et al, Phytochemistry, 1989, 28, 77. Br~Cl

cJM',
ClI

M 320.483

36
1,4-Dibromo-5-chloro-2-(2-... - Chrysanthemic acid Mo-00205 - Mo-00211

Constit. of Plocamium cartilagineum. Constit. of Plocamium violaceum. Oil. [IX]~ -105° (c, 4.57
Norton, R.S. eta/, Tetrahedron Lett., 1977, 3905 (cmr) in CHCI 3).
Crews, P. eta/, J. Org. Chern., 1984, 49, 1371 (cmr, struct) Crews, P. eta/, J. Org. Chern., 1978, 43, 116.

1,4-Dibromo-5-chloro-2-(2-chloroethenyl)- Mo-00205
1,5-dimethylcyclohexane, 9CI
[66321-23-1]

Br~C1
Cyclopropane
/M'ar
a
monoterpenoids
C 10H 14Br2C12 M 364.934
(1 R,2S,4S,5R)-form
Constit. of Plocamium cartilagineum. Mp 86-87°. [1X:fr?
-36° (c, 1.13 in CHC1 3).
2-Acetyl-1-isopropyl-1- Mo-00209
Higgs, M.D. eta/, Tetrahedron, 1977, 33, 2775 (isol, pmr, ir, uv,
cyclopropanecarboxylic acid
ms, cmr)
Norton, R.S. eta/, Tetrahedron Lett., 1977, 3905 (isol, cmr)
Gonzalez, A.G. eta/, Phytochemistry, 1978, 17, 947 (nmr, ir, ahs
conjig)

Plocamene B Mo-00206
4,5-Dich/oro-1-(2-ch/oroethenyl)-2,4-dimethy/cyc/ohexene,
9C/
[58207-70-8] C9H 140 3 M 170.208
(1R,2R)-form
a~Cl Umbel/ulonic acid
Obt. from 11,12,15-Trihydroxy-16-kauren-19-oic acid,
a~ I
Di-01644. Cryst. (pet. ether). Mp 102°. [1X]n + 378°
(CHCI 3).
C 10H 13Cl3 M 239.571 Guha, P.C. et a/, Ber., 1938, 71, 2665.
Constit. of Plocamium cartilagineum. Mp 100-101°. [1X]n
-48°.
Artemisiole Mo-00210
Crews, P. eta/, J. Org. Chern., 1975, 40, 2568; 1978, 43, 116 (isol, 6-Etheny/-1 ,4,4-trimethyl-3-oxobicyc/o[3.1.0]hexane, 9C/.
struct, pmr, cmr, abs conjig)
1,4,4-Trimethyl-6-vinyl-3-oxabicyc/o[3 .1.0]hexane
[60485-46-3]
Plocamene C Mo-00207
1-Bromo-4,5-dich/oro-2-(2-ch/oroethenyl)-1 ,5-
dimethy/cyc/ohexane. Vio/acene 2
[57 566-88-8]

C 10H 160 M 152.236

Constit. of Artemisia tridentata. Oil.
Noble, T.A. eta/, Tetrahedron Lett., 1977, 3931 (iso/, struct)
Banthorpe, D.V. eta/, J. Chern. Soc., Perkin Trans. I, 1981, 105
C10H 14BrCI3 M 320.483 (synth)
Constit. of Microc/adia spp. and Plocamium violaceum.
Cryst. (EtOH). Mp 43.5-44.5°, Mp 78.5-79°. [1X]~ -84°
(c, 0.32 in CHCI 3) •. Chrysanthemic acid Mo-00211
2,2-Dimethy/-3-(2-methy/-1-propenyl)cyc/opropanecarboxylic
Mynderse, J.S. et a/, Tetrahedron Lett., 1975, 2175 (cryst struct) acid, 9CI. 3-Isobutenyl-2 ,2-dimethy/-1-
Crews, P. eta/, J. Org. Chern., 1978, 43, 116 (struct, pmr, cmr)
cyc/opropanecarboxylic acid.
Mynderse, J.S. et a/, Phytochemistry, 1978, 17, 237 (isol)
Chrysanthemummonocarboxylic acid. Chrysanthemumic acid
[10453-89-1]
Plocamene E Mo-00208
1,2-Dich/oro-4-(2-ch/oroethenyl)-1-methyl-5-
methy/enecyc/ohexane, 9CI
[63866-51-3]

a~ a

Cl~ I
C 10H 160 2 M 168.235
Esters of both cis- and trans-forms are widely used in
M 239.571 commercial insecticide preparations.
I> GZ1270000.

37
Chrysanthemol - Pyrethrin I Mo-00212- Mo-00217

(1R,3R)-form [4638-92-0] Cinerin I Mo-00214

(+)-trans-form [97-12-1]
Occurs as pyrethrolone ester as one of the pyrethrins.
Cryst. or liq. Mp 17-21°. [IX]~ + 14.2° (EtOH).
(1S,3S)-form [2259-14-5]
(-)-trans-form
Cryst. Mp 17-21°. [1X] 0 -14° (EtOH).
(1RS,3SR)-form [15259-78-6]
( ± )-cis-form
Cryst. (EtOAc). Mp 115-116°.
Pattenden, G. et aJ, Tetrahedron Lett., 1973, 133 (biosynth) R = CH 3
Cameron, A.F. et aJ,j (;hem. Soc., Perkin Trans. 2, 1975, 1567 C 10H 280 3 M 316.439
(cryst struct, abs config) Constit. of Chrysanthemum cinerariaefolium. A natural
Arlt, D. et al, Angew. Chern., Int. Ed. Engl., 1981, 20, 703 (rev)
Franck-Neumann, M. et aJ, Tetrahedron Lett., 1982, 23, 1409
insecticide (pyrethrin). BPo.oos 132°.
(synth) Crombie, L. eta/, J. Chern. Soc., 1950, 1152 (synth)
DeVos, M.J. et aJ, Tetrahedron Lett., 1983, 24, 103 (synth) Godin, P.J. eta/, J. Chern. Soc. C, 1966, 332 (struct)
d'Angelo, J. et al, Tetrahedron Lett., 1983, 24, 2103 (synth) Bramwell, A.F. et a/, Tetrahedron, 1969, :ZS, 1727 (pmr)
Mukaiyama, T. et al, Chern. Lett., 1983, 385 (synth)
Torii, S. et al, J. Org. Chern., 1983, 48, 1944 (synth, bib/)
Buisson, D. et aJ, Tetrahedron Lett., 1984, :ZS, 6005 (synth)
Cinerin ll Mo-00215
Cameron, A.G. et al, Tetrahedron Lett., 1985, 26, 3503 (synth) [121-20-0]
Funk, R.L. et aJ, J. Org. Chern., 1985, 50, 707 {synth) As Cinerin I, Mo-00214 with
Mann, J. eta/, Tetrahedron Lett., 1986, 27, 3533 (synth)
d'Angelo, J. et al, J. Org. Chern., 1986, 51, 40 (synth) R = COOMe
~IH280S M 360.449
Cbrysanthemol Mo-00212 Constit. of Chrysanthemum cinerariaefolium. A natural
2,2-Dimethyl-3-(2-methyl-1-propeny()cyclopropanemethanol, insecticide (pyrethrin). Bp0.001 182-184°. [IX]~ + 16°
9CI (2,3,3-trimethylpentane).
[5617-92-5] Bramwell, A.F. eta/, Tetrahedron, 1969, 25, 1727 (bib/)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 506.

Pyrethric acid Mo-00216

(26767-71-5]

CIOHI80 M 154.252
Constit. of the leaves of Artemisia ludoviciana. Oil. [1X] 0 MeOOC .-9 X
+49.7°.
Alexander, K. et aJ, J. Org. Chern., 1975, 40, 2576 (isol)
~'COOH
Crombie, L. et aJ, J. Chern. Soc., Perkin Trans. I, 1975, 913 (cmr) C 11 H 160 4 M 212.245
Banthorpe, D.V. eta/; Phytochemistry, 1977, 16, 85 (biosynth) Degradn. prod. of pyrethrins. Oil. [1X]i;' +88.7° (c, 0.67 in
Babin, D. et al, Tetrahedron, 1981, 37, 325 (synth) CHC13).
Takano, S. eta/, J. Org. Chern., 1985, 50, 931 (synth) Sugiyama, T. et a/, Agric. Bioi. Chemf, 1972, 36, 365 (synth)
Pattenden, G. et al, Org. Mass Spectrom., 1973, 7, 719 (ms)
Cbrysanthemumdicarboxylic acid Mo-00213 Crombie, L. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1500 (cmr)
3-(2-Carboxy-1-propeny()-2,2-
dimethy/cyclopropanecarboxylic acid, 9CI Pyrethrin I Mo-00217
[497-95-0] [121-21-1]

HOOC
~--~H ~-~~,
Absolute
C 1ofl 140 4 M 198.218 R = CH3 configuration
Degradn. prod. and structural component of the
pyrethrins. Cryst. Mp 206-208°. [1X] 0 + 27.8° (MeOH). C 21 H 280 3 M 328.450
Constit. of pyrethrum flowers (Chrysanthemum
Abou Donia, S.A. eta/, Tetrahedron Lett., 1973, 3477 (biosynth)
cinerariaefolium). Natural insecticide. Oil. Bp 0.0005 146-
Sharf, H.-D., Chern. Ber., 1978, 111, 2206 (synth)
1500. [IX]~ -14° (2,2,3-trimethylpentane).
I>GZ1725000.
2,4-Dinitrophenylhydrazone: Cryst. Mp 129-131°. (1X]i?
-204° (c, 0.16 in C 6H 6).
4' ,5' -Dihydro: [4466-14-2]. Jasmo/in I
C 21 H 300 3 M 330.466
Minor constit. of flowers of C. cinerariaefolium.

38
Pyrethrin II - 3-Acetyl-2,2-dimethylcyclobutanecarb... Mo-00218 - Mo-00221

Crowley, M.P. eta/, Biochirn. Biophys. Acta, 1962, 60, 312

(biosynth)
Godin, P.J. et al, J. Chern. Soc., 1966, 332 (isol, struct, deriv)
Bramwell, A.F. eta/, Tetrahedron, 1969, 25, 1727 (prnr)
Begley, M.J. et a/, J. Chern. Soc., Chern. Cornrnun., 1972, 1276 (abs
Cyclobutane
monoterpenes
config)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 947.

Pyrethrin ll Mo-00218
[121-29-9]
3-Acetyl-2,2-dimethylcyclobutaneacetic Mo-00220
As Pyrethrin I, Mo-00217 with
acid, 9CI
R = COOMe Pinonic acid
[473-72-3]
CnH280 5 M 372.460
Constit. of pyrethrum flowers (Chrysanthemum
cinerariaefolium). Natural insecticide. Oil. Bp0 . 007 192- nCH2COOH
1930. [IX]~ + 14.7° (2,2,3-trimethylpentanejEt20). (1S,3S)-form
I> GZ0700000.
2,4-Dinitropheny/hydrazone: Cryst. Mp 65-66°. H3COC
HcH3
CH3
Absolute
configuration

4',5'-Dihydro: Jasmolin II C 10H 160 3 M 184.235

CnH300 5 M 374.476
Minor constit. of flowers of C. cinerariaefolium. I> GU0350000.
Crowley, M.P. eta/, Biochirn. Biophys. Acta, 1962, 60, 312
(JR,3R)-form [52305-34-7]
(biosynth) / (-)-cis-form
Godin, P.J. eta/, J. Chern. Soc., 1966, 332 (isol, struct, deriv) Prisms (H 20 or C6H 6 jpet. ether). Mp 68-69°. [IX]~
Bramwell, A.F. et a/, Tetrahedron, 1969, 25, 1727 (prnr) -90.6o (CHC1 3).
Begley, M.J. eta/, J. Chern. Soc., Chern. Cornrnun., 1972, 1276 (abs (JS,3S)-form [64396-97-0]
config) (+)-cis-form
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Degradn. prod. of (+)-IX-Pinene. Cryst. (pet. ether). Mp
Van Nostrand-Reinhold, 1979, 947.
69°. Bp 12 168°. [1X]i;l +92.6° (CHC1 3).
Semicarbazone: Large octahedra (MeOH). Mp 232°.
Rothrockene Mo-00219
1-( 1-Methylethenyl)-2-(2-methy/-1-propenyl)cyc/opropane, (JRS,3RS)-form [17879-35-5]
(±)-cis-form
9CI
Plates or prisms (MeOH). Mp 104-105°. Bp 14 180-187°.
[80082-35-5]
(JS,3R)-form
(-)-trans-form
Absolute Oil.
configuration [61376-92-9, 61826-55-9]
Ruzicka, L. eta/, Helv. Chirn. Acta, 1920, 3, 762 (synth)
C 10H 16 M 136.236 Komppa, G. et al, Justus Liebigs Ann. Chern., 1941, 547, 185
Constit. of Artemisia tridentata rothrockii. Oil. [1X]n -64° (synth)
(c, 1.33 in CHCI 3). Komppa, G. et al, CA, 1947, 41, 425 (synth)
Harispe, M. et al, Bull. Soc. Chirn. Fr., 1964, 1035 (config)
Barbachyn, M.R. et a/, J. Org. Chern., 1984, 49, 2746 (synth, abs
config) Vanderhoff, P.A. eta/, Acta Crystallogr., Sect. C, 1986, 42, 1766
Epstein, W.W. eta/, J. Org. Chern., 1984, 49, 2748 (isol, struct)
(cryst struct)
Takano, S. et al, J. Org. Chern., 1985, 50, 931 (synth)
3-Acetyl-2,2- Mo-00221
dimethylcyclobutanecarboxylic acid, 9CI
Pinononic acid

A
[473-68-7]
COOH
(1R,3S)-form

CH3
H 3COC CH3
C9H 140 3 M 170.208
(JR,3S)-form [22571-78-4]
(+)-cis-form
Degradn. prod. of ( + )-IX-Pinene. Cryst. (H 20). Mp 131°.
[1X]n + 73.7° (c, 4 in CHC1 3).
Semicarbazone: Mp 212°.
(JS,3R)-form
(-)-cis-form
Prisms (CHC1 3). Mp 129°.

39
2,2-Dimethyl-3-(1-methylethenyl) ... - Lineatin Mo-00222 - Mo-00225

Me ester: Rosini, G. et al, Tetrahedron, 1985, 41, 4633 (synth)

C 10H 160 3 M 184.235 Roemming, C. eta/, Acta Chern. Scand., Ser. B, 1986, 40, 434
Bp 13 127°. (synth)
Demuth, M. eta/, Angew. Chern., Int. Ed. Engl., 1986, 25, 1117
Oxime: (synth)
C,H15N03 M 185.222 Meyers, A.l. et al, J. Am. Chern. Soc., 1986, 108, 306 (synth)
Prisms (Et20). Mp 178-180°. Webster, F.X. et al, J. Org. Chern., 1986, 51, 5226 (synth)
(JR,JR)-form Rosini, G. et a/, Tetrahedron, 1986, 42, 6027 (synth)
(-)-trans-form Aljancic-Solaja, I. eta/, Helv. Chim. Acta, 1987, 70, 1302 (synth)
Mori, K. et al, Tetrahedron, 1987, 43, 2229 (synth)
Results from alkaline equilibration of (1R,3S)-form. Mp
Kametani, T. eta/, J. Chern. Soc., Perkin Trans. I, 1988, 2433
75°. [1X]n -79° (c, 3 in C 6H 6). (synth)
[22571-79-5, 28587-39-5] Kim, D. eta/, J. Chern. Soc., Perkin Trans. I, 1990, 3221 (synth)
Kerschbaum, M., Ber., 1900, 33, 891 (synth)
Guha, P.C. eta/, CA, 1935, 29, 5818 (synth) Junionone Mo-00224
Harispe, M. eta/, Bull. Soc. Chim. Fr., 1964, 1035 (abs config)
4-(2,2-Dimethylcyclobutyl)-3-buten-2-one
[51847-79-1]
2,2-Dimethyl-3-(1- Mo-00222
methylethenyl)cyclobutanemethanol, 9CI
1-Hydroxymethyl-3-isopropenyl-2,2-dimethylcyclobutane

-r+CH,OH C 10H 160 M 152.236

Cons tit. of the fruit oil of Juniperus communis.
Thomas, A.F., J. Chern. Soc., Chern. Commun., 1973, 746.
Gaoni, Y., Tetrahedron Lett., 1982, 23, 5219 (synth)
C 10H 180 M 154.252 Gaoni, Y. et a/, J. Org. Chern., 1985, 50, 2948 (synth)
(JR,JS)-form
Ac: Lineatin Mo-00225
CnH200 2 M 196.289 3,3,7-Trimethyl-2,9-dioxatricyclo(3.3.1.04 •1]nonane, 9CI
Sex pheromone of citrus mealybug Plenococcus citri. Oil.
BPts 110-lUO. [1Xm 3 +148°.
Bieri-Leonhardt, B.A. eta/, Tetrahedron Lett., 1981, 389 (isol.
synth, spectra)
Gaoni, Y., Tetrahedron Lett., 1982, 23, 5215 (synth)
Carlsen, P.H.J. et al, Acta Chern. Scand., Ser. B, 1984, 38, 501 CtoHt 60 2 M 168.235
(synth) (+)-form [65035-34-9]
Pheromone from Tryptodendron lineatum. Oil. [IX]~
1-(2-Hydroxyethyl)-2-isopropenyl-1- Mo-00223 + 36° (pentane).
methylcyclobutane (±)-form [71899-16-6]
1-Methyl-2-( 1-methylethenyl)cyclobutaneethanol, 9CI Oil. Bp20 110°.

d-CH,CH,OH Mori, K. eta/, Tetrahedron, 1980, 36, 2197; 1983, 39, 1735 (synth,
cryst struct, abs conjig)

,r
McKay, W.R. eta/, Can. J. Chern., 1982, 60, 872 (synth, spectra)
White, J.D. eta/, J. Am. Chern. Soc., 1982, 104, 5486 (synth)
( 1R,2S)-form Johnston, B.D. eta/, J. Org. Chern., 1985, 50, 114 (synth, bib!)
Kandil, A.A. eta/, J. Org. Chern., 1985, 50, 5649 (synth)
Skatteboel, L eta/, Acta Chern. Scand., Ser. B, 1985 . 39, 291
C 1oH180 M 154.252 (synth)
Ailjancic-Solaja, I. eta/, Helv. Chim. Acta, 1987, 70, 1302 (synth)
(1R,1S)-form [26532-22-9] Grandisol Kametani, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 2433
Sex attractant of the male boll weevil (Anthonomus (synth)
grandis). Oil. Bp 1 50-60°. [1X]n + 18.SO (c, 1 in hexane).
(JR*,2R*)-form [30346-21-5] Fragranol
Constit. of Artemisia fragrans. Oil. Bp 12 120°.
Ac: [51117-22-7].
CnH200 2 M 196.289
From A. fragrans. Bp 12 120°.
2-Methylpropanoyl:
C 14H240 2 M 224.342
From A. fragrans. Bp 12 120-130°.
Bohlmann, F. eta/, Chern. Ber., 1973, 106, 2904 (isol)
Thorpe, M.C. et al, J. Magn. &son., 1973, 10, 316 (cmr)
Mitlin, N. eta/, J. Insect Physiol., 1974, 20, 1825 (biosynth)
Kosugi, H. et al. Bull. Chem. Soc. Jpn .• 1976. 49, 520 (synth)
Hobbs, P.D. et al, J. Am. Chern. Soc., 1976, 98, 4594 (synth)
Trost, B.M. eta/, J. Am. Chern. Soc., 1977, 99, 3088 (synth)
Mori, K., Tetrahedron, 1978, 34, 915 (synth)
Webster, F.X. et al, ACS Symp. Ser., 1982, 190, 87 (rev)
Jones, J.B. et al, Can. J. Chern., 1982, 60, 2007 (synth)

40
Adoxosidic acid - Antirrhinoside Mo-00226 - Mo-00229

Antirrhinoside Mo-00229

Iridoids
[20770-65-4]

Adoxosidic acid Mo-00226

C 15H 220 10
~
M 362.333
1~ H OGle

~H Constit. of Antirrhinum spp., Linaria japonica and

Cymba/aria muralis. Amorph. [IX]~ -79° (dioxan).

HOH2/1'(~c
Penta-Ac: Cryst. (Me 2COfhexane). Mp 138-139°.
Hexa-Ac: Mp 174°.
10-Hydroxy: [54835-65-3]. Macfadienoside
C 16H 240 10 M 376.360 C15H 220 11 M 378.332
Constit. of Castilleja integra and Fouquieria columnaris. Constit. of Macfadyena cinancoides. Amorph. powder.
Me ester: [42830-26-2]. Adoxoside (IX]~ -30° (c, 2 in MeOH).
C 17H 21;010 M 390.386 10-Hydroxy, 5-0-P-v-glucopyranoside: [75005-96-8].
Constit. of Adoxa moschatellina. Amotph. Calycinoside
Me ester, penta-Ac: Cryst. Mp 140.5-141.SO. [1X]i_; -63° (c, C21 H 320 16 M 540.474
1 in CHC1 3). Constit. of Antirrhinum orontium. Amorph. powder. [1X]n
6P-Hydroxy, Me ester: [110559-86-9]. 6P-Hydroxyadoxoside -75° (c, 0.8 in MeOH).
C 17H 260 11 M 406.386 5-Epimer: [20486-27-5]. Procumbide
Constit. of C. integra. Foam. [1X]i; -83.4° (c, 0.43 in C15H 220 10 M 362.333
MeOH). Constit. of root of Harpagophytum procumbens. Cryst.
6p, 81X-Dihydroxy: [80666-55-3]. Unedide (EtOH). Mp 210-2W. [1X]i? -80.9° (c, 2.8 in EtOH).
C 16H 240 12 M 408.358 5-Epimer, penta-Ac: Cryst. (EtOH). Mp 136-137°. [1X]i?
Constit. of Arbutus unedo. Amorph. (1X]i,S -83° (c, 4.5 in -79° (c, 0.7 in CHCI 3).
MeOH). 5-Epimer, 6' -0-(p-Hydroxycinnamoyl): [87686-76-8]. 6' -0-
Jensen, S.R. et al, Biochem. Syst. Ecol., 1979, 7, 103 (iso[) p-Coumaroylprocumbide
Davini, F. eta/, Phytochemistry, 1981, 20, 1583 (Unedide) C24 H 280 12 M 508.478
Damtoft, S. eta/, Phytochemistry, 1981, 20, 2717 (cmr) Constit. of roots of H. procumbens. Hygroscopic
Jensen, S.R. et al, Phytochemistry, 1982, 21, 1623 (iso[)
Gardner, D.R. et al, J. Nat. Prod. (Lloydia), 1987, 50, 485 (iso[)
powder. [1X]i_; -58.2° (c, 0. 78 in MeOH).
5-Deoxy: [30688-55-2]. Galiridoside
C 15H 220 9 M 346.333
Allobetonicoside Mo-00227 Constit. of Galeopsis tetrahit. Cryst. Mp 189.5-191.SO.
[128581-46-4] [1X]n -78° (c, 1 in Hp).
5-Deoxy, 2' -0-(p- Hydroxy- E-cinnamoyl): [111394-29-7].
Decumbeside A
C24H 280 11 M 492.479
Constit. of Ajuga decumbens. Amorph. powder. [IX]~
-60° (c, 0.52 in MeOH).
5-Deoxy, 2' -0-(p-Hydroxy-Z-cinnamoyl): [111466-44-5].
C21 H 300 14 M 506.460 Decumbeside B
Constit. of Betonica officina/is. Amorph. powder. [1X]i? C24H 280 11 M 492.479
-53.3° (c, 0.34 in MeOH). Constit. of A. decumbens. Amorph. powder. (IX]~ -13°
(c, 0.59 in MeOH).
Jeker, M. et al, Helv. Chim. Acta, 1989, 72, 1787 (isol, pmr, cmr)
Scarpati, M.L. et al, Gazz. Chim. /tal., 1968, 98, 177
(Antirrhinoside)
Alyscialactone Mo-00228 Sticher, 0., Helv. Chim. Acta, 1970, 53, 2010 (Galiridoside)
Kitagawa, I. et al, Chern. Pharm. Bull., 1973, 21, 1978 (isol, struct)
Bianco, A. et al, Gazz. Chim. /tal., 1974, 104, 731; 1979; 109, 561
. (Macfadienoside, Calycinoside)
Kapoor, S.K. et al, Phytochemistry, 1974, 13, 1018 (iso[)
Bendall, M.R. et al, Aust. J. Chern., 1979, 32, 2085 (Procumbide)
Bianco, A. et al, Gazz. Chim. /tal., 1981, 111, 201 (cmr)
Kikuchi, T. eta/, Chern. Pharm. Bull., 1983, 31, 2296 (p-
Coumaroylprocumbide)
CtoH 160 4 M 200.234 Damtoft, S., Phytochemistry, 1983, 22, 1929 (biosynth)
Constit. of Alyscia reinwardti. [1X]n + 132° (c, 0.5 in Takeda, Y. et al, Phytochemistry, 1987, 26, 2303 (Decuombersides)
CHC1 3).
4-Epimer: 4-Epialysdq,/actone
C 10H 160 4 M 200.234
Constit. of A. reinwardti. Cryst. Mp 110-111°. [1X]n -53°
(c, 0.6 in CHC1 3).
Topcu, G. eta/, Phytochemistry, 1990, 29, 3197 (isol, pmr, cmr)

41
Antirride - Argylioside Mo-00230 - Mo-00235

Antirride Mo-00230 Arbortristoside D Mo-00233

1,4a,5,6,7,7a-Hexahydro-6-hydroxy-7- [129277-51-6]
methy/enecyclopenta[e]pyran-1-yi-P-D-glucopyranoside, 9CI
[27935-00-8] HO H COOMe

HOW H ~
HO

H2C H OGle
C15H 22 0 8 M 330.334 HQ:::::,...
Constit. of Antirrhinum tortusum and of Linaria japonica. OH
Cryst. Mp 85-87°. [1X]i;l -116° (e, 0.42 in dioxan).
C 26H 3z0 15 M 584.530
Penta-Ac: Mp 154-155°. [1X]i;l -155° (e; 1.05 in dioxan). Constit. of Nyctanthes arbor-tristis. Amorph. powder
Scarpati, M.L. et al, Gazz. Chim. /tal., 1969, 99, 807; CA, 72, (MeOH). [1X]i,S -84.6° (e, 1 in MeOH).
90815 (isol, struct)
Rathore, A. et a/, Phytochemistry, 1990, 29, 1917 (isol, pmr, cmr)
Kitagawa, I. et al, Chern. Pharm. Bull., 1973, 21, 1978 (isol, struct)

Aralidioside Mo-00231 Arbortristoside E Mo-00234

[129277-52-7]
[78693-92-2]

~~ H~~
C18 H240 13
MeOOC
M 448.380
HOGle

Constit. of Aralidiumpinnati.fidum. Foam. [1X]i;' -211° (e,

0.3 in MeOH).
MeOV
~cooZj,c
OH
: 0

Penta-Ac: Cryst. Mp 188-190°. [1X]i;' -232° (e, 0.5 in HO

MeOH). OH
Jensen, S.R. eta/, Phytochemistry, 1980, 19, 2685.
Damtoft, S. eta/, Phytochemistry, 1981, 20, 2436 (cmr)
C27H 340 13 M 566.558
Constit. of Nyctanthes arbor-tristis. [1X]i? -105.4° (e, 1 in
MeOH).
Arborside C Mo-00232 Rathore, A. et al, Phytochemistry, 1990, 29, 1917 (isol, pmr, cmr)
[128450-80-6]

rno Hco
Argylioside Mo-00235
~Me [1 02822-10-6]
PhCOO-
waH~
°
OGle
C24H 300u M 510.494 0 0 I H
Constit. of Nyctanthes arbor-tristis. Needles H HOH2C OGle
(EtOAejhexane). Mp 210-212°. [1X]i,S -102° (e, 1 in 10 OGle
MeOH). C31H440 18 M 704.678
6-Benzoy/: [128450-78-2]. Arborside A Constit. of Argylia radiata. Amorph. powder. [1X]i;' -126°
C31 H 340 13 M 614.602 (e, 0.5 in MeOH).
Constit. of N. arbor-tristis. Needles (as tetra-Ae). Mp Nona-Ac: Cryst. (EtOH). Mp 175-176°.
138° (tetra-Ae). [1X]i,S +9.7° (e, 1.9 in CHC1 3) (tetra-Ae). 8P-Hydroxy: [104363-10-2]. Radiatoside
6-Deoxy: [128450-79-3]. Arborside B C31H440 19 M 720.677
C 24H 300 11 M 494.494 Constit. of A. radiata. Amorph. powder. [1X]i;' -48.9° (e,
Constit. of N. arbor-tristis. Amorph. powder (as tetra- 1.5 in MeOH).
Ae). [1X]i,S + 7.3° (e, 0.3 in CHC13) (tetra-Ae). 8,10-Didehydro: [111514-50-2]. Radiatoside C
[128572-06-5] C31H420 18 M 702.662
Srivastava, V. et a/, J. Nat. Prod. (Lloydia), 1990, 53, 303 (isol, Constit. of A. radiata. Amorph. powder. [1X]i!' -125.3°
pmr, cmr) (e, 1 in MeOH).
7,8-Didehydro, 10-hydroxy: [111514-49-9]. Radiatoside B
C3tH42019 M 718.661
Constit. of A. radiata. Amorph. powder. [IX]~' -138.6°
(e, 1 in MeOH).
Bianco, A. et a/, Phytochemistry, 1986, 25, 946 (Argylioside)

42
Asperuloside - Aucubigenin Mo-00236 - Mo-00239

Bianco, A. eta/, J. Nat. Prod. (Lloydia), 1986, 49, 519 Asystasioside E Mo-00238
(Radiatoside)
Bianco, A. eta/, Planta Med., 1987, 53, 385 (Radiatoside B, [126005-85-4]
Radiatoside C)

Asperuloside Mo-00236 Cl~}h

w;
Rubichloric acid
[14259-45-1] HO)rtyO
HOH2C OGle
CtsH23Cl0to M 398.793
Constit. of Asystasia bella. Foam. [a:]~ -140° (e, 0.3 in
MeOH).

AcOH~le
Demuth, H. eta/, Phytochemistry, 1989, 28, 3361 (isol, pmr, cmr)

Aucubigenin Mo-00239
C18Hu011 M 414.365 Rhinanthogenin
lsol. from Asperula, Galium, Crucianella, Coprosma, [64274-28-8]
Escallonia, Daphniphyllum spp. and other plants. Mp
131-132° (125-127°). [a:]~ -204° (H20).
Tetra-Ac: Mp 154.5-155°. [a:Jh' -128.6° (EtOH). HWOH
2' -0-(p-Hydroxyphenylpropanoyl): J12 lridoid 0
C17H:14.013 M 562.526 HOH2 H
Constit. of G. verum. Cryst. (Me2 CO). Mp 145-150°. OH
Briggs, L.H. et a/, J. Chern. Soc., 1965, 2595 (struct) C9H 120 4 M 184.191
Swiatek, L. eta/, Herba Pol., 1972, 18, 168 (occur)
Oil. Unstable.
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, 1-0-P-D-Glucopyranoside: [479-98-1]. Aucubin. Aucuboside.
no. 1136 (occur) Rhinanthin
Damtoft, S. et al, Phytochemistry, 1981, 20, 2717 (cmr) C15H:zz09 M 346.333
Bojthe-Homith, K. et al, Tetrahedron Lett., 1982, 23, 965 (V2 Constit. of Plantago lanceolata and Aucuba japonica.
lridoid) Widespread in the Serophulariaeeae. Cryst. + lH 20
Bojthe-Homith, K. et al, Tetrahedron Lett., 1982, 23, 965 (V2 (EtOH aq.). Mp 181°. [a:]~ -171.4° (H 20).
lridoid)
Uesato, S. et al, Phytochemistry, 1986, 25, 2515 (biosynth) 1-0-P-Cellobioside:
C21 H 320 14 M 508.475
Constit. of Odontites verna. Amorph. powder. [a:]i,S
Asystasioside B Mo-00237 -92.0° (e, 0.7 in MeOH).
[126005-82-l] 1-0-P-Gentiobioside:
COOGle C21H320 14 M 508.475
Constit. ofO. verna. Cryst. (EtOH). Mp 180-181°. [a:]i,S

~
-45° (e, L5 in MeOH).
1-0-P-D-(2' -Benzoylglucopyranosyl): 2' -0-Benzoylaucubin
C22H 21;0 10 M 450.441
Constit. of 0. verna. Amorph. powder. [a:]i,S -124.8° (c,
10 OGle
0.4 in MeOH).
C:zzH320 14 M 520.486 6-Epimer, 1-0-P-D-glucopyranoside: 6-Epiaucubin
Constit. of Asystasia bella. Cryst. (as octa-Ae). Mp 186- C 15H 220 9 M 346.333
1870 (octa-Ac). [a]~ -18° (c, 0.5 in CHC1 3) (octa-Ac). Constit. of Tecoma chrysantha. Amorph. powder. [a]i,S
7,8P-Dihydro: [126005-81-0]. Asystasioside A -58.9° (e, 0.7 in MeOH).
C:zzH340 14 M 522.502 1-0-P-D-Glucopyranoside, 10-0-(p-hydroxybenzoyl): [11027-
Constit. of A. bella. Cryst. (EtOH) (as octa-Ac). Mp 63-7]. Agnuside. Agnoside
183-184° (octa-Ac). [a:]~ -62° (e, 0.5 in CHCl 3). C:zzH21;011 M 466.441
118•10-Jsomer: [126005-83-2]. Asystasioside C lsol. from Vitex agnus-castus, V. negundo, V. trifolia, V.
C:zzH320 14 M 520.486 lucens and other V. spp., also Rhinanthus spp. Cryst.
From A. bella. Foam. Mp 200-201° (as octa-Ac). [a:]~ (Hp). Mp 146°. [a:]~ -9l.SO (EtOH).
-40° (e, 0.4 in CHCl 3) (oeta-Ae). 6-Deoxy, 1-0-P-D-glucopyranoside: [62133-72-6]. Bartsioside
Demuth, H. et al, Phytochemistry, 1989, 28, 3361 (isol, pmr, cmr) C15H 220 8 M 330.334
Constit. of Bartsia trixago. Mp ll8-l20°. [a:]i,S -89°
(MeOH).
1-0-P-D-Glucopyranoside, 6-0-(3-0-cinnamoyl-a-L-
rhahmopyranoside): [83529-68-4]. Nigroside 1
C30H 380 14 M 622.622
Isol. from Verbascum nigrum. Amorph. [a:]~ -140° (e,
0.52 in MeOH).
1,10-Di-0-D-Glucopyranoside: 10-0-Giucosylaucubin
C21 H 320 14 M 508.475
Constit. of Linaria sp. Cryst. Mp 248-250° dec. [a:]~
-122° (e, l in Hp).

43
Boschnialactone - Cachineside IV Mo-00240 - Mo-00243

1-0-[p-D-Glucopyranosy/(1 -+ 6)-P-D-glucopyranoside]: Callant, P. eta/, Tetrahedron Lett., 1983, 24, 5797 (synth)
[67708-72-9]. Ulmositk Wang, T.-F. eta/, J. Chern. Soc., Chern. Commun., 1989, 1876
C21H320 14 M 508.475 (synth)
Constit. of Eucommia ulmoides. Amorph. [ex]~ -16.6° Hanquet, B. et a/, Can. J. Chern., 1990, 68, 620 (synth, pmr, cmr)
(c, 2.5 in MeOH).
1-0-P-D-Glucopyranoside, 10-Cinnamoyl: [2565-86-8]. Brasoside Mo-00241
lsoscrophulariositk

11$
C24H 280 10 M 476.479
Constit. of Penstemon eriantherus. Cryst. M p 98-101 °.
1-0-P-D-Glucopyranoside, 6-0-ex-L-rhamnopyranoside:
[78053-02-8]. Sinuatol
C21H320 13 M 492.476
Constit. of Verbascum sinuatum. Amorph. [ex]~ -158°
(c, 0.3 in H 20). OGle
!-0-(6-0-Cinnamoyl-P-D-glucopyranoside): [75235-86c8]. Ct6H2209 M 358.344
Scrophulariositk Constit. of Verbena spp. Amorph. [ex]~ -170° (c, 0.97 in
C24H 280 10 M 476.479 EtOH).
Constit. of Scrophularia spp. Amorph. [ex]~ -93° (c, Tetra-Ac: Cryst. Mp 185-187°.
0. 74 in MeOH). Rimpler, H. eta/, Z. Naturforsch., C, 1979, 34, 311, 319 (isol, pmr,
1-0-P-D-Glucopyranoside, 6-0-(2-0-cinnamoyl-ex-L- struct)
rhamnopyranoside): [83529-69-5]. Nigroside 2
C30H380 14 M 622.622 Cachineside I Mo-00242
Constit. of V. nigrum. Amorph. [ex]i;l -142° (c, 1.27 in
[81927-53-9]
MeOH).
6-Deoxy, 1-10-di-0-P-D-glucopyranoside: 10- H CHO
Giucosylbartsioside
HO~
C2tH320t, M 556.474
Constit. of Chaenorrhinum minus. Amorph. [ex]~ -64° 'ft-yo
(c, 0.7 in MeOH). HOGle
Inouge, H. eta/, Chern. Pharm. Bull., 1964, 12, 901. C16H 240 9 M 360.360
Hansel, R. et a/, Phytochemistry, 1965, 4, 19 (Agnuside)
Constit. of Campsis chinensis. Amorph. powder. [exln
Esposito, P. eta/, Gazz. Chim. /tal., 1970, 100, 836
(Glucosylaucubin)
- 136° (c, 0.25 in MeOH).
Karrer, W. eta/, Konstitution und Vorkommen der Organischen 7-0-Cinnamoyl: [79637-89-1]. Campenoside
Pf/anzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, C25 H 300 10 M 490.506
no. 1791 (occur) Constit. of C. chinensis. Cryst. Mp 165-167°. [ex]~
Bianco, A., Gazz. Chim. Ita/., 1976, 106, 725; 1978, 108, 17 -59.5° (MeOH).
(Bartsioside, Ulmoside)
Bialbeul, F. eta/, Phytochemistry, 1977, 16, 723 (cmr) 7-Deoxy, 8-epimer: [72963-55-4]. Boschnalositk
Bianco, A. eta/, Tetrahedron, 1977, 33, 847; 1982, 38, 362 (isol) Ct6H240 8 M 344.361
El-Nagger, L.J. et al, J. Nat. Prod. (Lloydia), 1980, 43, 649 (rev) Constit. of Boschniakia rossica. Cryst. (Me2CO). Mp
Bianco, A. eta/, Gazz. Chim. /tal., 1981, 111, 91, 479; 1982, 112, 102-103°. [ex]~ -134.SO (c, 1 in MeOH).
227 (isol) ~
Murai, F. eta/, Chern. Pharm. Bull., 1980, 28, 1730
Junior, P., Planta Med., 1981, 43, 34 (Isoscrophu/arioside) (Boschnialoside)
Bianco, A. eta/, Planta Med., 1981, 75, 75 (Sinuatol) Kobayashi, S. eta/, Heterocycles, 1981, 16, 1475 (Campenoside)
Seifert, K. eta/, Helv. Chim. Acta, 1982, 65, 1678 (Nigroside) Damtoft, S. eta/, Phytochemistry, 1981, 20, 2717 (cmr, deriv)
Damtoft, S., Phytochemistry, 1983, 22, 1929 (biosynth) Imakura, Y. eta/, Phytochemistry, 1984, 23, 2263 (Cachineside I)
Breinholt, J. eta/, Phytochemistry, 1990, 29, 3865 (10-
g/ucosy/bartsioside)
Cachineside IV Mo-00243
Boscbnialactone Mo-00240 [104931-19-3]

HOW
Hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one, 9CJ
HO CHO
[17957-87-8]

HO \HOGle
C16H 240 11 M 392.359
Constit. of Campsis chinensis.
C,H140 2 M 154.208 2',3',4',6',7-Penta-0-Ac: Cryst. (EtOH). Mp 118-120°. [exln
Constit. of Boschniakia rossica. Shows marked -138° (c, 0.5 in CHC1 3).
physiological activity towards cats. Oil. Bp6 105-112°. 7-Cinnamoyl: [83459-43-2]. Pondraneoside
[ex]i;l -18.2° (c, 2.10 in CHC1 3). C25 H 300 1:z M 522.505
(±)-:form [16802-11-2] Constit. of Pondranea ricasoliana. Amorph. powder. [exln
Mp 24.5°. The 3 other stereoisomeric (±)-forms have -69.2° (c, 3.2 in MeOH).
been synthesised. 7-0-(4-Hydroxycinnamoy{): [104931-18-2]. Cachineside Ill
[16802-12-3, 16802-13-4, 16802-14-5] C25H 300 13 M 538.504
Sakan, T. eta/, Tetrahedron, 1967, 23, 4635 (isol) From C. chinensis. Amorph. powder. [exln -103.2° (c,
Sisido, K. eta/, Tetrahedron Lett., 1967, 1553 (synth) 0.2 in MeOH).

44
Catalpol - Catalpol Mo-00244 - Mo-00244

7-0-(4-Hydroxycinnamoyl), 2' ,3' ,4' ,4",6'-pen ta-O-Ac: Cryst. 6-(4-Hydroxy-3-methoxycinnamoyl): [64461-95-6]. Picroside
(MeOH). Mp 231-232°. [1X]n -120° (c, 0.3 in CHC1 3). Ill
5-Deoxy: [104931-20-6]. Cachineside V C:zsH300 13 M 538.504
C 16H 140 10 M 376.360 Constit. of P. kurrooa. Mp 154-155°. [IX]~ -78°
Constit. of C. chinensis. Cryst. (EtOH) (as penta-Ac). (CHC1 3). May be 10-substd.
Mp 197-199° (penta-Ac). [1X]n -113° (c, 0.3 in 10-((E)-4-Hydroxycinnamoyl): [58286-53-6]. Scutellarioside
CHC1 3)(penta-Ac). II
5-Deoxy, 7-0-cinnamoy/: [94079-78-4]. Campsiside. 8P- C14H 280 12 M 508.478
Hydroxycampenoside From S. a/tissima. Powder. [IX]~ -80.1° (c, 0.5 in
C 25H;11,011 M 506.505 EtOH).
Constit. of leaves of C.chinensis. Amorph. powder. [IX]~ 6-Deoxy: [99499-99-7]. 6-Deoxycatalpol
-68.SO (c, 0.43 in MeOH). clsHzzO, M 346.333
7-Deoxy: [76994-07-5]. Euphroside Constit. of Utricularia australis, Catilleja miniata and
C 16H 140 10 M 376.360 Cistanche salsa. Cryst. (EtOH), needles (MeOH). Mp
Constit. of Euphrasia sa/isburgensis. [IX]~ -167.3° (c, 212.5-2W (204-206°). [1X)~ -47° (c, 0.4 in MeOH), [1Xjl8
0.63 in MeOH). -50.0° (c, 1.0 in MeOH). Also descr. as a foam. n

7-Deoxy, penta-Ac: Cryst. (EtOH). Mp 157-158°. [IX]~ 0 6-Me: Methylcatalpol

-120° (c, 0.82 in CHC1 3). Ct6H:w0 10 M 376.360
Isol. from leaves of B. g/obosa and B. variabilis. Cryst.
5,7-Dideoxy: [58514-30-0]. lxoroside
(Hp). Mp 236-238°. [1X]~· 5 -122° (c, 1.64 in 90%
C 16H 140 9 M 360.360
EtOH aq.).
Constit. of lxeris chinensis. Amorph. powder. [IX]~
- 102.6° (c, 0.64 in MeOH). 6-0-(4-Hydroxybenzoyl): [6736-85-2]. Catalposide
C22H 260 12 M 482.440
5,7-Dideoxy, tetra-Ac: Cryst. (EtOH). Mp 156-157°.
Constit. of ripe fruit of Catalpa spp. Mp 215-217°. [IX}i:
Takeda, Y. et a/, Phytochemistry, 1975, 14, 2647 (Ixorosdide) -184° (c, 0.9 in MeOH).
Sticher, 0. eta/, Helv. Chim. Acta, 1981, 64, 78 (Euphroside)
Damtoft, S. eta/, Phytochemistry, 1981, 20, 2717 (cmr) 6-0-P-D-Ga/actopyranoside: (81720-06-1 ]. Rehmannioside B
Guiso, M., J. Nat. Prod. (Lloydia), 1982, 45, 462 (Pondraneoside) C 21 H 3P 15 M 524.475
Imakura, Y. eta/, Chern. Pharm. Bull., 1985, 33, 2220 (Campsiside) Constit. of Rehmannia glutinosa. Powder. [IX]~ -8.8° (c,
Imakura, Y. eta/, Heterocycles, 1986, 24, 2593 (Cachinesides) 0.5 in MeOH).
6-0-Benzoy/: [50981-09-4]. Veronicoside
Catalpol Mo-00244 C 22 H 260 11 M 466.441
[2415-24-9] Constit. of V. officina/is. Cryst. (MeOH). Mp 168°.
6-0-Benzoy/, penta-Ac: Cryst. (EtOH). Mp 172°. [IX]~
- 105° (c, 0.64 in CHC1 3).
6-0-Cinnamoy/: [72514-90-0]. Specioside
C14H 280u M 508.478
Constit. of C. speciosa. Cryst. Mp 244-245°. [1X]i,l -203°
(c, 0.4 in MeOH).
6-0-(3,4-Dihydroxycinnamoyl): [50932-19-9). Verminoside
CtsH220 10 M 362.333 C14H 280 13 M 524.477
Constit. of Plantago /anceo/ata, Buddleia globosa and B. Constit. of V. officina/is. Amorph. [IX]~ -180.8° (c, 0.7
variabilis. Mp 207-209° dec. [IX]~ -122° (EtOH aq.). in MeOH).
10-(E)-Cinnamoy/: [1399-49-1). Globularin. Scutellarioside I 6-0-(3,4-Dihydroxycinnamoyl), hepta-Ac: Cryst. Mp 94°.
C14H 280 11 M 492.479 [IX]~ -102° (c, 0.7 in CHC13).
Constit. of Globularia alypum and Scutel/aria altissima.
6-0-(3-Hydroxy-4-methoxycinnamoyl): [51 005-44-8].
Cryst. (EtOH) or amorph. powder. Mp 115-117°. [IX]~
Minecoside
-64.9° (c, 0.81 in MeOH), [IX]~ -76.9° (c, 0.5 in C25H 300 13 M 538.504
EtOH). The stereochem. of Scutellarioside I was not
Constit. of V. officina/is. Cryst. Mp 142°. [IX]~ -182° (c,
detd. but it is prob. identical with Globularin.
0.64 in MeOH).
10-(Z)-Cinnamoy/: [76248-14-1 ). Globularicisin. Picroside I
6-0-(3-Hydroxy-4-methoxycinnamoyl), hexa-Ac: Cryst.
C14H 280 11 M 492.479
(EtOH). Mp 105°. [1X]~ -101° (c, 0.31 in CHC1 3).
Constit. of G. alypum and Picrorhiza kurrooa. Amorph.
[IX]~ -97.2° (c, 0.66 in CHC1 3). 6-0-(2-0-p-Hydroxycinnamoyi-IX-L-rhamnopyranoside):
[85819-35-8). Saccatoside
10-(Z)-Cinnamoy/, 3,4-dihydro: [70256-08-5). Globularidin
C30H 380 16 M 654.621
C14H 34,011 M 494.494
Constit. of Verbascum saccatum. Amorph. [IX]~ ~200°
Constit. of G. alypum. Amorph. [IX]~ -57.7° (c, 0.51 in
(c, 0.2 in MeOH).
MeOH).
1-0-Deg/ucosy/, 1-0-P-me/ibioside: Rehmannioside A
6-(3,4-Dihydroxybenzoyl): [50932-20-2]. Verproside
CnH320 15 M 524.475
C 22H:11;013 M 498.440 Constit. of R. g/utinosa. Powder. [IX]~ -0.1° (c, 0.5 in
Constit. of Veronica officina/is. Amorph. [IX]~ -164.8°
MeOH).
(c, 0.86 in MeOH). May be lO~substd.
1-0-Deg/ucosy/, 1-0-P-me/ibioside, nona-Ac: Cryst. (EtOH).
6-(4-Hydroxy-3-methoxybenzoyl): [39012-20-9]. Picroside II.
Mp 196°. [1X]i; +2.2° (c, 0.5 in CHC1 3).
Amphicoside
C 23H 280 13 M 512.466 10-(4-Hydroxy-3-methoxybenzoyl): [35988-27-3]. Kutkoside
Constit. of P. kurrooa. Mp 178-179°. [IX]~ -105° C 23 H 280 13 M 512.466
(CHC1 3). May be 10-substd. Constit. of P. kurrooa. Amorph. [1X]n -145° (c, 1 in
EtOH).

45
Cerberic acid - Decapetaloside Mo-00245 - Mo-00251

[58286-51-4] Cistanin Mo-00248

Bobbitt, J.M. et al, J. Org. Chern., 1961, 26, 3090; 1966, 31, 500 [91431-89-9]
(Catalposide)
Duff, R.B. et a/, Biochem. J., 1965, 96, I (Methylcatalpol) H
Inouye, H. et al, Chern. Pharm. Bull., 1971, 19, 1438 (abs config)
Singh, B. et al, Indian J. Chern., 1972, 10, 29 (Kutkoside)
Weinges, K. eta/, Justus Liebigs Ann. Chern., 1975, 2190; 1977, HO-w
1053 (Picrosides, Scutellariosides) HO \ HI
Sticher, 0. et a/, Helv. Chim. Acta, 1979, 62, 530, 535 '--0
( Veronicoside, Verminoside, M inecoside)
C9H 1P 4 M 186.207
Afifi-Yazar, F.-U. et al, Helv. Chim. Acta, 1980, 63, 1905
(Verproside) Constit. of Cistanche salsa. Needles (MeOH). Mp 123-
El-Naggar, S.F. eta/, J. Nat. Prod. (Lloydia), 1980, 43, 524 1260. [1X]i;l +62.6° (c, 1.33 in MeOH).
(Specioside) 7-Deoxy, 71X-ch/oro: [91431-88-8]. Cistachlorin
El-Naggar, L.J. et al, J. Nat. Prod. (Lloydia), 1980, 43, 649 (rev) C9H 13Cl03 M 204.653
Chaudhuri, R.K. eta/, Helv. Chim. Acta, 1981, 64, 3 (Globularin) Constit. of C. salsa. Needles (EtOAc). Mp 66-67°. [1X]i;l
Ohshio, H. eta/, Phytochemistry, 1982, 21, 133 (Rehmanniosides) +59.1° (c, 0.17 in MeOH).
Mnatsakanyan, V.A. et al, Khim. Prir. Soedin., 1983, 19, 38
(Saccatoside) Kobayashi, H. et al, Chern. Pharm. Bull., 1984, 32, 1729.
Kobayashi, H. eta/, Chern. Pharm. Bull., 1985, 33, 3645 (6-
Deoxycatalpol) Cyclopenta(c)pyran-7-carboxaldehyde, 9CI Mo-00249
Arslanian, R.L. eta/, J. Nat. Prod. (Lloydia), 1985, 48, 957 (6-
Deoxycatalpol) Norviburtinal
Damtoft, S. et al, Phytochemistry, 1985, 24, 2281 (6-Deoxycatalpol) [85051-41-8]

Cerberic acid Mo-00245 ~

[65597-44-6] ~6
CHO

co
COOR 2 C9H 60 2 M 146.145
Constit. of root bark of Kigelia pinnata. Yellow needles
(pet. ether). Mp 58°.
RI Joshi, K.C. eta/, Tetrahedron, 1983, 38, 2703.
R = COOH, R2
= Me
C 11H 80 5 M 220.181 Decaloside Mo-00250

q)OH
Constit. of Cerbera manghas. Cryst. (Me2CO). Mp 213- [50334-38-8]
2230 dec. 11
Abe, F. et al, Chern. Pharm. Bull., 1977, 25, 3422.

Cerberinic acid Mo-00246

[65597-43-5] HOGle
As Cerberic acid, Mo-00245 with
C15H120 9 M 346.333
R 1 = CHO, R 2 = H Constit. of Mentzelia decapetala. Cryst. (EtOAc). Mp 193°.
[1X]i] -137.9° (c, 0.5 in MeOH).
CIOH604 M 190.155 11-Deoxy: [83889-88-7]. Loasaside
Constit. of Cerbera manghas. Yellow solid. C 15H 220 8 M 330.334
Me ester: [65597-42-4]. Cerbinal Constit. of Mentzelia decapetala. Cryst.
C 11 H 80 4 M 204.182 (MeOH/CHC1 3). Mp 216-220° dec. [1X]i] -150° (c, 1.3 in
Constit. of C. manghas. Yellow needles (MeOH). Mp Hp).
188-189°. Danielson, T.J. et al, Can. J. Chern., 1973, 51, 1737 (Decaloside)
Abe, F. et al, Chern. Pharm. Bull., 1977, 25, 3422. El-Naggar, L.J. et al, J. Nat. Prod. (Lloydia), 1982, 45, 539
(Loasaside)
Chaenorrhinoside Mo-00247
Decapetaloside Mo-00251
[78808-68-1]

C 15H 180 9 M 342.302

Constit. of Chaenorrhinum minus. Cryst. (H 20). Mp 218-
2190 dec. [IX]~ + 133° (c, 0:6 in Hp). C16H 260 8 M 346.377
HOH2 C
~ OGle

Breinholt, J. et al, Phytochemistry, 1990, 29, 3865 (isol, pmr, cmr)
Constit. of Mentzelia decapeta/a and Viburnum
betulifolium. Oil or syrup. [iXJli -71° (c, 5 in MeOH).
Penta-Ac: Cryst. (EtOH). Mp 114-115°. [1X]i;l -90° (c, 3.7
in CHCI 3).
El-Naggar, L.J. eta/, J. Nat. Prod. (Lloydia), 1982, 45, 539 (isol)
Jensen, S.R. et al, Phytochemistry, 1985, 24, 487 (isol)

46
Dehydroiridodial - Dolichodial Mo-00252 - Mo-00257

Dehydroiridodial Mo-00252 Deutziol Mo-00255

[66537-23-3] [60352-72-9]

H~

ctoH140 2 M 166.219
C 15H 240 9
H~~c
M 348.349
Constit. of Actinidia polygama. Oil. [1X]i: +80.0° (c, 1.0 in
CHC1 3). Constit. of Deutzia scabra. Needles (EtOH). Mp 108-110°.
1-Epimer: [63808-11-7). Chrysomelidial [1X]i,S -150° (c, 0.6 in MeOH).
C 10H 140 2 M 166.219 71X-Chloro: [83889-82-1 ]. 7-Chlorodeutziol
Constit. of defence secretions of Gastrophysa cyanea and CtsH 23Cl09 M 382.794
Plagiodera versicolora. Oil. Constit. of Mentzelia decapetala. Cryst.
[73052-87-6, 76375-87-6] (MeOH/CHC1 3). Mp 126-128° dec. [IX]~ -132° (c, 2.2 in
MeOH).
Yoshihara, K. eta/, Chern. Lett., 1978, 433 (isol)
Meinwald, J. eta/, J. Am. Chern. Soc., 1978, 100, 1883 (synth) 6-Deoxy: [83889-89-8). Strictoside
Sakai, T. eta/, Tetrahedron, 1980, 36, 3115 (abs conjig) CtsH240 8 M 332.350
Jones, T.H. eta/, Tetrahedron Lett., 1980, 1701 (synth) Constit. of M. decapetala. Oil. Mp 149-150° (as penta-
Takeshita, H. eta/, Chern. Lett., 1982, 1153 (synth) Ac). [1X]i,S -118° (c, 3.7 in CHC1 3) (penta-Ac).
Hewson, A.T. et a/, J. Chern. Soc., Perkin Trans. 1, 1985, 2625 Esposito, P. eta/, Gazz. Chim. !tal., 1976, 106, 57.
(synth) El-Naggar, L.J. eta/, J. Nat. Prod. (Lloydia), 1982, 45, 539.
Uesato, S. et al, J. Chern. Soc., Chern. Commun., 1987, 1020
(synth)
Dihydronepetalactone Mo-00256
Dehydroiridodiol Mo-00253 [17672-81-0]
[76792-78-4] ,u
H•

CtoHtsOz M 170.251
Constit. of Actinidia po/ygama. Attractive to cats and male
c1oH16ol
S1?
M 168.235
Constit. of Actinidia polygama and Nepeta cataria.
adult lacewings. Oil. [IX]~ -16.7° (c, 1.00 in CHC1 3). Attractive to cats. Oil. Bp 1 107-110°. [1X]i,S + 72°.
[73088-69-4, 76792-79-5] 4-Epimer: [17672-96-7]. lsodihydronepetalactone
Sakai, T. eta/, Tetrahedron, 1980, 36, 3115 (abs config)
CtoHt60 2 M 168.235
Kimura, H. eta/, Chern. Pharm. Bull., 1982, 30, 723 (synth) Constit. of A. polygama and N. cataria. Attractive to
Nakayama, M. et a/, Chern. Lett., 1983, 147 (synth) cats. Oil. [1X]i,S + 2. 73°.
4,11-Didehydro: [60419-56-9]. Dolicholactone
Deoxyloganic acid Mo-00254 CtoHt40 2 M 166.219
1,5 ,9-Epideoxyloganic acid Constit. of Teucrium marum. Bp0_5 80-82°.
[92842-56-3] 8,9-Didehydro: see Neonepetalactone, Mo-00309
Sakan, T. et a/, Tetrahedron Lett., 1965, 4097 (isol)
Wolinsky, J. et al, J. Org. Chern., 1972, 37, 3376 (synth)
HcooH Pagnoni, U.M. eta/, Aust. J. Chern., 1976, 29, 1375

~
(Dolicholactone)
Ficini, J. et al, Tetrahedron Lett., 1976, 687 (synth)
Grandi, R. eta/, Phytochemistry, 1983, 22, 2723 (biosynth, deriv)
Fleming, J. eta/, Tetrahedron Lett., 1984, 25, 5103 (synth)
OGle
C16H2409 M 360.360 Dolichodial Mo-00257
Constit. of Nepeta cataria. Needles. Mp 106° dec. [1X]n
+85.1° (c, 1.1 in MeOH). Formerly designated 5- [5951-57-5]
Epideoxyloganic acid. The abs. config. shown appears to
be the correct one (see w.r.t. Loganic acid, Mo-00296).
Murai, F. et al, Chern. Pharm. Bull., 1984, 32, 2809.

c1oH14oz M 166.219
Constit. of Dolichoderus acanthoclinea, Teucrium marum
and lridomyrmex humilis. Liq. Bp2 96°. [IX]~ -72°.
I> Lachrymator.
Bis-2,4-dinitropheny/hydrazone: Cryst. Mp 239-242°.
2-Epimer: [3671-76-9]. Anisomophal
CtoHt•O, M 166.219

47
Ebuloside - Furcatoside A Mo-00258 - Mo-00263

Constit. of D. acanthoclinea, T. marum and/. humilis. Eranthemoside Mo-00261

Oil. Bp2 96°. [ex)~ +3.S0. [113447-40-8]
2-Epimer, bis-2,4-dinitropheny/hydrazone: Cryst. Mp 176-
1770. H

~
Cavill, G.W.K. eta/, J. Insect Physio/., 1974, 20, 2049 (isol)
Pagnoni, U.M. eta/, Aust. J. Chem., 1976, 29, 1375 (isol)
Bellesia, F. eta/, Phytochemistry, 1983, 22, 2197 (biosynth)
HOH2C '. H OGle
OH
Ebuloside Mo-00258
C 15H 220 9 M 346.333

W
[103553-93-1) Constit. of Eranthemum pu/chellum. Amorph. powder. [ex]~
-98° (c, 0.9 in EtOH).
HcHpG1c
Penta-Ac: Cryst. (EtOH). Mp 104-105°. [ex]~ -109° (c, 0.4
0 in CHC1 3).
0 Jensen, H.F.W. eta/, Phytochemistry, 1987, 26, 3353.

roH
Hoo~ Forsythide Mo-00262
C 11H 320 10 M 444.478 [43043-09-0)
Constit. of Sambucus ebulus. Amorph. powder. [ex]~
-169.1° (c, 0.64 in MeOH).
6' -0-Apiosyl: [1 07882-65-5]. 6' -0-Apiosylebuloside
C 26H 400 14 M 576.594
From S. ebulus. Amorph. powder. [ex]~ -215.5° (c, 0.51 HOOCH OGle
in H 20).
C 16H 220 11 M 390.343
7ft-Alcohol: 7,7-0-Dihydroebu/oside
Constit. of Forsythia viridissima. Powder. [ex)~ --64.7° (c, 1
C 11H 340 10 M 446.494
From S. ebulus. Amorph. [ex]~ -73.8° (c, 0.6 in MeOH). in MeOH).
7ft-Alcohol, penta-Ac: Cryst. Mp 112°. [ex]~ -65.2° (c, 0.45 8-Me ester: [42830-21-7].
C 17H 240 11 M 404.370
in CHC1 3).
Constit. of F. viridissima. Powder. [ex]~ -51.9° (c, 1 in
Gross, G.-A. eta/, Helv. Chim. Acta, 1986, 69, !56; 1987, 70, 91 MeOH).
(isol)
Di-Me ester: Cryst. Mp 141.5-142.SO. [ex]~ -58 . 2° (c, 1 in
MeOH).
Eccremocarpol A Mo-00259
6-0xo, di-Me ester: [71035-06-8]. Griselinoside
[121561-58-8]

l.P,OM<
C 18H240 12 M 432.380
Constit. of Griselina littoralis. Foam. [ex]i,l - 117° (c, 0.3
in MeOH).
6-0xo, di-Me ester, tetra-Ac: [71035-08-0].
Cryst. (EtOH). Mp 118.5-119°. [ex]i,l -122° (c, 0.3 in
CHC1 3).
HOI~C OMe Inouye, H. eta/, Chem. Pharm. Bull., 1973, 21, 497.
Jensen, S.R. eta/, Phytochemistry, 1980, 19, 2685 (Griselinoside)
C 11 H 180 6 M 246.260 Takemoto, T. eta/, Chem. Lett., 1982, 1931 (synth)
Constit. of Eccremocarpus scaber. Oil. [ex]~ -29° (MeOH). Damtoft, S. eta/, J. Chem. Soc., Perkin Trans. I, 1983, 1943
(biosynth, deriv)
1,3-Diepimer: [128443-55-0]. Jioglutin D
C 11H 180 6 M 246.260
lsol. from Rehmannia glutinosa. Amorph. powder. [ex]~ Furcatoside A Mo-00263
+ 54.9° (c, 1.23 in MeOH). [97941-28-1]
Garbarino, J.A. eta/, Heterocycles, 1989, 28, 697 (Eccremocarpol
A)
Morota, T. eta/, Phytochemistry, 1990, 29, 523 (Jioglutin D)

Eccremocarpol B Mo-00260
[121561-57-7]

~OMe
H~;:clli
OH.
6
OMe
C 11H 200 7 M 264.275
Constit. of Eccremocarpus scaber. Oil. [ex]~ -18.SO
(MeOH).
Garbarino, J.A. eta/, Phytochemistry, 1989, 28, 697.
M 650.675

48
Furcatoside C - Genipic acid Mo-00264 - Mo-00269

Constit. of Viburnum furcatum. Amorph. powder. [1Xln Gelsemide Mo-00267

-103° (c, 0.16 in MeOH). [110309-27-8]
Z-lsomer: [97995-98-7]. Furcatoside B
C3zH420 14 M 650.675
From V. furcatum. Amorph. powder. [1X]i,"' -26.6° (c,
O.o75 in MeOH).
Hase, T. eta/, Phytochemistry, 1985, 24, 1323.

Furcatoside C Mo-00264
[97941-29-2] C 10 H 12 0~ M 212.202
Constit. of Gelsemium sempervirens. Cryst. (EtOH). Mp
As Furcatoside A, Mo-00263 with
179-180°. [1X]~0 -343° (c, 0.9 in MeOH).
R = P-v-allose 7-P-v-G/ucopyranoside: [11 0322-49-1].
C16H 220 10 M 374.344
C23H 360 12 M 504.530 From G. sempervirens. Foam. [IX]~ -199° (c, 0.6 in
Constit. of Viburnum furcatum. Amorph. powder. [IX]~
MeOH).
-58.1° (c, 0.031 in MeOH).
7-P-v-G/ucopyranoside, tetra-Ac: Cryst. (toluenejEtOH).
Hase, T. et a/, Phytochemistry, 1985, 24, 1323.
Mp 134-136°. [IX]~ -179° (c, 0.5 in CHC1 3).
Jensen, S.R. eta/, Phytochemistry, 1987, 26, 1725 (isol, cryst
Gardenoside Mo-00265 struct)

.rrr
[24512-62-7]
Gelsemiol Mo-00268
[110414-77-2]

HOH2 C"J;tr(OGle
C 17H 240 11 M 404.370
Constit. of Gardeniajasminoides. Powder. Mp 118-120°.
[1X]n - 100.8° (MeOH).
10-A/dehyde: 10-Dehydrogardenoside C 10H 160 4 M 200.234
C17H 220 11 M 402.354 Constit. of Gelsemium sempervirens. Cryst. Mp 91-93°. [IX]~
Constit. of Randia canthioides. + 13° (c, 0.5 in MeOH).
10-A/dehyde, Penta-Ac: Amorph. powder. 1-0-P-v-G/ucopyranoside: [110309-32-5].
Inouye, H. eta/, Tetrahedron Lett., 1970, 3351 (biosynth) C 16H 260 9 M 362.376
Ueda, S. et a/, Chern. Pharm. Bull., 1972, 20, 1305 (biosynth) From G. sempervirens.
Bailleul, A. eta/, Phytochemistry, 1977, 16, 723 (cmr) 3-0-P-v-G/ucopyranoside: [110309-33-6].
Damtoft, S. et a/, Phytochemistry, 1981, 20, 2717 (cmr) C16H 260 9 M 362.376
Uesato, S. eta/, Phytochemistry, 1982, 21, 353 (iso[)
Kobayashi, K. et a/, Chern. Pharm. Bull., 1985, 33, 4228 (biosynth) From G. sempervirens.
Jensen, S.R. eta/, Phytochemistry, 1987, 26, 1725.
Gardoside Mo-00266
8,10-Dehydro/oganic acid Genipic acid, 9CI Mo-00269
[54835-76-6] 2-Hydroxy-3-oxabicyclo[3.3.0]oct-1(5)-eneacetic acid

HOW
[6902-76-7]
HCOOH

HOGle
C16H 220 10 M 374.344
Constit. of Gardenia jasminoides. Powder. [1X]i; -33.6° (c, C9H 120 4 M 184.191
0.4 in MeOH). lsol. from the jagua fruit Genipa americana. Shows
Penta-Ac: Cryst. (EtOH). Mp 209-211°. [1X]i; -54.4° (c, 0.6 antibiotic props. Amorph. hygroscopic powder. [1X]i,"'
in CHC13). -105° (c, 1 in EtOH).
Inouye, H. eta/, Phytochemistry, 1974, 13, 2219. NH4 salt: Cryst. Mp 125-130° dec.
Me ester: Oil.
Tallent, W.H., Tetrahedron, 1964, 20, 1781 (isol, ir, uv, nmr, struct)
Whitesell, J.K. eta/, J. Org. Chern., 1978, 43, 1650 (synth)

49
Genipinic acid - Harpagide Mo-00270 - Mo-00275

Genipinic acid Mo-00270 Gibboside Mo-00273

[108906-56-5]
MeOOC@COOH

~~~0
OH

I o
HOH 2 C H
C 11H 140 6 M 242.228
lsol. from the jagua fruit Genipa americana. Shows Ct6H 260 9 M 362.376
antibiotic props. Amorph. powder. [ali? -126° (c, 1 in Constit. of Patrinia gibbosa. Amorph. powder. [xln -22.1 o
EtOH). (c, 1 in MeOH).
Tallent, W.H., Tetrahedron, 1964, 20, 1781 (isol, ir, uv, nmr, struct) Penta-Ac: Needles (EtOH). Mp 156.5-157.SO. [a] 0 -3.87°
(c, 1 in CHC1 3).
Geniposidic acid Mo-00271 Uesato, S. et al, Phytochemistry, 1987, 26, 561 (isol, cryst struct)
Xie, S. et al, J. Nat. Prod. (Lloydia), 1989, 52, 701 (biosynth)
[27741-01-1]

HOHro
H COOH Glutinoside Mo-00274
[103744-80-5]
HO H

.me:
to OGle
C16H 220 10 M 374.344 Cl-J-tn
Constit. Genipa americana. [a]i;' + 19.3° (c, 1 in MeOH).
Me ester: [24512-63-8]. Geniposide. Genipin ]-glucoside HO OGle
C17H 240 10 M 388.371 C15H 23Cl010 M 398.793
Constit. of Gardenia jasminoides. Cryst. (Me 2CO). Mp Constit. of dried roots of Rehmannia glutinosa
163-164°. [aln + 7.SO. (Rehmanniae Radix). Hygroscopic powder. [a]~ -79.2°
Me ester, 10-Ac: [62218-50-2]. (MeOH).
C 19H 260 11 M 430.408 Yoshikawa, M. eta[, Chern. Pharm. Bull., 1986, 34, 1403.
Constit. ofG.jasminoides. Cryst. (EtOH). Mp 173-175°.
[a]~ +22.1° (c, 2.7 in MeOH).
Harpagide Mo-00275
P-v-Giucopyranosyl ester: [126005-84-3]. A.systasioside D

Hm
C22 H310 15 M 536.486 [6926-08-5]
Isol. from A.systasia bella. Cryst. (as nona-Ac). Mp 177-
1790 (nona-Ac). [a]~ -7° (c, 0.4 in CHC1 3) (nona-Ac).
Aglycone, Me ester: [6902-77-8]. Genipin
C11 H 140 5 M 226.229
Constit. of Genipa americana. Cryst. (MeOH). Mp 120-
1210. [aJn +135° (MeOH).
H~c
Bentley, T.W. et al, J. Chern. Soc. C, 1967, 2234 (ms) CtsHl40to M 364.349
Inouye, H. et al, Chern. Pharm. Bull., 1972, 20, 1287 (biosynth) Constit. of Melittis melissophy/lum.
Endo, T. et al, Chern. Pharm. Bull., 1973, 21, 2684 (biosynth) 8-0-Ac: [6926-14-3].
Takeda, Y. et al, Phytochemistry, 1975, 14, 2647 (biosynth) Ct7Hu0 11 M 406.386
Takeda, Y. et al, Chern. Pharm. Bull., 1976, 24, 2644 (deriv) Constit. of M. melissophy/lum. Cryst. Mp 154-156°. [a]~
Buyuk, G., Tetrahedron Lett., 1978, 3803 (synth, bib/)
Uesato, S. et al, Phytochemistry, 1986, 25, 2515 (biosynth)
- 132° (MeOH).
Demuth, H. eta[, Phytochemistry, 1989, 28, 3361 (Asystasioside B) Hepta-Ac: Cryst. Mp 187-188°.
8-0-Cinnamoyl: [19210-12-9]. Harpagoside
Gentioside Mo-00272 C24H300 11 M 494.494
Constit. of M. melissophy/lum and Harpagophytum
[35930-28-0] procumbens. Amorph. Mp 117-121°. [ali: -27.7° (c, 0.19
in CHC1 3), [aJn -42.6° (c, 0.99 in MeOH).
8-0-Cinnamoyl, hexa-Ac: Cryst. Mp 193-194°.
8-0-(3,4-Dimethoxybenzoyl): [72933-37-0]. Tecoside. 8-0-
Veratroylharpagide
C24H310 13 M 528.509
Constit. of Tecome/la undulata. Hygroscopic powder.
C 17H 240 11 M 404.370 Mp 139-142°. [ali? -159.3° (c, 0.4 in Meom.
Constit. of Gentiana spp. Cryst. (as hexa-Ac). Mp 191-192°
8-0-(4-Hydroxycinnamoyl): 8-0-p-Coumaroylharpagide
(hexa-Ac). [a]~ -102° (CHC1 3) (hexa-Ac).
C24H 300u M 510.494
Popov, S. et al, Phytochemistry, 1971, 10, 3077. Constit. of roots of Harpagophytum procumbt•ns.
Amorph. powder. [a]i;1 -30.SO (c, 1.09 in MeOH).
7a-Chloro: [35927-36-7]. Linarioside
C15H 23Cl010 M 398.793
Constit. of Linaria japonica. Pale-yellow hygroscopic
amorph. solid. [a]i;' - 140° (wet dioxan). Unstable.

50
Hastatoside - Iridodial Mo-00276 - Mo-00280

m
6-Deoxy, 8-Ac: [53839-03-5]. Reptoside Hygrophiloside Mo-00278
Ct,H11;010 M 390.386 [96888-14-1]
Constit. of Ajuga reptans. Amorph. powder. [ex]i7 -45°
(c, 0.7 in MeOH). HO
6-Deoxy, hexa-Ac: Cryst. (MeOH). Mp 127-128°. [ex]i7
-114° (c, 0.3 in Me 2CO). 0
7ex-Hydroxy: [79549-53-4]. Avicennioside OH H
C 1sH240 11 M 380.348 OGle
Constit. of Avicennia officina/is. Oil. C 15H 200 9 M 344.318
7ex,JO-Dihydroxy: [80666-56-4]. Cynanchoside Constit. of Hygrophila difformis.
C 15H 240 12 M 396.347 Jensen, S.R. eta/, Phytochemistry, 1985, 24, 602.
Constit. of Macfadyena cynanchoides. Amorph. [ex]i;l
-126° (c, 1 in MeOH).
lpolamiide Mo-00279
Scarpati, M.L. et al, Tetrahedron Lett., 1965, 3439 (struct)
Lichti, H. et al, Helv. Chim. Acta, 1966, 49, 1552 (struct)
[27934-98-1]
Kitagawa, I. eta/, Chern. Pharm. Bull., 1973, 21, 1978 (Linarioside)
Guiso, M. et al, Gazz. Chim. Ita/., 1974, 104, 403 (Reptoside) IY)Me
Verma, K.S. et al, J. Chern. Soc., Perkin Trans. I, 1979, 2473 (isol)
Bianco, A. eta/, Gazz. Chim. Ita/., 1981, 111, 201 (cmr)
Bonini, C. et al, Phytochemistry, 1981, 20, 1587 ( Cynanchoside) HO~l
Damtoft, S. et al, Phytochemistry, 1981, 20, 2717 (cmr) ' OGle
Kikuchi, T. eta/, Chern. Pharm. Bull., 1983, 31, 2296.
Konig, G. et al, Phytochemistry, 1987, 26, 423 (Avicennioside) Ct 7Hu011 M 406.386
Constit. of Stachytarpheta mutabilis and Lamium
amplessicaule. Cryst. (Me2CO aq.). Mp 144-145°. [ex]:;
Hastatoside Mo-00276 -136° (c, 0.5 in dioxan).
[50816-24-5] 8-Ac: [62421-28-7]. lpolamiidoside
C 19H 11P 12 M 448.423

~:Mo From L. amplessicaule. Amorph. [ex]b6 -60° (c, 0.7 in

dioxan).
6P-Hydroxy: 6fJ-Hydroxyipolamiide
Ct,H 260 12 M 422.385
HOGle Constit. of S. mutabilis. Cryst. (MeOH/Me 2CO). Mp
Ct7H240 11 M 404.370 192-193°. [ex]i;l -161° (c, 0.2 in MeOH).
Constit. of Verbena officina/is. [ex]i:' -320° (Hp). 7P-Hydroxy: see Lamiide, Mo-00292
Tetra-Ac: Cryst. Mp 180-182°. [ex]~ -245° (c, 0.4 in 6P,7P-Dihydroxy: [55732-45-1]. Phlomiol
CHC1 3). C1 7H 260 13 M 438.385
Umehata, Y. eta/, Tetrahedron Lett., 1975, 3195 (isol) Constit. of Phlomis fruticosa. Cryst. (EtOH). Mp 150-
Bianco, A. et al, Gazz. Chim. Ita/., 1981, 111, 201 (cmr) 151°. [ex]i;l -112° (c, 0.5 in MeOH).
Damtoft, S. et al, J. Chern. Soc., Perkin Trans. 1, 1983, 1943 Scarpati, M.L. eta/, Gazz. Chim. Ita/., 1969, 99, 1150 (lpolamiide)
(biosynth) Bianco, A. et a/, Gazz. Chim. /tal., 1975, 105, 185; 1981, 111, 201
(Phlomiol)
Tantisewie, B. eta/, Phytochemistry, 1975, 14, 1462 (isol)
Hop ether Mo-00277 Bianco, A. et al, Gazz. Chim. /tal., 1976, 106, 947 (Ipolamiide,
Hexahydro-1 ,J-dimethy/-4-methy/ene-JH-cyclopenta[clfuran, lpolamiidoside)
9CI. 2,2-Dimethyl-6-methy/ene-3-oxabicyc/o[J .3 .O]octane De Luca, C. et al, Phytochemistry, 1983, 22, 1185 (isol)
[19901-95-2]
Iridodial Mo-00280

~0
2-Formy/-ex,3-dimethylcyclopentaneacetaldehyde, 9CI
[550-45-8]

C 10H 160 M 152.236

Volatile constit. of Japanese hops. Oil. Bp 15 50-53°.
Naya, Y. et al, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1968,
89, 1113 (isol)
Naya, Y. et al, Tetrahedron Lett., 1968, 1645 (isol)
Imagawa, T. eta/, Tetrahedron Lett., 1979, 1691 (synth)
YcHo~
)-tcHO

C 10H 160 1 M 168.235

s=P OH

From lridomyrmex spp. Defensive secretion of Rove

Absolute
configuration

Johnson, C.R. et al, Tetrahedron Lett., 1982, 23, 5005 (synth)

beetles (Staphylinus olens). Oil. BPt.o 90-92°.
Tanimori, S. eta/, Agric. Bioi. Chern., 1990, 54, 1875. (synth)
Bis-2,4-dinitropheny/hydrazone: Cryst. (EtOH). Mp 224-
2250 dec.
8-Epimer: see 3-Myodeserten-1-ol, Mo-00306
Cavill, G.W. et al, Chern. Ind. (London), 1956, 465 (struct, isol)
Clark, K.J. et a/, Tetrahedron, 1959, 6, 217 (abs con.fig)
Achmad, S. et a/, Proc. Chern. Soc., London, 1963, 166 (struct)
Achmad, S.A. eta/, Aust. J. Chern., 1965, 18, 1989 (synth)
Ritterskamp, P. eta/, J. Org. Chern., 1984, 49, 1155 (synth)
Uesato, S. et al, Tetrahedron Lett., 1986, 27, 2896 (biosynth)

51
Iridomyrmecin - lxoside Mo-00281- Mo-00285

Uesato, S. eta/, J. Chern. Soc., Chern. Commun., 1987, 1020 Oxime:

(synth) C10H 17NO M 167.250
Uesato, S. eta/, Tetrahedron Lett., 1987, 28, 4431 (biosynth) Viscous syrup or cryst. Mp 117°. [1X]ii + 10.97° (c, 1.0 in
MeOH).
Iridomyrmecin Mo-00281 2,4-Dinitrophenylhydrazone: Long, dark red cryst.
[485-43-8] (MeOH/CHC1 3). Mp 137.SO. [IX]!: +31° (c, 1.0 in
CHC13).
(±)-form [17615-80-4]
Semicarbazone: [16741-94-9].
Cryst. (MeOH). Mp 205-220°.
Short, A.G. eta/, J. Chern. Soc., 1939, 1040 (synth)
Edwards, D.J., J. Org. Chern., 1967, 32, 2561 (synth)
C,oH 1602 M 168.235 Wolinsky, J. eta/, Tetrahedron, 1969, 25, 3767 (synth)
Constit. of Iridomyrmex humilis. Insecticidal ant secretion. Kempter, G. eta/, J. Prakt. Chern., 1972, 314, 543 (synth)
Cryst. (pet. ether). Mp 60-61°. [1X]n +210° (EtOH). Allen, K.G. eta/, Phytochemistry, 1976, 15, 101 (biosynth)
Matatabilactone was a mixt. of Iridomyrmecin and Schumacher, J.N. eta/, J. Agric. Food Chern., 1977, 25, 310 (isol,
ir, ms, pmr)
Isoiridomyrmecin.
4-Epimer: [573-94-4]. Isoiridomyrmecin. Iridolactone
From /. spp. Prisms (pet. ether). Mp 57.5-58°. [IX]~ Isovaltrate Mo-00284
-56° (c, 1.09 in CC14). [31078-10-1]
Kerr, R.W. et a/, Aust. J. Chern., 1961, 14, 276.
McConnell, J.F. et a/, Tetrahedron Lett., 1962, 445 (cryst struct)
Wolinsky, J. eta/, Tetrahedron, 1965, 21, 1247 (synth)
Matthews, R.S. et al, J. Org. Chern., 1975, 40, 3312 (synth)
Yamada, Y. eta/, Chern. Lett., 1978, 1405 (synth)
Callant, P. eta/, Tetrahedron, 1980, 36, 2085 (synth)
Wender, P.A. eta/, Tetrahedron Lett., 1983, 24, 4543 (synth)
Wang, T.F. eta/, J. Chern. Soc., Chern. Commun., 1989, 1876
(synth)
C22H 34P 8 M 422.474
2-Isopropenyl-5- Mo-00282 Constit. of Valeriana officina/is. Oil. [IX]~ + 151° (MeOH).
methylcyclopentanecarboxaldehyde Deacetyl: [53773-14-1]. Deacetylisovaltrate
Photocitral A C20 H 280 7 M 380.437
Constit. of V. officina/is. Oil. [1X]i? + 35° (MeOH).

&CHO
[43219-98-3]
Thies, P.W. eta/, Tetrahedron, 1973, 29, 3213 (struct)
Popov, S. eta/, Phytochemistry, 1974, 13, 2815 (isol)

Ixoside Mo-00285
;=
\
[58514-31-1]

~H
C10H,60 M 152.236
Oil. Bp8 87°.
Cookson, R.C. et a/, Tetrahedron, 1963, 19, 1995 (synth)
Biichi, G. et al, J. Am. Chern. Soc., 1965, 87, 1589 (synth)
Sakai, T. eta/, J. Org. Chern., 1981, 46, 4774 (synth)
HOO~ HOGle
C,6H200u M 388.327
4-Isopropyl-2,3-dimethyl-2-cyclopenten-1- Mo-00283 Constit. of Ixeris chinensis. Powder. [IX]~ + 33.6'' (c, 1.2 in
one, SCI H 20).
2,3-Dimethyl-4-(1-methylethyl)cyc/opent-2-en-1-one, 9CI Tetra-Ac: Cryst. (EtOH). Mp 236-237°.
[3 779-64-4] 10-Me ester: [106847-83-0]. /0-Methy/ixoside
C17H 220 11 M 402.354
Constit. of Randia dumetorum. Cryst. (MeOH). Mp 215-
2170.
Takeda, Y. eta/, Phytochemistry, 1975, 14, 2647 (isol)
Sati, O.P. et al, Phytochemistry, 1986, 25, 2658 (isol, pmr, cmr)

CIOHI60 M 152.236
Found in tobacco.
(+)-form
Pale greenish-yellow, mobile liq. Bp 10 73°. [1X]i;l +80.8°
(homogeneous).
(-)-form
Bp 13 89°.
Semicarbazone: Amorph. solid (MeOH aq.). Mp 155-156°.
[IX]!: + 55° (c, 1.0 in MeOH).

52
Jiofuran - Lamiide Mo-00286 - Mo-00292

Jiofuran Mo-00286 Kickxioside Mo-00290

[110906-83-7]

C,H110 4 M 184.191 t
tf>
COO OH
Constit. of Rehmannia g/utinosa. Arnorph. powder. [a]i;4
-30.4° (c, 0.19 in MeOH).
Morota, T. et al, Phytochemistry, 1989, 28, 2385 (isol, pmr, cmr)

Jioglutin E Mo-00287 OGle

[128397-37-5] C25 H 360 11 M 528.552
Constit. of Kickxia spuria. [a]n -63.2° (e, 0.7 in MeOH).
HO H Nicoletti, M. eta/, Planta Med., 1987, 295.
~~OMe
H):tyo Lamalbide
Lamiridoside
[52212-87-0]
Mo-00291

1
OMe
C 11H 24,05 M 232.276
Constit. of Rehmannia glutinosa. Arnorph. powder. [a]i?
-118.2° (c, 0.95 in MeOH). HO~Me
H~~c
Morota, T. et al, Phytochemistry, 1990, 29, 523 (iso/, pmr, cmr)

Jioglutolide Mo-00288
C 17H 21;011 M 422.385
OHH Constit. of Lamii a/hi. Arnorph. powder. Mp 125-128°.
[ali? - 124° (H 20).

H~tt
Hepta-Ac: Cryst. Mp 195°.
Brieskom, C.H. et al, Tetrahedron Lett., 1973, 4037 (isol)
Eigtved, P. et a/, Acta Chern. Scand., Ser. B, 1974, 28, 85 (isol)

C,H140 4 M 186.207
Constit. of Rehmannia glutinosa. Needles (Me2CO). Mp
Lamiide Mo-00292
141-142°. [a]n -8.4° (c, 1.19 in MeOH). [27856-54-8]
Morota, T. eta/, Phytochemistry, 1989, 28, 2385 (isol, pmr, cmr,
cryst struct)
H~Me
Kanokoside A
[64703-85-1]
Mo-00289
HO~O
OGle
R Ct,HuOu M 422.385
H CH2 0Glc
Constit. of Lamium amplessicau/e. Arnorph. [a]i; -127° (c,
R' 1.1 in MeOH).
10 0 7-Cinnamoy/: [53526-67-3]. Durantoside I
HOCH2__ H
HO OOC~ C26 H 320 13 M 552.531
Constit. of Duranta repens. Arnorph. Mp 199-204° (as
RR' = - 0 - penta-Ac).
C21H32011 M 476.477 7-(4-Hydroxy-E-cinnamoyl): [64597-22-4]. Lamiidoside
Constit. of Valeriana officina/is root. Amorph. Mp 58-62° C26 H 320 14 M 568.530
(as penta-Ac). [a]n -87.SO (MeOH)(penta-Ac). Constit. of Pho/omis fruticosa. Arnorph., cryst. (as
10-0-P-v-G/ucopyranoside: [64703-87-3]. Kan.okoside C penta-Ac). Mp 199-200° (penta-Ac). [a]~ -80° (c, 0.34
C27H 420 17 M 638.619 in MeOH)(penta-Ac).
From V. officina/is root. Arnorph. Mp 102-105° (as 7-(4-Methoxy-E-cinnamoyl): [53526-66-2). Durantoside II
penta-Ac). [a]n -51.SO (MeOH)(penta-Ac). C27H 340 14 M 582.557
Endo, T. eta/, Chern. Pharm. Bull., 1977, 25, 2140. Constit. of D. repens. Arnorph. Mp 161-166° (penta-Ac).
7-(3,4-Dimethoxy-E-cinnamoyl): [53526-65-1]. Durantoside
lll
C28H 360 15 M 612.583
Constit. of D. repens. Arnorph.
Aglycone: Lamiigenin
Needles (Me 2CO). Mp 119-121°. [a]~ +46.SO (c, 0.8 in
Me2CO).

53
Lamiol - Loganic acid Mo-00293 - Mo-00296

5-Deoxy: Ctll'yoptositk. 5-Desoxylamiide Constit. of Rehmannia glutinosa. Powder. [exW -11.3°

C 17H 160 11 M 406.386 (c, 0.5 in MeOH).
Constit. of Caryopteris sp. Mp 137-139° (as penta-Ac). 6-Epimer, 8-0-P-D-galactopyranoside, nona-Ac: Plates
Scarpati, M.L. et al, Gazz. Chim. /tal., 1969, 99, 1150 (Lamiide) (EtOH). Mp 156-157°. [ex]~ -10.8° {c, 0.5 in CHC1 3).
Rimp1er, H. et al, Z. Naturforsch., C, 1974, 29, 111 (Durantosides) 6-Epimer, 6-Ac: 6-Acetylmioporoside
Bianco, G. et al, Gazz. Chim. /tal., 1977, 107, 67 (Lamiidoside) C17H 160 10 M 390.386
E1-Naggar, L.J. et al, J. Nat. Prod. (Lloydia), 1980, 43, 649 (rev,
Caryoptoside) Constit. of Betonica officina/is. Amorph. [ex]i? -165.3°
(c, 0.33 in MeOH).
6-Deoxy: [55941-48-5]. Gluroside
Lamiol Mo-00293
C 1 ~H 240 8 M 332.350
[30987•52-1] Constit. of Galeopsis pubescens and G. tetrahit. Amorph.
[ex]i? -178.SO (H20).
H~ 6-Deoxy,penta-Ac: Cryst. Mp 113.3-114.3°. [ex]~0 -124.1°
(CHC1 3).
fub Weinges, K. et al, Justus Liebigs Ann. Chem., 1973, 566 (isol, ir,
pmr)
HO' HOGle Guiso, M. et al, Gazz. Chim. /tal., 1974, 104, 25 (isol)
Bianco, A. et al, Gazz. Chim. /tal., 1975, lOS, 175 (Mioporoside)
C16H 160 10 M 378.375 Schilling, G. et al, Justus Liebigs Ann. Chem., 1975, 230 (cmr)
Constit. of Lamium amplexicaule. Hygroscopic arnorph. Sticher, 0. et al, Tetrahedron Lett., 1975, 291 (Gluroside)
powder. [ex] 0 -153° (dioxan). Agostini, A. et al, Gazz. Chim. /tal., 1982, 112, 9 (struct)
8-Ac: [19228-19-4]. Lamiositk Davini, E. et al, Gazz. Chim. /tal., 1982, 112, 57 (struct)
Weinges, K. et al, Justus Liebigs Ann. Chem., 1985, 1063 (cryst
C18H 280 11 M 420.413
struct, abs corifig)
Constit. of L. amplexicaule. Hygroscopic amorph. Jeker, M. et al, HCA, 1989, 72, 1787 (6-Acetylmioporoside)
powder~ [ex]~ -125° (c, 0.5 in dioxan).
Hexa-Ac: Cryst. (EtOH). Mp 205-207°. [ex] 0 -116°
(dioxan).
Linaride Mo-00295
8-Ac, 6-deoxy: 6-Deoxylamioside [63879-67-4]

'+)
C18H 280 10 M 404.413
From L. amplexicaule. Amorph.
5-Deoxy: 5-Deoxy/amiol

~c
C16H 160 9 M 362.376
Constit. of Satureia vulgaris. Amorph. powder.
Scarpati, M.L. et al, Tetrahedron, 1967, 23, 4709 (isol)
Inouye, H. et al, Phytochemistry, 1977, 16, 1669 (biosynth) C 1 ~Hn0 8 M 330.334
Bianco, A. et al, Gazz. Chim. /tal., 1981, 111, 201 (cmr) Constit. of Linaria muratis. Amorph.
Agostini, A. et al, Gazz. Chim. /tal., 1982, 112, 9. Penta-Ac: Cryst. (EtOH). Mp 122-122.SO. [ex]~ --178° (c,
Guiso, M. et al, J. Nat. Prod. (Lloydia), 1983, 46, 157.
3.3 in dioxan).
Bianco, A. et al, Phytochemistry, 1984, 23, 121 (deriv)
Bianco, A. et al, Gazz. Chim. /tal., 1977, 107, 83.

Leonuride Mo-00294
Ajugol Loganic acid Mo-00296
[52949-83-4] [22255-40-9]

HOW
H COOH
H~
HO~C HOGle
' OGle
C 16H 240 10 M 376.360
C 1 ~H 240 9 M 348.349
Constit. of Ajuga reptans, Melittis melissophyllum and Constit. of Swertia caroliniensis.
Leonurus cardiaca. Amorph. powder. Me ester: Loganin. Meliatin
C17H 160 10 M 390.386
8-Ac: [52916-96-8]. Ajugositk
Constit. of, inter alia, Strychnos nux-vomica and
C17H 160 10 M 390.386
Menyanthes trifolia. Key intermed. in biosynth. of many
Constit. of A. reptans, M. melissophyllum and L.
alkaloids. Cryst. (EtOH). Mp 223°. [ex] 0 -83° (Hp).
cardiaca. Amorph. powder.
Penta-Ac: Cryst. Mp 168°.
Hexa-Ac: [50515-38-3].
Mp 174-175°. [ex]i; -200° (c, 2 in CHC1 3). 7-Ketone, Me ester: [152-91-0]. Dehydrologanin.
Ketologanin
6-Epimer: [55781-48-1]. Myoporoside. Mioporoside
C17H 240 10 M 388.371
Constit. of Myoporus insulare. Amorph. Struct. revised
From Vinca rosea and S. nux-vomica. Cryst. Mp 194-
in 1985.
1950. [ex]i,l -110° (H 20).
6-Epimer, Penta-Ac: Cryst. (EtOH). Mp 157-158°.
Me ester, aglycone: [29748-10-5]. Loganetin
6-Epimer, 8-0-P-D-galactopyranoside: [81720-07-2]. C 11 H 16 0~ M 228.244
Relmuumioside C Amorph. [ex]i? -24° (EtOH).
C 11H 340 14 M 510.491
Me ester, 5-deoxy: [26660-57-1]. 5-Deoxyloganin
C 17H 160 9 M 374.387

54
Matatabiether - 2-Methyl-5-(1-methylethylidene) ... Mo-00297 - Mo-00300

Constit. of S. nux-vomica. In vivo precursor of Loganin. Wolinsky, J. et al, Tetrahedron, 1969, 25, 3767 (synth)
Cryst. (as tetra-Ac). Mp 115-116° (tetra-Ac). Sakai, T. et al, Tetrahedron, 1980, 36, 3115 (abs corifig)
Kato, N. et al, Heterocycles, 1990, 30, 341 (synth)
7-0-(4-0-P-D-Glucopyranosyloxy-3-methoxycinnamoyl):
[96681-56-0]. Periclymenosidic acid
C3zH4z01a M 714.673 Mentzeloside Mo-00298
Consit. of Lonicera coerulea. Amorph. powder. [ac]i:' Deutzioside
-54.7° (c, 0.56 in MeOH). [41753-47-3]
7-0-(4-0-P-D-Glucopyranosyloxy-3-methoxycinnamoyl), Me
ester: [89332-48-9]. Periclymenoside
C33H440 18 M 728.700
H~
Constit. of L. periclymenum. Amorph. powder. [at:Ji:'
--'54.2° (c, 0.7 in MeOH). 0~6
7-0-[6-0-(2,3-Dihydroxybenzoyl)-P-D-glucopyranoside], 2,3- HOGle
dihydroxybenzoyl ester: [96935-16-9]. Depressoside ClsH110 9 M 346.333
C35H 410 10 M 782.705 Constit. of Mentzelia decapetala. Cryst. (EtOH). Mp 271-
Constit. of Gentiana depressa. Noncryst. [at:Jn -31° (c, 273.50 dec. [ac]~ -97° (c, 0.5 in Hp).
0.175 in MeOH).
Danielson, T.J. et al, Can. J. Chern., 1973, 51, 760 (iso[)
7- Epimer, 7-0-(3-hydroxybenzoyl): [96087 -14-8]. Esposito, P. et al, Gazz. Chim. Ita/., 1976, 106, 57 (struct)
Swertiaside A. Swertiaside Inouye, H. et al, Phytochemistry, 1977, 16, 1669 (biosynth)
C13H180 11 M 496.467 Uesato, S. et al, Phytochemistry, 1986, 25, 2515 (biosynth)
Constit. of Swertia japonica. Amorph. [ac]i; -109.1° (c,
3.17 in MeOH). 4-Methylantirrhinoside Mo-00299
7-Ketone, 3-(4-hydroxyphenyl)propanoyl ester: [29118-80-7].
Syringopicroside
Constit. of leaves of Syringa vulgaris. Amorph., plates
(EtOH)(as penta-Ac). Mp 156-156.SO (penta-Ac). [ac]i:'· 5
-116.SO (c, 1 in CHC1 3) (as penta-Ac).
7-Epimer, 7-0-(3-hydroxybenzoyloxybenzoyl): [109770-92-
5]. Senburiside II
C30H 310 14 M 616.574 C16H140 10 M 376.360
Constit. of Swertiajaponica. [at:Ji? -88.6° (c, 0.79 in Constit. of Satureia vulgaris. Amorph. powder. [acJn - 61°
MeOH). (c, 0.1 in MeOH).
Birch, A.J. et al, J. Chern. Soc., 1961, 1407 (struct) Bianco, A. et al, Phytochemistry, 1984, 23, 121.
Bentley, T.W. et al, J. Chern. Soc. C, 1967, 2234 (ms)
Asaka, Y. et al, Tetrahedron, 1970, 26, 2365 (Syringopicroside)
Battersby, A.R., Alkaloids (London), 1971, 1, 31 (biosynth) 2-Methyl-5-(1-
Bhakuni, D.S. et al, Indian J. Chern., 1972, 10, 454 (iso[) methylethylidene)cyclopentanecarboxylic
Partridge, J.J. et al, J. Am. Chern. Soc., 1973, 95, 532 (synth)
Biichi, G. et al, J. Am. Chern. Soc., 1973, 95, 540 (synth) acid, 9CI Mo-00300
Bisset, N.G. et al, Phytochemistry, 1974, 13, 265 (iso[) 2-lsopropylidene-5-methylcyclopentanecarboxylic acid.
Heckendorf, A.H. et al, J. Org. Chern., 1976, 41, 2045 (cmr) Pulegenic acid
Au-Yeung, B.-W. eta/, J. Chern. Soc., Chern. Commun., 1977, 81
(synth)
Kon, K. et al, Helv. Chim. Acta, 1983, 66, 755 (synth)
Calis, I. et al, Helv. Chim. Acta, 1984, 67, HjO (Periclymenoside)
Ikeshiro, Y. et al, Planta Med., 1984, SO, 485; 1987, 158
(Swertiaside A, Senburiside II)
Hewson, A.T. et al, J. Chern. Soc., Perkin Trans. I, 1985, 2625 CIOHI601 M 168.235
(synth) (JS,2R)-form [7712-68-7]
Chulia, A.J. et al, J. Nat. Prod. (Lloydia), 1985, 48, 54 Pale yellow oil. Bp 12 144-146°. [at:Ji:' +48.2°.
(Depressoside)
Calis, I. et al, J. Nat. Prod. (Lloydia), 1985, 48, 108 Me ester: [30165-01-6].
(Periclymenosidic acid) C 11 H 180 1 M 182.262
Vandewalle, M. et a/, Tetrahedron, 1986, 42, 4035 (synth) Bp5 105-110°.
Amide:
Matatabietber Mo-00297 CIOHI7NO M 167.250
1,4-Dimethyl-8-methylene-2-oxabicyclo[3 .2.J]octane, 8CI Needles (H 20 or EtOH aq.). V. sol. EtOH, Et20. Mp
123°. [ac]1:;'1 +29.1° (MeOH).
[21700-60-7]
Riipe, H. et al, Helv. Chim. Acta, 1928, 11, 463 (synth)
I Reusch, W. et al, Tetrahedron, 1967, 23, 1953 (synth, ir, pmr)

~
Kalnikawa, T. eta/, Tetrahedron, 1970, 26, 4561 (synth, ir)
Wolinsky, J. et al, Tetrahedron, 1976, 32, 1335 (synth)

H
C1oH1,o M 152.236
Constit. of Actinidia polygama. Oil. Bp 16 67°. [at:]i; -147.3°
(c, 1.03 in CHC1 3).
[24189-95-5]
lsoe, S. et al, Tetrahedron Lett., 1968, 5319 (isol, synth)

55
Mitsugashiwalactone - Monotropein Mo-00301 - Mo-00304

Mitsugashiwalactone Mo-00301 Constit. of Lamiastrum galeobdolon. Amorph. powder.

Hexahydro-7-methylcyclopenta(c]pyran-1(3H)-one, 9CI [a:Jn -60.SO (c, 1 in MeOH).
[60363-05-5] 6-Epimer: 6-Epimonomelittoside
C1sH110 10 M 362.333
Constit. of Tecoma heptaphyl/a. Amorph. [a:]~ -47° (c,

~
1.0 in MeOH).
6-(4-Hydroxy-E-cinnamoy/): [30358-89-5]. Odontosidet
C24H180 11 M 508.478
Ho Constit. of Odontites serotina. Cryst. Mp 145-147°. [a:]~
-92° (c, 0.1 in EtOH).
C9H 140 1 M 154.208
Constit. of Boshniakia rossica. Cat attractant. Oil. 10-Benzoyl: [73248-91-6]. Globularifolin
C11H 160 11 M 466.441
8-Epimer: [60363-04-4]. Onikulactone
Constit. of Globularia cordifo/ia. Amorph. [a:Ji? -122.8°
C9H 140 1 M 154.208
(c, 1.2 in MeOH).
lsol. from Menyanthes trifoliata. Cat attractant. Oil.
10-0-(4-Hydroxycinnamoy/): [85802-33-1]. Eurostoside
7p-Hydroxy: [85502-19-8]. Boonein
C24H 180 11 M 508.478
C,H140 3 M 170.208
Constit. of Euphrasia rostkoviana. Amorph. [a:)~
lsol. from bark of Alstonia boonei. Cryst.
-128.1 o (MeOH).
(EtOAcjhexane). Mp 95-96°. [a:]~ +28.6° (c, 0.5 in
CHC1 3). 5-0-P-Sophoroside: [81720-08-3]. Rehmannioside D
C17H41010 M 686.617
Sakan, T. et at, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1969,
90, 507 (isol)
Constit. of Rehmannia glutinosa. Powder. [a:Jii -27.1 o
Ohta, H. eta/, J. Org. Chern., 1977, 42, 1231 (synth, ir, pmr, ms) (c, 0.5 in Hp).
Marini-Bettolo, G.B. et al, Tetrahedron, 1983, 39, 323 (isol, cryst 5-0-P-Sophoroside, dodeca-Ac: Cryst. Mp 236°. [a:]~ -9.3°
struct, Boonein) (c, 0.5 in CHC1 3).
Lee, T.V. eta/, J. Chern. Soc., Chern. Commun., 1985, 371 (synth,
Scarpati, M.L. et al, Gazz. Chim. /tal., 1967, 97, 1209 ( Melittoside)
Boonein) Scarpati, M.L. et al, Ric. Sci., 1967, 37, 840 (Monomelittoside)
Nugent, W.A. et a/, J. Org. Chern., 1986, 51, 3376.
Degot, A.V. et a/, Khim. Prir. Soedin., 1970, 6, 474; Chern. Nat.
Amri, M. eta/, Tetrahedron Lett., 1987, 28, 5521 (synth)
Compd. (Engl. Trans/.), 489 (Odontoside)
Chaudhuri, R.K. et al, Helv. Chim. Acta, 1980, 63, 117
Mollugoside Mo-00302 (Globularifolin)
Oshio, H. et a/, Phytochemistry, 1982, 21, 133 (Rehmannioside D)

ill
[82526-63-4] Bianco, A. et al, Phytochemistry, 1983, 22, 1189; 1986, 25, 1981
HCOOMe (derivs)
Salama, 0. et a/, Planta Med., 1983, 47, 90 (Eurostoside)
Saadi, H. et al, Phytochemistry, 1990, 29, 3938 (10-
Acetylmonomelittoside)
HOOC O
OGle Monotropein Mo-00304
C17H 110 11 M 418.354 [5945-50-6]
Constit. of Galium mol/ugo. Amorph. powder.

~H
Me ester: Amorph. [a:]i,S -88.7° (c, 0.83 in MeOH).
Iavarone, C. et al, Phytochemistry, 1983, 22, 175.

Monomelittoside Mo-00303 HOH2~ 0~ OGle

[20633-72-1]
C16H110 11 M 390.343
Constit. of Monotropa hypopithys, M. uniflora,
H~ Liquidambar styraciflua, L. orientale and Pyrola
renifolia. Widespread in the Pyro1aceae. Cryst. + 1H20

HOH2C
1;>-ty<
OGle
(Hp). Mp 175° dec. [a:]~ -127.7° (H 20).
Me ester, penta-Ac: Cryst. Mp 147-148°. [a:]~ -76.2°
(EtOH).
C15H110 10 M 362.333 10-0-(p-Hydroxycinnamoy/): [36138-58-6]. Vaccinoside
Constit. of Melittis melissophyl/um. Amorph. powder. V. C15H180 13 M 536.488
sol. Hp. Mp 158-160° (Hepta-Ac). [a:]~ -180° (c, 0.7 lsol. from flowers of Vaccinium 'bracteatum. Mp 150-
in Hp). 1530. [a:]~ -75.2° (c, 1 in H 20).
10-Ac: 10-Acetylmonomelittoside 8-Deoxy, Me ester: [77856-55-4]. Apodantheroside
C17H 240 11 M 404.370 C17H 240 10 M 388.371
Constit. of Plantago media. Amorph. powder. Constit. of Feretia apodanthera. Cryst. (Etpjhexane)
5-0-P-D-Glucopyranoside: [19467-03-9]. Melittoside (as penta-Ac). Mp 126° (penta-Ac).
C11 H310 15 M 524.475 8-Epimer, Me ester: see Gardenoside, Mo-00265
Isol. from M. melissophyl/um. Prisms or amorph. Bobbitt, J.M. eta/, Chern. Ind. (London), 1964, 931 (pmr)
powder. V. sol. Hp. Mp 167-168°. [a:]~ -29° (c, 1.6 in Inouye, H. et al, Chern. Pharm. Bull., 1964, 12, 255, 888 (isol, uv,
Hp). ir, pmr, struct)
Masaki, N. et al, Tetrahedron Lett., 1967, 2367 (cryst struct)
5-0-P-D-Glucopyranoside, deca-Ac: Mp 149-149.5°.
Rimpler, H. eta/, Phytochemistry, 1970, 18, 1891 (isol)
5-0-P-D-Glucoyranoside, 10-deoxy: 10-Deoxymelittoside
C11H310 14 M 508.475

56
Mussaenosidic acid - Neonepetalactone Mo-00305 - Mo-00309

Sakakibara, J. et al, Chern. Pharm. Bull., 1971, 19, 1979 FromM. deserti. Cryst. (pentane). Mp 17°. [1X]n +273°
( Vaccinoside) (c, 2.7 in CHC1 3).
Bailleul, F. et al, Phytochemistry, 1980, 19, 2763 (Apodantheroside)
Grant, H.G. et al, Aust. J. Chern., 1980, 33, 853; 1985, 38, 325.
Damtoft, S. et al, Phytochemistry, 1981, 20, 2717 (cmr)
Murai, F. et al, Planta Med., 1982, 46, 45 (Boschniaside)

Mussaenosidic acid Mo-00305

Nardostachin Mo-00307
H CX>OH [114687-82-0]

Ct6H240to
H~,
M 376.360 H~
HCHpOC~

Constit. of Melampyrum cristatum. Foam. [1X]i,l' -118° (c,

0. 7 in MeOH). Hooc~
Me ester: [64421-27-8]. Mussaenoside
C 17H 260 10 M 390.386 C20H 320 6 M 368.469
Isol. from Mussaenda parvifiora, M. arvense and M. Constit. of Nardostachys chinensis. Oil. [1X]n -80.9° (c, 0.4
shikokiana. Powder. [1X]i;' -106° (c, 0.6 in MeOH). in CHC1 3).
2' -(4-Hydroxybenzoyl): 2' -(p-Hydroxybenzoyl)mussaenosidic Bagchi, A. et al, Planta Med., 1988, 54, 87.
acid
C23H 280 12 M 496.467 Neomatatabiol Mo-00308
Constit. of Vitex negundo. Needles (MeOH). Mp 160- [21699-53-6]

w
1620. [1X]i;l -117.6° (c, 3 in MeOH).
I
6' -(4-Hydroxybenzoyl): 6' -(p-Hydroxybenzoyl)mussaenosidic H•
acid
C23H 280 12 M 496.467
From V. negundo. Solid. [1X]i;' -120° (c, 3 in MeOH).
6'-(3,4-Dihydroxycinnamoyl), Me ester: [76994-10-0].
Ladroside OH
C26H 320 13 M 552.531 CIOH1802 M 170.251
Constit. of Veronica sp. Amorph. [1X]i,l' -68.93° (c, 0.72 Constit. of Actinidia polygama. Potent attractant for male
in MeOH). adults of Chrysopa septempunctata (7-spot ladybird) and
Takeda, Y. et al, Phytochemistry, 1977, 16, 1409 (isol, struct) other C. spp. Oil. Bp5 95°. [1X]:,S +21.3°.
El-Naggar, L.J. et al, J. Nat. Prod. (Lloydia), 1980, 43, 649 (rev, 9-Epimer: [34258-02-1]. lsoneomatatabiol
Ladroside) CIOH1801 M 170.251
Sehgal, C.K. et al, Phytochemistry, 1982, 21, 363; 1983, 22, 1036 Constit. of the leaves of A. polygama. Attractant for C.
(derivs) spp.
Dam toft, S. et al, Phytochemistry, 1984, 23, 2387 (isol)
Hyeon, S.B. et al, Tetrahedron Lett., 1968, 5325.

3-Myodeserten-1-ol Mo-00306
Neonepetalactone Mo-00309

>1?
[24190-25-8]

~
(lR)-form
OH
CtoHI602 M 168.235
0
(JR)-form
Ac: [95585-89-0]. JS-Acetoxy-3-myodesertene CIOH1402 M 166.219
C 12H 180 3 M 210.272 Constit. of Actinidia polygama. Attractive to cats. Oil. [1X]i:
-166.8° (c, 0.31 in CHC1 3).
Constit. of Myoporum deserti. Oil. [1X]n -183° (c, 7.7 in
CHC1 3). 4-Epimer: [76549-18-3]. Isoneonepetalactone
Me ether: [19479-28-8]. 1-Methoxy-3-myodesertene. CIOH1401 M 166.219
Myodesertin (obsol.)
Constit. of A. po/ygama. Oil. [1X]n -66° (CHC1 3).
C 11H 180 2 M 182.262 Wolinsky, J. et al, Tetrahedron, 1969, 25, 3767 (isol)
Isol. from M. deserti. Bp2 67°. [1X]n -165° (neat). ni;' Sakai, T. et al, Bull. Chern. Soc. Jpn., 1980, 53, 3683 (isol)
Sakai, T. et al, Tetrahedron, 1980, 36, 3115 (abs config)
1.4752. Taber, D.F. et al, J. Org. Chern., 1988, 53, 2984 (synth)
1-0-P-D-Glucopyranoside: Boschniaside
Ct6H 260 7 M 330.377
Constit. of Boschniakia rossica. Amorph., cryst. (as
tetra-Ac). Mp 131-132° (tetra-Ac). [1X]~4 -140.8° (c, 1.25
in CHC1 3) (tetra-Ac).
(JS)-form
Ac: [95585-88-9]. JR-Acetoxy-3-myodesertene
C 12H 180 3 M 210.272

57
Nepetalactone - Nyctanthoside Mo-00310 - Mo-00314

Nepetalactone Mo-00310 Cryst. Mp 157.5-158°. [exJn + 18.6° (CHC1 3 /EtOH).

5,6,7,7a-Tetrahydro-4,7-dimethylcyclopenta[c]P.yran-1(4aH)- (1R,2R,3S,l'R)-form (32603-ll-5]
one, 9CI Constit. of oil of catnip. Cryst. Mp 85°.
(1R,2R,3S,l' S)-form [32603-10-4]

~
Constit. of oil of catnip. Cryst. M p 117°.
(1R,2S,3R,l' R)-form [50429-13-5]
(4aS, 7S, 7aR)-form Cryst. Mp 121.5-122°. [exJn -52° (CHC13 /EtOH).
Ho (1R,2S,3R,l' S)-form [50429-10-2]
Cryst. Mp 123.SO. [exJn -39° (CHC1 3/EtOH).
C1ofi140 1 M 166.219 (1R,2S,3S,l' R)-form [32603-12-6]
(4aS,7S,7aR)-form [21651-62-7] Cryst. Mp 115°.
Constit. of Nepeta cataria. Oil. [ex]i: +37° (c, 27 in (1R,2S,3S,l' S)-form [485-06-3]
CHC1 3). Cryst. Mp 111°,
6,7-Didehydro: (66644-99-3]. Gastrolactone Bates, R.B. et al, J. Am. Chem. Soc., 1958, 80, 3420.
C.ofi120 1 M: 164.204 Trave, R. et al, Gazz. Chim. Ita/., 1970, 100, 1061 (synth, struct)
Found in larvae of Gastrophysa cyanea. Oil. [ex]~ Grant, H.G. et al, Aust. J. Chem., 1973, 26, 2183 (synth)
-32.SO. Sakai, T. et al, J. Org. Chem., 1981, 46, 4774 (cmr, synth)
(4aS,7S,7aS)-form [17257-15-7]
Constit. of N. cataria. Oil. [ex]i: -24.4° (c, 6.2 in Nepetaside Mo-00313
CHC1 3). [114076-56-1]
(4aR,7S,7aS)-form [21651-53-6]

GloO-w
Constit. of N. mussini. Oil. Bp0 _1 60°. [ex]~ +81° (c, 0.04
in CHC1 3).
(4aR,7R,7aS)-form [105660-81-9]
Constit. of N. el/iptica. Oil. [ex]i;' -222° (c, 0.84 in
CHC1 3). Ho
(#JR,7S,7aR)-form Cl6H160 8 M 346.377
Constit. of Nepeta nuda. Constit. of Nepeta cataria. Needles (EtOH). Mp 204-205°.
[4581-79-7, 21651-48-9, 108944-20-3] [ex]i;1 -52.5° (c, 0.6 in MeOH).
Achmad, S.A. et al, Proc. Chem. Soc., London, 1963, 166 (synth) Xie, S. eta/, Phytochemistry, 1988, 27, 469.
Eisenbraun, E.J. et al, J. Org. Chem., 1980, 45, 3811 (struct, bib/)
Jones, T.H. eta/, Tetrahedron Lett., 1981, 22, 4373 (Gastrolactone)
Bellesia, F. et al, Phytochemistry, 1984, 23, 83 (biosynth) Nyctanthoside Mo-00314
Bottini, A.T. et al, Phytochemistry, 1987, 26, 1200 (isol) [57575-16-3]
DePooter, H.L. et al, Phytochemistry, 1987, 26, 2311 (isol)

Nepetalic acid
I COOH
Mo-00311
H~~
HOH2 C
10
OGle
OCCHO (1' R)-form
C 17H 160 12 M 422.385
H : Constit. of Nyctanthes arbor-tristis. Resin. [ex]i? --65.1°
C10H 160 3 M 184.235 (MeOH).
(l'R)-form [21651-54-7] 6-0-(3,4-Dihydroxycinnamoyl): [97145-54-5]. Arbortristoside
Constit. of Nepeta cataria. Cryst. (Et20fpet. ether). Mp B
73-75°. C16H 310 15 M 584.530
(1' S)-form [32203-60-4] Constit. of N. arbor-tristis. Powder. [exln -69° (c, 1.66
Oil. in MeOH).
Taylor, W.l. eta/, Cyclopentanoid Terpene Derivs., Marcel Dekker, 10-Deoxy, 6-0-(4-methoxycinnamoyl): [97145-52-3].
1969, 206 (rev) Arbortristoside A
Trave, R. et al, Gazz. Chim. Ita/., 1970, 100, 1061 (synth, struct) C17H 340 13 M 566.558
Eisenbraun, E.J. eta/, J. Org. Chem., 1981, 46, 3302 (isol) Constit. of N. arbor-tristis. Cryst. Mp 226-228°. [exln
-90° (c, 1.16 in MeOH).
Nepetalinic acid Mo-00312 10-Deoxy, 6,7-Di-Ac: [83348-25-8]. Barbatoside
2-Carboxy-ex,3-dimethylcyclopentaneacetic acid, 9CI C11 H 300 13 M 490.460
Constit. of Penstemon barbatus. Cryst. Mp 91-94°.
OOH Rimpler, H. et al, Tetrahedron Lett., 1975, 2423.
2 Junior, P., Planta Med., 1982, 45, 127 (Barbatoside)
COOH Puroshothaman, K.K. et al, Phytochemistry, 1985, 24, 773
H I
(Arbortristosides)
I

C1ofi160 4 M 200.234
(1R,2R,3R,l' R)-form [50429-20-4]
Cryst. Mp 68°. [exJn -36° (CHC1 3/EtOH).
(1R,2R,3R,l' S)-form [50429-18-0]

58
Octahydro-6-hydroxy-7-methyl-1-... - Penstemide Mo-00315 - Mo-00319

Octahydro-6-hydroxy-7-methyl-1- Mo-00315 Gering, B. eta/, J. Nat. Prod. (Lioydia), 1987, 50, 1048
(Patrinalloside)
oxocyclopenta(c)pyran-4-carboxylic acid Xie, S. eta/, J. Nat. Prod. (Lioydia), 1989, 52, 701 (biosynth)

H~H Paulownioside
[81026-61-1]
Mo-00318

C 10H 140 5 M 214.218

Me ester: [23847-82-7].
HO~
H~(
C11H 160 5 M 228.244 HOH2 C OGle
10
Constit. of Jasminum spp. Cryst. (C 6H 6). Mp 103.5-104°.
[oc] 0 +21° (e, 1.3 in CHC1 3). C 15H 240 11 M 380.348
Hart, N.K. eta/, Aust. J. Chern., 1969, 22, 1283. Constit. of Paulownia tomentosa. Amorph. solid. [ex]i;'
-65° (e, 2.5 in MeOH).
10-Cinnamoy/: [73343-11-0]. G/obuhuinin
Paederosidic acid Mo-00316 C24H300 12 M 510.494
(18842-98-3] Constit. of G/obularia alypum. Amorph. [ex]i,O -84.SO (e,
0.64 in MeOH).
Hm~
HCOOH 7-Epimer, 10-cinnamoy/: [73366-19-5]. Globularimin
C24H 300 12 M 510.494
0 Constit. of G. alypum. Amorph. [ex]i,O -106° (e, 0.64 in
MeSCOOH2 H MeOH).
OGle 8-Epimer, 6-0-ex-L-rhamnopyranoside: [89139-30-0].
CtsH240 12S M 464.446 Verbascoside B
Constit. of Paederia scandens. Solid + 2H20. [ex]i: +28.2° CztH34015 M 526.491
(MeOH). Constit. of Verbascum georgicum. Amorph. [ex]~ - 108°
y-Lactone: [20547-45-9]. Paederoside (e, 0.12 in MeOH).
C18H 220 11 S M 446.431 Chaudhuri, R.K. eta/, Helv. Chim. Acta, 1981, 64, 3 (Globu/arinin,
Constit. of P. scandens and P. foetida. Cryst. + 2H 20. Globularimin)
Mp 122-123°. (ex] 0 -195.6° (MeOH). Adriani, C. eta/, J. Nat. Prod. (Lioydia), 1981, 44, 739
(Panlownioside)
y-Lactone, tetra-Ac: Cryst. + 2H 20. Mp 153.5-154°. Arutyunan, L.S. et a/, Khim. Prir. Soedin., 1983, 29, 573
Inouye, H. eta/, Chern. Pharm. Bull., 1969, 17, 1949 (synth) ( Verbascoside B)
Kapadia, G.J. eta/, Tetrahedron Lett., 1979, 1937 (struct)
Penstemide Mo-00319

m
Patrinoside Mo-00317 [62853-37-6]
(53962-20-2]
HCH2 0Gle
HO~OGle 0
HOH2 H
HOH2f6~;cJ__ oocr
C11H 340 11 M 462.493 CztH310 10 M 444.478
Constit. of Patrinia scabiosaefolia. Amorph. Constit. of Penstemon deutus. Antitumour agent. [ex]i,O
-24° (e, 0.9 in MeOH).
I> LZ5901000.
Penta-Ac: [ex]~ -24° (e, 0.7 in MeOH).
8-Epimer: (113349-26-1]. Patrilllll/oside
C11H 340 11 M 462.493 4' -0-P-v-A/lopyranoside: [113332-15-3]. Confertoside
Constit. of Penstemon hirsutus. Powder (CHC1 3jMeOH). C17H4zOts M 606.620
Mp 63°. [ex]i,O -69° (e, 0.64 in MeOH). Constit. of P. confertus. Powder (CHC1 3jMeOH). Mp
100-101°. [ex]i,O -57° (e, 0.147 in MeOH).
8-Epimer, 6' -0-P-v-g/ucopyranoside: [64703-88-4].
Kanokoside D 4' -0-P-v-G/ucopyranoside: [1 09291-58-9]. Penstebioside
C17H 440 16 M 624.635 C17H 420 15 M 606.620
Constit. of Valeriano officina/is root. Amorph., eryst. as Constit. of P. richardsonii. Yellow amorph. powder
nona-Ae. Mp 179-181° (nona-Ae). [ex] 0 -30° (CHC1 3 jMeOH). Mp 84-86°.
(MeOH)(nona-Ae). A gentiobioside. 6' -0-P-v-G/ucopyranoside: [95152-93-5]. Serrulatoside
10-Deoxy, 8,10-didehydro: [95260-25-6]. Serrulatoloside C17H 41 0 15 M 606.620
C11H 310 10 M 444.478 Constit. of P. serrulatus. Cryst. Mp 92-94°.
Constit. of P. serrulatus. Jensen, S.R. eta/, Tetrahedron Lett., 1979, 3261 (struct)
Junior, P. eta/, Planta Med., 1984, 50, 417 (Serru/atoside)
Taguchi, H. eta/, Chern. Pharm. Bull., 1974, 22; 1935; 1979, 27,
Gering, B. et a/, Phytochemistry, 1987, 26, 753, 3011
1275 (isol, cryst struct)
(Penstebioside, Confertoside)
En~o, T. eta/, Chern. Pharm. Bull., 1977, 25, 2140 (Kanokoside D)
Jumor, P., P/anta Med., 1984, 50, 438 (Serru/atoloside)

59
Penstemonoside - Pulchelloside I Mo-00320 - Mo-00326

Penstemonoside Mo-00320 Constit. of P. latifolia. Cryst. Mp 157-159°. (oc]i; +7.2°

(c, 1.2 in MeOH). Stereochem. uncertain.
[81203-56-7]
Chao, P.D.L. et al, J. Nat. Prod. (Lloydia), 1980, 43, 5'71.

H¢15~ Premnoside B Mo-00324

C1,H160 10 M 390.386
! H OGle

Constit. of Penstemon barbatus. Amorph. [oc]~ -140.2° (c,

H~~
~lc
HaC G
0.55 in MeOH). COO OOC
5P-Hydroxy: [81203-55-6]. Penstemoside
C17H160 11 M 406.386
Constit. of P. barbatus. Amorph. [oc]~ -100.0° (c, 0.72
in MeOH).
8-Epimer: Dihydrocornin HO OH
C17H 160 10 M 390.386 C39H 440 19 M 816.765
Constit. of Comus nuttallii and C. .florida. Mp 90-100°. May have the alternative struct. with cinnamoyl residues
Jensen, S.R. et al, Acta Chern. Scand., 1973, 27, 2585. interchanged. Deriv. of Catalpol, Mo-00244. Constit. of
Chaudhuri, R.K. et al, Tetrahedron Lett., 1981, 22, 4061. Premna odorata. Amorph. powder. [ocln + 19.4° (c, 0.38
in MeOH).
Physoside Mo-00321 3n-Me ether: Premnoside D
C40H 460 19 M 830.792

HOm
[125290-14-4] Constit. of P. odorata. Sl. yellow amorph. powder. (ocln
+ 14.0° (c, 0.3 in MeOH).
3"'-Hydroxy: Premnoside A
C39H 440 20 M 832.765

Hoilio 1
OGle
Consit. of P. odorata. Sl. ydlow amorph. powder. [oc]~
+24.8° (c, 0.27 in MeOH).
3"'-Methoxy: Premnoside C
C1sH2401o M 364.349 C40 H 460 20 M 846.791
Constit. of Physostegia virginiana. Cryst. (EtOH). Mp Constit. of P. odorata. Amorph. powder. [ocln + 25.9° (c,
222°. (oc]~ -232° (c, 0.5 in H 20). 0.36 in CHC1 3).
Hexa-Ac: [125357-07-5]. Otsuka, H. et al, Phytochemistry, 1989, 28, 3063 (isol, pmr, cmr)
Cryst. (EtOH). Mp 134-135°. (oc]~ -164° (c, 0.4 in
CHC1 3). Procumboside Mo-00325
Jensen, S.R. et al, Phytochemistry, 1989, 28, 3055 (isol, pmr, cmr) [87686-78-0]

Plagiolactone

4??
Mo-00322
(63808-10-6]

r+Jyo Absolute clsH 220 10 M 362.333

\ HOGle

configuration Constit. of roots of Harpagophytum procumbens.

~0 Hygroscopic powder. [oc]i;1 -112° (c, 0.64 in MeOH).
CIJI120l M 164.204 Kikuchi, T. et al, Chern. Pharm. Bull., 1983, 31, 2296.
Constit. of larvae of Chrysomelid beetles. Oil.
Meinwa1d, J. et al, J. Am. Chern. Soc., 1978, 100, 1883. Pulchelloside I Mo-00326
[67244-49-9]
Posoquenin Mo-00323
[7 5853-66-6]

C17H 160 12 M 422.385

Constit. of Verbena pulchella. Amorph. solid. [oc]~ - 148°
(c, 1 in EtOH).
C 11 H 140 7 M 25!t227
Constit. of Posoqueria latifolia. Cryst. Mp 150-151°. (oc]i; Hexa-Ac: Cryst. Mp 166-169°.
-7.4° (c, 1 in MeOH). 5-Deoxy: 5-DeoxypulcheUoside I
3,4-Dihydro, stereoisomer: [75853-64-4]. Latifonin C17H160 11 M 406.386
C 11H 160 7 M 260.243 Constit. of Citharexylum fruticosum.

60
Randioside - Scandoside Mo-00327 - Mo-00332

Milz, S. eta/, Tetrahedron Lett., 1978, 895 (iso/, struct) Constit. of dried root of Rehmannia glutinosa (Rehmanniae
Bianco, A. eta/, Gazz. Chim. Ita/., 1981, 111, 201 (cmr) Radix). Oil. [a:]~ -51.4° (MeOH).
Ganapaty, S. et a/, Planta Med., 1988, 54, 42 (deriv)
Yoshikawa, M. eta/, Chern. Pharm. Bull., 1986, 34, 1403.

Randioside Mo-00327
Scabroside Mo-00330
[82345-53-7]
[51848-03-4]

C16H 200 10 M 372.328

Constit. of Randia canthioides. Hygroscopic powder. [a:]:;'
-29.4° (c, 0.2 in MeOH).
CtsH2P 1o M 362.333
lP HOGle

Constit. of Deutzia scabra. Cryst. (EtOH). Mp 218-220°.

Tetra-Ac: Cryst. (EtOH). Mp 129-131°. [a:]~ -56.8° (c, [a:]:,S -80.5° (c, 0.5 in MeOH).
0.56 in CHC1 3). Hexa-Ac: Cryst. Mp 209-212°.
Uesato, S. eta/, Phytochemistry, 1982, 21, 353. Esposito, P. et a/, Gazz. Chim. /tal., 1973, 103, 517 (isol)
Bianco, A. eta/, Gazz. Chim. /tal., 1981, 111, 201 (cmr)
Rehmaglutin A Mo-00328
[103744-82-7] Scabrosidol Mo-00331
[88313-36-4]
HO H

H~ID Absolute
configuration
HO-H~
C9H 140 5
HO

M 202.207
Jt)
\ __

C 15H 240 11 M 380.348

~G~c
Constit. of dried root of Rehmannia glutinosa (Rehmanniae
Radix). Cryst. Mp 134-136°. [a:]~ +43.6° (MeOH). Constit. of Deutzia scabra. Arnorph. [a:]i; -109° (c, 1 in
MeOH).
3P-Methoxy: Jioglutin C
C 10H 160 6 M 232.233 Esposito, P. eta/, J. Nat. Prod. (Lloydia), 1983, 46, 614.
Constit. of R. glutinosa. Arnorph. powder. [a:Jn + 58.1 o
(c, 0.89 in MeOH). Scandoside Mo-00332
7-Deoxy, 7a:-chloro: [103744-84-9]. Rehmaglutin D [18842-99-4]

HOIDH
C9H 13C104 M 220.652
Constit. of R. glutinosa. Cryst. Mp 132-133°. [a:]~
+ 60.6° (MeOH).
7-Deoxy, 7a:-chloro, 3P-hydroxy: [103744-83-8].
Rehmaglutin B
C,H 13C105 M 236.651 10 OGle
Constit. of R. glutinosa. Mp 152-153°. [a:]~ + 33.8°
(MeOH). Ct,H220n M 390.343
Constit. of Paederia scandens. Hygroscopic powder. Mp
7-Deoxy, 7a:-chloro, 3P-methoxy: Jioglutin A 139-143°. [a:Ji? -53.3° (H 20).
C 10H 15CI0 5 M 250.678
Me ester: [27530-67-2]. Feretoside
Constit. of R. glutinosa. Amorph. [a:Jn +63.3° (c, 1 in
C17H 240 11 M 404.370
MeOH).
Constit. of Gardenia jasminoides and Feretia
7-Deoxy, 7P-chloro, 3P-methoxy: Jioglutin B apodanthera. Powder. [a:Jt' -56.1° (c, 2.4 in MeOH).
C 10H 15CI05 M 250.678
Me ester, hexa-Ac: Cryst. (EtOH). Mp 134°. [a:Jn -78° (c,
Constit. of R. glutinosa. Arnorph. [a:Jn -63.2° (c, 0.94 in
0.5 in MeOH).
MeOH).
6-Epimer: [14259-55-3]. Deacetylasperulosidic acid
Kitagawa, I. et a/, Chern. Pharm. Bull., 1986, 34, 1399
(Rehmaglutins) C16H 220 11 M 390.343
Morota, T. et a/, Phytochemistry, 1989, 28, 2385 (Jioglutins) Isol. from Rubia peregrina and R. tinctorum. Arnorph.
[a:Ji? +26° (c, 1.7 in MeOH).
6-Epimer, 10-Ac: [25368-11-0]. Asperulosidic acid
Rehmaglutin C Mo-00329
C 18H 240 12 M 432.380
[103744-81-6] Constit. of R. peregrina and R. tinctorum. Arnorph. [a:Ji?

(i}o
+ 13.3° (c, 1.2 in MeOH).
6-Epimer, 10-Ac, Me ester: [14260-99-2]. Daphylloside
Constit. of Daphniphyllum macropodum. Cryst. (MeOH).
Mp 94-98°. [a:]~ + 19.7° (c, 1.42 in Hp).
HOH2C CH20H 6-Deoxy: see Geniposidic acid, Mo-00271
Inoye, H. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1966, 86,
M 200.191 943 (Daphylloside)
Inouye, H. eta/, Chern. Pharm. Bull., 1972, 26, 1305 (biosynth)

61
Semperoside - Specionin Mo-00333 - Mo-00337

Inouye, H~ et a/, Phytochemistry, 1974, 13, 2219 (isol) Shanzhiside Mo-00336

Balleul, A. et a/, Phytochemistry, 1977, 16, 723 (Feretoside) (1-P-v-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-5,7-
Bianco, A. eta/, Gazz. Chim. /tal., 1978, 108, 13 (Asperulosidic
dihydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid, 9CI

Hg)H
acid, Deacetylasperulosidic acid)
[29836-27 -9]
Semperoside Mo-00333
[110344-57-5]
0

OGle HO \ HOGle
C16H 240 11 M 392.359
9 0 Constit. of Gardeniajasminoides. Cryst. Mp 82-90°. [1X] 0
H -81.7° (EtOH).
C16H 240 9 M 360.360 Penta-Ac: Cryst. Mp 111-112°.
Constit. of Gelsemium sempervirens. Cryst. (EtOH). Mp Me ester: [64421-28-9].
179-181°. [1X]i:' +52° (c, 0.3 in MeOH). C17H 260 11 M 406.386
9P-Hydroxy: [110309-28-9]. 9-Hydroxysemperoside Constit. of Mussaenda parvifiora and Salvia digitaloides.
C1 6H 240 10 M 376.360 Powder. [IX]~ -110.8° (c, 0.42 in MeOH).
From G. sempervirens. Cryst. (EtOH). Mp 132-135°. Me ester, 6'-0-P-v-glucosyl: Shanzhisin methyl ester
[1X]i:' + 58° (c, 1.1 in MeOH). gentiobioside
7P-Hydroxy: [113358-20-6]. Vebraside C22 H 360 16 M 556.517
CI6H240 10 M 376.360 Constit. of Canthium subcordatum. Cryst.
Constit. of Verbena brasiliensis. Mp 131-133°. [1X]it (MeOHfCHC1 3). Mp > 150° dec. [1X]i:' -56° (MeOH).
+80.7° (c, 0.195 in CHC1 3). 6-(4-Hydroxy-3,5-dimethoxybenzoyl), 8-Ac, Me ester:
Jensen, S.R. eta/, Phytochemistry, 1987, 26, 1725 (Semperoside) [86450-76-2].
Franke, A. et a/, Phytochemistry, 1987, 26, 3015 (Vebraside) C28H 360 16 M 628.583
Constit. of Chinese drug Bai-Yun-Shen (S. digitaloides).
Serruloside Mo-00334 Powder. [1X]i;' -71.0° (c, 1.01 in MeOH).
8-Ac, Me ester: [57420-46-9]. Barlerin
[95152-92-4]
C19H 280 12 M 448.423
Constit. of Barleria prionitis. Cryst. (EtOAc). Mp 180°.

~~~OCH2 [1X] 0 -8.SO (c, 0.8 in MeOH).

6,8-Di-0-Ac, Me ester: [57420-45-8]. Acetylbarlerin

H6)-(
0 OH
T

H
C21 H 300 13

2.0 in MeOH).
M 490.460
From B. prionitis. Hygroscopic powder. [1X] 0 -99° (c,

6-Ac, Me ester: [110186-13-5]. 6-0-Acetylshanghiside

methyl ester
C19H280 12 M 448.423
Constit. of B. lupulina. Needles (MeOH/EtOAc). Mp
427-228°. [1X]i? -118.7° (c, 0.17 in MeOH).
C21 H 300 10 M 442.462 Inouye, H. eta/, Tetrahedron Lett., 1970, 3581 (isol)
Constit. of Penstemon confertus. Cryst. Mp 61°. Taneja, S.C. et a/, Tetrahedron Lett., 1975, 1995 (Barlerin)
7,81X-Dihydro: [113332-14-2]. Dihydroserruloside Takeda, Y. eta/, Phytochemistry, 1977, 16, 1401 (isol)
C21 H 320 10 M 444.478 Achenbach, H. et a/, Tetrahedron Lett., 1980, 3677 (iso()
Damtoft, S. eta/, Phytochemistry, 1981, 20, 2717 (cmr)
Constit. of P. serrulatus. Yellow amorph. powder. Mp Damtoft, S. et a/, Tetrahedron Lett., 1982, 23, 4155 (isof)
61°. Tanaka, T. eta/, Chern. Pharm. Bull., 1983, 31, 780 (isol)
Junior, P., Planta Med., 1984, SO, 417 (Serruloside) Byrne, L.T. eta/, Aust. J. Chern., 1987, 40, 785 (iso/, cryst struct)
Gering, B. eta/, Phytochemistry, 1987, 26, 3011
(Dihydroserruloside)
Specionin Mo-00337
[96944-53-5]
Sesamoside Mo-00335
[117479-87-5]

H4VO
HO COOMe
HoQcooJ--hoEt
~6
I HI
0 0 HOH2 C OEt
H C20 H 260 8 M 394.421
OGle
lsol. from leaves of Catalpa speciosa. Antifeedant against
C.,H140 11 M 420.369 Eastern spruce budworm.
Constit. of Sesamum angolense. Amorph. powder.
Vander Eycken, E. eta/, Tetrahedron Lett., 1985, 26, 367; 1987,
Penta-Ac: Prisms (CH 2Cl2/Et2 0fhexane). Mp 151-153°. 28, 3519 (isol, synth)
Potterat, 0. eta/, Phytochemistry, 1988, 27, 2677.

62
Stansioside - Suspensoside A Mo-00338 - Mo-00343

Vander Eycken, E. et al, Tetrahedron, 1986, 19, 5385 (synth, Suspensolide A Mo-00341
struct)
Hussain, N. et al, Tetrahedron Lett., 1987, 28, 4871 (synth) [80839-82-3)

Stansioside Mo-00338 AcO~OGlc

[79617-00-8)
HO CHO
AcOH2 c?r1tfc
HO OOC~

C 16H 1•.09 M 360.360

~'
Constit. of Tecoma stans. [IX)~ -124.SO (c, 0.7 in MeOH).
C:z5H380 14 M 562.567
Constit. of Viburnum suspensum. Hygroscopic amorph.
powder. [IX)~ -42.9° (c, 0.35 in MeOH).
Hexa-Ac: Cryst. Mp 108-1UO. [IX]~ -20° (c, 0.50 in
MeOH).
Tetra-Ac: Cryst. (EtOH). Mp 170-171°. [IX)~ -91.7° (c, 0.4
in Me2CO). Aglucone:
C 19Hza09 M 400.425
8-Epimer: [72396-01-1). Yuheinoside. Plantarenaloside Constit. of V. suspensum. Amorph. Mp 87° (as tri-Ac).
C 16H 140 9 M 360.360
Constit. of T. stans and Leucocarpus perfoliatus. Hase, T. eta/, Chern. Lett., 1982, 13.
Amorph. [1X)~ -188.8° (c, 1.2 in MeOH).
8-Epimer, tetra-Ac: Cryst. (EtOH). Mp 186-187°. [IX)~ Suspensolide F Mo-00342
-129.6° (c, 1.4 in Me 2CO).
Ozaki, Y. eta/, Helv. Chim. Acta, 1979, 62, 2708 (Yuheinoside)
Damtoft, S. et al, Phytochemistry, 1981, 20, 2717 (cmr)
Bianco, A. et al, Gazz. Chim. !tal., 1982, 112, 199 (isol, struct)

Stilbericoside Mo-00339
[53852-43-0)
C 11 H 340u M 478.492

2P
Constit. of Viburnum suspensum. Amorph. powder. [1X)n
-25° (c, 0.053 in MeOH).
7-Ac: [126006-64-2). Suspenso/ide D
C 13H 360 13 M 520.530
Constit. of V. suspensum. Amorph. powder. [1X)n -8.9°
OGle (c, 0.083 in MeOH).
C 14Hli,010 M 348.306 10-Ac: [126006-65-3). Suspensolide E
Constit. of Stilbe ericoides. Glass. [IX)~ -61.5° (c, 0.2 in Constit. of V. suspensum. Amorph. powder. [1X)n -42.7°
H 20). (c, 0.107 in MeOH).
6-Epimer: 6-Epistilbericoside Stereoisomer: [64703-86-2). Kanokoside B
Ct4Hzo010 M 348.306 lsol. from valerian root. Mp 110-111° (as hexa-Ac). [1X)n
Constit. of Thunbergia alata. Foam. [IX)~ -67° (c, 0.5 in -27.7° (EtOH)(hexa-Ac). May be identical with
EtOH). Supensolide F or its C-7, C-8 epimer.
6-Epimer, penta-Ac: Cryst. (EtOH). Mp 156-157°. [IX)~ Endo, T. eta/, Chern. Pharm. Bull., 1977, 25, 2140 (isol)
-87° (c, 0.7 in CHCl 3). Iwagawa, T. eta/, Phytochemistry, 1990, 29, 310 (isol, pmr, cmr)
Rimpler, H. eta/, Z. Naturforsch., C, 1974, 29, 368.
Jenson, S.R. et al, Phytochemistry, 1989, 28, 3059 (isol, pmr, cmr) Suspensoside A
8-Hydroxydecapetaloside
Strictoloside Mo-00340 [126006-66-4)
[98619-23-9)

Hw HOH,Cft>
HO COOMe

HO OGle
OGle C 16H 160 9 M 362.376
C 16Hn0u M 406.343 Isol. from leaves of Viburnum suspensum. Amorph.
Constit. of Penstemon strictus. Cryst. Mp 88-91°. powder. [1X)n -73.4° (c, 0.47 in MeOH).
Junior, P., Planta Med., 1985, 229. Penta-Ac: Needles (EtOH). Mp 112-113.9°.
lwagawa, T. eta/, Phytochemistry, 1990, 29, 310 (isol, pmr, cmr)

63
Syringenone - Teucrein Mo-00344 - Mo-00348

Syringenone Mo-00344 Penta-Ac: Cryst. (Et20jpet. ether). Mp 127-129°. [ex]i;'

[58546-53-5] -2.3° (c, 0.6 in CHCI 3).
Takeda, Y. et al, Chern. Pharm. Bull., 1976, 24, 1216.

OwH~pMe
Kobazashi, K. eta/, Chern. Pharm. Bull., 1985, 33, 4228 (biosynth)

~8 0 Tecomoside Mo-00347
[55732-44-0]
H
OGle
HO CHO
C17H 1•.09 M 372.371
lsol. from Syringa vulgaris. Amorph.
7P,8P-Epoxide: [56222-02-7]. Syringoxide
C17H140 10 M 388.371
HO~'
Constit. of S. vulgaris. Amorph.
C16H140 10 M 376.360
Popov, S.S. eta/, Dokl. Bolg. Akad. Nauk, 1975, 28, 1509. Constit. of Tecoma capensis. Amorph. powder. [ex]i;' -118°

p
(c, 2 in MeOH).
Syringopicrogenin A Mo-00345 Penta-Ac: Cryst. (EtOH). Mp 124-125°.
7-(4-Hydroxybenzoyl):
C23 H180u M 496.467

ow
Constit. ofT. capensis. Amorph. powder. [ex]~; -64.7°
(c, 0.1 in MeOH).
7-Cinnamoyl: 7-0-Cinnamoyltecomoside. 5-
Hydroxycampenoside
C15H 34,0u M 506.505
Constit. ofT. capensis and Campsis chinensis. Amorph.
powder, needles (EtOH). Mp 191-192°. [ex]i;' -69.8° (c,
H OH 0.1 in MeOH). The two samples have not been
compared. Mp refers to 5-hydroxycampenoside, opt.
C18H 100 6 M 332.352
Constit. of Syringa reticulata. [ex]~ -75° (c, I in CHCI 3)(as rotn. refers to 7-cinnamoyltecomoside.
di-Ac). 7-(4-Hydroxycinnamoyl):
3n-Hydroxy: Syringopicrogenin B C15H 300u M 522.505
C18H100 7 M 348.352 Constit. ofT. capensis. Amorph. powder. [ex]i;' -64.9°
From S. reticulata. [ex]~ -65.2° (c, 0.5 in CHCI 3)(as tri- (c, 0.1 in MeOH).
Ac). 7-(4-Methoxycinnamoyl):
3'-Methoxy, 3n-hydroxy: Syringopicrogenin C Cl6H3z0u M 536.532
C19Hn08 M 378.378 Constit. ofT. capensis. Amorph. powder. [ex)i; -63.8°
From S. reticulata. [ex]~ -36.3° (c, 0.8 in CHCI 3)(as tri- (c, 0.1 in MeOH).
Ac). 7-Deoxy: see Stansioside, Mo-00338
Bianco, A. et a/, Gazz. Chim. /tal., 1975, 105, 195 (isol)
3n-Hydroxy, 8-0-P-v-glucopyranoside: [107783-23-3]. Damtoft, S. et al, Phytochemistry, 1981, 20, 2717 (struct, cmr)
Syringopicroside B Bianco, A. et al, J. Nat. Prod. (Lioydia), 1983, 46, 314 (isol)
C14H:11,0u M 510.494 Imakura, Y. et al, Phytochemistry, 1984, 23, 2263 (5-
From S. reticulata. Cryst. (as tri-Ac). Mp 76-78° (tri- Hydroxycampenoside)
Ac). [ex]~ -8l.l 0 (c, 2.1 in CHCI3)(tri-Ac).
3'-Methoxy, 3n-hydroxy, 8-0-P-v-glucopyranoside: [107783- Teucrein Mo-00348

s:t;Ok
24-4]. Syringopicroside C [89289-90-7]
C15H 310 13 M 540.520
From S. reticulata. Cryst. (as hexa-Ac). Mp 74-76°
(hexa-Ac). [ex]~ -86.9° (c, 1.7 in CHCI 3)(hexa-Ac).
Kikuchi, M. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1987,
107, 23.

ro
OAc
Tarennoside Mo-00346
[61081-59-2] C14H100 5 M 268.309
Constit. of Teucrium marum. Oil. Bp0 . 5 125-130°. [ex]~
HCHO -73.SO (c, 0.3 in C6H6).
Bellesia, F. et al, J. Chern. Res. (S), 1983, 328.
0
HOH2 H
OGle
C16Hn09 M 358.344
Constit. of Tarenna kotoensis. Amorph. powder. [ex]i;'
+42.1° (c, 1 in MeOH).

64
Teucrium lactone C - Valtrate Mo-00349 - Mo-00355

Teucrium lactone C Mo-00349 Undulatin Mo-00352

Hexahydro-7-methyl-4-methylenecyclopenta[c]pyran-3(1H)-
one, 9CI. Allodolicholactone H

HOH,A?
[60419-55-8]

ct=to
0 ~
H
CtoH140 2 M 166.219
Constit. of Teucrium marum. Oil. [1X]i? + 145.3° (c, 4.5 in OH
C6H6).
Pagnoni, U.M. eta/, Aust. J. Chern., 1976, 29, 1375 (isol)
Callant, P. et al, Tetrahedron Lett., 1983, 24, 5797 (synth)

Teuhircoside Mo-00350
C23 H 280 9
HO
"
M 448.469
Constit. of Tecomella undulata. Cryst. + 1Hz0. Mp 227-
[80 l3 5-40-6] 2280. [1X]i? -177.7° (c, 0.63 in MeOH).
Verma, K.S. eta/, Planta Med., 1986, 359.

Unedoside Mo-00353
[38965-81-0]

C15H 100 9

C21 H:lC,013
M 344.318
Constit. of Teucrium arduini and T. hyrcanicum. Cryst. Mp
213°. [1X]i,l -400.7° (c, 0.08 in MeOH).
5-0-Rhamnoside: [78280-92-9]. Teucardoside
M 490.460
Constit. of T. arduini and T. hircanicum. Amorph. [1X]i,l
C14H 200 9 M 332.307
alP HOGle

Constit. of Arbutus unedo and Stilbe spp. Solid. Mp 232-

-183.SO (c, 0.1 in MeOH). 2340.
Ruhdorfer, J. eta/, Z. Naturforsch., C, 1981, 36, 697.
Penta-Ac: Plates. Mp 168.5-169°.

ro
Geissman, T.A. et al, Tetrahedron Lett., 1966, 1245 (struct)
Theveside Mo-00351 Rimpler, H. et a/, Phytochemistry, 1972, 11, 3096 (isol)
[29781-29-1] Rimpler, H. et al, Z. Naturforsch., C, 1974, 29, 368 (struct)
Weinges, K. et a/, Justus Liebigs Ann. Chern., 1982, 872 (abs
HOCOOH config)

0 Valerosidatum Mo-00354
HOH [29505-31-5]
OGle
C16Hn011 M 390.343
Constit. of Thevetia peruviana. Amorph.
HO~OGlc
Me ester: [23407-76-3]. Theviridoside
C17H 140 11 M 404.370
Constit. ofT. peruviana. Amorph. [1X]n -23° (H20). HO~~
Me ester, penta-Ac: Cryst. Mp 122.8-123.3°. [1X]n -16° C21 H 340 11 M 462.493
(CHC1 3). Constit. of Valeriana spp. Amorph. powder. Mp 78-80°.
Sticher, 0. et al, Helv. Chim. Acta, 1969, 52, 478 (isol) [1X]i? -102° (HzO).
Sticher, 0., Tetrahedron Lett., 1970, 3195 (isol)
Inouye, H. et al, Chern. Pharm. Bull., 1972, 20, 1305 (biosynth) Inouye, H. et al, Tetrahedron, 1974, 30, 2317.

Valtrate Mo-00355
Valepotriate. Valepotriatum. Valtratum
[18296-44-1]

CnH300 8 M 422.474
Constit. of Valeriana spp. Sedative. Oil. [1X]i,l + 172.7°
(MeOH).

65
Vebraside- Villoside Mo-00356 - Mo-00360

I> EK7902000. P-D-Glucoside, tetra-Ac: Cryst. (EtOH aq.). Mp 133.SO.

3'-Acetoxy: [25161-41-5). Acevaltrate, INN. Acevaltratum. Biichi, G. eta/, Tetrahedron, 1962, 18, 1049 (iso/, struct)
Acetoxyvalepotriate Bentley, T.W. eta/, J. Chern. Soc. C, 1967, 2234 (ms)
C24H 320 10 M 480.511 Sakan, T. et a/, Tetrahedron Lett., 1968, 2471 (synth)
Prod. by V. spp. and by Centranthus ruber. Hypnotic, Inouye, H. eta/, Chern. Pharm. Bull., 1972, 20, 1287 (biosynth)
sedative. Needles (hexane). Mp 83-84°. [ex)i;l + 163.7° Bailleal, F. eta/, Phytochemistry, 1977, 16, 723 (cmr)
Callant, P. et a/, Tetrahedron, 1980, 36, 2089 (synth)
(MeOH). One of the 3-methylbutanoyl residues carries Damtoft, S. eta/, J. Chern. Soc., Perkin Trans. 1, 19H3, 1943
an OAc substit. at the 3-posn. (biosynth)
5P,6-Dihydro: Dihydrovaltrate. Didrovaltratum. Damtoft, S. et al, Phytochemistry, 1983, 22, 695; 2614 (biosynth)
Dihydrovalepotriate Jensen, S.R. eta/, Phytochemistry, 1989, 28, 97 (biosynth)
C22H320 8 M 424.490
lsol. from V. spp. Cryst. (EtzOjhexane). Mp 63-64°. Viburnalloside Mo-00358
[exJi? -80°. [96853-48-4)

H?t'vr
Isomer: lsovaltrate. Isovaltratum
C22H 300 8 M 422.474
lsol. from V. edulis. The acyl groups on 0 7 and au are
interchanged.

~CH
Isomer, 5P,6-dihydro: [58560-51-3). lsodihydrovaltrate.
Iodidrovaltratum

A~~
C22H 320 8 M 424.490
lsol. from V. vaginata. [ex)~ -72° (c, 1 in MeOH).
Thies, P.W. et al, Tetrahedron Lett., 1966, 1155, 1163 (5,6-

U8c~
Dihydrovalepotriate)
Thies, P.W. et al, Tetrahedron, 1968, 24, 313; 1973, 29, 3213
(struct)
Verzar-Petri, G. et al, Acta Pharm. Hung., (Suppl.), 1974, 44, 54;
CA, 81, 16644ls (biosynth) C23 H 380 13 M 546.567
Hoelzl, J., Planta Med., 1975, 28, 301 (biosynth) Constit. of Viburnum betulifolium. Syrup. [ex]:,S --86° (c, 1.4
Tittel, G. et al, J. Chromatogr., 1978, 148, 459 (hplc, deriv) in MeOH).
Bock, K. et al, Phytochemistry, 1978, 17, 753 (cmr)
Kucaba, W. et al, Tetrahedron, 1980, 19, 575 (Isodihydrovaltrate) Jensen, S.R. et a/, Phytochemistry, 1985, 24, 487.
Schnieder, G. et al, Arch. Pharm. (Weinheim, Ger.), 1982, 315, 691
(pharmacol) Viburtinal Mo-00359
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1,989, 14008. 4-M ethylcyclopenta[c]pyran-7-carboxaldehyde, 9CI
Khandzbieva, N. eta/, Int. J. Mass Spectrom. Ion Phys., 1983, 48, [63661-79-0)

Q5
181 (m,v)

'W
Vebraside Mo-00356

o----fo
H' OGle C 10H 80 2 M 160.172
Prod. from hydrol. of esters present in Viburnum tinus and
HO V. opulus. Yellow cryst. (HzO). Mp 90-92°.
H 11-Acetoxy: [18234-46-3). Baldrinal
C 12H 100 4 M 218.209
C16H 240 10 M 376.360 Pyrolysis or acid hydrol. prod. from Valtrate, Mo-
Constit. of Verbena brasiliensis. Mp 131-133°. [ex]~ +80.7° 00355. Yellow-brown cryst. (EtzOfpet. ether). Mp 112-
(c, 0.195 in CHC1 3). 1130.
Franke, A. et al, Phytochemistry, 1987, 26, 3015. Thies, P.W., Tetrahedron, 1968, 24, 313 (Baldrinal)
Godeau, R.-P. eta/, Phytochemistry, 1977, 16, 604 (isol, struct, uv)
Verbenalol Mo-00357 Godeau, R.-P. et al, CA, 1979, 90, 183192q (occur)
Brayer, J.-L. eta/, J. Chern. Soc., Chern. Commun., 1983, 257
[479-48-1) (synth)

~~ Villoside Mo-00360

q)OGk
[50276-99-8)

HOH
C 11H 140 3 M 226.229
Aglycone of Verbenalin. Cryst. (EtOAc). Mp 125-128° dec.
[ex]i;l -21° (EtOH).
0-P-D-Glucopyranoside: [548-37-8). Verbena/in.
Ho
Verbenaloside. Cornin C 16H 260 8 M 346.377
C 17H 240 10 M 388.371 Constit. of Patrinia villosa.
lsol. from Verbena officina/is, V. stricta and other V.
spp. and Cornus florida. Cell growth inhibitor. Cryst.
Mp 182.SO. [exln -173° (c, 3.98 in H 20).

66
Virginioside - Allamcin Mo-00361 - Mo-00366

Tetra-Ac: Cryst (EtOH). Mp 112-113°. ClsH 160 7 M 308.287

Taguchi, H. et a/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1973, Constit. of A. neriifolia. Prisms (MeOH). Mp 170-173°.
93,607. [1X]j,8 + 187.SO (c, 0.16 in MeOH).
Kupchan, S.M. et al, J. Org. Chern., 1974, 39, 2477 (isol, struct)
Virginioside Mo-00361 Abe, F. et al, Chern. Pharm. Bull., 1984, 32, 2947 (isol, deriv)
[125290-15-5]
Allamandin Mo-00364

cy-h [51820-82-7]

Hollio
OGle
C 15H 220 10 M 362.333
Constit. of Physostegia virginiana. Amorph. powder. [IX]~
-170° (c, 0.5 in EtOH).
Tetr(l-Ac: [125410-53-9].
Cryst. (EtOH). Mp 203-204°. [1X]i,l -127° (c, 0.9 in
ClsHI,O, M 308.287
CHC1 3).
Constit. of Allamanda cathartica. Antitumour agent. Cryst.
Jensen, S.R. eta[, Phytochemistry, 1989, 28, 3055 (isol, pmr, cmr) (MeOH/EtOAc). Mp 212-2W. [1X]i,l + 15° (c, 0.06 in
MeOH).
Kupchan, S.M. et al, J. Org. Chern., 1974, 39, 2477 (isol)
Trost, B.M. eta/, Tetrahedron Lett., 1985, 26, 1807 (synth)
Parkes, K.E.B. et al, J. Chern. Soc., Perkin Trans. 1, 1988, 1119

10-Alkyliridoids (synth)

Allamcidin B Mo-00365
P-Allamcidin
[93452-24-5]
Allamancin Mo-00362
[93376-05-7]
COOMe

rYrOH
0~()
0~0 C 15H180 7 M 310.303
HO Constit. of Allamanda neriifolia. Prisms (EtOH).
Di-Ac: Cryst. (EtOAcfhexane). Mp 161-163°. [1X)j,8 +38.0°
ClsHia08 M 326.302
(c, 0.30 in CHC1 3).
Constit. of Allamanda neriifolia. Solid. [1X]j,8 + 74.5° (c, 0.80
in CHC1 3). 1-0-P-v-G/ucopyranoside: [93376-12-6].
C21H 280 11 M 472.445
0 3-Me:
Constit. of A. neriifolia. Cryst. powder. Mp 135-138°.
C 16H 200 8 M 340.329
[IX)~ +49.4° (c, 0.75 in MeOH).
Constit. of A. neriifolia. Solid. [1X]j,8 + 112.3° (c, 1.64 in
CHC1 3). 1-Epimer: [93376-06-8]. Alllllncidin A. IX-Allamicidin
ClsH 180 7 M 310.303
Abe, F. et al, Chern. Pharm. Bull., 1984, 32, 2947.
Constit. of A. neriifolia. I sol. as mixt.
Abe, F. et al, Chern. Pharm. Bull., 1984, 32, 2947.
Allamandicin Mo-00363
[51838-83-6)
Allamcin Mo-00366
[93452-23-4]

~:M•
0~
HO'~H
ClsHI,07 M 308.287 C 13H 140 5 M 250.251
Constit. of Allamanda cathartica. Cryst. (Etpjhexane). Constit. of Allamanda neriifolia. Needles (MeOH). Mp
Mp 117-118°. [1X)i,l +293° (c, 0.42 in CHC1 3). 198-2WO dec. [IX]~ +65.6° (c, 0.50 in Py).
11 ,13-Diepimer: [93452-27-8]. Isoalkunandicin Me ether:

67
Allamdin - Plumieride Mo-00367 - Mo-00370

C14H160 5 M 264.277 Albers-Schonberg, G. eta/, Helv. Chim. Acta, 1961, 44, 1447 (isol,
Constit. of A. neriifolia. Needles (MeOH). Mp 138-140°. uv,pmr)
[IX]~ +48.4° (c, 0.29 in MeOH). Kupchan, S.M. et al, J. Org. Chern., 1977, 39, 2477 (isol)
Trost, B.M. et a/, J. Am. Chern. Soc., 1983, 105, 6755 (synth)
Abe, F. et al, Chern. Pharm. Bull., 1984, 32, 2947. Martin, G.E. eta/, J. Org. Chern., 1985, 50, 2383 (prnr)
Parkes, K.E.B. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 1119
Allamdin Mo-00367 (synth)
[51820-84-9]
Plumieride Mo-00370

ow~
Agoniadine
[511-89-7]
H COOMe
O~HOH

C15H 160 6 M 292.288

CH2 CH3

Constit. of Allamanda cathartica. Cryst. (Et20jhexane).

~
LJH OGle
Mp 131-132° dec. [1X]i: -35° (c, 0.46 in CHC13). 6' ):.oH
Kupchan, S.M. et al, J. Org. Chern., 1974, 39, 2477. I!
C2tH26012 M 470.429
Oruwacin Mo-00368 Constit. of Plumeria spp. Cryst. Mp 224-225°. (1X]b' -114°
[70368-12-6] (c, 0.54 in H 20).
13-Ac:
C23H 280 13 M 512.466
Constit. of Allamanda neriifolia. Solid. [1X]b' -· 37.8° (c,
2.07 in MeOH).
13-0-(4-0-P-n-G/ucopyranosy/oxycinnamoyl): [80396-57-2].
0 Protoplumericin A
C36H420 19 M 778.716
Constit. of Allamanda neriifolia. Solid. [1X]i,S -89.9° (c,
1.09 in MeOH).
13-0-(4-0-P-n-G/ucopyranosyloxy-3-hydroxycinnamoyl):
[93343-68-1]. Protoplumericin B
C21 H 180 8 M 398.368 C36H 420 20 M 794.716
Constit. of Morinda Iucida. Cryst. (MeOH). Mp 223°. [1X]i,S Constit. of A. neriifolia. Solid. [1X]b' -61.2° (c. 1.41 in
+ 193° (CHCl3). MeOH).
Adesogan, E.K., Phytochemistry, 1979, 18, 175. 6P.7P-Epoxide: [93343-67-0]. Plumiepoxide
C21H260 13 M 486.429
Plumericin Mo-00369 Constit. of A. neriifolia. Needles (EtOH). Mp 224-225°.
[IX]~ -129.SO (c, 0.28 in MeOH).
[77-16-7]
Albers-Schiinberg, G. eta/, Helv. Chim. Acta, 1961, 44, 1447
(struct)
Yeowell, D.A. eta/, Experientia, 1964, 20, 250 (biosynth)
Yamauchi, T. eta/, Chern. Pharrn. Bull., 1981, 29, 3051 (isol)
Abe, F. eta/, Chern. Pharm. Bull., 1984, 32, 2947 (derivs)

CtsH140, M 290.272
lsol. from Plumeria spp. and from Cliona caribboea. Shows
antibiotic, antifungal and antitumour activity. Platelike
needles (C6H6). Mp 212.5-213.SO sl. dec. [IX]~ + 204°
(CHCl 3). Related to Plumieride, Mo-00370.
(JJZ)-lsomer: [31298-76-7]. /soplumericin
C15H 140 6 M 290.272
lsol. from roots of P. rubra. Cryst. (CH 2Cl2/toluene).
Mp 200.5-201.SO. [1X]i,S +216.4° (c, 1.01 in CHC1 3).
11S,13-Dihydro: P-Dihydroplumericin
C15H 160 6 M 292.288
Isol. from roots of P. rubra. Cryst. (Et20/pentane or by
subl.). Mp 150-151°. [1X]i;1· 5 +275.5° (CHCl 3).
11S,13-Dihydro, parent acid: P-Dihydroplumericinic acid
Ct4Ht40 6 M 278.261
lsol. from roots of P. rubra. Mp 189-190° dec.
Little, J.E. eta/, Arch. Biochem., 1951, 30, 445 (isol)

68
Abelioside B - Foliamenthin Mo-00371 - Mo-00377

Eustomorusside Mo-00374
[74213-77-7]
Secoiridoids
~:
H 0
Abelioside B Mo-00371 R•
[99891-73-3] R2 H 2 C HOGle

H 0 R1 =R2 =0H

~xw
C 16H 240 12 M 408.358
Constit. of Eustoma russellianum and Gentiana campestris.
Powder. [IX]~ -72.3° (c, 1.1 in MeOH).
Uesato, S. et al, Phytochemistry, 1979, 18, 1981.
,~6 Mpondo, E.M. et al, Phytochemistry, 1990, 29, 1687 (isol, pmr,
cmr)
fl OGle
C:zsH360 12 M 528.552 Eustomoside Mo-00375
Constit. of Abelia grandiflora. [74213-75-5]
Penta-Ac: Cryst. (EtOH). Mp 211-213°. [1X]i; -38° (e, 0.5 As Eustomorusside, Mo-00374 with
in CHC13).
7-A/dehyde: [99891-69-7]. Abelioside A R 1,R2 = -0- (epoxide)
C:zsH 340 12 M 526.536 C 16H 22 0 11 M 390.343
From A. grandiflora. Powder. [IX]~ -38° (c, 1.3 in Constit. of Eustoma russellianum and Gentiana campestris.
MeOH). Amorph. powder. [1X]n - 123.2° (c, 1 in MeOH).
7-A/dehyde, Tetra-Ac: Cryst. (EtOH). Mp 170-172°. [1X]i; 5-Deoxy: 5-Desoxyeustomoside
-41 o (e, 0.5 in CHC1 3). C 16H 220 10 M 374.344
Murai, F. eta[, Phytochemistry, 1985, 24, 2329. Constit. of G. campestris.
Uesato, S. et al, Phytochemistry, 1979, 18, 1981.
Cantheyoside Mo-00372 Mpondo, E. eta[, Phytochemistry, 1990, 29, 1687 (isol, pmr, cmr)
[32455-46-2]
Eustoside Mo-00376

OHC::PH~M•
[74213-76-6]
As Eustomorusside, Mo-00374 with
R 1 = OH, R 2 = Cl
=::::,.. OGle C 16H 13Cl011 M 426.804
H Constit. of Eustoma russellianum and Gentiana campestris.
OGle Powder. [1X]i,l -100° (c, l in MeOH).
C 33H 460 19 M 746.715 Uesato, S. eta[, Phytochemistry, 1979, 18, 1981.
Constit. of Cantleya corniculata. Mpondo, E. eta[, Phytochemistry, 1990, 29, 1687 (isol, pmr, cmr)
Octa-Ac: Cryst. (MeOH). Mp 144-145°. [1X]~ -93° (c, 0.5
CHC1 3). Foliamenthin Mo-00377
Sevenet, T. et al, Tetrahedron, 1971, 27, 663. [21848-66-8]

Diderroside Mo-00373 8' 16' 12'

[86989-19-7] HOH,~COOlt(

~~ ~6
HOGle
C 1,H:za0 13 M 464.422 C 26 H 360 12 M 540.563
Constit. of stem bark of Nauclea diderrichi. Amorph. Constit. of Menyanthes trifoliata. Cryst. Mp 194-196°. [1X]n
powder. [1X]n -34.6° (e, 1.16 in MeOH). -63° (MeOH).
0-De-Ac, Me ester: [79916-78-2]. Alpigenoside 2' ,3'-Dihydro (R- ): [22314-48-3]. Dihydrofolitunenthin
C 18H:za0 12 M 436.412 C26H 380 12 M 542.579
Constit. of Lanicera alpigena. Amorph. Constit. of M. trifoliata. Amorph. [1X]n -65° (MeOH).
Bailleu1, F. et al, J. Nat. Prod. (Lloydia), 1981, 44, 573 8'-Deoxy, !:!.?'-isomer, 6'-hydroxy: [19351-64-5]. Menthiafolin
(Alpigenoside) C26H 360 12 M 540.563
Adeoye, A.O. et al, Phytochemistry, 1983, 22, 975 (Diderroside)
Constit. of M. trifoliata. Cryst. Mp 186°. [1X]n -68°
(MeOH).

69
Gentioftavoside - Isoligustroside Mo-00378 - Mo-00383

Loew, P. et al, J. Chem. Soc., Chem. eommun., 1968, 1276 (struct, Grandifloroside Mo-00381
biosynth)
Battersby, A.R. et al, J. Chem. Soc., Chem. Colflmun., 1968, 1277 [61186-24-1]
(derivs)
HO~coo2p
Gentioflavoside Mo-00378 HOV H~H
[34239-17-3]
::::,... 0

~
H
OGk
C25H 34,013 M 538.504
b~b Constit. of Anthocleista grandijlora. Amorph. yellow
powder.
0 Hexa-Ac: Cryst. Mp 118-119°.
C16Hn010 M 374.344 Me ester:
Constit. of Gentiana punctata. CuH310 13 M 552.531
Penta-Ac: Cryst. (EtOH). Mp 126-128°. [1X]i? -108° From A. grandijlora.
(CHC1 3). 3'-Me ether: Methylgrandijloroside
Popov, S.S. eta/, Chem. Ind. (London), 1971, 655. CuHJzOt3 M 552.531
Constit. of A. grandijlora. Amorph.
Mo-00379 3'-Me ether, penta-Ac: Cryst. Mp 89-90°.
Gentiolactone
Chapelle, J.-P., Phytochemistry, 1976, 15, 1305.
[65853-15-8]
Haenkeanoside Mo-00382

0~
[119944-56-8)

b~b 0
C1oflu05 M 212.202
(±)-form
Constit. of Gentiana purpurea. Cryst. (EtOH). Mp ll9-
l20.SO.
Suhr, I.H. et al, Phytochemistry, 1978, 17, 135.

Gentiopicroside Mo-00380
Gentiopicrin C26H 310 13 M 552.531
[20831-76-9) Constit. of lsertia haenkeana.
7-Me ether: [119944-57-9]. 0-Methylhaenkeanoside

(:( Cz,H340 13 M 566.558

Constit. of I. haenkeana.
Z-isomer: [119943-44-1]. /sohllenkeanoside
,~~6 C26H 310 13 M 552.531
Constit. of /. haenkeana.
OGle Z-isomer, 7-Me ether: [119864-05-0]. 0-
Methylisohllenkeanoside
C 16H 100 9 M 356.329
C17H340 13 M 566.558
Widespread in the Gentianaeeae, eg. Swertia and Gentiana
spp. Cryst. Mp 191° (from EtOAc), Mp 122° (from Constit. of /. haenkeana.
H 20). [1X]n -196.3° (Hp). The nat. prods. Erytaurin, [119864-04-9, 119943-43-0, 119943-47-4, 119944-58-0)
Gentiamarin and Sabbatin were said to be identical with Rumbero-Sanchez, A. et al, Heterocycles, 1988, 27, 2863.
Gentiopicroside (Korte, 1954-55). However this work is
unreliable (Tomita 1960). Isoligustroside Mo-00383
Aglucone: Mesogentiogenin [1 08789-18-0]
C1ofl100 4 M 194.187
Oil. ~OH
Tomita, Y., Nippon Kagaku Kaishi (J. Chem. Soc. Jpn.), 1960, 81,
1726 (pmr, struct)
Inouye, H. et a/, Tetrahedron Lett., 1968, 4429 (pmr, struct)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Meo~oc
coo~
Pflanzensto.ffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985
(occur) 0
Das, S. eta/, Phytochemistry, 1984, 23, 908 (isol)
c
C25 H310 11 M 524.521
Constit. of Syringa vulgaris.

70
Isonuezhenide - Jasmolactone A Mo-00384 - Mo-00389

Penta-Ac: [1 08789-15-7]. Jasminint Mo-00387

Cryst. Mp 45-50°. [a]~ -122.7° (e, 1.1 in CHCI3). Jasmine /actonet
Kikuchi, M. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.}, 1987, [30 164-93-3]
107, 245.

Isonuezhenide Mo-00384
[112693-22-8]

dB~
C26H 380 12 M 542.579
Constit. of Jasminum primulinum. Cryst. Mp 159-161°. [IX]~
-245° (e, 1 in EtOH). The name Jasminin has also been

~~:' -. OH
used for an alkaloid.
0-P-D-G/ucopyranoside: Jasminin 10"-0-P-D-glucoside
C32H 480 17 M 704.721
Constit. of J. mesnyi. Needles. Mp 153-154°. [IX]~
-236.7° (e, 0.49 in Py).
Tamikawa, T. et al, Tetrahedron, 1970, 26, 4561 (struct)
OGle Asaka, Y. et a/, Tetrahedron, 1974, 30, 3257 (synth)
Inouye, H. eta/, Chem. Pharm. Bull., 1974, 22, 676 (biosynth)
C32H4.,018 M 716.689 Utaka, M. eta/, Chem. Lett., 1983, 911 (synth)
Constit. of Ligustrum japonicum. Powder. [1X]n -85° (e, Tanahashi, T. eta/, Phytochemistry, 1989, 28, 1413 ~eriv)
1.15 in EtOH).
Fukuyama, Y. et al, Planta Med., 1987, 53, 42?. Jasminoside Mo-00388
[82451-18-1]
Isosweroside Mo-00385
[104777-65-3]
MeOOJ?1
COOH
;v)OG!e ((X)H 2C 0
;=I
Ph OGle
ifl__:)V~ C 26H:li,013 M 550.515
C 16H 220 9 M 358.344 Constit. of Jasminum humile. Cryst. (MeOH). Mp 116.5-
Constit. of Sambucus ebulus. Amorph. [1X]i? + 52.8° (e, 0.97 118.00. [1X]n -194.7° (e, 1 in MeOH).
in MeOH). Inoue, K. eta/, Phytochemistry, 1982, 21, 359.
Gross, G.-A. et al, Helv. Chim. Acta, 1986, 69, 1113.
Jasmolactone A Mo-00389
Jasmesosidic acid Mo-00386 [125339-15-3]

~~Me
I

~ COOH
2,
HO \.__/ CH2COOC:x;~
' ,.9- 0
o"-(tyo
)-CH20H
"· OGle HOOCH2CH20 H OH
C 26H 400 13 M 560.594
C 19H 220 8 M 378.378
Me ester: [97777-70-3]. Jasmesoside
Constit. of Jasminum multiflorum. Pale yellow solid. [1X]i,B
C 27H 420 13 M 574.621
Constit. of Jasminum mesnyi. Powder. [1X]i: -156° (e, + 122.4° (e, 1 in CHCI3).
0.73 in MeOH). 3'-Hydroxy: [125339-16-4]. Jasmolactone B
9"-Hydroxy: 9"-Hydroxyjasmesosidic acid Ct9Hzz09 M 394.377
C 26H 400 14 M 576.594 Constit. of J. multi.florum. Pale yellow gum. [1X]i,B
Constit. of J. mesnyi. Powder. [1X]n -161° (e, 0.65 in + 100.1° (e, 0.1 in MeOH).
MeOH). Shen, Y.-C. et a/, J. Nat. Prod. (Lioydia), 1989, 52, 1060 (isol, pmr,
cmr)
9"-Hydroxy, Me ester: 9"-Hydroxyjasmesoside
C 27H 420 14 M 590.620
Constit. of J. mesnyi. Powder. [ctln -164.9° (e, 0.49 in
MeOH).
Inoue, K. et a/, Phytochemistry, 1985, 24, 1299 (isol, struct)
Tanahashi, T. eta/, Phytochemistry, 1989, 28, 1413 (isol, struct)

71
Jasmolactone C - Morroniside Mo-00390 - Mo-00395

Jasmolactone C Mo-00390 Laciniatoside V Mo-00393

[125339-17-5]

~~
HOH2(:/'-¢~ OH
/ 0
me
[ OGle
C17H 380 14 M 586.589
Constit. of Dipsacus laciniatus. Amorph. [1X]i; --98° (e,
C26H 180 10 M 500.501 0.67 in MeOH).
Constit. of Jasminum multiflorum. Gum. [IX]~ +48.6° (e, 1 1'-0-P-v-Glucopyranoside: [71431-22-6]. Sylvestroside I
in MeOH). C33H 480 19 M 748.731
3'-Hydroxy: [125339-18-6]. Jasmolactone D Constit. of D. sylvestris. Syrup. [1X]i;l -106° (e, 0.4 in
C26H 280 11 M 516.501 EtOH).
Constit. of J. multiflorum. Gum. [IX]~ +28.SO (e, 1 in 1'-0-P-v-Glucopyranoside, 7-Ac: [71431-23-7]. Sylvestroside
MeOH). II
Shen, Y.-C. eta/, J. Nat. Prod. (Lioydia), 1989, 52, 1060 (isol, pmr, C35 H 500 10 M 790.768
cmr) Constit. of D. sylvestris. Foam. [IX]~ -99° (e, 1.5 in
MeOH).
Jasmoside Mo-00391 1'-0-P-v-Glucopyranoside, deca-Ac: Cryst. (EtOH). Mp
[97763-17-2] 154-155°. [IX)~ -85° (e, 0.4 in CHC1 3).
7-Aldehyde: [71431-24-8]. Sylvestroside Ill
CHzOOC COOMe C17H 360 14 M 584.573

--< j)~0 .0
Constit. of D. sylvestris. Foam. [IX]~ -85° (c, 0.4 in
MeOH) .
Jensen, S.R. eta/, Phytochemistry, 1979, 18, 273 (Syll•estrosides)
~c
Podanyi, B. eta/, J. Nat. Prod. (Lioydia), 1989, 52, 135
(Lacinatroside)

Ligustaloside B Mo-00394
u 0 [85527-08-8]

Gle HO~
C43H 61,022 M 928.934
Constit. of Jasminum mesnyi. Powder. [IX]~ -236.4° (e, ~ooc
l
'Q
0.85 in MeOH). COOMe
Inoue, K. eta/, Phytochemistry, 1985, 24, 1299.
/ 0
Kingiside Mo-00392 r
CHO OGle
[25406-67 -1]
Cl!!H310 13 M 540.520
Constit. of Ligustrum japonicum. Powder. [IX]~ --120° (e,
0~Me 0.95 in MeOH).

oyfyo 3' -Hydroxy: [85527-07-7]. Ligustaloside A

Cl!!H310 14 M 556.519
: HOGle Constit. of L. japonicum. Powder. [IX]~ -120.1 o (e, 1 in
MeOH).
C 17H1,,0 11 M 404.370 Inoue, K. eta/, Phytochemistry, 1982, 21, 2305.
Constit. of Lonicera alpigena. Noneryst. [IX]~ -90°
(MeOH).
Tetra-Ac: Mp 165-166°. [1X] 0 -80° (e, I in CHC1 3).
Morroniside Mo-00395
Aglucone: [74848-77-4]. Kingiside aglucone
[61849-88-51
C 11H 140 6 M 242.228
Constit. of Strychnos spinosa. Oil. [IX]~ + 137° (e, 7.5 in HOwH~Me
MeOH). 0 0
6' -(4-Hydroxy-3-methoxybenzoyl): 6'- Vanilloylkingiside
Cl!!H300 14 M 554.504 HOGle
Constit. of Gentiana pyrenaica.
C 17H 260 11 M 406.386
Souzu, I. eta/, Tetrahedron Lett., 1969, 2725 (isol) Constit. of Lonicera morrowii. Amorph. [1X] 0 -72° (e, 1 in
Bailleul, F. eta/, J. Nat. Prod. (Lioydia), 1981, 44, 573 (isol)
EtOH).
Msonthi, J.D. eta/, Phytochemistry, 1985, 24, 771 (isol)
Garcia, J. eta/, Phytochemistry, 1990, 29, 3353 (Vanilloylkingiside)

72
Multitloroside - Oleuropein Mo-00396 - Mo-00401

Penta-Ac: Cryst. Mp 148-151°. [exln -73.5° (c, 0.97 in Oleonuezhenide Mo-00399

CHC1 3). [112693-21-7]

OOCU
Souzu, I. et al, Tetrahedron Lett., 1969, 2725 (isol, struct)
Inouye, H. et al, Tetrahedron Lett., 1971, 4069 (biosynth)

Multifloroside Mo-00396
2C
~Me O~H
Jyo HO ~
I
OH
OGle
ooc~Me
Jy6
C32Hl8016 M 678.643 OGle
Constit. of Jasminum multiflorum. Pale yellow powder. [exln C49H 660 18 M 1103.044
-40.9° (c, 1 in MeOH). Constit. of Ligustrum japonicum. Amorph. powder. [exln
Shen, Y.-C. et al, Phytochemistry, 1990, 29, 2905 (isol, pmr, cmr) +62.3° (c, 0.83 in EtOH).
Fukuyama, Y. eta/, Planta Med., 1987, 53, 427.
Naucledal Mo-00397
4a,5 ,6-Tetrahydro-6-methyl-1-oxo-JH,JH -pyrano[3 ,4- Oleoside Mo-00400
c]pyran-5-carboxaldehyde, 9CI [60539-23-3]
[38965-50-3]
7

--CQ
OHC MeOOC
L,_~OMe

~0
OGle
0
C18H 160 11 M 418.3.97
C10H 120 4 M 196.202 Constit. of Olea europaea. [ex]~ -121° (c, 1 in MeOH).
Constit. of Nauc/ea diderrichi. Unstable syrup. 7-Acid, 7P-v-glucopyranosyl ester: Methyl glucooleoside
Oxime: Cryst. Mp 175-183°. C13H340 16 M 566.512
McLean, S. et al, Can . .t. Chem., 1972, 50, 1496 (isol, ir, ms, pmr, Constit. of Ligustrum japonicum. Powder. [ex]~ -164.7°
uv) (c, 0.51 in MeOH).
Purdy, J. eta/, Can. J. Chem., 1977, 55, 4233 (synth, pmr, abs
config) Garibo1di, P. et al, Phytochemistry, 1986, 25, 865 (0/eoside)
Kuwajima, H. et al, Phytochemistry, 1989, 28, 1409 (deriv)

Neoleuropein Mo-00398 Oleuropein Mo-00401

[108789-16-8]
[32619-42-4]

HO ~OH OH
HO~ I HO~
~ooc
L__ Ao coo : : ,. . OH
_.. ooc~M' Absolute
configuration

~c 10~0
C3zH380 15 M 662.643 OGle
Constit. of Syringa vulgaris. Amorph. [ex]~ -73.5° (c, 0.5
in CHC1 3). C15H31013 M 540.520
Bitter principle of olives, Olea europaea, isol. also from
Kikuchi, M. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1987, Fraxinus japonicus. Cryst. (EtOAc). Mp 89-91°. [ex]~
107, 245. -168° (c, 0.67 in MeOH). Artifact.
Tetra-Ac: Cryst. (EtOH). Mp 58-59°. [exln -62° (c, 1 in
AcOH).
3n -Deoxy: [35897-92-8]. Ligustroside
C15H310 11 M 524.521
Found in Ligustrum obtusifolium. Noncryst. [exln
.-110.7° (c, 1 in EtOH).
10-Hydroxy: [84638-44-8]. 10-Hydroxyo/europein
C15H310 14 M 556.519
Constit. of L.japonicum. Powder. [ex]~ -153.7° (c, 0.38
in MeOH).
10-Acetoxy: 10-Acetoxyo/europein

73
Oleuroside - Secologanol Mo-00402 - Mo-00406

C17H 340 15 M 598.557 SecogaUoside Mo-00404

Constit. of Osmanthus fragrans. Powder. [IX]~ -191° (c, [61774-57-0]
1.1 in MeOH).
10-Acetoxy, 3"-deoxy: [57799-95-8]. 10-Acetoxyligustroside H COOMe
C17H 340 14 M 582.557
Constit. of 0. fragrans. Powder. [IX]~ -143.9° (c, 1 in a o
MeOH).
H
10-Hydroxy, 4'-P-D-glucopyranoside: Muhiroside 1 OGle
C31 H420 19 M 718.661 OH
lsol. from Jasminum multiflorum. Amorph. powder. [oc]n C 17Hu011 M 420.369
-108.6° (c 1 in MeOH). Constit. of Galium album and G. mollugo. Powder. [IX]~
Shasha, B. eta/, J. Org. Chern., 1961, 26, 1948 (isol) -82° (c, 0.2 in EtOH).
Panizzi, L. et a/, Gazz. Chim. Ita/., 1965, 95, 1279 (isol) Penta-Ac: Cryst. (EtOH). Mp 171-172.5°. [oc]~ -73° (c, 0.3
Asaka, Y. eta/, Chem. Lett., 1972, 141 (isol, struct)
Inouye, H. et a/, Chern. Pharm. Bull., 1974, 22, 676 (biosynth)
in CHC1 3).
Inouye, H. eta/, Tetrahedron, 1974, 30, 201 (abs config) Bock, K. et al, Acta Chern. Scand., Ser. B, 1976, 30, 743 (isol,
Inouye, H. eta/, Phytochemistry, 1975, 14, 304 (isol) struct, cmr)
Inouye, H. eta/, Phytochemistry, 1975, 14, 2029 (10- Uesato, S. eta/, Phytochemistry, 1984, 23, 2535 (isol)
Acetoxyoleuropein, 10-Acetoxyligustroside) Uesato, S. et al, Phytochemistry, 1986, 25, 2515 (biosynth)
Inouye, H. eta/, J. Chromatogr., 1976, 118, 201 (ms)
Inoue, K. eta/, Phytochemistry, 1982, 21, 2305 (deriv)
Shen, Y.-C. et al, Phytochemistry, 1990, 29, 2903 (Multiroside)
Secologanin Mo-00405
Loniceroside
[19351-63-4]
Oleuroside Mo-00402
[116383-31-4] H COOMe
OHC~
H00 OH
~0

~oocl{~~r-
HOGle
C17H2o.Oto M 388.371
Constit. of Strychnos nux-vomica, and Lonicera morrowii,
precursor of indole alkaloids. Oil. [oc]n -96° (MeOH).

~c
Tetra-Ac: Cryst. Mp 115-116°. [1X]n -102° (c, I in CHC1 3).
Battersby, A.R. eta/, J. Chern. Soc. C, 1969, 1187 (synth)
Souzu, I. eta/, Tetrahedron Lett., 1970, 191 (isol)
C15H 320 13 M 540.520 Bisset, N.G. eta/, Phytochemistry, 1974, 13, 265 (isol)
Constit. of Olea europaea. Powder. [oc]~ -83.7° (c, 1.03 in Guamaccia, R. et al, J. Am. Chern. Soc., 1974, 96, 7079 (biosynth)
MeOH). Takeda, Y. et a/, Chern. Pharm. Bull., 1976, 24, 79 (biosynth)
Hexa-Ac: Needles (EtOH). Mp 122-123° ,Joe]~ -82.8° (c, 1 Nakane, M. eta/, J. Org. Chern., 1980, 45, 4233 (synrh)
Brown, R.T. et al, J. Chern. Soc., Chern. Cornrnun., 1986, 1818
in CHC1 3). (synth)
Kuwajima, H. eta/, Phytochemistry, 1988, 27, 1757. Inoue, K. eta/, Phytochemistry, 1989, 28, 2971 (biosynth)

Sarracenin Mo-00403 Secologanol Mo-00406

(59653-37-1]
7 H COOMe
HOH2C~

~c
C11H 140 5 M 226.229 C 17H 260 10 M 390.386
Constit. of the insectivorous plant Sarracenia .flava. Cryst. Constit. of Gentiana verna.
Mp 127-128°. [oc]~ -68.8° (CHC13). 7-Ac: 7-Acetylsecologanol
Miles, D.H. et a/, J. Am. Chern. Soc., 1976, 98, 1569 (cryst struct)
C19H 280 11 M 432.424
Gross, P.M. eta/, J. Am. Chern. Soc., 1982, 104, 1132 (synth) Constit. of G. verna.
Tietze, L.-F. eta/, Angew. Chem., Int. Ed. Engl., 1982, 21, 70 7-(2,5-Dihydroxybenzoyl):
(synth) CuH31,013 M 526.493
Takano, S. et a/, Tetrahedron Lett., 1983, 24, 401 (synth) Constit. of G. verna.
Mpondo, E.M. eta/, J. Nat. Prod. (Lioydia), 1989, 52, 1146 (isol,
prnr, cmr)

74
Stryspinolactone - Xylomollin Mo-00407 - Mo-00412

Stryspinolactone Mo-00407 2' -0-(2,3' ,5-Trihydroxybiphenylcarboxylate): Amaroswerin

[81426-88-2] C19H 300 14 M 602.548
lsol. from S. Japonica and Gentiana spp. Highly bitter
principle. [ali? -13° (MeOH).
Koch, M. eta/, Bull. Soc. Chim. Fr., 1964, 403 (pmr)
Inouye, H. et al, Tetrahedron Lett., 1968, 4429 (struct)
Inouye, H. et al, Chern. Pharm. Bull., 1970, 18, 1856, 2043 (isol,
biosynth)
Inoye, H. et a/, Tetrahedron, 1971, 27, 1951 (Amaroswerin)
C 12H 160 7 M 272.254
Constit. of Strychnos spinosa. Cryst. (MeOH). Mp 108- Sylvestroside IV Mo-00410
1100. [71431-25-9]
Adesogan, E.K. et al, Phytochemistry, 1981, 20, 2585.

Sweroside
[14215-86-2]
Mo-00408
OH~,0~
%
0 H

"~ OGle
C17H360 14 M 584.573
Constit. of Dipsacus sylvestris. Foam. [ali? -57° (c, 0.4 in
MeOH).
" OGle Tetra-Ac: Cryst. (EtOH). Mp 137-139°. [a]~ -60° (c, 0.4
C 16H 120 9 M 358.344 in CHCI 3).
Constit. of Swertiajaponica. Powder. [a]~ -236° (Hp).
Jensen, S.R. et al, Phytochemistry, 1979, 18, 273.
2' -0-(3 ,3'-Dihydroxy-2-biphenylcarboxylate): [52811-25-3].
Anuuopanin. Deoxyamarogentin
c~34Pu M 570.549 Vogeloside Mo-00411
Constit. of roots of Gentiana pannonica. Mp 178°. [a]~ [60077-47-6]
-101.25° (c, 0.47 in MeOH).
2' -0-(3,3' ,5-Trihydroxy- 2-biphenylcarboxylate): [21 018-84-
8]. Anuuogentin
M~rx
C19H 3cP13 M 586.548
lsol. from G. sp. and S. japonica. V. bitter substance.
Mp 229-230°. [a]i? -116.6° (MeOH).
4' -0-(2-Hydroxy-3-glucosyloxybenzoyl), 2' ,3' ,6' -tri-Ac:
~~6
OO!c
[53823-10-2]. Trijloroside
C35H 410 20 M 782.705 C 17H 140 10 M 388.371
Constit. of G. triforora var. japonica. Amorph. [ali: Constit. of Anthocleista vogelii. Amorph.
-122.8° (c, 0.52 in MeOH). Chapelle, J.P., Planta Med., 1976, 29, 268.
2'-0-(3-Hydroxybenzoyl), 3'-Ac: [59193-73-6]. Centapicrin
C15H 280u M 520.489 Xylomollin Mo-00412
Constit. of Erythraea centaurium. Cryst. Mp 234-237°.
[61229-34-3]
[ali: -213° (c, 0.5 in Py).
Inoye, H. eta/, Tetrahedron Lett., 1966, 5229; 1967, 3221; 1968,
4429 (isol, biosynth, struct)
Inouye, H. et al, Tetrahedron, 1971, 27, 1951; 1974, 30, 571 owc~~~e
(Amarogentin, Trifloroside)
Wagner, H. et al, Phytochemistry, 1974, 13, 615 (Amaropanin)
0 I
0
Sakina, K. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1976, 96, I H OH
683 ( Centapicrin)
Ikeda, T. eta/, J. Org. Chern., 1984, 49, 2837 (synth) CuH 180 7 M 274.270
Constit. ofthe fruits of Xylocarpus moluccensis. Cryst.
Swertiamarin Mo-00409 (EtOH). Mp 138-139°.
[17388-39-5] Kubo, I. et a/, J. Am. Chern. Soc., 1976, 98, 6704 (isol)
Nakare, M. eta/, J. Am. Chern. Soc., 1978, 100, 7079 (cryst struct)
Whitesell, J.K. et al, J. Org. Chern., 1983, 48, 2511 (synth)
Whitesell, J.K. et al, J. Am. Chern. Soc., 1986, 108, 6802 (synth)

C 16H 120 10 M 374.344

Constit. of Swertia japonica, Anthocleista procera and
Ericostemma litorale. Cryst. (EtOH/CHC1 3/Et20). Mp
110-112°. [aln -127°.

75
1-Acetyl-4-isopropenylcyclopentene- 1,2-Dimethyl-1,3-... Mo-00413 - Mo-00418

Meyer, W.L. eta/, J. Org. Chern., 1967, 32, 1754.

Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1980, 8,

Other Cyclopentane 74.

Campholenic alcohol Mo-00416

monoterpenoids 2,2,3-Trimethyl-3-cyclopentene-1-ethanol. 4-(2-
Hydroxyethyl)-1 ,5,5-trimethylcyclopentene
[1901-38-8]

1-Acetyl-4-isopropenylcyclopentene Mo-00413
1-[4-( 1-Methylethenyl)-1-cyclopenten-1-y~ethanone, 9CI
[2704-76-9]
C 10H 180 M 154.252
Constit. of Juniperus communis. Oil. [1X] 0 -l.SO (c, 8 in
CC14).
Ac:
C12H 200 2 M 196.289
Constit. of J. communis. Oil. [1X] 0 -1 o (c, 8 in CC14).
Aldehyde: 2,2,3- Trimethyl-3-cyclopenten-1-ylacetaldehyde.
CIOH140 M 150.220 Campholenic aldehyde
lsol. from oil of Eucalyptus globulus. Oil. Bp 738 225-225.5°, C10Ht,o M 152.236
Bp1. 5 67-68°. n~· 5 1.4965. Found in J. communis. Pyrolysis prod. of camphor. Oil.
2,4-Dinitrophenylhydrazone: Red plates (EtOH). Mp 178- Bp 10 77°. [IX]~ -3.1° (CC14).
1800. Aldehyde, 3,4-epoxide: [36789-60-3]. 1,2,2-Trimethyl-6-
Semicarbazone: Cryst. (MeOH). Mp 195-196°. oxabicyclo[3 .1.0]hexane-3-acetaldehyde, 9CI.
Schmidt, H., Chern. Ber., 1947, 80, 528, 533 (isol) Epoxycampholenic aldehyde
Wolinsky, J. eta/, J. Am. Chern. Soc., 1960, 82, 636 (struct, synth) CtoHt,Ol M 168.235
Conia, J.M. eta/, Bull. Soc. Chim. Fr., 1964, 1963 (synth, uv, ir, Constit. of J. communis. Oil. Bp 10 101-102°. [IX]~ -0.83°
pmr) (CHC1 3). Assigned trans-config. of epoxide ring relative
Vig, P. eta/, Indian J. Chern., 1968, 6, 564 (synth) to - CH 2CHO group.
Thomas, A.F., Helv. Chim. Acta, 1972, 55, 815.
Adriadysi~lide Mo-00414
[113540-73-1] IX-Campholide Mo-00417
1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octan-2-one
[507-96-0]

C 10H 120 3 M 180.203

Constit. of a Dysidea sp. of the Adriatic Sea. Powder. Mp CIOH1602 M 168.235
76-77°. [1X]~g5 +2.1° (c, 0.625 in MeOH). Cryst. Mp 168.5-171.SO. [1X] 0 -43.0°.
Mancini, I. eta/, Helv. Chim. Acta, 1987, 70, 2011. Hirata, T. et a/, Bull. Chern. Soc. Jpn., 1970, 48, 2588.

co-Camphanic acid Mo-00415 1,2-Dimethyl-1,3-cyclopentanedicarboxylic Mo-00418

4,7,7-Trimethyl-2-oxabicyclo[2.2.1]heptanecarboxylic acid. acid
1-Hydroxy-2,2,3-trimethyl-1 ,3-cyclopentanedicarboxylic acid
lactone
[13429-83-9] v/
x~H
\
(IS,2R,3R)-form

COOH
C9H 140 4 M 186.207
(JS,2R,3R)-form
cis-Santenic acid
C 10H 140 4 M 198.218 Oxidn. prod. of Santenol or Santenone. Cryst. (Hp).
Reagent for asymmetric induction. Mp 170-171°. [1XH;l +38.31° (EtOH).
(+)-form Di-Me ester:
Cryst. (Hp). Mp 200°. [1X] 0 +9.1°. C 11 H 180 4 M 214.261
Cryst. Mp 120-123°.
(-)-form
Cryst. (Hp). Mp 201°. [1X] 0 -9.3°. Anhydride:
C9H 120 3 M 168.192
Cryst. Mp 129-130°.

76
2,2-Dimethyl-1,3-... - 2-Isopropylcyclopentanone Mo-00419 - Mo-00425

(JS,2R,3S)-form Sato, K. et al, J. Org. Chern., 1973, 38, 551 (synth)

trans-Santenic acid Cookson, R.C. et al, J. Chern. Soc., Chern. Cornrnun., 1976, 804
Cryst. (HzO). Mp 129-130°. (synth)
Dianilide:
C21 H 24N 20 2 M 336.433 Eucommiol Mo-00422
Cryst. (EtOH/C 6H 6). Mp 221°. [55930-44-4]
(1 S,2S,3R)-form
OH

Q-·"-rn,OH
cis-Allosantenic acid. lsosantenic acid
Cryst. Mp 151-152°.
(1 S,2S,3S)-form Absolute
trans-Al/osantenic acid configuration
Cryst. Mp 166-167°. HOH2C CHzOH
Alder, K. et al, Chern. Ber., 1956, 89, 2198. ~H 160 4 M 188.223
Constit. of Eucommia ulmoides. Viscous liq. [cx]i,S -30.5°
2,2-Dimethyl-1,3-cyclopentanedicarboxylic Mo-00419 (c, 1.08 in MeOH).
acid Bianco, A. eta/, Tetrahedron, 1974, 30, 4117.

!; \
COOH
(1RS,3RS)-form
Hexahydro-3a,6a-dimethyl-1-oxo-1H-
cyclopenta(c)furan-4-carboxylic acid,
SCI
trans-n-Camphanic acid
[31230-36-1]
Mo-0042~

C,H140 4 M 186.207

HOOC~o
(JRS,3RS)-form
(±)-trans-form
Cryst. (HzO). Mp 190-191°.
(JRS,3SR)-form
cis-form 0
Cryst. (HzO). Mp 204°. CIOHI404 M 198.218
Anhydride: Not stereoisomeric with "cis-n-Camphanic acid" (see
C,H 120 3 M 168.192 Hexahydro-3a,4-dimethyl-1-oxo-1H-cyclopenta[c]furan-
Cryst. (EtOH). Mp 178°. 4-carboxylic acid, Mo-00424). Cryst. (EtOAcfpentane).
Beckmann, S. et al, Justus Liebigs Ann. Chern., 1951, 574, 65 Mp 167°. [cxli? +9.85°.
(synth) Breinne, M.-J. et al, Tetrahedron, l970, 26, 5087 (synth)
Adhaya, R.N. et al, J. Chern. Soc., 1956, 358 (synth) Hudson, D.W. et al, J. Chern. Soc., Chern. Cornrnun., 1972, 647
(cryst struct)
3,4-Dimethyl-1,2-cyclopentanedione, 9CI Mo-00420
2-Hydroxy-3,4-dimethyl-2-cyclopenten-1-one Hexahydro-3a,4-dimethyl-1-oxo-1H-
[13494-06-9] cyclopenta( c)furan-4-carboxylic acid,
SCI Mo-00424

~0
cis-n-Camphanic acid
[31147-45-2]

C7H 100 2 M 126.155

Constit. of coffee. Mp 71-72°.
Gianturco, M.A. et al, Tetrahedron, 1963, 19, 2039, 2051 (isol,
synth, struct)
CIOH1404 M 198.218
Not stereoisomeric with "trans-n-Camphanic acid" (see
3,5-Dimetbyl-1,2-cyclopentanedione, 9CI Mo-00421 Hexahydro-3a,6a-dimethy1-1-oxo-1H-cycl,openta[c]furan-
2-Hydroxy-3,5-dimethyl-2-cyclopenten-1-one, 9CI 4-carboxylic acid, Mo-00423). Cryst. (MeOH). Mp
[13494-07-0] 234°. [ex]~ +47.7° (c, 4 in EtOH).
Brienne, M.-J. et al, Tetrahedron, 1970, 26, 5087.

~0 2-Isopropylcyclopentanone, SCI
2-(1-M ethylethyl)cyclopentanone, 9CI
[14845-55-7]
Mo-00425

C7HI002 M 126.155
Constit. of coffee. Flavouring agent. Mp 91-92°.
Gianturco, M.A. et al, Tetrahedron, 1963, 19, 2039, 2051 (isol,
synth, struct)

M 126.198

77
3-lsopropyl-2-cyclopenten-1-one - 3-lsopropyl-1-methylcyclopentanol Mo-00426 - Mo-00431

Constit. of Japanese mint oil from Mentha arvensis. Oil 2-Isopropylidene-5-methylcyclopentanone Mo-00428
with strong ethereal odour. Bp 175°. 2-Methyl-5-(1-methylethylidene)cyc/opentanone, 9CI.
Semicarbazone: [40564-33-8]. Camphorone
Mp 189.4°. [6784-16-3]
Oxime:
C.H15NO M 141.213
Mp 42.5°.
2,4-Dinitropheny/hydrazone: Mp 154°.
Onogaki, T., CA, 1963; 59, 3780 (isol, synth)
Marr, D.H. eta/, Can. J. Chern., 1967, 45, 225 (cmr)
~H 140 M 138.209
ljirna, A. eta/, Chern. Pharm. Bull., 1973, 21, 215 (synth) (±)-form [56326-33-1]
Larcheveque, M. eta/, J. Organomet. Chern., 1975, ff7, 25 (synth) Liq. Bp20 90°.
Semicarbazone: Mp 197°.
3-Isopropyl-2-cyclopenten-1-one, SCI Mo-00426 2,4-Dinitropheny/hydrazone: [31089-19-7].
3-(1-Methylethy/)-2-cyc/openten-1-one, 9CI Mp 203°.
[1619-28-9] Ca1as, R., Compt. Rend. Hebd. Seances Acad. Sci., 1937, 204, 984,
1374 (synth)
Naves, Y.R. eta/, Bull. Soc. Chim. Fr., 1957, 1213 (synth)
Vig, O.P. eta/, J. Sci. Ind. Res., Sect. B, 1962, 21, 345 (synth, uv)

3-Isopropyl-1-methyl-1- Mo-00429
cyclopentanecarboxylic acid
Fencho/ic acid. Dihydro-P-fencholenic acid
C 8H 120 M 124.182 [512-77-6]
Used in perfumery and also as a flavouring agent for
· tobacco. Yellow oil with a spicy, aromatic odour. Sol.
pentane. Bp3 75-76°. Steam-volatile.
Semicarbazone: Plates (EtOH or H20). Mp 180-181°.
Crombie, L. eta/, J. Chern. Soc., 1964, 5640 (synth)
Fanta, W.l. eta/, J. Org. Chern., 1968, 33, 1656 (synth)
Fense1au, C. et a/, J. Am. Chern. Soc., 1969, 91, 112 (ms)
Rohela, L.C. et a/, Indian J. Chern., Sect. B, 1978, 16, 435 (synth) C 10H 180 2 M 170.251
(JS.JR)-form
3-lsopropylidene-1-methyl-1- Mo-00427 Cryst. Mp 18-19°. Bp 255-259°. [1X]n +2.3°.
cyclopentanecarboxylic acid (lR.JS)-form
1-Methyf.3-(1-methy/ethy/idene)cyclopentanecarboxylic acid, Cryst. Mp 16-18°. Bp 13 144-145°. [1X]~ -3.66°.
9CI. P-Fencholenic acid Humbert, F. eta/, Bull. Soc. Chim. Fr., 1966, 2867.

q_H
[6750-42-1]
2-Isopropyl-5-methylcyclopentanol Mo-00430
2-Methy/-5-(1-methy/ethy/)cyc/opentano/, 9CI

(1R,2R,5R)-form

Ct.,H 160 2 M 168.235 c,H,8o M 142.241

(+)-form Liq. Bp 185-192°, Bp 15 82°. ni; ~ 1.4501.
Cryst. (ligroin). Sol. EtOH, Et20, spar. sol. C6H6,
(1R,2R,5R)-form
AcOH. Mp 72-73°. Bp 12 140.5-141.SO. [IX]~ +25.85°
Cryst. (pentanejEtp). Mp 40-41°. [1XJ;~8 + 12.7° (c, 2.0
(Et20). in dioxane).
Me ester:
(1 S,2S,5S)-form
C 11H 180 2 M 182.262
Mp 40°. [1Xms -15.3°.
Oil. Bp 97-99°.
Calas, R., Bull. Soc. Chim. Fr., 1939, 6, 1374, 1382 (synth, derivs)
Amide: Varech, D. eta/, Bull. Soc. Chim. Fr., 1965, 1662 (synth)
C 1.,H 17NO M 167.250 Sisido, S. eta/, J. Org. Chern., 1966, 31, 2795 (synth)
Cryst. Sol. EtOH, Etp. Mp 86.5-87.SO.
(±)-form 3-Isopropyl-1-methylcyclopentanol Mo-00431
Amide: Cryst. Mp 87-88°. 1-Methy/-3-( 1-methylethy/)cyc/opentano/
Semmler, F.W., Ber., 1906, 39, 2851. C 9H180 M 142.241
Tarbell, D.S. et a/, J. Am. Chern. Soc., 1958, 80, 1963.
(-)-form
Cryst. Mp 76°. Bp 185-187°. Subl. in needles.
(±)-form
Cryst. Mp 43-44°. Bp 185-186°. Subl. in needles.
Wallach, 0. eta/, Justus Liebigs Ann. Chern., 1912, 388, 49 (synth)

78
2-lsopropyl-2-methylcyclopentanone ... - P.,Necrodol Mo-00432- Mo-00437

2-Isopropyl-2-methylcyclopentanone, SCI Mo-00432 (R)-form

2-Methy/-2-(methylethyl)cyc/opentanone, 9CI Oil. Bp 135-136°. [ali? + 76.48° (neat).
[32116-65-7] (±)-form
Oil. Bp 138-139°.
Nitrosochloride: 1-Ch/oro-1-isopropy/-3-methy/-2-
nitrosocyc/opentane
Cryst. Mp 74-75°.
Wallach, 0. et al, Justus Liebigs Ann. Chern., 1903, 327, 125
C,H160 M 140.225 (synth)
Sisido, K. et al, J. Org. Chern., 1966, 31, 2795 (synth)
Oil. Bp45 97 .SO. Ohloff, G. et al, Tetrahedron, 1966, 22, 309 (synth)
Semicarbazone: Mp 170-172°.
Comubert, R. et al, Bull. Soc. Chirn. Fr., 1930, 47, 958 (synth) 4-Isopropyl-1-methylcyclopentene Mo-00435
Larcheveque, M. et a[, Cornpt. Rend. Hebd. Seances Acad. Sci.
Sect. C, 1975, 280, 309 (synth)
Apofenchene
Larcheveque, M. et al, J. Organornet. Chern., 1975, frT, 25 (synth)

2-Isopropyl-5-methylcyclopentanone Mo-00433
2-Methy/-5-( 1-methy/ethyl)cyc/opentanone, 9CI.
Dihydropu/egenone. Dihydrocamphorone
[6784-18-5]
C9H 16 M 124.225
(S)-form
(2R,5R)-form Oil. Bp 139-140°. [cxJn + 53°.
Absolute Nitrosochloride: Cryst. (CHC1 3). Mp 115°. [a]bS -272°
configuration (CHC1 3).
C,H 160 M 140.225 Wallach, 0., Justus Liebigs Ann. Chern., 1911, 379, 182 (synth)
Oil. Sol. C6H6, Etp. Bp 184-185°. Varech, D. et al, Bull. Soc. Chirn. Fr., 1965, 1662 (synth)
Oxime:
C,H 17NO M 155.239 2-Isopropyl-5-methyl-2-cyclopenten-1-one, Mo-00436
Cryst. Mp 71-72°. SCI
Semicarbazone: Cryst. (EtOH). Mp 209°. Two forms 5-Methyl- 2-( 1-methylethy/)-2-cyc/openten-1-one, 9CI.
known. Pulegenone
2,4-Dinitropheny/hydrazone: Cryst. (EtOH). Mp 170-171.5°. [5587-79-1]
(2R,5R)-form
Oil. [ahs +60.4° (c, 0.5 in MeOH).
(2S,5S)-form
(-)-cis-form
Oil. [ahs -75.2° (c, 0.5 in MeOH).
(2RS,5RS)-form [10499-69-1] c,H 1P M 138.209
(±)-cis-form Found in citronella and peppermint oils. Useful raw
Oil. Bp 179.7°. material in the manuf. of perfumes. Oil. Bp 188.5-189°.
Semicarbazone: Cryst. (EtOH). Mp 198°. Oxime:
C,H15NO M 153.224
(2RS,5SR)-form [10499-68-0] Oil. Bp 237-242°.
(±)-trans-form
Oil. Bp 179.8°. Oxime, 0-benzoyl: Cryst. (MeOH). Mp 104-105°.
Semicarbazone: Microcryst. Mp 198-200° (209°). Semicarbazone: Cryst. (MeOH). Mp 183-184°.
2,4-Dinitropheny/hydrazone: Orange needles (ligroin). Mp Wallach, 0. et al, Justus Liebigs Ann. Chern., 1919, 418, 36 (synth)
Vig, O.P. et al, Indian J. Chern., 1963, 1, 365 (synth)
176-178°. Conia, J.M. et al, Bull. Soc. Chirn. Fr., 1970, 2972 (ir, prnr, uv)
Wallach, 0., Justus Liebigs Ann. Chern., 1918, 414, 296 (synth) Saxena, A.K. et al, Indian Perfum., (1-B), 1976, 20, I (isol)
Cookson, R.C. et al, Tetrahedron, 1963, 19, 1995 (synth)
Varech, D. et al, Bull. Soc. Chirn. Fr., 1965, 1662 (synth)
Caine, D. et al, J. Org. Chern., 1973, 38, 3663 (synth) jl-Necrodol Mo-00437
Kulkarni, B.S. et al, Org. Prep. Proced. Int., 1978, 10, 73. 2,2,3-Trimethyl-4-methylenecyc/opentanemethanol
[104086-70-6]
1-Isopropyl-3-methylcyclopentene Mo-00434
3-Methy/-1-(J-methy/ethyl)cyclopentene, 9CI. Pulegene
[5112-02-7]

M 124.225
0 \
(R)-form
C10H 180 M 154.252
Constit. of the defensive secretion of a carrion beetle. Oil.
[cxln -18.05° (c, 1.59 in CHC1 3).
114 •5-Isomer: rx.-Necrodol
C 10H 180 M 154.252

79
1,2,2,3-Tetramethylcyclopentanecarbo •.. - 1,2,2-Trimethyl-1,3-... Mo-00438 - Mo-00443

Constit. of the defence spray of the carrion beetle. Oil. 1,2,3-Trimethylcyclopentanecarboxylic Mo-00441

crH
[104113-51-1, 125276-85-9, 125276-88-2] acid
Jacobs, R. et a/, Tetrahedron Lett., 1983, 24, 2441 (isol)
Oppolzer, W. et al, Helv. Chim. Acta, 1986, 69, 1817 (synth)
Eisner, T. eta/, J. Chern. Ecol., 1986, 12, 1407 (isol)
Schulte-E1te, K.H. eta/, Helv. Chim. Acta, 1989, 72, 1158 (synth,
bib/)

1,2,2,3-Tetramethylcyclopentanecarboxylic Mo-00438 C.,Ht,02 M 156.224

acid (+)-form
Campholic acid Laurolanic acid
[464-88-0] Bp!OO 178°. [1X]i;· 5 + 1.74°.
Amide:
(1R, 3S)-form C,H 17NO M 155.239
,_A,COOH Absolute Mp 50-51°.
Lr configuration Noyes, W.A. eta/, J. Am. Chern. Soc., 1912, 34, 174 (synth)

CtoHtsOz M 170.251
2,2,3-Trimethylcyclopentanecarboxylic Mo-00442
(1 R,3S)-form
Cryst. (Hp). Mp 106°. Bp 255°. [IX]~ +49.8° (EtOH).
acid, SCI
pK. 5.6. [36394-20-4]
(JS,3R)-form
Prisms. Mp 106-107°. Bp 250°. [IX)~ -49.1° (EtOH).
(1RS,3SR)-form
Cryst. Mp 109°.
Briene, M.-J. eta/, Tetrahedron, 1970, 26, 5087.
C9H 160 1 M 156.224
1,2,3,3-Tetramethylcyclopentene Mo-00439 (+)-form
Campholene Lauronic acid. Camphoceanic acid
[65378-75-8] Oil. [1X]i;1 + 36.5° (pet. ether).
Amide:
C9H 17NO M 155.239
Plates (pet. ether). Mp 86.SO. [1X]i;' +21.2° (pet. ether).
(±)-form
Norisocampho/ic acid
Liq. Bp 12 130°.
C,H16 M 124.225
Constit. of oil of Cinnamomum kanahirai. Bp 134-135°. N-Ethylamide: Cryst. (Et20). Mp 68-69°.
Naito, T., Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1943, 64, Noyes, W.A., J. Am. Chern. Soc., 1912, 34, 1067 (synth)
1024 (isol) v. Braun, J. et al, Ber., 1928, 61, 2276 (synth)

1,2,4-Trimethylcyclopentane, 9CI Mo-00440 1,2,2-Trimethyl-1,3- Mo-00443

[2815-58-9] cyclopentanedicarboxylic acid
(1R,3R)-form
<(H3 HOO~~~COOH
~-CH3
c.oHI,o4 M 200.234
H3~
(lcx,2cx,4~)-form
I> Irritant, orally toxic.
C.H16 M 112.214 (JR,3R)-form [595-32-4]
Two stereoisomers characterised. Occurs in petroleum. (- )-/socamphoric acid
Cryst. (EtOH aq.). Mp 173°. [1X]n -48° (EtOH).
(lrx.,2rx.,4f/)-form [4850-28-6]
d 20 0.763. Bp 116.8°. ~ 1.4185. (JR,JS)-form [124-83-4]
(+)-Camphoric acid
(lrx.,2P,4rx.)-form [16883-48-0] Cryst. (EtOH aq.). Mp 187°. [1X]n +47.7° (EtOH). pK.
d 20 0.746. Bp 109.2°. n~ 1.4101.
4.65 (25°), pK. 4.85 (25°).
Zelinsky, N.D., Bull. Soc. Chim. Fr., 1904, 32, 747.
Anhydride:
· Chiurdoglu, G. et al, Bull. Soc. Chim. Be/g., 1950, 59, 140.
Birch, S.F. eta/, J. Chern. Soc., 1951, 1493. C10H 140 3 M 182.219
Nazarov, N., Izv. Akad. Nauk SSSR, Ser. Khim., 1951, 295; CA, Bp >270°. [1X]n -7.7° (C6H 6).
46, 915. Imide: 1,8,8-Trimethy/-3-azabicyc/o[J .2.l]octane-2,4-dione.
Bazhu1in, P.A. eta/, CA, 1955, 49, 10866 (synth, raman) Camphorimide
Adams, J.Q. eta/, Prepr.-Am. Chern. Soc., Div. Pet. Chern., 1972, C10H 15N02 M 181.234
17, C4 (cmr) Needles (AcOH aq.). Sol. hot H 20. Mp 248°. Bp 300°.
Go1ovkina, L.S. et al, Izv. Akad. Nauk SSSR, Ser. Khim., 1979,
73; CA, 90, 151183 (ms)
[1X]ii + 1.6° (CHC1 3). Subl. above 120°.

80
2,2,3-Trimethyl-3-... - 2,3,3-Trimethyl-1-cyclopentene-1-... Mo-00444- Mo-00447

1-[1-(4-Methylphenyl)ethylj ester: [115-66-2]. Tocamphyl, 2,2,3-Trimethyl-3-cyclopentene-1- Mo-00446

INN. Bilagen. Biliphorin. Gallogen. Hepasynthyl. carboxylic acid
Hepatoxane. Licarbin. Lymethol. Syncurna. Syntabil. a-Campholytic acid
Synthobilin
C 19H 260 4 M 318.412
Choleretic drug. Administered as diethanolamine salt.
(1S,3R)-form
(-)-Camphoric acid
Cryst. (EtOH aq.). Mp 187°. [cxJii -48° (EtOH).
Anhydride: Cryst. (EtOH). Mp 223.SO. C9H 1P 2 M 154.208
(1S,3S)-form (+)-form
( + )-Isocamphoric acid Oil. [cx]i,6 +66.4°.
Cryst. (EtOH aq.). Mp 171-172°. [cxln -47.6° (EtOH (-)-form [33877-35-9]
aq.). Oil. Bp 240-243°. [ex]~ -60.4°.
(JRS,3SR)-form (±)-form
(±)-Camphoric acid Cryst. Mp 40.SO. Bp45 162-164°.
Anhydride: [7216-27-5]. Me ester:
Cryst. (EtOH), rhombohedra. Mp 226°. C 10H 160 2 M 168.235
Imide: Needles (Hp). Mp 249° (245°). Oil. Bp 200°.
Perkin, W.H. et a/, J. Chern. Soc., 1906, 89, 795 (anhydrides) Amide:
Evans, W.C. eta/, J. Chern. Soc., 1910, 97, 2237 (imide) C9H 15NO M 153.224
Toivonen, N.J. eta/, Acta Chern. Scand., 1948, 2, 597 (anhydrides) Leaflets (Hp). Mp 103°.
Gunter, M.J. eta/, J. Pharmacol. Exp. Ther., 1950, 99, 465
(Tocamphyl) Nitrile:
Takahashi, T. eta/, Yakugaku Zasshi (J. Pharm. Sac. Jpn.), 1964, C 9H 13N M 135.208
84, 911; CA, 62, 4055 (imide) Oil. Bp 200-205°.
Baker, K.M. et a/, Tetrahedron, 1968, 24, 1663 (pmr) Bessiere-Chretian, Y. et a/, Compt. Rend. Hebd. Seances Acad. Sci.
Brienne, M.-J. et a/, Tetrahedron, 1970, 26, 5087 (abs config) Sect. C, 1971, 273, 272.
Filippo, J.S. eta/, J. Org. Chern., 1976, 41, 1077 (synth)
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 3750 (Tocamphyl) 2,3,3-Trimethyl-1-cyclopentene-1- Mo-00447
Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed., carboxylic acid
Van Nostrand-Reinhold, 1979, 466. P-Campholytic acid. Isolauronolic acid. Isolaurolenic acid
[5587-63-3]
2,2,3-Trimethyl-3-cyclopenteneacetic acid Mo-00444
a-Campholenic acid

(R)-form
C,H 140 2 M 154.208
Cryst. Mp 135°. Bp 255-256°.
CIOHI602 M 168.235 Me ester:
(R)-form [28973-89-9] CIOHI602 M 168.235
Oil. Bp 15 149-150°. [cxln +8.8° (neat). Oil. Bp 203-204°.
(±)-form Shive, B. et a/, J. Am. Chern. Soc., 1940, 62, 2744.
dA5 1.009. Bp40 169°. n:,S 1.4746.
Suga, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1972, 258 (synth)
Teresa, J.-P. et a/, An. Quim., 1973, 69, 217 (synth)
Gream, G.E. eta/, Aust. J. Chern., 1974, 27, 567 (synth)

1,2,3-Trimethyl-2-cyclopentene-1- Mo-00445
carboxylic acid
Laurolenic acid

{(H
[10333-98-9]

C9H 140 2 M 154.208

(R)-form
Cryst. Mp 13°. Bp1. 5 75-80°. [alii' + 155° (c, 0.64 in
CHC1 3).
Meyer, W.L. eta/, J. Org. Chern., 1967, 32, 1754 (synth)
Snatzke, G. et a/, Helv. Chim. Acta, 1968, 51, 986 (abs config)

81
3-Amino-p-menthane - Bottrospicatol Mo-00448 - Mo-00450

B,HCI: Cryst. (ligroin). Sol. most org. solvents. Mp 184-

1850.
Menthanes N-Ac: Needles (EtzO/ligroin). Mp 160-161°.
N-Formyl: Prisms (Et20jligroin). Sol. org solvs.; more sol.
than (+)-form. Mp 86°.
(/ RS,3RS,4SR)-form [20706-70-1]
(±)-Menthylamine
3-Amino-p-menthane Mo-00448 Bp7 70°. Steam-volatile.
5-Methyl-2-(1-methylethyl)cyc/ohexanamine, 9Cl. 2- B,HCI: Needles (MeOHjMe 2CO). Mp >250°.
/sopropyl-5-methylcyc/ohexylamine
N-Benzoyl:
[21411-81-4] C 17H 25NO M 259.391
Prisms (MeOH). Mp 145-146°.
Read, J., Chern. Rev., 1930, 7, I (rev)
(1R,3R,4R)-form Feltkamp, H. eta/, Justus Liebigs Ann. Chern., 1967, 707, 78,87
(synth, pmr)
O~amoto, K. et al, Bull. Chern. Soc. Jpn., 1968, 41, 1426 (resoln)
King, J.P. et al, Can. J. Chern., 1973, 51, 3914 (resoln)
Smith, H.E. eta/, J. Org. Chern., 1974, 39, 2309 (resoln)
C 10H 21 N M 155.283 Demially, G. eta/, Tetrahedron Lett., 1977, 1885 (synth)
Fir!, J. eta/, Justus Liebigs Ann. Chern., 1978, 87 (cmr)
(IR,3R,4R)-form [16934-77-3]
(+ )-Neoisomenthylamine
Bp 14.5 89o. [1X]:i +9° (CHC1 3). Ascaridole Mo-00449
B,HCI: Needles (Me 2CO/MeOH). Mp >250°. [1X]:i +20.9° 1-Methyl-4-( 1-methylethyl)-2,3-dioxabicyclo[2 .2.2]oct-5-ene,
(HzO). 9CI. 1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]hept-2-ene. 1,4-
Epidioxy-p-menth-2-ene. Kebal II. Uncinacina. Ascapurin.
N-Benzoyl: [16934-78-4].
Ascarisin
Needles (EtOH). Mp 151°. [1X]:i -10.4° (CHC1 3),
[512-85-6]
(JR,3R,4S)-form [2216-54-8]
(- )-Menthylamine
BP12 80°. [IX]~ -34.2°.
B,HCI: Needles (HzO). Mp >280°. [1X]n -36.6° (HzO).
3,5-Dinitrobenzoyl: Deep-yellow cryst. Mp 193°. [1X]!,7·5
-60°.
(IS,3S,4R)-form [20706-69-8]
( + )-Menthylamine c.oHI602 M 168.235
+ 15.5° (homogeneous).
[1X]~ 26 Main constit. of oil of Chenopodium spp. Also said to be
Benzylidene: [63764-99-8].
the major constit. of oil of Peurrzus boldus. Anthelmintic.
Cryst. (hexane). Mp 70-72°. [1X]n -132.SO (CHC1 3). Oil. d~0 1.010. Mp 3.3°. Bp 15 115°, Bp0 .2 39-40°.
Unstable.
(IR,3S,4R)-form [4894-99-9]
t> Explodes on heating or on treatment with acids. Highly
(+ )-/somenthylamine toxic. OT0175000.
Bp13. 5 87o. [1X]i,5 + 29.0°.
N-Formyl: Beckett, A.H. eta/, J. Pharm. Pharmacal., 1955, 7, 55 (purifn)
Swern, D. et al, Anal. Chern., 1969, 41, 412 (pmr)
C 11H 21 NO M 183.293 Bernhard, R.A. et al, Phytochemistry, 1971, 10, 177 (isol)
Mp 45-46°. Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)
N-Benzoyl: [16934-76-2]. Haynes, R.K., Aust. J. Chern., 1978, 31, 131 (synth)
Mp 97-98°. Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 761.
(1S,3R,4S)-form Masilamani, D. eta/, J. Org. Chern., 1983, 48, 4918 (svnth)
(- )-Isomenthylamine Zagorski, M.G. eta/, J. Org. Chern., 1985, 50, 4484 (c:mr, 0-17
N-Benzoyl: Mp 121°. nmr)
(1 S,3R,4R)-form Sax, N.l., Dangerous Properties of Industrial Materials, 6th Ed.,
(- )-Neomenthylamine Van Nostrand-Reinhold, 1984, 325.
[IX]~-26 -37° (c, 2.0 in CHC13).
N-Formyl: Cryst. (EtOH). Mp 116-117°. [IX]~ -53.6° Bottrospicatol Mo-00450
(CHC1 3). 4,7-Dimethyl-6-oxabicyclo[3.2.1]oct-3-ene-7-methanol, 9CI.
6,8-Epoxy-p-menth-1-en-9-ol
(IR,3S,4S)-form [7231-40-5]
( + )-Neomenthylamine [84453-40-7]

Q;o
Bp 13 84°. [1X]i,O + 15.73° (CHC1 3).
B,HCI: Prisms Qigroin). Mp 189°. [1X]:i +2l.SO (H 20).
N~Ac: [881-28-7].
C 12H 23NO M 197.320 Absolute
Mp 169-170°. [1X]:i +53° in CHC1 3• configuration
N-Benzylidene: Mp 45-46°. [1X]:i +61.7° in CHC1 3• ' CH20H
(JRS,3RS,4RS)-form [23399-21-5] M 168.235
( ± )-Neomenthylamine

82
9,10-Cyclo-p-menthane-2,4-diol - 2,5-Dihydroxy-4-isopropylbenzyl ... Mo-00451 - Mo-00457

Produced by microbial transformation of carveol by 2,3-Dihydro-2-hydroxy-6-methyl-3- Mo-00455

Streptomyces bottropensis. Oil. [oc]~ +63.7° (c, 0.056 in methylenebenzofuran
CHC1 3). 2,3-Dihydro-6-methy/-3-methy/ene-2-benzofuranol, 9CI, 8CI.
Nishimura, H. et al, Agric. Bioi. Chern., 1983, 47, 2697. 3,8-Epoxy-p-mentha-1 ,3,5 ,8( JO)tetraen-9-o/
[31722-11-9]
9,10-Cyclo-p-menthane-2,4-diol Mo-00451

H,Co:;$-~OH
1-Cyc/opropy/-4-methy/-1 ,3-cyc/ohexanedio/, 9CI
[83133-21-5]
(R)-fo'm

HO,q
I

C10H 100 1 M 162.188

(R)-form [28330-05-4]

JaH
Absolute
configuration From roots of various He/enium spp. Mp 74-76°.
(±)-form [26414-11-9]
Me ether: Bp0. 5 105-110°.
C1Jl180 1 M 170.251 Bohlmann, F. et al, Tetrahedron Lett., 1969, 4703 (isol, pmr, uv,
struct)
Constit. of Pistacia vera. Oil. [ocln + 21° (c, 1.2 in CHC1 3). Divakar, K.J., Indian J. Chern., Sect. B, 1977, 15, 849 (synth)
Mangoni, L. eta/, Phytochemistry, 1982, 21, 811.
3,10-Dihydroxy-5,11-dielmenthadiene-4,9- Mo-00456
9,10-Cyclo-p-menth-1-en-4-ol Mo-00452 elione
1-Cyc/opropy/-4-methyl-3-cyc/ohexen-1-ol, 9Cl
[106623-23-8]

C 10H 160 M 152.236

C10H 180 4 M 332.439
(S)-form [83133-20-4] Constit. of Callitris mac/eayana. Cryst. (heptane). Mp 149-
Constit. of Pistacia vera. 1500. [oc]i? +55.1° (c, 0.55 in CHC1 3).
Monaco, P. eta/, Phytochemistry, 1982, 21, 2408 (isol) Carman, R.M. et al, Aust. J. Chern., 1986, 39, 1843; 1987, 40, 333
Mangoni, L. et al, Phytochemistry, 1982, 21, 811 (synth) (isol, cryst struct, synth)

Cymbodiacetal Mo-00453 2,5-Dihydroxy-4-isopropylbenzyl alcohol Mo-00457

[111534-64-6] 2-(Hydroxymethyl)-5-(1-methy/ethyl)-1 ,4-benzenediol. p-

_0$0--t.
Cymene-2,5,7-trio/, 8CI. p-Mentha-1,3,5-triene-2,5,7-trio/

~r HO 0

C10H 380 4 M 334.455

Constit. of the essential oil of Cymbopogon martini. Cryst.
(CHC1 3). Mp 206-207°. [<X]i,S +26° (c, 0.12 in CHC1 3). CIOH1403 M 182.219
Menthane numbering shown.
Bottini, A.T. et al, Phytochemistry, 1987, 26, 2301 (isol, cryst
struct) 2,5-Di-Me ether, 7-(2-methylpropanoyl): [34272-56-5].
c.,HzP4 M 280.363
Constit. of the root of Inula salicifolia. Oil. Bp0 . 1 95-
1,2:3,4-Diepoxy-p-menth-8-ene Mo-00454 1050.
1,2:3,4-Bisepoxy-p-menth-8-ene
Anthonsen, T. et al, Acta Chern. Scand., 1971, 25, 390.
[120749-18-0]

C 10H 140 1 M 166.219

Constit. of parsley leaves (Petrose/inum crispum).
Nitz, S. eta/, Phytochemistry, 1989, 28, 3051 (isol, pmr, ms, ir)

83
3,6-Dihydroxy-p-mentha-3,6-diene-... - 8,9-Epoxy-3,10-dihydroxy-p-mentha-... Mo-00458 - Mo-00464

3,6-Dihydroxy-p-mentha-3,6-diene-2,5- Mo-00458 C 15H 110 4 M 266.336

dione Constit. of Blumea wightiana. Oil.
2,5-Dihydroxy-3-methyl-6-(1-methy/ethyl)-2,5- 7-Et ether: [72247-75-7].
cyc/ohexadiene-1 ,4-dione. 2,5-Dihydroxy-3-isopropy/-6- C 12H 200 3 M 212.288
methy/-1 ,4-benzoquinone. 3,6-Dihydroxythymoquinone Constit. of B. wightiana. Oil. Bp0_1 150°. [1X]~4 + 59.3° (c,
[2654-70-8] 4.7 in CHC13).

oAoH
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1062.

HOyo 1,4-Epidioxy-p-mentha-2,8-diene
[120749-17-9]
Mo-00462

C 10H 120 4 M 196.202

lsol. from heartwood of Juniperus chinensis. Red needles
(EtOH aq.). Mp 223-224°. .
Pilo, C. eta/, Acta Chern. Scand., 1960, 14, 353 (isol)
Joseph-Nathan, P. eta/, Org. Magn. Reson., 1981, 15, 311 (cmr)
C 10H 1P 1 M 166.219
Constit. of parsley leaves (Petroselinum crispum).
1,2-Dihydroxy-p-menth-3-en-5-one Mo-00459 Nitz, S. eta/, Phytochemistry, 1989, 28, 3051 (isol, pmr, ms, ir)
4,5-Dihydroxy-5-methy/-2-(1-methy/ethyl)-2-cyc/ohexen-1-
one, 9CI. 4,5-Dihydroxy-2-isopropy/-5-methy/-2-cyc/ohexen-

2
1-one 3,6-Epidioxy-p-menth-1-ene Mo-00463
5-Methyl-7-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene,
[87441-65-4]
9CI. Phellandrene 3,6-endoperoxide

e
0H [5951-54-2]
HO

0
(3cx,4cx,6cx}:form
I

C 1.,H1,03 M 184.235
Constit. of Calea hispida. Oil. [1X]n + 10° (c, 0.1 in CHC13). A
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2899. C10H 160 1 M 168.235
(3«,4«,6«)-form [61616-16-8]
1,3-Dihydroxy-p-menth-3-en-2-one Mo-00460 Constit. of Chenopodium multifidum. Oil. [1X]n -23° (c,
2,6-Dihydroxy-6-methy/-3-( 1-methy/ethyl)-2-cyc/ohexen-1- 1.46 in CHC1 3).
one, 9CI (3P,4«,6/1)-form [61616-15-7]
[57125-34-5] Constit. of Ca/lilepis /aureola and Chenopodium
multifidum. Oil. [1X]n -45.SO (c, 1.38 in CHC1 3).
De Pascual Teresa, J. eta/, Phytochemistry, 1981, 20, 163 (isol)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 139 (isol)

8,9-Epoxy-3,10-dihydroxy-p-mentha-1,3,5- Mo-00464
trien-7-al

C 1.,H1,03 M 184.235
Constit. of Buchu leaf oil.
Kaiser, R. et a/, J. Agric. Food Chern., 1975, 23, 943 (isol)

5,7-Dihydroxy-p-menth-1(6)-en-2-one Mo-00461
4-Hydroxy-2-(hydroxymethyl)-5-(1-methy/ethyl)-2-
cyc/ohexen-1-one. 4-Hydroxy-2-hydroxymethy/-5-isopropy/- C 10H 100 4 M 194.187
2-cyc/ohexen-1-one 3-0-(2-M ethylpropanoyl), 10-0-cinnamoy/: [1 04900-62-l].
Areo/al
C23H 220 6 M 394.423
Constit. of Pipotrix areolare. Oil.
Hernandez, J.D. eta/, Phytochemistry, 1986, 25, 1743.

C 10H 160 3 M 184.235

(4R* ,5R*)-form
5, 7-Dihydroxycarvotanacetone
7-Tig/oy/: [72247-76-8].

84
3,9-Epoxy-p-mentha-1,4(8)-diene - 1,4-Epoxy-p-menthane-2,3-diol Mo-00465 - Mo-00469

3,9-Epoxy-p-mentha-1,4(8~diene
2,4,5,7a-Tetrahydro-3,6-dimethylbenzofuran, 9CI. Linden
ether
Mo-00465 Isol. from Laurus nobilis oil and from the opisthonotal
gland secretion of the mite Caloglyphus rodriguezi. Oil.
Bp40 78-80°. [tx)~ -53° (c, 3 in EtOH). Props. refer to
synthetic material. Opt. rotn. and abs. config. of nat.
isolates not reported.

~0
3-0xo: [101221-23-2]. 1,3,3-Trimethyl-2-
oxabicyclo[2.2.2)octan-2-one, 9CI. 3-0xo-1,8-cineole
cloH1,0 2 M 168.235
Constit. of Peaeonia a/biflora flowers.
[58264-16-7, 63025-72-9, 66113-06-2]
C1.,H 140 M 150.220 Coxen, J.M. et al, Chern. Ind. (London), 1968, 652 (synth)
Isol. from Tilia cordata (linden). Achilladelis, B. et al, Phytochemistry, 1968, 7, 1317 (biosynth)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
[125811-37-2] Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
Blank, I. et al, Z. Lebensm.- Unters. Forsch., 1989, 189, 426 (isol) no. 570 (occur)
Blank, I. et al, Helv. Chim. Acta, 1990, 73, 1250 (struct, pmr) Hogg, J.W. et al, Phytochemistry, 1974, 13, 868 (isol,
dehydrocineole)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
1,4-Epoxy-p-menthane, SCI Mo-00466 Bondavalli, F. et al, J. Chern. Soc., Perkin Trans. 1, 1977, 430;
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane, 9CI. 1978, 804 (synth)
1-Isopropyl-4-methylbicyclo[2.2.1]heptane. 1,4-Cineole. Orsini, F. et al, Gazz. Chim. Ita/., 1980, 110, 553 (biosynth)
lsocineo/e Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
[470-67-7] Pharmaceutical Press, London, 1982/1989, 4629.
Ayorinde, F.O. et al, Tetrahedron Lett., 1984, 25, 3525 (isol, synth,
Dehydrocineole)
Kumar, N. et al, Phytochemistry, 1986, 25, 250 (3-0xocineole)

6,8-Epoxy-p-mentbane Mo-00468
4, 7, 7- Trimethyl-6-oxabicyclo[3 .2.1]octane. Dihydropinol
[5718-77-4]
C1.,H180 M 154.252
Constit. of Alpinia speciosa, Juniperus spp., Polygonum
hydropiper, Artemisia spp., Shorea meranti wood, Piper
cubeba and Cannabis sativa oil. d20 0.90. Bp 173-174°.
n~ 1.4470.
2-Hydroxy: 1,4-Epoxy-p-menthan- 2-o/. 2- Hydroxy-l ,4- C10H 180 M 154.252
cineo/e Minor constit. of caraway oil.
C 10H 180 2 M 170.251
[55822-05-4]
Constit. of Ferula jaeschkeana. Cryst. Mp 75°.
Stereochem. not detd. Schmidt, H., Ber., 1955, 88, 453.
Siemieniuk, A. et al, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1974,
Wallach, 0., Justus Liebigs Ann. Chern., 1907, 356, 197 (isol, 22, 1009.
struct)
Austerweil, M.G., Bull. Soc. Chim. Fr., 1929, 45, 862 (synth)
Naves, Y.R. et al, Bull. Soc. Chim. Fr., 1950, 673 (isol) 1,4-Epoxy-p-meiltbane-2,3-diol Mo-00469
Matsubara, Y. et al, Nippon Kagaku Zasshi (Jpn. J. Chern.), 1970, 1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane-2,3-diol.
91, 762; CA, 73, 120762a (isol, purifn) Mullilam diol
Takahashi, H. et al, Chern. Lett., 1979, 373 (synth, pmr)
[6790-83-6]

JroH
Garg, S.N. et al, Phytochemistry, 1989, 28, 634 (deriv)

1,8-Epoxy-p-menthane Mo-00467

):'OH
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, 9CI. 1 ,8-Cineole.
Eucalyptol. Eucapur. Soledum. Terpane. Zineol. Cineole.
Cyneol. Cajeputol
[470-82-6]
C10H 180 3 M 186.250
Constit. oflhe essential oil of Zanthoxylum rhetsa. Cryst.
(EtOH). Mp 172°.
Mathur, R.K. et al, Tetrahedron, 1967, 23, 2495.

CtoH180 M 154.252
Occurs in eucalyptus, lavender and many other oils.
Inhalational expectorant (vet. use); used in perfumery
and flavour industries. Antiseptic. Oil with
camphoraceous odour. Mp l.SO. Bp 176-177°. n~ 1.455.
t> OS9275000.
2,3-Didehydro: [92760-25-3]. Dehydro-1,8-cineole
C 10H 160 M 152.236

85
1,2-Epoxy-p-menthan-3-one - 6,8-Epoxy-p-menth-2-ene Mo-00470 - Mo-00475

1,2-Epoxy-p-menthan-3-one, SCI Mo-00470 Ct,HuOs M 334.411

6-M ethy/-3-( J-methylethyl)-7-oxabicyc/o[4 .l.O]heptan-2-one, Constit. of roots of G. aristata. Oil. Bp 0 .005 130°.
9CI. 2,3-Epoxy-6-isopropy/-3-methy/cyc/ohexanone. Bohlmann, F. eta/, Chern. Ber., 1969, 102, 864.
Piperitone oxide
[5286-38-4] 9,10-Epoxy-p-mentha-1,3,5-triene-2,5,9- Mo-00473
triol

C10H 160 1 M 168.235

Stereochem. not clear. Isol. from ,Mentha sy/vestris oil and
other essential oils. Cryst. (hexane). d~~ 1.01. Mp 14.5- C10H 110 4 M 196.202
15.50. [IX]~ -177.0° (c, 0.96 in EtOH). ni? 1.4624. Poss.
identical with Dihydrolippione. 2-Me ether, 5,9-bis(2-methylpropanoyl): [68776-56-7].
C19H 160 6 M 350.411
Semicarbazone: Cryst. Mp 199-200°. [1X]n +213° (c, 0.29 in
Constit. of Porophyllum riedelii. Oil.
95% EtOH aq.).
2-Me ether, 5,9-ditig/oy/: [87667-74-1].
2,4-Dinitropheny/hydrazone: Cryst. Mp 115-117°.
C11H 160 6 M 374.433
[4713-37-5, 4713-38-6, 5056-09-7, 20303-83-7, 57130-28-6, 103476- From P. riedelii. Oil.
50-2)
2-Me ether, 5-(2-methy/propanoy/), 9-tigloyl: [87667-75-2].
Reitsema, R.H. et a/, J. Am. Chern. Soc., 1956, 78, 3792 (isol) C20H 160 6 M 362.422
Nigam, I.C. et al, Can. J. Chern., 1963, 41, 1535 (occur)
From P. riedelii. Oil.
Klein, E. et al, Tetrahedron, 1963, 19, 1091 (synth)
Gacs-Baitz, E. et al, Org. Magn. Reson., 1984, 22, 738 (pmr, cmr) 2-Me ether, 5-tigloyl, 9-(2-methylpropanoy/): [87667-76-3].
C20 H160 6 M 362.422
From P. riedelii. Oil.
4,8-Epoxy-p-menthan-3-one Mo-00471
2-Me ether, 5-tigloyl, 9-Ac: [82425-41-0].

A
CtaH210 6 M 334.368
Constit. of Mikania purpurascens. Gum.
(IR,4R)-form Bohlmann, F. et al, Phytochemistry, 1982, 21, 705; 1983, 22, 1035.

~0 4,8-Epoxy-p-menth-1-ene Mo-00474
[4584-23-0]
C 10H 160 1 M 168.235
Isol. from Mentha arvensis.
(1R,4R)-form [7599-90-8]
Cryst. (pet. ether). Mp 54-55°. [1X]i? -18.8° (c, 2.4 in
EtOH).
(1R,4S)-form [7599-91-9]
Cryst. (pet. ether). Mp 59°. [1X]i? +46.6° (c, 0.3 in
MeOH). C10H 160 M 152.236
[13902-36-8) lsol. from Zanthoxylum piperitum.
von Rudloff, E. et al, Can. J. Chern., 1966, 44, 2015 (isol) Sakai, T. eta/, Bull. Chern. Soc. Jpn., 1968, 41, 1945 (isol)
Katsuhara, J., J. Org. Chern., 1967, 32, 797 (synth, abs config)
6,8-Epoxy-p-menth-2-ene Mo-00475
8,9-Epoxy-p-mentha-1,3,5-triene-3,7-diol Mo-00472 4,7,7-Trimethyl-6-oxabicyc/o[3.2.J]oct-2-ene
4-(1 ,2-Epoxy-1-methylethy/)-3-hydroxybenzyl alcohol, 8CI [52812-45-0]

C 10H 160 M 152.236

lsol. from Laurus nobilis.
Hogg, J.W. et al, Phytochemistry, 1974, 13, 868 (isol, ms, pmr)
C10H 110 3 M 180.203
Bis(2-methylpropanoyl): [22571-39-7].
CtaH140 5 M 320.385
Constit. of roots of Gaillardia aristata and Helenium
spp. Oil. Bp0 _005 130°. [1XU~8 -74° (c, 1. 75 in Et20).
3-(2-Methy/propanoy/), 7-(2-methy/butanoy/): [22571-40-0].

86
1,2-Epoxy-p-menth-4(8)-en-3-one - 2-Hydroxy-4-isopropylbenzyl alcohol Mo-00476 - Mo-00481

1,2-Epoxy-p-menth-4(8)-en-3-one Mo-00476 (R)-form [529-63-5]

6-M ethyl-3-(1-methylethylidene)-7-oxabicyclo[4 .1.0]heptan-2- Constit. of Evodia hortensis. Cryst. (MeOH). Mp 74-75°.
one, 9CI. 2,3-Epoxy-6-isopropylidene-3- [IX]~ -59.8° (EtOH).
methylcyclohexanone. Rotundifolone. Piperitenone oxide 6ft-Hydroxy: Desacetylcalaminthone

y
[5945-46-0] C 10H 120 3 M 180.203
Constit. of Calamintha ashei. Cryst. (CHC1 3). Mp 102-
1030. [IX]~ + 37.SO (c, 0.012 in MeOH).
Absolute 6ft-Acetoxy: [113412-11-6]. Calaminthone
Configuration C12H 140 4 M 222.240
0 Constit. of C. ashei. Oil.
(±)-form [30557-66-5]
Mp 72-73°.
CIOH1402 M 166.219 Stetter, H. eta/, Chern. Ber., 1960, 93, 603.
Constit. of Mentha rotundifolia and other M. spp. Cryst. Miyashita, M. et at, J. Org. Chern., 1980, 45, 2945 (synth)
Mp 27.5°. Bp1 86°. [1X]~ + 166.SO (MeOH). Masaki, Y. eta/, Chern. Lett., 1981, 1283 (synth, abs config)
[5056-08-6, 35178-55-3] Juo, R.-R. eta/, J. Org. Chern., 1985, 50, 700 (synth)
Tanrisever, N. eta/, Phytochemistry, 1988, 27, 2523 (Calaminthone)
Shimizu, S. eta/, Agric. Bioi. Chern., 1966, 30, 89. Srikrishna, A. eta/, Indian J. Chern., Sect. B, 1989, 28, 852 (synth)
Macias, F.A. eta/, Phytochemistry, 1989, 28, 79
1,6-Epoxy-p-menth-8-en-2-one Mo-00477 (Desacetylcalaminthone)
2,3-Epoxy-5-isopropenyl-2-methylcyclohexanone. Carvone
oxide 2-Hydroxy-4-isopropylbenzaldehyde Mo-00480
[35178-55-3] 2-Hydroxy-4-(1-methylethyl)benzaldehyde, 9CI. 4-
Isopropylsalicylaldehyde, 8CI. 2-Hydroxy-p-mentha-1 ,3,5-

0~
trien-7-al. Macropone

CIOH1402 M 166.219 C 10H 120 2 M 164.204

Constit. of Catasetum maculatum fragrance. Oil. [1X]i? -44° Isol. from oil of Eucalyptus cneorifolia and Thujopsis
(c, 0.002 in hexane). dolabrata. Oil. Bp2 108°. n~4 1.5480.
Lindquist, N. eta/, Phytochemistry, 1985, 24, 863. Semicarbazone: Mp 214°.
2,4-Dinitrophenylhyrazone: Red needles. Mp 251°.
Evodone Mo-00479 Birch, A.J. eta/, Aust. J. Chern., 1953, 6, 369.
6, 7- Dihydro-3,6-dimethyl-4(5H)-benzofuranone, 9C1. 5,9- Yoshikoshi, A., Nippon Kagaku Zasshi (Jpn. J. Chern.), 1960, 81,
Epoxy-p-mentha-4,8-dien-3-one, 8CI 981; CA, 56, 6104 (isol)

2-Hydroxy-4-isopropylbenzyl alcohol Mo-00481

2-Hydroxy-4-(1-methylethyl)benzenemethanol. p-Mentha-
1,3,5-triene-2,7-diol. p-Cymene-2,7-diol

M 164.204

CIOH!Pl M 166.219
2-Me ether: [3556-84-1]. 4-Isopropyl-2-methoxybenzyl
alcohol. 2-Methoxy-4-(1-methylethyl)benzenemethanol. 2-
Methoxy-p-cymen-7-ol. 2-Methoxy-p-mentha-1,3,5-trien-
7-ol
C 11 H 160 2 M 180.246
d~0 1.04. Mp 29-30°. Bp0 . 15 91.SO.
Thomas, A.F., Helv. Chim. Acta, 1965, 48, 1057 (synth)
Bourgeois, G. eta/, Bull. Soc. Chim. Fr., 1972, 4324.

87
3-Hydroxy-4-isopropylbenzyl alcohol... - 1-Hydroxy-p-menthan-3-one Mo-00482 - Mo-00488

3-Hydroxy-4-isopropylbenzyl alcohol, SCI Mo-00482 Reitsema, R.H., J. Am. Chem. Soc., 1956, 78, 5022; 1957, 79, 4465
3-Hydroxy-4-(1-methylethyl)benzenemethanol, 9Cl. 5- (isol, synth)
Naves, Y.-R., Helv. Chim. Acta, 1966, 49, 2012 (struct, pmr)
(Hydroxymethyl)-2-isopropylphenol. p- M entha-1 ,3,5-triene-
Nagell, A. et al, Phytochemistry, 1972, 11, 3359 (struct)
3,7-diol. p-Cymene-3,7-diol
[77311-68-3]
2-Hydroxy-p-mentha-1,8-dien-6-one Mo-00485
3-Hydroxy-2-methyl-5-(1,-methylethenyl)-2-cyclohexen-1-one.
6-Hydroxycarvone
[51200-86-3]

C 10H 140 1 M 166.219

Bis(2-methylpropanoyl):
CtaH160 4 M 306.401
Obt. from roots of Gaillardia aristata. Oil. Bp0.005 120°.
3-Me ether: [66498-33-7]. 4-/sopropyl-3-methoxybenzyl C 10H 140 1 M 166.219
alcohol. 3-Methoxy-4-(1-methylethyl)benzenemethanol, lsol. from spearmint oil.
9Cl. 3-Methoxy-p-cymen-7-ol, 8Cl. 3-Methoxy-p-mentha- Tsuneya, T. et al, Koryo, 1973, 23 (synth, isol)
1,3,5-trien-7-ol
C 11H 160 1 M 180.246
Oil. Bp0.5 94°.
5-Hydroxy-p-mentha-6,8-dien-2-one Mo-00486
4-Hydroxy·2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one,
3-Me ether, 7-0-(2-methylpropanoyl): [33280-65-8].

2
9Cl
C 15H 110 3 M 250.337
[56423-48-4]
lsol. from lnula viscosa roots. Oil.
3-Me ether, 7-0-(3-methylbutanoyl): [33280-66-9].
C 16H 140 3 M 264.364 0
lsol. from /. viscosa roots. Oil.
Bohlmann, F. et al, Chem. Ber., 1969, 102, 864. HO
Shtacher, G. et al, Tetrahedron, 1971, 27, 1343 (derivs)
~
5-Hydroxy-p-mentha-1,4-diene-3,6-dione Mo-00483 C 10H 140 1 M 166.219
2-Hydroxy-6-methyl-3-( 1-methylethyl)-2,4-cyc/ohexadiene- lsol. from spearmint oil.
1,4-dione, 9Cl. 2-Hydroxy-3-isopropyl-5-methyl-1,4-
Canova, L., Ann. Acad. Bras. Cienc., 1972, 44, 273 (isol)
benzoquinone. 3-Hydroxy-p-mentha-1( 6),3-diene-2,5-dione.
3-Hydroxythymoquinone

No
1-Hydroxy-p-menthan-2-one Mo-00487
2-Hydroxy-2-methyl-5-(1-methylethyl)cyclohexanone. 2-
Hydroxy-5-isopropyl-2-methylcyclohexanone. 1-

Q
Hydroxycarvomenthone
o~OH OH
0

C 10H 110 3 M 180.203 (1S,4R)-form

From the heartwood of Juniperus chinensis. Orange needles 4

(EtOH aq.). Mp 168-170°. I

Pilo, C. et al, Acta Chem. Scand., 1960, 14, 353 (isol) A

Joseph-Nathan, P. et al, Org. Magn. Reson., 1981, 15, 311 (cmr) C 10H 180 1 M 170.251
(JS,4R)-form [1975-33-3]
2-Hydroxy-p-mentha-1,4(8)-dien-3-one Mo-00484 Oil. [ex]~ +23.SO.
2-Hydroxy-3-methyl-6-( 1-methylethylidene)-2-cyc/ohexen-1- (JS,4S)-form [20549-31-9]
one. Lippillphenol. Diosphenolene. /sorotundifolone Oil.
[13854-90-5] [35866-83-2, 57457-93-9]
Suga, T. et al, Bull. Chem. Soc. Jpn., 1968, 41, 944; 1972, 45, 570
(synth)

yo
AoH
1-Hydroxy-p-menthan-3-one Mo-00488
3-Hydroxy-3-methyl-6-(1-methylethyl)-cyc/ohexanone, 9Cl.
3-Hydroxy-6-isopropyl-3-methylcyc/ohexanone
CtoH 140 1 M 166.219

~0
lsol. from Mentha rotundifolia. Cryst. (pet. ether). Mp 74-
74.50. Orig. thought to be 3-Hydroxy-p-mentha-3,8(9)-
dien-2-one.

88
2-Hydroxy-p-menthan-3-one- 3-Hydroxy-p-menth-1-en-6-one Mo-00489 - Mo-00494

CtoH 1802 M 170.251 2,4-Dinitropheny/hydrazone: Orange. Mp 131°.

(1 RS,4RS)-form (1RS,4RS)-form [54164-92L0]
Ac: [58315-85-8]. 1-Acetoxy-p-menthan-3-one (±)-trans-form
C 12H 200 3 M 212.288 Bp0 _05 81-82°.
lsol. from Mentha gentilis. [a]~ + 192.2° (c, 0.21 in 2,4-Dinitropheny/hydrazone: Orange. Mp 136°.
CHC1 3). n~ 1.4652. Rupe, H. et al, Ber., 1906, 39, 1119 (synth)
Nagasawa, T. et al, Agric. Bioi. Chern., 1975, 39, 2083 (isol, abs Pinder, A.R. et at, J. Chern. Soc., 1963, 2773 (synth)
config) McCormick, J.P. et al, Tetrahedron, 1978, 34, 325 (synth, prnr, ir)
Biichi, G. et al, J. Org. Chern., 1979, 44, 546 (synth, prnr, ir)

2-Hydroxy-p-menthan-3-one
2-Hydroxy-3-methyl-6-(1-methy/ethyl)cyclohexanone. 2-
Hydroxy-6-isopropyl-3-methylcyclohexanone
[57074-29-0]
Mo-00489
8-Hydroxy-p-menth-1-en-7-oic acid Mo-00492
4-( 1-Hydroxy-1-methy/ethyl)-1-cyclohexene-1-carboxylic
acid, 9CI. 4-( 1-Hydroxyisopropyl)-1-cyclohexene-1-
carboxylic acid. 0/europeic acid
[76509-35-8]

9H
COOH

C 1oH 180 2 M 170.251

Oil. Bp 17 139°. CtoH160 3 M 184.235
[57129-11-0] (S)-:form [5027-76-9]
Kaiser, R. et al, J. Agric. Food Chern., 1975, 23, 943 (synth) Aglycone from Olea europaea. Cryst. Mp 162-165°. [a]~
-116.6° (c, 0.3 in MeOH).
4-Hydroxy-p-menthan-3-one Mo-00490 (±)-form [33746-68-8]
2-Hydroxy-5-methy/-2-(1-methylethyl)cyclohexanone. 2- Cryst. (EtzO/hexane). Mp 152-154°.
Hydroxy-2-isopropy/-5-methylcyclohexanone Panizzi, L. et al, Gazz. Chirn. !tal., 1965, 95, 1279 (struct)
Drabdina, A.A. et at, Zh. Obshch. Khirn., 1971, 41, 1412; CA, 75,

ro
A
88770h (synth)

(1R,4R)-:form 2-Hydroxy-p-menth-1-en-3-one Mo-00493

2-Hydroxy-3-methy/-6-(1-methy/ethyl)-2-cyclohexen-1-one.
HOI 2-Hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one.
~ Buchucamphor. Diospheno/
C 10H 180 2 M 170.251 [490-03-9]
(1R,4R)-form [7616-79-7]
Oil. Bp6 87-88°. [ali; -32.5° (neat).
(1R,4S)-form [7599-80-6]
Oil. Bp6 86-88°. [a]i;" + 72.5°.
[55102-25-5, 55122-53-7]
Suga, T. et at, J. Org. Chern., 1967, 32, 965 (synth)
Suga, T. et al, Bull. Chern. Soc. Jpn., 1969, 42, 3284 (abs config)
Kaiser, R. et at, J. Agric. Food Chern., 1975, 23, 943 (synth) C 10H 160 2 M 168.235
Constit. of oil of buchu (Barosma spp.), Cymbopogon
densiflorus, Mentha rotundifolia. Cryst. by subl. Mp 83-
8-Hydroxy-p-menthan-2-one Mo-00491 840. Bp 10 110°.
5-(1-Hydroxy-1-methy/ethyl)-2-methylcyclohexanone, 9CI. p-
Ohashi, M. et al, Bull. Chern. Soc. Jpn., 1976, 49, 2292 (synth, bibl)
Menthan-8-o/-2-one, 8CI. Dihydrocarvone hydrate. 8-
Hydroxytetrahydrocarvone

60
[7712-37-0] 3-Hydroxy-p-menth-1-en-6-one Mo-00494
4-Hydroxy-2-methy/-5-( 1-methy/ethyl)-2-cyc/ohexen-1-one.
4-Hydroxy-5-isopropyl-2-methyl-2-cyclohexen-1-one

02
[78391-96-5]
(1R,4R)-form

+
I

4 3 (3R,4R)-:form
OH 'OH
C 1gH180 2 M 170.251
(JR,4R)-form [35866-66-1]
(-)-trans-form C1oHt60 2 M 168.235
Oil. Bp 0 _5 83°. [a]~ -18.SO (EtOH). (3R,4R)-form [78085-73-1] 3rx-Hydroxycarvotagenone
(1S,4S)-form [68566-77-8] Constit. of Kaunia saltensis and oil of Chenopodium
(+)-trans-form multifidum. Oil. [1X]~4 -53° (c, 0.3 in CHC1 3), [1X]n
Oil. Bp0 _05 81-82°. [a]~ + 18.4° (c, 2.1 in CHC1 3). -76.7° (c, 0.9 in CHC1 3).

89
3-Hydroxy-p-menth-3-en-2-one - 8-Hydroxy-p-menth-4-en-3-one Mo-00495 - Mo-00500

(3R,4S)-form [78085-72-0] 5-Hydroxy-p-menth-1-en-6-one Mo-00498

From C. multifidum. Oil. [1X]n +61.9° (c, 1.4 in CHC13). 6-Hydroxy-2-methyl-5-(1-methylethyl)-2-cyclohexen-1-one.
[61570-81-8, 61570-82-9, 81176-19-4] 6-Hydroxy-5-isopropyl-2-methyl-2-cyclohexen-1-one
De Pascual Teresa, J. et al, Phytochemistry, 1981, 20, 163 (isol)
Bohlmann, F. et al, Phytochemistry, 1981, 20, 2375 (isol)

3-Hydroxy-p-menth-3-en-2-one Mo-00495
No
2-Hydroxy-6-methyl-3-( 1-methylethyl)-2-cyclohexen-1-one, X'OH
9C1. lfi-Diosphenol. Pseudodiosphenol
[54 783-36-7]
CIOH1601 M 168.235
(4R* ,5R*)-form
Angeloyl: [60756-53-8]. 5-Angelyloxycarvotagetone
CtsH140 1 M 236.353
Constit. of Pluchea odorata. Oil. [a]i;4 -117° (c, 1.8 in
CHC1 3).
Bohlmann, F. et al, Chern. Ber., 1976, 109, 2653 (isol)
C10H 160 1 M 168.235 Umemoto, K. et al, Nippon Nogei Kagaku Kaishi, 1977, 51, 245
Constit. of Agathosma betulina leaf oil. Oil. Bp5 93-98°. (synth)
Kaiser, R. et al, J. Agric. Food Chern., 1915, 23, 943 (isol)
Ohashi, M. et al, Bull. Chern. Soc. Jpn., 1916, 49, 2292 (synth, ir, 8-Hydroxy-p-menth-1-en-6-one Mo-00499
pmr) 5-( 1-Hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one,
Utaka, M. eta/, Chern. Lett., 1980, 779. 9CI. 8- Hydroxy-p-menth-1 (6)-en-2-one
[7712-46-1]
4-Hydroxy-p-menth-1-en-3-one Mo-00496

0~
6-Hydroxy-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one,
9CI. 6-Hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one
[1197-72-4] (R)-:form

OH
CIOH1601 M 168.235
lsol. from Nicotiana tabacum.
(R)-form [34182-03-1]
C10H 160 1 M 168.235 Cryst. (Etp). Mp 42°. [a]i;l -42° (EtOH).
(S)-form [55050-05-0] (±)-form [67738-03-8)
lsol. from Mentha gentilis. Bp 10 155-170°.
Nagasawa, T. et al, Nippon Nogei Kagaku Kaishi, 1914, 48, 467 Oxime: Cryst. (EtOH). Mp 133-134°.
(isol) Semicarbazone: Cryst. (MeOH). Mp 175°.
[60593-11-5]
4-Hydroxy-p-menth-8-en-3-one Mo-00497 Demole, E. et al, Helv. Chim. Acta, 1972, 55, 1866 (isol)
2-Hydroxy-5-methyl-2-(1-methylethenyl)cyclohexanone Siemieniuk, A. et al, Pol. J. Chern. (Rocz. Chern.), 1978, 52, 727
[18194-21-3] (synth)
Buchi, G. et al, J. Org. Chern., 1979, 44, 546 (synth)

~~
8-Hydroxy-p-menth-4-en-3-one Mo-00500
(1R,4R)-:form 2-( 1-Hydroxy-1-methylethyl)-5-methyl-2-cyclohexen-1-one,
9CI

C10H 160 1 M 168.235

lsol. from Buchu leaf oil.
(1R,4R)-form [35736-68-6]
Mp ca. 20°. [a]i? -132° (c, 10 in CHC1 3).
(1R,4S)-form [35736-67-5]
[ali? + 216.9° (c, 10 in CHC1 3). C10H 160 1 M 168.235
[57129-19-8] (R)-form [35736-66-4]
Schulte-E1te, K.H. et al, Helv. Chim. Acta, 1971, 54, 1870 (synth) lsol. from Mentha gentilis. [a]i;l -65.8° (c, 0.53 in CC14).
Kaiser, R. et a/, J. Agric. Food Chern., 1975, 23, 943 (isol)
Schulte-E1te, K.H. et al, Helv. Chim. Acta, 1971, 54, 1870 (synth)
Nagasawa, T. et al, Agric. Bioi. Chern., 1915, 39, 553 (isol)

90
9-Hydroxy-p-menth-4(8)-en-3-one - 4-lsopropyl-2-cyclohexen-1-ol Mo-00501 - Mo-00508

9-Hydroxy-p-menth-4(8)-en-3-one Mo-00501 C12H 160 2 M 192.257

2-(2-Hydroxy-1-methylethylidene)-5-methylcyclohexanone, Constit. of peppermint oil. Cryst. (EtOH). Mp 71-72°.
9CI Sakurai, K. et al, Agric. Bioi. Chern., 1983, 47, 1249.
I
I
2-(2-Hydroxy-4-methylphenyl)-1,3- Mo-00505
propanediol, 9CI
p-Mentha-1,3,5-triene-3,9,10-triol. 9,10-Dihydroxythymol

HOC2° [128286-92-0]

HOH,:t~~OH
C 10H 160 2 M 168.235
(S,E)-form
Oil. [ex]~ -31.4° (c, 0.5 in EtOH).
0-P-v-Glucoside: [105351-69-7]. Schizonepetoside C
C16H 260 7 M 330.377
Constit. of spikes of Schizonepeta tenuifolia. CIOHIPJ M 182.219
Hygroscopic amorph. powder. [ex]~ -48.9° (c, 0.7 in Consit. of Perityle emoryi. Oil.
EtOH). Zdero, C. eta/, Phytochemistry, 1990, 29, 891 (isol, pmr)
P-v-Glucoside, Tetra-Ac: Needles (Etpjhexane). Mp 75.5-
760. [ex]i; -43.9° (c, 0.3 in EtOH).
4-Isopropenylbenzaldehyde Mo-00506
Kubo, M. et al, Chern. Pharm. Bull., 1986, 34, 3097. 4-(1- M ethylethenyl)benzaldehyde, 9Cl. p- M entha-1 ,3 ,5,8-
tetraen-7-al
4-Hydroxy-2-methoxy-p-menth-1-en-3-one Mo-00502 [10133-50-3]
6-Hydroxy-2-methoxy-3-methyl-6-(1-methylethyl)-2-

2
cyclohexen-1-one, 9CI CHO
[57074-41-6]

C 10H 100 M 146.188

Constit. of Roman camomile oil (Anthemis nobilis). Oil.
BPo.oi lOOo.
C 11 H 180 3 M 198.261 Semicarbazone: Cryst. (2-propanol). Mp 240-242°.
lsol. from Buchu leaf oil. Thomas, A.F. eta/, Helv. Chim. Acta, 1981, 64, 2393.
Kaiser, R. eta/, J. Agric. Food Chern., 1975, 23, 943.
Isopropylcyclohexane, SCI Mo-00507
3-(2-Hydroxy-4-methylphenyl)-2-butanone, Mo-00503 1-Methylethylcyclohexane, 9CI
9CI [696-29-7]
[8381 0-64-4]

C9H 18 M 126.241
Found in Carica papaya. Oily liq. Fp -89.8°. Bp 154.7°
(150-153°).
I> GV5030000.
C 11H 140 2 M 178.230 Matsubara, K. eta/, J. Chern. Soc., 1905, 661 (synth)
Constit. of peppermint oil. Cryst. (EtOH). Mp 67-68°. Adams, J.Q. eta/, Prepr.-Am. Chern. Soc., Div. Pet. Chern., 1972,
Sukari, K. et al, Agric. Bioi. Chern., 1983, 47, 1249. 17, C4 (cmr)
Green, M.M. et al, Adv. Mass Spec/rom., 1978, 7A, 149 (ms)
Miller, L.L. et al, J. Org. Chern., 1978, 43, 2059 (synth)
2-(2-Hydroxy-4-methylphenyl)-3- Mo-00504
pentanone, 9CI
4-Isopropyl-2-cyclohexen-1-ol Mo-00508
[86843-15-4] 4-(1- Methylethyl)-2-cyclohexen-1-ol. Cryptol

6
OH

(IR,4'S)-form

A
M 140.225

91
4-lsopropyl-2-cyclohexen-1-one - 1-lsopropyl-4-methylbenzene Mo-00509 - Mo-00512

(JR,4S)-form [33531-22-5] 4-Isopropyl-3-cyclohexen-1-one, SCI Mo-00510

(+)-trans-form 4-(1-M ethylethyl)-3-cyclohexen-1-one, 9CI
Bp 2 72°. [alii' + 146.4° (c, 2.0 in EtOH). [5259-66-5]
4-Nitrobenzoyl: Cryst. (MeOH). Mp 84°. [a]ii' + 174° (c,
2.0 in CHC1 3).
(JRS,4SR)-form
(±)-trans-form
Bp4 90°.
4-Nitrobenzoyl: Needles (MeOH). Mp 76.SO.
3,5-Dinitrobenzoyl: Plates (MeOH). Mp 108°.
(JRS,4RS)-form [64233-69-8] C9H 140 M 138.209
(±)-cis-form Oil. Bp7 77-78°.
Bp6 86°. 2,4-Dinitrophenylhydrazone: Golden yellow cryst. Mp 105-
4-Nitrobenzoyl: Plates (MeOH). Mp 34.5-35.SO. 1060. Thermolabile.
3,5-D!nitrobenzoyl: Needles (MeOH). Mp 96.5°. Semicarbazone: Mp 177-178°.
Gillespie, D.T.C. eta/, J. Chern. Soc., 1938, 1820; 1939, 1531 Nelson, N.A. et al, J. Org. Chern., 1957, 22, 1146 (synth, ir, uv)
(synth) Green, M.M. et al, J. Am. Chern. Soc., 1970, 92, 6368 (synth)
Macbeth, A.K. et al, J. Chern. Soc., 1939, 264 (synth)
4-lsopropylidene-1-methyl-1- Mo-00511
4-Isopropyl-2-cyclohexen-1-one, SCI Mo-00509 vinylcyclohexane
4-(1-M ethylethyl)-2-cyclohexen-1-one, 9CI. Cryptone 1-Ethenyl-1-methyl-4-( 1-methylethylidene)cyclohexane, 9CI.
[500-02-7] 1- Vinyl-p-menth-4(8)-ene
[77820-38-3]

(R)-form

C9H 140 M 138.209

Present in many plants incl. Angelica root, black pepper,
cardamom, and lavender.
(R)-form [2158-59-0]
Present in many plants incl. Angelica root, black
pepper, cardamom, and lavender, Eucalyptus spp.
Xanthoxylum rhetsa, Santo/ina chamaecyparissus. Oil
with characteristic woody odour. Bp 10 98-100°. [1X] 0
-119.3° (EtOH).
Semicarbazone: Cryst. (MeOH). Mp 186°. [a] 0 -27° (c,
2.0 in CHC1 3).
2,4-Dinitrophenylhydrazone: Cryst. (MeOH). Mp 135-136°
(132°). [a]i,O +4.8° (c, 5.0 in CHC1 3).
(S)-form
[1X] 0 +64.57° (EtOH).
(±)-form [2158-61-4]
Liq. with characteristic, woody odour. Bp2 _8 78°.
Semicarbazone: Plates (MeOH). Mp 196-196.5° dec.
2,4-Dinitrophenylhydrazone: Orange-red plates (EtOH). Mp
136-136.5°.
Galloway, A.S. eta/, J. Chern. Soc., 1936, 1595 (isol)
Berry, P.A. et al, J. Chern. Soc., 1937, 1448 (isol, S-form)
Birch, A.J., Annu. Rep. Prog. Chern., Sect. B, 1950, 47, 190 (abs
config)
Naves, Y.R., Perfum. Essent. Oil Rec., 1950, 41, 441; CA, 45, 4889
(isol)
Soffer, M.D. et al, J. Am. Chern. Soc., 1955, 77, 1003 (synth, uv)
Stadler, P.A., Helv. Chim. Acta, 1960, 43, 1601 (isol)
Mukherji, G. et al, J. Chern. Soc., 1963, 2402 (synth, uv)
Naves, Y.R. eta/, Bull. Soc. Chim. Fr., 1969, 588 (synth)
Fisher, R.D. et a/, J. Am. Chern. Soc., 1973, 95, 3646 (synth, ir,
pmr)
Friedrich, E. et al, Angew. Chern., 1977, 89, 426 (synth)
CllH:zo M 164.290
Constit. of Mentha citrata. Oil.
Singh, S.B. et al, Phytochemistry, 1980, 19, 2466.
1-Isopropyl-4-methylbenzene Mo-00512
1-Methyl-4-(1 -methylethyl)benzene, 9CI. p-M entha-1 ,3,5-
triene. p-Cymene. p-lsopropyltoluene. Camphogene (obsol.).
Camphene (obsol.)
[99-87-6]
CIOH14 M 134.221
V. widely distributed in plant oils eg. terpentine and citrus
oils and many others. Used in perfumery and flavour
industries. Liq. Mp -67.94°. Bp 177.10°.
I> Mod. toxic, flammable. GZ5950000.
Allen, R.H. et al, J. Am. Chern. Soc., 1961, 83, 2799 (synth)
Hall, S.S. et al, J. Org. Chern., 1972, 37, 760 (synth)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzensto.ffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 39 (occur)
Olah, G.A. et al, J. Org. Chern., 1974, 39, 2430 (synth)
Hino, M. et al, Chern. Lett., 1977, 277 (synth)
Lee, E.W., Ethel Browning's Toxicity and Metabolism of Industrial
Solvents, (Snyder, R., Ed.), 2nd Ed., Elsevier, 1990, 1, 105 (rev,
tox)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 533.

92
2-Isopropyl-5-methyl-1,4-... - 5-lsopropyl-2-methylphenol Mo-00513 - Mo-00516

2-Isopropyl-5-methyl-1,4-benzenediol Mo-00513 Treibs, W. eta/, Ber., 1931, 64, 2184; J. Prakt. Chern., 1933, 138,
2-Methyl-5-(1-methylethyl)-1,4-benzenediol, 9CI. p- Mentha- 284 (synth)
De Fenik, I.J.S. et al, CA, 1975, 83, 103138 (isol)
1,3,5-triene-2,5-diol. 2,5-Dihydroxy-p-cymene. Thymoquinol.

2
2-/sopropyl-5-methylquinol. Hydrothymoquinone. Thymoilol
[2217-60-9] 2-Isopropyl-5-methylphenol Mo-00515
5-Methyl-2-(1 -methylethyl)phenol, 9CI. p- M entha-1 ,3,5-
trien-3-ol. p-Cymen-3-ol, 8CI. 6-/sopropyl-m-cresol. 3-
0H Hydroxy-4-isopropyltoluene. 3-Hydroxy-p-cymene. Thymol.

HO
I Thymianic acid (obsol.). Thymianic camphor (obsol.)
[89-83-8]
CtoHt40 M 150.220
Found in many essential oils. Esp. found in the Labiateae.
c1oH14o1 M 166.419 Rich sources are thyme oil, seed oil of Ptychotis ajowan
Menthane numbering shown. Constit. of oil from Monarda and oils of Monarda punctata and Ocimum spp.
spp. and of cedar heartwood. Also from Eupatorium Perfumery and flavour ingredient. Plates (EtOAc or
japonicum leaves and heartwoods of Juniperus chinensis AcOH or Me 20) with odour of thyme. Mp 51 .SO. Bp
and Libocedrus decurrens. Has antihistaminic and 233.SO, Bp!O 115°.
antifungal props. Prisms (H 20). Mp 143° (139.SO). I> XP2275000.
I> MX6680000. Ac: [528-79-0].
5-Ac: 4-Acetoxy-5-isopropyl-2-methylphenol. 5- C 11H 160 1 M 192.257
Hydroxyacetylthymol Bp 242-243°.
C 11H 160 3 M 208.257 Benzoyl: [6380-29-6].
Constit. of Pulicaria undulata. Oil. cl,Hla01 M 254.328
Di-Ac: Mp 73-75°. Plates. Mp 33°.
2-/Je ether: 5-/sopropyl-4-methoxy-2-methylphenol. p- 0-P-D-Glucopyranoside:
M ethoxycarvacrol C 16H 2,p6 M 312.362
C 11H 160 1 M 180.246 Constit. of Jasonia montana.
lsol. from L. decurrens. Cryst. (hexane). Me ether: [1076-56-8]. 1-/sopropyl-2-methoxy-4-
4-Me ether: 2-/sopropyl-4-methoxy-5-methylphenol. p- methylbenzene. 2-/sopropyl-5-methylanisole. Thymol
Methoxythymol methyl ether
C 11 H 160 1 M 180.246 C 11 H 160 M 164.247
lsol. from trunkwood of L. decurrens. Bp25 155-156°. Naturally occurring, e.g. in oil of Crithmum maritimum
Di-Me ether: [14753-08-3). 1-/sopropyl-2,5-dimethoxy-4- and Orthodon hadai, Citrus spp., Pulicaria dysenterica,
methylbenzene. 2,5-Dimethoxy-p-mentha-1,3,5-triene Arnica montana. Oil with ethereal odour. Bp 745 211-212°,
C 11H 180 1 M 194.273 Bp 15 94-96°.
Constit. ef oil from Apium leptophyllum, also from Et ether: [4732-12-l ]. 2-Ethoxy-1-isopropyl-4-methylbenzene
Arnica montana and Eupatorium spp. d 22 0.998. Bp 248- C 11H 180 M 178.274
2500, Bp!O 120-121°. Bp 224-228°.
Fichter, F. et al, Ber., 1914, 47, 2003 (synth) Austerweil, G. et al, Bull. Soc. Chim. Fr., 1927, 41, 454.
Sherk, D.C.L., J. Am. Pharm. Assoc., 1921, 10, 97 (isol) Fujita, Y., CA, 1947, 41, 3585 (isol, deriv)
Zavarin, E. et a/, J. Org. Chern., 1955, 20, 82 (isol, synth, derivs) v. Sydow, E., Acta Chern. Scand., 1963, 17, 2504 (ms)
Pilo, C. et al, Acta Chern. Scand., 1960, 14, 353 (isol) Schulte, K.E. et al, Arch. Pharm. (Weinheim, Ger.), 1963, 2%, 353
Chow, Y.-L. eta/, Acta Chern. Scand., 1962, 16, 1291 (isol, deriv) (isol, synth, deriv)
Minoru, U. et al, CA, 1967, 66, 36728v. Yamazaki, M. et al, Chern. Pharm. Bull., 1963, 11, 363 (biosynth)
Park, R.J. eta/, Aust. J. Chern., 1969, 22, 495 (ir, uv, nmr, deriv) Kraus, M. et al, Collect. Czech. Chern. Commun., 1963, 28, 1877
Svischchuk, A.A. eta/, CA, 1971, 75, 35333m (synth) (synth)
Metwally, M. et al, Chern. Pharm. Bull., 1986, 34, 378 (isol, deriv) Uldrickies, J. et al, CA, 1965, 63, Jl408 (synth)
Morris, W.W., J. Assoc. Off Anal. Chern., 1973, 56, 1037 (ir)
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (glycoside)
5-Isopropyl-2-methyl-1,3-benzenediol Mo-00514 Sax, N.J., Dangerous Properties of Industrial Materials, 5th Ed.,
2-Methyl-5-( 1-methylethyl)-1,3-benzenediol, 9CI. p-Cymene- Van Nostrand-Reinhold, 1979, 1032.
2,6-diol. p-Mentha-1,3,5-triene-2,6-diol. Cymorcin. 5-
Hydroxycarvacrol
5-lsopropyl-2-methylphenol Mo-00516
[4389-62-2] 2-Hydroxy-4-isopropyl-1-methylbenzene. p- M entha-1 ,3,5-
trien-2-ol. Carvacrol. 2-Hydroxycymene. Cymophenol. p-
Cymen-2-ol. 5-/sopropyl-o-cresol
[499-75-2]

CtoHt40:z M 166.219
Isol. from essential oil of Pseudocaryophyllus guili. Mp
130-132°. Bp 294°.
Dibenzoyl: Mp 80°. M 150.220
Di-Me ether: Bp20 142°.

93
3-Libocedroxythymoquinone - p-Mentha-1,8-dien-7-al Mo-00517 - Mo-00520

Constit. of many essential oils. Esp. found in the
Labiateae. Thyme oil ( -70%) and Origanum oil
( -80%) are rich sources. Liq. Mp 3.SO. Bp 237-238°,
Bp 1o ll3°.
I> Fll225000.
3,5-Dinitrobenzoyl: Cryst. Mp 76-77°.
Me ether: 4-Isopropyl-2-methoxy-1-methylbenzene
C 11H 160 M 164.247
lsol. from heartwoods of Cupressus spp. and
Chamaecyparis thyoides. Bp 216°, Bp 15 94°.
Guenther, E., The Essential Oils, Van Nostrand, N.Y., Vol. 2,
1949, 503 (rev)
Ritter, G., J. Am. Chem. Soc., 1950, 72, 2381 (s~th)
Carpenter, E., J. Org. Chem., 1955, 20, 401 (isol)
Enzell, C. eta/, Acta Chem. Scand., 1960, 14, 81; 1961,.15, 1313
(isol, deriv)
Beckley, H.D. eta/, Org. Mass Spectrom., 1968, 1, 47 (ms)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 174 (occur)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)
3-Libocedroxythymoquinone Mo-00517
(±)-form [7705-14-8] Dipentene
Constit. of Oleum cinae, pine needle oil and many
essential oils. Obt. comly. as by prod. in hydration of
turpentine. Oil. Bp 178°.
I> Irritant, flammable.
[6876-12-6]
Thomas, A.F. eta/, Helv. Chim. Acta, 1964, 47, 475 (ms)
Pawson, B.A. eta/, J. Chern. Soc., Chern. Commun., 1968, 1057
(abs config)
Verghese, J., Perfum. Essent. Oil Rec., 1968, 59, 439 (rev)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
nos. 53,54 (occur)
Nijaura, N. eta/, Chem. Lett., 1974, 1411 (synth)
Org. Synth., 1977, 56, 101 (synth)
Thomas, A.F. eta/, Nat. Prod. Rep., 1989, 6, 291 (rev)
Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 621, 772.
Hazards in the Chemical Laboratory, (Bretherick, L., Ed.), 3rd Ed.,
Royal Society of Chemistry, London, 1981, 313.
Limonenecarboxylic acid Mo-00519
3-(4-Methyl-3-cyc/ohexen-1-yl)-2-butenoic acid, 9CI. p-
Mentha-1,8-diene-9-carboxy/ic acid
[51373-21-8]

HOOC
CuH160 2 M 180.246
C32H400, M 520.664 Constit. of Cedrus deodara. Cryst. (pet. ether). Mp 108-
Isol. from heartwood of Heyderia (Librocedrus) decurrens. 1090. [cxJn + 19.1° (c, 0.9 in CHCl 3).
Dark-red cryst. (MeOH). Mp 155°. Me ester: [38142-44-8].
Zavarin, E., J. Org. Chem., 1958, 23, 1198 (isol, pmr, ir, uv) Bp8 130-135°. [ex]~ +25.6° (c, 2.5 in CHCl3).
[57129-56-3, 57129-57-4]
Limonene Mo-00518 Krishnappa, S. eta/, Tetrahedron, 1978, 34, 599.
1-Methyl-4-(1-methylethenyl)cyc/ohexene, 9Cl. 4-
Isopropenyl-1-methylcyc/ohexene. p- M entha-1 ,8-diene. p-Mentha-1,8-dien-7-al Mo-00520
Citrene. Hesperidene. Diisoprene. Terpilene. Kautschine. 4-(1-M ethylethenyl)-1-cyclohexene-1-carboxaldehyde, 9Cl. 4-
Cinene. Cynene. Cajeputene. Isoterebentine. Carvene Isopropeny/-1-cyclohexene-1-carboxaldehyde. PeriUaldehyde.
[138-86-3] Peril/aaldehyde

6
[2111-75-3]

(R)-form
I

A (R)-form
C1oH16 M 136.236 I

The most important and widespread terpene known. ~

Extensively used in the perfumery and flavour industries
C1oH 140 M 150.220
and in manuf. of polymers and adhesives.
I> Irritant.
(R)-form [5989-27-5]
Major constit. of oil of orange rind, dill oil, oil of (R)-form [5503-12-8]
cumin, neroli, bergamot, caraway and lemon (Citrus, lsol. from Siler trilobum, Sium latifolium, Citrus
Anethum, Juniperus, Peucedanum spp.) Obt. comly. from reticulata and other plants. Oil. Bp9 99-104°. [cxln
orange oil on a large scale (ca. 50000 Tja). Important + 137°.
chiral starting material for org. synth. Shows insecticidal Oxime:
props. Oil. Bp20 7l o. [ cxJi:' + 126.8°. C10H15NO M 165.235
I> GW6360000. Cryst. Mp 102°.
(S)-form [5989-54-8] 7-Carboxylic acid: [7694-45-3]. p-Mentha-1,8-dien-1-oic
Constit. of pine needle oil. Oil. Bp 177.6-177.8°. [cxJn acid. PeriUic acid
-122.6°. C1oH1402 M 166.219
I> 088350000.

94
p-Mentha-1,3-diene - p-Mentha-1,5-diene
Isol. from Salvia dorisiana. Cryst. (EtOH). Mp 132-133°.
Bp 10 164-165°. [ex]~ -146°.
7-Carboxy/ic acid, Me ester: [54298-90-7].
Bp0 _5 81-83°.
(S)-form [18031-40-8]
CIOHI~NO M 165.235
Constit. of oil of Perilla nankinensis and gingergrass oil.
Oil. Bp 10 104-105°. [ex]~ -145.8°.
(E)-Oxime: Perilla sugar. Perillartine
C 10 H 1 ~NO M 165.235
Sweetening agent. V. sweet cryst. Mp 102°. Bp 12 147-
1480.
(Z)-Oxime: Cryst. Mp 129°.
[6611-91-2]
Ritter, J.J. et al, J. Am. Chern. Soc., 1950, 72, 2381 (synth, Perillic
acid)
Vig, O.P. et al, J. Indian Chern. Soc., 1968, 45, 615 (synth)
Acton, E.M. et al, Experientia, 1970, 26, 473 (struct)
Suga, T. et al, Bull. Chern. Soc. Jpn., 1972, 45, 545 (stereochem)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)
Tori, K. et al, Tetrahedron Lett., 1975, 2199 (pmr)
Regan, J.W. eta/, J. Agric. Food Chern., 1976, 24, 377 (Peri/lie
acid)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 893.
p-Mentha-1,3-d.iene Mo-00521
1-Methyl-4-(1 -methylethyl)-1 ,3-cyc/ohexadiene. 1-/sopropyl-
4-methy/-1 ,3-cyc/ohexadiene. ac- Terpinene
[99-86-5]
CIOH16 M 136.236
Constit. of many essential oils e.g. Citrus, Eucalyptus,
Juniperus and Pinus spp. Oil with lemon odour. Bp755
173.5-174.8°.
I> 088060000.
Thomas, A.F. eta/, Helv. Chim. Acta, 1964, 47, 475 (ms)
Degny, E. et a[, Bull. Soc. Chim. Fr., 1972, 4770 (synth)
Verghese, J., Flavour Ind., 1972, 3, 252 (rev)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
p-Mentha-1,4(8)-d.iene Mo-00522
1-Methyl-4-(1-methylethylidene)cyclohexene, 9CI. 4-
/sopropy/idene-1-methylcyc/ohexene. Terpinolene
[586-62-9]
CIOHI6 M 136.236
Constit. of many essential oils e.g. Citrus, Mentha,
Juniperus, Pinus spp. Alarm pheromone for termites.
Perfumery and flavouring ingredient. Oil. Bp 186°.
I> Flammable. WZ6870000.
Thomas, A.F. et a/, Helv. Chim. Acta, 1964, 47, 475 (ms)
Wrolstad, R.E., J. Agric. Food Chern., 1964, 12, 507 (isol, ir)
Verghese, J., Perfum. Essent. Oil Rec., 1967, 58, 638 (rev)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhauser Verlag, Basel, 1972-1985,
no. 51 (occur)
95
Mo-00521 - Mo-00524
Krapcho, A.P. et al, J. Org. Chern., 1974, 39, 1322 (synth)
Mathew, C.P. et al, J. Indian Chern. Soc., 1975,.52, 997 (synth)
Sax, N.J., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 1010.
p-Mentha-1,4-d.iene Mo-00523
1-Methyl-4-(1-methylethyl)-1 ,4-cyc/ohexadiene, 9CI. 1-
/sopropyl-4-methyl-1 ,4-cyclohexadiene. p- Terpinene.
Crithmene. Moslene
[99-85-4]
CIOH16 M 136.236
Constit. of many essential oils e.g. Citrus, Eucalyptus,
Juniperus, Mentha, Pinus spp. Oil. Bp 183°.
I> 088070000.
Briggs, L.H. et al, J. Org. Chern., 1948, 6, I (isol)
Ryhage, R. et al, Acta Chern. Scand., 1963, 17, 2025 (ms)
Wrolstad, R.E. et al, J. Agric. Food Chern., 1964, 12, 507 (ir)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkbauser Verlag, Basel, 1972-1985,
no. 47 (occur)
Verghese, J., Indian Perfum., 1974, 18, 53 (rev)
p-Mentha-1,5-d.iene Mo-00524
2-Methyl-5-(1 -methylethyl)-1 ,3-cyc/ohexadiene. 5-/sopropyl-
2-methyl-1 ,3-cyclohexadiene. ac-Phellandrene
[99-83-2]
(R)-form
CIOHI6 M 136.236
(R)-form [4221-98-1]
Constit. of oils of pimento, bay and Eucalyptus
phelandra and other essential oils, (Citrus, Juniperus,
Mentha and Pinus spp.). Oil. Bp 174°. [ex]~ -217°.
(S)-form [2243-33-6]
Constit. of many essential oils including bitter fennel,
elemi and ginger-grass oils. Flavour ingredient. Oil. Bp
175-176°. [exln +49.1°.
I> Mod. irritant.
[13811-01-3]
Ryhage, R. et al, Acta Chern. Scand., 1963, 17, 2025 (ms)
Snatzke, G. ·et al, Tetrahedron Lett., 1966, 4551 (abs config)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 48 (occur)
Singaram, B. et al, Perfum. Flavor., 1978, 2, 33 (rev)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 896.
p-Mentha-1(7),2-diene - p-Mentha-2,4-diene Mo-00525 - Mo-00530

p-Mentha-1(7),2-diene Mo-00525 C10H 16 M 136.236

3-Methylene-6-(1-methylethyl)cyc/ohexene. 3-/sopropyl-6- Oil. Bp!O 105-108°.
methylenecyc/ohexene. fJ-Phellandrene Vig, O.P. et a/, J. Indian Chem. Soc., 1968, 45, 369.
[555-10-2]

6
p-Mentha-1(7),8-diene Mo-00528
1-Methylene-4-(1-methylethenyl)cyc/ohexane. 1-/sopropenyl-
4-methylenecyc/ohexane. lfJ-Limonene. Pseudolimonene
(R)-form [499-97-8]
I

~
C 1olf16 M 136.236
Widely distributed in essential oils (Angelica, Eucalyptus,
Lavandula, Mentha, Pinus spp.). Flavour ingredient.
(R)-form [6153-17-9]
CIOH16 M 136.236
Constit. of Juniperus and Pinus spp. Oil. Bp 172-174°.
Oil. Bp!OO 105°.
[1X]n -74.4°. ni,<' 1.4826.
Verghese, J., Perfum. Essent. Oil Rec., 1967, 58, 868 (rev)
(S)-form [6153-16-8] Von Buenau, G. et al, Fresenius' Z. Anal. Chem., 1969, 244, 7 (ms)
Constit. of oils of Bupleurum fruticosum and Juniperus
spp. Oil. Bp 171-172°. [1X]n +75°.
~Mentha-2,4(8)-diene Mo-00529
[51941-36-7]
3-Methyl-6-( 1-methylethylidene)cyclohexene. 3-
Acheson, G.G. et al, J. Chem. Soc., 1949, 812 (struct) /sopropy/idene-6-methylcyclohexene. /soterpino/ene
Mitzner, B.M. et al, J. Org. Chem., 1962, 27, 3359 (synth)
Ryhage, R. eta/, Acta Chem. Scand., 1963, 17, 2025 (ms) [586-63-0]
Deorha, D.J. eta/, Reel. Trav. Chim. Pays-Bas (J. R. Neth. Chem.
Soc.), 1965, 82, 137 (synth)
Verghese, J. et a/, Perfum. Essent. Oil Rec., 1967, 58, 868 (rev)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 49 (occur)
Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 791. CIOH16 M 136.236
I sol. from leaf oil of Juniperus horizontalis.
p-Mentha-1(7),3-diene Mo-00526 (R)-form [43124-56-7]
4-Methylene- I-( 1-methylethyl)cyc/ohexene. 1-/sopropyl-4- Oil. Bp 764 . 5 184-186°. [1X]:I +49.1°. ni,<' 1.5026.
methylenecyc/ohexene. fJ- Terpinene Ohloff, G. et al, Justus Liebigs Ann. Chem., 1959, 625. 206 (synth,
[99-84-3] uv, abs config)
Thomas, A.F. et al, Helv. Chim. Acta, 1964, 47, 475 (ms)
Couchman, F.M. et al, Can. J. Chem., 1965, 43, 1017 (isol)
Verghese, J., Perfum. Essent. Oil Rec., 1967, 58, 868 (rev)
Bark, S. eta/, J. Org. Chem., 1968, 33, 221 (synth)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)

p-Mentha-2,4-diene Mo-00530
5-Methyl-2-(1 -methylethyl)-1 ,3-cyc/ohexadiene. 2-/sopropyl-
CIOH16 M 136.236
5-methyl-1 ,3-cyc/ohexadiene
Constit. of Juniper and Myrica gale oils. Also from
Pittosporum tenuiflorum, Dacrydium biforme and [586-68-5]
Leptospermum ericoides. Oil. Bp 173-174°. [1X]i,<' +3.0°.
Wallach, 0., Justus Liebigs Ann. Chem., 1908, 362, 288.
Corbett, R.E. et al, J. Sci. Food Agric., 1959, 10, 198 (isol)
Mitzner, B.M. et al, J. Org. Chem., 1962, 27, 3359 (synth)
Thomas, A.F. et al, Helv. Chim. Acta, 1964, 47, 475 (ms)
Verghese, J., Indian Perfum., 1974, 18, 39 (rev)

C10H 16 M 136.236
p-Mentha-1(7),4(8)-diene Mo-00527 Constit. of Valencia orange oil. Oil. Bp25 56°.
1-Methylene-4-( 1-methylethylidene)cyclohexane. 1-
Hunter, G.L.K. eta/, J. Org. Chem., 1964, 29, 498.
/sopropylidene-4-methylenecyclohexane
[6876-10-4]

96
p-Mentha-3,8-diene - p-Mentha-1(7),8-dien-2-ol Mo-00531 - Mo-00536

p-Mentha-3,8-diene Mo-00531 Isol. from lemongrass oil. Bp 2.5 64-65°. Obt. as a mixt. of
4-Methyl-1-(1-methylethenyl)cyclohexene, 9CI. 1- cis and trans-forms. No props. of individual
/sopropenyl-4-methylcyclohexene stereoisomers reported.
[586-67-4] [55820-19-4, 58461-28-2)
Naves, Y.R., Bull. Soc. Chirn. Fr., 1961, 1881 (iso/)
Cant, P.A.E. eta/, Aust. J. Chern., 1975, 28, 621 (synth, prnr)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (crnr)

p-Mentha-1(7),2-dien-4-ol Mo-00534
4-Methylene-1-(1-methylethyl)-2-cyclohexen-1-ol, 9CI. 1-
1sopropyl-4-methylene-2-cyclohexen-1-o/
C 10H 16 M 136.236
Found in pine needles.
(R)-form [62192-80-7]
Bp 12 70°. [(J(]i,O + 120.2°. ni,<' 1.4934.
[62433-77-6]
Ohloff, G. et a/, Justus Lieqigs Ann. Chern., 1959, 625, 206 (synth,
uv)
Thomas, A.F. eta/, Helv. Chirn. Acta, 1964, 47, 475 (rns) C 10H 160 M 152.236
Rykowski, Z. eta/, Pol. J. Chern. (Rocz. Chern.), 1976, SO, 1901. Isol. from black pepper oil.
Debrauwere, J. eta/, Bull. Soc. Chirn. Be/g., 1975, 84, 167 (iso/,
p-Mentha-3,6-diene-2,5-dione, SCI Mo-00532 ms, prnr)
2-Methyl-5-(1-methylethyl)-2,5-cyclohexadiene-1,4-dione,.
9CI. 2-/sopropyl-5-methyl-1 ,4-benzoquinone. p-Cymene-2,5- p-Mentha-1(7),5-dien-2-ol Mo-00535
dione. Thymoquinone. Thymoil 2-Methy/ene-5-(1-methy/ethyl)-3-cyclohexen-1-o/, 9CI.
[490-91-5] Yabunikkeol

fro
6
[30681-15-3]

,0H

0~
C 10H 120 2 M 164.204
A (2RAR)-form
Occurs in woods of Callitris quadrivalvis and M onarda
CtoHt60 M 152.236
fistulosa. Also from Juniperus cedrus, Tetraclinis
articulata and Nepeta leucophylla. Major constit. of seed (2R,4R)-form [29332-99-8]
oil of Nigella sativa (24%). Bright-yellow cryst. (+)-cis-form
(pentane) with penetrating odour. Mp 44-45°. Steam- Constit. of the essential oil of Cinnamomum japonium.
volatile. Cryst. Mp 41-42° (34°). Bp 228°. [(J(Ji? + 56° (c, 1.0 in
CHC1 3), [(J(]i,O +35° (c, 0.30 in EtOH).
I> GU5330000.
(2S,4R)-form [29332-98-7]
Dioxime:
(- )(EtOH)-trans-form
C 10H 14NP 2 M 194.233
Constit. of C. japonium and Piper nigrum. Oil. Bp 226°.
Cryst. (EtOH). Mp 235°.
[(J(Ji? -28° (c, 0.52 in EtOH), [(J(Ji? +5° (c, 0.81 in
Henderson, G.G. eta/, J. Chern. Soc., 1910, 1659 (synth) CHC13).
Org. Synth., Col/. Vol., 1, 1932, 498, 511 (synth)
Flaig, W. eta/, Z. Naturforsch., B, 1955, 10, 668 (uv) Ac:
Flaig, W. eta/, Justus Liebigs Ann. Chern., 1959, 626, 215 (ir) C12H 180 2 M 194.273
El-Dakhakhny, M., Planta Med., 1963, 11, 465 (isol) Constit. of Angelica archangelica. Oil. [(J(]i,O -55° (c, 0.8
Norris, R.K. eta/, Aust. J. Chern., 1966, 19, 617 (prnr) in CHC1 3).
Jacobsen, N., J. Chern. Soc., Perkin Trans. 2, 1979, 569 (synth, Fujita, Y. eta/, Bull. Chern. Soc. Jpn., 1970, 43, 1599 (isol)
prnr, ms) Debrauwere, J. eta/, Bull. Soc. Chirn. Be/g., 1975, 84, 167 (iso/,
prnr)
p-Mentha-1(6),8-dien-3-ol Mo-00533 Escher, S. et a/, Helv. Chirn. Acta, 1979, 62, 2061 (iso/, synth, uv,
3-Methyl-6-(1-methylethenyl)-3-cyclohexen-1-ol, 9CI. p- ir, prnr)
Montiel, V. et a/, Synth. Cornrnun., 1987, 17, 993 (synth)
M entha-1 ,8-dien-5-ol
[200 19-62-9]
p-Mentha-1(7),8-dien-2-ol Mo-00536
2-Methylene-5-(1-methy/ethenyl)cyclohexano/, 9CI

~OH
[35907-10-9]

(2R,4R)-form
M 152.236

97
p-Mentha-1(7),8-dien-3-ol- p-Mentha-1,8-dien-7-ol Mo-00537- Mo-00541

ciOH 1,0 M 152.236 Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (crnr)
(2R,4R)-form [10374-04-6] Naya, Y. et a/, Heterocycles, 1978, 10, 29 (isol)
Delay, F. et al, Helv. Chirn. Acta, 1979, 62, 2168 (synth, prnr)
lsol. from Cymbopogon densiflorus.
(2S,4R)-form [2102-62-7]
lsol. from C. densiflorus and Zanthoxylum piperitum. p-Mentha-1,8-dien-6-ol Mo-00540
2-Methy/-5-(1-methy/ethenyl)-2-cyc/ohexen-1-ol. 5-
[21391-84-4, 22626-43-3]
/sopropenyl-2-methyl-2-cyc/ohexen-1-o/. Carveol
Ohloff, G. eta/, Angew. Chern., 1961, 73, 578 (synth)
[99-48-9]
Sakai, T. et al, Bull._ Chern. Soc. Jpn., 1968, 41, 1945 (isol)

p-Mentha-1(7),8-dien-3-ol Mo-00537 }y/oH

5-M ethy/ene-2-(1-methy/ethenyl)cyc/ohexano/, 9Cl
~ (4R,6R)-form
I

:{OH
A
CIOH160 M 152.236
Present in oil of Citrus paradisi, C. reticulata, Herac/eum
canescens, Cymbopogon martini and others.
I> OS8400000.
C 10H 1,0 M 152.236 (4R,6R)-form [2102-59-2]
Isol. from Cymbopogon spp. (-)-cis-form
[58789-01-8] Constit. of valencia orange oil. Flavouring agent. Cryst.
Banthorpe, D.V. et al, Planta Med., 1976, 29, 10. (hexane). Mp 24-25°. [1X]n -30.0° (c, 2.1 in MeOH).
(4S,6R)-form [18383-51-2]
p-Mentha-1,8-dien-3-ol Mo-00538 (+)-trans-form
3-Methy/-6-(1 -methy/ethenyl)-2-cyc/ohexen-1-o/, 9CI. 6- Oil. Bp4 80-80.SO. [IX)~ +217.1°.
/sopropeny/-3-methy/-2-cyc/ohexen-1-o/. Isopiperitenol (4S,6S)-form [7632-16-8]
[491-05-4] (+)-cis-form
Constit. of dill seed oil. Oil. Bp 5.5 87-88°. [1X)n + 30.4° (c,
2 in MeOH).

HO~
(4R,6S)-form [2102-58-l]
(-)-trans-form
Constit. of valencia orange essence oil. Oil. Bp 10 102.2-
102.40. [1X]n -213°.
(4RS,6RS)-form
CtoH160 M 152.236 (±)-cis-form
Individual stereoisotp.ers not v. well characterised. Occurs Bp 16 108°. n~ 1.4779.
in oils of Cymbopogon martini and C. densiflorus and in 4-Nitrobenzoyl: Mp 94°.
citrus oils. An autoxidn. prod. of limonene. Bp0 _9 98°. (4SR,6SR)-form [5157-78-8)
(4017-76-9, 65733-29-1, 65733-30-4, 74410-00-7, 96555-02-1] (±)-trans-form
Schenk, G.O. et al, Justus Liebigs Ann. Chern., 1965, 687, 26 Bp 16 108°. n~ 1.4956.
(synth) 4-Nitrobenzoyl: Mp 101°.
[1197-06-4, 1197-07-5]
p-Mentha-1,8-dien-4-ol Mo-00539 Naves, Y.R., Helv. Chirn. Acta, 1964, 47, 1617 (synth)
4-M ethy/-1-( 1-methy/ethenyl)-3-cyc/ohexen-1-ol, 9CI Grandi, R. et al, Tetrahedron, 1974, 30, 4037 (synth)
[3419-02-l] Voisin, D. et al, Bull. Soc. Chirn. Fr., 1975, 375 (synth)

p-Mentha-1,8-dien-7-ol Mo-00541
4-(1-Methyletheny/)-1-cyc/ohexene-1-methanol, 9Cl. 1-
Hydroxymethyl-4-isopropenylcyc/ohexene. Perilla alcohol.
(R)-form Perillyl alcohol. Dihydrocuminyl alcohol

OOH
[536-59-4]

C 10H 1,0 M 152.236

lsol. from Zanthoxylum piperitum, Citrus junos, C. iyo,
Ledum pa/ustre and spearmint oils.
(R)-form [38630-70-5] ' (R)-form
[IX]~ + WO (c, l in EtOH).
(±)-form [28342-82-7]
A
C 10H 1,0 M 152.236
Bp 5 81-82°.
I> OS8395000.
[73069-45-1]
(R)-form [57717-97-2]
Sakai, T. et al, Bull. Chern. Soc. Jpn., 1968, 41, 1945 (isol)
Isol. from caraway seed oil and oil of Cymbopogon
Birch, A.J. et al, Aust. J. Chern., 1969, 22, 2037 (synth)
Jensen, H.P. eta/, J. Org. Chern., 1975, 40, 264 (synth) polyneuros. [1X]n + 73°.
(S)-form [18457-55-l]

98
p-Mentha-1,8-dien-10-ol - p-Mentha-1,8-dien-3-one Mo-00542 - Mo-00547

Occurs in a variety of essential oils, e.g. lavender, p-Mentha-3,8-dien-1-ol Mo-00545

Ocimum gratissimum. Oil. Bp 244.SO, Bp 11 118-121°. 1-Methyl-4-( 1-methylethenyl)-3-cyclohexen-1-ol, 9CI
Naphthylurethane: Cryst. Mp 146-147°. [55708-38-8]
[66141-69-3]
Kergomard, A. et al, Bull. Soc. Chim. Fr., 1958, 393 (synth)
Naves, Y.-R. et al, Compt. Rend. Hebd. Seances Acad. Sci., 1959,
249, 306 (isol)
Biichi, G. et al, J. Am. Chern. Soc., 1969, 91, 6473 (abs conjig)
v. Sydow, E. et al, Arch. Mass Spectral Data, 1970, 1, 436 (ms)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)

p-Mentha-1,8-dien-10-ol Mo-00542 c1oH1,o M 152.236

4-Methyl-a.-methylene-3-cyclohexeneethanol. p-Mentha- Isol. from black pepper oil.
1,8(10)-dien-9-ol Sakuda, Y., Nippon Kagaku Zasshi (Jpn. J. Chern.), 1960, 81, 1891;
1961, 82, 117 (synth)
Debrauwer, J. et al, Bull. Soc. Chim. Belg., 1975, 84, 167 (isol, ms,
pmr)

p-Mentha-1,4(8)-dien-3-one Mo-00546
3-Methyl-6-(1-methylethylid.ene)-2-cyclohexen-1-one, 9Cl. 6-
lsopropylidene-3-methyl-2-cyclohexenone. Piperitenone.
Pulespenone
C 10H 1,0 M 152.236 [491-09-8]
(R)-form [38142-45-9]
Bp8 _5 101-103°. [a.Ji:· 5 + 51.6°.
(S)-form
[a.]i; -65.SO {9, 0.74 in EtOH).
Ac: [15593-88-1].
ni;· 5 1.4993. A
yo
lsol. from grapefruit, lemon and mandarin oils. Bpu
102-104°. [a.Jn -46.8° (c, 0.72 in EtOH).
CIOH140 M 150.220
Ruegg, R. et al, Recherches, 1966, 15, 3 (synth, pmr)
Moshonas, M.G., J. Agric. Food Chern., 1971, 19, 769 (isol) Constit. of Lippia and Mentha spp. and of oil of
Nomura, M. et al, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), Cymbopogon martini. Oil. Bp 14 120-122°.
1979, 305 (synth) Nigam, M.C. et al, Can. J. Chern., 1965, 43, 521 (isol)
Beereboom, J.J. et al, J. Org. Chern., 1966, 31, 2026 (synth)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
p-Mentha-2,8-dien-1-ol Mo-00544
Naves, Y.R., Riv. !tal. Essenze, Profumi, Piante Off., Aromi,
1-Methyl-4-(1-methylethenyl)-2-cyclohexen-1-ol, 9CI. 4- Saponi, Cosmet., Aerosol, 1976, 58, 136 (rev)
lsopropenyl-1-methyl-2-cyclohexen-1-ol
p-Mentha-1,8-dien-3-one, SCI Mo-00547
3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-one, 9Cl. 6-
lsopropenyl-3-methyl-2-cyclohexen-1-one. lsopiperitenone
(1R,4R)-form [529-01-1]
I

~
cloH1,o M 152.236
(1R,4R)-form [52154-82-2]
Isof. from gingergrass oil (Cymbopogon martini) and
various Citrus oils. Metabolic and oxidn. prod. of
limonene. Bp6. 5 86.SO. ni? 1.4881. This is the cis-form CIOH140 M 150.220
ace. to most authors but the trans-form in CA. lsol. from oil of Mentha spp.
(1S,4R)-form [22972-51-6] (S)-form (16750-82-6]
Isol. from Cymbopogon and Citrus oils. Mp 18°. Bp 12 · · Alarm pheromone of the acarid mite Tyrophagus simills.
90°. [a.Ji? + 67.3°. ni? 1.4900. Oil. d~0 0.961. [a.Ji? +39.1° (c, 0.169 in hexane), [a.ln
[3886-78-0, 7212-40-0, 22771-44-4] +83° (synthetic). ni? 1.5037.
Naves, Y.R. et al, Bull. Soc. Chim. Fr., 1960, 37 (isol) 2,4-Dinitrophenylhydrazone: Mp 162-163°.
Schenk, G.O. et al, Justus Liebigs Ann. Chern., 1964, 674, 93
(63844-92-8]
(synth)
Handa, K.L. et al, J. Polym. Sci., 1964, 53, 1407 (isol)
Schenk, G.O. et al, Justus Liebigs Ann. Chern., 1965, 687, 26
(synth)
Kuwahara, Y. et a!, Agric. Bioi. Chern., 1987, 51, 3441 (isol)

99
 p-Mentha-3,8-dien-2-one - p-Menthane-1,2-diol Mo-00548 - Mo-00552

p-Mentha-3,8-dien-2-one Mo-00548 Karrer, W. eta/, Konstitution und Vorkommen der Organischen

6-Methy/-3-(1-methy/ethenyl)-2-cyc/ohexen-1-one, 9CI Pf/anzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, i972-1985,
no. 557 (occur)
(66309-78-2] Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7;426 (cmr)
Oonk, H.A.J. et a/, Acta Crystallogr., Sect. B, 1976, 32, 500 (cryst
struct)
Akhita, A. et al, Phytochemistry, 1980, 19, 1433 (biosynth)
Sax, N.J., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 473.

p-Menthane Mo-00551
CIOHI40 M 150.220 1-Methyl-4-( 1-methy/ethyl)cyc/ohexane. 1-lsopropyl-4-
Found in tobacco smoke. methy/cyc/ohexane
Newell, M.P. et al, TOBS, 1978, 22, 6 (isol) [99-82-l]

p-Mentha-4(8),6-dien-3-one Mo-00549
3-Methy/-6-( 1-methy/ethy/idene)-3-cyc/ohexen-1-one, 9CI.
Pulespenone
6A (1RS,4RS)-form

C10H 10 M 140.268
Menthane numbering shown. lsol. from essential oils, e.g.
turpentine and from fossil resins, prob. as artifact.
(JRS,4RS)-form [1678-82-6]
trans-form
C 10H 140 M 150.220 Oil. Bp 170.55°. ni? 1.4352.
Isol. from Mentha pu/egium. Bp 15 122-125°. ni? 1.5230.
(JRS,4SR)-form [6069-98-3]
2,4-Dinitropheny/hydrazone: Cryst. (EtOH). Mp 134-135°. cis-form
de Pascual Teresa, J. et al, An. R. Soc. Esp. Fis. Quim., Ser. B, Oil. Bp725 170.9°. ni? 1.4414.
1962, 58, 351 (isol)
Cocker, W. et a/, J. Chern. Soc. C, 1966, 946 (synth)
Senda, Y. eta/, Tetrahedron, 1975, 31, 2905 (cmr)
p-Mentha-6,8-dien-2-one Mo-00550
2-Methy/-5-(1-methy/ethenyl)-2-cyc/ohexen-1-one, 9CI. 5- p-Menthane-1,2-diol Mo-00552
lsopropeny/-2-methy/-2-cyc/ohexen-1-one. Carvone. Carvo/ 4-Isopropy/-1-methyl-1 ,2-cyc/ohexanedio/
(obso/.)
(33669-76-0]
[99-49-0]

o0J (1 ~OH
, OH

X (R}fo~ X 4
(lp,2a,4<)-fo~

C10H 140 M 150.220 CIOH:zoOl M In.267

(R)-form [6485-40-1] (1 p,1«,4~)-form
Constit. of spearmint (Mentha crispa) and kuromoji and Constit. of Ferula jaeschkeana. Oil. [a]~ + 7° (c, 1.5 in
other oils. Flavour ingredient. Oil. Bp 230-231°. [1X]n MeOH).
-62.46°. (JP,1P,41;)-form
t> 088650000. From F. jaeschkeana.
Oxime: Garg, S.N. eta/, Phytochemistry, 1989, 28, 634.
C10H 15NO M 165.235
Cryst. (MeOH). Mp no. [a]~ -39.3° (EtOH).
(S)-form [2244-16-8]
Constit. of dill (Anethum graveo/ens) and caraway
(Carum carvz) oils. Also in oils of Lippia carviodora,
.Orthodon carvoriferum and Artemisa spp. Flavour
ingredient. Oil. Bp 230°. [a]i? + 61.2°.
t> OS8670000.
Oxime: Cryst. (MeOH). Mp no. [a]~ +39.SO (EtOH).
(±)-form [22327-39-5]
Constit. of gingergrass oil and of oil of Litsea
guatema/ensis and others. Oil. Bp 231°.
Oxime: Cryst. (MeOH). Mp 93-94°.
Ronayne, J. et al, J. Am. Chern. Soc., 1966, 88, 5288 (pmr)
Honwad, V.K. eta/, Indian J. Chern., 1967, 5, 234 (synth)
Schevitz, R.W. eta/, J. Chern. Soc., Chern. Commun., 1969, 711
(abs config)

100
p-Menthane-1,4-diol- p-Menthane-2,5-diol Mo-00553 - Mo-00557

p-Menthane-1,4-diol Mo-00553 p-Menthane-2,3-diol Mo-00555

1-Methyl-4-( 1-methylethyl)-1 ,4-cyclohexanediol. 1-1sopropyl- 3-Methyl-6-(1 -methylethyl)-1 ,2-cyclohexanediol. 3-1sopropyl-
4-methyl-1 ,4-cyclohexanediol 6-methyl-1 ,2-cyclohexanediol
OH

x--oH
r+rOH (1S,2R,3R,4R)-form
(1RS,4RS)-form

H
C 10H 100 2 M 172.267
C 10H 100 2 M 172.267 (1S,2R,3R,4R)-form [51745-19-8]
(1RS,4RS)-form [1753-42-0] Oil. [rxln + 115°.
trans-form (JR,2S,3S,4R)-form [51745-21-2]
Constit. of Ferula jaeschkeana. Cryst. (MeOH aq.). Mp lsol. from peppermint oil. Oil. [rxln + 32.4°.
137-138°, Mp 153°.
Katsuhara, J. et al, Kogyo Kagaku Zasshi, 1966, 69, 1170 (isol)
(JRS,4SR)-form Seeman, J.I. eta/, J. Org. Chern., 1974, 39, 2444 (synth)
cis-form
Cryst. (MeOH aq.). Mp 119-120°.
p-Menthane-2,4-diol Mo-00556
Hudec, J. eta/, Tetrahedron Lett., 1967, 3175 (synth)
4-M ethyl-1-(1 -methylethyl)-1 ,3-cyclohexanediol. 1-/sopropyl-
Rybinski, S., CA, 1968, 72, 32042 (synth)
4-methyl-1 ,3-cyclohexanediol

$2
Garg, S.N. et al, Phytochemistry, 1989, 28, 634 (isol)
[13835-34-2]
p-Menthane-1,8-diol, SCI Mo-00554
4-Hydroxy-rx,rx,4-trimethylcyclohexanemethanol, 9Cl. 4-(1- /0H
Hydroxy-1-methylethyl)-1-methylcyclohex(Uio/.
Dipenteneglycol. Terpin, BAN. Terpinolt ( 1R,2R,4 R)-form
[80-53-5]
H

2
C 10H 100 2 M 172.267
(JR,2R,4R)-form [1845-62-1]
(1RS,4RS)-form Cryst. (hexane). Mp 76.SO.
(JR,2R,4S)-form [22556-03-2]
Cryst. (hexane). Mp 115-116°.
OH (JS,2R,4R)-form [1845-63-2]
C 10H 100 2 M 172.267 Liq.
(JRS,4RS)-form [565-48-0] (JS,2R,4S)-form [22556-02-1]
cis-form Cryst. (hexane). Mp 153°.
lsol. from leaves of Cupressus torulosa and fruits of [42962-94-7, 42962-95-8, 42962-96-9, 42962-97-0]
Schinus molle. Expectorant. Prisms or plates (EtOAc). Sakuda, Y., Bull. Chern. Soc. Jpn., 1969, 42, 475.
Spar. sol. H 20. Mp 104-105°. Bp 263-265°. Originally
assigned the trans-config. p-Menthane-2,5-diol Mo-00557
Monohydrate: [2451-01-6]. 2-Methyl-5-( 1-methylethyl)-1 ,4-cyclohexanediol. 2-/sopropyl-
Rhombic pyramids (H 20). Mp 116-117°. 5-methyl-1 ,4-cyclohexanediol

O
(JRS,4SR)-form [565-50-4] [38618-26-7]
trans-form
Found in Myrocarpus silvestris, Protinium brasiliensis ,OH
Chinese anise and sweet fennel oil. Mp 158-159°. Bp (1R,2R,4R,5R)-form
258°. Hygroscopic, forms hydrate, Mp 123° (sealed
tube), which loses Hp at 70-80°. Originally assigned the HO'
I
cis-config.
A
Di-Ac: Bp 14 145°.
C 10H 100 2 M 172.267
[2451-01-6, 16485-15-7]
(1R,2R,4R,5R)-form [27525-54-8]
Barnes, C.S., Aust. J. Chern., 1958, 11, 134 (conjig, bib[)
Peyron, L. et al, Bull. Soc. Chim. Fr., 1969, 399 (isol)
Cryst. (C6H 6). Mp 156.5-157°. [rx]iJ -42° (c, 6.88 in
Perto1di, M. eta/, CA, 1970, 73, 91168 (isol) EtOH).
Suga, T. eta/, Bull. Chern. Soc. Jpn., 1982, 55, 914 (cryst struct) (JR,2R,4R,5S)-form [27525-58-2]
Martindale, The Extra Pharmacopoeia, 28th/29th Ed., Constit. of Mentha arvensis. Cryst. (hexane/Et20). Mp
Pharmaceutical Press, London, 1982/1989, 2029. 144-144.SO. [rx]i,S +20° (c, 0.876 in EtOH).
Hassan, M.M.A. eta/, Anal. Profiles Drug Subst., 1985, 14, 273
(rev, synth, pharmacol, anal) (1R,2S,4R,5R)-form [27525-56-0]
Ho, T.-I. eta/, Acta Crystallogr., Sect. C, 1986, 42, 1787 (cryst Cryst. (hexane/Etp). Mp 128.5-129°. [rx]~ +20° (c, 7.86
struct) in EtOH).
(1R,2S,4R,5S)-form [27525-52-6]
Cryst. (hexane/Et20). Mp 177-177.SO. [rx]i,S +87° (c,
0.874 in EtOH).
(JS,2R,4R,5R)-form [27525-53-7]

101
p-Menthane-2,9-diol- p-Menthane-1,2,4-triol Mo-00558 - Mo-00563

Cryst. (C 6H 6). Mp 132-133.SO. [ex]i,6 +23° (c, 7.70 in (1R,3R,4R)-form (3564-98-5]

EtOH). trans-form
(IS,2R,4R,5S)-form [27525-57-1] Mp 60-61°.
Cryst. (hexanejEtp). Mp 168.5-169.SO. [ex]~ +65° (c, (JR,3S,4R)-form [3564-95-2]
0.942 in EtOH). cis-form
(JS,2S,4R,5R)-form [27525-55-9] Mp 73-74°.
Cryst. (hexane/Etp). Mp 120.5-121°. [ex]~ +20° (c, 5.53 (JS,3R,4S)-form [19956-48-0]
in EtOH). Mp 65-66°.
(IS,2S,4R,5S)-form [27525-51-5] Barbier, P. eta/, Compt. Rend. Hebd. Seances Acad. Sci., 1897,
Cryst. (hexane/Etp). Mp 136.5-137°. [ex]i; +34° (c, 7.46 124, 1309 (synth)
in EtOH). Grignard, V. eta/, Compt. Rend. Hebd. Seances Acad. Sci., 1928,
187, 273 (synth)
Hashizume, T. eta/, Tetrahedron Lett., 1967, 3355 (isol) Shishibori, T., Bull. Chern. Soc. Jpn., 1968, 41, 1170 {synth, ir)
Sto1ow, R.D. eta/, J. Org. Chern., 1971, 36, 960 (synth) Chabudzinski, Z. eta/, Pol. J. Chern. (Rocz. Chern.), 1968, 42, 283
(synth)
p-Menthane-2,8-d.iol, SCI Mo-00558
3-Hydroxy-P,4-dimethylcyclohexaneethano/, 9CI. 5-(2- p-Menthane-4,9-d.iol Mo-00561
Hydroxy-1-methy/ethyl)-2-methylcyc/ohexanol 1-Hydroxy-ex,4-dimethylcyclohexanemethanol. 1-(2-Hydroxy-

!
[57685-12-8] 1-methy/ethyl)-4-methy/cyc/ohexanol
I
I
OH
2
4

OH C 10H 200 2 M 172.267

C 10H 20 0 2 M 172.267 Oil. Bp4 120-121°.
(1 S,2~ ,4S)-form Di-Ac: Oil. Bp5 125-127°.
Liq. Bp0 _4 115-117°. [exJn -14.1° (c, 1.2 in CHC1 3). Eschinari, H.E. eta/, J. Org. Chern., 1955, 20, 1666 (synth)
Clemo, G.R. eta/, J. Chern. Soc., 1952, 3839 (synth)
Brown, H.C. eta/, J. Am. Chern. Soc., 1967, 89, 5475 (synth)
p-Menthane-1,2,3-triol Mo-00562
1-Methy/-4-isopropy/-1 ,2,3-cyc/ohexanetrio/
p-Menthane-3,4-d.iol Mo-00559

~OH
4-M ethyl-1-(1-methylethyl)-1 ,2-cyc/ohexanedio/. 1-Isopropyl-
4-methy/-1 ,2-cyc/ohexanedio/
[4053-64-9]
:COH
(1R,3R,4R)-form
Absolute C 10H 200 3 M 188.266
configuration
(IS,2R,3S,4R)-form [66767-24-6]
Metab. of Fusicoccum amygdali. Cryst. (C6 H 6 ). Mp 86-
870.
CIOH2002 M 172.267 Casinovi, C.G. eta/, Experientia, 1978, 74, 298.
(JR,3R,4R)-form [7647-94-1] Randazzo, G. eta/, Phytochemistry, 1981, 20, 2177 (biosynth)
Cryst. Mp 75-76°. [ex]i? -6° (c, 2 in MeOH).
(IR,3S,4R)-form [6070-07-1] p-Menthane-1,2,4-triol Mo-00563
Cryst. Mp 80-81°. [ex]i? + 13° (c, 1 in MeOH). 1-Methy/-4-( 1-methylethyl)-1 ,2,4-cyc/ohexanetriol. 4-
[42962-98-1, 42962-99-2, 42963-00-8, 42963-01-9, 55102-23-3] Isopropy/-1-methyl-1 ,2,4-cyc/ohexanetriol
Suga, T. et a/, J. Org. Chern., 1967, 32, 965. [62137-86-4]

p-Menthane-3,8-d.iol, SCI Mo-00560

2-Hydroxy-ex,ex,4-trimethylcyclohexanemethanol, 9CI.
Menthog/ycol. Isopu/egol hydrate
[42822-86-6]

~OH
CIOH2003 M 188.266
(1R,3R,4R)-form (IS,2S,4S)-form [36150-04-6]
(1 ex,2p,4fJ)-form

+
I
Constit. of the volatile oil of Zanthoxylum bundruga
fruits. Cryst. (Et20). Mp 173-174°. [exln +31° (c, 0.5 in
OH EtOH).
M 172.267

102
p-Menthane-1,2,8-triol- p-Menthan-3-ol Mo-00564 - Mo-00567

[22555-54-0] C 10H 200 M 156.267

Garside, P. et al, J. Chern. Soc. C, 1969, 716 (synth) (JR,2R,4R)-form [1126-39-2] (- )-Carvomenthol
Thappa, R.K. et al, Phytochemistry, 1976, 15, 1568 (isol) Oil. [ali? -24.2°.
3,5-Dinitrobenzoyl: Cryst. (pet. ether). Mp 106-107°. [ocln
p-Menthane-1,2,8-triol Mo-00564 -52.1 o (c, 2 in CHC1 3).
4-( 1-Hydroxy-1-methy/ethyl)-1-methy/-1 ,2-cyc/ohexanedio/, (JR,2R,4S)-form [3858-43-3] (- )-lsocarvomenthol
9CI Oil. Bp 17 106°. [a]~ -17.72°.
[58506-22-2] 3,5-Dinitrobenzoyl: Yellow cryst. Mp 111°. [ocln -26.7°.
(JR,2S,4R)-form
(+ )-Neocarvomenthol
Oil. [ali? + 37.5°.
3,5-Dinitrobenzoyl: Cryst. (pet. ether). Mp 128-129°. [1X]n
+23° (c, 1.6 in CHC1 3).
(1R,2R,4R)-form (JR,2S,4S)-form [3858-45-5] (- )-Neoisocarvomenthol
Oil. [alb' -34.7°.
3,5-Dinitrobenzoyl: Yellow cryst. Mp 71-72°. [1X]n -16°.
(JS,2R,4R)-form [1126-41-6] ( + )-Neoisocarvomenthol
Oil. [alb' +34.7°.
3,5-Dinitrobertzoy/: Cryst. Mp 102°. [ocln -9° (CHC1 3).
(JS,2R,4S)-form [3858-49-9] (- )-Neocarvomenthol
Oil. Bp 18 102°. [IX]~ -41.7°.
3,5-Dinitrobenzoyl: Cryst. Mp 129°. (ali? -22° (CHC1 3).
(JS,2S,4R)-form
( + )-Isocarvomenthol
Oil. [ali? + 19.3°.
3,5-Dinitrobenzoyl: Cryst. (pet. ether). Mp 110°. [ocln +26°
(CHC1 3).
[54145-82-3] (JS,2S,4S)-form
Carman, R.M. eta/, Aust. J. Chern., 1984, 37, 2129 (synth, bib/) (+ )-Carvomenthol
Oil. Bp 14 101.8-102°. [a]~ +27.69°.
p-Menthan-1-ol Mo-00565 3,5-Dinitrobenzoy/: Cryst. (EtOHjEtOAc). Mp 107°. (a]~
1-Methy/-4-(1 -methy/ethyl)cyc/ohexano/, 9CI. 4-/sopropy/-1- + 52.8° (CHC1 3).
methy/cyc/ohexanol (1 RS,2SR,4RS)-form
[21129-27-1] ( ± )-Neocarvomenthol
Oil. ni? 1.4637.
3,5-Dinitrobenzoyl: Leaflets (EtOH). Mp 101°.
(JRS,2RS,4SR)-form
(1RS,4RS)-form ( ± )- /socarvomenthol
Bp20 110°. n);! 1.4669.
3,5-Dinitrobenzoyl: Yellow prisms. Mp 85.5°.
[499-69-4, 1126-39-2, 1126-40-5, 1126-41-6, 3127-80-8, 3858-43-3,
C 10H 200 M 156.267 3858-45-5, 20752-34-5, 42846-32-2]
Isol. from spearmint oil. Oritani, T. et al, Agric. Bioi. Chern., 1973, 37, 1691 (synth)
(1RS,4RS)-form [3901-95-9] Noma, Y. eta/, Agric. Bioi. Chern., 1974, 38, 1637 (synth)
cis-form Brown, H.C. et al, Tetrahedron, 1975, 31, 925 (synth)
Needles. Mp 41-43°. Kartha, G. et al, J. Chern. Soc., Perkin Trans. 2, 1976, 717 (pmr)
(1 RS,4SR)-form [390 1-93-7]
trans-form p-Menthan-3-ol Mo-00567
Bp 5 74°. ni? 1.4595. 5-Methy/-2-(1-methylethyl)cyclohexano/. 2-lsopropy/-5-
[3901-93-7] methylcyc/ohexano/
Chabudzinski, Z. et al, Pol. J. Chern. (Rocz. Chern.), 1963, 37, [1490-04-6]
1571 (synth)

:tOH
Tsukamoto, Y. et al, Agric. Bioi. Chern., 1975, 39, 617 (synth)

p-Menthan-2-ol Mo-00566
2-Methy/-5-(1-methy/ethyl)cyc/ohexano/. 5-Isopropyl-2- (1R,3R,4R)-form
methylcyc/ohexanol
C 10H 200 M 156.267
Found in many essential oils.
I> Irritant, allergen.
(1R,2R,4R)-form
(1R,3R,4R)-form [20752-34-5]
(+ )-Neoisomenthol
Oil. Mp -8°. Bp 214.6°. [a]);! +3.8° (c, 6 in EtOH).

103
p-Menthan-4-ol - p-Menthan-8-ol Mo-00568- Mo-00570

(1R.JR,4S)-form [2216-51-5] (-)-Menthol. Menthacamphor. p-Menthan-4-ol Mo-00568

Peppermint camphor 4-M ethy/-1-( 1-methy/ethyl)cyc/ohexano/. 1-Isopropy/-4-
Present in large amts. in peppermint oil (Mentha methy/cyc/ohexanol
piperita), also in other M. spp., Artemisia spp., [470-65-5]
Glechoma hederacea andothers. Used in confectionery,
perfumery, menthol cigarettes, inhalers, etc. Mild local

H~
anaesthetic, analgesic, antipruritic and internally as a
carminative. Cryst. (MeOH) with strong peppermint
odour. Sl. sol. Hp, v. sol. org. solvs. Mp 42.5-43°. Bp
216°. [ex]~ -50.0° (c, 2 in CHC1 3). Exists in four cryst. (IRS,4RS)-form
modifications; Mp given is the highest Component of
Larylgan. C 10H:11P M 156.267
I> OT0700000. Present in turpentine from Pinus sy/vestris and isol. from
(JR.JS,4R)-form [23283-97-8] Mentha spp.
(+ )-Isomenthol (JRS,4RS)-form [3239-02-9]
Cryst. (MeOH). Mp 82.5°. Bp 218°. [ex]~ +25.9° (c, 1.56 cis-form
in CHC1 3). Cryst. Mp 52-53°.
(JR.JS,4S)-form [2216-52-6] Phenylurethane: Cryst. Mp 131-141°.
(+ )-Neomenthol (1RS,4SR)-form [3239-03-0]
Constit. of Japanese peppermint oil. Oil. Mp -22°. Bp 14 trans-form
83-84°. [ex]~ + 18.02° (neat). Oil.
(JS.JR,4R)-form [20747-49-3] Pheny/urethane: Cryst. Mp 99-100°.
(- )-Neomenthol
Bowman, R.M. et al, J. Chern. Soc. C, 1966, 612 (synth)
Oil. Bp 10 97.6°. [ex]~ -20.7° (EtOH). Murphy, R. et al, Aust. J. Chern., 1976, 29, 617 (synth)
(1S.JR,4S)-form [20752-33-4]
(- )-Isomenthol
Cryst. (MeOH). Mp 82.SO.
p-Menthan-7-ol Mo-00569
4-(1-Methy/ethyl)cyc/ohexanemethanol, 9CI. 1-
(1S.JS,4R)-form Hydroxymethyl-4-isopropy/cyc/ohexane
(+)-Menthol
Cryst. (MeOH). Mp 38-40°. [ex] 0 +48.3° (EtOH). [5502-75-0]
(1S.JS,4S)-form
(- )-Neoisomenthol
Isol. from geranium bourbon oil (Pe/argoniwn roseum).
(lRS,4RS)-form
(JRS.JSR,4RS)-form
( ± )- Isomenthol
Needles. Mp 53-54°. Bp 218.5-218.6°.
(JRS,3SR,4SR)-form
(±)-Neomenthol C10H 100 M 156.267
Plates (pet. ether). Mp 51°. Bp 163 212°. (1RS,4RS)-form [13674-19-6]
(1RS,3RS,4RS)-form trans-form
( ± )-Neoisomenthol Insect pheromone from Anthonomus grandis. Viscous liq.
Mp W. Bp6 81°. n~ 1.4676. Bp 13 115°. n:i 1.4632.
(1RS.JRS,4SR)-form [15356-20-4] (1RS,4SR)-form [13828-37-0]
(±)-Mentho/ cis-form
Flavour ingredient. Needles (pet. ether). Mp 34°. Bp Viscous liq. Bp21 126-127°. n:i 1.4677.
216°. van Bekkum, H. et al, Reel. Trav. Chim. Pays-Bas (J. R. Neth.
Katsuhara, J. et al, Bull. Chern. Soc. Jpn., 1966, 39, 617 (synth, Chern. Soc.), 1962, 81, 833 (synth)
menthol) Mitzner, B.M. et al, Appl. Spectrosc., 1968, 22, 34 (ir)
Hashimoto, A. et al, Agric. Bioi. Chern., 1970, 34, 1843 (synth, Hedin, P.A. et al, J. Insect Physiol., 1974, 20, 2135 (isol)
isomenthol)
Oritani, T. et al, Agric. Bioi. Chern., 1973, 37, 1695 (synth, p-Menthan-~1 Mo-00570
neoisomenthol) ex,ex,4- Trimethylcyc/ohexanemethanol, 9CI. 1-(1-Hydroxy-1-
Leffingwell, J.C. et al, Cosmet. Perfum., 1974, 89, 69 (rev) methylethyl)-4-methy/cyc/ohexane. Menthanol. Dihydro-ex-
Yamaguchi, S. et al, Tetrahedron Lett., 1977, 89 (abs config)
Nakatani, Y. et al, Synthesis, 1978, 147 (synth) terpineo/
Dauzonne, D. et al, Org. Magn. Reson., 1981, 17, 18 (cmr) (498-81-7)

6
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 266.
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 791.
(lRS,4RS)-form

+
I

OH
C 10H100 M 156.267
Present in Pinus spp., lemon and spearmint oils. Fragrance
intermed.
(JRS,4RS)-form [29789-01-3]

104
p-Menthan-9-ol - p-Menthan-3-one Mo-00571- Mo-00573

trans-form p-Menthan-2-one Mo-00572

Plates or needles with floral odour. Mp 35°. BPt.s 63- 2-Methyl-5-( 1-methylethyl)cyclohexanone. 5-Isopropyl-2-
650. methylcyclohexanone
p-Nitrobenzoyl: Cryst. (EtOHjEtOAc). Mp 98.5-99.SO. [59471-80-6]

No
Phenylurethene: Long needles (pet. ether). Mp ll5°.
(1 RS,4SR)-form

X
cis-form
Mp 46-47° (25°). Bp30 l10°.
p-Nitrobenzoyl: Cryst. (EtOH/EtOAc). Mp 88-88.SO. (lR,4S)-form
Phenylurethene: Short needles. Mp 114°.
[29789-01-3] C10H 180 M 154.252
Perkin, W.H. eta/, J. Chern. Soc., 1905, 87, 639 (synth) (JR,4S)-form [13163-74-1]
Zeitschel, 0. eta/, Ber., 1927, 60, 1372 (isol, synth) (- )-Isocarvomenthone
Keats, G.H. et a/, J. Chern. Soc., 1937, 2003 (synth)
Co1onge, J. et a/, Bull. Soc. Chim. Fr., 1959, 1505 (synth)
Oil. Bp 220-221°. [ex]i,O -1.4° (CHC1 3).
Von Rudloff, E. eta/, Can. J. Chern., 1963, 41, I, 2615 (isol, synth, Semicarbazone: Cryst. (pet. ether). Mp 105°.
glc) (JS,4S)-form [13163-73-0] (- )-Carvomenthone
Gollnick, K. et a/, Tetrahedron, 1966, 22, 123 (synth, struct, ir) lsol. from oils of Blumea malcolmii, B. eriantha, Mentha
Opdyke, D.L.J., Food Cosmet. Toxicol., 1974, 12, 529 (rev, use, arvensis and Tanacetum vulgare. Oil. Bp 220°. [ex]~
tox)
Carman, R.M. eta/, Aust. J. Chern., 1976, 29, 133 (synth, pmr)
-27.95° (MeOH).
Simpson, R.F. et a/, Phytochemistry, 1976, 15, 328 (isol) Semicarbazone: Cryst. (EtOH). Mp 193°.
Hugel, H.M. eta/, Aust. J. Chern., 1977, 30, 1287 (synth) [499-70-7, 3901-91-5, 5206-83-7]
Dauzonne, D. et a/, Org. Magn. Reson., 1981, 17, 18 (cmr)
Bazyl'chik, V.V. eta/, J. Chromatogr., 1982, 248, 321 (pmr, glc) Simonson, J.L. et al, J. Chern. Soc., 1922, 876 (isol)
Willhalm, B. eta/, J. Chern. Soc., 1965, 6478 (ms)
Barieux, J.-J. et a/, Bull. Soc. Chim. Fr., 1971, 3978 (synth)
p-Menthan-9-ol, SCI Mo-00571 Fringuelli, F. eta/, J. Chern. Soc. C, 1971, 297 (synth)
p,4-Dimethylcyclohexaneethanol, 9CI
[5502-76-1] p-Menthan-3-one Mo-00573
5-Methyl-2-(1-methylethyl)cyclohexanone. 2-/sopropyl-5-

~
methylcyclohexanone
[10458-14-7]

~~OH A
(R)-cis-form

J:o
(1R,4R)-form

C 10H 200 M 156.267

lsol. from the oil of Artemisia tridentata.
(R)-cis-form [13844-68-3] C 10H 180 M 154.252
Oil. [exln - 1.2°. (JR,4R)-form [1196-31-2] ( + )-/somenthone
Ac: [13844-69-4]. Found in pennyroyal oil (Hedeoma pulegioides), Mentha
C12H 220 2 M 198.305 arvensis, Pelargonium tomentosum and other essential
Oil. [exln -7.8°. oils. Oil. Bp 212°. [exln +95°. ni,O 1.4530.
(R)-trans-form [13844-70-7] Semicarbazone: Cryst. Mp 264°.
Oil. [exln -0.8°. (1R,4S)-form [14073-97-3] (- )-Menthone
Ac: [13844-71-8]. Occurs with menthol in many essential oils including
Oil. [exln -7.8°. peppermint and geranium oils. Used in flavour
(S)-cis-form [13844-62-7] compositions. Liq. with peppermint odour. Spar. sol.
Oil. [exln + 1°. Hp. Mp -6°. Bp 207°. [ex]i,O -24.8°. ni] 1.4490.
Ac: [13844-63-8]. Semicarbazone: Cryst. (EtOH). Mp 185-187°. [exln -64°
Oil. [exln +5.9°. (chloral hydrate).
(S)-trans-form [13844-64-9] (1S,4R)-form [3391-87-5] ( + )-Menthone
Oil. [exln +0.9°. Found in some essential oils, e.g. those of Barosma
Ac: [13844-65-0]. pulchellum, M. sachalinensis. Less common than the
Oil. [exJn + 5.6°. (-)-form. Oil. Bp 204°. [ex]:.! + 24.85°.
(±)-cis-form [5113-95-1] Semicarbazone: Cryst. (EtOH). Mp 187-189°.
Oil. Bp22 127-128°. (JS,4S)-form [18309-28-9] (- )-/somenthone
3,5-Dinitrobenzoy/: Mp 52-52.SO. lsol. from oils of M. arvensis, M. pulegium, H.
pulegioides and others. Bp7 79-80°. [ex]i,O -94.3°.
(±)-trans-form [5113-94-0]
Oil. Bp 13 l14-ll5°. (JRS,4RS)-form [36977-92-l]
3,5-Dinitrobenzoyl: Mp 77-78.SO.
( ±)- M enthone. Thymomenthone
Spar. sol. Hp. Bp 205° (212°).
[24398-94-5, 24399-12-0]
Oxime:
Kinney, C.R. et al, J. Org. Chern., 1941, 6, 612 (isol) C 10H 19NO M 169.266
Schulte, H. eta/, Helv. Chim. Acta, 1966, 49, 2150 (synth) Needles (EtOH). Mp 80°.
Albaiges, J. et al, J. Org. Chern., 1966, 31, 3507 (synth)

105
p-Mentha-1,3,5,8-tetraene - p-Mentha-1,3,5-triene-2,3,5-trio I Mo-00574- Mo-00580

2,4-Dinitrophenylhydrazone: Yellow leaflets or needles. Mp p-Mentha-1,3,5-triene-2,8-diol Mo-00577

141-142°. 3-Hydroxy-oc,oc,4-trimethylbenzenemethanol, 9Cl. 3-Hydroxy-
[89-80-5, 491-07-6, 1074-95-9, 36977-92-1) oc,oc,4-trimethylbenzyl alcohol
Brown, H.C. et al, J. Am. Chern. Soc., 1961, 83, 2952 (synth) [4397-18-6]
Wellman, K.M. et a/, J. Am. Chern. Soc., 1965, 87, 66 (cd)

20H
Willhalm, B. eta/, J. Chern. Soc., 1965, 6478 (ms)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
nos. 545, 546 (occur)
Hibino, K. et al, Tetrahedron Lett., 1974, 1295 (synth)
Liang, L.Y. eta/, Agric. Bioi. Chern., 1989, 53, 2517 (synth)

p- Mentha-1,3,5,8-tetraene
1-Methyl-4-(1-methylethenyl)benzene, 9CI. p,oc-
Dimethylstyrene, 8CI. 1-Methyl-4-isopropenylbenzene. p-
/sopropenyltoluene. 2-(4-M ethylphenyl)propene
[1195-32-0]
OH
Mo-00574
C 10H 140 2 M 166.219
Constit. of Lavandula gibsonii. Cryst. Mp 105-108°.
8-Me ether: [88544-85-8]. 8-Methoxy-p-mentha-1,3,5-trien-
2-ol. 5-(1-Methoxy-1-methylethyl)-2-methylphenol, 9CI
C 11 H 160 2 M 180.246
Constit. of L. gibsonii. Cryst. (pet. ether). Mp 89-92°.
Leitich, J. et al, Monatsh. Chern., 1964, 95, 129 (synth)
Patwardhan, S.A. eta/, Phytochemistry, 1983, 22, 2081 (isol)

p-Mentha-1,3,5-triene-2,3,5,7-tetrol Mo-00578

C 10Hu M 132.205
Occurs in Chamaecyparis, Citrus, Eucalyptus, Juniperus
and Ribes sp. oils. Mp -20°. Bp 184-185°.
Nitrosochloride: Cryst. (MeOH). Mp 100-102°.
Perkin, W.H. et al, J. Chern. Soc., 1905, 87, 639.
Tiffeneau, M., Ann. Chim. (Paris), 1907, 10, 194.
Attaway, J.A. eta/, Phytochemistry, 1966, 5, 1273 (isol) C 10H 1P 4 M 198.218
2,3-Di-Me-ether: 2,3-Dimethoxy-p-mentluz-1,3,5-triene-5,7-
p-Mentha-1,3,5,8-tetraen-2-ol Mo-00575 dio/
2-Methyl-5-(1-methylethenyl)phenol, 9CI. 5-/sopropenyl-2- CuH 180 4 M 226.272
methylphenol. 3-Hydroxy-oc,4-dimethylstyrene Constit. of Relhania squarosa.
[56423-47-3] Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (tsol)

p-Mentha-1,3,5-triene-3,8,9,10-tetrol Mo-00579
2-(1-Hydroxymethyl-1 ,2-dihydroxyethyl)-5-methylphenol. 2-
(2-H ydroxy-4-methylphenyl)-1 ,2,3-propanetriol

C 10Hu0 M 148.204
Constit. of Lavandula gibsonii. Yellow viscous liq. Bp0. 6
120-125°.
Patwardhan, S.A. et al, Phytochemistry, 1983, 22, 2080.

p-Mentha-1,3,8-triene Mo-00576 C 10H 1P 4 M 198.218

1-Methyl-4-(1-methylethenyl)-1 ,3-cyclohexadiene, 9CI. 1- Menthane numbering shown.
/sopropenyl-4-methyl-1 ,3-cyclohexadiene 9-0-(2-Methylpropanoyl):
[18368-95-1] Ct4Hz00 5 M 268.309
Constit. of Brasilia sickii. Gum.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1213.

p-Mentha-1,3,5-triene-2,3,5-triol Mo-00580
6- Methyl-3-(1-methylethyl)-1 ,2,4-benzenetriol. 3- /sopropyl-6-
methyl-1 ,2,4-benzenetriol

C 10H 14 M 134.221
lsol. from Petroselinum sativum (Yugoslavian parsley). Bp 5
65°. n~ 1.5395.
Gamero, J. eta/, Bull. Soc. Chim. Fr., 1967, 4679 (isol)
AoH
HOXOH
Birch, A.J. et al, Aust. J. Chern., 1969, 22, 2037 (synth)
Thomas, A.F. et al, Helv. Chim. Acta, 1970, 53, 770 (synth)
M 182.219

106
p-Mentha-1,3,5-triene-3,8,9-triol- p-Menth-3-ene Mo-00581 - Mo-00585

2,3-Di-Me ether: 2,3-Dimethoxy-p-mentha-1,3,5-trien-5-ol Thomas, A.F. et a/, Helv. Chim. Acta, 1964, 47, 475 (ms)
C 12H 180 3 M 210.272 Schnelle, F.J. et a/, Planta Med., 1968, 16, 48 (isof)
Constit. of Relhania squarosa. Sakota, N. et a/, Bull. Chern. Soc. Jpn., 1971, 44, 485 (abs config)
Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 3173 (isol)
p-Menth-2-ene Mo-00584
3-Methyl-6-(1-methylethyl)cyclohexene. 3-/sopropyl-6-
p-Mentha-1,3,5-triene-3,8,9-triol Mo-00581
methylcyclohexene
2-(2-Hydroxy-4-methylphenyl)-1 ,2-propanediol, 9CI. p-
Cymene-3,8,9-triol. Eupatriol [5256-65-5]
[99481-57-9]

20H
HO CH2 0H
CIOHI8 M 138.252
(IR,4R)-form [31658-04-5]
(1R,4R)-form

(+)-cis-form
CIOHI403 M 182.219 Oil. Bp 10 46.8°. [oc]i? +45.2°.
Constit. of Eupatorium tashiroi. Oil. [oc]i?+ oo (c, 0.5 in
MeOH). (IR,4S)-form [5113-93-9]
(+)-trans-form
Wu, T.-S. eta/, Chern. Pharm. Bull., 1985, 33, 4005.
Oil. Bp 16 55S. [oc]i;l + 109° (neat).
(IS,4R)-form [5056-00-8]
p-Menth-1-en-7-al Mo-00582 (-)-trans-form
4-( 1-Methylethyl)-1-cyclohexene-1-carboxaldehyde. 4- · Oil. [oc]i;l -108° (neat).
1sopropyl-1-cyclohexene-1-carboxaldehyde. Phellandral
[1124-26-1, 2230-85-5]
[21391-98-0]
Sakai, T. eta/, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1962,

2
CHO 83, 745 (isof)
Thomas, A.F. et a/, Helv. Chim. Acta, 1964, 47, 475 (ms)
Schnelle, F.J. et a/, Planta Med., 1968, 16, 48 (isof)
Sakota, N. eta/, Bull. Chern. Soc. Jpn., 1971, 44, 485 (synth, abs
config)
Kreft, A., Tetrahedron Lett., 1977, 1035 (synth)

CIOHI60 M 152.236 p-Menth-3-ene Mo-00585

(S)-form 4-M ethyl-1-( 1-methylethyl)cyclohexene. 1-Isopropyl-4-
Constit. of water-fennel oil (Phellandrium aquaticum). methylcyclohexene. Menthomenthene
Also obt. from Eucalyptus spp., Anethum sowa,
[500-00-5]
Haplopappus laricifolius, Lavandula spp. and others. Oil.
Bp 220-230°. [ocJn -139° (CHC1 3).
Semicarbazone: Cryst. (MeOH). Mp 204-205°.
[536-58-3, 23963-70-4]
Frank, R.L. eta/, J. Am. Chern. Soc., 1949, 71, 3889 (synth)
Gillespie, D.T.C. et al, J. Chern. Soc., 1955, 665.
Stadler, P.A., Helv. Chim. Acta, 1960, 43, 1601 (isof)
CIOHI8 M 138.252
p-Menth-1-ene Mo-00583 Isol. from thyme and peppermint oil.
1-Methyl-4-( 1-methylethyl)cyclohexene. 4-/sopropyl-1- I> OS9800000.
methylcyclohexene. Carvomenthene (R)-form [619-52-3]
[5502-88-5] Oil. Bp 168°. [ocln +116.74°.

6
(±)-form
Bpi4 55o.
[22564-83-6]
Thomas, A.F. eta/, He/v. Chim. Acta, 1964, 47, 475 (ms)
I Rodd's Chern. Carbon Compd. (2nd Ed.), 2nd Ed., Vol. liB. 1967,
A 219 (bib[)
Sakota, N. eta/, Bull. Chern. Soc. Jpn., 1971, 44, 485.
CIOHI8 M 138.252 Hutchins, R.O. eta/, J. Org. Chern., 1975, 40, 923 (synth)
(R)-form [1195-31-9] Posner, G.H. et a/, J. Org. Chern., 1976, 41, 578 (synth)
Constit. of Rosa rugosa oil. Oil. Bp 175-177°. [ocln Brieger, G. eta/, J. Org. Chern., 1979, 44, 1340 (synth)
+ 118° (neat). ni; 1.4557.
(S)-form [499-94-5]
Isol. from Mentha requieni and Skimmia /aureola oil.
[61585-35-1]
Newhall, W.F., J. Org. Chern., 1958, 23, 1274 (synth)
Sakai, T. eta/, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), 1962,
83, 745 (isol)

107
p-Menth-4(8)-ene- p-Menth-1-ene-6,8-diol Mo-00586 - Mo-00590

p-Menth-4(8)-ene Mo-00586 p-Menth-1-ene-5,6-diol Mo-00589

1-Methyl-4-(1-methylethylidene)cyclohexane. 1- 3-Methy/-6-( 1-methy/ethyl)-3-cyclohexene-1 ,2-dio/. 6-
Isopropylidene-4-methylcyclohexane Isopropy/-3-methy/-3-cyclohexene-1 ,2-dio/. p- M enth-1 (6)-
[1124-27-2] ene-2,3-dio/

~
CIOHIB M 138.252 C 10H 180 1 M 170.251
Constit. of Sideritis linearifolia. Oil. Bp 172-174°. (2S.JR,4S)-form
Thomas, A.F. eta/, Helv. Chim. Acta, 1964, 47, 475 (ms) lsol. from Mentha gentilis. Mp 51-52°. [rx]i:· 5 -18.8° (c,
Mitzner, B.M. et ai, App/. Spectrosc., 1965, 19, 169 (ir) 0.5 in CHCI 3).
Weinberg, D.S. eta/, J. Org. Chern., 1966, 31, 115 (synth, ms)
Umemoto, K. eta/, Nippon Nogei Kagaku Kaishi, 1977, 51, 245
(isol)
p-Menth-8-ene Mo-00587
1-Methyl-4-(1-methylethenyl)cyclohexane. 1-Isopropenyl-4- p-Menth-1-ene-6,8-diol Mo-00590
methylcyclohexane. P-Dihydrolimonene
5-Hydroxy-rx,rx,4-trimethyl-3-cyclohexene-1-methanol, 9CI. 5-
[6252-33-1] (1-Hydroxy-1-methy/ethyl)-2-methyl-2-cyclohexen-1-o/. 6,8-

6
Carvomenthenedio/. Sobrerol. Cutepin. Lysmucol. Mucofiux.
Sobrepin. Pinol hydrate. PR-Sf 109
[498-71-5]
(1RS,4RS)-form

HO~
I

A (4R,6R)1"orm
CIOHIB M 138.252
(JRS,4RS)-form [1124-25-0]
trans1"orm
Bp 170-171°. ni? 1.4551. OH
(JRS,4SR)-form [1879-07-8] C 10H 180 1 M 170.251
cis1"orm Abs. configs. given in primary lit. are based on incorrect
Bp 174-175°. ni? 1.4580. abs. config. for (+)-ex-Pinene. Respiratory stimulant.
[22472-45-3] (4R,6R)-form
Thomas, A.F. eta/, Helv. Chim. Acta, 1964, 47, 475 (ms) (- )-cis1"orm
Borowiecki, L. eta/, Pol. J. Chern. (Rocz. Chern.), 1964, 38, 1505; Mp 106-108°. [rx]i? - W (EtOH).
CA, 62, 9177h (synth) (4R,6S)-form
Vig, O.P. eta/, J. Indian Chern. Soc., 1968, 45, 1026 (synth) (-)-trans-form
Bardyshev, 1.1. eta/, Zh. Org. Khim., 1973, 9, 1670 (synth)
lsol. from Bordeaux terpentine (Pinus maritimus). Mp
148-149°. [rx]i? -150° (EtOH).
p-Menth-1-ene-3,CHtiol Mo-00588 (4RS,6RS)-form
2-Methyl-5-(1-methylethyl)-2-cyclohexene-1,4-diol. 5- (±)-cis-form
1sopropyl-2-methyl-2-cyclohexene-1 ,4-dio/ Mp 105-106°.
(4S,6R)-form (38235-58-4]
HO~ (+ )-trans1"orm
Mp 149°. [rx]i? + 150° (EtOH).
~OH I
Benzoyl: Mp 117-118°.
(4S,6S)-form
A (+)-cis-form
C10H 180 1 M 170.251 Mp 108-108.SO. [rx]i? + 15.SO (EtOH).
(3S,4S,6R)-form [38301-95-0] (4RS,6SR)-form [32226-54-3]
Constit. of Eupatorium macrocephalum and E. ( ± )- trans1"orm
erythropappum. Cryst. (EtOAcjpet. ether). Mp 169-170°. Mp 131-13l.SO.
[rx]i? + 11.7° (c, 2.48 in EtOH), [rx]i; -77°. Benzoyl: Mp 93-94°.
6-0-P-n-G/ucopyranoside: Phthaloyl: Mp 142.5-143.SO.
C 16H 180 7 M 332.393 [42370-41-2, 54164-89-5]
Constit. of Eupatorium tinifolium.
Dupont, G., CA, 1922, 16, 4340 (isol)
Gonzalez, A.G. eta/, An. Quim., 1972, 68, 319 (isol) B1umann, A. eta/, J. Chern. Soc., 1952, 4420 (synth)
Talapatra, S.K. et a/, J. Indian Chern. Soc., 1985, 62, 999 (isol) Schmidt, H., Chern. Ber., 1953, 86, 1437 (synth, bib/, abs config)
De1ord, J.J. et al, Acta Crysta/logr., Sect. C, 1988, 44, 765 (cryst Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
struct) Martindale, The Extra Pharmacopoeia, 28th/29th Ed ,
D'Agostino, M. eta/, Phytochemistry, 1990, 29, 3656 (glucoside) Pharmaceutical Press, London, 1982/1989, 13239.

108
p-Menth-1(7)-ene-2,8-diol - p-Menth-3-ene-1,2-diol Mo-00591 - Mo-00596

Ventura, P. et al, Xenobiotica, 1985, 15, 317 (metab) p-Menth-2-ene-1,4-diol Mo-00594

Braga, P.C. et al, Int. J. Clin. Pharmacal. Res., 1987, 7, 381 (rev, 1-Methy/-4(1 -me thy/ethyl)-2-cyc/ohexene-1 ,4-dio/. 1-
pharmacal) lsopropy/-4-methy/-2-cyc/ohexene-1 ,4-dio/
[40735-19-1]
p-Menth-1(7)-ene-2,8-diol Mo-00591
5-(1-Hydroxy-1-methy/ethyl)-2-methy/enecyc/ohexanol
[26963-80-4]

?,OH
(1RS,4RS)-form

Relative
configuration C10H 180 1 M 170.251
(1RS,4RS)-form
cis-form
OH
Mp 80°.
C 10H 180 1 M 170.251
(1RS,4SR)-form [21473-37-0]
Cryst. (C6H 6). Mp 129.5-130°.
trans-form
Scott, W.E. et al, J. Org. Chern., 1971, 36, 63 (synth, cryst struct) Isol. from peppermint oil. Cryst. (Etpjhexane). Mp
101°. Bpu 75-77°. [IX]~ -1.2° (c, 0.1 in MeOH).
p-Menth-1-ene-7,8-diol Mo-00592 Schenck, G.O. et al, Justus Liebigs Ann. Chern., 1964, 674, 93
[19894-91-8] (synth)
Katsuhara, J. et al, Kogyo Kagaku Zasshi, 1966, 69, 1170 (isol)
Pierson, G.O. eta/, J. Org. Chern., 1969, 34, 3654 (synth)

p-Menth-2-ene-1,7-diol Mo-00595
1-Hydroxy-4-( 1-methy/ethyl)-2-cyc/ohexene-1-methano/, 9CI.
1-Hydroxymethy/-4-isopropy/- 2-cyc/ohexen-1-o/
[97857-20-0]

C 10H 180 1 M 170.251

Mp 130°. [1X]~ -163.4° (EtOH).
Sato, T., Nippon Kagaku Zasshi (Jpn. J. Chern.), 1965, 86, 252;
1967, 88, 1005 (synth)

p-Menth-1-ene-8,9-diol Mo-00593 C 10H 180 1 M 170.251

2-(4-Methy/-3-cyc/ohexen-1-yl)-1,2-propanedio/, 9CI. Constit. of Senecio affinis. Oil.
Uroterpenol
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1249.
[6252-35-3]
p-Menth-3-ene-1,2-diol Mo-00596

~
1-Methyl-4-(J-methylethyl)-3-cyc/ohexene-1,2-dio/, 9CI. 4-
lsopropy/-1-methy/-3-cyc/ohexene-1 ,2-dio/

~CH2 0li
(4R,SR}f"""

OH
C 10H 180 1 M 170.251
Natural Uroterpenol is a mixture of (4R,8R)- and (4R,8S)-
forms. Constit. of human urine.
(4R,BR)-form [56031-82-4] C 10H 180 1 M 170.251
Gum. [1X]i;5 +94.8° (c, 6.1 in EtOH). (lfJ,2f/)-form [98857-38-6]
9-(p-Nitrobenzoyl): Cryst. (EtOH aq.). Mp 74-76°. [1X]i;5 Constit. of oil from Feru/a jaeschkeana. Viscous mass.
+37.9° (c, 3.9 in EtOH). [1X]i;5 -2.SO (c, 2 in CHC13).
(4R,8S)-form [56031-83-5] Suga, T. eta/, Bull. Chern. Soc. Jpn., 1968, 41, 944 (synth)
Gum. [1X]i;5 + 78.8° (c, 2.7 in EtOH). Kapahi, B.K. eta/, Pafai, 1985, 7, 23 (isol)
Garg, S.N. et al, Phytochemistry, 1988, T/, 936 (isol)
9-(p-Nitrobenzoyl): Liq. [1X]i;5 +20.4° (c, 2.3 in EtOH).
[13275-37-1]
Wade, A.P. eta/, Biochem. J., 1966, 101, 727 (isol, struct)
Kergomard, A. eta/, Tetrahedron, 1977, 33, 2215 (synth, abs
config)
Carman, R.M. et al, Aust. J. Chern., 1986, 39, 21 (cryst struct)

109
p-Menth-4-ene-1,2-diol- p-Menth-1-en-7-oic acid Mo-00597 - Mo-00602

p-Mentb-4-ene-1,2-diol Mo-00597 Piatkawski, K. et al, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1975,
1-Methyl-4-(1 -methylethyl)-4-cyc/ohexene-1 ,2-diol, 9CI. 4- 23, 503, 883 (synth, abs config)
Garg, S.N. et al, Phytochemistry, 1988, 27, 936 (isol)
/sopropyl-1-methyl-4-cyc/ohexene-1 ,2-diol

p-Mentb-1-ene-8-tbiol Mo-00600
or:,or:,4- Trimethyl-3-cyc/ohexene-1-methanethiol, 9Cl. 4-(1-
Mercapto-1-methylethyl)-1-methylcyc/ohexene. 8-Mercapto-
p-menth-1-ene
[71159-90-5]

ClOHI802 M 170.251
(JR* ,2R*)-form [66965-46-6]
A (R}fo~
Constit. of oil from Ferula jaeschkeana. Viscous mass.
[or:]i;l +4.8° (c, 4 in MeOH).
(1 R* ,2S*)-form
From F. jaeschkeana. Oil.
XsH
C10H 18S M 170.318
[21473-37-0, 94492-01-0) Powerful flavour constit. of grapefruit juice detectable at
Kapahi, B.K. et al, Pafai, 1985, 7, 23 (isol) w-4 ppb (equiv. to I0-4 mg per ton of water). Opt.
Garg, S.N. et al, Phytochemistry, 1988, 27, 936 (isol) activity of natural enantiomer not known.
(R)-form [83150-78-1]
'p-Mentb-5-ene-1,2-diol Mo-00598 Oil. [or:Ji? +82.0°.
2-Methyl-5-(1-methylethyl)-3-cyc/ohexene-1 ,2-diol, 9Cl. 5- (S)-form [83150-77-0]
/sopropyl-2-methyl-3-cyc/ohexene-1 ,2-diol Oil. [or:]i? -82.0°.
Demole, E. et al, Helv. Chim. Acta, 1982, 65, 1785.

2
~H~OH p-Mentb-3-ene-3-tbiol, SCI Mo-00601
(1R,2R,4S)-form 5-Methyl- 2-( 1-methylethyl)cyc/ohexanethione. 2- lsopropyl-5-
4
methylcyc/ohexanethione. Thiomenthone
[25946-28-5]
C 10H 180 2 M 170.251
(JR,2R,4S)-form
Constit. of Eucalyptus dives. Cryst. Mp 54°. [or:Jn -34.1°
(CHC1 3).
(JR,2S,4R)-form [89771-40-4]
From Chenopodium multifidum. Cryst. (C 6H 6). Mp 114°.
[or:Jn - 8.SO (c, 1.17 in CHC1 3). C 10H 18S M 170.318
(1S,2R,4S)-form [89771-42-6] Flavouring ingredient. Intensely red liq. with strong smell.
Constit. of C. multifidum. Cryst. (C 6H 6). Mp 135-136°. Bp763 215-216°. Dec. on standing, evolving H 2S.
[or:Jn +40° (c, 0.92 in CHC1 3). Paquer, D. et al, Bull. Soc. Chim. Fr., 1969, 3595 (synth)
(JS,2S,4S)-form [89771-41-5]
From C. multifidum. Cryst. (CHC1 3). Mp 163-164°. [or:Jn p-Menth-1-en-7-oic acid Mo-00602
+ 54.5° (c, 0.66 in CHC1 3). 4-(1-M ethylethyl)-1-cyc/ohexene-1-carboxy/ic acid. 4-
Blumann, A. et al, Aust. J. Chern., 1962, 15, 290 (isol) lsopropyl-1-cyc/ohexene-1-carboxy/ic acid. Phellllndric acid.
Stolow, R.D. et al, Tetrahedron, 1965, 21, 1889 (isol) Tetrahydrocumic acid
Stolow, R.D. et al, J. Org. Chern., 1971, 36, 960 (struct)
De Pascual Teresa, J. et al, Phytochemistry, 1983, 22, 2749 (isol) COOH

p-Mentb-8-ene-1,2-diol Mo-00599
1-Methyl-4-(1-methylethenyl)-1 ,2-cyc/ohexanediol, 9Cl. 4-
/sopropenyl-1-methyl-1 ,2-cyc/ohexanediol
0~
I
(R)-form

[1946-00-5] CIOH1602 M 168.235

(ZOH
lsol. from leaves of Bursera microphylla (no opt. rotp..
reported, prob. artefact).
(R)-form
Cryst. (EtOH aq.). Mp 144-145°. [or:Ji? + 112.8° (c, 2.083
in MeOH).
p-Bromophenacyl ester: Needles. Mp 86°. [or:Ji? +68.JO
(CHC1 3).
C10H 180 2 M 170.251 (S)-form
Constit. of Ferula jaeschkeana. Needles (MeOH). Mp 74°. Cryst. (EtOH aq.). Mp 144-145°. [or:Ji? -112.6° (MeOH).
[or:]i;l + 29° (c, 2 in MeOH). (±)-form [586-88-9]
[38630-75-0, 39904-09-1, 59121-76-5, 59121-82-3) Cryst. (MeOH aq.). Mp 143-144°.
Royals, E.E. et al, J. Org. Chern., 1966, 31, 1937 (synth) p-Bromophenacyl ester: Mp 143-144°.

110
p-Menth-1-en-3-ol - p-Menth-1(7)-en-8-ol Mo-00603 - Mo-00607

Cooke, R.G. et al, J. Chern. Soc., 1940, 808 (synth, abs config)
Bradley, C.E. eta/, J. Am. Pharm. Assoc., 1951, 40, 591 (isol)
Camps, F. eta/, J. Org. Chern., 1967, 32, 2563 (synth, ir, pmr)
p-Menth-1-en-3-ol Mo-00603
3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-ol, 9CI. 6-
lsopropyl-3-methyl-2-cyclohexen-1-ol. Piperitolt
[491-04-3]
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 298 (occur)
Willson, C.W. et a/, J. Org. Chern., 1973, 38, 1684 (synth)
Thomas, A.F., Helv. Chim. Acta, 1974, 57, 2062 (synth)
p-Menth-1-en-5-ol Mo-00605
3-Methyl-6-( 1-methylethyl)-3-cyclohexen-1-ol. 6-Isopropyl-3-
methyl-3-cyclohexen-1-ol. p- Menth-1(6)-en-3-ol. 1-Terpinen-

0
5-ol
[55708-42-4]
(3R,4R)-form

~OH
4
HO~
I

~
C10H 180 M 154.252
(3R,4R)-form [65733-27-9]
(-)-cis-form
Mp 30o. [<X]n -246° (C6H6). C10H 180 M 154.252
lsol. from Melaleuca alternifolia and Piper nigrum.
(3R,4S)-form [25437-28-9]
(-)-trans-form [29801-64-7, 71933-06-7)
lsol. from essential oils of Mentha and Eucalyptus spp. Debrauwere, J. et al, Bull. Soc. Chim. Be/g., 1975, 84, 167 (isol,
Oil. Bp 15 98°. [a]~ -25° (c, 2.1 in C6H6). pmr)
(3S,4R)-form [65733-28-0]
(+)-trans-form p-Menth-1(7)-en-4-ol Mo-00606
Reported from an Andropogon sp. Bp 16 101-104°. [a]g; 1-Isopropyl-4-methylenecyclohexanol. 4-Methylene- I-( 1-
+40.22° ( +28°). methylethyl)cyclohexanol. 1(7)-Terpinen-4-ol
(3S,4S)-form [34350-53-3] [18479-63-5]
(+)-cis-form
Oil. Mp UO. Bp 15 96°. [a]~ +218.3° (c, 2.1 in C6H 6).
[16721-38-3, 16721-39-4, 75363-64-3, 75363-65-4)
Macbeth, A.K. et al, J. Chern. Soc., 1952, 2852 (synth)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 297 (occur)
Prasad, R.S. et a/, Tetrahedron, 1976, 32, 1437 (synth, bib/) C10H 180 M 154.252
Oil. Bp 10 108-109°.
Mitzner, B.M. et al, J. Org. Chern., 1966, 31, 2419 (pmr)
p-Menth-1-en-4-ol Mo-00604
Vig, O.P. et al, Indian J. Chern., 1971, 9, 899 (synth)
4-Methyl- I-( 1-methylethyl)-3-cyclohexen-1-ol. 1-Isopropyl-4-
methyl-3-cyclohexen-1-ol. Terpinen-4-ol. 4-Carvomenthenol.
Origanol p-Menth-1(7)-en-8-ol Mo-00607
[562-74-3] <X,<X-Dimethyl-4-methylenecyclohexanemethanol. b- Terpineol
[17023-62-0]

C10H 180
Perfumery ingredient.
H~
M 154.252
(R)-form

C10H 180 M 154.252

~H
lsol. from Umbellularia californica, Amomum spp. and
(R)-form [20126-76-5] Zanthoxylum piperitum. Oil.
lsol. from Eucalyptus dives, Xanthoxylum rhetsa and [7299-42-5)
other essential oils. Oil. Bp 208-210°. [a]i{ -36° (c, 1.44
Mitzner, B.M. et al, J. Org. Chern., 1966, 31, 2022.
in EtOH). Lawrence, B.M. et a/, Phytochemistry, 1974, 13, 2009 (isol)
(S)-form [2438-10-0]
Occurs in many essential oils, e.g. lavender, Cupressus
macrocarpa. Oil. Bp 208-210°. [a]~ +24.SO.
(±)-form [28219-82-1]
Obt. from Liquidambar formosana. Liq. Bp 212-214°.
Ohloff, G. et al, Helv. Chim. Acta, 1965, 48, 10 (abs config)
Verghese, J., Perfum. Essent. Oil Rec., 1966, 57, 694 (rev)

111
p-Menth-1-en-7-ol- p-Menth-4(8)-en-3-ol Mo-00608- Mo-00613

p-Menth-1-en-7-ol Mo-00608 (4R,8R)-form [13835-30-8)

4-(1-M ethylethyl)-1-cyc/ohexene-1-methanol. 1- Bp0 _2 64-69°. [a:]~ + 104° (neat).
Hydroxymethyl-4-isopropylcyc/ohexene. 7-Carvomenthenol. (4R,8S)-form [13835-75-1]
PheUandrol Bp0 . 25 75-82°. [a:]~ +97.3° (c, 1 in CHC1 3).
[5502-72-7] (4S,8R)-form [26462-90-8]
Bp0. 2 75-80°. [a:]~ -94° (c, 0.92 in CHC1 3).
(4S,8S)-form [26462-81-7]
Bp0 . 15 70-78°. [a:]~ -103.1° (c, 4.8 in C 6H 6).
Schulte-Elte, K.H. et al, Helv. Chim. Acta, 1966, 49, 2150.
Pawson, B.A. eta/, J. Am. Chern. Soc., 1970, 92, 336 (synth, pmr)

C 10H 180 M 154.252 p-Menth-3-en-1-ol Mo-00611

Constit. of Buchu leaf oil. [a:]i,<' + 102.8°. ni,<' 1.4830. 1-Methyl-4-( 1-methylethyl)-3-cyc/ohexen-1-ol. 4-lsopropyl-1-
p-Nitrobenzoyl: Mp 65.5-66.SO. methyl-3-cyc/ohexen-1-ol. Terpinen-1-ol
Camps, F. eta/, An. Quim., 1968, 64, 401 (synth) [586-82-3)
Gaiffe, A. eta/, Compt. Rend. Hebd. Seances Acad. Sci. Sect. C,
1971, 272, 96.
Kaiser, R. et a/, J. Agric. Food Chern., 1975, 23, 943 (isol)

p-Menth-1-en-8-ol Mo-00609
a:,a:,4- Trimethyl-3-cyc/ohexene-1-methanol, 9CI. 4-(1-
Hydroxy-1-methylethyl)-1-methylcyc/ohexene. at:- Terpineol.
Terpinolt C1oH180 M 154.252
[98-55-5] Constit. of Origanum vulgare, Ferula penninervis, lime oil
(Citrus aurantifolia) and others. Oil. Bp 208-210°. n~

6+
1.4760.
Kovats,.E., Helv. Chim. Acta, 1963, 46, 2705 (isol)
(R)-form Brieskom, C.H. et al, Planta Med. (Suppl.), 1967, 96 (iso/)
Goryaev, M.I. et al, CA, 1969, 70, 70998a (isol)
I
Accrombessi, G. et al, Tetrahedron, 1981, 37, 3135 (synth)

OH p-Menth-4(8)-en-1-ol
C 10H 180 M 154.252
All stereoisomers occur widely in essential oils (Artemisia,
Cinnamomum, Juniperus, Eucalyptus and Mentha spp.).
Important perfumery ingredient. Acetate and other
simple esters are also used in perfumery and flavourings.
I> WZ6700000.
(R)-form [7785-53-7]
Cryst. Mp 37°. Bp 15 104°. [a:]~ + 100.SO.
(S)-form [10482-56-l]
Cryst. Mp 37°. Bp 15 104°. [oc]~ -100.5°.
(±)-form [2438-12-2]
Cryst. Mp 40-41°. Bp 12 99-100°.
Freudenberg, K. et al, Justus Liebigs Ann. Chern., 1955, 594, 76
(abs config)
Prelog, V. eta/, Justus Liebigs Ann. Chern., 1957, 603, I (synth)
Mitzner, B.M. et al, Am. Perfum. Cosmet., 1966, 81, 25 (ir)
Beckey, H.D. eta/, Org. Mass Spectrom., 1968, 1, 47 (ms)
Karrer, W. et al, Konstitution und Vorkommen der Organischen p-Menth-4(8)-en-3-ol
Pjlanzenstoffe, 2nd Ed., Birkhauser Verlag, Basel, 1972-1985,
no. 299 (occur)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)
Mo-00612
1-Methyl-4-(1 -methylethylidene )cyclohexanol, 9Cl. 4-
Isopropylidene-1-methylcyc/ohexanol. r- Terpineol
[586-81-2]
C 10H 180 M 154.252
lsol. from carrot oils and from Cinnamomum zeylanicum,
Pinus sylvestris, Ferula penninervis. Cryst. (Etp). Mp
68-70°.
Bayer, A., Ber., 1894, 27, 436, 444 (synth)
Verghese, J., Indian Perfum., 1972, 16, 35 (rev)
Mo-00613
5-Methyl-2-(1-methylethy/idene)cyclohexanol. 2-
lsopropylidene-5-methylcyclohexanol. Pulegol
[529-02-2]

~OH
p-Menth-1-en-9-ol Mo-00610
[18479-68-0)

618

~CH20H
(4R,8R)-form C 10H 180 M 154.252
(1R,3R)-form [22472-80-6]
lsol. from Mentha gentilis and M. spirata. Oil. Bp 2 75-
760. [a:)~ -80°.
[18649-91-7, 18675-29-1, 22472-79-3, 28582-41-4, 29910-20-1]
C 10H 180 M 154.252 Eschinasi, E.H. eta/, J. Org. Chern., 1970, 35, 2010.
Constit. of Vaccinium myrtillus (bilberry) and tangerine oil. Marshall, J.A. eta/, J. Org. Chern., 1975, 40, 1162 (synth)

112
p-Menth-4(8)-en-7-ol- p-Menth-8-en-7-ol Mo-00614 - Mo-00619

p-Menth-4(8)-en-7-ol Mo-00614 p-Menth-8-en-2-ol Mo-00617

4-( 1-Methylethylidene )cyclohexanemethano/, 9CI 2-Methy/-5-( 1-methy/ethenyl)cyclohexano/. 5-/sopropenyl- 2-
[57074-30-3] methy/cyclohexano/
[17699-09-1]
I
I

HOn41
X (1R,2R,4R)-/o""

C 10H 180 M 154.252

lsol. from Buchu leaf oil. C10H 180 M 154.252
Kaiser, R. eta/, J. Agric. Food Chern., 1975, 23, 943 (isol)
Occurs in Mentha spp., Piper /ongum, Heracleum candicans
and other essential oils. Not all stereoisomers fully
characterised. Stereoisomeric mixt. used as flavour
p-Menth-6-en-2-ol Mo-00615 ingredient.
2-Methy/-5-( 1-methy/ethyl)-2-cyc/ohexen-1-o/. 5-/sopropy/-2- (JR,2R,4R)-form [20549-47-7] (- )-Dihydrocarveol
methyl-2-cyc/ohexen-1-o/. Carvotanacetol Occurs in caraway oil. Oil. Bp 10 99-99.5°. [ex]~ -34.15°
[586-23-2] (neat).
(1R,2S,4R)-form [20549-48-8]
(+ )-Neodihydrocarveol

H0'2 (2R,4R)-f<Nm
Viscous liq. Bp 19 107-107.9°. [ex]~ +35.16° (neat).
[619-01-2, 18675-33-7, 18675-34-8, 18675-35-9, 22567-21-1, 22567-
22-2, 36237-64-6, 38049-26-2, 51773-45-6, 53796-77-3, 53796-80-8]
Shishibori, T. et al, Bull. Chern. Soc. Jpn., 1968, 41, 1170 (synth)
Ladwa, P.H. eta/, Indian J. Chern., 1968, 6, 765 (synth)
C 1oH180 M 154.252 Vig, O.P. eta/, J. Indian Chern. Soc., 1972, 49, 159 (synth)
(2R,4R)-form [31269-75-7]
Oil. Bp 15 122-123°. [ex]i;1 -28.2° (c, 2.5 in MeOH). p-Menth-8-en-3-ol Mo-00618
(2R,4S)-form [22472-56-6] 5-Methyl-2-(1-methy/ethenyl)cyc/ohexano/. 2-/sopropenyl-5-
Oil. Bp 22 115°. [exln + 151.4° (c, 2 in MeOH). methy/cyc/ohexano/
(2S,4R)-form [31269-74-6] [7786-67 -6]
Oil. Bp 22 115°. [ex]i;1 -152.0° (c, 2 in MeOH).

A
(2S,4S)-form [536-30-1]
Oil. Bp 15 122-123°. [ex]i;1 + 28.4° (c, 2.3 in MeOH).
(1R,3R,4S)-:form
[59905-51-0, 59905-52-1]
Grandi, R. et al, Tetrahedron, 1974, 30, 4037. ~OH I

~
p-Menth-8-en-1-ol Mo-00616
C 10H 180 M 154.252
1-Methy/-4-( 1-methy/ethenyl)cyc/ohexano/. 4-/sopropeny/-1-
Various stereoisomers occur in essential oils.
methylcyclohexano/. fJ- Terpineol
(JR,JR,4S)-form [89-79-2] (- )-/sopulegol
[138-87-4]
lsol. from Ceratocystis coerulescens (fungus). Oil. Bp 3
65-66°. [ex]~ -22.5° (neat).
(JR,3S,4S)-form [20549-46-6] ( + )-Neoisopulegol
Constit. of Leptospermum liversidgei. Oil. Bp9 81-81.2°.
[ex]~ +32.3° (neat).
[89-79-2, 21290-09-5, 29141-10-4, 50373-36-9, 59905-53-2, 59905-
54-3]
Shishibori, T., Bull. Chern. Soc. Jpn., 1968, 41, 1170 (synth)
C 1oH180 M 154.252 Sakai, K. et al, Tetrahedron Lett., 1972, 4375 (synth)
Constit. of several essential oils. Oil with hyacinth odour. He1mchen, G., Tetrahedron Lett., 1974, 1527 (abs config)
Mp 32-33°. Bp 10 90°. Koch, W.-G. et al, Z. Naturforsch., C, 1987, 42, 159 (isol)
I>OT0175130.
[7299-40-3, 7299-41-4] p-Menth-8-en-7-ol Mo-00619
Vig, O.P. eta/, J. Indian Chern. Soc., 1971, 48, 993 (synth) 4-(1-Methy/ethenyl)cyc/ohexanemethano/, 9CI. Shisool
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (crnr) [18479-64-6]

(1RS,4RS)-form

M 154.252

113
p-Menth-8-en-9,3-olide - p-Menth-1(7)-en-2-one Mo-00620 - Mo-00624

(IRS,4RS)-form [22451-48-5] p-Menth-1-en-5-one Mo-00622

trans-form 3-Methy/-6-(1 -methy/ethyl)-3-cyc/ohexen-1-one, 9CI. 2-
lsol. from Buchu leaf oil and Perilla acuta. Oil. Bp 225°. Isopropy/-5-methy/-4-cyc/ohexen-1-one. p- Menth-1(6)-en-3-
3,5-Dinitrobenzoy/: Mp 79.5°. one
(IRS,4SR)-form [94268-63-0]
cis-form
3,5-Dinitrobenzoy/: Mp 73°.
Iskenderov, M.A., J. Gen. Chern. USSR (Engl. Trans/.), 1937, 7,
1429 (synth)
Kayahara, H. et al, Agric. Bioi. Chern., 1969, 33, 86 (synth)
Fujita, Y. et al, Bull. Chern. Soc. Jpn., 1970, 43, 2637 (isol)

p-Menth-8-en-9,3-olide Mo-00620 CIOH160 M 152.236

Constit. of Pulicaria undulata. Oil.
Hexahydro-6-methyl-3-methylene-2(3H)-benzofuranone, 9CI.
p-Menthenolide · (64853-97-0]
Sacco, T. et al, Planta Med., 1983, 47, 49 (isol)

Qo
Metwally, M. et al, Chern. Pharrn. Bull., 1986, 34, 378 (isol)

p-Menth-1-en-6-one Mo-00623
2-Methyl-5-(1-methylethyl)-2-cyc/ohexen-1-one. 5-/sopropyl-
\___ I (IR,3R,4S)-form
.f"o 2-methyl-2-cyc/ohexen-1-one. Carvotanacetone .
Carvotagetone
C 10H 140 1 M 166.219 [499-71-8]
(IR,3R,4S)-form

0~
trans-form
Oil. Bp0_2 120-123°.

X
(IR,3S,4S)-form
cis-form
Oil. Bp0 _3 112-116°. (R)-:form
Bal, B.S. et al, Heterocycles, 1981, 16, 2091 (synth, bib£)
CIOH160 M 152.236
(R)-:form [33375-08-5]
p-Menth-1-en-3-one Mo-00621
Constit. of Piper nigrum. Also from Tanacetum vulgare,
3-Methy/-6-(1 -me thy/ethyl)-2-cyc/ohexen-1-one. 6-Isopropy/-
Eucalyptus deglupta and Cymbopogon nardus. Oil. Bp
3-methy/-2-cyc/ohexen-1-one. Piperitone
227-229°.
[89-81-6]
Semicarbazone: Cryst. (EtOH). Mp 135°. [IX]~ -·114°
(CHC1 3).
(S)-form [22567-12-0]
(S)-:form lsol. from oil of Blumea spp., Pulicaria mauritanica,
Artemisia kurramensis and Sium latijugum. Oil. Bp 227-
2280. [1X]i;l +49.SO.
Semicarbazone: Cryst. (EtOH). Mp 173-174°. [1X]i!
CIOHI60 M 152.236 +114.7°.
(R)-form [4573-50-6] [2244-15-7, 43205-82-9]
Constit. of Eucalyptus dives oil and other E. spp., Simonsen, J.L. et al, J. Chern. Soc., 1922, 876 (isol, struct)
Mentha spp. and Zanthoxylum piperitum oil. Bp 15 Sutherland, M.D. et al, Aust. J. Chern., 1960, 13, 357 (isol)
llO.SO. [1X]i,O -51.53°. Org. Synth., 1973, 53, 63 (synth)
(S)-form [6091-50-5] Noma, Y. et al, Agric. Bioi. Chern., 1974, 38, 1637 (synth)
Constit. of oils from Andropogon jwarancusa and Debraumere, J. et al, Bull. Soc. Chirn. Belg., 1975, 84, 167 (isol,
Cymbopogon senarensis. A commonconstit. of Mentha struct)
spp. oils. Alarm pheromone from Tyrophagus simi/is
(acarid mite). Oil with camphoraceous odour. Bp 20 116- p-Menth-1(7)-en-2-one Mo-00624
118.SO. [1X]i,O +49.13°. 2-Methylene-5-( 1-methylethyl)cyc/ohexanone. 5-Isopropyl-2-
Semicarbazone: Cryst. Mp 193-194°. [1X]i? -216.8°. methylenecyc/ohexanone. rx.-Santolineone

60
[6091-52-7] [15297-07-1]
Thomas, A.F. et al, J. Chern. Soc. B, 1967, 392 (ms)
Nagasawa, T. et al, Agric. Bioi. Chern., 1975, 39, 2083 (abs con.fig)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (crnr)
Kuwahara, Y. et al, Agric. Bioi. Chern., 1987, 51, 3441 (isol)
' (R)-form
~
C 10H 160 M 152.236
(R)-form
Reported as a constit. of Santo/ina chamaecyparissus on
dubious evidence. Oil. [1X]i? +98° (c, 0.24 in CHC1 3).

114
p-Menth-3-en-2-one - p-Menth-8-en-2-one Mo-00625 - Mo-00628

(±)-form p-Menth-4(8)-en-3-one Mo-00627

Oil. Bp 233-235°. 5- Methyl-2-(1-methylethy/idene)cyc/ohexanone. 2-
Oxime: Cryst. + H 20 (EtOH aq.). Mp 222-223°. Isopropy/idene-5-methylcyc/ohexanone. Pulegone. P-
Sato, T. et al, Tetrahedron, 1967, 23, 1791 (synth) Pulegone
Guella, G. et al, Helv. Chim. Acta, 1984, 67, 1248 (synth) [15932-80-6)

:co
~
p-Menth-3-en-2-one Mo-00625
6-Methyl-3-(1-methylethyl)-2-cyc/ohexen-1-one. 3-Isopropyl- (R)-form

2' (R)-fo~
6-methyl-2-cyc/ohexen-1-one. Carvenone
[499-74-1)

C10H 160 M 152.236

(R)-form [89-82-7]
0
Occurs in oils of Mentha spp., Hedeoma pulegioides and
many other essential oils. Oil with pleasant peppermint
odour. Bp 224°. [oc]i? +23° (c, 5 in EtOH).
I> OT0261000.
C 10H 160 M 152.236 Semicarbazone: Cryst. (EtOH). Mp 174°.
(R)-form [23733-65-5) (S)-form [3391-90-0]
Oil. Bp 232-234°. [oc)i,S +45.4°. Occurs in Agastache formosanum and Glechoma
(S)-form [10395-45-6] hederacea. Oil. Bp22 104-108°. [oc]i;1 - 22.SO (neat).
Oil. BP4.5 72°. [oc)D -41.0°. [3285-04-9]
(±)-form [23733-68-8) Black, C. et al, J. Chern. Soc., 1956, 2971 (synth)
Bp 233°, Bp27 121°. n~ 1.4838. Banthorpe, D.V. et al, J. Chern. Soc., Perkin Trans. I, 1972, 1532
2,4-Dinitrophenylhydrazone: Mp 165°. (isol, biosynth)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Fujita, K., Bull. Chern. Soc. Jpn., 1961, 968 (synth) Pjlanzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
Barieux, J.-J. et al, Bull. Soc. Chim. Fr., 1971, 3978 (synth) no. 549 (occur)
Suga, T. et al, Bull. Chern. Soc. Jpn., 1972, 45, 2060 (synth) Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
Bohlmann, F. et I!l, Org. Magn. Reson., 1975, 7, 426 (cmr) Corey, E.J. et al, J. Org. Chern., 1976, 41, 380 (synth)
Sadasivam, V. et al, Indian J. Chern., Sect. B, 1979, 17, 549 (synth) Allen, K.G. et al, Phytochemistry, 1976, 15, 101 (biosynth)

p-Menth-3-en-5-one Mo-00626 p-Menth-8-en-2-one Mo-00628

5- Methyl- 2-( 1-methylethyl)-2-cyc/ohexen-1-one. 2-Isopropyl- 2-Methyl-5-(1-methylethenyl)cyc/ohexanone, 9CI. 5-
5-methyl-2-cyc/ohexen-1-one Isopropenyl-2-methylcyc/ohexanone. Dihydrocarvone
[5113-66-6) [7764-50-3)

A
yo (R)-form
~0
~
I
(1R,4R)-form

~
C 10H 160 M 152.236 C,0H 160 M 152.236
(R)-form [1753-40-8] Used in pe.f"umery.
Oil. Bp22 98°. [oc)i! + 67.2° (CHCI 3). (JR,4R)-form [5524-05-0]
(S)-form (53798-08-6] Oil. Bp 221-222°. [<X]n + 17.SO.
Oil. Bp 10 77°. [oc)~ -67.2° (CHCI 3). Oxime: Cryst. Mp 88-89°. [ocli? -9.25°.
(±)-form (JS,4S)-form [6909-25-7]
Bp8 81-82°. Constit. of caraway oil. Also from other oils such as
2,4-Dinitrophenylhydrazone: Mp 145-146°. Anathum sowa (dill), Lippia alba, Mentha spp. and
Semicarbazone: Cryst. (EtOH aq.). Mp 145-146° and 160- Cymbopogon martini. Oil. Bp 220-221°. [1X)n -19°.
161° (double Mp). Oxime: Cryst. Mp 88-89°. [1Xln +9.45°.
[22427-14-1] [619-02-3, 3792-53-8, 5948-04-9, 53796-79-5]
Eshinazi, H.E. et al, J. Am. Chern. Soc., 1956, 78, 1176 (synth) Nigam, M.C. et al, Can. J. Chern., 1965, 43, 521 (isol)
Brannock, K.C. et al, J. Org. Chern., 1966, 31, 980 (synth) Noma, Y. et al, Agric. Bioi. Chern., 1974, 38, 735 (synth)
Shono, T. et al, Tetrahedron Lett., 1974, 1295 (synth) Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
Vig, O.P. et al, J. Indian Chern. Soc., 1976, 53, 50 (synth)
Verghese, J., Perfum. Flavor., 1980, 5, 23 (rev)

115
p-Menth-8-en-3-one - Paeoniftorigenone Mo-00629 - Mo-00634

p-Menth-8-en-3-one Mo-00629 Constit. of Mentha piperita oil. Oil. [rx]~ - 51.8' (c, 10 in
5-Methyl-2-(1-methylethenyl)cyclohexanone. 2-Isopropenyl- EtOH).
5-methylcyclohexanone. Isopukgone. rx-Pulegone 3-Epimer: [75684-66-1]. /somintlactone
[529-00-0] From M. piperita. Cryst. Mp 77-79°. [rx]i; + 76.9° (c, 5

2-0
in EtOH).
Takahashi, K. eta/, Agric. Bioi. Chern., 1980, 44, 1535 (isol)
Cory, R.M. eta/, Tetrahedron Lett., 1990, 31, 6789 (synth)
(IR,4R)£o.m
2-Nitro-p-mentha-1,5-diene Mo-00632
2-Methyl-5-( 1-methylethyl)-1-nitro-1 ,3-cyclohexadiene. 5-
/sopropyl-2-methyl-1-nitro-1 ,3-cyclohexadiene
C 10H 160 M 152.236 [73041-74-4]
(JR,4R)-form [3391-89-7]
(+ )-cis:form. lsoisopulegone
Oil. Bp 10 84°. [rx]~ + 144.36°. n~ 1.4700.
Semicarbazone: Cryst. (MeOH aq.). Mp 157.5-158.SO.
(JR,4S)-form [57129-09-6]
(- )-trans:form
lsol. from oil of Hedeoma pulegioides (pennyroyal),
Mentha spp. and others, usually with Pulegone. Oil. C,oH15N0 2 M 181.234
Bp 13 98-100°. [rx]i; -7.9° (neat), [rx]~ -13.5° (c, 1.04 in (R)-form
CHC1 3). ni; 1.4670. Constit. of Angelica archangelica. Oil. [rx]~ - 161° (c, 0.5
Semicarbazone: Cryst. Mp 173-174° dec. in CHC1 3).
[3391-89-7, 17882-43-8, 29606-79-9, 52152-10-0] Escher, S. eta/, Helv. Chim. Acta, 1979, 62, 2061.
Ohloff, G. eta/, Chern. Ber., 1962, 95, 1400 (synth, config)
Watanabe, S., Bull. Chern. Soc. Jpn., 1973, 46, 1546 (synth, cd) 6-Nitro-p-mentha-1(7),2-diene Mo-00633
Vig, O.P. eta/, J. Indian Chern. Soc., 1976, 53, 50 (synth) 3-Methylene-6-(1-methylethyl)-4-nitrocyclohexene. 6-
Isopropyl-3-methylene-4-nitrocyclohexene
Menthofuran Mo-00630
4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, 9CI. 3,9-Epoxy-
p-mentha-3,8-diene
[494-90-6]
I

~0
~
C,oH 15N0 2 M 181.234
(4R*,6R*)-form [73069-40-6]
cis:form
Constit. of Angelica archangelica. Oil.
C 10H 140 M 150.220 (4R*,6S*)-form [73041-75-5]
(R)-form [17957-94-7] trans-form
Constit. of Mentha piperita and other M. spp. Oil. Bp 18 Constit. of A. archangelica. Oil.
80°. [rx]i; +92.SO. Escher, S. eta/, Helv. Chim. Acta, 1979, 62, 2061.
5-0xo: see Evodone, Mo-00479
(±)-form [59553-66-1] Paeoniflorigenone Mo-00634
Oil. [80454-42-8]
Treibs, W., Ber., 1937, 70, 85 (abs config)
Eastman, R.H., J. Am. Chern. Soc., 1950, 72, 5313 (isol)
Nigam, I.C. eta/, J. Pharm. Sci., 1964, 53, 1008 (occur)
Tori, K. et a/, Tetrahedron Lett., 1975, 4583 (cmr)
0~
Vig, O.P. eta/, J. Indian Chern. Soc., 1976, 53, 50 (synth)
Tsuboi, S. et a/, J. Org. Chern., 1980, 45, 1517 (synth)
HO~CH2 00CPh
Juo, R.-R. eta/, J. Org. Chern., 1985, 50, 700 (synth)
C 17H 180 6 M 318.326
Isol. from root of Paeonia albi.flora. Viscous oil. [rx]i;
Mintlactone Mo-00631 +4.3° (c, 0.69 in MeOH).
5 ,6, 7, 7a- Tetrahydro-3 ,6-dimethyl-2(4H)-isobenzofuranone,
9CI. p-Menth-4(8)-en-9,3-olide Me ether: Mp 121-122°. [rx]i; -14.0° (c, 1 in MeOH).
[38049-04-6] Shimizu, M. eta/, Chern. Pharm. Bull., 1983, 31, 577 (isol, cryst
struct, uv, pmr, ms)

~0 0
M 166.219

116
Paeonilactone A- 3,5,7-Trihydroxy-p-menth-1-en-6-one Mo-00635 - Mo-00640

Paeonilactone A Mo-00635 Schizonepetoside A Mo-00638

Tetrahydro-6-hydroxy-3,6-dimethyl-2,5(3H,4H)- [78887-75-9]
benzofurandione, 9CI
I
[98751-79-2] I

oilio
HO
H

H
9

~
GlcO
CIOH1404 M 198.218
Constit. of Paeony root. Needles (Et20jMeOH). Mp 128- C16H:z607 M 330.377
1290. [rx]~ -18.8° (MeOH). Constit. of spikes of Schizonepeta tenuifolia. Amorph.
7,9-Didehydro: [98751-78-1]. Paeonilllctone B [rx]i;'+ oo (c, 1.02 in MeOH).
CIOHIZ04 M 196.202 Tetra-Ac: Needles (Et20jpet. ether). Mp 132-133°. [rx]~4
Constit. of Paeony root. Needles (EtOAc). Mp 88-89°. -15.4° (c, 1.16 in CHC1 3).
[rx]~ +23.2° (MeOH). Sasaki, H. eta/, Chern. Pharm. Bull., 1981, 29, 1636.
9-(Benzoyloxy): [98751-77-0]. Paeonilllctone C
C17H 180 6 M 318.326 Schizonepetoside B Mo-00639
Constit. of Paeony root. Needles (MeOH aq.). Mp 132-
1330. [rx]~ -31.6° (MeOH). [78897-60-6]
Hayashi, T. et al, Tetrahedron Lett., 1985, 26, 3699.
Richardson, D.P. eta/, Tetrahedron Lett., 1990, 31, 5973 (synth)

Peperinic acid Mo-00636

2,4,5,6,7,7a-Hexahydro-7a-hydroxy-3,6-dimethyl-2-
benzofuranone. 3-Hydroxy-p-menth-4(8)-en-9,3-olide
[514-93-2]

(!_,OH

~0 C16H:z607 M 330.377
Constit. of spikes of Schizonepeta tenuifolia. Plates (MeOH
0 aq.). Mp 270° dec. [rx]~ + 8.6° (c, 0.69 in Py).
CIOH1403 M 182.219 Sasaki, H. et al, Chern. Pharm. Bull., 1981, 29, 1636.
Constit. of Bursera graveolens and Bystropogon mol/is.
Also isol. from aged peppermint oil. Cryst. (MeOH or
3,5,7-Trihydroxy-p-menth-1-en-6-one Mo-00640
C6H6). Mp 191° (188-189°). [rx]i;' +60.7°. Prob. artifact
3,5,7- Trihydroxycarvotacetone
of oxidn. of Menthofuran, Mo-00630.
Fester, G.A. et al, An. Asoc. Quim. Argent., 1949, 37, 197; 1952,
40, 246; CA, 40, 4636; 48, 1974 (isol)
Woodward, R.B. eta/, J. Am. Chern. Soc., 1950, 72, 399 (isol)
Crowley, K.J. et al, J. Chern. Soc., 1964, 4254 (isol)

Pinol Mo-00637
4,7,7-Trimethyl-6-oxabicyclo[3.2.1)oct-3-ene, 9CI. 6,8-
Epoxy-p-menth-1-ene CIOH1604 M 200.234
[2437-97-0] (3P.Srx.)-form [128988-32-9]
Constit. of Sphaeranthus bullatus. Gum.
3,7-Ditigloyl: [128988-31-8].
Absolute C20H 280 6 M 364.438
configuration Constit. of S. bullatus. Oil.
3,7-Ditigloyl, 5-Ac: [128988-33-0].
c10H160 M 152.236 C22 H 300 7 M 406.475
Isol. from lime oil (Citrus aurantifolia). Oil. d 20 0.948. Bp Constit. of S. bullatus. Oil.
183-184°. [rx]i? +92° (c, 2.5 in EtOH). ni? 1.4692. 3-Tigloyl, 7-Ac: [128988-34-1].
[497-31-4, 55822-06-5] Ct,H240 6 M 324.373
Kovats, E., Helv. Chim. Acta, 1963, 46, 2705 (isol, synth) Gum.
Garver, L. eta/, J. Org. Chern., 1976, 41, 2773 (synth) 5-Tigloyl: [115967-42-5].
Bondavalli, F. eta/, J. Chern. Soc., Perkin Trans. I, 1977, 430 C15H 220 5 M 282.336
(synth) Constit. of S. bullatus and S. suaveolens. Oil.
6ft-Alcohol: [128988-35-2]. p-Menth-l-ene-3ft,5rx,6ft,7-tetrol
CIOH1804 M 202.250
Constit. of S. bullatus. Gum.
Eid, F. et al, Pharmazie, 1988, 43, 347 (deriv)

117
m-Cineole - 4-lsopropyl-2-methylphenol Mo-00641 - Mo-00647

Jakupovic, J. eta/, Phytochemistry, 1990, 29, 1213 (isol, pmr) C11H 160 M 164.247
Bp 213-214°, Bp2. 5 62.SO.
Guillaumin, C., Bull. Soc. Chim. Fr., 1910, 7, 332 (synth)
Fr. Pat., I 523 471, (1970); CA, 72, 43136 (synth)
U.S. Pat., 3 683 030, (1972); CA, 77, 126225 (synth)

m-Menthanes
Bohlmann, F. et al, Phytochemistry, 1979, 18, 489 (isol)
Dinge, A.S. eta/, Indian J. Chern., Sect. B, 1981, 20, 245 (synth)

2-Isopropyl-6-methylphenol Mo-00645
2-Methyl-6-(1-methylethyl)pheno/, 9CI. m-Cymen-2-ol, 8CI.
6-/sopropyl-o-cresol. 2-Hydroxy-m-cymene. 2-Hydroxy-3-
m-Cineole Mo-00641 isopropyl-1-methylbenzene. m- M entha-1 ,3 ,5-trien-2-ol
5,7,7-Trimethyl-6-oxabicyc/o[3.2.1]octane. 1,8-Epoxy-m-
[3228-04-4]
menthane
C10H 140 M 150.220
[33730-45-9] Pale green liq. Mp -14.SO. Bp 225-226°, Bp 2.5 68°.
Me ether: 1-/sopropyl-2-methoxy-3-methylbenzene
C11 H 160 M 164.247
Bp 210-211°, Bp 2.5 52°.
Guillaumin, C., Bull. Soc. Chim. Fr., 1910, 7, 332.
Carpenter, M.S. eta/, J. Org. Chern., 1955, 20, 4014.
c.o~~ ••o M 154.252 Lamertine, A. eta/, Bull. Soc. Chim. Fr., 1969, 437.
Oil. Bp 177-178°. Kozlova, L.M. eta/, CA, 1973, 79, 78282.
Abraham, P.M. eta/, Curr. Sci., 1971, 40, 348.
3-Isopropyl-5-methylphenol Mo-00646
1-Isopropyl-3-methylbenzene Mo-00642 3-Methyl-5-(1-methylethyl)phenol, 9Cl. m-Cymen-5-ol, 8Cl.
1-Methyl-3-(1-methylethyl)benzene, 9Cl. m-lsopropyltoluene. 5-Isopropy/-m-creso/. 5-Hydroxy-m-cymene. 5-Hydroxy-3-
m-Cymene. m-Cymol. m-Mentha-1,3,5-triene isopropyl-1-methy/benzene. sym- Thymol. m-Mentha-1 ,3,5-
[535-77-3] trien-5-ol
C10H 14 M 134.221 [3228-03-3)
Present in oil of Ribes nigrum. Liq. d 20 0.862. Mp C10H 140 M 150.220
-63.75°. Bp 175.W. ni? 1.4922. Mp 54° (50°). Bp 241°, Bp 3. 5 102-103°.
I> GZ5949800. 4-Nitrobenzoy/: Plates. Mp 87-88°.
Allen, R.H. et al, J. Am. Chern. Soc., 1961, 83, 2799 (synth) Knoevenage1, E., Ber., 1894, 27, 2347 (synth)
Andersson, J. eta/, Acta Chern. Scand., 1964, 18, 1105 (isol) Carpenter, M.S. eta/, J. Org. Chern., 1955, 20, 401 (synth)
Org. Synth., Coli. Vol., 5, 1973, 332 (synth) Ger. Pat., 2 242 628, (1974); CA, 80, 145750.
Olah, G.A. eta/, J. Org. Chern., 1974, 39, 2430 (synth) Japan. Pat., 75 130 726, (1975); CA, 84, 89815.
Hino, M. eta/, Chern. Lett., 1977, 277 (synth)
4-Isopropyl-2-methylphenol Mo-00647
2-Isopropyl-6-methyl-1,4-benzoquinone Mo-00643 2-Methyl-4-(1-methylethyl)phenol, 9Cl. m-Cymen-6-ol, 8CI.
2-Methyl-6-( 1-methylethyl)-2,5-cyc/ohexadiene-1 ,4-dione, 4-/sopropyl-o-cresol. 6-Hydroxy-m-cymene. 6-Hydroxy-3-
9CI. m-Mentha-3,6-diene-2,5-dione, 8CI isopropyl-1-methylbenzene. m- M entha-1 ,3 ,5-trien-6-ol
[17603-88-2] [1740-97-2]

ho C 10H 140 M 150.220

Found in many oils. Insect repellant. Cryst. in two forms.
d 0 1.00. Mp 8.6° (form 1), Mp 28.5° (form II). Bp 3 83°.

0~
Me ether: 4-/sopropyl-1-methoxy-2-methylbenzene
C11 H 160 M 164.247
Bp 217°, Bp 3 66°.
C1oH 110 1 M 164.204 Et ether: [33641-89-3]. 1-Ethoxy-4-isopropyl-2-
Yellow oil. Bp0. 6 56-56.5°. ni:·5 1.5142.
methylbenzene
Jacobsen, N., J. Chern. Soc., Perkin Trans. 2, 1979, 569 (synth, C11H 180 M 178.274
pmr, ms) Bp 227-229°.
U.S. Pat., 1 782 966, (1931); CA, 25, 303.
2-Isopropyl-4-methylphenol Mo-00644 Carpenter, M.S. eta/, J. Org. Chern., 1955, 20, 401.
4-Methyl-2-(1-methylethyl)phenol, 9Cl. m-Cymen-4-ol, 8Cl. Lamartine, R. eta/, Bull. Soc. Chim. Fr., 1969, 437.
2-/sopropyl-p-creso/. 4-Hydroxy-m-cymene. 4-Hydroxy-3- Koz1ova, L.M. et a/, CA, 1973, 79, 78282.
isopropyl-1-methy/benzene. /sothymol. m- M entha-1 ,3 ,5-
trien-4-ol
[4427-56-9]
C1oH140 M 150.220
lsol. from Neurolaena oaxacane. Needles (AcOH). Mp 36°.
t>SL7175000.
4-Nitrobenzoyl: Mp 97-98°.
Me ether: [31574-44-4]. 2-/sopropyl-1-methoxy-4-
methylbenzene

118
m-Mentha-1,3(8)-diene - m-Menthane-1,8-diol Mo-00648 - Mo-00653

m-Mentha-1,3(8)-diene Mo-00648 C10H 160 M 152.236

1-Methyl-3-(1-methylethylidene)cyclohexene, 9CI. Isol. from Cannabis sativa.
Sylveterpinolene Stahl, E. eta/, Tetrahedron Lett., 1973, 2841 (prnr)
[17092-80-7]
m-Menthane Mo-00652
1-Methyl-3-( 1-methylethyl)cyclohexane. 1-1sopropyl-3-
methylcyclohexane
[16580-24-8]

C 1Jl16 M 136.236
lsol. from Pinus sylvestris. Bp 88°. ni,O 1.5132.
(1R,3R)-form
Cocker, W. et a/, J. Chern. Soc. C, 1968, 489 (synth)
Muraleedharan, N.V. et al, J. Indian Chern. Soc., 1972, 49, 289
(synth) C 10H 10 M 140.268
Bardyshev, 1.1. et al, Khirn. Prir. Soedin., 1974, 10, 318; Chern. (1R,3R)-form [13837-67-7]
Nat. Cornpd. (Engl. Trans/.), 325 (isol) (+)-trans-form
Oil. [a]i,O +4.1° (C 6HJ.
m-Mentha-1(6),8-diene Mo-00649 (1S,3R)-form [13837-66-6]
5-/sopropenyl-1-methylcyclohexene. Sylvestrene (+)-cis-form
Oil. [a]i,O + 12.7° (C 6H 6).
[17066-65-8, 17066-66-9, 19906-92-4, 19906-93-5]
Cocker, W. eta/, J. Chern. Soc. C, 1966, 946 (prnr)
Gollnick, K. et al, Tetrahedron Lett., 1966, 5157 (synth)
Bardyshev, 1.1. et al, Dokl. Akad. Nauk SSSR, 1968, 178, 1313
C 10H 16 M 136.236 (synth)
Gollnick, K. et a/, Justus Liebigs Ann. Chern., 1969, 721, 133 (abs
(R)-form [1461-27-4] config, synth)
Oil. Bp 20 95o. [a]i;l + 115.6° (C6H 6).
Gollnick, K. eta/, Justus Liebigs Ann. Chern., 1969, 721, 133 (abs
config, synth)
m-Menthane-1,8-diol, SCI Mo-00653
Johny, K.P. et al, Indian J. Chern., 1972, 10, 792 (synth) 3-Hydroxy~a,a,3-trimethylcyclohexanemethanol, 9CI.
Sylvterpin. Carveterpin
[38227-36-0]

6
m-Mentha-1,8-diene Mo-00650
1-Methyl-3-(1-methylethenyl)cyclohexene, 9CI. 3- HO I
lsopropenyl-1-methylcyclohexene. Carvestrene
[38738-60-2] (IR,3R)-fo~
(R)-form '(oH
Absolute C10H 100 2 M 172.267
configuration
(JR,3R)-form [38227-34-8]
CtoHt6 M 136.236 (+)-cis-form
(R)-form [17066-60-3] Needles (pet. ether). Sol. Hp, EtOH. Mp 138°. [a]~
Generated from carene hydrocarbons during isoln. from +26.7° (CHC1 3). Formerly thought to have the trans-
essential oils of Pinus spp. Oil. Bp 751 175°. [1X]n +94.SO config.
(c, 2 in C 6H 6). (JS,3R)-form [38227-35-9]
(S)-form (+)-trans-form
Oil. Bp 176-178°. [am -68.2° (EtOAc). Woolly mass (Etp or C6H 6). Mp 84° (94°). [IX]~ +20°
(±)-form [499-03-6] (CHC1 3). Formerly thought to have the cis-config.
Carvestrene (1RS,3RS)-form
Oil. Bp 178°. (±)-cis-form
{644-99-5, 20111-86-8] Mp 127°.
Vig, O.P. et al, Indian J. Chern., 1968, 6, 188 (synth) (IRS,3SR)-form
Gollnick, K. et a/, Justus Liebigs Ann. Chern., 1969, 721, 133 (abs (±)-trans-form
config, synth) Mp 94°.
Abraham, P.M. eta/, Indian J. Chern., 1972, 10, 140 (stereochern,
m-Mentha-1(6),8-dien-3-ol Mo-00651 bib/)
3-Methyl-1-(1-methylethenyl)-3-cyclohexen-1-ol
[50868-57-0]

119
m-Menthan-5-ol - m-Menth-8-ene Mo-00654 - Mo-00660

m-Menthan-5-ol Mo-00654 m-Menth-1(6)-ene Mo-00657

3-Methyl-5-( 1-methylethyl)cyclohexanol. 3-1sopropyl-5- 1-Methyl-5-( 1-methylethyl)cyclohexene. 5-/sopropyl-1-
methylcyclohexanol methylcyclohexene
[17066-64-7]

0
I
I

(1R,3S,5R)-form

HO/ '(

C 10H 280 M 156.267

(1R,3S,5R)-form [28767-45-5] C10H 18 M 138.252
Oil. [ex]~ -0.98° (c, 0.5 in EtOH). (R)-:form [13837-70-2]
3,5-Dinitrobenzoyl: Cryst. (MeOH). Mp 82-83°. [ex]~ Oil. [ex]:: + 114.SO (C 6H 6).
-13.5° (c, 0.515 in EtOH). Gollnick, K. eta/, Justus Liebigs Ann. Chern., 1969, 721, 133.
(1R,3S,5S)-form [28587-74-8]
Oil. [ex]~ -5.3° (c, 0.53 in EtOH). m-Menth-1-ene Mo-00658
3,5-Dinitrobenzoyl: Cryst. (EtOH). Mp 130°. [ex]~ +2.35° 1-Methy/-3-(1 -methylethyl)cyclohexene. 3-Isopropyl-1-
(c, 0.51 in EtOH). methylcyclohexene
Carson, M.F. eta/, J. Chern. Soc. C, 1970, 1447. [13828-31-4]

m-Menthan-8-ol, SCI Mo-00655

ex,cx,3- Trimethylcyclohexanemethanol, 9Cl.
Dihydrosilveterpineol

6" 'foH
[23171-84-8]
C 10H 18 M 138.252
(R)-form
(IR,3R)-[D'm Oil. [ex]~ -13.7° (C 6HJ.
Gollnick, K. eta/, Justus Liebigs Ann. Chern., 1969, 721, 133.

C 1.,H280 M 156.267 m-Menth-3(8)-ene Mo-00659

(JR,3R)-form [49593-74-0] 1-Methyl-3-(1 -methylethylidene)cyclohexane, 9Cl. 1-
trans-form /sopropylidene-3-methylcyclohexane
lsol. by glc, not fully characterised. [13828-34-7]
(JS,3R)-form [49593-71-7] I
(+)-cis-form I

d~ 0.906. Bp0 . 12 97°. [ex]i,S +8.38° (c, 2.1 in C6H 6). n~

1.4652. ('! (S)-:form
[5208-54-8]
Gollnick, K. et a/, Tetrahedron, 1966, 22, 139 (synth, ir, prnr, abs
config)
~
C 10H 18 M 138.252
Gollnick, K. et al, Justus Liebigs Ann. Chern., 1969, 721, 133
(synth, ir, prnr, abs config) (S)-form [5208-56-0]
d~0 0.829. [ex] 0 + 50.4° (C6H 6). n~ 1.4674.
(±)-:form
m-Menthan-5-one Mo-00656
d~0 0.821. Bp 173-175°. n~ 1.4670.
3-Methyl-5-(1 -methylethyl)-cyclohexanone, 9Cl. 3-/sopropyl-
5-methylcyclohexanone [24399-14-2]
[23978-62-3] Wallach, 0., Justus Liebigs Ann. Chern., 1908, 360, 77 (synth)
K.ishner, N., Zh. Russ. Fiz-Khirn. O-va., 1911, 43, 1139 (synth)
Gollnick, K., Tetrahedron Lett., 1966, 327 (abs config)

m-Menth-8-ene Mo-00660
1-Methy/~3-( 1-methy/ethenyl)cyclohexane. 1-/sopropenyl-3-
methylcyclohexane
[16605-36-0]
C 10H 180 M 154.252
(3S,5R)-form
(-)-cis-form
Oil. [ex]~ -2.01° (c, 0.55 in CHC1 3). n~ 1.4543.
Semicarbazone: Cryst. (MeOH). Mp 170-171°. [ex]~ -11°
(c, 0.23 in CHC1 3).
(3RS,5SR)-form
(±)-cis-:form C 10H 18 M 138.252
Bp 10 102°. n~ 1.4522. (JS,3R)-form [5208-55-9]
Carson, M.S. et al, J. Chern. Soc. C, 1970, 1447. Oil. Bp 170°. [ex]~ + W (C 6H 6).

120
m-Menth-1(6)-en-8-ol - 2-Isopropyl-3-methylphenol Mo-00661 - Mo-00667

[24399-15-3, 24399-16-4]
Gollnick, K. eta/, Justus Liebigs Ann. Chern., 1969, 721, 133
(synth, struct)
Bardyskev, 1.1. et a/, Zh. Org. Khim., 1971, 7, 2307 (synth) o-Menthanes
m-Menth-1(6)-en-8-ol Mo-00661
rx,rx,3- Trimethyl-3-cyc/ohexene-1-methanol, 9CI. or:-
Sylveterpineol 1-Isopropyl-2-methylbenzene Mo-00664
[29545-90-2] 1-Methyl-2-(1 -methylethyl)benzene, 9CI. o-Isopropyltoluene.
o-Cymene. o-Mentha-1,3,5-triene
[527-84-4]

C 10H 180 M 154.252

C 1oH14 M 134.221
(R)-form [22625-86-1]
Isol. from Citrus aurantium (sour orange). Liq. Mp
Constit. of oil from Pinus sylvestris; isol. from Laggera -71.54°. Bp 178.15°.
aurita. Bp 1 65-66°. [rx]~ + 108.2° (c, 2.7 in C6H 6). n~
1.4846. I> GZ5949900.
[25094-54-6, 29789-41-1] Allen, R.H. eta/, J. Am. Chern. Soc., 1961, 83, 2799 (synth)
Parham, W.E. eta/, Synthesis, 1976, 116 (synth, use)
Chabudzinski, Z., Pol. J. Chern. (Rocz. Chern.), 1961, 35, 985 (isol) Hino, M. eta/, Chern. Lett., 1977, 277 (synth)
Gollnick, K. et a/, Justus Liebigs Ann. Chern., 1969, 721, 133
(synth, config)
Kaima1, K. eta/, J. Indian Chern. Soc., 1971, 48, 759. 2-Isopropyl-3-methyl-1,4-benzoquinone Mo-00665
Zutshi, S.K. et a/, Indian J. Chern., Sect. B, 1976, 14, 64 (isol) 2-Methyl-3-(1-methylethyl)-2,5-cyc/ohexadiene-1,4-dione,
9CI. o-Mentha-1 ,4-diene-3,6-dione
m-Menth-1-en-8-ol Mo-00662 (39511-03-0]
rx,rx,3- Trimethyl-2-cyc/ohexene-1-methanol, 9CI
0
[24220-40-4]
AcH(CH3)2

c\OH
ycH3
0
C 10H 120 2 M 164.204
Yellow needles. Mp 65-65.SO.
C 10H 180 M 154.252
Jacobsen, N., J. Chern. Soc., Perkin Trans. 2, 1979, 569 (synth,
Constit. of oil from Pinus sylvestris. Bp 3 84°. [rx]~ +46.2°. pmr, ms)
Chabudzinski, Z., Pol. J. Chern. (Rocz. Chern.), 1961, 35, 985 (isol)
1-Isopropyl-2-methylcyclohexane Mo-00666
m-Menth-8-en-1-ol Mo-00663 1-Methyl-2-(1-methylethyl)cyc/ohexane, 9CI. o-Menthane
1-Methyl-3-( 1-methylethenyl)cyc/ohexanol, 9CI [16580-23-7]
[36386-54-6]

(1RS,2RS)-form
(1R,3R)-form
C 10H 20 M 140.268
(JRS,2RS)-form [19489-02-2]
C 10H 180 M 154.252 (±)-cis-form
Oil.
(JR,JR)-form [53538-30-0]
(-)-trans-form (JRS,2SR)-form [19489-03-3]
Constit. of turpentine from Pinus sylvestris. Mp 48-49°. (±)-trans-form
[rx)ii -0.2° (c, 4.6 in C 6H 6). Oil.
[6750-68-1, 22625-87-2, 53538-30-0] Cocker, W. eta/, J. Chern. Soc. C, 1966, 946.

Bardyshev, 1.1. et a/, Khim. Prir. Soedin., 1968, 4, 384; Chern. Nat.
Compd. (Engl. Trans/.), 325.
Gollnick, K. eta/, Justus Liebigs Ann. Chern., 1969, 721, 133.
2-Isopropyl-3-methylphenol Mo-00667
3-Methyl-2-(1-methylethyl)phenol, 9CI. o-Cymen-3-ol, 8CI.
2-/sopropyl-m-cresol. 3-m-Cymenol. 3-Hydroxy-2-isopropyl-
1-methylbenzene. vic-Thymol. o-Mentha-1,3,5-trien-3-ol
[3228-01-1]

121
3-lsopropyl-2-methylphenol- o-Menth-1-ene Mo-00668 - Mo-00675

CIOH140 M 150.220 Phenylsemicarbazone: Cryst. Mp 144.5-145.5°. [rx)~ +3.75°

Mp 70-71°. (c, 0.4 in CHC13).
4-Nitrobenzoyl: Mp 108°. Thomas, A.F., Helv. Chirn. Acta, 1967, 50, 963 (abs conjig)
Carpenter, M.S. et al, J. Org. Chern., 1955, 20, 401 (synth) Ferretti-Alloise, M.-G. et al, Helv. Chirn. Acta, 1970, 53, 201
Uenaka, F. et al, Kagaku to Kogyo (Osaka), 1960, 34, 485 (synth) (synth)

3-Isopropyl-2-methylphenol Mo-00668 o-~entha-1(7),5,8-triene Mo-00672

2-Methyl-3-(1-methy/ethyl)pheno/, 9CJ. o-Cymen-6-o/, 8CJ. 3-Methy/ene-4-( 1-methy/ethenyl)cyc/ohexene, 9CI
3-Isopropy/-o-creso/. 6-m-Cymeno/. 2-Hydroxy-6-isopropy/- [76786-83-9]
1-methy/benzene. o-Mentha-1 ,3 ,5-trien-6-o/
[4371-48-6]
CIOHI40 M 150.220
Needles. Mp 82-83°. Bp 242.SO.
4-Nitrobenzoy/: Mp 53-54°.
Me ether: 1-Isopropy/-3-methoxy-2-methy/benzene CIOH14 M 134.221
Bp5 59.5-60°.
C 11H 160 M 164.247
Mp -O.SO. Bp3 67°. (R)-form [23733-91-7]
lsol. from oil of Ledum palustre.
Carpenter, M.S. et al, J. Org. Chern., 1955, 20, 401.
Lamartine, R. et al, Bull. Soc. Chirn. Fr., 1969, 437. Tattje, D.H.E. et al, Planta Med., 1981, 41, 303 (isol)
Bazyl'chik, V.V. et al, Zh. Org. Khirn., 1981, 17, 320; J. Org.
Chern. USSR (Engl. Trans/.), 268 (synth, prnr, ir)
3-Isopropyl-4-methylphenol Mo-00669
4-Methyl-3-(1-methy/ethyl)pheno/, 9CI. o-Cymen-4-o/, 8CI.
3-Isopropy/-p-cresol. o-Mentha-1 ,3,5-trien-4-o/ o-~entha-1(7),4,8-triene-3,6-diol Mo-00673
5- M ethylene-6-( 1-methy/ethenyl)-2-cyc/ohexene-1 ,4-diol, 9CI.
[4371-46-4]
5- Isopropenyl-6-methylene-2-cyc/ohexene- I ,4-dio/. Piquerol
CIOH140 M 150.220 A
Fine needles. Mp 39-40°. BPo.s-I.o 89-90°. [32151-10-3]
4-Nitrobenzoy/: Mp 109-110°.
Carpenter, M.S. et al, J. Org. Chern., 1955, 20, 401 (synth)
Newman, M.S. et al, J. Org. Chern., 1963, 28, 2804.
Fr. Pat., I 523 471 (1970); CA, 72, 43136 (synth)

4-lsopropyl-3-methylphenol Mo-00670
3-Methy/-4-(1-methylethyl)pheno/, 9CI. o-Cymen-5-o/, 8CI. c10H 140 2 M 166.219
4-Isopropy/-m-creso/. p- Thymol. o- Mentha- I ,3,5-trien-5-o/ Constit. of Piqueria trinervia. Seed germination inhibitor
and insecticide. Cryst.
[3228-02-2]
[32151-11-4, 32151-12-5]
CIOH140 M 150.220
Mp 112°. Romo, J. et al, Rev. Latinoarn. Quirn., 1970, 1, 72 (isol, struct)
Soriano-Garcia, M. et al, Chern. Lett., 1983, 617 (cryst struct)
4-Nitrobenzoyl: Mp 143-144°.
Me ether: [5436-42-0]. 1-Isopropy/-4-methoxy-2-
o-~entha-1(7),4,8-trien-3-ol Mo-00674

ex:
methylbenzene
5-Methylene-6-(1-methy/ethenyl)-2-cyclohexen-1-ol, 9CI
C 11 H 160 M 164.247
Bp 3 82°.
Carpenter, M.S. et al, J. Org. Chern., 1955, 20, 401 (synth)
Burmistrov, S.I. et al, Zh. Org. Khirn., 1965, 1, 1835 (synth)
Rudol'fi, T.A., CA, 1968, 68, 118165 (ir)
Ger. Pat., 2 139 622, (1973); CA, 78, 110895 (synth)
CIOHI40 M 150.220
o-~enthan-3-one Mo-00671 (2R,3S)-form [23734-06-7]
2-Isopropyl-3-methy/cyc/ohexanone Ac: [32151-09-0].
C 12H 160 2 M 192.257
lsol. from Baccharis dracunculifolia and B. genistel/oides.
Romo, J. et al, Rev. Latinoarn. Quirn., 1970, 1, 72.
(2S,3S)-form Bauer, L. et al, CA, 1980, 92, 169030v (isol)

C 10H 180 M 154.252 o-~enth-1-ene Mo-00675

(2S,3S)-form [28357-23-5] 1-Isopropyl- 2-methylcyc/ohexene
(-)-cis-form. Isocarquejanone [15582-48-6]
Oil. Bp 9 81-82°. [rx]~ -60.2° {c, I in CHCI 3).
Pheny/semicarbazone: Cryst. Mp 157-158°. [rx]~ +68.9° (c,
0.66 in CHCI 3).
(2R,3S)-form [15358-74-4]
(+)-trans-form. Carquejanone
Oil. Bp9 80-81°. [rx]~ +47.9° (c, I in CHCI 3).

122
o-Menth-2(8)-ene - tX-Cyclogeraniol Mo-00676 - Mo-00681

C 10H 18 M 138.252
Oil with peppermint odour. Bp 165-168°.
Bazyl'chik, V.V. et al, CA, 1974, 80, S3264q.
Other cyclohexane
o-Menth-2(8)-ene
1-Methyl-2-(1-methylethylidene)cyclohexane, 9C1. 1-
/sopropylidene-2-methylcyclohexane
Mo-00676
monoterpenoids
[15733-49-0]

4-Acetyl-1,4-dimethyl-1-cyclohexene Mo-00679
1-(1,4-Dimethyl-3-cyclohexenyl)ethanone
[43219-68-7]
C 1oH18 M 138.252

~0
(±)-form
d~0 0.843. Bp 15 59-59.SO. n~ 1.4691.
Wallach, 0., Justus Liebigs Ann. Chern., 1908, 360, SO.
Bazyl'chik, V.V., Vestsi. Akad. Navuk. BSS,R, Ser. Khim. Nauk.,
1973, 6, 104.

C 10H 160 M 152.236

o-Menth-1-en-8-ol Mo-00677 Constit. of oil of Juniperus communis. Oil. [rx]~ +2.1° (c, 1
rx,rx,2- Trimethyl-1-cyclohexene-1-methanol, 9Cl. 1-(1- in CC14).
Hydroxy-1-methylethyl)-2-methylcyclohexene
Thomas, A.F., Helv. Chim. Acta, 1973, 56, 1800 (isol)
Kreiser, W. eta/, Helv. Chim. Acta, 1974, 57, 164 (synth)
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1976, 14, 932 (synth)

Cantharidin Mo-00680
Hexahydro-3a, 7a-dimethyl-4, 7-epoxyisobenzofuran-1 ,3-
C 10H 180 M 154.252
dione, 9CI. Cantharides camphor. Cantharone
Oil. Bp3s 110-111°.
[56-25-7]
Kay, F.W. et a/, J. Chern. Soc., 1905, 1fT, 1066 (synth)

[ft)o
0
o-Menth-1-en-~ne Mo-00678
2-/sopropyl-3-methyl- 2-cyclohexen-1-one
[7291-87-4]
0
C 10H 120 4 M 196.202
Occurs in Lytta vesicatoria and many other insects. Has
reputed aphrodisiac props. Vesicant, counterirritant and
diuretic. Plates. Mp 218°.
C 10H 160 M 152.236 I> Skin irritant and tumour promoting agent. RN857 5000.
Oil. Bp 217-219°. Stork, G. et al, J. Am. Chern. Soc., 1953, 75, 384 (synth)
Nasipuri, D. eta/, J. Chern. Soc., Perkin Trans. 1, 1975, 2052. Peter, M.G. eta/, Helv. Chim. Acta, 1977, 60, 2756 (biosynth)
Zehnder, M. eta/, Helv. Chim. Acta, 1977, 60, 740 (cryst struct)
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 12518.
Woggon, W.-D. eta/, J. Chern. Soc., Chern. Commun., 1983, 272
(biosynth)
Dauben, W.G. et a/, J. Org. Chern., 1985, 50, 2576 (synth)

IX-Cyclogeraniol Mo-00681
2,6,6-Trimethyl-2-cyclohexene-1-methanol, 9CI. 3-
Hydroxymethyl-2,4,4-trimethylcyclohexene
[6627-74-3]

OcCH,OH (R)-form

C 10H 180 M 154.252

(R)-form [52645-30-4]
Viscous oil with pleasant odour. Bp 213-217°. [rx]n
+ 122° (EtOH).
!:J. 1-Isomer: fJ-Cyclogeraniol. 2,6,6- Trimethyl-1-cyclohexene-
1-methanol, 9CI

123
5,5-Dimethyl-4-methylene-2-... - Hexahydro-3,7a-dihydroxy-3a,7-... Mo-00682- Mo-00687

C 1JI180 M 154.252 c.,H220s M 306.358

Needles with eucalyptus odour. Mp 43-44°. Bp 11 101- Constit. of F. hispanica. Oil. Bp0 _1 140°. [ali:' --64.SO (c,
1020. 5 in Et20).
(S)-form [52646-93-2] 0-(4-Acetoxy-3-methyl-2-butenoyl): [28333-41-7].
Viscous oil with pleasant odour. Bp 213-217°. [<Xln C 17H 240 5 M 308.374
- 122° (EtOH). Constit. of Ligusticum seguieri and S. carvifolium. Liq.
Biichi, G. eta/, J. Am. Chern. Soc., 1964, 86, 2884. [ali:' +81° (c, 1 in CC14) (+44°).
Shibasaki, M. eta/, Chern. Pharm. Bull., 1975, 23, 279. 0-(4-Hydroxy-3-methyl-2-butenoyl): [33579-66-7].
C 15H 220 4 M 266.336
5,5-Dimethyl-4-methylene-2-cyclohexene- Mo-00682 Constit. of L. seguieri and S. carvifolium. [a]i,O + 37° (c,
1-carboxylic acid 1.2 in CC14).
Shonanic acidt 0-(3-Methyl-2-butenoyl): [33530-15-3].
C1 5H 220 3 M 250.337
[618-55-3]
Constit. of L. seguieri. Oil. [ali:' + 15° (c, 1 in CHCI 3).
[41628-55-1]
Bohlmann, F. eta/, Chern. Ber., 1969, 102, 2211; 1971, 104, 1957;
1974, 107, 1769.
Lemmich, J. eta/, Acta Chern. Scand., 1971, 25, 995.
C 10H 140 2 M 166.219
Constit. of Libocedrus formosana. Cryst. (pet. ether). Mp Filifolide A Mo-00685
40-41°. Bp 754 264°. [<X]~ -0.75° (EtOH). [50585-61-0]
Ichikawa, N., Bull. Chern. Soc. Jpn., 1936, 11, 759; 1937, 12, 267
(isol, struct)
A
8,8-Dimethyl-2-methylene-6-
oxabicyclo(3.2.1)octane
Mo-00683

C 10H 140 2 M 166.219

ltk
Karaluura ether
[19901-96-3] Constit. of Artemisia filifolia and A. di.ffusa. [ali: -33.2°
(c, 0.4 in CHCI 3).
Torrance, S.J. eta/, J. Org. Chern., 1974, 39, 1068.
Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 2723 (isol, pmr, cmr)
Relative
configuration
Filifolide B Mo-00686
[50585-62-1]
CioHI60 M 152.236
Constit. of "Shinshu-wase" hops. Oil. Bp 15 50-53°.
Naya, Y. eta/, Tetrahedron Lett., 1968, 1645 (isol) Absolute
Coates, R.M. et a/, J. Org. Chern., 1970, 35, 865 (synth) configuration
Mukaiyama, T. eta/, Chern. Lett., 1979, 1175 (synth)
Armstrong, R.J. eta/, Can. J. Chern., 1983, 61, 214; 1986, 64, 584
(synth) CIOH1402 M 166.219
Mori, K. eta/, Tetrahedron, 1985, 41, 5487 (synth) Constit. of Artemisiafilifolia. Oil. [ali: +43.8° (c. 1.2 in
CHCI 3).
Ferulol Mo-00684 Torrance, S.J. et a/, J. Org. Chern., 1974, 49, 1068.
3-Hydroxy-4,6,6-trimethyl-1 ,4-cyclohexadiene-1-
carboxaldehyde Hexahydro-3,7a-dihydroxy-3a,7-dimethyl- Mo-00687
[55568-77-9] 1,4-isobenzofurandione, 9CI

~CHO

CIOH1402 M 166.219
~ OH

Derivs. are known with both positive and negative specific CIOH1405 M 214.218
~ 0 OH

rotations and may belong to opposite enantiomeric (3R,3aR,7R,7aR)-form

series. Constit. of the roots of Selinum carvifolium. Di-Ac: [115783-47-6]. 3,7a-Diacetoxyhexahydro-2-oxa-3a,7-
Derivs. of Ferulol reported from Astrantia, dimethyl-1 ,4-indanedione
Cenolophium, Eryngium, Ferula, Hacquetia, Hladnikia, C 14H 180 7 M 298.292
Ligusticum, Peucedanum, Selinum and Silaum spp. Oil. Constit. of Nepeta tuberosa. Oil. [a]~ + 113.8° (c, 4.9 in
[a]i,O + 15° (c, 1 in CHC1 3). CHCI 3).
Angeloyl: [28333-43-9]. (3R,3aR,7S,7aR)-form
C 15H 200 3 M 248.321 Di-Ac: [115783-49-8].
Constit. of Ferula hispanica. Oil. Bp 0 . 1 130°. [ali:' -52° Constit. of N. tuberosa. Oil. [a]~ + 34.8° (c, 2.4 in
(c, 4.5 in Etp).
CHCI 3).
2-(Acetoxymethyl)-2-butenoyl(Z-): [28333-44-0].

124
5-Hydroxy-4,6,6-trimethyl-1,3-... - 2,6,6-Trimethyl-1,3-cyclohexadienal Mo-00688 - Mo-00694

(3S,3aR,7R,7aR)-form 3-Hydroxy-2,6,6-trimethyl-1- Mo-00691

Di-Ac: [115783-48-7]. cyclohexenecarboxylic acid
Constit. of N. tuberosa. Oil. [1X]i; +21.35° (c, 2.13 in

~H
CHC1 3).
(3S,3aR,7S,7aR)-form
Di-Ac: [115783-50-1].
Constit. of N. tuberosa. Oil. [1X]i; + 17.47° (c, l. 75 in
I
CHC1 3). OH
Drones, J.G. et al, Phytochemistry, 1988, 27, 1525. C10H 160 3 M 184.235
0-P-v-G/ucopyranoside: [104056-82-8]. Rehmapicroside ·
5-Hydroxy-4,6,6-trimethyl-1,3- Mo-00688 C 16H 260 8 M 346.377
cyclohexad.iene-1-carboxaldehyde Constit. of dried root of Rehmannia glutinosa
[34143-99-2] (Rehmanniae Radix). Prisms. Mp 127-129°. [1X]i? + 8.5°
(MeOH).

HO.DCHO Yoshikawa, M. et al, Chern. Pharm. Bull., 1986, 24, 2294.

4-Hydroxy-2,6,6-trimethyl-1- Mo-00692
cyclohexenecarboxylic acid
C 10H 140 2 M 166.219 Picrocrocinic acid
Constit. of Selinum carvifolium. Oil. [1X]i? +45° (c, 1 in
CHC1 3).
0-(4-Hydroxy-3-methy/-2-butenoyl): [33530-22-2]. XcooH
Ct5H200 4 M 264.321
Constit. of Ligusticum seguieri. Liq. [1X]i? + 126° (c, 1.2 HO'u
in CC14).
C10H 160 3 M 184.235
0-(4-Acetoxy-3-methy/-2-butenoyl):
C 17H 220 5 M 306.358 0-P-v-G/ucopyranoside: [62218-53-5].
Constit. of L. seguieri. Oil. [1X]n + 103° (c, 1.2 in CC14). Ct6H260 8 M 346.377
Constit. of Gardenia jasminoides. Hygroscopic amorph.
Lemmich, J. et al, Acta Chern. Scand., 1971, 25, 995. powder. [IX]~ -28.2° (c, 1.1 in MeOH).
0-P-v-G/ucopyranoside, tetra-Ac: Cryst. Mp 137-138".
2-Hydroxy-2,6,6-trimethylcyclohexanone Mo-00689

ex
Takeda, Y. et al, Chern. Pharm. Bull., 1976, 24, 2644.
[7 500-42-7]
Palasonin Mo-00693
Hexahydro-3a-methyl-4, 7-epoxyisobenzofuran-1 ,3-dione,
9CI. Demethylcantharidin
[11043-72-4]
OH
H 0
C9H 160 2 M 156.224
Constit. of the aroma of black tea. ~0 Absolute
Muggler-Chavan, F. et al, Helv. Chim. Acta, 1969, 52, 549. ~ configuration
Ragoussis, N. et al, Synthesis, 1985, 489 (synth)
H3C 0
4-Hydroxy-2,6,6-trimethyl-1- Mo-00690 C9H 100 4 M 182.176
cyclohexenecarboxaldehyde Constit. of the seeds of Butea frondosa. Mp 109-111 o.
[138-55-6] N-Phenylimide: Mp 204.SO.
Peter, M.G. et al, Helv. Chim. Acta, 1974, 57, 32 (abs conjig)
Stevens, A.D., Diss. Abstr. Int., B, 1975, 36, 1230; CA, 84, 30937
XcHo (synth)
Chandra, J.S. et al, Indian J. Pharm. Sci., 1978, 40, 97 (isol)
HO'u
2,6,6-Trimethyl-1,3-cyclohexadienal Mo-00694
M 132.202
Safranal. Dehydro-p-cyclocitra/
0-P-v-G/ucopyranoside: Picrocrocin. Safranbitter.
[116-26-7]
Saffronbitter
Ct6H260 7 M 330.377
Isol. from saffron (stamens of Crocus sativus). Cryst. XvcHO
(MeOH/CHC1 3/Et20). Mp 156°. [1X]i? -58° (H 20).
Duquenois, P., Bull. Soc. Pharm. Strasbourg, 1972, 155, 149 (rev)
Buchecker, R. et al, Helv. Chim. Acta, 1973, 56, 1121 (struct)
lJl
C 10H 140 M 150.220
Hydrol. prod. of Picrocrocin. Characteristic aroma of
saffron. Liq. Bp760 172°, Bp 1 70°.
Oxime:
C 10H 15NO M 165.235
Cryst. (pet. ether). Mp 65°.

125
2,6,6-Trimethyl-1,3-cyclohexadiene-... - 2,2,4-Trimethyl-3-cyclohexene-1-... Mo-00695 - Mo-00700

Semicarbazone: Cryst. (MeOH). Mp 175°. 1,2,2-Trimethyl-3-cyclohexene-1- Mo-00698

Konst, W.M.B. et al, Tetrahedron Lett., 1974, 3175 (synth) carboxylic acid, 9CI
Kametani, T. et a/, J. Chern. Soc., Chern. Cornrnun., 1979, 1128 Carnphorenic acid
(synth)
Kametani, T. et al, Chern. Pharrn. Bull., 1981, 29, 105 (synth) [4720-85-8]

2,6,6-Trimethyl-1,3-cyclohexadiene-1- Mo-00695
carboxylic acid, 9CI
Sqfranic acid

6
[4430-99-3] ctoH 160 1 M 168.235
(+)-form
Needles (EtOH). Mod. sol. hot Hp. Mp 161°. [rx.m
COOH
+ 179.4° (CHC13). Subl., steam-volatile.
CH3 Me ester:
C10H 140 1 M 166.219 CuHtaOz M 182.262
Prisms (pet. ether). Mp 63-64°. Bp 215°.
Biichi, G. eta/, Helv. Chim. Acta, 1971, 54, 1767 (synth, nrnr, ir,
Anhydride:
uv, ms) C10H 300 3 M 318.455
Plates (EtOH). Insol. H 20. Mp 84-85°. Steam-volatile.
2,4,4-Trimethyl-1-cyclohexene-1- (±)-form
Mo-00696
Mp 165-166° (pet. ether/C6H 6).
carboxaldehyde, 9CI
Amide:
P-Cyclolavandulal
CIOH17NO M 167.250
[5939-87-7] Mp 164-165°.
Shive, B. et a/, J. Am. Chern. Soc., 1941, 63, 2979.

~ CHO
1,3,4-Trimethyl-3-cyclohexene-1-
carboxylic acid, 9CI
[68826-24-4]
Mo-00699

c>:H
CIOH160 M 152.236
Constit. of Seseli indicum. Oil. Bp 10 100-105° (bath).
2,4-Dinitrophenylhydrazone: Cryst. (CHC1 3 jMeOH). Mp
187-188°.
Carboxylic acid: [18088-97-6]. 2,4,4-Trimethyl-1-
cyclohexene-1-carboxylic acid, 9CI. P-Cyclolavandulic acid
cloHt,oz M 168.235 CIOH1602 M 168.235
Isol. from S. indicum. Cryst. (MeOH aq.). Mp 110-111°. (±)-form
Brenner, A. eta/, Helv. Chirn. Acta, 1952, 35, 1615 (synth) Cryst. (AcOH aq.). Mp 55.5-56S.
Ferrero, C. eta/, Helv. Chirn. Acta, 1956, 39, 2109 (synth) Me ester: [68826-23-3].
Dixit, S.M. et a/, Chern. Ind. (London), 1967, 1256 (isol) C 11H 180 1 M 182.262
Logani, M.K. et al, Tetrahedron Lett., 1967, 2645 (isol) d~0 0.97. Bp20 103.0-103_50.
Amide: [68826-25-5].
2,6,6-Trimethyl-2-cyclohexene-1- Mo-00697 C10H 17NO M 167.250
carboxaldehyde Cryst. (cyclohexane). Mp 105-106°.
rx.-Cyclocitral Kealy, T.J. et al, J. Org. Chern., 1961, 26, 3126 (synth)
[14505-74-9]

(f:HO
2,2,4-Trimethyl-3-cyclohexene-1- Mo-00700
carboxylic acid, 9CI, SCI
[13746-43-5]

C 10H 160 M 152.236

(R)-form
Oil. Bp 10 75-77°. [rx.Ji? -637°.
Semicarbazone: Cryst. Mp 206°.
Buchecker, R. eta/, Helv. Chirn. Acta, 1973, 56, 2548 (abs config) C 10H 160 1 M 168.235
Mikhailov, B.M. et al, J. Organornet. Chern., 1978, 154, 131
(synth) (±)-form
Needles (AcOH aq.). Mp 86-87°.
Me ester: [19766-10-0].
C 11 H 180 1 M 182.262
Bp7_5 127°.
Erman, W.F. et al, J. Org. Chern., 1969, 34, 2196 (synth, ir, nrnr)
Torrance, S.J. et al, J. Org. Chern., 1974, 39, 1068 (synth, ir, ms)

126
2,2,6-Trimethyl-3-cyclohexene-1-... - 2,7-Dihydroxy-4-isopropyl-2,4,6-... Mo-00701 - Mo-00706

2,2,6-Trimethyl-3-cyclohexene-1- Mo-00701 2,6,6-Trimethyl-3-cyclohexene-1- Mo-00704

carboxylic acid, 9CI, SCI carboxylic acid, 9CI

CIOH1602 M 168.235 C10H 160 2 M 168.235

Prisms (EtOAc or ligroin). Mp 102°. Bp6 123°. Mp 75-76°.
Et ester: [22463-50-9]. Et ester: [22463-51-0].
C12H 200 2 M 196.289 C12H 200 2 M 196.289
Bp6 94°. Perfumery agent. Liq. Bp8 87-88°.
A1konyi, I. et al, Chern. Ber., 1969, 102, 709 (synth) Merling, G., Ber., 1908, 41, 2064 (synth)
Ger. Pat., 2 305 140, (1973); CA, 79, 115743 (synth)
2,6,6-Trimethyl-1-cyclohexene-1- Mo-00702
carboxylic acid, 9CI, SCI
[471-90-9]

Cycloheptane
CIOHI602 M 168.235
monoterpenoids
Prisms or plates (ligroin). Spar. sol. Hp. Mp 104-106°.
Me ester: [49815-58-9].
C12H 200 2 M 196.289
Bp0 .05 46-48°. 2,7-Dihydroxy-3-isopropyl-2,4,6- Mo-00705
Heather, J.B. et al, J. Am. Chern. Soc., 1976, 98, 3661 (synth, nmr,
cycloheptatrien-1-one
t) 2, 7- Dihydroxy-3-( 1-methy/ethyl)-2,4,6-cycloheptatrien-1-one,
9CI. 7-Hydroxy-6-isopropy/tropo/one. 7-Hydroxy-3-
isopropy/tropo/one. IX- Thujaplicinol
2,6,6-Trimethyl-2-cyclohexene-1- Mo-00703
[16643-33-7]
carboxylic acid, 9CI, SCI
[564-24-9]
HO~OH.
u
~COOH (R)-form 0-(
CIOH1203 M 180.203
CIOH1602 M 168.235 Constit. of the heartwood of Cupressus pygmaea. Oil. d~2
(R)-form [52646-90-9] 1.184. ni;l.6323.
[1X]i? + 338.5° (EtOH). 2-Me ether: 7-Hydroxy-3-isopropy/-2-methoxy-2,4,6-
Me ester: [52567-44-9]. cycloheptatrien-1-one. 4-/sopropy/-3-methoxytropo/one.
C11H 180 2 M 182.262 Pygmaein
[1X]i? + 314.2° (EtOH). C11 H 140 3 M 194.230
(S)-form [24190-30-5] Constit. of the heartwood of C. pygmaea. Cryst.
[IX]~ - 335.SO (EtOH). (hexane). Mp 39-40°.
Me ester: [52567-43-8]. 7-Me ether: 2-Hydroxy-3-isopropy/-7-methoxy-2,4,6-
[1X]i? -315.7° (EtOH). cycloheptatrien-1-one. 3-Isopropy/-7-methoxytropo/one.
(±)-form [64599-73-1] Isopygmaein
Plant growth inhibitor. Needles (ligroin). Spar. sol. Hp. C11 H1P 3 M 194.230
Mp 106°. Bp20 160-161°. Constit. of the heartwood of Papuacedrus torrice/lenis.
Cryst. (2,2,4-trimethylpentane). Mp 111-112°.
Me ester: [28043-10-9].
Oil. Bp 14 89°. Zavarin, E. et al, J. Org. Chern., 1961, 26, 173, 1679; 1962, 27,
3368 (isol, ir, uv, pmr, struct, synth)
Amide: [61900-00-3].
CIOH17NO M 167.250
Cryst. (C6H 6/pet. ether). Mp 120-121°. 2,7-Dihydroxy-4-isopropyl-2,4,6- Mo-00706
Unde, G. et al, Helv. Chim. Acta, 1973, 56, 2548 (synth) cycloheptatrien-1-one
Bedoukian, R.H. eta/, J. Org. Chern., 1975, 40, 2154 (synth, ir, 2, 7- Dihydroxy-4-( 1-methy/ethyl)-2 ,4,6-cycloheptatrien-1-one,
pmr) 9CI. 7-Hydroxy-4-isopropy/tropo/one. 4-Hydroxy-7-
isopropyltropolone. P- Thujaplicinol
CIOH1203 M 180.203
Fairly widespread constit. of the Cupressaceae. Pale-yellow
cryst. (hexane or EtOH). Mp 57.5-58°.
Cu chelate: Mp 237-238°.

127
4,4-Dimethyl-1,6-•.. - IJ-Dolabrin Mo-00707 - Mo-00713

Gardner, J.A.F. et al, Can. J. Chern., 1957, 35, 1039 (isol, ir, uv, Probable struct. Constit. of the essential oil of Libocedrus
struct) formosana. Mp 44-46°, Mp 87-87.5°.
Zavarin, E. et al, Phytochemistry, 1967, 6, 1387 (isol, occur)
Pasto, D.J., J. Org. Chern., 1962, 27, 2787 (struct, bib[)

4,4-Dimethyl-1,6- Mo-00707
5,5-Dimethyl-1,3,6-cycloheptatriene-1- Mo-00711
cycloheptadienecarboxylic acid
carboxylic acid, 9CI
Thujic acid. Dehydroperillic acid

~H [499-89-8]

9
COOH

CtoHt40l M 166.219
Isom. prod. of 4,4-Dimethyl-2,6-cycloheptadienecarboxylic
acid, Mo-00709; poss. constit. of the essential oil of C 10H 120 2 M 164.204
Libocedrus formosana. Mp 79-80°. Constit. of the heartwood of Thuja plicata. Also from T.
orienta/is and Libocedrus formosana. Cryst. (pet. ether).
Cheng, Y. et al, J. Chin. Chern. Soc. (Taipei), 1961, 8, 103; CA, 58,
5529h. Mp 88-89°. Unstable.
Pasto, D.J., J. Org. Chern., 1962, 77, 2787. Me ester:
C 11 H 140 2 M 178.230
4,4-Dimethyl-2,5- Mo-00708 lsol. from T. plicata. Mp 34-35°.
cycloheptadienecarboxylic acid Gripenberg, J., Acta Chern. Scand., 1949, 3, 1137 (isol, struct)
Kurth, E.F., J. Am. Chern. Soc., 1950, 72, 5778 (isol, ester)
SlwiUlllic acidt Gripenberg, J., CA, 1952, 46, 5005 (synth)

¢_"
Davis, R.E. et al, J. Am. Chern. Soc., 1966, 88, 4583 (cryst struct)
Hack, V. et al, Can. J. Chern., 1973, 51, 3230 (isol)
Guenther, H. et al, Org. Magn. Reson., 1974, 6, 388 (pmr)

4,4-Dimethyl-2-cyclohepten-1-one Mo-00712
[36295-77 -9]
CtoHt40l M 166.219
Probable struct. Isol. from essential oil of Libocedrus
formosana. Mp 40-41°. Mp. not certain.
Pasto, D.J., J. Org. Chern., 1962, 27, 2787 (struct, bib/)

4,4-Dimethyl-2,6- Mo-00709
cycloheptadienecarboxylic acid C,H140 M 138.209
Constit. of the oleoresin of Abies ba/samea. Liq. isol. by
glc.

~H Balogh, B. et al, Phytochemistry, 1972, 11, 1481.

IJ-Dolabrin Mo-00713
2-Hydroxy-4-(1-methylethenyl)-2,4,6-cyc/oheptatrien-1-one,
9CI. 4-/sopropeny/tropo/one
c1oH14o2 M 166.219 [4570-11-0]
Isom. prod. of Thujic acid, prob. a constit. of the essential
oil of Libocedrus formosana. Cryst. (pet. ether at low
temp.). Mp 58-59.5°. V. unstable, readily isom. and dec.
Cheng, Y. et al, J. Chin. Chern. Soc. (Taipei), 1961, 8, 103; CA, 58,
5529h.
Pasto, D.J., J. Org. Chern., 1962, 27, 2787.

5,5-Dimethyl-1,3- Mo-00710
cycloheptadienecarboxylic acid C 10H 100 2 M 162.188
lsoslwnanic acid Present in essential oil of Thujopsis dolabrata. Also from
Juniperus spp. Cupressus spp. and Thuja plicata. Pale-
yellow needles. Mp 58-59°.
Nozoe, T. et al, Chern. Ind. (London), 1957, 1070 (isol, uv, struct)
Zavarin, E. et al, J. Org. Chern., 1959, 24, 1318 (isol)
Hart, D.E. et al, J. Am. Chern. Soc., 1978, 100, 4393 (synth)

M 166.219

128
t~-Dolabrinol - 1,1,4-Trimethylcycloheptane Mo-00714 - Mo-00720

~X-Dolabrinol Mo-00714 2-Hydroxy-5-isopropyl-2,4,6- Mo-00717

2,3-Dihydroxy-4-(1-methylethenyl)-2,4,6-cycloheptatrien-1- cycloheptatrien-1-one
one, 9Cl. 7-Hydroxy-3-isopropenyltropolone 2-Hydroxy-5-( 1-methylethyl)-2,4,6-cycloheptatrien-1-one,
[16643-34-8] 9CI. 5-Isopropyltropolone. -y- Thujaplicin
[672-76-4]
0 C 10H 120 2 M 164.204
H06OH; Occurs in the heartwood of Cupressus stephensonii and of
~ ~ Thuja plicata, other T. spp., other C. spp., Tetraclinis
articulata and others. Antifungal. Needles (pet. ether).
- ~ Mp 82°.
C 10H 100 3 M 178.187 t> GU4580000.
Present in heartwood of Cupressus pygmaea. Bp 1_2 140- Cu complex: Mp 259-260°.
1600.
Erdtman, H. et al, Acta Chern. Scand., 1948, 2, 625 (isol, struct)
Zavarin, E., J. Org. Chern., 1962, 27, 3368 (synth) Cook, J.W. et al, J. Chern. Soc., 1951, 695 (synth)
Smith, L.V. et al, Phytochemistry, 1967, 6, 1387 (isol) Zavarin, E. et al, J. Org. Chern., 1959, 24, 1318 (isol)
Chow, Y.-L. et al, Acta Chern. Scand., 1962, 16, 1291 (isol)
2-Hydroxy-3-isopropyl-2,4,6- Mo-00715 Berg, J.-E. et al, Acta Crystallogr., Sect. B, 1976, 32, 3121 (cryst
struct)
cycloheptatrien-1-one Takaya, H. et al, J. Am. Chern. Soc., 1978, 100, 1778 (synth)
2-Hydroxy-3-(1-methylethyl)-2,4,6-cycloheptatrien-1-one,
9CI. 3-Isopropyltropolone. rr.-Thujaplicin
4-Isopropyl-2,4,6-cycloheptatrienone Mo-00718
[1946-74-3] 4-Isopropyltropone. Nezukone
0 [13656-81-0]

C 1oH120 2 M 164.204
Occurs in Juniperus conferta and the heartwood of Thuja
plicata. Also from T. occidentalis, T. dolabrata, T.
standishii, Cupressus spp., and Juniperus spp. Antifungal.
C 10H 120 M 148.204
Needles (pet. ether). Mp 82° (34°). Bp0.001 80° (bath).
Constit. of Thuja standishii. Unstable pale-yellow oil. dl~
Me ether: Mp 71.5-72.SO. Bp4 118-120°. 1.017. Bp 5 127-128°. nii
1.5691.
Gripenberg, J., Acta Chern. Scand., 1948, 2, 639 (isol) Semicarbazone: Red cryst. Mp 174-176°.
Cook, J.W. et al, J. Chern. Soc., 1951, 695 (synth)
Zavarin, E. et al, J. Org. Chern., 1959, 24, 1318 (isol) Takaya, H. et al, J. Am. Chern. Soc., 1978, 100, 1778 (synth, bibl)
Bredenberg, J.B., Acta Chern. Scand., 1961, IS, 961 (isol) Wenkert, E. et al, Helv. Chim. Acta, 1987, 70, 2159 (synth, bibl)
Takaya, H. et al, J. Am. Chern. Soc., 1978, 100, 1778 (synth)
2,6,6-Trimethyl-2,4-cycloheptadien-1-one Mo-00719
2-Hydroxy-4-isopropyl-2,4,6- Mo-00716 Eucarvone. Eucarvol
cycloheptatrien-1-one [503-93-5]
2-Hydroxy-4-( 1-methylethyl)-2 ,4,6-cycloheptatrien-1-one,
9CI. 4-Isopropyltropolone. fJ- Thujaplicin. Hinokitiol
[499-44-5]
C 10H 120 2 M 164.204
Occurs in Juniperus conferta, in the oil of the wood of the
Hinoki tree (Chamaecyparis obtusa) and in the C 10H 1P M 150.220
heartwood of Thuja plicata. Widespread in the Isol. from oil of Asarum sieboldii. Oil with odour
Cupressaceae. Antifungal substance. Cryst. (pet. ether). resembling menthone. Bp8 82.5-84°.
Mp 52-52.SO.
Oxime: [1845-26-7].
t> GU4200000. C 10H 15NO M 165.235
Cu complex: Mp 177°. Cryst. (MeOH). Mp 106°.
Anderson, A.B. et al, Acta Chern. Scand., 1948, 2, 644 (isol, struct) Corey, E.J. et al, J. Am. Chern. Soc., 1956, 78, 174 (synth)
Tanaka, K. et al, Tetrahedron, 1971, 27, 4889 (synth) Childs, R.F. et al, Can. J. Chern., 1977, SS, 3495 (pmr)
Derry, J.E. et al, J. Chern. Soc., Perkin Trans. 2, 1972, 694 (cryst Blanco, L. et al, Tetrahedron Lett., 1981, 645 (synth)
struct)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, 1,1,4-Trimethylcycloheptane, 9CI, SCI Mo-00720
no. 573 (occur) Eucarvane
Noyori, R. et al, J. Org. Chern., 1975, 40, 806 (synth) [2158-55-6]
Tamura, Y. et al, Tetrahedron Lett., 1977, 4075 (synth)
Neumann, M. et al, Tetrahedron Lett., 1978, 5033 (synth)
Miyashita, M. et al, J. Org. Chern., 1987, 52, 2602 (synth)

129
2,6,6-Trimethylcycloheptanone - 2,3-Bornanediol Mo-00721 - Mo-00725

C 10H 20 M 140.268
(±)-form
d~0 0.80. Bp720 162-163°.
Christl, M. et al, J. Org. Chern., 1972, 37, 3443 (synth, pmr, cmr)
Camphanes
2,6,6-Trimethylcycloheptanone, 9CI Mo-00721
Tetrahydroeucarvone
Bornane Mo-00724
[4436-59-3] 1, 7,7- Trimethylbicyclo[2 .2 .1]heptane. Camphane
[464-15-3]

C1oH180 M 154.252
(±)-form
Liq. with peppermint odour. d~0 0.91. Bp 208-209°, Bp 18 ClOHlB M 138.252
76-77°. Cryst. Mp 158-159°.
Semicarbazone: 2 forms: cryst. (EtOAc), needles (EtOH). Th?mas, A.F. et al, Helv. Chim. Acta, 1964, 47, 475 (ms)
Tmvonen, H. et al, Tetrahedron Lett., 1971, 3203.
Cryst. spar. sol. EtOAc, needles sol. EtOAc. Mp 200-
2010 (cryst.), Mp 162-165° (needles).
McMurry, J.E. et al, J. Org. Chern., 1973, 38, 2821 (synth, ir, pmr) 2,3-Bomanediol Mo-00725
1,7,7-Trimethylbicyclo[2.2.1]heptane-2,3-diol. 2,3-
Camphanediol
1,4,4-Trimethylcycloheptene, 9CI Mo-00722
Eucarvene

~H
[4755-36-6]

OH
(1R,2R,3R)-form
CtoH180 1 M 170.251
CtoH 18 M 138.252
Liq. d~0 0.82. Bp 168.5-169°. (IR,2R,3R)-form
( + )-endo,exo-form
Barbier, H., Helv. Chim. Acta, 1940, 23, 528 (synth) ~ryst. (C6H 6 jpet. ether). Mp 254-256°. [cxln + 15° (c, 1.5
Welch, S.C. et al, J. Org. Chern., 1978, 43, 2717 (synth)
m EtOH).
2-Ac: [61586-52-5]. Vulgarole
2,2,5-Trimethyl-4-cyclohepten-1-one, 9CI Mo-00723 CuH 200 3 M 212.288
Karalumaenone Constit. of oil of Artemisia vulgaris. Thick oil. Rel.
[19822-67-4] config. only detd., could be the enantiomer.
(1R,2R,3S)-form
(+ )-endo,endo-form
Cryst. (pet. ether). Mp 255.5-256.SO. [ex] +31.3° (c, 6 in
EtOH). D

C10H 160 M 152.236 .
Minor constit. of the essential oil of 'Shinshuwase' hops.
Liq. Bp 15 55-63°.
Alcohol: [68224-52-2]. 2,2,5-Trimethyl-4-cyclohepten-1-ol.
Karalumaenol
C1oH180 M 154.252
Oil. Bp 15 ll0°.
Naya, Y. et al, Tetrahedron Lett., 1968, 1645 (isol, struct)
Demole, E. et al, Helv. Chim. Acta, 1971, 54, 456 (synth)
Wender, P.A. et al, J. Org. Chern., 1976, 41, 3490 (synth)
Hashimoto, S. et al, J. Am. Chern. Soc., 1977, 99, 4192 (synth)
Cairns, P.M. et al, Tetrahedron Lett., 1982, 23, 1405 (synth)
Wang, D. et al, J. Chern. Soc., Chern. Commun., 1984, 1273 (synth)
Uneyeyama, K. et al, J. Org. Chern., 1985, SO, 3161 (synth)
(1R,2S,3S)-form [28357-12-2]
( + )-exo,endo-form
Cryst. (C 6H 6). Mp 250.5-252.0°. [cxln + 5.SO (c, 3 in
EtOH).
(1R,2S,3R)-form [59599-25-6]
(- )-exo,exo-form
Cryst. (pet. ether). Mp 256.5-258.SO. [cxln -17.4° (c, 6 in
EtOH).
Coulombeau, C. et al, Bull. Soc. Chim. Fr., 1970, 1199 (synth)
Nano, G.M. et al, Planta Med., 1976, 30, 211 (Vulgarole)
Burgstahler, A.W. et al, Tetrahedron, 1976, 32, 309 (svnth)
Angyal, S.J. et al, Aust. J. Chern., 1984, 37, 661 (cmr: cryst struct)
Allen, M.S. et al, Can. J. Chern., 1984, 62, 2707 (pmr, bib[)

130
2,5-Bornanediol- 2,9,10-Bornanetriol Mo-00726 - Mo-00732

2,5-Bornanediol Mo-00726 C 10H 180 1 M 170.251

1,7,7- Trimethylbicyclo[2.2.J]heptane-2,5-diol. 5- Constit. of Artemisia spp. Cryst. Mp 180°.
Hydroxyborneol Huneck, S. et al, Phytochemistry, 1986, 25, 883.

2,3-Bornanedione Mo-00730
1,7,7-Trimethylbicyclo[2.2.1]heptane-2,3-dione.
Camphorquinone
[465-29-2]

~
C 10H 180 1 M 170.251
(IS,2R,5S)-form [64911-68-8] Angelicoidenol
Constit. of Pleurospermum angelicoides and Hedycarya
angustifolia. Cryst. (CHC1 3). Mp 255-257°. [cx)ii -16.12°
0
(c, 0.46 in MeOH).
C 10H 140 1 M 166.219
Marquet, A. et al, Bull. Soc. Chim. Fr., 1967, 128 (synth)
Allen, M.S. et al, Can. J. Chern., 1979, 57, 733 (synth) (-)-form [10334-26-6]
Mahmood, U. et al, Phytochemistry, 1983, 22, 774 (isol) Yellow cryst. by subl. Mp 199°. [cx]i,O -105.4° (CHC1 3).
Gunawardana, Y.A.G.P. et al, J. Nat. Prod. (Lloydia), 1988, 51, 3-0xime: lsonitrosocamphor
142 (isol, cmr, pmr)
C 10H 1sN0 2 M 181.234
Cryst. (C6H 6jpet. ether). Mp 153°. [cx]i,4 +200° (EtOH).
2,8-Bornanediol Mo-00727 Hiicke1, W. et al, Justus Liebigs Ann. Chern., 1962, 652, 81 (synth)
2-Hydroxy-l ,7-dimethylbicyclo[2.2.J]heptane-7-methanol, Fleming, I. et al, J. Chern. Soc. C, 1968, 1289 (synth)
9CI Luk, C.K. et al, J. Am. Chern. Soc., 1974, 96, 2006 (uv)
[85610-81-7] Faure, R. et al, Acta Crystallogr., Sect. C, 1986, 42, 838 (cryst
struct, oxime)

H~ 2,3,10-Bornanetriol
J-(Hydroxymethyl)-7,7-dimethylbicyclo[2.2.1]heptane-2,3-
diol, 9CI. 3,10-Dihydroxyborneol
Mo-00731

H~
OH
C 10H 180 1 M 170.251
Constit. of Ichthyothere terminalis. Cryst. Mp 275°. (IS,2S,3R)-fo'm
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2317.
HO CHPH
2,9-Bornanediol Mo-00728 C1oH180 3 M 186.250
Vicodio/ (IS,2S,3R)-form [114437-17-1]
[128898-66-8] Constit. of Florestina tripteris. Oil. [ex]~ -40° (c, 0.5 in
CHC1 3).

~
(JS,2S,3S)-form [114489-85-9]
Constit. of F. tripteris. Oil. [cx]i;' + 21° (c, 0.1 in CHC1 3).
3-Ketone: [114437-19-3]. 3-Hydroxy-4-(hydroxymethyl)-7,7-
dimethylbicyclo[2.2.J]heptan-2-one, 9CI. 2,10-Dihydroxy-
3-bornanone. 10-Hydroxy-3-oxoborneol
OH C 10H 160 3 M 184.235
C 10H 180 1 M 170.251 Constit. of F. tripteris. Oil.
Constit. of Vicoa indica. Cryst. (CHC1 3 jhexane). Mp 242- Dominguez, X.A. et al, Phytochemistry, 1988, 27, 613.
2440. [cx]n -17° (c, 1 in CHC13).
Vasanth, S. et al, J. Nat. Prod. (Lloydia), 1990, 53, 354 (isol, pmr, 2,9,10-Bornanetriol Mo-00732
cmr, cryst struct) 1, 7- Bis(hydroxymethyl)-7-methylbicyclo[2 .2.J]heptan-2-ol.
9,10-Dihydroxyborneol
2,10-Bornanediol Mo-00729

~~
10-Hydroxyborneol. 2-Hydroxy-7,7-
dimethylbicyclo[2.2 .l]heptane-1-methanol

H
X
~
Abwlure
configuration
CioH180 3 M 186.250
OH CH20H

OH CH20H (IS,2R)-form

131
2-Bornanol - 2-Bornene Mo-00733 - Mo-00736

Constit. of Florestina tripteris. Oil. [1X]i;4 - 10° (c, 0.36 in 3-Bornanol Mo-00734
CHC1 3). 1,7,7-Trimethylbicyclo[2.2.l]heptan-3-ol
Dominguez, X.A. et al, Phytochemistry, 1988, 27, 613.

2-Bornanol Mo-00733 X OH
(IR,3R,4R)-form
Absolute

~
1, 7,7- Trimethylbicyclo[ 2.2./]heptan- 2-ol. 2-Hydroxybornane configuration
[10385-78-1]
CIOH180 M 154.252

~OH
(JR,3R,4R)-form [33016-93-2]
(+ )-Epiisoborneol
Cryst. by sub!. Mp 196-196.SO. [IX]~ + 12.6° (c, 1.1 in
toluene).
H (IR,2R)-form (JS,3R,4S)-form [22553-62-4]
(- )-Epiborneol
ClOHI80 M 154.252 Cryst. (pet. ether). Mp 181-182.SO. [IX]~ -4.9° (c, 1.5 in
Both Borneol and Isobomeol and their acetates are used toluene).
in the perfumery industry.
0-(4-Hydroxy-3-methoxycinnamoyl): Cleistophostaudin
(JR,2R)-form [10334-13-1] (- )-Isoborneol. P-Camphol. C 20H 21;04 M 330.423
/socamphol lsol. from Cleistopholis staudtii. Amorph. solid.
Found in Achillea .filipendulina, Cymbopogon goeringii
(1 S,3S,4S)-form [28974-20-1]
and others. Cryst. (pet. ether). Mp 212° (sealed tube).
(- )-Epiisoborneol
[IX]~ -32.30° (MeOH).
Cryst. by sub!. Mp 196-196.SO. [1X]n -lO.SO (c, 10 in
(JS,2S)-form [16725-71-6] EtOH).
(+ )-lsoborneol Heiniinen, E. et al, Suom. Kemistil. B, 1969, 42, 53; 1970, 43, 462;
Cryst. (pet. ether). Mp 214°. [1X]n +33.89° (EtOH). 1971, 44, 379 (synth, struct)
(JR,2S)-form [464-43-7] (+)-Borneol. ( + )-Bornyl alcohol. Tane, P.. et al, Phytochemistry, 1988, 27, 3986 (Cleistophostaudin)
Borneo camphor
Constit. of Curcuma aromatica and Cinnamomum 3-Bornanone Mo-00735
camphora and other plants. Cryst. (pet. ether). Mp 208°.
1,7,7- Trimethylbicyclo[2.2.J]heptan-3-one. Epicamphor. P-
Bp 212°. [IX]~ +37.7° (c, 5 in EtOH).
Camphor
~ ED7060000.
(JS,2R)-form [464-45-9] (-)-Borneol. Linderol. Ngai camphor
Constit. of A. filipendulina, Blumea balsamifera, Lindera
strychnifera etc. Cryst. (pet. ether). Mp 208-209°. Bp
212°. [IX]~ -37.74° (c, 5 in EtOH). (-)-form
~ DT5095000.
0-(3-Hydroxy-4-methoxybenzoyl): [70476-15-2]. Rubaferin
C 18H 1,.04 M 304.385 CIOH160 M 152.236
Constit. of Ferula rubroarenosa. Mp 106-107°. [1X]n (+)-form [13854-85-8]
-45.08° (c, 0.06 in CHC1 3). Cryst. Mp 182°. [1X]n + 58.4° (C 6H 6).
(JRS,2RS)-form [6627-72-1] (-)-form [10292-98-5]
( ± )-Isoborneol Cryst. Mp 186-187°. Bp 213°. [1X]n -58.0° (c, 2.8 in
Plates (pet. ether). Prac. insol. Hp. Mp 212° (sealed MeOH).
tube). Heinanen, E., Suom. Kemistil. B, 1969, 42, 53 (synth)
(JRS,2SR)-form [24393-70-2] Takeshita, H. et al, Bull. Chern. Soc. Jpn., 1969, 42, 2068 (synth)
(±)-Borneol Bartlett, L. et al, J. Chern. Soc. C, 1970, 2678 (abs config)
Mp 210-215°. Boust, C. et al, Bull. Soc. Chim. Fr., 1974, 877 (synth)
[124-76-5, 507-70-0]
Karrer, W. et al, Konstitution und Vorkommen tier Organischen 2-Bornene Mo-00736
Pflanzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, 1,7,7-Trimethylbicyclo[2.2.l]hept-2-ene. Bornylene
nos. 312, 313 (occur)
Oratani, T. et al, Agric. Bioi. Chern., 1974, 38, 1961 (synth)
Gream, G.E. et al, Aust. J. Chern., 1974, 27, 567 (synth) (+)-form
Helmchen, G., Tetrahedron Lett., 1974, 1527 (abs corifig)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr)
Tadesa, K. et al, Agric. Bioi. Chern., 1976, 40, 1069 (biosynth)
Stothers, J.B. et al, Can. J. Chern., 1976, 54, 1211 (cmr, biosynth)
Yamaguchi, S. et al, Tetrahedron Lett., 1977, 89 (conjig, pmr) CIOH16 M 136.236
Golovina, L.A. et al, Khim. Prir. Soedin., 1978, 712 (Rubaferin) (+)-form [18383-34-1]
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed., Cryst. (EtOH). Mp 109-lWO. Bp 146°. [1X]n +30.5°
Van Nostrand-Reinhold, 1979, 426.
(toluene).
(-)-form [2437-75-4]
Cryst. Mp 113°. Bp 750 146°. [1X]n -22.3° (C6H 6).
Boroweicki, L. et al, Bull. Soc. Chim. Fr., 1967, 2364 (synth)
Sakota, N. et al, Bull. Chern. Soc. Jpn., 1971, 44, 485 (abs corifig)
Org. Synth., 1971, 51, 66 (synth)

132
2-Bromobornane- Camphor-tO-sulfonic acid Mo-00737 - Mo-00740

2-Bromobornane
2-Bromo-1,7,7-trimethylbicyclo[2.2.J]heptane. Camphene
hydrobromide. Isobornyl bromide
Mo-00737 Banthorpe, D.V. et al, J. Chern. Soc. C, 1970, 2694 (biosynth)
Allan, F.H. et al, J. Chern. Soc. B, 1971, 632 (abs config)
Fairley, J.C. et al, J. Chern. Soc., Perkin Trans. 1, 1973, 2109
(synth)
Verbrugge, P.A., Chern. Tech. (Amsterdam), 1975, 40, 6 (rev)

~H
Rudakov, G.A., Chemistry and Technology of Camphor, 2nd Ed.,
1976 (rev)
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Relative Pharmaceutical Press, London, 1982/1989, 263.
configuration Mossa, J.S. et al, Anal. Profiles Drug Subst., 1984, 13, 27 (rev)
Trimble, L.A. et al, J. Am. Chern. Soc., 1985, 107, 2175 (pmr, cmr)
Br
Hazards in the Chemical Laboratory, (Bretherick, L., Ed.), 3rd Ed.,
C10H 17Br M 217.148 Royal Society of Chemistry, London, 1981, 228.
(JR* ,28*)-form [22339-10-2] Sax, N.l., Dangerous Properties of Industrial Materials, 6th Ed.,
Van Nostrand-Reinhold, 1984, 625, 626.
( + )-endo-form
Cryst. Mp 7(i.5-78.0°. [1X]n +21.2°.
(IS* ,2R*)-form Camphor-S-sulfonic acid Mo-00739
(- )-endo-form Camphor-n-sulfonic acid
Cryst. Mp 87-92°. [1X]n -24.6°.
Heikman, H. et al, Acta Chern. Scand., 1968, 22, 2034 (synth)
Boroweicki, L. et al, Pol. J. Chern. (Rocz. Chern.), 1970, 44, 531
(synth)
Barthelemy, M. et al, Bull. Soc. Chim. Fr., 1974, 1703 (synth)

Camphor, USAN Mo-00738

1, 7,7- Trimethylbicyclo[2.2.J]heptan- 2-one. 2-Bornanone. 2-
Camphanone. Alcanfer. Camphilen. Canforal. Canforetil
C10H 160 4S M 232.300
[76-22-2]
Resolving agent.
(+)-form
NH4 salt: Long needles. [1X]n +80S (EtOH).
Chloride:
C 10 H 1 ~Cl0 3 S M 250.745
Cryst. Mp 137-138°. [1X]): + 128.7° (CHC1 3).
Amide:
C1oH160 M 152.236 C10H 17N0 3S M 231.315
I> Irritant, mod. toxic orally, TLV 12. EX1225000. Cryst. Mp 136-137°. [1X]~ +93.6° (EtOH).
(+)-form [464-49-3] (-)-form
Japan camphor. Laurene camphor NH4 salt: Long needles. [1X)n -80.1° (EtOH).
Widespread, found esp. in the Camphor tree, Pope, W.J. et al, J. Chern. Soc., 1910, 97, 987.
Cinnamomum camphora and common in the Lauraceae,
Labiateae and Compositae. Also manuf. from Pinene.
Used in perfumery. Analeptic, respiratory stimulant, Camphot-10-sulfonic acid Mo-00740
topical analgesic, antipruritic and antirheumatic. Camphor-P-sulfonic acid. Camphor-ro-sulfonic acid
Rhombohedra or cubic cryst. Spar. sol. Hp. Mp 179°.
Bp 204°. [1X]i? + 54.9° (c, 5 in EtOH). Subl., v. steam-
volatile. Volatile at r.t.
I> EX1260000.
Oxime:
C1oH17NO M 167.250
Needles or prisms. Mp 118°. Bp 249-254° dec. [1X]i?
-42.4° (EtOH). Triboluminescent. H03S
Semicarbazone: Needles. Mp 247-248°. C10H 160 4S M 232.300
(-)-form [464-48-2] (+)-form [3144-16-9]
Constit. of Matricaria parthenium and many other oils, Resolving agent. Cryst. (AcOH). Mp 193-195° dec. [1X]i?
less common than the (+)-form. Cryst. Mp 179°. [1X]n +2l.SO (c, 4.3 in H 20).
-44.2° (EtOH). Chloride:
I> EX1250000. C 10 H 1 ~Cl0 3 S M 250.745
(±)-form Resolving agent for alcohols and amines. Cryst. (Etp).
Manuf. synthetically but also reported from Mp 67-68°. [1X]i? +32.2° (CHC13).
Chrysanthemum sinense and C. indicum. Plasticiser, (-)-form [35963-20-3]
preservative, component of celluloid plastics etc. ( + )- Cryst. (AcOH). Mp 193-195° dec. [1X]i? -20.75° (H20).
Form also freq. used. Has minor pharmaceutical uses,
e.g. topical antiinfective. Cryst. Mp 179°. (±)-form
Cryst. (AcOH). Mp 202° dec.
Kirk-Othmer Encycl. Chern. Techno/., 2nd Ed., Wiley, N.Y., 1963-
1971, 4, 54 (rev) Chloride: Cryst. (pet. ether). Mp 83-84°.
v Sydow, E., Acta Chern. Scand., 1964, 18, 1099 (ms) Pope, W.J. et al, J. Chern. Soc., 1914, 105, 800 (synth)
Bays, D.E. et al, J. Chern. Soc. B, 1966, 885 (cd)

133
2-Chlorobornane - 7,7-Dimethyl-2-oxobicyclo[2.2.1] ... Mo-00741 - Mo-00747

Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1967, 1, Cryst. by subl. Mp 108-108.SO.
109; 4, 68. 2-Ketone: [7492-82-2]. P-Santenone
Org. Synth., Coli. Vol., 5, 1973, 196 (chloride)
Mueller, D.M. et al, J. Pralct. Chern., 1975, 317, 689 (synth) Cryst. Mp 48-49°.
Hatfield, L.D. et al, J. Org. Chern., 1967, 32, 844 (synth)
Stothers, J.B. et al, Can. J. Chern., 1976, 54, 1211 (cmr)
2-Chlorobomane Mo-00741
2-Chloro-1, 7,7-trimethylbicyclo[2.2.1]heptane
7,7-Dimethylbicyclo[2.2.1 ]heptan-2-one Mo-00744
a-l'enchocamphorone

~CI H
(1R,2R,4R)-form
Absolute
configuration

C1oH17Cl M 172.697
(IR,2R,4R)-form [27720-69-0] C 9H 140 M 138.209
(- )-exo-form. Isobornyl chloride. Camphene Cryst. Mp 108°. (tx] 0 -60° (EtOH).
hydrochloride
Coulombeau, C. et al, Bull. Soc. Chim. Fr., 1966, 3752.
Cryst. (pentanol). Mp 161.SO.
(IR,2S,4R)-form [30462-53-4]
(+ )-endo-form. Bornyl chloride. Pinene hydrochloride 7,7-Dimethylbicyclo[2.2.1 ]hept-2-ene, 9CI Mo-00745
Leaflets with camphoraceous odour. Mp 133-134°. Bp 7, 7-Dimethyl-2-norbornene
207°. [a]J: +31° (EtOH). (6541-60-2]
Hanach, M. et al, Chern. Ber., 1962, 95, 193 (synth)
Floutt, T.J. et al, J. Am. Chern. Soc., 1963, 85, 3212 (synth)

3,3-Dibromo-2-bornanone, SCI Mo-00742

3,3-Dibromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 9Cl.
3,3-Dibromocamphor
C9H 14 M 122.210
[514-12-5] Liq. Mp 35.5-36°. Bp 135-140°.
Komppa, G. et al, Justus Liebigs Ann. Chern., 1922, 429, 175;

x~r n.
1932, 497, 116 (synth)
Lipp, P. et al, Ber., 1936, 69, 586, 2251 (synth)
Brown, R.C. et al, J. Org. Chern., 1970, 35, 1360 (synth)

~ 0
7,7-Dimethylbicyclo[2.2.1 ]hept-5-ene-2,3-
dione
Mo-00746
C 10H 14Br20 M 310.028
[60526-42-3]
(IR,4S)-form
Cryst. (ligroin or EtOH). Mp 61°. [ali? + 39.6° (c, 17 in

~0
C6H 6). Not v. stable, steam-volatile.
Burgess, H. eta/, J. Chern. Soc., 1923, 123, 1867 (synth)
Eck, C.R. et a/, J. Chern. Soc., Perkin Trans. 1, 1975, 251 (synth,
nmr, ir)
Carman, R.M. et al, Aust. J. Chern., 1979, 32, 2331 (synth)
C9 H 100 2 M 150.177
1,7-Dimethylbicyclo[2.2.1 ]heptan-2-ol Mo-00743 Yellow cryst. (pet. ether). Mp 124-126°.
1,7-Dimethylnorbornanol Blankespoor, R.L. et al, J. Org. Chern., 1977, 42, 63 (synth)

~:
7,7-Dimethyl-2-oxobicyclo[2.2.1 ]heptane- Mo-00747
1-carboxylic acid
(1RS,2RS,4RS, 7RS)-form Ketopinic acid

~OH Relative
configuration
[40724-67-2]

~
H
C9H 160 M 140.225
(I RS,2RS,4RS,7RS)-form [509-11-5] (+)cfwm
exo,anti-form. a-Santenol
Cryst. by subl. Mp 84-85°.
2-Ketone: [7492-83-3]. 1,7-Dimethyl-2-norbornanone. a-
COOHO
Santenone CIOH1403 M 182.219
C,H 140 2 M 154.208 Useful resolving agent.
Cryst. Mp 55°. (+)-form
(IRS,2RS,4RS,7SR)-form [509-12-6] Cryst. (HzO). Mp 226-228°. [a] 0 + 25.8° (c, 0.65 in
exo,syn-form. P-Santenol MeOH).

134
2-Hydroxy-3-bornanone - 7-Hydroxymethyl-1,7-dimethylbicyclo[... Mo-00748- Mo-00753

(-)-form 4-Hydroxy-2-bornanone Mo-00750

Cryst. (H 20). Mp 227-229°. [exln -28° (c, 1.5 in 4-Hydroxy-1,7,7-trimethylbicyc/o[2.2.1]heptan-2-one. 4-
MeOH). Hydroxycamphor
Chloride: [55784-66-2]
C 10H 13Cl02 M 200.664
Resolving agent. Mp 112°. [exln -41 o (c, 1.9 in CHC1 3).

~
Kokke, W.C.M.C. eta/, J. Org. Chern., 1974, 39, 1653 (synth)
Haslanger, M.F. eta/, Synthesis, 1981, 801 (synth, bib[)

2-Hydroxy-3-bornanone Mo-00748
3-Hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 9Cl. 2- 0
Hydroxyepicamphor C,oH,60 2 M 168.235
Cryst. (pet. ether). Mp 250°. [ex]:.J -16°.

~H
Houben, J. eta/, Justus Liebigs Ann. Chern., 1931, 489, 193 (synth)
Morris, D.G. et a/, J. Chern. Soc., Perkin Trans. 2, 1976, 1579
(!S,3R,4R),{o'm (crnr)

5-Hydroxy-2-bornanone Mo-00751
OH 5-Hydroxy-1 ,7,7-trimethylbicyc/o[2.2.1]heptan-2-one. 5-
C10H,60 2 M 168.235 Hydroxycamphor
Bornane numbering shown. [1126-88-1]
(1S.3R,4R)-form [28357-10-0]

A'W"OH
( + )-endo-form
Cryst. Mp 221°. [ex]~ + 10.2° (c, 2.1 in EtOH).
Ac: [15795-10-5].

~
Mp 60-61°.
(1S.3S,4R)-form [25671-14-1]
(- )-exo-form
Cryst. (cyclohexane). Mp 228-230° (204-205°). [ex]i;' CIOHI602 M 168.235
+ 115° (c, 2.2 in EtOH). Cryst. (pet. ether). Mp 222.5-223.5°. [exJ:ju +41° (EtOH).
[22759-34-8]
Probably known only in impure andjor config.
inhomogenous form.
Coulombeau, C. et a/, Bull. Soc. Chirn. Fr., 1966, 3752 (cd)
Fleming, I. et al, J. Chern. Soc. C, 1968, 1289 (synth) Heiniinen, E. et al, Suorn. Kernistil. B, 1969, 42, 53 (synth, bib[)
Thoren, S., Acta Chern. Scand., 1970, 24, 93 (synth)
Coulombeau, C. et al, Bull. Soc. Chirn. Fr., 1970, 1199 (synth) 1-Hydroxymethyl-7,7- Mo-00752
Bartlett, L. et al, J. Chern. Soc. C, 1970, 2678 (abs co'!fig)
dimethylbicyclo[2.2.1 ]heptan-2-one
10-Hydroxycamphor. P- Hydroxycamphor
3-Hydroxy-2-bornanone, SCI Mo-00749
3-Hydroxy-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 9CI. 3-

~0
Hydroxycamphor
[1 0373-81-6]

C,0H 160 2 M 168.235

Cryst. (pet. ether). Mp 220°. [ex]~ + 51.9° (EtOH).
Dallacker, F. et al, Justus Liebigs Ann. Chern., 1961, 647, 23
C 10H 160 2 M 168.235 (synth)
Tori, K. eta/, Chern. Pharrn. Bull., 1964, 12, 924 (prnr)
(1R,3R,4S)-form [22759-33-7]
(+ )-exo-form
Mp 226-229°. [ex]~ + 131° (C6H6). 7-Hydroxymethyl-1,7- Mo-00753
Ac: dimethylbicyclo[2.2.1 ]heptan-2-one
C 12H 180 3 M 210.272 n-Hydroxycamphor
Mp 149-150°.
(1R.3S,4S)-form [21488-68-6]
(- )-endo-form
(1R,4R,1R)-form
Mp 192-197°. [ex]~ -11.9° (CHC1 3).
Absolute
Ac: Mp 57-58°.
configuration
Bartlett, L. et a/, J. Chern. Soc. C, 1970, 2678 (ord, cd)
Thoren, S., Acta Chern. Scand., 1970, 24, 93.
C10H 160 2 M 168.235
(1R,4R,7R)-form [10334-06-2]
(+)-anti-form. 8-Hydroxy-2-bornanone. 8-
Hydroxycamphor
Cryst. (EtzOjpentane). Mp 243.5-244°. [exJn +63.1°.

135
3-Hydroxymethylene-2-bornanone - 1,4,7,7-Tetramethylbicyclo[2.2.1] ... Mo-00754- Mo-00758

(JR,4R,7S)-form Karahadian, C. et al, J. Agric. Food Chern., 1985, 33. 339.

(+)-syn-form. 9-Hydroxy-2-bornanone. 9- Toyota, M. et al, Phytochemistry, 1990, 29, 2334 (isol, pmr, cmr,
Hydroxycamphor synth)
Cryst. {pet. ether). Mp 233-234°. [rx]~ +40.7°.
Meyer, W.L. et al, J. Org. Chern., 1967, 32, 1754. 3-Nitro-2-bornanone Mo-00756
3-Nitro-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-one. 3-
Nitrocamphor
3-Hydroxymethylene-2-bornanone, SCI Mo-00754
3-Hydroxymethylene-1, 7,7-trimethylbicyclo[2.2.1]heptan-2- [2243-88-1]
one, 9CI. 3-Hydroxymethy/enecamphor. 3-Formy/camphor.

~xi
3-A/dehydocamphor. Camphoraldehyde
[15051-75-9]

~OH C 10H 15N03 M 197.233

0

Cryst. {C6HJ. Mp 103°. [rx]~ -26° (EtOH).

0 Lowry, T.M. et al, J. Chern. Soc., 1915, 1040 (synth)
C11H 160 1 M 180.246 Shvarts, I.Sh. et al, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 1674
(+)-form [14681-31-3] (synth)
Sol. hot H20. Mp 81-82°. Bp 251°, Bp 11 105°.
Cu deriv.: Greenish-yellow needles (ligroin). Mp 166-167°. 1,3,7,7-Tetramethylbicyclo[2.2.1)heptan-2- Mo-00757
Ac: [24398-98-9]. one, 9CI
C13H 180 3 M 222.283 1,3,7,7-Tetramethy/-2-norbornanone, SCI. 3-Methy/-2-
Mp 63-64°. Bp0 _4 110°. [rxJn + 167.4° (c, 1 in EtOH). bornanone. 3-Methy/camphor
Me ether: [17287-15-9]. [5811-48-3]
CuH 180 1 M 194.273
Mp 40°. Bp 262°, Bp 12 141°.
(-)-form (1R,3R,4R)-form
Mp 81-82°. [rx]i,'l -195° (EtOH). Absolute
(±)-form [53625-89-1] configuration
Mp 80-81°.
Bishop, A.W. et al, Justus Liebigs Ann. Chern., 1894, 281, 314 C11 H 180 M 166.263
(synth) (IR,3R,4R)-form
Pope, W.J. et al, J. Chern. Soc., 1913, 103, 446 (synth)
Daniel, A. et al, Tetrahedron Lett., 1967, 1145 (pmr) ( + )-exo-form
Terentov, A.P. et al, Zh. Org. Khim., 1970, 40, 1398; CA, 67, Mp 51.5-52.0°. [rx]i,'l +69.2° (c, 10 in EtOH).
16475 (synth) Oxime:
C 11 H 19NO M 181.277
2-Methyl-2-bornanol Mo-00755 Mp 92.5-93.0°. [rx]i,'l -59.SO (c, 5 in EtOH).
1,2,7,7- Tetramethylbicyc/o[2.2.1]heptan-2-ol, 9CI. 1,2,7,7- (IR,3S,4R)-form [51100-01-7]
Tetramethylnorbornan-2-ol, SCI. 2-Methylisoborneol ( + )-endo-form
Plates (EtOH aq.). Mp 38-39°. Bp 220-221°, Bp85 88-89°.
Oxime: Mp 57.5-58.0°. [rx]:,O +30.4° (c, 5 in EtOH).
Avela, E., CA, 1957, 51, 10430 (synth)
Daniel, A. et al, Bull. Soc. Chim. Fr., 1971, 1060 (synth)
Stothers, J.B. et al, Can. J. Chern., 1973, 51, 2893 (cmr)

1,4,7,7-Tetramethylbicyclo[2.2.1)heptan-2- Mo-00758
C11 H 100 M 168.278 one, 9CI
(1R,2R)-form 1,4,7,7-Tetramethyl-2-norbornanone, SCI. 4-Me.thy/-2-
Metab. of Streptomyces spp., Penicillium sp., bornanone. 4-Methy/camphor
Actinomadura spp. and Lophocolea heterophylla. Found [1 0309-50-9]
in polluted water, causes objectionable odour of water

~0
supplies. Mp 170°. [rx]:,O -11.8° (c, 10 in EtOH).
4-Nitrobenzoy/: [13389-79-2).
Mp 138°.
[2371-42-8, 28405-88-1, 68330-44-9)
Capmau, M.L. et al, Bull. Soc. Chim. Fr., 1968, 3233 (synth)
Toivonen, H., Tetrahedron Lett., 1968, 3041 (synth)
Gerber, N.N., J. Antibiot., 1969, 22, 508 (isol) C11 H 180 M 166.263
Wood, N.F. et al, J. Chromatogr., 1977, 132, 405.
Croteau, R. et al, J. Nat. Prod. (Lloydia), 1981, 44, 261 (biosynth) (-)-form [20536-81-6]
Kimura, T. et al, Appl. Environ. Microbial., 1982, 43, 654 (isol) Cryst. (EtOH). Mp 168°. Bp 213-213.SO. [rx]i,2 -14.50°
(c, 10 in EtOH).
Oxime:

136
1,6,7,7-Tetramethylbicyclo[2.2.1] ... - 1,3,3-Trimethylbicyclo[2.2.1]heptan-... Mo-00759 - Mo-00763

C 11 H 19NO M 181.277 (+)-form [7787-20-4]

Needles (MeOH aq.). Mp 132-133°. V. volatile. Widespread in plants, e.g. found in fennel oil
Semicarbazone: Plates (EtOH). Mp 257-259° dec. (Foeniculum vulgare), Blumea lacera, Prunella vulgaris.
Can be used as H acceptor in dehydrogenations. Oil
[76966-82-0]
with camphoraceous odour. Prac. insol. H 20, v. sol.
Bredt-Savelsberg, M. et al, Ber., 1931, 64, 600 (synth) EtOH. Mp 3-5°, Fp 5-6°. Bp 193.SO. [ex]~ +63°.
Toivonen, H., Tetrahedron Lett., 1968, 3041 (synth)
Morris, D.G. et al, J. Chern. Soc., Perkin Trans. 2, 1976, 1579 Oxime:
(crnr) CIOH17NO M 167.250
Jacobsen, N. et al, Nouv. J. Chirn., 1978, 2, 331 (synth) Cryst. (MeOH). Mp 158-159°.
(-)-form [4695-62-9]
1,6,7,7-Tetramethylbicyclo(2.2.1)heptan-2- Mo-00759 lsol. from various essential oils e.g. Thuja occidentalis
one, SCI and Artemisiafrigida. [cxln -67°.
1,6,7,7- Tetramethyl-2-norbornanone, 9Cl. 6-Methyl-2- (±)-form [18492-37-0]
bornanone. 6-Methylcamphor Bp 192-194°.
[17981-54-3] Oxime: Mp 158-159°.
Komppa, G. et al, Ber., 1935, 68, 2001 (synth)
Bays, D.E. et al, J. Chern. Soc. B, 1966, 885 (cd)
Thomas, A.F. eta/, Helv. Chirn. Acta, 1967, 50, 826 (ms)
Baker, K.M. eta/, Tetrahedron, 1968, 24, 1663 (prnr)
Lipman, E. et al, Org. Magn. Reson., 1970, 2, 581 (crnr)
Boyle, P.H. eta/, J. Chern. Soc. C, 1971, 2136 (synth)
Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1980, 8,
228.
C11 H 180 M 166.263 Buchbauer, G. et al, Justus Liebigs Ann. Chern., 1981, 2093 (synth)
Cryst. Mp 167-168°.
Oxime: 1,3,3-Trimethylbicyclo(2.2.1)heptane Mo-00762
C11 H 19NO M 181.277 b-Fenchane
Mp 125-127°.

ck
[6248-88-0]
Semicarbazone: Mp 255° dec.
Treibs, W., Tetrahedron Lett., 1967, 4703 (synth)

(-),{onn

CIOH18 M 138.252
Fenchanes (-)-form
Oil. Bp765 151-152°. [cxln -18°.
Rerat, C., Cornpt. Rend. Hebd. Seances Acad. Sci. Sect. C, 1968,
266, 612.

5,5-Dimethylbicyclo(2.2.1)heptan-2-one Mo-00760 1,3,3-Trimethylbicyclo(2.2.1)heptan-2-ol Mo-00763

Isocamphenilone. P-Fenchocamphorone Fenchol. Fenchyl alcohol
[534-36-1] [1632-73-1]

(1S,2S,4R)-form

C10H 180 M 154.252

C9H 140 M 138.209 Various stereoisomers isol. from turpentines and other
Cryst. Mp 66°. [cx]n -7.1° {EtOH). plant sources e.g. Ferula, Juniperus, Clausena spp. Used
Mattinen, V., Ann. Acad. Sci. Fenn., Ser. A, 1961, lOS, 1 (synth) in perfumery.
Cou1ombeau, C. et al, Bull. Soc. Chirn. Fr., 1966, 3752 (abs config) (JS,2S,4R)-form [2217-02-9]
Schneider, H.-J. eta/, Tetrahedron, 1975, 31, 2125 (prnr) (- )-endo-form. (- )-cx-Fenchol
Cryst. Mp 43.7-48.SO. Bp 20 94°. [cx]i? -11.0° (EtOH).
Fenchone Mo-00761 Hydrogen phthalate: Mp 146°.
1,3,3-Trimethylbicyclo[2.2.J]heptan-2-one, 9CI. Fenchol
p-Nitrobenzoyl: Mp 108°.
(obsol.)
(1R,2R,4S)-form [512-13-0]
[1195-79-5] ( + )-endo-form. ( + )-cx-Fenchol
Cryst. Mp 47-47.SO. [cx]i? + 12.SO.
Hydrogen phthalate: Mp 145°.
(+)-form p-Nitrobenzoyl: Mp 107°.
(1R,2S,4S)-form
(+)-exo-form. ( + )-P-Fenchol
CIOH160 M 152.236 Mp 26-27°. [cx]i)1 + 33.2° (EtOH).
Fp 5-6°. I> RB7650000.
I> RB7875000.

137
1,5.5·Trimethylbicyclo[2.2.1]heptan-... - Cedronellone Mo-00764 - Mo-00768

Hydrogen phthalate: Mp 151°. (-)-form [17957-95-8]

Phenylurethane: Mp 89°. Oil. Bp 200-201°. [cx] 0 -6.7° (EtOH).
(JS,2R,4R)-form [470-08-6] v. Pfrunder, B. et al, Helv. Chim. Acta, 1969, 52, 1630.
(- )-exo-form. (- )-P-Fenchol
Oil. Mp 7-8° (3-4°). Bp 18 91°. [cx]~ -31.0°. 1,5,5-Trimethylbicyclo(2.2.1 )hept-2-ene Mo-00766
Hydrogen phthalate: Mp 154°. t5-Fenchene. /sofenchene
p-Nitrobenzoyl: Mp 82°. [534-31-6]
Phenylurethane: Mp 89°.
(JRS,2RS,4SR)-form [36386-49-9]
( ± )-endo-form. ( ± )-cx-Fenchol
Mp 38°. Bp 200°.
Hydrogen phthalate: Mp 169°.
C 10H 16 M 136.236
Phenylurethane: Mp 104°.
Oil. Bp 139-140°. [cx] 0 -68.8° (EtOH).
(JRS,2SR,4SR)-form [36386-50-2]
Castanet, Y. et al, Bull. Soc. Chim. Fr., 1976, 1583.
( ± )-exo-form. ( ± )-P-Fenchol
Mp 6°. Bp 201°.
Hydrogen phthalate: Mp 153°.
Phenylurethane: Mp 90°.
[14575-74-7, 22627-95-8]
Rotkfs Chern. Carbon Compd. (2nd Ed.), 2nd Ed.,' Vol. II', 238
(bib[)
Pinanes
Hiickel, W. et al, Justus Liebigs Ann. Chern., 1963, 664, 31.
Bosworth, N. et al, J. Chern. Soc., Perkin Trans. I, 1972, 943
(synth)
Teisseire, P., Recherches, 1974, 19, 232 (rev) Albiftorin Mo-00767
Stothers, J.B. et al, Can. J. Chern., 1976, 54, 1211 (cmr) 9-[(Benzoyloxy)methy~-J-(p-n-g/ucopyranosyloxy)-4-
hydroxy-6-methyl-7-oxatricyclo[4.3.0.03·'1nonan-8-one, 9CI
1,5,5-Trimethylbicyclo(2.2.1 )heptan-2-ol Mo-00764 (390 11-90-0]
Isofenchyl alcohol
0
[6168-62-3] GlcO 0
Absolute
HO~ ( 1S,2R,4S)-form H configuration

lJk
Absolute PhCOOCH2
configuration
CDH280u M 480.468
C 1ofl180 M 154.252 Constit. of the oriental drug Shaoyao from Paeonia
(JS,2R,4S)-form a/biflora root. Hygroscopic powder. [cx]i,2 -19.9° (c, 0.95
(- )-cx-form. (- )-exo-form in EtOH).
Cryst. Mp 60.5-61°. Bp 197-199°. [cx] 0 -27.0° (EtOH). Kaneda, M. et al, Tetrahedron, 1972, 28, 4309 (struct, uv)
Yamasaki, K. et al, Tetrahedron Lett., 1976, 3965 (cmr)
(JR,2SR,4RS)-form [534-34-9] Vollmer, K.O. et al, Z. Naturforsch., C, 1986, 41, 115 (hplc, metab)
( ± )-cx-form. ( ± )-exo-form
Oil. Bp 15 89°.
(JS,2S,4S)-form
Cedronellone Mo-00768
( + )-P-form. ( + )-endo-form [113473-19-1]
Oil. Mp 8°. Bp 196-197°. [cx] 0 + 15.3° (EtOH aq.).
(JRS,2RS,4RS)-form [534-35-0]
( ± )-P-form. ( ± )-endo-form
Cryst. Mp 43°. Bp 202-203°.
Hiickel, W. et al, Justus Liebigs Ann. Chern., 1965, 687, 40 (synth)
Thomas, A.F. et al, Tetrahedron Lett., 1965, 1309 (synth)
Schneider, H.J. et al, Tetrahedron, 1975, 31, 2125 (pmr, cmr)
C 20 H 280 2 M 300.440
1,5,5-Trimethylbicyclo(2.2.1)heptan-2-one Mo-00765 Constit. of Cedrone/la canariensis. Cryst. (MeOH). Mp
lsofenchone 106-107°. [cx]~ +79.3° (c, 0.916 in CHC1 3).
Stereoisomer(?): Aritasone

0~
llJ< (-)-form
C20H 280 2 M 300.440
Constit. of Chenopodium ambrosioides. Cryst. (pet.
ether). Mp 105-106°. [ex]~ -118.6°. No stereochem.
assigned, clearly not identical with Cedronellone, could
C 10H 160 M 152.236 be the enantiomer.
(+)-form [10293-22-8] Nakajima, T., Yakugaku Zasshi (J. Pharm. Soc. Jpn.). 1962, 82,
Oil. Bp 201°. [cx] 0 +90.35°. 1278 (Aritasone)
Carreiras, M.C. eta/, Phytochemistry, 1987, 26, 3351
(Cedronellone)

138
6,6-Dimethylbicyclo[3.1.1]heptan-2-... - Pinane Mo-007:69- Mo-00774

6,6-Dimethylbicyclo(3.1.1)heptan-2-one Mo-00769 Oguri, T. eta/, Chem. Pharm. Bull., 1978, 26, 803 (synth)
7,7-Dimethyl-2-norpinanone. Nopinone. 2-Apopinanone. P- Fieser and Fieser's Reagents for Organic Synthesis, Wiley, 1979, 7,
177 (synth, use)
Pinone
[24903-95-5]
2-Hydroxy-4-pinanone Mo-00771
4-Hydroxy-4,6,6-trimethylbicyclo[3 .l.l]heptan-2-one, 9Cl
[85527-26-0]
(+)-form

C,H140 M 138.209
I> Potentially hazardous synth.
(+)-form [38651-65-9] C 10H 160 2 M 168.235
Obt. by ozonisation of (- )P-pinenene. [a]i; +20.3°. Constit. of lchthyothere terminalis. Oil.
2a-Alcohol: 2a-Hydroxyapopinane. P-Nopinol Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2317.
Cryst. Mp 37-37.5°. [a]n -15.2° (c, 0.7 in MeOH).
2P-Alcohol: 2P-Hydroxyapopinane. a-Nopinol
Cryst. (MeOH). Mp 103.5-104°. Bp 204-205°.
Nopinic acid Mo-00772
2-Hydroxy-7, 7-dimethylbicyclo[3 .J.J]heptane-2-carboxylic
(-)-form acid
Isol. from oil of Lavandula officina/is. Bp 11 85°. [aln
-18.35° (semisynthetic). ni] 1.4772. HO COOH
2,4-Dinitrophenylhydrazone: Mp 148.5-149.5°.
(±)-form [30469-48-8]
Liq.
@
(31147-63-4, 31147-64-5, 51703-63-0, 53767-58-1, 70223-29-9,
CIOH1603 M 184.235
70223-30-2, 74984-18-2, 74984-19-3]
Cryst. (Hp). Mp 126-128°. [a]~ - W (Et20).
Stadler, P.A., Helv. Chim. Acta, 1960, 43, 1601 (isol)
Herz, W. eta/, J. Org. Chem., 1962, 27, 1032.
Hirata, T., Bull. Chem. Soc. Jpn., 1972, 45, 3169, 3458 (synth, abs
corifig)
Grover, S.H. eta/, Can. J. Chem., 1975, 53, 1351 (cmr) Paeoniflorin Mo-00773
Fallis, A.G., Can. J. Chem., 1975, 53, 1657 (synth) Peonifiorin
Thomas, M.T. eta/, J. Am. Chem. Soc., 1976, 98, 1227 (synth)
Murthi, G.S.S. eta/, Indian J. Chem., Sect. B, 1981, 20, 339 [23180-57-6]
(synth) ·
Lavallee, P. eta/, J. Org. Chem., 1986, 51, 1362 (synth)
Ferreira, J.T.B., Chern. Eng. News, Dec. 10, 1990, 4 (haz)
PhCOO~C~O
GlcO-
2-Hydroxy-3-pinanone Mo-00770
2-Hydroxy-2,6,6-trimethylbicyclo[3.l.J]heptan-3-one, 9Cl HO
[l 0 136-65-9] C23H 280 11 M 480.468
Constit. of Paeonia albifiora. Also from P. japonica, P.
suffruticosa and P. officina/is. Amorph. [a]~ -12.8° (c,
4.6 in MeOH).
(!S,2S,5S)-form I> RT1200000.
Penta-Ac: Cryst. Mp 158°. [a]~ + 13.5° (c, 4.1 in MeOH).
C 1.,H160 2 M 168.235 Aimi, N. eta/, Tetrahedron, 1969, 25, 1825 (isol)
Kaneda, M. eta/, Acta Crystal/ogr., Sect. B, 1972, 28, 1411 (cryst
I> TK4586000. struct)
(1S,2S,5S)-form [1845-25-6] Yamasaki, K. et a/, Tetrahedron Lett., 1976, 3965 (pmr)
Used in asymmetric synth. of amino acids. Prisms Yu, J. eta/, Phytochemistry, 1990, 29, 3859 (cmr)
(pentane). Mp 31-32°. Bp 17 113-115°. [a]i; -38.9° (c,
2.64 in CHCl 3). Pinane Mo-00774
Ac: [29333-13-9]. 2,7,7- Trimethylbicyclo[3.l.J]heptane
C 12H 180 3 M 210.272 [473-55-2]
Needles (hexane). Mp 42-44°. [a]i;' +2.08° (c, 2 in
CHCl 3). I
I (!R,2R,5R)-form
Absolute

~
Oxime: [67617-36-1].
C 10H 17N0 2 M 183.250 configuration
Prisms (hexane). Mp 117-118°. [a]~ + 16.6° (c, 3 in
CHC1 3).
C 10H 18 M 138.252
(1 S,2R,5S)-form [20536-50-9] Intermed. used in manuf. of terpene alcohols.
Oil. Bp0 _15 53-55°. [a]i; +90.41 o (c, 5 in CHC13).
(1R,2R,5R)-form [4863-59-6]
Ac: Cryst. (pentane). Mp 50-51°. [a]i; -0.33° (c, 12 in (+)-trans-form
CHCI 3). Oil. [a]n + W.
Carlson, R.G. eta/, J. Org. Chem., 1971, 36, 2319 (synth, use) (1R,2S,5R)-form [4795-86-2]
de Pascuel, T. eta/, An. Quim., 1977, 73, 1377 (synth)
(+)-cis-form

139
2-Pinanol - 10-Pinanol Mo-00775 - Mo-00778

Oil. Bp 169°. [1X] 0 + 19°. ( + )-Neopinocampheo/

(JS,2R,5S)-form [4755-33-3] Cryst. Mp 27°. [1X] 0 + 17o (C 6H 6).
(-)-cis-form (1 S,2S,3R,5R)-form
Oil. [1X]D -19.3°. (- )-Neoisopinocampheo/
(JS,2S,5S)-form [10281-53-5] Cryst. Mp 48°. Bp 217°. [1X] 0 -36°.
(-)-trans-form (JS,2S,3S,5R)-form [24041-60-9]
Oil. [1X] 0 -12.4°. (+ )-lsopinocampheol
Zweifel, G. eta/, J. Am. Chern. Soc., 1964, 86, 393 (synth) Mp 57°. Bp 219°. [1X] 0 -36°.
Filliatre, C. eta/, Bull. Soc. Chim. Fr., 1968, 4141 (synth) Banthorpe, D.V. et a/, Chern. Rev., 1966, 66, 643 (rev)
Wesley, C. eta/, Bull. Trans. Nat/. Inst. Sci. India, 1968, 56 (synth) Hiickel, W. eta/, Justus Liebigs Ann. Chern., 1966, 697, 69 (synth,
Holden, C.M. eta/, Org. Magn. Reson., 1975, 7, 125 (cmr) config, bib!)
Teisseire, P. eta/, Recherches, 1967, 59 (struct)
Brown, H.C. eta/, J. Org. Chern., 1971, 36, 387 (synrh)
2-Pinanol Mo-00775 Hirata, T. eta/, Bull. Chern. Soc. Jpn., 1972, 45, 599 (pmr)
2,6,6-Trimethylbicyclo[3.1.1]heptan-2-ol. Methylnopinol.
Hydroxypinane
4-Pinanol Mo-00777
I
I (1R,2R,4R,5R)-form

~OH
(IR,2R)-form Absolute
configuration
CIOH180 M 154.252
Intermed. used in the manuf. of terpene alcohols. CIOH180 M 154.252
(JR,2R)-form [35408-04-9] (JR,2R,4R,5R)-form [24739-64-8]
(-)-trans-form. Pinene hydrate Neoverbanol
Mp 59-60°. Bp 10 80-82°. [IX)~ -4.30°. Cryst. Mp 40.SO.
(JR,2S)-form [35519-42-7] (JR,2R,4S,5R)-form [515-88-8]
(-)-cis-form Verbano/
Mp 78-79°. Bp 1 ~ 85-87°. [IX)~ -24.0°. Cryst. (EtOH aq.). Mp 62.5°. [1X] 0 +24.4°.
Dickinson, W. eta/, J. Am. Chern. Soc., 1959, 81, 245 (config) (IR,2S,4R,5R)-form [473-64-3]
Hiickel, W. eta/, Justus Liebigs Ann. Chern., 1959, 625, 12 (synth) Neoisoverbanol
Nedumparambil, A.A., Ann. Chim. (Paris), 1960, 5, 961 (synth) Cryst. Mp 69.SO.
Sauers, R.R. et al, J. Org. Chern., 1961, 26, 964 (synth) (JR,2S,4S,5R)-form [473-65-4]
Whitman, G.H., J. Chern. Soc., 1961, 2232 (synth)
Jsoverbanol
Bessiere-Chnltien, Y. eta/, Bull. Soc. Chim. Fr., 1972, 1000 (abs
config) Cryst. Mp 87°.
Hirata, T., Bull. Chern. Soc. Jpn., 1972, 45, 3169 (pmr) Regan, A.F., Tetrahedron, 1969, 25, 3801 (synth)
Texter, J. et al, J. Org. Chern., 1979, 44, 3222 (conformn) Bessiere-Chretien, Y. et a/, Bull. Soc. Chim. Fr., 1972, 1000 (abs
Weigand, E.F. eta/, Org. Magn. Reson., 1979, 12, 637 (cmr) config)
Hobbs, P.D. et a/, J. Chern. Soc., Perkin Trans. I, 1973, 2876 (abs
config)
3-Pinanol Mo-00776
2,7,7- Trimethylbicyclo[3.1.J]heptan-3-o/, 9CI
10-Pinanol Mo-00778
(IR,2R,3R,5S)-form 6,6-Dimethylbicyclo[3.3.J]heptane-2-methanol. Myrtanol. 10-
Absolute Hydroxypinane
configuration [514-99-8]

CIOH180 M 154.252 (1R,2R,5R)-form

(JR,2R,3R,5S)-form [1196-00-5] Absolute
(- )-/sopinocampheo/ configuration
Cryst. Mp 55.6-56.0°. Bp 219°. [1X]i:> -32.3° (c,. 9.7 in
C6H6). CIOH180 M 154.252
(JR,2R,3S,5S)-form [2734-31-8] Rare natural occurrence.
( + )-Neoisopinocampheo/ (1R,2R,5R)-form [53369-17-8]
Cryst. Mp 47.6-49.0°. Bp 217°. [1X]i:> +33.8° (c, 9.9 in
(-)-trans-form
C6H6). Oil. Bp 14 113-1W. [1X]~· 5 -27.1°.
(JR,2S,3R,5S)-form [19889-95-3] (JR,2S,5R)-form [473-01-8]
(- )-Neopinocampheol Benihiol
Cryst. Mp 28.4-29.0°. [1X]i:> -16.1° (c, 9.4 in C6H 6). Isol. from Chamaecyparis formosensis. Oil. Bp 3 77-79°.
(1R,2S,3S,5S)-form [19889-94-2] [1X]i:> + 39.6°.
( + )- Pinocampheol (JS,2R,5S)-form [51152-12-6]
Cryst. Mp 64-65.5°. [1X]i:> +59.2° (c, 7.5 in C6H 6). (-)-cis-form
(JS,2R,3R,5R)-form [35997-96-7] Oil. Bp0.2 65-67°. [<X]~ -19.SO.
(- )-Pinocampheol Sebe, Y., CA, 1943, 37, 4064 (Benihiol)
Occurs in oils of Hyssopus officina/is, Michelia champaca Brown, H.C. et a/, J. Am. Chern. Soc., 1964, 86, 393 (synth)
and Perovskia angustifolia. Cryst. Mp 67°. Bp 217°. [1X] 0
-55°.
(JS,2R,3S,5R)-form [36129-11-0]

140
3-Pinanone - P-Pinene Mo-00779 - Mo-00782

Borowiecki, L. eta/, Pol. J. Chern. (Rocz. Chern.), 1971, 45, 573 Hobbs, P.D. et al, J. Chern. Soc., Perkin Trans. I, 1973, 2879 (abs
(synth) con.fig)
Lane, C.F., J. Org. Chern., 1974, 39, 1437 (synth) Fallis, A.G., Can. J. Chern., 1975, 53, 1657 (synth)
Ben, H. et al, Justus Liebigs Ann. Chern., 1974, 189 (synth)
rx-Pinene Mo-00781
3-Pinanone Mo-00779 2,6,6-Trimethylbicyclo[3.J.J]hept-2-ene, 9Cl. 2-Pinene.
2,6,6- Trimethylbicyclo[ 3 .J.l]heptan-3-one, 9CI Australene. Firpene. Terebenthene
[80-56-8]
(1R,2R,5S)-form

~0 Absolute

C10H 160 M 152.236

configuration
~ (-)£•~
(JR,2R,5S)-form [473-62-1] C 10H 16 M 136.236
(+ )-/sopinocamphone Main constit. of turpentine. Both enantiomers widely
Oil. Bp 213°. [IX]~ +lOS. distributed in conifers and other plants. V. widely
Semicarbazone: Cryst. Mp 219-220°. distributed in plants. Important intermed. in manuf. of
(1R,2S,5S)-form [18492-59-6] synthetic aroma compds., flavouring ingredient.
(+ )- Pinocamphone I> Irritant, flammable. DT7000000.
Oil. Bp 211-2ll.SO. [IX]~ +21.3°. (+)-form [7785-70-8]
Semicarbazone: Cryst. Mp 227°. Oil. Mp -50°. Bp 155-156°. [1X]n +51.P.
(1S,2R,5R)-form [22339-21-5] (- )-Pinocamphone (-)-form [7785-76-4]
Constit. of the oils of Hyssopus officina/is and ground Oil. Bp 155-156°. [1X]n -51.3°.
ivy. Also from Tanacetum fastigiatum, Luvunga scandens (±)-form [2437-95-8]
and others. Oil. Bp 212-214°. [1X]i;5 -15.2° (c, 0.42 in Occurs with the (+)-form, eg. in Eucalyptus spp. Bp
MeOH). 156.2°. n~ 1.4658.
Semicarbazone: Cryst. (MeOH aq.). Mp 227.5-228.0°.
Ryhage, R. et al, Acta Chern. Scand., 1963, 17, 2025 (ms)
(JS,2S,5R)-form [14575-93-0] (- )-lsopinocamphone Banthorpe, D.V. et a/, Chern. Rev., 1966, 66, 643 (rev)
Constit. of Mentha aquatica. Oil. Bp 211-2ll.SO. [1X]:,S Bates, R.B. eta/, J. Org. Chern., 1968, 33, 1730 (pmr)
-7.3°. Sakota, N. et al, Bull. Chern. Soc. Jpn., 1971, 44, 485 (abs config)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Semicarbazone: Cryst. Mp 232°.
Pflanzenstojfe, 2nd Ed., Birkltiiuser Verlag, Basel, 1972-1985,
Banthorpe, D.V. eta/, Chern. Rev., 1966, 66, 643 (rev) no. 62 (occur)
Hiickel, W. eta/, Justus Liebigs Ann. Chern., 1966, 697, 69 (synth, Bohlmann, F. et al, Org. Magn. Reson., 1972, 4, 489 (cmr)
con.fig, bib[) Thomas, M.T. et al, J. Am. Chern. Soc., 1976, 98, 1227 (synth)
Brown, H.C. et al, J. Org. Chern., 1971, 36, 387 (synth) Stenstro0m, Y. eta/, Acta Chern. Scand., Ser. B, 1980, 34, 131
(synth)
Gleizes, M. eta/, Phytochemistry, 1982, 21, 2641 (biosynth)
4-Pinanone Mo-00780
Banthorpe, D.V. et a/, Phytochemistry, 1984, 23, 291 (biosynth)
I Sax, N.I., Dangerous Properties of Industrial Materials, 5th Ed.,
I (1R,2R,5R)-form Van Nostrand-Reinhold, 1979, 916.

~0
Absolute
configuration ~Pinene Mo-00782
6,6-Dimethyl-2-methylenebicyclo[3 .l.l]heptane, 9CI. 2(1 0)-
CtoH 160 M 152.236 Pinene. Nopinene. Pseudopinene. Orthodene
(JR,2R,5R)-form [515-90-2] [127-91-3]
(- )- Verbanone
Oil. Bp 222°. [1X]n -52.SO.
Semicarbazone: Cryst. (EtOH aq.). Mp 230° dec.
(JR,2S,5R)-form [473-66-5]
(+ )-/soverbanone
·~ 5
(+)-form

Oil. Bp0_1 62°. [1X]n +27.8°. C 10H 16 M 136.236

Semicarbazone: Cryst. Mp 258°.
I> DT5077000.
(JS,2R,5S)-form [38651-60-4] (+)-form [19902-08-0]
(- )-Isoverbanone
Oil. Bp 163-164°. [1X]n +22°.
Oil. Bp0_1 59-61°. [1X]i;5 -47.8° (neat).
(-)-form [18172-67-3]
Oxime:
Constit. of turpentine. Important in termed. in manuf. of
C1oH17NO M 167.250 synthetic aroma compds. Flavouring ingredient. Oil. Bp
Cryst. (pet. ether). Mp 88°. 163-164°. [1X]n -22°.
(JS,2S,5S)-form (±)-form [23089-32-9]
( + )- Verbanone Bp 166°.
Oil. Bp 222°, Bp0 _05 38-43°.
Sakota, N. et al, Bull. Chern. Soc. Jpn., 1971, 44, 485 (abs config)
Muklstiidt, M. et a/, Tetrahedron, 1968, 24, 1611 (synth) Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Regan, A.F., Tetrahedron, 1969, 25, 3801 (synth) Pflanzenstojfe, 2nd Ed., Birkltiiuser Verlag, Basel, 1972-1985,
Bessiere-Chretien, Y. eta/, Bull. Soc. Chim. Fr., 1970, 3103 (synth) no. 63.
Hirata, T., Bull. Chern. Soc. Jpn., 1972, 45, 3458 (synth) Richards, G.F., J. Org. Chern., 1974, 39, 86 (cryst struct)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (cmr)

141
2-Pinene-4,6-diol - 2-Pinen-6-ol Mo-00783 - Mo-00787

Thomas, M.T. et al, J. Am. Chern. Soc., 1976, 98, 1227 (synth,
pmr)
Gleizes, M. et al, Phytochemistry, 1982, 21, 2641 (biosynth)
Andricanome, M. eta/, J. Chern. Soc., Chern. Commun., 1985,
1203 (synth)
Kulkarni, Y.S. et al, J. Org. Chern., 1987, 52, 1568 (synth)
Brown, H.C. eta/, J. Org. Chern., 1988, 53, 4059 (synth)
CIOH1402 M 166.219
Constit. of A. gypsacea. Oil. [1X]i;' -24° (c, 1.2 in
CHC13). No stereochem. indicated.
Teresa, J. de P. et a/, An. Quim., 1979, 75, 323.
Huneck, S. eta/, Phytochemistry, 1986, 25, 883.
Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 1535.

2-Pinene-4,6-diol Mo-00783 2-Pinen-4-ol Mo-00786

4,7,7-Trimethylbicyclo[3.1.1Jhept-3-ene-2,6-diol Verbenol
[473-67-6]
(!R,4R,5R)-form

~OH
Absolute
HO'.@_OH configuration
CIOH1602 M 168.235
(4S,6S)-form CIOH160 M 152.236
Present in essential oils, e.g. terpentine, frankincense, as
Di-Ac: [71372-30-0]. 4S-Acetoxychrysanthemyl acetate
autoxidn. prod.
C 14H 200 4 M 252.310
Constit. of Diotis maritima. Oil. [cxJn -17.4° (c, 0.6 in I> YX7525000.
CHC1 3). (JR,4R,5R)-form [18881-04-4]
Teresa, J., de P. eta), An. Quim., 1979, 75, 323. (-)-cis-form
Cryst. Mp 72.5°. [cxJn -4°.
2-Pinene-4,10-diol Mo-00784 (JR,4S,5R)-form [22339-08-8]
4-Hydroxy-6,6-dimethylbicyclo[ 3 .l.l]hept-2-ene-2-methanol, (+)-trans-form
9CI. 4-Hydroxymyrtenol Component of sex attractant of Ips confusus which
bores into Pinus ponderosa. Oil. Bp9 88°. [cx]i,4 + 141° (c,
[85526-79-0] 0.65 in CHC1 3).
(JS,4R,5S)-form [19890-02-9]
(-)-trans-form
Oil. [cx]i,S - 135° (c, 0.8 in CHC1 3).
4-Nitrobenzoyl: Cryst. Mp 98-99°.
(JS,4S,5S)-form [13040-03-4]
C 10H 160 2 M 168.235 (+)-cis-form
Constit. of Cineraria fruticulorum. Solid. [cx]i,4 -48° (c, Component of sex attractant of/. confusus. Cryst. Mp
0.24 in CHC1 3). 69°. [cx]i,l + 7.6° (c, 2.5 in Me 2CO).
4-0-P-D-Glucopyranoside: Banthorpe, D.V. et al, Chern. Rev., 1966, 66, 643 (rev)
C 16H 260 7 M 330.377 Reece, C. A. et al, Tetrahedron, 1968, 24, 4249 (synth)
Constit. of C. dieterlenii. Uzarewicz, I. eta/, Pol. J. Chern. (Rocz. Chern.), 1970, 44, 1205
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2531 (isol) (synth)
Gonser, P. eta/, Phytochemistry, 1990, 29, 3940 (deriv) Hirata, T., Bull. Chern. Soc. Jpn., 1972, 45, 3169 (synth)
HQiden, C.M. et a/, Org. Magn. Reson., 1975, 7, 125 1cmr)
Mori, K., Agric. Bioi. Chern., 1976, 40, 415 (synth)
2(10)-Pinene-3,6-diol Mo-00785
2-Methylene-7, 7-dimethylbicyclo[3.3 .l]heptane-3 ,6-diol. 3,6-
Dihydroxy-p-pinene
2-Pinen-6-ol Mo-00787
2, 7, 7- Trimethylbicyclo[3 .3 .l]hept-2-ene-6-ol. Chrysanthenol
[38043-83-3]
(3S,6S)-form

C 10Ht60 2
(3S,6S)-form
M 168.235
CIOH160
~OH
M 152.236
Absolute
configuration

6-Ac: [71372-32-2]. 3S-Hydroxyisochrysanthenyl acetate Oil. [cx]i? -50.4° (CHC1 3).

C 12H 180 3 M 210.272 Ac: [50764-55-1].
Constit. of Diotis maritima. Oil. [cxJn + 3° (c, 0.6 in C 12H 180 2 M 194.273
CHC1 3). Constit. of Centipeda cunninghamii. Oil. Bp8 84°. [cxJi?
(3R* ,6S*)-form -30.3° (CHC1 3).
!sol. from Artemisia spp. Oil. Ketone: 2-Pinen-6-one. Chrysanthenone
3-Ketone: [102907-26-6]. 6r~.-Hydroxy-2(10)-pinen-3-one. 7- C 10H 140 M 150.220
Hydroxy-6,6-dimethyl-2-methylenebicyclo[3.1.1Jheptan-3- Constit. of Zieria smithii and Chrysanthemum sinense.
one, 9Cl. 6cx-Hydroxy-P-pinen-3-one Bp 14 83-85°. [cx]46 -88°.
CIOHI402 M 166.219 Ketone, 2,4-dinitropheny/hydrazone: Mp 188-189".
From A. spp. Oil.
Hurst, J.J. et al, J. Chern. Soc., 1960, 2864.
6-Ketone: Jr~.-Hydroxy-2(10)-pinen-6-one. 3-Hydroxy-7,7- Pinhey, J.T. eta/, Aust. J. Chern., 1971, 24, 1311.
dimethyl-2-methylenebicyclo[3.1.1Jheptan-6-one. 3- Kulkarni, Y.S. et al, J. Org. Chern., 1985, 50, 2809; 1987, 52, 1568
Hydroxy-6-oxo-P-pinene (synth)

142
2-Pinen-8-ol - 2(10)-Pinen-3-one Mo-00788 - Mo-00792

2-Pinen-8-ol Mo-00788 lsol. from oil of C. spp. Cryst. Mp 53.5-55°. [IX]~ + 55°
2,6-Dimethylbicyclo[3 .1./)hept-2-ene-6-methano/, 9CJ (c, 0.8 in EtOH).
[90128-93-1] (-)-form
Bp 11 101-102°. [IX)~ -47.1° (EtOH).

~~OH
Ac:
C11H 180 1 M 194.273
lsol. from Valeriana officina/is.
3-Methy/butanoy/: (- )-Myrtenyl isovalerate
C1.,H 160 M 152.236 lsol. from oil of V. officina/is.
Constit. of Aristolochia /onga. Oil. [1X]n -37.9° (c, 0.95 in 10-A/dehyde: [18486-69-6].
CHC1 3). Unstable oil. Bp 220-221°. [1X]n -15.3°.
Ac: [90024-30-9]. 8-Acetoxy-2-pinene (±)-form
C 11H 180 1 M 194.273 Oil. n~ 1.4963.
From A. longa. Oil. [1X]n -40° (c, 1.25 in CHC1 3).
Hydrogen phthalate: Mp 120.5°.
De Pascual Teresa, J. eta/, Phytochemistry, 1983, 22, 2753.
[19250-17-0]
Stoll, A. et al, Helv. Chim. Acta, 1957, 40, 1205 (acetate,
2(1 0)-Pinen-3-ol Mo-00789 isovalerate)
6,6-Dimethyl-2-methy/enebicyclo[3 .l.l]heptan-3-o/. Couchman, F.M. eta/, Tetrahedron, 1964, 20, 2037 (isol)
Pinocarveol. Piny/ alcohol. /socarveol Banthorpe, D.V. eta/, Chern. Rev., 1966, 66, 643 (rev)
Bates, R.B. eta/, J. Org. Chern., 1968, 33, 1730 (pmr)
(1R,3R,5R)-form Borowiecki, L. et al, Pol. J. Chern. (Rocz. Chern.), 1971, 45, 573
HO Absolute (Myrtenic acid)
configuration Kergomard, A. et al, Bull. Soc. Chirn. Fr., 1974, 2572 (synth)
Rauchschwalbe, G. et al, Helv. Chim. Acta, 1975, 58, 1094 (synth)
Bohlmann, F. eta/, Org. Magn. Reson., 1975, 7, 426 (crnr)
CIOH160 M 152.236
(1R,JR,5R)-form [3917-59-7] 2-Pinen-4-one Mo-00791
(-)-cis-form Verbenone
Cryst. Mp 49-50°. [IX)~ -37.4° (c, 3.6 in MeOH).
(1R,3S,5R)-form [19894-98-5]
(+)-trans-form
Oil. [1X]~ +60.7° (c, 1.6 in MeOH).
(1S,JR,5S)-form [547-61-5]
~O (+}fo~
(-)-trans-form C10H 140 M 150.220
Constit. of oil of Eucalyptus globulus. Also from Sium (+)-form [18309-32-5]
/atijugum, Tori/is japonica and Costus speciosus. Oil. Mp
Constit. of Spanish Verbena oil and Eugenia pseudomata
5°. Bp 209-210°, Bp 1 72°. oil. Oil. Mp 6.5°. Bp 227-228°. [IX]~ +249.6°.
(1S,JS,5S)-form [19889-99-7] I> TK5075000.
(+)-cis-form Oxime:
Constit. of Ledum oils. Cryst. Mp 49°. [1X]n +47°.
C10H 15NO M 165.235
Bose, A.K., J. Org. Chern., 1955, 20, 1003 (struct) Cryst. (pet. ether). Mp 120-121°. [1X]n + 80° (Et20).
Banthorpe, D.V. eta/, Chern. Rev., 1966, 66, 643 (rev)
Teisseire, P. et al, Recherches, 1967, 59 (synth)
(-)-form [1196-01-6]
Hirata, T., Bull. Chern. Soc. Jpn., 1972, 45, 3169 (prnr, synth) Oil. Bp 253.5°. [1X]D -144°.
Org. Synth., 1977, 56, 25 (synth) Banthorpe, D.V. et a/, Chern. Rev., 1966, 66, 643 (rev)
Bates, R.B. et al, J. Org. Chern., 1968, 33, 1730 (prnr)
Fallis, A.G., Can. J. Chern., 1975, 53, 1657 (synth)
2-Pinen-10-ol Mo-00790
Myrtenol. Darwinol
[515-00-4] 2(10)-Pinen-3-one Mo-00792
6,6-Dimethy/-3-methylenebicyclo[3.1.1]heptan-3-one, 9CI.
PinocariJone. Carvopinone. Isocarvone. 3-Nopinenone
[16812-40-1)

0~
lV (+)-form
C10H 160 M 152.236
(+)-form [6712-78-3]
lsol. from oil of Myrtus communis, Darwinia grandiflora, C10H 140 M 150.220
Leptospermum /anigerum, Chamaecyparis formosensis (+)-form [34413-88-2]
and others. Oil. Bp 11 103-104°. [1X]n +45.5°. Sex attractant for pine beetle. Oil. Bp4 84-85°. [1X]n
10-A/dehyde: [23727-16-4). MyrteiUll +63°.
CIOH140 M 150.220 Oxime: Cryst. Mp 132-133°.
Occurs in eucalyptus and other plant oils. Unstable oil
(-)-form [19890-00-7]
with cinnamon odour. Bp 15 99-100°. [IX]~ + 14.75°.
lsol. from oils of Eucalyptus g/obulus, Chenopodium
10-Carboxy/ic acid: [601-74-1]. 2-Pinen-10-oic acid. ambrosioides and Nepeta ciliaris. Sex attractant for the
Myrtenic acid pine beetle. Oil. Mp -1.8°. Bp4 67-69°. [1X]n -68.5°.
C10H 140 1 M 166.219 Oxime: Cryst. Mp 131-132°.

143
Carane - 3-Caren-2-one Mo-00793 - Mo-00798

Banthorpe, D.V. et al, Chern. Rev., 1966, 66, 643 (rev)
Bessiere-Chretien, Y. et al, Bull. Soc. Chim. Fr., 1971, 2591 (synth)
Jefford, C.W. et al, Helv. Chim. Acta, 1973, 56, 2649 (synth)
(-)-form [20296-50-8]
lsol. from root oil of Kaempferia galanga and from
Cedrus deodara. Oil. [ex]~ -5.72°.
Simonsen, J., J. Chern. Soc., 1920, 117, 570 (struct)
Sandberg, R., Ark. Kemi, 1960, 16, 255 (abs co'!fig)
Ryhage, R. et al, Acta Chern. Scand., 1964, 47, 475 (ms)
Wrolstad, R.E. et al, J. Agric. Food Chern., 1964, 12, 507 (ir)

Caranes Schweers, W., Tetrahedron Lett., 1968, 4425 (biosynth)

Banthorpe, D.V. et al, Phytochemistry, 1976, 15, 109 (biosynth)
Cocker, W. et al, J. Chern. Soc., Perkin Trans. l, 1978, 1370
(synth)
Akhi1a, A. et al, Phytochemistry, 1980, 19, 1691 (biosynth)
Johnson, C.R. et al, J. Org. Chern., 1987, 52, 1493 (synth)
Carane Mo-00793
3,7,7- Trimethylbicyclo[4.J.O]heptane, 9CI 3-Caren-10-oic acid Mo-00796
[554-59-6] 7,7-Dimethylbicyclo[4.l.O]hept-3-ene-3-carboxylic acid, 9CI

COOH

( 1S,3S,6R)-form
Absolute
y(j (+)-form

configuration
C1oH1402 M 166.219
C1.,H18 M 138.252 (+)-form [498-12-4] Clulminic acid
(JS,3S,6R)-form [18968-24-6] Constit. of Chamaecyparis nootkatensis. Cryst. (pet.
(-)-cis-form ether). Mp 104-105°. [ex] 0 +6° (c, 3.9 in MeOH).
[ex]~ -37.7°. n~ 1.4550. (-)-form [554-58-5]
(JS,3R,6R)-form (18968-23-5] Jsochamic acid
(+)-trans-form Mp 105-106°. [ex] 0 -6°.
[ex]~ + 63.SO (c, 1.8). n~ 1.4565. Norin, T., Ark. Kemi, 1964, 22, 123 (abs co'!fig)
Cocker, W. et al, J. Chern. Soc. C, 1966, 41, 946 (synth) Gensler, W.J. et al, J. Org. Chern., 1973, 38, 1726 (synth, bib£)
Gollnick, K. et al, Tetrahedron Lett., 1966, 5157 (synth)
4-Caren-10-oic acid Mo-00797
2-Carene Mo-00794 7,7-Dimethylbicyclo[4.J.O]hept-4-ene-3-carboxylic acid, 9CI.
3,7,7- Trimethylbicyclo[4.l.O]hept-2-ene. 4-Carene (obsol.) Clulmic acid
[554-61-0] [498-14-6]
COOH
I

~
Absolute
configuration

C1oH1, M 136.236
(JS,6R)-form C 10H 140 2 M 166.219
Widespread in plants. Oil. Bp80 96°. [ex]~ + 76° (neat). Constit. of Chamaecyparis nootkatensis. Also in Juniperus
depressa and J. oblonga. Oil. Bp8 142°. (ex]~ +257.SO (c,
Shun-ichi, Y. et al, Chern. Pharm. Bull., 1975, 23, 2539 (synth)
Brunetti, P. et al, Gazz. Chim. /tal., 1977, 107, 433 (synth)
1.4 in MeOH).
Cyclohexylamine salt: Cryst. Mp 165-166°. [ex]~ + 164.SO
(c, 2.9 in MeOH).
3-Carene Mo-00795
3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene. ex-Carene. Jsodiprene Erdtman, H. et al, Acta Chern. Scand., 1956, 10, 1381.
Norin, T., Ark. Kemi, 1964, 22, 123 (abs co'!fig)
[13466-78-9] Goryaev, M.l. et al, CA, 1965, 62, 3880 (isol)

3-Caren-2-one Mo-00798
Al6""<:::, [53585-45-8]

No
~ (+)-fMm

C 10H 16 M 136.236 ~ (-)-fonn

I> FH8400000.
(+)-form [498-15-7]
Widespread plant product, found esp. in turpentine C 10H 140 M 150.220
(from Pinus spp.). Also from Abies, Citrus and Juniperus
spp. Oil with pleasant odour. Bp200 123-124°, Bp7_5 168- (+)-form
1690. Oxidises in air. Oil. [ex]~ +243° (c, 0.15 in CHC1 3).
(-)-form

144
3-Caren-5-one - Secothujene Mo-00799 - Mo-00803

Constit. of Zieria aspalathoides. Oil. [1X]n -324° (c, 4.6

in CHC1 3).
Cocker, W. et al, J. Chern. Soc. C, 1968, 3073 (synth, pmr)
Lassak, E.V. et al, Aust. J. Chern., 1974, 27, 2061 (isol)
Thujanes
3-Caren-5-one Mo-00799
4,7,7-Trimethylbicyclo[4.1.0]hept-3-en-2-one, 9CI
[81800-50-2] 5-Isopropylbicyclo(3.l.O]hexan-2-one, SCI Mo-00802
5-(1-M ethylethyl)bicyclo[3 .1.0]hexan-2-one, 9CI. Sabina
ketone

(-)-form

C1ofl 140 M 150.220 I

Constit. of Kaempferia galanga. Oil. No. opt. rotn. ~

reported for natural isolate. C9H 140 M 138.209
(-)-form [22327-32-8] (-)-form [4498-01-5]
Oil. Bp0_5 58°. [1X]i:' -271° (c, 3.1 in CHC1 3). Liq. or prisms (Hp). Characteristic odour. Spar. sol.
Semicarbazone: Prisms (EtOH). Mp 170° (159-161 °). Hp, sol. EtOH. Mp 17°. Bp 17 97.5°. [1X]i;t. 6 -25.64°
Cocker, W. et al, J. Chern. Soc. C, 1968, 3073; 1971, 1073 (synth, (homogeneous).
pmr) Semicarbazone: Amorph. powder or cryst. (MeOH). Mp
Kiuchi, F. eta[, Phytochemistry, 1987, 26, 3350 (isol) 135-137°. [1X]::,S· 6 + 137.SO (c, 1.0 in MeOH).
2,4-Dinitrophenylhydrazone: Orange needles
4,5-Epoxy-3-hydroxy-2-caranone Mo-00800 (MeOH/CHC1 3). Mp 124°. [1X]n + 135.2° (c, 1.0 in

?ro
CHC1 3).
(±)-form [38981-64-5]
Sol. Hp, Etp. Bp5 70°.
Semicarbazone: Cryst. (MeOH aq.). Mp 156-157°.
0:~ 2,4-Dinitrophenylhydrazone: [28892-22-0].
Orange-red needles (CHC1 3fMeOH). Mp 175-176.SO.
Short, A.G. et al, J. Chern. Soc., 1939, 1415 (synth)
C 10H 140 3 M 182.219 Daly, J.W. et al, J. Am. Chern. Soc., 1958, 60, 6330 (abs config)
(1 R* .JS",48" ,58",68")-form Wheeler, J.W. et al, J. Org. Chern., 1969, 34, 545 (synth, ir, pmr)
Asarinol A Mori, K. et al, Tetrahedron, 1970, 26, 2821 (synth, ir, pmr)
Constit. of Asiasari Radix from an Asiasarum sp. Russell, G.A. et al, J. Am. Chern. Soc., 1971, 93, 1452 (synth, ir,
Prisms. Mp 92-94°. pmr)
Alexandre, C. et al, Bull. Chern. Soc. Jpn., 1972, 45, 2241 (synth)
Hashimoto, K. et al, Phytochemistry, 1990, 29, 3571 (isol, pmr, Gaoni, Y., Tetrahedron, 1972, 28, 5525 (synth, ms, pmr)
cmr, cryst struct)
Secothujene No-00803
5-Hydroxy-3-caren-2-one Mo-00801 2-Acetyl-1-(1-methylethyl)cyclopropaneacetic acid, 9Cl. 2-
Acetyl-1-isopropylcyclopropaneacetic acid

0 _.4~-l
Y' ~COOH
C10H 160 3 M 184.235
C1.,H1402 M 166.219 (JS,2S)-form [4700-82-7]
(1 R* ,58" ,68")-form Constit. of Brocchia cinerea. Oil, cryst. on standing. Mp
Asarinol A 62°. [1X]n -164° (c, 4.2 in Et20). The nat. isolate was
Constit. of Asiasari Radix from an Asiasarum sp. descr. as an oil, no opt. rotn. given. Prob. identical with
Needles. Mp 80-82°. the semisynthetic prod. obt. by oxidn. of thujene.
Hashimoto, K. et al, Phytochemistry, 1990, 29, 3571 (isol, pmr, Shrivastava, R.D. et al, CA, 1965, 64, 6696g (synth)
Jakupovic, J. et al, Phytochemistry, 1988, 27, 2219 (isol, ms, pmr,
cmr, cryst struct)
cmr) '

145
2,4(10)-Thujadiene - 3-Thujanone Mo-00804 - Mo-00808

2,4(10)-Thujadiene Mo-00804 (1S,3S,4R,5R)-form [21653-20-31

1-lsopropy/-4-methy/enebicyclo[3 .1.0lhex-2-ene (- )-3-Neoisothujanol. (- )-3-Thujol
[36262-09-61 Cryst. (pet. ether). Mp 66-67°. [a)i: -22.SO (c. 2 in
EtOH).
(JS,3S,4S,5R)-form [7712-79-01
( + )-3-Thujano/. ( + )-3-Isothujol
Liq. Bp 14 98-99°. [ali: + 108° (c, 2 in CHC1 3).
(JR,3R,4R,5S)-form [20126-29-81
(- )-3-Thujanol. (- )-Isothujol
Liq. Bp1. 8 72°. [al~· 5 -46.7° (c, 20 in CC14).
CtoHt4 M 134.221 (JR,3R,4S,5S)-form [3284-85-31
(±)-form
( + )-3-Neoisothujanol. ( + )-Thujol
Liq.
Oil.
(JR,3S,4R,5S)-form [33766-34-61
Chung, R.H. eta/, J. Am. Chern. Soc., 1972, 94, 2183 (synth)
Wheeler, J.W. eta/, Org. Mass Spectrom., 1974, 9, 1173 (ms)
(- )-3-Neothujanol. (- )-Neoisothujol
Liq.
(JR,3S,4S,5S)-form [33766-31-31
Thujane Mo-00805 ( + )-3-Isothujanol. ( + )-Neothujol
4-Methyl-1-(J-methylethyl)bicyclo[3.1.0lhexane, 9CI. 1-
Liq.
lsopropyl-4-methylbicyc/o[3 .1.0lhexane. Sabinane
Banthorpe, D.V. et a/, J. Chern. Soc. B, 1968, 1356 (synth, config)
Acharya, S.P. eta/, J. Org. Chern., 1969, 34, 3015 (synth, abs
config)
Whittaker, D. eta/, Chern. Rev., 1972, 72, 305 (rev)
Hoch, V., J. Org. Chern., 1977, 42, 1616 (synth)
(1R,4R,5R)-form
I

~ 4-Thujanol Mo-00807
2-Methyl-5-(1 -methylethyl)bicyclo[3 .1.0lhexan-2-ol, 9CI. 5-
C 10H 18 M 138.252
lsopropyl-2-methylbicyclo[3 .1.0lhexan-2-ol. Sabina hydrate.
Mobile oil with faint odour. Bp 758 157°.
Sabinene hydrate
(JR,4R,5R)-form [5523-91-11
[546-79-21
(+)-trans-form
[ali; +84.3° (c, 20 in CHC13).
(JR,4S,5R)-form [5523-90-01
(-)-cis-form
[al~· 5 -10.05° (c, 20 in CC14).
H~ (1R,4R,5R)-form
(JS,4R,5S)-form [7712-66-51 I
(+)-cis-form ~
[aln +6.7°.
C10H 180 M 154.252
(JS,4S,5S)-form [20126-20-91
(-)-trans-form (JR,4R,5R)-form
[aln -37.3° (c, 10 in CC14). Cryst. Mp 36.5-37.2°. [ali; +47.2° (c, 10 in EtOH).
Acharya, S.P. eta/, J. Org. Chern., 1964, 34, 3015 (synth, nomencl) (1 R,4S,5R)-form
Ohloff, G. et a/, Tetrahedron, 1966, 22, 309 (synth, abs config, pmr) Constit. of the essential oil of American peppermint and
other Mentha spp. Cryst. by subl. Mp 61°. [ali; +32.2°
(c, 4.2 in EtOH).
3-Thujanol Mo-00806
[7712-82-5, 15537-55-0, 15826-82-1, 17699-16-0, 58117-61-6]
4-M ethy/-1-(1 -methylethyl)bicyclo[3 .1.0lhexan-3-ol, 9CI. 1-
lsopropyl-4-methylbyclo[3.1.0lhexan-3-o/. 3-Sabinano/. Daly, J.W. eta/, J. Am. Chern. Soc., 1958, 80, 6330 (isol, synth)
Tanacetyl alcohol. P-Thujyl alcohol Ohloff, G. eta/, Tetrahedron, 1966, 22, 309 (abs config, synth)
Fanta, W.l. eta/, J. Org. Chern., 1968, 33, 1656 (synth)
I
I

3-Thujanone Mo-00808
H O3 ' O
5
4-M ethyl-1-(1 -methylethyl)bicyclo[3 .1.0lhexan-3-one, 9CI. 1-
2 I
(1S,3R,4R,5R)-form lsopropyl-4-methylbicyclo[3 .1.0lhexan-3-one. 3-Sabinanone.
I Tanacetone. Absinthone. Salvone. Chrysanthone

0'0
A (1125-12-8]
C 1gH180 M 154.252
Occurs free and combined as ester in several essential oils,
esp. Artemisia spp. and also Thuja wareana, Glycyrrhiza
triphylla and Juniperus depressa. (1S,4S,5R)-form
(JS,3R,4R,5R)-form [21653-18-91 I
(- )-3-lsothujanol. (- )-3-Neothujol
Low-melting solid. Mp 22°. Bp 50-52°. [ali? -9.0° (c, 2
A
in EtOH). C 10H 160 M 152.236
Widespread in oils of Pinaceae, Labiateae and
(JS,3R,4S,5R)-form [21653-19-01 Compositae.
( + )-3-Neothujanol. ( + )-3-Neoisothujol
Liq. Bp0 _3 53-54°. [ali: +41.SO (c, 2 in CHC1 3). (JS,4S,5R)-form [471-15-81
( + )-3-Thujone. ( + )-lsothujone. ( + )-P-Thujone

146
3-Thujene - 3-Thujen-2-one Mo-00809 - Mo-00812

Constit. of many essential oils. Liq. Bp 201-202°. [1X]n C 10H 16 M 136.236

+ 72.46° (neat). (+)-form [2009-00-9]
I> X09630000. Constit. of various essential oils, e.g. Juniperus sabina,
(1R,4R,5S)-form Myristicafragrans. Bp 160 163-165°. [1X]n +95° (c, 20 in
(- )-3-Thujone CC14).
Liq. [1X]D -27.8°. (-)-form [10408-16-9]
I> X09625000. Constit. of Laurus nobilis, Pinus muricata and some
(1S,4R,5R)-form [546-80-5] other plants. Liq. Bp 162-166°. [1X]n -89°.
(- )-3-/sothujone. (- )-IX-Thujone Jaureguiberry, G. et al, Bull. Soc. Chirn. Fr., 1962, 1985 (isol, ir,
Constit. of many essential oils including Western Red prnr)
Cedar leaf oil (Thuja plicata). Liq. Bp 12 78°. [IX]~ -20.SO Ryhage, R. eta/, Acta Chern. Scand., 1963, 17, 2025 (ms)
(c, 2 in CHC1 3). Banthorpe, D.V. eta/, J. Chern. Soc., Chern. Cornrnun., 1966, 177
I> X09625000. (biosynth)
Fanta, W.l. eta/, J. Org. Chern., 1968, 33, 1656 (synth)
(1R,4S,5S)-form Acharya, S.P. et al, J. Org. Chern., 1969, 34, 3015 (abs conjig)
( + )-3-/sothujone Whitaker, D. et al, Chern. Rev., 1972, 72, 305 (rev)
Liq. Bp 12 78°. [1X]~ +20° (c, 1 in CHC13). Karrer, W. et al, Konstitution und Vorkornrnen der Organischen
I> X09630000. Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
[58501-78-3) no. 60 (occur)
v. Sydow, E., Acta Chern. Scand., 1964, 18, 1099 (rns)
Acharya, S.P. eta/, J. Org. Chern., 1969, 34, 3015 (synth, abs 4(10)-Thujen-3-ol Mo-00811
config) 4-Methylene- I-( J-methylethyl)bicyclo[3 .J.O]hexan-3-ol, 9CI.
Whittaker, D. et al, Chern. Rev., 1972, 72, 305 (rev) J-/sopropyl-4-methylenebicyclo[3.J.O]hexan-3-ol. Sabino/
Norin, T. eta/, Acta Chern. Scand., 1973, 27, 1579 (prnr)
Abraham, R.J. et al, Org. Magn. Reson., 1974, 6, 184 (crnr) [471-16-9]

HO'O
Hach, V., J. Org. Chern., 1977, 42, 1616 (synth)

3-Thujene Mo-00809
2-Methyl-5-(1-methylethyl)bicyclo[3 .1.0. ]hex-2-ene, 9CI. 5- Absolute
/sopropyl- 2-methylbicyclo[3 .J.O]hex-2-ene. IX- Thujene. configuration
I
Origanene
~
[2867-05-2]
C10H 160 M 152.236
Constit. of Juniperus and Sabina spp. Also from Artemisia
kaschgarica. Oil. Bp 208°. [IX]~ + 16.2° (c, 21 in CHC13).
Acid phthalate: Cryst. (pet. ether). Mp 101-102°. [IX]~
(-)-form - 17.SO (MeOH).
I Ac: [3536-54-7]. Sabinyl acet(lte
~ C12H 180 2 M 194.273
CtoHt, M 136.236 Constit. of J. spp. Oil. Bp 18 113-114°. [IX]~ +80° (c, 20
lsol. from Boswellia serrata, Eucalyptus spp., dill, juniper, in EtOH).
coriander and many other plant oils. (Opt. rotn. Norin, T. eta/, Acta Chern. Scand., 1962, 16, 640 (abs config)
frequently not reported). Banthorpe, D.V. et a/, J. Chern. Soc. B, 1968, 1356 (isol, struct)
(+)-form [563-34-8] Norin, T. et al, Acta Chern. Scand., 1973, 27, 1579 (prnr)
Liq. Bp 151-153°. [1X]n +38.84°.
(-)-form [3917-48-4] 3-Thujen-2-one Mo-00812
lsol. from oil of Thuja occidentalis and other essential 4-Methyl- I-( J-methylethyl)bicyclo[3 .l.O]hex-3-en-2-one. J-
oils. Bp 150.5-152.SO. [1Xln -14.76°. ni? 1.4559. /sopropyl-4-methylbicyclo[3.J.O]hex-3-en-2JP1le· Umbellulone.
Umbellol. Oreodaphnol
Shaw, A.C., Can. J. Chern., 1953, 31, 277 (isol)
Norin, T., Acta Chern. Scand., 1962, 16, 640 (abs config) [24545-81-1]
Thomas, A.F. eta/, Helv. Chirn. Acta, 1964, 47, 475 (ms)
Wrolstad, R.E. et a/, J. Agric. Food Chern., 1964, 12, 501 (ir)
Acharya, S.P. et al, J. Org. Chern., 1969, 34, 3015 (abs config)
Karrer, W. et a/, Konstitution und Vorkornrnen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 59 (occur)

4(10)-Thujene Mo-00810 C10H 140 M 150.220

4-Methylene-J-(1-methylethyl)bicyclo[3.J.O]hexane, 9CI. J- Oil.
/sopropyl-4-methylenebicyclo[3.J.O]hexane. Sabinene
I> XP0200000.
[3387-41-5]
(-)-form [546-78-1]
Constit. of the essential oil of Umbellularia californica.
Bp70 138.5°. [1X]n -37°.
Semicarbazone: Cryst. (MeOH). Mp 238-239° dec.
(+)-form Smith, H.E. eta/, J. Org. Chern., 1956, 21, 830 (struct)
I Massey, E.H. et al, J. Org. Chern., 1966, 31, 684 (abs config)
~ Abraham, R.J. et a/, Org. Magn. Reson., 1974, 6, 184 (cmr)
Baeckstrom, P. et al, J. Org. Chern., 1985, 50, 3728 (synth)

147
3-Thujylamine - 3,3-Dimethylbicyclo[2.2.1]heptan-2-... Mo-00813 - Mo-00818

3-Thujylamine Mo-00813 2,3-Dimethylbicyclo(2.2.1)heptan-2-ol Mo-00815

4-Methyl-l-(l-methylethyl)bicyclo[3.1.0]hexan-3-amine. 3- JJ-Santenol. Santene hydrate
Amino-J-isopropyl-4-methylbicyclo[3 .J.O]hexane. 3- [59432-92-7]
Aminothujane
I
OH
(\lf-CH3
~Nr) (lS,3R,4R,5R)-form
l_pi'CH3

I
C9H 160 M 140.225
.A Constit. of Santalum album. Cryst. Mp 102-103°. Mp
refers to synthetic racemate. No indication of opt. rotn.
C 1.,H19N M 153.267 of nat. prod. All 4 racemates are known synthetically.
(1S,3R,4R,5R)-form [5033-80-7] Beckman, S. et al, Chem. Ber., 1961, 94, 1905 (synth)
(- )-Neothujylamine. (- )-a.-Thujylamine Demote, E. et a/, Helv. Chim. Acta, 1976, 59, 737 (isol)
Oil. Bp 196.7°. [a.]~ -14.W (neat).
(1S,3R,4S,5R)-form [5033-82-9] 3,3-Dimethylbicyclo(2.2.1)heptan-2-ol Mo-00816
( + )-Neoisothujylamine. ( + )-ft-Thujylamine Camphenilol
Oil. Bp 199.6°. [a.]~ +27.8° (neat).
[5957-68-6)
(1S,3S,4R,5R)-form [5033-79-4]
(- )-Thujylamine. (- )-/so-a.-thujylamine
Oil. Bp 202.2°. [a.]~ -22.1° (neat).
(1S,3S,4S,5R)-form [5033-81-8]
( + )-/sothujylamine. ( + )-Iso-P-thujylamine
HA
H<)~ (1RS,2RS,4SR)-form
Oil. Bp 193.4°. [a.]~ +94.9° (neat).
Massey, E.H. et al, J. Org. Chem., 1966, 31, 684 (abs config, synth) C,H 160 M 140.225
Smith, H.E. eta/, J. Org. Chem., 1966, 31, 690 (pmr)
(JRS,2RS,4SR)-form [640-54-0]
(±)-endo-form
Cryst. (EtOH). Mp 76-77°.
(JRS,2SR,4SR)-form [515-28-6]
( ± )-exo-form
Miscellaneous bicyclic Cryst. (EtOH). Mp 151-153.SO.
Schneider, H.-J. et al, Tetrahedron Lett., 1970, 5197 (cmr)

monoterpenoids
Stothers, J.B. eta/, Can. J. Chem., 1976, 54, 1211 (cmr, synth)

5,5-Dimethylbicyclo(2.2.l)heptan-2-ol Mo-00817
/socamphenilol. 5-Camphenilo/
[497-34-7]
Camphene Mo-00814

H~
2,2-Dimethyl-3-methylenebicyclo[2.2.J]heptane
[79-92-5]

(+)-form H
Absolute
c,H 1,o M 140.225
configuration
(1RS,2SR,4RS)-form
( ± )-exo-form
C 1oH1, M 136.236 Mp 60-61°.
t> EX1055000. Ac:
(+)-form [5794-03-6] CuHlaOl M 182.262
Widespread natural product found in many essential Bp 214°.
oils. Used in perfumery. Cryst. Mp 51°. Bp 158-160°, McGreer, D.G., Can. J. Chem., 1962, 40, 1554.
Bpl7 52o.
(-)-form
3,3-Dimethylbicyclo(2.2.1)heptan-l-one Mo-00818
Widespread natural product. Used in perfumery. Mp
49-50°. Bp 158-160°. [a.] 0 -119.1°. Camphenilone
Ryhage, R. et a/, Acta Chem. Scand., 1963, 17, 2025 (ms)
Karrer, W. et a/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birlliuser Verlag, Basel, 1972-1985,
no. 65 (occur)
Hana, G.W. eta/, Chem. Ber., 1978, 111, 2527 (synth, bib{)
Sax, N.l., Dangerous Properties of Industrial Materials, 5th Ed.,
Van Nostrand-Reinhold, 1979, 466. C,H140 M 138.209
(1R,4S)-form
Cryst. Mp 38.5-39.0°. Bp 193-194°, Bp 17 77.9°.
(1S,4R)-form [13211-15-9]

148
2,3-Dimethylbicyclo[2.2.1]hept-2-... - 5,5-Dimethyl-6-methylenebicyclo[... Mo-00819 - Mo-00824

Cryst. Mp 41°. Bp 191-192°. [a] 0 +49.2° (EtOH). 7,7-Dimethyl-2- Mo-00822

Berson, J.A. et al, J. Am. Chern. Soc., 1961, 83, 3986 (abs conjig) methylenebicyclo(2.2.l)heptane
Criegee, W. et al, Chern. Ber., 1963, 96, 1564 (synth) rx.-Fenclrene
Baker, K.M. et al, Tetrahedron, 1968, 24, 1663 (pmr)
Grutzner, J.B. et al, J. Am. Chern. Soc., 1970, 92, 7107 (cmr) [471-84-1]
de Botton, M. et al, Bull. Soc. Chim. Fr., 1973, 2472 (synth)
Stothers, J.B. et al, Can. J. Chern., 1973, 51, 2893 (cmr)

2,3-Dimetbylbicyclo(2.2.l)hept-2-ene Mo-00819 Relative

2,3-Dimethy/-2-norbornene. Slllltene configuration
[529-16-8)
CtoH 16 M 136.236
(-)-form [7378-37-2]
Constit. of Cinnamomum /aureiri and Mentha spp. Also
from Thuja plicata and Valeriano officina/is. Oil. Bp 155-
1600. [a] 0 -42.62° (EtOAc). n~ 1.4742.
Hucke!, W. et al, Justus Liebigs Ann. Chern., 1963, 664, 31.
C,H14 M 122.210
Kokke, W.C.M.C., J. Org. Chern., 1973, 38, 2989.
Constit. of sandalwood and pine oil. Also from Mentha
spp. and Furcraea gigantea. Oil. Bp 140-141°. nl:J 1.4688.
Ryhage, R. et al, Acta Chern. Scand., 1963, 17, 2025 (ms) 3,3-Dimethyl-2- Mo-00823
Degny, E. et al, Bull. Soc. Chim. Fr., 1972, 4770 (synth) methylenebicyclo(2.2.l)heptan-l-ol
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr) 1-Campheno/
[22780-14-9]
5,6-Dimethylbicyclo(2.2.l)hept-5-en-2-ol, Mo-00820
9CI
5,6-Dimethy/-5-norbornen-2-o/, SCI
[59300-41-3]

C 10H 160 M 152.236

Cryst. Mp 74°.
Paukstelin, J.V. et al, Tetrahedron, 1973, 29, 1955 (synth)
Morris, D.G. et al, J. Chern. Soc., Perkin Trans. 2, 1975, 539 (cmr)

C,H140 M 138.209
5,5-Dimetbyl-6- Mo-00824
(JR* ,2S*)-form
methylenebicyclo(2.2.l)heptan-2-ol
exo-form
6-Campheno/. Nojigiku alcohol
Constit. of the oil of Santalum album. Used as a
flavouring for tobacco and food. Liq. Bp 10 87°. [3570-04-5]
Demole, E. et al, Helv. Chim. Acta, 1976, 59, 737 (isol, synth)
Swiss Pat., 600 799, (1978); CA, 89, 414992m (synth)

2,2-Dimethyl-5- Mo-00821
methylenebicyclo(2.2.l)heptane
fJ-Fenclrene
ciOH 1,0 M 152.236
[33404-67-0]
(1S,2R,4S)-form [55925-49-0]
( + )-exo-form
Constit. of Chrysanthemum japonense. Cryst. Mp 59.5-
Absolute 60.50 (52-53°). Bp 11 98-99°. [ah6 + 0 26, +103.5, +12°.
configuration Ac: [55627-02-6].
C 12H 180 2 M 194.273
From C. japonense. [a) 0 + 20.9° (c, 0.6 in CHC13).
CtoH16 M 136.236
3,5-Dinitrobenzoy/: Mp 107-108°.
(+)-form
Constit. of Mentha spp. Oil. Bp 152-154°. [a]~ +62.SO. Matsuo, A. et al, Tetrahedron Lett., 1974, 4219 (synth)
Julia, M. et al, Tetrahedron Lett., 1976, 2141 (synth)
Dibromide: Cryst. Mp 81-82°. Uchio, Y. et al, Bull. Chern. Soc. Jpn., 1978, 51, 2342 (isol)
Bohlmann, F. et al, Org. Magn. Reson., 1975, 7, 426 (cmr) Darby, N. et al, Can. J. Chern., 1979, 57, 742 (synth)
Salveson, A. et al, Planta Med., 1976, 30, 93 (isol)

149
3,3-Dimethyl-2-methylenebicyclo[..• - 3,3,6-Trimethylbicyclo[2.2.1]heptan-... Mo-00825 - Mo-00831

3,3-Dimethyl-2- Mo-00825 Ranganathan, S. eta/, Tetrahedron, 1974, 30, 63 (synth, ir, pmr)
Morris, D.G. eta/, J. Chern. Soc., Perkin Trans. 2, 1975, 539 (cmr)
methylenebicyclo[2.2.1)heptan-6-one Begue, J.P. eta/, J. Chern. Res. (S), 1978, 52 (synth, pmr)
6-Camphenone

2,2,3-Trimethylbicyclo(2.2.1)heptane Mo-00829
Isobornane. Dihydrocamphene

C10H 140 M 150.220

~ (1R, 3S, 4S)-form
C 10H 18 M 138.252
(+)-form [55659-42-2] (IR,3S,4S)-form [38451-93-3]
Cryst. Mp 47-48°. [a:Jn +33.7° (c, 0.9 in CHC1 3). (- )-endo-forrn
Matsuo, A. et al, Tetrahedron Lett., 1974, 4219. Cryst. (EtOH). Mp 69-70°. [a:Jn -3.7° (c, 0.55 in
Julia, M. et a/, Tetrahedron Lett., 1976, 2141. CHC1 3).
(IS,3R,4R)-form
Lactiftorin Mo-00826 ( + )-endo-form
Cryst. (MeOH). Mp 62-63°. Bp750 166-166.SO. (a:]~

H~~o
+ 8.68° (C6H 6).
Grutzner, J.B. et a/, J. Am. Chern. Soc., 1970, 92, 7107 (cmr)
Vokac, K. eta/, Tetrahedron Lett., 1972, 1665.
Gream, G.E. eta/, Aust. J. Chern., 1974, 27, 603 (synth)

O CH2COOPh 2,7,7-Trimethylbicyclo(2.2.1)heptane Mo-00830

2, 7, 7- Trirnethylnorbornane. a:- Fenchane. Isobornylane
C23H 260 10 M 462.452 (obsol.)
Constit. of Paeonia lactifiora. Cryst. (CHC1 3/MeOH). Mp
207-209°. [a:)i; +37.2° (c, 0.01 in EtOH).
Yu, J. et al, Phytochemistry, 1990, 29, 3859 (isol, pmr, cmr)
Lang, H.Y. eta/, Tetrahedron, 1990, 46, 3123 (struct)

2-Methyl-3-methylenebicyclo(2.2.1)heptan- Mo-00827
2-ol, 9CI C 10H 18 M 138.252
2-Methyl-3-rnethylene-2-norbornanol Oil. Bp 12 60°. [a:]~ -41.9° (c, 1.24 in C6H 6). Mixt. of
diastereoisomers which are not well descr. in the lit.
[42836-45-3, 42836-46-4]
Hiickel, W. et al, Justus Liebigs Ann. Chern., 1963, 664, 31 (bib[)
Huisgen, R. eta/, Tetrahedron Lett., 1985, 26, 4431.

3,3,6-Trimethylbicyclo[2.2.1 )heptan-2-one Mo-00831

C9H 140 M 138.209 6- Methylcamphenilone. 3,3,6- Trirnethylnorbornan-2-one
(IR*,2S*,4S*)-form [59300-40-2]
·exo-form
Constit. of the oil of Santa/urn alb urn. Bp 10 70°. n~
1.4975.
Demole, E. eta/, Helv. Chim. Acta, 1976, 59, 737 (synth)
C10H 160 M 152.236
1-Nitrocamphene Mo-00828 Configurational identity of various samples unclear.
3,3-Dimethyl-2-methylene-1-nitrobicyclo[2.2.1]heptane, 9CI. Crystalline-form
3,3-Dimethyl-2-methylene-1-nitronorbornane, 8CI Mp 141-142°.
[6244-05-9] Sernicarbazone: Small prisms (MeOH). Mp 231-232°.
Oily-form
Bp 10 100°.
2,4-Dinitrophenylhydrazone: Cryst. Mp 154-155°.
Nametkin, S.S. eta/, Justus Liebigs Ann. Chern., 1923, 432, 227.
Beereboom, J.J., J. Org. Chern., 1965, 30, 4230 (synth)
C1.,H15N02 M 181.234 Hunter, D.H. et al, J. Am. Chern. Soc., 1972, 94, 8582 (synth)
(+)-form Stothers, J.B. et al, Can. J. Chern., 1973, 51, 2893 (cmr)
Prisms (EtOH) with faint odour. Sol. hot EtOH, CHCl 3,
C6H 6, ligroin; insol. Hp. Mp 66-67° (54-56°). [a:ln
+ 112° (EtOH).
Brunei, Y. eta/, Bull. Soc. Chim. Fr., 1964, 1895 (synth, ir, pmr,
uv)

150
3,6,6-Trimethylbicyclo[3.1.1]heptan-... - 7,7-Dimethyltricyclo[2.2.1.0 2•8] ••• Mo-00832 - Mo-00838

3,6,6-Trimethylbicyclo(3.1.1)heptan-2-one Mo-00832 2,6,6-Trimethylbicyclo(3.2.0)hept-2-en-7- Mo-00836

3, 7, 7- Trimethylnorpinan-2-one. M ethylnopinone one
Filifolone
[4613-37-0]

CIOHI60 M 152.236
(1R,3R,5S)-form [27040-88-6]
Oil. Bp 215-2W. [oc]i; + 59.7° (neat). C 10H 1P
& H
M 150.220
(+)-form
Absolute
configuration

Bessiere-Chretien, Y. et al, Bull. Soc. Chirn. Fr., 1970, 3103 (synth) (+)-form
Hirata, T. et al, J. Org. Chern., 1971, 36, 412 (struct)
Van der Gen, A. et al, Reel. Trav. Chirn. Pays-Bas (J. R. Neth.
Constit. of Zieria smithii. [01:]~4 +307°.
Chern. Soc.), 1971, 90, 1034 (synth) (-)-form
Hirata, T., Bull. Chern. Soc. Jpn., 1972, 45, 3458 (synth) Constit. of Artemisiafilifolia. [ocln -270°.
Chabudzinski, Z. et al, Pol. J. Chern. (Rocz. Chern.), 1973, 47, (±)-form
2305 (synth)
Oil. Bp 20 86-88°.
Semicarbazone: Cryst. (MeOH). Mp 199.6-201°.
2,5,5-Trimethylbicyclo(2.2.1)hept-2-ene Mo-00833
Bates, R.B. et al, J. Chern. Soc., Chern. Cornrnun., 1967, 1037
y-Fenchene (struct)
[497-33-6] Adams, D.R. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1741
(synth)
Hudlicky, T. et al, Tetrahedron Lett., 1980, 691 (synth)

CIOHI6 M 136.236
lsol. from Chenopodium botrys oils. Oil. Bp 145-147°.
Tricyclic
Castanet, Y. et al, Bull. Soc. Chirn. Fr., 1976, 1583.

2,7,7-Trimethylbicyclo(2.2.1)hept-2-ene Mo-00834
monoterpenoids
C-Fenchene
[514-14-7]
2,3-Dimethyltricyclo(2.2.1.0 2• 6)heptane Mo-00837
Cyclosantene

CIOHI6 M 136.236
Oil. Bp752 146.2-146.8°. [oc]i? -24.1°. C9H 14 M 122.210
Hiickel, W. et al, Justus Liebigs Ann. Chern., 1963, 664, 31. (±)-form
Castanet, Y. et al, Bull. Soc. Chirn. Fr., 1976, 1583.
Liq. with musty odour. Bp730 129-130°.
Beckmann, S. et al, Justus Liebigs Ann. Chern., 1951, 574, 76
3,6,6-Trimethylbicyclo(3.l.l)hept-2-ene Mo-00835 (synth)
[23978-81-6]
7,7-Dimethyltricyclo(2.2.1.0 2•6)heptane-1- Mo-00838
carboxaldehyde, 9CI
Tricyclal
CIOHI6 M 136.236 [512-59-4]
Liq. Bp746 155.5-156°. Formerly descr. under the name

~0
Orthodene as a nat. prod. This was P-pinene.
Burgstah1er, A.W. et at, Tetrahedron, 1968, 24, 2435.

CIOHI40 M 150.220
Mp 85-90°. Bp31 113-115°.
Semicarbazone: Needles (EtOH aq.). Mp 219-220° dec.
Lipp, P., Ber., 1920, 53, 778 (synth)

151
7 ,7-Dimethyltricyclo[2.2.1.02.8 ] ... - 4,7,7-Trimethyltricyclo[2.2.1.02.8 ] ... Mo-00839 - Mo-00843

7,7-Dimethyltricyclo(2.2.1.02•6)heptane-l- Mo-00839 Found in terpentine and other essential oils, e.g. Juniperus
carboxylic acid, 9CI communis, Ferula galbaniflua and Picea spp. Cryst.
Dehydrocamphenilic acid. Tricyc/enic acid (EtOH). Mp 67-68°. Bp 152-153°.

drH
[512-60-7] Lipp, P., Ber., 1920, S3, 779 (synth)
Komppa, G., Chem. Ber., 1929, 62, 1366 (synth)
Thomas, A.F. et a/, Helv. Chim. Acta, 1964, 47, 475 (ms)
Bardyshev, 1.1. eta/, CA, 1968, 70, 29076 (bib/)

3,3,4-Trimethyltricyclo(2.2.1.0 2•6)heptane Mo-00842

lsobornylene. /socyc/ene. P-Pericyc/ocamphane
C 1Jf140 2 M 166.219 [39546-15-1]
Plates (EtOH or C6 H 6). Mp 150-151°. Bp 262-264°, Bp 12
145°.
Me ester: [56694-97-4].
C 11H 160 2 M 180.246
Mp 45.SO. Bp 14 99°.
Chloride: C10H 16 M 136.236
C 10H 13Cl0 M 184.665 Cryst. Mp 117-118°. Bp 150-152°.
Mp 37.5-38.SO. Bp 15 116-117°. Bredt, J. et a/, J. Praia. Chem., 1917, 9S, 133 (synth)
Amide: Hirsjarvi, P. et a/, Suom. Kemistil. B, 1972, 4S, 379 (synth)
C 10H 15NO M 165.235
'Leaflets (C6H 6). Mp 117-118°. 4,7,7-Trimethyltricyclo(2.2.1.0 2•6)heptan-3- Mo-00843
Nitrile: one
C 1.,H13N M 147.219 lsocyc/enone. Pericyc/ocamphor
M p 65-70°. Bp 12 100-102°.
[875-99-0]
Lipp, P. eta/, Chem. Ber., 1939, 72, 2079 (synth)
Ranganathan, S. eta/, Tetrahedron Lett., 1968, 32, 99 (synth, ir,
nmr)

Teresantalol Mo-00840

dhH
2,3-Dimethyltricyc/o[2.2.1.0 2•6]heptane-3-methanol, 9CI
[29550-55-8]
C 10H 140 M 150.220
Cryst. (pet. ether). Mp 168-170°. Bp 205-207°.
Lippmaa, E. et a/, Org. Magn. Reson., 1973, S, 277 (cmr)
Brown, F.C. eta/, Synth. Commun., 1975, S, 477 (synth)

C 10H 160 M 152.236

Constit. of Indian sandalwood oil (Santa/urn album). Cryst.
(pet. ether/C 6H 6). Mp l15°. Bp9 95-98°. [a] 0 + 12.1°
(EtOH).
8-Aldehyde: [59300-39-9]. Teresantalal
C 1Jf140 M 15o.22o
Constit. of the oil of S. album.
8-Carboxylic acid: [562-66-3]. r~--Teresantalic acid
C 1oH 140 2 M 166.219
lsol. from S. album. Cryst. (EtOH). Mp 158°. Bp 20 157-
1580. [ex]~ -76.6° (C 6H 6).
Guha, P.C. et a/, J. Indian Chem. Soc., 1944, S9, 271 (iso/)
Demo1e, E. et a/, Helv. Chim. Acta, 1976, S9, 737 (isol)
Monti, S.A. eta/, J. Org. Chem., 1978, 43, 2282 (synth)

1,7,7-Trimethyltricyclo(2.2.1.02•6)heptane, Mo-00841
9CI
Tricyc/ene. Cyc/ene
[508-32-7]

M 136.236

152
Sesquiterpenoids

153
Agelasidine A - 5,10-Dihydroxy-2,6,10-trimethyl-... Sq-00001 - Sq-00007

Crocinervolide Sq-00004
[125204-36-6]
Simple farnesane
sesquiterpenoids ~
0
C 12H 180 3 M 210.272
Constit. of Calea crocinervosa. Oil. [1X]n +41.9° (c, 0.264 in
Agelasidine A Sq-00001 CHC13).
2-[[(1-Ethenyl-1 ,5,9-trimethyl-4,8- Ortega, A. et al, Phytochemistry, 1989, 28, 2735 (isol, pmr, cmr)
decadienyl)sulfony~ethyljguanidine, 9CI
[87853-53-0] 8,12-Dihydroxy-1 0-hydroxymethyl-2,6- Sq-00005
dimethyl-2,6,10-dodecatrienal
NH
r-NH~ 14 OH
15
CH20H
0 2 S_/ NH2
I I r~ r~l- cH2oH
~ OH~
12
C 18H 33N 30 2S M 355.544 Ct 5H 240 4 M 268.352
Isol. from the Okinawan sea sponge Age/as nakamurai and Farnesane numbering shown.
from a Pacific sponge A. sp. Shows antispasmodic and Tri-Ac: [126621-17-8].
antibacterial activity. Unstable yellow oil. C21 H 300 7 M 394.464
B,HCI: Cryst. + } H 20 (EtOAc). Mp 108-108.SO. [IX]~ Constit. of Arctotheca calendula.
+ 19.1° (c; 1 in MeOH). 9-Acetoxy, tri-Ac: [126621-18-9].
Capon, R.J. eta/, J. Am. Chern. Soc., 1984, 106, 1819 (isol, uv, ir, C23 H 3P 9 M 452.500
pmr, cmr, ms, struct) Constit. of A. calendula.
Nakamura, H. eta/, J. Org. Chern., 1985, 50, 2494 (isol, uv, ir,
pmr, cmr, struct) 5-Deoxy, 15-Ac, 14-acetoxy: [126621-27-0]. 6,10-
Bis(acetoxymethyl)-12-hydroxy-2-methyl-2,6,10-
dodecatrienal, 9CI
Bejarol Sq-00002 C 19H 280 6 M 352.427
Constit. of Arctotis auriculata.

},_,~
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 195 (iso/, pmr, cmr)

(3RW<,9R';fo'm
2,10-Dihydroxy-2,6,10-trimethyl-3,6,11- Sq-00006
C 15H 240 2 M 236.353 dodecatrien-5-one
3 Diastereoisomers known. [86584-07 -8]
(3R*,5R* ,9R*)-form [88861-88-5]
IX-trans-Bejarol HO~n ~- L - VOH /.
Constit. of Santo/ina oblongifolia. Oil. [1X]n -15.7° (c, /vy~~-......./
0.9 in CHC1 3). 0
(JR* ,5S* ,9S*)-form [88904-15-8]
P-trans-Bejarol C15H 240 3 M 252.353
From S. oblongifolia. Oil. [1X]n -9.SO (c, l.l in CHC1 3). Constit. of Artemisia douglasiana. Gum. [1X]i;' -27.1° (c,
0.21 in CHC1 3).
(3R*,5R*,9S*)-form [88504-16-9]
cis-Bejarol 11-Hydroperoxide: [8657 5-91-9]. 2-Hydroperoxy-10-
hydroxy-2,6,10-trimethyl-3,6,11-dodecatrien-5-one
From S. oblongifolia. Oil. [1X]n -41.4° (c, 0.76 in
CHC1 3). C15H 240 4 M 268.352
Constit. of A. douglasiana. Gum. [1X]~4 -20.9° (c, 0.48 in
de Pascual-Teresa, J. et al, Phytochemistry, 1983, 22, 2235 (isol) CHC1 3).
de Pascual-Teresa, J. eta/, Phytochemistry, 1984, 23, 2064 (struct)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2693.

Caulerpenyne Sq-00003
5,10-Dihydroxy-2,6,1 0-trimethyl-2,6,11- Sq-00007
[70000-22-5]
dodecatrien-4-one, 9CI
AcO Vernopolyanthone

~
[79081-59-7]

C21 H 260 6 M 374.433

OAc

Constit. of Caulerpa prolifera. Cryst. Mp 57-58°. [1X]i?

~ OH
+7.1° (c, 1 in EtOH). M 252.353
Amico, V. eta/, Tetrahedron Lett., 1978, 3593.

155
8,10-Dihydroxy-2,6,10-trimethyl-... - 4,8-Dimethyl-1,3,7-nonatriene Sq-00008 - Sq-00015

Constit. of Vernonia polyanthes. Oil. [1X]i;' +27.5° (c, 0.6 in 2,6-Dimethyl-1 0-methylene-6,11- Sq-00012
CHC1 3). dodecadiene-2,3-diol, 9CI
Bohlmann, F. et al, Phytochemistry, 1981, 20, 473. [88048-16-2]

8,10-Dihydroxy-2,6,10-trimethyl-2,6,11- Sq-00008
dodecanien-~one, 9CI
5-Hydroxy-9-oxonero/ido/
OH
C15H 260 2 M 238.369
Oil. [IX]~ + 15.4° (c, 3.31 in CHC1 3).
10-0-[/J-v-G/ucopyranosy/(1-+4)-P-v-g/ucopyranoside]:
C 15Hu03 M 252.353 C 27 H.41;0 12 M 562.653
(3S*,5R*)-form [94161-19-0] Constit. of Trillium tschonoskii. Oil. [IX]~ -21.9° (c, 1.00
Cons tit. of Ratibida columnifera. Oil. [1X]n - 39° in MeOH).
(CHC1 3). Nakano, K. et al, Phytochemistry, 1983, 22, 1249.
5-Ac: 5-Acetoxy-9-oxonero/ido/
C 17H 21;04 M 294.390 2,6-Dimethyl-1 0-methylene-2,6,11- Sq-00013
Constit. of Anthemis austriaca. Oil. Bp0_07 110°. [1X]i;'
-33.6° (c, 1.3 in CHC1 3).
dodecanienal
Bohlmann, F. et al, Chern. Ber., 1974, 107, 1074.
Herz, W. et al, J. Org. Chern., 1985, 50, 610.
OH
3,7-Dimethyl-2,6-decadiene-1,1 0-diol, 9CI Sq-00009 C 15H 120 M 218.338
(2E,6E)-form [3779-62-2] P-Sinensal

HOH2C~CH20H
Constit. of orange oil (Citrus sinensis). Flavour
ingredient. Oil. Bp0 _05 92-95°. A.max 227 nm (e 31 000).
2,4-Dinitropheny/hydrazone: Cryst. Mp 87-88°.
C 12H 120 2 M 198.305
Stevens, K.L. et a/, J. Org. Chern., 1965, 30, 1690 (isol. struct)
(E,E)-form [24048-35-9] Baumann, M. et al, Justus Liebigs Ann. Chern., 1976, 1626 (synth)
Pheromonal component of Monarch and Queen Vig, O.P. et a/, Indian J. Chern., Sect. B, 1979, 18, 33 (synth)
butterflies. Sato, K. et al, J. Chern. Soc., Perkin Trans. 1, 1981, 2411 (synth)
Mandai, T. et al, J. Org. Chern., 1983, 48, 5183 (synth)
Meinwald, J. eta/, Science (Washington, D.C.), 1969, 164, 1174
Fujisawa, T. et al, Tetrahedron Lett., 1984, 25, 3213 (synth)
(isol, ir, ms, pmr)
Miles, D.H. et al, Tetrahedron Lett., 1972, 3019 (synth)
Katzenellenbogen, J.A. et al, J. Org. Chern., 1974, 39, 3315 (synth, 7,11-Dimethyl-3-methylene-1,6,10- Sq-00014
pmr, ms) dodecaniene
P-Farnesene
4,8-Dimethyl-4,8-decadienolide Sq-00010

~0
~0
(E)-form
CisHu M 204.355
C 12H 180 2 M 194.273 (E)-form [18794-84-8]
(E,E)-form [86578-98-5] Constit. of hop, camomile and other essential oils.
Pheromone of the Rusty Grain beetle, Cryptolestes Alarm pheromone of aphids. Oil. Bp9 121-122°.
ferrugineus. (Z)-form [28973-97-9]
Oehlschlager, A.C. eta/, J. Org. Chern., 1983, 48, 5009 (synth, Oil.
pmr, cmr, ms) Naves, Y.R., Helv. Chim. Acta, 1966, 49, 1029 (uv, ir, pmr)
Brieger, G. et al, J. Org. Chern., 1969, 34, 3789 (synth)
Anet, E.F.L.J., Aust. J. Chern., 1970, 23, 2101 (synth)
3,7-Dimethyl-8,11-dioxo-2,6,9- Sq-00011 Tanaka, S. et al, J. Am. Chern. Soc., 1975, 97, 3252 (synth)
dodecanienal, 9CI Vig, O.P. et al, J. Indian Chern. Soc., 1975, 13, 1244 (synth)
Mandai, T. et al, J. Org. Chern., 1983, 48, 2601 (isol)

~CHO (All-E):form 4,8-Dimethyl-1,3,7-nonatriene Sq-00015

0
C 14H 180 3 M 234.294
(all-E)-form [36518-ll-3] Gyrinal. Gyrinidal
~
Constit. of defence secretion of Girindiae beetles. C 11 H 18 M 150.263
AriJ..,~S biosynthetically by degradation of nerolidol.
(2Z,6E,9E)-form [55806-39-8] lsogyrinidal
Constit. of defence secretion of Gyrindiae beetles. (E)-form
Constit. of essential oil of Elettaria cardamomum, Rosa
Schildknecht, H. eta/, Justus Liebigs Ann. Chern., 1972, 756, 155 spp., Magnolia li/iflora. Oil.
(struct, uv, ir, pmr, ms)
Meinwald, J. et al, Tetrahedron Lett., 1973, 281 (uv, pmr, ir, ms) [21214-62-0]

156
4-(4,8-Dimethyl-2,4,6-nonatrienyl}-... - 3-Hydroxymethyl-7,11-dimethyl-... Sq-00016 - Sq-00023

Pattenden, G. eta/, J. Chern. Soc. C, 1968, 1984 (synth) Flexilin Sq-00020

Maurer, B. et a/, Tetrahedron Lett., 1986, 27, 2111 (struct, synth)
Boland, W. eta/, Helv. Chim. Acta, 1989, 72, 247 (biosynth, bib/) [69625-33-8]

4-(4,8-Dimethyl-2,4,6-nonatrienyl)-2,6- Sq-00016
dioxabicyclo(3.1.0]hexan-3-one
[126030-33-9]
0 OAc
C 1,H:za04 M 320.428
Constit. of Caulerpa fie xi/is. Bp 0 _1 100°.
0 4-Acetoxy: [93888-65-4]. 4-A.cetoxyjiexilin
CtsH100 3 M 248.321 C 21 H 300 6 M 378.464
Constit. of a Euryspongia sp. Cryst. (Et20jpet ether). Mp Metab. of algae Penicillus capitatus and Udotea
50-51°. [1X]n -7° (c, 0.62 in CHC1 3). cyathiformis. Antibacterial and ichthyotoxin. Oil. [IX]~
+ 18.0° (c, 1.2 in CHC13).
Van Altena, I.A. et a/, Aust. J. Chern., 1989, 42, 2181 (isol, pmr,
cmr) Blackman, A.J. eta/, Tetrahedron Lett., 1978, 3063 (isol)
Paul, V.J. et al, Tetrahedron, 1984, 40, 2913 (isol, deriv)

5-(4,8-Dimethyl-2,4,6-nonatrienyl)-2,6- Sq-00017
dioxabicyclo(3.1.0]hexan-3-one 12-Hydroxy-6,10-dimethyl-6,10- Sq-00021
dodecadien-2-one
[126030-34-0] Oxocrinol
[60346-03-4]
0 0

C 15H 100 3
#
M 248.321
# #
~~CH2 0H
Constit. of a Euryspongia sp. Unstable cryst. [1X]n -41° Ct4H 240 2 M 224.342
(c,0.22 in CHC1 3). Constit. of Cystoseira crinita. Oil.
Van Altena, I.A. eta/, Aust. J. Chern., 1989, 42, 2181 (isol, pmr, Fattorusso, E. et al, Tetrahedron Lett., 1976, 937 (struct)
cmr) Kato, T. eta/, Chern. Lett., 1977, 8, IOOg (synth)

7-Ethyl-3,11-dimethyl-1,3,6,10- Sq-00018 5-(4-Hydroxy-2-methyl-2-butenyl)-3-(4-

dodecatetraene methyl-5-oxo-3-pentenyl)-2(4H)-
furanone Sq-00022

~
[126621-19-0]
12
OHC A A 1
C 16H 16 M 218.381
Constit. of the Dufour gland of the ant Myrmica rubra.
~CH2 0H
Oil.
0
[73690-00-3, 96890-21-0]
CtsH1004 M 264.321
Attygalle, A.B. eta/, J. Chern. Soc., Perkin Trans. I, 1982, 949 Famesane numbering shown. Constit. of A.rctotis
(isol, struct)
arctotoides.
A.c: [126621-20-3].
7-Ethyl-3,11-dimethyl-1,3,6,10- Sq-00019 C 17H 2z05 M 306.358
tridecatetraene Constit. of A. arctotoides.
[70234-77-4] 12-A/coho/, Di-A.c: [126621-21-4].
CI,Hl606 M 350.411

~
Cons tit. of A. arctotoides.
Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 195 (isol, pmr, cmr)

C 17H:za M 232.408
Constit. of the Dufour glands of the ant Myrmica rubra. 3-Hydroxymethyl-7,11-dimethyl-2,6,10- Sq-00023
Oil. dodecatriene-1,5-diol
Attygalle, A.B. eta/, J. Chern. Soc., Perkin Trans. I, 1982, 949 15
(isol, struct) OH CH20H
~CH2 0H
CtsHl603 M 254.369
1,15-Di-A.c: [87441-68-7].
Ct,H300 5 M 338.443
Constit. of Calea hispida. Gum. [1X]n -4° (c, 0.1 in
CHC13).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2899.

157
6-Hydroxymethyl-2,10-dimethyl-... - 6-Methyl-5-hepten-2-one Sq-00024 - Sq-00032

6-Hydroxymethyl-2,10-dimethyl-2,6,10- Sq-00024 v-Ionone Sq-00029

dodecatriene-1,12-diol 6,10-Dimethyl-3,5,9-undecatrien-2-one. Citrylideneacetone.
[126621-32-7] Pseudoionone
[141-10-6]
CH20H

HOCH2
~CH2 0H ~
C 15Hu,03 M 254.369 C13H 200 M 192.300
Constit. of Arctotis venusta. Constit. of tobacco. Shows juvenile hormone activity. Oil.
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 195 (iso/, pmr, cmr) Bp23 167-168°.
2,4-Dinitrophenylhydrazone: Cryst. Mp 146-147°.
3-Hydroxymethyl-7 ,11-dimethyl-2,6,11- Sq-00025 Org. Synth., Col/. Vol., 3, 1955, 747.
Zakharova, N.l. eta/, Zh. Org. Khim., 1973, 9, 1850 (synth)
dodecatriene-1,5,10-triol Englert, G. eta/, Helv. Chim. Acta, 1975, 58, 2367 (cmr)
15

~ - L 1H I~2~H
/~~~~~CH2 0H
Kobusimin A Sq-00030
7- Hydroperoxy-10-hydroxy-2,1 0-dimethyl-6-methylene-2,11-
dodecatrien-4-one, 9CI
OH [82900-97-8]
C 15H 260 4 M 270.368
1,15-Di-Ac: [87450-31-5]. 0 I
OH
C19H:ll,06 M 354.442
Constit. of Calea hispida. Gum. [1X] 0 -7° (c, 0.1 in
CHC1 3). OOH
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2899. C,5H 240 4 M 268.352
Constit. of Magnolia kobus. Oil. [1X] 0 +9.7° (c, 0.35 in
10-Hydroxy-2,6,10-trimethyl-2,5,7,11- Sq-00026 CC14).
dodecatetraen-4-one Iida, T. eta/, Phytochemistry, 1982, 21, 673.
[53098-73-0]
Kobusimin B Sq-00031
0 6-Hydroperoxy-10-hydroxy-2,6,10-trimethyl-2,7,11-
~ # # dodecatrien-4-one, 9CI
[82900-96-7]
C 15H 220 2 M 234.338
Constit. of Anthemis austriaca. Oil. Bp0_06 100° (bath). [1X]~4
-7.7° (c, 0.6 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 3362.
~
C,sH 240 4 M 268.352
Constit. of Magnolia kobus. Oil.
10-Hydroxy-2,6,1 0-trimethyl-2,6,11- Sq-00027
lida, T. eta/, Phytochemistry, 1982, 21, 673.
dodecatrienal
12-0xonerolidol
[7 5628-03-4] 6-Methyl-5-hepten-2-one, 9CI Sq-00032

OH H 3CCOCH 2CH 2CH=C(CH 3)2

OHC~ C8 H 140 M 126.198

Present in Ceylon citronella oil, lemon-grass oil and
C 15H 240 2 M 236.353 palmarosa oil. Produced by Endoconidiaphora
Constit. of Arctotis aspera. coerulescens and other spp. lsol. from the Australian
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 587 (synth, ir, ms) meat ant, lridomyrmex purpureus. Intermed. in the
Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 195 (isol, pmr, cmr) manuf. of terpene alcohols. Insecticidal agent. Bp 172-
1740 (161-162°), Bp 10 58.SO.
10-Hydroxy-2,6,10-trimethyl-2,6,11- Sq-00028 Oxime: [22418-73-1].
dodecatrien-5-one C8H 15NO M 141.213
8-0xonerolidol Bpi2 99o.
[86575-90-8] Semicarbazone: [16769-68-9].
Mp 135° approx.
2,4-Dinitrophenylhydrazone: [6147-43-9].
Mp 78°.
Birkinshaw, J.H. eta/, Biochem. J., 1950, 47, 55 (isol)
0 Mousseron, M. eta/, Bull. Soc. Chim. Fr., 1963, 376 (synth)
C,sH240z M 236.353 Saucy, G. eta/, Helv. Chim. Acta, 1967, SO, 2091 (synth)
Constit. of Artemisia douglasiana. Gum. Sato, K. et al, J. Org. Chern., 1970, 35, 565 (synth)
Boccara, N. eta/, Bull. Soc. Chim. Fr., 1972, 1448 (synth)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2693. Ishihara, T. eta/, Agric. Bioi. Chern., 1974, 38, 439 (synth, bibl)

158
Obtusenol - 2,6,10-Trimethyldodecane Sq-00033 - Sq-00040

Dennison, N.R. et al, Aust. J. Chern., 1975, 28, 1339 (synth) C15H 280 2 M 240.385
Savoia, D. et al, J. Org. Chern., 1978, 43, 2907 (synth) Constit. of caparrapi oil (from Ocotea caparrapz). Viscous
Kim, J.H. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 63 (biosynth) oil. [aJn + 8° (CHC1 3).
Del Castillo, J.B. eta/, Tetrahedron Lett., 1966, 3731 (isol, struct)
Obtusenol Sq-00033 Vig, O.P. et al, Indian J. Chern., 1975, 13, 1003 (synth)
[75479-00-4) Weyerstahl, P. et al, Chern. Ber., 1977, 108, 377 (synth)

BrYl ,pH 2,6,10-Trimethyl-6,11-dodecadiene-2,3,1 0- Sq-00038

trioI
--t--o~
Br I .PH
HOJ2
C15H 26Br20 2 M 398.177 ~ I
Constit. of Laurencia obtusa. Oil. [a]J: -50.2° (c, l. 7 in OH
CHC1 3), C15H 280 3 M 256.384
lmre, S. eta/, Phytochemistry, 1981, 20, 833. (3S,JOS)-form
Gonzalez, A.G. et al, Tetrahedron Lett., 1981, 22, 5071 (synth)
Oil. [a]~ -13.4° (c, 1.08 in MeOH).
3-0-P-n-Glucopyranoside: [108906-50-9]. Icariside C 1
Rbipocephalin Sq-00034 C21 H 380 8 M 418.526
[71135-78-9] Constit. of Epimedium grandiflorum var. thunbergianum.
Amorph. powder. [a]~ -22.5° (c, 1.00 in MeOH).
2-0-P-n-gtucopyranoside: [108906-49-6). Icariside C2
C21 H 380 8 M 418.526
,:::7 OAc Constit. of E. grandiflorum var. thunbergianum. Amorph.
OAc powder. [a]~ -19.3° (c, 0.96 in MeOH).
C21 H 280 6 M 376.449 10-0-P-n-Glucopyranoside: [108906-48-5]. lcariside C3
Constit. of Rhipocephalus phoenix. Fish antifeedant. Oil. C21 H380 8 M 418.526
[1X]n+ oo. Constit. of E. grandiflorum var. thunbergianum. Amorph.
powder. [a]~ ~34.7° (c, 0.88 in MeOH).
Sun, H.H. et al, Tetrahedron Lett., 1979, 685.
(3R,JOS)-form
Oil. [a]~ +44.5° (c, 0.64 in MeOH).
Rhipocephenal Sq-00035
3-0-P-n-Glucopyranoside: [109009-54-3]. Icariside C4
[71135-77-8] C21 H 380 8 M 418.526
Constit. of Epimedium grandiflorum var. thunbergianum.
HO~I I THO Amorph. powder. [a)~ +3.4° (c, 0.87 in MeOH).
~CHO Miyase, T. et al, Chern. Pharm. Bull., 1987, 35, 1109.
C 15H 200 3 M 248.321
Constit. of Rhipocephalus phoenix. Fish antifeedant. Oil. 3,7,11-Trimethyl-6,10-dodecadien-1-ol Sq-00039
Sun, H.H. et al, Tetrahedron Lett., 1979, 685. [37519-97-4]

3,4,7,11-Tetramethyl-1,3,6,10- Sq-00036 ~CH2 0H

dodectetraene
Homofarnesene C15H 280 M 224.386
(3S,6E)-form [51411-24-6]
2,3-Dihydrofarnesol. Terrestrol
Occurs in the heads of male bumble bees (Bombus
terrestris). Oil. [a)~ -4.4° (c, 20 in CHC1 3).
Stiillberg-Stenhagen, S., Acta Chern. Scand., 1970, 24, 358 (abs
config)
(3Z,6E)-form Ahlquist, L. et al, Acta Chern. Scand., 1971, 25, 1685 (synth)
C16H 26 M 218.381
(3Z,6E)-form [79383-34-9) 2,6, 10-Trimethyldodecane Sq-00040
Trail pheromone of Solenopsis invicta. Farnesane
(3Z,6Z)-form [79383-33-8] [3891-98-3]
Trail pheromone of S. invicta.
van der Meer, R.K. et al, Tetrahedron Lett., 1981, 1651 (isol,
struct)
Alvarez, F.M. eta/, Tetrahedron, 1987, 43, 2897 (synth) C15H 32 M 212.418
Constit. of oil shales and the resin of Dipterocarpus spp.
3,7,11-Trimethyl-1,1 0-dodecadiene-3,7-diol Sq-00037 Oil. Bp 15 126.5°.
Caparrapidiol Sorm, F. et al, Collect. Czech. Chern. Commun., 1949, 14, 699
[10208-67-0] (synth)
Bisset, N.G. et al, Phytochemistry, 1966, 5, 865 (isol)

~
159
3,7,11-Trimethyldodecanoic acid- 3,7,11-Trimethyl-1,4,6,10-... Sq-00041 - Sq-00048

3,7,11-Trimethyldodecanoic acid Sq-00041 3,7,11-Trimethyl-2,4,6,1 0-dodecatetraene Sq-00045

Allofarnesene
~COOH
C 1 ~H 300 3 M 258.400 ~ 6 4 2
(3R,7R)-form [13955-73-2]
Constit. of Californian petroleum. (2E,4E,6E)-form
p-Phthalimidophenacyl ester: Cryst. (Me2CO). Mp 99-100°. C 1 ~H 14 M 204.355
Isol. (without stereochemical distinction) from oil of
Cason, J. et al, Tetrahedron, 1965, 21, 471 (isol)
Cymbopogon nardus, Canaga odorata and others. Bp4 .4
Valentine, D. et al, J. Org. Chern., 1976, 41, 62 (struct)
Chan, K.-K. et al, J. Org. Chern., 1976, 41, 3497 (synth) 121-122°.
(1E,4E,6E)-form [6980-88-7]
Constit. of Perilla frutscens. Oil.
3,7,11-Trimethyl-1,3,5,8,10- Sq-00042
(1Z,4E,6E)-form [26560-15-6]
dodecapentaene
Constit. of P. frutscens. Oil.
Naves, Y.R., Helv. Chim. Acta, 1966, 49, 1029 (synth, uv, ir, pmr)
~ Brieger, G. et al, J. Org. Chern., 1969, 34, 3789 (synth)
Sakai, T. et al, Bull. Chern. Soc. Jpn., 1969, 42, 3615 (isol)
Miyaura, N. et al, Bull. Chern. Soc. Jpn., 1982, SS, 2221 (synth)
C 1 ~H 22 M 202.339
(3E,5E,8E)-form [73368-17-9]
Constit. of Plexaurel/a grisea. Oil. [a]~ +55.1° (c, 0.45 2,6,1 0-Trimethyl-2,7,9,11-dodecatetraene- Sq-00046
in CHC13). 4,6-diol
(3E,5E,BZ}-form [73368-16-8]
Constit. of P. grisea. Oil. [a]~ + 50.2° (c, 0.33 in
CHC1 3). # #
Gopichand, Y. et al, J. Org. Chern., 1980, 45, 2523.
(3E,5E)-form
2,6,10-Trimethyl-2,6,9,11-dodecatetraenal Sq-00043 C 1 ~H 14 0 1 M 236.353
rx.-Sinensaft. P-Sinensalt(obsol.) (3E,5E)-form
[17909-77-2] 4-Angeloyl: (E,E)-Semistriatin
C10H 300 3 M 318.455
Constit. of Ageratum fastigiatum.
OH 4-Ange/oy/, 6-Me ether:
CztH3z03 M 332.482
C 1 ~H 22 0 M 218.338 Constit. of Bejaranoa semistriata.
The prefixes a and p originally applied to indicate order of
discovery, were interchanged to correspond to P- and a- (3Z,5E)-form
Famesene. Constit. of orange oil. Oil. A.max 231 nm (log 4-Angeloyl: (E,Z)-Semistriatin
e 4.57). Rapidly polymerises on exp. to light and air. C10H 300 3 M 318.455
Flath, R.A. et al, Tetrahedron Lett., 1966, 295 (isol, struct) Constit. of A. fastigiatum. Oil.
Baumann, M. et al, Justus Liebigs Ann. Chern., 1976, 1626 (synth) 4-Ange/oy/, 6-Me ether: Constit. of B. semistriata.
[86948-51-8)
3,7,11-Trimethyl-1,3,6,1 0-dodecatetraene Sq-00044 Bohlmann, F. et al, Phytochemistry, 1981, 20, 1639; 1983, 22, 983.
rx.-Farnesene. Sesquicitronel/ene
[502-61-4] 3,7,11-Trimethyl-1,4,6,1 0-dodecatetraene- Sq-00047
3,8-diol

(3E,6E)-form
C 1 ~H 14 M 204.355 OH
(3E,6E)-form [21499-64-9]
C 1 ~H 14 0 1 M 236.353
Constit. of the natural coating of apples and pears and
other fruit. Insect attractant for codling moth larvae. 8-Ange/oy/: [53771-44-l].
Oil. C10H 300 3 M 318.455
Constit. of roots of Brickellia guatemaliensis.
(3Z,6E)-form [26560-14-5]
Constit. of the oil of Perilla frutscens. Oil. Bohlmann, F. et al, Tetrahedron Lett., 1969, 5109 (isol)
Bohlmann, F. et al, Chern. Ber., 1974, 107, 1773 (synth)
Brieger, G. et al, J. Org. Chern., 1969, 34, 3789 (synth)
Murray, K.E., Aust. J. Chern., 1969, 22, 197 (isol, synth)
Anet, E.F.L.J. et al, Aust. J. Chern., 1970, 23, 2101 (synth) 3,7,11-Trimethyl-1,4,6,10-dodecatetraene- Sq-00048
Vig, O.P. et al, J. Indian Chern. Soc., 1970, 47, 851 (synth) 3,9-diol
Sutherland, O.R.W. et al, J. Insect Physiol., 1973, 19, 723 (isol) 9-Hydroxy-4,5-dehydronero/ido/. 9-Hydroxybrickel/io/

160
3,7,11-Trimethyl-2,4,6,10-••• - 3,7,11-Trimethyl-1,6,10-.•• Sq-00049 - Sq-00056

C 15H:z..O:z M 236.353 2,6, 10-Trimethyl-2,6, 10-dodecatriene Sq-00052

9-Ange/oy/:
C:zoH300 3 M 318.455
Constit. of Brickellia diffusa and Carelia cistifolia. Oil. ~
Bp0 _1 140°. C 15H 16 M 206.370
10,11-Epoxide, 9-ange/oy/: [59806-18-7]. (2E,6E)-form [7681-88-1]
C:zoH300 4 M 334.455 Constit. of the oil of Santa/urn spicatum. Aphid alarm
Constit. of B. diffusa and B. veronicaefolia. Oil. Bp0 _1 pheromone. Oil.
130°. [IX]~ + 11.6° (c, 3.3 in CHC1 3).
Birch, A.J. et al, Aust. J. Chern., 1970, 23, 2337 (isol, struct)
10,11-Dihydro, 10,11-dihydroxy, 9,10-diange/oy/: Nishino, C. et a/, Tetrahedron, 1976, 32, 2875 (synth)
C:zsH380 6 M 434.572
Constit. of B. diffusa. Gum. [IX]~ -8.2° (c, 0.38 in
2,6,10-Trimethyl-2,6,11-dodecatriene-1,10- Sq-00053
CHC1 3).
diol
10,11-Dihydro, 10,11-dihydroxy, 9-ange/oy/, 10-tig/oy/:
C:zsH380 6 M 434.572
Constit. of B. diffusa. Gum.
10,11-Dihydro, 10,11-dihydroxy, 9,10-ditig/oy/:
C:zsH 380 6 M 434.572
(2E,6E)-form
Constit. of B. diffusa. Gum.
Bohlmann, F. et al, Chern. Ber., 1971, 104, 964; 1976, 109, 1436 C 15H 160 1 M 238.369
(isol) (2E,6E)-form [15628-02-3]12-Hydroxynerolidol
Bohlmann, F. et al, Phytochemistry, 1982, 21, 691 (isol) Constit. of Ursinia a/pina. Oil.
(2Z,6E)-form [15628-01-2]13-Hydroxynerolidol
3,7,11-Trimethyl-2,4,6,1 0-dodecatetraene- Sq-00049 Constit. of U. anethoides. Oil.
1,9-diol 1-Ange/oy/: [75628-00-1].
C:zoH 320 3 M 320.471
Constit. of U. anethoides. Oil.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 587.

C 15H 140 1 M 236.353 2,6,1 0-Trimethyl-3,6,11-dodecatriene-2,10- Sq-00054

9,10-Epoxide,8-angeloy/: [83161-55-1]. 9-Ange/oy/oxy-10,11- diol
epoxydehydrofarneso/ [54877-98-4]
C:zoH300 4 M 334.455
Constit. of Stomanthes africanus. Gum.
HO,I I \PH
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1155. ~
C 15H 160 1 M 238.369
3,7,11-Trimethyl-1,4,6,10-dodecatetraen-3- Sq-00050 Constit. of Geigeria ornativa and Solanum me/ongena. Oil.
ol [IX]~ + J40 (c, 1. 0 in CC14).
4,5-Didehydronero/ido/. 4,5-Dehydronero/ido/ Stoessl, A. et al, Can. J. Chern., 1975, 53, 3351 (isol, uv, ms, pmr)
[59121-99-2] Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr)

I I \pH 3,7,11-Trimethyl-1,5,10-dodecatriene-3,7- Sq-00055

~ diol
C 15H 140 M 220.354 [125289-86-3]
Constit. of Brickellia laciniata. Oil.

~
Bohlmann, F. et al, Phytochemistry, 1978, 17, 763.

3,7,11-Trimethyl-1,6,9,11-dodecatetraen-3- Sq-00051 C 15H 160 1 M 238.369

ol Constit. of Geigeria ornativa. Oil. [1X]~4 + 18° (c, 0.84 in
Fokienol CHC1 3).
[33440-00-5] Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (iso/, pmr)

OH
3,7,11-Trimethyl-1,6,10-dodecatriene-3,5- Sq-00056
# diol
C 15H 140 M 220.354 5-Hydroxynerolidol
Constit. of Fokienia hodgkinsii. Oil. Bp0 _07 102°. [80453-51-6]
Vig, O.P. et al, Indian J. Chern., Sect. B, 1976, 14, 926.

C 15H 160 2 M 238.369

Constit. of Calea teucrifolia. Oil.
5-Ac:

161
3,7,11-Trimethyl-1,6,10-... - 3,7,11-Trimethyl-1,6,10-dodecatrien-... Sq-00057 - Sq-00063

C 17H 280 3 M 280.406 Constit. of Tanacetum aucherianum. Oil. [oc]~~ -11.8° (c,
Constit. of C. teucrifolia. Oil. 3.2 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1643. Bohlmann, F. eta/, Chern. Ber., 1974, 104, 1074.

3,7,11-Trimethyl-1,6,10-dodecatriene-3,9- Sq-00057 3,7,11-Trimethyl-1,6,10-dodecatriene- Sq-00061

clioI 3,5,9-triol
9-Hydroxynero/ido/ 5,9-Dihydroxynerolidol

"""' #
C 15H 260 2 M 238.369 Ct5Hu03 M 254.369
9-Ac: 9-Acetoxynerolido/ Constit. of Geigeria aspera. Gum. [ocln + 11° (c, 0.11 in
C17H:11P 3 M 280.406 CHC1 3). Stereochem. of this isolate not detd.
Constit. of Dolich/asium /agascae and Phrodus bridgesii. (3R*,5S",6E,9S")-form [101629-23-6]
Oil. [ocJn +13.1° (c, 1.99 in EtOH). Constit. of Santo/ina oblongifolia. Oil. [ocln + 17.5° (c,
Gambaro, V. et a/, Phytochemistry, 1986, 25, 739 (isol) 1.03 in CHC1 3).
Zdero, C. eta/, Phytochemistry, 1986, 25, 2873 (isol) 9-Ac: [101629-24-7]. 9-Acetoxy-5-hydroxynero/ido/
C 17H 280 4 M 296.406
2,6,1 0-Trimethyl-2,6,10-dodecatriene- Sq-00058 From S. oblongifo/ia. Oil. [ocln + 18.9° (c, 1 in CHC1 3).
1,5,8,12-tetrol 5,9-Di-Ac: [101559-93-7]. 5,9-Diacetoxynero/idol
C19H300 5 M 338.443
From S. oblongifolia. Oil. [oc]n + 11.3° (c, 1.2 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679 (1.wl)
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 185 (isol)
OH
C 15H 260 4 M 270.368 3,7,11-Trimethyl-2,6,1 0-dodecatrienoic Sq-00062
(2E,6E,JOE)-form acid
5,8,12- Trihydroxyfarnesol Farnesenic acid. Farnesic acid. Farnesylic acid
Constit. of Cousinia adenostica. Oil. [7548-13-2]
l-Ac: 12-Acetoxy-5,8-dihydroxyfarnesol
C 17H 280 5 M 312.405
From C. adenostica. Oil.
~COOH
Rustaiyan, A. eta/, Phytochemistry, 1987, 26, 2635. C 15H 240 2 M 236.353
All isomers (E,E; E,Z; Z,E; and Z,Z) are known. Oil. Bp 16
202-206°.
2,6,10-Trimethyl-2,6,11-dodecatriene- Sq-00059
Me ester: [10485-70-8].
1,4,10-triol
Ct6H2602 M 250.380
9,13-Dihydroxynero/ido/
Juvenile hormone. Oil. Bp 10 177-185°.
HOH2 C OH OH 2,3-Dihydroxypropy/ ester:
C 18H 300 4 M 310.433
"""' """' # Constit. of Archidoris odhneri. Oil.
C 15H 260 3 M 254.369 2-Acetoxy-3-hydroxypropy/ ester:
4-Ac: 9-Acetoxy-13-hydroxynero/ido/ C 20 H 320 5 M 352.470
C 17H 280 4 M 296.406 Constit. of A. odhneri. Oil.
Constit. of Dolichlasium /agascae. Oil. [a:J:: +26° (c, 2.6 3-Acetoxy-2-hydroxypropy/ ester:
in CHC1 3). C 20H 320 5 M 352.470
1,4-Di-Ac: 9,13-Diacetoxynerolidol Constit. of A. odhneri. Oil.
C19H34,05 M 338.443 Me ester, 10,11-epoxide: [22963-93-5]. Juvenile hormone III
From D. /agascae. Oil. C 16H 260 3 M 266.380
Zdero, C. eta/, Phytochemistry, 1986, 25, 2873. Oil. Bp0.08 125-126°.
Ohki, M. eta/, Agric. Bioi. Chern., 1974, 38, 175 (synth)
3,7,11-Trimethyl-1,6, 10-dodecatriene- Sq-00060 Crombie, L. eta/, J. Chern. Soc., Perkin Trans. I, 1975, 913 (cmr)
Katzenellenbogen, J.A. eta/, J. Am. Chem. Soc., 1976, 98, 4925
3,5,8-triol (synth)
5,8-Dihydroxynerolidol Pitzele, B.S. eta/, Tetrahedron, 1976, 32, 1347 (synth)
Anderson, R.J. et a/, Tetrahedron Lett., 1980, 797 (isol, deriv)
Kuhnz, W. et a/, Org. Magn. Reson., 1981, 16, 138 (cmr)
Mori, K. eta/, Tetrahedron, 1987, 43, 4097 (synth)

OH 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol Sq-00063
CtsHu03 M 254.369 Nero/idol. Peruviol. Melaleuco/
5,8-Di-Ac: [53098-75-2]. 5,8-Diacetoxynero/ido/ [7212-44-4]
C 1,H300 5 M 338.443
HO
~
162
3,7,11-Trimethyl-2,6,10-dodecatrien-... - Artedouglasiaoxide Sq-00064 - Sq-00068

C 15H 11,0 M 222.370 Xanthophanic acid Sq-00066

(S)-form [142-50-7] [26535-08-0]
Constit. of orange blossom, Peru balsam and from
many other sources. Perfumery ingredient (acetate is
also used in perfumery). Bp0.2 97°, Bp 276°. [1X] 0 + 15.SO.
H 3 COC~ICOOH
Phenylurethane: Cryst. Mp 37-38°. o o I
Vlad, P. et al, Collect. Czech. Chern. Commun., 1962, 27, 1726
(abs, config) ~ OH
Naves, Y.R. et al, Helv. Chim. Acta, 1963, 46, 2551 (uv)
Borges, J. et al, Tetrahedron Lett., 1966, 3731 (isoT) ·
COOH
Hill, H.C. et al, J. Chern. Soc. C, 1968, 93 (ms) C1 4H 120 8 M 308.244
Karrer, W. et al, Konstitution und Vorkommen der Organischen Di-Me ester: [16475-81-3].
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, C16H 160 8 M 336.298
no. 124 (occur)
Julia, M. et al, Bull. Soc. Chim. Fr., 1976, 513 (synth)
Red needles (C 6H 6). Mp 185°.
Di-Et ester: [16475-78-8].
C 18H 200 8 M 364.351
3,7,11-Trimethyl-2,6, 10-dodecatrien-1-ol Sq-00064 Yellow cryst. (EtOH). Mp 145°.
Farnesol
Ac:
[4602-84-0] C16H 1p 9 M 350.281
Cryst. (EtOH/CHC1 3). Mp 165-166°.
~CH2 0H (2E,6E)-form Crombie, L. et al, Tetrahedron Lett., 1964, 2313; J. Chern. Soc. C,
6 2 1967, 757, 763; J. Chern. Soc., Chern. Commun., 1968, 1015.
C 15H 260 M 222.370
Used in perfumery industry.
I> JR4979000.
(2E,6E)-form [106-28-5]
Widespread. The main famesol isomer, e.g. > 90% of
the famesol component of the oil of Hibiscus Furanoid farnesanes
abelmoschus. Bp 3 137°.
Aldehyde: [502-67 -0]. 3, 7,11- Trimethyl-2,6, 10-dodecatrienal.
Farnesal
C 15H 240 M 220.354 Ageraborniol Sq-00067
Shows juvenile hormone activity. Oil. Bp 14 172-174°. Tetrahydro- 2,5 ,5-trimethyl-!X-(4-methyl, 1,3 ,5-hexatrienyl)-2-
Aldehyde, semicarbazone: Mp 133-135°. furanethanol, 9CI
(2Z,6E)-form [3790-71-4] [67832-26-2]
Minor constit. of various essential oils including

~
petitgrain oil. Bp3 135°.
(2E,6Z)-form [3879-60-5]
Bp3 132°.
(2Z,6Z)-form [16106-95-9] C15H2401 M 236.353
Bp 3 127°. Constit. of Ageratina aschenbornia. Oil.
Bates, R.B. et al, J. Org. Chern., 1963, 28, 1086 (isol, struct) Bohlmann, F. et al, Phytochemistry, 1978, 17, 566 (isol)
Burrell, J.W.K. et al, J. Chern. Soc. C, 1966, 2144 (synth)
Corey, E.J. et al, J. Am. Chern. Soc., 1967, 89, 4245 (synth)
Hill, H.C. et al, J. Chern. Soc. C, 1968, 93 (ms) Artedouglasiaoxide Sq-00068
Richards, J.B. et al, Biochem. J., 1972, 128, 1345 (biosynth) [54783-60-7]
Jacob, G. et al, Phytochemistry, 1972, 11, 1683 (biosynth)
Nilles, G. et al, J. Agric. Food Chern., 1973, 21, 342 (synth)
Evans, R.H. et al, J. Chern. Soc., Chern. Commun., 1973, 465
(biosynth)
Crombie, L. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 913 (cmr)
Pauling, H. et al, Helv. Chim. Acta, 1976, 59, 1233 (synth)
Cardillo, C.R. et al, J. Chern. Soc., Chern. Commun., 1976, 190
(synth)
Yoshioka, T. et al, Phytochemistry, 1990, 29, 3469 (biosynth) C 15Hn03 M 250.337
In CA, the name and struct. are confused with
Artedouglasiolide. lsol. from Artemisia douglasiana, A.
3,7,11-Trimethyl-1-dodecene-3,7,11-triol Sq-00065 pal/ens and A. laciniata. Gum. Four stereoisomers,
Caparrapitriol Artedouglasiaoxides A, B, C and D were characterised
[I 0208-68-1] from A. laciniata.
[86575-88-4, 115403-96-8, 115403-97-9, 115403-98-0, 115403-99-1]
HO~ Thomas, A.F., Helv. Chim. Acta, 1974, 57, 2081 (synth)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2691 (isol, struct)
C15H 300 3 M 258.400 Weyerstahl, P. et al, Justus Liebigs Ann. Chern., 1988, 917 (isol,
struct)
Constit. of caparrapi oil (from Ocotea caparrapi). Cryst.
Mp 96-97°. [1X] 0 +3° (CHCI 3).
Del Castillo, J.B. et al, Tetrahedron Lett., 1966, 3731 (isol, struct)
Gottschalk, F.-J. et al, Chern. Ber., 1975, 108, 2799 (synth)

163
Athanagrandione - Deisopropylngaione Sq-00069 - Sq-00077

Athanagrandione Sq-00069 Cycloeumorphinone Sq-00073

1-(3-Furanyl)-4-hydroxy-4,8-dimethy/-1 ,6-nonanedione, 9Cl. [68776-16-9]
4-Hydroxymyoporone

~
[69926-93-8]
0

~
Absolute
0
configuration
C 15H 100 4 M 264.321
Constit. of Eumorphia spp. Oil. [cx]i;' -40° (c, 7.2 in
C 15H 120 4 M 266.336 CHC13).
Constit. of Anthanasia and Pentzia spp. Prod.by sweet
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1155.
potatoes infected by Fusarium so/ani. Oil.
Burka, L.T. et al, Tetrahedron Lett., 1974, 4017 (struct)
Burka, L.T. et al, Phytochemistry, 1977, 16, 2077 (biosynth) Davana ether Sq-00074
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1595 (isol, struct) [35470-57-6]
Oba, K. et al, Plant Cell Physiol., 1979, 20, 819 (biosynth)
Dimitriadis, E. et al, Phytochemistry, 1984, 23, 1325 (abs config)
Cole, R.J., Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 736.

C1sHn02 M 234.338
Athanasin Sq-00070 Constit. of Artemisia pal/ens. Bp0 _001 71-75°.
[36518-04-4] Thomas, A.F. et al, Helv. Chim. Acta, 1974, 57, 2076.

Davanafuran Sq-00075
2-Ethenyltetrahydro-2-methy/-5-[1-(5-methy/-2-
¥ ~ furanyl)ethyljfuran, 9Cl. Davanfuran
0
ClsH180 3 M 246.305
Constit. of Athanasia crithmifolia. Oil. [cx] 0 -29.6° (c, 2.3
in CHC13).
~CH,
Bohlmann, F. et al, Tetrahedron Lett., 1972, 1039. C14H100 2 M 220.311
Constit. of the oil of Artemisia pal/ens. Bp0 _08 42-50°. Mixt.
Brachymeral Sq-00071 of stereoisomers which have been individually
5-[5-(3-Furanyl)-2-(hydroxymethyl)-1-pentenylj-3- characterised.
furancarboxa/dehyde, 9Cl [56469-38-6, 56586-05-1, 56586-06-2, 56586-07-3]
[84607-36-3] Thomas, A.F. et al, Helv. Chim. Acta, 1974, 57, 2066 (isol, synth)
Ger. Pat., 2 452 083, (1975); CA, 83, 96998 (synth)

n
OHC
yH20H f\ Davanone Sq-00076
1!....0~0 2-(5-Etheny/tetrahydro-5-methy/-2-furanyl)-6-methy/-5-
hepten-3-one, 9Cl
CtsHt604 M 260.289
Constit. of Brachymeris montana. Gum. [30810-99-2]
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1989.
Absolute
Brachymerolide Sq-00072 configuration
[84607-37-4]
CtsH2402 M 236.353
Constit. of Artemisia pal/ens. [cx]i;l + 77.7° (neat).
Thomas, A.F. et al, Helv. Chim. Acta, 1974, 57, 2055 (isol, struct)
Bartlett, P.A. et al, Tetrahedron Lett., 1983, 24, 1365 (synth)

Deisopropylngaione Sq-00077
C 15H 160 5 M 276.288 1-[5-(3-Furanyl)tetrahydro-2-methy/-2-furanylj-2-propanone,
Constit. of Brachymeris montana. Gum. 9Cl
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1989. [39878-04-1]

0
0 /I::X~ 0 0

C 12H 160 3 M 208.257

Constit. of Myoporum deserti. Oil. [cx] 0 -15° (CHC1 3).

164
Dendrolasin - 5-(2,6-Dimethyl-1,5,7-octatrienyl)-... Sq-00078 - Sq-00082

2,4-Dinitropheny/hydrazone: Pale-yellow cryst. (EtOH). Mp 2-(2,6-Dimethyl-5,7-octadienyl)-4- Sq-00081

161-162°. methylfuran, 9CI
Hamilton, W.O. et al, Aust. J. Chern., 1973, 26, 375. {85679-59-0]

~
Dendrolasin Sq-00078
3-(4,8-Dimethy/-3, 7-nonadienyl}furan, 9CI
{23262-34-2] 0 6

C15Hn0 M 218.338
Constit. of Sinularia capillosa. Oil.
7,8-Didehydro: 2-(2,6-Dimetltyl-1.5,7-octatrieny/)-4-
metltylfuran
C 15Hn0 M 218.338 C 15H 200 M 216.322
Constit. of the ant Lasius (Dendrolasius) fuliginosus and Constit. of S. capil/osa. Oil.
the wood of Torreya nucifera. Also in sweet potato. Oil. 7,8-Didehydro, 4Z-isomer: {85679-63-6].
Bp 16 148-150°. n~ 1.4860. Constit. of S. capil/osa. Oil.
12-Hydroxy: see Neotorreyo/, Sq-00099 6,7-Didehydro: {85679-61-4]. 2-(2,6-Dimetltyl-2,5,7-
Bemadi, R. et al, Tetrahedron Lett., 1967, 3893 (isol) octatrienyl)-4-metltylfuran
Waldner, E.E. et al, Helv. Chim. Acta, 1969, 52, 15 (biosynth) Constit. of S. capil/osa.
Kobayashi, M. et al, J. Org. Chern., 1980, 45, 5225 (synth)
Lee, E. et al, Tetrahedron Lett., 1981, 22, 2671 (synth) 6,7-Didehydro, 4Z-isomer: {85679-62-5].
Araki, S. et al, Chern. Lett., 1982, 177 (synth, bib/) Constit. of S. capil/osa. Oil.
Janis, S.P., Tetrahedron Lett., 1982, 23, 3115 (synth) Bowden, B.F. et al, Aust. J. Chern., 1983, 36, 371.
Belardini, M. et al, J. Nat. Prod. (Lioydia), 1983, 46, 481 (synth,
bib/)
Mandai, T. et al, J. Org. Chern., 1983, 48, 5183 (synth) 5-(2,6-Dimethyl-1,5,7-octatrienyl)-3- Sq-00082
Kraus, G.A. et al, J. Org. Chern., 1983, 48, 5356 (synth) furancarboxylic acid

5-(1,5-Dimethyl-1,4-hexadienyl)-2-methyl- Sq-00079 HOOC

~
(3E, 7E)-form
2-vinyltetrahydrofuran
5-(1 ,5-Dimethy/-1 ,4-hexadieny/)-2-etheny/tetrahydro-2-
methy/furan, 9Cl. 7,10-Epoxy-2,6,10-trimethy/-2,5,11- C1 5H 180 3 M 246.305
dodecatriene
(3E,7E)-form
Constit. of Sinularia capillosa. Cryst. Mp 94.5-95.SO.
(3S,6R, 7E)-form Me ester: {85679-64-7].
C 16H 200 3 M 260.332
Constit. of S. capillosa. Oil.
C 15H 240 M 220.354
7,8-Dihydro: [85679-68-l]. 5-(2,6-Dimethy/-5,7-octadieny/)-
(3S,6R,7E)-form {72523-42-3] 3-furancarboxylic acid
Constit. of Osmanthus absolute. Oil. CtsH200 3 M 248.321
(3S,6S,7E)-form {72505-38-5] Constit. of S. capillosa. Oil.
Constit. of 0. absolute. Oil. 7,8-Dihydro, Me ester: [85679-65-8].
Kaiser, R. et al, Helv. Chim. Acta, 1979, 62, 1887. C 16Hn03 M 262.348
Constit. of S. capillosa. Oil.
3-(4,8-Dimethyl-2,4,6-nonatrienyl)furan Sq-00080 (3Z,7E)-form [64597-82-6)
Deltydrodendrolllsin Constit. of S. gonotodes. Cryst. (pet. ether). Mp 99-100°.
Me ester: [64597-84-8].

~
Constit. of S. capillosa. Oil.
7,8-Dihydro: [85679-69-2].
0 Constit. of S. capillosa. Oil.
C 15Hzc.0 M 216.322 7,8-Dihydro, Me ester: [85679-66-9).
(5E,7E,9E)-form {41060-02-0] Constit. of S. capillosa. Oil.
Constit. of Pleraplysilla spinifera. Oil. [105072-13-7]
(5Z,7E,9E)-form {117569-45-6] Coli, J.C. et al, Tetrahedron Lett., 1977, 1539 (isol)
C 15H 200 M 216.322 Bowden, B.F. et al, Aust. J. Chern., 1983, 36, 371 (isol)
Constit. of Ceratosoma brevicaudatum. Oil. Reg. no.
refers to (Z,Z,E) isomer, apparently incorrectly.
Cimino, G. et al, Tetrahedron, 1972, 28, 4761 (isol, struct)
Ksebati, M.B. et al, J. Nat. Prod. (Lioydia), 1988, 51, 857 (isol,
struct, prnr, crnr)

165
Eremoacetal- Furocaulerpin Sq-00083 - Sq-00090

Eremoacetal Sq-00083 Fercoperol Sq-00086

[73204-33-8] [106533-43-1)

HO\ J \ j 1\F
7'-o_ro~
C15H 260 4 M 270.368
Constit. of Ferula communis subsp. communis. Gum.
Miski, M. et al, J. Nat. Prod. (Lloydia), 1986, 49, 916

C 15H 100 3 M 248.321

Constit. of Eremophila rotundifolia. Cryst. (pet. ether). Mp Freelingnite Sq-00087
62-63°. [ex]~ + 10.3° (c, 30 in CHC1 3). [5677 5-49-6)
Dimitriadis, E. et al, Aust. J. Chern., 1979, 32, 2003.

2-(5-Ethenyltetrahydro-5-methyl-2-
furanyl)-6-hydroxy-6-methyl-4-hepten-3-
~~
0
one, 9CI Sq-00084 C 15H 180 3 M 246.305
2-Hydroxy-2,6,1 0-trimethyl-7, 10-oxido-3 ,11-dodecadien-5- Constit. of Eremophila freelingii. Oil. [ex]i,S + 11.5" (c, 1.3 in
one dioxan).
[73395-08-1] Knight, D.W. eta/, Tetrahedron Lett., 1975, 1115 (isol)
Jefford, C.W. et a/, Tetrahedron Lett., 1990, 31, 5741 (synth)
~OH Relative
configuration Freelingyne Sq-00088
/ 0 li o
[6617-37-4)
C 15H 240 3 M 252.353
Terpenoid numbering shown. Constit. of Artemisia herba. 0
Oil. Bp0 .05 140°. !ex]i,S +43.7o (c, 1.65 in CHC1 3).
11-Hydroperoxide: [88125-07-9]. Arteincultone
C 15H 240 4 M 268.352
0 0
o/~0
-CH3

Constit. of Artemisia inculta. Gum. Stereochem. not

detd. C1sH,p3 M 240.258
Constit. of Eremophila freelingii. Yellow cryst. (C6H 6). Mp
11-Deoxy: [54927-85-4]. /sodavanone. 2-(5-
164°.
Ethenyltetrahydro-5-methyl-2-furanyl)-6-methyl-4-hepten-
3-one, 9CI Massy-Westropp, R.A. et al, Tetrahedron Lett., 1966, 1939 (isol,
C 15H 240 2 M 236.353 uv, ir, pmr)
Begley, M.J. et al, J. Chern. Soc., Perkin Trans. 2, 1975, 1863
Isol. from A. pal/ens. Oil. [ex]~ +29.7° (c, 10 in CHC1 3). (stereochem)
Stereochem. not fully detd. Knight, D.W. et al, J. Chern. Soc., Perkin Trans. I, 1975, 641
Thomas, A.F. et al, Helv. Chim. Acta, 1974, 57, 2081 (synth)
(Isodavanone)
Gordon, M.M. et al, J. Nat. Prod. (Lloydia), 1981, 44, 432.
Khafagg, S.M. et a/, Phytochemistry, 1983, 22, 1821 (Arteincultone) 1-(3-Furanyl)-6,7-dihydroxy-4,8-dimethyl- Sq-00089
1-nonanone
2,6, 10-Farnesatriene-1,15; 13,9-diolide Sq-00085 [66472-04-6)
5-[5-(2,5-Dihydro-5-oxo-3-furanyl)-2-methyl-2-pentenylj-3- 0 OH
methyl-2(5H)-furanone, 9CI
[124193-04-0]
0
C 15H 240 4
~
M 268.352
Stress metab. from Ipomoea batatas. Cryst.
0 (Etpjpentane). Mp 70-71°. [ex]i,6 + 17° (c, 1.6 in EtOH).
C 15H 180 4 M 262.305 Burka, L.T., Phytochemistry, 1978, 17, 317.
Compd. not named by authors. Constit. of Eremophila
miniata. Amorph. solid. [exJn +21.5° (c, 3 in CHC1 3).
Furocaulerpin Sq-00090
Dastlik, K.A. et al, Phytochemistry, 1989, 28, 1425.

h/1
[80155-00-6]

0
M 272.343

166
6-Hydroxycyclonerolidol - 4-[4-Methyl-5-(4-methyl-2-furanyl}-... Sq-00091 - Sq-00097

Constit. of Caulerpa prolifera. Oil. [cx:Ji? -15° (c, 1 in Linifolone Sq-00094

CHC1 3).
de Napoli, L. et a/, Experientia, 1981, 37, 1132.
(E)-form
6-Hydroxycyclonerolidol Sq-00091
6-Ethenyltetrahydro-2,6-dimethyl-2-(4-methy/-3-pentenyl)- C 15H 200 3 M 248.321
2H-pyran-3-o/, 9CI
(E)-form [54963-33-6]
Constit. of Athanasia spp. Cryst. (Etpjpet. ether). Mp
48°.
10,11-Dihydro, 10-acetoxy: [54963-34-7]. 10-Acetoxy-10,11-
dihydrolinifo/one
C1sH260 2 M 238.369 C 17H 240 5 M 308.374
6«.-form [113332-16-4] Constit. of A. spp. Oil. [cx:]i;l + 18.9° (c, 6.2 in CHC1 3).
Constit. of Asteriscus sericeus. Oil. [cx:] 0 + 16.SO (c, 0.27 (Z)-form [54999-55-2]
in CHC1 3). Constit. of A. spp. Cryst. (Etpjpet. ether). Mp 68°.
6-Ketone: [113332-18-6]. 6-0xocyc/onerolido/ Bohlmann, F. eta!, Chem. Ber., 1975, 108, 357.
C 15H 240 2 M 236.353
Constit. of A. sericeus. Oil.
Longifolin Sq-00095
Jakupovic, J. et al, Phytochemistry, 1987, 26, 2854. 3-Methyl-2-[3-methy/-4-(4-methy/-2-furanyl)-2-butenyljfuran,
9CI
Ipomeamaronol Sq-00092 [39007 -94-8]
[26767-96-4]

/ \ .. 0 CH2 0H
o·--Z._o~~
0
C15H 22 0 4 M 266.336 C,sH 1s0 2 M 230.306
Constit. of sweet potato infected with Ceratocystis Constit. of Actinodaphne longifolia. Oil.
fimbriata. Viscous oil. Abs. config. not detd., not clear Hayashi, N. et al, Chem. Ind. (London), 1972, 572.
whether it is a hydroxy1ated deriv. of Ngaione or
lpomeamarone (see Ngaione, Sq-00100).
Marislin Sq-00096
I> SA9070000.
[78284-85-2]
Yang, D.T.C. et al, Phytochemistry, 1971, 10, 1653 (isol, struct)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic

~~
Press, N.Y., 1981, 733.

Lasiosperman Sq-00093
2-[5-(3-Furanyl)-2-methylpentylj-4-methy/furan, 9CI C20H 240 4 M 328.407
[33853-92-8] Metab. of the shell-less mollusk Chromodoris marislae. Oil.
Hochlowski, J.E. eta!, Tetrahedron Lett., 1981, 22, 271 (isol, ir,
nmr)

4-(4-Methyl-S-(4-methyl-2-furanyl)-4- Sq-00097
pentenyl)-2(5H)-furanone, 9CI
7H,12H,13H-5-Dehydro-12-oxolasiosperman
C 15H 200 2 M 232.322
Constit. of Lasiospermum radiatum. Oil. 0

~
6E,7E-Didehydro: [33853-91-7]. Dehydro/asiosperman
C,sH 1802 M 230.306
Constit. of L. radiatum. Oil. Bp0 _01 90°.
4-0xo: [68776-21-6]. 4-0xo/asiosperman. 10- C 15H 1s03 M 246.305
0xolasiosperman (E)-form [54999-54-1]
C,5H 180 3 M 246.305 Constit. of Athanasia spp. Oil.
Constit. of Eumorphia spp. Oil. (Z)-form [54963-32-5]
Bomowski, H., Tetrahedron, 1971, 27, 4101 (isol) V. unstable oil.
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1155 (4- Bohlmann, F. et a!, Chem. Ber., 1975, 108, 357 (isol, ir, uv, ms)
0xolasiosperman)
Jefford, C.W. eta!, Tetrahedron Lett., 1990, 31, 5741 (synth)

167
Myoporone - Nordavanone Sq-00098 - Sq-00101

~yoporone Sq-00098 CtsHn03 M 250.337

1-(3-Furanyl)-4,8-dimethyl-1 ,6-nonanedione, 9CI (4S,7R)-form [581-12-4]
Constit. of Eremophila latrobei, Myoporum laetum and
0 M. acuminatum. Liq. Bp 27 183°. [a] 0 -27.6°.

~
t> SA9080000.
(S)-form Semicarbazone: Cryst. Mp 132.5-133°. (a] 0 -66.2° (C 6H 6).
0 10,11-Didehydro: [41059-84-1]. Dehydrongaione
C 1sHn03 M 250.337 C1sH 200 3 M 248.321
(S)-form [19479-15-3] Constit. of M. deserti. Pale-yellow oil. Bp0 _5 110°. [a]~
Constit. of Myoporum and Eremophila spp. Cryst. -12.5° (CHC1 3).
(MeOH). Mp 15.5-16.SO. [a] 0 -5.0° (c, 5.7 in CHC1 3). 10,11-Didehydro, 2,4-dinitrophenylhydrazone: Orange-red
(9R)-Alcohol: [72145-16-5]. Dihydromyoporone cryst. (EtOH). Mp 129.5-130.SO.
C,sH240 3 M 252.353 10,1 1-Didehydro, 12-acetoxy: 12-Acetoxy-10,11-
Stress metab. of sweet potato (Ipomoea batatas). Oil. didehydrongaione
[a]~ -3.6° (c, 1.95 in MeOH) (synthetic). C17H 220 5 M 306.358
10,11-Didehydro: [38462-36-1]. Dehydromyoporone Constit. of Stilpnophytum linifolium. Oil. [a]i;' -29° (c,
C15H:11,03 M 248.321 5.5 in CHC1 3).
Constit. of M. and E. spp. Cryst. (Etpjhexane). Mp (4R,7S)-form [494-23-5] Ipomeamarone. Ipomoeamarone
32.5-33.SO. [a] 0 -15°. Isol. from 1pomeama batatas. Light-yellow oil. Bp6 140-
10,11-Epoxy: [68776-17-0]. Eumorphinone 1440. [a]J;u +32.4° (c, 5.0 in EtOH).
C15H 200 4 M 264.321 t> Heptatotoxin. SA9082000.
Constit. of Eumorphia spp. Cryst. (Etpjpet. ether). Mp Semicarbazone: Cryst. Mp 131-132°. [a]~ +85° (c, 2 in
69.5°. Abs. config. not detd. C6HJ.
10C,-Hydroxy: [52259-61-7]. 10-Hydroxymyoporone 10,11-Didehydro: [52691-02-8]. Dehydroipomeamarone
Stress metab of the sweet potato. Oil. [alii + 12.3° (c, CtsH200 3 M 248.321
0.6 in MeOH). Stereochem. undefined. Isol. from I. batatas. Light-yellow oil. [a]~ + 14.7° (c,
Blackbume, I.D. eta/, Aust. J. Chern., 1972, 25, 1787 (isol) 0.12 in EtOH).
Burka, L. eta/, J. Org. Chern., 1974, 39, 3241 (7- (4S,7S)-form [27428-93-9] Epingaione
Hydroxymyoporone) Constit. of M. deserti. Oil. Bp0 _5 103°. [a]i;"' - 10.7°
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1155 (neat).
(Eumorphinone)
2,4-Dinitrophenylsemicarbazone: Yellow cryst. (EtOH). Mp
Burka, L. et a/, Phytochemistry, 1979, 18, 873 (iso/)
Still, W.C. eta/, J. Am. Chern. Soc., 1980, 102, 7385 (synth) 166°.
Reich, H. eta/, J. Am. Chern. Soc., 1981, 103, 3112 (synth, 7- 10,11-Didehydro: [39878-02-9]. Dehydroepingaione
Hydroxymyoporone) C15H 200 3 M 248.321
Johnson, W.S. eta/, Tetrahedron Lett., 1984, 25, 3951 (synth, abs Cons tit. of M. deserti. Pale-yellow oil. Bp0 _5 110-111°.
config) [a]~ -34.3° (CHC1 3).
Hess, T. eta/, Tetrahedron Lett., 1987, 28, 5643 (synth, abs config)
Hegarty, B.F. eta/, Aust. J. Chern., 1970, 23, 107 (abs config)
Oguri, I. eta/, Agric. Bioi. Chern., 1971, 35, 357 (biosynth)
Neotorreyol Sq-00099 Hamilton, W.D. et a/, Aust. J. Chern., 1973, 26, 375 (isol)
9-(3-Furanyl)-2 ,6-dimethyl-2,6-nonadien-1-ol, 9CI Burka, L.T. eta/, J. Org. Chern., 1974, 39, 2212 (synth)
[1786-16-9] Oguri, I. eta/, Phytochemistry, 1974, 13, 521 (isol, deriv)
Kondo, K. eta/, Tetrahedron Lett., 1976, 4363 (synth)
12 Burka, L.T. eta/, Phytochemistry, 1977, 16, 2022 (biosynth)
~CH2 0H Russell, C.A. eta/, Aust. J. Chern., 1982, 35, 1881 (abs config)
Schneider, J.A. eta/, J. Chern. Soc., Chern. Commun., 1983, 352
(abs con.fig)
0 Schneider, J. eta/, J. Chern. Soc., Chern. Commun., 1984, 372
Ct5 H120 2 M 234.338 (biosynth)
Constit. of Torreya nucifera. Bp0 _03 117-119°. Chinnock, R.J. et at, Phytochemistry, 1987, 26, 1202 (cmr)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
3,5-Dinitrobenzoyl: Cryst. Mp 95°. Press, N.Y., 1981, 734.
12-Aldehyde: [25529-78-6]. Torreyal Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1071 (!2-Acetoxy-
C15H 200 2 M 232.322 JO, II-didehydrongaione)
Constit. of wood ofT. nucifera. Oil. Bp0 _05 124-126°.
12-Aldehyde, semicarbazone: Cryst. Mp 132-133°. Nordavanone Sq-00101
Sakai, T. eta/, Bull. Chern. Soc. Jpn., 1965, 38, 381 (isol, ir, pmr, 3-(5-Ethenyltetrahydro-5-methyl-2-furanyl)-2-butanone, 9CI
ms, struct) [54933-91-4]
Thomas, A.F. eta/, J. Chern. Soc. C, 1970, 220 (synth)
Kondo, K. et a/, Tetrahedron Lett., 1976, 391 (synth)

Ngaione Sq-00100 ~ I H 0
4-M ethyl-1-(2,3 ,4,5- tetrahydro-5-methyl-[2 ,3'-bifuran]-5-yl)- C11 H 180 2 M 182.262
2-pentanone, 9Cl Constit. of Artemisia pal/ens. [a]~ + 54° (CHC1 3 ).
Thomas, A.F. eta/, Helv. Chim. Acta, 1974, 57, 2062.

0 ,&~
0 10 12

0
168
Phymaspermone- Vernopolyanthofuran Sq-00102 - Sq-00107

Phymaspermone Sq-001 02 Constit. of Greek tobacco. Oil.

9-(3-Furanyl)-2,6-dimethy/-2,5,7-nonatrien-4-one, 9CI 1",2"-Dihydro: [53093-97-3]. 2,3,4,5-Tetrahydro-2,5'-
[35944-00-4] dimethy/-5-(1-methy/ethyl)-2,2' -bifuran, 9CI
C13H200 2 M 208.300
Constit. of Greek tobacco. Oil.
~ 0
(2R* ,5S*)-form [53093-94-0]
cis-form
c.sH•aol M 230.306 Constit. of Greek tobacco. Oil.
Constit. of Phymaspermum parvifolium. r,2"-Dihydro: [53093-96-2].
Bohlmann, F. et al, Tetrahedron Lett., 1972, 851. 1 Constit. of Greek tobacco. Oil.
Almqvist, S. et a/, Acta Chern. Scand., Ser. B, 1974, 28, 528.
Pleraplysillin 2 Sq-00103
[53492-34-5] Vernopolyanthofuran Sq-001 07
6-Hydroxy-2,6-dimethyl-1-(4-methyl-2-furanyl)-7-octen-1-
one, 9CI

~COOCH2
0
[79081-60-0]

~
0
0
C 20H 2,.04 M 328.407 0
Constit. of Pleraplysilla spinifera. Liq.
C 15H 220 3 M 250.337
Cimino, G. et al, Experientia, 1974, 30, 846.
Cimino, G. et al, Tetrahedron Lett., 1975, 3727. Constit. of Vernonia polyanthes. Oil. [1X]i;' -1.4° (c, 3 in
Knight, D.W. eta[, J. Chern. Soc., Perkin Trans. 1, 1981, 1557 CHCl 3).
(synth) 6,7-Didehydro(E): [89913-43-9]. 6,7-
Dehydrovernopolyanthofuran
Prepenlanfuran Sq-00104 C 15H 200 3 M 248.321
From V. polyanthes. Oil. [1X]i;' -2.7° (c, 0.59 in CHCl 3).
[95653-78-4]
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 473; 1983, 22, 2863
(isof)

C 17H 240 3 M 276.375

Constit. of Dysidea fragilis. Oil. [1X]i,<' - 8.SO (c, 0.64 in
CHC1 3).
Guella, G. et al, Helv. Chim. Acta, 1985, 68, 39.

Sesquirosefuran Sq-001 05
2-(3,7-Dimethy/-2,6-octadienyl)-3-methy/furan
[39007-93-7]

C 15H 220 M 218.338

Constit. of the leaf oil of Actinodaphne longifolia. Oil.
Hayashi, N. et al, Chern. Ind. (London), 1972, 572 (isol, struct)
Gedge, D.R. et al, Tetrahedron Lett., 1977, 4443 (synth)
Takeda, A. et al, Bull. Chern. Soc. Jpn., 1977, 50, 1903 (synth)
Araki, S. eta/, Chern. Lett., 1982, 177 (synth)

2,3,4,5-Tetrahydro-2,5' -dimethyl-5-(1- Sq-00106

methylethenyl)-2,2'-bifuran, 9CI

Relative
configuration

C 13H 180 2 M 206.284

(2R* ,5R*)-form [53093-95-l]
trans-form

169
Artemone - 6-lsopropyl-3,9-dimethyl-5,8-... Sq-00108 - Sq-00113

Hyperolactone Sq-00111

Irregular acyclic H

sesquiterpenes Relative
configuration

Artemone Sq-001 08 C14H180 4 M 250.294

2-(5-Etheny/tetrahydro-5-methy/-2-furanyl)-4,4-dimethyl-5- Constit. of Hypericum chinense. Cryst. Mp 57°. [rxln
hexen-3-one, 9CI -228.93° (c, 0.13 in MeOH).
[30925-48-5] Tada, M. et a/, Chem. Lett., 1989, 683 (cryst struct)

~
6-Isopropenyl-3-methyl-9-decen-1-ol Sq-00112
3-Methy/-6-( 1-methy/etheny/)-9-decen-1-o/, 9CI

0~ ~CH 2 0H
I
I

C 15H 240 2 M 236.353 I

Constit. of Artemisia pal/ens. Liq. [rxln +41.4° (c, 1.9 in ~

CHC1 3).
C14H260 M 210.359
Naegeli, P. et at, Tetrahedron Lett., 1970, 5021 (isol, struct)
(3S,6R)-form
Akhila, A. et at, Tetrahedron Lett., 1986, 27, 5885 (biosynth)
Ac: [67601-06-3].
Ct,H2802 M 252.396
6,10-Dimethyl-9-methylene-5-undecen-2- Sq-00109 Component of the sex pheromone of the California red
one scale insect.
9-Jsopropy/-6-methy/-5 ,9-decadien-2-one 3,4-Didehydro, Ac: 6-Isopropeny/-3-methyl-3,9-decadien-1-o/
acetate
C16H 260 2 M 250.380
Component of the sex pheromone of the California red
scale insect.
Ct4Ht..0 M 208.343 [67601-04-1, 67601-07-4, 67601-10-9, 71424-34-5, 73395-36-5]
(E)-form [64854-44-0] Anderson, R.J. eta/, J. Org. Chem., 1980, 45, 2229 (synth, pmr,
Constit. of Costus root oil and root oil of Saussurea cmr)
lappa. Oil. Becker, D. eta/, Tetrahedron, 1988, 44, 4541 (synth, pmr, bib/)
[64854-46-2]
Maurer, B. et at, J. Chem. Soc., Chem. Commun., 1977, 353 (isol, 6-lsopropyl-3,9-dimethyl-5,8-decadien-1-ol Sq-00113
synth) 3,9-Dimethy/-6-(1-methylethy/)-5,8-decadien-1-ol. 9CI
Maurer, B. et at, Helv. Chim. Acta, 1977, 60, 6191.
Dubs, P. eta/, Helv. Chim. Acta, 1978, 61, 984 (isol, synth) ,H

~H,OH
Morizur, J.-P. et at, Tetrahedron Lett., 1982, 23, 5275 (synth)

Helepuberinic acid Sq-0011 0

9-(Hydroxymethy/)-2,6,10-trimethy/-6,10-undecadienoic acid, (3S,5E)-form
9CI. Helepuberic acid
[71051-84-8] C15H280 M 224.386
CH2 0H (3S,5E)-form
Ac: [80696-42-0].
HOOC~ C 17H 300 2 M 266.423
Sex pheromone of the yellow scale Aonidiella citrina.
C15H260 3 M 254.369 Oil. Bp0. 14 111-113°. [rx]i,l.S -11.9° (c, 3 in hexane).
Constit. of Helenium puberulum. Oil. [rx]i;4 + 3.8° (c, 2.5 in (3R,5E)-form
CHC1 3). Ac: [82571-05-9].
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 131. Oil. Bp0 . 13 107-111°. [rx]~ + 11.SO (c, 2.98 in hexane).
[71524-58-8, 72603-87-3]
Mori, K. et at, Tetrahedron, 1982, 38, 521 (synth)

170
Kumepaloxane - Chokol B Sq-00114 - Sq-00120

Kumepaloxane Sq-00114 Constit. of M. spp. Cryst. (pentane). Mp 15-16°. [ocln

[122666-10-8] -37° (c, 1.1 in CHC1 3).
10,11-Dihydro, enantiomer: (+)-Kim/on keto/
Constit. of M. spp. [ocln + 30° (c, 0.6 in CHC1 3).

vO~~aI I
10,11-Dihydro, stereoisomer(l): Carr's keto/
Constit. of M. betcheanum.
Br 10,11-Dihydro, stereoisomer(2): Jackson keto/
Constit. of M. deserti.
C 12H 10BrC10 M 295.646
Constit. of bubble shell Haminoea cymba/urn. Fish 10,11-Dihydro, stereoisomer: Warrego keto/
antifeedant. Oil. [ocln + 22.6° (c, 0.32 in CHC1 3). Constit. of M. deserti.
Poiner, A. et al, Tetrahedron, 1989, 45, 617. [125741-08-4, 125826-70-2, 125826-71-3, 125826-72-4, 125826-73-5,
125826-76-8]
Sutherland, M.D. et al, Aust. J. Chern., 1989, 42, 1995 (isol, pmr,
10-Sesquigeranic acid Sq-00115 cmr, ms, ord)

~ Caulolactone Sq-00118
I ll_COOH I

CtsH2402 M 236.353
Constit. of Conyza schimperi.
lrx-form
Zdero, C. et al, Phytochemistry, 1990, 29, 3167 (isol, pmr, cmr)

CtsH 220 2 M 234.338

lrz.-form [69010-38-4] Caulolactone B
Constit. of Asarum caulescens. Oil. [oc]i;l +8.8° (c, 0.2 in
Cyclopentane MeOH).
IP-form [68984-94-1] Caulolactone A
Constit. of A. caulescens. Cryst. Mp 97-98°. [oc]i; + 170°
sesquiterpenoids (c, 0.3 in MeOH).
Endo, J. et a/, Chern. Pharm. Bull., 1979, 27, 275.

Chokol A Sq-00119
4-(3-Hydroxy-2 ,3-dimethy/cyc/opentyl)-4-penten-1-ol
Bilobalide A Sq-00116
[99877-51-7]
[33570-04-6]

C12H 220 2 M 198.305

Constit. of fungus Epichloe typhina. Fungitoxin. [oc]i;1
C 15H 180 8 M 326.302 -26.6° (c, 1.0 in EtOH).
Constit. of leaves of Ginkgo biloba. Cryst. (HzO). Mp l-Ac: Chokol F
>300°. [oc]~ -66.6°. Ct4H2403 M 240.342
Nakanishi, K. et al, J. Am. Chern. Soc., 1971, 93, 3544 (isol, struct)
Constit. of E. typhina.
Weinges, K. et al, Justus Liebigs Ann. Chern., 1972, 759, 158 (pmr) Yoshihara, T. eta/, Tetrahedron Lett., 1985, 26, 5551 (isol, struct)
Oppolzer, W. et al, Tetrahedron Lett., 1986, 27, 5467 (synth)
Marsh, E.A., J. Org. Chern., 1987, 52, 4142 (synth, abs config)
Carney's ketol Sq-00117 Suzuki, T. et al, J. Chern. Soc., Chern. Commun., 1988, 1531
(synth)
Lawler, D.M. et al, Tetrahedron Lett., 1988, 29, 1207 (synth)
Koshino, H: et al, Agric. Bioi. Chern., 1989, 53, 789 (isol, struct,
pmr, cmr)

Chokol B Sq-00120
6-(3- Hydroxy-2,3-dimethy/cyclopentyl)-2-methyl-1 ,6-
heptadien-3-o/
C 15H 20 0 3 M 248.321 [99877-53-9]
Constit. of Myoporum spp. Cryst. (hexane). Mp 52.5-53°.
[ocJn -30° (c, 1 in CHC1 3).
Stereoisomer: Brigalow keto/
Constit. of M. spp. Gum.
10,11-Dihydro: (-)-Kim/on keto/
CtsH220 3 M 250.337

171
Chokol C - Cyclonerodiol oxide Sq-00121 - Sq-00127

CtsHu02 M 238.369 Cyclodehydromyopyrone A Sq-00124

Prod. by fungus Epichloe typhina. Fungitoxin. Syrup. [116512-31-3]
Yoshihara, T. eta/, Tetrahedron Lett., 1985, 26, 5551 (isol)
Koshino, H. eta/, Agric. Bioi. Chern., 1989, 53, 789 (isol, struct,
pmr, cmr)

Chokol C Sq-00121
6-(3-Hydroxy-2,3-dimethylcyclopentyl)-2-methyl-2,6-
heptadien-1-ol
[99877-52-8]

~---qOH
CtsHw03 M 248.321
Constit. of Eumorphia prostata.
Hess, T. eta/, Tetrahedron Lett., 1987, 28, 5643.

Cyclodehydromyopyrone B Sq-00125
)CH,OH
[116512-32-4]
C1sH260 2 M 238.369

g--Q"Y
Prod. by fungus Epichloe typhina. Mp 51-53°. [1X]~2 -32.0° 0 HO
(c, 0.25 in EtOH).
Z-Isomer: Chokol D
From E. typhina. Syrup. [1X]~4 -44° (c, 0.54 in EtOH).
I
Yoshihara, T. eta/, Tetrahedron Lett., 1985, 26, 5551 (isol) I

Koshino, H. eta/, Agric. Bioi. Chern., 1989, 53, 789 (iso/, struct, CtsHw03 M 248.321
pmr, cmr) Constit. of Eumorphia prostata.
Hess, T. eta/, Tetrahedron Lett., 1987, 28, 5643.
Chokolic acid A Sq-00122
Cyclonerodiol Sq-00126

H~~OH
[28834-06-2]

H(h
C 12H 200 4 M 228.288
Me ester: [125564-60-5]. Methyl chokolate
C 13H 220 4 M 242.314
~~OH
12
Metab. of Epichloe typhina. Fungitoxin.
C 15H 280 2 M 240.385
Kato, N. eta/, Heterocycles, 1990, 30, 341. Metab. of Trichothecium spp., Fusarium culmorum,
Gibberella fujikuroi and Trichoderma polysporum. [1X]n
Curcmnalactone Sq-00123 -20°.
[98263-92-4] 12-Hydroxy: [57689-00-6]. Cyclonerotriol
CtsH 280 3 M 256.384
Metab. of F. culmorum. Cryst. (Et20jpet. ether). Mp
113-1W. [1X]n -27.8° (c, 0.2 in MeOH).
Evans, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1976, 1214
(cyc/onerotriol)
Cane, D.E. eta/, Tetrahedron Lett., 1977, 3511 (abs config)
Cane, D.E. eta/, J. Am. Chern. Soc., 1981, 103, 914 (biosynth)
C 15H 240 2 M 236.353 Fujita, T. eta/, Chern. Pharm. Bull., 1984, 32, 4419 (isol, bib!)
Constit. of Curcuma wenyujin. Cryst. Mp 34-36°. [1X]i;'
-ll.o7° (c, 3.43 in CHC13). Cyclonerodiol oxide Sq-00127
Inayama, S. eta/, Chern. Pharm. Bull., 1985, 33, 2179 (cryst struct) [28834-16-4]

~OH
I

~H
C 15H 280 3 M 256.384
Metabolite of Trichoderma polysporum. Needles (pet.
ether). Mp 47-50°. [1X]i;1 -19.6° (c, 0.38 in MeOH).
10-Epimer: [94992-05-9]. Epicyclonerodiol oxide

172
Eumorphistonol - Myomontanone Sq-00128 - Sq-00135

Ct~H 28 0 3 M 256.384 3-lsopropyl-1-methyl-1,2- Sq-00132

Metabolite of T. polysporum. Oil. cyclopentanedicarboxylic acid
Fujita, T. eta/, Chem. Pharm. Bull., 1984, 32, 4419. 1-Methy/-3-( 1-methy/ethyl)-1 ,2-cyc/opentanedicarboxy/ic
acid, 9C1
Eumorphistonol Sq-00128 [66016-71-5]

f::
[68776-18-1)

~OOH
C 11 H 180 4 M 214.261
C 1 ~H~,0 3 M 248.321 lsol. from Turkish tobacco.
Constit. of Eumorphia spp. Oil. Di-Me ester: [71035-09-1).
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1155 (isol) C 1 ~H 11 0 4 M 242.314
Hess, T. eta/, Tetrahedron Lett., 1987, 28, 5643 (struct) [1X)d +44° (c, 0.045 in EtOH).
Chuman, T. et al, Agric. Bioi. Chem., 1978, 42, 203 (isol, ir, ms,
Gyrinidone Sq-00129 pmr)

w9
[55811-46-6)
Lactaronecatorin A Sq-00133
[58757-91-8)
0

C14H 200 3
~
M 236.310
~~H
Constit. of Gyrinid beetles. Oil. [IX)~ -69° (c, 0.06 in Ct~H 11 0 3 M 250.337
EtOH). Metab. of Lactarius necator and L. scrobiculatus.
Wheeler, J.W. et a/, J. Am. Chem. Soc., 1972, 94, 7589. Daniewsk:i, W.M. et a/, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1975,
23, 639 (isol)
Herbasolide Sq-00130 De Bernardi, M. eta/, Chim. Ind. (Milan), 1976, 58, 177 (isol)
[68299-91-2)
Myodesmone Sq-00134
0 [32531-47-8)

A~'J
o)__.J\..-
0 ~
C14H2004 M 252.310
~0 \L()
Constit. of Dysidea herbacea. Cryst. (Etpjpentane). Mp iO

97-98°. [1Xh6 +95° (c, 0.182 in CHC1 3). C 1 ~H 20 0 1 M 232.322

Charles, C. eta/, Bull. Soc. Chim. Be/g., 1978, 87, 481. Constit. of Myoporum spp. Yellow oil. [1X)n -108.5°
(CHC1 3).
Isomyodesmone Sq-00131 10,11-Didehydro: [39031-79-3). Dehydromyodesmone
1-[2-(3-Furanyl)-5-methy/-2-cyc/openten-1-ylj-3-methyl-1- C 1 ~H 18 0 1 M 230.306
butanone, 9C1. 3-(5-Isova/ery/-4-methy/cyc/opent-1- Constit. of M. deserti. Yellow oil. Bpi 118°. [1Xln -67°
eny{}furan (c, 0.6 in CHC1 3).
[32531-48-9) Blackbume, I.D. et a/, Aust. J. Chem., 1971, 24, 995; 1972, 25, 779
(isol, struct)
Dieter, R.K. et a/, J. Chem. Soc., Chem. Commun., 1983, 1378
(synth)

Myomontanone Sq-00135
3-Furany/[4-methy/-2-(2-methy/propyl)-1-cyclopenten-1-
yljmethanone, 9Cl
Ct~H 20 0 1 M 232.322 [86989-09-5]
Constit. of the essential oil of Myoporum spp. Cryst.
(MeOH). Mp 46.5-47°. Bpi 108°. [1X)n -193° (CHC1 3).
10,11-Didehydro: [38927-56-9).
C 1 ~H 18 0 1 M 230.306
Constit. of M. deserti. Pale-yellow cryst. (MeOH). Mp
25-27°, Mp 117°. [1X)n -254° (CHC1 3jEtOH). 0
Blackbume, I.D. eta/, Aust. J. Chem., 1971, 24, 995; 1972, 25,
1779.

173
Perillup ketol - Aeginetic acid Sq-00136 - Sq-00138

C15Hzo02 M 232.322
Constit. of leaves of Myoporum montanum. Cryst. (2,2,3-
trimethylpentane). Mp 45°. [oc]n +26° (c, 3.5 in CHC1 3).
A8-Isomer: [86989-08-4]. /somyomontanone
Cyclofarnesanes
CI5H21,02 M 232.322
From M. montanum. Oil.
Metra, P.L. et a/, Tetrahedron Lett., 1983, 24, 1749 (isol, struct)
Hess, T. eta/, Tetrahedron Lett., 1987, 28, 5643 (synth, abs conjig) Abscisic acid Sq-00137
Abscisin II
Perillup ketol Sq-00136 [21298-29-8]

C 15H 220 3 M 250.337

Constit. of Myoporum spp. Cryst. (hexane). Mp 99.5-100°.
[ocJn -52° (c, 0.5 in CHCl 3).
Stereoisomer(]): Redbank keto/
Constit. of M. spp. Cryst. (hexane). Mp 88-88.SO. [ocJn
+ 58° (c, 0.8 in CHC13).
Stereoisomer(2): Woogaroo keto/
Constit. of M. spp. Cryst. (hexane). Mp 95°. [ocJn -28°
(c, 0.7 in CHC1 3).
[125826-77-9, 125826-78-0, 125826-79-1)
Sutherland, M.D. et a/, Aust. J. Chem., 1989, 42, 1995 (isol, pmr,
cmr, ms)

Aeginetic acid Sq-00138

[53337-92-1]

~~H Absolute
configuration
'oH
C15H 240 4 M 268.352
Constit. of Aeginetia indica. Cryst. Mp 205°.
5-0-P-D-Glucopyranoside: [72896-58-3). Aeginetoside
C21 H 340 9 M 430.494
Constit. of A. indica. Cryst. Mp 188-191°. [ocl~ -61.2°
(c, 0.39 in EtOH).

174
Ancistrodial - Collybolidol Sq-00189 - Sq-00144

Dinghe, S.S. eta/, Indian J. Chern., 1973, 11, 404; 1974, 12, 413; Constit. of Laurencia palisada. Oil. [oc] 0 + 19.SO (c, 1.5 in
1977, 15, 546 (isol, struct) CHCl 3). Slowly oxid. to Aplysistatin in air.
Endo, T. eta/, Chern. Pharm. Bull., 1979, 27, 2807 (isol)
Eschenmoser, W. et al, Helv. Chim. Acta, 1982, 65, 353 (struct, abs
6P-Hydroxy: 6P-Hydroxyaplysistatin
config) C15H 21 Br0 4 M 345.232
Constit. of L. filiformis. Cryst. (MeOH). Mp 153.5-
l55.SO. [oc]i;l + 130° (c, 0.4 in MeOH).
Ancistrodial Sq-00139
Pettit, G.R. et al, J. Am. Chern. Soc., 1977, 99, 262.
[68398-28-7] Paul, V.J. eta/, Tetrahedron Lett., 1980, 2787 (deriv)

IY
Capon, R. et al, Tetrahedron, 1981, 37, 1613 (6P-
hydroxyaplysistatin, cryst struct, abs config)
?HO White, J.D. et al, J. Am. Chern. Soc., 1982, 104, 3923 (synth)
~10 Hoye, T.R. eta/, J. Am. Chern. Soc., 1982, 104, 6704 (synth)
Shieh, H.-M. eta/, Tetrahedron Lett., 1982, 23, 4643 (synth)
CHO Kraus, G.A. et al, J. Org. Chern., 1983, 48, 5356 (synth)
Gosselin, P. et a/, Tetrahedron Lett., 1983, 24, 5515 (synth)
C1sHn02 M 234.338 Tanaka, A. eta/, Agric. Bioi. Chern., 1984, 48, 2535; 1986, SO,
Constit. of Ancistrotermes cavithorax. 1069 (synth)
!!.?-Isomer: [85654-10-0]. 2-[(2,2-Dimethyl-6-
methylenecyclohexyl)ethylj-2-butenedial
C 15H 120 2 M 234.338
Bicyclolaurencenol Sq-00143
Constit. of marine alga Cau/erpa bikinensis. Cytotoxin, [79373-33-4]
ichthyotoxin and antifeedant. Oil. [oc] 0 + 8.SO (c, 0.8 in
CHCl 3).
Baker, R. eta/, J. Chern. Soc., Chern. Commun., 1978, 410.
Paul, V.J. eta/, Tetrahedron Lett., 1982, 23, 5017.

Ancistrofuran Sq-00140 C15H 240 M 220.354

Constit. of Laurencia intricata. Oil. [oc]i;l -16.1° (c, 0.67 in
[68326-20-5]
CHC13).

lb-a
Horsley, S.B. eta/, J. Org. Chern., 1981, 46, 5033.

Collybolidol Sq-00144
C 15H 220 2 M 234.338
Constit. of Ancistrotermes cavithorax.
Baker, R. eta/, J. Chern. Soc., Chern. Commun., 1978, 410, 981
Ag Absolute
configuration

~-o
(isol, synth)
Hoye, T.R. eta/, J. Org. Chern., 1981, 46, 1198 (synth)
Baker, R. et al, J. Chern. Soc., Perkin Trans. 1, 1985, 2463 (synth) 0 OH 0
Saito, A. eta/, Agric. Bioi. Chern., 1986, SO, 1309 (synth)
C15H 160 6 M 292.288
Anhydrotrisporone Parent compd. unknown. Hydrol. of Collybolide causes
Sq-00141
opening of the lactone ring.
0-Benzoy/: [33340-30-6]. Collybolide
C22H 200 7 M 396.396
Constit. of the basidiomycete Collybia macu/ata. Cryst.
(EtOH). Mp 210°. [oc] 0 + 17° (CHC1 3).
9-Epimer, 0-benzoy/.· [31199-75-4]. lsocoUybolide
C22 H 200 7 M 396.396
C1sH2002 M 232.322 Constit. of C. maculata. Mp 193°. [oc] 0 -17° (c, 1.7 in
Prod. by Choanephora trispora (Blakeslea trispora). Cryst. CHC1 3).
Mp 110°. [oc]i,O -84.5°. 7,9-Diepimer, 6-deoxy: [106794-13-2]. Deoxycollybolidol
Cainelli, G. et a/, Chim. Ind. (Milan), 1967, 49, 748.
CtsH160 5 M 276.288
Constit. of C. peronata. Cryst. (EtOAcjhexane). Mp
189-190°. [oc] 0 +21° (c, 0.1 in CHCl 3).
Aplysistatin Sq-00142 Pascard-Billy, C., Acta Crystallogr., Sect. C, 1972, 28, 331 (cryst
[62003-89-8] struct, Isocollybolide)

rro-b
Bui, A.M. eta/, Tetrahedron, 1974, 30, 1327 (isol, pmr, cmr, uv,
struct)
Fogedal, M. eta/, Phytochemistry, 1986, 25, 2661
(Deoxycollybolidol)

B~O
Ct5H 21 Br03 M 329.233
Constit. of Aplysia angasi. Cryst. Mp 173-175°. [oc]i;l
-375° (MeOH).
12-Deoxo: [77249-86-6]. 12-Deoxyap/ysistatin. Palisadin A
C 15H 23 Br02 M 315.249

175
1,4-Diacetoxy-2-[(2,2-dimethyl-6-... - Onchidal Sq-00145 - Sq-00151

1,4-Diacetoxy-2-((2,2-dimethyl-6- Suzuki, K.T. eta/, J. Chern. Soc., Chern. Cornrnun., 1971, 527 (y-
M onocyclofarnesol)
methylenecyclohexyl)ethyl)-1,3- Oritani, T. eta/, Agric. Bioi. Chern., 1985, 49, 2819 (zsol, props)
butadiene Sq-00145
2-[2-(2,2-Dimethyl-6-methylenecyclohexyl)ethylj-1 ,3-
3-Hydroxy-2-(2-(2,6,6-trimethyl-2- Sq-00148

80M
butadiene-1 ,4-diol diacetate, 9CI
[85654-09-7] cyclohexen-1-yl)ethyl)-2-buten-1-al
3-Formyl-5-(2,6,6-trimethyl-2-cyclohexenyl)-2-penten-1-ol

~~OH
AcO CHO
C 19H 280 4 M 320.428 c15H240z M 236.353
Constit. of marine alga Caulerpa bikinensis. Cytotoxin, Ac:
ichthyotoxin and antifeedant. Viscous oil. [1X]n -3° (c, C 17H 21;03 M 278.391
0.9 in CHC 3). Constit. of Caulerpa flexilis. Oil. Bp0.8 160°. [1X]n -59°
!l4 -Jsomer: [79689-22-8]. 1,4-Diacetoxy-2-[(2,6,6-trimethyl-2- (c, 12 in MeOH).
cyclohexenyl)ethylj-1 ,3-butadiene. 2-[2-(2 ,6,6- Trimethyl- 2- Capon, R.J. eta/, Aust. J. Chern., 1981, 34, 1775.
cyclohexen-1-yl)ethylj-1 ,3-butadiene-1 ,4-diol diacetate
Constit. of C. flexilis. Oil. Bp 0 _25 125°. [1X]n -47° (c, 9.5 Microcionin 3 Sq-00149
in MeOH).
[59805-79-7]
Capon, R.J. eta/, Aust. J. Chern., 1981, 34, 1775.
Paul, V.J. eta/, Tetrahedron Lett., 1982, 23, 5017 (isol, struct)

5-(1,4-Dihydroxy-2,2-dimethyl-6-
('( - .

methylenecyclohexyl)-3-methyl-2,4- ~u
pentadienoic acid, 9CI Sq-00146 Ct5Hz20 M 218.338
1' ,4'-Dihydroxy-y-ionylideneacetic acid Constit. of Microciona toxystila. Oil. [1X]n + 36.SO.
[9130 1-56-3] Cimino, G. et a/, Tetrahedron Lett., 1975, 3723 .

P-Monocyclonerolidol Sq-00150
.x..-...-laJOH
HOUOH ~ 1X-Ethenyl-IX,2,2-trimethyl-6-methylenecyclohexanepropano/,
9C/
C 15H 220 4 M 266.336 [83920-95-0]
Sesquiterpene antibiotic; abscisic acid analogue. Prod. by
Cercospora cruenta. Growth inhibitor of rice seedlings.
Oil. [1X]i: +2.S0 (c, 0.4 in EtOH).
1'-Deoxy: 4' -Hydroxy-y-ionylideneacetic acid
C15H 22 0 3 M 250.337
From a Stemphylum sp. Germination inhibitor. Powder. C15H 21;0 M 222.370
(1X]i,<' + 55° (EtOH). Constit. of Ptychanthus striatus. Viscous oil. [IX]~ + 3.2° (c,
Oritani, T. et a/, Agric. Bioi. Chern., 1984, 48, 1677; 1985, 49, 245; 0.66 in CHC1 3).
1987, 51, 275; 1988, 52, 2119; 1990, 54, 125 (isol, ir, crnr, struct, Takeda, R. eta/, Bull. Chern. Soc. Jpn., 1983, 56, 1125.
props, synth)
Sassa, T. et a/, Agric. Bioi. Chern., 1988, 52, 1625 (deriv)
Onchidal Sq-00151
[67656-42-2]
5-(2,2-Dimethyl-6-methylenecyclohexyl)-3- Sq-00147
methyl-2,4-pentadien-1-ol, 9CI
y-lonylideneethanol
[99297 -86-6) ::::,... CHO

~
(2Z,4E)-form OAc
CH2 0H
Ct7H 240 3 M 276.375
C15H 240 M 220.354 Constit. of Onchidella binneyi. Oil. [IX]~ + 17.2° (c, 1 in
Terpenoid antibiotic. Isol. from Cercospora cruenta. Plant CHC1 3).
growth inhibitor. Oil. Ireland, C. eta/, Bioorg. Chern., 1978, 7, 125.
3,5-Dinitrobenzoyl: Cryst. (Et20jhexane). Mp 98.SO. [1X]i;l
+ 18° (c, 0.1 in CHC1 3).
7,8-Dihydro: [33526-22-6). y-Monocyclofarnesol
C 15H:u.0 M 222.370
Formed from mevalonic acid by a Helminthosporium
siccans enzyme extract. Oil. [1X]n + 17.6° (EtOH).

176
Palisadin B - Ricciocarpin A Sq-00152 - Sq-00157

Palisadin B Sq-00152 Constit. of Dysideafragilis. Oil. [oc]i,O +6° (c, 0.3 in

(77249-85-5] CHC1 3).
!J.4 -Isomer: [56881-44-8]. Pa/lescensin 1
CtsH 220 M 218.338
Constit. of D. pallescens. Oil. [oc]n -89.SO (CHC1 3).
3,4-Didehydro: [56881-45-9]. Pal/escensin 2
C15H 200 M 216.322
Constit. of D. pallescens. Oil. [oc]n +39.SO.
C 15H 24 Brz0 M 380.162 8-0xo: [112137-03-8]. Pal/escensone
Constit. of Laurencia palisada. Oil. [oc]n + 8.8° (c, 1.3 in C15H 200 2 M 232.322
CHC1 3). Constit. of the sponge Dictyodendrilla cavernosa. Cryst.
5P-Acetoxy: [77250-04-5]. sp-Acetoxypalisadin B Mp 42.5-43°. (oc)n + 36° (c, 1 in CHC1 3).
C 17H 26Brz03 M 438.199 Cimino, G. et a[, Tetrahedron Lett., 1975, 1417 (isol, struct)
Constit. of L. palisada. Oil. [oc]n -131.7° (c, 0.6 in Tius, M.A. eta[, J. Org. Chern., 1982, 47, 3166 (synth)
CHC1 3). Matsumoto, T. et a[, Bull. Chern. Soc. Jpn., 1983, 46, 491 (synth)
Guella, G. et al, Helv. Chim. Acta, 1985, 68, 39 (isol)
12-Hydroxy: [77250-03-4]. 12-Hydroxypalisadin B Cambie, R.C. et al, J. Nat. Prod. (Lloydia), 1987, 50, 948
C 15H 24 Brz0 2 M 396.161 (Pallescensone)
Constit. of L. palisada. Oil. [oc]n + 19.7° (c, 0.4 in Kurth, M.J. eta[, Tetrahedron Lett., 1987, 28, 1031 (synth)
CHC1 3).
Paul, V.J. et al, Tetrahedron Lett., 1980, 2787. Phaseic acid Sq-00156
Tanaka, A. eta[, Agric. Bioi. Chern., 1986, 50, 1069 (synth) 5-(8-Hydroxy-l ,5-dimethyl-3-oxo-6-oxabicyclo[J .2 .l]oct-8-
y{)-3-methyl-2,4-pentadienoic acid, 9CI. Phaesic acid
Palisol Sq-00153 [24394-14-7]
[77249-84-4)

~CH,B<
~
COOH Absolute
configuration

C 15H 200 5 M 280.320

C 15H 23 Br0 M 299.250 Revised struct. From immature seeds of Phaseolus
Constit. of Laurencia palisada. Oil (as acetate). (oc)n -0.6° multiflorus. Mp 207-209°. [oc]n -3350° (MeOH).
(c, 0.51 in CHC1 3) (acetate). Me ester: [41670-48-8].
Paul, V.J. et al, Tetrahedron Lett., 1980, 2787. Cryst. (C 6H 6 jpet. ether). Mp 155-158°.
MacMillan, J. et al, J. Chern. Soc., Chern. Commun., 1968, 124
Pallescensin 3 Sq-00154 (isol)
Milborrow, B.V., J. Chern. Soc., Chern. Commun., 1969, 966 (pmr)
[56881-46-0) Milborrow, B.V., Phytochemistry, 1975, 14, 1045 (struct, abs,
config)
Takahashi, S. et al, Agric. Bioi. Chern., 1988, 52, 1633; 1989, 53,
2711 (synth)

Ricciocarpin A Sq-00157
[127350-71-4)
C 15H 200 3 M 248.321
Ho

9:J-o
Constit. of Dis idea pallescens. Oil.
4' ,5' -Dihydro: (85653-95-8). 3-[2-(2,2-Dimethyl-6-
methylenecyclohexyl)ethyl]-5-hydroxy-2(5H)-furanone,
9CI
C 15H 220 3 M 250.337
Constit. of marine alga Caulerpa bikinensis. Viscous oil. 0
(oc)n -5.6° (c, 0.8 in CHC1 3).
CtsH200 3 M 248.321
Cimino, G. et al, Tetrahedron Lett., 1975, 1417. Constit. of Ricciocarpus natans. Cryst. (EtOAcjhexane).
Paul, V.J. et al, Tetrahedron Lett., 1982, 23, 5017 (deriv) Mp 110-1W. (oc)i,O + 17.8° (c, 1.18 in CH 2Cl2).
Wurzel, G. et al, Phytochemistry, 1990, 29, 2565 (isol, pmr, cmr)
Penlanpallescensin Sq-00155
3-[2-(2,2-Dimethyl-6-methylenecyclohexyl)ethyljfuran, 9CI.
Dihydropallescensin 2

C 15H 220 M 218.338

(S)-form (83631-17-8]

177
Ricciocarpin B - Xanthoxin Sq-00158 - Sq-00162

Ricciocarpin B Sq-00158 Metab. of C. trispora. Liq.

[127350-72-5] 12-Deoxy, 2P-hydroxy: [29538-78-1]. Apotrisporin.
Apotrisporin E
C15Hzz0 3 M 250.337
Prod. by Phycomyces blakesleeanus and C. trispora. A.
max 235, 300 nrn.

Grasselli, P. eta/, Chim. Ind. (Milan), 1967, 49, 748; 1970, 52, 584
(iso[)
Uneyama, K. eta/, Tetrahedron Lett., 1976, 443 (synth)
Sutter, R.P., Exp. Myco/., 1986, 10, 256.
C 15H 20 0 4 M 264.321
Constit. of Ricciocarpus natans. Cryst. (EtOAcjhexane).
Mp 160-161°. [1X]i,<' +6.3° (c, 0.9 in CH 2Cl2). Xanthoxin Sq-00162
Wurzel, G. eta/, Phytochemistry, 1990, 29, 2565 (isol, pmr, cmr) [8066-07-7]

H~o
Ricciofuranol Sq-00159
[127419-66-3]

C 15H 110 3 M 250.337

Photooxidn. prod. of vio1axanthin and related substances.
Constit. of several marine and higher plants. Plant
growth inhibitor.
9E-Isomer: t-Xanthocin
C 15H 22 0 3 M 250.337 CtsHzz0 3 M 250.337
Constit. of Ricciocarpus natans. Oil. [1X]i,<' + 16.2° (c, 0,3 in Constit. of several marine and higher plants.
CH2ClJ. Burden, R.S. eta/, Tetrahedron Lett., 1970, 4071 (isol. struct)
Wurzel, G. eta/, Phytochemistry, 1990, 29, 2565 (isol, pmr, cmr) Oritani, T. eta/, Agric. Bioi. Chern., 1973, 37, 1215 (svnth)
Kienzle~ F. eta/, Helv. Chim. Acta, 1978, 61, 2616 (synth)
Kobayashi, M. eta/, Agric. Bioi. Chern., 1990, 54, 2723 (bib[)
P-Snyderol Sq-00160
[59403-81-5]

C 15H 25Br0 M 301.266

Constit. of Laurencia snyderae. Oil. [1X]n + 14.6° (c, 3.9 in
CHC1 3).
Ac: P-Snyderyl acetate
C 17H 27Br01 M 343.303
Metab. of L. obtusa. Oil. [1X]~4 -9° (c, 1 in CHC1 3).
114-Isomer: [59403-83-7]. rx-Snyderol
C15H 25 Br0 M 301.266
Constit. of L. obtusa. Oil. [1Xln + 10.4° (c, 4.65 in
CHC1 3).
Kato, T. eta/, J. Chern. Soc., Chern. Commun., 1976, 518 (synth)
Howard, B.M. et a/, Tetrahedron Lett., 1976, 41 (iso/, struct)
Gonzalez, A.G. eta/, Tetrahedron Lett., 1976, 137 (synth)
Murai, A. eta/, Chern. Lett., 1981, 1125 (synth)
Ayyad, S.-E.N. eta/, Phytochemistry, 1990, 29, 3193 (acetate)

Trisporone Sq-00161
[17928-77-7]

~moH CH2 0H
C 15Hzz03 M 250.337
Metab. of Choanephora trispora (Blakeslea trispora). Liq.
[1X]i,<' + 19.4°.
12-Deoxy: Deoxytrisporone. Apotrisporin C
C 15H 110 1 M 234.338

178
Dactylenol - Striatenone Sq-00163 - Sq-00169

3-Methyl-5-(2,3,6-trimethyl-2,5- Sq-00166
cyclohexadienyl)-1-penten-3-ol
Rearranged cx-Ethenyl-cx,2,3,6-tetramethyl-2,5-cyclohexadiene-1-propanol,
9CI. 3-(3-Hydroxy-3-methyl-4-pentenyl)-1 ,2,4-trimethyl-1 ,4-

cyclofarnesanes
cyclohexadiene
[59700-20-8]

Dactylenol Sq-00163
[58542-82-8)
C 15H 140 M 220.354
~H Sequiterpenoid from the marine alga Laurencia nidifica.
Oil.
~ l1
Sun, H.H. et al, Tetrahedron Lett., 1976, 585 (isol, ir, pmr, cmr,
struct)

C 15H 140 M 220.354 Microcionin 2 Sq-00167

Constit. of Aplysia dactylomela. Oil. [cxJn +203.8° (neat). [59805-78-6)
Ac:
C 17H 21;02 M 262.391
Constit. of A. dacty/ome/a. Oil. [cxln
CHC1 3).
+ 168° (c, 2.5 in (!_
Schmitz, F.J. et al, J. Org. Chem., 1978, 43, 4220. ~u
C 15H 220 M 218.338
Dactyloxene A Sq-00164 Constit. of Microciona toxystila. Oil. [cxln -58.3°.
[54990-54-4] !:!.2•13 -Isomer: [59805-80-0). Microcionin 4
C 15H 220 M 218.338

¢r=>~
Constit. of M. toxystila. Oil. Stereochem. undefined.
Cimino, G. eta/, Tetrahedron Lett., 1975, 3723.

Striatene Sq-00168
C 15H 140 M 220.354 1,5 ,6-Trimethyl-6-(3-methyl-2,4-pentadienyl)cyclohexene, 9CJ
Constit. of Ap/ysia dacty/ome/a. Oil. [cxJn -5.9° (c, 1.4 in
CHC1 3). [83920-96-1]
Schmitz, F.J. et al, J. Org. Chem., 1978, 43, 4220.

Dactyloxene B Sq-00165 Absolute

configuration
[54928-03-9]

CtsHu M 204.355
Constit. of Ptychanthus striatus. Oil. [cx]~4 + 72.7° (c, 1.19
in CHC1 3).
Takeda, R. et al, Bull. Chem. Soc. Jpn., 1983, 56, 1125.

C 15H 140 M 220.354

Constit. of Aplysia dactylomela. Oil. [cxln + 106° (c, 0.7 in Striatenone Sq-00169
CHC1 3). 2,3 ,4-Trimethyl-3-(3-methy/ene-4-pentenyl)-cyclohexanone,
9CI
5-Epimer: Dactyloxene C
CtsH140 M 220.354 [122872-01-9]
Constit. of A. dactylomela. Oil. [cxln +45.8° (c, 0.9 in
CHC1 3).
Schmitz, F.J. eta/, J. Org. Chem., 1978, 43, 4220 (isol, struct)
Maurer, B. et al, Helv. Chim. Acta, 1980, 63, 2503 (synth, abs
config)
C 15H 140 M 220.354
Constit. of Parella navicularis. Oil. [cxJn -9.1° (c, 0.11 in
CHC1 3).
1,6-Diepimer: [55790-40-4]. Balsamitone
CtsH 200 M 216.322
Constit. of Tanacetum balsamitoides. Oil. Bp0 . 1 100°.
Bohlmann, F. eta/, Chem. Ber., 1975, 108, 1369 (Balsamitone)
Toyota, M. et al, Phytochemistry, 1989, 28, 1661 (Striatenone)

179
Striatol - 1,10-Bisaboladiene-3,6-diol Sq-00170- Sq-00174

Striatol Sq-00170 Bilobanone Sq-00172

rx- Ethenyl-rx,l ,2,6-tetramethyl-2-cyclohexene-1-propanol, 9CI 2-Methyl-5-[5-(2-methy/propyl)-3-furanylj-2-cyclohexen-1-
[83920-97-2] one, 9CI

(I Absolute

~
configuration

C15H 260 M 222.370

Constit. of Ptychanthus striatus. Oil. [rx]i; +49.SO (c, 1.2 in
CHCI 3). C 15H100 1 M 232.322
Takeda, R. et al, Bull. Chern. Soc. Jpn., 1983, 56, 1125. (S)-form [170 15-33-7]
Constit. of Ginkgo biloba. Oil. Bp0 _09 118-122° (bath).
[rxJn + 6. 7°.
Oxime: Mp 64-65°.
Semicarbazone: Mp 142-144°.
Bisabolanes Irie, H. et al, J. Chern. Soc., Chern. Commun., 1967, 678 (struct)
Biichi, G. et al, J. Org. Chern., 1969, 34, 857 (synth)
Hegde, S.E. et al, J. Org. Chern., 1982, 47, 3148 (synth)

Biperezone Sq-00173
7-Amino-2,1 0-bisaboladiene Sq-00171 [119318-13-7]
7- Amino-7,8-dihydro-rx-bisabolene. 7- Aminobisabolene

(6R,7R)-form

C 15H 27N M 221.385

12
(6R,7R)-form [105281-34-3]
Constit. of Ciocalypta sp. Oil. [rxJn -15° (c, 0.4 in C30H 380 6 M 494.627
MeOH). Constit. of Coreocarpus arizonicus.
B,HCI: [105281-33-2]. 12,12'-Bis(2-methylbutanoy/oxy): [119285-24-4].
Yellow oil. [rx]~ -8.3° (c, 0.5 in MeOH). C40H 5•.010 M 694.861
(6R,7S)-form [105281-43-4] Constit. of C. arizonicus.
Constit. of a Halichondria sp. and a sponge Theone/la 12,12' -Bis(3-methylbutanoy/oxy): [119318-14-8].
sp. Oil. [rxJn + 39° (MeOH), [rx]i? + 59.9° (c, 3 in C40 H 5•.010 M 694.861
CHC1 3). Constit. of C. arizonicus.
!J.9-Jsomer, 11-hydroxy: 7-Amino-2,9-bisaboladien-11-ol. Jolad, S.D. et al, Phytochemistry, 1988, 27, 3545.
Aminobisabolenol
C 15H 27NO M 237.384 1,10-Bisaboladiene-3,6-diol Sq-00174
Constit. ofT. sp. Oil. [rxln +29° (MeOH).
!J. 11 -Jsomer, lOR-hydroxy: 7-Amino-2,11-biaboladien-JOR-ol.
lsoaminobisabolenol b
~f~LoH
'l ~
C 15H 27NO M 237.384
Constit. ofT. sp. Oil. [rxJn +40° (MeOH).
!J. 11 -Isomer, lOS-hydroxy: 7- Amino-2,11-bisabo/adien-JOS-o/. (3R,6R, 7S)-form
lsoaminobisabolenol a
C15H 27NO M 237.384 C 15H 21;01 M 238.369
Constit. ofT. sp. Oil. [rxJn +34° (MeOH). Incorrect numbering system used in reference.
Sullivan, B.W. et al, J. Org. Chern., 1986, 51, 5134 (isol) (3R,6R,7S)-form [119285-25-5]
Gulavita, N.K. et al, J. Org. Chern., 1986, 51, 5136 (isol) Constit. of Coreocarpus arizonicus. Oil.
Kitagawa, I. et al, Chern. Pharm. Bull., 1987, 35, 928 (cryst struct) (3S,4S,7S)-form [119364-23-7]
Constit. of C. arizonicus. Oil.
Jolad, S.D. et al, Phytochemistry, 1988, 27, 3545.

180
2,7(14)-Bisaboladiene-10,11-diol - 3,7-Bisaboladiene-2,8-dione Sq-00175 - Sq-00183

2,7(14)-Bisaboladiene-1 0,11-diol Sq-00175 2,11-Bisaboladiene-1,1 0-diol Sq-00179

2-Methyt-6-(4-methyt-3-cyc/ohexen-1-yl)-6-heptene-2,3-diot,

w
9CI
[88861-99-8]

C 15H 260 2 M 238.369

Constit. of Achillea odorata. Oil.
C15H 260 2 M 238.369 Barrero, A.F. et al, Phytochemistry, 1990, 29, 3213 (isol, pmr, cmr)
Constit. of Acritopappus confertus. Oil.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 2243. 2,11-Bisaboladiene-7,1 0-diol Sq-00180

~
2,9-Bisaboladiene-7 ,11-diol Sq-00176

C 15H 260 2 M 238.369

~
OH

Constit. of Achillea odorata. Oil. [aln -44.4° (c, 1 in

C 15H 260 2 M 238.369
Constit. of Achillea odorata. Oil. [aJn -45.0° (c, 1 in
CHCI 3).
Barrero, A.F. et al, Phytochemistry, 1990, 29, 3213 (isol, pmr, cmr)

CHC1 3). 2,10-Bisaboladiene-1,4-diol Sq-00181

Barrero, A.F. et al, Phytochemistry, 1990, 29, 3213 (isol, pmr, cmr)
I OH

~
1,10-Bisaboladiene-3,4-diol Sq-00177
[129673-87-6]

rlLH
)l "''b
C15H 260 2

1290.
M 238.369
Constit. of Curcuma tonga. Needles (hexane). Mp 126.5-

Ohshiro, M. et al, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr)

C 15H 260 2 M 238.369
Constit. of Curcuma tonga and Greenmaniella resinosa. 2,10-Bisaboladiene-1,9-dione Sq-00182
Viscous oil. [aln -31.7° (c, 0.23 in MeOH). 6-( 15-Dimethyt-3-oxo-4-hexenyl)-3-methyt-2-cyc/ohexen-1-
Ohshiro, M. et al, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr) one, 9CI. 1,9-Bisabotadione
[83217-93-0]
2,10-Bisaboladiene-7,15-diol Sq-00178

~
[116537-80-5]

0~~
C 15H 220 2 M 234.338
Constit. of Lynchnophora sellowii. Oil. [aln + 20° (c, 0.3 in
CHC1 3).
C15H 260 2 M 238.369
Constit. of Vanillosmopsis arborea. Oil. Bohlmann, F. et al, Phytochemistry, 1982, 21, 1087.
Matos, M.E.O. eta[, J. Nat. Prod. (Lloydia), 1988, 51, 780.
3,7-Bisaboladiene-2,8-dione Sq-00183
10,11-Dihydro-6-oxoattantone
[57095-92-8]

181
2,9-Bisaboladiene-7,11,12,15-tetrol - 2,10-Bisaboladien-7-ol Sq-00184 - Sq-00190

C 15H 120 2 M 234.338 2,6-Bisaboladien-1 0-ol Sq-00188

Constit. of Ginkgo biloba. 2-Methyl-6-(4-methyl-3-cyclohexen-1-ylidene )-3-heptanol,
Irie, H. et al, Chern. Pharm. Bull., 1975, 23, 1892. 9CI. Laggerol
[57689-22-2]
2,9-Bisaboladiene-7, 11, 12, 15-tetrol Sq-00184

~CH,OH
CH2 0H
C 15H 260 M 222.370
Constit. of Laggera aurita. Oil. Bp 3_5 109°. [1X]i? + 12.1°.
Zutshi, S.K. et al, Indian J. Chern., Sect. B, 1976, 14, 64.
C 15H 21;04 M 270.368
12,15-Di-Ac:
2,10-Bisaboladien-6-ol Sq-00189
C19H:14P 6 M 354.442
Constit. of Calea szyszylowiczii. Oil.
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227.
(6S,7S)-form
2,7-Bisaboladiene-10,11,12-triol Sq-00185
Yingzhaosu B
[73301-53-8]
C 15H 260 M 222.370
(6S,7S)-form [15352-77-9] P-Bisabolol
Constit. of Gossypium hirsutum oil and other essential
oils. Oil. Bp2 121-122°. [1X]i? + 7.16° (c, 0.28 in CHC1 3),
[1X]i? + 23.3° (CHC1 3).
(6R,7S)-form
OH 6-epi-P-Bisabolol
C15H 260 M 222.370
C 15H 260 3 M 254.369 Constit. of bergamot oil. [1X]i? -57° (c, 0.1 in CHC13).
Constit. of Artabotrys unciatus.
Minyard, J.P. et al, J. Org. Chern., 1968, 33, 909 (isol)
Zhang, L. et al, J. Chern. Soc., Chern. Commun., 1988, 523. Takaoka, D. et al, Phytochemistry, 1976, 15, 425 (isol)
Ohloff, G. et al, Helv. Chim. Acta, 1986, 69, 698 (abs config)
Frater, G. et al, Helv. Chim. Acta, 1989, 72, 653 (synth)
2,8-Bisaboladiene-8,12,13-triol Sq-00186
Yingzhaosu D
[121067-53-6] 2,10-Bisaboladien-7-ol Sq-00190
6- Methyl-2-( 4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol, 8CI

H~ (6R,7R)-form

OH
C 15H260 3 M 254.369 C 15H 260 M 222.370
Constit. of Artabotrys unciatus. Oil. [IX]~ -39.5° (c, 0.73 in I> MJ9685000.
CHC1 3). (6R,7R)-form [515-69-5] ( + )-IX.-Bisabolol
Zhang, L. et al, J. Chern. Soc., Chern. Commun., 1988, 523. Constit. of essential oil of Populus balsamifera and
Atalantia monophylla. Oil. Bp 12 154-156°. [IX]~ +53.8° (c,
2.6 in CHC1 3).
1,10-Bisaboladien-3-ol Sq-00187 I> MJ9685000.
Zingiberenol
(6S,7R)-form
[58334-55-7] 7-epi-IX-Bisabolol. (- )-Anymol
Isol. from wood oil of Myoporum crassifolium. Constit.
of Abies, Picea and Pinus spp. Oil. Bp 1 114°. [1X]n -69°
(c, 1.3 in EtOH).
p-Phenylazophenylurethane: Orange needles (pet. ether).
Mp 103-103.5°. [1X]n -7° (c, 1 in CHC1 3).
(6S,7S)-form [23089-26-1] (- )-IX.-Bisabolol. Levomenol, INN
C 15H 260 M 222.370 Isol. from essential oil of Matricaria chamomilla
Constit. of Zingiber officina/e, isol. by g1c. Oil. (chamomile oil). Antiinflammatory agent. Oil. d~0 0.921.
Terhune, S.J. et al, Can. J. Chern., 1975, 53, 3285 (isol) Bp 12 153°. [IX]~ -68.4° (c, 1.16 in EtOH). ni? 1.4936.
Paquette, L.A. et al, Tetrahedron Lett., 1982, 23, 131 (synth) Sorm, F. et al, Collect. Czech. Chern. Commun., 1951, 16, 626 (isol)

182
2,7(14)-Bisaboladien-10-one - 1,3,5,10-Bisabolatetraene Sq-00191 - Sq-00196

O'Brien, K.G. eta/, Aust. J. Chern., 1953, 6, 166; 1954, 7, 298 1,3,5,7(14),10-Bisabolapentaene-1,2,4,8- Sq-00194
(Anymol) tetrol
Yakovlev, V. eta/, Arzneim.-Forsch., 1969, 19, 615 (pharmacol,
tox)
Sampath, V. eta/, Indian J. Chern., 1969, 7, 1060 (isol) HO
Kergomard, A. eta/, Tetrahedron, 1977, 33, 2215 (synth)
Schwartz, M.A. et a/, J. Org. Chern., 1979, 44, 953 (synth, abs
config)
Babin, D. eta/, Tetrahedron, Suppl., No. I, 1981, I (synth, abs
config)
Ohloff, G. eta/, Helv. Chim. Acta, 1986, 69, 698 (isol)
O'Donnell, G.W. et a/, Aust. J. Chern., 1989, 42, 2021 (bib/, iso/, Ct5H200 4 M 264.321
deriv) 8-Angeloyl: [69868-02-6]. Senecioodontol
Carman, R.M. eta/, Aust. J. Chern., 1989, 42, 2035 (bib/, synth) C20H 260 5 M 346.422
Carman, R.M. eta/, Aust. J. Chern., 1989, 42, 2041 (cryst struct)
2-Me ether, 8-angeloyl: [69905-06-2]. 3-0-
Methylsenecioodentol
2,7(14)-Bisaboladien-10-one Sq-00191 C21 H 280 5 M 360.449
[87061-21-0] Constit. of Senecio oxyodontus. Oil.
2,4-Di-Me ether, 8-angeloyl: [69905-08-4]. 3,5-Di-0-
methylsenecioodontol
C22H 300 5 M 374.476
From S. oxyodontus. Oil.
2,8-Diangeloyl: [69905-11-9]. 3-0-Angeloylsenecioodontol
C25 H 3P 6 M 428.524
From S. oxyodontus. Oil.
1,4-Quinone, 2-Me ether, 8-angeloyl: [69905-05-1]. 2-0-
C 15HZ40 M 220.354
Constit. of Acritopappus confertus. Oil. [cc]~4 -81° (c,l.84 Methyl-1 ,4-dehydrosenecioodontol. 3-0-Methyl-2,5-
dehydrosenecioodentol
in CHC1 3).
C21 H 260 5 M 358.433
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243. From S. oxyodontus. Yellow oil. [cc]~4 + 12.4° (c, 0.6 in
CHC1 3).
2,10-Bisaboladien-1-one Sq-00192 Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1591.
1-Bisabolone
[61432-71-1] 1,3,5,7,10-Bisabolapentaen-1-ol Sq-00195
2-(1 ,5-Dimethyl-1 ,4-hexadienyl)-5-methylphenol, 9CI

C 15HZ40 M 220.354 C15H 200 M 216.322

Constit. of Stevia purpurea. Oil. Bp0 . 1 120°. [cc]i;l -37° (c, (E)-form
3. 7 in CHC1 3). Ac: [84753-68-4].
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 3366. C17H 220 2 M 258.360
Constit. of a Halichondria sp. Oil. Bp 0 . 1 94°.
Bisabolangelone Sq-00193 4-Hydroxy: [84743-24-8]. 1,3,5,7,10-Bisabolapentaene-1,4-
3,3a,7,7a-Tetrahydro-3-hydroxy-3,6-dimethyl-2-(3-methyl-2- diol. 2-(1 ,5-Dimethyl-1 ,4-hexadienyl)-5-methyl-1 ,4-
butenylidene)-4(2H)-benzofuranone, 9CI. Angelikoreanol benzenediol, 9CI
C15H200 2 M 232.322
[30557-81-4] Constit. of a H. sp. Cryst. (CH 2Cl2/pet. ether). Mp 76-
77.50.
(Z)-form
4-Hydroxy: [84743-23-7].
Constit. of a H. sp. Oil. Bp0 . 1 160°.
Capon, R.J. eta/, Aust. J. Chern., 1982, 35, 2583.
C15H200 3 M 248.321
Constit. of Angelica silvestris seeds. Cryst. (C 6H 6). Mp 148- 1,3,5,10-Bisabolatetraene Sq-00196
1490. [ccln +49.3° (c, 0.073 in dioxan). 1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene, 9Cl. 2-Methyl-
6-(4-methylphenyl)-2-heptene. rt-Curcumene. ar-Curcumene
Novotny, L. et at, Tetrahedron Lett., 1966, 3541 (iso/, struct)
Hata, K. eta/, Chern. Pharm. Bull., 1971, 19, 1963 (isol, struct) [644-30-4]
Riss, B.P. eta/, Tetrahedron Lett., 1986, 27, 4979 (synth)

(R)-form

M 202.339

183
1,3,5,11-Bisabolatetraene - 1,3,5,10-Bisabolatetraen-11-ol Sq-00197 - Sq-00201

(R)-form [4176-17-4] Constit. of Pseudopterogorgia rigida and Lasianthaea

Widespread occurrence in plants e.g. Curcuma
aromatica, Ambrosia spp. and Amorpha fruticosa. Liq.
Bp 17 137°. [exln -34.3°.
(S)-form [4176-06-1]
Liq. Bp 1 105-110° (bath). (exJn +40° (c, 3.3 in CHC1 3).
Naves, Y.-H., Bull. Soc. Chim. Fr., 1951, 987 (isol)
Honwad, V.K. et al, Tetrahedron, 1965, 21, 2593 (abs config)
Hall, S.S. et al, J. Org. Chern., 1975, 40, 3306 (synth)
Vig, O.P. et al, J. Indian Chern. Soc., 1976, 53, 54 (synth)
Tamao, K. et al, Tetrahedron Lett., 1979, 2155 (synth)
Nabeta, K. et al, Agric. Bioi. Chern., 1986, 50, 2915 (biosynth)
Takano, S. et al, J. Chern. Soc., Chern. Commun., 1988, 1539
(synth)
1,3,5,11-Blsabolatetraene Sq-00197
lso-cx-curcu~ne
[74183-92-9]
podocephala. Oil. [exln -7° (c, 3.65 in CHC1 3), [exln
-23.6° (CHC1 3).
Ac: Oil. [ex]i;' - UO (c, 0.4 in CHC13).
(S)-form
Constit. of the sponge Epipolasis sp. and of Didiscus
flavus. Oil. [ex]i; +29.1° (c, 3.13 in CHC1 3).
8,9-Didehydro (E-): 1,3 ,5,8,10- Bisabolapentaen-1-ol.
Dehydrocurcuphenol
C 15H100 M 216.322
Constit. of E. sp. Oil. [exm - 1.2° (c, 0.48 in CHC1 3).
Bohlmann, F. et al, Chern. Ber., 1978, 111, 843 (isol)
McEnroe, F.J. et al, Tetrahedron, 1978, 34, 1661 (isol, struct)
Ghisa1berti, E. et al, Aust. J. Chern., 1979, 32, 1627 (isol)
Fusetani, N. et al, Experientia, 1987, 43, 1234 (isol)
Wright, A.E. et al, J. Nat. Prod. (Lloydia), 1987, 50, 976 (isol)
Joseph-Nathan, P. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1116
(cmr)

1,3,5,10-Bisabolatetraen-2-ol Sq-00200
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol, 9CI.
Xanthorrhizol
[30 199-26-9]

ClsH11 M 202.339
Constit. of Curcuma aromatica. Oil.
Ho, T.-L. et al, Chern. Ind. (London), 1983, 862 (synth, bib[)

1,3,5,10-Bisabolatetraene-1,4-diol Sq-00198
\CXH
2-(1 ,5-Dimethyl-4-hexenyl)-5-methyl-1 ,4-benzenediol, 9CI clsHzzo M 218.338
Constit. of rhizomes of Curcuma xanthorrhiza. Oil. [ex]~
-52.5°.
Rimpler, H. et al, Z. Naturforsch., B, 1970, 25, 995 (isol, struct)
Mane, R.B. et al, Indian J. Chern., 1974, 12, 938 (synth)
John, T.K. et al, Indian J. Chern., Sect. B, 1985, 24, 35 (synth)
Garcia, G.E. et al, J. Nat. Prod. (Lloydia), 1987, 50, 1055 (synth)
Rane, R.K. et al, Indian J. Chern., Sect. B, 1987, 26, 572 (synth)
C 15H110 1 M 234.338 Joseph-Nathan, P. et al, J. Nat. Prod. (Lloydia), 1988,51, 1116
(R)-form [69301-25-3] Curcuhydroquinone (cmr)
Constit. of Pseudopterogorgia rigida (gorgonian sea
plume). Has antibiotic props. Viscous oil. [exln -21° (c, 1,3,5,10-Bisabolatetraen-11-ol Sq-00201
0.9 in CHC1 3).
I
1-0-(3-Methylbutanoyl): I

Czoll300 3 M 318.455

HOH,$?
Constit. of Perezia carpholepis. Oil. [exln -10° (c, 1 in
CHC1 3).
McEnroe, F.J. et al, Tetrahedron, 1978, 34, 1661 (isol, ir, pmr,
struct)
Sanchez, I.H. et al, J. Org. Chern., 1981, 46, 4666 (synth)
Joseph-Nathan, P. et al, Phytochemistry, 1982, 21, 669. C 15H1z0 M 218.338
Garcia, E. et al, J. Nat. Prod. (Lloydia), 1987, 50, 1055 (synth) (S)-form (39599-18-3] Nuciferol
Constit. of Torreya nucifera. Bp0 _05 131-132°. [ex]~
1,3,5,10-Bisabolatetraen-1-ol Sq-00199 +41.1 o.
2-(1,5-Dimethyl-4-hexenyl)-5-methylphenol, 9CI. 11-Aldehyde: [25532-74-5]. 1,3,5,10-Bisabolatetraen-11-al.
Curcuphenol Nuciferal
[17194-58-0] C 15H 100 M 216.322
Constit. ofT. nucifera. Bp 0 _03 107.5-108.SO. [ex]i~ +62.1°
(c, 16.5 in CHC13).
(R)-form 11-Aldehyde, 2,4-dinitrophenylhydrazone: Mp 138-139°.
Sakai, T. et al, Bull. Chern. Soc. Jpn., 1965, 38, 381 (isol, uv, ir,
pmr, ms, struct)
Gast, G. et al, Helv. Chim. Acta, 1971, 54, 1369 (synth)
Evans, D.A. et al, Tetrahedron Lett., 1973, 1389 (synth)
C 15H110 M 218.338 Depezay, J.-C. et al, Bull. Soc. Chim. Fr., II, 1981, 306 (synth)
Bianco, L. et al, Tetrahedron Lett., 1981, 645 (synth)
(R)-form [69301-27-5] Takano, S. et al, Tetrahedron Lett., 1982, 23, 5567 (synth)

184
1,3,5,10-Bisabolatetraen-9-one - 2,5,11-Bisabolatriene Sq-00202 - Sq-00207

Yoneda, R. et al, Chern. Pharm. Bull., 1987, 35, 913 (synth) Eschenmoser, A. et al, Helv. Chim. Acta, 1950, 33, 171 (isol,
Yoneda, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 3163 struct)
(synth) Arigoni, D. et al, Helv. Chim. Acta, 1954, 37, 881 (abs cotifig)
Joshi, G.D. eta/, Indian J. Chern., 1965, 3, 91 (synth)
1,3,5, 10-Bisabolatetraen-9-one Sq-00202
2-Methy/-6-(4-methy/phenyl)-2-hepten-4-one, 9CI. ar- 1,3(15),10-Bisabolatriene Sq-00205
Turmerone. Dehydroturmerone 3-(1 ,5-Dimethy/-4-hexenyl)-6-methy/enecyclohexene, 9CI. P-
Sesquiphellandrene
I
I [20307-83-9]

0~
C 15H 200 M 216.322
(R)-form [532-65-0] C15H 24 M 204.355
Constit. of essential oil from Curcuma tonga, C. amada Constit. of the oil of ginger (Zingiber officina/e). Oil. Bp 1
and C. domestica. Pale-yellow oil. Bp 10 159-160°. [1X]i? 90°. [1X]i? -3.99° (neat).
+82.2JO. Nitrosite: Cryst. (Me 2CO). Mp 88-90° dec. [1X]i? + 29° (c,
Semicarbazone: Cryst. (C 6H 6). Mp 106°. 1.5 in CHC1 3).
Rupe, H. et al, Helv. Chim. Acta, 1936, 19, 569 (isol) 12-0xo: [71939-69-0]. 1,3(1 5),10-Bisabo/atrien-12-a/. 12-
Honwad, V.K. et al, Tetrahedron, 1964, 20, 2921 (abs config) 0 xo-fi-sesquiphellandrene
Grieco, P.A. et al, J. Org. Chern., 1973, 38, 2909 (synth) C 15H 220 M 218.338
Gosselin, P. eta/, J. Org. Chern., 1979, 44, 2807 (synth)
Meyers, A.l. et al, Tetrahedron Lett., 1979, 2749 (synth)
Constit. of Tarchonanthus trilobus. Oil. [1X]n -9.3° (c,
El Jazouli, M. et al, J. Chern. Soc., Chern. Commun., 1985, 1598 0.15 in CHC1 3).
(synth) Connell, D.W. eta/, Aust. J. Chern., 1966, 19, 283 (ft-
Motoyoshiya, J. et al, J. Org. Chern., 1985, 50, 1326 (synth) Sesquiphellandrene)
Gharpure, M.M. eta/, Indian J. Chern., Sect. B, 1986, 25, 1214 Bohlmann, F. et al, Phytochemistry, 1979, 18, 677 (12-0xo-fJ-
(synth) sesquiphe/landrene)

1,3,5,11-Bisabolatetraen-10-one Sq-00203 5,7(14),8-Bisabolatriene Sq-00206

2-Methy/-6-(4-methy/phenyl)-1-hepten-3-one 1-(1 ,5-Dimethy/-2-hexenyl)-4-methy/cyc/ohexene, 9CI.
[76760-39-9] Gratissimene
[83324-74-7]

CisH 24 M 204.355
C 15H 200 M 216.322 Constit. of Ocimum gratissimum. Oil. Bp 5 97-98.5°. [1X]i?
Props. and registry nos. refer to racemates which were obt. -162.SO.
synthetically. Constit. of oil of Cinnamomum cassia. Oil.
Dembitskii, A.D. eta/, Khim. Prir. Soedin., 1982, 18, 398.
Bp0.01 71-74°.
11,12-Dihydro: [76760-40-2]. 1,3,5-Bisabo/atrien-10-one. 2-
M ethy/-6-(4-methy/phenyl)-3-heptanone 2,5,11-Bisabolatriene Sq-00207
C 15H 22 0 M 218.338 1-( 1,5-Dimethy/-5-hexenyl)-4-methy/-1 ,4-cyc/ohexadiene,
Constit. of the oil of C. cassia. Oil. Bp0.01 90°. 9CI. P-Curcumene
Thomas, A.F., Helv. Chim. Acta, 1980, 63, 1615 (isol, struct, ms, [451-56-9]
synth)

1,3,10-Bisabolatriene
Zingiberene
[495-60-3]
Sq-00204
~ (R),[~rn
C 15H 24 M 204.355
(R)-form [28976-67-2]
Absolute Constit. of, inter alia, the essential oil of Curcuma
configuration aromatica and C. xanthorrhiza. Liq. Bp 19 142°. [1X]n
-48.2°. The abs. config is as in CA but does not appear
to be explicitly stated in the lit.
CisH 24 M 204.355 (S)-form
Constit. of ginger oil. Also from Thymus serpyl/um, Piper
Constit. of Nectandra elaiophora. Bp 2. 2 98-100°. [1X]i?
longum and Curcuma zedoaria. Oil. Bp 11 128-130°. [1X]i;
+26.7°.
-61.7° (CHC1 3).
Naves, Y.-R., Bull. Soc. Chim. Fr., 1951, 987.
Nitrosoch/oride: Cryst. Mp 93-94°.

185
2,6,10-Bisabolatriene - 3(15),7(14),10-Bisabolatriene Sq-00208 - Sq-00212

2,6,10-Bisabolatriene Sq-00208 Not the same as 2,6,10-Bisabolatriene, Sq-00208 which

4-(1,5-Dimethyl-4-hexenylidene)-1-methylcyclohexene, 9CI. has been renamed (formerly a.-Bisabolene).
y-Bisabolene. a.-Bisabolenet (obsol.) (R,E)-form [70286-31-6]
[495-62-5] Oil. [a.]i? + 54.3° (c, 1 in EtOH).
(R,Z)-form [70286-33-8]

~
Oil. [a.]i? -12° (c, 1 in EtOH).
(S,E)-form [70286-32-7]
Oil. [a.]i? -38.9° (c, 1 in EtOH).
(E)-form
(S,Z)-form [58845-44-6]
Constit. of oil of Opoponax. Oil. Bp 12 155-157°. [a.]i?
12
+ 8.0° (c, 1 in EtOH).
C15H24 M 204.355 [25532-79-0, 29837-07-8, 70286-16-7, 70332-15-9, 73465-96-0]
(E)-form [53585-13-0] Delay, F. et al, Helv. Chim. Acta, 1979, 62, 369 (synth, bib[)
Constit. of Ayapana amygdalina and a Laurencia sp. Oil. Buss, A.D. et al, J. Chern. Soc., Perkin Trans. 1, 1987, 2569
[a.]~ -18.8° (c, 1 in CHC1 3). (synth)
2,3-Epoxide: [75744-73-9]. y-Bisabolene-2,3-epoxide Vig, O.P. et al, J. Indian Chern. Soc., 1987, 64, 756 (synth)
C 15H 240 M 220.354
Constit. of L. nipponica. Oil. [a.ln +37.3° (c, 2.2 in 2,7(14),10-Bisabolatriene Sq-00211
CHC1 3). Called y-Bisabolene 8,9-epoxide in the 1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyc/ohexene,
reference. 9CI. P-Bisabolene
12-Hydroxy: 2,6,10-Bisabolatrien-12-ol. 12-Hydroxy-y-
bisabolene
C 15H 240 M 220.354
Isol. from a Pseudopterogorgia sp. Oil.
(h (R)-form
(Z)-form [13062-00-5]
Constit. of oil of myrrh and oil of lime. Oil. ~~
Vig, O.P. et a/, Indian J. Chern., 1970, 8, 955 (synth)
Giraudi, E. et a/, Recherches, 1974, 19, 205 (synth) CtsH24 M 204.355
Overton, K.H. eta/, J. Chern. Soc., Chern. Commun., 1976, 105 (R)-form
(biosynth) Isol. from Chamaecyparis nootkatensis and Pinus
Wolinsky, J.E. et al, J. Org. Chern., 1976, 41, 697 (struct) sibirica. [a.]n + 75°. ni? 1.4879.
Delay, F. et al, Helv. Chim. Acta, 1979, 62, 369 (synth)
Bohlmann, F. et al, Phytochemistry, 1979, 80, 1997 (isol) (S)-form [495-61-4]
Suzuki, T. et al, Chern. Lett., 1980, 1267 (epoxide) Constit. of the essential oils of bergamot, lemon and
Buss, A.D. eta/, Tetrahedron Lett., 1983, 24, Ill (synth) wild carrot. Oil. Bp 10•5 129-130°. [a.]i? -84.4°.
Anastasis, P. et al, Can. J. Chern., 1984, 62, 2079 (biosynth, bib[) 10<:;,11<:;-Epoxide: [88861-98-7]. 10,11-Epoxy-2,7(14)-
Look, S.A. eta/, Experientia, 1984, 40, 931 (!2-Hydroxy-y- bisaboladiene
bisabolene)
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1989, 28, 617 (synth, C15H 240 M 220.354
deriv) Constit. of Acritopappus confertus. Oil. Bp0 . 1 120°. [a.]~
-89° (c, 11.1 in CHC1 3).
Pentegova, V.A. et al, Collect. Czech. Chern. Commun., 1961, 26,
2,7,9-Bisabolatriene Sq-00209 1362 (isol)
4-(1 ,5-Dimethyl-1 ,3-hexadienyl)-1-methylcyclohexene, 9CI. Manjarrez, A. et al, J. Org. Chern., 1966, 31, 348 (synth)
TheoneUine. Theonellin Andersen, N.H. eta/, Phytochemistry, 1970, 9, 1325 (isol)
[94663-92-0] Vig, O.P. et al, J. Indian Chern. Soc., 1971, 48, 993 (synth)
Crawford, R.J. et al, J. Am. Chern. Soc., 1972, 94, 4298 (synth)
Sakane, S. et al, J. Am. Chern. Soc., 1983, 105, 6154 (synth)
Bohlmann, F. et al, Phytochemistry, 1983, 22, 2243 (epoxide)
Sakurai, H. et al, Tetrahedron, 1983, 39, 883 (synth)
Nabeta, K. et a/, Agric. Bioi. Chern., 1986, SO, 2915 (biosynth)

C 15H 24 M 204.355 3(15),7(14),10-Bisabolatriene Sq-00212

Constit. of the sponge Theone/la cf. swinhoei. Oil. [a.]~ lsobisabolene
+ 23° (c, 0.26 in hexane).
[6009-90-1]
Nakamura, H. eta/, Tetrahedron Lett., 1984, 25, 5401.

2,7,10-Bisabolatriene Sq-00210
4-(1 ,5-Dimethyl-1 ,4-hexadienyl)-1-methylcyclohexene, 9CI.
a.-Bisabolenet
[17627-44-0]
C15H 24 M 204.355

~
Constit. of vetiver oil (Bharatpur variety) (Vetiveria
zizanioides). Oil. d~6 0.886. Bp8 99-102°. [a.]~ ·--47° (c,
(R,E),fo'm 4.6 in CHC1 3). n~ 1.4966.
Kalsi, P.S. et al, Tetrahedron, 1962, 18, 1165 (isol, struct)
Vig, O.P. eta/, J. Indian Chern. Soc., 1971, 48, 993 (synth)

M 204.355

186
1,3,5-Bisabolatriene-1,11-diol - 2,5,10-Bisabolatrien-9-one Sq-00213 - Sq-00220

1,3,5-Bisabolatriene-1, 11-diol Sq-00213 2,7(14),10-Bisabolatrien-12-ol Sq-00217

Curcudiol. 10,11-Dihydro-11-hydroxycurcuphenol Laneeo/
[109028-15-1] [10067-29-5]
I OH

~CH,
OH
C15H 240 M 220.354
C 15H 240 2 M 236.353 Constit. of Santa/urn tanceotatum and Osyris tenuifolia.
Constit. of the sponges Didiscus fiavus and an Epipolasis Bp 17 175-176°. [cxln -67.8°.
sp. Oil. [cx]~2 +9.2° (c, 10.8 in CHC1 3).
Manjarrez, A. et al, Tetrahedron, 1964, 20, 333 (struct)
Wright, A.E. et al, J. Nat. Prod. (Lloydia), 1987, 50, 976. Cazes, B. et al, Tetrahedron Lett., 1978, 4065 (synth)
Fuji, K. et al, J. Chern. Soc., Chern. Cornrnun., 1987, 449 (synth)
1,3,5-Bisabolatriene-1,7 ,15-triol Sq-00214
Sydonol 1,3, 10-Bisabolatrien-9-one Sq-00218
[77782-90-2] 2-Methyt-6-(4-methyt-2,4-cyc/ohexadien-1-yl)-2-hepten-4-ene,
9CI. ot- Turmerone
[82508-15-4]

C 15H 1•.03 M 252.353

Isol. from Aspergillus spp. Antifungal antibiotic. Needles
(EtOAcjhexane). Mp 65-67°. [cx]i? + 7.2° (c, 1 in C15H 220 M 218.338
MeOH). Constit. of turmeric (Curcuma tonga). Oil.
Nukina, M. et al, Agric. Bioi. Chern., 1981, 45, 789. Golding, B.T. et al, J. Chern.' Soc., Chern. Cornrnun., 1982, 363.

2,7(14),10-Bisabolatriene-1,9,12-triol Sq-00215 1,3(15),10-Bisabolatrien-9-one Sq-00219

1,9,12-Bisabolenetriol Cur/one. fJ- Turmerone
[87440-60-6]

(h_
o)L ~~
Absolute
configuration

M 252.353 C 15H 2z0 M 218.338

Tri-Ac: 1,9,12-Triacetoxybisabolene
C21 H 300 6 M 378.464
Constit. of Artemisia spp. Cryst. Mp 82°.
Huneck, S. et al, Phytochemistry, 1986, 25, 883.
2,7(14),9-Bisabolatrien-11-ol
Helianthol A
Constit. of Curcuma tonga and of turmeric. Oil. [cxln
-0.03° (c, 2.16 in CHC1 3). Props. refer to Curlone of
defined stereochem. from C. tonga. No stereochem.
indicated for P- Turmerone from turmeric.
[82508-14-3]
Golding, B.T. et al, J. Chern. Soc., Chern. Cornrnun., 1982, 363 (/J-
Sq-00216 Turrnerone)
Kiso, Y. et al, Phytochemistry, 1983, 22, 596 (Cur/one)

~
2,5, 10-Bisabolatrien-9-one Sq-00220
Turmerone. Tumerone

0\0
[56485-42-8]

HO
C 15H 24 0 M 220.354
(R)-form [72916-06-4]
Constit. of essential oil of Helianthus tuberosus. Oil. [cx]i?
+61.0° (c, 0.3 in EtOH).
C15H 220 M 218.338
Miyazawa, M. et al, Phytochemistry, 1983, 22, 1040. Constit. of Curcuma spp. Oil. Bp 10 125-126°.
Malingre, Th.M. et a/, Pharrn. Weekbl., 1975, 110, 601.

187
2,7,10-Bisabolatrien-9-one- Bisabolene oxide Sq-00221 - Sq-00226

2,7,10-Bisabolatrien-9-one Sq-00221 10,11-Dihydro, 11-hydroxy: 11-Hydroxy-3,7(14)-

2-Methyl-6-(4-methyl-3-cyclohexen-1-yl)-2,5-heptadien-4- bisaboladien-2-one
one, 9Cl. Atlantone. rx-Atlantone CtsH2402 M 236.353
Constit. of M. shushunensis. Oil. [a.]~4 -13.2° (C, 1.8 in
CHC1 3).
Nagahama, S. et a/, Bull. Chern. Soc. Jpn., 1964, 37, 1029 (isol)
Hodgson, G.L. eta/, J. Chern. Soc., Chern. Cornrnun., 1973, 236
(E)-form (synth)
Erdtman, H. eta/, Phytochemistry, 1979, 18, 1495 (isol1
C 15H 22 0 M 218.338 Mehta, G. eta/, Tetrahedron Lett., 1979, 2625 (synth)
(E)-form [26294-59-7) Gutierrez, A.B. eta/, Phytochemistry, 1988, 27, 3871 (derivs)
Major constit. of Cedrus deodara. Oil. Bp 1 142-145°
(bath). [a.Jn + 1.2° (c, 0.83 in CHC1 3). ni,D 1.5342. 2-Bisabolene-1,12-diol Sq-00224
10,11-Dihydro: [57130-01-5]. 2,7-Bisaboladien-9-one. 10,11- [117232-52-7)
Dihydroatlantone
Isol. from heartwoods of Ginkgo biloba and Atlas cedar.
Oil. Opt. inactive. Interconverts with the (Z)-form on
standing.
(Z)-form [56192-70-2]
Minor constit. of C. deodara. Oil. ni,D 1.5228.
10,11-Dihydro: [57130-00-4).
Found in G. biloba and A. cedar. Oil. Opt. inactive.
Pande, B.S. eta/, Tetrahedron, 1971, 27, 841 (iso/, struct) CtsH2802 M 240.385
Babler, J.H. eta/, J. Org. Chern., 1974, 39, 1656 (synth) Constit. of Vittadinia gracilis. Oil. [a.]i;4 + 6° (c, 0. 2 in
Plattier, M. eta/, Recherches, 1974, 19, 131 (Dihydroatlantone) CHC1 3).
Irie, H. eta/, Chern. Pharrn. Bull., 1975, 23, 1892 1-Ketone: [52589-23-8]. 12-Hydroxy-2-bisabolen-1-one.
(Dihydroatlantone) Ptilostemonol
Adams, D.R. eta/, J. Chern. Soc., Perkin Trans. I, 1975, 1741
CtsH260 2 M 238.369
(synth)
Motoyoshiya, J. et a/, J. Org. Chern., 1985, 50, 1326 (synth) Constit. of the roots of Ptilostemon chamaepuce. Oil.
Manville, J.F. et a/, Phytochemistry, 1989, 28, 3073 (prnr, crnr) [a.)ij -40.8° (c, 1.34 in CHC1 3). Stercochem. not defined.
]-Ketone, 12-aldehyde: [52589-29-4). 1-0xo-2-bisaholen-12-
Sq-00222 al. Ptilostemonal
2,7(14),10-Bisabolatrien-9-one
Constit. of roots of P. chamaepuce. Oil. [a.]~4 --20.1 o (c,
P-Atlantone
1.74 in CHC1 3). Stereochem. not defined.
[38331-79-2)
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 650 (Ptilosternonol,
Ptilosternonal)
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1979, 17, 295 (synth,
Ptilosternonol)
Zdero, C. eta/, Phytochemistry, 1988, 27, 2251 (2-Bisabo/ene-1,12-
diol)

10-Bisabolene-7,15-diol Sq-00225
C 15H 22 0 M 218.338
Constit. of Curcuma xanthorrhiza. Oil. [oc]~ -48.8° (c, 0.12
in EtOH).
Crawford, R.J. eta/, J. Am. Chern. Soc., 1972, 94, 4298 (synth)
Itokawa, H. eta/, Chern. Pharrn. Bull., 1985, 33, 3488 (isol)

3,7(14),10-Bisabolatrien-2-one Sq-00223
2-Methyl-5-(5-methyl-1-methylene-4-hexenyl)-2-cyclohexen- C 15H 280 2 M 240.385
1-one. Cryptomerione Constit. of Baccharis latifolia. Oil.
[5988-72-7] Zdero, C. eta/, Phytochemistry, 1989, 28, 531.

Bisabolene oxide Sq-00226

[38970-57-9]

C 15H 22 0 M 218.338
Constit. of Cryptomeria japonica. [a.Jn -38° (CHC1 3). ni:'
1.5050.
C 15H 240 M 220.354
10,11-Epoxide: [119765-82-1]. 10,11-Epoxy-3,7(14)- Constit. of Gossypium hirsutum. Oil.
bisaboladien-2-one
Hedin, P.A. eta/, Phytochemistry, 1972, 11, 2118.
C 15H2202 M 234.338
Constit. of Mikania shushunensis. Oil. [a.Jii' -18.9° (c,
2.1 in CHC1 3).

188
11-Bisabolene-7,10,15-triol - Deodarone Sq-00227 - Sq-00233

11-Bisabolene-7,10, 15-triol Sq-00227 8-Deoxy: Caespitane

C15H 15Br1Cl0 M 416.623
Constit. of L. caespitosa. Cryst. Mp 82-84°. [cx]n + 39.8°
(c, 0.89 in CHCl3).
6-Hydroxy: 6-Hydroxycaespitol
C 15H 15Br1Cl0 3 M 448.621
Constit. of L. caespitosa. Cryst. Mp 152-153°. [cxJn
+ 11.7° (c, 0.29 in CHC1 3).
8-Deoxy, 5P-hydroxy: [71679-25-9]. Deodactol
C 15Hlll0 3 M 256.384
C 15H 15Br1Cl01 M 432.622
Constit. of Baccharis /atifolia.
<i:onstit. of Aplysia dactylomela. Shows antineoplastic
Zdero, C. eta/, Phytochemistry, 1989, 28, 531. props. Cryst. (hexane). Mp 134-135°. [cx]n +40° (c, 0.2
in EtOH).
tx-Bisabolol oxide A Sq-00228 5P,6-Dihydroxy, 8-Ac: [72926-49-9]. Dihydroxydeodactol
[2256 7-36-8) monoacetate
C 17H 17Br1Cl0 5 M 506.658
Constit. of A. dactylomela. Cryst. (hexanejC 6H 6). Mp

U
H O n /'.. 168-169°. [cx)n +40.SO (CHCl 3).
/ -o- Gonzales, A.G. eta/, Tetrahedron Lett., 1974, 1249; 1976, 3051;
1979, 2719 (struct, biosynth, cmr)
Hollenbeak, K.H. eta/, Tetrahedron, 1979, 35, 541 (cryst struct,
abs conjig, Deodactol)
C 15H 260 1 M 238.369 Schmitz, F.J. et al, J. Org. Chern., 1980, 45, 1525
Constit. of Matricaria chamomilla. Liq. (Dihydroxydeodactol monoacetate)
Sampath, V. et al, Indian J. Chern., 1969, 7, 100 (struct) Chang, M. eta/, Phytochemistry, 1989, 28, 1417 (isol, cryst struct,
Schilcher, H. eta/, Arch. Pharm. (Weinheim, Ger.), 1976, 309 (isol, abs con.fig)
struct)
Deodardione Sq-00232
tx-Bisabolol oxide B Sq-00229 [68326-19-2]
[26184-88-3]

HO~
I 0 ~

C 15H 260 1 M 238.369 C 15H 110 3 M 250.337

Constit. of Matricaria chamomilla. Liq. Constit. of the essential oil of Cedrus deodara. Cryst. (pet.
Schilcher, H. et al, Arch. Pharm. (Weinheim, Ger.), 1976, 309.
ether). Mp 101-102°. [cx]n + 5.2° (c, l.l in CHCl 3).
Krishnappa, S. et a/, Tetrahedron, 1978, 34, 599.
tx-Bisabolol oxide C Sq-00230
[59861-08-4]
Deodarone Sq-00233
[41943-81-l]
0
ATYOH

\V'
CtsH260 1 M 238.369
Constit. of Matricaria chamomilla. Cryst. (EtOH). Mp 99- C 15H 140 1 M 236.353
1000. Constit. of Cedrus deodara. Oil. [cx]n +6.3° (CHCl 3).
Schilcher, H. eta/, Arch. Pharm. (Weinheim, Ger.), 1976, 309, 189. Adams, D.R. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1502
(synth)
Caespitol Sq-00231 Vig, O.P. eta/, Indian J. Chern., Sect. B, 1976, 14, 929 (synth)
Shankaranarayan, R. et al, Tetrahedron, 1977, 33, 1201 (isol)
[50656-64-9]

C 15H 15Br1Cl01 M 432.622

Constit. of Laurencia caespitosa. Cryst. (hexane). Mp 109-
1110.

189
3,4:10,11-Diepoxy-1,8-dihydroxy-... - Diperezone Sq-00234 - Sq-00239

3,4:10,11-Diepoxy-1,8-dihydroxy-7(14)- Sq-00234 2,5-Dihydroxy-2,5,10-bisabolatriene-1,4- Sq-00237

bisabolen-2-one dione
2-(1,5-Dimethy/-4-hexenyl)-3,6-dihydroxy-5-methyl-2,5-
OH cyclohexadiene-1 ,4-dione. Hydroxyperezone. Oxyperezone.

HO~~
Oxypipitzahoic acid
[16981-83-2]

C1sHnOs M 282.336
(1«,3P,4fl)-form
Diange/oy/:
C2!!H340 7 M 446.539 C15H100 4 M 264.321
Constit. of Senecio fulgens and S. abrotanifolius. Oil. Present in roots of Perezia spp. Red plates. Mp 143°.
[IX]~ -65.9° (c, 0.95 in CHC1 3). Configurational identity 2-Angeloyl: [55035-69-3].
of the two samples not clear. C10H160 5 M 346.422
Bohlmann, F. et al, Chern. Ber., 1976, 109, 2014.
Found in P. spp. Red oil. Bp 1 88°. [1X]n -15° (EtOH).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 469. 2-(3-Methylbutanoyl): [62885-90-9].
C10H 280 5 M 348.438
1,7-Dihydroxy-2,1 0-bisaboladien-4-one Sq-00235 From P. runcinata and P. hebeclada. Red oil. Isol. as a
mixt. with the 5-isomer.
1-Hydroxyrklobanone
5-(3-Methylbutanoyl): [62885-80-7].
[35334-41-9]
C10H 280s M 348.438
From P. runcinata and P. hebeclada. Red oil.

~CH,
Joseph-Nathan. P., eta/, Phytochemistry, 1972, 11, 1803; 1977, 16,
1086; 1982, 21, 1129 (isol, pmr)
Joseph-Nathan, P. et al, Tetrahedron, 1974, 30, 3461 (1sol, struct)

)LY 1,7-Dihydroxy-1,3,5-bisabolatrien-15-oic Sq-00238

C15H 1,.03 M 252.353 acid
Cryst. (Et20fhexane). Mp 97-98°. [1X]i: +33.9° (c, 0.6 in 3-Hydroxy-4-(1-hydroxy-1,5-dimethylhexyl)benzoic acid,
9CI. Sydonic acid. Sydnic acid
dioxan).
l-Ac: [35334-73-7]. [65967-73-9]
C17H160 4 M 294.390
Constit. of Lindera triloba. Oil. [IX]i: + 207° (c, 1.4 in
dioxan). H~O
~
Takeda, K. eta/, Tetrahedron, 1971, 27, 6049. I _.9COOH

11
5,11-Dihydroxy-3,7(14)-bisaboladien-2-one Sq-00236
Cryptomerone C15Hn04 M 266.336
[24112-89-8] Isol. from Aspergillus sydowi. Needles (C6H 6). Mp 158-
1590. [1X]n + 0°.
11-Hydroxy: [65967-72-8]. 1,7,11-Trihydroxy-1,3,5-
bisabolatrien-15-oic acid. Hydroxysydonic acid
C1sHnOs M 282.336
Prod. by A. sydowi. Needles (Etpjhexane). Mp 135-
1360.
Absolute
configuration Hamasaki, T. et al, Agric. Bioi. Chern., 1978, 42, 37 (isol, struct)
OH Murali, D. et al, Indian J. Chern., Sect. B, 1987, 26, 156 (synth)
C1sH240 3 M 252.353
Constit. of wood of Cryptomeria japonica. Diperezone Sq-00239
2,4-Dinitropheny/hydrazone: Cryst. Mp 194.5-195°.
Ito, S. et al, Tetrahedron Lett., 1969, 3185.

C30H 380 6 M 494.627

Constit. of Perezia alamani var. oolepis. Red viscous oil.
[1X]46 + 13o (c, 1 in CHC1 3).
Joseph-Nathan, P. eta/, Phytochemistry, 1982, 21, 1129.

190
Elvirol - Heterocurvistone Sq-00240 - Sq-00247

Elvirol Sq-00240 Constit. of Stevia purpurea. Oil. Bp0 _1 125°. [oc]i;' + 117° (c,
2-(1 ,5-Dimethyl-4-hexenyl)-4-methylphenol, 9CI. 2-(1 ,5- 6.35 in CHC1 3).
Dimethyl-4-hexenyl)-p-cresol, 8CI Bohlmann, F. et al, Chern. Ber., 1976, 109, 3366.
[23479-73-4]
7,10-Epoxy-11-hydroxy-2-bisabolen-15-oic Sq-00244

~
acid

C 15H 110 M 218.338

\~
Isol. from the roots of Elvira biflora. Oil. Bp0 _06 62°.
?u~H
OH
Ac: Bp0 _06 59-60°.
C 15H 140 4 M 268.352
Me ether: Bp0 _07 62-63°.
Me ester: [126622-77-3].
Bohlmann, F. et al, Chern. Ber., 1974, 107, 1777 (isol, synth) Ct6H160 4 M 282.379
Dennison, N.R. et al, Aust. J. Chern., 1975, 28, 1339 (synth)
Constit. of Podolepis rugata. Oil. [oc]i;' -29° (c, 1 in
Pednekar, P.R. eta/, Indian J. Chern., Sect. B, 1980, 19, 1076
(synth) CHC1 3).
Jaensch, M. eta/, Phytochemistry, 1989, 28, 3497 (isol, pmr)
2,3-Epoxy-7,10-bisaboladiene Sq-00241
4-( 1,5-Dimethyl-] ,4-hexadienyl)-1-methyl-7- Furoixiolal Sq-00245
oxabicyclo[4.J.O]heptane, 9CI. 2-(3,4-Epoxy-4-

~
methylcyc/ohexyl)-6-methyl-2,5-heptadiene

(2R,3S,6S, 7Z)-form
OHC
c1sH1 60 1 M 228.290
Constit. of Ixiolaena leptolepis. Oil.
C 15H 140 M 220.354 Lehmann, L. et al, Phytochemistry, 1988, 27, 2994.
(2R,3S,6S,7Z)-form
Sex pheromone of the Southern green stinkbug Nezora
viridula. Oil. [ocln -14.7° (c, 1.2 in CHC1 3).
15-(2-Furoyloxy)-2,1 0-bisaboladien-7-ol Sq-00246
[126647-28-7]
[111536-37-9, 111613-35-5, 111613-41-3, 111613-42-4)
Baker, R. eta/, J. Chern. Soc., Chern. Commun., 1987, 414. OH

3,4-Epoxy-7(14), 10-bisaboladiene-1,2,8-
triol
Sq-00242
(<(l
)l~rncxx:O' 2 0

OOM~H
\
C10H 180 4 M 332.439
Constit. of Podolepis rugata. Oil.
~- Jaensch, M. et a/, Phytochemistry, 1989, 28, 3497 (isol, pmr)

C 15H 140 4 M 268.352

Heterocurvistone Sq-00247
1,2-Diangeloyl, 8-Ac: [79236-26-3]. [79421-85-5]
C 17H 380 7 M 474.593
Constit. of Seneciofulgens. Oil. [oc]~4 -15.8° (c, 0.12 in
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1981, 20, 469.

2,3-Epoxy-10-bisabolen-1-one Sq-00243
2,3-Epoxy-2,3-dihydro-1-bisabolone C 15H 140 1 M 236.353
[61432-72-2) Constit. of Heterotropa curvistigma. Oil. [oc]i;' -49.5° (c, 1
in MeOH).

(i\o
Niwa, M. et al, Phytochemistry, 1981, 20, 1137.

~~
M 236.353

191
1-Hydroxy-2,10-bisaboladien-15-... - 7-Hydroxy-3,10-bisaboladien-2-one Sq-00248 - Sq-00255

1-Hydroxy-2,10-bisaboladien-15-oic acid Sq-00248 6-Hydroxy-2,10-bisaboladien-1-one Sq-00252

1-Hydroxy-15-bisabo/oic acid 6-Hydroxy-2-bisabo/en-1-one
[96400-35-0)

Ct~H 24 0 3 M 252.353
Constit. of Stevia salicifolia. Oil (as Me ester). [a:Jn +41.3° CtsH240 2 M 236.353
(c, 0.22 in CHC1 3) (Me ester). Constit. of Asteriscus graveolens. Oil.
Ac: El Dahmy, S. et al, Tetrahedron, 1985, 41, 309.
C 17H 260 4 M 294.390
From S. salicifolia. Oil (as Me ester). [a:Jn +95° (c, 0.25
in EtOH) (Me ester). 7-Hydroxy-2,10-bisaboladien-1-one Sq-00253
Hernandulcin
Calderon, J.S. et al, Phytochemistry, 1984, 23, 186.
[95602-94-1]
7-Hydroxy-2,10-bisaboladien-15-oic acid Sq-00249

H~
C 15H 240 2 M 236.353
Constit. of Lippia dulcis. More than 1000 times as sweet as
Ct5H 240 3 M 252.353 sucrose. [a:)i,S +109° (c, 0.11 in EtOH).
Me ester: [126783-60-6]. Compadre, C.M. et al, Science (Washington, D.C.), 19H5, 227, 417
Ct6H 260 3 M 266.380 (struct)
Constit. of Podolepis rugata. Oil. Mori, K. eta/, Tetrahedron, 1986, 42, 5895 (synth)
Jaensch, M. eta/, Phytochemistry, 1989, 28, 3497 (isol, pmr)
7-Hydroxy-2,10-bisaboladien-9-one Sq-00254
4-Hydroxy-2,10-bisaboladien-1-one Sq-00250 rx.-Bisabolo/one
4-Hydroxy-1-bisabo/one [62697-50-1)

HO H

~CH,
C 15H 240 2 M 236.353 C 1 ~H 24 0 2 M 236.353
Constit. of Chrysanthemum flosculosum. Oil. [a:Jro -20.8°
4rx.-form [73695-95-1) (c, 1 in CHC1 3).
Constit. of Chrysothamnus nauseosus. Oil. [a:]~4 -15.2°
(c, 0.64 in CHC1 3). Bohlmann, F. et al, Tetrahedron Lett., 1972, 1295 (isol, struct)
Malanco, F.L. et al, Synth. Commun., 1976, 6, 515 (synth)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1889. Kergomard, A. et al, Tetrahedron, 1977, 33, 2215 (synth, abs
config)
4-Hydroxy-2,1 0-bisaboladien-9-one Sq-00251
7-Hydroxy-3,1 0-bisaboladien-2-one Sq-00255

H\0:
Delobanone
[35346-20-4)

C 15H 240 2 M 236.353

Constit. of Curcuma tonga. Viscous oil. [1X)n +51 ° (c, 0.22
in MeOH).
Me ether, 5P-hydroxy: 5-Hydroxy-4-methoxy-2,10- C 15H 240 2 M 236.353
bisaboladien-9-one Constit. of Lindera triloba. Oil. [a:]i;' + 10.2° (c, I in
C 16H 260 3 M 266.380 dioxan).
Constit. of C. longa. Viscous oil. [a:Jn -7.4° (c, 0.11 in Takeda, K. et al, Tetrahedron, 1971, 27, 6049 (isol)
MeOH). Harwood, L.M. et al, Tetrahedron Lett., 1980, 1743 (synth)
Ohshiro, M. eta/, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr)

192
11-Hydroxy-2,7-bisaboladien-9-one - 5-Hydroxy-2,5,10-bisabolatriene-1,4-... Sq-00256 - Sq-00262

11-Hydroxy-2,7-bisaboladien-9-one Sq-00256 Constit. of wood of Abies sachalinensis. Needles

Atlantolone (EtOAc). Mp 98-102°. [1X]i,5 + 14.0° (c, 1.2 in EtOH).
(7R,9S,trans)-form [86333-79-1]

0~
Constit. of wood of A. sachalinensis. Needles (EtOAc).
Mp 123-129°. (1X]n +7.6° (c, 1.05 in EtOH).
Numata, A. et a/, Chern. Pharm. Bull., 1983, 31, 436.

12-Hydroxy-1,3,5,10-bisabolatetraen-15-al Sq-00260
OH 12-llydroxy-~-curcumen-15-al
C 15H 240 2 M 236.353

~CHO
Constit. of the wood of Cedrus deodara. Oil. Bp 1 150-155°.
[1X]n + 2.87° (c, 0.49 in CHC1 3).
Shankaranarayan, R. et a/, Tetrahedron, 1977, 33, 1201.

12-Hydroxy-2,1 0-bisaboladien-1-one Sq-00257

12-Hydroxy-1-bisabolone
C 15H 200 2 M 232.322
Ho Constit. of Gochnatia paniculata. Oil.

~
12-Aldehyde: 1,3,5,10-Bisabolatetraene-12,15-dial. ~­
Curcumene-12 ,15-dial
CtsH180 2 M 230.306
Constit. of G. paniculata. Oil.
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 191.
12

C 15H 240 2 M 236.353

2-Hydroxy-2,5, 10-bisabolatriene-1,4-dione Sq-00261
12-Ac: [81053-38-5]. 12-Acetoxy-1-bisabolone 5-( 1,5-Dimethyl-4-hexenyl)-3-hydroxy-2-methyl-2,5-
C17H 21;03 M 278.391 cyclohexadiene-1 ,4-dione, 9CI. 1soperezone

W
Constit. of Senecio smithii. Oil. [1X]i; -17.7° (c, 0.6 in
CHC1 3). [13120-66-6]
12-Aldehyde: [81053-37-4]. 1-0xo-2,10-bisaboladien-12-al.
1-0xo-12-bisabolal
C 15H 220 2 M 234.338 H
Constit. of S. smithii. Oil. I
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 2389.
0
15-Hydroxy-2,1 0-bisaboladien-1-one Sq-00258 C15H 200 3 M 248.321
15-Hydroxy-1-bisabolenone Yellow plates. Mp 97-98°.
[65526-72-9] Ac: 2-Acetoxy-2-desoxyperezone
Ct7Hzz04 M 290.358

~OH
Constit. of Coreopsis longipes. Yellow oil. Descr. as the
(R)-form in CA, but no evidence for this in the lit.
(97763-23-0]
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2858 (isol)
Garcia, G.E. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 1055 (synth)
Enksen, A. eta/, J. Org. Chern., 1990, SS, 1177 (synth)
CtsH240z M 236.353
Constit. of Stevia ovata. Oil.
5-Hydroxy-2,5,10-bisabolatriene-1,4-dione Sq-00262
Ac: [65526-71-8].

M
Ct7Hz603 M 278.391
Constit. of S. ovata.

XY
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 3572.

9-Hydroxy-15-bisabolanoic acid Sq-00259

4-(3-Hydroxy-l ,5-dimethylhexyl)-cyclohexanecarboxylic
acid, 9CI. Tetrahydrotodomatuic acid C 15H 200 3 M 248.321

M
(R)-form [3600-95-1] Perezone. Pipitzahoic acid
Constit. of Trixis piptzhuac, Perezia spp., Acoutria
(7R,9S-cis)-form thurberi, Jungia spectabilis, J. malvaefolia, Coreopsis
HO~~ ~COOH mitica and Bidens andicola (sometimes as isovalerate or
angelate). Golden-yellow leaflets (HzO). Mp 104-106°.
[1X]i? -17° (EtzO).
CtsH280 3 M 256.384 Me ether: [33418-02-9].
(7R,9S,cis)-form [86279-09-6] Ct6H 220 3 M 262.348
Constit. of C. spp. Yellow oil.

193
15-Hydroxy-2,7(14),10-bisabolatrien-... - 7-Isocyano-2,10-bisaboladiene Sq-00263 - Sq-00268

5-Deoxy: [69301-26-4]. 2,5,10-Bisabo/atriene-1,4-dione. 10-Hydroxy-3,7(14),11-bisabolatrien-2-one Sq-00265

Curcuquinone. 6-Deoxyperezone [119765-83-2]
C 15H 100 2 M 232.322
Constit. of Wyethia helenioides, Bidens spp. and the
gorgonian Pseudopterogorgia rigida. Yellow oil. [ex]i;'
-33.SO (c, 0.93 in CHC1 3) ( -1.3°).
5-Deoxy, 2-acetoxy: [89913-50-8]. 2-Acetoxycurcuquinone
C 17H 220 4 M 290.358
Isol. from aerial parts of C. fasciculata. Yellow oil.
[78964-28-0, 100761-40-8]
Arigoni, D. eta/, Helv. Chim. Acta, 1954, 37, 881 (abs config) C 15H 210 2 M 234.338
Joseph-Nathan, P. et a/, Org. Magn. Reson., 1971, 3, 23 (cmr) Constit. of Mikania shushunensis. Oil. [ex]~ -16.2° (c, 0.5
Joseph-Nathan, P., Rev. Soc. Quim. Mex., 1974, 18, 226 (rev) in CHCI 3).
Joseph-Nathan, P. et a/, Tetrahedron, 1977, 33, 1573 (struct, bib/)
McEnroe, F.J. et at, Tetrahedron, 1978, 34, 1661 (Curcuquinone) Gutierrez, A.B. eta/, Phytochemistry, 1988, 27, 3871.
Sanchez, I.H. eta/, J. Org. Chern., 1981, 46, 4666; 1985, 50, 5077
(synth) Isocaespitol Sq-00266
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2245; 1983, 22,
1286, 2858 (derivs) [53915-39-2]
Garcia, G.E. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 1055 (synth)
Enksen, A. eta/, J. Org. Chern., 1990, 55, 1177 (synth)
Br,x::o-OH

15-Hydroxy-2,7(14),10-bisabolatrien-12- Sq-00263 H' Br

oic acid ',
Brasilic acid I

Cl
C 15H 25 Br2Cl02 M 432.622
Constit. of Laurencia caespitosa. Cryst. (hexane). Mp 92-
930. [exln -15°.
Deoxy: [74323-44-7]. 8-Deoxyisocaespitol
C 15H 25Br2CIO M 416.623
Constit. of L. caespitosa. Cryst. Mp 95-96°. [exln -27°.
[74364-62-8]
C 15Hn03 M 250.337 Gonzalez, A.G. eta/, Tetrahedron, 1975, 31, 2449 (isol, struct)
15-Ac: Gonzalez, A. eta/, Tetrahedron Lett., 1976, 2279; 1979, 2719;
C 17H 240 4 M 292.374 1980, 187 (synth, iso/, cmr)
Constit. of Brasilia sickii. Gum. Chang, M. eta/, Phytochemistry, 1989, 28, 1417 (abs config)
15-Ac, Me ester: Gum. [ex]14 -55° (c, 0.87 in CHCI 3).
15-A/dehyde: [88321-04-4]. 15-0xo-2,7(14),10-bisabo/atrien- 7-Isocyanato-2, 10-bisaboladiene Sq-00267
12-oic acid 7- /socyanato-7,8-dihydro-ex-bisabo/ene
C 15H 100 3 M 248.321
Isol. from B. sickii. Gum.
15-Aldehyde, Me ester: Gum. [ex]i;' -70° (c, 2.4 in CHCI 3).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1213.

6-Hydroxy-2,7,1 0-bisabolatrien-9-one Sq-00264

6-Hydroxyatlantone. Atlanton-6-o/ C 16H 25NO M 247.380
(6R,7R)-form [105281-35-4]

~
Constit. of a Ciocalypta sp. Oil. [ex]~ -24.3° (c, 0.094 in
hexane).
Gulavita, N.K. eta/, J. Org. Chern., 1986, 51, 5136 (isol, cryst
struct)
C 15Hn02 M 234.338
(E)-form 7-Isocyano-2,1 0-bisaboladiene Sq-00268
Constit. of Cedrus libanotica. Oil. [ex]i;5 +0.15° (c, 1.2 in 7- /socyano-7,8-dihydro-ex-bisabo/ene
CHC1 3).
Avcibasi, H. et a/, Phytochemistry, 1987, 26, 2852.

C 16HzsN M 231.380
(6R,7R)-form [105281-36-5]

194
Lasiocarpenonol- 9-0xo-2,7-bisaboladien-15-oic acid Sq-00269 - Sq-00276

Constit. of a Ciocalypta sp. Oil. [cx]i; -49.9° (c, 0.033 in Constit. of Senecio digitalifolius. Oil. Bp 0 . 1 130°. [cx]i:
hexane). -39.4° (c, 4.1 in CHCI 3).
Gulavita, N.K. eta/, J. Org. Chern., 1986, 51, 5136. [71883-90-4, 71883-91-5]
Bohlmann, F. et a/, Phytochemistry, 1978, 17, 759 (isol)
Lasiocarpenonol Sq-00269 Vig, O.P. et al, Indian J. Chern., Sect. B, 1979, 18, 36 (synth,
spectra)
[125290-13-3]
6-(4-Methylphenyl)-1-hexene Sq-00273
1-Methyl-4-(1-methyl-5-hexenyl)benzene, 9CI. 6-p-Tolyl-1-
hexene. 5,6-Dehydrosenedigitalene. 13-Nor-1,3,5,11-
bisabolatetraene
[70329-63-4]

C 15H 200 3 M 248.321

Constit. of Abies lasiocarpa.
2-Deoxy: [55708-41-3]. Lasiocarpenone
C 15H2002 M 232.322
Constit. of A. lasiocarpa and A. balsamea.
Manville, J.F. eta/, Can. J. Chern., 1975, 53, 1579 (isol) C14H20 M 188.312
Manville, J.F. et al, Phytochemistry, 1989, 28, 3073 (isol, pmr, cmr)
(R)-form [68326-18-1]
Cons tit. of Senecio digitalifolius. Oil.
Libanotic acid Sq-00270
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 759 (isol)
4-( 1-Methyl-3-oxobutyl)-1-cyclohexene-1-carboxylic acid,
9CI. 11,12,13- Trinor-9-oxo-2-bisabolen-15-oic acid
[119765-97-8] Norbisabotide Sq-00274
Dihydro-5-methyl-5-(4-methyl-3-cyclohexen-1-yl)-2(3H)-

Oro<=H
furanone, 9CI
[55169-27-2]

C 12H 180 3 M 210.272

Constit. of Cedrus libani. Oil.
Avcibasi, H. et al, Phytochemistry, 1988, 27, 3967.
C 12H 180 2 M 194.273
4-(4-Methyl-3-cyclohexenyl)-3-penten-2- Sq-00271 Constit. of Atalantia monophylla. Oil. Bp0 . 3 130-135°.
one Shingapure, J.D. et al, Indian J. Chern., Sect. B, 1976, 13, 24 (isol,
struct)
[57819-74-6] Ho, T.-L., Synth. Commun., 1983, 13, 341 (synth)

1-0xo-2,10-bisaboladien-12~oic acid Sq-00275

1-0xo-12-bisabolic acid

H 0

~
C 12H 180 M 178.274
Constit. of Cedrus atlantica and C. deodara. Oil. Bp0.08
110°. [cx]~ +25° (CHCI 3).
Adams, D.R. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1502
(isol, synth)
Vig, O.P. et al, Indian J. Chern., Sect. B, 1976, 14, 378 (synth)
C 15H 220 3 M 250.337
3-Methyl-6-(1-methyl-5-hexenyl)-2- Sq-00272 Me ester: [70329-67-8].
cyclohexen-1-one C 16H 240 3 M 264.364
1,2-Dihydro-2-senedigitalone. 13-Nor-2,11-bisaboladien-1- Constit. of Baeria spp. Oil. [cx]i; - 14° (c, 3.9 in CHC1 3).
one Bohlmann, F. et al, Phytochemistry, 1978, 17, 2032.
[68326-17-0]
9-0xo-2,7-bisaboladien-15-oic acid Sq-00276
4-( 1,5-Dimethyl-3-oxo-1-hexenyl)-1-cyclohexene-1-carboxylic
Relative acid, 9CI. Atlantonic acid
configuration [1200 19-19-4]

M 206.327
~
8
UCOOH

195
9-0xo-15-bisabolanol- 9-0xo-2-bisabolen-15-oic acid Sq-00277 - Sq-00280

C 15H 120 3 M 250.337 Constit. of the wood of Pseudotsuga menziesii. Oil. [1X]~4
Constit. of Cedrus libani. Oil. + 85.7° (c, 0.25 in CHCI 3).
Avcibasi, H. eta/, Phytochemistry, 1988, 27, 3967. Sakai, T. eta/, Chern. Lett., 1973, 491.

9-0xo-15-bisabolanol Sq-00277 9-0xo-2-bisabolen-15-oic acid Sq-00280

Dihydropseudotsugonol Todomatuic acid. Dihydroatlantonic acid
[52363-42-5] [6753-22-6]

C 15H:zs0 2 M 240.385 C 15H 240 3 M 252.353

Constit. of Pseudotsuga menziesii. Oil. [1X]~4 +4.3° (c, 0.53 Constit. of Abies sachalinensis and Cedrus libani. Cryst.
in CHCI 3). (pet. ether). Mp 58 .SO. Bp 3 200-215°. [1X]~· 5 + 85.8°.
15-A/dehyde: [52363-41-4]. 9-0xo-15-bisabo/ana/. Me ester: [17904-27-7]. Juvabione
Dihydropseudotsugonal C 16H 260 3 M 266.380
C 15H 260 2 M 238.369 Constit. of the wood of A. spp. Shows juvenile hormone
Constit. of P. menziesii. activity. Oil. d~0 1.010. Bp 15 209-212°. [1X]i? + 79.SO (c,
Sakai, T. eta/, Chern. Lett., 1973, 825. 3.5 in CHCI 3). ni? 1.4803.
Sakai, T., Int. Congr. Essent. Oils, [Pap.], 6th, 1974, 152. 7-Epimer: Epitodomatuic acid
C15H 240 3 M 252.353
9-0xo-1,3,5-bisabolatrien-15-oic acid Sq-00278 Constit. of A. pinsapo. Oil. [1X]i;l + 71.2° (c, 1 07 in
4-(1 ,5-Dimethy/-3-oxohexyl)benzoic acid, 9CI CHCI 3).
[17844-11-0] 7-Epimer, 10,11-didehydro: 4'-Dehydroepitodomatuic acid
C 15H 120 3 M 250.337

rYJ
Constit. of A. pinsapo. Solid. Mp 56-58°. [1X]i~ +94.0° (c,
0.71 in CHCI 3).
7-Epimer, 9-A/coho/: 3'-Dihydroepitodomatuic acid
o~~COOH C15H 260 3 M 254.369
Constit. of A. pinsapo. Syrup. [1X]i;l +51.6° (c. 0.97 in
CHCI 3).
C15H 200 3 M 248.321 7-Epimer, 2,3-Dihydro: cis-Dihydroepitodomatuic acid
(R)-form C15H 260 3 M 254.369
ar-Todomatuic acid Constit. of A. pinsapo. Syrup.
Constit. of wood oil of Pseudotsuga menziesii. 9R-Alcohol, Me ester: [60497-70-3]. lsojuvabiol
Me ester: [25151-84-2]. ar-Juvabione C16H:zs0 3 M 268.395
C1 6H 120 3 M 262.348 Constit. of wood of A. balsamea. Oil.
Shows juvenile hormone activity. [1X]i;' -18.8° (c, 0.32 in 9S-Alcoho/, Me ester: [60134-56-7]. Juvabiol
EtOH). Cl6H:zs03 M 268.395
15-A/dehyde: [42719-56-2]. 9-0xo-1,3,5-bisabolatrien-15-a/. Constit. of the wood of A. spp.
ar-Pseudotsugonal 10,11-Didehydro, Me ester: Dehydrojuvabione
C 15H 200 2 M 232.322 C16H 240 3 M 264.364
Constit. of the wood of P. menziesii. Oil. [1X]~4 -23.9° (c, Constit. of A. balsamea. Shows juvenile hormone
0.57 in CHCI 3). activity. Oil. [1X]i? + 102.SO (c, 3.6 in CHCI 3).
(±)-form [120019-18-3]
Mp 77-78°. Bpu 177-182°. Sakai, T. eta/, Chern. Lett., 1973, 491 (struct)
Sakai, T. eta/, Chern. Lett., 1973, 491, 825 (isol, struct) Trost, B.M. eta/, Tetrahedron Lett., 1975, 3797 (synth)
Mane, R.B. et a/, Indian J. Chern., 1973, 11, 615 (synth) Manville, J.P. eta/, Can. J. Chern., 1976, 54, 2365; 1977, 55, 2547
Blanch, C. eta/, An. Quim., 1975, 71, 446 (synth) (isol, struct, cmr, derivs)
Kavitake, B.P. et a/, Indian J. Chern., Sect. B, 1986, 25, 178 (synth) Negishi, E. eta/, Tetrahedron, 1976, 32, 925 (synth)
Evans, D.A. et a/, J. Am. Chern. Soc., 1980, 102, 774 (synth)
Williams, D.R. eta/, J. Org. Chern., 1981, 46, 5452 (synth)
9-0xo-2-bisabolen-15-al Sq-00279 Morgans, D.J. et a/, J. Am. Chern. Soc., 1983, 105, 5477 (synth)
Pseudotsugonal Avcibasi, H. eta/, Phytochemistry, 1988, 27, 3967.
[42719-55-1] Barrero, A.F. eta/, Phytochemistry, 1989, 28, 2617 (derivs)
Fujii, M. eta/, Bull. Chern. Soc. Jpn., 1990, 63, 1255 (1ynth)

0~CHO
M 236.353

196
Paniculide A - Puertitol B Sq-00281 - Sq-00284

Paniculide A Sq-00281 7,14-Deepoxy, 7,14-dihydroxy, [3-0-acetyl-6-deoxy-P-D-

glucopyranosy/( 1-+ 2)-3-0-acetyl-6-deoxy-P-D-
[21764-32-9]
glucopyranosy~ester: [81558-17-0]. Phyllanthostatin 3
C 40 H~0 18 M 822.856
Isol. from P. acuminatus. Shows antitumour props.
Amorph. Mp 126-130°. [a]i;' + 15.7° (c, 0.76 in CHC1 3).
[4-0-Acetyl-6-deoxy-P-n-glucopyranosyl(l-+2)-3-0-acetyl-6-
deoxy-p-n-glucopyranosy~ ester: Phyllanthostatin 4
C 40 H~2 0 17 M 804.841
Constit. of P. acuminatus as aq., equilibration prod. of
Phyllanthoside. Amorph. solid + !H20. Mp 122-126°.
[a]~ + 14.7° (c, 0.95 in CHC1 3).
Ct~H 10 0 4 M 264.321
Prod. in tissue culture by Andrographis paniculata. Cryst. [4-0-Acety/-6-deoxy-P-n-glucopyranosy/(1-+2)-4-0-acetyl-6-
Mp 120-121°. deoxy-p-n-glucopyranosy~ ester: Phyllanthostatin 5
C40H 520 17 M 804.841
15-Hydroxy: [21764-33-0]. Paniculide B
Constit. of P. acuminatus as aq. equilibration prod.
C 15H 100 5 M 280.320
Amorph. solid. Mp 100-102°.
Prod. by A. paniculata. Cryst. Mp 145-146°. [aln +4°
(MeOH). [6-Deoxy-P-n-glucopyranosy/(1-+2)-P-n-g/ucopyranosy~
ester: Phyllanthostatin 6
15-Hydroxy, 8-ketone: [21764-34-1]. Paniculide C
C36 H 480 16 M 736.766
Ct5Hta05 M 278.304 Constit. of P. acuminatus. Amorph. Mp 136-139°. [a]i;'
Prod. by A. paniculata. Oil. [aJn + 37° (MeOH).
+ 12.0° (c, 0.25 in CH 2C12).
Allison, A.J. et al, J. Chern. Soc., Chern. Commun., 1968, 1493
(isol) Kupchan, S.M. eta/, J. Am. Chern. Soc., 1977, 99, 3199 (cryst
Smith, A.B. eta/, J. Org. Chern., 1981, 46, 4814 (synth) struct)
Kido, F. et al, J. Chern. Soc., Chern. Commun., 1982, 1209 (synth) Pettit, G.R. et a/, Can. J. Chern., 1982, 60, 544, 939 (struct)
Smith, A.B. et a/, J. Am. Chern. Soc., 1983, lOS, 575 (synth) McGuirk, P.R. eta/, J. Am. Chern. Soc., 1982, 104, 4496 (synth)
Jacobi, P.G. et a/, Tetrahedron Lett., 1984, 25, 4859 (synth) Williams, D.R. et a/, J. Am. Chern. Soc., 1984, 106, 2949 (synth)
Baker, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1985, 1509 (synth) Pettit, G.R. eta/, J. Org. Chern., 1984, 49, 4258; 1985, SO, 5060
Kido, F. et a/, Tetrahedron, 1987, 43, 5467 (synth) (isol, cryst struct)
Jacobi, P. eta/, Tetrahedron, 1987, 43, 5475 (synth) Burke, S.D. eta/, J. Org. Chern., 1985, SO, 3420 (synth)
Smith, A.B. eta/, J. Am. Chern. Soc., 1987, 109, 1269 (synth)
Martin, S.F. et al, J. Org. Chern., 1987, 52, 3706 (synth)
Phyllanthocic acid Sq-00282 Smith, A.B. eta/, Tetrahedron Lett., 1987, 28, 5591 (synth)
Pettit, G.R. et a/, J. Nat. Prod. (Lloydia), 1990, 53, 1406

~~
(Phyllanthostatin 6)
Burke, S.D. et a/, J. Org. Chern., 1990, SS, 2138 (synth)

~~~COOH
COO H
Puertitol A
2-Bromo-3-chloro-6,1 0-bisaboladien-9-ol
Sq-00283

;d [119736-67-3]
Ph
C24H 280 7 M 428.481
Phyllanthocic acid (so named as such here) has not been
well characterized.
Me ester: [62948-37-2]. Phyllanthocin
C25H 300 7 M 442.508
Key aglycone from phyllanthoside and
phyllanthostatins. Cryst. (Et20/hexane). Mp 126-127°. R 1 = Br, R2 = Cl
[a]~4 +25.2° (c, 2 in CC14). C 15H 24 BrC10 M 335.711
[3-0-Acetyl-6-deoxy-P-n-glucopyranosy/(1-+2)-3-0-acety/-6- Constit. of Laurencia obtusa. Oil. [aln -37° (c, 1.62 in
deoxy-P-n-g/ucopyranosy~ ester: [63166-73-4]. CHC13).
Phyllanthoside Vazquez, J.T. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 1257 (isol,
C40H52017 M 804.841 pmr, cmr, cd)
Constit. of Phyllanthus brasiliensis. Shows antitumour
props. Amorph. Mp 125-126°. [a]~4 + 19.2° (c, 2 in
CHC1 3). Undergoes equilibration with Phyllanthostatin 1 Puertitol B Sq-00284
in soln. 3-Bromo-2-ch/oro-6,10-bisabo/adien-9-o/
[3-0- Acetyl-6-deoxy-P-n-glucopyranosyl( 1-+ 2)-4-0-acety/-6- [119736-69-5]
deoxy-P-n-glucopyranosy~ ester: [82209-93-6]. As Puertito1 A, Sq-00283 with
Phyllanthostatin 1
C 40 H~ 2 0 17 M 804.841
R1 = C1, R 2 = Br
Constit. of P. acuminatus. Shows antitumour props. C 15H 24BrC10 M 335.711
Amorph. Mp 125-126°. [a]~ -3.6° (c, 0.83 in CHC1 3). Constit. of Laurencia obtusa. Oil. [aln +66° (c, 0.25 in
[3-0-Acetyl-6-deoxy-P-n-glucopyranosyl(1-+2)-3-0-acetyl-P- CHC1 3).
D-glucopyranosy~ ester: [81558-18-1]. Phyllanthostatin 1 Vazquez, J.T. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 1257 (isol,
C 40 H~ 2 0 18 M 820.840 pmr, cmr, cd)
Isol. from P. acuminatus. Shows antitumour props.
Amorph. Mp 134-136°. [a]i;' +9.33° (c, 0.75 in CHC1 3).

197
Senedigitalene - Yingzhaosu A Sq-00285 - Sq-00291

Senedigitalene Sq-00285 Theonelline formamide Sq-00288

1-Methyl-4-(1-methyl-5-hexenyl)-1 ,3-cyclohexadiene, 9CI. [94663-93-1)
13-Nor-3,5,11-bisabolatriene

~
[71046-97-4]

X
X= NHCHO
C 16H 27NO M 249.395
C14H22 M 190.328 Constit. of the sponge Theonella cf. swinhoei. Oil.
(R)-form [68326-21-6) Nakamura, H. eta/, Tetrahedron Lett., 1984, 25, 5401.
Norsesquiterpene from Senecio digitalifolius and S.
paludaffinis. Oil. Bp0 . 1 70°. [cxn:9 -32.6° (c, 1.38 in Theonelline isocyanide Sq-00289
CHC1 3). 4-(1 ,5-Dimethyl-1 ,3-hexadienyl)-1-isocyano-1-
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 759 (isol, struct) methylcyclohexane, 9CI. 3-Jsocyanotheonellin. 3-Isocyano-
7,9-bisaboladiene
Sesquicineol Sq-00286 [1 05281-40-1)
3,7-Epoxy-10-bisabolene. 3,7-0xido-10-bisabolene As Theonelline formamide, Sq-00288 with
[90 131-02-5]
X= NC
C16H 25 N M 231.380
Constit. of a Phyllidia sp. Oil.
Gulavita, N.K. eta/, J. Org. Chern., 1986, 51, 5136.

C 15H 260 M 222.370 Theonelline isothiocyanate Sq-00290

Constit. of Senecio subrubriflorus, Anthemis alpestris, [94663-94-2)
Aydendron barbeyana and Boronia megastigma. As Theonelline formamide, Sq-00288 with
Perfumery compound. Oil. Bp5 90-94°, Bp0 . 1 120°. [cx)i;'
-8.4° (c, 4.06 inCHC1 3). X= -NCS
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1697 (isol) C16H 25NS M 263.446
Pascual Teresa, J. de. eta/, Tetrahedron, 1988, 44, 5109 (synth, ir,
pmr, cmr, ms)
Constit. of the sponge Theonella cf. swinhoei. Oil.
Weyerstahl, P. et a/, Tetrahedron, 1990, 46, 3503 (synth) Nakamura, H. eta/, Tetrahedron Lett., 1984, 25, 5401.

Sydowic acid Sq-00287 Yingzhaosu A Sq-00291

Sydwic acid [7330 1-54-9)
OH
~COOH
+o) Hd='
C 15H 20 0 4 M 264.321
(-)-form [55708-43-5)
Metab. of Aspergillus sydowi. Cryst. (EtzO/hexane). Mp
151°. [cx]i} -6.4° (c, l.l in CHC1 3).
(±)-form [63087-77-4] C 1 ~H 260 4 M 270.368
Cryst. (EtOAcjhexane). Mp 144°. Constit. of Artabotrys unciatus.
Hamasaki, T. eta/, Agric. Bioi. Chern., 1975, 39, 2337 (iso/, struct) Zhang, L. eta/, J. Chern. Soc., Chern. Commun., 1988, 523.
Fukuyama, K. eta/, Agric. Bioi. Chern., 1976, 40, 7053 (cryst
struct)
Vijayasarathy, P.R. eta/, J. Chern. Soc., Perkin Trans. I, 1977, 34
(synth)
Hamasaki, T. et a/, Agric. Bioi. Chern., 1978, 42, 37 (iso/, synth)

198
Agglomerone - Cabreuva oxide Sq-00292 - Sq-00298

3,7-Bis(hydroxymethyl)-l-benzoxepin- Sq-00295
5(2H)-one
Miscellaneous [60355-21-7]
0
cyclohexane HOH2 C c
1 Q' CH2 0H

sesquiterpenoids C12H 120 4 M 220.224

"':::,.. 0

Constit. of Marasmiellus ramealis. Cryst. (EtOAcjpet.

ether). Mp 100-IOO.SO.
Holroyde, J.K. eta/, J. Chern. Soc., Perkin Trans. 1, 1978, 1490.
Agglomerone Sq-00292
[22595-43-3]
Sq-00296

Absolute
C13H 180 4 M 238.283 configuration
Tautomeric. Indexed under several different names in CA.
Oxo-form is shown. Obt. from leaves of Eucalyptus C12H 16BrC10 2 M 307.614
agg/omerata and E. mckieana. Cryst. (pet. ether). Mp Metabolite of red alga Laurencia caespitosa. Mp 122-123°.
74~75°. Bp 10 140°.
[exJn + 16.0° (c, 0.23 in CHC13).
Hellyer, R.O. eta/, Aust. J. Chern., 1964, 17, 1418 (isol, uv, pmr, Estrada, D.M. et a/, Tetrahedron Lett., 1987, 28, 687 (cryst struct)
struct)
Baigent, D.R. eta/, Aust. J. Chern., 1973, 26, 2065 (synth)
3-(3-Bromo-4-chloro-4-methylcyclohexyl)- Sq-00297
Andirolactone Sq-00293 4-oxo-2-pentenoic acid, 9CI
Cl

0~
I
Br

Absolute
0 ""<:::::,
C 11H 140 2 M 178.230 configuration
Constit. of Cedrus libanotica. Oil. [ex]~ + 3.2° (c, 2.1 in COOH
CHC1 3). C12H 16BrC103 M 323.613
Avcibasi, H. eta/, Phytochemistry, 1987, 26, 2852. Me ester: [112515-90-9].
C 13H 18BrC103 M 337.640
Antibiotic FR 65814 Sq-00294 Metabolite of red alga Laurencia caespitosa. Cryst. Mp
FR. 65814 52-53°. [exJn +37° (c,0.14 in CHC1 3).
[103470-60-6] Estrada, D.M. et a/, Tetrahedron Lett., 1987, 28, 687 (cryst struct)

Cabreuva oxide Sq-00298

3,4,4a,7,8,8a-Hexahydro-J ,1 ,3,6-tetramethy/-3-viny/-JH-2-
benzopyran

OH
C 15H2404 M 268.352 (3S,4aS,8aS)-:form
Prod. by Penicillium jensenii. Shows immunosuppressive
activity. Prisms (Etpjpet. ether). Mp 46-47°. [ex]i;
-38.4° (c, 2.4 in MeOH). Related to Fumagillin, Sq- C15H240 M 220.354
00303. (3S,4aS,8aS)-form
Japan. Pat., 86 38 181, (1986); CA, 105, 59452 (isol) Cabreuva oxide A
Hatanaka, H. eta/, J. Antibiot., 1988, 41, 999 (isol, struct) Constit. of cabreuva oil (Myrocarpus fastigiatus). Oil.
[ex]~ +28.4° (c, 1 in CHC1 3).
(3S,4aS,8aR)-form
Cabreuva oxide B
From cabreuva oil. Oil. [ex]~ + 115.4° (c, 1.4 in CHC1 3).
(3S,4aR,8aR)-form
Cabreuva oxide C

199
Conyaegyptin - Fumagillin Sq-00299 - Sq-00303

From cabreuva oil. Oil. [oc]~ -43.1° (c, 1.1 in CHC1 3). FraxineUone Sq-00302

co
(3S,4aR,8aS)-form [28808-62-0]
Cabreuva oxide D
From cabreuva oil. Oil. [oc]~ -178.5° (c, 0.9 in CHC1 3).
[107602-52-8, 107602-53-9, 107602-54-0, 107602-55-1)
Maurer, B. eta/, Helv. Chim. Acta, 1986, 69, 2026. I

Conyaegyptin Sq-00299 ~0
c14Hl,o3 M 232.279
Constit. of Dictamus a/bus. Cryst. (EtOH/EtzO). Mp 116°.
[ocJi? -44° (EtOH).
Pailer, M. eta/, Monatsh. Chern., 1965, 96, 1324 (uv, ir, pmr, ms)
Coggon, P. eta/, J. Chern. Soc. B, 1970, 1521 (cryst struct)
Fukuyama, Y. eta/, Tetrahedron Lett., 1972, 3401 (synth)
Tokoroyama, T. eta/, J. Chern. Soc., Perkin Trans. I, 1981, 1557
(synth)
C 35 H 540 7 M 586.807 Woo, W.S. eta/, Planta Med., 1987, 53, 399 (isol, use)
Constit. of Conyza aegyptica. Gum.
Zdero, C. eta/, Phytochemistry, 1990, 29, 3167 (isol) Fumagillin, BAN, INN Sq-00303
Phagopedin sigma. Amebaci/in. Fumidil. Fugillin. Amebex.
Cybrodol Sq-00300 Fumadil B. NSC 9168. U 5762
4-(Hydroxymethyl)-3-(3-hydroxy-2-methyl-1-propenyl)-2,6- [23110-15-8]
dimethy/benzeneethano/, 9CI
I
CHzOH

(E)-form
'OMe
I

OOC~COOH
CtsH22 0 3 M 250.337 C26H 340 7 M 458.550
(E)-form [75225-88-6] Isol. from Aspergillus fumigatus H3 and Penicillium
Constit. of Cyathus bulleri. Oil. nigricans. Antibiotic, with antiphage and amoebicidal
props. Inhibits RNA synthesis of Octosporea muscae-
]-Carboxylic acid: [75225-86-4]. Cybrodic acid
domesticae. Of limited use for the treatment of drug-
C 15H 200 4 M 264.321
resistant intestinal amoebiasis. Yellow needles (MeOH
Constit. of C. bulleri. Cryst. Mp 176-178°.
aq.). Sol. dil. alkalis; insol. hydrocarbons, Hp. Mp 189-
1,1'-Dia/dehyde: [75225-85-3]. Cybrodal 1940. [oc]~ -26.6° (MeOH). Best stored in dark, evac.
Ct5 H 180 3 M 246.305 ampoules at low temp.
Constit. of C. bul/eri. Oil.
I> H£1750000.
(Z)-form [75225-87-5]/socybrodol
Deacy/: [108102-51-8]. Fumagillol
From C. bulleri. Cryst. Mp 102-103°.
C 16H 260 4 M 282.379
Ayer, W.A. eta/, Can. J. Chern., 1981, 59, 2150, 2159 (isol, synth) Isol. from P. jensenii. Degradn. prod. of Fumagillin.
Carcinolytic agent. Immunosuppressant. Cryst.
Fraginol Sq-00301 (Etpjpet. ether). Mp 55.5-56°. [oc]i; -68.0° (c, 1.73 in
[34328-48-8] EtOH). Similar to FR 65814.
Decylamine salt: Mp 163-165°.
Dicyc/ohexylamine salt: Mp 147-148° dec.
HOAOH Me ester: Needles (MeOH aq.). Mp 151-152°.

~ 0 0
Bis-2,4-dinitropheny/hydrazone: Mp 123-126°.
Eble, T.E. eta/, Antibiot. Chemother., 1951, 1, 54.
Ross, J.M. eta/, J. Am. Chern. Soc., 1956, 78, 4675 (Fumagillol)
C 13H 180 4 M 238.283 Cross, A.D. eta/, J. Am. Chern. Soc., 1958, 80, 3682.
Constit. of Dryopteris fragrans. Cryst. Mp 78-80°. Carman, R.M. eta/, J. Am. Chern. Soc., 1959, 81, 31.51.
Molodozlmikova, L.M. eta/, Khim.-Farm. Zh., 1971, 5, 32; CA, Tarbell, D.S. eta/, J. Am. Chern. Soc., 1960, 82, 1005 (struct)
75, 115854x. Birch, A.J. eta/, J. Chern. Soc. C, 1969, 1473 (biosynth)
Corey, E.J. eta/, J. Am. Chern. Soc., 1972, 94, 2549 (~ynth)
Hatanaka, H. et a/, J. Antibiot., 1988, 41, 999 (Fumagillol)
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 810.
Sax, N.J., Dangerous Properties of Industrial Materials, 6th Ed.,
Van Nostrand-Reinhold, 1984, 1460.

200
Furocaespitane - Isofurocaespitane Sq-00304 - Sq-00312

Furocaespitane Sq-00304 14-Hydroxy-12, 13-dihydrosesquiterpineol Sq-00308

3-(3-Bromo-4-chloro-4-methy/cyclohexyl)-2-methy/furan
[51847-78-0] HO~

Br ~CHOH 14 2

C 15H 280 2 M 240.385

Constit. of Conyza aegyptica. Gum.
Absolute
14-0-X ylopyranoside:
configuration C20H 360 6 M 372.501
Constit. of C. aegyptica.
CuH 16BrCIO M 291.614 Zdero, C. et al, Phytochemistry, 1990, 29, 3167 (isol)
Constit. of Laurencia caespitosa. Cryst. (C 6H 6). Mp 83-85°.
Gonzalez, A.G. eta/, Tetrahedron Lett., 1973, 3625; 1979, 2719 4-(4-Hydroxy-4-methylpentyl)-3- Sq-00309
(isol, struct, cmr) cyclohexene-1-carboxaldehyde, 9CI
Estrada, D.M. et al, Tetrahedron Lett., 1987, 28, 687 (abs config)
[31906-04-4]
Furoventalene Sq-00305
3-Methyl-6-(4-methy/-3-pentenyl)benzo[blfuran ""' I r("yCHO
[25074-12-8] H~
C 13H 220 2 M 210.316
Major component of Lyra!, an important lilac lily
perfumery fragrance. Bp 1 126-130°.
Koyami, K. et al, Can. J. Chern., 1974, 52, 125 (synth)
Japan. Pat., 74 40 466, (1974); CA, 82, 155564d (synth)
C 15H 180 M 214.307 U.S. Pat., 4 007 137, (1977); CA, 87, 39008e (synth, use)
Constit. of Gorgonia ventalina. Oil. Ger. Pat., 2 730 176, (1978); CA. 88, 152126a (synth)
Weinheimer, A.J. eta/, Tetrahedron Lett., 1969, 3315 (isol, struct)
Kido, F. eta/, J. Org. Chern., 1981, 46, 4389 (synth) 6-Hydroxy-14-sesquilimonenoic acid Sq-00310
Bergstrom, D.E. eta/, J. Heterocycl. Chern., 1983, 20, 469 (synth)
Hagiwara, H. et al, J. Chern. Soc., Perkin Trans. I, 1984, 91 HO
(synth)

Himasecolone Sq-00306
~~H
6-(2-Hydroxy-5-methylphenyl)-6-methy/-2-heptanone, 9CI
[73582-69-1]
C15H 220 3 M 250.337
0 Constit. of Nidorel/a hottentotica. Gum.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1109.

Isocinariolide Sq-00311
[69904-90-1]

o><
C15H 220 2 M 234.338 0
Constit. of Cedrus deodara. Oil.
Agarwal, P.K. et al, Phytochemistry, 1981, 20, 1319.
Ho, T.-L. et al, Chern. Ind. (London), 1983, 566 (synth)
Trivedi, S.V. et al, Indian J. Chern., Sect. B, 1986, 25, 1160 (synth)

Humbertiol Sq-00307 c.sH•s02 M 230.306

Constit. of Cineraria spp. Oil.
[28625-25-4]
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1629.

Isofurocaespitane Sq-00312
3-(4-Bromo-3-chloro-4-methylcyclohexyl)-2-methy/furan
[73436-45-0]

Br
C15Hz..0 M 220.354
Constit. of Humbertia madagascariensis. Oil. [a]i; + 10.7° Cl
(c, 0.9 in CHCI 3).
Raulais, D. eta/, Bull. Soc. Chim. Fr., 1970, 2401. 0 CH3
CuH 16BrCIO M 291.614
Constit. of Laurencia caespitosa. Oil. [a] 0 -39°.
Gonzalez, A.G. et al, Tetrahedron Lett., 1979, 2719.

201
5-Isopropyl-2-(2-methylpropyl)-2-... - Ovalicin Sq-00313 - Sq-00319

5-Isopropyl-2-(2-methylpropyl)-2- Sq-00313 C 1 ~H 23 Br 2 Cl0 3 M 446.606

cyclohexen-1-one Constit. of L. caespitosa. Unstable.
5-( 1-Methylethyl)-2-(2-methylpropyl)-2-cyclohexen-1-one, Chang, M. et al, Phytochemistry, 1989, 28, 1417.
9CI
[79862-15-0] Nidorellaurinic acid Sq-00317
COOH

C 13H 22 0 M 194.316
Constit. of Anthemis nobilis. Oil.
[79862-34-3) C 1 ~H 20 0 2 M 232.322
Thomas, A.F. et al, Helv. Chim. Acta, 1981, 64, 1488. Me ester: [70387-31-4]. Methyl nidorellaurinate
CI,H 220 2 M 246.349
Constit. of Nidorella auriculata. Oil.
5-Isopropyl-2-propyl-2-cyclohexen-1-one Sq-00314
5-( 1-Methylethyl)-2-propyl-2-cyclohexen-1-one, 9CI 3,4-Dihydro, Me ester: [70387-30-3]. Methyl
dihydronidoreUaurinate
[79862-14-9] C 16H 240 2 M 248.364
Constit. of N. auriculata. Oil. [cx]i;' +99.8° (c, 0.5 in
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1769 (isol)
Sanyaiah, R. et al, Tetrahedron Lett., 1980, 2767 (synth)

Noroxopenlanfuran Sq-00318
3-(3-Furany/methyl)-4-( 1-methy/ethyl)-2-cyclohexen-1-one,
9CI
C 12H 200 M 180.289 [95653-79-5]
Constit. of Anthemis nobilis. Oil.
[79862-33-2)
Thomas, A.F. et a/, Helv. Chim. Acta, 1981, 64, 1488.

Laucopyranoid A Sq-00315
[124193-05-1]
Br CI4HisOz M 218.295
Constit. of Dysidea fragilis. Oil. [cxJi? -91.0° (c, 0. 79 in
CHC1 3).
Guella, G. et al, Helv. Chim. Acta, 1985, 68, 39.
Kato, M. et al, J. Chern. Soc., Chern. Commun., 1990, 1706 (synth)

Ovalicin Sq-00319
C 1 ~H 23 Br 2 Cl0 M 414.607 Graphinone
Constit. of Laurencia caespitosa. Cryst. Mp 118-120°. [cxln [19683-98-8]
+O.SO (c, 0.87 in CHC1 3).
Chang, M. eta/, Phytochemistry, 1989, 28, 1417.

Laucopyranoid B Sq-00316
[124264-18-2]

0
C 16H 240 5 M 296.363
Sesquiterpene antibiotic. Constit. of seeds of lettuce and
metab. of Pseudeurotium ova/is. Exhibits antibacterial,
antitumour and immunosupressive activity. Cryst.
(C 6 H 6 /hexane). Mp 93-94°. [cx]~ -75° (c. 1 in MeOH).
Structurally related to Fumagillin.
C 15H 23 Br2Cl0 3
~ RP3680500.
Constit. of Laurencia caespitosa. Cryst. Mp 97-98°. [cxJn
+ 11.0° (c, 1.12 in CHCI 3). Sassa, T. et al, Agric. Bioi. Chern., 1970, 34, 649 (struct)
Bollinger, P. et al, Helv. Chim. Acta, 1973, 56, 819 (cryst struct)
8-Epimer: [124192-95-6]. Laucopyranoid C

202
Penlanbutenolide - Xanthostemone Sq-00320 - Sq-00327

Cane, D.E. et al, J. Am. Chern. Soc., 1977, 99, 6132 (biosynth) Sesquichamaenol Sq-00324
Hartman, G.L. et al, Planta Med., 1978, 34, 231 (rev) 5-(2-Hydroxy-5-methylphenyl)-6-methyl-2-heptanone.
Corey, E.J. et al, J. Am. Chern. Soc., 1985, 107, 256 (synth, bib/) Sesquichamenol

Penlanbutenolide Sq-00320
OEt

\JX)
0 \ C 1 ~H:z:zO:z M 234.338
(±)-form [30543-91-0]
C 17H 2,p3 M 276.375
Constit. of Chamaecyparisformosensis. Mp 109-110°.
Isol. from Dysidea fragilis. Oil.
Ando, M. et al, J. Chern. Soc., Chern. Commun., 1970, 1538
[95653-88-6, 95653-89-7]
(struct, synth)
Guella, G. et al, Helv. Chim. Acta, 1985, 68, 39. Trivedi, S.V. eta/, Indian J. Chern., Sect. B, 1990, 29, 876 (synth)

Penlanfuran Sq-00321 Tasmanone Sq-00325

3-[(3-M ethylene-6-( 1-methylethyl)-1-cyclohexen-1- Tasmanol

Mw
y~methyl]furan, 9CI
[22595-52-4]
[87896-23-9]
OH O

C14H 200 4 M 252.310

Constit. of Eucalyptus oil (Eucalyptus tasmanica, E. risdoni
C 1 ~H 20 0 M 216.322 and E. camjieldii). Pale-yellow oil. Bp4 135°. n~ 1.5349.
Constit. of sponge Dysideafragilis. Oil. [ex]~ -68.0° (c, 2.4 Hellyer, R.O. eta/, Aust. J. Chern., 1963, 16, 703 (isol, uv, ir, pmr)
in CHC1 3). Bick, I.R.C. eta/, Aust. J. Chern., 1965, 18, 1405 (pmr)
Guella, G. et al, Tetrahedron Lett., 1983, 24, 3897 (isol) Birch, A.J. et al, J. Chern. Soc. C, 1966, 1337 (biosynth)
Mancini, I. et al, Helv. Chim. Acta, 1990, 73, 652 (abs config) Baigent, D.R. et al, Chern. Ind. (London), 1974, 747 (synth)

Pleraplysillin 1 Sq-00322 1-(3,6,6-Trimethyl-1-cyclohexen-1-yl)-2- Sq-00326

[41060-03-1] buten-1-one, 9CI
[80006-93-5]

C 1 ~H 20 0 M 216.322
Constit. of Pleraplysilla spinifera. Oil.
y~~
Cimino, G. et al, Tetrahedron, 1972, 28, 4761 (isol) C 13H 200 M 192.300
Masaki, Y. et a/, Bull. Chern. Soc. Jpn., 1984, 57, 3476 (synth) Occurs in fusel oil. Unique non-isoprenoid substn. pattern.
Witteveen, J.G. et al, Reel. Trav. Chim. Pays-Bas (J. R. Neth.
Prosopidione Sq-00323 Chern. Soc.), 1981, 100, 383 (synth, spectra)
2,4,4- Trimethyl-6-(3-oxo-1-butenyl)cyclohexanone, 9CI
[120166-32-7] Xanthostemone Sq-00327
6,6-Dimethyl-2-(2-methyl-1-oxopropyl)-4-cyclohexene-1 ,3-
dione, 9CI. 2-Isobutyryl-6,6-dimethyl-4-cyclohexene-1 ,3-
dione, 8CI
[2260 1-85-0]

C 13H 200 2 M 208.300

Constit. of Prosopis julifiora. Amorph. powder. Mp 202°
dec. [cx] 0 - 19.2° (MeOH).
Ahmad, V.U. et al, Phytochemistry, 1989, 27, 278.
CuH160 3 M 208.257
Isol. from the oil of Xanthostemon oppositifolius. Oil. Bp0 8
95-102°. ni; 1.5112. ·
2,4-Dinitrophenylhydrazone: Orange-red needles (MeOH).
Mp 239°.
Birch, A.J. eta/, Aust. J. Chern., 1956, 9, 238 (isol, uv, struct)

203
Nootkatin- Sesquisabinene Sq-00328 - Sq-00330

Cycloheptane Cyclobisabolanes
sesquiterpenoids
Sesquicarene Sq-00329
[204 79-23-6]
Nootkatin Sq-00328 H

~
2-Hydroxy-5-(3-methy/-2-butenyl)-4-(1-methy/ethyl)-2,4,6-
cycloheptatrien-1-one. 4-Isopropy/-5-preny/tropo/one. 6-
/sopropy/-5-preny/tropo/one
H
[4431-03-2]
C 1 ~H 24 M 204.355
Constit. of Schisandra chinensis. Oil. [1X]i,S -76.9° (c, 0.82
in CHC1 3).
7-Epimer: /sosesquicarene
CtsH 24 M 204.355
3'
Constit. of Haplopappus tenuisectus. Oil. [1X]~4 -11° (c,
0.1 in CHC1 3).
~- Ohta, Y. et a/, Tetrahedron Lett., 1968, 1251 (iso/, struct)
Garbers, C.F. et a/, Tetrahedron Lett., 1975, 3753 (synth)
C 1 ~H 10 0 2 M 232.322 Kitatani, K. et a/, J. Am. Chern. Soc., 1976, 98, 2362 (synth)
Tautomeric with the struct. having C=O and OH Bohlmann, F. et a/, Phytochemistry, 1979, 18, 1749 (isol,
interchanged (equivalent to isopropyl group at C-6). Isosesquicarene)
lsol. from Chamaecyparis nootkatensis and Cupressus Uyehara, T. et a/, Bull. Chern. Soc. Jpn., 1985, 58, 211, 861 (synth)
stephensonii, other C. spp., and from Juniperus spp. Johnson, C.R. eta/, J. Org. Chern., 1987, 52, 1493 (synth)
Widespread in the Cupressaceae. Cryst. (pet. ether). Mp
95°. Sesquisabinene Sq-00330
Me ether: Cryst. (pet. ether). Mp 72°. 1-(1,5-Dimethyl-4-hexenyl)-4-methylenebicyclo[3. l.O]hexane,
3' ,4'-Dihydro, 4' -hydroxy: [2492-08-2]. Nootkatinol. 9C/
Hydronootkatinol [58319-04-3]
Ct~H 22 0 3 M 250.337
Constit. of J. rigida and Cupressus lindleyi. Cryst.
(C 6H 6jpet. ether). Mp 107-108° (102-103°).
2n,3n-Didehydro: [552-96-5]. 2-Hydroxy-5-(3-methy/-2-
butenyl)-4-( 1-methylethenyl)-2 ,4,6-cycloheptatrien-1-one,
9Cl. 4- Isopropenyl-5-preny/tropo/one. 6- lsopropenyl- 5-
prenyltropolone. Procerint
Ct~H 18 0 2 M 230.306 C 1 ~H 24 M 204.355
Isol. from J. procera. Mp 71-72°. Constit. of Piper nigrum. Isol. by glc.
Duff, S.R. et a/, Chern. Ind. (London), 1954, 432 (struct) tl 3•4-Isomer: [58319-06-5]. Sesquithujene
Runeberg, J. eta/, Acta Chern. Scand., 1960, 14, 353, 797, 1985, C1~H 24 M 204.355
1991; 1961, IS, 645 (isol, ir, synth) lsol. from Zingiber officina/e.
Hirose, Y., Agric. Bioi. Chern., 1963, 27, 795.
Bicho, J. eta/, J. Org. Chern., 1963, 28, 2927 (isol, uv, ir, pmr, 3,15-Dihydro, 3-hydroxy (cis-): Sesquisabinene hydrate
synth, deriv) CtsH240 M 220.354
Kitahara, Y. et a/, Bull. Chern. Soc. Jpn., 1964, 37, 895 (synth, I sol. from essential oil of Z. officinale.
Procerin) 12-Acetoxy: 11-Sesquisabinenol acetate. 12-
Zavarin, E. eta/, Phytochemistry, 1967, 6, 1387 (isol, occur)
Senter, P. et a/, Phytochemistry, 1975, 14, 2233 (isol)
Acetoxysesquisabinene
C 17H 260 2 M 262.391
Constit. of Arctotis grandis, Haplocarpha scaposa and H.
lyrata. Oil.
12-0xo: [83161-51-7]. 11-Sesquisabinenal. 2-Methyl-6-(4-
methylenebicyclo[3 .1.0]hex-1-yl)-2-heptenal, 9Cl
C 1 ~H 22 0 M 218.338
Constit. of H. scaposa and H. lyrata. Oil.
13-Acetoxy: 13-Sesquisabinenol acetate. 13-
Acetoxysesquisabinene
C 17H 260 2 M 262.391
Constit. of H. scaposa and H. lyrata. Oil. [IX]~~ - 39.SO
(c, 0.2 in CHC13).
[83212-53-7]
Terhune, S.J. eta/, Can. J. Chern., 1975, 53, 3285 (isol. struct)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1157 (isol, struct)
Sharma, P.K. eta/, Phytochemistry, 1988, 27, 3471 (biosynth)

204
Sirenin - 8,15-Dihydroxy-1,3-elemadien-12,6-... Sq~00331 - Sq-00336

Sirenin Sq-00331 Curzerenone Sq-00334

[19888-27-8] Zedoarone
[20493-56-5]
H

HOH2 ~~~'
~/- JCHzOH ~0)
1(\
C15Hz..02 M 236.353
Sperm attractant produced by female gametes of the water C15H1s02 M 230.306
Consit. of Curcuma zedoaria. Oil. [1X]n + 0°.
mould Al/omyces. Faintly yellow oil. [IX]~ -45° (c, 1 in
CHC1 3). 5-Epimer: [20085-85-2]. 5-Epicurzerenone. 5-epi-
Curzerenone
Machlis, L. et al, Biochemistry, 1966, 5, 2147 (isol)
Nutting, W.H. et a/, J. Am. Chern. Soc., 1968, 90, 6434 (struct) C 15H180 2 M 230.306
Plattner, J.J. et a/, J. Am. Chern. Soc., 1971, 93, 1758 (synth, abs From C. zedoaria. Oil. [1X]n + 0°.
config) (19956-58-2]
Jaenicke, L. eta/, Fortschr. Chern. Org. Naturst., 1973, 30, 61 (rev) Fukushima, S. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1968,
Garbers, C.F. et al, Tetrahedron Lett., 1975, 3753 (synth) 88, 792 (isol)
Kitatani, K. et al, J. Am. Chern. Soc., 1976, 98, 2362 (synth) Hikino, H. et al, J. Chern. Soc., Perkin Trans. I, 1975, 478 (isol)
Du Preez, H.E. et al, S. Afr. J. Chern., 1980, 33, 21 (synth) Miyashita, M. eta/, J. Org. Chern., 1984, 49, 3728 (synth, bib[)
Mandai, T. et al, Tetrahedron Lett., 1983, 24, 1517 (synth)
Uyehara, T. et al, Bull. Chern. Soc. Jpn., 1985, 58, 211 (synth)
Harding, K.E. eta/, J. Org. Chern., 1988, 53, 4877 (synth, bib[) 8,11-Dihydroxy-1,3-elemadien-12,6-olide Sq-00335
: OH

Elemanes ~OH 0
Absolute
configuration

C15H 220 4 M 266.336

(ent-6rx.,7p,ap,11R)-form
Aoifuranone Sq-00332 11-Angeloyl, 6-Ac: [38733-34-5]. Isolaserolide
C22 H:l(,06 M 390.475
[58580-60-2]
Constit. of roots of Laser trilobum. Cryst. Mp 125-127°.
[1X]i? +81.1 o.
Holub, M. eta/, Collect. Czech. Chern. Commun., 1968, 33, 2911
(isol)

,
Holub, M. eta/, Tetrahedron Lett., 1984, 25, 3755; Collect. Czech.
Chern. Commun., 1985, 50, 1878 (struct)

915
C15H180 2 M 230.306 8,15-Dihydroxy-1,3-elemadien-12,6-olide Sq-00336
Constit. of Asarum caulescens. Cryst. Mp 118-119°. [IX]~
+43.9° {c, 1.5 in MeOH). ,OH
Endo, J., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1975, 95, 1321.
~ /

Bicycloelemene Sq-00333 HOH2 C 0 /

3-Ethenyl-3,7,7-trimethyl-2-(1-
0
methylethenyl)bicyclo[4.1.0]heptane, 9Cl. 2-Isopropenyl-3-
methyl-3-vinylbicyclo[4 .J.O]heptane C 15H 220 4 M 266.336
[32531-56-9] (6u.,8rx.,11 PH)-form [38049-38-6] Melitensin
Constit. of Centaurea melitensis and C. aspera var.
stenophylla. Cryst. Mp 167-168°. [1X]n +85°.
8-(3-M ethylbutanoyl): 11 p,JJ-Dihydroisoarbutifolin
C20H 300 5 M 350.454
Constit. of C. arbutifolia. Oil.
C15H24 M 204.355 11 ,13-Didehydro: 81X,l5-Dihydroxy-1,3,11(13)-elematrien-
Constit. of peppermint oil. Oil. [1X]i? -34°. 12,61X-olide. Dehydromelitensin
C15H200 4 M 264.321
Ulahov, R. et al, Collect. Czech. Chern. Commun., 1967, 32, 808
(isol)
Constit. of Onopordon corymbosum. Oil.
Takeda, K. eta/, J. Chern. Soc., Chern. Commun., 1971, 308 11 ,13-Didehydro, 8-(2-hydroxymethyl-2-propenoyl):
(struct) Dehydromelitensin 4-hydroxymethacrylate
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1976, 14, 852 (synth) C19H 240 6 M 348.395
Constit. of 0. corymbosum. Oil.
11 ,13-Didehydro, 8-(3-methylbutanoyl): [80442-34-8].
Isoarbutifolin
C 20H 280 5 M 348.438

205
11,15-Dihydroxy-1,3-elemadien-12,6-... - 6,9-Dihydroxy-15-oxo-1,3,11(13)-... Sq-00337 - Sq-00341

Constit. of C. arbutifo/ia. Oil. [ocln +42.2° (c, 3.9 in 6,9-Dihydroxy-15-oxo-1,3-elemadien-12,8- Sq-00340

CHC1 3) (as 15-Ac). olide
Gonzalez, A.G. et a/, An. Quim., 1971, 67, 1243; 1974, 70, 158
(isol, struct, synth) OH

~0
Gonzalez, A.G. eta/, Phytochemistry, 1981, 20, 1895
(lsoarbutifolin)
Tortajada, A. eta/, Phytochemistry, 1988, 27, 3547 (cryst struct)
Cardona, M.L. eta/, Phytochemistry, 1989, 28, 1264 (deriv)
OHC OH '
11,15-Dihydroxy-1,3-elemadien-12,6-olide Sq-00337
C15H:w05 M 280.320
(6ft,7P,9«,ll«)-form
6-(2-Methy/propanoyl): [33792-82-4]. Zinarosin
C 19H 260 6 M 350.411
Constit. of Zinnia acerosa. Cryst. Mp 151-153°. [ocln
+84°.
C 15H:zz04 M 266.336 Romo, J. eta/, Rev. Latinoam. Quim., 1971, 2, 24; CA, 75, 45670h.
(6«,11/1)-form [93372-86-2)11,15-Dihydroxysaussurea lactone
Constit. of Centaurea spp. Cryst. (EtOAcfhexane). Mp 6,9-Dihydroxy-15-oxo-1,3,11(13)- Sq-00341
138-140°. [oc]i,S +70° (c, 1.7 in CHCl 3). elematrien-12,8-olide
Gonzalez, A.G. eta/, Phytochemistry, 1984, 23, 2071.
OH
I

6,14-Dihydroxy-1,3,11(13)-elematrien- Sq-00338
12,8-olide
(6~, 7~,8cx,9cx)-form

;yyo~o C15H 180 5 M 278.304

Yb:i
(6ft,7«,8«,9«)-form
6,9-Dihydroxyzinamu/tifioride
6-(2-Methy/propenoyl): [73021-17-7].
C 15H 280 4 M 264.321 C 1,H:zz06 M 346.379
(6«,8«)-form [108863-71-4] Constit. of Zinnia spp. Oil.
Schkuhridin B 9-(2-Methy/propenoyl): [73021-19-9].
Constit. of Schkuhria schkuhrioides. Pale-yellow oil. [oc)i,S c.,H220 6 M 346.379
+60.54° (c, 0.18 in MeOH). Constit. of Z. spp. Oil.
14-(2-Hydroxy-3-methy/butanoyl): [108863-70-3). 6-Ange/oy/: [73021-16-6].
Schkuhridin A C2oH 240 6 M 360.406
C 28H 280 6 M 364.438 Constit. of Z. spp. Oil.
From S. schkuhrioides. Pale-yellow oil. [oc)i,S + 104.58° (c, 9-Ange/oy/: [73021-18-8].
0.1 in CHC1 3). ~H 240 6 M 360.406
Delgado, G. eta/, Phytochemistry, 1987, 26, 755. Constit. of Z. spp. Oil.
6-Ange/oy/, 9-Ac: [73021-20-2].
8,14-Dihydroxy-1,3,11(13)-elematrien- Sq-00339 C:zzH 260 7 M 402.443
12,6-olide Constit. of Z. spp. Oil.
9-Ange/oyl, 6-Ac: [73021-21-3].
C:zzH260 7 M 402.443
Constit. of Z. spp. Oil.
JS,2-Epoxide, 6-ange/oy/: [73021-23-5].
C28H 240 7 M 376.405
Constit. of Z. spp.
JS,2-Epoxide, 6-(2-methy/propenoyl): [73021-22-4].
C 19H 22Q7 M 362.379
C 15H:w04 M 264.321 Constit. of Z. spp. Oil.
(6«,8« )-form JS,2-Epoxide, 9-ange/oy/: [73088-53-6].
Constit. of Schkuhria anthemoidea var.wislizenii. C:wH240 7 M 376.405
14-Ac: Constit. of Z. spp. Oil.
C 17H:zz0 5 M 306.358 JS,2-Epoxide, 9-(2-methy/propenoyl): [73021-24-6].
From S. anthemoidea var. wislizenii. C 19H 220 7 M 362.379
8-(Z-2-Hydroxymethyl-2-butenoyl): [113412-0 1-4]. Constit. of Z. spp. Oil.
Elemajurinel/oide JS,2-Epoxide, 6-(2-methy/butanoyl):
C:wH260 6 M 362.422 C:wH 240 7 M 376.405
So far isol. only as derivs.; see under 8,14,15- Constit. of Z. spp. Cryst. (Et20). Mp 166°.
Trihydroxy-1 ,3, 11( 13)-e1ematrien-12,6-olide, Sq-00384.
JS,2-Epoxide, 6-(3-methy/butanoyl):
Stewart, E. eta/, Phytochemistry, 1985, 24, 2731. C:wH240 7 M 376.405
Rmtaiyan, A. eta/, Phytochemistry, 1987, 26, 2857 (deriv)

206
Disynaphiolide - 1,3-Elemadien-11-ol Sq-00342 - Sq-00346

Constit. of Z. spp. Oil. [1X]~4 + 51.8° (c, 1.2 in CHC13). C20H 240 6 M 360.406
(ent-6rx.,7rx.,Bp,9Jl)-form Constit. of C. chachapoyensis. Oil.
6-Angeloyl: [88907-73-7]. Zinajlorin V Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 240.
C20H 240 6 M 360.406
Constit. of Z. peruviana. Cryst. Mp 169-172°. 1,3-Elemadiene-8,11-diol Sq-00344
JR,2-Epoxide, 6-angeloyl: [57082-46-9]. Zinajlorin II 8-Hydroxyelemol
Cwli240 7 M 376.405
Constit. of Z. peruviana. ~,OH
JR,2-Epoxide, 6,9-diangeloyl: [57082-45-8]. Zinaflorin I
C:zsH300 8 M 458.507
Constit. of Z. peruviana. ~H
JR,2-Epoxide, 6-(2-methylpropenoyl): [73287-32-8]. C15H 260 2 M 238.369
Epoxyzinnamultijloride 8rx.-form [64373-81-5]
C19H 220 7 M 362.379 Constit. of Chenopodium graveolens. Cryst. (Et20). Mp
Constit. of Z. peruviana. 110°. [1X]n +0.01° (c, 0.78 in MeOH).
(ent-6p,7rx.,8rx.,9rx.)-form 8-Ac: [41370-57-4]. 8-Acetoxyelemol
JS,2-Epoxide, 6-angeloyl: Zinajlorin IV C17H 280 3 M 280.406
Constit. of Z. peruviana. Cryst. (Et20jhexane). Mp 190- Constit. of Parabenzoin praecox and Juniperus thurifera.
1920. [1X]n +96.2° (c, 5.1 in EtOH). Oil. [1X]n +32.9° (c, 0.8 in CHC1 3).
(6rx.,7p,Bp,9Jl)-form Ohara, K. et al, Bull. Chern. Soc. Jpn., 1973, 46, 641 (deriv)
3,4R-Epoxide, 6-(2-methylpropanoyl): [98644-41-8]. Teresa, J. de P. et al, An. Quim., 1977, 73, 151 (deriv)
Zempoalin C Mata, R. et al, Phytochemistry, 1987, 26, 191 (isol)

'
C19H 240 7 M 364.394

ffl
Constit. of Verbesina seattonii. Cryst. 1,3-Elemadien-6-ol Sq-00345
(Me 2COjhexanejdiisopropyl ether). Mp 119-122°. [1X]n
-27.3° (c, 0.139 in CHC1 3). Exists in soln. partly as
7
hemiacetal. Absolute
""- 6
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1343. configuration
Ortega, A. eta/, Chern. Lett., 1983, 1607. H
Ortega, A. eta/, Phytochemistry, 1985, 24, 1755 (Zempoalin C)
Miranda, R. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 1128 C15H 260 M 222.370
(Zinaflorin IV) 6P-form [35727-45-8] Shyobunol
Constit. of a Galbanum absolute. Oil. [1X]i? -9.3° (c, 1.1
Disynaphiolide Sq-00342 in CHC13).
[79404-33-4] Ac:
C 17H 280 2 M 264.407
Constit. of G. absolute. Oil. [1X]i? + 7.4° (c, 2.1 in
CHC13).
6-Ketone: [21698-44-2]. 1,3-Elemadien-6-one. Shyobunone
C 15H 240 M 220.354
Constit. of the rhizome of Acarus calamus. Oil.
Ketone, 7-epimer: [39020-72-9]. Epishyobunone. epi-
Shyobunone
C20H 200 7 M 372.374 C15H240 M 220.354
Constit. of Disynaphia halimifolia. Cryst. (Etpjpet. ether). Constit. of the rhizone of A. calamus. Oil. [1X]i? -179°
Mp 161°. [1X]i;l -58.6° (c, 0.35 in CHC13). (c, 1.4 in CHC1 3).
Yamamura, S. et al, Tetrahedron, 1971, 27, 5419, 5987 (isol, struct,
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1077.
synth)
Kaiser, R. eta/, Helv. Chim. Acta, 1978, 61, 2671 (isol, struct)
Elemacronquistianthusic acid Sq-00343 Frater, G., Helv. Chim. Acta, 1978, 61, 2709 (synth, struct)
[96850-14-5]
1,3-Elemadien-11-ol Sq-00346

~--
' 8 P-Elemol. Elemol
[639-99-6]
~
\
HOOC 0
0
CisHis04 M 262.305
8P-Angeloyloxy: [90039-38-6].
C20H 240 6 M 360.406 CisH 260 M 222.370
Constit. of Cronquistianthus chachapoyensis. Cryst. Constit. of many essential oils including Manila elemi and
Java citronella oils. Cryst. Mp 52.5-53.5°. [1X]n -5.8° (c,
(Et20jpet. ether). Mp 135°. [1X]i;l + 16.7° (c, 2.58 in
3.4 in CHC1 3).
CHC1 3).
Ha1sall, T.G. et a/, J. Chern. Soc., 1964, 1029 (struct)
8P- Tigloyloxy: [90039-39-7].

207
1,3-Elemadien-12,6-olide - 1,3,7(11)-Elematriene Sq-00347 - Sq-00354

Corey, E.J. eta/, Tetrahedron Lett., 1969, 1779 (synth) 1,3,7(11 ),8- Elematetraene Sq-00351
Kutney, J.P. eta/, Can. J. Chern., 1983, 61, II II (synth)
Baldwin, S.W. eta/, J. Org. Chern., 1985, 50, 5720 (synth) [107439-18-9]

1,3-Elemadien-12,6-olide Sq-00347

C15H22 M 202.339
Constit. of Baccharis salicifo/ia. Oil. [a:]~ +go (c. 2.9 in
CHC1 3).
Zdero, C. eta/, Phytochemistry, 1986, 25, 2841.
Ct5H 220 2 M 234.338
(6«,11«)-form [23527-07-3] Saussurea lactone
1,3,7(11 ),8- Elematetraen-12,8-olid-15-oic Sq-00352
From costus root oil (Saussurea lappa), probably formed
by pyrolysis of Dihydrocostunolide. Cryst. (MeOH). Mp acid
148-149°. [«Jn +66° (CHC1 3).
Rao, A.S. et a/, Tetrahedron, 1961, 13, 319 (struct)
Masayoshi, A. eta/, Chern. Lett., 1978, 617, (synth)
~o'>=o
Ando, M. eta/, J. Org. Chern., 1983, 48, 1210 (synth)
~
COOH
1,4-Elemadien-6-one Sq-00348
Ct5Ht,04 M 260.289
lsoshyobunone
Me ester: [128008-17-3].
[21698-46-4] Ct,H 180 4 M 274.316
Constit. of Pseudopterogorgia sp. Gum. [a:ln + 19° (c,
0.05 in CHC1 3).
Absolute Chan, W.R. et a/, Tetrahedron, 1990, 46, 1499 (isol, struct)
configuration
1,3,6-Elematriene Sq-00353
C 15H 24 0 M 220.354
o-E/emene
Constit. of the rhizomes of Acorus calamus. Oil.
[20307-84-0]
Iguchi, M. et al, Tetrahedron Lett., 1968, 5315 (isol, struct)
Alexandre, C. et al, Bull. Soc. Chim. Fr., 1977, 117 (synth)
Niwa, M. eta/, Chern. Lett., 1977, 1415 (abs config)

Elemane Sq-00349
1-Ethyl-2 ,4-diisopropyl-1-methylcyclohexane
C 15H 24 M 204.355
[515-12-8] Constit. of Dysoxylum fraseranum. Oil. Bp 10 107°. [1X]n +
oo.
Gough, J.H. eta/, Aust. J. Chern., 1964, 17, 1270.

1,3,7(11 )-Elematriene Sq-00354

1-E/emene
C15H30 M 210.402 [29873-99-2]
Liq. Bp8 117-119°. [a:Jn -13° (c, 0.15 in CHC1 3).
Ganter, C. eta/, Helv. Chim. Acta, 1971, 54, 183.

Elemanschkuhriolide Sq-00350
[90605-37-1]
C 15H 24 M 204.355
Constit. of Gurjun balsam oil. Oil. Bp0.01 44°. [1X]n + 3.93°
(c, 1 in CHC1 3).
Gough, J.H. et a/, Aust. J. Chern., 1964, 17, 1270 (synth)
Gauter, C. eta/, Helv. Chim. Acta, 1971, 54, 183 (synth)
Thomas, A.F., Helv. Chim. Acta, 1972, 55, 2429 (synth)
Kato, M. eta/, J. Chern. Soc., Perkin Trans. I, 1979, 2740 (synth)
C15H 180 4 M 262.305 Wakamatsu, T. et al, Heterocycles, 1987, 26, 1203 (synth)
Kim, D. eta/, J. Org. Chern., 1987, 52, 4633 (synth)
Constit. of Schkuhria schkuhrioides. Amorph. solid
(MeOHjdiisopropyl ether). Mp 127-128°. [a:]~ + 123.1°
(c, 0.116 in MeOH).
Delgado, G. eta/, J. Org. Chern., 1984, 49, 2994.

208
1,3,11-Elematriene- 1,3,11-Elematrien-12,8-olide Sq-00355 - Sq-00361

1,3,11-Elematriene Sq-00355 C 15H 140 M 220.354

fl-Elemene (5p,9p,1011.)-form
[33880-83-0] Constit. of Kadsura japonica. Oil. [oc]i;4 -13.1 o (c, 0.26 in
MeOH).

~I
(511.,9P,10f/)-form [20482-30-8] epi-~-Eiemenol
Constit. of K. japonica. Oil. [oc]i;4 + 184.1° (c, 1.23 in
~(-)-form MeOH).
Morikawa, K. eta/, Tetrahedron Lett., 1968, 2899; 1969, 869 (iso/,
C 15H 14 M 204.355 synth)
(-)-form
Constit. of sweet-flag and juniper oils, Chrysanthemum 1,3,11(13)-Elematrien-12-ol Sq-00359
spp., Mentha spp. Doona spp. and others. Oil. Bp 15 _5 Elemenal
117-124°. [oc]i? - 11.1 o (CHC1 3). [4584-28-5]
9P-Hydroxy: [38655-84-4]. 1,3,11-Elematrien-9P-ol. fl-
Elemen-9fl-ol
C 15H 140 M 220.354
Constit. of Achillea ageratum. Oil. Bp0 _3 113-115°. [oc]i:'
-19.9° (c, 2 in MeOH).
(+)-form C 15Hzz0 M 218.338
Isol. from Libanotis transcaucasica. [1X]n + 14.2°. ni? Constit. of Thujopsis dolabrata. Oil. [oc] 00 -11° (CHC1 3).
1.4945.
Ito, S. eta/, Tetrahedron Lett., 1965, 3777 (iso/)
Pigulevskii, G.V. eta/, J. Org. Chern. USSR (Engl. Trans/.), 1962, Maurer, B. eta/, Helv. Chim. Acta, 1977, 60, 2177 (isol)
32, 3054 (isol)
Irie, T. eta/, Bull. Chern. Soc. Jpn., 1964, 37, 1053 (isol, ir, pmr)
Hunter, G.L.K. eta/, J. Food Sci., 1964, 29, 25 (isol) 1,3,7(11)-Elematrien-12,8-olide Sq-00360
Patil, L.J. eta/, Tetrahedron Lett., 1967, 2273 (synth)
Grandi, R. eta/, Phytochemistry, 1972, 11, 3363 (deriv)
McMurry, J.E. eta/, Tetrahedron Lett., 1985, 26, 2171 (synth)

1,5,7(11)-Elematriene Sq-00356
11.-Eiemene C15H 100 1 M 232.322
[5951-67-7] 811.-form [20267-89-4] 1sogermafurenolide
Constit. of the root of Lindera strychnifolia. Cryst. (pet.
ether/Etp). Mp 85-85.5°. [oc]i? +5° (c, 0.3 in dioxane).
Takeda, K. eta/, J. Chern. Soc. C, 1968, 569.

1,3,11-Elematrien-12,8-olide Sq-00361
C 15H 14 M 204.355 Elemasteiractinolide
Constit. of Dysoxylumfraseranum. Oil. Bp7 120-130°. [1X]n
+ 1W (c, 15 in CHC1 3).
Paknikar, S.K. eta/, Tetrahedron, 1962, 18, 1509.

1,3,11-Elematriene-9,14-diol Sq-00357
OH C 15H 100 1 M 232.322

~
Parent compd. appears to be currently unknown.
(ent-811.)-form
11P,13-Dihydro: [66964-63-4]. ent-1,3-Elemadien-12,8oc-
olide. Callitrin
Constit. of Callitris columellaris. Cryst. (hexane). Mp
C 15H 140 1 M 236.353 82-83°. [1X]D +225°.
9fl-form [124223-94-5] Periplocadiol 15-Hydroxy: [100045-45-2]. ent-15-Hydroxy-1,3,11(13)-
Constit. of Periploca laevigata. Oil. [1X]n -19° (c, 12.4 in elematrien-12,8oc-olide. 15-Hydroxyelemasteiractinolide
CHC1 3). C•sH100 3 M 248.321
Askri, M. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 792 (isol, pmr, Constit. of Stevia achalensis. Oil.
cmr) 15-Hydroxy, 11P,J3-dihydro: [100045-46-3]. ent-15-
Hydroxy-1 ,3-elemadien-12,811.-olide
1,3,6-Elematrien-9-ol Sq-00358 CisHn03 M 250.337
~Elemen-9-ol Constit. of S. achalensis. Oil.
[20482-29-5] 11oc,l3-Dihydro: 1111.,13-Dihydroelemasteiractinolide
Constit. of Critonia quadrangularis. Oil. [oc]i? + 27° (c,

~
0.25 in CHC1 3).
3,4p-Epoxide: 3,4/l-Epoxyelemasteiractinolide

yvy (5~,9~,10tx)-form
C 15H 100 3 M 248.321
From C. quadrangularis. Oil.
Brecknell, D.J. eta/, Aust. J. Chern., 1979, 32, 2455 (isol)

209
1,3,11(13)-Elematrien-12,8-olide - 8-Hydroxy-1,3-elemadien-12,6-olide Sq-00362 - Sq-00366

Bohlmann, F. et at, Phytochemistry, 1985, 24, 1100 (isol) 9-Hydroxy-3,11(13)-elemadiene-12,8;15,6- Sq-00365

Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1986, 799 (isol)
Jakupovic, J. eta/, Phytochemistry, 1987, 26, 451 (isol) diolide

1,3,11(13)-Elematrien-12,8-olide Sq-00362
2 ,3-Seco-1 ,3,11 (13)-eudesmatrien-12 ,8-olide

(6cx, 7f3,8f3,9J3)-:form

C15H 160 5 M 276.288

C 15H 200 1 M 232.322 (6«,7P,8P,9fJ)-form
8P-form [69855-24-9] Elemanolide Tigloyl: [99956-53-3]. Zinajfavin B
Constit. of Liatris platylepis. Oil. C20H 210 6 M 358.390
11rx,13-Dihydro: 1,3-Elemadien-12,8-olide. 11«.,13- Constit. of Zinniafiavicoma. Cryst. (EtOAcjhexane).
Dihydroelemanolide Mp 196-198°. [rxln +29.6° (c, 0.18 in CHC1 3).
C 15H 110 1 M 234.338 2-Methylbutanoyl: [99956-52-2]. Zinafiavin A
Constit. of Critonia quadrangularis. Oil. [rx]~ + 17° (c, C20 H 140 6 M 360.406
0.4 in CHC1 3). From Z.fiavicoma. Cryst. (EtOAcjhexane). Mp 162-
81;-form [31002-16-1] lga/an 1650. .
Constit. of 1nula grandis. Cryst. (MeOH aq.). Mp 79- 1S,2-Epoxide, 9-(3-methylbutanoyl): [99956-54-4). Zinafiavin
79.50. [rxli? + 105° (c, 1.38 in CHC1 3). c
Nikanova, L.P. eta/, Khim. Prir. Soedin., 1970, 6, 508; CA, 74, C20H 140 7 M 376.405
50518y (lga/an) Constit. of Z. fiavicoma. Cryst. (Me2COjhexane). Mp
Bohlmann, F. et a/, Phytochemistry, 1979, 18, 1228; 1985, 24, 145-147°. [rxJn +3.2° (c, 0.15 in CHC1 3).
1100; 1987, 26, 451 (isol)
1S,2-Epoxide, 9-tigloyl: [99956-57-7]. Zinajlavin F
C20 H 110 7 M 374.390
Geijerene Sq-00363 Isol. from Z.fiavicoma. Cryst. (Me 2C0jhexane). Mp
4-Ethenyl-4-methyl-3-(1-methylethenyl)cyclohexene, 9CI. 3- 184-186°. [rxln -14.2° (c, 0.17 in CHC13).
Isopropenyl-4-methyl-4-vinylcyclohexene 1S,2-Epoxide, 9-(2-methylbutanoyl): [99956-55-5). Zinajlavin
[6902-73-4] D
C10H 140 7 M 376.405
Isol. from Z. fiavicoma. Cryst. (EtOAcjhexane). Mp
180-183°. [rxJn + 1.8° (c, 0.23 in CHC1 3).
1S,2-Epoxide, 9-Ac: [99956-56-6]. Zinajfavin E
Isol. from Z. fiavicoma. Cryst. (Me 2CO /hexane). Mp
CuH 18 M 162.274 222-224°. [rxJn -8.8° (c, 0.18 in CHC1 3).
Constit. of Geijera parviflora. Oil. Bp 100 131°, Bp 10 75°. (ent-6rx.,7«.,8P,9fJ)-form [73020-92-5] Zinniadilactone
Hexahydro: 1-Ethyl-2-isopropyl-1-methylcyclohexane Constit. of Z. acerosa. Cryst. (Et20). Mp 174°. [rx]i;'
CuH14 M 168.322 -52.1 o (c, 0.28 in CHC1 3).
Oil. Bp 20 96°. Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1343
Sutherland, M.D., Aust. J. Chern., 1964, 17, 75 (struct) (Zinniadilactone)
Robinson, D.J. eta/, J. Chern. Soc. B, 1970, 965 (cryst struct) Ortega, A. et a/, Phytochemistry, 1985, 24, 2635.
Kato, K. eta/, Tetrahedron Lett., 1971, 3513 (synth)
8-Hydroxy-1,3-elemadien-12,6-olide Sq-00366
Geijerone Sq-00364

~/~~
4-Ethenyl-4-methyl-3-(1-methylethenyl)cyclohexanone, 9CI.
3-lsopropenyl-4-methyl-4-vinylcyclohexanone

I
[41411-01-2]
b~ (6cx,8cx, llcx)-:form

CuH 180
~0
M 178.274
Absolute
configuration
C 15H 220 3 M 250.337
0

(6«.,8«.,11«.)-:form [67151-76-2] Temisin

Isol. from Artemisia maritima. Prisms (EtOH). Mp 228°.
Constit. of Juniperus communis. Bp0 _1 81-86°. [rx]i? -27.8° [rx]i? + 70° (CHC1 3).
(CClJ. (6«.,8«.,11«.)-(±)-form [67225-38-1]
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1976, 14, 564. Mp 196-198°.
Kato, M. et a/, J. Chern. Soc., Perkin Trans. I, 1979, 2740 (synth) Asahina, Y. eta/, Ber., 1941, 74, 952 (isol)
Kim, D. eta/, J. Org. Chern., 1987, 52, 4633 (synth) Nishizawa, M. et a/, J. Chern. Soc., Chern. Commun., 1978, 76
Wakamatsu, T. eta/, Heterocycles, 1987, 26, 1203 (synth) (struct, synth)

210
9-Hydroxy-1,3-elemadien-12,6-olide - Isolinderalactone Sq-00367 - Sq-00374

9-Hydroxy-1,3-elemadien-12,6-9lide Sq-00367 Isofischeric acid Sq-00371

[32180-37-3]

~
~
--
(6ct,9P,11ct)-form
C15H 180 3 M 246.305
YPJ
COOH
0
C15Hn03 M 250.337 Constit. of the root of Neolitsea fischeri. Mp 120°. [cxln +
oo.
(6«,9/l,ll«)-form [109972-13-6] Shonachalin D
Constit. of Artemisia fragrans. Cryst. (EtOH aq.). Mp Me ester: [19912-86-8]. lsosericenine
110-112°. C 16H 200 3 M 260.332
Constit. of the essential oil of Neolitsea sericea. Oil. Bp5
Serkerov, S.V. eta/, Khim. Prir. Soedin., 1987, 23, 84.
139°. [cxJn+ 0°.
Hayashi, S. et al, Tetrahedron Lett., 1968, 1999 (isol)
7-Hydroxy-1,3-elemadien-6-one Sq-00368 Takeda, K. et al, J. Chern. Soc. C, 1970, 1547 (struct)
Mogoltone Joshi, B.S. et al, Indian J. Chern., 1971, 9, 80 (isol, struct)

Isogermafurene Sq-00372
Isofuranogermacrene
[17910-09-7]
C 15H 2,.02 M 236.353
Constit. of Ferula mogoltavica and F. samarcandica. Cryst.
(Etp). Mp 95-96°. [cx]i,3 + 166° (c, 1.1 in CHC1 3).
Khasanov, T.Kh. eta/, Khim. Prir. Soedin., 1973, 617; Chern. Nat.
Compd. (Engl. Trans/.), 583. C 15H 200 M 216.322
Isolated from the root of Lindera strychnifolia. Oil. (cx]i?
8-Hydroxy-1,3,7(11)-elematrien-12,8-olide Sq-00369 -0.7° (c, 0.87 in CHC1 3). Probably an artifact.
Ishii, H. et al, Tetrahedron, 1968, 24, 625 (isol)
Hikino, H. et al, Chern. Pharm. Bull., 1970, 18, 752 (isol)
Miyashita, M. et al, Chern. Lett., 1981, 593 (synth)

Isohallerin Sq-00373
C 15H 200 3 M 248.321
8fl-form [20267-91-8]8-Hydroxyisogermafurenolide
~ooc;=!
Constit. of Lindera strychnifolia. Cryst. (Etpjpet.
ether). Mp 160-161°. [cx]i;1 +4.7° (c, 1 in dioxan). ~r 1~/
Takeda, H. et al, J. Chern. Soc. C, 1968, 569.
OH
8-Hydroxy-1,3,11(13)-elematrien-12,6- Sq-00370 C20H 300 4 M 334.455
Constit. of Laserpitium halleri as a rnixt. of 12-epimers.
olide
Me ether (12/1): [110201-81-5]. Methylisohallerin

%
Oil. [cx]i; + 30° (c, 1.83 in CHC1 3).
[88125-95-5, 88126-11-8]
Appendino, G. et al, Phytochemistry, 1987, 26, 1755.

0
lsolinderalactone Sq-00374
[957-66-4]
CtsH:zo03 M 248.321
(6r~.,8fl,ll «)-form
Ac: [56064-68-7]. Epitulipdienolide. epi- Tulipdienolide ~0)
~~
C 17Hn04 M 290.358
Constit. of Liriodendron tulipifera. Cryst. (C6H 6jhexane).
Mp 134-135°. [cx]i;1 +6° (c, 0.284 in MeOH). 0
Tulipdienolide appears to be unknown.
CtsH1603 M 244.290
Doskotch, R.W., Phytochemistry, 1975, 14, 769.
Constit. of the root of Lindera strychnifolia. Cryst.
(Me2CO). Mp 118-121°. [cxJn -224.7° (c, 0.52 in
dioxan).
3,4P-Dihydro: [19332-11-7]. Dihydroisolinderalactone
CtsH 180 3 M 246.305
Constit. of L. strychnifolia. Cryst. (MeoH). Mp 124-126°
dec.

211
Juniperin- 7,8,9-Trihydroxy-1,3-elemadien-12,6-... Sq-00375 - Sq-00381

3,4cx.-Dihydro: [19332-12-8]. 4-Epidihydroisolinderalactone. Occidenol Sq-00378

4-epi-Dihydroiso/inderalactone Occidiol
From L. strychnifolia. Cryst. (MeOH). Mp 124-126° dec. [27548-56-7]
Takeda, K. eta/, J. Chern. Soc., 1964, 4578 (isol)

~H
Takeda, K. eta/, J. Chern. Soc. C, 1969, 1491 (struct)
Tori, K. eta/, Tetrahedron Lett., 1975, 4583 (pmr)
Gopalan, A. eta/, J. Org. Chern., 1984, 49, 2317 (synth)

Juniperin Sq-00375
C 15H 240 2 M 236.353
[82800-42-8] Constit. of Thuja occidenta/is. Cryst. Mp 42-44°. [cx.ln
-139°.
Tomita, B. et al, Tetrahedron Lett., 1970, 235.

mo
Sericealactone Sq-00379
[19892-18-3]

C 24H 34p 9 M 462.496

Cons tit. of Zinnia juniperifolia. Cryst. (Me2 CO /2- COO Me
propanol). Mp 118-119°. [cx.Jn +32.66° (CHC1 2).
Ct 6H 200 5 M 292.331
8-0-Deangeloyl, 8-Ac: Constit. of the essential oil of Neolitsea sericea. Cryst.
C 21 H 260 9 M 422.431 . (CC14). Mp 150-151°.
!sol. from Z. grandiflora. Gum. Struct. not certam, the
8-Deoxy: [19892-19-4]. Deoxyserecialactone
0 6 and 0 8 acyl groups may be interchanged.
C 16H 200 4 M 276.332
Ortega, A. eta/, Phytochemistry, 1982, 21, 785 (struct) Constit. of N. sericea. Cryst. (CC14). Mp 137'
Herz, W. et a/, Phytochemistry, 1982, 21, 787 (deriv)
Hayashi, S. et al, Tetrahedron Lett., 1968, 2647.

Micordilin Sq-00376
Spirafolide Sq-00380
[61701-92-6]

0~=- HI
0
=-

0
C 15H 180 3 M 246.305
C 17H 200 7 M 336.341 Constit. of Spiracantha cornifolia. Gum.
Constit. of Mikania cordifolia. Cryst. (EtOAc). Mp 176- Hashemi-Nejad, N.M. et al, Phytochemistry, 1990, 29, 3030 (isol,
1780. pmr)
Herz, W. eta/, J. Org. Chern., 1977, 42, 1720.
7,8,9-Trihydroxy-1,3-elemadien-12,6-olide Sq-00381
Miscandenin Sq-00377

-:;::::--~~~
[23758-20-5]

--
0 /OH
-OH
0 0 ~/
=-- 1 H 0 (6~, 7cx,8cx,9~, 10~)-:form
1
0 0
0 C 15H 200 5 M 280.320
C 15H 140 5 M 274.273 (6P,7«,8«,9P,l Ofl)-form
Constit. of Mikania scandens. Cryst. (Me2C0jhexane). Mp
8-Angeloyl: [88010-55-3].
232-235°. [a]i;4 -181.4° (c, 1 in CHC1 3).
C 20H 260 6 M 362.422
IP,2P-Epoxide: [100652-33-3]. 1P,2fJ-Epoxymiscandenin Constit. of Montanoa atriplicifolia. Gum.
C 15H 140 6 M 290.272
Constit. of M. cynanchifolia. Cryst. Mp 228.5". [cx.]i;4
(6P,7«,8«,9P,10«)-form
- 167° (c, 0.2 in CHC1 3). 9-Angeloyl: [88010-57-5].
C 20 H 260 6 M 362.422
Herz, W. eta/, J. Org. Chern., 1970, 35, 1453 (isol)
Cox, P.J. et a/, J. Chern. Soc., Perkin Trans. 2, 1974, 1359 (cryst
Isol. from M. atriplicifolia. Gum.
struct) 9-(3-Methyl- 2-butenoy/): [880 10-56-4].
Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1099 (deriv) C 20H 260 6 M 362.422
Isol. from M. atrip/icifolia. Gum.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1223.

212
6,8,15-Trihydroxy-1,3,11(13)-... - Vernolepin Sq-00382 - Sq-00387

6,8,15-Trihydroxy-1,3,11(13)-elematrien- Sq-00382 Verafinin C Sq-00385

12-oic acid [58139-27-8]

8
OH

COOH

HOH2C OH
C 13H 22 0 3 M 282.336
(61T.,81T.)-form
8-0-(2-Hydroxymethylpropenoyl), Me ester: [105242-48-6]. C 19H 220 7 M 362.379
Elemacarmanin Constit. of Verbesina coahuilensis. Cryst. Mp 130-133°.
C20H 28 0 7 M 380.437 Guerrero, C. eta/, Rev. Latinoam. Quim., 1975, 6, 119; CA, 84,
Constit. of Onopordon carmanicum. Oil. 56484n.
Rustaiyan, A. et a/, Phytochemistry, 1986, 25, 1659.
Vernodalol Sq-0_0386
6,9,15-Trihydroxy-1,3,11(13)-elematrien- Sq-00383 [65388-17-2]
12,8-olide
~ CH20H
OH
~,0Yo\....o ?TT_o~
YY\( 0~
H OH COOMe
HOCH2 OH
C20H 240 8 M 392.405
(61T.,8p,9fJ)-form Constit. of Vernonia anthelmintica. Cryst. (CHC1 3). Mp
9-(2-Methylpropanoyl): [99956-58-8]. Zinajlavin G 133-134°. [cxJn +36.SO (c, 1 in CHC1 3).
C19H 21;06 M 350.411 Di-Ac: Cryst. (EtOH). Mp 133-134°.
Constit. of Zinnia fiavicoma. Gum. Asaka, Y. eta/, Phytochemistry, 1977, 16, 1838.
9-(2-Methylbutanoyl): [99956-59-9]. Zinajlavin H
C20H 280 6 M 364.438 Vernolepin Sq-00387
lsol. from Z. fiavicoma. Gum.
[18542-37-5]
15-Aldehyde: see 6,9-Dihydroxy-15-oxo-1,3,11(13)-
elematrien-12,8-olide, Sq-00341
Ortega, A. et a/, Phytochemistry, 1985, 24, 2635.

8,14,15-Trihydroxy-1,3,11(13)-elematrien- Sq-00384

;R;
12,6-olide

I4CH20sH/OH
ctsH 160 3 M 276.288
(+)-form
~ ,;:;- Constit. of Veronica hymenolepis. Has high antitumour
HOH2d5 0 activity. Cryst. (CHC1 3jpet. ether). Mp 181-182°. [ex]~
+ 72° (c, 1.04 in Me2CO).
0
Ac: Cryst. (MeOH/Et20). Mp 146-147°. [cx]i; + 134° (c,
CtsH 200 3 M 280.320
0.89 in CHC1 3).
(61T.,81T.)-form
2-Hydroxymethyl-2-propenooyl: [21871-10-3]. Vernodalin
8-(2Z-Hydroxymethyl-2-butenoyl): [113412-04-7]. 20- C19H 200 7 M 360.363
Hydroxyelemajurinelloide Constit. of V. amygdalina. Oil. [cx]~4 + 125° (c, 1.35 in
C20 H 260 7 M 378.421 CHC1 3).
lsol. from Jurinella moschus. Oil. [cxln + 38° (c, 0.2 in
CHC1 3). 11P,l3-Dihydro, 2-hydroxymethyl-2-propenoyl: [89354-71-2].
II ,IJ-Dihydrovernodalin
14-Aldehyde, 15-Ac: [126622-32-0]. Dicotomentolide C 19H 220 7 M 362.379
C 17H 200 6 M 320.341 lsol. from V. amygdalina. Oil.
Constit. of Dicoma tomentosa. Gum.
(±)-form
Rustaiyan, A. et a/, Phytochemistry, 1987, 26, 2857. Prisms (CHC1 3). Mp 206°.
Zdero, C. eta/, Phytochemistry, 1990, 29, 183 (iso/, pmr)
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3908 (iso/, struct)
McPhail, A.T. eta/, J. Chern. Soc. B, 1971, 198 (cryst struct)
Ganjian, I. eta/, Phytochemistry, 1983, 22, 2525 (isol, deriv)
Yoshida, K. eta/, J. Org. Chern., 1984, 49, 5257 (synth)
Wakamatsu, T. eta/, J. Org. Chern., 1985, SO, 108 (synth, bib£)

213
Vernomenin- 1,10;4,5-Diepoxy-3,6,8-trihydroxy-... Sq-00388 - Sq-00392

Vernomenin Sq-00388
[20107-26-0]
Simple germacranes

1,10:4,5-Diepoxy-6,11-germacranediol Sq-00390
C15H 160 5 M 276.288
Constit. of Veronica hymenolepis. Has high antitumour
activity. [cx]i; -62° (c, 1.44 in Me2CO).
Ac: Cryst. (CHCI 3/Etp). Mp > 300° (softens at 212-214°).
[cx]i,6 -135° (c, 4.0 in CHCI 3).
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3903 (iso/, struct)
Wakamatsu, T. eta/, J. Org. Chern., 1985, 50, 108 (synth, bib[)
C 15H 260 4 M 270.368
(JR,4R,5R,6R,JOR)-form
Cryst. Mp 129-130°.
Zempoalin D Sq-00389
6-(2-Methy/-2-butenoyl): [114176-07-7].
[98644-40-7] C20 H 320 5 M 352.470
OAc Constit. of Nanothamnus sericeous. Cryst. Mp 129-130°.
[cx]n -88° (c, 0.5 in CHCI 3).

~~o'o 14-Hydroxy: [114176-21-5]. 1,10;4,5-Diepoxy-6,11,14-

germacranetrio/

~
C 15H 260 5 M 286.367
Cryst. Mp 136-137°.

6ocy 6-(2-Methy/-2-butenoyl), 14-(2-methy/-2-butenoy/oxy):

[114176-09-9].
C15H 380 7 M 450.571
C11H 21;08 M 406.432 Constit. of N. sericeous. Gum.
Constit. of Verbesina seattonii. Cryst. (Me 2CO/diisopropyl Bhat, U.G. eta/, J. Chern. Soc., Perkin Trans. I, 1988. 657 (isol,
ether). Mp 183-184°. [cxln +98.5° (c, 0.203 in CHCI 3). pmr, cmr, cryst struct)
Ortega, A. eta/, Phytochemistry, 1985, 24, 1755.
1,10:4,5-Diepoxy-11(13)-germacrene- Sq-00391
3,8,9-triol

~OH
HO~
CISH2405 M 284.352
(1 P.JP,4cx,5P,8P,9P,l Ocx )-form
3,8-Diange/oy/, 9-Ac: Isorhombiodol acetate
C27 H 380 8 M 490.592
Constit. of Kleinia fulgens. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 251.

1,10;4,5-Diepoxy-3,6,8-trihydroxy-11- Sq-00392
germacren-9-one

H~
C15H 240 6
OH
M 300.351
(1 ~.3~,4a,5~,6a,8cx, IOa)-form

(1 P.J p,4cx,5P,6cx,8cx,l Ocx )-form

Triange/oy/: [64234-03-3]. Bcx-Angeloyloxyligularinone A
C30 H 400 9 M 544.641
Constit. of Ligularia spp. Oil. [cx]i: + 17.3° (c, 0.9 in
CHCI 3).
8-Deoxy, diange/oy/: [64185-20-2]. 1,10;4,5-Diepoxy-3,6-
dihydroxy-11-germacren-9-one diangelate. Ligularinone A

214
1,4-Epoxy-10(14),11-germacradiene-... - 4,5-Epoxy-1(10)-germacrene-6,8-diol Sq-00393 - Sq-00398

C15H 340 7 M 446.539 1,10-Epoxy-4,7(11)-germacradien-9-one Sq-00395

Constit. of L. spp. Oil.
(1P,3P,4«,5P,6«,8P,10«)-form
Triangeloyl: [64185-15-5]. 8/J-Angeloyloxyligularionone A
c~40o, M 544.641
Constit. of L. spp. Oil. [1X]i: + 1° (c, 2.7 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 2640.
C 15H 220 2 M 234.338
(1f.,4E,10l;)-form [52061-45-7] 1,10-Epoxygermacrone
1,4-Epoxy-10(14), 11-germacradiene-3,5- Sq-00393 Constit. of the roots of Smyrnium olusatrum. Oil. [1X]~4
diol + 313° (c, 0.8 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1973, 106, 3614.

4,5-Epoxy-1(10),7(11)-germacradien-8-one Sq-00396

C15H 240 3 M 252.353

(1«,3«,4«,5«)-form [53526-63-9] Chrysandiol
Constit. of Chrysanthemum morifolium. Cryst. Mp 177-
1800. [IX]~ + 12.3° (c, 1.1 in MeOH).
Osawa, T. eta/, Tetrahedron Lett., 1974, 1569.
4,5-Epoxy-1(10),11(13)-germacradiene- Sq-00394
9,12,14,15-tetrol
C15H 220 2
~
M 234.338
(l(JO)E,4P,5«)-form [92691-35-5] Germacrone 4,5-epoxide
Constit. of essential oil of Zedoariae Rhizoma. Also
from Smyrnium creticum. Biogenetic precursor of
sesquiterpenoid constits. of Zedoariae Rhizoma. Prisms
(hexane). Mp 59-60°. [IX]:,:' +399° (c, 1.05 in CHC1 3).
Yoshihara, M. eta/, Chern. Pharm. Bull., 1984, 32, 2059; 1986, 34,
434 (iso/, cryst struct)

~ 10,14-Epoxy-4(15),5-germacradien-9-one
0
Sq-00397

'¢ty
HOH 2 C CH2 0H
C 15H 240 5 M 284.352 Absolute
(1(10)Z,4«,5P,9/I)-form configuration
14-(3-Hydroxy-2-methy/butanoyl), 9-(2-methy/butanoyl), 12-
Ac: Jlautheriol 2-methylbutyrate C 15H 200 2 M 232.322
C17H420 9 M 510.623 There is considerable confusion in the lit. concerning the
Constit. of Trixis vautheri. Gum. [1X]i: -33.SO (c, 4.7 in nomenclature of the Periplaneta americana pheromones.
CHC1 3). Vautherio1 appears to be unknown. (5E,10«)-form
14-(3-Hydroxy-2-methy/butanoyl), 9-(3-methy/butanoyl), 12- Periplanone A
Ac: Jlau theriot isobutyrate Sex pheromone of Periplaneta americana.
C17H42 0 9 M 510.623 1P,2P-Epoxide: [61228-92-0]. 1,2:10,14-Diepoxy-4(15),5-
Constit. of T. vautheri. Gum. [1X]i: -30° (c, 0.6 in germacradien-9-one. Periplanone B
CHC1 3). Sex pheromone of P. americana.
14-(3-Hydroxy-2-methy/butanoyl), 9-ange/oy/, 12-Ac:
Persoons, C.J. eta/, J. Chern. Ecol., 1974, S, 221 (isol)
Jlautheriol angelate Persoons, C.J. eta/, Tetrahedron Lett., 1976, 2055 (isol)
C17H400 9 M 508.608 Still, W.C., J. Am. Chern. Soc., 1979, 101, 2493 (synth)
Constit. of T. vautheri. Gum. [1X]i: - 34.SO (c, 0.8 in Adams, M.A. eta/, J. Am. Chern. Soc., 1979, 101, 2495 (abs
CHC1 3). config)
14-(3-Hydroxy-2-methy/butanoyl), 9-tig/oy/, 12-Ac: Takahashi, T. eta/, J. Org. Chern., 1986, S1, 3393 (synth)
Jlautheriol tiglate Macdonald, T.L. eta/, Heterocycles, 1987, lS, 305 (synth)
Kitahara, T. eta/, Tetrahedron, 1987, 43, 2689 (synth)
C17H 400 9 M 508.608 Kurahara, S. eta/, Heterocycles, 1989, 28, 167 (synth)
Constit. of T. vautheri. Gum. Not sepd. from the Mori, M. eta/, J. Chern. Soc., Perkin Trans. I, 1990, 1769 (bib/,
senecioate. cryst struct)
14-(3-Hydroxy-2-methylbutanoyl), 9-(3-methy/-2-butenoyl), Persoons, C.J. eta/, Tetrahedron Lett., 1990, 31, 1747 (rev)
12-Ac: Jlautheriol senecioate
C17H 400 9 M 508.608 4,5-Epoxy-1(1 0)-germacrene-6,8-diol Sq-00398
Constit. of T. vautheri. Gum.
[80453-47-0] 0[0H
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1649.

~ (1(10)E,4a,5a,6~,8~}:form

C 15Hu;03 M 254.369
(l(JO)E,4«,5«,6P,BP}-form [20071-60-7]
Shiromodiol

215
1,10-Epoxy-11-germacrene-2,3,4,5,8 ... - 1(10)-Epoxy-3-hydroxy-4,11-... Sq-00399 - Sq-00401

Cryst. Mp 89°. 3,9-Diangeloyl, 8-(2-methylbutanoyl), 2-Ac: [793!13-75-8]. 2-

8-Ac: [20071-59-4]. Acetoxy-4,5-dihydroxykleinifulgin
C 17H 280 4 M 296.406 C32H 480 11 M 608.725
Constit. of the leaves of Parabenzoin trilobum. Constit. of Kleiniafulgens. Gum. [a]~4 -68.SC (c, 1.2 in
Antifeeding activity for the insect Prodenia litura. Cryst. CHC1 3). Kleinifulgin appears to be unknown.
Mp 80°. [a]i,S -44.8° (c, 0.34 in CHC1 3). 3,9-Diange/oy/, 8-(2-methy/butanoyl), 5-Ac: [793!13-74-7]. 5-
Di-Ac: [20071-58-3]. Acetoxy-2,4-dihydroxykleinifulgin
C 19H 34,05 M 338.443 C32H 480 11 M 608.725
Constit. of the leaves of P. trilobium. Shows antifeeding Constit. of K. fulgens. Gum. [a]i;l -45.3° (c, l.l in
activity towards P. litura and Trimeresia miranda. Cryst. CHC1 3).
Mp 112°. [a]i,S -61.9° (c, 1.06 in CHC1 3). 11,13-Epoxide, 3,9-diange/oyl, 8-(2-methylbutanoyl), 5-Ac:
8-(4-Hydroxybenzoyl): 8-p-Hydroxybenzoylshiromodiol [79383-77-0]. 5-Acetoxy-11,13-epoxy-2,4-
C12H 300 5 M 374.476 dihydroxykleinifulgin
Constit. of Ferula orienta/is. C32 H 480 12 M 624.724
8-(4-Hydroxy-3-methoxybenzoyl): 8- Vanilloylshiromodiol Constit. of K. fulgens. Gum.
C 23H 320 6 M 404.502 2-Deoxy, 3,9-diange/oy/, 8-(2-methy/butanoyl): [79383-72-5].
From F. orienta/is. 4,5-Dihydroxykleinifulgin
(l(JO)E,4P,5rz,6P,Brz)-form [60 108-79-4) Ugamdiol C30 H 460 9 M 550.688
Cryst. (pet. ether). Mp 88-89°. [aln +47.SO. Constit. of K.fulgens. Gum. [a]i;l -31.9° (c, 0.9 in
CHC1 3).
4-Hydroxybenzoy/: [70476-17-4]. Rubaferidin
CzzH 300 5 M 374.476 2-Deoxy, 3,9-diangeloy/, 8-(2-methy/butanoyl), 5-Ac: 5-
From Feru/a rubroarenosa. Cryst. (Et20fhexane). Mp Acetoxy-4-hydroxykleinifulgin
162-164°. [1X]n -40° (c, 1.1 in CHC1 3). C32H480to M 592.725
Constit. of K. fulgens. Gum.
4-Hydroxy-3-methoxybenzoy/: [70476-16-3]. Rubaferinin
C23H 320 6 M 404.502 [79383-70-3]
Constit. of F. rubroarenosa. Bohlmann, F. et al, Phytochemistry, 1981, 20, 251.
8-(3,4,5-Trimethoxybenzoyl): [63026-58-4). Ugaferin
C25H 360 7 M 448.555 7,10-Epoxy-4-germacren-6-ol Sq-00400
Constit. of Ferula ugamica . .Cryst. (EtP/EtOAc/pet.

~
ether). Mp 125-126°. [aln -24.5° (c, 1 in CHC1 3).
(l(JO)E,4P,5rx.,6p,8p)-form [102340-74-9]
Echinadiol
Cryst. (toluenejCHC1 3).
OH
8-Cinnamoy/: [102273-85-8]. Cinnamoylechinadiol
C24H 320 4 M 384.514 CtsH2602 M 238.369
Constit. of Echinacea purpurea. Oil. (4E,6rz,7i!,,l0i!,)-form
1P,10a-Epoxide: [102340-75-0]. 1,10:4,5-Diepoxy-6,8- 0-(4-Methoxybenzoyl): [73695-85-9]. Cyclachaenin
germacranedio/. Epoxyechinadiol C23 H 3z04 M 372.503
CtsH 260 4 M 270.368 Constit. of Iva xanthofolia. Oil. [a]i;l -89.6° (c, 1 in
Cryst. (to1uene/CHC1 3). CHC1 3).
1P,10a-Epoxide, 8-cinnamoy/: [102273-86-9]. Bohlmann, F. et al, Phytochemistry, 1979, 18, 1892.
Cinnamoylepoxyechinadiol
C24H 320 5 M 400.514 1(10)-Epoxy-3-hydroxy-4,11- Sq-00401
From E. purpurea. Oil. germacradien-9-one
Wada, K. et al, Tetrahedron Lett., 1968, 4673, 4677 (isol, struct,
abs config) oO

H~
Golovina, L.A. et al, Khim. Prir. Soedin., 1978, 712 (Ugamdiol)
Saidkhodzhaev, A.l. et al, Khim. Prir. Soedin., 1978, 14, 721;
Chern. Nat. Compd. (Engl. Trans/.), 614 (Ugamdiol, Ugaferin)
Bauer, R.F.X. et al, Helv. Chim. Acta, 1985, 68, 2355 (Echinadiol)
Miski, M. et al, J. Nat. Prod. (Lloydia), 1987, 50, 829 (derivs)
Appendino, G. et al, J. Chern. Soc., Perkin Trans. J, 1990, 2139
(bib/) CtsH2203 M 250.337
Makhumdov, M.K. et al, Khim. Prir. Soedin., 1990, 26, 198; (JP,3P,4E,10rz)-form
Chern. Nat. Compd. (Engl. Trans/.), !57 (cryst struct, Ugamdiol)
Angeloyl: [64185-22-4). Ligularinone B
C20H 280 4 M 332.439
1,10-Epoxy-11-germacrene-2,3,4,5,8,9- Sq-00399 Constit. of Ligularia spp. Oil.
hexol Bohlmann, F. et al, Chern. Ber., 1977, 110, 2640.

C 15H 280 7 M 320.382

(1 p,2P,3P,4rz,5rz,8P,9P,J Orz )-form

216
1(10),4-Germacradiene-6,8-diol - 1(10),4-Germacradien-6-ol Sq-00402 - Sq-00407

1(10),4-Germacradiene-6,8-diol Sq-00402 5,10(14)-Germacradiene-1,4-diol Sq-00405

01 ,0H

C 15H 260 2
~
M 238.369
(JE,4E,6P,8tT.)-jorm [98941-66-3] Tovarol
Constit. of Thapsia villosa, also as various esters. Cryst.
C 15H 260 2
H~
M 238.369
(lp,4p,5E)-form [63181-39-5]
(Et 20jhexane). Mp 161-163°. [cxln -64.SO (c, 0.78 in Isol. from Laurencia subopposita, Parthenium lozanianum
CHC1 3). and Wikstroemea sikokiana. Cryst. (Etp). Mp 118-120°.
(JE,4E,6tT.,8p)-form [56283-44-4] Angrendiol [cx]i? + 55° (c, 2.5 in CHC1 3), [ex]~ -13° (c, 1.3 in
Constit. of Ferula pal/ida and F. tschimganica. Cryst. CHC1 3). Discrepancy in opt. rotn. of the P. lozanianum
(Etp). Mp 135-136°. [cxJn -86.1° (c, 0.9 in EtOH). isolate is unexplained.
8-(4-Hydroxybenzoyl): [39380-12-6]. Ferolin l-Ac: [63181-40-8].
C22H3004 M 358.477 C 17H 280 3 M 280.406
Constit. of roots of F. pal/ida and F. tschimganica. Constit. of soft coral Lemnalia africana. Oil. [cxln + 23°
Cryst. Mp 189-190.SO. (c, 1.39 in CHC1 3).
8-(4-Hydroxy-3-methoxybenzoyl): Chimganidin. Wratten, S.J. eta/, J. Org. Chern., 1977, 42, 3343 (isol)
Tschimganidin Izac, R.R. et a/, Tetrahedron, 1982, 38, 301 (isol)
C23H320 5 M 388.503 Kitagawa, I. eta/, Chern. Pharm. Bull., 1987, 35, 124 (isol)
From roots of F. pal/ida. Cryst. Mp 140-141°. Jakupovic, J. eta/, Phytochemistry, 1987, 26, 761 (isol)

Saidkhodzhaev, A.l. eta/, Khim. Prir. Soedin., 1977, 13, 434 (isol)
Terasa, J. de P. eta/, Phytochemistry, 1985, 24, 1779 (isol) 1(10),4(15)-Germacradiene-1,5,11-triol Sq-00406
Makmudov, M.K. eta/, Khim. Prir. Soedin., 1986, 22, 406 (cryst
struct) HO

1(1 0),4-Germacradiene-6,9-diol Sq-00403

C1sH260 3 M 254.369
(l(JO)E,1P,5P}-form
l-Ac: [86787-28-2]. Tanacetol B
C 15H 26 0 2 M 238.369 C 17H 280 4 M 296.406
(l(JO)E,4E,6p,9p)-form [128530-00-7] Puliglene Constit. of Tanacetum vulgare. Cryst. (Etp). Mp 163°.
Constit. of Pu/icaria glutinosa. Prisms (EtOH). Mp 145- [cx]i; -65.4° (c, 1.5 in MeOH).
1460. [cxln -81° (c, 0.05 in MeOH). 5-Ketone, l-Ac: [86778-06-5]. 1-Acetoxy-11-hydroxy-
4fi,5fi-Epoxide: [128530-01-8]. Epoxypuliglene 1(10),4(15)-germacradien-5-one. Tanacetol A
C 15H 260 3 M 254.369 C17H 260 4 M 294.390
Constit. of P. glutinosa. Prisms (EtOH). Mp 148-149°. Constit. ofT. vulgare. Cryst. (EtOAcjC 6H 6). Mp 98°.
[cxln +24° (c, 0.05 in MeOH). [cx]i; -99° (c, 1 in CHC1 3).
Mossa, J.S. eta/, Phytochemistry, 1990, 29, 1595 (isol, pmr, cmr, Appendino, G. eta/, Phytochemistry, 1983, 22, 509.
cryst struct)
1(10),4-Germacradien-6-ol Sq-00407
1(10),5-Germacradiene-3,4-diol Sq-00404

HO~
~ CtsH260 M 222.370
CtsH 260 2 M 238.369
6P-form
(1 (1 O)E,3 p,4p,5E)-form
Leaflets (hexane). Mp 128°. [cx]i; -201° (c, 1.3 in 2-0-Acetyl-3-0-angeloyi-P-D-fucopyranoside: [126654-58-8].
CH 2Cl 2). Pittosporanoside B1
C28 H 440 7 M 492.651
3-Ac: 3-Acetoxy-1(10),5-germacradien-4-ol
Constit. of Pittosporum tobira. Cryst. Mp 135-136°. [cxln
C 17H 280 3 M 280.406
+40.6° (c, 1.9 in CHC1 3).
Constit. of Pallenis spinosa. Needles (hexane). Mp 113°.
[cx]i; -145° (c, 0.8 in CH 2Cl2). 2-0-Angeloyl-4-0-acetyi-P-D-fucopyranoside: [126654-59-9].
Pittosporanoside B2
Appendino, G. eta/, Phytochemistry, 1989, 28, 849.
C28 H 440 7 M 492.651
Constit. of P. tobira. [cxln +9.3° (c, 5.0 in CHC1 3).
2-0-Acetyl-3-0-senecioyi-P-JJ-fucopyranoside: [126654-60-2].
Pittosporanoside B 3
C28 H440 7 M 492.651
217
1(10),4-Germacradien-11-ol - 1(10),4,7(11)-Germacratriene Sq-00408 - Sq-00414

Constit. of P. tobira. [cxln +23.0° (c, 8.6 in CHCI 3). Constit. of Ferula communis. Oil. [cx]i;' + 181° (c, 1.5 in
4cx,5cx-Epoxide: [28892-14-0]. 4cx,5cx-Epoxy-l(l O)-germacren- CHCI 3).
6P-ol. Shiromool Valle, M.E. eta/, Phytochemistry, 1987, 26, 253.
CtsH260 2 M 238.369
lsol. from leaves of Parabenzoin trilobium. Shows insect 1(10),4(15)-Germacradien-6-one Sq-00411
antifeedant activity. Cryst. (pet. ether). Mp 72-73°. (cx]i;'
+89.SO (c, 0.84 in CHCI 3).
Ketone: [50281-45-3]. 1(1 0),4-Germacradien-6-one.
A.corgermacrone. Bacchascandone
CtsH240 M 220.354
Constit. of A.corus calamus and Baccharis scandens. Liq.
Bp0 _01 130°. [cx]~4 +28.SO (c, 0.95 in CHCI 3). CISH240 M 220.354
[74559-99-2] (E)-form [25645-19-6] Preisocalamendiol
Wada, K. et at, Agric. Bioi. Chern., 1970, 34, 941, 946 (Shiromool)
Constit. of Baccharis latifolia and Acorus calamus. Oil.
Niwa, M., Bull. Chern. Soc. Jpn., 1975, 48, 2930; 1976, 49, 3148 Yamamura, S. et al, Tetrahedron, 1971, 27, 5419 (isol)
(isol, synth) Kato, K. et a/, Tetrahedron, 1971, 27, 5987 (synth)
Still, W.C., J. Am. Chern. Soc., 1977, 99, 4186 (synth) Horibe, I. et al, Tetrahedron Lett., 1975, 2849 (pmr)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1993 (isol) Still, W.C., J. Am. Chern. Soc., 1977, 99, 4186 (synth)
. Takahashi, T. et at, Tetrahedron Lett., 1983, 24, 3485 (synth) Zdero, C. et al, Phytochemistry, 1989, 28, 531 (isol)
'Nozaki, H. et al, Chern. Lett., 1990, 219 (Pittosporanosides)
1,4(15),5,10(14)-Germacratetraen-9-one Sq-00412
1(10),4-Germacradien-11-ol Sq-00408

C 15H 260 M 222.370

(l(JO)E,4E)-form [21657-90-9] Hedycaryol
CISHlOO M 216.322
There is confusion over the names of these compds. in the
Constit. of Hedycarya angustifolia. Oil. [cx]i;' + 30.8°
lit.
(CHCI 3).
(JZ,5E)-form [123163-72-4] Periplanone C. Periplanone D 1
4-Nitrobenzoy/: Cryst. Mp 110-112°. [cx]i;5 +21.4° (CHCI 3).
Constit. of faeces of female cockroaches Periplaneta
Wharton, P.S. et al, J. Org. Chern., 1972, 37, 34 (synth) americana.
Kodama, M. et a/, Tetrahedron !Att., 1976, 1121 (synth)
108,14-Dihydro: [123062-72-6]. 1,4(15),5-Germacratrien-9-
one. Periplanone D
1(10),5-Germacradien-4-ol Sq-00409 C1sH220 M 218.338
Metab. of P. americana.
1 10
(111917-97-6]
1 (I(IO)E,4cx,5E)-form Biendl, M. et al, Tetrahedron Lett., 1989, 30, 2367 (iso[)
Persoons, C.J. eta/, Tetrahedron Lett., 1990, 31, 1747 (rev)
HO
CISH260 M 222.370 1(10),4,6-Germacratriene Sq-00413
(1(10)E,4cx,5E)-form [64197-30-4] 8-1sopropyl-1 ,5-dimethy/-1 ,5, 7-cyclodecatriene
Constit. of the soft coral Lemnalia africana. Oil. [ex]~
+ 122° (c, 1.22 in CHCI 3).
11-Hydroxy: [82443-68-3]. 1(10),5-Germacradiene-4,11-diol
C15H 260 2 M 238.369
lsol. from the gorgonian Pacifigorgia media. Cryst. Mp
172-173°. [cxln -1.3° (c, 0.99 in CHCI 3). CtsH24 M 204.355
(1(10)E,4p,5E)-form [74841-87-5] (1(10)E,4E,6E)-form [34323-15-4] Germacrene C
Constit. of Pseudobrickel/ia brasiliensis. Oil. [cx]i;' -109° Constit. of the dried fruits of Kadsura japonica. Oil.
(c, 0.02 in CHC1 3). [cx]~4 + 0° (c, 5.55 in CHC1 3).
Izac, R.R. et al, Tetrahedron, 1982, 38, 301 (isol) Morikawa, K. et al, Tetrahedron Lett., 1969, 1799; 1971, 1131
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1798 (isol) (isol, struct, biosynth)

1(10),5-Germacradien-11-ol Sq-00410 1(10),4,7(11)-Germacratriene Sq-00414

8-Isopropylidene-1 ,5-dimethylcyclodeca-1 ,5-diene

C 15H 260 M 222.370 C 1sH 24 M 204.355

(l(JO)E,5E)-form (1(10)E,4E)-form [15423-57-1] Germacrene B. Germacratriene
A.llohedycariol Constit. of the peel oil of Citrus junos. Oil.

218
1(10),4,11-Germacratriene - 4(15),5,10(14)-Germacratrien-1-ol Sq-00415 - Sq-00422

Ognyanov, I. et al, Collect. Czech. Chern. Commun., 1958, 23, 2033 4(15),1 0(14),11-Germacratriene-1,5,9-triol Sq-00419
(synth)
Allen, F.H. et al, J. Chern. Soc., Chern. Commun., 1967, 588 (cryst OH
struct) j
Nishimura, K. et al, Tetrahedron Lett., 1969, 3097 (isol)

1(10),4,11-Germacratriene Sq-00415

C 15H 140 3 M 252.353

C 15H 14 M 204.355
(1(10)E,4E)-form [28387-44-2] Germacrene A
Constit. of Eunicea mammosa. Alarm pheromone of the
spotted alfalfa aphid Therioaphis maculata. Oil. [cx]i,S
-3.2° (c, 4.4 in CHCl 3).
Weinheimer, W.J. et al, Tetrahedron Lett., 1970, 497 (isol, struct)
ltoh, A. et al, Tetrahedron Lett., 1978, 2903 (synth)
(1p,5p,9fl)-form [38022-97-8] Ageratriol
Constit. of Achillea ageratum. Cryst. Mp 195°. [cx]i?
+ 30.SO (c, 2 in MeOH).
Garanti, L. et al, Tetrahedron Lett., 1972, 1397 (isol)
Bellesia, F. et al, Phytochemistry, 1975, 14, 1737 (isol)
Bellesia, F. et al, Gazz. Chim. !tal., 1976, 106, 895 (struct)
Messerotti, W. et al, J. Chern. Soc., Perkin Trans. 2, 1978, 217
(cryst struct)

1(10),4(15),5-Germacratriene Sq-00416
3-/sopropy/-6-methyl-10-methy/ene-1 ,6-cyc/odecadiene
4(15),10(14),11(13)-Germacratriene- Sq-00420
1,5,12-triol

C 15H 14 M 204.355
~
~
CH,OH

(l(JO)E,5E)-form [23986-74-5] Germacrene D CtsH140 3 M 252.353

Constit. of the essential oil of Pseudotsuga japonica. Oil. Constit. of Artemisia herba-alba. Gum.
[cx]i? - 240°.
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 3661 (isol, pmr, cmr)
5,6-Dihydro: [64141-33-9].
Oil. [ex]~ -42.7° (c, 0.55 in CHC1 3).
1(10)4,11-Germacratrien-9-ol Sq-00421
Yoshihara, K. et al, Tetrahedron Lett., 1969, 2263 (isol)

Q:\
Niwa, M. et al, Chern. Pharm. Bull., 1980, 28, 997 (isol)
Kitahara, T. et al, J. Org. Chern., 1984, 49, 3281 (synth)

1(1 0),5,11-Germacratriene Sq-00417

C15H 140 M 220.354

(l(JO)E,4E,9fl)-form [50657-20-0] Agerol
Constit. of Achillea ageratum. Cryst. Mp 63-64°. [cx]i?
+ 11.8° (c, 2 in MeOH).
Grandi, R. et al, Tetrahedron Lett., 1973, 1765.
C 15H 14 M 204.355
(1(10)E,4Z)-form [75023-40-4] Helminthogermacrene 4(15),5,10(14)-Germacratrien-1-ol Sq-00422
Constit. of Helminthosporium sativum. Oil. [cx]i,S -28° (c,
0.5 in CC14). OH

QQy
I
Winter, R.E.K. et al, J. Org. Chern., 1980, 45, 4786 (isol, struct)
McMurry, J.E. et al, Tetrahedron Lett., 1985, 26, 2171 (synth)
(1a.,5E)-form
4,6,10(15)-Germacratriene Sq-00418
C15H 140 M 220.354
(lrx.,5E)-form [65882-79-3]
Constit. of Inula cuspidata. Oil. [cx]n -180.3° (CHCl 3).
Ac:
CtsH14 M 204.355 C17H 260 2 M 262.391
(4E,6E)-form [73695-86-0] p.Germacrene C Constit. of Dilophus fasciola. Oil. [cxln -106.SO (c, 1 in
Constit. of Chrysothamnus nauseosus. Oil. CHCl 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1889.
]-Ketone: [84002-60-8]. 4(15),5,10(14)-Germacratrien-1-one
C 15H 220 M 218.338
Constit. of Calea reticulata. Oil. [cxln + 30° (c, 0.1 in
CHC1 3).
(ent-1p,5E)-form
219
1(10),4,11-Germacratrien-15,6-olide- Neoliacinic acid Sq-00423 - Sq-00429

Constit. of Jackiella javanica. Oil. [cxln + 146° (c, 2.89 in 1(10)-Germacrene-5,8-dione Sq-00426
CHC1 3). 2-1sopropyl-5 ,9-dimethyl-8-cyclodecene-1 ,4-dione
(ent-Irx.,5E)-form
Constit. of J. javanica. Oil. [cxln + 88.4° (c, 2.41 in
CHC1 3).
Fattorusso, E. et al, Tetrahedron Lett., 1978, 4149 (isof)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 157, 1793 (isof)
Nagashima, F. et al, Phytochemistry, 1990, 29, 2169 (isol, pmr,
C 15H1P 1 M 236.353
cmr)
(l(IO)E,4rx.H,7PH)-form [13657-68-6] Curdione
Constit. of Zedoariae rhizoma and Curcuma wenyujin.
1(1 0),4, 11-Germacratrien-15,6-olide Sq-00423 Cryst. Mp 61-62°. [cx]i,S +26.0° (c, 1.00 in CHC1 3).

CO\
7,11-Didehydro: [38230-32-9]. 1(10),7(1 1)-Germacradiene-
5,8-dione. Dehydrocurdione
C 15Hzz0z M 234.338
From C. zedoaria. Oil. [cxln +67.9° (c, 0.5 in CHC1 3).
Hikino, H. eta/, Chern. Pharm. Bull., 1967, 15, 1390 (isof)
0 Hikino, H. eta/, Chern. Pharm. Bull., 1972, 20, 987 (isof)
C 15H 200 1 M 232.322 Inayama, S. eta/, Chern. Pharm. Bull., 1985, 33, 1323, 2179 (abs
(I(JO)E,6fl)-form [6790-85-8] Aristolactone conjig, cryst struct)
Constit. of Aristolochia reticulata and A. serpentaria.
Cryst. (Me 2CO aq.). Mp 110-1 UO. [cx]b4 + 156.4° (c, 1 in 1-Hydroperoxy-4(15),5,10(14)- Sq-00427
EtOH). germacratriene
Martin-Smith, M. eta/, Tetrahedron Lett., 1964, 2391 (isof)
Ferguson, G. eta/, J. Chern. Res. (S), 1982, 304 (cryst struct)
Marshall, J.A. et a/, J. Org. Chern., 1987, 52, 3883 (synth)
Marshall, J.A. eta/, Tetrahedron Lett., 1987, 28, 723, 3323 (synth,
abs config)

1(1 0),4,7(11 )-Germacratrien-8-one Sq-00424

C 15H1P 1

01:0
M 236.353
(lp,5E)-form
Constit. of Senecio glanduloso-pisolus. Oil. [cx]~4 -38° (c,

~
0.1 in CHCI 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2595.
C15Hzz0 M 218.338
(l(JO)E,4E)-form [6902-91-6] Germacrone. Germacrol (obsol.) 11-Hydroxy-1(10)-germacren-3-one Sq-00428
Constit. of oil from Geranium macrorhyzum and

~H
Rhododendron adamsii. Cryst. (MeOH). Mp 56-57°.
12-Hydroxy: [103994-29-2]. 12-Hydroxy-1(10),4,7(1 1)-
germacradien-8-one. 12-Hydroxygermacrone. 13-
Hydroxygermacrone
ci5HzzOz M 234.338 Ct5Hu0z M 238.369
Isol. from Curcuma zedoaria. Oil. 1(10)£-form [99957-12-7] Germacrenone
Ognajanov, I. eta/, Collect. Czech. Chern. Commun., 1958, 23, Constit. of Carissa edulis. Oil. [cx]i? + 173.2° (c, 1.1 in
2033 (isol, struct) CHCI 3).
Horibe, I. eta/, Tetrahedron Lett., 1975, 2849 (pmr) Achenbach, H. et a/, Phytochemistry, 1985, 24, 2325.
Takahashi, T. eta/, Tetrahedron Lett., 1983, 24, 3489 (synth)
Yoshihara, M. eta/, Chern. Pharm. Bull., 1984, 32, 2059 (cryst
struct, epoxide) Neoliacinic acid Sq-00429
Shiobara, Y. eta/, Phytochemistry, 1986, 25, 1351 (12- 1,5-Epoxy-4,7-dihydroxy-8-oxo-9-germacren-15,6-olid-12-oic
Hydroxygermacrone) acid
Ulubelen, A. eta/, Phytochemistry, 1987, 26, 312 (isof)

4,10(14),11-Germacratrien-1-one Sq-00425
[128718-17-2]

C 15H 180 8 M 326.302

Constit. of Neolitsea aciculata.
Me ester: [116428-57-0].
Plates (EtOAc). Mp 214.5-215.5" dec. [cxln -108° (c, 0.3
C 15Hzz0 M 218.338
Constit. of Dictyopteris divaricata. Oil. [cx]i;' + 33.5" (c, 0.76 in EtOAc).
in CHC1 3). Takaoka, D. eta/, J. Chern. Soc., Chern. Commun., 1987, 1861.
Segawa, M. eta/, Phytochemistry, 1990, 29, 973 (isol, pmr, cmr)

220
8-0xo-1(10),4,7(11)-germacratrien-... - 3-Chloro-1,10-epoxy-8-hydroxy-... Sq-00430 - Sq-00434

8-0xo-1(10),4,7(11 )-germacratrien-13-al Sq-00430

Germacrone-13-al
[129673-85-4] 12,6-Germacranolides
IY'l
Y'&o Acanthamolide Sq-00432
[64852-96-6]
C 1 ~H 20 0 1 M 232.322
Constit. of Curcuma longa. Viscous oil. CHO O
Ohshiro, M. et al, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr)
- ,NH~
Pittosporatobiraside A Sq-00431 OH
[115526-27-7]

C19H 1 ~NO~ M 347.410

Constit. of Acanthospermum glabratum. Cryst.
(C6H 6 /MeOH). Mp 249-251°.
Saleh, A.A. eta/, J. Chern. Soc., Perkin Trans. !, 1980, 1090.

Bisparthenolidine Sq-00433
[112078-76-9]

C 26 H 38 0~ M 430.583
Constit. of Pittosporum tobira. Cryst. Mp 88-90°. [a]i;'
+ 73.SO (c, 0.1 in MeOH).
3' -Deacyl, 3' -(3-methyl-2-butenoyl): [127610-67-7].
Pittosporatobiraside B
C26H 380 5 M 430.583
Constit. of P. tobira. Oil. [a]i;' + 34.8° (c, 0.29 in
MeoH).
Suga, T. et al, Chern. Lett., 1988, 445 (isol, ms, pmr, cmr)
Ogihara, K. eta/, Phytochemistry, 1989, 28, 3085 (isol, pmr, cmr)

C30H 43N06 M 513.673

Constit. of Paramichelia baillonii and Michelia rajaniana
(Magnoliaceae). Cryst. (CHC1 3). Mp 100-103°. [a]~
- 112° (CHC1 3).
Ruangrungsi, N. et al, J. Nat. Prod. (Lloydia), 1987, SO, 891; 1988,
Sl, 1230 (isol, pmr, cmr)

3-Chloro-1,10-epoxy-8-hydroxy-4,11(13)- Sq-00434
germacradien-12,6-olide

C15H 19CI0 4 M 298.765

(IP,3P,4Z,6rx.,Sp,IOrx.)-form
0-(2,3-Dihydroxy-2-methylbutanoyl): Lacinolide B
C20 H17C107 M 414.882
Constit. of Viguiera laciniata.
Gao, F. eta/, Phytochemistry, 1989, 28, 2409 (isol, pmr, cmr)

221
13-Chloro-3,10-epoxy-8,11,15-... - 1,10;14,15-Diepoxy-8,14-dihydroxy-... Sq-00435 - Sq-00440

13-Chloro-3,10-epoxy-8,11,15-trihydroxy- Sq-00435 1,10:2,3-Diepoxy-5,8-dihydroxy- Sq-00438

2,4-germacradien-12,6-olide 4(15),11(13)-germacradien-12,6-olide
0

C 15H 17Cl0 7 M 344.748 C 15H 180 6 M 294.304

(4Z,6rx.,8p,1 op,11POH)-form (1P,2rx.,3rx.,5P,6rx.,8rx.,10rx.)-form
8-Ange/oy/: 8-Ange/oy/: [65522-32-9]. Cordifene
C20H 23 Cl08 M 426.850 C20 H 240 7 M 376.405
Constit. of Ca/ea villosa. Gum. Constit. of Erlangea cordifolia. Cryst. (CH 2C1 2 /Etz0).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2593 (isol) Mp 206° dec.
4P,J 5-Epoxide: see 1,1 0;2,3;4,15- Triepoxy-5,8-dihydroxy-
15-Chloro-1,4-epoxy-5,8,9-trihydroxy- Sq-00436 11(13)-germacren-12,6-o/ide, Sq-00591
Rustaiyan, A. et a/, Phytochemistry, 1980, 19, 1230 (isol)
11(13)-germacren-12,6-olid-14-oic acid Begley, M.J. eta/, J. Chern. Soc., Perkin Trans. I, 1981, 2702 (isol,
cryst struct)
HOOC\ OH
I

1,10:2,3-Diepoxy-8,15-dihydroxy-4,11(13)- Sq-00439
germacradien-12,6-olide

C 15H 19Cl08 M 362.763

(1p,4p,sp,6rx.,8P,9rx.,JOPH)-form
8-(2-Hydroxymethy/propenoyl), Me ester: [119863-94-4].
Tetragonolide
C21 H 27Cl0 10 M 474.891
C 15H 200 6 M 296.319
8-(2-Hydroxymethy/propenoyl), 9-(2-methy/propanoyl), Me
ester: [119886-36-1]. Tetragonolide isobutyrate (1 p,2rx.,3rx.,4Z,6rx.,8p,1 0«. )-form
C25 H 33Cl0n M 544.982 8-(4-Acetoxy-2-methy/-2Z-butenoyl): [57 498-84-7].
Constit. of Tetragonotheca repanda and T. ludoviciana. Eleganint
Oil. C22 H 260 9 M 434.442
8-(2-Hydroxymethy/propenoyl), 9-(2-methy/butanoyl), Me Constit. of Liatris e/egans. Cryst. (EtOAc). Mp 142-
ester: [119863-95-5]. Tetragonolide 2-methylbutyrate 1430. [IX]~ -108°.
C21;H35Cl0n M 559.009 3061-0/CON.
Constit. of T. ludoviciana. Oil. Herz, W. et a/, Phytochemistry, 1975, 14, 1561.
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3881.
1,10;14,15-Diepoxy-8,14-dihydroxy- Sq-00440
Clibadiolide Sq-00437 4,11(13)-germacradien-12,6-olide
[116310-64-6] 0
CHzOAc
, ,
CHzOAc
0
C 15H 180 6 M 294.304
(1p,4Z,6rx.,8rx.,l 0«. )-form
8-(2-Methy/propenoyl): [27428-86-0]. Vernolide
Ct,H220 7 M 362.379
Constit. of Veronica colorata and V. amygdalina. Cryst.
0 (Me 2COjpet. ether). Mp 180-183°. [1X]i;l +230° (CHC1 3).
C44H 580 12 M 778.935 8-(2-Methy/propenoyl), 14-Ac: Cryst. Mp 175-177°.
Constit. of Clibadium pittierii. Gum. 8-(2-Hydroxymethy/propenoyl): [27470-84-4].
Tamayo-Castillo, G. eta/, Phytochemistry, 1988, 27, 1868. Hydroxyvernolide
C 19H 220 8 M 378.378
Constit. of V. co/orata. Cryst. Mp 150° dec. [1X]n + 135°
(dioxan).

222
2,14:4,5-Diepoxy-8,14-dihydroxy-... - 1,10;4,5-Diepoxy-11(13)-germacren-... Sq-00441 - Sq-00445

8-Deoxy: [95260-29-0]. 1,10;4,15-Diepoxy-14-hydroxy- C:zoH240 7 M 376.405

4,11 (13)-germacradien-12,6-olide. Juricanolide From E. tomentosus. Cytotoxin. Powder. [1X]n -8.6° (c,
C 15H 180 5 M 278.304 0.35 in CHC1 3).
Constit. of Jurinea albicaulis. Cryst. Mp 180-181°. [1XH~6 Hayashi, T. et al, Phytochemistry, 1987, 26, 1065 (isol, cryst struct)
+115° {c, 0.1 in CHC1 3).
Toubiana, R. eta/, Tetrahedron Lett., 1967, 1333 (isol) 3,10:11,13-Diepoxy-8,15-dihydroxy-2,4- Sq-00443
Ho, C.M. et al, Tetrahedron, 1970, 26, 941 (Hydroxyvernolide)
Mompon, B. et al, Tetrahedron, 1976, 32, 2545 (struct) germacradien-12,6-olide
Todorova, M. et al, Planta Med., 1984, 50, 452 (Juricanolide)
0
2,14:4,5-Diepoxy-8,14-dihydroxy- Sq-00441
1(10),11(13)-germacradien-12,6-olide

I
OH

0
C15H 160 7 M 308.287
(4Z,6rx.,8p,Jop,ll~)-form
8-Angeloyl:
C:zoH1z08 M 390.389
CtsH180 6 M 294.304 Constit. of Calea villosa. Cryst. Mp 93°. [1X]n -27°.
Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2593.
(2a.,4rz,5rz,6rz,8rz,14rz)-form
0 14-Me, 8-(2-methylpropenoyl): Orthopappolide
methacrylate 1,10;4,5-Diepoxy-2,8-dihydroxy-11(13)- Sq-00444
C:zoH 240 7 M 376.405 germacren-12,6-olide
Constit. of Elephantopus angustifolius. Cryst. Mp 85°.
Orthopappolide is unknown. HO,
0 14-Me, 8-(3-methyl-2-butenoyl): Orthopappolide senecioate
C21 H 260 7 M 390.432
From E. angustifolius. Cryst. Mp 89°.
0 14-Me, 8-tigloyl: Orthopappolide tiglate
C21 H 260 7 M 390.432 0
From E. angustifolius. Oil.
C 15H:zo06 M 296.319
(2P,4rz,5P,6rz,8rz,14~)-form
(lp,2rx.,4rz,5rT,,6rz,8rz,10rz)-form
0 14-Et, 8-(2-methylpropenoyl): [96627-10-0]. Nudaphantin
8-Angeloyl: [91161-84-1]. Cordifolia P2
C21 H 260 7 M 390.432
C:wH260 7 M 378.421
Constit. of Elephantopus nudatus. Cytotoxic agent. Oil.
Constit. of Erlangea cordifolia. Cryst. (MeOH). Mp 189-
[1X]n -16° (c,0.5 in CHC1 3). 1900.
Haruna, M. et al, J. Nat. Prod. (Lloydia), 1985, 48, 93
(Nudaphantin) Begley, M.J. eta/, J. Chern. Soc., Perkin Trans. I, 1984, 819.
Jakupovic, J. eta/, Phytochemistry, 1987, 26, 1467
( Orthopappolide) 1,10;4,5-Diepoxy-11(13)-germacren-12,6- Sq-00445
olide
2,15:4,5-Diepoxy-8,15-dihydroxy- Sq-00442
0
1(10),11(13)-germacradien-12,6-olide

C15H:w04
~
M 264.321
0

(1P,4rz,5P,6rz,10rz)-form [66392-96-9] Michelenolide

Constit. of Michelia compressa. Cryst. (Et20). Mp 160-
1620.
0
Ogura, M. et al, Phytochemistry, 1978, 17, 957.
CtsH 180 6 M 294.304
(1 (1O)Z,2rz,4rz,5rz,6rz,8rz,l5/I)-form
8-(2-Methylpropenoyl): [108864-23-9]. Tomenphantopin B
C 19H220 7 M 362.379
Constit. of Elephantopus tomentosus. Cytotoxin. Needles
(CHC1 3). Mp 114-116°. [1X]n -11.1° {c, 0.4 in CHC1 3).
15-Me ether, 8-(2-methylpropenoyl): [108864-22-8].
Tomenphantopin A

223
1,10:2,3-Diepoxy-8-hydroxy-... - 1,9-Dihydroxy-4,10(14)-germacradien-... Sq-00446 - Sq-00450

1,10:2,3-Diepoxy-8-hydroxy-2,4,11(13)- Sq-00446 1,15-Dihydroxy-9,11(13)-germacradiene- Sq-00448

germacradien-12,6-olide 12,6: 14,8-diolide

C20H 240 6 M 360.406

(1P,2«.,3«.,4Z,6«.,8P,10«.)-form
Ct5H 180 5 M 278.304
8-Angeloyl: 15-Deoxyliscundin
C20H 240 6 M 360.406 (1«.,4«.,6«.,8p)-form
lsol. from Trichogonia santosii. Oil. l-Ac: [56650-68-1]. 4«.,5-Dihydromelampodin B
8-(2-Hydroxymethyl-2Z-butenoyl): C17H 200 7 M 336.341
C20H 240 7 M 376.405 Constit. of Melampodium cinereum. Cryst. Mp 204-205°.
Constit. of T. santosii. Cryst. (H 20). Mp 172°. 1-(2-Methylpropanoyl): 4P,5-Dihydromelampodin C
8-(2,3-Epoxy-2-methylbutanoyl): Ct,H240 7 M 364.394
C20H 240 7 M 376.405 lsol. from M. leucanthum. Gum.
lsol. from T. santosii. Cryst. (Etp). Mp 198°. [exln 0 1-Et: 4P,5-Dihydrocinerenin
- 104° (c, 0.65 in CHC1 3). Ct,H22 0 6 M 322.357
15-Hydroxy, 8-angeloyl: [57498-86-9]. Liscundin Constit. of M. leucanthemum. Gum.
Constit. of Liatris secunda. Oil. [ex]~ -75° (c, 2 in Perry, D.L. et al, J. Org. Chern., 1975, 40, 3480 (isol)
CHC1 3). Quijano, L. et al, Phytochemistry, 1985, 24, 1747 (isol, cryst struct)
15-Hydroxy, 8-(2-acetoxymethyl-2Z-butenoyl): [57498-88-1].
Liscunditrin 1,3-Dihydroxy-4,9-germacradien-12,6- Sq-00449
C22H 260 9 M 434.442 olide
Constit. of L. secunda. Amorph. solid. Mp 161°. [ex]~
-so (CHC13).
Herz, W. et al, Phytochemistry, 1975, 14, 1561 (Liscundin,
Liscunditrin)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162.

1,10:4,5-Diepoxy-8-hydroxy-11(13)- Sq-00447 0
germacren-12,6-olide
C15H 220 4 M 266.336
(1«,3P,4Z,6«.,9Z,11PH)-form [120172-53-4]
Constit. of Pyrethrum santalinoides. Cryst. Mp 163°.
[ex]~4 + 154° (c, 0.13 in CHC1 3).
9P,JOP-Epoxide: [120181-04-6]. 9P,10P-Epoxy-1«.3P-
dihydroxy-4Z-germacren-12,6«.-olide
C1sH220s M 282.336
Constit. of P. santalinoides. Gum. [ex]~ + 34° (c, 0.21 in
C15H 200 5 M 280.320 CHC1 3).
(1 p,4«,5P,6«,8P,J 0«. )-form Abde1·Mogib, M. et al, Phytochemistry, 1989, 28, 268.
Ac: [39815-40-2]. Epitulipinolide diepoxide. epi-Tulipinolide
diepoxide 1,9-Dihydroxy-4,10(14)-germacradien- Sq-00450
C 17H 220 6 M 322.357 12,6-olide
Constit. of Liriodendron tulipifera. Cryst. (EtOH/Et 20).
Mp 214-215°. [ex]~ -55.7° (c, 0.525 in CHC1 3).

~--
Doskotch, R.W. et al, J. Chern. Soc., Chern. Commun., 1972, 1137
(synth)
Doskotch, R.W. et al, Phytochemistry, 1975, 14, 769 (isol)

0
C15H 220 4 M 266.336
(lp,4E,6«.,9p)-form
9-Ac: [87494-46-0]. Herbolide D
Ct 7H 240 5 M 308.374
Constit. of Artemisia herba-alba. Oil. [ex]~ -6.5° (c, 0.24
in CHC1 3).
11 ,13-Didehydro: 1,9-Dihydroxy-4,10(14),11(13)-
germacratrien-12 ,6-olide. 9P-Hydroxyartemorin
C 15H 200 4 M 264.321

224
2,8-Dihydroxy-4,10(14)-germacradien-... - 8,11-Dihydroxy-1(10),4-germacra ... Sq-00451 - Sq-00455

Constit. of Inula heterolepsis. Gum. 3,9-Dihydroxy-4,1 0(14)-germacradien- Sq-00453

Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1166 (isol) 12,6-olide
Segal, R. eta/, Phytochemistry, 1983, 22, 129 (isol)
HO

H0~--
2,8-Dihydroxy-4,1 0(14)-germacradien- Sq-00451
12,6-olide

HO I ;OH
z Y?
0
# /
\
C 1 ~H 22 0 4 M 266.336
0 (3P,4E,6rx.,9P,11PH)-form [95262-47-8] Herbolide F
0 Constit. of Artemisia herba-alba. Cryst. (CHCJ 3). Mp
C 1 ~H 22 0 4 M 266.336 179-181°. [a]~ + 198° (c, 0.5 in CHC1 3).
(2p,6rx.,8rx.,II S)-form Segal, R. et a/, Phytochemistry, 1984, 23, 2954.
II p,I3-Dihydroanhydroverlotorin
Constit. of Artemisia gypsacea. Gum. [a]~ + 83° (c, 0.45 3,14-Dihydroxy-1(1 0),4-germacradien- Sq-00454
in CHCI3). 12,6-olide
2-Ketone: 8a-Hydroxy-2-oxo-4, I O(J4)-germacradien-J2,6a-
olide. llp,I3-Dihydroartemorin
C 1 ~H 20 0 4 M 264.321
Constit. of A. gypsacea. Gum. [a]~ +48° (c, 0.3 in
CHCI3).
Rustaiyan, A. et a/, Phytochemistry, 1989, 28, 1535 (I(IO)Z,3~,4E,6a,II ~H)-form
0
3,8-Dihydroxy-1(10),4-germacradien-12,6- Sq-00452 C•~H 22 0 4 M 266.336
olide (l(IO)Z,3p,4E,6rx.,IIPH)-form
3 ,I4-Dihydroxy-II,I3-dihydrocostunolide
OH Constit. of Lactuca sativa. Cryst. Mp I10°. [IX]~ + Il0°
(c, 0.1 in MeOH).
HO' (l(IO)E,3p,4E,6rx.,IIPH)-form
0
1 (I (JO)E,3a,4E,6a,!ra, II ~):form 3-0-P-0-Glucopyranoside: Lactuside B
C21H3209 M 428.478
0 Isol. from L. laciniata. Amorph. [IX]~ + 21.9° (c, 0.98 in
C1~H2204 M 266.336 MeOH).
(I(I O)E,3rx.,4E,6rx.,8rx.,II /!,)-form 14-Aldehyde: [I02488-14-2]. 3-Hydroxy-14-oxo-1(10),4-
Di-Ac: [39262-27-6]. Millefin germacradien-12,6-olide. Lactulide A
C19H 21;06 M 350.41I From L. laciniata. Cryst. (MeOH). Mp 191.5-195°. [IX]~
Constit. of Achillea millefolium. Cryst. Mp 209-210°. -82.1° (c, 0.95 in Py).
(l(IO)E,3p,4Z,6rx.,8p,III!,)-form 14-Aldehyde,3-0-P-D-glucopyranoside: [106009-43-2].
8-(4-Hydroxy-2-hydroxymethyl-2£-butenoyl): II ,I3- Lactuside A
Dihydroeucannabinolide C21 H 300 9 M 426.463
GnH 34P 8 M 422.474 From L. laciniata. Amorph. [a]~ -73.8° (c, 0.84 in
Isol. from Stevia monardaefolia. Amorph. solid. Mp 5I- MeOH).
60o. [a] 0 -93.6° (CHCI3). Mahmoud, Z.F. eta/, Phytochemistry, 1986, 25, 747.
Nishimura, K. eta/, Phytochemistry, 1986, 25, 2375.
(I(IO)E,4Z,6rx.,8rx.,IIPH)-form
3-Ketone, 8-Ac: [99102-52-0]. 8a-Acetoxy-3-oxo-1(10)E,4Z-
germacradien-12,6-olide. Heliangolidin 8,11-Dihydroxy-1(1 0),4-germacradien- Sq-00455
C 17 H 22 0~ M 306.358 12,6-olide
Constit. of Artemisia canariensis. Cryst. (EtOAc). Mp
187-189°. [a] 0 +2I6.5o (c, 0.194 in CHCI 3).
Kasymov, Sh.Z. et a/, Khim. Prir. Soedin., 1972, 8, 246; CA, 77, al~H
85556y (Millefin)
Gomez, G.F. eta/, Phytochemistry, 1983, 22, 197
(Dihydroeucannabinolide)
T \~-OH
Breton, J.L. eta/, Tetrahedron, 1985, 41, 3141 (Heliangolidin) 0
CtsH 2z04 M 266.336
(I(IO)E,4E,6P,8rx.,IIrx.OH)-form
11-Angeloyl, 8-Ac: [26560-24-7]. Laserolide
Cz2H 300 6 M 390.475
Constit. of roots of Laser trilobum. Cryst. (diisopropyl
ether). Mp 140-141°. [ali? -234°.
Holub, M. eta/, Collect. Czech. Chern. Commun., 1970, 35, 284
(is of)
Holub, M. eta/, Collect. Czech. Chern. Commun., 1985, 50, 1878
(cryst struct)

225
8,15-Dihydroxy-1(10),4-germacradien-... - 1,3-Dihydroxy-4,10(14),11(13)-... Sq-00456 - Sq-00460

8,15-Dihydroxy-1(1 0),4-germacradien- Sq-00456 0 1-Et: [56650-62-5]. Cinerenin

12,6-olide Ct7Hw06 M 320.341
Constit. of M. cinereum and M. argophyllum. Cryst.
(EtOAc). Mp 161-163°.
4,5-Dihydro: see 1,15-Dihydroxy-9,11(13)-germacradiene-
12,6: 14,8-diolide, Sq-00448
Perry, D.L. et al, J. Org. Chern., 1975, 40, 3480.
Fronczek, F.R. et al, J. Chern. Soc., Perkin Trans. 1, 1980, 1425
(cryst struct)
C15H 220 4 M 266.336
(1(10)E,4E,6rz,J1PH)-form 1,2-Dihydroxy-4,10(14),11(13)- Sq-00459
8-(3-Methylbutanoyl): 11P,13-Dihydroarbutifolin germacratrien-12,6-olide
C20H 34,05 M 350.454
Constit. of Centaurea arbutifolia. Oil. [o:] 0 +95° (c, 5.2
in CHCl 3)(as acetate).
8-(2-Acetoxymethyl-2-propenoyl): 11p, 13-Dihydroamarin
C21H28 0 7 M 392.448
Constit. of C. amara. Oil.
Gonzal!ilez, A.G. et al, An. Quim., Ser. C, 1980, 76, 296
(Dihydroamarin)
Gonzalez, A.G. et al, Phytochemistry, 1981, 20, 1895
CtsHw04 M 264.321
(Dihydroarbutifolin) (1 p,2rz,6rz )-form
2rz-Hydroxyartemorin
Constit. of Artemisia hispanica. Needles (EtOH). Mp
8,15-Dihydroxy-1(10),11(13)- Sq-00457 220-221°.
germacradien-12,6-olid-14-oic acid
Sanz, J.F. et al, Phytochemistry, 1989, 28, 2163 (isol, pmr)
COOH

OOH~
1,3-Dihydroxy-4,10(14),11(13)- Sq-00460
germacratrien-12,6-olide
OH

0 (1 ~.3ME,6cxl:form

CtsHw06 M 296.319
(1(10)E,4P,6rz,8fl)-form
8-(2-Methylpropanoyl), Me ester: [67927-54-2]. Melnerin A 0
C20H 280 7 M 380.437 C15H 200 4 M 264.321
Constit. of Melampodium cinereum. (lp,Jp,4E,6rz)-form [28148-84-7] Ridentin
8-(2-Methylbutanoyl), Me ester: [67927-56-4]. Melnerin B Constit. of Artemisia spp. Cryst. Mp 215-218° dec. [o:]i;
C21H300 7 M 394.464 -113° (c, 0.46 in CHC 3).
Constit. of M. cinereum. 11P,l3-Dihydro: [117255-06-8]. 1,3-Dihydroxy-4,10(14)-
Watkins, S.F. et al, J. Chern. Soc., Perkin Trans. 2, 1978, 599. germacradien-12 ,6-olide. Dihydroridentin
CtsH220 4 M 266.336
1,15-Dihydroxy-4,9,11(13)- Sq-00458 Constit. of A. rupicola and A. tripartita. Cryst. Mp 193-
germacratriene-12,6;14,8-diolide 1940.
Jlo:,l3-Dihydro: [117232-58-3]. 11-Epidihydroridentin
0 CtsH2204 M 266.336
Constit. of A. lanata. Gum.
1-Ketone: [85921-40-0]. 3P-Hydroxy-1-oxo-4,10(14),11(13)-
germacratrien-12,6o:-olide. 3p-Hydroxyanhydroverlotorin
CtsHt80 4 M 262.305
Constit. of Tanacetum parthenium. Gum.
(1p,Jp,4Z,6rz)-form [92692-37-0] Pulverulide
Constit. of Leucanthemopsis pulverulenta. Oil. [o:] 0 +8.4°
C15H 160 5 M 276.288 (c, 0.83 in CHC13).
(1rx.,4Z,6rx.,8fl)-form 3-Ac: 3-Acetylpulverulide
C17H220 5 M 306.358
l-Ac: [51419-54-6]. Melampodin B
Constit. of Stevia alpina. Gum.
Ct7Ht80 7 M 334.325
Constit. of Melampodium spp. Cryst. (EtOAc). Mp 226- llo:,J3-Dihydro: 1,3-Dihydroxy-4,10(14)-germacradien-12,6-
2280. olide. 11,13-Dihydropulverolide
C 15H 220 4 M 266.336
1-(2-Methylpropanoyl): [56650-65-8]. Melampodin C
Constit. of Chrysanthemum lavandulifolium. Gum. [o:]~4
C 19H 220 7 M 362.379
+26° (c, 0.9 in CHC1 3).
Constit. -of M. argophyllum. Cryst. (EtOAcjEtp). Mp
199-201°. llo:,J3-Dihydro, 1-hydroperoxide:
CtsH 2004 M 264.321

226
1,8-Dihydroxy-4,10(14),11(13)-... - 2,8-Dihydroxy-1(10),4,11(13)-... Sq-00461 - Sq-00463

Constit. of C. lavandulifolium. Gum. 2,3-Dihydroxy-1(10),4,11(13)- Sq-00462

(1~,3~,4E,6rx.)-form[66322-62-l]Isoridentin germacratrien-12,6-olide
Constit. of Achillea biebersteinii.
Irwin, M.A. et al, Phytochemistry, 1969, 8, 2009 (isol)
Yusupov, M.l. et al, Khim. Prir. Soedin., 1977, 800 (Isoridentin)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2543 (isol)
De Pascual Teresa, J. eta/, Phytochemistry, 1984, 23, 1178
(Pulverulide)
Aguilar, J.M. et al, Phytochemistry, 1988, 27, 2229 (isol, struct)
de Heluani, C.S. et al, Phytochemistry, 1989, 28, 1931 0
(Acetylpulverulide) C 15H 200 4 M 264.321
Marco, J.A. eta/, Tetrahedron, 1990, 46, 6931 (Dehydropulverolide) (1rx.,3P,6rx.)-form
3-Ac: 3fi-Acetoxy-21X-hydroxy-l(l 0),4, ll(13)-germacratrien-
1,8-Dihydroxy-4,10(14),11(13)- Sq-00461 l2,61X-olide. 1rx.-Hydroxyhanphyllin 3-0-acetate
germacratrien-12,6-olide C 17H 220 5 M 306.358
Constit. of an Eriocephalus sp. Oil. [1X]~4 + 131° (c, 0.37
OH in CHC1 3).
I

Zdero, C. et a/, Phytochemistry, 1987, 26, 2763.

2,8-Dihydroxy-1(10),4,11(13)- Sq-00463
(lcx,4E,6cx,8~)-:form germacratrien-12,6-olide

C15H2o04 M 264.321 H0,%

8 OH

(1rx.,4E,6rx.,Bf/)-form fi .6 _...,
8-(3-Acetoxy-2-hydroxy-2-methylbutanoyl): [95653-76-2].
Ursanthemolide b
C 22H 300 8 M 422.474 0
Constit. of Ursinia anthemoides. Cryst. Mp 74-76°. [1X]i? C15H 200 4 M 264.321
-25.8°. (1(1 O)E,1rx.,4E,6rx.,8f/)-form [72229-33- 5]1rx.-Hydroxyeupatolide
8-(3-Acetoxy-2-hydroxy-2-methylbutanoyl), 1-Ac: [95653-73- Constit. of Eupatorium mikanioides. Cryst.
9]. Acetylursanthemolide (CHCl 3fMeOH). Mp 184-186°. [1X] 0 + 196.SO (c, 0.1 in
C 24H 320 9 M 464.511 Py).
From U. anthemoides. Cryst. Mp 115-117°. 2-Ac: 1rx.-Acetoxyeupato/ide
llfi,13-Dihydro: [97534-15-l]. 1fi,81X-Dihydroxy-4, IO(l4)- C17H 220 5 M 306.358
germacradien-l2,61X-olide. Shonachalin A Constit. of Mikania grazielae. Cryst. (Etpjpet. ether).
C 15H 220 4 M 266.336 [1X]i: +59° (c, 0.76 in CHC1 3).
Cons tit. of Artemisia fragrans. Oil. 8-(2-Hydroxymethyl-2Z-butenoyl): [38456-39-2].
11fi,13-Dihydro, 1-ketone: 8rx.-Hydroxy-1-oxo-4,10(15)- Deacetyleupaserrin
germacradien-11,6rx.-olide C20 H 2P 6 M 362.422
C15H 20 0 4 M 264.321 Constit. of E. mikanioides and E. semiserratum. Cryst.
lsol. from A. caerulescens. Oil. (EtOAcjhexane) (also descr. as unstable amorph. foam).
lliX,l3-Dihydro: 11-Epishonachalin A Mp 132-135°. [1X]i;' +75° (c, 0.9 in MeOH).
C 15H 200 3 M 248.321 8-(2R,3R-Epoxy-2-hydroxymethylbutanoyl): [72229-35-7].
lsol. from A. herba-alba. Gum. [1X]i: + 105° (c, 0.4 in C20 H 260 7 M 378.421
CHC1 3). Constit. of E. mikanioides. Cryst. (CHCI 3 /MeOH). Mp
(Ip,4E,6rx.,8rx.)-form 170-172°. [cx] 0 +97.8° (c, 0.027 in Py).
1-Hydroperoxide: [125675-21-0]. 1P-Hydroperoxy-8rx.- 8-(2S-Hydroxy-2-hydroxymethyl-3S-mercaptobutanoyl):
hydroxy-4,10(14)-germacradien-11,6rx.-olide [72229-36-8].
C 15H 22 0 5 M 282.336 C 20 H 280 7 S M 412.503
lsol. from A. herba-alba. Unstable viscous gum. [1X]i: Constit. of E. mikanioides. Cryst. (CHCI 3 /MeOH). Mp
+ 50° (c, 0.2 in CHC1 3). 180-181°. [1X] 0 + 102° (c, 0.02 in Py).
Kroszczynski, W. et al, Collect. Czech. Chern. Commun., 1985, 50, 8-(3S-Hydroxy-2-methylenebutanoyl): [72229-37-9].
94 (Ursanthemolide, Acetylursanthemolide) C20H 260 6 M 362.422
Serkerov, S.V. et al, Khim. Prir. Soedin., 1985, 196 (Shonachalin A) Constit. of E. mikanioides. Gum. [1X] 0 .+80S (c, 0.23 in
Marco, J.A. et al, Phytochemistry, 1989, 28, 3121 (derivs) CHC1 3).
Sanz, J.P. et a/, Phytochemistry, 1990, 29, 2913 (isol, bib[)
8-Angeloyl: [72704-04-2]. Mo/lisorin A
C 20 H 260 5 M 346.422
Constit. of H. mol/is and Tithonia rotundifolia. Oil or
gum. [1X]i: + 133.3° (c, 0.12 in CHC1 3).
8-(2-Acetoxymethyl-2Z-butenoyl): [38456-36-9]. Eupaserrin
C22H 280 7 M 404.459
Constit. of E. semiserratum. Shows tumour-inhibitory
props. Mp 153-154°. [1X]i;' +71.2° (c, 0.94 in MeOH).
8-(2R,3R-Epoxy-2-methylbutanoyl): [72229-34-6].
Mollisorin B
C 20H 260 6 M 362.422

227
3,8-Dihydroxy-1(10),4,11(13)-... - 3,8-Dihydroxy-1(10),4,11(13)-... Sq-00464 - Sq-00464

Constit. of E. mikanioides and Helianthus mol/is. Gum Constit. of E. sachalinense and of Schkuhria
or cryst. Mp 165-166°. [aln +67.7° (c, 0.2 in CHC1 3). anthemoidea. Cryst. Mp 149° dec., Mp 169-172°. [a]~
Identity of samples not established. + 119° (c, 0.22 in EtOH)( + 75°). Hiyodorilactone E and
Herz, W. eta/, J. Org. Chern., 1973, 38, 1260; 1980, 45, 489. Santhemoidin C have not been compared and their
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 267; 1982, 21, 1169. recorded props. are different.
8-(4-Acetoxy-2-acetoxymethyl-2E-butenoyl), 3-Ac: [72493-
3,8-Dihydroxy-1(10),4,11(13)- Sq-00464 42-6]. Hiyodorilactone F
germacratrien-12,6-olide C26 H 3z0 10 M 504.533
Cons tit. of E. sachalinense. Yellow oil. [aJi? -· 141° (c,
3,8-Dihydroxycostunolide
0.21 in EtOH).
OH l(JO)E,JP,4Z,6rr.,BP-form
(1 ( 1O)E,3cx,4E,6cx,8cx )-form 3-Ac: [68628-57-9]. Hiyodorilactone C
HO' C17H 2z0 5 M 306.358
I Constit. of E. sachalinense. Oil. [a]i; -109° (c, 0.91 in
0 EtOH).
0 8-(4-Hydroxy-2-methyl-2E-butenoyl), 3-Ac: [66148-25-2].
C 15H 200 4 M 264.321 Chromolaenide
(l(JO)E,3rr.,4E,6rr.,8rr.)-form C22H 280 7 M 404.459
Ac: [25739-42-8]. Chihuahuin lsol. from Chromolaena glaberrima. Cryst. (Etpjpet.
C 17H 220 5 M 306.358 ether). Mp 138°. [a]i; -146° (c, 0.7 in CHC1 3 ).
Constit. of Ambrosia confertiflora. Cryst. 8-(4-Hydroxy-2-methyl-2Z-butenoyl), 3-Ac: [68539-58-2].
(CH 2 Cl2 /isopropyl ether). Mp 168-170°. (a]i; + 112° (c, Hiyodorilactone B
4.8 in CHC1 3). C22 H 280 7 M 404.459
8-Tigloyl, 3-Ac: 3rr.-Acetoxy-8rr.-tigloyloxy-costunolide Constit. of E. sachalinense. Yellow oil. [a]~4 -140° (c,
C22H 28 0 6 M 388.460 0.67 in EtOH).
Constit. of Lasiolaena santosii. Gum. 8-(4-Hydroxy-2-hydroxymethyl-2E-butenoyl), 3-Ac: (38458-
(l(JO)E,3rr.,4E,6rr.,8/l)-form 58-1]. Eucannabinolide. Schkuhrin I.
Hydroxychromolaenide. Hiyodorilactone A
llrx.,13-Dihydro, Di-Ac: [56192-71-3]. Carmelin
C 19H 260 6 M 350.411 C22 H 280 8 M 420.458
Constit. of Stevia serrata. Cryst. Mp 176-177°. [aln Constit. of E. cannabinum and E. sachalinense. Gum or
+ 146.1°. yellow oil. [aJn -121° (CHCI 3).
8-(4-Acetoxymethyl-2-hydroxymethyl-2E-butenoyl), 3-Ac:
(1(10)E,Jp,4E,6p,Bfl)-form
Eucannabinolide 19-0-acetate
8-(2,3-Epoxy-2-methylbutanoyl): [52677-97-1]. Ursiniolide C C24H 300 9 M 462.496
C20H 26 0 6 M 362.422 Isol. from Isocarpha oppositifolia var. achyranthes. Pale-
Constit. of Ursinia anthemoides. Cryst. Mp 173-175°. yellow oil.
8-(2,3-Epoxy-2-methylbutanoyl), 3-Ac: [52677-96-0]. 8-[2-(2-Hydroxymethyl-2E-butenoy/oxy)-2E-butenoyij, 3-Ac:
Ursiniolide A [72057-04-6]. 4' -Deoxypro11incialin
C22H2807 M 404.459 C27H 340 9 M 502.560
Constit. of U. anthemoides. Cryst. Mp 140-142°. (a]i? Constit. of L. cylindracea. Oil. [a]i; -107.4° (c, 1.5 in
-237°. CHCI 3).
11P,13-Epoxide, di-Ac: 3P,8P-Diacetoxy-11P,13-epoxy- 8-[4-Hydroxy-2-(2-hydroxymethyl-2E-butenoy/oxy)-2E-
1(10),4-germacradien-12,6a-olide. 3P-Acetoxy-1lp,J3- butenoyl], 3-Ac: [40328-96-9]. Pro11incialin
epoxyepitulipinolide C2,H 340,0 M 518.560
C 19H 240 7 M 364.394 Constit. of L. provincia/is. Gum. [aJn -85° (c. 0.6 in
Isol. from Bartlettia karwinskiana. Oil. CHCI3).
8-(3-Acetoxy-2-hydroxy-2-methy/butanoyl), 3-Ac: (58857-01- 8-(2-Methy/propanoyl), 3-Ac: [56775-13-4]. Peucephyllin
5]. Ursiniolide B C21 H 280 6 M 376.449
C24H 320 9 M 464.511 !sol. from Peucephyl/um schottii. Cryst. (EtOAc). Mp
Constit. of U. anthemoides. Cryst. Mp 152-154°. [ali? 120.5-121.SO. [a]~ -140.9° (c, 1 in CHC1 3).
-217°.
9-(3-Furoyl), 3-Ac: [95260-95-0]. Santhemoidin A
(1(10)E,3P,4E,6rr.,8fl)-form C22H 240 7 M 400.427
8-(2-(2-Hydroxymethyl-2E-butenoyloxy)-2E-butenoyij: Constit. of S. anthemoidea. Cryst. Mp 167-169°. [aln
[72057-03-5]. Jp-Hydroxyliacylindrolide -184° (c, 0.22 in MeOH).
C25H 320 8 M 460.523 9-(2,5-Dihydro-58-methoxy-3-furoyl), 3-Ac: [95297-85-1].
Constit. of Liatris cylindracea. Oil. [a]~4 + 18.9° (c, 0.75 Santhemoidin B
in CHC1 3). C23 H 280 8 M 432.469
8-(4-Acetoxy-2-hydroxymethyl-2E-butenoyl): [72493-40-4]. From S. anthemoidea. Cryst. Mp 147-149°. [a]" -146°
Hiyodorilactone D (c, 0.18 in MeOH).
C22H 280 8 M 420.458 (l(JO)E,3rr.,4Z,6rr.,8/l)-form
Constit. of Eupatorium sachalinense. Yellow oil. [a]~ Desacetyleupaformonin
+81° (c, 0.36 in EtOH). lsol. from Bahia ambrosioides. Gum.
8-(2-Acetoxymethyl-4-hydroxy-2E-butenoyl): [72493-41-5]. 3-Ac: [55520-20-2]. Eupaformonin
Hiyodorilactone E. Santhemoidin C C17H 2z05 M 306.358
C22H 280 8 M 420.458 Constit. of E. formosanum. Cytotoxic agent. Cryst. Mp
216-218°.

228
3,8-Dihydroxy-4,9,11(13)-••• - 3,8-Dihydroxy-4(15),9,11(13)-.•• Sq-00465 - Sq-00467

8-[4-Hydroxy-2-(2-hydroxymethyl-2E-butenoyloxy)-2E- Constit. of flower heads of Chrysanthemum

butenoylj: [72075-27-5]. 4' -Deoxy-3-deacetoxy-3rx.- cinerariaefolium. Amorph. [IX]~ -27° (c, 1.5 in MeOH).
ltydroxyprovincia/in 11P,l3-Dihydro, di-Ac: Needles (EtOH). Mp 165-166°.
C 25H 310 8 M 460.523 Shafizadeh, F. eta/, J. Org. Chern., 1972, 37, 274 (isol)
Isol. from L. cy/indracea. Oil. [1X]i: -81.4° (c, 0.2 in Sashida, Y. eta/, Phytochemistry, 1983, 22, 1219 (isol)
CHC1 3).
8-[4-Hydroxy-2-(2-hydroxymethyl-2E-butenoyloxy)-2E-
3,8-Dihydroxy-4,10(14),11(13)- Sq-00466
butenoylj, 3-Ac: [72075-50-4]. 3-Epi-4' -deoxyprovincialin
C 17H 340 9 M 502.560 germacratrien-12,6-olide
lsol. from L. cylindracea. Artevasin
(1(10)E,3rx.,4Z,6rx.,8rx.)-form [41744-43-8]
8-(2-Methy/propenoyl): 3-Epinobilin

1-r
Czoll160 5 M 346.422 ~OH
lsol. from Anthemis nobilis flowers. Mp 137°.
(1(10)E,3P,4Z,6rx.,8rx.)-form
8-Ange/oy/: [31824-11-0]. Nobilin
HO' T
C 10H 160 5 M 346.422 0
Constit. of A. nobilis. Cryst. (EtOH). Mp 177-178°. C 15H 100 4 M 264.321
[1X]n + oo.
(3~,4E,6rx.,8~)-form
3-Ketone, 8-ange/oy/: [63529-14-6]. 3-Deltydronobilin Constit. of Artemisia tridentata. Cryst. Mp 209-210°.
C 10H 140 5 M 344.407 [1X]n +244° (c, 0.75 in EtOH).
lsol. from A. nobilis. Cytotoxic. Cryst. (EtOHfCHC1 3).
Mp 205°. [1X]i? + 136.6° (c, 0.526 in MeOH). Asplund, R.O. et a/, Phytochemistry, 1972, 11, 3542.

Renold, W. eta/, J. Org. Chern., 1970, 35, 4264 (Chihuahuin)

Benesova, V. eta/, Tetrahedron Lett., 1970, 5017 (Nobilin) 3,8-Dihydroxy-4(15),9, 11 (13)- Sq-00467
Herz, W. eta/, J. Org. Chern., 1973, 38, 2485 (Provincia/in) germacratrien-12,6-olide
Salmon, M. eta/, Rev. Latinoam. Quim., 1975, 6, 45 (Carmelin)
Begley, M.J. eta/, Tetrahedron Lett., 1975, 1105 (Peucephyllin)

~
H
McPhail, A.T. et a/, J. Chern. Soc., Perkin Trans. 1, 1976, 578
(Eupaformonin)
Holub, M. et a/, Collect. Czech. Chern. Commun., 1977, 42, 1053 HO (3~,6tx,8tx,9E)-form
(Nobilin, Epinobilin, Dehydronobilin) I
Bohlmann, F., Chern. Ber., 1978, 111, 408 (Chromolaenide)
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1978, 43, 2779 0
(Provincia/in) C 15H 100 4 M 264.321
Pettei, M.J. eta/, Heterocycles, 1978, 11, 471 (Schkuhrin I)
Takahashi, T. eta/, Chern. Pharm. Bull., 1979, 27, 2539 (isol) (3p,6rx.,8rx.,9E)-form [41653-76-3] Tatrid.in B
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 847 (3- Constit. of Artemisia spp. Gum.
Hydroxyliacylindrolide, Deacetylprovincialin) Dibenzoyl: Cryst. Mp 220-224°.
Samek, Z. eta/, Tetrahedron Lett., 1979, 2691 (Ursinio/ides)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613 (3-Acetoxy-8- 111X,l3-Dihydro: 3,8-Dihydroxy-4(15),9-germacradien-12,6-
tig/oy/oxycostuno/ide) o/ide
Still, W.C. eta/, J. Am. Chern. Soc., 1983, 105, 625 (synth) C 15Hn04 M 266.336
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 250. Constit. of flower heads of Chrysanthemum
Perez, A.L. eta/, Phytochemistry, 1984, 23, 2911 (Santhemoidins) cinerariaefolium. Needles (EtOH). Mp 166-168°. [IX]~
Perez, A.L. eta/, Phytochemistry, 1986, 25, 745 (Eucannabinolide +43° (c, 0.65 in MeOH).
19-acetate)
Gao, F. eta/, Phytochemistry, 1986, 25, 1231
111X,l3-Dihydro, 8-0-P-n-g/ucopyranoside:
(Acetoxyepoxyepitulipinolide) C21H 310 9 M 428.478
Zdero, C. eta/, Phytochemistry, 1990, 29, 205 From C. cinerariaefolium. Powder. [IX]~ -25° (c, 1.0 in
(Desacetyleupaformonin) MeOH).
11P,l3-Dihydro:
3,8-Dihydroxy-4,9,11(13)-germacratrien- Sq-00465 C 15H 110 4 M 266.336
12,6-olide Isol. from Artemisia herba. Cryst. (MeOH). Mp 199-
199.50.
OH 11P,l3-Dihydro, 3-ketone: 8rx.-Hydroxy-3-oxo-4(15),9-
germacrad.ien-12,6rx.-olide
(3~,4E,6tx,8tx,9E)-form C 15H 200 4 M 264.321
HO lsol. from A. herba. Cryst. (EtP/EtOAc). Mp 155-156°.
I
0 4,11,13,15- Tetrahydro, 3-ketone: see 8-Hydroxy-3-oxo-
0 1(1 0)-germacren-12,6-o/ide, Sq-00519
C 15H 100 4 M 264.321 Shafizadeh, F. eta/, Phytochemistry, 1973, 12, 857 (isol)
Gordon, M.M. et a/, J. Nat. Prod. (Lloydia), 1981, 44, 432 (iso/,
(3P,4E,6rx.,8rx.,9E)-form [41653-75-2] Tatrid.in A cryst struct)
Constit. of Artemisia arbuscu/a. Cryst. (MeOH). Mp Sashida, Y. eta/, Phytochemistry, 1983, 22, 1219 (isol)
176-177°. [IX]~ -49° (c, 1.1 in EtOH).
11P,J3-Dihydro: 3P,81X-Dehydroxy-4E,9E-germacradien-
12,61X-olide
C 15Hn04 M 266.336

229
3,9-Dihydroxy-1(10),4,11(13)-... - 8,14-Dihydroxy-1(10),4,11(13)-... Sq-00468 - Sq-00472

3,9-Dihydroxy-1(10),4,11(13)- Sq-00468 Constit. of M. hibiscifolia. Cryst. (CHC1 3/C 6 H6). Mp

germacratrien-12,6-olide 193-194°. [ex) 0 -200° (c, 0.06 in CHC13).
(l(JO)E,4E,6«,8P,9fJ)-form
OH 8-Tig/oy/:
C20H 260 5 M 346.422
Constit. of Lasiolaena santosii.
(1(10)E,3p,4E,6a,9P}:form (l(JO)E,4E,6«,8P,9~)-form
8-(2-Methy/butanoyl): [73021-14-4].
C20H 280 5 M 348.438
0 Constit. of Eupatorium mohrii. [ex] 0 + 50.3° (CHC1 3).
CtsH 200 4 M 264.321 Herz, W. eta/, Phytochemistry, 1979, 18, 1337.
(l(JO)E,JP,4E,6«,9fJ)-form Herz, W. et a/, J. Org. Chern., 1980, 45, 1113.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.
Di-Ac: [83725-52-4]. 3P-Acetoxyhaageanolide acetate Chandra, A. eta/, Phytochemistry, 1987, 26, 1463.
C 1,H140 6 M 348.395
Isol. from Ursinia saxatilis. Gum. [ex]~ +53° (c, 0.2 in
Et20). 8,13-Dihydroxy-1(10),4,7(11)- Sq-00471
(l(JO)E,3p,4E,6«,9«)-form
germacratrien-12,6-olide
llcx,J3-dihydro, di-Ac: [116988-15-9]. Sintenin
c.,Hu;06 M 350.411
Constit. of Achillea sintenisii. Amorph.
c:c:-~:rOH
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1357 (isol)
Goren, N. eta/, Phytochemistry, 1988, 27, 2346 (Sintenin)
1 b_:r-cHpH
0
3,13-Dihydroxy-1(10),4,7(11)- Sq-00469 CtsH2004 M 264.321
germacratrien-12,6-olide

HqCH,OH
(l(JO)E,4E,6«,8«)-form [126829-64-9]
Constit. of Pentzia pinnatisecta. Gum.
4ex,5 ex-Epoxide: [126854-16-8]. 4ex,5ex-Epoxy-Sex, 13-
dihydroxy-1(10)E, 7(11 )-germacradien-12,6ex-olide
C15H 200 5 M 280.320
Constit. of P. pinnatisecta. Cryst. Mp 182°.
0 4ex,5ex-Epoxide, 13-Ac: [126829-67-2]. 13-Acetoxv-4ex,5ex-
epoxy-8ex-hydroxy-1(iO), 7(11 )-germacradien-12,6ex-olide
C 15H 200 4 M 264.321
C 17H 220 6 M 322.357
(l(JO)E,JP,4E,6«)-form Constit. of P. pinnatisecta. Gum.
3-Ac: 4ex,5ex-Epoxide, 8-deoxy: [126829-68-3]. 4ex,5ex-Epoxy-13-
C 17Hn05 M 306.358 hydroxy-1 (10), 7(11 )-germacradien-12,6ex-o/ide
Constit. of Pentzia eenii. Gum. C 15H 200 4 M 264.321
13-Ac: Constit. of P. pinnatisecta. Gum.
C 17Hzz05 M 306.358 Zdero, C. eta/, Phytochemistry, 1990, 29, 189 (isol, pmr)
Constit. of P. eenii. Gum.
Di-Ac: [115346-31-1]. Artemisiaglaucolide 8,14-Dihydroxy-1(10),4,11(13)- Sq-00472
C 1,H140 6 M 348.395
Constit. of Artemisia afra. Oil. germacratrien-12,6-olide
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1129 (isol)
Zdero, C. eta/, Phytochemistry, 1990, 29, 189 (Artemisiaglaucolide)
(1(10)Z,4E,6a,8a)-form
8,9-Dihydroxy-1(10),4,11(13)- Sq-00470
germacratrien-12,6-olide
8,9-Dihydroxycostuno/ide
CtsH200 4 M 264.321

~(1(10)E,4E,6~,8a,9~),Mm
(l(JO)Z,4E,6«,8« )-form [60 147-79-7] Budlein B
Constit. of Viguiera buddleiaformis. Cryst. Mp 162°. [ex]~
+ 3.1 o (MeOH).
Di-Ac: [54153-69-4]. Zexbrevin D
C 19H 140 6 M 348.395
Constit. of Zexmenia brevifolia. Cryst. Mp 149-151°.
0
(l(JO)Z,4E,6«,8fJ)-form
CtsH 200 4 M 264.321 Deacetylovatifolin
(l(JO)E,4E,6P,8«,9fJ)-form Constit. of Podanthus mitiqui. Cryst. Mp 165''. [ex]i,O
9-(2R,3R-Epoxy-2-methylbutanoyl): [72638-72-3). -259° (c, 0.9 in MeOH).
C20H 260 6 M 362.422 14-Ac: [50886-56-1]. Ovatifolin
Constit. of Montanoa hibiscifolia. Oil. C17Hzz0 5 M 306.358
8-(2R,3R-Epoxy-2-methylbutanoyl), 9-Ac: [72690-77-8]. Constit. of P. ovatifolius. Cryst. (EtOAcjhexane). Mp
CnH280 7 M 404.459 131-134°. [ex) 0 -75° (c, 1.2 in CHC13).

230
8,15-Dihydroxy-1(10),4,11(13)-... - 9,15-Dihydroxy-1(10),4,11(13)-... Sq-00473- Sq-00474

(I(IO)Z,4E,6p,Bfl)-form Isol. from Onopordon acanthium. Cryst. (EtpjMe 2CO).

8-(2-Methy/butanoyl): [90039c64-8]. Mp 55-56°. [1X]i? + 166.8° (c, 0.277 in MeOH).
C 20H 280 5 M 348.438 8-(3-Hydroxy-2-methylpropanoyl): [19889-01-1]. Arctiopicrin
Constit. of Wunderlichia mirabi/is. Oil. C 19H 260 6 M 350.411
11P,l3-Dihydro: [102349-42-8]. 8rr.,14-Dihydroxy-1(10),4- Constit. of Artemisia minus and Arctium minus. Cryst.
germacradien-I2,6rr.-olide. SIX, 14-Dihydroxy-11, 13- Mp 115°. [1X]i? + 133°.
dihydrome/ampo/ide. Shonachalin C 8-(2,3-Epoxy-2-methy/propanoyl):
C 15H 22 0 4 M 266.336 C 19H 240 6 M 348.395
Constit. of Artemisia fragrans and A. gypsacea. Cryst. Constit. of Brachylaena transvaalensis and B. rotunda.
(EtP/hexane) or gum. Mp 203-205°. [rr.]~4 + 16° (c, 0.2 Gum.
in CHC1 3). Struct. revised in 1990. 15-Carboxy/ic acid, 3-(3-methyi-2E-pentenoyl): [70527-89-8].
14-A/dehyde: see 8-Hydroxy-14-oxo-1(10),4,11(13)- Euserotin
germacratrien-6,!2-o/ide, Sq-00577 C21H 260 6 M 374.433
14-Carboxy/ic acid: see 8-Hydroxy-1(!0),4,11(13)- Constit. of Eupatorium serotinum. Cryst.
germacratrien-!2,6-o/id-14-oic acid, Sq-00573 (CHC1 3fhexane). Mp 172-173°. [1X]i; +75.2° (c, 0.25 in
(I(IO)E,4E,6rr.,8rr.)-form CHC1 3). Contains unusual 3-methyl-2-pentenoic acid
Gnecco, S. eta/, Phytochemistry, 1973, 12, 2469 (Ovatifolin) residue.
Romo de Vivar, A. eta/, Phytochemistry, 1976, 15, 525 (Budlein B, 8-0-(4-Acetoxy-3-hydroxy-2-methy/enebutanoyl):
Zexbrevin D) Acetylcnicin
Gopalakrishna, E.M. eta/, J. Cryst. Mol. Struct., 1977, 7, 49 C 22 H 280 8 M 420.458
(cryst struct, Ovatifolin) Isol. from Centaurea malacitana. Oil.
Hoeneisen, M. et a/, Phytochemistry, 1980, 19, 2765
(Deacety/ovatifolin) 11 ,13-Dihydro: see 8, 15-Dihydroxy-1(1 0),4-germacradien-
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 228. 12,6-o/ide, Sq-00456
Sanz, J.F. et a/, Phytochemistry, 1990, 29, 2919 (Shonachalin C) Suchy, M. et a/, Tetrahedron Lett., 1964, 3907 (Arctiopicrin)
Drozdz, B. eta/, Collect. Czech. Chern. Commun., 1968, 33, 1730;
1972, 37, 1546 (Onopordopicrin, Eupatoriopicrin)
8,15-Dihydroxy-1(10),4,11(13)- Sq-00473 Samek, Z. eta/, Tetrahedron Lett., 1969, 2931 (Cnicin)
germacratrien-12,6-olide Yoshioka, H. eta/, J. Chern. Soc., Chern. Commun., 1970, 148
(Salonitenolide)
Tori, K. eta/, J. Chern. Soc. B, 1971, 1084 (Cnicin)
Vanhaelen-Fastre, R. eta/, Planta Med., 1974, 26, 375; 1976, 29,
179 (iso/, ir, pmr, pharmaco/, Salonitenolide)
Zakirov, S.Kh. et a/, Khim. Prir. Soedin., 1975, 11, 656; Chern.
Nat. Compd. (Engl. Trans/.), 690 (iso/, pmr, ir)
Herz, W. eta/, J. Org. Chern., 1979, 44, 2784 (Euserotin)
Bohlmann, F. et a/, Phytochemistry, 1979, 18, 95 (isol)
C 15H 200 4 M 264.321 Gonzalez, A.G. eta/, An. Quim., 1980, 76, 296 (isol)
Bohlmann, F.B. eta/, Phytochemistry, 1982, 21, 647 (isol)
(l(IO)E,4Z,6rr.,8rr.)-form [26931-94-2] Sa/onitenolide. 8rr.,15- Barrero, A.F. eta/, An. Quim., Ser. C, 1988, 84, 344 (Acetylcnicin)
Dihydroxycostunolide Miski, M. eta/, Phytochemistry, 1988, 27, 1417 (isol, pmr,
Constit. of Centaurea salonitana, Cnicus benedictus and Arctiopicrin)
Jurinea maxima. Toxic to leukaemia cells by DNA Turdybekov, K.M. eta/, Khim. Prir. Soedin., 1989, 25, 781; Chern.
complexation. Cryst. (CHCI 3 /Me 2CO). Mp 136°. [rr.]i? Nat. Compd. (Engl. Trans/.), 662 (iso/, cryst struct,
+ 199.4° (c, 0.38 in MeOH). Salonitenolide)
15-Ac: [80447-53-6]. I5-Acetoxy-8rr.-hydroxycostunolide
C 17H 22 0 5 M 306.358 9,15-Dihydroxy-1(1 0),4, 11 (13)- Sq~00474
lsol. from Dicoma schinzii. Gum. germacratrien-12,6-olide
8-0-(2-Acetoxymethy/-2-propenoyl): [77396-62-4]. Amarint
C 21 H 260 7 M 390.432
Constit. of Centaurea amara. Oil.
8-0-(3,4-Dihydroxy-2-methy/enebutanoyl): [24394-09-0].
Cnicin
CmH260 7 M 378.421
Isol. from Cnicus benedictus and Centaurea squarrosa.
Antibiotic, inhibitor of Trichomonas. Cryst. Mp 143°.
[rr.]i? + 158° (c, 2.3 in EtOH). CtsH200 4 M 264.321
8-(3-Methy/butanoyl): [80442-33-7]. Arbutifolin (l(IO)E,4Z,6rr.,9fl)-form [11054-57-2] Stenophyllolide
C 20H 280 5 M 348.438 Constit. of Centaura aspera and Hymenoxys turneri.
lsol. from Centaurea arbutifolia. Oil. [rr.Jn +84.8° (c, 0.5 Cryst. Mp > 200° dec. [1X]i? + 72.4° (MeOH).
in CHC13) (as acetate). Di-Ac: [11054-58-3]. 9p,I5-Diacetoxy-1(10),4,11(13)-
8-(4-Hydroxy-2-hydroxymethy/butanoyl): [6856-01-5]. germacratrien-12,61X-olide. /domain
Eupatoriopicrin C 19H 240 6 M 348.395
C 20H 260 7 M 378.421 Constit. of Gutenbergia cordifolia. Cryst. (MeOH). Mp
Constit. of Eupatorium cannabinum. Cryst. (EtOH). Mp 161-162°. [1X]i;' +83° (c, 0.13 in MeOH).
157-161°. [rr.]i? +95° (CHC1 3). 11P,l3-Dihydro: [95298-48-9]. 9,15-Dihydroxy-1(10),4-
8-(2-Hydroxymethylpropenoyl): [19889-00-0]. germacradien-12,6-o/ide. II p,I3-Dihydrostenophyl/olide
Onopordopicrin C15H 220 4 M 266.336
C 19H 240 6 M 348.395 Constit. of C. aspera. Cryst. Mp 144-147°.
Amo, M. eta/, An. Quim., 1984, 80, 277 (isol)

231
14,15-Dihydroxy-1(10),4,11(13)-... - 8,15-Dihydroxy-1(10),4,11(13)-... Sq-00475 - Sq-00477

Picher, M.-T. et al, Phytochemistry, 1984, 23, 1995, 2956 8-(2,3-Epoxy-2-methy/butanoyl), 9-Ac, Me ester. [24694-79-
(Stenophyllolidide, Dihydrostenophyllolide) 9). Uvedalin
Amigo, J.-M. eta/, Phytochemistry, 1984, 23, 1999 (cryst struct) C23H 280 9 M 448.469
Fujimoto, Y. eta/, Phytochemistry, 1987, 26, 2593 (!domain)
Constit. of leaves of P. uvedalia. Cryst. (EtOAc). Mp
Gao, F. eta/, Phytochemistry, 1990, 29, 2865 (iso/, pmr, cmr)
131-133°. [1X)~4 + 12.8°.
9-(2,3-Epoxy-2-methy/butanoyl), 8-Ac, Me ester. [74635-71-
14,15-Dihydroxy-1(10),4,11(13)- Sq-00475 5). lsouvedalin
germacratrien-12,6-olide C23H 280 9 M 448.469
Constit. of Sma/lanthus uvedalia. Oil.
8-(3-Acetoxy-2-hydroxy-2-methylbutnoyl), 9-(3-hydroxy-3-
methy/butanoyl), Me ester: [75627-92-8]. Tetrahelin E
(1(10)Z,4Z,6cx)-:form C28 H 380 12 M 566.601
Constit. of Tetragonotheca helianthoides. Gum.
8-(3-Acetoxy-2-hydroxy-2-methy/butanoyl), 9-(2-
C 15H 200 4 M 264.321 methylbutanoyl), Me ester: [75627-93-9). Tetrahelin C
C28 H 380 11 M 550.602
(l(JO)Z,4Z,6rz)-form [17909-97-6) Albicolide
Constit. of Jurinea albicaulis. Cryst. (EtOAc). Mp 104- Constit. ofT. helianthoides. Gum.
1050. [IX)~ + 73° (c, 0.5 in MeOH). 8-(2,3-Dihydroxy-2-methy/butanoyl), 9-Ac, Me ester:
15-Ac: [126647-24-3). 15-Acetoxy-14-hydroxycostunolide
[73522-62-0). Tetraludin A
C 17H 220 5 M 306.358 C23 H:l(,0 10 M 466.484
Isol. from Dicoma capensis and D. tomentosa. Gum. [1X)i;' Constit. ofT. ludoviciana. Oil.
+ 77° (c, 1.09 in CHC1 3). 8-(2,3-Dihydroxy-2-methylbutanoyl), 9-(3-hydroxy-2-
methylbutanoyl), Me ester(l): [73522-61-9). Tetraludin B
(l(JO)E,4Z,6rz)-form
C26H 360 11 M 524.564
15-Ac: [92122-89-9). Perymeniolide Constit. of T. /udoviciana.
C 17H 220 5 M 306.358
8-(2,3-Dihydroxy-2-methylbutanoyl), 9-(3-hydroxy-2-
Isol. from Perymenium mendezii. Oil. [1X)n + 241° (c,
methylbutanoyl), Me ester(2): [73489-04-0). Tetraludin C
0.153 in CHC1 3).
C26H 360 11 M 524.564
111X,l3-Dihydro: [94356-08-8). 14,15-Dihydroxy-1(10),4- Constit. ofT. ludoviciana. Cryst. (Etpjpet. ether). Mp
germacradien-12,6-olide. Ixerin L 172-173°. Diastereoisomeric with Tetraludin B.
C 15H 22 0 4 M 266.336
8-(2,3-Diacetoxy-2-methy/butanoyl), 9-Ac, Me ester: [75627-
Constit. of Ixeris tamagawaensis. Amorph. powder. [IX)~
95-1). Tetrahelin A
+ 23.SO (c, 0.37 in MeOH).
C27 H 340 12 M 550.558
11P,13-Dihydro: [91486-99-6). lxerin K Constit. of T. helianthoides. Gum.
C15H 2204 M 266.336
8-(3-Acetoxy-2-hydroxy-2-methylbutanoyl), 9-Ac. Me ester:
Constit. of I. tamagawaensis. Amorph. powder. [IX)~
-40.6° (c, 0.62 in MeOH). [73488-90-1). Tetrahelin D
C25 H 320 11 M 508.521
14-Aldehyde: see 15-Hydroxy-14-oxo-1(10),4,11(13)- Constit. of T. helianthoides. Gum.
germacratrien-12,6-olide, Sq-00578
Suchy, M. eta/, Collect. Czech. Chern. Commun., 1967, 32, 3934 (1(10)Z,4Z,6rz,BP,9p)-form
(Aibicolide) 8-Angeloyl: [102867-73-2). Douglasine
Stoecklin, W. eta/, Tetrahedron, 1970, 26, 2397 (uv) C20H 240 7 M 376.405
Asada, H. eta/, Chern. Pharm. Bull., 1984, 32, 3403 (1xerins) Isol. from Chaenactis douglasii. Oil.
Maldonado, E. eta/, Phytochemistry, 1984, 23, 813 (Perymeniolide)
Herz, W. et al, J. Org. Chern., 1970, 35, 2605 (Uvedalin)
Zdero, C. et al, Phytochemistry, 1990, 29, 183 (15-Acetoxy-14-
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 625 (Polymatins)
hydroxycostunolide)
Van, N.L. eta/, Phytochemistry, 1979, 18, 851 (Polymatins)
Quijano, L. eta/, Phytochemistry, 1979, 18, 1529 (Tetraludins)
8,9-Dihydroxy-1(10),4,11(13)- Sq-00476 Bohlmann, F. eta/, Phytochemistry, 1980, 19, 107 (Isouvedalin)
germacratrien-12,6-olid-14-oic acid Seaman, F.C. eta/, Phytochemistry, 1980, 19, 583 (Tetrahelins)
Stierle, D.B., Phytochemistry, 1986, 25, 743 (Doug/asine)
COOH
,OH 8,15-Dihydroxy-1(10),4,11(13)- Sq-00477
germacratrien-12,6-olid-14-oic acid

4
COOH

H
C 15H 180 6 M 294.304
IDH2C
,.
(l(JO)E,4E,6rz,8P,9rz)-form
8-Ange/oy/, Me ester: [72023-29-1]. Polymatin A 0
C21 H 260 7 M 390.432 . C 15H 180 6 M 294.304
Constit. of Polymnia macu/ata. Gum or 011. (l(JO)E,4E,6rz,8p)-form
8-Ange/oy/, 9-Ac, Me ester: [72023-37-1). Polymatin B 8-(2-Methylbutanoyl): 9-Desacetoxymelcanthin F
C23H 280 8 M 432.469 C20 H 260 7 M 378.421
Constit. of P. maculata. Gum or cryst. Mp 115°. [1X)~4 Constit. of Polymnia macu/ata. Gum.
+56.4° (c, 3.6 in CHC1 3). Malcolm, A.J. eta/, J. Nat. Prod. (Lioydia), 1987, 50, 167.

232
5,9-Dihydroxy-1-oxo-10(14),4(15)-... - 3,8-Dihydroxy-14-oxo-1(10),4,11(13)-.•. Sq-00478 - Sq-00482

5,9-Dihydroxy-1-oxo-1 0(14),4(15)- Sq-00478 8-Angeloyl, 10-Ac: 2,3-cis-Ereglomerulide

germacradien-12,6-olide C22H280 7 M 404.459
Constit. of Eremanthus glomerulatus. Cryst. (Etpjpet.
0 OH ether). Mp 189°. [1X]~ -29° (c, 0.3 in CHC1 3).

~
(2E,4rx.H,6rx.,8rx.,l 0/l)-form
8-Angeloyl, 10-Ac: 2,3-trans-Ereglomerulide
C22 H 280 7 M 404.459
Constit. of E. glomerulatus. Gum. [IX]~ -7° (c, 0.1 in
CHC1 3).
OH
(2Z,4rx.H,6rx.,8p,l Orx. )-form
C 15H 200 5 M 280.320
8-(3-Methylbutanoyl): [67506-31-4]. Neurolenin A
(5p,6rx.,9fl)-form C20H 280 6 M 364.438
Constit. of Artemisia herba-alba. Gum. Constit. of Neurolaena lobata. Cryst. (EtOAcjhexane).
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 3661 (isol, pmr) Mp 127-128°. [1X]i; -257.7° (c, 1.0 in CHC1 3).
Manchand, P.S. et al, J. Org. Chern., 1978, 43, 4352 (Nurolaenin
8,9-Dihydroxy-2-oxo-3, 11(13)- Sq-00479 A)
germacradien-12,6-olide Bohlmann, F. et al, Phytochemistry, 1981, 20, 1609; 1982, 21,
1087.
Martinez, M. et al, Phytochemistry, 1987, 26, 2104 (Caleins)

8,10-Dihydroxy-1-oxo-4,11(13)- Sq-00481
germacradien-12,6-olide

C 15H 200 5 M 280.320

(3Z,6rx.,8rx.,9P,l0fl)-form
9-Angeloyl: [81344-93-6]. Vicolide B
C20H260 6 M 362.422 0
Constit. of Vicoa indica. Cryst. (Me2C0jhexane). Mp C15H200 5 M 280.320
195-196°. [1X] 0 -110° (c, 1.0 in CHC1 3).
(4E,6rx.,8p,JOrx.)-form
9-(2R,3R-Epoxy-2-methylbutanoyl): [103425-22-5]. Vicolide
D 8-Angeloyl: [84886-36-2]. Trichomoriolide
C20H 260 7 M 378.421 C20 H 260 6 M 362.422
!sol. from V. indica. Cryst. (MeOH). Mp 214-216°. [1X] 0 Constit. of Trichogoniopsis morii. Gum. [IX]~ + 104° (c,
-80° (c, 1 in CHC1 3). 1.81 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2035.
Purushothaman, K.K. et al, J. Chern. Res. (S), 1981, 374 (cryst
struct, Vicolide B)
Purushothaman, K.K. et al, Indian J. Chern., Sect. B, 1986, 25, 3,8-Dihydroxy-14-oxo-1(10),4,11(13)- Sq-00482
417 (Vicolide D)
germacratrien-12,6-olide
8,10-Dihydroxy-1-oxo-2,11(13)- Sq-00480 CHO
germacradien-12,6-olide

O~\OH
I OH (2Z,4cxH,6cx,8~,10~)-form
8

ClsHiaOs M 278.304
(1(10)Z,3P,4Z,6rx.,8fl)-form
'o o 8-(2-Methylbutanoyl): [72948-01-7]. Eupachifolin A
ClsH 200 5 M 280.320 Constit. of Eupatorium chinense. Oil. [1X]i? -66.2° (c,
(2Z,4rx.H,6rz,8P,JOfJ)-form 0.21 in CHC1 3).
8-(2-Methylpropenoyl): [110300-73-7]. Calein E Ito, K. et al, Chern. Lett., 1979, 1473.
C 19H 240 6 M 348.395
Constit. of Calea zacatechichi. Cryst.
(Me 2CO/diisopropy1 ether). Mp 150-151°. [1X] 0 +47.4°
(CHC1 3).
8-Tigloyl: [110300-74-8]. Calein F
C2oH260 6 M 362.422
From C. zacatechichi. Cryst. Mp 141-143°.
(2Z,4rx.H,6rx.,8rx.,l 0/l)-form
8-(2-Methylpropenoyl), 10-Ac:
C21H260 7 M 390.432
Constit. of Lychnophora blanchetii. Gum.

233
5,8-Dihydroxy-2-oxo-1(10),3,11(13)-••• - 8,9-Dihydroxy-14-oxo-1(10),4,11(13)-... Sq-00483 - Sq-00486

5,8-Dihydroxy-2-oxo-1(10),3,11(13)- Sq-00483 4P,J5-Epoxide, 8-(2-methylpropenoyl): 4P,J5-Epoxy-9E-

germacratrien-12,6-olide mil/erenolide
C1,Hn07 M 362.379
FromM. quinqueflora. Cryst. Mp 196-198°. [IX)~ -131°
(c, 1.8 in CHC13).
(5p,6rx.,8p,9Z)-form
8-(2-Methylpropenoyl): 9Z-Mil/erenolide
Isol. from M. quinquejlora. Oil.
4P,l5-Epoxide: 4P,J5-Epoxy-9Z-millerenolide
C.,Iln07 M 362.379
FromM. quinquejlora. Oil. [ocln -27° (c, 0.35 in
C 15H 180 5 M 278.304 CHC1 3).
~ UD3470000. Jakupovic, J. et al, Phytochemistry, 1987, 26, 2011.
(1(10)E,3Z,5P,6a,8rx.)-form
8-(2-Methy/propenoyl): [50656-66-1). Moleplumtin 8,9-Dihydroxy-14-oxo-1(10),4,11(13)- Sq-00486
C1,Hn06 M 346.379
Constit. of Elephantus mol/is. Cryst. (EtOH). Mp 214-
germacratrien-12,6-olide
2160. CHO
Lee, K.-H. et al, J. Chem. Soc., Chern. Commun., 1973, 476. ,OH

5,8-Dihydroxy-14-oxo-1(10),4(15), 11(13)- Sq-00484

germacratrien-12,6-olide
CHO

C 15H 180 5 M 278.304

(l(JO)E,4E,6rx.,8p,9rx.)-form
8-(2-Methy/propanoyl): [75744-68-2). 9-
Hydroxyglllbratolide. 9-Desacylacanthosperma/ A.
Desacetylacanthospermal A (incorr.)
0 C 19H 140 6 M 348.395
C1sHla05 M 278.304 Constit. of Acanthospermum glabratum and Milleria
quinquejlora. Gum or oil.
(l(JO)E,5P,6rx.,8p)-form
8-(2-Methylpropanoyl), 0 9 -Me: [75744-64-8).
8-(2-Methylpropenoyl): [110601-24-6). 1(10)-Mil/erenolide
Acanthospermolide
C 19H 220 6 M 346.379
Constit. of Milleria quinqueflora. Oil. [oc)~ -255° (c, C10H:u;06 M 362.422
Constit. of A. glabratum. Cytotoxic agent. Cryst.
0.26 in CHC13).
(C6H 6/MeOH). Mp 154°.
8,9-Didehydro(E): l(JO)E,8E-Mil/erdienolide
9-(2-Methylpropanoyl): [72548-16-4]. Acantholide
C1,H100 6 M 344.363
C 19H140 6 M 348.395
FromM. quinqueflora. Oil. [oc)~ -260° (c, 0.43 in
Constit. of A. glabratum. Cryst. (MeOH). Mp 208°.
CHC1 3). An enol ester.
8-(2-Methylpropanoyl), 9-(2-hydroxy-2-methylpropanoyl):
8,9-Didehydro(E-),4P,J5-epoxide: 4P,J5-Epoxy-l(JO)E,8E-
[56689-33-9]. Acanthospermal A
mil/erdienolide
C23 H 300 8 M 434.485
C 19H 100 7 M 360.363
Isol. from A. australe. Gum. [oc)i;l + ,Hg -54" (c, 0.33 in
From M. quinquejlora. Oil. An enol ester.
CHC1 3).
Jakupovic, J. et al, Phytochemistry, 1987, 26, 2011.
8,9-Bis(2-methylpropanoyl): [75744-66-0]. Acanthoglllbrolide
C23 H 300 7 M 418.486
5,8-Dihydroxy-14-oxo-4(15),9,11(13)- Sq-00485 From A. glabratum. Gum.
germacratrien-12,6-olide 15-Hydroxy, 8-(2-methylbutanoyl), 9-Ac: [56679-19-7).
Acanthospermal B
CHO CnH2110 8 M 420.458
Isol. from A. hispidum. Gum. [oc]i;I+,Hg -33° (c, 0.09
in CHC1 3).
(5J3,6a,8J3,9E):form Herz, W. et al, J. Org. Chern., 1975, 40, 3486 (Acanthospermals)
Saleh, A.A. et al, J. Chern. Soc., Perkin Trans. 1, 1980, 1090.
Jakupovic, J. eta/, Phytochemistry, 1987, 26, 2011 (9-
Desacylacanthospermal A)
0
C 15H 180 5 M 278.304
(5p,6a.,8P,9E)-form
8-(2-Methylpropenoyl): [110601-29-1). 9E-Mil/erenolide
C1,Hn06 M 346.379
Constit. of Milleria quinquejlora. Oil. [oc)~ -5° (c, 0.6 in
CHC1 3).

234
8,10-Dihydroxy-3-oxo-1,4,11(13)-... - 1,10-Epoxy-3,8-dihydroxy-4,11(13)-... Sq-00487 - Sq-00489

8,10-Dihydroxy-3-oxo-1,4,11(13)- Sq-00487 1,10-Epoxy-3,8-dihydroxy-4,11(13)- Sq-00489

germacratrien-12,6-olide germacradien-12,6-olide
OH

~OH (lp,3cx,4Z,6cx,8P,10cx)-form

M)= 0
0
C 15H 200 5 M 280.320
C 15H 1805 M 278.304 (IP,3rx.,4Z,6rx.,Bp,10rx.)-form
(1 E,4Z,6rx.,Bp,J Orx. )-form 8-(2-Hydroxymethyl-2E-butenoyl), 3-Ac: [72984-74-8].
8-(2-Methy/propanoyl): [59979-56-5]. Tagitinin C Eupalinin C
C 19H 240 6 M 348.395 . C22H 280 8 M 420.458
Constit. of Tithonia diversifo/ia. Oil. [1X]n -204°. Constit. of Eupatorium lindleyanum. Oil. [1X]i!' -70° (c,
Pal, Ret a/, Indian J. Chern., Sect. B, 1977, 15, 208 (isol) 0.23 in MeOH).
Baruah, N.C. et at, J. Org. Chern., 1979, 44, 1831 (struct) 8-(4-Hydroxy-2-methyi-2Z-butenoyl), 3-Ac: [72984-73-7].
Eupalinin D
8,15-Dihydroxy-14-oxo-1(10),4,11(13)- Sq-00488 C22H 280 8 M 420.458
germacratrien-12,6-olide Constit. of E. lindleyanum. Oil. [1X]i!' -38.8° (c, 0.2 in
MeOH).
(IP,3P,4Z,6rx.,BP,IOrx.)-form [73035-83-3]
Helianginol
(1(10)Z,4Z,6cx,8cx}:form Cryst. Mp 232-235°.
8-(4-Hydroxy-2-methyl-2Z-butenoyl): [72947-93-4].
Eupalinin B
0 C20H 260 7 M 378.421
Ct5Ht80 5 M 278.304 Constit. of E. lindleyanum. Oil. [1X]i!' -68.6° (c, 0.3 in
(1(10)Z,4Z,6rx.,8rx.)-form MeOH).
Urospermal 8-(2-Hydroxymethyl-2E-butenoyl), 3-Ac: [72947-94-5].
Obt. from roots of Urospermum dalechampii/Cryst. Eupalinin A
(Me2C0fhexane or C6H 6). Mp 163-165°, Mp 191-193°. C22 H 280 8 M 420.458
[1X]n -2° (Me2SO). Mp's refer to two interconvertible Constit. of E. lindleyanum. Cryst. Mp 175-177°. [1X]i!'
conformational isomers, Urospermal A and B. -90° (c, 0.2 in MeOH).
8-(2-Methy/propenoyl): (62687-47-2]. Vernopectolide B 8-(2-Methylpropenoyl): [27542-17-2]. Eriojlorin
C19H 22 0 6 M 346.379 C 19H 240 6 M 348.395
Constit. of Vernonia pectoralis. Amorph. [1X]n +93° (c, 1 Constit. of Podanthus ovatifolius. Antileukaemic agent.
in CHC1 3). Cryst. (EtOAc). Mp 236-238° dec.
(l(JO)E,4E,6rx.,8p)-form 8-(2-Methylpropenoyl), 3-Ac: [27542-23-0].
8, 15-Dihydroxy-14-oxoacanthospermo/ide C21 H 260 7 M 390.432
8-(2-Methy/butanoyl): Constit. of P. ovatifolius. Cryst. (EtOAcjhexane). Mp
C20H 260 6 M 362.422 210-212°.
Constit. of Acanthospermum hispidum. Oil. 3,8-Bis(2-methylpropenoyl): [50816-66-5].
8-(3-Methy/butanoyl): [72948-02-8]. C13H 280 7 M 416.470
C20H 260 6 M 362.422 Isol. from P. ovatifolius. Cryst. (EtOAcjhexane). Mp
Constit. of A. hispidum. Oil. 155-158°. [1X]n -87° (c, 1 in CHC13).
(1(10)E,4Z,6rx.,8p)-form 8-(2-Methy/propanoyl): [59979-58-7]. Tagitinin E.
Desacetylviguiestenin
8-(2-Methylbutanoyl): [72023-17-7].
c.,H2606 M 350.411
Constit. of A. hispidum. Oil.
Isol. from Viguiera stenoloba and Tithonia rotundifolia.
8-(3-M ethylbutanoyl): [72023-18-8]. Cryst. Mp 212-214°. [1X]n -101.4°.
Constit. of A. hispidum. Oil. 8-(2-Methylpropanoyl), 3-Ac: [54153-71-8]. Viguiestenin
8-(2-Methy/butanoyl), 15-Ac: (72023-26-8]. C21H 280 7 M 392.448
C22 H 280 7 M 404A59 Constit. of V. stenoloba. Cryst. Mp 196-198°. [1X]n
Constit. of A. hispidum. Oil. -120°.
8-(3-Methy/butanoyl), 15-Ac: 8-(2R,3S-Epoxy-2-methylbutanoyl), 3-benzoy/: Lacinolide A
C22H 280 7 M 404.459 C27H 300 8 M 482.529
Constit. of A. hispidum. Oil. lsol. from V. laciniata. Cryst.
[28400-14-8, 28400-15-9] 8- Tigloyl: [13323-48-3]. Heliangin
Bentley, RK. et a/, J. Chern. Soc., Chern. Commun., 1970, 435 C20H 260 6 M 362.422
(Urospermal) Isol. from Helianthus tuberosus. Cryst. (MeOH). Mp
Mompon, B. et a/, Tetrahedron, 1976, 32, 2545 (Vemopectolide B) 227-229°. [IX]~ -1 WO (c, 0.5 in CHCl3).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 625.
8-Angeloy/: [73522-63-1]. Leptocarpin
C20H 260 6 M 362.422

235
1,10-Epoxy-5,8-dihydroxy-4(15)... - 4,5-Epoxy-8,13-dihydroxy-1(10),7(11) ... Sq-00490 - Sq-00493

Constit. of Leptocarpha rivularis. Cryst. 8-Ange/oy/, 14-Ac: 18-Methylsphaerocephalin

(EtOAcfcyclohexane). Mp 192-195°. [1X]n -99° (CHC1 3). C22H 280 7 M 404.459
41X,5-Dihydro, 8-ange/oy/: [101527-88-2]. Argophyllin C Constit. ofT. rotundifolia. Cryst. (EtzO). Mp 192-196°.
C20H 28 0 6 M 364.438 [1X]i;' + 29.1 o (c, 0.3 in CHC1 3), [1X]i,S + 11.3° 1MeOH).
lsol. from Helianthus spp. Cryst. (EtOAc). Mp 84-86°. 8-(2,3-Epoxy-2-methy/butanoyl), 14-Ac:
[1X]n -47.SO (c, 0.4 in CHC1 3). C22 H 280 8 M 420.458
(1P,3P,4Z,6rx.,8rx.,10rx.)-form Constit. ofT. rotundifolia. Cryst. (Et20). Mp 197-202°.
8-(2-Methylpropanoyl): Deacetylviguiestin 8-(2-Methylpropenoyl), 14-Ac: [75680-34-1].
Ct,Hu;06 M 350.411 Sphaerocephalin
lsol. from V. stenoloba. Mp 212-214°. C21 H 260 7 M 390.432
8-(2-Methy/propanoyl), 3-Ac: [69440-10-4]. Viguiestin Constit. of Viuiera sphaerocephala. Mp 223-225°. [1X]i?
C21 H 280 7 M 392.448 +50°.
Isol. from V. stenoloba. Ortega, A. et al, Phytochemistry, 1980, 19, 1545 (Sphaerocephalin)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 267.
Morimoto, H. eta/, Tetrahedron, 1966, 22, 3173 (Heliangin)
Romo de Vivar, A. et a/, Phytochemistry, 1982, 21, 375 (18-
Nishikawa, M. et a/, Tetrahedron, 1966, 22, 3601 (cryst struct, M ethylsphaerocephalin)
Heliangin)
Torrance, S.J. et al, Phytochemistry, 1969, 8, 2381 (isol, pmr, ms)
Neidle, S. et al, J. Chern. Soc., Chern. Commun., 1972, 140 (abs 4,5-Epoxy-2,8-dihydroxy-1(10),11(13)- Sq-00492
config, Heliangin) germacradien-12,6-olide
Kupchan, S.M. eta/, J. Chern. Soc., Chern. Commun., 1973, 842
(isol)
Gnecco, S. eta/, Phytochemistry, 1973, 12, 2469 (isol, pmr, ms)
Pal, R. et al, Indian J. Chern., Sect. B, 1977, 15, 533 (isol)
Romo de Vivar, A. et al, Rev. Latinoam. Quim., 1978, 9, 171 s -OH
(struct) ( 1( 1O)E,2cx,4cx,5cx,6cx,8cx )-form
Ito, K. et a/, Chern. Lett., 1979, 1469 (Eupalinins)
Barauh, N.C. eta/, J. Org. Chern., 1979, 44, 1831 (struct)
Martinez, R. eta/, Phytochemistry, 1979, 18, 1527 (Leptocarpin)
Chowdury, P.K. et a/, J. Org. Chern., 1980, 45, 535 (struct) 0
Ober, A.G. eta/, J. Nat. Prod. (Lloydia), 1985, 48, 302 (cryst C 15H 200 5 M 280.320
struct, Leptocarpin)
Watanabe, K. eta/, Phytochemistry, 1986, 25, 141 (Argophyllin C) (l(JO)E,1rx.,4rx.,5rx.,6rx.,Brx.)-form
Gao, F. et al, Phytochemistry, 1989, 28, 2409 (Lacinolide A) 8-(3-M ethyl-2-butenoyl):
C20H 260 6 M 362.422
1,10-Epoxy-5,8-dihydroxy-4(15),11(13)- Sq-00490 Constit. of Elephantopus angustifolius. Cryst. Mp 195°.
germacradien-12,6-olide (l(JO)E,1rx.,4rx.,5p,6rx.,Bf/)-form
8-Angeloyl: [77063-90-2]. Deltoidin B
C20 H 260 6 M 362.422
Constit. of Eupatorium deltoideum. Cryst.(EtzOfpet.
ether). Mp 170-171°. [1X]n -87.8° (CHC1 3).
11P,l3-Dihydro, 8-Ac: [114076-68-5]. Paramicholide
C 17H 240 6 M 324.373
Isol. from Paramichelia baillonii and Michelia rajaniana.
Oil. [1X]i;' -47° (c, 0.76 in CHC1 3).
(lp,sp,6rx.,8rx.,10rx.)-form Quijano, L. eta/, Phytochemistry, 1980, 19, 1975 (Deltoidin B)
Angeloyl: [91161-82-9]. Cordifolia 54 Jakupovic, J. et al, Phytochemistry, 1987, 26, 1467.
CmH260 6 M 362.422 Ruangrungsi, N. et al, J. Nat. Prod. (Lloydia), 1988, 51, 163, 1220
Constit. of Erlangea cordifolia. Amorph. powder. (Paramicholide)
31X-Acetoxy, 8-ange/oy/: [91161-81-8]. Cordifolia 55
C22H 280 8 M 420.458 4,5-Epoxy-8,13-dihydroxy-1(1 0),7(11 )- Sq-00493
Constit. of E. cordifolia. Cryst. Mp 150-152°. germacradien-12,6-olide
Begley, M.J. et al, J. Chern. Soc., Perkin Trans. I, 1984, 819.

1,10-Epoxy-8,14-dihydroxy-4,11(13)- Sq-00491
germacradien-12,6-olide

C 15H 200 5 M 280.320

(l(JO)E,4rx.,5P,6rx.,8rx.)-form
8-Tigloyl, 13-Ac: [11091-28-4]. Marginatin
C22 H 280 7 M 404.459
Constit. of Vernonia spp. Cryst. (C6H 6/Et20l. Mp 104-
C 15H 200 5 M 280.320 1050. [1X]i,S -6.0°.
(lp,4E,6rx.,8p,]Orx.)-form Padolina, W.O. et al, Phytochemistry, 1974, 13, 2225.
8-Ange/oy/:
C20H 260 6 M 362.422
Constit. of Tithonia rotundifolia. Gum. [1X]i;' + 10.3° (c,
0.3 in CHC1 3).

236
4,5-Epoxy-8,15-dihydroxy-1(10) ... - 3,10-Epoxy-3,8-dihydroxy-1,4,11(13)-... Sq-00494 - Sq-00497

4,5-Epoxy-8,15-dihydroxy-1(1 0), 11(13)- Sq-00494 2,5-Epoxy-2,8-dihydroxy-1(10),3,11(13)- Sq-00496

germacradien-12,6-olide germacratrien-12,6-olide

L:CYO:
HOH2~~1:r
0
C 13H 200 5 M 280.320
(1(10)E,4rz.SP.6rz,Bfl)-form
C 15H 180 5 M 278.304
8-0-[4-(JS-Hydroxyoctadecanoyloxy )-2-methyl- 2E-
butenoyl]: [57718-79-3]. Eupassofilin (1(10)Z,2P,5rz,6rz,8rz)-form
C 38H 600 9 M 660.887 02-Et, 8-(2-Methylpropenoyl): [55306-08-6]. Phantomolin
Constit. of Eupatorium hyssopifolium. Gum. [IX]~ -143° C11 H 260 6 M 374.433
(c, 0.14 in MeOH). Constit. of Elephantopus mollis. Oil.
I> UD3418000.
Herz, W. et a!, J. Org. Chern., 1976, 41, 1015.
McPhail, A.T. eta/, Tetrahedron Lett., 1974, 2739 (isol)
Lee, K.-H. eta/, J. Pharm. Sci., 1980, 69, 1050 (isol)
4,5-Epoxy-8,9-dihydroxy-1(1 0), 11(13)- Sq-00495
germacradien-12,6-olid-14-oic acid
3,10-Epoxy-3,8-dihydroxy-1,4,11(13)- Sq-00497
COOH germacratrien-12,6-olide

C 13H 180 7 M 310.303

C 15H 180 3 M 278.304
(1(10)E,4rz,5rz,6rz,8P,9rz)-form
(3rz,4Z,6rz,8P,10fl)-form
9-(2,3-Epoxy-2-methylpropanoyl), 8-Ac, Me ester: [72055-
8-(2-Acetoxymethyl-2Z-butenoyl): [34175-79-6]. Liatrin
90-4]. Polymatin C
C 13H 28 0 10 M 464.468 C 22 H 260 8 M 418.443
Isol. from Liatris chapmanii. Antileukaemic. Cryst.
Constit. of Polymnia maculata. Cryst. Mp 183°.
(CH 2Cl 2fhexane). Mp 130-132°. [1X]i;' -142° (c, 1.9 in
8-(2R,3R-Epoxy-2-methylpropanoyl), 9-Ac, Me ester: CHCI 3).
[51019-94-4]. Macullltin
2-Methylpropanoyl: [59979-57-6]. Tagitinin F
C 13H 280 10 M 464.468
C 19H 240 6 M 348.395
Isol. from P. maculata. Cryst. (EtOAcfhexane). Mp 226-
2280. [IX]~ -74.8° (c, 2.6 in CHC1 3). Constit. of Tithonia diversifolia. Cryst. Mp 128-130°.
[1X]o -144o.
8-(2-Methylpropenoyl), 9-Ac, Me ester: [38096-48-9].
8-(2-Methylpropenoyl): [93236-12-5]. 1 ,2-Dehydrozexbrevin
Fluctuadin
B
C 11Hu;09 M 434.442
C 19H 11o, M 346.379
Isol. from Enhydra.fluctuans. Cryst. (EtOHfpet. ether).
Mp 202-205°. [1X] 0 -18.4° (c, 1.1 in CHC1 3). Constit. of Viguiera greggii. Cryst. (C6H 6fhexane). Mp
192-194°.
8-Angeloyl, 9-Ac, Me ester: [38096-47-8]. Fluctuanin
C 13H 280 9 M 448.469 8-(2R,3R-Epoxy-2-methylbutanoyl): I ,2-Dehydroniveusin C
2' ,3'-epoxide
Isol. from E.jluctuans. Cryst. (EtOH). Mp 161-163°.
[1X] 0 -23.5° (c, 1.4 in CHC1 3). C20H 240 7 M 376.405
Isol. from V. microphylla.
8-Angeloyl, Me ester: [71135-31-4]. Longipilin
C 11H 260 8 M 406.432 1,2,4,5-Tetrahydro: see 3,10-Epoxy-3,8-dihydroxy-11(13)-
Isol. from Melampodium longipilum. Cryst. (2- germacren-12,6-olide, Sq-00500
Kupchan, S.M. eta!, J. Org. Chern., 1973, 38, 1853 (Liatrin)
propanolfpet. ether). Mp 170-173°. Baruah, N.C. eta/, J. Org. Chern., 1979, 44, 1831 (Tagitinin F)
9-(2S,3R-Epoxy-2-methylpropanoyl), 8-Ac, Me ester: Gershenzon, J. eta/, Phytochemistry, 1984, 23, 1281
[33880-85-2]. Enhydrin (Dehydroniveusin epoxide) . .
C 13H 280 10 M 464.468 Liu, Y.-L. eta/, Phytochemistry, 1984, 23, 1967 (Dehydrozexbrevm
Isol. from leaves of E . .fluctuans. Cryst. (Me 2C0fpet. B)
ether). Mp 185-186°. [1X] 0 -56.6° (c, 0.9 in CHC1 3). Chowdhury, P.K. eta/, Indian J. Chern., Sect. B, 1988, 22, 402
(abs conjig)
Krishnaswamy, N.R. eta!, Indian J. Chern., 1972, 10, 249
(Enhydrin)
Kartha, G. et a/, J. Chern. Soc., Chern. Commun., 1972, 1327 (cryst
struct, Enhydrin)
Ali, E. eta!, Tetrahedron, 1972, 28, 2285 (Fluctuadin, Fluctuanin)
Herz, W. eta/, Phytochemistry, 1973, 12, 1737 (Maculatin)
Seaman, F.C. eta/, Phytochemistry, 1978, 17, 2131 (Longipilin)
Van, N.L. eta/, Phytochemistry, 1979, 18, 851 (Polymatin C)

237
2,3-Epoxy-8,9-dihydroxy-1(10) ... - 9,10-Epoxy-5,8-dihydroxy-11(13)-... Sq-00498 - Sq-00502

2,3-Epoxy-8,9-dihydroxy-1(1 0),4, 11(13)- Sq-00498 2,3-Dihydro: see 4,5- Epoxy-8,9-dihydroxy-1 (1 0), II ( 13)-
germacratrien-12,6-olid-14-oic acid germacradien-12,6-olid-14-oic acid, Sq-00495
Fischer, N.H. et al, Phytochemistry, 1975, 14, 2241.

3,10-Epoxy-3,8-dihydroxy-11(13)- Sq-00500
germacren-12,6-olide
I

~OH
C 15H 160 7 M 308.287
HO~<~
(J(JO)E,211.,311.,4E,6«,8P,9«)-form
0
8-(3S-Acetoxy-2R-hydroxy-2-methylbutanoyl), Me ester: 9-
Deacetylme/ampodinin A C15H 220 5 M 282.336
C23H 280 11 M 480.468 (3«,4PH,6~t,8/l)-form
Constit. of Melampodium spp. Gum. 8-(2-Methylpropanoyl): [56377-67-4]. Tirotundin. Tagitinin
8-(3S-Acetoxy-2R-hydroxy-2-methylbutanoyl), 9-Ac, Me D
ester: [60295-53-6]. Melampodinin A C19H 280 6 M 352.427
C25H 300 12 M 522.505 Constit. of Tithonia rotundifolia. Cryst. (EtOAc). Mp
Constit. of M. spp. Cryst. Mp 208-210°. 141°. [1X]i? -77° (c, 2 in CHC1 3).
8-(3S-Acetoxy-2R-hydroxy-2-methylbutanoyl), 9-(2- 0 3-Et, 8-(2-methylpropanoyl): [56377-68-5].
methylbutanoyl), Me ester: [81915-80-2]. Me/ampodinin B C21 H 320 6 M 380.480
C28 H 360 12 M 564.585 Constit. ofT. rotundifolia. Cryst. (EtOAc). Mp 125°.
Constit. of M. spp. Cryst. Mp 205-206.SO. [1X]i? -55° (c, 1.2 in CHC1 3).
8-(3S-Acetoxy-2R-hydroxy-2-methylbutanoyl), 9-tigloy/, Me Herz, W. eta/, J. Org. Chern., 1975, 40, 3118; 1978, 43, 1268 (isol,
ester: [81915-81-3]. Melllmpodinin C cryst struct)
C28 H 340 12 M 562.569 Baruah, N.C. eta/, J. Org. Chern., 1979, 44, 1831 (struct)
Constit. of M. americanum. Gum.
8-(2R,3R-Epoxy-2-methylbutanoyl), Me ester: [35852-26-7]. 4,5-Epoxy-3,8-dihydroxy-1(1 0)-germacren- Sq-00501
Melampodin A. Melampodin 12,6-olide
C21 H 240 9 M 420.415
Constit. of M. leucanthum. Cryst. (EtOAc). Mp 218-
2200 dec. [1X]~4 + 155° (c, 0.7 in MeOH).
Neidle, S. et al, J. Chern. Soc., Chern. Commun., 1972, 140 (cryst
struct, Melampodin A)
Fischer, N.H. et al, Phytochemistry, 1975, 14, 2221 (isol)
Fischer, N.H. eta/, J. Org. Chern., 1976, 41, 3956 (isol, struct)
Malcolm, A. eta/, Phytochemistry, 1982, 21, 151 (isol, struct) C 15H 220 5 M 282.336
Fronczek, F.R. et al, J. Nat. Prod. (Lloydia), 1983, 46, 170 (cryst
struct) (l(JO)E,3P,4«,5P,6«,8P,JIPH)-form
8-Ange/oyl: [62197-60-8]. Euperfolin
C 10H 280 6 M 364.438
4,5-Epoxy-8,9-dihydroxy-1(10),2,11(13)- Sq-00499 Constit. of Eupatorium perfoliatum. Cryst.
germacratrien-12,6-olid-14-oic acid (EtOAcfhexane). Mp 173°. [1X]i? -13.9° (c, 0.228 in
MeOH).
HOOC
8-Angeloyl, Ac: [62197-61-9].
Cryst. (C6H 6/hexane). Mp 130°.
Herz, W. et al, J. Org. Chern., 1977, 42, 2264.

9,10-Epoxy-5,8-dihydroxy-11(13)- Sq-00502
germacren-12,6-olide
0
ClsH160 7 M 308.287
(l(JO)E,2Z,4«,5P,6«,8P,9«)-form
8-(2R,3R-Epoxy-2-methylbutanoyl), 9-Ac, Me ester: [58551-
57-8]. Leucanthin A
C23H 260 10 M 462.452
Constit. of Melampodium leucanthum. Cryst. Mp 211-
2130 dec. 9-Config. not certain, ambiguously drawn in
the paper. ClsH 220 5 M 282.336
21X,31X-Epoxide, 8-(2R,3R-epoxy-2-methylbutanoyl), 9-Ac, (4PH,5~t,611.,8«,9«,1 0/1)-form
Me ester: [58551-56-7]. Leucanthin B 5-Ac: [111545-48-3]. Blumealllctone C
C23H 260 11 M 478.452 C17H2406 M 324.373
Constit. of M. leucanthum. Cryst. (2-propanol). Mp 217- Constit. of Blumea balsamifera. Cryst. Mp 247-250°. [1X]n
2190. -4.85° (c, 1.55 in CHC1 3).

238
3,10-Epoxy-8,9-dihydroxy-1-oxo-... - 3,10-Epoxy-8,9-dihydroxy-1-oxo-... Sq-00503 - Sq-00506

8-(2-Methyl-2-butenoyl): [111545-46-1). Blumealactone A 3,10-Epoxy-5,8-dihydroxy-1-oxo- Sq-00505

CzJI280 6 M 364.438 2,4(15),11 (13)-germacratrien-12,6-olide
Constit. of B. balsamifera. Cryst. Mp 205-208°. [a]n
-45.9° (c, 0.88 in CHC1 3). 0
8-(3-Methyl-2-butenoyl): [111545-47-2]. Blumealactone B
C:zeH280 6 M 364.438
Constit. of B. balsamifera. Cryst. Mp 221-222°. [a]n
-34.2° (c, 0.58 in CHCl 3).
Fujimoto, Y. et al, Phytochemistry, 1988, 27, 1109.

3,10-Epoxy-8,9-dihydroxy-1-oxo-2,11(13)- Sq-00503
germacradien-12,6-olide c.sH.,o, M 292.288
(5rx.,6rx.,8rx.,10p)-form
0 8-Angeloyl: [80377-52-2]. lsocentratherin
C 20H 120 7 M 374.390
Constit. of Centratherum punctatum. Cryst. Mp 187-
1880. [a]~ -28.SO (c, 0.5 in CHCl3).
Bevelle, C.A. et al, Phytochemistry, 1981, 20, 1605 (isol)
Manchand, P.S. eta/, J. Org. Chem., 1983, 48, 4388 (cryst struct)
C 15H 180 6 M 294.304
(4pH,6rx.,8p,9p,JOp)-form 3,10-Epoxy-8,9-dihydroxy-1-oxo- Sq-00506
4,5-Dihydro-9P-hydroxyatripliciolide 2,4,11(13)-germacratrien-12,6-olide
8-(2-Methylpropenoyl): [89355-47-5].
C 1,H120 7 M 362.379 0
Constit. of Trichogonia prancii. Cryst. (Etp). Mp 174°.
[a]~ -39° (c, 0.5 in CHCl 3).
8-(2-Methylpropenoyl), 9-Ac: [89396-27-0].
C 21 H 240 8 M 404.416
Constit. ofT. prancii. Cryst. (Et20jpet. ether). Mp 171°.
[a]~4 +42° (c, 1.09 in CHC1 3).
Bohlmann, F. et al, Justus Liebigs Ann. Chem., 1984, 162.
C 15H 1,06 M 292.288
4,5-Epoxy-8,13-dihydroxy-14-oxo- Sq-00504

a
(4Z,6rx.,8P,9rx.,l Op)-form
1(10),7(11)-germacradien-12,6-olide 9- Hydroxyatripliciolide
8-( M ethylpropanoyl): [71 052-04-5].
CHO H C19H120 7 M 362.379
Constit. of Calea urticifolia. Oil.
8-(3-Methylbutanoyl): [84754-02-9]. Lobatin B
13
CH20H C 20H 240 7 M 376.405
Constit. of Neurolaena lobata. Oil. [a]~ -ll.SO (c, l. 7 in
CHCl 3).
0 0 0 (4Z,6rx.,8P,9P,l Op)-form
ClsH180, M 294.304 8-(Methylpropenoyl):
(1(10)E,4rx.,5p,6rx.,8rx.)-form C19H:ze07 M 360.363
8-(2-Methylpropanoyl), 13-Ac: Glaucogalamensolide Constit. of Trichogonia prancii. Gum.
isobutyrate 8-(Methylpropenoyl) 9-Ac:
C21 H 260 8 M 406.432 C21H120 8 M 402.400
Constit. of Vernonia galamensis. Cryst. Mp 183°. Constit. of T. prancii. Gum.
8-(3-Methylbutanoyl), 13-Ac: Glaucogalamensolide 8-Angeloyl:
isovalerate C:zeH120 7 M 374.390
C12H 280 8 M 420.458 Constit. ofT. prancii. Cryst. (pet. ether). Mp 75°.
Constit. of V. galamensis. Cryst. Mp 138°. [aJn -ll4° 9-(Methylpropenoyl):
(c, 0.6 in CHCl 3). C19H:ze09 M 392.362
Zdero, C. et al, Phytochemistry, 1990, 29, 3668 (isol, pmr) Constit. ofT. prancii. Cryst. Mp 164°. [a]~ -82.SO (c,
0.2 in CHCl 3).
IIP,13-Epoxide, 8-(methylpropenoyl), 9-Ac:
C21H120u M 450.398
Constit. of T. prancii. Gum.
8-(2-Hydroxymethyl-lE-butenoyl): [76235-74-0].
Conoprasiolide
C:zeH120 8 M 390.389
Isol. from Conocliniopsis prasiifolia. Gum.
8-(2-Acetoxymethyl-2E-butenoyl):
C12H 240 9 M 432.426

239
3,10-Epoxy-8,15-dihydroxy-1-oxo-... - 4,5-Epoxy-1-hydroperoxy-10(14) ... Sq-00507 - Sq-00510

Constit. of C. prasiifolia. Gum. [IX]~ -29.6° (c, 3.7 in Isol. from V. pinnatilobata. Cryst. Mp 175-176°. [1X]n
CHCI 3)(as acetate). -82.4°.
4,5-Dihydro: see 3,10- Epoxy-8,9-dihydroxy-1-oxo- 2, II ( 13)- 8-(2-M ethylpropenoyl): 17,18-Dehydroviguiepinin
germacradien-12,6-o/ide, Sq-00503 C 19H 100 7 M 360.363
Bohlmann, F. et al, Phytochemistry, 1979, 18, 119; 1980, 19, 1547; Constit. of V. eriophora. Cryst. (EtOAcjdiisopropyl
1981, 20, 1323. ether). Mp 164°. [1X]i] -70.12° (c, 0.241 in MeOH).
Borges-del-Castillo, J. eta/, J. Nat. Prod. (Lloydia), 1987, 45, 762
(lobatin B) Vichnewsk:i, W. eta/, Phytochemistry, 1976, 15, 191
(Goyazensolide)
Romo de Vivar, A. et al, Rev. Latinoam. Quim., 1978, 9, 171
3,10-Epoxy-8,15-dibydroxy-1-oxo- Sq-00507 ( Viguiepinin)
2,4,11(13)-germacratrien-12,6-olide Le Quesne, P.W. eta/, J. Org. Chern., 1982, 47, 1519
(Lychnophorolides)
0 Herz, W. eta/, J. Org. Chern., 1982, 47, 2798 (cryst struct,
Goyazensolide)
Delgado, G. eta/, Phytochemistry, 1982, 21, 1305
(Dehydrovigueipinin)

4,5-Epoxy-1(10),11(13)-germacradien- Sq-00509
12,6-olide

l:(l
Ct5Ht60 6 M 292.288
(4E,6a.,8rx.,JO/f)-form )(fJ6_:r
8-Angeloy/: [71939-83-8]. Centratherin 0
C 10H:zz07 M 374.390 C 15H100 3 M 248.321
Constit. of Centratherum punctatum. Cryst. (EtOAc).
Mp 105-110°. Originally formulated as 12,8-olide. (l(JO)E,4rx.,5P,6a.)-form [20554-84-1] Parthenolide
Constit. of Chrysanthemum parthenium and Michelia
Vichnewski, W. et al, Phytochemistry, 1976, 15, 1775 (isol)
champaca. Cryst. (diisopropyl ether). Mp 116.5-117°.
Ohno, N. et al, Phytochemistry, 1979, 18, 681 (isol)
Herz, W. eta/, J. Org. Chern., 1982, 47, 2798 (structW) [1X]i:' -81.4° (c, 1.04 in CHCI 3).
11 p,JJ-Dihydro: (66397 -64-6]. 41X,5P-Epoxy-! (1 O)-
germacren-12,61X-olide. Dihydroparthenolide
3,10-Epoxy-8,15-dihydroxy-1-oxo- Sq-00508
C 15H 220 3 M 250.337
2,4, 11(13)-germacratrien-12,6-olide Constit. of M. lanuginosa and M. compressa. Cryst.
0 (Et20jhexane). Mp 127°. [1X]n -68.SO.
Govindachari, T.R. eta/, Tetrahedron, 1965, 21, 1509 (isol, struct)
Quick, A. eta/, J. Chern. Soc., Perkin Trans. 2, 1976, 465 (cryst
struct)
Ogura, M. eta/, Phytochemistry, 1978, 17, 957 (isol)
(4E,6cx,8cx, I 0~)-:form
4,5-Epoxy-1-hydroperoxy-10(14),11(13)- Sq-00510
germacradien-12,6-olide

¢Rr
Ct5Ht60 6 M 292.288 HOO
(4E,6rx.,8rx.,l0f/)-form
8-Ange/oy/: [80795-27-3]. Lychnophorolide A
C:zoli:zz07 M 374.390
Found in Lychnophora affinis. Cryst. (EtOHjEtOAc).
Mp 165.5-166.5°. [IX]~ -34° (c, 1.4 in EtOH).
8-Tig/oy/: [80795-28-4]. Lychnophorolide B 0
C10H:zz07 M 374.390 . C 15H 100 5 M 280.320
Constit. of L. affinis. (lp,4rx.,5p,6rx.)-form [64845-91-6] Peroxyparthenolide
8-(2-Methylpropenoy/): [60066-35-5]. Goyazensolide Constit. of Magnolia grandiflora. Cryst. (Me2CO/Et20).
C1,H100 7 M 360.363 Mp 190° dec. [1X]i] +27° (c, 0.21 in Me2CO).
lsol. from Eremanthus goyazensis. Cryst. (C6H 6). Mp El-Feraly, F.S. et a/, J. Org. Chern., 1979, 44, 3952.
175-!77°. (IX]~ -22.S0.
(4E,6rx.,8p,J 0/f)-form
8-Ange/oyl: [59481-48-0]. Budlein A
C10H 220 7 M 374.390
Constit. of Viguiera buddleiaformis. Cryst.
(Me2CO/diisopropyl ether). Mp 106-108°. [1X]i] -82.3°
(MeOH).
8-(2-Methy/butanoyl): 17,18-Dihydrobudlein A
C10H 1,.07 M 376.405
Constit. of V. hemsleyana. Cryst. (C6H 6/CHCI 3).
8-(2-Methy/propanoyl): [69296-76-0]. Viguiepinin
C1,H 220 7 M 362.379

240
4,5-Epoxy-1-hydroperoxy-8-hydroxy-... - 4,5-Epoxy-8-hydroxy-1(10),11(13)-... Sq-00511 - Sq-00515

4,5-Epoxy-1-hydroperoxy-8-hydroxy- Sq-00511 1,10-Epoxy-8-hydroxy-4,11(13)- Sq-00513

10(14), 11(13)-germacradien-12,6-olide germacradien-12,6-olide
0

H~
C 15H 100 6 M 296.319
0
C 15H100 4
~
M 264.321
0

(lp,4E,6«,8P,l0«)-form
(1P,4«,5P,6«,8f/)-form 8-Hydroxytithifolin
Ac: [61228-73-7]. Peroxyferolide
8-Angeloyl:
Constit. of Liriodendron tulipifera. Cryst. Mp 190° dec.
C10H 260 5 M 346.422
[1X]~ +20° (MeOH). .
Constit. of Tithonia rotundifolia. Gum. [1X]i;' + 35.5° (c,
Doskotch, R.W. eta/, J. Chern. Soc., Chern. Commun., 1976, 402. 0.1 in CHC1 3).
8-(2,3-Epoxy-2-me thylbutanoyl):
4,5-Epoxy-8-hydroxy-1(10),11(13)- Sq-00512 C10H 260 6 M 362.422
germacradiene-12,6;14,2-diolide Constit. of T. rotundifolia. Gum. [1X]~4 + 8° (c, 0.1 in
CHC1 3).
0 Bohlmann, F. et al, Phytochemistry, 1981, 20, 267.

1,10-Epoxy-14-hydroxy-4,11(13)- Sq-00514
germacradien-12,6-olide

(2a,4a,5a,6a,8a)-form
0
C 15H 160 6 M 292.288
(2«,4«,5«,6«,8«)-form
8-(2-Methylpropenoyl): [110268-35-4]. lsoelephantopin
C19H100, M 360.363 CtsH100 4 M 264.321
Constit. of Elephantopus angustifolius. Gum. (lp,4E,6r~.,10«)-form[93930-16-6] Melampomagnolide A
8-(3-Methyl-2-butenoyl): Desacylisoelephantopin senecioate Constit. of Magnolia grandiflora. Cryst. (Etp). Mp 177-
C10H 22 0 7 M 374.390 1780. [1X]n -19° (c, 0.12 in CHC1 3).
From E. angustifolius. Oil. El·Feraly, F.S., Phytochemistry, 1984, 23, 2372.
8- Tigloyl: Desacylisoelephantopin tiglate
C10H 220 7 M 374.390 4,5-Epoxy-8-hydroxy-1(10),11(13)- Sq-00515
From E. angustifolius. Oil. germacradien-12,6-olide
(2P,4«,5P,6«,8«)-form
8-(3-Methyl-2-butenoyl): [21899-50-3]. Elephantin
C10H 220 7 M 374.390
Isol. from E. elatus. Shows antitumour props. Cryst.
242-244°. [1X]i,7 -380° (c, O.Q15 in MeOH).
8-(2-Methylpropenoyl): [13017-11-3]. Elephantopin. NSC
100046
C19H100 7 M 360.363 CtsH100 4 M 264.321
Constit. of E. e/atus and E. nudatus. Shows antitumour (l(JO)E,4«,5P,6«,8«)-form (34175-72-9] Stizolin
props. Cryst. (MeOH). Mp 262-264°. [1X]ii -398° (c, Constit. of Stizolophus balsamita. Cryst. (C 6H 6). Mp
0.016 in MeOH). 184.5-186.5° dec. [IX]~ -30.46° (c, 2.68 in CHC1 3).
8-(2-Methy/propanoyl): Dihydroelephantopin Ac: 11 ,13-Dehydrolanuginolide
C 19H 220 7 M 362.379 Ct,H 220 5 M 306.358
Constit. of E. tomentosus. Isol. from Michelia lanuginosa. Cryst. (CHC1 3/pet.
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3867 (Elephantin) ether). Mp 168° dec. [1X]n -96.SO (c, 0.74 in CHC1 3).
Kupchan, S.M. eta/, J. Med. Chern., 1971, 14, 1147 (pharmacol) 4-Hydroxy-2-hydroxymethyl-2E-butenoyl: [30994-28-6].
Watson, W.H. et al, Acta Crystallogr., Sect. B, 1982, 38, 511 (cryst Stizolicin
struct) C10H 260 7 M 378.421
Haruna, M. et al, J. Nat. Prod. (Lloydia), 1985, 48, 93 (isol)
Zhang, D. eta/, Phytochemistry, 1986, 25, 899 (synth)
Constit. of S. coronopifolius. Cryst. (EtOH). Mp 152-
Jakupovic, J. et al, Phytochemistry, 1987, 26, 1467 153.SO. [1X]ii -32.4° (c, 2.19 in EtOH).
(lsoelephantopin) 11P,l3-Dihydro: 41X,5P-Epoxy-81X-hydroxy-1 (10)-germacren-
12,61X-olide. Desacetylanuginolide
CtsH220 4 M 266.336
Constit. of M. fuscata. Oil.
11P,I3-Dihydro, Ac: [31025-59-9]. Lanuginolide

241
4,5-Epoxy-9-hydroxy-1(10),11(13)-... - 1,2-Epoxy-5-hydroxy-10(14)-... Sq-00516 - Sq-00519

C 17H 240 5 M 308.374 Budesinsky, M. eta/, Collect. Czech. Chern. Commun .. 1984, 49,
Constit. of M. lanuginosa and M. compressa. Cryst. 637.
(EtzO). Mp 185°. [exJn -57°. Ruangrungsi, N. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 163.
(l(JO)E,4~,5p,6~,8f/)-form
Ac: [41059-80-7]. Lipiferolide 4,5-Epoxy-14-hydroxy-1(10),11(13)- Sq-00517
C 17H 220 5 M 306.358 germacradien-12,6-olide
Constit. of Liriodendron tulipifera. Cryst.

~
(EtOHjhexane). Mp 118-119°. [ex]~ -125° (c, 0.06 in
MeOH).
Angeloyl: [77096-83-4]. Deltoidin A
C20H 260 5 M 346.422
Constit. of Eupatorium deltoideum. Cryst. Mp 159-161°.
[exJn -145° (CHC1 3).
0
8-(4-Hydroxy-2-methyl-2E-butenoyl): [57718-81-7].
Eupassopilin C1sH2004 M 264.321
C20H 260 6 M 362.422 (l(JO)E,4~,5P,6~)-form [93930-15-5] Melampomagnolide B
Constit. of E. hyssopifolium. Gum. [ex]~ -161 o (c, 0.3 in Constit. of Magnolia grandifiora. Cryst. (Et20). Mp 174-
MeOH). 1750. [exln -40° (c, 0.18 in CHC1 3).
(l(JO)E,4~,5~,6~,8f/)-form El-Feraly, F.S., Phytochemistry, 1984, 23, 2372.
(4-Hydroxy-2-hydroxymethyl-2Z-butenoyl): [57526-55-3].
Liatripunctin 1,10-Epoxy-8-hydroxy-2,4,11(13)- Sq-00518
C2oH2607 M 378.421 germacratrien-12,6-olide
Isol. from Liatris punctata. [ex]~ -41.7°.
Talapatra, S.K. eta/, J. Chern. Soc., Chern. Commun., 1970, 1534
(Lanuginolide)
Mukhametzhanov, M.N. eta/, Khim. Prir. Soedin., 1970, 6, 505;
1971, 7, 405; Chern. Nat. Compd. (Engl. Trans/.), 525, 386 (isol,
Stizo/in, Stizolicin)
Talapatra, S.K. eta/, Phytochemistry, 1973, 12, 1827
(Dehydrolanuginolide)
Doskotch, R.W. eta/, Phytochemistry, 1975, 14, 769 (Lipiferolide)
Herz, W. eta/, Phytochemistry, 1975, 14, 1561 (Liatripunctin) CtsHts04 M 262.305
Herz, W. eta/, J. Org. Chern., 1976, 41, 1015 (Eupassopilin) (Jp,2Z,4Z,6~,8p,JOrr.)-form
Quijano, L. et a/, Phytochemistry, 1980, 19, 1975 (Deltoidin A) 8-Deacyl-15-deoxypunctatin
lida, T. eta/, Phytochemistry, 1982, 21, 701 (Desacetyllanuginolide)
Cassady, J.M. eta/, Experientia, 1984, 40, 930 (iso/, cmr, struct, 8-Angeloyl: 5' ,15-Bisdeoxypunctatin
Stizolin, Stizolicin) C20 H 240 5 M 344.407
Constit. of Hartwrightia fioridana. Gum.
4,5-Epoxy-9-hydroxy-1(10),11(13)- Sq-00516 8-(2-Hydroxymethyl-2Z-butenoyl): 15-Deoxypunctatin
C20H 240 6 M 360.406
germacradien-12,6-olide Constit. of H. fioridana. Gum.

eRr
OH 8-(2-Methyl- 2,3-epoxybutanoyl):
C20H 240 6 M 360.406
Constit. of Trichogonia santosii. Cryst. (EtzO). Mp 173°.
[cx]i;' -422° (c, 0.09 in CHC1 3).
15-Hydroxy, 8-0-(2-hydroxymethyl-2Z-butenoyl). [49776-
54-7]. Punctaliatrin. Punctatin
0 C20 H 240 7 M 376.405
C 15H 200 4 M 264.321 Constit. of Liatris punctata. Cryst. Mp 163-165°.
(l(JO)E,4~,5P,6~,9~)-form [78146-51-7] 9~­ 2a:,3a:-Epoxide: see 1,1 0:2,3-Diepoxy-8-hydroxy-2,4, 11(13)-
Hydroxypartheno/ide. NSC 290497 germacradien-12,6-olide, Sq-00446
lsol. from Anvillea garcini and Zoegea baldschuanica. Herz, W. et a/, Phytochemistry, 1973, 12, 1421 (Puncta/iatrin)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 843.
Shows antitumour props. Cryst. (CHC1 3 jpet. ether). Mp Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 162 (iso[)
141-143°. [ex]~ -57° (MeOH).
Jlft,J3-Dihydro: [114076-73-2]. 4ex,5ft-Epoxy-9ex-hydroxy-
1(10)-germacren-12,6ex-olide. 9~­ 1,2-Epoxy-5-hydroxy-1 0(14)-germacren- Sq-00519
Hydroxydihydropartheno/ide 12,6-olide
C15H 220 4 M 266.336
Constit. of Paramichelia baillonii. Oil. [ex]~ -60°
(CHC1 3).
(l(JO)E,4~,5p,6~,9f/)-form
Ac: [55249-44-0]. 9-Acetoxypartheno/ide
Ct7Hn0s M 306.358
Constit. of Matricaria suffructicosa. Oil. [ex]~ -59.7° (c,
4.7 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1975, 108, 437. M 266.336
Tyson, R.L. eta/, Experientia, 1981, 37, 441.

242
4,5-Epoxy-2-hydroxy-1(10)-germacren-... - 3,10-Epoxy-8-hydroxy-1-oxo-... Sq-00520 - Sq-00524

(1rz,4rz,5P,6rz,11PH)-form C19H 220 6 M 346.379

Constit. of Achillea millefolium. Constit. of Viguiera greggii and Zexmenia brevifolia.
Ulubelen, A. et al, Phytochemistry, 1990, 29, 3948 (isol, pmr) Cryst.
Angeloyl: [109361-82-2]. Ladibranolide
4,5-Epoxy-2-hydroxy-1(10)-germacren- Sq-00520 C:wH 240 6 M 360.406
Constit. of V. /adibractate. Prisms (EtOAc).
12,6-olide
Liu, Y.-L. eta/, Phytochemistry, 1984, 23, 1967 (Zexbrevin)
Gao, F. eta/, Phytochemistry, 1987, 26, 779 (Ladibranolide)

3,10-Epoxy-8-hydroxy-1-oxo-2,4,11(13)- Sq-00524
germacratrien-12,6-olide
0
C1sH22 0 4 M 266.336
(1(10)E,2rz,4rz,5P,6rz,11PH)-form [114076-72-1] 2rz-
Hydroxydihydroparthenolide
Constit. of Paramichelia baillonii. Oil.
Ruangrungsi, N. et al, J. Nat. Prod. (Lloydia), 1988, 51, 163.

(4E,6a,8~, 1O~}:form
4,5-Epoxy-3-hydroxy-1(1 0)-germacren- Sq-00521
12,6-olide
CtsHt60 5 M 276.288

HO~,I
(4E,6rx.,8P,l 0/1)-form
2-Methylpropenoyl: [30412-86-3]. Calaxin
01 C 19H:w06 M 344.363
0
Constit. of Helianthus ciliaris and Ca/ea axillaris. Cryst.
0 Mp 180-182°. [ocJn -ll5°.
C 15H 220 4 M 266.336 2-Methy/propanoyl: [30412-87-4]. Ciliarin
(1(10)E,3P,4rz,5rz,6rz,11S)-form [126829-69-4] Ct9H 180 6 M 342.348
3P-Hydroxy-11oc, 13-dihydroparthenolide Constit. of H. ciliaris. Cryst. Mp 148°. [ocln -143°.
Constit. of Pentzia incana. Cryst. Mp 186°. [oc]i;l + 38° (4Z,6rx.,8rx.,1 0/1)-form
(c, 2.44 in CHC1 3). 6-Hydroxygoyazenso/anolide
Zdero, C. et al, Phytochemistry, 1990, 29, 189 (isol, pmr) 6-Angeloy/: [77448-64-7]. Lychnopholide
C:wH22 0 6 M 358.390
4,9-Epoxy-5-hydroxy-11(13)-germacren- Sq-00522 Constit. of Lychnophora hakeaefolia. Cryst. (Etpjpet.
12,6-olide ether). Mp 128°. [oc]~4 -56.9° (c, 0.26 in CHC13).
5-Hydroxy-4,9-oxido-11(13)-germacren-12,6-olide 6-Tigloyl:
CzoH 220 6 M 358.390
Constit. of Eremanthus bico/or. Gum. [oc]i;l -54.3° (c, 2
in CHC1l).
6-(2,3-Epoxy-2-methylbutanoyl): Epoxylychnopholide. 6oc-
(2,3- Epoxybutyryloxy)goyazensolanolide (inc orr.)
C:wH220 7 M 374.390
lsol. from Proteopsis argentea. Cryst. (Et20jpet. ether).
Mp 168°. [ocJn -15.8° (c, 0.38 in CHCI 3).
2-Methy/propenoyl: [62569-46-4]. 15-Deoxygoyazensolide
C 15H 22 0 4 M 266.336
Ct9H:w06 M 344.363
(4P,5P,6rz,9P,1 OrzH)-form Constit. of Vanillosmopsis erythropappa. Cryst. Mp 132-
Constit. of Cyathocline lutea. Cryst. (EtOH). Mp 136- 1340. [ocJii. -38°.
1380. [oc]~ + 53.3° (c, 0.6 in CHC1 3). (4Z,6rz,8P,10/l)-form [67815-63-8] Atripliciolide
Sohoni, J.S. et al, Phytochemistry, 1984, 23, 1181.
8-(2-Methylbutanoyl): [71939-66-7].
CzoH240 6 M 360.406
3,10-Epoxy-8-hydroxy-1-oxo-2,11(13)- Sq-00523 Constit. of H. lehmannii. Oil.
germacradien-12,6-olide 8-Ange/oy/: [79306-95-9]. 15-Deoxybudlein A
C:wH220 6 M 358.390
OH Constit. of C. /antanoides. Cryst. (C6H 6). Mp 132-134°.
4,5-Dihydro: see 3, 10-Epoxy-8-hydroxy-1-oxo-2, 11 (13)-
germacradien-12,6-olide, Sq-00523
Vichnewski, W. eta/, Phytochemistry, 1976, 15, 1775; 1982, 21,
464 (15-Deoxygoyazensolide, 15-Deoxybudlein B)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 676 (Atripliciolide)
CtsHts0 5 M 278.304 Chawdhury, P.K. eta/, J. Org. Chern., 1980, 45, 4993 (Calaxin,
Ciliarin)
(4rzH,6rz,8P,l 0/1)-form
2-Methy/propenoy/: [28644-86-2]. Zexbrevin

243
4,5-Epoxy-1-oxo-10(14),11(13)-... - 3,10-Epoxy-1,3,8,15-tetrahydroxy-... Sq-00525 - Sq-00527

Bohlmann, F. et al, Phytochemistry, 1980, 19, 2381, 2663; 1981, Constit. of Vernonia saltensis. Oil. [1X]i;' + 36.3" (c, 4.1 in
20, 739 (isol) CHC1 3). Identity of the two samples not certain.
Herz, W. et al, J. Org. Chern., 1982, 47, 2798 (struct) Hirsutinolide is unknown.
1,8,13-Tri-Ac: [72712-42-6]. 8fJ.-Acetoxy-IOfJ.-
4,5-Epoxy-1-oxo-10(14),11(13)- Sq-00525 hydroxyhirsutinolide I ,I3-0-diacetate
germacrad.ien-12,6-olide C11 H:u;0 10 M 438.430
Constit. of V. saltensis. Oil. [1X]n -3° (c, 0.6 in CHC1 3).
0
8-Propanoyl, 13-Ac: [71305-86-7]. 8fJ.-Propionyloxy-IOP-
hydroxyhirsutinolide-I3-0-acetate
C20 H:u;09 M 410.420
Constit. of V. scorpioides. Oil. [1X]~4 + 63.SO (c, 0.5 in
CHC1 3).
8-Propanoyl, 1,13-di-Ac: [79081-71-3]. 8fJ.-Propionyloxy-IOfJ.-
0 hydroxyhirsutinolide I ,I3-di-O-acetate
CISHI804 M 262.305 CzzHza010 M 452.457
Constit. of V. scorpioides. Oil.
(4«.,5P,6« )-form [71277-23-1] Anhydroverlotorin-4«.,5P-epoxide
CISHI804 M 262.305 0 1-Me, 8-propanoyl, 13-Ac: [71305-76-5]. 8-Propionoyloxy-
Constit. of Tanacetum parthenium. Gum. [1X]n + 135° (c, IOfJ.-hydroxy-I-O-methylhirsutinolide-I3-0-acetate
0.2 in CHC1~). C11 Hza09 M 424.447
Constit. of V. scorpioides. Oil. C8-config. uncertain.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2543 (isol)
8,10,13-Tri-Ac: [72748-29-9]. ap,IOfJ.-Diacetoxyhirsutinolide
I3-0-acetate
1,4-Epoxy-1,8,10,13-tetrahydroxy-5,7(11)- Sq-00526 CnH:u;0 10 M 438.430
germacrad.ien-12,6-olide Constit. of Stokesia laevis. Oil. Occurs with the 1-
epimer.
0 1-Me, 8,10,13-tri-Ac: [72778-10-0]. BP,IOfJ.-Diacetoxy-I-0-
methylhirsutinolide I3-0-acetate
( 1cx,4Ji,8 p, 1Ocx )-form C11Hza010 M 452.457
Constit. of S. laevis. Oil. Occurs with the 1-epimer.
Bohlmann, F. et al, Phytochemistry, 1978, 17, 475; 1979, 18, 289,
987 (isol, pmr)
Rustaiyan, A.N. et al, Fitoterapia, 1919, 50, 243 (Hirsutolide)
C 15H 200 7 M 312.319 Cowall, P.L. et al, J. Org. Chern., 1981, 46, 1108 (isol)
(I«,4P,BP,IO«.)-form [119089-44-0] Herz, W. et al, Phytochemistry, 1983, 22, 1286 (isol)
Piptocarphol
8-(Methylpropenoyl), 13-Ac: [76248-63-0]. Piptocarphin A 3,10-Epoxy-1,3,8,15-tetrahydroxy- Sq-00527
C11 H:u;09 M 422.431 4,11(13)-germacradien-12,6-olide
Constit. of Piptocarpha chontalensis. Oil.
8-Tigloyl, 13-Ac: [76215-49-1]. Piptocarphin B I
OH
CuHza09 M 436.458
Constit. of P. chontalensis. Oil.
8-(Methylpropenoyl): [76215-50-4]. Piptocarphin C
C 19H 140 8 M 380.394
Constit. of P. chontalensis. Oil.
13-Ac: [76215-51-5]. Piptocarphin D
C 17Hu08 M 354.356
Constit. of P. chontalensis. Oil. 0
8-(Methylpropenoyl), l-Et ether, 13-Ac: [76215-52-6]. C15H 200 7 M 312.319
Piptocarphin E (I«,3«,4Z,6«,8P,IO«.)-form
C 13H 300 9 M 450.485 8-Ange/oyl: [75680-26-1]. Niveusin A
Constit. of P. chontalensis. Oil. CzoH:u;08 M 394.421
13-Et ether, 8-(methylpropenoyl): [76215-53-7]. Piptocarphin Constit. of Helianthus niveus. Cryst. (EtOAc). Mp 127-
F 1280.
C11Hza08 M 408.447 [80482-71-9]
Constit. of P. chontalensis. Oil.
Ohno, N. et al, Phytochemistry, 1980, 19, 609.
13-Tigloyl: Piptocarphin G
C20H:u;08 M 394.421
Constit. of P. opaca. Oil.
13-(2-Methylpropenoyl): Piptocarphin H
C 1,H140 8 M 380.394
Isol. from P. opaca. Oil.
(I«,4P,8P,JOJI)-form
8,13-Di-Ac: [72712-41-5]. 8P-Acetoxy-10P-
hydroxyhirsutinolide 13-0-acetate. Hirsutolide
C19H140 9 M 396.393

244
3,4-Epoxy-2,5,8,9-tetrahydroxy-•.. - 1,10-Epoxy-4,8,11-trihydroxy-5,7(11)... Sq-00528 - Sq-00532

3,4-Epoxy-2,5,8,9-tetrahydroxy-11(13)- Sq-00528 8-(2-Hydroxymethy/propenoyl), 13-Ac: 8P-(2-

germacren-12,6-olide Hydroxymethylacryloyloxy)hisutinolide 13-0-acetate
C11 H160 9 M 422.431
Constit. of V. spp. Cryst. (Et20/pet. ether). Mp 72°.
[a]~ + lll.2° (c, 1.3 in CHC1 3).
8-(2-Hydroxymethylpropenoyl), 14-hydroxy, 13-Ac: 8/J-(2-
Methylacry/oyloxy )-14-hydroxyhisutino/ide 13-acetate
~ 1 H 16 0 10 M 438.430
lsol. from V. spp. Oil. Misnamed in the paper.
8-(2-Methy/propenoyl), 13-Ac: 8P-(2-
Methylacryloy/oxy)hirsutinolide 13-0-acetate
(2«)«,4«.5P,6«,8«,9P,10«H)-form
CuH160 8 M 406.432
8-(2-Methy/butanoyl), 9-Ac: [81623-28-1]. Vicolide C Isol. from V. spp. Oil. [a]~ + l9.SO (c, 1.0 in CHC1 3).
C21H 300 9 M 438.474
Constit. of Vicoa indica. Cryst. (Me2COfhexane). Mp 8-(2,3-Epoxy-2-methylpropanoyl), 13-Ac: 8P-(2-Methyl-2,3-
202-204°. [1X]n -100° (c, 2.0 in CHC13). epoxypropionyloxy)hirsutinolitle 13-0-acetate
CuH160 9 M 422.431
Purushothaman, K.K. eta/, J. Chem. Res. (S), 1981, 374 (cryst Isol. from V. spp. Oil. [a]~ + 18.3° (c, 2.05 in CHC1 3).
struct)
[68024-72-6)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 475; 1979, 18, 289,
1,2-Epoxy-3,8,10-trihydroxy-4,11(13)- Sq-00529 987 (isol, pmr)
germacradien-12,6-olide
1,10-Epoxy-3,8,14-trihydroxy-4,11(13)- Sq-00531
germacradien-12,6-olide

C15H 100 6 M 296.319

(1P,2P.JP,4E,6«,8P,10«)-form C15H:zo06 M 296.319
8-Ange/oy/: [56377-69-6]. Tifruticin (1P.JP,4Z,6rt,8P,1fh)-form
C:zoll160 7 M 378.421 8-Ange/oy/, 14-Ac: [82451-45-4]. Rotundint
Constit. of Tithoniafruticosa. Cryst. (EtOAc). Mp 141°. CnH280 8 M 420.458
[a]i;1 -22° (c, l.l in CHC1 3). Constit. of Trithonia rotundifolia. Cryst.
15-Hydroxy, 3-ketone, 8-ange/oy/: [119889-30-4]. 15-' (Me2CO/diisopropyl ether). Mp 255-257°. [a]~ -259.SO
Hydroxy-3-dehydrotifruticin (MeOH).
C:zoll240 8 M 392.405 Romo de Vivar, A. et al, Phytochemistry, 1982, 21, 375.
Constit. of T. pedunculata. Pale yellow oil.
Herz, W. eta/, J. Org. Chem., 1975, 40, 3118 (isol) 1,10-Epoxy-4,8,11-trihydroxy-5,7(11)-
Baruah, N.C. eta/, J. Org. Chem., 1979, 44, 1831 (conjig)
Sq-00532
Perez, A.L. et al, Phytochemistry, 1988, 27, 3897 (isol, deriv) germacradien-12,6-olide

1,4-Epoxy-1,8,13-trihydroxy-5,7(11)- Sq-00530
germacradien-12,6-olide

C15H:zo06 M 296.319
(1P,4«.5E,8rt,10«)-form
8-Hydroxycompactifloride
8-0-Hexanoyl: 8-Caproyloxycompactij/oride
C15H:zo06 M 296.319 C11 H 300 7 M 394.464
(1«,4P.SE,8p,JOPH)-form Constit. of Vernonia compactiflora and V. monocephala.
8-(2-Methylpropenoyl): 8/J-(2-Methy/acry/oxy)hirsutinolitle Gum (as di-Ac). [a]~ -102.5° (c, 0.89 in CHC1 3) (di-
C19H 240 7 M 364.394 Ac). Compactifloride appears to be unknown.
Isol. from V. spp. Cryst. (Et20/pet. ether). Mp 184°. Bohlmann, F. et al, Phytochemistry, 1982, 21, 695.
[afn4 -6.9° (c, l.l in CHC1 3).
8-(2,3-Epoxy-2-methylpropanoyl): 8/J-(2-Methyl-2)-
epoxypropiony/oxy)hirsutino/ide
C1,H240 8 M 380.394
Isol. from V. spp. Cryst. (Et20fpet. ether). Mp 170°.
[a]~ +0.7° (c, l.l in CHC1 3).

245
1,10-Epoxy-8,14,15-trihydroxy-... - 3,10-Epoxy-1,3,13-trihydroxy-4,7(11) ... Sq-00533 - Sq-00536

1,10-Epoxy-8,14,15-trihydroxy-4,11(13)- Sq-00533 Constit. of Helianthus niveus, H. annuus and H.

germacradien-12,6-olide maximiliana. Cryst. (EtOAc) or oil. Mp 88-89°, Mp 125-
1260. [oc]n -148° (c, 0.28 in MeOH).
8-(2R,3R-Epoxy-2-methylbutanoyl):
C10H 260 8 M 394.421
Isol. from Viguiera rnicrophylla. Prisms
(Et0Acjdiisopropy1 ether). Mp 190-192°. [oc)i;' -108° (c,
0.315 in CHC1 3).
8-(3-Methy/propenoyl): [34302-19-7]. Zexbrevin B
C 19H 240 7 M 364.394
C 15H 100 6 M 296.319 Constit. of V. greggii and Zexrnenia brevifolia. Cryst.
(Jp,4Z,6r~.,8«,10«)-form 4,5-Dihydro: see 3,1 0-Epoxy-1 ,3,8-trihydroxy-11 ( 13)-
8-(2-Methy/propenoJ!l)~ 14-Ac: [62687-46-1). Vernopectolith gerrnacren-12,6-o/ide, Sq-00545
A (1P,3«,4Z,6r~.,8p)-form
C21H260 8 M 406.432 8-(2-M ethylbutanoyl):
Constit. of Vernonia pectoralis. Amorph. [ocJn + 78° (c, 1 C10H 280 7 M 380.437
in CHC1 3). Constit. of C. oxy/epis. Gum.
Mompon, B. eta/, Tetrahedron, 1976, 32, 2545. 8-Angeloyl: 8-Deacy/-1P-hydroxyzacatechinolide-8-ange/ate.
8-Deacylzacatechino/ide 8-angelate (incorr.)
3,8-Epoxy-2,3,8-trihydroxy-4,11(13)- Sq-00534 C10H 260 7 M 378.421
Isol. from V. cordata. Oil.
germacradien-12,6-olide
8-(2-Methy/propenoyl), l-Ac: [64173-38-2]. lP-
Acetoxyzacatechinolith
C21 H 260 8 M 406.432
Constit. of C. zacatechichi. Cryst. (Et20). Mp 199°. [ocln
-222° (c, 1.35 in CHC1 3).
1-Ketone, 8-0-(2-rnethylbutanoyl):
C20H 260 7 M 378.421
Constit. of C. oxylepis. Gum.
1-Ketone, 8-(2-rnethy/propenoyl): [64173-40-6). 1-
C 15H 100 6 M 296.319
0xozacatechinolide
(2P,3«,4Z,6r~.,8p)-form CI,H 220, M 362.379
8-(2-Methy/propanoyl): [59979-59-8]. Tagitinin B Constit. of C. zacatechichi. Cryst. (Et20). Mp 167°. [oc]~
C1,H 260 7 M 366.410 -263° (c, 1.7 in CHC1 3).
Constit. of Tithonia diversifolia. Cryst. (lrT-,3«,4E,6r~.,8p)-form
(Me 2C0jisopropy1 ether). Mp 125°. [oc)n -142° (c, 1 in
8-(2-Methylpropanoyl): [34367-14-1]. Orizabin
CHC1 3).
C19H 260 7 M 366.410
8-(2-Methy/propanoyl), 2-Ac: [33143-54-3]. Woodhousin Constit. of T. tubae-forrnis and Z. brevifolia. Cryst. Mp
C21H2808 M 408.447 84-85°. [oc)n - 140°.
Constit. of Bahia woodhousei. Cryst. (EtOAcjhexane).
Bohlmann, F. et al, Phytochemistry, 1977, 16, 1065 (IjJ-
Mp 183-184.SO. [ocJn -206.3° (c, 4.26 in CHC13).
Acetoxyzacatechinolide, 1-0xozacatechinolide)
Herz, W. eta/, J. Org. Chern., 1972, 37, 906; 1978, 43, 4887 Chawdhury, P.K. eta/, J. Org. Chern., 1980, 4S, 4993 (Orizabin)
( Woodhousin) Ohno, N. et al, Phytochemistry, 1980, 19, 609 (Niveusm C)
Pal, R. et al, Indian J. Chern., Sect. B, 1976, 14, 77 (isol) Bohlmann, F. et al, Phytochemistry, 1982, 21, 1164.
Barauh, N.C. eta/, J. Org. Chern., 1979, 44, 1831 (struct) Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 495 (deriv)
Liu, Y.-L. et al, Phytochemistry, 1984, 23, 1967 (Zexbrevin B)
3,10-Epoxy-1,3,8-trihydroxy-4,11(13)- Sq-00535
germacradien-12,6-olide 3,10-Epoxy-1,3,13-trihydroxy-4,7(11)- Sq-00536
germacradien-12,6-olide
OH
I
(lcx,3cx,4Z,6cx,8~)-form

C 15H 280 6 M 296.319 C 15H 280 6 M 296.319

(1«,3«,4Z,6r~.,8p)-form (JP,3rT-,4E,6rT.,10p)-form
8-(2-Methy/butanoyl), l-Ac: 1-Hydroxy-8- 1-Tig/oy/, 3,13-di-Ac: [78835-07-1]. Chrestanolith
thsacylzacatechinolide C24H 300 9 M 462.496
C22 H 31P 1 M 422.474 Constit. of Chresta sphaerocephala. Gum. [oc]i~ -2.4° (c,
Constit. of Calea oxylepis. Gum. [oc]~ -161° (c, 0.09 in 0.5 in CHC1 3).
CHC13). Bohlmann, F. et al, Phytochemistry, 1981, 20, 518.
8-Ange/oy/: [75680-27-2]. Niveusin C. Annuithrin
C10H 260 7 M 378.421

246
3,10-Epoxy-2,8,9-trihydroxy-4,11(13) ... - 4,5-Epoxy-8,9,15-trihydroxy-1(10) ... Sq-00537 - Sq-00542

3,10-Epoxy-2,8,9-trihydroxy-4,11(13)- Sq-00537 4,5-Epoxy-2,8,13-trihydroxy-1(10),7(11)- Sq-00540

germacradien-12,6-olide germacradien-12,6-olide

HO,~'<::::
8 /0H

13
'0 ~ CH2 0H
0
0
C 15H 200 6 M 296.319
CtsH2006 M 296.319 (l(JO)E,2rx.,4rx.,5P,6rx.,8rx.)-form
(2P,3P,4Z,6rx.,Bp,9p,JofJ)-form 8-(2,3-Epoxy-2-methylpropanoyl), 2,13-di-Ac: [52229-58-0].
8-(2-Methylbutanoyl), 2,9-di-Ac: 2p,9rx.-Diacetoxy-3,10- Glauco/ide D
anhydrobrasiloide 8-(2-methylbutanoate) C23 H 280 10 M 464.468
C24H 32 0 9 M 464.511 Constit. of Vernonia unifiora. Cryst. Mp 187-188°. [1X]n
Constit. of Brasilia sickii. Cryst. Mp 148°. [1X]i; -34° (c, -90.
0.57 in CHC1 3). C-8 and C-9 ester groups may be Taylor, I.F. eta/, Acta Crystallogr., Sect. B, 1976, 32, 107 (cryst
interchanged. struct)
Gopolakrishna, E.M. eta/, Cryst. Struct. Commun., 1977, 6, 201
Bohlmann, F. et at, Phytochemistry, 1983, 22, 1213. (cryst struct)

3,10-Epoxy-3,8,14-trihydroxy-4,11(13)- Sq-00538 2,5-Epoxy-2,8,9-trihydroxy-1(1 0),3, 11 (13)- Sq-00541

germacradien-12,6-olide germacratrien-12,6-olid-14-oic acid
CH20H COOH

HO~ 0 0
CtsH2006 M 296.319
(3rx.,4Z,6rx.,8fJ)-form
C 15H 160 8 M 324.287
8-(2-Methylbutanoyl): [106533-67-9]. Tithonint
C20 H 28 0 7 M 380.437 (1(10)E,5p,6rx.,8p,9rx.)-form
Constit. of Tithonia rotundifolia. Cryst. (Et20jMe 2CO). 8-Angeloyl, 9-Ac, Me ester: [85527-47-5].
Mp 134-135°. [1X]~ -121.3° (c, 0.45 in MeOH). lchthyotherminolide
0 3-Me, 8-(2-Methylbutanoyl): [106533-68-0]. 0- C23H 260 10 M 462.452
Methyltithonin Constit. of Ichthyothere terminalis. Gum. [1X]i; -25° (c,
C21 H 300 7 M 394.464 0.3 in CHCI 3).
From T. rotundifolia. Oil. Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2317.
Alonso-L6pez, M. eta/, J. Chern. Soc., Perkin Trans. I, 1986,
2017. 4,5-Epoxy-8,9,15-trihydroxy-
1(10),2,11(13)-germacratrien-12,6-olid-
3,10-Epoxy-3,8, 15-trihydroxy-4,11(13)- Sq-00539 14-oic acid Sq-00542
germacradien-12,6-olide
HO

C 15H 160 8 M 324.287

C 15H 200 6 M 296.319 (1(10)Z,2Z,4rx.,5p,6rx.,8p,91;)-form
(3rx.,4Z,6rx.,Bp,JOrx.)-form 8-(2,3-Epoxy-2-methylbutanoyl), 15-Ac, Me ester: [78432-
79-8]. Melfusin
8-Angeloyl: [75680-25-0]. Niveusin B
C23 H 260n M 478.452
C20H 260 7 M 378.421 Constit. of Melampodium diffusum. Gum.
Constit. of Helianthus niveus. Oil.
Quijano, L. eta/, J. Nat. Prod. (Lloydia), 1981, 44, 266.
Ohno, N. eta/, Phytochemistry, 1980, 19, 609.

247
1,10-Epoxy-3,4,8-trihydroxy-11(13)-... - 4,5-Epoxy-1,8,13-trihydroxy-7(11)-... Sq-00543 - Sq-00546

1,10-Epoxy-3,4,8-trihydroxy-11(13)- Sq-00543 3,10-Epoxy-1,3,8-trihydroxy-11(13)- Sq-00545

germacren-12,6-olide germacren-12,6-olide

I
OH

C,sH 220 6 M 298.335

(1P.3P,4rx,6rx,8P,10rx)-form
8-Angeloyl: [81686-17-1]. Argophyllin A C 15H 220 6 M 298.335
C20 H 28 0 7 M 380.437 (1«.3«,4PH,6rx,8P,JOp)-form
Constit. of Helianthus argophyllus. Cryst. (MeOH). Mp
8-(2-Methylpropanoyl): [59979-61-2]. Tagitinin A
190-192°. [a:]i,l -157.0° (c, 0.10 in CHCI 3).
C 19H 180 7 M 358.347
Watson, W.H. eta/, Acta Crystallogr., Sect. B, 1982, 38, 834 (cryst Isol. from Tithonia diversifolia. Shows insectidica1 props.
struct) Cryst. (CHC1 3 jpet. ether). Mp 168-170°. [a:] 0 -154° (c,
Watanabe, K. eta/, Phytochemistry, 1982, 21, 709 (cryst struct)
1 in EtOH).
8-(2-Methylbutanoyl): [76627-97-9]. Viguilenin
1,10-Epoxy-3,8,15-trihydroxy-11(13)- Sq-00544 C20H 300 7 M 382.453
germacren-12,6-olide Constit. of Viguiera linearis. Cryst. (EtP/2-propano1).
Mp 168-169°. [a:]i;' -107° (MeOH).
Baruah, N.C. eta/, J. Org. Chern., 1979, 44, 1831 (Tagitinin A)
de Vivar, A.R. eta/, Phytochemistry, 1980, 19, 1795 (Viguilenin)
Sarma, J.C. eta/, Phytochemistry, 1987, 26, 2406 (cryst struct,
Tagitinin A)

4,5-Epoxy-1,8,13-trihydroxy-7(11)- Sq-00546
C15H 200 6 M 296.319 germacren-12,6-olide
(1P.3P,4Z,6rx,8P,JOrx)-form

H~~OH (lo,4o<,5p,6o,8o,lo.H)-fo~
8-Angeloyl: 15-Hydroxyleptocarpin
C20H 260 7 M 378.421
Constit. of Tithonia rotundifolia. Gum. [a:] 0 -84,50 (c,
0.24 in MeOH).
8-Angeloyl, 3-Ac: 3-Acetyl-15-hydroxyleptocarpin
C22H 280 8 M 420.458 0 0
Constit. of T. rotundifolia. Cryst. (CHC1 3/diisopropy1 C,sH 220 6 M 298.335
ether). Mp 213-214". [a:] 0 -118.3° (c, 0.16 in CHC1 3). (1rx,4rx,5P,6rx,8rx,10rxH)-form
8-(2-Methylpropenoyl), 3-Ac: 15-Hydroxyacetyleriojlorin Tri-Ac: [27479-41-0]. Confertolide
C21 H 260 8 M 406.432 C21 H 280 9 M 424.447
Constit. of Viguiera linearis. Cryst. (diisopropy1 Constit. of Vernonia conferta. Cryst. Mp 185-188°. [a:] 0
etherfMe 2CO). Mp 244-248°. [1X]i;' -69.4° (c, 0.167 in -82°.
MeOH). 8-(2-Methylpropenoyl), 13-Ac:
4a:,5-Dihydro, 8-angeloyl: [81686-18-2]. C21 H 280 8 M 408.447
C20H 280 7 M 380.437 Constit. of Stilpnopappus tomentosus. Gum. [1X]i;' -35°
Isol. from Helianthus argophyllus. Cryst. (CHC1 3). Mp (c, 0.3 in CHC1 3).
63-69°. [a:]i,l -137.5° (c, 0.14 in CHC1 3). 8-Tigloyl, 13-Ac:
4a:,5-Dihydro, 3-ketone, 8-angeloyl: [96087-11-5]. C22H 300 8 M 422.474
Argophyllone B Constit. of S. tomentosus. Gum.
C20H 260 7 M 378.421 8-(2-Methylpropenoyl), di-Ac:
Isol. from H. argophyllus. Cryst. (C 6H 6). [a:]i,l -158° (c, C23H 300 9 M 450.485
0.66 in EtOH). lsol. from S. tomentosus. Gum.
Watanabe, K. eta/, Phytochemistry, 1982, 21, 709 (Argophy/lin B) 8-Tigloyl, di-Ac:
Perez, C.A.L. et a/, Phytochemistry, 1984, 23, 823 (15-
C24H 320 9 M 464.511
Hydroxyleptocarpin)
Stipanovic, R.D. eta/, Phytochemistry, 1985, 24, 358 (Argophyllone lsol. from S. tomentosus. Gum.
B) 1-Ketone, 8-tigloyl, 13-Ac: [83182-58-5]. 8-
Delgado, G. eta/, Phytochemistry, 1985, 24, 2736 (15- Tigloylstilpnotomentolide
Hydroxyacety/erioftorin) C22H 280 8 M 420.458
Constit. of S. spp. Gum. Sti1pnotomentolide is
unknown.
1-Ketone, 8-(2-methylpropenoyl), 13-Ac:
C21 H 260 8 M 406.432
Constit. of S. tomentosus and S. pickelii. Gum [1X]i;'
- W (c, 0.27 in CHC1 3).

248
4,5-Epoxy-2,3,8-trihydroxy-1(10)-... - 4,5-Epoxy-3,8,13-trihydroxy-1-oxo-... Sq-00547 - Sq-00551

1-Ketone, 8,13-di-Ac: [99211-72-0]. Vernofultanin 3,10-Epoxy-3,8,9-tribydroxy-1-oxo- Sq-00549

C1,H240 8 M 380.394 4,11(13)-germacradien-12,6-olide
Constit. of Vernonia fulta. Cryst. (EtOAcjhexane). Mp
156-157°. 0
(1«,4«.SfJ,6«,8«,10fJH)-form
1-Ketone, 8,13-di-Ac: [99132-87-3]. lsovernofuhanin
C19H 240 8 M 380.394
Constit. of V. fulta. Gum.
Toubiana, R. et al, Tetrahedron Lett., 1974, 1755 (Confertolide)
Bohlmann, F. eta[, Phytochemistry, 1982, 21, 1045, 1445.
Catalan, C.A.N. et al, Phytochemistry, 1985, 24, 2113
(Vernofultanin, Isovernofultanin) CisHia07 M 310.303
(3«,4Z,6«,8fJ,9fJ,l0«)-form
4,5-Epoxy- 2,3,~tribydroxy-1(1 0)- Sq-00547 8-Ange/oy/: 1-Desoxy-9/J-hydroxy-1-oxoniveusin C
germacren-12,6-olide C20H 240 8 M 392.405
Constit. of Viguiera cordata. Oil.
HO~~OH Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 495.

HO , -- 3,10-Epoxy-8,9,15-tribydroxy-1-oxo- Sq-00550
0,
0 2,4, 11(13)-germacratrien-12,6-olide
0 0
C 15Hzz06 M 298.335
(1(10)E,2«.3/l,4«.SfJ,8fJ,11 fJH)-form
8-Ange/oy/: [62197-54-0]. Euperfolitin
C 20H 280 7 M 380.437
lsol. from Eupatorium perfo/iatum. Amorph. Mp 190-
1920. [1X]~ -5.81° (c, 0.119 in MeOH).
Herz, W. et al, J. Org. Chern., 1977, 42, 2264.

5,10-Epoxy-3,8,15-tribydroxy-11(13)- Sq-00548 C•sHI607 M 308.287

germacren-12,6-olide (4E,6«,8/l,9«,1 0/l)-form
9,15-Dihydroxyatripliciolide
9-(3-Methylbutanoyl), 8-(2-methy/propenoyl): [71 052-05-6].
C24H 280 9 M 460.480
Constit. of Calea urticifolia. Oil.
9-(3-Methy/-2-butenoyl), 8-(2-methy/propenoyl): [71052-07-
8].
C24H 260 9 M 458.464
C 15Hzz05 M 282.336 Constit. of C. urticifolia. Oil.
(3«,4fJH,5fJ,6«,8fJ,JOfl)-form 9-Ange/oy/, 8-(2-methylpropenoyl): [71 052-06-7].
C24H 260 9 M 458.464
8-(2-Acetoxymethyi-2Z-butenoyl), 15-Ac: [57800-56-3].
Constit. of C. urticifolia. Oil.
Chapliatrin
C24H 320 10 M 480.511 Bohlmann, F. et al, Phytochemistry, 1979, 18, 119.
Constit. of Liatris chapmanii and L. gracilis. Gum. [IX]i;.
-35°. 4,5-Epoxy-3,8,13-trihydroxy-1-oxo-7(11)- Sq-00551
8-(2-Acetoxymethyl-2Z-butenoyl), 3-Ac: [57800-57-4]. germacren-12,6-olide
Isochapliatrin
C24H3z010 M 480.511
Constit. of L. chapmanii. Cryst. (EtOAc/hexane). Mp
162-162.SO. [1X]n -74.1°.
8-(2-Acetoxymethyl-2Z-butenoyl), 3,15-di-Ac: [57843-10-4].
Acetylchapliatrin
C26H 340 11 M 522.548
Constit. of L. gracilis. Cryst. (hexane). Mp 142-144°.
C15H2007 M 312.319
[IX)ii• -35°.
(3fJ,4«.SfJ,6«,8«,10«H)-form
Herz, W. et al, Phytochemistry, 1975, 14, 1803; 1984, 23, 373 (isol,
cryst struct) 8-(4-Acetoxy-3-methyi-2Z-butenoyl), 13-Ac: 3-
Hydroxystilpnotomentolide 8-0-4-acetoxy-3-methyl-2-
butenoate
C24H 300 11 M 494.494
Constit. of Vernonia staehelinoides. Gum. [1X]~4 -100° (c,
0.8 in CHCI 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1445.

249
4,5-Epoxy-8,10,13-trihydroxy-1-oxo-••. - 1(10),4,11(13)-Germacratrien-12,6-•.. Sq-00552 - Sq-00556

4,5-Epoxy-8,10,13-trihydroxy-1-oxo- Sq-00552 1(10),4,11(13)-Germacratriene-12,6;14,8- Sq-00554

7(11 )-germacren-12,6-olide diolide
0

~OH
--~~OH
0
C 15H 200 7 M 312.319
C 15H 160 4 M 260.289
(4P,5«,6P,8P,10/1)-form
(l(JO)E,4E,6«,8f/).jorm [99132-88-4] Maximileolide
8-(2-Methylpropenoyl): Constit. of Helianthus maximiliani. Oil.
C1,H240 8 M 380.394
Constit. of Stilpnopappus glomeratus. Gum. Stewart, E.S. et al, Phytochemistry, 1985, 24, 2116.

8-(2-Methylpropenoyl), 10,13-di-Ac: [11091-29-5].

Glauco/ide A 1(10),4,11(13)-Germacratrien-12,6-olide Sq-00555
C13H 280 10 M 464.468
Constit. of Vernonia spp. Cryst. (MeOH). Mp 153-154°.
[ex]i,S -29° (c, 0.5 in CHC1 3).
8-(2-Hydroxymethylpropenoyl), 10,13-di-Ac: [68799-60-0]. (1(10)E,4E,6cx).jorm
19-Hydroxyglaucolide
C13H 280 11 M 480.468 0
Constit. of Erlangea remifolia. Gum. [ex]~4 -22.9° (c, 3.1 C 15H200 2 M 232.322
in CHC1 3). (1(10)E,4E,6«)-form [553-21-9] Costunolide
8,10,13-Tri-Ac: [11091-27-3]. Glauco/ide B Constit. of costus root (Saussurea lappa) and Artemesia
C21 Hu;010 M 438.430 balchanorum. Also from Talauma mexicana and Cosmos
lsol. from V. spp. Cryst. (Et20jpet. ether). Mp 75-77°. sulphureus. Piscicide. Cryst. (MeOH). Mp 106-107°. [exln
[ex]i,S -50° (c, 0.5 in CHC1 3). + 128° (c, 0.45 in CHC13).
Watson, W.H. et al, Cryst. Struct. Commun., 1974, 3, 697 (cryst 11P,13-Dihydro: see 1(10),4-Germacradien-12,6-o/ide, Sq-
struct) ~ 00553
Cox, P.J. et al, J. Chern. Soc., Perkin Trans. 2, 1975, 455 (cryst
3,4-Dihydro: see 3-Hydroxy-1(10)-germacren-12,6-olide,
struct)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1190; 1982, 21, 1045
Sq-00575
(isol) (1(10)E,4E,6f/)-form
C, 5H 200 2 M 232.322
Constit. of Geigeria rigida. Oil. [ex]~ -164° (c, 0.91 in
1(10),4-Germacradien-12,6-olide Sq-00553 CHC1 3).
(l(JO)Z,4E,6«)-form [125514-73-0] Melampolide

~13 lsol. from Aristolochia yunnanensis. Plates (Etp). Mp

144-145°. [ex]~ + 1.4° (c, 0.84 in CHC1 3).
I b~,. (1(10)E,4E,6cx,lli3H).:form Rao, A.S. et al, Tetrahedron, 1960, 9, 275 (isol)
Bouill, M.J. eta/, Acta Crysrallogr., Seer. B, 1976, 32, 3203 (cryst
0 struct)
C 15H 210 2 M 234.338 Kanasaki, T. et al, Agric. Bioi. Chern., 1976, 40, 1239.
Grieco, P.A. et al, J. Org. Chern., 1977, 42, 1717 (synth)
(I(10)E,4E,6r~.,11PH)-form [2225-79-8] Dihydrocostunolide Shibuya, H. et al, Chern. Lett., 1986, 85 (synth)
Constit. of Saussurea lappa. Cryst. (hexanejEtp). Mp Takahashi, T. et al, Tetrahedron, 1987, 43, 5499 (synth)
78°. [ex]n + 110.8° (CHC1 3). Ming, C.W. et al, Phytochemistry, 1989, 28, 3233 (isol, pmr, cmr,
13-Methoxy: 13-Methoxy-1(10),4-germacradien-12,6-o/ide. ir, cryst struct, Melampolide)
13-Methoxydihydrocostunolide
C16H 240 3 M 264.364 1(10),4,11(13)-Germacratrien-12,6-olid-14- Sq-00556
lsol. from S. lappa. Needles (MeOH). Mp 127-128°. [exln oic acid
+ 115° (CHC13).

~u (l(IO)E,4E,6a~fo""
(1(10)E,4E,6r~.,11«,11«H)-form
11 r~.,JJ-Dihydrocostunolide
C 15H 210 2 M 234.338
Constit. of Artemisia herba-alba. Needles (Et 20fhexane).
Mp 76-77°. 0
Kulkarni, G.H. et al, Tetrahedron, 1961, 12, 178 (13-
Methoxydihydrocostunolide) C15H 180 4 M 262.305
Rao, A.S. et al, Tetrahedron, 1961, 13, 319 (isol) (1(10)Z,4E,6r~.)-form
Corey, E.J. et al, J. Am. Chern. Soc., 1963, 85, 4033; 1965, 87, Taraxinic acid. Taraxin acid
5736 (uv, ir, pmr, synth) lsol. from Ainsliaea acerifolia. Cryst. Mp 156-157°. [ex]~
Fujomoto, Y. et al, Chern. Pharm. Bull., 1979, 27, 923 (synth, bib[) -34.SO (c, 1 in MeOH).
Raucher, S. et al, J. Org. Chern., 1986, 51, 5503 (synth)
Sanz, J.F. et al, Phytochemistry, 1990, 29, 541 (Dihydrocostunolide) P-n-Glucopyranosyl ester:
C21 H 280 9 M 424.447

250
4,9,11(13)-Germacratrien-12,6-olid-... - 8-Hydroxy-3,9-germacradien-12,6-... Sq-00557 - Sq-00560

Constit. of Taraxacum officina/e. Cryst. 11 ,13-Didehydro: [64845-92-7]. 1P-Hydroxy-4,!0(14),11(13)-

(CH 2Cl 2/MeOH). Mp 84-86°. germacratrien-12,6ex-olide. Artemorin.
11,13-Dihydro, P-v-glucopyranosyl ester: Deoxyperoxycostunolide
C21 H 300 9 M 426.463 C1sH200 3 M 248.321
Constit. of T. officina/e. Cryst. Mp 84-86°. Constit. of A. verlotorum and others. Cryst.
(l(JO)E,4E,6rx.)-form [106794-14-3] Perydiscolic acid (CH 2Cl 2/Etp). Mp I20-12l [exJn +89°.
0
•

Isol. from Perymenium discolor. Yell ow gum. 1-Ketone: [6907 5-68-9]. 1-0xo-4(1 0),14-germacradien-12 ,6rx.-
P-v-Glucopyranosyl ester: [93303-17-4]. Ainsliaside B olide
C21 H 280 9 M 424.447 CISH2003 M 248.321
lsol. from A. acerifolia. Needles (MeOH). Mp 157-161°. Isol. from A. herba-a/ba. Oil. [ex]~ + 83° (c, 0.2 in
[ex]); +83.4° (c, 0.51 in MeOH). CHCI3).
11,13-Didehydro, 1-ketone: [32619-90-2]. J-Oxo-
Hansel, R. et al, Phytochemistry, 1980, 19, 857.
Jin, H., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1982, 102, 911 4,10(14),11(13)-germacratrien-12,6ex-olide.
(Taraxinic acid) Anhydroverlotorin
Miyase, T. et al, Chern. Pharm. Bull., 1984, 32, 3043 (Ainsliaside CISHI803 M 246.305
B) Constit. of A. verlotorurn. Cryst. (Et20). Mp 123-124°.
Maldonado, E. et al, Phytochemistry, 1987, 26, 205 (Perydiscolic (lp,6rx.,11PH)-form [69075-77-0] Gallicin
acid)
Constit. of A. maritima. Mp 114-116°. [exln + 121° (c, 0.3
in CHCI3).
4,9, 11(13)-Germacratrien-12,6-olid-14-oic Sq-00557 1-Ketone: [125675-20-9].
acid CISH2003 M 248.321
From A. maritima. Cryst. Mp 132°.
1-Ketone, 10ex,l4-dihydro: 1-0xo-4-germacren-12 ,6rx.-olide
CISH2203 M 250.337
0 Isol. from E. maritima. Oil.
11 ,13-Didehydro, 1-hydroperoxide: (31105-79-0). lP-
Hydroperoxy-4, 10(14), II (13)-germacratrien-12,6-o/ide.
Verlotorin. Peroxycostunolide
CISH2004 M 264.321
CISHI804 M 262.305 Constit. of Magnolia grandiflora. Cryst. (Et20/EtOH).
(4Z,6rx.,9Z)-form Mp 141°. [ex]~ + 171° (c, 0.2 in Me 2CO).
P-v-Glucopyranosyl ester: [84294-92-8]. Ainslioside [8I679-95-0]
C21H 280 9 M 424.447 Geissman, T.A., Phytochemistry, 1970, 9, 2377 (Anhydroverlotorin,
Constit. of Ainsliaea acerifolia. Cryst. Mp 180-182°. [ex]~ Artemorin)
-55.7° (c, I in MeOH). Gonzalez, A.G. et al, J. Chern. Soc., Perkin Trans. I, I978, I243
Jin, H., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1982, 102, 9Il. (Gallicin)
El-Feraly, F.S. et al, J. Org. Chern., 1979, 44, 3952 (Verlotorin)
Gonzalez, A.G. et al, Tetrahedron Lett., I979, 3769 (conformn,
Hallerin Sq-00558 Gallicin)
[88125-88-6] Gordon, M.M. et al, J. Nat. Prod. (Lloydia), 1981, 44, 432 (isol)
Shimizu, T. et al, Heterocycles, 1982, 17, 53 (synth)
Pathak, V.P. et al, Phytochemistry, 1987, 26, 2I03 (isol, derivs)
Marco, J.A. et al, Phytochemistry, I989, 28, 3121 (isol, pmr)

8-Hydroxy-3,9-germacradien-12,6-olide Sq-00560

C 20H 300 4 M 334.455

Constit. of Laserpitium halleri. Pale-yellow pungent oil.
[ex]~ -68° (CHCI 3). Saponification gives 8,12-Epoxy-
1(1 0),4-germacradiene-6, 12-diol, Sq-00642.
Appendino, G. et al, J. Chern. Soc., Perkin Trans. I, I983, 2017. ClsH 220 3 M 250.337
Struct. not certain.
1-Hydroxy-4,1 0(14)-germacradien-12,6- Sq-00559 (3Z,6rx.,8rx.,9E,11rx.H)-form
olide lsobakhanolide
Constit. of Artemisia balchanorum. Cryst. (diisopropyl
etherfMe 2CO). Mp 133°. [ex]~ + 122° (c, 2.08 in CHC1 3).
Herout, V. et al, Collect. Czech. Chern. Commun., 1961, 26, 2612.

13 (1~,6cx,11cxH)-form

CISH2203 M 250.337
(1 p,6rx.,11 rx.H)-form.
Constit. of Artemisia herba. Oil.

251
9-Hydroxy-4,10(14)-germacradien-... - 1-Hydroxy-4,9,11(13)-germacratrien-... Sq-00561 - Sq-00565

9-Hydroxy-4,1 0(14)-germacradien-12,6- Sq-00561 C20H 220 6 M 358.390

olide Constit. of B. dichotoma. Gum. [1X]i; + 30.4° (c, 0.8 in
CHC1 3).
11fl,13-Dihydro: 8p-Hydroxy-1(10),4-germacradiene-
12,6;14,2-diolide
Ct5H 180 5 M 278.304
Constit. of B. dichotoma. Gum.
(2~,4E,6rx,8~)-form
8-(2-M ethylpropenoyl): Isodeoxyelephantopin
Ct9Hz00 6 M 344.363
C 15H 2P 3 M 250.337 Constit. of E. scaber. Cryst. (CH 2Cl2 jhexane). Mp 150-
(4E,6rx,9P,11Pll)-form [97649-05-3] Herbolide H 1530. [1X] 0 + 188.4° (c, 1.1 in CHC1 3).
Constit. of Artemisia herba-alba. Oil. [1X]i,2 + 179° (c, Govindachari, T.R. eta/, Indian J. Chern., 1970, 8, 762; 1972, 10,
0.69 in CHC1 3). 272 (isol)
Segal, R. eta/, Phytochemistry, 1985, 24, 1381. Kurokawa, T. eta/, Tetrahedron Lett., 1970, 2863 (struct)
McPhail, A.T. eta/, J. Chern. Soc., Perkin Trans. 2, 1972, 1313
(abs config)
11-Hydroxy-1(10),4-germacradien-12,6- Sq-00562 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 263 (isol, struct)
olide de Silva, L.B. eta/, Phytochemistry, 1982, 21, 1173 (iso/)

8-Hydroxy-1(10),4,11(13)-germacratriene- Sq-00564
12,6; 14,9-diolide
0

C 15H 22 0 3 M 250.337
(1(10)E,4E,6P,11rx(Oll))-form
Angeloyl: 8-Deacetoxylaserolide
C20H 280 4 M 332.439
Constit. of Laser trilobum. Cryst. Mp 105-107°. [1X]i?
-138.6°. 0
Holub, M. eta/, Collect. Czech. Chern. Commun., 1970, 35, 284; Ct5Ht 60 5 M 276.288
1985, 50, 1878.
(4E,6rx,8p,9p)-form
8-Hydroxygrazielolide
8-Hydroxy-1(10),4,11(13)-germacratriene- Sq-00563 8-Angeloyl:
12,6;14,2-diolide C20 H 220 6 M 358.390
Constit. of Grazielia intermedia. Gum. [1X]i; -74.SO (c,
0 0.22 in CHC1 3).
8-(2 ,3-Epoxy-2-methylbutanoyl):
C20 H 220 7 M 374.390
-OH (2~,4E,6cx,8cx)-form Constit. of G. intermedia. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1069.
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2045.

1-Hydroxy-4,9,11(13)-germacratrien-12,6- Sq-00565
C 15H 160 5 M 276.288 olide
I> LY 4250000.
OH
(2P,4E,6rx,8rx)-form I
I

~
2-Methylpropenoyl: [29307-03-7]. Deoxyelephantopin
Constit. of Elephantopus scaber and E. carolinianus.
Antitumour principle. Cryst. Mp 198-200°. [1X] 0 -54.6°.
11 ,13-Dihydro, 8-(2-methylpropenoyl): 81X-Hydroxy-1(10),4-
germacradiene-12,6; 14,2-diolide. 11, 13-
Dihydrodeoxyelephantopin 0
C19H 2P 6 M 346.379 C 15H 200 3 M 248.321
Constit. of E. scaber. Cryst. (CHC1 3jpet. ether). Mp (1rx,4E,6P,10(14)E)-form [125290-01-9]
234°. Constit. of Geigeria rigida. Gum.
(2P,4E,6rx,8p)-form Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (iso/, pmr)
8p-Hydroxyblainvilleolide
Constit. of Blainvillea dichotoma. Gum.
8-(2-M ethylbutanoyl):
C20 H 24 0 6 M 360.406
Constit. of B. dichotoma. Gum. [1X]~4 +65.2° (c, 0.62 in
CHC1 3).
8-(3-Methyl-2-butenoyl):

252
2-Hydroxy-1{10),4,11{13)-••. - 8-Hydroxy-1{10),4,11{13)-... Sq-00566 - Sq-00569

2-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00566 3-Ketone: [88675-08-5]. 3-0xo-1(10),4Z,11(13)-

12,6-olide germacratrien-12,6a-olide. Hispanolide
CISH1803 M 246.305
From L. pulverulenta. Cryst. (CHCI 3/Et20). Mp 130-

HO,~ (1(10)E,2a,4E,6a)ofo'm
1310. [aln + 148° (c, 0.47 in CHCI 3).
Ip,JOa-Epoxide: 1,10-Epoxy-3P-hydroxy-4,11(13)-
germacradien-12,6a-olide. I ,10-Epoxy-3-
hydroxygermacrano/ide
0 ClsH 200 4 M 264.321
C1sH2003 M 248.321 From L. pulveru/enta. Cryst. (EtzG). Mp 168-170°. [a]n
- 23.SO (c, 1.8 in CHCI 3).
(l(JO)E,2rx.,4E,6rx.)-form [19888-11-0] Tamaulipin A
Constit. of Ambrosia confertiflora. Cryst. (CHCI 3). Mp Jp,JOa-Epoxide, Ac:
159-160°. [a]n + 171° (c, 1.08 in MeOH). C11H 220 5 M 306.358
From L. pulverulenta. Gum. [a]n -47° (c, 1.7 in
11P,J3-Dihydro: 2a-Hydroxy-1(10)E,4E-germacradiene-
CHCI3).
12,6a-olide. Dihydrotamaulipin A. 2a-Hydroxycostunolide
C15H 220 3 M 250.337 Fischer, N.H. et al, J. Chern. Soc., Chern. Commun., 1967, 1235
(Tamaulipin B)
lsol. from A. confertiflora. Cryst. (EtzG). Mp 119-120°. Akhmedov, I.S. et al, Khim. Prir. Soedin., 1970, 6, 691; Chern.
11P,13-Dihydro, Ac: Cryst. (Et20). Mp 140°. [a]n + 133° Nat. Compd. (Engl. Trans/.), 703 (Artabin)
(c, 0.85 in MeOH). Irwin, M.A. et al, Phytochemistry, 1973, 12, 875 (Novanin)
(l(JO)Z,2rx.,4Z,6rx.)-form [62948-60-1] Tarasov, V.A. eta/, Khim. Prir. Soedin., 1976, 12, 263; 1978, 14,
lsol. from Chrysanthemum poteriifolium. 78; Chern. Nat. Compd. (Engl. Trans/.), 236, 62 (Hanphyllin)
Bohlmann, F. et al, Chern. Ber., 1977, 110, 3572.
(l(JO)Z,2rx.,4Z,6b)-form Abdullaev, U.A. et al, Khim. Prir. Soedin., 1980, 16, 636; Chern.
Constit. of Geigeria rigida. Gum. Nat. Compd. (Engl. Trans/.), 454 (ms)
Fischer, N.H. eta/, Tetrahedron, 1968, 24, 4091 (isol, struct) De Pascual Teresa, J. eta/, Phytochemistry, 1983, 22, 1985.
Bhacca, N.S. et al, J. Chern. Soc., Chern. Commun., 1969, 68 Mata, R. et al, Phytochemistry, 1985, 24, 1515 (cryst struct,
(struct) Hanphyllin)
Bohlmann, F. et al, Phytochemistry, 1977, 16, 137 (isol) Nishimura, K. et al, Chern. Pharm. Bull., 1986, 34, 2518 (Picriside
Witt, M.E. et al, J. Chern. Soc., Perkin Trans. 2, 1978, 204 (cryst C)
struct) Makhmudov, M.K. eta/, Khim. Prir. Soedin., 1989, 25, 775;
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr) Chern. Nat. Compd. (Engl. Trans/.), 675 (cryst struct,
Hanphyllin)
Turdybekov, K.M. et al, Khim. Prir. Soedin., 1989, 25, 781; Chern.
3-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00567 Nat. Compd. (Engl. Trans/.), 662 (cryst struct, Hanphyllin)
12,6-olide ·
7-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00568
12,6-olide
HO'CJ.O
~ 1-7
....--

~
(1(10)E,30!,4E,60!}:form
0
CISH2003 M 248.321
(l(JO)E,3rx.,4E,6rx.)-form [18045-83-5] Tamaulipin B 0
lsol. from Ambrosia confertiflora. Cryst. Mp 140-142°. CisH200 3 M 248.321
[a]~ +99°.
(l(IO)E,4E,6rx.,7rx.)-form
(l(JO)E,Jp,4E,6rx.)-form [60268-40-8] Hanphyllin. 3P- 7-Hydroxycostuno/ide
Hydroxycostunolide. Artabin Constit. of Decachaeta ovatifolia. Cryst. Mp 153° dec.
Constit. of Handelia trichophyl/a, Artemisia spp., Porella
De Luengo, D.H. eta/, Phytochemistry, 1986, 25, 1917.
japonica and others. Cryst. (Me2COjdiisopropyl ether)
or oil. Mp 180°. [aln + 103.8° (c, 2.6 in CHC1 3). Props.
refer to Hanphyllin. Identity of all samples not certain. 8-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00569
Ac: [41743-61-7]. Novanin 12,6-olide
CI7Hn04 M 290.358
Constit. of A. nova. Unstable oil.
0-P-D-Glucopyranoside: [104778-13-4]. Picriside C
C21 H 34P 8 M 410.463 (1(10)E,4E,60!,80!)-form
lsol. from Picris hieracioides var. japonica. Amorph.
powder. [aln +57.1° (c, 0.28 in MeOH).
(l(JO)E,3P,4Z,6rx.)-form [65556-51-6]3-Hydroxygermacrano/ide C1sH2003 M 248.321
Constit. of Tanacetum tanacetiodes. Cryst. (EtzGjpet.
(l(IO)E,4E,6rx.,8rx.)-form
ether). Mp 136-137°. [a]~ -80° (c, 0.2 in CHCI 3). The
name 3-hydroxygermacranolide is confusing. Ac: [24164-12-3]. Tulipinolide
Ac: 3-Acetoxygermacranolide C17H 220 4 M 290.358
Constit. of Liriodendron tulipifera and Artemisia
C17Hn04 M 290.358
Constit. of Leucanthemopsis pulverulenta. Gum. [a]n mexicana. Shows cytotoxic activity. Mp 181° dec. [a]~
-21 o (c, 0.45 in CHCI 3). +249°.
8-0-[[2-[(3,4-Dihydroxy-2-methy/enebutanoyl)oxy]methylJ-4-
hydroxy-2E-butanoy1J: Caudatol

253
9-Hydroxy-1(10),4,11(13)-... - 9-Hydroxy-1(10),4,11(13)-... Sq-00570- Sq-00570

ClSH320 9 M 476.522 C20H 260 5 M 346.422

lsol. from Pericome caudata. From P. senegalensis. Gum. Obt. only as mixt with the
11P,13-Dihydro: [6895-46-1]. 8-Hydroxy-1(10),4- 2-hydroxymethyl isomer below.
germacradien-12,6-o/ide. Mucronin. Balchanolide 8-(2-Hydroxymethyl-2E-butenoyl):
C15H220 3 M 250.337 C20H 260 5 M 346.422
Constit. of Tanacetopsis mucronata and A. balchanorum. From P. senegalensis. See above.
Cryst. (EtOAcjhexane). Mp 154° (132°). [ex]~ +23.7° (c, 8-(4-Hydroxy-2-hydroxymethyl-2E-butenoyl):
0.28 in CHC1 3), [ex]~ + 183° (c, 1.84 in CHC1 3). C20H 260 7 M 378.421
11P,13-Dihydro, Ac: From P. senegalensis. Cryst. Mp 106°. (ex]~ -113° (c,
Ct7Hz..04 M 292.374 0.64 in CHC1 3).
Constit. of yarrow (Achillea millefolium). Cryst. 8-(2,5-Dihydro-5-hydroxy-2-furoyl):
(diisopropyl ether). Mp 125°. [ex]~ + 128.1° (c, 3.8 in C20H240 6 M 360.406
CHC1 3). From P. senega/ensis. Gum.
(1(10)E,4E,6«,8f/)-form [6750-25-0] Eupatolide 8-(3-Furoyl):
Constit. of Eupatorium formosanum and E. cannabinum. C20 H220 5 M 342.391
Antitumour agent. Cryst. (EtOAcjEt20). Mp 187-188°. From P. senegalensis. Gum. (ex]~4 -124° (c, 0.3 in
[ex]~ +20° (c, 0.011 in Me2CO). CHC1 3).
Ac: [24164-13-4]. Epitulipinolide 0-(2,3-Dihydroxy-2-methylbutanoyl): [95653-77-3].
C17H 220 4 M 290.358 Ursiniolide D
lsol. from L. tulipifera. Cryst. (pet. ether). Mp 91-92°. C20H 180 6 M 364.438
[ex]~ + 75° (c, 3.2 in CHC1 3). lsol. from U. anthemoides. Cryst. (Me 2COfhexane). Mp
8-(2-Hydroxymethyl-2E-butenoyl): [70550-00-4]. 119-121°. [ex]~ -199° (c, 0.1 in CHC1 3).
C20H260 5 M 346.422 0-(3-Acetoxy-2-hydroxy-2-methylbutanoyl): 3-
Constit. of E. serotinum. Cryst. (MeOH). Mp 110°. [ex]~ Deacetoxyursinio/ide B
+47.SO (c, 0.12 in CHC1 3). C22 H300 7 M 406.475
8-(2-Acetoxymethyl-2E-butenoyl): [70550-01-5]. From U. anthemoides. Cryst. (Me 2COjhexane). Mp 116-
C22H 180 6 M 388.460 1180. [ex]~ -170° (c, 0.1 in CHC1 3).
Constit. of E. serotinum. Cryst. (MeOH). Mp 162-163°. llochmannova, J. eta/, Collect. Czech. Chern. Commun .• 1961, 26,
[ex]~ +90° (c, 0.14 in CHC1 3). 1826 (Balchanolide)
4ex,5P-Epoxide, 8-tigloyl: [70527-88-7]. Herout, V. eta/, Collect. Czech. Chern. Commun., 1961. 26, 2612
C20H260 5 M 346.422 (Balchanolide)
Doskotch, R.W. eta/, J. Org. Chern., 1970, 35, 1928 (Balchanolide,
Constit. of E. serotinum. Cryst. (MeOH). Mp 134-135°.
Tulipinolide)
(ex]~ -120° (c, 0.15 in CHC1 3).
Brozdz, B. eta/, Collect. Czech. Chern. Commun., 1972, 37, 1546
8-(3-Acetoxy-2-hydroxy-2-methylbutanoyl): [75628-04-5]. 3- (isol)
Deacetoxyursinolide B Lee, K.-H. eta/, J. Pharm. Sci., 1972, 61, 629 (props)
C22H300 7 M 406.475 McPhail, A.P. eta/, J. Chern. Soc., Perkin Trans. 2, 1975, 1798
Isol. from Ursinia. spp. Cryst. (Etpjpet. ether). Mp (cryst struct)
1W. [ex]~ -167° (c, 0.7 in CHC13). Herz, W. eta/, J. Org. Chern., 1979, 44, 2784 (isol)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 847; 1985, 24, 1263
11P,J3-Dihydro, 8-Ac: 11p,J3-Dihydroepitulipinolide (Liacylindrolides)
C17H240 4 M 292.374 Bohlmann, F. eta/, Phytochemistry, 1980, 19, 587 (3-
Constit. of Bartlettina karwinskiana. Oil. Deacetoxyursino/ide B)
11P,13-Epoxide, 8-Ac: 11P,13-Epoxyepitulipinolide Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1637 (isol, esters)
Abduazimov, B. eta/, Khim. Prir. Soedin., 1984, 20, 314
C 17H 220 5 M 306.358
(Mucronin)
From B. karwinskiana. Oil. Kroszczynski, W. eta/, Collect. Czech. Chern. Commun., 1985, SO,
0-[[2-(2-Hydroxymethyl-2E-butenoyloxy)methyl]-2E- 94 (Ursiniolides)
butenoyl]: [72055-91-5]. Liacylindrolide Gao, F. eta/, Phytochemistry, 1986, 25, 1231 (isol)
ClSH320 7 M 444.524 Jolad, S.D. eta/, Phytochemistry, 1990, 29, 3024 (Caudatol)
Constit. of Liatris cylindracea. Oil. (ex]~4 + 22.9° (c, 0.8
in CHC1 3). 9-Hydroxy-1(1 0),4, 11 (13)-germacratrien- Sq-00570
0-([2-(2-Hydroxymethyl-2Z-butenoyloxy)methyl]-2E- 12,6-olide
butenoyl]: 2nZ-Liacylindrolide
ClSH320 7 M 444.524
Constit. of Eupatoriastrum nelsonii. Oil.
0-[[4-Hydroxy-2-[2-hydroxymethyl-2E-butenoyloxy]methyl]-
2E-butenoyl]: 4' ~Hydroxyliacylindrolide
ClSH310 8 M 460.523
Isol. from E. nelsonii. Cryst. (EtpjCHC13). Mp 92°.
0-[[4-Hydroxy-2-[2-hydroxymethyl-2Z-butenoyloxy]methyl]-
2E-butenoyl]: 4' -Hydroxy-2nZ-liacylindrolide C15H200 3 M 248.321
ClSH320 8 M 460.523 (1(10)E,4E,6«,9p)-form [68715-67-3] Haageanolide. 9P-
From E. nelsonii. Cryst. (Et20/CHC1 3). Mp 95°. Hydroxycostunolide
(I(IO)E,4E,6P,Bp)-form [88198-94-1] Constit. of Zinnia haageana and lnula spp. Amorph.
Constit. of Pegolettia senegalensis, occurring with powder or oil. [exJn +38.6° (c, 1 in CHC1 3).
various esters. Cryst. Mp 130°. [ex]~ -90° (c, 0.4 in Ac: [64562-23-8]. Herbolide A
. CHC1 3). Ct7H 240 4 M 292.374
8-(4-Hydroxy-2-methyl-2E-butenoyl):

254
14-Hydroxy-1(10),4,11(13)-... - 8-Hydroxy-1(10),4,11(13)-... Sq-00571 - Sq-00573

Constit. of Artemisia herba-alba. Cryst. (EtOH). Mp C 17H1:z04 M 290.358

162-163°, Mp 196-197°. [a]i,S +84° (c, 0.2 in CHC1 3). Constit. of Magnolia sieboldii and Dicoma schinzii.
Mp of 162-163° refers to Herbolide A, Mp 196-197° Cryst.(Et20/2-propanol). Mp 100°.
refers to acetate of Haageanolide. 2-Methylpropanoyl:
IP,JOa-Epoxide: IP,10a-Epoxy-9P-hydroxy-4,11(13)- c.,Hu04 M 318.412
germacradien-12,6a-o/ide. 1P,10rx.-Epoxyluuzgeanolide lsol. from Fitchia speciosa. Gum.
C 15H100 4 M 264.321 2-Methylbutanoyl:
Constit. of/. hetero/epsis. Gum. [a]i;' + 7.SO (c, 0.24 in C10H 180 4 M 332.439
CHC13). lsol. from F. speciosa. Gum.
Ip,JOa-Epo~ide, Ac: [64562-24-9]. Herbolide B np,13-Dihydro, 0-P-D-glucopyranoside: [94356-11-3].
C 17H1,.0s M 308.374 Ixerin H
Constit. of A. herba-a/ba. Cryst. (EtOH). Mp 209° dec. C11 H 320 8 M 412.479
[a]i,S +23° (c, 0.4 in EtOH). Constit. of Ixeris tamagawaensis. Amorph. [a]i,S +43.6°
4,5p-Epoxide, Ac: [64562-25-0]. Herbolide C (c, 0.51 in MeOH).
C 17H140 5 M 308.374 (1(10)E,4E,6rx.)-form
Constit. of A. herba-a/ba. Cryst. (EtOH/pet. ether). Mp
IS-Carboxylic acid: [126721-45-7]. 1(10)E,4E,11(13)-
197-198°. [a]i,S -26° ( c, 0.1 in EtOH).
Ger1111lcratrien-11,6rx.-olid-15-oic acid
IIP,J3-Dihydro, 0-P-v-g/ucopyranoside: [126005-75-2]. C 15H 180 4 M 262.305
Plucheoside A lsol. from Arctotis revoluta.
C11H 310 8 M 412.479
Bohlmann, F. et al, Phytochemistry, 1977, 16, 1832; 1980, 19,
Constit. of Pluchea indica. Amorph. powder. [1X]~4 1141.
+21.6° (c, 1.16 in MeOH). Asada, H. et al, Chern. Pharm. Bull., 1984, 32, 3403 (Ixerin H)
Segal, R. et al, Phytochemistry, 1977, 16, 1237. Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 240
Kisrel, W., Phytochemistry, 1978, 17, 1059 (iso/) (Cronquistianthusic acid)
Jones, P.O. et-al, Acta Crystallogr., Sect. B, 1979, 35, 1273 (cryst Nishimura, K. et al, Chern. Pharm. Bull., 1986, 34, 2518 (Picriside
struct) B)
Bohlmann, F. et al, Phytochemistry, !982, 21, 1166, 1357 (isol, Zdero, C. et al, Phytochemistry, 1990, 29, 183 (isol, pmr)
deriv) Tsichritzis, F. et al, Phytochemistry, 1990, 29, 195 (Germacratrien-
Takahashi, T. et al, Tetrahedron, 1987, 43, 5499 (synth) !2,6-olid-15-oic acid)
Uchiyama, T. et al, Phytochemistry, !989, 28, 3369 (Plucheoside A)
8-Hyd.roxy-1(10),4,11(13)-germacratrien- Sq-00573
14-Hyd.roxy-1(10),4,11 (13)-germacratrien- Sq-00571 12,6-olid-14-oic acid
12,6-olide
COOH

0-oto~-
~ (I(IO)E,4E,6a,8P)cfo'm

C 15H100 3 M 248.321 0
(1(10)E,4E,6rx.)-form [71748-67-9] Soulangianolide A ClsH180 5 M 278.304
Constit. of Clibadium surinamense and of a Magnolia sp. (1(10)E,4E,6rx.,8f/)-form
Cryst. Mp 90-91°, Mp 1399 dec. [1X]n +23° (c, 0.32 in
MeOH). The two isolates have not been compared and 3S-Acetoxy-2R-hydroxy-2-methylbutanoy/: [60295-56-9].
the reported Mp's differ considerably. Melampolidin
C23H 300 9 M 450.485
Czerson, H. et al, Phytochemistry, 1979, 18, 257 (iso/) Constit. of Melampodium /eucanthum. Gum.
El-Feraly, F.S., Phytochemistry, 1983, 22, 2239 (iso/)
(1(10)Z,4E,6rx./l/l)-form
Angeloyl: [79435-34-0]. Grazie/ia acid
15-Hyd.roxy-1(10),4,11(13)-germacratrien,- Sq-00572
C10H 1P 6 M 360.406
12,6-olide Constit. of Grazielia intermedia. Gum.

m.
(1(10)Z,4E,6rx.,8~)-form
2-Methy/butanoy/: [54927-90-1]. Germanin A

HOHI 1--T 0
(1(10)E,4Z,6a}:form C10H 260 6 M 362.422
Constit. of lnula germanica. Cryst. Mp 150-153°. [1X]n
+17.8°.
Konova1ova, O.A. et al, Khim. Prir. Soedin., 1974, 10, 578; Chern.
C15H 100 3 M 248.321 Nat. Compd. (Engl. Trans/.), 59! (Germanin A)
(1(10)E,4Z,6rx.)-form [65400-30-8] 15-Hydroxycostuno/ide. 8- Fischer, N.H. et al, J. Org. Chern., 1976, 41, 3956 (Melampolidin)
Deoxysa/onitenolide Bohlmann, F. et al, Phytochemistry, 1981, 20, 1069 (Grazielia acid)
Constit. of Platycarpha glomerata. Cryst. (Etpjpet.
ether). Mp 102°. [a]i;' +93° (c, 0.22 in CHCI 3).
0-P-v-G/ucopyranoside: [104778-12-3]. Picriside B
C11 H:34,08 M 410.463
Constit. of Picris hieracioides var. japonica. Amorph.
powder. [1X]n +43.1° (c, 1.01 in MeOH).
Ac: 15-Acetoxycostuno/ide

255
8-Hydroxy-1(10),4,11(13)-... - 15-Hydroxy-14-oxo-1(10),4,11(13)-... Sq-00574 - Sq-00578

8-Hydroxy-1(1 0),4,11(13)-germacratrien- Sq-00574 8-Hydroxy-14-oxo-1(10),4,11(13)- Sq-00577

12,6-olid-15-oic acid germacratrien-12,6-olide

C15H 180 5
%
M 278.304
0
~ (I(I0)£,4£,6a,8~)-fo""
0
(l(JO)E,4Z,6«,8«)-form C 15H 180 4 M 262.305
0-Ange/oy/: 8-Angeloyloxycronquistanthusic acid (l(JO)E,4E,6rr.,8p)-form
C 20H 140 6 M 360.406 Constit. of Helianthus maximiliani.
Occurs in Cronquistianthus chachapoyensis. Oil. [ac]i: 2-Methy/propanoy/: [75744-65-9]. Glabratolide
+ 133° (c, 0.8 in CHC13). Opt. rotn. refers to a mixt. C19HuOs M 332.396
with the tiglate. Cronquistanthusic acid is not known. Constit. of Acanthospermum glabratum.
0- Tigloyl: 8- Tigloyloxycronquistanthusic acid (1(10)Z,4E,6p,8fJ)-form
C20H 140 6 M 360.406
2-Methy/butanoyl:
Occurs in C. chachapoyensis.
C20H 260 5 M 346.422
Bohlmann, F. et a/, Justus Liebigs Ann. Chern., 1984, 240. Constit. of Wunderlichia mirabilis. Oil. [1X]i: -138° (c,
0.5 in CHC1 3).
3-Hydroxy-1(10)-germacren-12,6-olide Sq-00575 (1(10)E,4E,6p,8fJ)-form
2-Methylbutanoyl:
C20H 260 5 M 346.422
Constit. of W. mirabilis. Oil. [1X]n + 176° (c, 0.2 in
HO' CHC13).
Tigloyl: [80368-05-4]. Wunderolide
C20H 140 5 M 344.407
C15H 140 3 M 252.353 lsol. from W. mirabi/is.
(l(JO)E,3rr.,4PH,6rr.,llrr.H)-form [17909-94-3] Hydroxypeleno/ide (l(JO)E,4E,6rx.,8rx.)-form
Constit. of Artemisia absinthium. Cryst. Mp 108° (98°). 11fi,13-Dihydro: 8rx.-Hydroxy-14-oxo-l(JO)E,4E-
[1X]n -4lo. germacradien-12 ,6rx.-olide
3-Ketone: [17909-92-1]. 3-0xo-1(10)-germacren-12,6-o/ide. C1sHw04 M 264.321
Ketopelenolide a. Oxopelenolide a Constit. of Artemisia oliveriana. Needles (EtpjMeOH).
C1sH220 3 M 250.337 Mp 165-168°. [1X]i: -9° (c, 1.84 in CHC13).
From A. absinthium. Cryst. Mp 114°. Saleh, A.A. et al, J. Chern. Soc., Perkin Trans. 1, 1980, 1090
(l(JO)E,4rx.H,6rr.,ll «H)-form (Glabratolide)
Bohlmann, F. eta/, Justus Liebigs Ann. Chem., 1984, 228.
3-Ketone: Ketopelenolide b. Oxope/enolide b Stewart, E. et al, Phytochemistry, 1985, 24, 2733.
C15H 110 3 M 250.337 Sanz, J.F. et al, Phytochemistry, 1990, 29, 2919.
From A. absinthium. Cryst. Mp 172°.
Suchy, M. et a/, Collect. Czech. Chern. Commun., 1967, 32, 3917. 15-Hydroxy-14-oxo-1(10),4,11(13)- Sq-00578
Bates, R.B. et a/, J. Org. Chem., 1970, 35, 3960.
germacratrien-12,6-olide
13-Hydroxy-3-oxo-1(10),7(11)- Sq-00576 14
CHO
germacradien-12,6-olide

0%~ CHPH
I
I 0
I
0
0 ClsH180 4 M 262.305
C 15H 200 4 M 264.321 (1(10)E,4Z,6rr.)-form
(l(JO)E,4pH,6rr.)-form [128366-59-6] 8-Desoxyurospermal A
Constit. of Ajania achil/eoides. Amorph. [ac]i: + 144° (c, Isol. from Ixeris tamagawaensis. Amorph. powder. [ac]i,3
7.58 in CHC1 3). -40.6° (c, 0.32 in CHC1 3).
Ac: [128366-60-9]. 15-0-P-D-Giucopyranoside: [91486-97-4]. Ixerin B
C 17H 220 5 M 306.358 C11 H180 9 M 424.447
Constit. of A. achilleoides. Gum. Constit. of I. tamagawaensis. Amorph. [1Xji,3 - -11.9° (c,
Zdero, C. et al, Phytochemistry, 1990, 29, 1585 (iso/, prnr) 2.0 in MeOH).
15-0-(6-0-p- Hydroxyphenylacetyl-P-D-glucopyranoside ):
[91486-98-5]. Ixerin C
C19H 340n M 558.581
Constit. of I. tamagawaensis. Amorph. [1X]i,3 + 3.8° (c,
0.40 in MeOH).

256
8-Hydroxy-3-oxo-1(10)-germacren-... - 1,3,8,15-Tetrahydroxy-4,9,11(13)-... Sq-00579 - Sq-00584

15-0-(2-0-p-Hydroxyphenylacetyl-P-n-glucopyranoside): From P. senegalensis. Cryst. Mp 137-138°. [1X]i;' -190°

[93236-47-6]. Ixerin G (c, O.o7 in CHCI3).
C2.,H340 11 M 558.581 (1(10)E,4E,6p,71X)-form
Constit. of I. tamagawaensis. Amorph. powder. [1X]i,2 From P. senegalensis. Gum. [1X]i;' + 149° (c, 0.14 in
-15.1° (c, 0.11 in MeOH). CHCI 3).
JJp,JJ-Dihydro: [91486-96-3]. 15-Hydroxy-14-oxo-1(10),4- Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1637.
germacradien-12,61X-olide. lxerin A
C 15H 200 4 M 264.321
Iso1 from I. tamagawaensis. Prisms (MeOH). Mp 134- Parthenolidine Sq-00582
1380. [1X]~ -54.6° (c, 0.18 in CHCI 3).
11P,J3-Dihydro,O-P-n-glucopyranoside: [94356-09-9]. Ixerin
J
C21 H 300 9 M 426.463
Constit. of I. tamagawaensis. Prisms. Mp 113.5-115.SO.
[1X]i;5 -54.0° (c, 0.68 in MeOH).
Asada, H. et a/, Chern. Pharm. Bull., 1984, 32, 1724, 3036, 3403. C15H 23N03 M 265.352
N-Ac: [119766-96-0]. N-Acetylparthenolidine
8-Hydroxy-3-oxo-1 (1 0)-germacren-12,6- Sq-00579 C 17H 25N04 M 307.389

0%/0H
olide Constit. of Michelia rajaniana (Magnoliaceae). Oil. [1X]~4
+ 23° (c, 0.67 in CHCI 3).
Ruangrungsi, N. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 1220 (isol,
pmr, cmr)

I
I
I
0 3,8,9,10-Tetrahydroxy-4,11(13)- Sq-00583
0 germacradien-12,6-olide
C 15H 220 4 M 266.336
(1(10)E,4PH,6rx,8rx,llrxH)-form
Deacetylargentiolide B
Constit. of Artemisia argentea. Cryst. (Et20). Mp 183°.
[1X]n + 142.6° (c, 0.82 in CHCI 3).
Ac: [75911-34-1]. Argentiolide B
C 17H 240 5 M 308.374
Constit. of A. argentea. Cryst. (Et20). Mp 177°. C 15H 220 6 M 298.335
El-Emary, N.A. eta/, Phytochemistry, 1980, 19, 845; 1987, 26, 314. (3P,4Z,6rx,8P,91X.,l01X.)-form [88320-79-0] Brasiloide
8-(2-Methylbutanoyl), 9-Ac:
8-0xo-1(10),4,7(11 )-germacratrien-12,6- Sq-00580 C22 H 3z08 M 424.490
olide Constit. of Brasilia sickii. Cryst. Mp 208°. [1X]i;' -37° (c,
0.2 in CHCI 3). C-8 and C-9 ester groups may be
interchanged.
8-(2-Methylbutanoyl), 3,9-di-Ac:
C24H 340 9 M 466.527
From B. sickii. Cryst. Mp 158°. [1X]i;' -87° (c, 0.1 in
CHCI 3). C-8 and C-9 ester groups may be interchanged.
8-(2-Methylpropanoyl), 3,9-di-Ac:
C15H 180 3 M 246.305 C23 H 320 9 M 452.500
(1(10)E,4E,6fl)-form [70224-78-1] From B. sickii. Cryst. Mp 19ZO. [1X]i;' -58° (c, 0.08 in
Constit. of Wunderlichia mirabilis. Cryst. (hexane). Mp CHC1 3). C-8 and C-9 ester group may be interchanged.
116-118°.
Bohlmann, F. et a/, Phytochemistry, 1983, 22, 1213.
Vichnewski, W. eta/, J. Org. Chern., 1979, 44, 2575.
1,3,8,15-Tetrahydroxy-4,9,11(13)- Sq-00584
8-0xo-1(1 0),4,11(13)-germacratrien-12,6- Sq-00581 germacratrien-12,6-olide
olide
OH

~"
I

(I(IO)E,4E,6~)-form
OH
0
cl5H 180, M 246.305
(1(10)E,4E,6fl)-form
Constit. of Pegolettia senegalensis. Cryst. (EtzOjpet. C 15H 200 6 M 296.319
ether). Mp 98°. [1X]i;' -3J40 (c, 0.5 in CHCI 3). (lrx,3P,4Z,6rx,8P,9Z)-form
11P,l3-Dihydro: 8-0xo-1(10),4-germacradien-12,6P-olide 8-(2S-Methylbutanoyl), 3-Ac: [66922-25-6]. Eurecurl/in
C 15H 200 3 M 248.321

257
2,4,8,13-Tetrahydroxy-1(10),5,7(11)-... - 3,8,9,10-Tetrahydroxy-1-oxo-4,11(3)-... Sq-00585 - Sq-00588

C22H 31P 8 M 422.474 14-Aldehyde, 8-(2-methylpropenoyl), 9-Ac: [72704-05-3].

Constit. of Eupatorium recurvans. Cryst. Orienta/ide
(EtOAcfMeOH). Mp 183-185°. [aJn +42.3° (c, 3.01 in C21 H 240 8 M 404.416
CHC1 3). Isol. from Siegesbeckia orientalis. Noncryst. [a]i,S +41.2°
Herz, W. et al, J. Org. Chern., 1978, 43, 3559. (c, 0.034 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 625.
Baruah, R.N. et al, Phytochemistry, 1979, 18, 991 (Orienta/ide)
2,4,8,13-Tetrahydroxy-1(10),5,7(11)- Sq-00585 Seaman, F.C. et al, Phytochemistry, 1979, 18, 1065 (Longipin)
germacratrien-12,6-olide
HO 2,8,9,15-Tetrahydroxy-1(10),4,11(13)- Sq-00587
germacratrien-12,6-olid-14-oic acid
HOOC

0 HO
C 15H 200 4 M 264.321
(1(10)E,2P,4a.,5Z,8a.)-form
8-(2-Methylpropenoyl), 2-Ac: [76010-19-0]. lsorolandrolide HOH2 C 0
C21 H 260 8 M 406.432
Constit. of Rolandra fruticosa. Gum. CtsHt80 8 M 326.302
8-(2-Methylpropenoyl), 0 13 -Et, 2-Ac: [76010-18-9]. (1(10)E,2P,4E,6a.,8p,9fJ)-form
Ethoxyisorolandrolide 8,9-Bis(2-methylpropenoyl), Me ester: [84507-59-5].
C23H 300 8 M 434.485 Me/rosin A
Constit. of R. fruticosa. Noncryst. The name C24 H 28 0 10 M 476.479
ethoxyisoro1androlide is not strictly correct. Constit. of Melampodium rosei. Cryst. Mp 159-161°.
Herz, W. et al, J. Org. Chern., 1981, 46, 761 (isol) 8-(2-Methylpropanoyl), 9-(2-methylpropenoyl), Me ester:
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1937 (struct) [88099-90-5]. Me/rosin B
C24H 300 10 M 478.495
8,9, 14,15-Tetrahydroxy-1(1 0),4, 11 (13)- Sq-00586 Constit. of M. rosei. Gum.
germacratrien-12,6-olide 8-Angeloyl, 9-Ac, Me ester: [68024-36-2]. Melcanthin B
C23 H 280 10 M 464.468
Isol. from M. leucanthum. Cryst. (CHC1 3fdiisopropyl
ether). Mp 83-84°.
8-(2-Methylpropanoyl), 9-Ac, Me ester: [68024-39-5].
Melcanthin C
C22 H 280 10 M 452.457
From M. leucanthum. Gum.
8,9-Bis(2-methylpropanoyl), Me ester: [84507-60-8].
Longicornin A
C24H 320 10 M 480.511
C 15H 200 6 M 296.319 FromM. longicorne. Cryst. (EtOAc). Mp 145-147°.
(1(10)E,4Z,6a.,8P,9a.)-form 8-(2-Methy/propanoyl), 9-(2-methy/butanoyl), Me ester:
9-Ac, 8-(2-methylbutanoyl): (56679-24-4]. 8,9,14,15- [89900-55-0]. Longicornin C
Tetrahydroxyacanthospermolide C25 H 340 10 M 494.538
C22H 300 8 M 422.474 From M. longicorne. Gum.
Constit. of Acanthospermum hispidum. Oil. [a]~ -32° (c, Fischer, N.H. eta/, J. Org. Chern., 1978, 43, 4984 (Melcanthins)
0.5 in Cl:lC1 3). Fischer, N.H. eta/, J. Chern. Soc., Chern. Commun., 1982, 1243
14-Aldehyde, 8-(2-methylbutanoyl): [72023-19-9]. (Me/rosin A, Longicornin A)
C20H 260 7 M 378.421 Olivier, E.J. eta/, Phytochemistry, 1983, 22, 1453 (Me/rosin B)
Constit. of A. hispidum. Oil.
14-Aldehyde, 9-hexadecanoyl, 8-(2-methylbutanoyl): [72023- 3,8,9,10-Tetrahydroxy-1-oxo-4,11(3)- Sq-00588
21-3]. germacradien-12,6-olide
C36H 56 0 8 M 616.834
Constit. of A. hispidum. Oil.
14-Aldehyde, 9-octadecanoyl, 8-(2-methylbutanoyl): [72023-
22-4].
C38 H 600 8 M 644.887
Constit. of A. hispidum. Oil.
14-Aldehyde, 9-(9,12-octadecadienoyl), 8-(2-methylbutanoyl):
[72023-23-5].
C38 H 560 8 M 640.856 C 15H 200 7 M 312.319
Constit. of A. hispidum. Oil. (3a.,4E,6a.,8p,9p,JOfJ)-form
14-Aldehyde, 9-octadecatrienoyl, 8-(2-methylbutanoyl): 8-Angeloyl: [89355-51-1].
[72023-24-6]. C20 H 260 8 M 394.421
C38H 540 8 M 638.840
Constit. of A. hispidum. Oil.

258
4,5,8,9-Tetrahydroxy-3-oxo-1(10) ... - 1,3,8-Trihydroxy-4,9,11(13)-... Sq-00589 - Sq-00593

Constit. of Trichogonia salviaefolia. Oil. [IX]~ +31° (c, Constit. of E. cordifolia. Cryst. (MeOH). Mp 225-227°
0.7 in CHC1 3). dec.
8-Angeloyl, 9-Ac: [89355-52-2]. Rustaiyan, A. et al, Phytochemistry, 1980, 19, 1230 (isol)
C 22H:zs09 M 436.458 Begley, M.J. et al, J. Chern. Soc., Perkin Trans. 1, 1981, 2702;
Isol. from T. salviaefolia. Oil. 1984, 819 (isol, cryst struct)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162.
3,8,10-Trihydroxy-4,11(13)-germacradien- Sq-00592
4,5,8,9-Tetrahydroxy-3-oxo-1(10),11(13)- Sq-00589 12,6-olide
germacradien-12,6-olide

r0oH
OH

0~
HOHO 0 0
C 1 ~H 22 0~
HOM)=

M 282.336
0

C 1 ~H 20 0 7 M 312.319
(3P,4Z,6rx.,BP,10rx.)-form
(1(10)E,4rx.,5p,6rx.,Bp,9fl)-form
8-Angeloyl:
8-(2-Methylpropenoyl): [89355-59-9]. C 20 H:zs06 M 364.438
C 19H 240 8 M 380.394 Constit. of Helianthus rnaxirniliana and H. niveus. Cryst.
Constit. of Trichogenia hirtifolia. Oil. (CHC1 3jhexane). Mp 158-159° (88-89°). [1X]n -50.7° (c,
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162. 0.51 in MeOH).
8-(2-Methylpropanoyl):
3,8,9,10-Tetrahydroxy-1-oxo-11(13)- Sq-00590 C 19H 280 6 M 352.427
germacren-12,6-olide Constit. of Syncretocarpus sericens. Cryst. (EtzO). Mp
164°. [IX]~ -107° (c, 0.71 in CHC1 3).
Ohno, N. et al, Phytochemistry, 1980, 19, 609 (angelate)
Herz, W. et al, Phytochemistry, 1981, 20, 93 (angelate)
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1288 (isobutyrate)

1,3,8-Trihydroxy-4,9,11(13)- Sq-00593
germacratrien-12,6-olide
C 1 ~H 22 0 7 M 314.335
(3rx.,4rx.H,6rx.,8P,9rx.,10fl)-form
8,9-Dihydroxyternifolin
8-Angeloyl, 9-Ac: BP-Angeloyloxy-91X-acetoxyternifolin
C 21H 300 9 M 438.474
Constit. of Calea ternifolia. Glass.
8-Angeloyl, 9-(2-rnethylbutanoyl):
C 25H 360 9 M 480.554 C 22 H:zs07 M 404.459
Constit. of C. ternifolia. Cryst. (Et20). Mp 55-60°. (1«,3P,4Z,6rx.,Bp,9Z)-form
Lee, 1.-Y. et al, Phytochemistry, 1982, 21, 2313. 8-Angeloyl, 3-Ac: [33854-15-8]. Eupacunin
C 22 H 280 7 M 404.459
1,10;2,3;4,15-Triepoxy-5,8-dihydroxy- Sq-00591 Constit. of Eupatorium cuneifoliurn. Shows anti1eukaernic
11(13)-germacren-12,6-olide props. Needles (MeOH/EtzO). Mp 166-167°. [1X]i,6 +55°
(c, 1.2 in Me2 CO).
0 8-0-(2,3-Epoxy-2-rnethylbutanoyl), 3-Ac: [33853-88-2].
' Eupacunoxin
C21H 280 8 M 420.458
Constit. of E. cuneifoliurn. Needles (EtzO). Mp 171-172°.
[1X]i,6 -209° (c, 1.0 in Me 2CO).
15-Hydroxy, 8-angeloy/, 3-Ac: [79491-59-1]. Eupacunolin
C22 H:zs08 M 420.458
0 Isol. from E. cuneifoliurn. Needles
Ct~Ht 8 0 7 M 310.303 (Me2COjMeOHjCHC1 3). Mp 164-165°. [1X]i,6 +46° (c,
(1P,2«,3«,4P,5p,6rx.,Brx.,l Orx. )-form 1.02 in Me 2CO).
8-(2-Methylpropenoyl): [91161-83-0]. Cordifolia 31 [39152-57-3]
C 19H 220 8 M 378.378 Kupchan, S.M. et al, J. Org. Chern., 1973, 38, 2189.
Constit. of Erlangea cordifolia. Cryst. (MeOH). Mp 246-
2470.
8-Angeloyl: Cordifene oxide
CwH 240 8 M 392.405

259
1,3,8-Trihydroxy-4,10(14),11(13)-... - 2,8,9-Trihydroxy-1(10),4,11(13)-... Sq-00594 - Sq-00597

1,3,8-Trihydroxy-4,10(14),11(13)- Sq-00594 Constit. of A. afra. Afrag1auco1ide is unknown.

germacratrien-12,6-olide 1,3-Di-Ac: Achillolide B
Ct9H2407 M 364.394
OH I sol. from Achillea fragrantissima. N oncryst. Itx]i; - 1.4°
(c,0.5 in EtOH).
1-Ketone: [126025-04-5]. 3fi,13-Dihydroxy-1-oxo-
4, 7(11),!0(14)-germacratrien-12,6tx-olide. 1,13-Bis-0-
desacetyl-1-oxoafraglaucolide
C 1 ~H 18 0~ M 278.304
lsol. from Achillea fragrantissima. Oil.
1-Ketone, 3-Ac: [126025-03-4].
C 1 ~H 20 0~ M 280.320 C 17H 200 6 M 320.341
(1P,3P,4Z,6rx.,8f/)-form Isol. from A. fragrantissima. Oil.
8-Angeloyl: [103001-38-3]. Jamaicolide C 1-Ketone, di-Ac: [115367-46-9]. Oxoafraglaucolide
C 20H 21,06 M 362.422 C19H 220 7 M 362.379
Constit. of Calea jamaicensis. Gum. From A. fragrantissima. Oil.
8- Tigloyl: [97233-10-8]. Calbertolide C (lp,3p,4E,6rx.)-form
C 20H 21,06 M 362.422 3-Ac: 13-Desacetyl-1P-hydroxyafraglaucolide
Constit. of C. berteriana. Gum. C 17H 220 6 M 322.357
Ober, A.G. eta/, Phytochemistry, 1985, 24, 1743; 1986, 25, 877. Constit. of A. judaica. Oil.
3,13-Di-Ac: [115346-39-9]. 1P-Hydroxyafraglaucolide
1,3,13-Trihydroxy-4,7(11),9- Sq-00595 C19H240 7 M 364.394
germacratrien-12,6-olide Constit. of A. afra.
(3p,4E,6f/)-form
1-Ketone: 3fi,13-Dihydroxy-1-oxo-4,7(11),10(14)-
germacratrien-12,6fi-olide. Achillolide A
C 17H 200 6 M 320.341
Constit. of A. fragrantissima. Cryst.(Me 2CO jpet.ether).
Mp 144-145°. [tx]i; -37.4° (c, 0.5 in EtOH).
[115346-35-5]
S,ega1, R. eta/, Tetrahedron, 1987, 43, 4125 (Achillolides)
Khafagy, S.M. eta/, Phytochemistry, 1988, 27, 1125 (lsol)
C 1 ~H 20 0~ M 280.320 Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1129 (isol)
Abde1-Mogib, M. eta/, Phytochemistry, 1989, 28, 3528 (isol, pmr)
(lrx.,3P,4E,9Z)-form
3-Ac: [115338-11-9]. 13-Desacetyl-1P-
hydroxyisoafraglaucolide 2,8,9-Trihydroxy-1(10),4,11(13)- Sq-00597
C 17H 22 0 6 M 322.357 germacratrien-12,6-olide
Constit. of Artemisia judaica. Cryst. Mp 207°. [tx]i;l + 52°
(c, 0.25 in CHC1 3).
3,13-Di-Ac: [115346-38-8]. 1rx.-Hydroxyisoafraglaucolide
C19H 240 7 M 364.394
Constit. of A. afra. Isoafraglauco1ide is currently
unknown.
[115346-34-4]
Khafagy, S.M. eta/, Phytochemistry, 1988, 27, 1125 (isol) C 15H 200 5 M 280.320
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1129 (isol)
(1(10)E,2p,4E,6rx.,8rx.,9f/)-form
8-Angeloyl: [72065-36-2]. Montafrusin A
1,3,13-Trihydroxy-4,7(11),10(14)- Sq-00596 C20H 260 6 M 362.422
germacratrien-12,6-olide Constit. of Montanoa frutescens. Cryst. (EtOAcjCHC1 3).
Mp 184-186°.
OH
I 8-(3-Methyl-2-butenoyl): [102607-36-3]. Montafrusin B
C20 H 260 6 M 362.422
(1cx,3~,4E,6cx)-form From M.frutescens. Cryst. (Et20). Mp 175-176°. [txln
+23.2°.
(1(10)E,2p,4E,6rx.,81;)-form
9-Ketone: 2P,91;-Dihydroxy-8-oxo-1(10),4,11(13)-
0 germacratrien-12,6rx.-olide
C 1 ~H 20 0~ M 280.320 C 15H 180 5 M 278.304
(1rx.,3P,4E,6rx.)-form Isol. from Tanacetum vulgare. Oil.
3-Ac: [115334-66-2]. 13-Desacetyl-1rx.-hydroxyafraglaucolide Quijano, L. eta/, Phytochemistry, 1979, 18, 843 (Montafrusin A)
C 17H 220 6 M 322.357 Quijano, L. eta/, Phytochemistry, 1986, 25, 695 (Montafrusin B,
cryst struct)
Constit. of Artemisia judaica.
Chandra, A. eta/, Phytochemistry, 1987, 26, 1463 (ketone)
3,13-Di-Ac: [115367-47-0]. 1rx.-Hydroxyafraglaucolide
C19H240 7 M 364.394

260
2,8,13-Trihydroxy-1(10),4,7(11)-... - 3,8,10-Trihydroxy-1,4,11(13)-... Sq-00598 - Sq-00602

2,8,13-Trihydroxy-1(10),4,7(11 )- Sq-00598 C20H 260 6 M 362.422

germacratrien-12,6-olide Constit. of C. chachapoyensis. Cryst. (EtzOjpet.
ether)(as di-Ac). Mp 112° (di-Ac).
8-Tigloy/:
C20H 260 6 M 362.422
Constit. of C. chachapoyensis. Cryst. (Et20jpet.
ether)(as di-Ac). Mp 109° (di-Ac). [ex]i;' -153° (c, 0.04 in
CHC1 3)(di-Ac).
Bohlmann, F. et a/, Justus Liebigs Ann. Chern., 1984, 240.
CtsH2005 M 280.320
(l(JO)E,2rt.,4E,6rt.,8rt.)-form 3,8,9-Trihydroxy-1(10),4,11(13)- Sq-00601
Tri-Ac: germacratrien-12,6-olide
C21 H 260 8 M 406.432
Constit. of Vernonia cotoneaster. Gum. [ex]~4 -81° (c,
0.41 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 695.

2,8,14-Trihydroxy-1(10),4,11(13)- Sq-00599
germacratrien-12,6-olide
0
HO,
(1(10)E,3ME,6cx,8P,9P)-form
C21 H 280 8 M 420.458
(l(JO)E,3P,4E,6rt.,8P,9fl)-form
0 8-Tig/oy/, 3-Ac:
C22 H 280 7 M 404.459
CtsH200s M 280.320
Constit. of Lasiolaena santosii. Cryst. (EtzO). Mp 207.SO.
(l(JO)Z,2rt.,4E,6rt.,8/l)-form [1X]i;' + 130.4° (c, 1.5 in CHC1 3).
2ex, 14-Dihydroxyeupatolide
(J(JO)Z,3P,4Z,6rt.,BP,9fl)-form
8-Angeloyl, 2-Ac:
C21H 280 7 M 404.459 8-Ange/oy/, 3-Ac: [33853-87-1]. Eupatocunin
Constit. of Tithonia rotundifolia. Gum. [ex]i;' +65.4° (c, C22H 280 7 M 404.459
0.3 in CHC1 3). !sol. from Eupatorium cuneifolium. Cytotoxic agent.
Prisms (MeOHjEtzO). Mp 163-164°. [ex]i,S -129° (c, 1.36
8-(2-Methylpropenoyl): Eriofertopin in Me 2CO).
Ct,H1•.06 M 348.395
Constit. of Eriophyllum confertifiorum. Shows 8-0-(2,3-Epoxy-2-methylbutanoyl), 3-Ac: [39204-36-9].
antileukaemic props. Foam. [ex]i;1 + 89° (c, 0.9 in Eupatocunoxin
CHC1 3). C22 H 280 8 M 420.458
Constit. of E. cuneifolium. Cytotoxic. Needles (Me 2CO).
8-(2-Methylpropenoyl), 2-Ac: Mp 200-201°. [1X]~ -209° (c, 1 in Me 2CO).
C 21 H 260 7 M 390.432
Constit. of E. confertifiorum. Foam. [ex]~ + 29° (c, 0.83 (l(JO)E,3rt.,4Z,6rt.,8rt.,9/l)-form
in CHC13). 8-Ange/oy/: [85526-58-5]. Zoapatanolide A
Kupchan, S.M. et a/, Phytochemistry, 1977, 16, 1834.
C20H 260 6 M 362.422
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 267. Isol. from Montanoa tomentosa. Mp 194-196°. [ex]
-~.~. D

9-Angeloyl: [84886-37-3]. Zoapatanolide B

2,8,15-Trihydroxy-1(10),4,11(13)- Sq-00600
C20 H 260 6 M 362.422
germacratrien-12,6-olide Constit. of M. tomentosa and Blainvillea latifolia.
2,8,15- Trihydroxycostunolide
Kupchan, S.~. eta/, J. Org. Chern., 1973, 38, 2189 (Eupacunoxin,
Eupatocunm)
HO,~OH Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.
Cluijano, L. et al, Phytochemistry, 1982, 21, 2041 (Zoapatanolides)

1-{
Smgh, P. et a/, Phytochemistry, 1988, 27, 609 (Zoapatanolide B)
HOH]'
0 3,8,10-Trihydroxy-1,4,11(13)- Sq-00602
CtsH200s M 280.320 germacratrien-12,6-olide
(l(JO)E,2rt.,4Z,8fl)-form
2-Ange/oy/:
c~260 6 M 362.422
Constit. of Croquistianthus chachapoyensis.
2-Tigloy/:
C20H 260 6 M 362.422
Constit. of C. chachapoyensis.
(l(JO)E,2rt.,4E,8fl)-form
CtsH 200 5 M 280.320
8-Angeloyl:
(1 E,3P,4Z,6rt.,8P,l Ort.)-form

261
7,8,9-Trihydroxy-1(10),4,11(13)-... - 8,14,15-Trihydroxy-1(10),4,11(13)-... Sq-00603 - Sq-00605

8-Angeloyl: [56377-63-0]. Deoxytifruticin (l(JO)Z,4E,6p,8cx,9fl)-form

C20H 260 6 M 362.422 8-Angeloyl: [112356-33-9]. Gigantanolide A
Minor constit. of Tithonia fruticosa. Gum. C20H 260 6 M 362.422
1,2-Epoxide: see 1,2-Epoxy-3,8, 10-trihydroxy-4, 11(13)- Constit. of Montanoa gigas. Cryst. Mp 118-1.22°. [cx] 0
germacradien-12,6-olide, Sq-00529 - 152° (CHC1 3).
Herz, W. et al, J. Org. Chern., 1975, 40, 3118; 1979, 44, 1831. 9-Angeloyl: [112372-88-0]. Gigantanolide B
C20 H 260 6 M 362.422
7,8,9-Trihydroxy-1(10),4,11(13)- Sq-00603 From M. gigas.
germacratrien-12,6-olide 9-(2-Methylbutanoyl): [112356-38-4]. Gigantanolide C
C2oH 280 6 M 364.438
From M. gigas.
Rojatkar, S.R. et al, J. Chern. Res. (S), 1986, 272 (iso/, cryst
struct)
Quijano, L. et al, Phytochemistry, 1987, 26, 2589 (derivs)

8,14,15-Trihydroxy-1(10),4,11(13)- Sq-00605
germacratrien-12,6-olide
C 15H 200 5 M 280.320
(1 E,4E,6p,7cx,8cx,9fl)-form
8-Angeloyl:
C2oH 260 6 M 362.422 (1(10)Z,4Z,6a,8cx)-form
Constit. of Montanoa atriplicifolia. Gum.
9-Angeloyl:
0
C20H 260 6 M 362.422
Isol. from M. atriplicifolia. Gum. C 15H 2o0 5 M 280.320
8-(3-Methyl-2-butenoyl): (l(JO)Z,4E,6cx,8cx)-form
C20 H 260 6 M 362.422 8-(2-Methylpropenoyl): [50656-62-7]. Pectorolide
Isol. from M. atriplicifolia. Gum. C19H 240 6 M 348.395
9-(3-M ethyl-2-butenoyl): Constit. of Vernonia pectoralis. Amorph. [cx] 0 +243° (c,
C20H 260 6 M 362.422 1.05 in CHC1 3).
Isol. from M. atriplicifolia. Gum. 8-(2-Methylbutanoyl): [70855-63-9]. Bcx-(2-
9-(2-Methylpropanoyl): [103425-50-9]. Leucanthanolide Methylbutanoyloxy )albicanolide
C19H 260 6 M 350.411 C20 H 280 6 M 364.438
Constit. of M. leucantha. Cryst. Mp 85-87°. [cx] 0 Isol. from Cnicothamnus /orentzii. Oil.
-153.3° (c, 1.18 in CHC1 3). 8-Angeloyl: [113412-02-5]. Jurinelloide
9-(2R,3R-Epoxy-2-methylbutanoyl), 8-Ac: [72690-78-9]. C2oH2606 M 362.422
C22H280 8 M 420.458 Isol. from Jurinella moschus. Oil. [cx] 0 + 135° (c, 0.2 in
Isol. from M. hibiscifolia. Cryst. (EtOAc). Mp 166-167°. CHCI 3).
[cx] 0 -216.5° (c, 0.04 in CHC1 3). 8-(2-Hydroxymethyl-2Z-propenoyl): 20-Hydroxyjurine/loide
Herz, W. et al, J. Org. Chern., 1980, 45, 1113. C2oH 260 7 M 378.421
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1223. Constit. of J. moschus. Oil.
Oshima, Y. et al, J. Nat. Prod. (Lloydia), 1986, 49, 313 8-(2-Methylpropanoyl): [41929-10-6]. Alatolide
( Leucanthanolide) C19H 260 6 M 350.411
Constit. of Jurinea alata. Cryst. Mp 59-61°. [:x]i;l +64.4°.
8,9,14-Trihydroxy-1(10),4,11(13)- Sq-00604 8-(4-Hydroxy-2-methyl-2E-butenoyl): [22419-78-9].
germacratrien-12,6-olide Jurineolide
C20 H 260 7 M 378.421
OH Isol. from leaves of J. cyanoides. Cryst. (EtOAc). Mp
OH 170-172°. [cx] 0 + 134.9° (c, 0.17 in MeOH). Readily
(1(10)Z,4E,6a,8~,9~)-:form polymerises.
14-Aldehyde: see 8,15-Dihydroxy-14-oxo-1(10),4.11(13)-
germacratrien-12,6-olide, Sq-00488
(J(JOZ),4Z,6cx,8fl)-form
0
14-(Methylpropanoyl), 15-Ac: [75683-61-3]. Linearilobin A
CisHw05 M 280.320 C21 H 280 7 M 392.448
(l(JO)Z,4E,6cx,8p,9fl)-form Constit. of Melampodium linearilobum. Cryst. Mp 144-
8-(2-Methylpropanoyl), 14-Ac: 14-Acetoxy-9p-hydroxy-8P- 1450.
(2-methylpropanoyloxy)-1 (1 0),4, 11 ( 13)-germacratrien- 14-(2-Methylbutanoyl), 15-Ac: [75683-60-2]. Linearilobin B
12,6cx-olide C22H 300 7 M 406.475
C21 H 280 7 M 392.448 Constit. of M. linearilobum. Cryst. Mp 151-152°.
Constit. of Blainvillea latifolia. Cryst. (Me 2C0jpet. 8-(4-Hydroxy-2-methyl-2Z-butenoyl), 15-Ac: [75683-57-7].
ether). Mp 159-160°. [cx] 0 -47.8° (CHC1 3). Linearilobin C
14-Aldehyde: see 8,9-Dihydroxy-14-oxo-1(10),4, 11(13)- C22H280 8 M 420.458
germacratrien-12,6-o/ide, Sq-00486 Constit. of M. linearilobum. Gum.
14-Carboxylic acid: see 8,9-Dihydroxy-1(10),4,11(13)- 8-(Methylpropenoyl), 15-Ac: [75683-58-8]. Linearilobin D
germacratrien-12,6-olid-14-oic acid, Sq-00476 C21 H 260 7 M 390.432

262
3,8,9-Trihydroxy-1(10),4,11(13)-... - 8,9,15-Trihydroxy-1(10),4,11(13)-•.. Sq-00606 - Sq-00608

Constit. of M. lineariloburn. Gum. 8-(2R,3R-epoxy-2-rnethylbutanoyl), 9-Ac, Me ester: [60295-

14-(Methy/propenoyl), 15-Ac: [75683-59-9]. Linearilobin E 54-7]. Leucanthinin
C 21 H 260 7 M 390.432 C 23H 180 10 M 464.468
Constit. of M. lineariloburn. Gum. Constit. of Melarnpodiurn leucanthurn. Cryst.
15-(2-Methylbutanoyl): [75683-54-4]. Linearilobin F (CHC1 3/Etz0). Mp 163-164°.
C 20H 180 6 M 364.438 Fischer, N.H. et a/, J. Org. Chern., 1976, 41, 3956.
Constit. of M. lineariloburn. Gum.
14-Carboxy/ic acid, 15-(2-rnethylbutanoyl): [75683-53-3]. 5,8,9-Trihydroxy-1(10),4(15),11(13)- Sq-00607
Lineari/obin G germacratrien-12,6-olid-14-oic acid
C1,H200 6 M 308.330
From M. lineariloburn. Gum. COOH
8-Ac: 8-Acetoxy-14,15-dihydroxycostunolide
C 17H 2z0 6 M 322.357
Constit. of Dicorna anornala. Gum.
8,15-Di-Ac: 8,15-Diacetoxy-14-hydroxycostunolide
CI,H:u07 M 364.394
Constit. of D. anornala.
14-(2-Methy/-3-hydroxybutanoyl), 8-Ac:
C 22H 300 8 M 422.474 C1sH1s07 M 310.303
Constit. of D. anornala. Gum. (1(10)E,5P,6rz,8P,9rz)-form
(1(10)Z,4E,6rz,8fl)-form 9-Angeloyl, 8-Ac, Me ester: [92356-80-4]. Repandin E
14-(Methylpropenoyl), 8-Ac: [75683-56-6]. Linearilobin H Cz3H 280 9 M 448.469
C 21 H 26 0 7 M 390.432 Constit. of Melarnpodiurn longipilurn. Cryst.
Constit. of M. lineariloburn. Gum. (CHC1 3/Et20). Mp 172-174°.
15-(2-M ethyl-4-oxo-2-butenoyl), 8-Ac: [7 5683-55-5]. 9-(2-Hydroxyrnethyl-2£-butenoyl), 8-(2-rnethylpropanoyl),
Linearilobin I Me ester: [71155-66-3]. Repandin A
C 22 H 260 8 M 418.443 C 25 H 320 10 M 492.522
Constit. of M. lineariloburn. Gum. !sol. from Tetragonotheca repanda. Cryst. (EtzO). Mp
(1(10)Z,4Z,6rz,8rz)-form 132-133°.
8-Ac: Brz-Acetoxy-14,15-dihydroxycostunolide 9-(2-Hydroxyrnethyl-2E-butenoyl), 8-(2-rnethylbutanoyl), Me
CI7Hzz06 M 322.357 ester: [71138-42-6].
Constit. of D. anornala. Gum. Cz,H340Io M 506.549
Constit. ofT. repanda. Cryst. Mp 127-128°.
8,15-Di-Ac: 8rz,15-Diacetoxy-14-hydroxycostunolide
C 1,H24 0 7 M 364.394 9-(2R,3R-Epoxy-2-rnethylbutanoyl), 8-(2-rnethylpropanoyl),
Constit. of D. anornala. Gum. Me ester: [71138-44-8]. Repandin C
C25 H 3z010 M 492.522
14-(3-Hydroxy-2-rnethylbutanoyl), 8-Ac:
Constit. of T. repanda. Gum.
C 22H 300 8 M 422.474
Constit. of D. anornala. Gum. 9-(2R,3R-Epoxy-2-rnethylbutanoyl), 8-(2-rnethylbutanoyl),
Me ester: [71138-45-9]. Repandin D
Suchy, M. et a/, Collect. Czech. Chern. Commun., 1969, 34, 229
C 26 H 340 10 M 506.549
(Jurineolide)
Drozdz, B. et a/, Collect. Czech. Chern. Commun., 1973, 38, 727 Constit. of T. repanda. Gum.
(Alatolide) Seaman, F. eta/, J. Org. Chern., 1979, 44, 3400.
Mompon, B. eta/, Tetrahedron, 1976, 32, 2545 (Pectorolide) Quijano, L. eta/, Phytochemistry, 1984, 23, 829.
Cox, P.J. et a/, J. Chern. Soc., Perkin Trans. 2, 1977, 255 (cryst
struct, Alatolide)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 95 (2- 8,9,15-Trihydroxy-1(10),4,11(13)- Sq-00608
M ethylbutanoyloxyalbicano/ide) germacratrien-12,6-olid-14-oic acid
Seaman, F.C. eta/, Phytochemistry, 1980, 19, 849 (Linearilobins)

61
Rustaiyan, A. eta/, Phytochemistry, 1987, 26, 2857 (Jurinelloide,
20- Hydroxyjurinelloide)
Zdero, C. eta/, Phytochemistry, 1990, 29, 183 (isol, pmr, cmr)

3,8,9-Trihydroxy-1(10),4,11(13)- Sq-00606
germacratrien-12,6-olid-14-oic acid
HO~C 0 0
HOOC
CisHis07 M 310.303
(l(JO)E,4E,6rz,8P,9fl)-form
8,9-Bis-(2-rnethylpropenoyl), Me ester: [88099-89-2].
Me/rosin C
C24 H 280 9 M 460.480
Constit. of Melarnpodiurn rosei. Gum.
0 8-Angeloyl, 9-Ac, Me ester: [68024-34-0]. Melcanthin A
C23H 280 9 M 448.469
C 15H 200 7 M 312.319
!sol. from M. leucanthurn. Gum.
(1(10)E,3rz,4E,6rz,8P,9rz)-form
8-(2-Methylpropenoyl), 9-Ac, Me ester: [79405-87-1].
Mekanthin D

263
8,14,15-Trihydroxy-4-germacren-12,6-... - 3,8,10-Trihydroxy-1-oxo-4,11(13)-... Sq-00609 - Sq-00611

CnH21;09 M 434.442 Constit. of Siegesbeckia orienta/is. Glass. [rxJi~' -130.2°

FromM. cinereum. (c, 0.9 in EtOH).
8-(2-Methy/propanoyl), 9-Ac, Me ester: [79405-86-0]. Rybalko, K.S. et a/, Khim. Prir. Soedin., 1976, 12, 394; Chem. Nat.
Melctu~thin E Compd. (Engl. Trans/.), 346.
CuH 280 9 M 436.458
From M. cinereum. Gum. 1,8,10-Trihydroxy-3-oxo-4,11(13)- Sq-00610
8-(2-Methy/butanoyl), 9-Ac, Me ester: [79405-85-9]. germacradien-12,6-olide
Melctu~thin F
C13H 300 9 M 450.485
From M. cinereum. Gum. Obt. as mixt. with Melcanthin
G.
9-(2-Methy/butanoyl), 8-Ac, Me ester: [79405-84-8].
Melctu~thin G
C13H 300 9 M 450.485
From M. cinereum. Gum. Obt. as mixt. with Melcanthin
F. 0
8,9-Bis(2-methylpropanoyl), Me ester: [89900-56-1].
Longicornin B CtsHta06 M 294.304
C14H 320 9 M 464.511 (1 p,4Z,6«.,8P,J 0«. )-form
Isol. from M. /ongicorne. Cryst. (EtOAc). Mp 135- 8-(2-Methy/butanoyl): [110397-67-6]. Resinoso/ide
136.SO. C19H 260 7 M 366.410
8-(2-Methy/propanoyl), 9-(2-methy/butanoyl), Me ester: Constit. of Greenmaniel/a resinosa. Gum.
[89900-54-9]. Longicornin D Zdero, C. et a/, Phytochemistry, 1987, 26, 1999.
C:!!H 340 9 M 478.538
. FromM. longicorne. Gum. 3,8,10-Trihydroxy-1-oxo-4,11(13)- Sq-00611
(l(JO)E,4Z,6«.,8P,9«)-form germacradien-12,6-olide
8-(2R,3R-Epoxy-2-methylbutanoyl), 15-Ac, Me ester:
[72943-99-8]. Longipin
C13H 280 10 M 464.468
Constit. of M. longipes. Cryst. (EtOAc). Mp 203-206°.
8-(2,3-Diacetoxy-2-methy/butanoyl), 9-Ac, Me ester: [75627-
94-0]. Tetrahelin B
C27H 340 13 M 566.558
Constit. of Tetragonotheca helianthoides. Gum. C15H 200 6 M 296.319
8-(3-Acetoxy-2-hydroxy-2-methy/butanoyl), 9-Ac, Me ester: (3«.,4E,6«.,8P,JO«.)-form
[75627-91-7]. Tetrahelin F 8-Ange/oy/: [84886-55-5]. 3«.-Hydroxytrichomoriolide
C:!!H320 2 M 364.527 C20H 260 7 M 378.421
Constit. of T. helianthoides. Gum. Constit. of Trichogoniopsis morii. Gum.
4oc,5-Dihydro, 8-(2-methy/propanoyl), 9-Ac, Me ester: 8-Ange/oy/, 3-Ac: [84886-56-6]. 3«.-Acetoxytrichomorio/ide
[74562-62-2]. 9«.-Acetoxyme/nerin A CnH280 8 M 420.458
CuH 300 9 M 438.474 Constit. ofT. morii. Cryst. Mp 151°. [rx]i;' +104° (c,
Constit. of M. /eucanthum. Cryst. Mp 149-151°. 0.55 in CHC1 3).
4rx,5-Dihydro, 8-(2-methy/butanoyl), 9-Ac, Me ester: [74562- (3«.,4E,6«.,8ft,l0p)-form
66-6]. 9«.-Acetoxyme/nerin B 8- Tigloyl: 3-Hydroxybejartu~olide
C13H 320 9 M 452.500 C20H 260 7 M 378.421
Constit. of M. leucanthum. Cryst. Mp 136-138°. lsol. from Bejaranoa semistriata. Gum. [rx]~4 + 57° (c, 1
Fischer, N.H. eta/, J. Org. Chem., 1978, 43, 4984 (Me/canthin A) in CHC1 3).
Seaman, F.C. eta/, Phytochemistry, 1979, 18, 1065; 1980, 19, 583. 4P,5-Dihydro, 8-ange/oy/, 10-Ac: [83731-11-7].
Olivier, E.J. eta/, J. Org. Chem., 1980, 45, 4028; 1983, 22, 1453. Piptospermolide
Klimash, J.W. eta/, Phytochemistry, 1981, 20, 840 (Melcanthins D- CuH300 8 M 422.474
G) Constit. of Piptolepis leptospermoides. Gum.
Malcolm, A.J. eta/, Phytochemistry, 1983, 22, 2759 (Longicornins)
(3«.,4Z,6«.,8P,10«.)-form
8,14,15-Trihydroxy-4-germacren-12,6- Sq-00609 8-Ange/oy/: [84886-57-7].
Constit. ofT. morii. Cryst. Mp 180°. [rx]i;' -25° (c, 0.04
olide in CHCI 3).
(3«.,4Z,6«.,8P,10p)-form
8-Tig/oy/: Constit. of B. semistriata. Gum. [rx]~4 -30° (c,
0.35 in CHC1 3).
(3P,4Z,6«,8P,JOp)-form
8-Tig/oy/: Constit. of B. semistriata. Gum. [rx]i;' -34° (c,
0 0.5 in CHC1 3).
C15Hn05 M 282.336 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1639; 1982, 21,
(4Z,6~,8~,10~)-form 1439, 2035.
8-(2-Methy/propenoyl): [60485-60-1]. Orientin
C19H260 6 M 350.411

264
5,8,10-Trihydroxy-1-oxo-2,11(13)-... - 8,10,13-Trihydroxy-1-oxo-4,7(11)-... Sq-00612 - Sq-00615

5,8,10-Trihydroxy-1-oxo-2,11(13)- Sq-00612 Constit. of C. urticifolia. Cryst. (Etp). Mp 168°. [o:]i;'

germacradien-12,6-olide -26.SO (c, 0.5 in CHC1 3). Caleurticolide is unknown.
8,9-Bis(2-methylpropenoyl): [71652-12-5]. Caleurticolide 2-
' \ OH methylacrylate
C23H210a M 432.469
Constit. of C. urticifolia. Oil.
8-(2-Methylpropenoyl), 9-angeloyl: [71052-13-6].
Caleurticolide angelate
C24H:14P 8 M 446.496
Constit. of C. urticifolia. Cryst. (Etp). Mp 158.5°. [o:]24
0 -27° (c, 0.25 in CHC1 3). n
Manchand, P.S. et a/, J. Org. Chern., 1978, 43, 4352 (Neurolenin
C 15H 100 6 M 296.319 B)
Gum. Bohlmann, F. eta/, Phytochemistry, 1979, 18, 119 (Caleurticolides)
(2E,4PH,5P,6rx.,Bp,JOfl)-form Quijano, L. eta/, Phytochemistry, 1979, 18, 1745 (Caleins)
8-Angeloyl, 10-Ac: [79306-90-4]. Piptolepolide Del Castillo, J.B. et a/, J. Nat. Prod. (Lloydia), 1981, 44, 348
(Juanislamin)
C22H 280 8 M 420.458
Ober, A.G. et a/, Phytochemistry, 1986, 25, 467 (Desacetylcalein A)
Constit. of Piptolepis ericoides.

q:
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 731.
8,9,10-Trihydroxy-1-oxo-4,11(13)- Sq-00614
germacradien-12,6-olide
8,9,10-Trihydroxy-1-oxo-2,11(13)- Sq-00613
germacradien-12,6-olide \OHOH
OH
8

h
I
0
-
0
CtsHzo06 M 296.319
CtsH100 6 M 296.319 (4E,6rx.,ap,9p,JOfl)-form
(2Z,4rx.H,6rx.,BP,9rx.,l Orx. )-form 8-Deacyl-9-hydroxybejaranolide
9-Angeloyl: Desacetylcalein A 8-(3-Methylbutanoyl): [89355-48-6].
C10H 260 7 M 378.421 C10H 280 7 M 380.437
Constit. of Calea leptocephala. Cryst. Mp 198.SO. Constit. of Trichogonia prancii. Cryst. (Etp). Mp 246°.
9-Angeloyl, 8-Ac: [63194-22-9]. Calein A 8-(3-Methylbutanoyl), 9-Ac: [89355-49-7].
C22H 280 8 M 420.458 C22H 34,08 M 422.474
Constit. of C. zacatechichi. Cryst. Mp 180-182°. Constit. ofT. prancii. Cryst. (Etpjpet. ether). Mp 161°.
[o:]i;' +66° (c, 0.27 in CHC1 3).
8-Angeloyl, 9-Ac: [63194-23-0]. Calein B
C22H 280 8 M 420.458 8-Angeloyl: [89355-50-0].
Constit. of C. zacatechichi. Cryst. Mp 180-182°. C10H 260 7 M 378.421
Constit. of T. salviaefolia. Oil.
8-(2-Methylpropenoyl), 9-Ac: [73723-68-9]. Calein C
C21 H 260 8 M 406.432 Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162.
Isol. from C. zacatechichi.
9-(2-Methylpropenoyl), 8-Ac: [73723-67-8]. Calein D 8,10,13-Trihydroxy-1-oxo-4,7(11)- Sq-00615
C11H 260 8 M 406.432 germacradien-12,6-olide
Isol. from C. zacatechichi.
8,9-Bis(2-methylpropenoyl): [75628-10-3]. Juanislamin
C:z3H280 8 M 432.469
Constit. of C. urticifolia. Cryst. (Et 20). Mp 136-138°.
[o:Jn -320° (c, 0.25 in CHC1 3).
2a.,3o:-Epoxide, 8,9-bis(2-methylpropenoyl):
C:z3H 280 9 M 448.469
Constit. of C. urticifolia. Cryst. (Etp). Mp 146-148°.
[o:]n -221° (c, 0.5 in CHC1 3). 0
8-(2-Methylbutanoyl), 9-Ac: [67506-30-3]. Neurolenin B CtsHzo06 M 296.319
C22 H:lfPs M 422.474
Constit. of N. lobata. Cryst. (EtOAcjhexane). Mp 165-
(4E,6rx.,8rx.,10rx.)-form
1660. [o:]i,S -350.0° (c, 0.76 in CHC13). 8-(2-Methylpropenoyl), 10,13-di-Ac: [79404-44-7]. Disyfolide
Constit. of Disynaphia halimifolia. Gum. [o:]i;' -6° (c, 1
(2Z,4PH,6rx.,8p,9rx.,10f/)-form
10-Config. ambiguously drawn, not certain. in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1077.
8-(2-Methylpropenoyl), 9-Ac: [71060-21-4]. Caleurticolide
acetate
C21 H 260 8 M 406.432

265
1,5,8-Trihydroxy-14-oxo-4(15) ... - 5,8,10-Trihydroxy-1-oxo-11(13)-... Sq-00616 - Sq-00619

1,5,8-Trihydroxy-14-oxo-4(15),9,11(13)- Sq-00616 8-(2-Methylpropenoyl), 10-Ac:

germ~cratrien-12,6-olide C21 H 280 8 M 408.447
Constit. of Lychnophora blanchetii. Gum.
OH 3-Me ether, 8-(2-methylpropenoyl), 10-Ac:
C22H 300 8 M 422.474
Isol. from L. blanchetii. Gum.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1609; 1982, 21,
1087.

5,8,10-Trihydroxy-1-oxo-11(13)- Sq-00619
germacren-12,6-olide
0
CtsH180 6 M 294.304
(lfl,5JJ,6«,8fl.9Z)-form
0 1-Et: 1-Etlwxy-9Z-millerenolide
C21H21;07 M 390.432
lsol. from Milleria quinque.flora.
4/1,15-Epoxide, 0 1-Me: 4fl,l5-Epoxy-lfl-methoxy-9Z-
millerenolide
C20H 240 8 M 392.405 CtsHn06 M 298.335
From M. quinque.flora. Oil. (4rxH,5fl,6rx,8rx,lOrxOH)-form
4/1,15-Epoxide, 0 1-Et: 4fl,l5-Epoxy-lfl-etlwxy-9Z- 8-(2-Methylpropenoyl), 10-Ac: [128700-83-4]. Lychnostatin
millerenolide 1
C21H260 8 M 406.432 C21 H 28 0 8 M 408.447
From M. quinque.flora. Oil. Constit. of Lychnophora anti/lana. Shows cytostatic
Jakupovic, J. eta/, Phytochemistry, 1987, 26, 2011. props. Cryst. (Me 2COfhexane). Mp 228-230°. [ex]i;l +89°
(c, 1 in CHCI3).
5-Deoxy, 8-(2-methylpropenoyl), 10-Ac: [128700-84-5].
8,9,10-Trihydroxy-1-oxo-3,11(13)- Sq-00617 Lychnostatin 1
germacratrien-12,6-olide C21H 280 7 M 392.448
Constit. of L. anti/lana. Needles (Me 2COfhexane). Mp
190-193°. [ex]~ +20.9° (c, 0.67 in CHC1 3).
Pettit, G.R. et al, J. Nat. Prod. (Lloydia), 1990, 53, 382 (isol, pmr,
cmr, cryst struct)

C1sH200 6 M 296.319
(3Z,6«.,8fl.9«,10«.)-form
8-(3-Methylbutanoyl), 9-Ac: [84754-03-0]. Lobatin A
C22H 300 8 M 422.474
Constit. of Neurolaena lobata. Cryst. (hexane). Mp 154-
1550. [ex]~ -304° (c, 0.5 in CHC1 3).
Borges-del-Castillo, J. et a/, J. Nat. Prod. (Lloydia), 1982, 45, 762.

3,8,10-Trihydroxy-1-oxo-11(13)- Sq-00618
germacren-12,6-olide

CtsH220 6 M 298.335
(3fl,4«.H,6«.,8«.,10«.)-form
8-Angeloyl, 10-Ac: 1,3-Dihydro-Jfl-hydroxyereglomerulide
C22H 300 8 M 422.474
Constit. C?f Eremanthus glomerulatus. Cryst. (Et20jpet.
ether). Mp 105°. [ex]~4 -4.6° (c, 0.7 in CHC1 3).

266
1,10:14,15-Diepoxy-6,14-dihydroxy-... - 1,10:4,5-Diepoxy-11(13)-germacren-... Sq-00620 - Sq-00625

1,10:8,12-Diepoxy-4,7, 11-germacratrien- Sq-00623

15,6-olide
12,8-Germacranolides
and furanogermacranes ~ (la,6a,!Oa)cfo'm

C15H 160 4 M 260.289

1,10:14,15-Diepoxy-6,14-dihydroxy-
4,11(13)-germacradien-12,8-olide
C15H 180 6 M 294.304
(Jp,4E,61X.,81X.,101X.)-form
6-(2-Methylpropanoyl): [21871-14-7]. Vernomygdin
C1,Il:w07 M 364.394
Constit. of leaves of Veronica amygdalina. Cryst.
(Me 2COjpet. ether). Mp 208-210°. [ex]~ +65° (c, 1 in
Sq-00620 (1«,6«,10«)-form [20082-45-5] Pseudoneolinderane
Constit. of Neolitsea aciculata. Cryst. (CH 2C12 /Etp).
Mp 200-202°. [exln +90.3° (c, 0.94 in CHC1 3).
(1p,6«,1 0/1)-form [15004-50-9] Neolinderane
Constit. of N. zeylanica. Cryst. (CH 2Cl 2/Etp). Mp
170°. [ex]~ +31.5°.
Joshi, B.S. eta/, Tetrahedron, 1967, 23, 261, 267 (isol, struct)
Takeda, K. eta/, J. Chern. Soc., Chern. Commun., 1968, 1168 (abs
con.fig)
Takeda, K. eta/, J. Chern. Soc. C, 1970, 973 (Pseudoneolinderane)
Joshi, B.S. eta/, J. Sci. Ind. Res., 1976, 35, 239 (rev)
4,5:8,12-Diepoxy-1(10),7,11- Sq-00624
germacratrien-6-one

~
Me 2CO).
Kupchan, S.M. et al, J. Org. Chern., 1969, 34, 3908.

1,8:4,5-Diepoxy-7(11 ),9-germacradiene- Sq-00621 / 0 0

12,8: 14,6-diolide Ct5Hta03 M 246.305
(l(JO)E,4P,5fl)-form [7727-79-9] Zederone
Constit. of the crude drug Zedoary, prepared from the
rhizome of Curcuma zedoaria. Cryst. (EtOAc). Mp
153.5-154°. [exln +265.8° (c, 0.5 in CHCI 3).
Hikino, H. et al, J. Chern. Soc. C, 1971, 688 (isol)
Shibuya, H. eta/, Chern. Pharm. Bull., 1987, 35, 924 (abs config,
cryst struct)
Ct5Ht 40 6 M 290.272
(JS,4P,5P,6«,8«)-form [88653-68-3] Neoliacine 1,10:4,5-Diepoxy-11(13)-germacren-12,8- Sq-00625
Constit. of Neolitsea aciculata. Cryst. Mp 283° dec. [exln olide
+ 7.3° (c, 5.4 in Py).
Nozaki, H. et a/, J. Chern. Soc., Chern. Commun., 1983, 1107 (isol,
cryst struct)

1,10:2,3-Diepoxy-4,11(13)-germacradiene- Sq-00622
12,8:14,6-diolide 13

C15H 1u07 M 312.319

o~o
(1«,4«,5P,8«,10«)-form [87441-73-4]11,13-Dehydroeriolin
0 CtsHn04
C15H 140 6 M 290.272
(1«,2P,3P,6«,8«,10/1)-form [17928-61-9] Mikanolide
Constit. of Mikania scandens. Cryst. (Me2COjhexane).
Mp 226-228°. [ex]i: + 53.4° (c, 1.12 in dioxan).
11ft,13-Dihydro: [23758-04-5]. 1,10:2,3-Diepoxy-4-
germacrene-12,8: 14,6-diolide. Dihydromikanolide
C15H 160 6 M 292.288
Constit. of M. scandens. Cryst. (Me 2CO/hexane). Mp
240-244°. [exln +91.1° (dioxan).
Herz, W. eta/, J. Org. Chern., 1970, 35, 1453 (isol)
Cox, P.J. eta/, J. Chern. Soc., Perkin Trans. 2, 1974, 1355 (cryst
struct)
Constit. of Schkuhria spp. Cryst. (Me 2CO/Et20). Mp
173-174°. [exJn -36o (CHCI 3).
Jlex,J3-Dihydro: [11014-50-9]. 1,10;4,5-Diepoxy-12,8-
germacranolide. lvaxillin
M 266.336
Constit. of Iva axillaris. Cryst. (CHCI 3 jhexane). Mp
181-182°.
11~,13~-Dihydro: [27542-21-8]. Eriolin
C15Hu04 M 266.336
Constit. of Eriophyllum confertiflorum. Cryst. Mp 238-
2400. [exln -42°.
Herz, W. et al, J. Org. Chern., 1966, 31, 3232; 1982, 47, 3991
(lvaxillin)
Torrance, S.J. et al, Phytochemistry, 1969, 8, 2381 (isol)
Romo de Vivar, A. et al, Phytochemistry, 1982, 21, 2905 (isol)
Calderon, J.S. eta/, Phytochemistry, 1987, 26, 1747 (cryst struct)

267
1,10:4,5-Diepoxy-8-hydroxy-7(11)-... - 1,6-Dihydroxy-4,10(14),11(13)-... Sq-00626 - Sq-00629

1,10:4,5-Diepoxy-8-hydroxy-7(11)- Sq-00626 Sq-00629

germacren-12,8-olide

~0 (1~,4cx,5~,8cx0H,10~)-form

C 15H 200 5 M 280.320

(1P,4«,5P,8«0H,10«)-form C 15H 200 4 M 264.321
8-(2-Methylpropyl): 1P,10«:4«,5P-Diepoxy-8«- (1 «,4E,6«,8« )-form
isobutoxyglechomanolide 1«-Hydroxy-1-desoxotamirin
CI,H2805 M 336.427 Isol. from Tanacetum polycephalum. Gum. [a]i;* +50° (c,
Constit. of Smyrnium perfoliatum. Amorph. 0.5 in CHC1 3).
(JP,4«,5P,BPOH,10«)-form 6-Ac: Dihydrochrysanolide
8-(2-Methylpropyl): 1P,10«:4«,5fl-Diepoxy-8fl- C17H110 5 M 306.358
isobutoxyglechomanolide Constit. of Liriodendron tulipifera. Cryst. (EtOAc). Mp
Ct9H 280 5 M 336.427 163-163.SO. [a]i;* +8.6° (c, 0.09 in MeOH).
From S. perfoliatum. Cryst. Mp 155°. 1-Ketone: [52591-19-2]. 6a-Hydroxy-1-oxo-4,10( l4),11(13)-
Goren, N. et al, Phytochemistry, 1987, 26, 2585.
germacratrien-12,8a-olide. Tamirin
C,sH 180 4 M 262.305
Constit. ofT. spp. Cryst. Mp 167-168°. [ali? -36.SO.
1,3-Dihydroxy-4,9,11(13)-germacratriene- Sq-00627 1-Ketone, 6-Ac: [34226-88-5]. Chrysanolide
12,8;14,6-diolide C17H1o05 M 304.342
Constit. of Chrysanthemum cinerariaefolium. Cryst.
(diisopropy1 ether). Mp 204-205°. [a]i; -52° (c, 0.3 in
MeOH).
1-Hydroperoxide: la-Hydroperoxy-6a-hydroxy-
4,10(14),11(13)-germacratrien-12,8a-olide. 1«-
Hydroxyperoxy-1-desoxodesacetylchrysanolide
C15H100 5 M 280.320
Constit. of Mikania goyazensis. Gum. [aJ14 -22° (c, 0.29
C 15H 160 6 M 292.288 in CHC1 3).
(1«,3P,6«,8«,9Z)-form [1 00760-63-2] Mikaperiplocolide (1«,4E,6«,8p)-form [60362-95-0] Tanachin
Constit. of Mikania periplocifolia. Constit. ofT. pseudoachillea. Cryst. (EtOAc). Mp 158-
Gutierrez, A.B. et al, Phytochemistry, 1985, 24, 2967. 1590. [a]~ + 34.8° (c, 1.84 in MeOH).
1-Hydroperoxide: IP-Hydroperoxy-6a-hydroxy-
1,6-Dihydroxy-4,9, 11(13)-germacratrien- Sq-00628 4,10(14),11(13)-germacratrien-12,8a-olide. 1/l-
12,8-olide Hydroperoxy-1-desoxodesacetylchrysanolide
C1sH1P 5 M 284.352
OH Constit. of M. goyazensis.
I
(1P,4E,6rx.,8rx.)-form
cm6lo,4E,60<,8•,9E)fo'm 1ft-Hydroxy-1-desoxotamirin
Isol. from T. polycephalum. Gum. [aJ14 + 38° (c, 0.2 in
CHC1 3).
OH Doskotch, R.W. et al, Can. J. Chern., 1971, 49, 2103
( Chrysanolide)
C,sH2004 M 264.321 Mnatsakanyan, V.A. et al, Khim. Prir. Soedin., 1974, 396
(1«,4E,6«,8«,9E)-form [71030-09-6] Tavulin (Tamirin)
Constit. of Tanacetum vulgare. Cryst. Mp 160-161°. Yunusov, A.I. et al, Khim. Prir. Soedin., 1976, 263, 462; CA, 85,
(1P,4E,6«,8«,9Z)-form 177643t, 177660w (Tanachin)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1349
6-Ac: [72811-84-8]. Tulirinol (Pydorperoxides)
c,7H110 5 M 306.358 El-Feraly, F.S. et al, J. Chern. Soc., Perkin Trans. I, 1983, 355
Constit. of Liriodendron tulipifera. Cryst. (Et20/CHC1 3). (synth)
Mp 204-206°. [a]~ -51° (c, 0.3 in MeOH). Doskotch, R.W. et al, J. Nat. Prod. (Lloydia), 1983, 46, 923
(1 p,4E,6«,8P,9Z)-form (Dihydrochrysanolide)
Makhmudov, M.K. et al, Khim. Prir. Soedin., 1989, 25, 198;
6-(2-Methylpropanoyl): [111625-64-0]. Subcordatolide D Chern. Nat. Compd. (Engl. Trans/.), 168 (cryst struct)
C19H 11;05 M 334.411 Rustaiyan, A. et al, Phytochemistry, 1990, 29, 3022 (I·Hydroxy-I-
Constit. of Calea subcordata. Cryst. (CHC1 3/hexane). desoxotamirins)
Mp 246° dec.
El-Feraly, F.S. et al, J. Chern. Soc., Perkin Trans. I, 1973, 355
(synth)
Yunusov, A.I. et al, Khim. Prir. Soedin., 1979, 101 (Tavulin)
Doskotch, R.W. et al, J. Org. Chern., 1980, 45, 1441 (Tulirinol)
Ober, A.G. et al, J. Nat. Prod. (Lloydia), 1987, 50, 604
(Subcordatolide D)

268
2,6-Dihydroxy-1(10),4,11(13)-... - 6,15-Dihydroxy-1(10),4,11(13)-... Sq-00630 - Sq-00634

2,6-Dihydroxy-1(10),4,11(13)- Sq-00630 6,14-Dihydroxy-1(10),4,11(13)- Sq-00633

germacratrien-12,8-olide germacratrien-12,8-olide
14
Ho,{)l_o>=o CH20H
~O (I(IO)E,4E,6a,8o)-fo~
TY:\ OH
C15H 100 4 M 264.321
(1(10)E,2rz,4E,6rz;Brz)-form C15H 100 4 M 264.321
6-Ac: 2rz-Hydroxylllurenobiolide (1(10)E,4E,6rz,Brz)-form
C17H 120 5 M 306.358 6-Ac: [88861-90-9]. Soulangianolide B
Constit. of Gnephosis arachnoidea. Gum. [1X]~4 +49° (c,
C17H 220 5 M 306.358
0.21 in CHC1 3). Isol. from a Magnolia sp. Oil. [1X] 0 -63° (c, 0.53 in
Di-Ac: 2rz-Acetoxylllurenobiolide MeOH).
C 19H 240 6 M 348.395 11 p,13-Dihydro: [127054-49-3]. 6rz,14-Dihydroxy-1(1 O)E,4E-
Constit. of Mikania grazielae. Gum. [1X]i;' + 56° (c, 0.37 germacradien-12,8rz-olide
in CHC1 3). Isol. from Schkuhria pinnata. Oil.
Jakupovic, J. et al, Phytochemistry, 1988, 27, 3181.
11P,13-Dihydro, 14-aldehyde: [127072-56-4]. 6rz-Hydroxy-
14-oxo-1(1O)E,4E-germacradien-12,8rz-olide
2,15-Dihydroxy-1(10),4,11(13)- Sq-00631 C15H100 4 M 264.321
germacratrien-12,8-olide From S. pinnata. Oil.
(l(JO)E,4E,6rz,Bfl)-form
HO~-O)=o 14-(2-Methylbutanoyl): [87441-79-0]. Schkuhrioidin
C19H 260 5 M 334.411

~
CHPH
Constit. of Schkuhria schkuhrioides. Pale-yellow oil. [IX]i?
+ 86.5" (MeOH).
(1(10)Z,4E,6rz,Brz)-form
C 15H100 4 M 264.321 14-(2-Hydroxymethylpropenoyl): [114927-44-5].
(l(JO)E,2~,4Z,Brz)-form Gochnatolide
Constit. of Arctotis aspera. C19H 240 6 M 348.395
15-Ac: 15-Acetoxy-2<!-hydroxy-1(10),4,11(13)- Constit. of Gochnatia hypoleuca. Cryst.
germacratrien-12,81X-olide (Me 2COjhexane). ,Mp 107-109°. [1X]i;5 +8.89° (c, 0.169 in
C17H 220 5 M 306.358 CHC1 3).
Constit. of A. aspera. Romo de Vivar, A. et al, Phytochemistry, 1982, 21, 2905
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 195 (isol, pmr, cmr) (Schkuhrioidin)
El-Feraly, F.S., Phytochemistry, 1983, 22, 2239 (Soulangiolide B)
Maldonado, E. et al, Phytochemistry, 1988, 27, 861 (Gochnatolide)
3,6-Dihydroxy-1(10),4,11(13)- Sq-00632 Ganzer, U. et al, Phytochemistry, 1990, 29, 535 (isol, pmr, derivs)
germacratrien-12,8-olide
6,15-Dihydroxy-1(10),4,11(13)- Sq-00634
~-0>= germacratrien-12,8-olide
HO'Y0 O
OH ~-o'>=o
C 15H 100 4 M 264.321
(l(JO)E,3rz,4E,6rz,Brz)-form [24112-94-5] Chamissonin
~
HOH2 C
OH
lsol. from Ambrosia chamissonis. Cryst. (C6H 6). Mp 124- C15H100 4 M 264.321
1250. (1X]i;5 -19.8° (c, 2.2 in EtOH).
(l(JO)E,4Z,6rz,Brz)-form [26931-87-3] Artemisiifolin
3-Ac: 3-Acetylchamissonin Constit. of Ambrosia artemisiifolia, other A. spp. and
C17H 220 5 M 306.358 Centaurea serides. Cryst. (EtOAc). Mp 131°. (1X]i;5
Constit. of Viguiera deltoidea. Cryst. Mp 160-161°. + 54.6° (MeOH).
3-Ketone: [75911-35-2]. 6rz-Hydroxy-3-oxo-1(10)-germacren- Di-Ac:
12,8rz-olide. !Argentiolide A C19H 240 6 M 348.395
CtsH 180 4 M 262.305 Constit. of Mattfeldanthus nobilis. Gum.
Constit. of Artemisia argentea. Cryst. (Etp). Mp 197-
1990. 6-(2,3-Dihydroxy-2-methylpropanoyl), 15-Ac: [20055-57-6].
Scabiolide
L'Homme, M.F. et al, Tetrahedron Lett., 1969, 3161 (Chamissonin) C11 H180 8 M 408.447
E1-Emary, N.A. et al, Phytochemistry, 1980, 19, 845 (Argentiolide
Constit. of C. scabiosa and other C. spp. Cryst. (Etp).
A)
Gao, F. et al, Phytochemistry, 1986, 25, 137 (cryst struct, Mp 118-120°. [1X]i? + 101.0° (c, 3.7 in CHC13).
Acetylchamissonin) 15-(2-Hydroxymethyl-2E-butenoyl):
C10H 260 6 M 362.422
Constit. of Gochnatia discoidea. Gum.
15-(2-Acetoxymethyl-2E-butenoyl):
C 22 H 180 7 M 404.459

269
9,10-Dihydroxy-5-oxo-11(13)-... - 8,12-Epoxy-2,5-dihydroxy-1(10),7,11-... Sq-00635 - Sq-00640

Constit. of G. discoidea. Gum. Constit. of Tanacetum polycephalum. Gum. [1X]i;' -48°

15-(4-Hydroxy-2-methyl-2E-butenoyl): (c, 0.3 in CHCI 3).
Czoll:u;06 M 362.422 Rustaiyan, A. eta/, Phytochemistry, 1990, 29, 3022.
Constit. of G. discoidea. Gum.
6-(4-Hydroxy-2-methyl-2E-butenoyl): 4,5-Epoxy-1,6-dihydroxy-10(14),11(13)- Sq-00638
C20H:u;06 M 362.422 germacradien-12,8-olide
Constit. of G. discoidea. Gum.
Porter, T. eta/, Phytochemistry, 1970, 9, 199. OH
I
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2473; 1981, 20, 109 I

(isol)
0
9,10-Dihydroxy-5-oxo-11 (13)-germacren- Sq-00635
12,8-olide
Ct5H 200 5 M 280.320
(1 rx.,4rx..Srx.,6rx.,8rx. )-form
1rx.-Hydroxy-1-desoxotamarin 4rx.,5p-epoxide
Isol. from Tanacetum polycephalum. Gum. [1X]i;' -24° (c,
0.2 in CHCI 3).
Rustaiyan, A. eta/, Phytochemistry, 1990, 29, 3022.

C 15H 110 5 M 282.336

9,10-Epoxy-5,6-dihydroxy-3,11(13)- Sq-00639
germacradien-12,8-olide
(4rx.H,8rx.,9p,1 Orx. )-form
8-(2R-Methylbutanoyl): [75102-67-9]. lneupatorolide A
C20H 300 6 M 366.453
Constit. of lnula eupatorioides. Oil.
8-Angeloyl: [75102-68-0]. lneupatorolide B 0
C20H 280 6 M 364.438
Constit. of I. eupatorioides. Oil.
Herz, W. eta/, J. Org. Chern., 1980, 45, 4838.

CtsH 200 5 M 280.320

1,5-Epoxy-4,6-dihydroxy-1 0(14),11(13)- Sq-00636 (3Z,5p,6rx.,9P,10f/)-form
germacradien-12,8-olide 6-(3-Methy/-2-butenoyl): [61264-10-6]. Balsamin
[32557-05-4] C20 H 260 6 M 362.422
Constit. of Stizolophus balsamita. Cryst. (EtOH). Mp
242-244°. [IX]~ -45.7° (c, 1.9 in CHCI 3).
Rybalko, K.S. et a/, Khim. Prir. Soedin., 1976, 467; Chern. Nat.
Compd. (Engl. Trans/.), 412.

0 8,12-Epoxy-2,5-dihydroxy-1(10),7,11- Sq-00640
germacratrien-6-one
CtsH2005 M 280.320
(1 rx.,4P.Srx.,6rx.,8rx. )-form
Badgerin
HO~o
s I J 2

Constit. of Artemisia arbuscula. Cryst. (CHC1J1Etp).

Mp 207-208°. [IX]}! +8.S0 (c, 1.2 in EtOH). 0
Shafizadeh, F. eta/, J. Org. Chern., 1972, 37, 274.
OH
C 15H 200 4 M 264.321
4,5-Epoxy-1,6-dihydroxy-9,11(13)- Sq-00637 (1(10)E,11:,.51:,)-form
germacradien-12,8-olide 0 2-Me, 5-Ac: 5-Acetoxy-1-methoxy-1(10)E-
furanogermacren-~one
C18H 240 5 M 320.385

Hh-0~0
Constit. of oil of myrrh (Commiphora molmol). Cryst.

w
Mp 116°.
Brieskom, C.H. eta/, Tetrahedron Lett., 1980, 1511.

C 1sH2005 M 280.320
(1rx.,4rx..SP,6rx.,8rx.,9Z)-form
1rx.-Hydroxydesacetylirinol-4rx..5fl-epoxide

270
3,10-Epoxy-5,6-dihydroxy-1-oxo-... - 8,12-Epoxy-1(10),4,7,11-... Sq-00641 - Sq-00647

3,10-Epoxy-5,6-dihydroxy-1-oxo- Sq-00641 (lrx.,4E,8rx.,l0fl)-form

2,4(15),11(13)-germacratrien-12,8-olide Cons tit. of Critonia quadrangular is. Oil.
Jakupovic, J. et al, Phytochemistry, 1987, 26, 451.

4,5-Epoxy-1(10),11(13)-germacradien- Sq-00645
12,8-olide

0 [IT-O'J=
C 15H 160 6 M 292.288
~ 0 (1(10)E,4cx,5cx,8cx)-/orm
(5rx.,6rx.,8rx.,10fl)-form C15H 200 3 M 248.321
5,6-Dihydroxy-4(15)-isogoyazensenolide (1(10)E,4rx.,5rx.,8rx.)-form [110269-98-2] Quadrangolide
6-Angeloyl: Constit. of Eupatorium quadrangulare. Cryst. (MeOH).
C 20H 220 7 M 374.390 Mp 118-!20°. [oc]i;1 +227°.
Constit. of Lychnophora sellowii. Cryst. (Etp). Mp (1(10)E,4P,5rx.,8rx.)-form [87480-83-9]
172°. [oc]~ -43° (c, 1.0 in CHC1 3). lsol. from Calea szyszylowiczii. Oil.
(5p,6rx.,8rx.,l0fl)-form Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227.
6-Angeloyl: Constit. of L. sellowii. Gum. Hubert, T.D. et al, Phytochemistry, 1987, 26, 1751 (Quadrangolide)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1087.
8,12-Epoxy-1(10),4,7,11-germacratetraene Sq-00646
8,12-Epoxy-1(1 0),4-germacradiene-6,12- Sq-00642 [19912-61-9]
diol

C15H 200 M 216.322

(1(10)E,4E)-form
C1sH2403 M 252.353 Furanodiene. Isofuranodiene
(1(10)E,4E,6p,8rx.,llrx.H,12fl)-form [88125-18-2] Constit. of Curcuma zedoaria and Stenocylax michelii.
Hallerol Cryst. Mp 66°.
Obt. by saponification of Hallerin, Sq-00558. Cryst.
Hikino, H. et al, Chern. Pharm. Bull., 1970, 18, 752 (isol)
(EtOAcjEtp). Mp 149-150°. [oc]i,S -64° (c, 1.2 in Riicker, G. et al, Phytochemistry, 1971, 10, 221 (isol)
CHC1 3).
Calleri, M. et al, J. Chern. Soc., Perkin Trans. 1, 1983, 2027 (cryst
struct) 8,12-Epoxy-1(10),4,7 ,11-germacratetraen- Sq-00647
15-oic acid
1,10-Epoxy-4,11(13)-germacradiene- Sq-00643
12,8;15,6-diolide
/0

~0 CisH180 3 M 246.305
(1(10)E,4E)-form [21678-23-9] Sericenic acid
Constit. of Neolitsea sericea. Powder. Mp 203°.
0 Me ester: [21678-22-8]. Sericenine
C 15H 160 5 M 276.288 C 16H 200 3 M 260.332
(1 rx.,6rx.,8rx.,l Ofl)-form Constit. of N. sericea. Cryst. Mp ll5°.
Deoxymikanolide (1(10)E,4Z)-form [32180-36-2] Fischeric acid
Constit. of Mikania scandens. Cryst. (Me 2COjhexane). Constit. of Neolitsea fischeri. Cryst. Mp 158°.
Mp 198-200°. [oc]i,S +98.9° (c, 1.6 in dioxan). Me ester: [29292-34-0]. Neosericenine
Herz, W. et al, J. Org. Chern., 1970, 35, 1453. C 16H 200 3 M 260.332
lsol. from N. sericea. Bp0_2 80-85° (bath).
1,10-Epoxy-4,11(13)-germacradien-12,8- Sq-00644 Hayashi, N. et al, Tetrahedron Lett., 1968, 4957 (isol)
olide Takeda, K. et al, J. Chem. Soc. C, 1970, 985, 1547 (isol, struct)
Joshi, B.S. et al, Indian J. Chern., 1971, 9, 80 (Fischeric acid)
Tori, K. et al, Tetrahedron Lett., 1971, 4355 (pmr)
Honan, M.-C. et al, J. Org. Chern., 1985, 50, 4326.

M 248.321

271
8,12-Epoxy-1(10),4,7,11-... - 1,10-Epoxy-2,4,11(13)-... Sq-00648 - Sq-00653

8,12-Epoxy-1(1 0),4,7, 11-germacratetraen- Sq-00648 Constit. of L. strychnifolia. Cryst. (Me 2CO). Mp 190-
2-ol 191° dec. [1X]i;' + 180.3° (c, 1 in dioxan).
2-Hydroxyfuranodiene (1(1 O)Z,6rx )-form [263 79-18-0] Neolinderalactone
Constit. of L. strychnifolia. Prisms (MeOH). Mp 116-
1180. [1X]i;' + 100° (c, 1.09 in EtOH).
Joshi, B.S. et a/, Tetrahedron, 1967, 23, 261 (struct)
Takeda, K. et a/, J. Chern. Soc. C, 1969, 1491, 2786 (iso/, struct,
abs conjig)
Tori, K. et a/, Tetrahedron Lett., 1975, 4583 (cmr)
C15H 20 0 2 M 232.322 Gopa1an, A. eta/, J. Org. Chern., 1984, 49, 2317 (synth)
(1(10)E,2rx,4E)-form

w
Ac: 8,12-Epoxy-1(10),4,7,11-germacratetraen- Sq-00651
C17H 22 0 3 M 274.359 6-one
Constit. of Commiphora myrrh. Shows ixodicidal
activity. Cryst. Mp 82-83°. [1X]n + 75° (c, 0.93 in CHCI 3).
Me ether: 8,12-Epoxy-2-methoxy-1(10),4,7,11-
germacratetraene. 2-Methoxyfuranodiene (I(IO)E,4E)-[O<m
Ct6H220 2 M 246.349
0
Constit. of C. myrrh. Shows ixodicidal activity. Cryst.
Mp 84-85°. [1X]n +68° (c, 1.106 in CHCI 3). Ct5Ht80 2 M 230.306
(1(10)E,2~,4E)-form (l(JO)E,4E)-form [24268-41-5] Furanodienone
Ac: Constit. of Curcuma zedoaria. Cryst. Mp 89.5-90.5".
C17H2203 M 274.359 (l(JO)E, 4Z)-form [24268-42-6] lsofuranodienone
!sol. from essential oil of myrrh. Wax. Constit. of C. zedoaria. Cryst. (pet. ether). Mp 70-71°.
Me ether: 4,5-Dihydro: 8,12-Epoxy-1(10),7,11-germacratrien-6-one
Ct6H220 2 M 246.349 Ct5H20 0 2 M 232.322
!sol. from essential oil of myrrh. Needles. Mp 58-59°. From essential oil of myrrh Commiphora mukul. Liq.
Maradufu, A., Phytochemistry, 1982, 21, 677. (1(10)Z,4Z)-form
Brieskorn, C.H. et a/, Phytochemistry, 1983, 22, 1207. Constit. of essential oil of myrrh C. mukul. Liq.
Hikino, H. eta/, J. Chern. Soc., Perkin Trans. 1, 1975, 478
8,12-Epoxy-1(10),4,7,11-germacratetraen- Sq-00649 (Isofuranodienone, Furonodienone)
Brieskorn, E.H. eta/, Phytochemistry, 1983, 22, 1270.
15-ol

M
8,12-Epoxy-1(10),4,7,11-germacratetraen- Sq-00652
9-one

CH20H
C15H 200 2 M 232.322
(l(JO)E,4Z)-form [30645-24-0) (1(10)E,4E)-form
Neosericenol
Ac: Neosericenyl acetate Ct5Hta02 M 230.306
C17H 22 0 3 M 274.359 (l(JO)E,4E)-form [58511-21-0] Furanocaulesone A
Constit. of Lindera strychnifolia. Cryst. (Etp). Mp 68- Constit. of Asarum caulescens. Cryst. Mp 105-106°.
690. (l(JO)Z,4E)-form [58535-46-9] Furanocaulesone B
15-Carboxylic acid: see 8,12-Epoxy-1(10),4,7,11- From A. caulescens. Cryst. Mp 95-96°.
germacratetraen-I5-oic acid, Sq-00647 (l(JO)Z,4Z)-form [58511-22-1] Furanocaulesone C
Tada, H. eta/, J. Chern. Soc. C, 1971, 1070. From A. caulescens. Cryst. Mp 97-98°.
Endo, J., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1975. 95, 1321.
8,12-Epoxy-1(1 0),4,7, 11-germacratetraen- Sq-00650

9{
15,6-olide 1,10-Epoxy-2,4,11(13)-germacratriene- Sq-00653
12,8;14,6-diolide
(I(IO)E,6o)-fonn

C 15Ht 60 3 M 244.290
(1(10)E,6rx)-form [728-61-0] Linderalactone 0
Constit. of Lindera strychnifolia. Cryst. (MeOH). Mp
140°. [IX]~ + 102° (c, I in dioxan). c.5HI4o5 M 274.273
4P,5P-Epoxide: [13476-25-0]. 4,5;8,12-Diepoxy-1(10),7,11- (lp,2Z,6rx,8rx,10rx)-form [114742-71-1] Anhydroscandenolide
germacratrien-15 ,6-olide. Linderane Constit. of Mikania urticifolia. Cryst. Mp 73-75°.
Ct5Ht60 4 M 260.289 Gutierrez, A.B. eta/, Phytochemistry, 1988, 27, 938.

272
8,12-Epoxy-1(10),7,11-germacratrien-... - 1,10-Epoxy-6-hydroxy-4,11(13)-... Sq-00654 - Sq-00659

8,12-Epoxy-1(10),7,11-germacratrien-5- Sq-00654 1,10-Epoxy-5-hydroxy-4(15),11(13)- Sq-00657

one germacradien-12,8-olide

0
C 15H 20 0 2 M 232.322
(l(JO)E,4rx.H)-form [81678-18-4] Furanogermenone
Constit. of Zedoariae rhizoma. Cryst. Mp 46.5-47.5°. OH
[1X]i,2 + 135° (CHCI 3). C 15H 200 4 M 264.321
Shibuya, H. et al, Heterocycles, 1982, 17, 215. (1 p,5p,8rx.,1 Orx. )-form
Constit. of Calea szyszylowiczii. Oil.
1,10-Epoxy-3-hydroxy-4,11(13)- Sq-00655 Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227.
germacradiene-12,8; 15,6-diolide
1,10-Epoxy-6-hydroxy-3,11(13)- Sq-00658

HO'~O mo
germacradien-12,8-olide
0

0
CisHI60 6 M 292.288 OH
(1 rx.,3rx.,6rx.,8rx.,1 Of/)-form C 15H 200 4 M 264.321
Ac: [23758-16-9]. Scantknolide (1~,4Z,6P,8rx.,10~)-form
C 17H 180 7 M 334.325 Angeloyl: [72165-11-8]. Tanadin
Constit. of Mikania scandens. Cryst. C20 H 260 5 M 346.422
(Me 2CO/diisopropyl ether). Mp 230-234°. [<X]:,S + 62° (c, Cryst. (EtOH). Mp 146-147°. [1X]i,2 +42° (c, 1.2 in
1.1 in dioxan). MeOH).
JJC,,J3-Dihydro, Ac: [23758-17-0]. 3<X-Acetoxy-1,10-epoxy-4- Yunusov, A.l. et al, Khim. Prir. Soedin., 1979, 411.
germacrene-12,8: 15,6-diolide. Dihydroscandenolide
C 17H 200 7 M 336341
1,10-Epoxy-6-hydroxy-4,11(13)- Sq-00659

Mo (I~.4E,6a,8",
Constit. of M. scandens. Cryst. (Me 2COjhexane). Mp
278-280° dec. [<X]i,S + 83.3° (c, 0.54 in dioxan). germacradien-12,8-olide
Herz, W. et al, J. Org. Chern., 1970, 35, 1453.

4,5-Epoxy-6-hydroxy-1(10),11(13)- Sq-00656
IO"),{o'm
germacradiene-12,8; 14,2-diolide
OH
0
C1sH2004 M 264.321
(1P,4E;6rx.,8rx.,10rx.)-form
1,10-Epoxydesacetyllaurenobiolitk
Constit. of Mikania pohlii. Gum. [1X]~4 -28° (c, 0.05 in
CHCI 3).
0
Ac: [28272-18-6]. Pyrethrosint. Chrysanthin
C 17H 220 5 M 306.358
C1sH1606 M 292.288 Isol. from Chrysanthemum cinerariaefolium. Cryst. Mp
(1p,4rx.,5p,6rx.,8rx.)-form [10247-71-9] 198-200°. [1X]n -31° (c, 1.73 in CHC1 3).
Elephantol Angeloyl: [57138-50-8]. Tanacin
Produced by alkaline hydro!. of Elephantopin and C20 H 260 5 M 346.422
Elephantin Cryst. Mp 282-284°. [<X]i,' ;+ 274°. Constit. of Tanacetum pseudoachillea. Cryst. (EtOH).
Kupchan, S.M. et al, J. Org. Chern., 1969, 34, 3867 (synth) Mp 128-129°. [IX]~ -74° (c, 1.0 in MeOH).
McPhail, A.T. et al, J. Chern. Soc., Perkin Trans. 2, 1972, 1313
(1 p,4E,6rx.,8P,1 Orx. )-form
(cryst struct)
1,1O-Epoxy-6rx.-hydroxyinunolitk
Constit. of M. pohlii and M. goyazensis. Gum. [rxln
-28° (c, 0.05 in CHCI 3).
Iriuchijima, S. et al, Tetrahedron Lett., 1967, 1965 (Pyrethrosin)
Gabe, E.J. et al, J. Chern. Soc., Chern. Commun., 1971, 559 (cryst
struct, Pyrethrosin)
Yunusov, AI. et al, Khim. Prir. Soedin., 1976, 170 (Tanacin)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1349.
Makhmudov, M.K. et al, Khim. Prir. Soedin., 1988, 59; Chern.
Nat. Compd. (Engl. Trans/.), 49 (cryst struct)

273
4,5-Epoxy-2-hydroxy-1(10),11(13)-... - 8,12-Epoxy-9-hydroxy-1(10),4,7,11-... Sq-00660 - Sq-00665

4,5-Epoxy-2-hydroxy-1(10),11(13)- Sq-00660 8,12-Epoxy-1-hydroxy-5,7,9,11- Sq-00664

germacradien-12,8-olide germacratetraen-15,6-olide

C 15H 100 4 M 264.321

(l(JO)Z,2rz,4rz,Sfl,8JI)-form [27875-37-2] Baileyin
Constit. of Baileya pleniradiata. Cryst. Mp 189°. c.sH.,04 M 260.289
Herz, W. et a/, J. Org. Chern., 1979, 44, 1873. (lfl,6rz,9Z)-form
Ac: [13657-60-8]. Zeylanine
4,5-Epoxy-6-hydroxy-1(10),11(13)- Sq-00661 C 17H 180 5 M 302.326
germacradien-12,8-olide Constit. of the roots of Neo/itsea zey/anica and N.
aciculata. Cryst. (CH 2Cl2 /Et20). Mp 175-177°. [ex]~
(YYO)= +271° (c, 2.5 in dioxan).

~
4P,5P-Epoxide, Ac: [20149-41-1]. Zeylanane
0
(1(10)E,4a,5P,6a,8P)-/orm C 17H 180 6 M 318.326
OH Constit. of N. aciculata. Cryst. (CH 2C12/Etp). Mp 150-
C 15H 100 4 M 264.321 1520. [exln +231.2° (c, 0.99 in CHC1 3).
(1(10)E,4rz,Sfl,6rz,8JI)-form [63597-81-9] Simsiolide Joshi, B.S. et a/, Tetrahedron, 1967, 23, 261, 278 (isol. struct)
Takeda, K. et a/, J. Chern. Soc., Chern. Commun., 1968, 940 (abs
Constit. of Simsia dombeyana. Oil. config)
Ac: Cryst. (Etp). Mp 168-170°. Tori, K. et al, J. Chern. Soc., Chern. Commun., 1968, 943 (pmr)
(1(10)E,4fl,Srz,6rz,8rz)-form [41653-77-4] Spiciformin Takeda, K. et al, J. Chern. Soc. C, 1970, 973 (isol)
Constit. of Artemisia spp. Gum. [exln +81.7° (c, 1.63 in Joshi, B.S., J. Sci. Ind. Res., 1976, 35, 239 (rev)
CHC1 3).
Ac: Mp 154-155°. 8,12-Epoxy-9-hydroxy-1(10),4,7,11- Sq-00665
Shafizadeh, F. eta/, Phytochemistry, 1973, 12, 857 (Spiciformin) germacratetraen-15,6-olide
Bohlmann, F. eta/, Phytochemistry, 1977, 16, 776 (Simsiolide)
OH
I

4,5-Epoxy-6-hydroxy-10(14),11(13)- Sq-00662
germacradien-12,8-olide

("<T~o>=o
0
~
OH
C 15H 160 4 M 260.289
(1(10)E,6rz,9rz)-form
C 15H 100 4 M 264.321
Ac: [20149-38-6]. Litsealactone
(4«,5P,6«,8«)-form C 17H 180 5 M 302.326
4,5-Epoxy-1-desoxodesacetylchrysano/ide Constit. of Neo/itsea aciculata. Cryst. (CH 2Cl 2/Etp).
Constit. of Mikania goyazensis. Gum. Mp 157-159°. [exJi? +57.SO (c, 0.8 in dioxan).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1349. 4P,5P-Epoxide, Ac: [20149-39-7]. Litseaculane
C 17H 180 6 M 318.326
Sq-00663 Constit. of N. aciculata. Cryst. Mp 145-146°. [ex]~
+ 76.1 o (c, 0.4 in dioxan).
IP,JOP:4P,5P-Disepoxide, Ac: [20082-46-6]. Linderatline
C 17H 180 1 M 254.328
Constit. of N. aciculata. Cryst. Mp 130-132°. [ex]i;'
-68.7° (c, 0.3 in dioxan).
(1(10)E,6rz,9JI)-form
Ip,IOex-Epoxide, Ac: [13761-05-2]. Zeylanicine
C 17H 180 6 M 318.326
C 15H 100 4 M 264.321 Isol. from roots of N. zeylanica. Cryst. (CH 2C12/Etp).
[ex]~ -153° (c, 3.13 in dioxan).
(lfl,3Z,Sfl,8rz,10rz)-form [82425-24-9] Purpurascenolide
Constit. of Mikania purpurascens. Cryst. Mp 171-172°. IP,4P:5P,IOex-Diepoxide: Deacetylzeylanidine
[ex]~ -14.3° (c, 0.7 in CHC1 3). c.sH.,o, M 292.288
Constit. of N. zey/anica. Cryst. Mp 207-209°. [cxln +62°
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 705.
(c, 0.36 in CHC1 3).
IP,4P:5P,IOex-Diepoxide, Ac: [13761-06-3]. Zeylanidine
C 17H 180 7 M 334.325
Constit. of N. zeylanica. Cryst. (CH 2Cl2 /Et20). Mp
220°. [ex]~ -174° (c, 3.2 in dioxan).

274
8,12-Epoxy-3-hydroxy-1,7,10(14),11-... - Furanotriene Sq-00666 - Sq-00671

Joshi, B.J. et al, Tetrahedron, 1967, 23, 261, 273 (Zeylanicine, 1,5-Epoxy-5,6,9, 10-tetrahydroxy-11(13)- Sq-00669
Zeylanidine) germacren-12,8-olide
Takeda, K. et al, J. Chern. Soc. C, 1970, 973 (Litsealactone,
Litseaculane, Linderadine)
Das, K.G. et al, Org. Mass Spectrom., 1971, 5, 187 (ms)
Li, W.-S. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1581 (isol, pmr,
cmr, struct)

8,12-Epoxy-3-hydroxy-1,7,10(14),11- Sq-00666
0
germnacratetraen-~ne

C1sH 210 7 M 314.335

(4«H,6«,8«,9P,l Ofl)-form
6,9-Bis(2-methylpropanoyl): [81915-77-7]. lncaspitolide E
C 23 H 340 9 M 454.516
CtsH180 3 M 246.305 Constit. of lnula cuspidata. Gum. [a]i;l -5.1° (c, 0.7 in
CHC1 3).
(1Z.3~,4~)-form
Bohlmann, F. et al, Phytochemistry, 1982, 21, 157.
Me ether: 3-MethoxyfuranogerTTUlCra-1 ,10(14)-dien-6-one
C 16H 200 3 M 260.332
Constit. of oil of myrrh Commiphora molmol. Liq. 2,5-Epoxy-5,6,9,10-tetrahydroxy-11(13)- Sq-00670
Brieskom, C.H. et al, Tetrahedron Lett., 1980, 1511. germnacren-12,8-olide

8,12-Epoxy-2-hydroxy-1(10),7,11- Sq-00667
germacratrien-6-one

HO~o
I,
0 C 15H 210 7 M 314.335
C 15H 200 3 M 248.321 (2«,4«H,5«,6«,8«,9P,10fl)-form
(1(10)E,2~)-form
6-Angeloyl, 9-(2R-methybutanoyl): [75102-66-8].
lneupatolide
Me ether: 2-MethoxyfuranogerTTUlCra-1(10)-en-6-one
C25 H 360 9 M 480.554
C 16H 210 3 M 262.348
Constit. of Inula eupatorioides. Cryst. (EtOAc). Mp 195-
Constit. of oil of myrrh (Commiphora molmol). Cryst.
1960. [aJn -18.3° (c, 0.05 in CHC1 3).
Mp 92°.
(2P,4«H,5P,6«,8«,9P,l0fl)-form
Brieskom, C.H. et al, Tetrahedron Lett., 1980, 1511.
6-(3-Methylbutanoyl), 9-angeloyl: [126616-75-9]. Divaricin
A
5,10-Epoxy-9-hydroxy-11(13)-germacren- Sq-00668 C25H 360 9 M 480.554
12,8-olide Constit. of Carpesium divaricatum. Cryst. (C6HJ. Mp
197-198°. [a]i,O + 13° (c, 0.1 in CHC1 3).
6-(3-Methyl-2-butenoyl), 9-angeloyl: [126582-72-7].
Divaricin C
C25H 340 9 M 478.538
Constit. of C. divaricatum. Cryst. (C 6H 6). Mp 205-207°.
[oc]i? +46° (c, 0.10 in CHC1 3).
6,9-Diangeloyl: [79721-99-6]. Divaricin B
CtsH1z04 M 266.336 C25H 340 9 M 478.538
(4«H,5«,8«,9P,l0«)-form [84 782-38-7] Dittrichiolide Constit. of C. divaricatum, lnula eupatorioides and /.
2-Methylpropanoyl: cappa. Cryst. (C6H 6). Mp 224-225° (178°). [a]i,O + 18° (c,
C 19 H~,0 5 M 338.443 ,_. 0.17 in CHC1 3).
Constit. of Dittrichia viscosa. Gum. Herz, W. et al, J. Org. Chern., 1980, 45, 4838.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1443. Baruah, N.C. et al, J. Org. Chern., 1982, 47, 137 (isol, pmr, ms)
Goswami, A.C. et al, Phytochemistry, 1984, 23, 367 (pmr)
Maruyama, M. et al, Phytochemistry, 1990, 29, 547 (isol, pmr, cmr)

Furanotriene Sq-00671
8,12-Epoxy-J(JO)E,4(15),5E,7,11-germacrapentaene

~
M 214.307

275
1(10),4(15),5,11(13)-... - 1(10),4,11(13)-Germacratrien-12,8-... Sq-00672 - Sq-00678

Struct. revised in 1990. Constit. of the sea plume Constit. of G/echoma hederacea. Cryst. Mp 110°. [a]~
Pseudopterogorgia americana. Oil. + l20.SO (CHCl 3).
Izac, R.R. et a/, Tetrahedron, 1982, 38, 301 (isol) Stahl, E. et a/, Justus Liebigs Ann. Chern., 1972, 757, 2.1 (isol)
Chan, W.R. eta/, Tetrahedron, 1990, 46, 1499 (isol, struct)
1(10),4,7(11)-Germacratrien-12,9-olide Sq-00676

C((Qo
1(10),4(15),5,11(13)-Germacratetraen- Sq-00672
12,8-olide

~0
C 15H 200 2 M 232.322
C 15H 180 2 M 230.306
(1(10)E,4E,9«.)-form [63426-84-6] Cauleslactone
(1(10)E,5E,8«.)-form Constit. of Asarum caulescens. Oil.
Germacrene D lactone
Constit. of Inula spp. Cryst. (Etpjpet. ether). Mp 142°. Endo, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1977, 97,
393.
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1165.

1(10),4,11 (13)-Germacratrien-12,8-olide Sq-00677

1(10),4, 11(13)-Germacratriene-12,8;14,3- Sq-00673 Desacetoxylaurenobiolide
d.iolide

~~0'>=
~0
C 15H 200 1 M 232.322
C 15H 160 4 M 260.289
(l(JO)E,4E,8«.)-form [57759-35-0]
(l(IO)Z,3«.,4E,8«.)-form [82003-39-2] Pertilide Constit. of a Ferreyranthus sp., Callitris columellaris and
Constit. of Pertya glabrescens. Cryst. Inula racemosa. Oil or cryst. Mp 132-133°.
(Me2CO/diisopropyl ether). Mp 186-187°. [a]~ + 1.4° (c, (l(IO)E,4E,8p)-form [22617-75-0] lnunolide
1.5 in CHCl 3). Constit. of Stevia polyphylla. Gum or cryst. Mp 85-86°.
(l(IO)Z,3p,4E,8«.)-form [a]i,2 + 54.4° (c, 4.0 in CHCl 3).
3-Epipertilide 11P,13-Dihydro: [22617-76-l]. 1(10),4-Germacradien-12,8-
From P. glabrescens. Oil. [a]J; + 52° (c, 0.1 in CHCl 3). olide. Dihydroinunolide
Nagumo, S. eta/, Chern. Pharm. Bull., 1982, 30, 586 (cryst struct, C 15Hn0z M 234.338
abs config) Constit. of/. racemosa. Cryst. (EtOH). Mp 128-129°.
Nagumo, S. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1984,
[a]i,S + 120.1° (c, 3.4 in CHCl 3).
104, 1223 (Epipertilide)
Takeda, K. eta/, J. Chern. Soc., Perkin Trans. I, 1975, 870 (synth)
Ravindranath, K.R. eta/, Indian J. Chern., Sect. B, 1978, 16, 27
1(10),4,11 (13)-Germacratriene-12,8;15,6- Sq-00674 (iso/, struct)

80
d.iolide Brecknell, D.J. eta/, Aust. J. Chern., 1979, 32, 2455 (isol)
Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1669 (isol)
Watson, W.H. eta/, J. Org. Chern., 1986, 51, 2521 (struct)
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835 (isol)
Paknikar, S.K. eta/, Planta Med., 1988, 54, 186 (strucn

0 1(10),4,11(13)-Germacratrien-12,8-olid-14- Sq-00678
oic acid
CtsH1604 M 260.289
(1(10)E,6«.,8p)-form [22391-22-6] Isabelin COOH
From leaves of Ambrosia psilostachya. Cryst. (EtOAc).
Mp 170°. [a]i,S -57.2° (c, 0.87 in CHCl 3). Exists in a
10:7 ratio of two conformers. (l(lO)E,4E,8cx):form
0
Yoshioka, H. eta/, J. Chern. Soc., Chern. Commun., 1968, 1679
(isol)
Yoshioka, H. et a/, Tetrahedron, 1969, 25, 4767 (struct)
Tori, K. eta/, J. Chern. Soc. B, 1971, 1084 (config) C 15Ht80 4 M 262.305
Wender, P.A. eta/, J. Am. Chern. Soc., 1980, 102, 6340 (synth)
(l(IO)E,4E,8«.)-form [126621-22-5]
Cons tit. of Actotis arctotoides.
1(10),4,7(11)-Germacratrien-12,8-olide Sq-00675
(l(IO)Z,4E,8«.)-form [87741-69-3] Pertic acid
Needles (Me2C0jdiisopropyl ether). Mp 152-153°. [a]~
-72.7° (c, 0.4 in CHCl 3).
P-D-Glucopyranosyl ester: [87764-21-4].
Cl1H 280 9 M 424.447

CtsHll,Oz M 232.322
(l(IO)E,4E,8~)-form [38146-68-8] Glechomanolide

276
6-Hydroxy-4,9-germacradien-12,8-... - 15-Hydroxy-1(10),4,11(13)-... Sq-00679 - Sq-00685

Constit. of leaves of Pertya glabrescens. Amorph. 5-Hydroxy-1(10),4(15),11(13)- Sq-00683

powder. [1X]i;' -48.6° (c, 0.5 in EtOH). germacratrien-12,8-olide
Nagumo, S. et al, Chern. Pharm. Bull., 1983, 31, 2302.
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 195 (isol, pmr, cmr)
~~~-o)=o

~
6-Hydroxy-4,9-germacradien-12,8-olide Sq-00679

~,o'>=o C15H 200 3 M 248.321

CtsH 20 0 3
Y"0
M 248.321
(l(JO)E,5P,8rz)-form
Constit. of Calea szyszylowiczii. Cryst. (Et20/pet. ether).
Mp 163°.
5-Ketone: 5-0xo-1(10)E,4(15),11(13)-germacratrien-12,8rz-
(4E,6rz,8rz,9E)-form olide
Constit. of Mikania goyazensis. Gum. C15H 180 3 M 246.305
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1349. From C. szyszylowiczii. Oil.
lfi,l01X-Epoxide: see I,IO-Epoxy-5-hydroxy-4(!5),!!(!3)-
3-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00680 germacradien-!2,8-olide, Sq-00657

H00
(1(10)E,5p,8fJ)-form
12,8: 15,6-diolide
Ac: [71609-01-3]. Maroniolide
C1sH2o04 M 264.321
lsol. from Munnozia maronii. Cryst. (Et20jpet. ether).
Mp 160°. [1X]14 -45° (c, 0.2 in CHCI 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 334 (Maroniolide)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227.
0
CtsH 160 5 M 276.288 6-Hydroxy-1(10),4,11(13)-germacratrien- Sq-00684
(1(10)E,3P,6rz,8fJ)-form 12,8-olide
3P-Hydroxyisabelin
Constit. of Mikania cynanchifolia. Cryst. [1X]t' +4° (c,
0.15 in CHCI 3).
Ac:
Ct,Ht80 6 M 318.326
~0 (I(IO)E,4E,6a,8a)-form

From M. cynanchifolia. Cryst. Mp 163.SO. [1X]14 + 7° (c, OH

0.3 in CHCI 3). CtsH200 3 M 248.321
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1099. (1(1 O)E,4E,6rz,8rz )-form [3500 1-24-2] DesacetyUaurenobiolide
C 15H 200 3 M 248.321
2-Hydroxy-l (1 0),4,11 (13)-germacratrien- Sq-00681 Constit. of Artemisia spp. Gum. [1X]n + 34.5° (c, 1.6 in
12,8-olide CHCI 3).
Ac: [35001-25-3]. Laurenobiolide
C 17H 220 4 M 290.358
HOY'r[-O)=o Constit. of Laurus nobilis. Cryst. (Et 20/hexane). Mp
101-103°. [1X]n +17.1° (EtOH).

~ (1(10)E,4E,6P,8rz)-form
6-Epidesacetyllaurenobio/ide
C 15H 20 0 3 M 248.321 Constit. of Montanoa grandiflora. Cryst. (CHC1 3jpet.
(1(10)E,2p,4E,8r~.)-form [125290-02-0] ether). Mp 117-118°.
Constit. of Geigeria rigida. Gum. Tada, H. et al, J. Chern. Soc., Chern. Commun., 1971, 1391 (struct)
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr) Shafizadeh, F. et al, Phytochemistry, 1973, 12, 857 (isol)
Tada, H. et al, Chern. Pharm. Bull., 1976, 24, 667 (isol)
Tori, K. et al, Tetrahedron Lett., 1976, 387 (cmr)
3-Hydroxy-1(1 0),4,11(13)-germacratrien- Sq-00682 Bohlmann, F. et al, Phytochemistry, 1982, 21, 1169 (isol)
12,8-olide Quijano, L. et al, Phytochemistry, 1984, 23, 1971 (isol)

01'0'>= 15-Hydroxy-1(1 0),4,11(13)-germacratrien., Sq-00685

m
HO~O 12,8-olide

C 15H 20 0 3 M 248.321
(1(10)E,3P,4E,8rz)-form
Constit. of Pegolettia senegalensis. Gum. ;,;,OH \ O
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1637.
Ct5H 200 3 M 248.321
(1(10)E,4Z,8rz)-form
Constit. of Arctotis aspera.
Ac: [126621-23-6]. 15-Acetoxy-1(10),4,11(13)-germacratrien-
12,81X-olide

277
3-Hydroxy-1(10),4,11(13) ... - Tanargyrolide Sq-00686 - Sq-00692

C 17H 220 4 M 290.358 1-0xo-4,10(14),11(13)-germacratrien- Sq-00689

Constit. of A. aspera. 12,8-olide
11P,13-Dihydro: 15-Hydroxy-1(10),4-germacradien-12,8fJ.-
olide
C 15H 220 3 M 250.337
Constit. of A. aspera.
(J(JO)E,4E,8r~.)-form
15-A/dehyde: [75088-73-2]. 15-0xo-1(10),4,11(13)-
germacratrien-12 ,8fJ.-olide. Liabinolide C 15H 180 3 M 246.305
!sol. from Liabum .floribundum. Oil.
(4E,8r~.)-form
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 579 (Liabinolide) Constit. of Calea szyszylowiczii. Oil.
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 195 (isol, pmr, cmr)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2227.

3-Hydroxy-1(10),4,11(13)germacratrien- Sq-00686
12,8-olid-14-oic acid 14-0xo-1(10),4,11(13)-germacratrien- Sq-00690
12,8-olide
CHO

C 15H 180 5 M 278.304

[87741-73-9] 3r~.-Hydroxypertic acid
(l(JO)Z,3r~.,4E,8r~.)-forin
~0
Needles (Me 2COjdiisopropyl ether). Mp 250-252°. [fJ.]:i C15H 200 3 M 248.321
+ 1.6° (c, 1.0 in CHC13). (1(JO)E,4E,8r~.)-form[36790-43-9] Frutescin
P-v-Glucopyranosy/ ester: [87741-70-6]. Constit. of Ivafrutescens. Cryst. Mp 158-160°
C21 H 280 10 M 440.446
Herz, W. eta/, Phytochemistry, 1972, 11, 1829 (isol)
Isol. from Pertya glabrescens. Amorph. powder. [fJ.]::i Herz, W. eta/, J. Org. Chern., 1982, 47, 2206 (cryst struct)
-10.9° (c, 2.0 in Py).
Nagumo, S. et a/, Chern. Pharm. Bull., 1983, 31, 2302.
3-0xo-1(1 0)-germacren-12,8-olide Sq-00691
15-Hydroxy-1-oxo-4,10(14),11(13)- Sq-00687
germacratrien-12,8-olide ~o'=o
0~

~o'-o
: I

C 15H 220 3 M 250.337

(4PH,8P,llPffl-form

C 15H 180 4
~
M 262.305
Constit. of Stevia yaconensis. Cryst. Mp 103-104°.
Gil, R. eta/, Phytochemistry, 1990, 29, 3881 (isol, pmr, cmr)

(4Z,8Jl)-:form Tanargyrolide Sq-00692

Ac: (98644-44-1]. Calbertolide A I fJ.,4fJ.- Epoxy-5fJ.,6fJ.-dihydroxy-I (I 0), II ( I3)-germacradien-
12,8fJ.-o/ide
C 17H 200 5 M 304.342
Constit. of Calea berteriana. Gum. [128530-11-0]
4fJ.,5fJ.-Epoxide, Ac: (98659-28-0]. Calbertolide B
C 17H 200 6 M 320.341
From C. berteriana. Gum.
Ober, A.G. eta/, Phytochemistry, 1985, 24, 1743. 0

Isofuranotriene Sq-00688 I

8,12-Epoxy-3,5,7,10(14),11-germacrapentaene HO
C15H 200 5 M 280.320
Constit. of Tanacetum argyrophyllum var. argyrophyllum.
Oil.
Goren, N. eta/, Phytochemistry, 1990, 29, 1467 (iso/, pmr)

C1sH180 M 214.307
This struct. prev. assigned to Furanotriene, Sq-00671.
Constit. of sea plume Pseudopterogorgia americana.
Yellow oi~
Chan, W.R. ;; at, Tetrahedron, 1990, 46, 1499 (isol, struct)

278
2,6,10,13-Tetrahydroxy-3,7(11),8-••• - 6,14,15-Trihydroxy-1(10),4,11(13)-... Sq-00693 - Sq-00698

2,6,10,13-Tetrahydroxy-3,7(11),8- Sq-00693 6,9,15-Trihydroxy-1(10),11(13)- Sq-00696

gennacratrien-12,8-olide gennacradien-12,8-olide

HO#O
OH

H~o
(>H 13CHpH
C15H 220 5 M 282.336
(2oc,3Z,6oc,JOocOH)-form
(l(JO)E,4ocH,6fl,8~,9~)-form
6-(2-Methylpropenoy/), 2-Ac: [76010-17-8]. Rolandrolide
6-(2-Methylbutanoy/): [80368-04-3]. Zinangustolide
CztH160 8 M 406.432
C10H 300 6 M 366.453
Constit. of Rolandra fruticosa. Noncryst.
Constit. of Zinnia angustifolia. Gum. [oc]~ +21.3° (c, 8.3
6-(2-Methy/propenoyt:), 2,13-di-Ac: [76010-16-7]. in CHC1 3).
C13H 180 9 M 448.469
llp,JJ-Dihydro, 6-(2-methylbutanoy/): llfl,13-
Constit. of R.fruticosa. Cryst. (EtOAc). Mp 174-175°.
Dihydrozinangustolide
[oc] 0 +60.6° (c, 0.05 in CHC1 3).
C10H 3z06 M 368.469
Herz, W. eta/, J. Org. Chern., 1981, 46, 761. Constit. of Z. angustifolia. Gum. [oc]~ -19.8° (c, 0.42 in
CHC1 3).
5,6,9,10-Tetrahydroxy-1-oxo-11(13)- Sq-00694 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1623.
gennacren-12,8-olide
3,6,9-Trihydroxy-1(10),4(15),11(13)- Sq-00697
gennacratrien-12,8-olide

C 15H 220 7 M 314.335

(4ocH,5fl,6oc,8oc,9fl,lOp)-form
0

C 15H 100 5
HO#O
M 280.320
(l(JO)E,3fl,6fl,8oc,9p)-form
5,9-Bis-(2-methylpropanoy/): [81915-78-8]. Incaspitolide D Mp 77°. +7.
C13H 340 9 M 454.516
6(or 9)-Angeloyl, 9(or 6)-Ac: [1.02907-30-2]. Jamaicolide D
Constit. of Inula cuspidata. Cryst. Mp 229-231°. [oc]~4
C 22 H 180 7 M 404.459
-95° (c, 0.3 in CHC1 3).
Constit. of Caleajamaicensis. Gum.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 157.
Ober, A.G. eta/, Phytochemistry, 1986, 25, 877.

1,10:4,5:8,12-Triepoxy-7,11- Sq-00695 6,14,15-Trihydroxy-1(10),4,11(13)- Sq-00698

germacradiene gennacratrien-12,8-olide
0 CH20H

CISH1003
~
M 248.321
0

(lfl,4«,5fl,l0oc)-form [38146-67-7] Glecho11Ulfuran. HOH2

Alexandrofuran
Constit. of Smyrnium o/usatrum and G/echoma C 15H 100 5 M 280.320
hederacea. Cryst. (pet. ether). Mp ll5°. [oc]i? + 151.5° (1(10)E,4E,6oc,8«)-form
(CHC1 3). 14-Hydroxy-cis,cis-artemisifolin
Stahl, E. et al, Justus Liebigs Ann. Chern., 1972, 757, 23 (isol) 6-Tigloyl:
Oksuz, A. U.S. et al, J. Nat. Prod. (Lloydia), 1983, 46, 490 (cryst C10H 160 6 M 362.422
struct) Constit. of Gochnatia discoidea. Gum.
Gonzalez, A.G. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 1307 (cryst
struct) Bohlmann, F. eta/, Phytochemistry, 1981, 20, 109.

279
6,9,10-Trihydroxy-5-oxo-11(13)-... - 16-(1-Methyl-1-propenyl) ... Sq-00699 - Sq-00704

6,9,10-Trihydroxy-5-oxo-11(13)- Sq-00699 Constit. of Eremanthus e/aeagnus. Cryst. M p 181-183 °. [cx] 0

germacren-12,8-olide + 65° (EtOH).
Raffauf, R.F. eta/, J. Am. Chern. Soc., I975, 97, 6884 1cryst
struct)

Eremantholide B Sq-00702
0 [69883-96-1]
As Eremantholide A, Sq-00701 with
0 R = CH(CH 3)CH 2CH 3
C 15H 120 6 M 298.335 C10H 260 6 M 362.422
(4«.H,6«.,8«.,9P,J 0/1)-form Constit. of Eremanthus e/aeagnus. Cryst. Mp 233°. [cx] 0
6-Hydroxy-9-desacy/ineupatoro/ide + 60° (EtOH).
9-(3-Methyl-2E-pentenoyl): Le Quesne, P.W. eta/, J. Chern. Soc., Perkin Trans. I, 1978, I572.
C11 H 300 7 M 394.464
Constit. of Dittrichia viscosa. Cryst. (EtzO/pet. ether). Eremantholide C Sq-00703
Mp 191-192°. [cx]i;l +44° (c, 0.5 in CHC1 3) (as 6-Ac). 16cx-lsopropenyleremantholanolide
6,9-Bis(2-methylpropanoyl): [81915-79-9]. lncaspitolide A [69883-97-2]
C23H 340 8 M 438.517
Isol. from Inula cuspidata. Cryst. Mp 158-159°. [cx]~4 As Eremantholide A, Sq-00701 with
+42° (c, 0.2 in CHCI3). R = t7C(CH3)=tscH2
Bohlmann, F. eta/, Phytochemistry, I982, 21, I57,I443.
C 19H 120 6 M 346.379
Constit. of Eremanthus elaeagnus. Cryst. (EtOH). Mp 229-
2300. [cx] 0 -12.7° (EtOH).
15-Hydroxy: 15-Hydroxyerenumtholide C
C 19H120 7 M 362.379
Nor- and Constit. of Piptolepis leptospermoides.
4P,5-Dihydro: 16«.-lsopropenyi-4P,5-

homogermacranes dihydroerenumtholanolide
C19H 240 6 M 348.395
Constit. of E. bicolor. Cryst. (EtzOjpet. ether). Mp 245°.
4p,5,17,18-Tetrahydro:
C 19H 260 6 M 350.411
Constit. of E. bicolor. Gum.
Caleamyrcenolide Sq-00700
Le Quesne, P.W. eta/, J. Chern. Soc., Perkin Trans. I, 1978, I572.
[84749-85-9] Bohlmann, F. eta/, Phytochemistry, I980, 19, 2663; I982, 21, I439
(derivs)

16-(1-Methyl-1- Sq-00704
propenyl)eremantholanolide
0

(17£)-form
C30H 380 6 M 494.627
Constit. of Ca/ea hymenolepis. Gum.
Bohlmann, F. eta/, Phytochemistry, I982, 21, 2045.
C10H 240 6 M 360.406
(17£)-form
Eremantholide A Sq-00701 Constit. of Eremanthus bicolor. Cryst. (Et 20jpet. ether).
[58030-93-6] Mp 222°. [cx]~4 -42° (c, 0.6 in CHCI3).
4P,5-Dihydro:
0
C10H 260 6 M 362.422
Constit. of E. bico/or. Cryst. (Et20/pet. ether). Mp 227°.
[cx]i;l +40.9° (c, 0.22 in CHC1 3).
(17Z)-form
15-Hydroxy: 15-Hydroxy-16-(l-methyl-1-
propenyl)ere11Ulntholide
C10H 240 7 M 376.405
R = CH(CH 3)2 Isol. from Lychnophora bahiensis and L. crispa. Gum.
[cx]~4 -20° (c, 0.3 in CHCI 3).
M 348.395 15-Acetoxy:

280
Mikagoyanolide - 8,9-Epoxy-8,9-seco-1(10),4,7(11)-... Sq-00705 - Sq-00711

C22H 260 8 M 418.443

lsol. from L. bahiensis. Gum.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2663; 1982, 21,
1087.
Secogermacranes
~agoyaooHde Sq-00705
[83790-32-3)
AntheioduroHde A Sq-00708
[130252-70-9]

C30H 400 6 M 496.642 C15H 100 4 M 264.321

Constit. of Mikania goyazensis and M. pohlii. Gum. [()()~4 Isol. from Anthemis pseudocotula. Oil.
-26° (c, 0.4 in CHCI 3). El-Ela, M.A. eta/, Phytochemistry, 1990, 29, 2704 (isol, pmr, cmr)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1349.
AntheioduroHde B Sq-00709
11,12,13-Trioor-1(10),4,6-germacratrieoe Sq-00706 [130252-69-6]
1,5-Dimethyl-} ,5,7-cyclodecatriene
[20082-17-1)

C12H 18 M 162.274
CtsH 180 5 M 278.304
(l(JO)E,4E,6Z)-form A seco-germacranolide from Anthemis pseudocotu/a. Oil.
Pregeijerene
El-Ela, M.A.- eta/, Phytochemistry, !990, 29, 2704 (isol, pmr, cmr)
Constit. of Geijera parvijlora, Ruta graveolens and Rubus
rosifolius. Oil. Bp5 82°.
AgN0 3 adduct: [21687-41-2). AnthepseudoHde Sq-00710
Cryst. (EtOH). Mp 121-123°. [130252-68-5)
Jones, R.V.H. eta/, Aust. J. Chern., 1968, 21, 2255.
CHO
Coggon, P. eta/, J. Chern. Soc. B, 1970, 1024 (cryst struct)

~0
Kubeczka, K.H., Phytochemistry, 1974, 13, 2017.

Uvarisesquiterpeoe A Sq-00707
[117176-62-2]
C 15H 100 4 M 264.321

&~'T
Isol. from Anthemis pseudocotula. Oil.
Ac: [130252-63-0]. Antlu!pseudolide acetate
C17H 120 5 M 306.358
Constit. of A. pseudocotula. Oil.
El-Eia, M.A. eta/, Phytochemistry, 1990, 29, 2704 (isol, pmr, ms)

C22H 310 1 M 328.494 8,9-Epoxy-8,9-seco-1(1 0),4,7(11 )- Sq-00711

Constit. of Uvaria angolensis. Amorph. [()() 0 -16° (c, 0.12 germacratrien-12,8-oHde
in CHCI 3).
Muhammad, I. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 719.

C15H 100 3 M 248.321

(l(JO)E,4E)-form [94444-44-7) 8,9-Epoxy-8,9-
secoglechomonolide
Constit. of Smyrnium rotundifolium. Cryst. Mp 138°.
Goren, N. eta/, Phytochemistry, 1984, 23, 2281.

281
8-Hydroxy-2,3-seco-4,11(13)-... - 2,3,8-Trihydroxy-2,3-seco-1(10) ... Sq-00712 - Sq-00718

8-Hydroxy-2,3-seco-4,11(13)- 8-(3-Acetoxymethyl-2Z-butenoyl), 13-Ac, Me ester: [104017-

germacradiene-3,10;12,6-diolid-2-oic 79-0]. Poskeanolide
acid Sq-00712 Constit. of Vernonia poskeana. Oil.
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 1359.

HOOC~H
0
0' 1,8,9-Trihydroxy-2,3-seco-4,11(13)- Sq-00716
-I
I
germacradiene-3,10; 12,6-diolide
0

C1sH1a07 M 310.303
(4Z,6«,8P,JOfJ)-form
Tigloyl: [73971-74-1]. 8-Tigloyloxy-2.3-seco-4,11(13)-
heliturgadiene-3,10;12,6-dio/id-2-oic acid
C20H2,.08 M 392.405
Constit. of Picradeniopsis woodhousei. Oil. [ocln -132°
(c, 0.26 in CHC1 3).
Herz, W. et al, J. Org. Chern., 1980, 45, 3163.
C15H 200 7 M 312.319
(1S,4Z,6«,8P,9P,JOS)-form
2-0xo-1,2-seco-1(10),3,8-germacratrien- Sq-00713
8-(2-Methylpropenoyl): [79953-87-0]. lsotrichogoniolide
12,6-olide 8-(2-Methylprop'imoyl), 9-Ac:
C21 H260 9 M 422.431
Constit. of Trichogonia prancii. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1323.

OHC
8,9,10-Trihydroxy-2,3-seco-4,11(13)- Sq-0071i
germacradiene-3,1;12,6-diolide
(3E,8E)-form

C1sH1803 M 246.305
(3E,8E)-form [94662-99-4]
Constit. of Helianthus giganteus and H. hirsutus. Oil.
(3Z,8E)-form [94663-00-0]
Isol. from H. giganteus and H. hirsutus. Oil.
Melek, F.R. et a[, Phytochemistry, 1984, 23, 2573. C15H200 7 M 312.319
(1R,4Z,6«,8P,9P,10«)-form
Salvifoliolide Sq-00714 8-Deacyhrichogonio/ide
8-Angeloyloxy-9,13-epoxy-1-oxo-2 ,3-seco-4-germacrene- 8-Angeloyl:
3,10R;12,6oc-diolide C20H 260 8 M 394.421
[89355-56-6] Constit. of Trichogonia villosa. Oil.
8-Angeloyl, 9-Ac:

\ooc)
0 C22 H280 9 M 436.458
0
Constit. of T. histifolia. Oil.
8-(2-Methylpropenoyl): [79694-65-8]. Trichogoniolide
0 C19H240 8 M 380.394
-H Constit. of T. prancii. Gum.
8-(2-Methylpropenoyl), 9-Ac:
C21 H 260 9 M 422.431
C20H240 8 M 392.405 Constit. ofT. prancii. Cryst. (Et20). Mp 215°. [oc]~
Constit. of Trichogonia salviaefolia. Oil. -246° (c, 0.7 in CHC1 3).
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162. Bohlmann, F. et al, Phytochemistry, 1981, 20, 1323 (iso[)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162 (isol)
4,8,13-Trihydroxy-1-oxo-2,3-seco-5,7(11)- Sq-00715
germacradien-12,6-olid-3-oic acid 2,3,8-Trihydroxy-2,3-seco-1(10),4,11(13)- Sq-00718
germacratrien-12,6-olide

HOH2 C~OH
HOH2 C -::?
~

b
0
C15H200 8 M 328.318 C15H220 5 M 282.336
(1(10)E,4E,6r~.,8fJ)-form
(4«,5Z,8r~.,10«H)-form

282
Crispolide - Bicyclogermacrene Sq-00719 - Sq-00724

8-Ange/oy/: [55306-05-3]. Pycnolide

C:zoH280 6 M 364.438
Constit. of Liatris pycnostachya. Gum. [a]i; +39.8° (c,
1.1 in CHC1 3). Lepidozanes and
bicyclogermacranes
Herz, W. et a/, J. Org. Chern., 1976, 41, 1248.

Cyclogermacranes Anthroplalone
2,2-Dimethy/-3-(3-methyl-7-oxo-3-
Sq-00721
octenyl)cyc/opropanecarboxa/dehyde
[100762-47-8]
Crispolide Sq-00719
1P-Hydroperoxy-5p-hydroxy-4,14-cyc/o-9 ,11-germacradien-
12,6a-olide
[83217-86-1]

~
C15H140 2 M 236.353
Metab. of Anthop/eura pacifica. Cytotoxic. Pale yellow oil.
[aJn -4.4° (c, 0.09 in CHC1 3).
Deformyl: Noranthoplone
C14H140 M 208.343
0 Metab. of A. pacifica. [aln -lOS (c, 0.56 in CHC1 3).
[100693-05-8)
CtsH2005 M 280.320
Constit. of Tanacetum vulgare var. crispum. Amorph. McMurry, J.E. et at, J. Org. Chern., 1987, 52, 4885 (synth)
powder. [a]i;' -20° (c, 0.90 in Py). Zheng, G.-C. et at, Tetrahedron Lett., 1990, 31, 2617 (isot, struct)
Appendino, G. et at, Phytochemistry, 1982, 21, 1099.
1(10),4-Bicyclogermacradien-13-oic acid Sq-00722
8-Hydroxypegolettiolide Sq-00720
8-Hydroxy-8,14-cyc/o-1( 10),4, 7(11)-germacratrien-12,6P-
olide
l:()_H
[88152-98-1] YJ<l--cooH
C15H 220 2 M 234.338
Constit. of Helichrysum chionosphaerum. Oil.
Jakupovic, J. et at, Phytochemistry, 1989, 28, 1119.

13-Bicyclogermacrenal Sq-00723
Ct5Ht80 3 M 246.305 [118855-37-1]
Constit. of Pego/ettia senegalensis. Cryst. Mp 155°. [aln +
0° (c, 0.3 in CHC1 3). Pegolettiolide is unknown.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1637. H
-CHO

C15H 220 M 218.338

Constit. of Conocephalum conicum. Oil. [a]~ -52° (c, 0.4
in CHC1 3).
Toyota, M. et at, Phytochemistry, 1988, 27, 3317.

Bicyclogermacrene Sq-00724
[24703-35-3]

C15H14 M 204.355
Constit. of the peel oil of Citrus junos. Oil. [aln + 61°
(CHC1 3).
Nishimura, K. et at, Tetrahedron, 1973, 29, 271 (iso/, struct)
McMurry, J.E. et a/, J. Org. Chern., 1987, 52, 4885 (synth)

283
Coralloidin B- 1(10),4-Lepidozadien-15-al Sq-00725 - Sq-00731

CoraUoidin B Sq-00725 Oil. [ex]~4 + 34.8° (c, 0. 77 in CHC1 3).

[105708-64-3] Angeloyl: [54878-84-1].
C20 H:l(,0 2 M 302.456
Isol. from Othonna spp. Oil. Bp0 . 1 130°.
Bohlmann, F. et a/, Chern. Ber., 1974, 107, 3928.
Bowden, B.F. et a/, Tetrahedron Lett., 1980, 3105.

8-Hydroxybicyclogermacrene Sq-00729

CROH
C 17H:u;02 M 262.391 Bicyclogermacren-8-ol
Constit. of Alcyonium coralloides. Oil. [ex]i? -33.2° (c, 0.3
in cyclohexane).
Guierriero, A. eta/, J. Nat. Prod. (Lloydia), 1986, 49, 608.

2,3-Dihydroxybicyclogermacrene Sq-00726
2,3-Bicyclogermacrenediol ClsH 240 M 220.354
8rx-form
Constit. of Acritopappus hagei. Oil.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695.

Isobicyclogermacrenal Sq-00730
7,11,11- Trimethylbicyclo[8.1.0]undeca-2,6-diene-3-
ClsH 240 2 M 236.353 carboxaldehyde, 9CI
(2P,3rx)-form
2-Ac: [86176-42-3].
C 17H 260 3 M 278.391
Constit. of Calypogeia granulata. Oil. [ex]~ -10.3° (c, 0.8
~ (+)jo'm
in CHC1 3). OHC~
3-Ac: [86160-99-8].
C 17H:u;03 M 278.391 C 15H 220 M 218.338
Constit. of C. granulata. Oil. [ex]~ + 63.2° (c, 1.2 in
(+)-form [110268-36-5]
CHC1 3).
Constit. of Aristolochia manshuriensis. Cryst. Mp 54-56°.
Takeda, R. et a/, Bull. Chern. Soc. Jpn., 1983, 56, 1265. [ex]i? +341° (c, 0.7 in CHC1 3).
(-)-form [73256-82-3]
1,10-Epoxy-15-hydroperoxy-4-lepidozene Sq-00727 Constit. of Lepidozia vitrea. Oil. [exln -168° (c, 1 in
CHC1 3).

~H
Matsuo, A. et a/, J. Chern. Soc., Perkin Trans. 1, 1984. 203 (isol,
struct)
Magari, H. eta/, J. Chern. Soc., Chern. Commun., 1987. 1196
(synth)
Riicker, G. eta/, Phytochemistry, 1987, 26, 1529 (isol, cryst struct)
HOOH2C
ClsH240 3 M 252.353 1(10),4-Lepidozadien-15-al Sq-00731
(lrx,4E,JOrx)-form [126979-95-1]
Constit. of Anthopleura pacifica. Oil. [exln -143° (c, 0.12
in CHC1 3).
Zheng, G.-C. et a/, J. Org. Chern., 1990, 55, 3677 (iso/, pmr, cmr)

3-Hydroxybicyclogermacrene Sq-00728
Bicyclogermacren-3-ol C15H 220 M 218.338
(l(JO)E,4E,6S,7R)-form [74033-93-5] Lepidozenal

HO~
Constit. of Lepidozia vitrea and Anthopleura pacifica.
Oil. [exJn -169° (c, 1.11 in CHC1 3).
~j-- 15-Alcohol: 1(1 0),4-Lepidozadien-15-ol. Lepidozenol
C 15H240 M 220.354
C 15H 240 M 220.354 Constit. of L. vitrea and A. pacifica. Oil. [exln -104° (c,
1.75 in CHC1 3).
(3P,6rx,7rx)-form
Constit. of Parerythropodium fulvum. Cryst. Mp 116- Matsuo, A. eta/, J. Chern. Soc., Perkin Trans. 1, 1984, 203 (isol,
pmr)
1170. [exln -49.5° (c, 0.11 in CHC1 3). Zheng, G.C. et a/, J. Org. Chern., 1990, 55, 3677 (isol, l'mr, cmr)
Ac: 3-Acetoxybicyclogermacrene
C 17H 260 2 M 262.391
Constit. of P. fulvum. Oil. [exln -25.1° (c, 0.2 in CHC1 3).
(3p,6f.,7f.)-form

284
1(10),4(15)-Lepidozadien-5-ol - 6,7-Epoxy-2-humulene-1,10-diol Sq-00732 - Sq-00737

1(1 0),4(15)-Lepidozadien-5-ol Sq-00732 San Feliciano, A. et a/, Tetrahedron, 1984, 40, 873 (isof)
El Dahmy, S. et a/, Tetrahedron, 1985, 41, 309 (struct)
[127062-42-4] San Feliciano, A. et al, Tetrahedron, 1985, 41, 5711 (cryst struct)

~-H
2,3- Epoxy-6,9-humuladiene Sq-00734
Humulene epoxide I
[19888-33-6]

C 15H 240 M 220.354

(5p,l(JO)E)-form
Constit. of Anthopleura pacifica. Oil. [aln -35° (c, 0.24
in EtOH).
1a,JOa-Epoxide: [126979-97-3]. 1a, 1Oa-Epoxy-4(15)- C 15H 240 M 220.354
lepidozen-5P-ol Constit. of hops and Zingiber zerumbet. Oil. d~0 0.954.
Ct 5H 240 2 M 236.353 Bp1. 5 104-105°. [a]i,O -22.8° (c, 3.6 in CHC1 3). ni,O
Constit. of A. pacifica. Oil. [aln -76° (c, 0.09 in 1.4953.
CHC1 3). Damodaran, N.P. et al, Tetrahedron, 1968, 24, 4123.
5-Hydroperoxide: [126979-98-4]. 5-Hydroperoxy-
1(10),4( 15)-lepidozadiene
6,7-Epoxy-2,9-humuladiene Sq-00735
CtsH2402 M 236.353 Humulene epoxide II
Constit. of A. pacifica. Oil. [1X]n -20.4° (c, 0.23 in
EtOH). [19888-34-7]
5-Hydroperoxide, 1a,JOa-epoxide: [126979-96-2]. l«.,l0«.-
Epoxy-5P-hydroperoxy-4(15)-lepidozene
C 15H 240 3 M 252.353
Constit. of A. pacifica. Oil. [aJn -68.1° (c, 0.07 in
EtOH).
Zheng, G.-C. et al, J. Org. Chern., 1990, 55, 3677 (isol, prnr, crnr)
C15H 240 M 220.354
Constit. of hops and Zingiber zerumbet. Oil. d~0 0.947.
Bp 15 105-106°. [a]i,O -31.2° (c, 4.2 in CHC1 3). ni,O
1.4962.
Humulanes Damodaran, N.P. et al, Tetrahedron, 1968, 24, 4123 (isof)
Picket, J.A. et a/, Chern. Ind. (London), 1977, 30 (synth)

9,10-Epoxy-2,6-humuladiene Sq-00736
Humulene epoxide III
Asteriscunolide Sq-00733 [21624-36-2]
8-0xo-2,6,9-humulatrien-15,1-olide

~
~ (2Z,6E,'JZ)-f"m C 15H 240 M 220.354
Constit. of Dipterocarpus pilosus. Oil. Bp 15 120-130°. [1X]n
C 15H 180 3 M 246.305
+2.15° (c, 1.25 in CHC1 3).
Famesane numbering shown.
Gupta, A.S. et al, Tetrahedron, 1971, 27, 635 (isof)
(2Z,6Z,9Z)-form [83488-75-9] Asteriscunolide A Sattar, A. et al, Tetrahedron Lett., 1976, 1403 (synth)
Constit. of Asteriscus aquaticus and A. graveolens. Cryst.
(Etp). Mp 158°. [a]i;' -335.5° (c, 1.4 in CHC1 3).
(2Z,6E,9Z)-form [90383-29-2] Asteriscunolide B
6,7-Epoxy-2-humulene-1,10-diol Sq-00737
Constit. of A. aquaticus and A. graveolens. Cryst. _o
(Et20). Mp 175°. [a]i;' -381° (c, 0.98 in CHC1 3).
(2Z,6Z,9E)-form [96726-87-3] Asteriscunolide C ~ (1S,6S,7S,10S)-form
Constit. of A. aquaticus and A. graveolens. Cryst.
(Et20). Mp 164°. [a]i;' -260° (c, 0.90 in CHC1 3). )=./)('oH
(2Z,6E,9E)-form [96726-86-2] Asteriscunolide D CtsHu03 M 254.369
Constit. of A. aquaticus and A. graveolens. Cryst.
(1S,6S,7S,JOS)-form [98155-86-3] Caucalol
(Etp). Mp 145°. [a]i;' -158° (c, 0.37 in CHC1 3).
Di-Ac: [5172-19-0].
San Feliciano, A. eta/, Tetrahedron Lett., 1982, 23, 3097 (isof)
Ct9H300 5 M 338.443

285
6,7-Epoxy-2-humulen-1-ol - 1,3(15),6-Humulatriene Sq-00738 - Sq-00743

Constit. of Caucalis scabra. Cryst. Mp 121-122°. [1X]);I· 5 C22 H 300 4 M 358.477

+ 33.4° (CHC1 3). Constit. of Ferula juniperina. Cryst. (EtOAcjhexane).
(1 S,6R,7R,JOS)-form Mp 90-91°. [1X]i? + 120.4° (c, 0. 77 in EtOH).
Neocaucalol l-Ac, 0 4-(4-hydroxybenzoyl): [70494-82-5]. Juniferidin
Di-Ac: [98243-51-7]. C24H 320 5 M 400.514
Constit. of C. scabra. Needles. Mp 169-171°. [1X] 0 Constit. of roots of F. juniperina. Cryst.
-108.3° (c, 0.29 in CHCl 3). (EtOAcfhexane). Mp 162-163°. [IX]~ +2.1° (c, 0.65 in
MeOH).
Sasaki, S. et a/, Tetrahedron Lett., 1966, 623.
ltokawa, H. et a/, Chern. Pharm. Bull., 1985, 33, 2204 (abs config) 0 4 -(4-Hydroxy-3-methoxybenzoyl): [61116-35-6]. Juniferin
CnH3P 5 M 388.503
From F. juniperina. Cryst. (EtOAcjhexane). Mp 85-86°.
6,7-Epoxy-2-humulen-1-ol Sq-00738
[1X]i? -1.6° (c, 5.8 in EtOH).
4,7,7,11- Tetramethyl-12-oxabicyclo[9.J.O]dodec-4-en-6-o/,
9Cl Sagitdinova, G.V. et a/, Khim. Prir. Soedin., 1977, 790; 1978, 809.

2,9-Humulad.ien-7-ol Sq-00741
Humulol
Absolute
configuration [24405-58-1]

CisH2602 M 238.369
(JS,2Z,6S,7S)-form [87989-23-9]
Constit. of fruit of Tori/is scabra. Cryst. Mp 125-130°.
[1X] 0 + 30.9° (c, 0.22 in CHCI 3).
Ac: [87989-22-8]. 15-Acetoxy-6S,7S-epoxy-2Z-humulene
M
\-(
C17H11P 3 M 280.406
Constit. ofT. scabra. Cryst. Mp 125-130°. [1X] 0 +21.4° C15H 260 M 222.370
(c, 0.36 in CHCl 3). Constit. of hop oil. Oil. [1X]~4 -1.2° (c, 0.9 in MeOH).
(JS,2Z,6R,7R)-form Naya, Y. et a/, Bull. Chern. Soc. Jpn., 1969, 42, 2405 (isol)
Naya, Y. eta/, Chern. Lett., 1973, 133 (synth)
Ac: From T. scabra. Oil. [1X] 0 -175.5° (c, 0.33 in CHCl3).
ltokawa, H. et a/, Chern. Lett., 1983, 1581 (cryst struct)
ltokawa, H. eta/, Chern. Pharm. Bull., 1985, 33, 2204 (cryst struct, 2,9-Humulad.ien-6-one Sq-00742
abs corifig) Humuladienone
[24405-90-l]
Fexerol Sq-00739
6,7-Epoxy-2-humu/ene-1,4-dio/
[66295-66-7]

CisHu03 M 254.369
0~
Constit. of Ferula tschatkalensis. Cryst. Mp 141-142°.
C15H240 M 220.354
Constit. of hops. Oil. [IX]~ +5° (c, 0. 7 in CHCl3).
Naya, Y. eta/, Bull. Chern. Soc. Jpn., 1969, 42, 2088.

1,3(15),6-Humulatriene Sq-00743
1-Tig/oy/: [89803-99-6]. Chatferin 1,8,8-Trimethy/-5-methy/ene-1 ,6-cycloundecadiene. y-
C20H 320 4 M 336.470 Humulene. /sohumulene
Constit. of F. tschatkalensis. Oil. [1X]i? + 6.2° (c, 1.53 in [26259-79-0]
EtOH).
Sagitdinova, G.V. eta/, Khim. Prir. Soedin., 1977, 13, 665; 1983,
19, 721 (iso/, struct, synth)
Makmudov, M.K. eta/, Khim. Prir. Soedin., 1986, 22, 39 (cryst
struct)

2,6-Humulad.iene-1,4-d.iol Sq-00740
C1sH24 M 204.355

HO~
Constit. of Artemisia princeps and Othonna coronop!folia.
Oil. Bp0 _1 90°.

:N
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 3928 (iso/, cmr)
Yano, K. eta/, Phytochemistry, 1974, 13, 1207 (isol)

C 15H 260 2 M 238.369

Famesane numbering shown.
0 4-(4-Hydroxybenzoyl): [61116-36-7]. Juniferinin

286
2,6,9-Humulatriene- 1,3(15),6-Humulatrien-14-ol Sq-00744- Sq-00749

2,6,9-Humulatriene Sq-00744 1,3(15),6-Humulatrien-9-ol Sq-00747

2,6,6,9- Tetramethy/-1 ,4,8-cyc/oundecatriene. rx.-Humulene. rx.-

~OH
Caryophyl/ene (obsol.)
[6753-98-6)

C1sH140 M 220.354
0-(4-Hydroxybenzoyl): [70629-76-4]. Juferin
C22H 280 3 M 340.461
C15H14 M 204.355 Constit. of Ferula juniperina. Cryst. (Me2CO). Mp 90-
Famesane numbering shown. Constit. of many essential
910. [rx.]~ + 120.4° (c, 0.77 in EtOH). Relationship of
oils including hops and cloves. Oil. Bp 10 123°.
Juferin to Ferocin not clear. May be the enantiomer or
AgN0 3 complex: Cryst. (EtOH). Mp 175°. a geom. isomer.
6,7-Episu/fide: [65563-96-4]. 1,5,5,8-Tetramethyl-12- (E,E)-form
thiabicyc/o[9.1.(Jjdodeca-3,7-diene, 9CI Fecerol
CtsH14S M 236.421 Mp 82-83°.
Constit. of hops. Oil.
0-(4-Hydroxybenzoyl): [65638-03-1 ]. Ferocin
9,10-Episu/fide: [74841-84-2]. 3,7,7,10-Tetramethyl-12- C22H 280 3 M 340.461
thiabicyc/o[9.1.0)dodeca-3,7-diene, 9CI lsol. from roots of Feru/a ceratophylla. Cryst. (hexane).
C1 5H 14S M 236.421 Mp 127-128°. [rx.]~ -200° (c, 1.0 in C6H 6).
Constit. of hops. Oil.
0-(4-Hydroxy-3-methoxybenzoyl): [65638-04-2]. Ferocinin
McPhail, A.T. eta/, J. Chern. Soc. B, 1966, 112 (cryst struct) C23H 300 4 M 370.488
Dev, S. eta/, J. Am. Chern. Soc., 1968, 90, 1246 (pmr) lsol. from roots of F. ceratophylla. Cryst. (hexane). [rx.]~
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
-197° (c, 1.0 in C6H 6).
Pjlanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 1929 (occur) Golovina, L.A. eta/, Khim. Prir. Soedin., 1911, 13, 796; Chern.
Cradwick, M.E. eta/, J. Chern. Soc., Perkin Trans. 2, 1973, 404 Nat. Compd. (Engl. Trans/.), 671.
(conformn) Sagitdinova, G.V. eta/, Khim. Prir. Soedin., 1978, 14, 809.
Vig, O.P. eta/, Indian J. Chern., Sect. B, 1976, 14, 855 (synth)
Kitagawa, Y. eta/, J. Am. Chern. Soc., 1977, 99, 3864 (synth)
Peppard, T.L. eta/, J. Chern. Soc., Perkin Trans. I, 1980, 311
1,3(15),6-Humulatrien-10-ol Sq-00748
(isol) Fervanol
McMurry, J.E. eta/, Tetrahedron Lett., 1982, 23, 2723 (synth) [11 0309-08-5]

WOH
Shirahama, H. et a/, Chern. Lett., 1983, 281 (synth)
McMurry, J.E. eta/, Tetrahedron, 1987, 43, 5489 (synth)

2,7(14),9-Humulatriene Sq-00745
1,4,4-Trimethy/-8-methy/ene-1 ,5-cyc/oundecadiene. P-
Humu/ene M 220.354
[116-04-1] Benzoyl: Fervanol benzoate
C22H 280 2 M 324.462
Constit. of Ferula haussknechtii. Gum.
4-Hydroxybenzoy/: Fervanol p-hydroxybenzoate
C22H 280 3 M 340.461
From F. haussknechtii. Gum.
4-Hydroxy-3-methoxybenzoy/: Fervanol vanillate
C 23H 300 4 M 370.488
C 15H 14 M 204.355 From F. haussknechtii. Gum.
Constit. of hops and Lindera strychnifolia. Oil. Miski, M. eta/, Phytochemistry, 1987, 26, 1733.
Naya, Y. eta/, Chern. Lett., 1973, 727.
1,3(15),6-Humulatrien-14-ol Sq-00749

yq_
3(15),7(14),9-Humulatriene-2,6-diol Sq-00746 y- Humulen-14-ol

C15H 140 M 220.354

Ac:
C15H 140 2 M 236.353 C17H 21;02 M 262.391
Metab. of red alga Laurencia obtusa. Cryst. Mp 104.5- Constit. of Acritopappus prunifolius. Oil. Bp0 _1 130°.
1070. Occurs as racemate resolvable into enantiomers. Ange/oyl:
[127760-78-5, 127760-79-6, 127760-80-9) C 20H 32 0 2 M 304.472
Takeda, S. et a/, Chern. Lett., 1990, 155 (isol, struct) Constit. of A. prunifolius. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 147.

287
2,6,9-Humulatrien-14-ol- Humulene bromohydrin Sq-00750 - Sq-00755

2,6,9-Humulatrien-14-ol Sq-00750 Constit. of Zingiber zerumbet. Oil. Bp 3. 5 128-130°. [ali?

«-Humulen-14-ol +25.9° (c, 1.8 in CHC1 3).
[75678-90-9] Damodaran, N.P. eta/, Tetrahedron, 1968, 24, 4133.

1,3(15),6-Humulatrien-8-one Sq-00753
2,9 ,9-Trimethy/-6-methy/ene-2, 7-cyc/oundecadien-1-one, 9CI.
y-Humulen-9-one
[85526-80-3]
C15H240 M 220.354

c;Q
Constit. of Helichrysum chionosphaerum. Oil. 0
Ac:
C 17H 11;02 M 262.391
Constit. of Lychnophora columnaris. Oil.
14-A/dehyde: [75678-91-0]. «-Humulen-14-al
C 15H 220 M 218.338
Constit. of L. columnaris. Oil. C 15H 220 M 218.338
Famesane numbering shown. Constit. of Cineraria
14-Carboxy/ic acid: «-Humulen-14-oic acid
fruticulorum. Oil. [1X]n -102° (c, 1.05 in CHC1 3).
CtsH 22 0 2 M 234.338
Constit. of L. columnaris. Cryst. (pet. ether). Mp 93°. 6,7-Dihydro: [85526-84-7]. 1,3(15)-Humuladien-8-one
C 15H 240 M 220.354
6a, 7P-Epoxide: [8290 1-25-5]. 6a, 7P-Epoxy-2,9-humu/adien-
Constit. of C. fruticu/orum. Oil. [1X]n -32° (c, 0.05 in
14-o/. 1a, 1op-Epoxy-a-humu/en-14-o/
CHC1 3).
C 15H 240 2 M 236.353
Constit. of L. columnaris. Oil. [a]~ + 13.SO (c, 0.68 in Bohlmann, F. et al, Phytochemistry, 1982, 21, 2531.
CHC1 3).
14-A/dehyde, 6rx.,7P-epoxide: [82901-26-6]. 6a,7p-Epoxy-2,9- 2,6,9-Humulatrien-8-one Sq-00754
humuladien-14-al. 1a, 1OP-Epoxy-a-humu/en-14-a/ Zerumbone
CtsH22 0 2 M 234.338 [471-05-6]
Constit. of L. co/umnaris. Oil. [a]~ + 13° (c, 0.24 in
CHC1 3).
14-Carboxy/ic acid, 9P,J0a-epoxide: [82900-99-0]. 9P,10a-
Epoxy-2,6-humu/adien-14-carboxy/ic acid.
Lychnocolumnic acid
C 15H 22 0 3 M 250.337
Constit. of L. columnaris. Gum (as Me ester). [a]~ -32° C 15H 220 M 218.338
(c, 0.51 in CHC1 3) (Me ester). Constit. of the rhizomes of wild ginger (Zingiber
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 869; 1982, 21, 685. zerumbet). Cryst. Mp 66-67°. Bp 10 165-167°.
Oxime: Cryst. (EtOH aq.). Mp 178.SO.
2,7(14),9-Humulatrien-6-ol Sq-00751 Semicarbazone: Cryst. (EtOH aq.). Mp 163°.
Humulenol 11 21;,,31;,-Epoxide: [22471-70-1]. 2,3-Epoxy-6,9-humu/adien-8-
[19888-00-7] one. Zerumbone oxide
CtsH 220 2 M 234.338
Constit. of Z. zerumbet. Cryst. Mp 100°.
Dev, S., Tetrahedron, 1960, 8, 171 (isol)
Damodaran, N.P. et al, Tetrahedron Lett., 1965, 1977 (struct)
Dev, S. et al, J. Am. Chern. Soc., 1968, 90, 1246 (pmr)
Chabra, B.R. et al, Indian J. Chern., 1975, 13, 222 (Zerumbone
oxide)
Hall, S.R. et al, Aust. J. Chern., 1981, 34, 2243 (cryst struct)
C15H240 M 220.354
Constit. of Zingiber zerumbet. Oil. Bp 1 115-116°. [ali?
+ 30° (c, 3.6 in CHC1 3). Humulene bromohydrin Sq-00755
Damodaran, N.P. et al, Tetrahedron, 1968, 24, 4133 (isol) [13474-49-2]
Picket, J.A. eta/, Chern. Ind. (London), 1977, 30 (synth)
Namikawa, M. et a/, Bull. Chern. Soc. Jpn., 1978, 51, 3616 (synth) Br
I

3(15),6,9-Humulatrien-2-ol
Humu/eno/1
[19888-01-8]
Sq-00752
OOH
11~(

C 15H 25 Br0 M 301.266

Cryst.
Allen, F.H. eta/, J. Chern. Soc. B, 1968, 1047 (cryst struct)
Greenwood, J.M. et al, J. Chern. Soc. C, 1968, 3004 (synth)

M 220.354

288
1-Hydroxy-2,6-humuladien-15-al- Rudbeckianone Sq-00756 - Sq-00760

1-Hydroxy-2,6-humuladien-15-al Sq-00756 1-Deoxy: 8-0xo-2,6,9-humulatrien-15-oic acid

Kurubasch aldehyde ClsH200 3 M 248.321
Constit. of A. graveolens. Oil (as Me ester).
(1P,2Z,6E,9Z)-form
Ac: Constit. of A. graveolens. Oil (as Me ester).
6-Deoxy: Constit. of A. graveolens. Oil (as Me ester).
(1P,2Z,6Z,9E)-form
C 15H 240 2 M 236.353 Ac: Constit. of A. graveolens. Oil (as Me ester).
Farnesane numbering shown.
1-Deoxy: Constit. of A. graveolens. Oil (as Me ester).
Benzoyl: Kurubasch aldehyde benzoate
C22 H 28 0 3 M 340.461 (1P,2Z,6Z,9Z)-form
Constit. of Ferula haussknechtii. Gum. Ac: Constit. of A. graveolens. Oil (as Me ester).
4-Hydroxy-3-methoxybenzoyl: Kurubasch aldehyde vanillate 1-Deoxy: Constit. of A. graveolens. Oil (as Me ester).
C 23H 300 5 M 386.487 El Dahmy, S. eta/, Tetrahedron, 1985, 41, 309.
From F. haussknechtii. Gum.
15-Carboxylic acid, 0-angeloyl: Kurubashic acid angelate Manshurolide Sq-00759
C20H 300 4 M 334.455
From F. haussknechtii. Gum.
15-Carboxylic acid, benzoyl: Kurubashic acid benzoate
C22 H 280 4 M 356.461
From F. haussknechtii. Gum.
15-Carboxylic acid, 6fi,10rx.-epoxide, angeloyl: 6fi,10rx.-
Epoxykurubashic acid angelate
C 20H 300 5 M 350.454 0
From F. haussknechtii. Gum. C 15H 200 2 M 232.322
15-Carboxylic acid, 6fi,10rx.-epoxide, benzoyl: 6fi,10rx.- Constit. of Aristolochia manshuriensis. Needles (hexane).
Epoxykurubashic acid benzoate Mp 128-130°. [rx.] 0 +56° (c, 0.79 in EtOH).
C22 H 28 0 5 M 372.460 Riicker, G. eta/, Phytochemistry, 1990, 29, 983 (iso/, pmr, cmr,
From F. haussknechtii. Gum. cryst struct)
15-Carboxylic acid, 6rx.,10fi-epoxide, benzoyl: 6rx., 1Ofi-
Epoxykurubaschic acid benzoate
Rudbeckianone Sq-00760
C22H 28 0 5 M 372.460
15-N or-1 ,6-humuladien-3-one
From F. haussknechtii. Gum.
[70329-65-6]
Miski, M. eta/, Phytochemistry, 1987, 26, 1733.

11-Hydroxy-14-lychnenoic acid Sq-00757

ClsH 22 0 3
0
M 250.337
CH20H

Ac: 11-Acetoxy-14-/ychnenoic acid

C14H2P M 206.327
Constit. of Rudbeckia laciniata. Oil.
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 2034.

C1 7 H 240 4 M 292.374
Constit. of Lychnophora columnaris. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 685.

1-Hydroxy-8-oxo-2,6,9-humulatrien-15-oic Sq-00758
acid

HO~
~
C 15H 200 4 M 264.321
Farnesane numbering shown.
(lp,2Z,6E,9E)-form
Ac:
C 17H 220 5 M 306.358
Constit. of Asteriscus graveolens. Oil.

289
3(15),6-Caryophylladiene - 3,7(14)-Caryophylladien-6-ol Sq-00761 - Sq-00764

3(15),6-Caryophylladiene-5,9-diol Sq-00762
2,8-Caryophyllenediol
Caryophilanes

3(15),6-CaryophyUadiene Sq-00761

ctsH:w02 M 236.353
(5p,9fJ)-form
(E)-form
9-Benzoyl, 5-Ac: [77355-65-8].
C24 H 300 4 M 382.499
C 15H 24 M 204.355 Constit. of Solidago nemoralis. Oil.
(E)-form [87-44-5] P-Caryophyllene. P-Humulene (obsol.). 3oc,l5-Epoxide, 9-benzoyl, 5-Ac: [77396-70-4].
Caryophyllene C24H 300 5 M 398.498
Constit. of clove, cinnamon and many other oils Constit. of S. nemoralis. Oil.
(Artemisia, Caryopteris, Cinnamomum, Citrus, Bohlmann, F. et a/, Phytochemistry, 1980, 19, 2655.
Eucalyptus, Juniperus, Lavandula, Mentha, Pinus, Salvia
and Thymus spp.). Oil with v. faint odour. Bp9 . 7 118- 3(15),6-Caryophylladien-14-oic acid Sq-00763
1190. [oc]i,l -15.0° (c, 2.60 in CHC1 3). 15-Caryophyllenoic acid
I> Skin irritant. DT8400000.
2-Epimer: [68832-35-9]. 2-Epicaryophyllene. 9PH-
Caryophyllene
C 15H 24 M 204.355
Isol. from Dacrydium cupressinum. Waxy solid. [ocln
+ 196° (CHC1 3).
14-Hydroxy, 2-epimer: [123355-03-3]. 14-Hydroxy-2-epi-P-
caryophyllene. ! 14-Hydroxy-9-epi-P-caryophyllene CtsH2202 M 234.338
C 15H 240 M 220.354 (Z)-form
Constit. of oil of Juniperus oxycedrus. Oil. [ocln -13.5°. Constit. of Lychnophora salicifolia. Gum.
Exists in two major conformations at r.t. Me ester: Oil. [oc]i;' +2.8° {c, 3.2 in CHC1 3).
Jp,JS-Epoxide: [88395-50-0]. 3,15-Epoxy-6-caryophyllene 6,7-Dihydro: 3(15)-Caryophyllen-14-oic acid
C 15H 240 M 220.354 C 15H 240 2 M 236.353
Constit. of clary sage oil (Salvia sclarea). Oil. [ocln + 40° Constit. of L. salicifolia. Oil (as Me ester). [oc]i~ -4.4°
(c, 3.4 in CHC1 3). (c, 10.4 in CHC1 3) (Me ester).
(Z)-form [118-65-0] y-Caryophyllene. /socaryophyllene 14-Alcohol, 61;, 7I;-epoxide: [9490 1-71-0]. 6,7-Epoxy-3(15)-
Widespread in plants (Jasminum, Origanum and caryophyllen-14-ol. 14-Hydroxycaryophyllene-4 .5-oxide
Pimpinella spp.). Oil. Bp 14. 5 125°. [oc]~4 -27°. C 15H 240 2 M 236.353
[33993-33-8, 54061-81-3, 61217-74-1] Constit. of Betula pubescens. Oil. [oc]:,S -34.6° (c, 0.5 in
Corey, E.J. et a/, J. Am. Chern. Soc., 1964, 86, 485 (synth, bib[) CHC1 3).
Hill, H.C. et a/, J. Chern. Soc. C, 1968, 93 (ms) Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2381.
Gollnick, K. eta/, Tetrahedron Lett., 1968, 689 (synth) Pokhilo, N.D. eta/, Khim. Prir. Soedin., 1984, 20, 598; Chern. Nat.
Croteau, R. eta/, Phytochemistry, 1972, 11, 1055 (biosynth) Compd. (Engl. Trans/.), 563.
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzensto.ffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 1929 (occur) 3,7(14)-Caryophylladien-6-ol Sq-00764
Wamhoff, E.W. et a/, Can. J. Chern., 1973, 51, 3955 (purifn) 2,10,10- Trimethyl-6-methylenebicyclo[7.2 .O]undec-2-en-5-ol,
Morris, W.W., J. Assoc. Off Anal. Chern., 1973, 56, 1037 (ir) 9CI. rx.-Betulenol. oc-Betulol

?OH
Robertson, J., Int. Rev. Sci.: Phys. Chern., Ser. Two, 1975, 11, 57
(rev) [487-86-5]
Kumar, A. eta/, Synthesis, 1976, 461 (synth)
Peyron, L., Riv. Ita/. Essenze, Profumi, Piante Off, Aromi, Saponi,
Cosmet., Aerosol, 1977, 59, 603 (rev)
Mauer, B. et a/, Helv. Chim. Acta, 1983, 66, 2223 (epoxide)
McMurry, J.E., Tetrahedron Lett., 1983, 24, 1885 (synth)
Ohtsuka, Y. eta/, J. Org. Chern., 1984, 49, 2326 (synth)
Berry, K.M. et a/, Phytochemistry, 1985, 24, 2893 (2-
Epicaryophyl/ene) C 15H 240 M 220.354
Barrero, A.F. et a/, Tetrahedron Lett., 1989, 30, 247 (14-Hydroxy- Constit. of the essential oil of Betula lenta and B. alba.
2-epi-P-caryophyl/ene) Oil. Bp 20 154-156°. [oc]i? -19.SO. nn 1.5148.
Sax, N.l. et a/, Dangerous Properties of Industrial Materials, 7th
Ac:
Ed., Van Nostrand-Reinhold, 1989, 729.
Ct,H260 2 M 262.391
Constit. of B. alba. Oil. [oc]i? +20.2° (pure liq.). ni?
1.4946.
Holub, M. et a/, Collect. Czech. Chern. Commun., 1959. 24, 3730
(struct)
Treibs, W. eta/, Justus Liebigs Ann. Chern., 1960, 634, 124 (synth)

290
3(15),6-Caryophylladien-1-ol - 12,14-Dihydroxy-3(15),6-... Sq-00765 - Sq-00771

3(15),6-Caryophylladien-1-ol Sq-00765 6-Ketone: 3(15),7-Caryophylladien-6-one

10-Caryophyl/enol C15H 220 M 218.338
lsol. from Fleischmannia viscidipes.
6-Ketone, 14-hydroxy: 14-Hydroxy-3(15),7-caryophylladien-
6-one
C15H 220 1 M 234.338
From F. viscidipes.
(6ft,7E)-form [32214-89-4] Caryophyllenolll
C 15H 240 M 220.354 From D. pilosus. Cryst. (MeCN). Mp 89-90°. [ocln
+ 176.9° (c, 0.3 in CHCI 3).
]a.-form
(6f.,7E)-form [34298-3!-2]a.-Multijugenol
Constit. of Leucanthemum maximum. Oil.
Constit. of Copaifera multijuga. Viscous oil. [ocln + 115°.
Bohlmann, F. et at, Phytochemistry, 1980, 19, 2469. From its opt. rotn., appears to be identical with
Caryophylleno1 II, but this requires confirmation.
3(15),6-Caryophylladien-4-ol Sq-00766 Gupta, A.S. eta/, Tetrahedron, 1971, 27, 635.
6,10,10- Trimethyl-2-methylenebicyclo[7.2.0]undec-5-en-3-ol, Monache, G.D. eta/, Tetrahedron Lett., 1971, 659.
9CI. P-Betulenol Stahl, E. eta/, Tetrahedron Lett., 1973, 2841 (isol)
[487-87-6] Groweiss, A. et at, Tetrahedron, 1983, 39, 3385 (synth, pmr, cmr,

-tW
ms, config)
Bohlmann, F. eta/, Rev. Latinoam. Quim., 1984, 15, 1; CA, 102,
3198f (derivs)
Absolute
configuration 6-Caryophyllen-15-al Sq-00769
6,10,10- Trimethylbicyc/o[7.2 .O]undec-5-ene-2-

-rrr
carboxaldehyde, 9C/
C15H 240 M 220.354
Constit. of the essential oil of Betula spp., Perovskia spp.
and oil of peppermint (Mentha piperita) and palmarosa.
Oil. Bp 20 157-158°. [oc]~ -36°.
(3R,6E)-form
[6040-49-9, 20296-32-6]
Holub, M. eta/, Collect. Czech. Chern. Commun., 1959, 24, 3730 CHO
(struct)
Treibs, W. eta/, Justus Liebigs Ann. Chern., 1960, 634, 124 (synth) CisH 240 M 220.354
Naves, Y.R., Parfums, Cosmet. Savons Fr., 1970, 13, 354 (props) (3R,6E)-form [88395-49-7]
Constit. of Clary sage oil (Salvia sclarea). Oil. [ocln
3(15),6-Caryophylladien-9-ol Sq-00767 +6.7° (c, 1.1 in CHCI 3).
8-Caryophyl/enol (3S,6E)-form [88424-68-4]
From Clary sage oil. Oil. [ocln -21.9° (c, 1.1 in CHCI 3).
Maurer, B. et at, Helv. Chim. Acta, 1983, 66, 2223.

3(15)-Caryophyllen-5-one Sq-00770
Buddledin E
[68373-70-6]

cl5H24o M 220.354
9P-form
Benzoyl:
C22H 280 1 M 324.462
Constit. of Solidago nemoralis. Oil.
3oc,15-Epoxide, benzoyl: CisH 240 M 220.354
C22 H 280 3 M 340.461 Constit. of the root bark of Buddleja davidii. Oil. [ocln -6°
Constit. of S. nemoralis. Oil. (c, 1.33 in CHCI 3).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2655. Yoshida, T. et al, Chern. Pharm. Bull., 1978, 26, 2543.

3(15),7-Caryophylladien-6-ol Sq-00768 12,14-Dihydroxy-3(15),6-caryophylladien- Sq-00771

8-one

~-OH
12,14-Dihydroxy-9-caryophyl/enone. 14,15-Dihydroxy-3-
caryophyl/enone

(6a, 7E)-form
C 15H 240 M 220.354
(6a.,7E)-form [32214-88-3] Caryophyllenoll
Constit. of Dipterocarpus pi/osus. Also in cannabis oil. (E)-form
Cryst. (MeCN). Mp 73.5-75°. [ocJn -101.4° (c, 0.5 in
CHC1 3).

291
3,7-Epoxycaryophyllane - 9-Hydroxy-3(15),6-caryophylladien-... Sq-00772 - Sq-00775

C15H 210 3 M 250.337 Constit. of oil of cloves (Eugenia caryophyllata). Also in

Several numbering systems in use. oils of Betula alba, Mentha piperita and others. Major
(6E)-form prod. of epoxidn. of Caryophyllene. Cryst. Mp 63.5-64°.
Constit. of Pulicaria dysenterica. Gum. [rx]~ -79.4° (c, 2.32 in CHC1 3).
12-Ac: (6S,7S)-form
Ct,H240 4 M 292.374 Caryophyllene fJ-oxide
Constit. of P. dysenterica and Inula spiraefolia. Oil or Minor prod. of epoxidn. of Caryophyllene. Mp 29-31°
gum. [rx]~ -37.2° (CHC1 3). approx. [rx]n + 0° (c, 2.46 in CHC1 3). Warnhoff appears
14-Ac:
to show the wrong configs.
C17H 240 4 M 292.374 Treibs, W., Chern. Ber., 1947, 80, 56 (synth)
Constit. of P: dysenterica and /. spiraefolia. Oil or gum. Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pfianzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
[rx]~ -30.7° (CHC1 3).
no. 1930 (occur)
12-Deoxy: 14-Hytkoxy-3(15),6-caryophiUadien-8-one. !14- Wamhoff, E.W. eta/, Can. J. Chern., 1973, 51, 3955 (synth, pmr)
Hydroxy-3(15),6-caryophyl/adien-8-one Gati1ov, Yu.A. eta/, Khim. Prir. Soedin., 1982, 18, 715; Chern.
C15H 210 2 M 234.338 Nat. Compd. (Engl. Trans/.), 677 (cryst struct, bib[)
Constit. of P. scabra. Gum. [rx]~4 -272° (c, 0.9 in
CHC1 3). 6,7-Epoxy-3(15)-caryophyllen-12-ol Sq-00774
(6Z)-form 1,10-Epoxycaryophyl/en-12-ol. 12-Hydroxycaryophyl/ene-
12-Ac: Constit. of P. dysenterica. Gum. 1,10-oxide
14-Ac: Constit. of P. dysenterica and P. arabica. Gum. [73510-14-2]
12,14-Di-Ac:
CI,H2605 M 334.411
Constit. of P. dysenterica and P. arabica. Gum. [rx]~ HOH=~vH,~
-135.8° (c, 1.22 in CHC1 3). Absolute
12-Deoxy: Constit. of P. scabra, P. arabica and Jasonia Hf configuration
glutinosa. Gum. [rx]~ -196° (c, 0.5 in CHC1 3), [rx]n
-122.5° (c, 1.33 in CHC1 3). C1sH2402 M 236.353
12-Deoxy, 14-Ac: Several numbering systems in use. Constit. of Lactarius
C1,H 240 3 M 276.375 camphoratus. Amorph. Mp 48-53°. [rx]ii -69.9° (c, 1 in
Constit. of P. dysenterica, P. scabra and P. arabica. CHC1 3).
Gum. [rx]~ -167.SO (c, 1.58 in CHC1 3). Daniewski, W.M. eta/, Phytochemistry, 1981, 20, 2733.
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 2529; 1982, 21,
1659; 1987, 26, 3356. 9-Hydroxy-3(15),6-caryophylladien-14-oic Sq-00775
De Pascual Teresa, J. eta/, Acta Quim. Compostelana, 1982, 72,
317. acid
Jeremic, D. eta/, Tetrahedron Lett., 1982, 23, 1009.

3,7-Epoxycaryophyllane
Caryophyllane-2 ,6-oxide
Sq-00772 -W->-COOH
~
W
[60269-11-6)

H " C15H 210 3 M 250.337

(6Z,9/1)-form [68945-57-3] Lychnopholic acid
Constit. of Lychnophora affinis. Cryst.
I
I
Ac:
C15H 260 M 222.370 Ct,H 240 4 M 292.374
Constit. of Lippia citriodora. [rx]n -75.4° (c, 1.1 in CHC1 3). Constit. of L. salicifolia. Cryst. (Et20). Mp 170°. [rx]~4
Kaiser, R. eta/, Helv. Chim. Acta, 1976, 59, 1803. +40.SO (c, 3.2 in CHC1 3).
Deoxy: [77836-74-9]. 3(15),6-Caryophyl/adien-14-oic acid.
Sq-00773 Lychnophoric acid
6,7-Epoxy-3(15)-caryophyllene
C15H 220 2 M 234.338
Epoxycaryophyl/ene. Caryophyllene oxide.
Isol. from L. affinis. Mp 119-120°.
Epoxydihydrocaryophyllene
Raffauf, R.F. et a/, J. Am. Chern. Soc., 1978, 100, 7437
[13877-94-6] (Lynnopholic acid)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2381 (isol)
Le Quesne, P.W. eta/, J. Org. Chern., 1982, 47, 1519
(Lychnophoric acid)
(6R, 7 R)-form

C15H 240 M 220.354

(6R,7R)-form [1139-30-6] Caryophyllene rx.-oxide

292
6-Hydroxy-3(15),7(14)-... - Kobusone Sq-00776 - Sq-00780

6-Hydroxy-3(15),7(14)-caryophylladien-8- Sq-00776 C15H 220 M 218.338

one Constit. of the root bark of B. davidii. Cryst. Mp 129-
1300. [(Xln -316° (c, 0.54 in CHC1 3).
6Z-form
9-Deoxy: [62413-96-1]. Buddledin D
CISHlp M 218.338
6a.-form From B. davidii. Syrup. [(Xln -164° (c, 0.92 in CHC1 3).
Yoshida, T. eta/, Chern. Pharm. Bull., 1978, 26, 2543.

6-Hydroxy-6,7-seco-3(15)-caryophyllen-7- Sq-00778
C15H 22 0 2 M 234.338
one
6«-form 5-Hydroxy-5,6-seco-2(12)-caryophyllen-6-one
Me ether: 6«-Methoxy-3(15),7(14)-caryophylladien-8-one [90042-17-4]
C16H 240 2 M 248.364
lsol. from Jasonia glutinosa. Oil. [(Xln + 56.5° (c, 1 in
CHC1 3).
12-Hydroxy: 6rz,12-Dihydroxy-3(15),7(14)-caryophylladien-
8-one
C15H 220 3 M 250.337
Isol. from Pulicaria arabica. Oil.
12-Acetoxy, Me ether: C15H 260 2 M 238.369
C18Hu04 M 306.401 Constit. of Monactis macbridei. Oil. Bp0 . 1 170° (bath). [(Xln
From P. arabica. Oil. +21.1° (c, 0.39 in CHC1 3).
6P-form Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 503.
Me ether: 6P-Methoxy-3(15),7(14)-caryophyUadien-8-one
Ct6H2402 M 248.364 lsokobusone Sq-00779
From J. glutinosa. Oil. [(Xln -137.1° (c, 0.23 in CHC1 3). 6-Hydroxy-15-nor-7( 14)-caryophyllen-3-one

V
12-Hydroxy: 6,12-Dihydroxy-3(15),7(14)-caryophyUadien-8- [24173-72-6]
one
C15H 22 0 3 M 250.337 H #
lsol. from P. arabica.
OH
12-Hydroxy, 6-Me ether: 12-Hydroxy-6P-methoxy-
I
3(15),7(14)-caryophylladien-8-one H
C16H 240 3 M 264.364 0
From P. arabica. Oil.
C14H220 2 M 222.327
12-Acetoxy, Me ether: Constit. of Cyperus rotundus. Cryst. (Et20). Mp 108-109°.
CtsHu04 M 306.401 [(J(Jn -40.1° (c, 3.1 in CHC1 3).
From P. arabica. Oil.
Hikino, H. eta/, Chern. Pharm. Bull., 1969, 17, 1390.
6~-jorm
7?;, ,14-Dihydro: 6-Hydroxy-3(15)-caryophyUen-8-one
C15H 240 2 M 236.353 Kobusone Sq-00780
lsol. from Premna spp. Liq. 6,7-Epoxy-15-nor-3-caryophyllanone. Caryophyllene keto

v-
epoxide
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2529; 1987, 26,
3356. [24173-71-5]
De Pascual Teresa, J. eta/, An. Quim., Ser. C, 1982, 78, 317.
Rao, C.B. eta/, Indian J. Chern., Sect. B, 1985, 24, 403.

9-Hydroxy-3(15),6-caryophylladien-8-one Sq-00777

{f
0
C14H 220 2 M 222.327
Constit. of Cyperus rotundus. Also in lavender oil. Cryst.
(pet. ether). Mp 60-61°. [(J(Jn -142.2° (c, 3.6 in CHC1 3).
Barton, D.H.R. et at, J. Chern. Soc., 1957, 2988 (synth)
Hikino, H. et at, Chern. Pharm. Bull., 1969, 17, 1390 (isol, struct)
Kaiser, R. eta/, Helv. Chim. Acta, 1983, 66, 1843 (iso/)
C15H 220 2 M 234.338
(6E,9fJ)-form [62346-21-8] Buddledin B
Constit. of the root bark of Buddleia davidii. Cryst. Mp
139-141°. [(J(Jn -3W (c, 0.54 in CHC1 3).
Ac: [62346-20-7]. Buddledin A
Ct,H240 3 M 276.375
Constit. of B. davidii. Cryst. Mp 94-95°. [(Xln -245° (c,
0. 74 in CHC1 3).
9-Deoxy: [62346-22-9]. 3(15),6-Caryophylladien-8-one.
Buddledin C

293
Lychnosalicifolide- Punctaporonin B Sq-00781- Sq-00786

Lychnosalicifolide Sq-00781 Parvinolide Sq-00784

[87385-29-3] Caryophyllen-9p,10-olide
[95930-42-0]

CtsH220 3 M 250.337
~
HOH2C
o~
6):;01
HJ
Constit. of Lychnophora sa/icifo/ia. Cryst. (Et20fpet. C15H 220 2 M 234.338
ether). Mp 98°. [oc]i: + 100° (c, 0.39 in CHC13). Constit. of Pogostemon parviflorous. Cryst. (C6 H6fpet.
3-Epimer: 3-epi-Lychnosalicifo/ide. 3-Epilychnosa/icifo/ide ether). Mp 134-135°. [1X]n +204.83° (c, 0.033 in CHC13).
CtsH 220 3 M 250.337 6,7-Epoxide: [102227-61-2]. Epoxyparvinolide
Constit. of L. salicifolia. Oil. C15H 220 3 M 250.337
Bohlmann, F. et a/, Justus Liebigs Ann. Chern., 1983, 1455. From P. parviflorus. Cryst. (C6H 6 jpet. ether). Mp 180-
1820. [ocln +37.59° (c, 0.47 in CHC1 3).
Nanda, B. eta/, J. Chern. Res. (S), 1984, 394 (cryst struct)
Naematolin Sq-00782

aH
Nanda, B. eta/, Phytochemistry, 1985, 24, 2735 (isol)
[11054-16-3]
HO OH Puliscabrin Sq-00785

jj-EQ:HI
I Absolute
OAc configur~tion 0 CH20 6' I
I

0 H:f" H
C17H2405 M 308.374 0
Metab. of Hypholoma elongatipes, H. fasciculare, H.
sublateritium and of the fungus Naematoloma C30 H 420 3 M 450.660
fasciculare. Cytotoxic. Cryst. Mp 144-145°. [oc]i,2 -370° (E)-form [84122-92-9]
(c, 1.0 in CHC1 3), [oc]i,2 -330°. Rare example of cis-fused Constit. of Pulicaria scabra. Gum. [oc]i: -74° (c, 0.8 in
caryophyllane. CHC1 3).
I> Qll275000. (Z)-form
8-Ketone: [92121-62-5]. Naematolone Constit. of P. scabra. Gum.
Ct7Hz20 5 M 306.358 6'-Epimer:
Metab. of H. elongatipes, H. capnoides and H. C30H 420 3 M 450.660
sublateritium. Cytotoxic. Weakly active against gram- Constit. of P. scabra. Gum.
positive bacteria, fungi and yeasts. Oil. [oc]i,2 + 116° (c, Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1659.
0.46 in CHC1 3).
13-Hydroxy: [102167-68-0]. Naematolin B Punctaporonin B Sq-00786
Ct 7H 240 6 M 324.373 Punctatin B. M 95154. Antibiotic M 95154
Metab. of N. fasciculare. Cryst. Mp 122-123°. [oc]i;' [93697-36-0]
-352°.
Ito, Y. eta/, Chern. Pharm. Bull., 1967, IS, 2009 (isol)
Backens, S. eta/, Justus Liebigs Ann. Chern., 1984, 1332 (struct)
Tsuboyama, S. eta/, Bull. Chern. Soc. Jpn., 1986, S9, 1921 (cryst
struct)

14,14' -Oxybis[3(15),6-caryophylladien-8- Sq-00783

one) CtsH2403 M 252.353
Metab. of Poronia punctata and Hypoxylon terricola.
Cryst. (EtOAc). Mp 187.5-188.SO. [ali? -221° (c, 1 in
MeOH). Not to be confused with homoisoflavone
Punctatins.
Kende, A.S. eta/, J. Am. Chern. Soc., 1988, 110, 6265 (synth)
Anderson, J.R. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 823
(iso/, struct)
Edwards, R.L. eta/, J. Chern. Soc., Perkin Trans. 1, 1989, 57 (isol)
C30H 42 0 3 M 450.660
lsol. from Pulicaria arabica. Oil.
Hafez, S. eta/, Phytochemistry, 1987, 26, 3356.

294
Punctaporonin G - Cupalaurenol Sq-00787 - Sq-00793

Punctaporonin G Sq-00787
1p,7P- Epoxy-3 ,5-caryophyl/adien-15-ol
[126637-61-4] Cuparanes

14(7-+ 6)-Abeo-4-cuparen-3-ol Sq-00790

C 15H110 2 M 234.338
Metab. of Poronia punctata. Pale yellow waxy solid. Mp
32-38°. [1X)i;l -231° (c, 1 in MeOH).
HOoy
Ac: [126637-62-5]. C 15Hu;0 M 222.370
Needles. Mp 65-66°. Constit. of Demotarisia linguifolia. Oil. [1X]n -39.6° (c, 4 in
Edwards, R.L. et a/, J. Chern. Soc., Perkin Trans. I, 1989, 1939 CHCI 3).
(isol, pmr, cmr) Nagashima, F. eta/, Phytochemistry, !990, 29, 3230 (isol)

~-Bro01ocuparene Sq-00791
[57794-64-6]

Bicyclohumulanes
C 15H 21 Br M 281.235
Constit. of Laurencia spp. Oil. [1X]n + 23° (c, 0.95 in
2,6-Bicyclohumulanedione Sq-00788 CHCI 3).
I ,5,8,8-Tetramethylbicyclo[8.1.0]undecane- 2,6-dione, 9CI.
I ,5-Bicyclohumulenedione 10-Epimer: [57766-60-6]. r,.-lsobromocuparene
C15H 21 Br M 281.235
[880 I 0-66-6] Constit. of L. spp. Oil. [1X]n +91° (c, 0.87 in CHCI 3).
Suzuki, T. eta/, Tetrahedron Lett., 1975, 3057.

2-(3-Bromo-1,2,2-trimethylcyclopentyl)-5- Sq-00792
methylphenol
[125092-26-4]

H,Co:f"'
C15H240 2 M 236.353
Constit. of leaves of Lippia integrifolia. Needles (EtOH).
Mp 183°. [1X]i? -29.1° (c, 9.6 in CHCI 3).
Catalan, C.A. et a/, Phytochemistry, 1983, 22, 1507.

2-Bicyclohumulen-6-one Sq-00789 C 15H 21 Br0 M ~7.234

Metab. of Laurencia implicata. Oil. [1X]n -9.02° (c, 0.013 in
CHCI3).
Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1685 (isol, pmr, cmr)
(+)-form
Cupalaurenol Sq-00793
4-Bromo-2-methyl-5-( I ,2,2-trimethyl-3-cyclopenten-I-
C 15H240 M 220.354 yl)phenol, 9CI
(+)-form [71493-03-3] Bicyclohumulone [103439-84-5]
Constit. of Plagiochila acanthophyl/a. Cryst. (EtOH).
Mp 76°. [1X]D +60°.
2,4-Dinitrophenylhydrazone: Cryst. Mp 174-176°.
(-)-form
1-Acripruninone
Constit. of Acritopappus prunifolius. Gum. [1X]i;' -41.7° CISH19Br0 M 295.218
(c, 0.2 in CHCI 3). Constit. of Aplysia dactylomela. Oil. [1X]i? + 87.9° (c, 1 in
[77 480-09-2] CHCI 3).
Matsuo, A. eta/, J. Chern. Soc., Chern. Commun., 1979, 174 (iso/, Ac: [103456-69-5]. Cupalaurenol acetate
cryst struct, abs corifig) C 17H 21 Br02 M 337.256
Shirahama, H. et a/, Tetrahedron Lett., 1980, 4835 (synth) From A. dactylomela. Oil. [1X]i? + 65.1° (c, 1 in CHCI3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 147 (1- Ichiba, T. eta/, J. Org. Chern., 1986, 51, 3364.
Acripruninone)

295
Cuparene - P..Cuparenone Sq-00794 - Sq-00797

Cuparene Sq-00794 Constit. of Radula perrottetii and Helicobasidium

Widdrene II mompa. Cryst. Mp 72-73°, Mp 124-125°. [1X]I> -57.4°
(CHC1 3). The name 2,3-Cuparenediol is from the
alternative numbering scheme. 2,3-Cuparenediol and
(R)-form HM4 have not been compared, but identical structs.
Absolute were assigned although the Mp's are widely different.
configuration Opt. rotn. refers to HM4.
C15H 22 M 202.339 5-Hydroxy: HMJ
(R)-form [16982-00-6] C15H 220 2 M 234.338
Constit. of Bazzania pompeana. Oil. [1X]n -27.6° (c, 3.6 Metab. of H. mompa. Needles. Mp 139.5-140°. [1X]n
in CHC1 3). -55.0° (CHC1 3).
2-Hydroxy: see <5-Cuparenol, Sq-00795 Hopkins, B.J. eta/, J. Chern. Soc., Perkin Trans. 1, 1974, 32 (isol)
15-Hydroxy: [4584-25-2]. y-Cuparenol Matsuo, A. eta/, Phytochemistry, 1975, 14, I037 (abs config)
C15H 220 M 218.338 Asakawa, Y. eta/, Phytochemistry, 1982, 21, 248I (!,2-
Cuparenediol)
Constit. of Thujopsis dolabrata. Oil. Bp0 _5 110° (bath). Kajimoto, T. eta/, Chern. Lett., 1989, 527 (HM1, HM4)
[1X]i] + 92°.
15-Hydroxy, 4-nitrobenzoyl: Cryst. Mp 65°.
Ot-Cuparenone Sq-00796
(S)-form [56324-31-3]
2,2,3-Trimethy/-3-(4-methylphenyl)cyclopentanone, 9CI
Constit. of Chamaecyparis thyoides, Biota orienta/is,

H,CO?o
Widdringtonia spp. and Jungermannia rosulans. Also (16196-32-0]
from Juniperus, Cupressus and Torulopsis spp. Oil. Bp 19
138°. [1X]n +35°.
2-Hydroxy: see <5-Cuparenol, Sq-00795
Ito, S. eta/, Tetrahedron Lett., I965, 3777 (y-Cuparenol)
Vig, O.P. eta/, Indian J. Chern., I973, 11, 98I (synth) C15H 200 M 216.322
de Mayo, P. eta/, J. Chern. Soc., Perkin Trans. I, I974, 2559
Constit. of the wood of "Mayur pankhi" (Thuja orienta/is
(synth)
Bird, C.W. eta/, Synthesis, I974, 27 (synth) or T. compacta). Cryst. Mp 52-53°. [IX]~ +177.1°.
Matsuo, A. et a/, Phytochemistry, I975, 14, I037 (isol, abs config) Semicarbazone: Cryst. (MeOH aq.). Mp 212-215°.
Matsuo, A. eta/, Tetrahedron Lett., I977, 38, 2I (isol) lOIX-Alcohol: [21730-87-0]. 11.-lsocupareno/
Kametani, T. et a/, J. Chern. Soc., Perkin Trans. I, I980, 759; C15H 22 0 M 218.338
I984, 1305 (synth)
Nabeta, K. eta/, Agric. Bioi. Chern., I984, 48, 3I4I; 1986, 50,
Isol. from Biota orienta/is essential oil. Cryst. Mp 78.5°.
2915 (biosynth) (IX]~ +81" (CC14).
Ishibashi, H. eta/, J. Chern. Soc., Chern. Commun., 1988, 827 lOP-Alcohol.· [21730-88-1]. 11.-Cupareno/
(synth) CISH220 M 218.338
Kametani, T. eta/, J. Chern. Soc., Perkin Trans. 1, I988, 193 Constit. of B. orienta/is essential oil. Cryst. Mp 73°. [IX]~
(synth) - 11.6° (CC14).
Chetty, F.-L. et a/, Tetrahedron Lett., 1964, 73 (isol)
0-Cuparenol Sq-00795 Irie, T. eta/, Tetrahedron Lett., 1967, 3187 (abs conjig)
2-Methyl-5-(1 ,2,2-trimethylcyclopentenyl)phenol, 9CI. 2- Tomita, B. et a/, Tetrahedron Lett., 1968, 843 (11.-Cupareno/s)
Hydroxycuparene Leriverina, P. eta/, Bull. Soc. Chim. Fr., 1973, 3498 (synth)
Ha1azy, S. et a/, Tetrahedron Lett., 1982, 23, 4385 (synth)
Greene, A.E. eta/, J. Org. Chern., 1983, 48, 4763 (synth, bib/)
Anand, R.C. eta/, Indian J. Chern., Sect. B, 1984, 23, 1054.
Posner, G.H. eta/, Tetrahedron Lett., 1984, 25, 383 (synth, bib/)
(R)-form Ei1bracht, P. et a/, Chern. Ber., 1985, 118, 825 (synth)
Anand, R.C. eta/, Indian J. Chern., Sect. B, 1985, 24, h73 (synth)
Taber, D.F. eta/, J. Am. Chern. Soc., 1985, 107, 196 (synth)
Takano, S. eta/, J. Chern. Soc., Chern. Commun., 1989, 271 (synth)
C15H 22 0 M 218.338 Srikrishna, A. eta/, Indian J. Chern., Sect. B, 1990, 29 . 879 (synth)
(R)-form [52554-81-1]
Bp0_05 100-110° (bath). (1X]n + 58° (CHC1 3). IJ-Cuparenone Sq-00797
Ac: [28152-91-2]
C17H 240 2 M 260.375
Cryst. Mp 38-39°.
(S)-form (38412-84-9]
Constit. of Marchantia polymorpha, Bazzania pompeana
and Cascarilla spp. Bp0_05 100° (bath). [1X]n -65° (c, 1.2
in CHC1 3). CtsH200 M 216.322
Constit. of the wood of "Mayur pankhi" (Thuja spp.).
Ac: Cryst. Mp 37.5-38.SO.
Bp0 _8 114-115°. [IX]~ +48°. n~ 1.5292.
]-Hydroxy: (85526-56-3]. 1,2-Cuparenedio/. 3-Methyl-6-
Semicarbazone: Cryst. Mp 213.5-215°.
(1 ,2,2-trimethylcyclopentyl)-1 ,2-benzenediol, 9CI. 2,3-
Cuparenediol. HM4 91X-Alcohol: P-Cuparenol
C15H 220 M 218.338
lsol. from Biota orienta/is. Oil. [IX]~ +63.8° (CHC1 3).
Tomita, B. et a/, Tetrahedron Lett., 1968, 843 (JJ-Cuparenol)
Mane, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1973, 1806 (synth)
Casares, A. eta/, Synth. Commun., 1976, 6, 11 (synth)

296
e-Cuprenene - Laurebiphenyl Sq-00798 - Sq-00804

Jung, M.E. et al, Tetrahedron Lett., 1980, 4397 (synth) Helicobasidin Sq-00802
Halazy, S. et al, Tetrahedron Lett., 1982, 23, 4385 (synth) 2,5-Dihydroxy-3-methy/-6-( 1,2 ,2-trimethy/cyc/opentyl)-1 ,4-
Greene, A.E. et al, J. Org. Chern., 1984, 49, 931 (synth) benzoquinone
[13491-25-3]
e-Cuprenene Sq-00798
2-Methy/-5-(1 ,2,2-trimethy/cyc/opentyl)-1 ,3-cyc/ohexadiene, HO O

H3C~
9C/
[66389-23-9]
~H K Absolute
configuration

C 15H 24
~
M 204.355
CtsH2004 M 264.321
Fungal pigment from He/icobasidium mompa. Orange-red
cryst. Mp 190-192°. [cx]i; -123° (c, 1 in CHCI 3).
Constit. of Marchantia polymorpha. Oil. [1X]n + 168°. 4-Deoxy: [13491-69-5]. Helicobasin
CtsH200 3 M 248.321
/1 3•15 -Isomer: [66389-22-8]. ~Cuprenene. 3-Methy/ene-6- Isol. from H. mompa. Yellow needles. Mp 194-195°. [cx]i;
(1 ,2,2-trimethy/cyclopentyl)cyclohexene, 9CI -186.SO (CHC1 3).
Constit. of M. po/ymorpha. Oil. [1X]n -40° (c, 1.3 in
Natori, S. et al, Chern. Pharm. Bull., 1964, 12, 236; 1967, 15, 380
CHC1 3).
(isol, struct)
Matsuo, A. et al, Phytochemistry, 1985, 24, 777. Adams, P.M.~et al, J. Chern. Soc., Perkin Trans. !, 1972, 586
(biosynth, bib/)
Cuprenenol Sq-00799 Tanabe, M. et al, Tetrahedron Lett., 1973, 4723 (biosynth)
1-Methy/-4-( 1,2 ,2-trimethy/cyc/opentyl)-2-cyc/ohexen-1-o/,
9C/ Lagopodin A Sq-00803
[66389-06-8] 2-Methy/-5-( 1,2,2-trimethy/-4-oxocyc/opentyl)-2,5-
cyc/ohexadiene-1 ,4-dione, 9CI
[62185-66-4]

C 15H 260 M 222.370

Constit. of Jungermannia rosulans. Cryst. Mp 95-96.SO. [1X]n
+640.
H,C~O
Matsuo, A. et al, Tetrahedron Lett., 1977, 3821. C 15H 180 3 M 246.305
Benzoquinone antibiotic. Constit. of Coprinus lagopus.
Cuprenolide Sq-00800 Active against gram-positive bacteria. Yellow cryst. [cxJn
[127350-69-0] -10° (CHC1 3). V. labile in soln.
5-Hydroxy: [62512-03-2]. Lagopodin B
CtsH 180 4 M 262.305
Constit. of C. /agopus. Antimicrobial agent. V. labile in
soln. [cxJn + 17° (CHC1 3).
2,5-Dihydroxy: Hydroxylagopodin B
C15H 180 5 M 278.364
Constit. of C. macrorrhizus. Shows antimicrobial
C 15H 110 2 M 234.338
activity. Orange-red cryst. (C 6H 6 jhexane). Mp 184-186°.
Constit. of Ricciocarpus natans. Cryst. (EtOAcjhexane).
[cxJi? + 24.4° (c, 1.04 in CH 2Cl 2). Bottom, C.B. et al, Phytochemistry, 1975, 14, 1433
(Hydroxylagopodin B)
14-Hydroxy: [127350-70-3]. Cuprenolidol Bu'Lock, J.D. et al, Phytochemistry, 1976, 15, 2004 (struct, pmr)
C 15H 110 3 M 250.337
Constit. of R. natans. Oil. [cxJi? + 38.7° (c, 0.35 in
CH 2C12). Laurebiphenyl Sq-00804
Wurzel, G. et al, Phytochemistry, !990, 29, 2565 (isol, pmr, cmr) [97649-04-2]

Grimaldone Sq-00801
q~
f;[Ya
CH,

Ho0:!:joH
C15H 110 M 218.338
Absolute configuration

Constit. of Manniafragrans. Cryst. (pentane). Mp 91-92°.

0 H,C

[cx]i;4 +49.6° (c, 0.635 in CHC1 3).

Huneck, S. et al, Phytochemistry, 1988, 27, 1405. C30H 380 2 M 430.629
Constit. of Laurencia nidifica. Cryst. (C 6H 6 jhexane). Mp
232-232.SO. [cx]i; + 15.2° (c, 0.092 in CHC1 3).
Shizuri, Y. et al, Phytochemistry, 1985, 24, 1385.

297
1-Methyl-4-(1,2,2-... - 4-(1,2,2-Trimethylcyclopentyl) ... Sq-00805 - Sq-00810

1-Methyl-4-(1,2,2-trimethylcyclopentyl)- Sq-00805 Tochuinol Sq-00809

1,3-cyclohexadiene 1,2-Dimethyl-2-(4-methylphenyl)cyclopentanemethanol, 9CI.
2-Cuprenene 12-Hydroxycuparene
[5046-93-5]

C 15Hn0 M 218.338
C 15H 24 M 204.355
Constit. of, inter alia, Thujopsis dolabrata. Oil. Bp 140- Ac: [111621-35-3]. Tochuinyl acetate
1410. Cuprenene is a mixt. of this with 1-Methy1-4- C 17H 240 1 M 260.375
(1,2,2-trimethy1cyclopenty1)-1 ,4-cyclohexadiene, Sq- Constit. of Tochuina tetraquetra. Oil. [cx]i,S -42.SO (c,
00806. 1.09 in CH 2C12).
1,4-Dihydro, Ac: [111621-36-4]. Dihydrotochuinyl acetate
Dauben, W.G. eta/, J. Org. Chern., 1966, 31, 315.
C 17H 260 1 M 262.391
Constit. of T. tetraqueta. Oil. [cx]i,S -29.3° (c, 1.11 in
1-Methyl-4-(1,2,2-trimethylcyclopentyl)- Sq-00806 CH 2C12).
1,4-cyclohexadiene Williams, D.E. et al, Can. J. Chern., 1987, 65, 2244.
4-Cuprenene
[4895-23-2] 4-(1,2,2-Trimethylcyclopentyl)benzoic acid Sq-0081 0
Cuparenic acid

HCX>C~
C 15H 24 M 204.355
Constit. of, inter alia, Thujopsis dolabrata. Oil. Bp 140- C 15H 200 1 M 232.322
141°. [cxJn + 50° (c, 1.1 in CHC1 3).
(R)-form [509-02-4]
Dauben, W.G. et al, J. Org. Chern., 1966, 31, 315. Constit. of Chamaecyparis thyoides and Widdringtonia
spp. Cryst. (pet. ether). Mp 158-160°. [cxln +63° (c, 2.4
Rosulantol Sq-00808 in CHC1 3).
4-Hydroxy-2-methyl-5-( 1,2 ,2-trimethylcyclopentyl)-2- (±)-form
cyclohexen-1-one, 9C/ Mp 151-154°.
[66389-07 -9] Enzell, C. et a/, Tetrahedron, 1958, 4, 361.
Parker, W. et al, Proc. Chern. Soc., London, 1961, 74 (synth)
0

~c0--9
OH
C 15H 240 1 M 236.353
Constit. of Jungermannia rosulans. Cryst. Mp 125-126°.
[cxln -lOo.
Matsuo, A. et al, Tetrahedron Lett., 1977, 3821.

298
Cyclolaurene - Herbertenolide Sq-00811 - Sq-00814

Cyclolauranes Herbertanes

Cyclolaurene Sq-00811 Herbertene Sq-00813

1,2-Dimethyl-2-(4-methylphenyl)bicyclo[3.l.O]hexane, 9CI 1-Methyl-3-(1 ,2,2-trimethylcyclopentyl)benzene, 9CI. 1,2,2-
[103439-82-3] Trimethyl-1-(3-me thylphenyl)cyclopentane

~D~
H3cU r
C 15H 10 M 200.323 C15H 22 M 202.339
Constit. of Aplysia dactylomela. Oil. [exJn -9.0° (c, 0.22 in (S)-form [80322-46-9]
CHC1 3). Constit. of Herberta adunca. Oil. [exln -48.3° (c, 1.31 in
7-Bromo, 10-hydroxy: [103439-83-4]. Cyclolaurenol CHC1 3).
ClsH19BrO M 295.218 3-Hydroxy: [81784-09-0]. 2-Methyl-4-(1,2,2-
Constit. of A. dactylomela. Cryst. Mp 109-109.SO. [ex]~ trimethylcyclopentyl)phenol, 9CJ. 1-(4-Hydroxy-3-
-9.3° (c, 4.04 in CHC1 3). methylphenyl)-1,2,2-trimethylcyclopentane. P-Herbertenol
7-Bromo, 10-acetoxy: [103456-68-4]. Cyclolaurenol acetate ClsH220 M 218.338
C 17H 21 Br0 2 M 337.256 From H. adunca. Cryst. Mp 77-78°. [exln -47°.
From A. dactylomela. Oil. [ex]~ -9.2° (c, 0.82 in 1-Hydroxy: [81784-10-3]. 4-Methyl-2-(1,2,2-
CHC1 3). trimethylcyclopentyl)phenol, 9CI. 1-(2-Hydroxy-5-
7-Hydroxy: Debromolaurinterol methylphenyl)-1 ,2,2- trimethylcyclopentane. rx.-Herbertenol
Constit. of L. intermedia. [ex]i? -12.2° (CHC1 3). C15H 220 M 218.338
8-Bromo, 7-hydroxy: Neolaurinterol Constit. of H. adunca. Oil. [exln -55°.
C 15H 19Br0 M 295.218 l-Hydroxy,l2-aldehyde: [81784-18-1]. 4-Hydroxy-3-(1 ,2,2-
Constit. of Laurencia okamurai. Cryst. Mp 62-63°. [exln trimethylcyclopentyl)benzaldehyde, 9CJ. rx.-
~ W (c, 0.57 in CHC1 3). Formylherbertenol
/0-Bromo, 7-hydroxy: Laurinterol C15H 100 2 M 232.322
ClsH19BrO M 295.218 Constit. of H. adunca. Cryst. Mp 134-135°. [exln -66°.
Constit. of L. intermedia. Cryst. (MeOH). Mp 54-55°. 1,2-Dihydroxy: [86996-95-4]. Herbertenediol
[exJn + 13.3° (c, 1.9 in CHC1 3). Constit. of H. adunca. Cryst. Mp 90.5-91.5°. [exln
Cameron, A.F., J. Chern. Soc. B, 1969, 692 (abs corifig, -46.SO.
Laurinterol) Matsuo, A. eta/, J. Chern. Soc., Chern. Commun., 1981, 864 (isol,
Irie, T. eta/, Tetrahedron, 1970, 26, 3271 (isol, Laurinterol, struct)
Debromolaurinterol) Matsuo, A. et a/, Chern. Lett., 1982, 463, 1041 (derivs)
Feutrill, G.l. et al, Aust. J. Chern., 1973, 26, 345 (synth, Frater, G., J. Chern. Soc., Chern. Commun., 1982, 521 (synth)
Laurinterol) Leriverend, M.-L., J. Chern. Soc., Chern. Commun., 1982, 866
Suzuki, M. et al, Tetrahedron Lett., 1978, 2503 (Neolaurinterol) (synth)
lchiba, T. et al, J. Org. Chern., 1986, 51, 3364 (Cyclolaurene, Chandrasekaran, S. et al, Tetrahedron Lett., 1982, 23, 3799 (synth)
Cyclolaurenol, Cyclolaurenol acetate) Matsuo, A. eta/, J. Chern. Soc., Perkin Trans. 1, 1986, 701 (isol,
struct)
Frater, G. eta/, J. Chern. Soc., Chern. Commun., 1988, 1198
Laurequinone Sq-00812 (biosynth)
[94418-42-5] BaneJjee, A.K. eta/, J. Chern. Soc., Perkin Trans. I, 1988, 2485

'91)
(synth)
0
Herbertenolide Sq-00814
2,3,3a,9b- Tetrahydro-3a,8,9b-
trimethylcyclopenta(c](l]benzopyran-4(1H)one, 9CI
[86996-94-3]
v

C15H 180 2 M 230.306

Constit. of Laurencia nidifica. Pale-yellow oil. [ex]i,l -53.5° H,C <""'?£:( Absolute
(c, 0.91 in CHC1 3).
Shizuri, Y. eta/, Phytochemistry, 1984, 23, 2672. Uo~o configuration

ClsHJa02 M 230.306
Constit. of Herberta adunca. Cryst. Mp 95.5-96.SO. [exln
-86.4°.
Matsuo, A. et al, J. Chern. Soc., Perkin Trans. I, 1986, 701 (isol,
struct)

299
HM 2 - 12-Bromo-4(13),6,9-lauratriene Sq-00815 - Sq-00820

HM 2 Sq-00815

Lauranes
[121043-28-5]

OA;~
HOO-\J
H3C
Aplysin Sq-00819
C 17H 240 3 M 276.375
Metab. of Helicobasidium mompa. Oil. [1X]n -37.0° [6790-63-2]
(CHC1 3).
Kajimoto, T. et a/, Chern. Lett., 1989, 527.
Br~,
HM3 Sq-00816
H3cUo~'
C15H 19Br0 M 295.218

0\J
Constit. of Aplysia kurodai. Cryst. (MeOH). Mp 85-86°.
[1X]i," -85.4° (CHC1 3).
Debromo: [23444-68-0]. Debromoaplysin
H 3C OH C 15H 200 M 216.322
Constit. of A. kurodai. Oil.
C 17H 240 3 M 276.375
13-Hydroxy: [6790-64-3]. Aplysinol
(S)-form [121043-29-6] C15H 19Br0 2 M 311.218
Metab. of Helicobasidium mompa. Needles. Mp 158.5- Constit. of A. kurodai. Cryst. (CC14). Mp 158-160°. [IX]~
160.00. [1X]n -8.1° (CHC1 3). -55.6° (CHC1 3).
Kajimoto, T. et a/, Chern. Lett., 1989, 527. 13-0xo: [64052-99-9]. Aplysinal
C15H 17Br0 2 M 309.202
Mastigophorene C Sq-00817 Constit. of Marginosporum aberrans.
[118584-11-5] Debromo, 13-bromo: [68773-08-0]. lsoaplysin
C 15H 19Br0 M 295.218
Constit. of L. nipponica. Oil. [1X]n -33° (c, 0.69 in
CHC1 3).
Yamamura, S. et al, Tetrahedron, 1963, 19, 1485 (isol)
Cameron, A.F. et al, J. Chern. Soc. B, 1969, 692 (struct)
Yamada, K. et al, Tetrahedron, 1969, 25, 3509 (synth)
McMillan, J.A. et al, Tetrahedron Lett., 1976, 4219 (struct,
Aplysinol)
Ronald, R.C. et a/, Tetrahedron Lett., 1976, 4413 (synth, deriv,
C30H 42 0 4 M466.659 bib£)
Constit. of Mastigophora die/ados. Oil. [IX]~ -46.7° (c, 0.4 Ohta, K. eta/, Phytochemistry, J977, 16, 1062 (Aplysinal)
in CHC1 3). Ronald, R.C. et al, J. Org. Chern., 1980, 45, 2224 (synth)
Goldsmith, D.J. et a/, J. Org. Chern., 1980, 45, 3989 (synth)
Fukuyama, Y. eta/, J. Chern. Soc., Chern. Commun., 1988, 1341
Suzuki, M. eta/, Bull. Chern. Soc. Jpn., 1986, 59, 3981 (Isoaplysin)
(isol, pmr, cmr)
Ghosh, A. et al, J. Chern. Soc., Chern. Comrnun., 1988. 1421
(synth)
Mastigophorene D Sq-00818 Biswas, S. et al, J. Org. Chern., 1990, 55, 3498 (synth)
[118584-12-6]
12-Bromo-4(13),6,9-lauratriene Sq-00820
1-[3-(Bromomethyl)-1-methyl-2-methy/enecyclopentyl]-4-
methyl-1 ,4-cyclohexadiene, 9CI
[93395-09-6]

C30H 420 4 M 466.659

Constit. of Mastigophora die/ados. Cryst. Mp 201-203°.
[IX]~ -46.1° (c, 0.5 in CHC1 3).
Fukuyama, Y. eta/, J. Chern. Soc., Chern. Commun., 1988, 1341
(isol, pmr, cmr)

C 15H 21 Br M 281.235
Constit. of red alga Laurencia pinnatifida. Unstable oil.
[1X]n +2.3° (c, 2.15 in CHC1 3).
8,11-Didehydro: [93395-10-9]. 12-Bromo-4(13),6,8,10-
lauratetraene. 1-[3-(Bromomethyl)-1-methyl-2-
methylenecyclopentyl]-4-methylbenzene, 9CI
C15H 19Br M 279.219
Constit. of L. pinnatifida. Oil. [1X]n +4.7° (c, 3.19 in
CHC1 3).
Gonzalez, A.G. et al, Tetrahedron, 1984, 40, 2751.

300
10-Bromo-3-laurene-7,12-diol- Isolaurinterol Sq-00821 ~ Sq-00827

10-Bromo-3-laurene-7,12-diol Sq-00821 12-1odo: [72030-67-2]. lodoether A

10-Bromo-7,12-dihydroxy-3-laurene C 15H 18Br10 M 421.115
[72008-58-3] Constit. of L. nana. Cryst. Mp 99-102° dec. [ocJn +29°
(c, 0.94 in CHC1 3).
Debromo,12,12-dibromo: Bromoether A
C18H 18Br10 M 410.148
Constit. of L. glandu/ifera. Cryst. (MeOH). Mp 125-
1260. [oc)i;l + 79° (c, 0.4 in CHCI 3).
Debromo, 6-bromo: [235226-41-2]. 2-(Bromomethyl)-2,3,4,5-
tetrahydro-5,8,10-trimethyl-2,5-met/umo-1-benzoxepin,
9CI
C15H 19Br02 M 311.218 C15H 19Br0 M 295.218
Constit. of Laurencia nana. Cryst. Mp 141-145°. [oc]n lsol. from L. glandulifera.
+ 100° (c, 1.2 in CHC1 3). Debromo, 6,6-dibromo: [63001-94-5]. 2-(Dibromomethyl)-
Izae, R.R. et al, J. Am. Chern. Soc., 1979, 101, 6136. 2,3,4,5-tetrahydro-5,8,10-trimethy/-2,5-met/umo-1-
benzoxepin, 9CI
Caraibical Sq-00822 C 15H 18Br10 M 374.115
lsol. from L. glandulifera. Cryst. (MeOH). Mp 125-126°.
[79383-37-2]
[oc)i;l + 79° (c, 0.38 in CHC1 3).
Kazlauskas, R. et al, Aust. J. Chern., 1976, 29, 2533 (iso/)
Suzuki, M. et al, Bull. Chern. Soc. Jpn., 1979, 52, 3349 (derivs)
Izae, R.R. eta/, J. Am. Chern. Soc., 1979, 101, 6136 (Iodoether A)
Goldsmith, D.J. et al, J. Org. Chern., 1980, 45, 3989 (synth)

C 15H 17Br01 M 309.202 Isolaurene Sq-00825

Constit. of Laurencia caraibica. Cryst. Mp 106-108°. [oc]n 1-Methy/-4-(1,2,3-trimethyl-2-cyclopenten-1-yl)benzene, 9CI
+42° (c, 1.01 in CHC1 3).
[4608-39-3]
lzac, R.R. et al, Tetrahedron Lett., 1981, 1799.

Curcumene ether Sq-00823 H,C~

[24048-43-9]

C 15H 20 M 200.323
Constit. of Laurencia g/andulifera and L. nipponica. Oil.
C 15H 200 M 216.322 Bp21 140-142°. [oc]n + 108.7° (c, 1.4 in CHC13).
Tentative struct. Kametani et a/ synthezise the original Irie, T. et a/, Tetrahedron, 1969, 25, 459.
pyran struct. assigned in 1969without commenting on
the revision of Kirtany et a/. The CA name also follows Isolaurenisol
the original struct. Constit. of Biota orienta/is. Oil. [oc)~
Sq-00826
+28°. . [93236-38-5]
[97265-18-4)
.Kirtany, J.K. et al, Indian J. Chern., 1974, 12, 1202 (struct)
Kametani, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1984, 1305.

Filiformin Sq-00824
[62311-75-5]

C1sH19BrO M 295.218
Constit. of Laurencia distichophylla. Oil. [oc]~ -42° (c, 2.5
in CHC1 3).
Blunt, J.W. eta/, Phytochemistry, 1984, 23, 1951.

C 15H 19Br0 M 295.218 Isolaurinterol Sq-00827

Constit. of Laurenciafiliformis. Cryst. (pet. ether). Mp [29424-17. 7]
86.4-87.3°. (oc]n -20° (c, 1 in CHC13). Prob. artefact of
cyclisation of A11olaurinterol.
6-Hydroxy: [62311-76-6]. Filiforminol
C15H 19Br01 M 311.218
Constit. of L. fi/iformis. Oil. {oc]n -13.7° (c, 1.1 in
CHQ3).
C 15H 19Br0 M 295.218
6-Bromo: [63001-93-4]. 7-Bromo-2-(bromomethyl)-2,3,4,5-
Minor constit. of Laurencia intermedia. Oil. Bp1. 3 144°. [ocJn
tetrahydro-5,8,10-trimethy/-2,5-methano-1-benzoxepin, 9CI -82° (c, 1.5 in CHC13).
C 15H 18Br10 M 374.115
Isol. from L. g/andulifera. Cryst. (MeOH). Mp 86-87°. Ac: Oil. [oc]n -70° (c, 1.42 in CHCI 3).
[oc)i;l +22° (c, 1.16 in CHC1 3).

301
Laurene - Baccharinoid Bl Sq-00828 - Sq-00830

Iiie, T. et al, Tetrahedron, 1970, 26, 3271. Izae, R.R. et al, J. Am. Chern. Soc., 1979, 101, 6136 (10-Bromo-7-
Capon, R.J. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1302 (isol, hydroxy-11-iodolaurene)
pmr, ir) Jaber, D.F. et al, Tetrahedron Lett., 1980, 2779 (synth)
Suzuki, T. et al, Bull. Chern. Soc. Jpn., 1982, 55, 1561 (Laurena/,
Laurena/ acetate, Laurena/, lsodihydro/aurene)
Laurene Sq-00828 Gewali, M.D. et al, J. Org. Chern., 1982, 47, 2792 (synth,
1,2-Dimethyl-3-methylene-1-(4-methylphenyl)cyclopentane A/lolaurinterol)
[18452-41-0] Kametani, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, 193
(synth)

Laurenisol Sq-00829
[23526-39-8]

C15HlG M 200.323
Constit. of Laurencia glandulifera. Oil. Bp21 131-133°. [IX]~
+48.7° (EtOH).
5-Epimer: [18452-45-4]. Epilaurene
C15H2G M 200.323
From L. glandulifera and L. nipponica. Oil. [1X]n -31° C 15 H 1 ~r0 M 295.218
(c, 2.1 in CHC1 3). Constit. ()f Laurencia nipponica. Unstable oil. [1X]n +85.9°
15-Hydroxy: [82486-71-3). Laurenol
(CHC1 3).
C 15H 100 M 216.322 Ac: Cryst. Mp 102.5-103°. [1X]n +85.1° (CHC1 3).
Constit. of L. nipponica. Oil. [1X)n +34.7° (c, 0.20 in 10-Bromo: [72782-83-3]. 10-Bromolaurenisol
CHC1 3). C15H 18Br20 M 374.115
15-Acetoxy: [82486-74-6]. Laurenol acetate Constit. of L. glandulifera. Oil. [tX]i? + 74° (c. 0.6 in
C 17H 22 0 2 M 258.360 CHC13).
Constit. of L. nipponica. Oil. [1X]n +23.6° (c, 0.42 in Irie, T. eta/, Tetrahedron Lett., 1969, 1343.
CHC1 3). Suzuki, M. et al, Bull. Chern. Soc. Jpn., 1979, 52, 3349 (!0-
Bromolaurenisol)
15-0xo: [82486-72-4]. Laurena/
Capon, R.J. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1302 (10-
C15H 180 M 214.307 Bromo/aurenisol)
Constit. of L. nipponica. Oil. [1X)n + 33.2° (c, 0.23 in
CHC1 3).
7,8-Dihydro: [62311-77-7]. Dihydrolaurene
C 15H 22 M 202.339
Constit. of L. filiformis. Pale-yellow oil.
8,11-Dihydro: [82486-70-2). Isodihydrolaurene
C 15H 22 M 202.339
Trichothecanes
Constit. of L. nipponica. Oil. [1X]n +33.SO (c, 1.24 in
CHC1 3).
8,11-Dihydro, 15-hydroxy: (82486-69-9]. lsodihydrolaurenol
C 15H 220 M 218.338 Baccharinoid Bl Sq-00830
Constit. of L. nipponica. Oil. (1X]n +40° (c, 1.52 in [71695-69-7]
CHC1 3).
8,11-Dihydro, 15-acetoxy: 0-Acety/isodihydrolaurenol
C 17H 240 2 M 260.375
Constit. of L. nipponica. Oil. [1X]n +40° (c, 0.21 in
CHC13).
7-Hydroxy: [63181-28-2]. 7-Hydroxylaurene
C 15H100 M 216.322
Isol. from L. subopposita. Shows antibiotic props. [tX]i?
+45° (c, 2.5 in CHC13).
7-Hydroxy, 10-bromo, 11-iodo: [72008-57-2]. 10-Bromo-7-
hydroxy-11-iodolaurene
C15H 18Brl0 M 421.115
Constit. of L. nana. Cryst. Mp 147-153° dec. [1X]n +225°
(c, 0.24 in CHC13). ~H 44,0 10 M 548.629
10-Bromo, 7-hydroxy: [62311-74-4]. AUolaurinterol Constit. of Baccharis megapotamica. Cryst.
C 15H 19Br0 M 295.218 (EtOAcjhexane). Mp 162-164°. [1X]n -52.0° (c, 0.2 in
Constit. of L. filiformis and L. subopposita. Pale-yellow CHC1 3), [1X]i;l + 100° (c, 1.4 in CH 2Cl2).
viscous oil. [1X]n +22° (c, 1.7 in CHC1 3). 13'-Epimer: [71748-64-6]. Baccharinoid B2
Irie, T. et al, Tetrahedron, 1969, 25, 459 (struct) C~ 400 10 M 548.629
McMurry, J.E. et al, Tetrahedron, 1974, 30, 2027 (synth) Constit. of B. megapotamica. Cryst. (CH2C12/Etp). Mp
Kazlauskaus, R. et al, Aust. J. Chern., 1976, 29, 2533 177-180°. [1X]i;l + 116° (c, I in CHP2).
(Allolaurinterol, Dihydrolaurene)
Wratten, S.J. eta/, J. Org. Chern., 1977, 42, 3343 (7- 4'-Deoxy, 2'fi-hydroxy: [71718-23-5). Baccharinoid B7
Hydroxylaurene, A/lolaurinterol) C~400 10 M 548.629
Posner, G.H. et al, Tetrahedron Lett., 1977, 3215 (synth)

302
Baccharinoid B9 - Baccharinoid B25 Sq-00831 - Sq-00834

Constit. of B. megapotamica. Cryst. (EtOH). Mp 229- Baccharinoid B16 Sq-00833

2310. [cx]i,S + 150° (c, 0.66 in CH 2Cl0. [105563-59-5]
4'-Deoxy, 2'P-hydroxy, 13'-epimer: [72074-16-9].
Baccharinoid B3
C29H400 10 M 548.629
Constit. of B. megapotamica. Cryst. (Me2C0jhexane).
Mp 172-180°. [cx]i,S + 164° (c, 0.58 in CH 2Cl2).
Jarvis, B.B. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 815.

Baccharinoid B9 Sq-00831
[71695-68-6)

~H 380 10 M 546.613
Constit. of Baccharis megapotamica. Cryst.
(EtOHjhexane). Mp 160-161°. [1X]i,S +63.SO (c, 0.47 in
MeOH).
2',3'-Dihydro: Baccharinoid B13
C29H 400 10 M 548.629
From B. megapotamica. Glass. [1X]i;" + 113.5° (c, 0.9 in
MeOH).
2',3'-Dihydro, 13'-epimer: Baccharinoid B14
C~ 38 0 10 M 546.613 ~H 400 10 M 548.629
Constit.. of Baccharis megapotamica. Cryst. (CH 2Cl 2/Et20). From B. megapotamica. Glass. [1X]i,S +90.8° (c, 1.36 in
Mp 216-218°. [cx]i,S +2.4° (c, 0.68 in CH 2Cl 2). MeOH).
13'-Epimer: [105617-46-7]. Baccharinoid BJO [105660-73-9]
c~ 38 0 10 M 546.613 Jarvis, B.B. et al, J. Org. Chern., 1987, 52, 45.
From B. megapotamica. Cryst. (CH 2Cl2/Etp). Mp 157-
1580. [cx]i,S +8.1° (c, 0.62 in CHC1 3). Baccharinoid B25 Sq-00834
13'-Epimer, 2',3'-Dihydro: [105563-55-1]. Baccharinoid B10 [I 05581-68-8]
C29H400 10 M 548.629
From B. megapotamica. Cryst. (Me2COjhexane). Mp
170-172°. [cx)i,S +39.9° (c, 1.44 in CHCI 3).
rlo~
Jo
Jarvis, B.B. et a/, J. Org. Chern., 1987, 52, 45.

Baccharinoid B13 Sq-00832 Ho~ n~j ~-

[105563-56-2]
0:::.... 1

o I
HO
0
C:z7H320 10 M 516.544
Constit. of Baccharis megapotamica. Cryst.
(CH2Cl2/hexane). Mp 205°. [1X]i;" +214° (c, 0.7 in
MeOH).
Jarvis, B.B. et al, J. Org. Chern., 1987, 52, 45.

C29H380 10 M 546.613
Constit. of Baccharis megapotamica. Cryst. (EtOAc). Mp
218-219°. [cx]i,S + 130° (c, 0.74 in MeOH).
13'-Epimer: [105617-47-8]. Baccharinoid BU
c~38olo M 546.613
Constit. of B. megapotamica. Cryst. (EtOAcjhexane).
Mp 149-151°. [cx]i,S + 72.4° (i:, 0.76 in MeOH).
13'-Epimer, 8-Ketone: [105563-58-4). Baccharinoid B17
c~36olo M 544.597
Constit. of B. megapotamica. Cryst. (CH 2Cl2 jhexane).
Mp 165°. [1X]i,S + 5.4° (c, 0.4 in MeOH).
Jarvis, B.B. et a/, J. Org. Chern., 1987, 52, 45.

303
Baccharinol - 1,4-Dimethyl-4-(1-methyl-2-... Sq-00835 - Sq-00839

Baccharinol Sq-00835 Adams, P.M. eta/, J. Chern. Soc., Chern. Commun., 1970, 1569
Baccharinoid B4 (biosynth)
Czugler, M. eta/, Acta Crystallogr., Sect. B, 1975, 31, 1204 (cryst
[63783-94-8] struct)
Ellison, R.A. eta/, J. Org. Chern., 1976, 41, 576 (cmr)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 195, 196.

I
I
I
Deoxytrichodermadiene Sq-00837
I

\ [85957-00-2]

4lL
olo~H OH

H~O

]
0 : 13'

C:wH380 11 M 562.613
Constit. of Baccharis megapotamica. Cryst.
(MeOHjCHC1 3 jEtp). Mp 259-263°. (oc]i;' + 165° (c, 0.5
in MeOH). ).max 260 nm (e 20 400) (EtOH).
Tri-Ac: Mp 255-257°.
13'-Epimer: [63814-57-3]. Isobaccluuinol. Baccharinoid B6 C23H 300 4 M 370.488
C29H 380 11 M 562.613 Constit. of Myrothecium verrucaria. Shows antimicrobial,
From B. megapotamica. Cryst. (Me2COjhexane). Mp cytotoxic and mycotoxic props. Oil. [oc]i;' -5.6° (c, 0.95
249-251°. [oc]i;' + 149° (c, 0.66 in MeOH). in CHC1 3).
8-Deoxy, 9P,IOP·epoxide: [61251-97-6]. Baccharin. Jarvis, B.B. eta/, J. Org. Chern., 1983, 48, 2576.
Baccharinoid B5
C29H 380 11 M 562.613 7~,8~:2 1 ,3' -Diepoxyroridin H Sq-00838
Constit. of B. megapotamica. Exceptionally active in in 7'- Deoxo-2' -deoxy-2' ,3': 7,8-diepoxy-7' ,5'-
vitro antitumour tests. Cryst. (CH 2Cl2 jMeOH). Mp 200- (ethylidenoxy)verrucarin A, 9CI
2300. {oc]~4 +4l.SO (c, 2.2 in CHC1 3). (64687-84-9]
8~Deoxy, 9ft,JOP-epoxide, 13'-epimer: [63814-58-4].
Isobaccharin. Baccharinoid BB 1;10 H
C29H 380 11 M 562.613
From B. megapotamica. Antileukaemic factor. Cryst.
(Me 2COjhexane). Mp 228-230°. [cx]i;' +42° (c, 0.36 in
0
I

CHC1 3). I

ot: o
Kupchan, S.M. eta/, J. Am. Chern. Soc., 1976, 98, 7092 (cryst
struct, deriv) I 2
o
Kupchan, S.M. eta/, J. Org. Chern., 1977, 42, 4221 (isol, struct)
Still, W.C. eta/, J. Am. Chern. Soc., 1984, 106, 260 (synth)
Cole, R.J., Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 246.

Crotocol Sq-00836 6~0

7fi,8P: 12,13-Diepoxy-4fi-trichothecenol. 7fi,8fi-Epoxy-4p-
scirpenol 0
[21445-21-6] C29H34010 M 542.582
Metab. of a Cylindrocarpon sp. Shows antibiotic props.
Prisms. Mp 291-293° dec.
Matsumoto, M. eta/, J. Antibiot., 1977, 30, 681 (iso[)
Matsumoto, M. eta/, Tetrahedron Lett., 1977, 4093 (struct, ir, uv,
pmr, cmr)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 245.

C15H 200 4 M 264.321 1,4-Dimethyl-4-(1-methyl-2- Sq-00839

Inhibitor of protein synth. Cryst. Mp 154°. [oc]i? -6.4° (c, methylenecyclopentyl)cyclohexene, 9CI

-oY
2 in CHC1 3).
0-(2Z-Butenoyl): [21284-11-7]. Crotocin. Antibiotic T
C1,H240 5 M 332.396 (1S,1 1 S)-form
Antifungal antibiotic from Cephalosporum crotigenum.
Cryst. (MeOH). Mp 126°. [oc]i? + 13.SO (c, 1 in CHC1 3). C15H 24 M 204.355
t> YD0117000. (JS,l' S)-form [28624-60-4] Trichodiene
Gbiz, E.T. et a/, Nature (London), 1966, 212, 617 (iso[) Prod. by strains of Trichothecium roseum. Biogenetic
Gyimesi, J. eta/, Tetrahedron Lett., 1967, 1665 (struct) precursor of all trichothecenes. Oil. [ocln +21° (c, 1.35 in
CHC1 3).

304
12,13-Epoxy-9-trichothecene - Miotoxin D Sq-00840 - Sq-00843

(JR,l'S)-form [24493-43-4) Bazzanene Miotoxin B Sq-00842

Constit. of Bazzania pompeana. Bp 2 102-103°. [1X)n +48° [93633-90-0)
(CHC1 3).
(JRS,l' RS)-form [61505-17-7)
Bp0 _5 65-70°.
Evans, R. eta/, J. Chern. Soc., Perkin Trans. I, 1966, 326
(biosynth)
Matsuo, A., Tetrahedron, 1971, 27, 2757 (isol, Bazzanene)
Nozoe, S. eta/, Tetrahedron, 1972, 28, 5105 (isol)
Evans, R. eta/, J. Chern. Soc., Perkin Trans. I, 1976, 1212
(biosynth)
Matsuo, A. et a/, J. Chern. Soc., Chern. Commun., 1977, 566
(struct, Bazzanene)
Andersen, N.H. eta/, Phytochemistry, 1977, 16, 1731 (struct)
Welch, S.C. et a/, J. Org. Chern., 1980, 45, 4077 (synth)
Cane, D.E. eta/, J. Am. Chern. Soc., 1981, 103, 2136 (biosynth)
Suda, M., Tetrahedron Lett., 1982, 23, 427 (synth)
Schlessinger, R.H. et a/, J. Org. Chern., 1983, 48, 407 (synth) OH
Snowden, R.L. et a/, J. Org. Chern., 1984, 49, 1464 (synth)
Kraus, G.A. eta/, J. Org. Chern., 1986, 51, 503 (synth, bib/) C29H 380 9 M 530.614
Van Middlesworth, F.L., J. Org. Chern., 1986, 51, 5019 (synth) Not to be confused with Mytoxin B, Sq-00846. Constit. of
Zamir, L.O. eta/, J. Chern. Soc., Chern. Commun., 1989, 598 Baccharis cordifolia.
(biosynth) 3'-Acetoxy, 4'-a/coho/: [93633-91-1). Miotoxin C
Pearson, A.J. eta/, J. Org. Chern., 1989, 54, 4663 (synth) C31H 4z0 11 M 590.666
Gilbert, J.C. eta/, Tetrahedron Lett., 1989, 30, 4193 (synth) Constit. of B. cordifolia. Stereochem. undetermined.
Harding, K.E. eta/, J. Org. Chern., 1990, 55, 4403 (synth)
Habermehl, G.G. eta/, Justus Liebigs Ann. Chern., 1984, 1746.
12,13-Epoxy-9-trichothecene Sq-00840
Trichothecene. Scirpene Miotoxin D Sq-00843
[96540-64-6]

C 15H 220 2
~'
M 234.338
I
I
I
I
I

12rx.-form [37133-74-7) Hz{':: 0

Metab. of Trichothecium roseum. Cryst. (MeOH aq.).
Mp 54-57°. [1X)i;' + 16.7° (c, 0.03 in CHCJ 3) (synthetic). I
BP-Hydroxy: ap-Hydroxytrichothecene
CtsH 220 3 M 250.337
Prod. by F. sporotrichioides. Cytotoxic. Oil.
ox20 3'
[114882-97-2] HO~ 0 H
Machida, Y. eta/, Tetrahedron, 1972, 28, 5113 (isol, biosynth)
Masuoka, N. et a/, Tetrahedron Lett., 1976, 1691 (synth)
Frazier, K.A., Diss. Abstr. Int., B, 1981, 42, 1454 (synth, derivs)
Synform, 1984, 2, 260 (rev) C29H 400 9 M 532.630
Corley, D.G. eta/, Tetrahedron Lett., 1986, 27, 4133 (deriv) Constit. of Baccharis cordifolia.
Hua, D.H. eta/, J. Am. Chern. Soc., 1988, 110, 4741 (synth)
Pearson, A.J. eta/, J. Org. Chern., 1989, 54, 4663 (synth) 3' -Epimer: [96540-65-7]. /somiotoxin D
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic C29H 400 9 M 532.630
Press, N.Y., 1981, 197. Constit. of B. cordifolia.
2',3'-Didehydro: [90790-03-7]. Miotoxin A
Isotrichodiol Sq-00841 C29H 380 9 M 530.614
[130369-84-5] From B. cordifolia.
Habermehl, G.G. eta/, Justus Liebigs Ann. Chern., 1985, 633.

CtsH2403 M 252.353
Metab. of Fusarium culmorum. An intermediate in the
biosynthesis of trichothecenes.
Hesketh, A.R. eta/, J. Chern. Soc., Chern. Commun., 1990, 1184
(iso/, struct, biosynth)

305
Myrotoxin A- Neosolaniol Sq-00844 - Sq-00847

Myrotoxin A Sq-00844 Mytoxin B Sq-00846

[99499-16-8]

~
~0
0 OH
C27H 320 9 M 500.544
Trichothecene antibiotic. Prod. by Myrothecium roridum. C29H 360 9 M 528.598
Shows cytotoxic props. Mp 220-222°. [oc]~ + 122° (c, Trichothecene antibiotic . Not to be confused with
0.50 in CH 2Cl2). Similar to Mytoxin A, Sq-00845. Miotoxin B, Sq-00842. Prod. by Myrothecium roridum.
8oc-Acetoxy: [99486-49-4]. Myrotoxin B Acutely cytotoxic. Mp 158-161°. [oc]~ +15.4° (c, 0.78 in
C29H 340 11 M 558.581 CH 2Cl2).
Prod. by M. roridum. Shows cytotoxic props. Mp 195- I> Highly toxic.
1970. [oc]~ + 101.7° (c, 0.60 in CH 2Cl2). Jarvis, B.B. et al, Bull. Soc. Chirn. Be/g., 1986, 95, 681 (isol, struct)
Jarvis, B.B. et al, Tetrahedron Lett., 1985, 26, 4859 (isol, struct,
nrnr)
Neosolaniol Sq-00847
12,13-Epoxytrichothec-9-ene-3,4,8,15-tetrol 4,15-diacetate,
Mytoxin A Sq-00845 9CI. 3,4,8,15-Scirpenetetrol 4,15-diacetate. Solaniol.
[l 05049-16-9] Neozolaniol
[36519-25-2]

l;f 0 H OH
,0
HO
15 : OAc
CH20Ac
C19H 260 8 M 382.410
Trichothecene antibiotic. Prod. by several Fusarium spp.
Inhibitor of protein synthesis. Shows toxic and cytotoxic
props. Cryst. (EtOAcjhexane). Mp 171-172°.
I> YD0080000.
8-Ac: Acetylneosolaniol
C29H 360 10 M 544.597 C21 H 280 9 M 424.447
Trichothecene antibiotic. Prod. by Myrothecium roridum. Prod. by F. spp. Needles (C 6H 6/heptane). Mp 190-
Shows acute cytotoxicity. [oc]~ + 22.9° (c, 0.96 in 190.50.
CH 2Cl2). Similar to Myrotoxin A, Sq-00844.
15-0-Deacetyl: see 3,4,8,15-Scirpenetetrol, Sq-00862
12'-Epimer: [105ll8-8l-8]. Mytoxin C Harri, E. et al, Helv. Chirn. Acta, 1962, 45, 839 (isol)
C29H 360 10 M 544.597 Blight, M.M. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1691
Prod. by M. roridum. Acutely cytotoxic. Mp 181-185°. (isol)
[oc]~ -4.0° (c, 0.83 in CH 2Cl 2). Smalley, E.B. et al, Mycotoxins, (I.F.H. Purchase, Ed.), Elsevier,
1974, 199 (isol)
Jarvis, B.B. et al, Bull. Soc. Chirn. Belg., 1986, 95, 681 (isol, struct)
Ueno, Y. et al, Jpn. J. Exp. Med., 1977, 47, 177.
Lansden, J.A. et al, J. Agric. Food Chern., 1978, 26, 246 (isol)
Ishii, K. et al, Appl. Environ. Microbial., 1981, 42, 541 (isol)
Brumley, W.C. et al, Biorned. Mass Spectrorn., 1982, 9, 451 (ms)
Kaneko, T. et a/, J. Med. Chern., 1982, 25, 579 (synth, props)
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 175, 178.

306
Roridin A - Roridin E Sq-00848 - Sq-00850

Roridin A Sq-00848 Roridin D Sq-00849

7' -Deoxo-7' -(1-hydroxyethyl)verrucarin A, 9CI 7'-Deoxo-2' -deoxy-2' ,3' -epoxy-7' -(1-hydroxyethyl)verrucarin
[14729-29-4] A, 9CI
[14682-29-2]
0 H
16~1;1
I
0
0 I
I
I
0
I
I
2

0 0 )
HO}- O
0~0
-~13'
C~ 40 0 9 M 532.630
Metab. of Myrotheciurn spp. Exhibits antifungal and C29H 380 9 M 530.614
cytostatic activity. Short needles (Me2COjEtp). Mp Trichothecene. lsol. from Myrotheciurn verrucaria and M.
198-204°. (IX)~ + 130° (c, 1.36 in CHC1 3). ).max 263 nm. roridurn. Needles (Me 2COjEtp). Mp 232-235°. (1X]i,3
I> VL0355000. + 29° (c, 2.71 in CHCI 3).
13'-Epirner: [84773-08-0]. lsororidin A 9P,JOP-Epoxide: [105563-52-8]. Baccharinoid B17
c~ 40 09 M 532.630 C29H 380 10 M 546.613
Metab. of M. verrucaria. Cryst. (CH 2Cl2/hexane). Mp Constit. of Baccharis rnegapotarnica. Cryst.
183-185°. [1X]i;5 +6.7° (c, 3.3 in CHC1 3). (CH 2Cl2/Et20). Mp > 300°. [1X]i;5 + UO (c, 0.68 in
CH 2Cl2).
9P,JOP-Epoxide: [74516-67-9]. 9P,IOP-Epoxyroridin A
C29H 400 10 M 548.629 8P-Hydroxy: [105563-54-0]. Baccharinoid B21
Semisynthetic. Antileukaemic agent. C29H 380 10 M 546.613
From B. rnegapotarnica. Cryst. (CH 2Cl2/Et20). Mp 259-
9p,Jop-Epoxy, 16-hydroxy: [87532-33-0). 9p,IOp-Epoxy-16-
2600. [1X]i;5 + 73.SO (c, 0.68 in CH 2Cl2).
hydroxyroridin A
Cz,H 340 11 M 534.559 3-Hydroxy: [105563-53-9]. Baccharinoid B12
Semisynthetic. Antileukaemic agent. Mp 138-142°. C29H 380 10 M 546.613
From B. rnegapotarnica. Cryst. (Me2CO/hexane). Mp
8P-Hydroxy: [87583-91-3). 8p-Hydroxyroridin A
248-250°. [1X]i;5 + 12.6° (c, 0.54 in MeOH).
c~400 10 M 548.629
Semisynthetic. Antileukaemic agent. Mp 237-239°. Bohner, B. et a/, Helv. Chirn. Acta, 1965, 48, 1079 (isol, uv, ir)
Snatzke, G. eta/, He/v. Chim. Acta, 1967, 50, 1618 (cd)
16-Hydroxy: [87532-28-3]. 16-Hydroxyroridin A Breitenstein, W. eta/, Helv. Chirn. Acta, 1975, 58, 1172 (crnr)
c~400 10 M 548.629 Jarvis, B.B. eta/, J. Org. Chern., 1987, 52, 45 (isol, struct, derivs)
Semisynthetic. Antileukaemic agent. Mp 206-207°. Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Harri, E. eta/, Helv. Chirn. Acta, 1962, 45, 839 (isol) Press, N.Y., 1981, 236.
Breitenstein, W. et a/, Helv. Chirn. Acta, 1975, 58, 1172 (crnr)
Muller, B. eta/, Helv. Chirn. Acta, 1975, 58, 453, 471 (biosynth) Roridin E Sq-00850
Eppley, R. eta/, J. Org. Chern., 1977, 42, 240 (nrnr)
2' ,3'-Didehydro-7' -deoxo-2' -deoxy-7' -( 1-
Jarvis, B.B. eta/, J. Med. Chern., 1980, 23, 1054; 1984, 27, 239
(derivs, props) hydroxyethyl)verrucarin A, 9CI. Satratoxin D
Jarvis, B.B. et a/, J. Nat. Prod. (Lloydia), 1982, 45, 440 (cryst [16891-85-3]
struct, isol)
Pohland, A.E. eta/, Pure App/. Chern., 1982, 54, 2220 (uv, ir, prnr,
ms, cd)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 230.

C29H 380 8 M 514.614

lsol. from Myrotheciurn verrucaria and M. roridurn.
Antibiotic. Cryst. in two forms. Mp 183-184°, Mp 220-
2220 (dimorph.). [1X]i,3 -16° (CHC1 3).
6' andfor 13'-Epirner: [64726-84-7]. lsororidin E
C29H 380 8 M 514.614

307
Roridin H - Roridin L2 Sq-00851 - Sq-00853

Metab. of Cyc/indrocarpon spp. Prisms (EtOAc). Mp Roridin J Sq-00852

200-202°. [1X]i;' -65.1 o (CHC1 3). 2' ,3'-Didehydro-7' -deoxo-2' -deoxy-7' ,5'-(ethylideneoxy )-4'-
6' andfor 13'-Epimer, 7P,8P-epoxide: [64687-83-8]. 7p,Bp.. hydroxyverrucarin A, 9CI
Epoxyisororidin E [74072-83-6]
C:zJf380 9 M 530.614
Metab. of C. spp. Prisms (Me2CO). Mp 216-219°. [1X]i;'
-69.9° (CHC1 3).
Bohner, B. et al, Helv. Chim. Acta, 1965, 48, 1079 (isol)
Traxler, P. et al, Helv. Chim. Acta, 1970, 53, 2071 (struct)
Eppley, R.M. et al, Science (Washington, D.C.), 1973, 181, 758
(stereochem)
Matsumoto, M. eta/, J. Antibiot., 1977, 30, 681 (derivs)
Matsumoto, M. et al, Tetrahedron Lett., 1977, 4093 (cmr, struct)
Still, W.C. et al, J. Am. Chern. Soc., 1984, 106, 260 (synth)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 237, 242, 243.

Roridin H
2' ,3'-Didehydro-7' -deoxo-2' -deoxy-7' ,5'-
(ethylideneoxy)verrucarin A, 9CI. Verrucarin H
[29953-50-2]
Sq-00851
C 29 H 360 9 M 528.598
Trichothecene antibiotic. Isol. from Myrothecium
verrucaria. Shows antileukaemic activity. Cryst.
(CH 2Cl 2jhexane). Mp 281-285°. [IX]~ + 21.8° (c, 0.65 in
CHC1 3).
Ac: [74098-61-6].
Cryst. (CH 2Cl 2/Et20). Mp 230-235°. [1X]~ -40.6° (c,
0.55 in CHC1 3).
9P,JOP-Epoxide: [87532-25-0]. 9P,10P-Epoxyverrucarin J
C 29 H 360 10 M 544.597
Semisynthetic. Shows antileukaemic props.
Jarvis, B.B. et al, J. Org. Chern., 1982, 47, 1117 (isol, ut, pmr, cmr)
Jarvis, B.B. et al, J. Med. Chern., 1984, 27, 239 (deriv)

Roridin L2 Sq-00853
C:zJI360 8 M 512.599 [85124-22-7]
lsol. from Myrothecium verrucaria. Shows antileukemic
activity. Needles. Mp >325°. [1X]i;l +31° (c, 1.16 in
CHC1 3).
7P,8P-Epoxide: [64687-85-0]. 7P,8P-Epoxyroridin H
C 2,H340 9 M 526.582
Metab. of Cyc/indrocarpon spp. Amorph. powder.
9P,JOP-Epoxide: [87532-26-1]. 9P,lOP-Epoxyroridin H
Semisynthetic. Shows antileukemic props.
Bohner, B. et a/, Helv. Chim. Acta, 1965, 48, 1079 (isol)
Traxler, P. et a/, Helv. Chim. Acta, 1970, 53, 1846 (struct)
Breitenstein, W. eta/, Helv. Chim. Acta, 1975, 58, 1172 (nmr)
Matsumoto, M. et al, J. Antibiot., 1977, 30, 681 (deriv)
Matsumoto, M. eta/, Tetrahedron Lett., 1977, 4093 (stereochem)
Jarvis, B.B. et al, J. Org. Chern., 1982, 47, 1117 (isol, struct)
Jarvis, B.B. et al, J. Med. Chern., 1984, 27, 239 (epoxide)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 239, 244. C29H 380 9 M 530.614
Metab. of variant of Myrothecium roridum. Shows
antibacterial and antitumour props. Solid. Mp 93-97°.
[1X]n + 83.6° (c, 1.0 in CHC1 3).
16-Hydroxy: [87292-18-0]. 16-Hydroxyroridin L2
C29H 380 10 M 546.613
Prod. by M. roridum. Shows similar props. to parent
compd. Oil. [1X]i; + 58.4° (c, 0.19 in CHC1 3}: A.m••, 261
nm.
Bloem, R.J. et al, Tetrahedron Lett., 1983, 24, 249 (isol, struct)
Jarvis, B.B. et a/, Tetrahedron Lett., 1983, 24, 3539 (deriv l

308
Sambucinol - 3,15-Scirpenediol Sq-00854 - Sq-00858

Sambucinol Sq-00854 Satratoxin H Sq-00857

11 ,12-Epoxytrichothec-9-ene-3,13-dio/, 9CI [53126-64-0]
[90044-33-0]

Y'frOH
~OH
C 15H 120 4 M 266.336
Tricothecene antibiotic. Metab. of Fusarium sambucinum.
Possible cytostatic activity. Cryst. (Me2CO). Mp 227°.
[rx]D -22.6° (c, 1.3 in Py). The first cl5-trichothecene.
Mohr, P. et al, Helv. Chim. Acta, 1984, 67, 406 (isol, struct)
Zamir, L.O. et al, Tetrahedron, 1989, 35, 2277 (biosynth)

Sambucoin Sq-00855 C29H 360 9 M 528.598

Trichothecene antibiotic. Metab. of Stachybotrys atra and
[90044-34-1]
S. chartarum. Cryst. Mp 162-166°.
Stereoisomer: [90365-51-8]. /sosatratoxin H. PD 113326.
Antibiotic PD 113326
C29H 360 9 M 528.598
From Myrothecium roridum. Active against tumours and
yeasts. Cryst. (CH 2Cl2 jcyclohexane). Mp 168-171°.
Stereoisomeric at one or more of the 6', 12' and 13'-
C 15H 220 3 M 250.337 positions.
Trichothecene antibiotic. Metab. of Fusarium sambucinum. [93860-23-2]
Shows possible cystatic activity. Cryst. (Me 2C0fpet.
Eppley, R.M. et al, J. Org. Chern., 1977, 42, 240.
ether). Mp 205-210°. Related to Trichothecenes. Harrach, B. et al, Appl. Environ. Microbiol., 1981, 41, 1428 (isol)
8cx-Hydroxy: [112468-60-7]. Brx.-Hydroxysambucoin Smitka, T.A. et al, J. Antibiot., 1984, 37, 823.
C 15H 220 4 M 266.336 Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Metab. of F. sporotrichioides. Glass. Press, N.Y., I981, 227.
BP-Hydroxy: [112531-13-2]. ap-Hydroxysambucoin
C 15H 220 4 M 266.336 3,15-Scirpenediol Sq-00858
Metab. of F. sporotrichioides. Glass. 12,13-Epoxy-9-trichothecene-3,15-dio/
Mohr, P. et al, Helv. Chim. Acta, 1984, 67, 406 (isol, struct) [38818-51-8]
Corley, D.G. et al, J. Nat. Prod. (Lloydia), 1987, 50, 897 (derivs)

Satratoxin G
2' ,3' -Epoxy-2' ,3' -dihydrosatratoxin, 9CI
Sq-00856 yto~,OH
[53126-63-9]
H~
C 15H 220 6 M 298.335
3rx.-form
3-Ac: [38818-66-5]. 15-Deacetylcalonectrin
C 17 H 24 0~ M 308.374
Metab. of Calonectria nivalis. Cryst. (Et20jpet. ether).
Mp 184-186°. [rx]n + 11.2° (c, 1 in CHC1 3).
3,15-Di-Ac: Calonectrin
C 19H 260 6 M 350.411
Metab. of C. nivalis. Mycotoxin. Cryst. (EtzOjpet.
ether). Mp 83-85°. [rx]i; + 14.6° (c, 1 in CHC1 3).
Gardner, D. et al, J. Chern. Soc., Perkin Trans. I, I972, 2576 (isol,
C29H 360 10 M 544.597 struct)
Trichothecene antibiotic. Prod. by Stachyobotrys atra. Hanson, J.R. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1033
(cmr)
Cryst. (CHC1 3jhexane). Mp 167-170° (132-136°). A.max Brumley, W.C. et al, Biomed. Mass Spectrom., 1982, 9, 451 (ms)
256 nm. Kraus, G.A. et al, J. Am. Chern. Soc., I982, 104, 1114 (synth)
13'-Ketone: [73513-01-6]. Satratoxin F. 13'-Deoxy-2',3'- Jeker, N. et al, Tetrahedron Lett., I984, 25, 5637 (synth)
epoxy- 2' ,3' -dihydro-13 '-oxosatratoxin H, 9CI Cameron, S. et al, J. Chern. Soc., Perkin Trans. I, I989, 887
C29H 340 10 M 542.582 (synth)
Prod. by S. atra. Cryst. (CHClJihexane). Mp 140-143°. Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 192, 193.
Eppley, R.M. et al, J. Org. Chern., 1980, 45, 2522 (struct, pmr,
cmr)
Harrach, B. et al, Appl. Environ. Microbiol., 1981, 41, 1428; 1983,
45, 1419 (isol)

309
4,15-Scirpenediol - 3,4,8,15-Scirpenetetrol Sq-00859 - Sq-00862

4,15-Scirpenediol Sq-00859 8-Ketone: [23282-20-4]. 31X,4P,71X,l5-Tetrahydroxy-8-

12,13-Epoxy-9-trichothecene-4,15-diol, 9CI scirpenone. 3,12,13-Epoxy-31X,4P,71X,l5-tetrahydroxy-9-
trichothecen-8-one, 9CI. Nivalenone. Nivalenol
Toxic principle from Fusarium nivale. Cryst. (MeOH).
Mp 223-225°. [IX]~ + 21.54° (c, 1.3 in EtOH).
I> YD0165000.
8-Ketone, 4-Ac: [32204-36-7]. Fusarenone X
C 17H 220 8 M 354.356
lsol. from F. spp. Cryst. Mp 181-184°. [1X]i; + 58° (c, 1
C 13H 22 0 4 M 266.336 in MeOH).
4fJ-form [2198-92-7] 8-Ketone,4,15-di-Ac: [14287-82-2]. Saubinine I. Nil!alenol
Verrucarol diacetate
Hydro!. prod. of Verrucarins. Shows antifungal activity. C 19H 240 9 M 396.393
Needles (Me 2CO/Etz0). Mp 155-158°. [1X]i;"l -39° (c, Constit. of F. nivale and F. equiseti, also isol. from
1.069 in CHC1 3). Gibberella saubinetii. Active against tumours and
viruses. Cryst. Mp 135-136°, Mp 129°. [IX]~ +64.3° (c, 1
Di-Ac: [2198-94-9]. Diacetylverrucarol
in EtOH).
C 19H 160 6 M 350.411
I> Toxic. YD0165500.
From Myrothecium verrucaria. Antifungal. Needles
(Me2CO/Et20jpet. ether). Mp 148-150°. [1X]i; -17° (c, 8-Ketone, 4-deoxy: see 3,7,15-Trihydroxy-8-scirpenone, Sq-
1.22 in CHC1 3). 00877
Grove, J.F., J. Chern. Soc. C, 1970, 375 (struct)
Dibenzoyl: Cryst. (Et 20jpet. ether). Mp 151-152°. [1X]~4 Saito, M. et al, Microb. Toxins, 1971, 7, 293 (rev)
-64° (c, 1.13 in Me 2CO). Fujimoto, Y. et al, Chern. Pharm. Bull., 1972, 20, 1194 lstruct)
15-(5-Hydroxy-3-methyl-2E-pentenoyl): [84412-91-9]. Verrol Blight, M.M. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1691
C 21 H 300 6 M 378.464 (is of)
Prod. by M. verrucaria. Shows antimicrobial, cytotoxic Ishii, K. et al, Phytochemistry, 1975, 14, 2469 (isol)
Brumley, W.C. et al, Biomed. Mass Spectrom., 1982, 9, 451 (ms)
and mycotoxic props. Oil. [1X]~4 -41° (c, 0.572 in
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
CHC1 3). Press, N.Y., 1981, 206, 213, 221.
4fJ-(±)-form [80514-49-4]
Cryst. (C6H 6 jhexane). Mp 170-171.5°.
3,4,7, 15-Scirpenetetrol Sq-00861
Harri, E. eta/, Helv. Chim. Acta, 1962, 45, 839. 12,13-Epoxy-9-trichothecene-3,4,7,15-tetrol
Gutzwiller, T. et al, Helv. Chim. Acta, 1962, 45, 1726; 1963, 46,
1786.
Fetz, E. et al, Helv. Chim. Acta, 1965, 48, 1669 (synth, Verrol)
McPhail, A.T. et al, J. Chern. Soc., Chern. Commun., 1965, 350
(struct, abs config)
Achini, R. et al, J. Chern. Soc., Chern. Commun., 1971, 404 I
I
(biosynth) I I

Breitenstein, W. et al, Helv. Chim. Acta, 1975, 58, 1172 (nmr) HO:
White, J.D. et al, J. Org. Chern., 1981, 46, 3376 (synth) CH20HOH
Ong, C.W., Heterocycles, 1982, 19, 1685 (rev)
C 13H 220 6 M 298.335
Schlessinger, R.H. et al, J. Am. Chern. Soc., 1982, 104, 1116
(synth) (3rx.,4P,7rx.)-form
Trost, B.M. et al, J. Am. Chern. Soc., 1982, 104, 6110 (synth) 4,15-Di-Ac: [59121-84-5]. 4P,l5-Diacetoxy-31X,71X-
McDougal, P.G., Diss. Abstr. Int., B, 1983, 43, 3245 (synth, rev) scirpenediol. 4p, 15-Diacetoxy-12, 13-epoxy-9-
Nugent, R.A., Diss. Abstr. Int., B, 1983, 44, 1831 (synth, rev) trichothecene- 31X, 71X-dio/
Roush, W.R. et al, J. Am. Chern. Soc., 1983, 105, 1058 (synth)
Metab. of Fusarium spp. Cryst. Mp 201-203°.
Jarvis, B.B. et al, J. Org. Chern., 1983, 48, 2576 (isol, Verrol)
Trost, B.M. et al, J. Am. Chern. Soc., 1984, 106, 383 (synth) Saito, M. et al, Microb. Toxins, 1971, 7, 293 (rev)
Koreeda, M. et al, J. Org. Chern., 1988, 53, 5586 (synth) Blight, M.M. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1691
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic (isol)
Press, N.Y., 1981, 157, 189. Ishii, K., Phytochemistry, 1975, 14, 2469 (isol)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 190, 191.
3,4,7,8, 15-Scirpenepentol Sq-00860
12,13-Epoxy-9-trichothecene-3,4,7,8,15-pentol
3,4,8, 15-Scirpenetetrol Sq-00862
12,13-Epoxy-9-trichothecene-3,4,8,15-tetrol, 9CI

-OH
I
I
I
I

HOHi: OH
15

C 13H 220 7 M 314.335

(3rx.,4p,7rx.,8rx.)-form C13H 22 0 6 M 298.335
4,15-Di-Ac: [25861-69-2]. 4P,l5-Diacetoxy-3rx.,7rx.,8rx.- I> YC9980000.
scirpenetriol. 4P, 15-Diacetoxy-12, 13-epoxy-9-
(3rx.,4p,Brx.)-form [34114-99-3] Toxin T2 tetrol. T2 tetrol
trichothecene- 31X, 71X,81X-trio/
Isol. from Fusarium poae and F. sporotrichioides.
C 19H 160 9 M 398.409
Mycotoxin.
Metab. of F. spp. Cryst. Mp 167-169°.

310
 3,4,15-Scirpenetriol - 3-Scirpenol
4-Ac: (76348-84-0]. NT 2 Toxin. Toxin NT 2
C17Hz,c07 M 340.372
From F. sporotrichioides and F. tricinctum. Mycotoxin.
Potent inhibitor of protein synth. Needles
(EtOAcfhexane). Mp 172-173°.
8-Ac: B-Acetyl-T2 tetrol
C17Hz.c07 · M 340.372
From F. sporotrichioides. Cytotoxic.
15-Ac: 4-Deacety/neoso/aniol. TMR 1. Toxin T1
C17Hz.c07 M 340.372
Prod. by F. heterosporum. Mycotoxin. Also a metab.
prod. of T2-toxin. LD 50 > 10 mgfkg (p.o. mice).
4,8-Di-Ac: [65180-29-2]. 4,8-Diacetyl-T2-tetrol. NT 1 Toxin
c.,H:uPs M 382.410
Prod. by F. sporotrichioides, F. tricinctum and
Haemophilus parainjluenzae. Toxin. Cryst.
(C6H 6/hexane). Mp 172.5-173.5°.
8-(3-Methy/butanoyl): [34114-98-2]. T2 Trio/
30
Czoll 0 7 M 382.453
From F. sporotrichiel/a. Mycotoxin.
I> YD0105000.
8-(3-Methy/butanoyl), 4,15-di-Ac: [20181-53-7].
Cz,cH340 9 M 466.527
lsol. from F. spp. Mycotoxin. Needles (C6H 6/pet. ether).
Mp 151-152°. [a]~ +15° (c, 2.58 in EtOH).
8-(3-Hydroxy-3-methy/butanoyl):
<;.a30o. M 398.452
From F. heterosporum and prod. as a T2 toxin metab.
Mycotoxin.
8-Ketone, 4,15-di-Ac: [77620-47-4]. B-Oxodiacetoxyscirpe110l
C 1,Hz,c08 M 380.394
From F. sporotrichioides and F. crookwellense. Oil.
Bamburg, J.R. et al, Tetrahedron, 1968, 24, 3329 (iso/, struct)
Smalley, E.B. et al, Mycotoxins, (I.F.H. Purchase Ed.), Elsevier,
N.Y., 1974, 199 (bib/)
Ellison, R.A. et al, J. Org. Chern., 1976, 41, 576 (cmr)
llus, T. et al, Phytochemistry, 1977, 16, 1839 (deriv)
Yoshizawa, T. et al, Appl. Environ. Microbiol., 1980, 39, ll72; 40,
901; 1984, 47, 130.
Ishii, K. et al, Appl. Environ. Microbiol., 1981, 42, 541.
Cole, R.J. et al, J. Nat. Prod. (Lioydia), 1981, 44, 324.
Brumley, W.C. et al, Biomed. Mass Spectrom., 1982, 1J, 451 (ms)
Tutel'yan, V.A. et al, Dokl. Akad. Nauk SSSR, Ser. Khim., 1984,
274, 727; Dev. Food Sci., 1984, 7, 282 (isol)
Berger, W.W.A. et al, Appl. Environ. Microbiol., 1985, 50, 656
(deriv)
Oltz, E.M. et al, Tetrahedron, 1986, 42, 2615 (deriv)
Lauren, D.R. et al, J. Agric. Food Chern., 1987, 35, 884 (8-
0xodiacetoxyscirpenol)
Corley, D.G. et al, J. Org. Chern., 1987, 52, 4405 (8-
0xodiacetoxyscirpenol)
Colvin, E.W. et al, J. Chern. Soc., Chern. Commun., 1990, 1200
(synth)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 162.
3,4,15-Scirpenetriol Sq-D0863
12,13-Epoxy-9-trichothecene-3,4,15-trio/, 9CI
C15H220 5 M 282.336
(3rz,4fl)-form (2270-41-9] Angrddol
311
Sq-00863 - Sq-00864
Constit. of Fusarium roseum, F. equiseti and F.
sporotrichie/la. Mycotoxin. Cryst. (AcOH). Mp 189-
1910. [a]~ -10° (c, 0.76 in CHQ3).
4-Ac:
C 17Hz,c06 M 324.373
From F. roseum and F. su/phureum. Oil. [1X]n + 10.3° (c,
lin Me2CO).
15-Ac: [2623-22-5]. MoiiOflCetoxysdrpenol
C17Hz,c06 M 324.373
Isol. from Fusarium roseum and F. sulphureum. Cryst.
(EtOAc/2,2,4-trimethylpentane). Mp 172-173°.
15-Ac, 4-0-a-D-glucopyranoside:
C:13H340 11 M 486.515
From F. sulphureum. Pale-yellow gum. [IX]~ + 79.5° (c,
0.585 in MeOH). Less toxic than other trichothecen.es.
4,15-Di-Ac: [2270-40-8]. Diacetoxyscirpe110l. Anguidin.
ANG 66. NSC 141537
C19H 260 7 M 366.410
Constit. of F. spp. Insecticide, fungicide, antiviral and
cytostatic. Cryst. (EtOAc). Mp 161-162°. (a):,' +20° (c, 1
in Me2CO).
I> YD0112000.
3,4,15-Tri-Ac: Cryst. (EtOH). Mp 124-125°. [a]~ +44° (c,
1 in Me2CO).
Sigg, H.P. et al, Helv. Chim. Acta, 1965, 48, 962 (struct)
Tidd, B.K., J. Chern. Soc. C, 1967, 218 (pmr)
Bamburg, J.R. et al, Tetrahedron, 1968, 24, 3329 (deriv)
Cole, M. et al, Appl. Microbiol., 1972, 24, 660 (use)
Ripperger, H. et al, Phytochemistry, 1975, 14, 2298 (isol)
Pathre, S.V. et al, J. Agric. Food Chern., 1976, 24, 97 (isol)
Ellison, R.A. et al, J. Org. Chern., 1976, 41, 576 (cmr)
Steyn, P.S. et al, Phytochemistry, 1918, 17, 949 (isol)
Hartmann, G.R. et al, Planta Med., 1978, 34, 231 (rev, Anguidin)
Brumley, W.C. et al, Biomed. Mass Spectrom., 1982, 9, 451 (ms)
Pohland, A.E. et al, Pure Appl. Chern., 1982, 54, 2220 (uv, ir, pmr,
ms, cd)
Brooks, D.W. et al, J. Am. Chern. Soc., 1983, 105, 4472 (synth,
deriv)
Gorst-Allman, C.P. et al, J ..Chern. Soc., Perkin Trans. I, 1985,
1553 (deriv)
Roush, W.R. et al, J. Org. Chern., 1985, 50, 3224 (deriv)
Anderson, D.W. eta/, Tetrahedron Lett., 1987, 28, 2661 (Anguidin)
Ziegler, F.E. et al, J. Am. Chern. Soc., 1990, ll:Z, 2749 (synth)
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 160, 168, 111.
3-Scirpenol
Sq-00864
12,13-Epoxy-9-trichothecen-3-o/, 9CI
3«-form [104155-10-4] 3-Hydroxytrichothecene
C15H2203 M 250.337
Isol. from Fusarium sp. Dec. prod. of trichotriol.
Mycotoxin. No phys. props. reported.
Ac: [91423-90-4]. Isotrichodermin
C17Hz,c04 M 292.374
From F. cu/morum and F. roseum. Mycotoxin.
Greenhalgll, R. et al, J. Agric. Food Chern., 1984, 32, 1261; 1986,
34, 98 (deriv)
Greenhalgll, R. et al, J. Agric. Food Chern., 1987, 1, 125, 137 (isol)
Corley, D.G. et al, J. Org. Chern., 1987, 52, 4405 (isol, struct)
4-Scirpenol - Toxin FS2 Sq-00865 - Sq-00869

4-Scirpenol Sq-00865 Sporol Sq-00866

12,13-Epoxy-9-trichothecen-4-o/ [101401-88-11

~H
C 15H 110 4 M 266.336
Mycotoxin from Fusarium sporotrichioides MC-72083. Oil.
C15H 110 3 M 250.337 Related to Sambucinol, Sq-00854.
4fl-form [2198-93-81 Triclwdermol. Roridin C. 4-Scirpeno/ Corley, D.G. et al, Tetrahedron Lett., 1986, 27, 427 (isol)
Metab. of Myrothecium roridum, Trichothecium roseum Ziegler, F.E. et al, Tetrahedron Lett., 1988, 29, 1665 (struct)
and Trichoderma spp.
Ac: [4682-50-21. Trichodermin. WG 696 Sporotrichiol Sq-00867
C 17H 240 4 M 292.374 12,13-Epoxy-9-trichothecene-3,8,15-trio/ 8-(3-
Metab. of Trichothecium roseum, M. roridum, a methy/butenoate), 9CI
Dendrostilbella sp. and Trichoderma spp. Antifungal and
[101401-89-21
antineoplastic antibiotic. Cryst. (pentane). Mp 45-46°
(58-60°). Bp0 .05 110-112°. [ali? -10.2° (c, 1.0 in CHC1 3).
I> YD0120000.
2Z-Butenoyl: [117831-27-31. 12,13-Epoxy-4-(1-oxo-2-
buteny/oxy )trichothecene
C1,H260 4 M 318.412
From T. roseum. Antifungal agent.
6S,7R-Epoxy-6-methyi-2Z,4E-octadienoy/: [75323-72-7].
Triclwdernuu/iene C10H 300 6 M 366.453
C24H 310 5 M 400.514 Trichothecene antibiotic. Prod. by Fusarium
Constit. of M. verrucaria. Cryst. (Etp). Mp 145-146°. sporotrichioides. Mycotoxin (less toxic than T-2 toxin).
[ali? + 17.7° (c, 3.2 in CHC13). Oil.
4-Ketone: [2077-58-91. Trichodermone Corley, D.G. et al, Tetrahedron Lett., 1986, 27, 427 (isol, struct,
C 15H 100 3 M 248.321 nmr)
Semisynthetic. Cryst. (Etpjhexane). Mp 154-155°. [ali? Wani, M.C. et al, J. Org. Chern., 1987, 52, 3468 (synth)
-42.3° (c, 1 in CHC1 3).
7a-Hydroxy: 7rx.-Hydroxytriclwdermol Toxin FSl Sq-00868
C 15H 110 4 M 266.336 FS1 Toxin
From M. roridum. Mycotoxin. Cryst. (EtOAcfhexane).
Mp 214-215°. [aln -7.SO (c, 0.15 in MeOH).
Gutzwiller, J. et al, Helv. Chim. Acta, 1964, 47, 2234 (struct, ir,
rz(OH~C~H
pmr, ms)
Godtfredsen, W.O. et al, Acta Chern. Scand., 1965, 19, 1088 (isol)
Abrahamsson, S. et al, Acta Chern. Scand., 1966, 20, 1044 (cryst
~0
struct) C 15H 110 3 M 250.337
Colvin, E.W. et al, J. Chern. Soc., Perkin Trans. I, 1973, 1989, Modified trichothecene. Prod. by Fusarium sporotrichioides.
(synth) Cytotoxic. Oil.
Hanson, J.R. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1033
(cmr) 2-Ketone: Toxin FS3. FS3 toxin
Bamburg, J.R., Adv. Chern. Ser., 1976, 149 (rev) C 15H 100 3 M 248.321
Riisom, T. et al, Acta Chern. Scand., Ser. B, 1978, 32, 499 (pmr, From F. sambucinum. Glass.
cmr, biosynth) Corley, D.G. et al, Tetrahedron Lett., 1986, 27, 4133 (iso.l, struct)
Stiel, W.C. et al, J. Am. Chern. Soc., 1980, 102, 3654 (synth) Sanson, D.R. et al, J. Org. Chern., 1989, 54, 4313 (FS3)
Jarvis, B.B. et al, Tetrahedron Lett., 1980, 787 (isol)
Ong, C.W., Heterocycles, 1982, 19, 1685 (rev)
Jarvis, B.B. et al, J. Org. Chern., 1982, 47, 1117 (isol, pmr, cmr) Toxin FS2 Sq-00869
Jarvis, B.B. et al, Appl. Environ. Microbiol., 1985, 50, 1225 (deriv) 1,4-Dimethy/-4-[4-hydroxy-2-(hydroxymethyl)-1-merhy/-2-
Cutler, H.G. et al, Agric. Bioi. Chern., 1986, 50, 2667 (deriv) cyc/opentenyl]-2-cyc/ohexen-1-o/. FS 2 Toxin
Plattner, R.D. et al, J. Chern. Res. (S), 1988, 311 (isol, derivs)
O'Brien, M.K. et al, J. Am. Chern. Soc., 1989, 111, 1499 (synth) CH20H
Pearson, A.J. et al, J. Org. Chern., 1989, 54, 4663 (synth)
Harding, K.E. et al, J. Org. Chern., 1990, SS, 4403 (synth, bib/)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic HO
'OH
Press, N.Y., 1981, 155, 164, 224.
Sax, N.l. et al, Dangerous Properties of Industrial Materials, 7th C 15H 240 3 M 252.353
Ed., Van Nostrand-Reinhold, 1989, 2633. Isol. from Fusarium sporotrichioides. Mycotoxin. No phys.
props. reported. Related to Trichodiol.
10-Epimer: Epi FS2
C 15H 240 3 M 252.353
From F. sporotrichioides. Mycotoxin.
10-Ketone: Toxin FS4. FS4 toxin
C15H110 3 M 250.337

312
Toxin HT2 - Trichothecolone Sq-00870 - Sq-00873

From F. sambucinum. Glass. Trichothecin Sq-00872

Corley, D.G. et al, J. Org. Chern., 1987, 52, 4405 (isol, struct) 12,13-Epoxy-4p-hydroxytrichothec-9-en-8-one crotonate,
Sanson, D.R. eta/, J. Org. Chern., 1989, 54, 4313 (derivs) 9CI, 8CI
[63 79-69-7]
Toxin HT2 Sq-00870
12,13-Epoxy-9-trichothecene-3,4,8,15-tetrol 15-acetate 8-(3-
methylbutanoate), 9Cl. HT2 Toxin. Mycotoxin HT2. 4-
Deacetyl T2 Toxin
[26934-87-2]
H
I 0 H ~OH

y
coo C19H 240 5 M 332.396
lsol. from Trichothecium roseum. Protein synth. inhibitor.
HzOAcOH Slender needles (pet. ether). Sol. CHCI 3, C 6H 6 , EtOH,
Me2CO. Mp ll8°. [ex]~ +44° (c, I in CHC1 3).
C22H 320 8 M 424.490 I> YD0175000.
Prod. by Fusarium sp. Shows some antitumour props. 2,4-Dinitrophenylhydrazone: Orange needles (EtOH). Mp
Shows similar toxicity to T-2 Toxin. Yellow oil. 200°.
I> LD 50 9.0 mgfkg (i.p. mice). YD0050000. Jones, E.R.H. eta/, J. Chern. Soc., 1960, 3959 (biosynth)
Godtfredsen, W.O. eta/, Acta Chern. Scand., I965, 19, 1088 (isol,
4-Ac: see 12 Toxin, Sq-00878 struct, prnr)
4-Propanoyl: Gutzwiller, J. eta/, Tetrahedron Lett., I965, 4495 (struct, nmr)
C~H 36 0 9 M 480.554 Adams, P.A. eta/, J. Chern. Soc., Chern. Cornrnun., I970, I569
From F. sporotrichioides. Cytotoxic. Needles. Mp 141- (biosynth)
1420. Machida, Y. et a/, Tetrahedron, I972, 28, 5113 (biosynth)
3'-Hydroxy: [78368-54-4]. 3'-Hydroxy HT2 toxin. TC3 Evans, R. et a/, J. Chern. Soc., Perkin Trans. I, 1976, I2I2
(biosynth, nrnr)
toxin
Brumley, W.C. et a/, Biorned. Mass Spectrorn., I982, 9, 45I (ms)
C22 H 320 9 M 440.489 Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Prod. by F. heterosporum and as T-2 Toxin metab. Press, N.Y., I98I, 217.
Mycotoxin.
I> LD 50 8.5 mgfkg (p.o. mice). YC9990000.
Trichothecolone Sq-00873
3',7-Dihydroxy: [91860-55-8]. TC6 toxin
12,13-Epoxy-4-hydroxytrichothec-9-en-8-one, 9Cl. 4-
CuH3zOto M 456.489 Hydroxy-8-scirpenone
Product of Toxin T2 metabolism.
[2199-06-6]
Cole, R.J. et al, J. Nat. Prod. (Lloydia), 1981, 44, 324 (isol, deriv)
Yoshizawa, T. eta/, Appl. Environ. Microbiol., 1984, 47, 130.
Pawlosky, R.J., J. Agric. Food Chern., 1984, 32, 1420, 1423 (isol,
deriv, rns)
Corley, D.G. et al, Tetrahedron Lett., 1986, 27, 4133 (deriv)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 181.

Trichodiol A Sq-00871 C,5H 200 4 M 264.321

[28381-39-7] Trichothecene. Isol. from Fusarium roseum and
Trichothecium roseum. Hydrol. prod. of Trichothecin,

HOO{j
Sq-00872. Needles (C 6H 6 jpet. ether). Mp 183-184°. [cx]:,'l· 5
+22.SO (c, 1 in CHC1 3).
Ac: [4682-54-6].
Prisms (MeOH). Mp 148-149°.
C,5H2403 M 252.353
2,4-Dinitrophenylhydrazone: Deep orange rods
An artefact from the broth of Trichothecium roseum.
(EtOH/CHC1 3). Mp 261-262°.
Cryst. (Et20/hexane). Mp 81-83°. [cxln + 52° (CHCJ 3).
Freeman, G.G. et a/, J. Chern. Soc., I959, II05 (isol, ir, struct,
Machida, Y. eta/, Tetrahedron Lett., 1972, 1969 (biosynth) bib!)
Nozoe, S. eta/, Tetrahedron, 1972, 28, 5105.
Fishman, J. eta/, J. Chern. Soc., I960, 3948 (props)
Gyimesi, J. eta/, Tetrahedron Lett., I967, 1665 (prnr)
Hanson, J.R. eta/, J. Chern. Soc., Perkin Trans. I, I974, I033
(crnr)
Brumley, W.C. et a/, Biorned. Mass Spectrorn., 1982, 9, 45I (rns)
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., I981, 222.

313
Trichotriol- 3,7,15-Trihydroxy-8-scirpenone Sq-00874- Sq-00877

Trichotriol Sq-00874 C23H 320 7 M 420.502

[109890-37-1] Prod. by M. verrucaria. Oil. [1X]i; -25° (c, 0.5 m
CHCI 3).
7'-Epimer: [76685-83-1]. Trichoverrol B
Isol. from M. verrucaria. Oil. [1X]i: -3.3° (c, O.. W in
CHCI3).
7' -Epimer, 15-0-(E-5-Hydroxy-3-methyl-2-pentenoyl):
[76685-82-0]. Trichoverrin B
C15H 2,.04 M 268.352 C29H 400 9 M 532.630
lsol. from Fusarium sporotrichioides. Mycotoxin. Oil. lsol. from M. verrucaria. Precursor for macrocyclic
3-Deoxy: [40522-81-4]. Trichodiol trichothecenes. Oil. [1X]i: -32.2° (c, 0.57 in CHCI3).
C15H 240 3 M 252.353 7'-Epimer, 15-deoxy: [76685-81-9]. Trichodermadienediol B
lsol. from the broth of Trichothecium roseum. Artefact. C23 H 320 6 M 404.502
Nozoe, S. eta/, Tetrahedron, 1972, 28, 5105. Isol. from M. verrucaria. Oil. [1X]i: -15.8° (c, 0.8 in
Corley, D.G. eta/, J. Org. Chem., 1987, 52, 4405. CHCI 3).
7' -Epimer, 15-deoxy, 16-hydroxy: [86023-75-8]. 16··
Trichoverritone Sq-00875 Hydroxytrichodermadienediol B
[87292-19-1] C23 H 320 7 M 420.502
Prod. by M. verrucaria. Oil. [1X]i; -19.4° (c, 1.2 in

YJo'iH CHCI 3).

Jarvis, B.B. eta/, J. Am. Chem. Soc., 1981, 103, 472 (struct)

~j
Jarvis, B.B. et a/, J. Org. Chem., 1982, 47, 1117 (isol)
Jarvis, B.B. eta/, J. Antibiot., 1983, 36, 459 (derivs)
Roush, W.R. eta/, Tetrahedron Lett., 1983, 24, 3693 (synth)
~coo/ ooc

~ OY"::7
3,7,15-Trihydroxy-8-scirpenone Sq-00877
12,13-Epoxy-3,7,15-trihydroxy-9-trichothecen-8-om·
H

0 ~-OH
C35 H 460 11 M 642.742
Trichothecane antibiotic. Metab. of Myrothecium roridum. CH:zOH
Shows antibacterial and antileukaemic props. C15H 200 6 M 296.319
Mycotoxin. Oil. [1X]i; +45.0° (c, 0.2 in CHC13).
(3rx.,7rx.)-form [51481-10-8] Deoxynivalenol. Rd toxin.
Jarvis, B.B. et a/, Tetrahedron Lett., 1983, 24, 3539. Vomitoxin
Prod. by Fusarium graminearum and F. roseum.
Trichoverrol A Sq-00876 Mycotoxin. Cryst. (EtOAcjpet. ether). Mp 151-153°.
[76739-71-4] [IX]~ +6.35° (c, 0.07 in EtOH).
I> YD0167000.
H Semicarbazone: Mp 199-201°.
16 I 0 H OH

~7o~;
3-Ac: [50722-38-8]. Acetyldeoxynivalenol
C17H 220 7 M 338.357
Toxin from infected barley. Cryst. (Et20jpentane). Mp
185.5-186°
0

HOCH 2 OOC I> YD0150000.

15 #
3,7,15-Tri-Ac: Needles (EtOAcfpet. ether). Mp 155-157°.
C23H 320 7 M 420.502 Yoshizawa, T. eta/, Agric. Bioi. Chem., 1973, 37, 2933 (isol)
lsol. from Myrothecium verrucaria. Cryst. (Et20/pet. Blight, M.M. eta/, J. Chem. Soc., Perkin Trans. I, 1974, 1691
ether). Mp 177-179°. [IX)i! +37.7° (c, 0.45 in CHC13). (isol)
Shows lower toxicity than macrocyclic trichothecenes. Brumley, W.C. et al, Biomed. Mass Spectrom., 1982, 9, 451 (ms)
15-0-(E-5-Hydroxy-3-methyl-2-pentenoyl): [76739-70-3]. Miller, J.D. et al, Can. J. Microbial., 1983, 29, 1171 (isol)
Cameron, S. et al, J. Chem. Soc., Perkin Trans. I, 1989, 887
Trichoverrin A
(synth)
C;z,H400 9 M 532.630 Zamir, L.O., Tetrahedron, 1989, 45, 2277 (biosynth, deriv)
Isol. from M. verrucaria. Precursor of macrocyclic Jarvis, B.B. eta[, J. Org. Chem., 1990, 55, 3660 (cmr)
trichothecenes. Cryst. (EtOAcjpet. ether). Mp 78-79°. Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
[1X]i: - 2l.SO (c, 0.39 in CHCI3). Press, N.Y., 1981, 202.
15-Deoxy: [76740-74-4]. Trichodermadienediol A
C23H 320 6 M 404.502
Isol. from M. verrucaria. Biosynth. intermed. in
Verrucarin formation; weak antileukaemic agent. Cryst.
(CH 2Cl2jhexane). Mp 184-185°. [1X]i: +26.3° (c, 0.39 in
CHCI 3).
15-Deoxy, 16-hydroxy: [86004-56-0]. 16-
Hydroxytrichodermadienediol A

314
T2 Toxin - Verrucarin B Sq-00878 - Sq-00880

T2 Toxin Sq-00878 2',3'-Didehydro: Dehydroverrucarin A

12,13-Epoxy-9-trichothecene-3,4,8,15-tetro/4,15-diacetate 8- Cz7H320 9 M 500.544
(3-methylbutanoate), 9CI. Neosolaniol 4,15-diacetate 8-(3- Isol. from M. roridum. Shows similar activity to that of
methylbutanoate). Fusariotoxin T2. Insariotoxin. Mycotoxin Verrucarin A. Needles (Me2CO/Et20). Mp 233-240°.
T2 [IX]~ + 118° (CHCI 3).
[21259-20-l] 9,10-Epoxy, 16-hydroxy: [87532-32-9]. 9,10-Epoxy-16-
hydroxyverrucarin A
H C27 H340u M 534.559

~,OH
Semisynthetic. Antileukaemic agent. Mp 294-298°.
8-Hydroxy: [74608-63-2]. 8-Hydroxyverrucarin A
C27 H 340 10 M 518.560

~COO A<OH,C OA<

Semisynthetic. Antileukaemic agent. Cryst.
(Me2COfhexane). Mp >300°. [oc]~ +229° (c, 1.37 in
MeOH).
C24H 340 9 M 466.527 16-Hydroxy: [74516-64-6]. 16-Hydroxyverrucarin A
Trichothecene antibiotic. Isol. from Fusarium spp. and C27H340 10 M 518.560
Trichoderma lignorum. Important mycotoxin occurring Semisynthetic. Antileukaemic agent. Cryst.
naturally in various agricultural products. Needles. Mp (Me 2COfhexane). Mp > 300°. [oc]~ + 169° (c, 1.65 in
151-152°. [1X]i} -15.5° (CHCI 3). MeOH).
I> YDO I00000. Tamm, Ch. et al, Helv. Chim. Acta, 1962, 45, 1726; 1963, 46, 1786
3'-Hydroxy: [84474-35-1]. 3'-Hydroxy T2 Toxin (isol)
Zurcher, W. et a/, Helv. Chim. Acta, 1966, 49, 2594 (isol, deriv)
C24H 340 10 M 482.527
McPhail, A.T. et al, J. Chern. Soc. C, 1966, 1394 (cryst struct)
From F. sporotrichiella poae. Metab. of T2 Toxin. Breitenstein, W. et al, Helv. Chim. Acta, 1975, 58, 1172 (nmr)
Mycotoxin. Miiller, B. eta/, Helv. Chim. Acta, 1975, 58, 453, 471 (biosynth)
I> YD0090000. Jarvis, B.B. et al, J. Med. Chern., 1980, 23, 1054; 1984, 27, 239
Bamburg, J.R. et al, Tetrahedron, 1968, 24, 3329; Phytochemistry, (derivs)
1969, 8, 2405 (isol, props) Still, W.C. eta/, J. Org. Chern., 1981, 46, 5242 (synth)
Smalley, E.B. et al, Mycotoxins, (I.F.H. Purchase. Ed.), Elsevier, Mohr, P. eta/, Helv. Chim. Acta, 1982, 65, 1412 (synth)
New York, 1974, 199. McDougal, P.G., Diss. Abstr. Int., B, 1983, 43, 3245 (synth)
Ellison, R.A. et al, J. Org. Chern., 1976, 41, 576 (cmr) Kemppainen, B.W. eta/, Food Chern. Toxicol., 1987, 25, 379
Yoshizawa, T. et al, Agric. Bioi. Chern., 1982, 46, 2613 (deriv) (toxicol)
Pohland, A.E. et al, Pure Appl. Chern., 1982, 54, 2219 (uv, ir, pmr, Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
cd, ms) Press, N.Y., 1981, 247.
Eller, K.l. et al, Dokl. Akad. Nauk SSSR, Ser. Khim., 1985, 283,
1481 (deriv) Verrucarin B Sq-00880
Wani, M.C. et a/, J. Org. Chern., 1987, 52, 3468 (synth)
Gilardi, R. eta/, Acta Crystallogr., Sect. C, 1990, 46, 645 (cryst 2'-Deoxy-2',3'-epoxyverrucarin A, 9CI
struct) [2290-ll-l]
Van Middlesworth, F. eta/, J. Org. Chern., 1990, SS, 1237 As Verrucarin A, Sq-00879 with
(biosynth, cmr)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic XY = -O-
Press, N.Y., 1981, 185.
C17H3209 M 500.544
Isol. from Myrothecium verrucaria and M. roridum. Shows
Verrucarin A, 9CI Sq-00879 antifungal and cytostatic activity. Needles
Muconomycin A. VER-A. 397 Y
(Me2CO/Et20). Mp >330°. [oc]~ +94° (c, 0.99 in
[3148-09-2] CHCI3), [oc]~ + 147° (c, 1.06 in C6H6). ).max 258.5 nm
(EtOH).

J
~~6
1;10 H I> YX9825000.
Hiirri, E. et al, Helv. Chim. Acta, 1962, 45, 839 (isol)
o Gutzwiller, J. et al, Helv. Chim. Acta, 1965, 48, 177 (ir, pmr)

tn
I Breitenstein, W. et al, Helv. Chim. Acta, 1975, 58, 1172 (cmr)

I 2
I Breitenstein, W. et al, Helv. Chim. Acta, 1979, 62, 2699 (cryst
struct, abs corifig)
coo Jarvis, B.B. eta/, J. Nat. Prod. (Lloydia), 1982, 45, 440 (synth)

x/~o
Roush, W.R. et al, J. Org. Chern., 1984, 49, 4332 (synth)
Cole, R.J. et a/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 253.
0
X =OH, Y=H
C17H 340 9 M 502.560
CA numbering shown. Trichothecene antibiotic. From
Myrothecium verrucaria. Inhibitor of protein synth. in
fungi. Antineoplastic and insecticide. Cryst. Mp > 330°.
[1X]n +260° (CHCI 3), +208° (dioxan). ).max 260 nm
(EtOH).
I> WH1316810.
0-Ac: Needles (Me2CO/Et20). Mp 212-215°. [1X]~ + 132.5°
(c, 1.18 in CHCI 3).

315
Verrucarin J- Vertisporin Sq-00881 - Sq-00884

Verrucarin J Sq-00881 Verrucarin L Sq-00883

2',3'-Didehydro-2'-deoxyverrucarin A, 9Cl. Muconomycin B 2' ,3' -Didehydro-2' -deoxy-8-hydroxyverrucarin A, 9CI
[4643-58-7] [77101-87-2]

16

C27H 320 8 M 484.545

Trichothecene antibiotic. Metab. of Myrothecium C27 H 320 9 M 500.544
verrucaria and M. roridum. Cytotoxic. Cryst. Trichothecene antibiotic. Isol. from Myrothecium
(CHCI 3/Etp). Mp 315°. [a]i;1 +22° (c, 1.01 in CHC1 3), verrucaria. Antileukemic. Mp 230-235°. [a]i,? + 15° (c,
[IX]~ +41 ° (c, 0.78 in C6H 6).
0.92 in CHC1 3).
I> YX9822000. 8-Ac: [77101-88-3]. 8-Acetylverrucarin L
8-Hydroxy: see Verrucarin L, Sq-00883 C29H340 10 M 542.582
16-Hydroxy: [87532-29-4]. 16-Hydroxyverrucarin J Isol. from M. verrucaria. Mp 132-135°. [a]i,? +29.7° (c,
C27 H 320 9 M 500.544 0.52 in CHC1 3).
Semisynthetic. Antileukaemic agent. Mp > 300°. Jarvis, B.B. et a/, J. Antibiot., 1981, 34, 120 (isol, struct)
13'-Hydroxy: [90297-50-0]. 13'-Hydroxyverrucarin J. PD Jarvis, B.B. eta/, J. Org. Chern., 1982,47, 1117.
113325. Antibiotic PD 113325
C27 H 320 9 M 500.544 Vertisporin Sq-00884
FromM. roridum. Active against tumours and yeasts.
Cryst. (CH 2Cl2 /cyclohexane). Mp > 250°. [57100-32-0]
Bohner, B. eta/, Helv. Chirn. Acta, 1965, 48, 1079, 1669 (isol, uv,
ir, prnr)
Vittimberga, J.S. eta/, J. Org. Chern., 1965, 30, 746 (isol)
White, J.D. eta/, J. Org. Chern., 1982, 47, 929 (struct)
Esmond, R. eta/, J. Org. Chern., 1982, 47, 3358 (synth)
Roush, W.R. eta/, J. Org. Chern., 1983, 48, 758; 1984, 49, 1772
(synth)
Smitka, T.A. et a/, J. Antibiot., 1984, 37, 823 (deriv)
Jarvis, B.B. et a/, J. Med. Chern., 1984, 27, 239 (deriv)
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 259.

Verrucarin K Sq-00882
[63739-93-5]
I
OH
C29H 360 10 M 544.597
From Verticimonosporium diffractum. Amorph. powder.
Mp 176-183°. [IX]~ +62.SO. Amax 216 nm (e 19 500)
(EtOH).
Di-Ac: Mp 145-155°.
7',8'-Didehydro: [102852-48-2]. Roritoxin A
C29H 340 10 M 542.582
Prod. by Myrothecium roridum. Mycotoxin. Mp 220-
2250. [a]i] + W (c, 0.51 in CHC1 3). Side chain
sterochem. of the Roritoxins not indicated. Prob the
C27 H 340 8 M 486.561
From Myrothecium verrucaria. Antibiotic. Cryst. same as in Vertisporin.
I> Acutely cytotoxic.
(CH 2Cl 2/Etp). Mp > 320° dec. [a]~ +218° (c, 0.58 in
CHC1 3). A.max 259 nm (loge 4.19) (EtOH). 7',8'-Didehydro, 2',3'-epoxide: [102852-49-3]. Roritoxin B
C29H 340 11 M 558.581
I> YX9821000.
From M. roridum. Mycotoxin. Cryst. (EtOAc). Mp 262-
Ac: Needles (Me 2CO/Etpjpet. ether). Mp 199-202°. [a]~ 2650 dec. [a]i] + 2.6° (c, 0.6 in CHC1 3).
+ 143° (c, 0.83 in CHC1 3). I> Most toxic of the reported trichothecenes.
Breitenstein, W. eta/, Helv. Chirn. Acta, 1977, 60, 1522 (isol, 7',8'-Didehydro, 2',3'-epoxide, 14'-ketone: [102852-51-7].
spectra) Roxitoxin D
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 260.
C29H 320 11 M 556.565
FromM. roridum. Mycotoxin. Cryst. (MeOH). Mp 294-
2970. [a]i] + 30° (c, 0.1 in CHC1 3).

316
Acanthellin 1- 1-Bromo-7-eudesmen-4-ol Sq-00885 - Sq-00891

I> Acutely cytotoxic. 1-Bromo-6-chloro-4-eudesmanol Sq-00888

7' ,8'-Didehydro, 2' ,3' ;9p,JOP-diepoxide, 14' -ketone: [102852-
50-6]. Roritoxill C Br
I

M 572.565

H~-~
C~ 32 0 11
Prod. by M. roridum. Mycotoxin. Cryst. (EtOAc). Mp
288-290° dec. [cx]~ +8.9° (c, 0.40 in CHC1 3). Acutely
cytotoxic.
Hayakawa, S. et a/, J. Antibiot., 1975, 28, 550.
Minato, H. eta/, Tetrahedron Lett., 1975, 2579. C 1 ~H 26 BrClO M 337.726
Jarvis, 8.8. et al, J. Org. Chern., 1986, Sl, 2906 (Roritoxins) (1 «.,4«.5P,6P,7«.,1 0«. )-form [657 46-13-6] Heterocladol
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic Constit. of Laurencia filiformis. Cryst. (pet. ether). Mp
Press, N.Y., 1981, 241. 78-79°. [cxln + 13.8° (c, l in CHC1 3).
Kazlauskas, R. et al, Aust. J. Chern., 1977, 30, 2679 (cryst struct)

wy
1-Bromo-4,6-eudesmanediol Sq-00889

Simple eudesmanes
Absolute
configuration
Acanthellin 1 Sq-00885 HO OH
[54462-52-l] Ct~H 27 Br0 2 M 319.281
(1 p,4«.,6«.,7«. )-form

~
Austradiol
6-Ac: [82731-83-7]. Austradiol acetate
C 17H 29Br03 M 361.318
Constit. of Laurenciafi/iformis. Oil. [cx]~ + l4.SO (c, 1.75
C16H15N M 231.380 in CHC1 3).
Constit. of Acanthella acuta. Oil. [cxln -41.2° (c, 5 in 4,6-Di-Ac: [82731-84-8]. Austradiol diacetate
CHC1 3). C 19H 31 Br04 M 403.355
Minale, L. et al, Tetrahedron, 1974, 30, 1341. Constit. of L. fi/iformis. Cryst.
Brennan, M.R. et al, J. Org. Chern., 1982, 47, 3917.
Benghalensin A Sq-00886
[87174-91-2] 1-Bromo-4(15)-eudesmen-11-ol Sq-00890
Br

Ct~H 20 0 4 M 264.321
Constit. of Meriandra benghalensis. Cryst. (EtOAcjpet.
<P-foH
C 1 ~H 15 Br0 M 301.266
(lj3,7cx}:form

ether). Mp 123°. [cx]~ - 3UO (c, 0.44 in CHC1 3).
Perales, A. eta/, J. Org. Chern., 1983, 48, 5318.
Benghalensin B
[87174-92-3]
(1P,7«)-form [72154-34-8] lsobrasudol
!sol. from Aplysia brasiliana. Mp 105-107°. [cx]i,6 + 10.3°.
(lp,7Jl)-form [72154-35-9] Brasudol
From A. brasiliana. Exhibits potent fish antifeedant
Sq-00887 activity. Mp 105-106°. [cx]i,6 + l6.SO.
Dieter, R.K. eta/, Tetrahedron Lett., 1979, 1645 (isol, struct)

1-Bromo-7-eudesmen-4-ol Sq-00891
Br

M
I

C 1 ~H 20 0 4 M 264.321

H~
Constit. of Meriandra benghalensis. Cryst. (EtOAcjpet.
ether). Mp 163°. [cx]~ -ll4.SO (c, 0.131 in CHCl 3).
Perales, A. et al, J. Org. Chern., 1983, 48, 5318.
C 1 ~H 15 Br0 M 301.266
Oil.
(1«.,4«.5P,10«.)-form [62264-66-8]
ent-1P-Bromo-4P-hydroxy-7-se/inene
Constit. of Laurencia spp. [cx]~ + 52.6° (c, 4.62 in
CHC1 3).

317
Carindone - 3,4-Dihydroxy-7(11)-eudesmen-8-one Sq-00892 -- Sq-00898

7,8-Dihydro, 7P-chloro: [68690-87-9]. ent-1P-Bromo-7rz.- Constit. of Parsonia heterophylla. Cryst. Mp 132-133°. [rx.Ji?
chloro-4fJ-eudesiiUllfol. ent-IP-Bromo-7rx.-ch/oro-4P- +47.9° (c, 0.37 in EtOH).
hydroxyse/inane Eggers, N.J. et al, Tetrahedron Lett., 1979, 3053.
C 15H:u;BrC10 M 337.726
Metab. of L. spp. Cryst. (hexane). Mp 128-131° dec.
[rx.Jn +32.7° (c, 1.07 in CHC1 3). 4,6-Dihydroxy-11(13)-eudesmen-12-oic Sq-00896
Howard, B.M. et al, J. Org. Chern., 1977, 42, 2518 (isol, struct)
acid
Rose, A.F. et al, Tetrahedron Lett., 1977, 2935; 1978, 2533 (isol, [27652-24-0]
struct)

Carindone
[38045-62-4]
Sq-00892
~
C>H
HO' H COOH
C 15H 240 4 M 268.352
(4rz.,6rz. )-form
Arbusculin E
OH Constit. of Artemisia arbuscula. Cryst. (Et20). Mp 159-
1600. [rx.]i;' +3° (c, 0.75 in CHC1 3).
Me ester:
0 C16H:u;04 M 282.379
C31 H 440 6 M 512.685 Constit. of Rudbeckia grandiflora. Gum.
Constit. of Carissa carandas. Cryst. Mp 262°. Irwin, M.A. et al, Phytochemistry, 1969, 8, 2411 (isol)
Singh, B. et al, Phytochemistry, 1972, 11, 1797. Yamakawa, K. eta/, Heterocycles, 1977, 8, 103 (synth)
Vasquez, M. et al, Phytochemistry, 1988, 27, 2195 (isol, deriv)

5,6:7,8-Diepoxyeudesmane Sq-00893
2,11-Dihydroxy-4-eudesmen-3-one Sq-00897
5,6:7,8-Bisepoxyeudesmane

C 15H 240 3 M 252.353

C 15H 240 2 M 236.353
2rz.-:form [99957-09-2] rz.-Carissanol
(5«,6«,7«,8«)-form Constit. of Carissa edulis. Oil. [rx.Ji? + 124° (c, 0.07 in
Constit. of Liabumfloribundum. Oil. [rx.]i;' -21° (c, 0.41 CHC1 3).
in CHC13).
Achenbach, H. et al, Phytochemistry, 1985, 24, 2325.
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1800.

3,4-Dihydroxy-7(11)-eudesmen-8-one Sq-00898
3,5-Dihydroxy-4(15),11(13)-eudesmadien- Sq-00894
12-oic acid
3 ° (3a,4a)-:form

~ril
HO' I ::::::,..

HO H
COOH
HO~ C 15H 240 3 M 252.353
(3«,4«)-:form [52483-04-2] Cuauhtemone
CtsH 220 4 M 266.336 lsol. from Pluchea odorata. Plant growth inhibitor.
(3«,5«)-:form Cryst. Mp 140°. [rx.ln + 59.2°.
3rz.,5rz.-Dihydroxycostic acid 3-Ange/oyl: [60756-54-9].
Constit. of Jasonia montana. Gum. C20 H 300 4 M 334.455
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (isol, pmr) Constit. of P. odorata. Cryst. (Etpjpet. ether). Mp
111°.
1,12-Dihydroxy-5,11(13)-eudesmadien-3- Sq-00895 3-(2-Acetoxy-3-hydroxy-2-methylbutanoy[), 4-Ac: [ ll9347-
18-1]. Argutin
one C24H 380 8 M 454.559
Heterophyllol
Constit. of P. arguta. Cryst. Mp 108°. [ali? +82.3°
[73537-23-2] (MeOH).
(3P,4«)-:form
3-Epicuauhtemone. 3-epi-Cuauhtemone
Cryst. (Et20jpet. ether). Mp 68-69°.
3-Ange/oyl: Isol. from P. suaveolens. Oil. [1X]~4 +42° (c, 7.3
in CHC1 3).
3-Angeloy/, 4-Ac:
M 250.337 C22 H 320 5 M 376.492
Constit. of P. suaveolens. Oil. [a]i;' +45.1° (c, 6.5 in
CHC13).

318
6,11-Dihydroxy-3-eudesmen-2-one - 4,11-Epoxyeudesmane Sq-00899 - Sq-00905

lvie, R.A. et al, Acta Crystal/ogr., Sect. B, 1974, 30, 2891 (cryst 3,4-Dihydroxy-8-oxo-11(13)-eudesmen-12- Sq-00902
struct) oic acid
Nakanishi, K. et al, J. Am. Chern. Soc., 1974, 96, 609 (isol, cmr)
Bohlmann, F. eta[, Chern. Ber., 1976, 109, 2653 (isol)
Goldsmith, D.J. et al, J. Org. Chern., 1976, 2095 (synth)
Bohlmann, F. et al, Phytochemistry, 1980, 19, 969 (isol, derivs) 110~0 COOH

~
Ahmad, V.U. et al, Planta Med., 1988, 54, 462 (Argutin)

6,11-Dihydroxy-3-eudesmen-2-one Sq-00899
6,11-Dihydroxy-3-se/inen-2-one C15H 220 5 M 282.336
(3P,4r~.)-form

O~
3-(2,3-Epoxy-3-methylbutanoyl), Me ester: [122398-18-9].
Plucheicinin
OH C21 H 300 7 M 394.464
~ Constit. of Pluchea arguta. Gum. [1X]i:' -201° (c, 0.01 in
MeOH).
CISH2403 M 252.353 Ahmad, V.U. eta[, Phytochemistry, 1989, 28, 3081 (isol, pmr, cmr)
6«-form [70902-19-1] r~.-Chenopodiol-2-one
Constit. of Chenopodium botrys. Cryst. Mp 104°. [1X] 0
-130°.
2,5-Epidioxy-3,11-eudesmadien-1-one Sq-00903
2,5-Peroxy-3,11-eudesmadien-1-one
6-Ac: [74799-30-7]. 61X-Acetoxy-11-hydroxy-3-selinen-2-one
C.7H 21;04 M 294.390
Constit. of C. botrys. Cryst. (hexane). Mp 59-60°. [1X] 0
+ 77.1° (c, 0.9 in CHC13).
de Pascual Teresa, J. et al, Tetrahedron, 1980, 36, 371.

6,11-Dihydroxy-4-eudesmen-3-one Sq-00900
C 15H 200 3 M 248.321

om
Carissanol
(2r~..5r~.)-form
Constit. of Artemisia caerulescens. Gum. [1X]i: + 239° (c,
0.22 in CHC1 3).

~OH Sanz, J.F. et al, Phytochemistry, 1990, 29, 2913 (isol, pmr, cmr)

C 15H 240 3 M 252.353 5,8-Epidioxy-6-eudesmene Sq-00904

6r~.-form[99957-10-5] 6-Eudesmene 5 ,8-endoperoxide
Constit. of Carissa edulis. Oil. [1X]i:' + 66.4° (c, 0.25 in
CHC1 3).
6P-form [99957 -11-6]
From C. edulis. Cryst. Mp 115-118°. [1X]i:' + 10° (c, 0.3
in CHC1 3).
Achenbach, H. eta[, Phytochemistry, 1985, 24, 2325. CISH2402 M 236.353
(5r~.,8r~.)-form

8,11-Dihydroxy-3-eudesmen-2-one Sq-00901 Constit. of 1socoma coronopifolia. Oil.

Dominguez, X.A. et al, Phytochemistry, 1986, 25, 2893.

O~OH 4,11-Epoxyeudesmane Sq-00905

5 (5a.,8a.)-:form
::::,..
H OH
[53840-54-3]

CISH2403 M 252.353
(5r~.,8r~.)-form
Constit. of Eremophila scoparia. Cryst. (EtOAc). Mp
125.5-126.5°. [1X] 0 + 85.SO (CHC1 3).
8-Ac: 8-Acetoxy-11-hydroxy-3-eudesmen-2-one
C 17H 21,04 M 294.390 CISH21;0 M 222.370
From E. scoparia. Cryst. Mp 131.5-l33.SO. Constit. of the frontal gland secretion of Amitermes
(5P,Br~.)-:form evuncifer. Oil.
From E. scoparia. Cryst. Mp 154-155°. Wadhams, L.J. et al, Tetrahedron Lett., 1974, 1697 (isol)
Babidge, P.J. et al, Aust. J. Chern., 1984, 37, 629. Paknikar, S.K. et al, Tetrahedron Lett., 1975, 1293 (struct)
Baker, R. et al, J. Chern. Soc., Chern. Commun., 1977, Ill (synth)
Scheffrahn, R.H. et al, Experientia, 1984, 40, 1136 (isol)

319
6,15-Epoxy-1,4-eudesmanediol- 4,11-Eudesmadiene Sq-00906 -- Sq-00912

6,15-Epoxy-1,4-eudesmanediol Sq-00906 Constit. of essential oil of hops (Humulus lupulus). Oil.

Buttery, R.G. eta/, Chern. Ind. (London), 1966, 1225 (isol, struct)
HO Brown, E. D. et a/, J. Chern. Soc., Perkin Trans. I, 1975, 2326

HQ;:y
(synth)
Wilson, S.R. eta/, J. Am. Chern. Soc., 1978, 100, 6289 (synth)
Banerjee, G.K. et a/, J. Chern. Res. (S), 1984, 284 (synth)
Lee, S.-J. eta/, J. Chern. Soc., Chern. Commun., 1988, 1188 (synth)

'---0
3,11-Eudesmadiene Sq-00910
C 15H 260 3 M 254.369
3,11-Se/inadiene
(lp,4fl)-form [118243-71-3]
[473-13-2]
Constit. of Ageratina saltillensis.
Fang, N. eta/, Phytochemistry, 1988, 27, 3187.

1,4-Epoxy-6-eudesmanol Sq-00907 (Sa, 7~, 10~)-Jorm

r;;Jl (la,4cx,5a,6~, 10~)-:form C,sH24 M 204.355

't1:Y
[oc]i? - 14.SO (c, 1 in CHC1 3).
(51X,7p,JOfl)-form
1¥.-Se/inene. oc-Eudesmene
C,sH260 2 M 238.369 Occurs in celery oil and in various other esst:ntial oils,
(11Y.,41Y.,51Y.,6P,l Ofl)-form e.g. Cannabis sativa, Humulus lupulus, Anthocephalus
Ac: 6P-Acetoxy-11Y.,41Y.-epoxyeudesmane cadamba (earlier isolates not separated from P-selinene).
C 17H 28 0 3 M 280.406 Also present in liverworts. Oil. Bp 268-272°. [ocJi?
Constit. of Sideritis varoi. Gum. [oc]i? -17.6° (c, 1 in -14.5° (c, 1 in CHC1 3).
CHC1 3). (51X,7P,l01Y.)-form [66141-13-7]1¥.-Helmiscapene
(1 p,4p,sp,6p,l 01¥. )-form C1sH24 M 204.355
Constit. of Scapania undulata and Helminthosporium
6-Cinnamoyl: [119364-26-0]. 61Y.-Cinnamoyloxy-Jp,4p-epoxy- sativum. Oil.
1P,l01Y.-eudesmane
C24H 320 3 M 368.515 (5P,7P,101Y.)-form [28290-23-5]
Constit. of Ambrosia artemisioides. Oil. Constit. of Dipterocarpus alatus. Oil. [oc]i? +2.10°.
6-(4-M ethoxybenzoyl): [119285-47 -1]. 61¥.-Anisoyloxy-1 p,4P- (5p,7p,JOfl)-form [83378-03-4]
epoxy-lp,J 01¥.-eudesmane Constit. of the defence secretion of Amitermes excel/ens.
C23H 320 4 M 372.503 Chetty, G.L. eta/, Tetrahedron, !966, 22, 2311 (synth}
Constit. of A. artemisioides. Oil. Klein, E. eta/, Tetrahedron Lett., 1970, 279 (isol)
Stevens, K.L. eta/, J. Org. Chern., 1971, 36, 2422 (synth)
Cabrera, E. et a/, Phytochemistry, 1988, 27, 183. Maurer, B. et a/, Helv. Chim. Acta, 1977, 60, 2177 (isol, pmr, ir)
Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551. Anderson, N.H. eta/, Phytochemistry, 1977, 16, 1731 (isol)
Naya, Y. eta/, Tetrahedron Lett., 1982, 23, 3047 (isol)
Eudeshonokiol Sq-00908 Kutney, J.P. eta/, Can. J. Chern., 1984, 62, 1407 (synth)
Caine, D. eta/, J. Org. Chern., 1988, 53, 4124 (synth)
[126654-55-5]
4,7(11 )-Eudesmadiene Sq-00911

~OH
4,7(1 1)-Se/inadiene

C 1sH 24 M 204.355
Constit. of Laurencia nidifica. Unstable oil. [oc]i;' + 34° (c,
C33H 440 3 M 488.709 0.9 in CHC1 3).
Constit. of bark of Magnolia obovata. [oc]n -48.6° (c, 0.45 [95343-73-0]
in EtOH). Sun, H.H. et al, J. Org. Chern., 1978, 43, 1613.
Fukuyama, Y. et al, Chern. Lett., 1990, 295 (isol, struct) Banerjee, A.K. et a/, J. Chern. Res. (S), 1984, 284 (synth)

3,7(11 )-Eudesmadiene Sq-00909 4,11-Eudesmadiene Sq-00912

3,7(1 1)-Se/inadiene 4,11-Se/inadiene

A
[6813-21-4] I

C,sH24 M 204.355
M 204.355 (7P,101Y.)-form [28290-20-2]

320
4(15),7(11)-Eudesmadiene - 4,7(11)-Eudesmadiene-12,13-diol Sq-00913 - Sq-00919

Constit. of Dipterocarpus alatus and Diplophyllum spp. Govindachari, T.R. et al, Indian J. Chem., Sect. B, 1973, 11, 971
Oil. [1X]i? -108.6°. (isol, struct)
Andersen, N.H. et al, Phytochemistry, 1977, 16, 1731 (/J-
Klein, E. et al, Tetrahedron Lett., 1970, 279 (isol, struct) Helmiscapene)
Huffman, J.W. et al, J. Org. Chem., 1976, 41, 3710 (synth) Naya, Y. et al, Tetrahedron Lett., 1982, 23, 3047 (isol)
Ohta, Y. et al, Tetrahedron, 1977, 33, 617 (isol) Wijnberg, J.B.P.A. eta/, J. Org. Chem., 1983, 48, 4380 (synth)
Caine, D. et al, J. Org. Chem., 1988, 53, 4124 (synth)
4(15),7(11)-Eudesmadiene Sq-00913
4(1 5), 7(1 1)-Selinadiene 4,11(13)-Eudesmadiene-12,15-dial Sq-00916
[515-17-3] 4,11-Selinadiene-12,15-dia/

(]17
~CHO
CtsH14 M 204.355 CtsH200 2 M 232.322
Constit. of essential oil of hops (Humulus /upulus). Oil. Constit. of Libanothamnus granatesianus. Oil. [IX]i; + 66.7°
Buttery, R.G. eta/, Chem. Ind. (London), 1966, 1225 (isol) (c, 5.2 in CHC1 3).
Andersen, N.H. et al, Tetrahedron Lett., 1970, 1759 (struct) Bohlmann, F. et al, Phytochemistry, 1980, 19, 1145.
Brown, E.D. et al, J. Chem. Soc., Perkin Trans. I, 1975, 2326
(synth)
Posner, G.H. et al, Tetrahedron Lett., 1975, 1373 (synth) 3,11-Eudesmadiene-1,13-diol Sq-00917
3,11-Selinadiene-1 ,13-diol
4(15),7-Eudesmadiene Sq-00914 OH
4(15),7-Selinadiene I

~ H CH 2 0H
13

CtsH14 M 204.355 C 15H 140 2 M 236.353

(5p,lOa.)-form [28102-71-8] Vetiselinene lrx.-form [70855-58-2] Cnicothamnol
Minor constit. of vetiver oil. Oil. Constit. of Cnicothamnus lorentzii. Oil.
Andersen, N.H., Tetrahedron Lett., 1970, 1755, 1759 (synth, isol) 13-A/dehyde: [70855-60-6). 11X-Hydroxy-3,11-eudesmadien-
Garrat, P.J. eta/, J. Org. Chem., 1986, 51, 5450 (synth) 13-a/. Cnicothamnal
CtsHn0 2 M 234.338
4(15),11-Eudesmadiene Sq-00915 Constit. of C. lorentzii. Oil.
4(15),11-Selinadiene Bohlmann, F. et al, Phytochemistry, 1979, 18, 95.

3,11(13)-Eudesmadiene-12,15-diol Sq-00918
3,11(13)-Se/inadiene-12,15-diol
(5a,7~,10~)-:form

CtsH14 M 204.355
(5a.,7p,JOJI)-form [17066-67-0] P-Selinene. Cyperene II
Constit. of celery oil. Also from Cyperus rotundus and
~~OH
CHPH
Humulus lupulus. Oil. Bp6 121-122°. [1X] 0 +61°.
(5p,7a.,10rx.)-form [473-12-1] CtsHl402 M 236.353
ent-4( 15), 11- Eudesmadiene. ent-4(15), 11-Selinadiene Constit. of Libanothamnus granatesianus. Oil. [1X]i; -84.8°
Constit. of the essential oils of Libanotis transcaucasica (c, 0.4 in CHC1 3).
and Seseli indicurn. Oil. Bp 1_2 70-115°. [1X] 0 -46° (c, 10 Bohlmann, F. et al, Phytochemistry, 1980, 19, 1145.
in CHC1 3).
(5p,7p,JOrx.)-form [29868-52-8] 4,7(11 )-Eudesmadiene-12,13-diol
Constit. of Aristo/ochia indica. Oil. Bp0. 3 80-85°. [1X] 0
Sq-00919
4,7(1 1)-Se/inadiene-12,13-dio/

MCH,OH
-71.63° (c, 4.61 in CHC1 3).
(5p,7p,JOJI)-form [83434-35-9]
Constit. of the defence secretion of Amitermes excel/ens.
(5a.,7P,10a.)-form [66141-12-6] fJ-Helmiscapene
lsol. from Scapania undulata and Helminthosporium
sativum. Oil. CHPH
Trivedi, B. et al, Collect. Czech. Chem. Commun., 1964, 29, 1675 C 15H 140 2 M 236.353
(isol)
Marshall, J.A. et al, J. Org. Chem., 1966, 31, 2933 (synth) Di-Ac: [110299-95-1]. Coralloidin D
Dixit, S.M. et al, Chem. Ind. (London), 1967, 1256 (iso[) C 19H 280 4 M 320.428
Vig, O.P. eta/, J. Indian Chem. Soc., 1968, 45, 1033 (synth) Constit. of Alcyonium coral/aides. Oil. [1X]i? -14.1 o (c,
Stevens, K.L. et a/, J. Org. Chem., 1971, 36, 2422 (synth) 0.227 in EtOH).
D'Ambrosio, M. et al, Helv. Chim. Acta, 1987, 70, 612.

321
4(15),11(13)-Eudesmadiene-7,12-diol - 4(15),11(13)-Eudesmadien-12-... Sq-00920 -- Sq-00923

4(15),11(13)-Eudesmadiene-7,12-diol Sq-00920 From A. spectabilis.

4(15),11(13)-Se/inadiene-7,12-dio/ [69978-82-1]
Bohlmann, F. et al, Chern. Ber., 1977, 110, 301 (isol)
Cruz, R. et al, Aust. J. Chern., 1982, 35, 451 (synth)
Zdero, C. et al, Phytochemistry, 1990, 29, 3201 (epoxides)

4(15),11(13)-Eudesmadien-12-oic acid Sq-00923

C 15H 240 2 M 236.353 4(15),11(13)-Se/inadien-12-oic acid. fl-Costic acid. Costus
7rx.-form [86703-05-1] 7-Hydroxycostol acid
Phytoa1exin from Ipomoea batatas infected with [3650-43-9]
Ceratocystis jimbriata. Oil. [(J(ln + 15° (c, 2 in CH 2C1 2).
12-A/dehyde: (86703-04-0]. 7()(-Hydroxy-4(15),11(13)-
eudesmadien-12-a/. 7-Hydroxycostal
C 15H 220 2 M 234.338
Phytoalexin from I. batatas. Cryst. Mp 123-124°. [(J(ln
+2° (c, 0.4 in CH 2Cl2). ClsH220 2 M 234.338
12-Carboxy/ic acid: 7-Hydroxy-4( 15),11 ( 13)-eudesmadien- Constit. of the root of costus (Saussurea lappa) and minor
12-oic acid. 7-Hydroxycostic acid constit. of Ambrosia ilicifolia. Cryst. (EtOH aq.). Mp
C 15H 220 3 M 250.337 87-88°. (aJn +23.4° (c, 3 in CHC1 3).
Constit. of Cassia longifolia. Cryst. Mp 220°. [a]i;' +21° 9a-Hydroxy: 9a-Hydroxy-4(15), 11 (13)-eudesmadien-12-oic
(c, 3.03 in CHC1 3). acid. 9rx.-Hydroxycostic acid
[96479-42-4, 96479-43-5, 96647-97-1] C 15H 220 3 M 250.337
Schneider, J.A. et al, J. Chern. Soc., Chern. Commun., 1983, 353 Constit. of Flourensia macrophylla. Oil.
(isol) 9fi-Hydroxy: [94190-55-3]. 9fi-Hydroxy-4(15),11(13)-
Cuomo, J., J. Agric. Food Chern., 1985, 33, 717 (synth) eudesmadien-12-oic acid. 9/J-Hydroxycostic acid
Wijnberg, J.B.P.A. et al, J. Org. Chern., 1985, SO, 2650 (synth) C 15H 220 3 M 250.337
Zdero, C. et al, Phytochemistry, 1987, 26, 187 (7-Hydroxycostic
Constit. of F. macrophylla.
acid)
Tanaka, A. eta/, Agric. Bioi. Chern., 1988, 52, 2043 (synth) 9-0xo: 9-0xo-4(15),11(13)-eudesmadien-13-oic acid. 9-
0xocostic acid
C 15H 200 3 M 248.321
3,11(13)-Eudesmadien-12-oic acid Sq-00921 From F. macrophylla. Cryst. (as Me ester). Mp 46° (Me
3,11(13)-Selinadien-12-oic acid ester).

q:y
[28399-17-9]
4()(,15-Epoxide: 4a,15-Epoxy-II(I3)-eudesmen-I2·oic acid.
4rx.,15-Epoxycostic acid
ClsH2z03 M 250.337
lsol. from Apalochlamys spectabilis. Oil (as Me ester).
[a]i;' -33° (c, 0.18 in CHC1 3) (Me ester).
H COOH 8fi,9P-Dihydroxy: [94190-56-4]. 8fi,9P-Dihydroxy·
C 15H 220 2 M 234.338 4( 15), 11 ( 13)-eudesmadien-12-oic acid. 8P,9fl-
Constit. of Stevia acha/ensis and Schistostephium Dihydroxycostic acid
crataegifolium. C15H 2z04 M 266.336
From F. macrophylla. Cryst. (as Me ester). Mp 53° (Me
I> LE3100000. ester). [()(]~4 + 34° (c, 0.35 in CHC1 3) (Me ester).
3a,4a-Epoxide: (108907-00-2]. 3a,4a-Epoxy-11(13)-
8fi-Acetoxy: BP-Acetoxy-3, 11 (13)-eudesmadien-12-oic acid.
eudesmen-12-oic acid. Jliscosic acid 8fl-Acetoxycostic acid
C15H 220 3 M 250.337 C 17H 240 4 M 292.374
Constit. of Inula viscosa. Oil. Constit. of Geigeria rigida.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1632 (isol) 1fi,9P-Dihydroxy: [94190-57-5]. Jfi,9P-Dihydroxy-
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1986, 799 (isol)
Ulube1en, A. et al, Phytochemistry, 1987, 26, 1223 (Viscosic acid) 4(15),11(13)-eudesmadien-12-oic acid. Jp,9JJ-
Dihydroxycostic acid
C 15H 220 4 M 266.336
4,11(13)-Eudesmadien-12-oic acid Sq-00922 From F. macrophylla. Oil (as Me ester). [a]~4 + 17° (c,
Isocostic acid 0. 7 in CHC1 3) (Me ester).
[62458-44-0] 2a-Hydroxy: 2a-Hydroxy-4(15), 11 (13)-eudesmadien-12-oic

Q)ycooH
acid. 2rx.-Hydroxycostic acid
ClsH220 3 M 250.337
Constit. of Sphaeranthus indicus and Gratysty/,is
cenocephala, also present as various esters. Cryst. Mp
187-189°.
C 15H 220 2 M 234.338 3a-Hydroxy: [100664-47-9]. 3-Hydroxy-4(15),11(13)-
Constit. of Ageratina g/abrata. Oil. eudesmadien-12-oic acid. 3a-Hydroxycostic acid. Jliscic
4a,5a-Epoxide: 4rx.,5rx.-Epoxy-11(11)-eudesmen-12-oic acid acid
C 15H 22 0 3 M 250.337 C15H 220 3 M 250.337
Isol. from Apalochlamys spectabilis. Constit. of Dittrichia viscosa. Gum.
4fi,5fi-Epoxide: 4P,5fl-Epoxy-11(11)-endesmen-12-oic acid I U{.,l3-Dihydro: [72944-20-8]. 4(15)-Eudesmen-12-oic acid.
C 15H 220 3 M 250.337 4(15)-Selinen-12-oic acid. 11,11-Dihydrocostic acid
C 15H 240 2 M 236.353

322
1,3-Eudesmadien-11-ol - 3,11(13)-Eudesmadien-12-ol Sq-00924 - Sq-00929

Constit. of F. heterolepis. [cx]i;' +55.1° (c, 1 in CHC1 3) 3,11-Eudesmadien-1-ol Sq-00926

(as Me ester). 3,11-Se/inadien-1-ol
(±)-form
Mp ll5-1W.
Bawdekar, A.S. eta/, Tetrahedron, 1965, 21, 1521 (isol, struct)
Herz, W. eta/, J. Org. Chern., 1966, 31, 1632 (isol)
Marshall, J.A. eta/, J. Org. Chern., 1966, 31, 2933 (synth)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1189 (11,13-
Dihydrocostic acid)
Bohlmann, F. et a/, Phytochemistry, 1984, 23, 1445 (derivs) CtsH 240 M 220.354
Ceccherelli, P. et a/, Phytochemistry, 1985, 24, 2987 (3-
Hydroxycostic acid) 1fJ-form
U1ubelen, A. eta/, Phytochemistry, 1987, 26, 1223 (Viscic acid) rx.-Dictyopterol
Sohoni, J.S. eta/, J. Chern. Soc., Perkin Trans. 1, 1988, !57 (2- Constit. of Dictyopteris divaricata. Oil.
Hydroxycostic acid) Kurosawa, E. eta/, Bull. Chern. Soc. Jpn., 1966, 39, 2509 (isol,
Zdero, C. eta/, Phytochemistry, 1988, 27, 865 (2-Hydroxycostic struct)
acid)
Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (8-Acetoxycostic
acid) 3,11-Eudesmadien-6-ol Sq-00927
Zdero, C. eta/, Phytochemistry, 1990, 29, 3201 (epoxide) 3,11-Se/inadien-6-ol

1,3-Eudesmadien-11-ol
1,3-Se/inadien-11-ol
Sq-00924
rt1
~
C15H240 M 220.354
(5rx.,6rx. )-form
Ac: [67996-63-8].
C 15H 240 M 220.354 C 17H 260 2 M 262.391
(5rx.,7fJ,JOrx.)-form [473-17-6] Occidentalol Constit. of Chenopodium botrys. Oil.
Constit. of Thuja occidenta/is. Cryst. (pet. ether). Mp Teresa, J. de P. et a/, An. Quim., 1978, 74, 1023.
95°. [cx]i;' +361° (c, 2.4 in CHCl 3).
(5rx.,7fJ,JOfJ)-form 3,11-Eudesmadien-8-ol Sq-00928
trans-Occidentalol 3 ,11-Se/inadien-8-ol
Stress compd. from Nicotiana rustica.
Suga, T. eta/, Bull. Chern. Soc. Jpn., 1972, 45, 3502 (struct)
Hortmann, A.G. et a/, J. Org. Chern., 1973, 38, 728 (synth)
Ando, M. eta/, Bull. Chern. Soc. Jpn., 1982, SS, 1588 (synth)
Baldwin, S.W. eta/, Tetrahedron Lett., 1982, 23, 4443 (synth)
Mizuno, Y. eta/, J. Chern. Soc., Perkin Trans. 1, 1982, 2849
(synth)
Uegaki, R. eta/, Phytochemistry, 1985, 24, 2445 (deriv)
C15H240 M 220.354
(ent-8/l)-form [130395-68-5]
Constit. of Bazzania spira/is. Oil. [cxln +40.SO (c, 0.74 in
3,5-Eudesmadien-1-ol Sq-00925 MeOH).
3,5-Se/inadien-1-ol
Kondo, K. et a/, Phytochemistry, 1990, 29, 2197 (isol, pmr, cmr)

3,11(13)-Eudesmadien-12-ol Sq-00929
3,11(13)-Se/inadien-12-ol. rx.-Costol
[65018-15-7]

CtsH 240 M 220.354

1/l-form [95457-17-3]
Constit. of Sideritis varoi. Cryst. Mp 48-50°. [cx]i? -7°
(c, 1 in CHC1 3).
Garcia-Granados, A. eta/, Phytochemistry, 1985, 24, 97 (synth)
Cabrera, E. et a/, Phytochemistry, 1988, 27, 183 (isol)
rh CHpH
~
C15H240 M 220.354
Constit. of Chamaecyparis formosensis and Saussurea
lappa. Oil. Bp0 _5 145°. [cxln + 32.8° (c, 4.3 in CHC1 3).
12-Aldehyde: [4586-01-0]. 3,11(13)-Eudesmadien-12-al.
3,11(13)-Se/inadien-12-al. rx.-Costal. P-Costal (obsol.)
CtsH220 _ M 218.338
Occurs with P-Costal in essential oils.
Ito, S. eta/, Tetrahedron Lett., 1965, 3777.
Mauer, B. et al, Helv. Chim. Acta, 1977, 60, 2177.
Liu, H.-J. et al, Can. J. Chern., 1986, 64, 658 (synth)

323
4,7(11)-Eudesmadien-8-ol - 4(15),11-Eudesmadien-3-ol Sq-00930 -- Sq-00937

4,7(11 )-Eudesmadien-8-ol Sq-00930 Constit. of Vetiveria zizanioides. OiL Bp0 _2 105-107°. [1X]i;
4,7(11)-Selinadien-8-o/ -11.2° (c, 3.3 in CHC1 3).
Karkhanis, D.W. et al, Indian J. Chern., Sect. B, 19U, 16, 260.

4(15),7(11)-Eudesmadien-9-ol Sq-00934
4(15),7(11)-Selinadien-9-o/
OH

g\
C 15H 2•.0 M 220.354
8P-form [97530-58-0]
Constit. of soft coral Nephthea sp. Cryst. Mp 59-60°.
[1X]n -10o.
8-Ketone: [97530-59-1]. 4,7(11)-Eudesmadien-8-one
C 15H:z:z0 M 218.338 C15H 240 M 220.354
Constit. of N. sp. OiL [1X]n + 99°. 9P-form [35688-11-0]
Coli, J.C. et a/, Tetrahedron, 1985, 41, 1085. Produced by Streptomycesfradiae. Cryst. Mp 91-92°.
Gerber, N.N., Phytochemistry, 1972, 11, 385.
4,11-Eudesmadien-3-ol Sq-00931
4,11-Se/inadien-3-o/ 4(15),7-Eudesmadien-12-ol Sq-00935
4(15), 7-Selinadien-12-o/

C15H 2•.0 M 220.354

3«-form [20084-99-5] Cyperol C 15H 240
~,OH
M 220.354
Constit. of Cyperus rotundus. Cryst. (pet. ether). Mp (5P,10«,11R)-form [28102-68-3] Vetiselinenol
111.5-112°. [1Xln +131.4° (c, 6.2 in CHC1 3). Constit. ofvetiver oiL OiL [IX]~ -18.1° (CHC1 3).
41X,51X- Epoxide: [61248-42-8]. 4«,5«-Epoxy-11-eudesmen-3«- Homma, A. et a/, Tetrahedron Lett., 1970, 231 (iso[)
ol Andersen, N.H., Tetrahedron Lett., 1970, 1755 (struct)
Constit. of C. rotundus. Cryst. (pet. ether). Mp 6l.SO. Karkhanis, D.W. et a/, Indian J. Chern., Sect. B, 1978. 16, 260
[1X]n + 37.3° (c, 4.7 in CHC1 3). (iso[)
Hikino, H. et al, Chern. Pharm. Bull., 1967, 15, 1929.
Hikino, H. et al, Phytochemistry, 1976, 15, 1265 (epoxide) 4(15),11-Eudesmadien-1-ol Sq-00936
4(15),11-Se/inadien-1-o/
4,11(13)-Eudesmadien-12-ol Sq-00932
4,11(13)-Selinadien-12-o/. y-Costol
[65018-14-6]

C 15H 240 M 220.354

1P-form [87332-43-2] P-Dictyopterol
C 15H 2,.0 M 220.354 Constit. of Dictyopteris divaricata. Cryst. Mp 71-73°.
Constit. of Saussurea lappa. OiL [1X]i:' + 37° (c, 1 in 1-Ketone: 4(15),11-Eudesmadien-1-one. Dictyopte;rone
CHC1 3). C15H 2:z0 M 218.338
12-A/dehyde: 4(11),13-Eudesmadien-12-a/. 4(11),13- From D. divaricata. OiL [1X]i,' -12S (c, 2.16 in CC14 ).
Selinadien-12-a/. y-Costal. /so-P-costal Kurosawa, E. eta/, Bull. Chern. Soc. Jpn., 1966, 39, 2509 (isol,
C 15H:z:z0 M 218.338 struct)
Constit. of S. lappa and Fitchia speciosa. OiL [1X]n Wijnberg, J.B.P.A. et a/, J. Org. Chern., 1983, 48, 4380 (synth)
+ 71 .SO (c, 1 in CHC1 3).
Mauer, B. eta/, Helv. Chim. Acta, 1977, 60, 2177. 4(15),11-Eudesmadien-3-ol Sq-00937
Bohlmann, F. et al, Phytochemistry, 1980, 19, 1141. 4(15),11-Selinadien-3-o/

4(15),7-Eudesmadien-2-ol Sq-00933

HOlh

~ C 15H 240 M 220.354

3«-form [20085-00-1] Isocyperol
C 15H 2•.0 M 220.354 Constit. of Cyperus rotundus. OiL [1X]n -5.4° (c, 4.5 in
(2f.,5P,10«)-form [67690-36-2] Isovetiselinenol CHC1 3).
Hikino, H. eta/, Chern. Pharm. Bull., 1967, 15, 1929.

324
4(15),11(13)-Eudesmadien-12-ol - 3,11-Eudesmadien-2-one Sq-00938 - Sq-00944

4(15),11(13)-Eudesmadien-12-ol Sq-00938 5,7-Eudesmadien-11-ol Sq-00941

4(15),11(1 3)-Selinadien-12-o/ 5,7-Selinadien-11-o/
[515-20-8]

C 15H 240
~OH
M 220.354
I

(4«.,1 Of/)-form
C 15H 2,.0 M 220.354
Ac: [110299-96-2]. Coralloidin E
(5«.,7P,10f/)-form
C17H 21;02 M 262.391
P-Costol. Sesquibenihiol
Constit. of Alcyonium coral/aides. Cryst. Mp 55°. [1X]i?
Constit. of the essential oil of costus, Chamaecyparis
+ 305° (c, 0.09 in EtOH).
formosensis and of Saussurea lappa. Oil. Bp0 . 5 145°
(bath). [1X]n +32.8° (c, 4.3 in CHC1 3). D'Ambrosio, M., Helv. Chirn. Acta, 1987, 70, 612.
12-A/dehyde: [3650-40-6]. 4(15),11(13)-Eudesmadien-12-a/.
4(1 5),11(1 3)-Selinadien-12-a/. P-Costal 11(13)-Eudesmadien-12-ol Sq-00942
C 15H 220 M 218.338 11(13)-Selinadien-12-o/
Constit. of Thujopsis dolabrata and Chamaecyparis

~CH,OH
formosensis. Oil. Bp 15 164-166°. [1X]n +24°. Originally
called IX-Costal.
12-A/dehyde, semicarbazone: Cryst. (EtOH). Mp 223°.
Bawdekar, A.S. eta/, Tetrahedron, 1965, 21, 1521; 1967, 23, 1993
(isol, struct) C 15H 260 M 222.370
Marshall, J.A. eta/, J. Org. Chern., 1966, 31, 2933 (synth) (4P,5«)-form
Klein, E. eta/, CA, 1969, 70, 4301 (synth) Agaroft
Maurer, B. eta/, Helv. Chirn. Acta, 1977, 60, 2177 (iso/, prnr, ir) Constit. of fungus infected Aquilaria agallocha. Oil.
Garratt, P.J. eta/, J. Org. Chern., 1986, 51, 5450 (synth) Bp0 _9 117°. [IX]~ -21.8° (c, 7.25 in CHC1 3).
Jain, T.C. eta/, Tetrahedron Lett., 1959, No. 9, 13.
5,7(11)-Eudesmadien-8-ol Sq-00939
5,7(11)-Selinadien-8-o/
3,7(11 )-Eudesmadien-2-one Sq-00943
3,7(11)-Se/inadien-2-one

owYI ~
I
~

C 15H 240 M 220.354 H

8P-form C 15Hn0 M 218.338
Oil. [1X]i? + 262° (c, 0.07 in cyclohexane).
(5«.,10«.)-form [86917-82-0]
Ac: [105708-62-1]. Coralloidin A Constit. of grapefruit, Citrus paradisi. Cryst. (pentane).
C 17H 21;02 M 262.391 Mp 92-92.SO. [1X]i? +83° (c, 0.82 in CHC13).
Constit. of Alcyonium coral/aides. Oil. [1X]i? + 225° (c,
Demole, E. et a/, He/v. Chirn. Acta, 1983, 66, 1381.
0.08 in cyclohexane).
Guerriero, A. et a/, J. Nat. Prod. (Lloydia), 1986, 49, 608.
3,11-Eudesmadien-2-one Sq-00944
3,11-Selinadien-2-one
5,7(11)-Eudesmadien-14-ol Sq-00940
5,7(11)-Selinadien-14-o/

0~
~
(SIX, 7J3, lOiX)-form

C15H 2:z0 M 218.338

I
(5«,7P,10«.)-form [86941-63-1]
C 15H 240 M 220.354 Constit. of grapefruit, Citrus paradisi. Oil. [1X]i? + 128°
(4«.,10/1)-form [110299-97-3] (c, 0.6 in CHC1 3).
Oil. [1X]i? -172.9° (c, 0.14 in EtOH). (5p,7p,10«.)-form [86917-81-9]
Ac: [110299-91-7]. Coralloidin C Constit. of C. paradisi. Oil. [1X]i? -70° (c, 0.64 in
C 17H 21;02 M 262.391 CHC1 3).
Constit. of Alcyonium coral/aides. Oil. [1X]n -168.7° (c, (5p,7p,]Of/)-form [86917-80-8]
0.34 in CHC1 3). Constit. of C. paradisi. Cryst. Mp 38°. [1X]i? -61° (c,
D'Ambrosio, M. eta/, Helv. Chirn. Acta, 1987, 70, 612. 0.87 in CHC1 3).
[86917-79-5]
Demole, E. eta/, Helv. Chirn. Acta, 1983, 66, 1381.

325
4,11-Eudesmadien-3-one- 5,11-Eudesmanediol Sq-00945 -· Sq-00950

4,11-Eudesmadien-3-one Sq-00945 Constit. of bark of Magnolia obovata. [ocln -74.8° (c, 9.2
4,11-Selinadien-3-one. rz-Cyperone in CHC1 3).
[473-08-5] Fukuyama, Y. et al, Chern. Lett., 1990, 295 (isol, struct)

4,6-Eudesmanediol Sq-00948
4,6-Selinanediol
(+)-form

C 15H 22 0
(+)-form
M 218.338

Constit. of Cyperus rotundus, C. scariosus and Juniperus

horizontalis. Bp 177°. [oc] 0 + 138°.
H~y
CtsH 280 2 M 240.385
(4ct.,6ct.,7ct.)-form

Semicarbazone: Cryst. Mp 216°. (4rz,6rz,7rz)-form

13-Hydroxy: [56423-80-4]. 13-Hydroxy-4,11-eudesmadien-3- Constit. of Frullania tamarisci. Cryst. Mp 107-108°. [ocln
one. 11-Hydroxy-rz-cyperone + 14.7° (c, 2.18 in CHC13).
C 15H 22 0 2 M 234.338 (4rz,6rz,7f/)-form [35932-55-9]
lsol. from Artemisia afra. Oil. Constit. of Picea ajanensis. Cryst. Mp 59-60° [oc]~
1,2-Didehydro: [17081-85-5]. 1,4,11-Eudesmatrien-3-one. -34.8° (c, 0.9 in dioxan).
1,4,11-Selinatrien-3-one. 1 ,2-Dehydro-rz-cyperone (4rz,6P,7fl)-form [35932-60-6] Verbesindiol
C 15H 20 0 M 216.322 Cryst. (CHC1 3 jhexane). Mp 96-97°. [oc] 0 -35° (c, 0.25 in
Constit. of Lycium chinense. Oil. [oc] 0 -172.4° (c, 0.003 CHC1 3).
in MeOH).
6-(4-Hydroxycinnamoyl):
(-)-form
C24 H 340 4 M 386.530
ent-rz-Cyperone
Constit. of Verbesina myriocephala. Oil. [oc] 0 ·-23° (c,
Constit. of Marchantia polymorpha. [oc] 0 -138° (CHC1 3). 0.5 in CHC1 3).
Adamson, P.S. et al, J. Chern. Soc., 1937, 1576 (struct)
Babkin, V.A. et al, Khim. Prir. Soedin., 1971, 7, 736; Chern. Nat.
Naves, Y.-R., Bull. Soc. Chim. Fr., 1954, 332 (isol) Compd. (Engl. Trans/.), 714 (Ajanol)
Howe, R. et al, J. Chern. Soc., 1955, 2423 (synth)
Herz, W. et al, Phytochemistry, 1981, 20, 247 (Verbesindiol)
Caine, D. et al, J. Org. Chern., 1974, 39, 2154 (synth)
Herz, W. et al, J. Org. Chern., 1982, 47, 1785 (cryst struct)
Sannai, A. et al, Phytochemistry, 1982, 21, 2986 (Dehydro-rx-
Toyota, M. et al, Phytochemistry, 1990, 29, 3664 (isol, pmr, cmr)
cyperone)
Jakupovic, J. et al, Phytochemistry, 1988, 27, 1129 (!2-Hydroxy-rx.-
cyperone) 4,11-Eudesmanediol Sq-00949
Asakawa, Y. et al, Phytochemistry, 1990, 29, 1577 (ent-rx-Cyperone) 4,11-Selinanedio/

4(15),7(11 )-Eudesmadien-8-one Sq-00946

4(1 5), 7(1 1)-Selinadien-8-one
[54 707-4 7-0]

CtsH28 0 2 M 240.385
4rz-form [4666-84-6] Cryptomeridiol. Proximadiol
Constit. of Cryptomeria japonica and Cympobogon
proximus. Also Widdringtonia dracomontana, Fokienia
CtsHzzO M 218.338 hodgkinsii, Callitris columellaris and others.
Constit. of Atractylodes japonica. Antiinflammatory. Oil. Antispasmodic. Cryst. Mp 138° (134.5-135.SO). [ocln
Endo, K. et al, Bull. Chern. Soc. Jpn., 1979, 52, 2439 (struct)
-33.3° (CHC1 3).
Endo, K. et al, Chern. Pharm. Bull., 1979, 27, 2954 (isol) Cruz, A. et al, Phytochemistry, 1973, 12, 2549 (isol)
Banerjee, A.K. et al, Indian J. Chern., Sect. B, 1983, 22, 1259 Irwin, M.A. et al, Phytochemistry, 1973, 12, 849 (isol)
(synth) Reno1d, W. et al, Helv. Chim. Acta, 1979, 62, 985 (synth)
Banerjee, A.K. et al, J. Chern. Res. (S), 1984, 284 (synth) Evans, F.E. et al, Phytochemistry, 1982, 21, 937 (isol)
Kawamata, T. et al, Bull. Chern. Soc. Jpn., 1988, 61, 3770 (synth)
Eudesmagnolol Sq-00947
[126654-54-4] 5,11-Eudesmanediol Sq-00950
5,11-Selinanedio/

=~OH
I
I

~~~ (4ct.,5P,7P,10ct.)-:form

~H
C 15H 280 2 M 240.385
(4rz,5P,7P,JOrz)-form
Constit. of Alpinia japonica. Needles (hexane). Mp 130-
1320. [oc] 0 -21.8° (c, 0.12 in CHC1 3).
~ (4p,sp,7p,JOrz)-form [121817-19-4]
M 488.709

326
1,4,6,15-Eudesmanetetrol- 3-Eudesmene-1,6-diol Sq-00951 - Sq-00957

Constit. of Cymbopogon distans. Cryst. (Me2CO). Mp 4,6,11-Eudesmanetriol Sq-00954

120-l21°. [o:]~ -9.0° (c, 0.8 in CHC1 3). 4,6,11-Se/inanetrio/

H%0H
Itokawa, H. et al, Chern. Pharm. Bull., 1987, 35, 1460 (isol)
Mathela, C.S. et al, Phytochemistry, 1989, 28, 936 (isol, cryst
struct)

1,4,6,15-Eudesmanetetrol Sq-00951
1,4,6,15-Se/inanetetro/
C15H 280 3 M 256.384
OH

(h
(4rz,6rz)-form [41929-25-3] Pygmol
Constit. of Chenopodium botrys and Artemisia pymaea.
Cryst. Mp 153° (149-150.SO). [a]n -13.SO.
4-Ac: [74799-31-8].
HOH2C"~ C 17H 300 4 M 298.422
Constit. of C. botrys. Cryst. Mp 84°. [a]n +6.3° (c, 0.7
C1sH:11.04 M 272.384 in MeOH).
(lrz,4P,5/l,6P,7P,JOrz)-form [64305-95-9] Rupestrinol Irwin, M.A. et al, Phytochemistry, 1973, 12, 849.
Constit. of Verbesina rupestris. Cryst. (EtOAC). Mp de Pascual Teresa, J. et al, Tetrahedron, 1980, 36, 371.
179-180°. (tx)n + 11°.
9o:-Hydroxy: [35964-51-3]. 1a.,4p,6p,9o:,15-Eudesmanepentol. 4,8,11-Eudesmanetriol Sq-00955
Rupestrol
C1sH280 5 M 288.383 ~,OH
Cryst. Mp 206-207°. [o:]n + 11°.
9o:-Hydroxy, 15-cinnamoy/(E-): [35938-59-1]. 15-
. Cinnamoylrupestrol ~H
C24H 340 6 M 418.529
Constit. of V. rupestris. Cryst. Mp 222-224°. ClsH2803 M 256.384
Box, V.G.S. et al, Phytochemistry, 1977, 16, 987 (Rupestrinol)
(4rz,8rz )-form
Box, V.G.S. et al, Tetrahedron Lett., 1977, 4371 (Rupestrol) 8-Ac: 8a-Acetoxy-4a,ll-eudesmanediol. 8a-
Acetoxycryptomeridiol
C17H 300 4 M 298.422
3,4,6,11-Eudesmanetetrol Sq-00952
Constit. of Chenopodium graveolens. Cryst. Mp 70°. [a]n
3,4,6,11-Selinanetetro/
+0.1 o (c, 2 in CHCI3).
Mata, R. et al, Phytochemistry, 1987, 26, 191.

HO'~~~
~H
4(15),7(11 ),8-Eudesmatriene
4( 15), 7( 11),8-Se/inatriene
Sq-00956

CuH280 4 M 272.384 [74634-83-6)

(3rz,4rz,6«)-form [74841-83-1] Chenopotetrol
Constit. of Chenopodium botrys. Cryst. (Et 20). Mp 185°.
(o:Jn +5.7° (c, 0.7 in MeOH).
(3P,4rz,6rz)-form [74799-34-1] 3-epi-Chenopotetrol. 3-
Epichenopotetro/
C 15Hn M 202.339
Constit. of C. botrys. Cryst. (Etp). Mp 197°. [o:]n + 19°
Constit. of Aster umbel/atus. Oil. [a]i,4 -290° (c, 0.1 in
(c, 0.9 in MeOH).
CHCI 3).
de Pascual Teresa, J. et al, Tetrahedron, 1980, 36, 371.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 435.

2,4,11-Eudesmanetriol Sq-00953 3-Eudesmene-1,6-diol Sq-00957

2,4,11-Se/inanetrio/
3-Se/inene-1 ,6-dio/
HO,'('l] HO

C 15H280 3
H~OH
M 256.384
~
Y!:Y (la,5a,6P,l0Pl£o'm

(2rz,4rz)-form [52801-07-7] Pterocarptriol

Constit. of the heartwood of Pterocarpus santalinus. C15H 260 2 M 238.369
Cryst. (CHC1 3jMeOH). Mp 168°. [a]~ -38° (c, 1 in (1 P,5rz,6P,l 0/1)-form
MeOH). . 6-Cinnamoy/: [77355-61-4].
2-Ketone: [52801-08-8]. 4a,11-Dihydroxy-2-eudesmanone. C24H 320 3 M 368.515
Pterocarparolone Constit. of Solidago nemoralis.
Constit. of P. santalinus. Viscous liq. [a]~ + 11° (c, 0.8 (lrz,5P,6P,10rz)-form
in CHC1 3). 1-Cinnamoyl:
Kumar, N. et al, Phytochemistry, 1974, 13, 633. C24H 3P 3 M 368.515

327
3-Eudesmene-1,9-diol- 4(15)-Eudesmene-2,11-diol Sq-00958 - Sq-00963

Constit. of Ambrosia artemisioides. Oil. 4(15)-Eudesmene-1,6-diol Sq-00961

6-Cinnamoy/: 4,(1 5)-Se/inene-1 ,6-dio/
C24H 320 3 M 368.515

%
Constit. of A. artemisioides. Oil. HO
6-(4-M ethoxybenzoyl):
C 23 H 32 0 4 M 372.503
Constit. of A. artemisioides. Oil. (1 p,5rx,6rx, 1OP)-form
6-0-P-n-G/ucopyranoside:
C 21 H 360 7 M 400.511
Constit. of A. artemisioides. Gum. CtsH 260 2 M 238.369
[77355-61-4] (JP,5«.,6«.,10p)-form
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2655 (isol) Voleneol. Spathulenolt
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3551 (deriv) Constit. of Senecio microglossus, Helianthus
microcephalus, Lepidotrichilia volensii and Ageratina
glechonophyl/a. Gum. [1X]i;' + 7° (c, 0.1 in CHCI 3).
3-Eudesmene-1,9-diol Sq-00958
3-Se/inene-1 ,9-dio/ Di-Ac: Cryst. (EtzO). Mp 99.5-100.SO.
6-Me ether: [64784-78-7]. 61X-Methoxy-4(!5)-eudesmen-1P-
ol. 1P-Hydroxy-61X-methoxy-4( 15)-eudesmene
C 16H 280 2 M 252.396
Constit. of Tori/is japonica. Amorph. [1X]n + 7.8°.
(1«,5P,6P,JO«.)-form [64305-97-1] Chaenocephalol
Cryst. (Me2CO aq.). Mp 115-116°.
6-Angeloyl: 6P-Angeloyloxy-11X-hydroxy- 5, 10-bisepi-4(15)-
C 15H 260 2 M 238.369 eudesmene
(1 p,9p)-form C 20 H 320 3 M 320.471
9-Cinnamoy/: Constit. of Verbesina rupestris. Oil.
C 24H 320 3 M 368.515 6-Cinnamoyl:
Constit. of Solidago nemoralis. C 24H 320 3 M 368.515
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 1656. Constit. of V. rupestris.
(1«,5P,6«.,10«.)-form [58556-80-2] Platambin
3-Eudesmene-6,7-diol Sq-00959 Constit. of the defence secretion of Platambus
3-Se/inene-6,7-dio/ maculatus. Cryst. (CHCI 3). Mp 62-63°.

WY
Schildknecht, H. eta/, Justus Liebigs Ann. Chern., 1975, 1850
(Platambin)
Box, V.G.S. eta/, Phytochemistry, 1977, 16, 987 (isol)
Hoffmann, J.J. et a/, J. Org. Chern., 1978, 43, 1254 (isol, struct)
ltokawa, H. eta/, Chern. Lett., 1983, 1253 (isol)
OH Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1675 (isol)
Gutierrez, A.B. et a/, Phytochemistry, 1988, 27, 2225 (isol)
C 15H 260 2 M 238.369 Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3551 (deriv)
(6P,7«)-form Gonzalez, A. G. eta/, Phytochemistry, 1989, 28, 2520 (isol, pmr)
Constit. of Lepidozia reptans. Cryst. (EtzOjpentane).
Mp 94-95°. [1X]14 +34.6° (c, 2.2 in CHC1 3). 4(15)-Eudesmene-1,11-diol :Sq-00962
Connolly, J.D. et a/, Phytochemistry, 1986, 25, 1745. 4(15)-Se/inene-1,11-diol

~H
3-Eudesmene-6,11-diol Sq-00960

(II
~
OH
C 15H 260 2 M 238.369
C 15H 260 2 M 238.369 1P-form [83217-89-4]
Constit. of Pterocarpus marsupium. Cryst. Mp 156-157°.
6«.-form [67996-31-0] «.-Chenopodiol
[IX]~ + 56.4° (c, 1.5 in CHCI 3).
Constit. of Chenopodium botrys. Cryst. (EtzO/hexane).
Mp 168°. [1X]n + 115° (c, 1.2 in EtOH). Cordano, G. eta/, J. Indian Chern. Soc., 1978, 55, 1148 (isol)
Adinarayana, D. eta/, Phytochemistry, 1982, 21, 1083.
De Pascual Teresa, J. eta/, An. Quim., 1978, 74, 91. Anglea, T.A. eta/, Tetrahedron, 1987, 43, 5537 (synth)

4(15)-Eudesmene-2, 11-diol Sq-00963

4(1 5)-Selinene-2,11-diol

HO,Ttl

~OH
M 238.369

328
4(15)-Eudesmene-3,11-diol - 7-Eudesmene-11,12-diol Sq-00964 - Sq-00970

2rz-form [21677-80-5] Pterocarpol 4(15)-Eudesmene-8, 11-diol Sq-00967

Constit. of the heartwood of Pterocarpus macrocarpus
and other P. spp. Cryst. (C 6H 6). Mp 104-105°. [1X]n ftT~OH
+ 39° (c, 1.05 in CHC1 3).

~OH
Bah!, C.P. et al, Tetrahedron, 1968, 24, 6231 (isol, struct)
Kukla, A.S. et al, Indian J. Chern., Sect. B, 1976, 14, 905 (abs
config)
C 15H 260 1 M 238.369
4(15)-Eudesmene-3,11-diol Sq-00964 Brz-form [36061-ll-7]
4(15)-Selinene-3,11-diol 5-Desoxylongilobol. Arctiol
Constit. of Laggera alata and Arctium lappa. Cryst. Mp

HO'~OH
160° (157.5-159°). [oc]~4 + 73° (c, 0.2 in CHCl 3).
Naya, K. et al, Chern. Lett., 1972, 235.
Zdero, C. eta/, Phytochemistry, 1989, 28, 3097 (isol, pmr)

4(15)-Eudesmene-11,12-diol Sq-00968
C 15H 21;01 M 238.369
4(15)-Selinene-11 ,12-diol
3rz-form
Constit. of Chenopodium botrys. Cryst. (C 6H 6). Mp 107-
1080. [1X]n -4.SO (c, 0.6 in CHCl3).
de Pascual Teresa, J. et al, Tetrahedron, 1980, 36, 371.

4(15)-Eudesmene-5,11-diol Sq-00965 CtsH260 1 M 238.369

5-Hydroxy-p-eudesmo/ [oc]n + 72.9° (CHCl 3).
I
(JJR)-form [70142-90-4] Kudtdio/
Constit. of Jasonia glutinosa. Cryst. (CH 2Cl2 jhexane).

~OH
Mp 90°.
4oc,15oc-Epoxide: 4oc, 15-Epoxy-11 R, 12-eudesmanediol. rz-
(5cx, lOcx )-form Epoxykudtdiol
CISH2603 M 254.369
C 1sH 21;01 M 238.369 Constit. of J. glutinosa. Oil. [1X]n -6° (c, 0.9 CHCl3).
(5rz,10rz)-form 111;-form [73035-82-2]
lsol. from Jasonia montana. Oil. Constit. of Flourensia heterolepis. Oil. [oc]i;l + 50.4° (c,
5-Hydroperoxide: 5-Hydroperoxy-4(15)-eudesmen-11-o/ 1.6 in CHCl 3).
Constit. of Albinia japonica. Needles (hexane). Mp 146- Teresa, J. de P. et al, Tetrahedron Lett., 1978, 4141 (Kudtdiol)
1470. [oc]n -48.6° (c, 0.21 in CHCl 3). Bohlmann, F. et al, Phytochemistry, 1979, 18, 1189 (isol)
(5P,10rz)-form Teresa, J. de P. et al, Phytochemistry, 1980, 19, 2155 (epoxide)
!sol. from J. montana. Oil.
5-Hydroperoxide: Constit. of A. japonica. Needles 7-Eudesmene-1,4-diol Sq-00969
(hexane). Mp 131-133°. [1X]n -52.0° (c, 0.2 in CHC13). 7-Selinene-1 ,4-diol
Itokawa, H. et al, Chern. Pharm. Bull., 1987, 35, 1460 HO
(hydroperoxides)

~
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 3658 (isol, pmr)

4(15)-Eudesmene-6, 11-diol Sq-00966

4(1 5)-Selinene-6,11-diol
C 15H 260 1 M 238.369

~H
(lp,4f/)-form [13902-62-0] Op/odiol
Constit. of Oplopanax japonicus. Cryst. (Et20jpet.
ether). Mp 106-107°. [IX]~ -51.9° (c, 0.5 in dioxan).
Minato, H. eta/, J. Chern. Soc. C, 1967, 423 (struct)
Takahashi, K. eta/, Chern. Pharm. Bull., 1976, 24, 2000 (cmr)
CtsH260z M 238.369
6a.-form [68127-21-9] p-Chenopodio/
Constit. of Chenopodium botrys. Cryst. Mp 168°. [1X]n
7-Eudesmene-11,12-diol Sq-00970
7-Selinene-11 ,12-diol
+ 115°.
[83991-66-6]
Ac: [74841-79-5]. 6oc-Acetoxy-4(15)-selinen-11-ol
C 17H 280 3 M 280.406
Constit. of C. botrys. Cryst. (hexane). Mp 68°. [1X]n
-38° (c, l.l in MeOH). ~ CHPH
de Pascual Teresa, J. et al, Tetrahedron, 1980, 36, 371.
~OH
C15H 260 1 M 238.369
Constit. of Epaltes brasiliensis. Gum. [1X]n +8° (c, 2 in
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1795.

329
11-Eudesmene-1,5-diol - 4(15)-Eudesmene-5,11,12-triol Sq-00971 -· Sq-00978

11-Eudesmene-1,5-diol Sq-00971 Constit. of Iva annua. Oil. [1X]i;' -28.SO (c, 3.6 in
11-Se/inene-1 ,5-diol CHC1 3).
1,2-Di-Ac, 6-benzoyl: [73809-94-6].
HOI C26H 340 6 M 442.551

(Dy
Constit. of /. annua. Oil.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 2034.

4(15)-Eudesmene-1,5,6-triol Sq-00975
C,sHu;02 M 238.369 4(1 5)-Selinene-1 ,5,6-triol
(1«,5«)-form [113540-91-3] «-Corymbolol
HO
Constit. of Cyperus articulatus. Oil. [1X]i: + 43° (c, 2.9 in

~
CHC1 3).
(lft,5«)-form
P-Corymbolol
Oil. [1X]i: + 25° (c, 0.35 in CHC1 3).
1-Ketone: [97094-19-4]. 51X-Hydroxy-11-eudesmen-1-one.
Corymbolone C,sH2603 M 254.369
C 1sH 240 2 M 236.353 (lft,5«,6fJ)-form
Constit. of C. corymbosus. Cryst. (hexane). Mp 136.5- 6-Ac: 6ft-Acetoxy-4(15)-eudesmene-IP,51X-diol
1370. [1X]i: + 57.9° (c, 0.84 in CHC1 3). C 17H 280 4 M 296.406
Garbarino, J.A. eta/, J. Nat. Prod. (Lloydia), 1985, 48, 323 Constit. of Sideritis varoi.
( Corymbolone) Cabrera, E. eta/, Phytochemistry, 1988, 27, 183.
Nyasse, B. eta/, Phytochemistry, 1988, 27, 179 (Corymbolols)

4(15)-Eudesmene-3,6,11-triol Sq-00976
11(13)-Eudesmene-4,12-diol Sq-00972 4(15)-Selinene-3,6,11-triol
11(13)-Selinene-4,12-diol

~OH
(3a.,6a.)-form
HO~
OH
OH
C,sHu;02 M 238.369 C,sH260 3 M 254.369
4«-form [72715-02-7] (3«,6«)-form [70902-38-4] Chenopotriol
11,13-Selinene-4,12-diol. 1/icol Constit. of Chenopodium botrys. Cryst. Mp 136-137°.
Constit. of Flourensia oolepis. Cryst. Mp 134-135°. [1X] 0 [1X] 0 -30° (c, 0.75 in MeOH).
-43.3° (c, 1.9 in CHC1 3). (3ft,6«)-form [74799-33-0] 3-epi-Chenopotriol
Guerreiro, E. eta/, Phytochemistry, 1979, 18, 1235. Constit. of C. botrys. Cryst. Mp 163°. [1X] 0 - 12° (c, 0.5
in MeOH).
4- Eudesmene-3,6, 11-triol Sq-00973 de Pascual Teresa, J. et a/, Tetrahedron, 1980, 36, 371.
4-Selinene-3,6,11-triol
4(15)-Eudesmene-5,8, 11-triol Sq-00977

iJi
4(1 5)- Selinene-5,8, 11-trial

HO'
~OH
OH
(']'~'(OH
C 15H 21;03 M 254.369 ~H
(3«,6«)-form [74799-43-2]/sochenopotriol C 15H 260 3 M 254.369
Constit. of Chenopodium botrys. Cryst. (Etp). Mp 110°. (5«,8«)-form [50656-60-5] Longilobol
[1X] 0 +35° (c, 1.3 in MeOH). Constit. of Artemisia longilobia. Cryst. Mp 176-177°.
de Pascual Teresa, J. eta/, Tetrahedron, 1980, 36, 371. [IX]~ +95° (c, 0.8 in MeOH).
Shafizadeth, P. eta/, Tetrahedron Lett., 1973, 2171.
4(15)-Eudesmene-1,2,6-triol Sq-00974
HO 4(15)-Eudesmene-5, 11,12-triol Sq-00978
4(15)-Selinene-5,11 ,12-triol
HO~,
~OH
C 15H 260 3 M 254.369 C, 5H 260 3 M 254.369
(1«,2P,5ft,6p,7p,JO«)-form (5«,11R)-form [77521-40-5] Kudtriol
2-Ac, 6-benzoyl: [73809-95-7]. lvanuol Constit. of Jasonia glutinosa. Oil. [1X] 0 + 76.SO ~c. 1 in
C 24H 320 5 M 400.514 CHC1 3).

330
7-Eudesmene-1,2,4-triol- 4(15)-Eudesmen-5-ol Sq-00979 - Sq-00984

(5p,IIR)-form C1sH 240 M 220.354

5-Epikudtriol Constit. of the rhizomes of Acorus calamus. Oil.
Constit. of J. glutinosa. Oil. [1X) 0 -10.4° (c, 0.8 in (5ft,6rx.)-form
CHC1 3). rx.- Verbesinol
de Teresa, J.P. et al, Phytochemistry, 1980, 19, 2155 (isol, struct) Liq. Bp0_2 82-83°. [1X)i,l -15.3°.
Harapanhalli, R.S. et a/, J. Chern. Soc., Perkin Trans. 1, 1988, 4-Hydroxycinnamoyl:
3149 (synth) C24H 3z03 M 368.515
Constit. of roots of Verbesina virginica. Mp 116-122°.
7-Eudesmene-1,2,4-triol Sq-00979 [IX)~ +49°. Data refers to mixt. with the deriv. of P-
7-Selinene-1 ,2,4-triol Verbesinol.
Gardner, P.D. eta/, J. Am. Chern. Soc., 1961, 83, 1511.
Niwa, M. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 2930.
HO,Q=yHO Toyota, M. eta/, Phytochemistry, 1988, 27, 2155.
3 I
4
3-Eudesmen-11-ol Sq-00982
HO\ 3-Selinen-11-ol
C 15H 21;03 M 254.369 [473-16-5)

rh
(1 p,2rx.,4f/)-form
Cryst. Mp 120-121°.
4-Cinnamoyl: 4P-Cinnamoyloxy-1P,21X-dihydroxy-7-
eudesmene
C24H 320 4 M 384.514 ~OH
Constit. of Verbesina virgata. Cryst. (Me2COfhexane). C15H 260 M 222.370
Mp 170-171°. [1X)~ -21.1° (CHC1 3). (5rx.,7p,l0f/)-form
Martinez, M. eta/, Phytochemistry, 1982, 22, 979 (isol, cryst rx.-Eutksmol. Selinelol. Atractylol
struct) Occurs with 4(15)-Eudesmen-11-ol, Sq-00986 in various
eucalyptus oils. Cryst. by subl. Mp 75°. Bp 10 156°. [1X) 0
7-Eudesmene-1,3,4-triol Sq-00980 + 28.6° (c, 1.86 in CHC1 3).
7-Selinene-1 ,3,4-triol (5rx.,7rx.,10f/)-form
7-Epi-rx.-eutksmol
HO CisH 260 M 222.370
Constit. of Amyris balsamifera oil. Oil.

C 15H 260 3
HO'AHO '
M 254.369
McQuillan, F.J. eta/, J. Chern. Soc., 1956, 2973 (isol, struct)
Humber, D.C. eta/, Tetrahedron Lett., 1966, 4985 (synth)
Kutney, J.P. eta/, Can. J. Chern., 1984, 62, 1407 (synth)
Schwartz, M.A. eta/, J. Org. Chern., 1985, 50, 1359 (synth)
Van Beek, T.A. et a/, Phytochemistry, 1989, 28, 1909 (isol)

(lft,3rx.,4f/)-form
4-Cinnamoyl: 4P-Cinnamoyloxy-1p,31X-dihydroxy-7-
4-Eudesmen-11-ol Sq-00983
4-Selinen-11-o/. y-Eutksmol
eudesmene
C24H 32 0 4 M 384.514 [1209-71-8)
Constit. of Verbesina virgata. Cryst. (Me 2C0fhexane).

C(byOH
Mp 133-135°. [1X)~ -24.6° (CHC1 3).
(lp,3p,4f/)-form
3ft-Hydroxyoplodiol
Constit. of Pallenis spinosa. Gum.
3-Ac: 3P-Acetoxyoplodiol C15H 260 M 222.370
C17H 280 4 M 296.406 Constit. of oils of Neocal/itropsis araucaroides (Araucaria
Constit. of P. spinosa. Gum. oil), Thuja occidentalis, Callitris columellaris and others.
Martinez, M. eta/, Phytochemistry, 1982, 22, 979 (isol, struct) Oil. Bp0 _1 83-86°. [1X)i,S + 66.7° (neat). n~ 1.5087.
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3355 (isol, pmr) Bates, R.B. eta/, Chern. Ind. (London), 1962, 1759 (isol, struct)
Marshall, J.A. et al, Tetrahedron Lett., 1966, 4989 (synth)

%
3-Eudesmen-6-ol Sq-00981
3-Selinen-6-ol 4(15)-Eudesmen-5-ol Sq-00984
4( 15)-Selenen-5-ol
(5a,6~)-fo'm

OH
C 15H 260 M 222.370 CisH260 M 222.370
(5rx.,6f/)-form [74144-55-1) 5rx.-form [70387-51-8]
Constit. of Bazzania fauriana. Oil. [1X] 0 -35° (c, 1.1 in Constit. of Laurencia nipponica. Oil. [1X] 0 +97.2° (c, 3 in
CHC1 3). CHC1 3).
6-Ketone: 3-Eudesmen-6-one. 3-Selinen-6-one. lsoacolamone Suzuki, M. et al, Phytochemistry, 1985, 24, 2011.

331
4(15)-Eudesmen-6-ol- 11-Eudesmen-4-ol Sq-00985 -- Sq-00991

4(15)-Eudesmen-6-ol Sq-00985 5-Eudesmen-11-ol Sq-00987

4(15)-Se/inadien-6-ol 5-Se/inen-11 -ol

(5cx,6cx, 7p, IOP)-form

C,sH260
~OH
M 222.370
C 15H 260 M 222.370
(4«,7fl,10«)-form-form [63891-61-2] Rosifoliol
(5«,6«,7P,10/1)-form [472-07-1] Junenol
Constit. of Rubus rosifolius. Cryst. Mp 84°. [ocJn + 105°.
Constit. of the juniper berry (Juniperus communis) and
black dammar resin. Cryst. (pet. ether or by subl.). Mp Southwell, I.A., Tetrahedron Lett., 1977, 873.
Beagley, B. eta/, Acta Crystal/ogr., Sect. B, 1982, 38, 1391 (cryst
62.5-63°. Bp 1 121-122°. [ocJn +52° (c, 3.35 in CHC1 3).
struct)
6-Ketone: [39012-14-1]. 4(15)-Eudesmen-6-one. 4(15)-
Se/inen-6-one. Acolamone
C 15H 140 M 220.354 6-Eudesmen-4-ol Sq-00988
Constit. of Acorus calamus. Liq. 6-Se/inen-4-ol
(5fl,6P,7«,10«)-form [30951-17-8] ent-Junenol. Laevojunenol

H~
Constit. of Indian vetiver oil. Cryst. (EtOH or pet.
ether). Mp 65°. [ocln -57° (c, 1.18 in EtOH).
(5«,6«,7P,1 0« )-form [62358-38-7] 10-epi-Junenol. 10- Epijunenol
Constit. of galbanum resin. Cryst. Mp 31°. [ocln + 85.7°
(c, 6 in EtOH). C 15H 260 M 222.370
(5fl,6«,7fl,10/1)-form [75109-68-1] P-Verbesinol (4«,5«,10/1)-form [118173-08-3]
4-Hydroxycinnamoyl: Constit. of Ageratina sa/til/ensis.
C14H 320 3 M 368.515 (4p,5p,10«)-form
Constit. of Verbesina virginica. Constit. of Abies alba. Cryst. (MeOH). Mp 89-90°. [ocJi?
Gardner, P.D. eta/, J. Am. Chern. Soc., 1961, 83, 1511 (ft- + 15.SO (c, 4.3 in CHC1 3).
Verbesinol) Khan, V.A. eta/, Khim. Prir. Soedin., 1988, 24, 712; Chern. Nat.
Shaligram, A.H. et a/, Tetrahedron, 1962, 18, 969 (isol) Compd. (Engl. Trans/.), 606 (iso/, pmr, cmr)
Theobald, D.W., Tetrahedron, 1964, 20, 2593 (struct) Fang, N. eta/, Phytochemistry, 1988, 27, 3187 (isol)
Hinge, V.K. eta/, Tetrahedron, 1965, 21, 3197 (isol)
Schwartz, M.A. eta/, J. Am. Chern. Soc., 1972, 94, 4361 (synth)
Niwa, M. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 2930 (Aco/amone) 6-Eudesmen-11-ol Sq-00989
Thomas, A.F. eta/, Tetrahedron, 1976, 32, 2261 (iso/, struct) 6-Se/inen-11-ol
Wender, P.A. eta/, J. Am. Chern. Soc., 1978, 100, 4321 (synth)
Banerjee, A.K. eta/, J. Chern. Soc., Perkin Trans. I, 1982, 2547

~OH
(synth)

4(15)-Eudesmen-11-ol Sq-00986
4(15)-Se/inen-11-ol. P-Eudesmol
[473-15-4] C 15H 260 M 222.370
Constit. of Laurencia nipponica. Cryst. (MeOH). Mp 49-
500. [ocJi? +5.1° (c, 0.83 in CHC1 3).

~OH
Fukuzawa, A. eta/, Phytochemistry, 1990, 29, 2337 (iso/, pmr, cmr)

7(11 )-Eudesmen-4-ol Sq-00990

7(11)-Se/inen-4-ol
C 15H 260 M 222.370
Constit. of eucalyptus oils. A widely distrib. constit. of
essential oils, freq. not differentiated from oc-Eudesmol.
Cryst. by subl. Mp 80-82°. Obsolete synonyms for
Eudesmol mixture are Uncineol, Machilol, Selinenol,
Cryptomeridol and Sagittol.
oc-L-Arabopyranoside: [21615-76-9].
C 15H 260 M 222.370
C20H 340 5 M 354.486 4«-form
Constit. of Machaeranthera ·tanacetifo/ia. Cryst. Constit. of Acritopappus prunifolius. Oil.
(EtpjMe 2CO). Mp 129-130°. [oc]~4 .+37.1° (c, 0.25 in Bohlma.nn, F. eta/, Phytochemistry, 1982, 21, 147.
EtOH).
Yoshioka, H. eta/, J. Org. Chern., 1969, 34, 3697 (deriv) 11-Eudesmen-4-ol Sq-00991

Hwf
Karrer, W. eta/, Konstitution und Vorkommen der Organischen 11-Se/inen-4-ol
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 1891 (occur, bib[)
Miller, R.B. et a/, J. Org. Chern., 1973, 38, 4424 (synth) (4cx,5cx, 7ex, IOP)-form
Bhedi, D.N. eta/, Indian J. Chern., Sect. B, 1976, 14, 22 (synth)
Wijnberg, J.B.P.A. eta/, J. Org. Chern., 1983, 48, 4380 (synth)
Schwartz, M.A. eta/, J. Org. Chern., 1985, 50, 1359 (synth)
Vite, G.D. eta/, J. Org. Chern., 1988, 53, 2555 (synth) C 15H 260 M 222.370
(4«,5«,7«,1 0/1)-form [71963-78-5] lsointermedeol

332
11-Eudesmen-5-ol- Eudesobovatol A Sq-00992 - Sq-00996

Constit. of Cymbopogon jlexuosus. Solid. Mp 40-41°. 4-Eudesmen-6-one Sq-00994

[exJn +2° (c, 3.3 in MeOH). 4-Se/inen-6-one. Neoacolamone
(4rx.,5rx.,7p,JO/I)-form [16641-47-7] Kongol [1209-63-8]
Constit. of essential oil of Podocarpus dacrydioides and
of Japanese valerian. Cryst. Mp 94-96°. [ex]~ -18°.
(4rx.,5p,7p,JO/I)-form [83378-02-3] Amiteol
Constit. of the defence secretion of Amitermes excel/ens.
Oil. [exJ;4 +8° (CHC1 3).
(4P,5rx.,7p,JO/I)-form [5945-72-2] Neointermedeol C 15H 240 M 220.354
Constit. of Bothriochloa intermedia. Oil. Bp0 . 5 85-87°. Constit. of Chloranthus serratus. Oil. [ex]i,S + 69° {c, 0.22 in
[ex]i,S + 7.5° (c, 2.6 in EtOH). CHC1 3).
(4p,5p,7p,JOrz)-form [6168-59-8] Intermedeol. Paradisiol 7ex-Hydroxy: [97606-10-5]. 7ex-Hydroxy-4-eudesmen-6-one.
Constit. of B. intermedia and Citrus spp. Cryst. Mp 47- 7rx.-Hydroxyneoacolamone
480. [ex]~ + 10.7° (c, 0.957 in EtOH). C15H 240 2 M 236.353
4-0-P-D-Fucopyranoside: From C. serratus. Cryst. (hexane). Mp 77-77.SO. [ex]~
C21 H 360 5 M 368.512 +212° (c, 0.57 in CHC1 3).
Constit. of Carthamus lanatus. Cryst. (CH 2Cl 2/Etz0). Kawabata, J. et a/, Agric. Bioi. Chern., 1985, 49, 1479.
Mp 179°. [ex]~ -13.6° (c, 0.32 in CHC1 3).
4-0-(2-(2S-M ethylbutanoyl)-P-D-fucopyranoside]: 4(15)-Eudesmen-9-one Sq-00995
C25 H440 6 M 440.619 4(15)-Se/inen-9-one. Canarone
Constit. of C. lanatus. Cryst. Mp 86-88°. [ex]~ -10.9° (c,
0.73 in CHC1 3). [4586-67-8]

ctY
[41664-11-3) 0
Corbett, R.E. et al, Tetrahedron Lett., 1967, 1009 (Kongol)
Chetty, G.L. et al, Tetrahedron Lett., 1968, 3223 (synth, struct)
Hoffmann, J.W. et al, Tetrahedron Lett., 1973, 751
(Neointermedeol)
Hoffmann, J.W. et al, J. Org. Chern., 1976, 41, 3705 (synth)
Zalkow, V.B. et al, J. Org. Chern., 1976, 41, 3710 (synth)
Thappa, R.K. et al, Phytochemistry, 1979, 18, 671 (Isointermedeol)
CJsH240 M 220.354
Naya, Y. et al, Tetrahedron Lett., 1982, 23, 3047 (Amiteol) Constit. of Conarium strictum. Oil. Bp0 .02..oo.oJ 98-105°. [exJn
Kawamata, T. et al, Bull. Chern. Soc. Jpn., 1988, 61, 3770 (synth) +34.78° (c, 3.45 in CHC1 3).
San Feliciano, A. et al, Phytochemistry, !990, 29, 3204 (deriv) Semicarbazone: Cryst. Mp 191-192°.
Lacoume, B. et al, Tetrahedron Lett., 1966, 5881.
11-Eudesmen-5-ol Sq-00992
5-Eudesmo/. 11-Se/inen-5-o/ Eudesobovatol A Sq-00996

ltl~
~
C 15H 260 M 222.370
(4P,5rz)-form
Constit. of Kleinia pendula. Oil. [exJn + 32.8° (c, 0. 7 in
CHC1 3).
Elmi, A.H. et al, Phytochemistry, 1987, 26, 3069.

C33H440 4 M 504.708
3-Eudesmen-8-one Sq-00993 Constit. of Magnolia obovata. Neurotrophic agent. [exJn
3-Se/inen-8-one -40.3° (c, 2.5 in CHC1 3).
Fukuyama, Y. et al, Tetrahedron Lett., 1989, 30, 5907.

C1sH 240 M 220.354

Constit. of Conyza ulmifo/ia. Oil. [ex]i;l -17° (c, 0.5 in
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1367.

333
Eudesobovatol B- 4-Hydroperoxy-2-eudesmene-1,6-diol Sq-00997 - Sq-01003

Eudesobovatol B Sq-00997 7-Hydroperoxy-3,4-dihydroxy-11- Sq-01000

eudesmen-8-one

C,5H2405 M 284.352
(3p,4rx.)-form [122398-16-7] Odontin
Constit. of Pluchea arguta. Gum. [ocJi? - 180" (c, 0.04 in
MeOH).
Ahmad, V.U. et al, J. Nat. Prod. (Lloydia), 1989, 52, 561 (isol,
C33H 440 4 M 504.708 pmr)
Constit. of Magnolia obovata. Neurotrophic agent. [ocln
-26.1° (c, 1.15 in CHC1 3).
3-Hydroperoxy-4-eudesmene-1,6-diol Sq-01001
Fukuyama, Y. et al, Tetrahedron Lett., 1989, 30, 5907.
OH
I

(il
6-Formamido-4(15)-eudesmene Sq-00998

HOO~
OH
C 15H 160 4 M 270.368
C 16H 27NO M 249.395 (1rx.,3P,5P,6P,10rx.)-form
(6rx.,10rx.)-form [110044-92-3] 6-Cinnamoyl: [119364-25-9]. 6P-Cinnamoyloxy-3,6-
Constit. of Axinella cannabina. Oil. hydroperoxy-5, 10-bisepi-4-eudestnen-1 oc-ol
C24H 320 5 M 400.514
Isocyanide: [ ll 0044-90-l]. 6-Isocyano-4(15)-eudesmene Constit. of Ambrosia artemisioides. Oil.
C16H 25N M 231.380
Constit. of A. cannabina and A. acuta. Cryst. Mp 78- 3-Ketone, 6-cinnamoyl: [119285-46-0]. 6P-Cinnamoyloxy-1 oc-
790. [ocln +92.9° (c, 1.8 in CHC1 3). Has -NC replacing hydroxy- 5, l 0-bisepi-4-eudesmen-3-one
-NHCHO. C24H 300 4 M 382.499
Constit. of A. artemisioides. Oil.
Isothiocyanate: 6-Isothiocyano-4(15)-eudesmene
C 15H 25NS M 251.435 Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551.
Constit. of A. cannabina and A. acuta. Cryst. Mp 52-
530. [ocln +88.4° (c, 1 in CHC1 3). Has -NCS replacing 3-Hydroperoxy-4(15)-eudesmene-1,6-diol Sq-01002
-NHCHO.
OH
Ciminiello, P. et al, J. Nat. Prod. (Lloydia), 1987, SO, 217.

11-Formamido-5-eudesmene Sq-00999
HOO~
~
C 15Hl604 M 270.368
(lrx.,3p,5p,6p,10rx.)-form
6-Cinnamoyl: 6P-Cinnamoyloxy-3p-hydroperoxy-l oc-
C16H 27NO M 249.395
hydroxy-5, 1O-bisepi-4(15)eudesmene
(4p,7rx.,JOfJ)-form C24H 320 5 M 400.514
Constit. of Axinella cannabina. Oil. Constit. of Ambrosia artemisioides. Oil. Mol. formula
Isocyanide: 11-Isocyano-5-eudesmene given incorrectly.
C16H 25N M 231.380 Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551.
Constit. of A. cannabina. Oil. [ocJn -85.7° (c, 0.8 in
CHC1 3). Has -NC replacing -NHCHO.
/so thiocyanate: 11-lsothiocyano-5-eudesmene
4-Hydroperoxy-2-eudesmene-1,6-diol Sq-01003
C16H 25NS M 263.446 HO
Constit. of A. cannabina. Oil. [ocJn -89.7° (c, 0.8 in I I

H~
CHC1 3). Has -NCS replacing -NHCHO.
Ciminiello, P. eta/, Can. J. Chern., 1987, 65, 518.

C 15H160 4 M 270.368
(1rx.,4P,5P,6P,JOrx.)-form
6-Cinnamoyl: [119285-45-9]. 6P-Cinnamoyloxy-4fJ~
hydroperoxy- 5, l 0-bisepi-2-eudesmen-1 oc-ol

334
2-Hydroxy-4,11(13)-eudesmadien-15-... - 5-Hydroxy-3,11(13)-eudesmadien-12-... Sq-01004- Sq-01008

C24H 320 5 M 400.514 2-Hydroxy-3, 11(13)-eudesmadien-12-oic Sq-01006

Constit. of Ambrosia artemisioides. Oil. acid
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3551.
HO,Ttl
2-Hydroxy-4,11(13)-eudesmadien-15-al Sq-01004
~COOH
HO,tpy
C 15H 220 3 M 250.337
# 7
2«.-form [88153-64-4]2-Hydroxyisocostic acid. 2-Hydroxy-3,4-
6
CHO I dehydro-4, !5-dihydrocostic acid
Constit. of Schistostephium crataegifolium and Dittrichia
C 15H 22 0 2 M 234.338 viscosa. Gum. [cx]i: + 11 o (c, 0.1 in CHCI 3).
2«.-form [119863-97-7] 2-Ketone: [88153-65-5]. 2-0xo-3,11(13)-eudesmadien-12-oic
C,5H 22 0 2 M 234.338 acid. 2-0xoisocostic acid
Constit. of Tetragonotheca ludoviciana. Oil. [cx]i: +51 o C 15H 200 3 M 248.321
(c, 0.7 in CHC1 3). Constit. of S. crataegifolium. Gum. [cx]i: + 31 o (c, 0.08 in
6,7- Didehydro: [72712-39-1]. 2«.-Hydroxy-4,6-eudesmadien- CHCI 3).
15-al Bohlmann, F. et a/, Phytochemistry, 1983, 22, 1623.
C15H 200 2 M 232.322 Ceccherelli, P. eta/, Phytochemistry, 1985, 24, 2987.
Constit. of Baccharis latifolia. Oil. [cx]~4 +242° (c, 1.3 in
CHCI 3). 3-Hydroxy-4,11(13)-eudesmadien-12-oic Sq-01007
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1011. acid
Jakupovic, J. et a/, Phytochemistry, 1988, 27, 3881.
3-Hydroxyisocostic acid

1-Hydroxy-4(15),11(13)-eudesmadien-12- Sq-01005
oic acid
1-Hydroxycostic acid
(i] COOH
HO~
HOI
C 15H 220 3 M 250.337
~ COOH 3P-form [100045-52-1]

~
C,5H2P3 M 250.337
Constit. of Stevia achalensis. Oil.
3-Ketone: [62458-42-8]. 3-0xo-4,11(13)-eudesmadien-12-oic
C 15H 22 0 3 M 250.337 acid. 3-0xoisocostic acid
(1«.,7/l)-form [72944-24-2] C 15H 200 3 M 248.321
Cons tit. of Flourensia hetero/epis. Constit. of S. achalensis and A. glabrata. Cryst.
Me ester: Oil. [cx]~4 +48° (c, 0.4 in CHCI 3). (Etpjpet. ether). Mp 153°.
1-Ange/oy/: [72944-22-0]. [62458-44-0]
C20 H 280 4 M 332.439 Hikino, H. eta/, Phytochemistry, 1976, 15, 1265 (epoxide)
Constit. of F. hetero/epis. Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1986, 799.
1-Ketone: [72944-23-1]. 1-0xo-4(15), 11(13)-eudesmadien-
12-oic acid 5-Hydroxy-3, 11(13)-eudesmadien-12-oic Sq-01008
C 15H 20 0 3 M 248.321 acid
Constit. of F. hetero/epis. Oil (as Me ester). [cx]~4 + 82.2°
(c, 1 in CHCI 3) (Me ester).
11 ,13-Dihydro: [72944-21-9]. 1«.-Hydroxy-4(15)-eudesmen-
12-oic acid ('il COOH
C 15H 240 3 M 252.353
Constit. of F. heterolepis. Oil (as Me ester). [cx]~4 + 65.2°
(c, 0.5 in CHCI 3) (Me ester).
~
C,5H2203 M 250.337
(lp,7«.)-form 5«.-form
Me ester: 5«.-Hydroxyisocostic acid. 5cx-Hydroxy-P-costic acid
C 16H 240 3 M 264.364 Constit. of Jasonia montana and Apa/ochlarnys
Constit. of Losiolaena santosii. Oil. spectabilis. Gum.
(lp,7fl)-form Zdero, C. eta/, Phytochemistry, 1990, 29, 3201 (iso[)
Me ester: From L. santosii. Oil. Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (iso/, pmr)

Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1189; 1981, 20,

1613.

335
5-Hydroxy-4(15),11(13)-eudesmadien-... - 1-Hydroxy-4,11-eudesmadien-3-one Sq-01009 - Sq-01015

5-Hydroxy-4(15),11(13)-eudesmadien-12- Sq-01009 9-Hydroxy-4,11(13)-eudesmadien-12-oic Sq-01012

oic acid acid
5-Hydroxycostic acid
OH

rh
~
COOH 5a.-form
c1\COOH
C 15H 2P 3 M 250.337 C 15H 220 3 M 250.337
5rx.-form 9P-form
Constit. of Jasonia montana, Artemisia herba-alba and Constit. of Tessariafastigiata. Cryst. Mp 131-132°.
Apalochlamys spectabilis. Gum. Ac: [111394-37-7]. 9P-Acetoxy-4,11(13)-eudesmadien-12-oic
Me ester: Cryst. or oil. Mp 93°. [IX]~ +99° (c, 1.82 in acid. 9P-Acetoxy-4,5-dehydro-4(15)-dihydrocoszic acid
CHC1 3) ( + 66°). C 17H 240 4 M 292.374
41X,l5-Dihydro: 5rx.-Hydroxy-11(13)-eudesmen-12-oic acid. Constit. of Artemisia tournefortiana. Oil. [1X]~4 +48° (c,
51X-Hydroxy-41X, 15-dihydrocostic acid 0.3 in CHC1 3).
C15H 240 3 M 252.353 9-Ketone: [111394-35-5]. 9-0xo-4,11(13)-eudesmadien-12-oic
Constit. of A. spectabilis. Cryst. (as Me ester). Mp 83° acid. 9-0xo-4,5-dehydro-4(15)-dihydrocostic acid
(Me ester). [IX]~ +31° (c, 1.3 in CHC1 3) (Me ester). C15H 200 3 M 248.321
5P-form From A. tournefortiana.
Constit. of J. montana and A. spectabilis. Gum. Rustaiyan, A. et a/, Phytochemistry, 1987, 26, 2307.
Me ester: Oil. [1X]~4 -48° (c, 0.25 in CHC1 3). Guerreiro, E. eta/, Phytochemistry, 1990, 29, 877 (iso/, pmr, cmr)
Sanz, J.F. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 940 (isol, pmr,
cmr) 13-Hydroxy-4(15),7(11)-eudesmadien-12- Sq-01013
Zdero, C. eta/, Phytochemistry, 1990, 29, 3201 (isol) oicacid
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (isol, pmr)

6-Hydroxy-4(15), 11(13)-eudesmadien-12-
oic acid
Sq-01010
rh COOH

~OH
~H
2

C15H2P3 M 250.337
Constit. of Cassinia longifolia. Cryst. Mp 156°. (IX)~ +21°
(c, 0.22 in CHC1 3).
C 15H220 3 M 250.337 Zdero, C. et a/, Phytochemistry, 1987, 26, 187.
6rx.-form
61X-Hydroxycostic acid 15-Hydroxy-4,11(13)-eudesmadien-12-oic Sq-01 014
Me ester: [81373-87-7]. Quadrangulin A acid
C 16H 240 3 M 264.364 15-Hydroxyisocostic acid
Constit. of Eupatorium quadrangulare and Rudbeckia [100343-61-1]
grandiflora. Intermed. in biosynth. of the
eudesmanolides. Oil. Mol. formula incorrectly given as
c21H2403.
Gonzalez, A.G. eta/, Phytochemistry, 1985, 24, 1847 (isol)
Vasquez, M. eta/, Phytochemistry, 1988, 27, 2195 (isol) HO~COOH
8-Hydroxy-4,11(13)-eudesmadien-12-oic Sq-01011 C15H2203 M 250.337
Constit. of Pluchea dioscoridis. Oil (as Me ester).
acid
15-Aldehyde: 15-0xo-4,11(13)-eudesmadien-12-oic acid. 15-
0xoisocostic acid
C15H 2003 M 248.321
Constit. of P. dioscoridis. Oil (as Me ester).
Dawidar, A.-A. eta/, Chern. Pharm. Bull., 1985, 33, 5068.

C 15H2203 M 250.337
1-Hydroxy-4,11-eudesmadien-3-one Sq-01015
Brx.-form
Constit. of Artemisia pectinata. Oil.
Ac: 81X-Acetoxy-4, 11 (13)-eudesmadien-12-oic acid
C 17H 240 4 M 292.374
From A. pectinata. Oil. [1X]~4 +42° (c, 0.9 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 995.

M 234.338

336
5-Hydroxy-3,11-eudesmadien-2-one - 3-Hydroxy-4(15)-eudefimen-12-... Sq-01016 - Sq-01023

Ligucylperonol. lP-Hydroxy-rx.-cyperone 3-Hydroxy-1,4(15),11 (13)-eudesmnatrien- Sq-01020

Constit. of Artemisia caerulescens and Ligularia dentata. 12-oic acid
Needles (Etpjpentane). Mp 121-123°. [rx.Ji: -75° (c, 3-Hydroxy-1 ,2-dehydrocostic acid
0.94 in CHC1 3), [rx.Ji? +85° (c, 1.1 in CHC1 3). The
opposite opt. rotns. reported are unexplained.
Naya, K. eta/, Bull. Chern. Soc. Jpn., 1990, 63, 2239.
Sanz, J.F. eta[, Phytochemistry, 1990, 29, 2913 (iso/, pmr, cmr)

5-Hydroxy-3,11-eudesmnadien-2-one Sq-01016
C 1 ~H 20 0 3 M 248.321

0~~ 3fJ-form
Me ester:
~ C 16H 220 3 M 262.348
Constit. of Centaurea arguta. Oil.
C 1 ~H 22 0 2 M 234.338 3-Ketone: [96861-60-8]. 3-0xo-1,4(15),11(13)-eudesmatrien-
5«-form [24405-56-9]«-Rotunol 12-oic acid. 1,2-Dehydro-3-oxocostic acid
Constit. of tubers of nut grass, Cyperus rotundus. Cryst. C 1 ~H 18 0 3 M 246.305
(Etp). Mp 87.5-88.SO. Constit. of Montanoa speciosa and Arctotis arctotoides.
5fJ-form [24405-57-0] fJ-Rotunol Gum.
Constit. of tubers of nut grass, C. rotundus. Cryst. 3-Ketone, Me ester:
(Etp). Mp 118-119°. [rx.] 0 +44.8° (c, 5.8 in CHC1 3). C 16H 200 3 M 260.332
Hikino, H. eta/, Tetrahedron, 1971, 27, 4S31 (iso/, struct) Constit. of C. arguta. Oil.
Murai, A. eta/, J. Am. Chern. Soc., 1978, 100, 7751 (synth) Seaman, F.C. et a/, Phytochemistry, 1985, 24, 607 (isol)
Murai, A. eta/, Bull. Chern. Soc. Jpn., 1982, SS, 1195 (synth) Tsichritzis, F. eta/, Phytochemistry, 1989, 28, 195 (isol, pmr, cmr)
Gadeschi, E. eta/, Phytochemistry, 1989, 28, 2204 (iso/, pmr)
6-Hydroxy-1,4-eudesmnadien-3-one Sq-01017

001
1-Hydroxy-1,4,11-eudesmnatrien-3-one Sq-01021
1-0xo-«-cyperone

T'CY
[38043-97-9]

C 1 ~H 22 0 2
6fJ-form
M 234.338

Constit. of Sideritis varoi. Gum. [rx.]i,U +98.4° (c, 1.7 in

CHC1 3).
C 1 ~H 20 0 2
o¢=\
M 232.322
Cabrera, E. et a/, Phytochemistry, 1988, 27, 183. Constit. of tobacco. Cryst. (pentane). Mp 76-76.SO. [rx.] 0
-154° (CHC1 3).
11-Hydroxy-3,5-eudesmnadien-2-one Sq-01 018 Roberts, D.L., Phytochemistry, !972, 11, 2077.
11-Hydroxy-3,5-selinadien-2-one. Chenopodienolone
[7 4 799-42-1] 5-Hydroxy-1,4(15),7-eudesmnatrien-6-one Sq-01022
5-Hydroxy-l ,4(15), 7-se/inatrien-6-one

C 1 ~H 22 0 2 M 234.338
Constit. of Chenopodium botrys. Oil. [rx.] 0 -13.6° (c, 1.1 in
MeOH).
Ct~H 20 0 2
Qh
M 232.322
5«-form [91897-23-3] Stemonolone
de Pascual Teresa, J. eta/, Tetrahedron, 1980, 36, 371. Constit. of Pogostemon plectranthoides. Cryst. (pet.
ether). Mp 112-114°. [rx.]~ + 155.5° (c, 0.64 in CHC1 3).
2-Hydroxy-1,4,6-eudesmnatriene-3,8-dione Sq-01 019 Phadnis, A.P. eta/, J. Chern. Soc., Perkin Trans. !, 1984, 937.

~
3-Hydroxy-4(15)-eudesmnen-12-oic acid Sq-01023
3-Hydroxy-11 ,13-dihydrocostic acid
[72944- 25- 3]

M 246.305
(ll
C 1 ~H 18 03
Constit. of Baccharis boliviensis. Cryst. Mp 96°. [rx.]i;' COOH
+ 123° (c, 0.49 in CHC1 3).
HO~
Zdero, C. eta/, Phytochemistry, 1989, 28, 531.
C 1 ~H 24 0 3 M 252.353
3fJ-form
Constit. of Flourensia heterolepis.
Me ester: Oil. [oc]i;' + 72.8° (c, 0.5 in CHCI 3).

337
4-Hydroxy-11(13)-eudesmen-12-... - 11-Hydroxy-4-eudesmen-3-one Sq-01024 - Sq-01029

3-Methy/-2-butenoy/: [72944-26-4]. 9-Hydroxy-11-eudesmen-1-one Sq-01026

C20H 300 4 M 334.455
Constit. of F. hetero/epis.
Angeloyl: [72944-27-5].
C20H 300 4 M 334.455
Constit. of F. heterolepis.
Tigloy/: [72984-50-0].
C20H 300 4 M 334.455
Constit. of F. heterolepis. CisH:w02 M 236.353
Methylpropanoy/: [72944-28-6]. (4rx.,9rx.)-form [99933-34-3]/socorymbolone
C1,H280 4 M 320.428 Constit. of Cyperus corymbosus. Oil.
Constit. of F. heterolepis. Ac: Cryst. (EtOAcjpet. ether). Mp 102°. [ex]i; - H.9° (c,
3-Methy/butanoy/: [72944-29-7]. 0.728 in CHC1 3).
CwH 32 0 4 M 336.470 Garbarino, J.A. eta/, Phytochemistry, 1985, 24, 2726.
Constit. of F. hetero/epis.
3-Pheny/propanoy/: [72944-30-0]. 11-Hydroxy-1-eudesmen-3-one Sq-01027
C24H 320 4 M 384.514
Constit. of F. heterolepis.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1189.

4-Hydroxy-11(13)-eudesmen-12-oic acid Sq-01 024

C 15H140 3
HlACX>lH
M 252.353
4a.-form CisH:w02
4rx.-form
M 236.353
4P-form

4-epi-Aubergenone. 4-Epiaubergenone
Cryst. Mp 105-107°. [oc] 0 -53.5°.
4rx.-form [4586-68-9]/licic acid. Vachanic acid
Constit. of Ambrosia ilicifolia. Cryst. (EtOH aq.). Mp 4P-form [69427-35-6] Aubergenone
176-177°. [exW -35.1° (c, 1.372 in CHC1 3). Found in diseased eggplant Solanum melongena. Oil. [ex] 0
-4° (CHC1 3).
Me ester:
CI,H260 3 M 266.380 Stoessl, A. et at, Can. J. Chern., 1975, 53, 3351 (isol)
Constit. of Artemisia herba-alba. Oil. [ex)i: -34° (c, 3.3 Kelly, R.B. eta/, Can. J. Chern., 1978, 56, 2508 (synth, struct)
Murai, A. eta/, Bull. Chern. Soc. Jpn., 1982, SS, 1191 (synth)
in CHC1 3). Gulge, R. eta/, Indian J. Chern., Sect. B, 1985, 24, 605 lsynth)
4P-form
Epiilicic acid
Constit. of A/eantara ekmaniana. Gum.
11-Hydroxy-3-eudesmen-2-one Sq-01028
lsopterocarpolone
Herz, W. eta/, J. Org. Chern., 1966, 31, 1632 (iso/, struct)
Jain, T.C. eta/, Chern. Ind. (London), 1969, 378 (abs config) [5280 1-06-6]
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 456 (isol)
Daniewski, W.M. et at, Collect. Czech. Chern. Commun., 1986, 51,
1710 (cryst struct)
Sanz, J.F. et at, Phytochemistry, 1990, 24, 541 (ester, pmr, cmr)

5-Hydroxy-6-eudesmen-8-one Sq-01025 CisH:w02 M 236.353

Constit. of the heartwood of Pterocarpus santalinus.

~
Viscous liq. [ex]i? +47° (c, 0.9 in CHC1 3).
Kumar, N. et at, Phytochemistry, 1974, 13, 633.

11-Hydroxy-4-eudesmen-3-one Sq-01029
C 15H 240 2 M 236.353 Carissone
(4P.5« )-form [473-10-9]
Constit. of Labiumfloribundum. Oil. [ex]~ +9° (c, 0.15 in
CHC1 3).
Bohlmann, F. et at, Phytochemistry, 1984, 23, 1800.
001
YfoH
CisH:w0 2 M 236.353
Constit. of Carissa lanceolota andEucalyptus macarthuri.
Cryst. (Et20jpet. ether). Mp 78-79°. [ex]);~ + 136 6° (c,
1.025 in CHC1 3).
McQuillan, F.J. eta/, J. Chern. Soc., 1954, 3492 (synth)
Sathe, V.M. eta/, Indian J. Chern., 1971, 9, 95 (synth)
Kutney, J.P. eta/, Can. J. Chern., 1982, 60, 1842 (synth)

338
12-Hydroxy-11(13)-eudesmen-2-one - 1,6,8-Trihydroxy-15-oxo-11(13)-..• Sq-01030 - Sq-01035

12-Hydroxy-11(13)-eudesmen-2-one Sq-01030 3,4,11-Trihydroxy-6-eudesmen-8-one Sq-01 034

0~ HO'
0
OH
(3cx,4cx)-form

: H CH2 0H HO
C 15H 240 2 M 236.353 C,5H2404 M 268.352
Constit. of Vernonia lanuginosa. Oil. [1X]i: +41 ° (c, 0.25 in (3«,4«)-form [71539-78-1] Plucheinol
CHC1 3). Constit. of Pluchea chingoyo. Cryst. (C 6H6 /Et0Ac). Mp
111;,,13-Dihydro: 12-Hydroxy-2-eudesmanone 86-88°.
C 15H 260z M 238.369 3-(2,3-Epoxy-2-methylbutanoyl), 4-Ac: [68799-58-6]. 4-
Constit. of V. lanuginosa. Oil. [1X]i: +20" (c, 0.22 in Epiargutkinin
CHC1 3). C22 H3z07 M 408.491
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 473. Isol. from P. foetida. Oil.
(3«,4/1)-form
4-Epip/ucheino/
2-Hydroxy-3-oxo-4,11(13)-eudesmadi~n- Sq-01031 C,5H240 4 M 268.352
12-al From P. arguta. Cryst. (C 6H 6). Mp 80°. [1X]n + 50°
2-Hydroxy-13-oxo-rx.-cyperone

H:xrt\CHO
(CHC1 3).
3-(2,3-Epoxy-2-methylpropanoyl), 4-Ac: Arguticinin
C22H 320 7 M 408.491
Constit. of P. arguta. Gum. [IX]~ +98° (c, 0.04 in
MeOH).
(3P,4«)-form
C15H200 3 M 248.321 3rx.H-Piucheinol
2fJ-form C,5H240 4 M 268.352
Constit. of Artemisia herba-alba. Gum. Constit. of P. chingoyo.
3-Angeloyl:
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3661 (isol, pmr)
C20H34.05 M 350.454
Constit. of P. suaveolens. Oil.
8-Hydroxy-3-oxo-1,4,11(13)-eudesmatrien- Sq-01 032 3-Angeloyl, 4-Ac:
12-oic acid C22 H320 6 M 392.491
Constit. of P. suaveolens. Oil.
(i[OH 3-(2,3-Dihydroxy-2-methylbutanoyl), 11-hydroperoxide:
[122398-17-8]. Odonticin
0~COOH C20H320 8 M 400.468
Constit. of P. arguta. Syrup. [IX]~ + 178° (c, O.Ql in
C15H 180 4 M 262.305 MeOH).
8fJ-form Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1189; 1980, 19, 969
(derivs)
Yomoginic acid
Chiang, M.T. eta/, Phytochemistry, 1979, 18, 2033 (iso/)
Me ester: Methyl yomoginate Zabel, V. et a/, Acta Crystal/ogr., Sect. B, 1982, 38, 584 (cryst
C16H200 4 M 276.332 struct)
Constit. of Ferreyranthus fruticosus. Oil. Ahmad, V.U. eta/, Phytochemistry, 1986, 25, 949; 1988, 27, 1861
(iso/, derivs)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113.
Ahmad, V.U. et a/, J. Nat. Prod. (Lioydia), 1989, 52, 861
(Odonticin)
8-Hydroxy-3-ox0-1,4(15),11(13)- Sq-D1033
eudesmatrien-12-oic acid .1,6,8-Trihydroxy-15-oxo-11(13)-eudesmen- Sq-01 035
12-oic acid
OH
H

C,5HI804 M 262.305 COOH

8fJ-form
CHO OH
8-Ac, Me ester: [73723-66-7]. Gerin
C18H 22 0 5 M 318.369 C,5H220 6 M 298.335
Constit. of Gerea viscida. Cryst. (EtzO). Mp 140-141.SO. (lp,4rx.,6rx.,8rx. )-form
[1X]~4 -243° (c, 0.5 in CHC1 3). 8-(2-Hydroxymethyl-2-propenoyl), Me ester: [104407-37-6].
Rodriguez, E. eta/, Phytochemistry, 1979, 18, 1741. Carmanin
C20 H280 8 M 396.436
Constit. of Onopordon carmanicum. Oil.
(IP,4P,6rx.,8rx.)-form
8-(2-Hydroxymethyl-2-propenoyl), Me ester: 4-epi-
Carmanin. 4-Epicarmanin

339
Uvarisesquiterpene B - 1,2-Dihydroxy-5,11(13)-eudesmadien-... Sq-01036 - Sq-01041

C20 H 280 8 M 396.436 1,2-Dihydroxy-4,11(13)-eudesmadien-12,8- Sq-01 039

From 0. carm'anicum. Oil. olide
Rustaiyan, A. eta/, Phytochemistry, 1986, 25, 1659.

Uvarisesquiterpene B Sq-01036
[117176-79-1] (lp,2cx,8cx)form

&~
C 15H 200 4 M 264.321
(I p,2~t,8~t )-form
2-Ac: [80931-30-2]. 2~t-Acetoxy-8-epiivangustin
C 17H 2p 5 M 306.358
Consit. of Eriophyllum lanatum. Gum. [a]i;' + 50° (c,
O.o3 in CHC1 3).
C22 H 300 M 310.478
(IP,2~t,8/l)-form
Constit. of Uvaria angolensis. Amorph.
2~t-Hydroxyivangustin .
Muhammad, I. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 719. Constit. of Gnephosis arachnoidea. Gum. [a]i;' + 39° (c,
1.09 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2239 (isol)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3181 (isol)

12,8-Eudesmanolides 1,2-Dihydroxy-4(15), 11 (13)-eudesmadien-

12,8-olide
Sq-01 040

and furanoeudesmanes OH
I

HO,('i!O):
~ 0 (lcx,2cx,8P)-form

1,2:3,4-Diepoxy-11(13)-eudesmen-12,8- Sq-01037
C 15H 200 4 M 264.321
olide
{l~t,2~t,8/l)-form
1,2:3,4-Bisepoxy-11(13)-eudesmen-12,8-olide
Di-Ac: l~t,2~t-Diacetoxyalantolactone

0~
Q C1,H240 6 M 348.395
Constit. of Inezia integrifolia. Gum. [a]~4 + 68° (c, 0.11
I
. 0 in CHC1 3).
6~ \ (IP,2~t,8/l)-form [5956-43-4] lvasperin
Constit. of Iva spp. and Ambrosia polystachya. Prisms
C 15H 180 4 M 262.305 (EtOAc). Mp 157-159°. [a]~+ 121° (CHC1 3).
(l~t,2~t,3~t,4~t,8fJ)-form Herz, W. eta/, J. Org. Chern., 1964, 29, 1022 (isol, stru,·t, uv, ir,
Constit. of Ferreyranthus fruticosus. Cryst. Mp 192°. pmr)
Vichnewzki, W. et at, Phytochemistry, 1976, 15, 1531 (isol)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113. Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2743
(Diacetoxyalantolactone)
1,2-Dihydroxy-3,11(13)-eudesmadien-12,8- Sq-01 038
olide 1,2-Dihydroxy-5,11(13)-eudesmadien-12,8- Sq-01041
olide

HO,¢cq=O
HO
HO,~o'Fo OH

~
C 15H 200 4 M 264.321
(IP,2~t,8/l)-form C15H2004 M 264.321
1-(2-Methylbutanoyl): [90039-66-0]. 3,4-Dehydro-5,6- (I P,2~t,8/l)-form
dihydro-2a-hydroxy-1P-(2- I ,2-Dihydroxyalantolactone
methylbutyroyloxy)alantolactone 2-Ac:
C20H 280 5 M 348.438 C17H 220 5 M 306.358
Constit. of Wunderlichia mirabilis. Oil. [a]~4 + 93° (c, 0.2 Constit. of Eriophyllum lanatum. Mp 170°. [ali;' + 112°
in CHC1 3). (c, 0.23 in CHC1 3).
Bohlmann, F. et a/, Justus Liebigs Ann. Chern., 1984, 228. Bohlmann, F. et at, Phytochemistry, 1981, 20, 2239.

340
1,3-Dihydroxy-4(15),11(13)-... - 2,3-Dihydroxy-4(15),11(13)-... Sq-01042 - Sq-01046

1,3-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01 042 C 20H 260 5 M 346.422

12,8-olide Constit. of C. cinerariaefolium. Cryst.
(EtOH/diisopropy1 ether). Mp 202-204° dec. [1X]i,S +80°
HO (c, 0.2 in MeOH).
I
6-(2-Methylpropanoyl): [95732-44-8]. Subcordatolide C

HO'~O
C,9H 260 5 M 334.411
Constit. of Galea subcordata. Cryst. Mp 196-197° dec.
11 p,JJ-Dihydro: .1p,61X-Dihydroxy-4( 15)-eudesmen-12,81X-
olide
C 15H 20 0 4 M 264.321 C 15H 220 4 M 266.336
(1~,3~,8/1)-form [40737-97-1] Granilin Consit. of Lasiolaena santosii, Mikania goyazeum and
Constit. of lnula grandis. Cryst. (MeOH). Mp 197-198°. Artemisia gypsacea. Gum. [1X]~4 +20° (c, 0.32 in CHC1 3).
[1X]i,S + 147.9° (c, 1 in Me 2CO). Originally thought to be the corresponding eudesmen-
12,6-olide.
Maruyama, M. eta/, Phytochemistry, !975, 14, 2247 (struct)
Vichnewski, W. eta/, Phytochemistry, 1976, 15, 1531 (cmr) llp,JJ-Dihydro, 6-Ac.' [16822-17-6]. Dihydro-P-
cyclopyrethroidin
C 17H 240 5 M 308.374
1,6-Dihydroxy-4,11(13)-eudesmadien-12,8- Sq-01 043 Constit. of Chrysanthemum cinerariaefolium. Cryst.
olide (EtOH/diisopropyl ether). Mp 212-213°. [1X]i,S + 72.4° (c,
0.24 in CHCI 3).

h.-~~O
Doskotch, R.W. eta/, Can. J. Chern., 1969, 47, 1139; 1971, 49,
2103 (/J-Cyc/opyrethrodin, Chrysanin)

Y0
Ober, A.G. eta/, J. Nat. Prod. (Lloydia), 1984, 47, 920
(Witt,Sn)-fo'm (Subcordatolide C)
Cardona, M.L. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 1042
(struct)
C 15H 200 4 M 264.321
(lp,6~,8~)-form 1,8-Dihydroxy-3,7(11 )-eudesmadien-12,8- Sq-01 045
6~-Hydroxy-8-epiivangustin
olide
Constit. of Gnephosis arachnoidea. [1X]i;l -25° (c, 0.58 in
CHC1 3).
6-Ac: 6~-Acetoxy-8-epiivanagustin
C 17H 220 5 M 306.358
Constit. of G. arachnoidea. [1X]i;l -25° (c, 0.58 in
~o\:o
CHC1 3).
Di-Ac:
~
C 19H 240 6 M 348.395 C 15H 200 4 M 264.321
Constit. of G. arachnoidea. Gum. [1X]i;l -20° (c, 0.58 in (Jp,Sfl)-form
CHC1 3). l-Ac: [108044-19-5]. 1P-Acetoxy-8p-hydroxy-3,7(11)-
(1 p,6p,8fl)-form eudesmadien-12,8-olide
6P-Hydroxyivangustin C 17H 22 0 5 M 306.358
6-Tig/oy/: Constit. of Smyrnium ga/aticum. Amorph.
C 20H 260 5 M 346.422 Ulube1en, A. eta/, J. Nat. Prod. (Lloydia), 1986, 49, 1104.
Constit. of Steiractinia mol/is. Oil. [1X]~4 +43.2° (c, 2 in
CHC1 3). 2,3-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01 046
6-Tigloy/, l-Ac: 12,8-olide
C 12H 28 0 6 M 388.460
Constit. of S. mol/is. Oil. [1X]i;l + 49° (c, 1 in CHC1 3).
Ho,~0)= 0
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 971 (isol)
Jakaporic, J. eta/, Phytochemistry, 1988, 27, 3181 (isol)
HO~
1,6-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01 044 CtsH2004 M 264.321
12,8-olide (1~,3p,8fl)-form[22850-59-5] Pulchellin C
Constit. of Gaillardia pulchella. Cryst. Mp 199-202°. [IX]~
+ 125° (c, 1.55 EtOH).
2-Ac: [6754-36-5]. Pulchellin B
0 C 17H 220 5 M 306.358
Constit. of G. pulchella. Cryst. Mp 215-218°. [1X]i;"
+92.7° (c, 1.54 in EtOH).
(lp,6~,8~}-form 3-Ac: [22660-69-1]. Pulchellin E
C 17H 220 5 M 306.358
6-Ac: [22553-66-8]. P-Cyclopyrethrosin
Constit. of G. pulchella. Cryst. (Me 2COjpet. ether). Mp
C 17H 120 5 M 306.358
181-183°. [IX]~ +43.8° (c, 1 in EtOH).
Constit. of Chrysanthemum cinerariaefolium. Cryst.
(EtOH aq.). Mp 166-167°. [1X]i,S +58.2° (c, 0.5 in 2-Tigloy/: [22850-61-9]. Pulchellin F
MeOH). C 20H 260 5 M 346.422
6-Tig/oyl: [34226-89-6]. Chrysanin

341
3,5-Dihydroxy-4(15),11(13)-... - 1,8-Dihydroxy-2-oxo-3,7(11)-... Sq-01047 - Sq-01053

Constit. of G. pulchella. Cryst. (Me 2COjpet. ether). Mp 1,4-Dihydroxy-11(13)-eudesmen-12,8-olide Sq-01 050

144-146°. [a]~ +91.7° (c, 1.08 in CHCI 3).
2-(3-Methy/-2-butenoyl): 3fJ-Hydroxy-2«- OH

(l):to
I
senecioyloxyisoalantolllctone
C10H 260 5 M 346.422
Constit. of Inula caspica. Cryst. (EtOH). Mp 222-223°.
Herz, W. et al, Tetrahedron, 1964, 20, 341 (isol)
Herz, W. et al, Phytochemistry, 1969, 8, 661 (isol) HO
Yoshioka, H. eta/, J. Org. Chern., 1970, 35, 627 (struct) CisHn04 M 266.336
Adekenov, S.M. et al, Collect. Czech. Chern. Commun., 1990, SS,
(1«,4«,8/1)-form [5945-43-7] Microcephalin
1568 (isol, pmr, cmr, cryst struct)
Constit. of Iva microcephala and I. axillaris. Cryst.
(EtOAc). Mp 206-208°. [am + 75° (c, 1.3 in CHC1 3).
3,5-Dihydroxy-4(15), 11(13)-eudesmadien- Sq-01 047 (1fl,4«,8f/)-form
12,8-olide 1-(2-Methylbutanoyl):
C10H:lC,0 5 M 350.454
('t1(o'>=o Constit. of Wunderlichia mirabilis. Oil. [a]i: +26° (c,
0.18 in CHC1 3).
HO'~ (3cx,5cx,8P)-:form
Herz, W. et al, J. Org. Chern., 1964, 29, 1700; 1966, 31, 3232 (isol,
uv, ir, struct)
C•sH100 4 M 264.321 Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 228 (deriv)

0
(3«,5«,8/1)-:form

Hm
1«,5«-Dihydroxyisoalantolllctone 4,6-Dihydroxy-11-eudesmen-12,8-olide Sq-01051
Constit. of Artemisia iwayomogi. Cryst. Mp 178°. [a]n
+ 159° (c, 0.15 in CHC1 3).
3-Hydroperoxide: 3a-Hydroperoxy-5a-hydroxy-4(l5),ll(l3)-
eudesmadien-l2,8P-olide. 5a-Hydroxy-3a-peroxy-
4(l5), ll ( l3)-eudesmadien-l2,8P-olide. 3a- Peroxy- 5a-
hydroxyisoalantolactone
C15H 100 5 M 280.320 CisHn04 M 266.336
From A. iwayomogi. Oil. The structs. given here are not certain due to errors in the
(3«,5fl,8f/)-form paper (named as eudesmanolides).
3-Hydroperoxide: 3a-Hydroperoxy-5p-hydroxy-4(l5), ll(l3)- (4fl,6«,8«)-form
eudesmadien-l2,8P-olide. 5P-Hydroxy- 3a-peroxy- Constit. of Tanacetum ferulaceum. Needles
4(15),ll(l3)-eudesmadien-l2,8P-olide. 3a-Peroxy-5p- (EtOAcjhexane). Mp 222-224°.
hydroxyisoa/antolactone 4-Deoxy, 4,15-didehydro: 6-Hydroxy-4(/ 5),1 1-eudesmadien-
C 15H100 5 M 280.320 12,8-olide
From A. iwayomogi. Oil. CisH100 3 M 248.321
Greger, H. et al, Phytochemistry, 1986, 2S, 891. Constit. of T. ferulaceum. Gum.
Gonzalez, A.G. et al, Phytochemistry, 1990, 29, 2339 (isol, pmr)
5,8-Dihydroxy-4(15),7(11 )-eudesmadien- Sq-01048
12,8-olide 1,5-Dihydroxy-2-oxo-3,11(13)- Sq-01052
eudesmadien-12,8-olide
OH

~0
OH
I
0
0
C15H100 4 M 264.321
(5«,8flOH)-form C15H 180 5 M 278.304
Constit. of Lophocolea heterophylla. Cryst. Mp 216-217°.
(1«,5«,8/1)-:form
Toyota, M. et al, Phytochemistry, 1990, 29, 2334 (isol, pmr, cmr) 1«,5«-Dihydroxypinnatifidin
Constit. of Ferreyranthus fruticosus. Oil.
1,5-Dihydroxy-2,4(15),11(13)- Sq-01049 Jakupovic, J. et al, Phytochemistry, 1988, 27, 1113.
eudesmatrien-12,8-olide
HO 1,8-Dihydroxy-2-oxo-3,7(11 )-eudesmadien- Sq-01 053
I
12,8-olide
0 HO
I I OH
o~~o 0
....... ::::,...
C•sH180 4 M 262.305
(1«,5«,8/1)-:form H
Constit. of Ferreyranthus fruticosus. Oil. C15H 180 5 M 278.304
Jakupovic, J. et al, Phytochemistry, 1988, 27, 1113. (ent-1 fl,Bfl)-form

342
2,3-Epoxy-1,4-dihydroxy-7(11),8-... - 4,11(13)-Eudesmadien-12,8-olide Sq-01054 - Sq-01060

Constit. of Salvia palaefolia. 1,4(15)-Eudesmadien-12,8-olide Sq-01058

l-Ac: 1;4( 15)-Se/inadien-12 ,8-o/ide
C 17H 200 6 M 320.341 I

fir >=o
Constit. of S. pa/aefolia. Cryst. Mp ~15-120°.
Gonzalez, A. G. eta/, Phytochemistry, 1990, 29, 3581 (isol, pmr, 0
cmr, abs co'!fig)
~
2,3-Epoxy-1,4-dihydroxy-7(11),8- Sq-01054 C15H 200 1 M 232.322
eudesmadien-12,8-olide (5p,7p,llrx.,8rx.,10rx.)-form [66964-62-3] Callitrisin
Constit. of Callitris columel/aris. Cryst. (MeOH). Mp

o:~o
163.5-164.SO. [a.Jn -41°.
1,~-Dihydro: [66964-61-2]. ent-4(15)-Eudesmadien-12,8a.-
o/ide. Dihydrocallitrisin
C 15H 220 1 M 234.338
HO Constit. of C. columellaris. Cryst. (hexane). Mp 127-
C 15H 180 5 M 278.304 1280. [a.Jn -39°.
(1 P,2rx.,3rx.,4rx. )-form Brecknell, D.J. eta/, Tetrahedron Lett., 1978, 73 (isol)
Brecknell, D.J. eta/, Aust. J. Chern., 1979, 32, 2455 (isol)
Constit. of Smyrnium perfoliatum. Amorph. Godfrey, H.D. et a/, Tetrahedron Lett., 1979, 3241 (synth)
Goren, N. eta/, Phytochemistry, 1987, 26, 2585. Schultz, A.G. eta/, J. Am. Chern. Soc., 1980, 102, 2414 (synth)
Tada, M. et a/, Chern. Lett., 1982, 441 (synth)
3,4-Epoxy-1,11(13)-eudesmadien-12,8- Sq-01055
olide 3,11(13)-Eudesmadien-12,8-olide Sq-01059

~0
CtsHt80 3 M 246.305 CtsH200 2 M 232.322
(1rx.,4rx.,8/l)-form [75627-96-2] Ursialpinolide (5rx.,7P,8P,10/I)-form [64395-76-2] lsoa/loalantolllctone
Constit. of Ursinia alpina. Cryst. (Etpjpet. ether). Mp Constit. of Inula racemosa and Artemisia iwayomogi.
165°. Cryst. Mp 70°. [a.Jn +98° (c, 0.11 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 587. (5p,7rx.,8rx.,10rx.)-form [56632-84-9]
ent-3, 11 (13)- Eudesmadien-12,8P-olide. Diplophyllolide A
1,2-Epoxy-3-hydroxy-4,11(13)- Sq-01056 Constit. of Diplophyllum a/bicans. Cryst. Mp 60-62°.
eudesmadien-12,8-olide Benesova, V. eta/, Collect. Czech. Chern. Commun., 1975, 40, 1966
(Diplophyl/olide A) •
Kaur, B. eta/, Phytochemistry, 1985, 24, 2007 (isol)
Greger, H. eta/, Phytochemistry, 1986, 25, 891 (isol)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3551 (derivs)

4,11(13)-Eudesmadien-12,8-olide Sq-01060
CtsH 180 4 M 262.305
(1 rx.,2rx.,3rx.,8/l)-form
Constit. of Ferreyranthus fruticosus. Cryst. Mp 166°.
~o'>=o
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113.
~
2,3-Epoxy-1,4,8-trihydroxy-7(11)- Sq-01057. C 15H 200 2 M 232.322
eudesmen-12,8-olide (7p,8p,10/l)-form [64340-41~6] Alloalantolllctone
Constit. of Inula helenium and/. racemosa. Oil. [a.Jn
+ 35.2° (c, 0.5 in CHC1 3).
OH OH
3a.,l5-Dihydroxy: [119285-38-0]. 3a.,15-Dihydroxy-4,11(13)-
o:Qj}o eudesmadien-12,8P-olide. 3rx.,15-
Dihydroxyalloa/antolllctone
C 15H 200 4 M 264.321
HO Constit. of Ambrosia artemisioides. Oil.
C 15H 200 6 M 296.319 15-Acetoxy, 3a.-hydroperoxy: [119285-37-9]. 15-Acetoxy-1rx.-
(1P,2rx.,3rx.,4rx.,8/l)-form hydroperoxyalloalantolllctone
8-Me ether: 2a.,3a.-Epoxy-1p,4a.-dihydroxy-8P-methoxy- C 17H 220 6 M 322.357
7(11 )-eudesmen-12,8-o/ide Constit. of A. artemisioides. Oil.
Ct,H2206 M 310.346 15-Hydroxy, 3-oxo: [119285-39-1]. 15-Hydroxy-3-oxo-
Constit. of Smyrnium perfoliatum. Amorph. [a.]i;' 4,11 (13)-eudesmadien-12,8P-olide. 15-Hydroxy-3-
-33.6°. oxoalloa/antolllctone
Goren, N. eta/, Phytochemistry, 1987, 26, 2585. CtsHt80 4 M 262.305
Constit. of A. artemisioides. Oil.

343
4(15),7(11)-Eudesmadien-12,8-olide - 5,7(11)-Eudesmadien-12,8-olide Sq-01061 - Sq-01064

4P,5P-Epoxide: 41J,5fJ-Epoxy-11(13)-eudesmen-12,8fJ-olide 4(15),11(13)-Eudesmadien-12,8-olide Sq-01063

C 15H2e,03 M 248.321
Constit. of Calea szyszylowiczii. Cryst. (Et 20jpet. ether).
Mp 115°.
(7rz,8rz,10rz)-form
ent-4,11(13)-Eudesmadien-12,8P-olide. ent-
~0
AIIoalantolactone. Diplophyllin C 15H 200 1 M 232.322
Constit. of Diplophyllum albicans and D. taxifolium. 8/J-form [470-17-7]/soalllntolactone. Isohelenin
Shows antitumour activity against human epidermoid Constit. of the essential oil of lnula helenium, f.
carcinoma. Cryst. Mp 30-31.SO. [ocln -108° (pentane). racemosa and Telekia speciosa. Cryst. (EtOH aq.). Mp
11 oc,13-Dihydro: [73039-16-4]. ent-4- Eudesmen-12,8P-olide. 115° (109-110°). [ocJn + 172° (CHC1 3).
ent-Dihydrodiplophyllin 1-0xo: J-Oxo-4(15),11(13)-eudesmadien-12,8P-olide. 1-
C 15Hn01 M 234.338 0xoisoalllntolactone
Constit. of D. a/bicans. Oil. [ocln -43.8° (c, 1.8 in C 15H 180 3 M 246.305
CHC1 3). The name ent-Dihydrodiplophyllin is Constit. of Flourensia macrophylla. Cryst. Mp 164°.
misleading. Incorrectly called 1-0xoalantolactone in the lit.
Ohta, Y. eta/, Tetrahedron, 1977, 33, 617 (Diplophyllin) 9oc-Hydroxy: 9oc-Hydroxy-4(15), 11 (13)-eudesmadit•n-12,8P-
Ananthasubramanian, L. et a/, Indian J. Chern., Sect. B, 1978, 16, olide. 9rz-Hydroxyisoalantolactone
191 (synth) C 15H 200 3 M 248.321
Bohlmann, F. et at, Phytochemistry, 1978, 17, 1165
Constit. of F. macrophylla. Oil. Incorrectly called 9-
(Ailoalantolactone)
Asakawa, Y. et a/, Phytochemistry, 1979, 18, 1007 (ent-
Hydroxyalantolactone.
Dihydrodiplophyllin) 9P-Hydroxy: 9P-Hydroxy-4(15),11(13)-eudesmadien-12,8P-
Bhandari, P. et at, Indian J. Chern., Sect. B, 1983, 22, 286 olide. 9/J-Hydroxyisoalantolactone
(Ailoalantolactone) C 15H 200 3 M 248.321
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2227 lsol. from F. macrophylla. Cryst. Mp 171°. [oc]i'~ + 78° (c,
(epoxide) 1.9 in CHC1 3).
Jakupovic, J. eta/, Phytochemistry,' 1988, 27, 3551 (derivs)
9-0xo: 9-0xo-4(15),11(13)-eudesmadien-12,8P-olide. 9-
0xoisoalllntolactone
4(15),7(11)-Eudesmadien-12,8-olide Sq-01061 C,sH 180 3 M 246.305
4(15), 7(11)-Se/inadien-12 ,8-o/ide lsol. from F. macrophyl/a. Cryst. Mp 118°. Incorrectly

Q=X(o
called 9-0xoalantolactone.
4oc,J5-Epoxy: 4oc,15-Epoxy-4(15), 11(13)-eudesmadien-12,8P-
olide. 4rz,15-Epoxyisoalantolactone
(8a.)-form C15H 200 3 M 248.321
Constit. of Ambrosia artemisioides. Oil.
C 15H 200 1 M 232.322 4rx,J5-Epoxy, Joe-hydroxy: 4rz,15-Epoxy-3rz-
8rz-form [73069-14-4] Asterolide. Atractylenolide II hydroxyisoalantolactone
Constit. of Aster umbel/atus and A. japonica. Oil. [oc]i;' C 15H 200 4 M 264.321
+471.6° (c, 0.2 in CHC1 3). Constit. of A. artemisioides. Oil.
8/J-form [16641-51-3] 8-Epiasterolide Jloc,13-Dihydro: 4(15)-Eudesmen-12,8P-olide.
Constit. of A. umbellatus. Oil. [oc]i;' -100° (c, 0.12 in Dihydroisoalantolactone
CHC1 3). C 15H 110 1 M 234.338
8,9-Didehydro: [73069-13-3]. 4(15),7(1 1),8-Eudesmatrien- Isol. from roots of/. helenium. Needles (EtOH). Mp
12,8P-olide. Atractylenolide I. 8,9-Dehydroastero/ide 172-173°.
c,5H,80 1 M 230.306 Asselineau, C. eta/, Compt. Rend. Hebd. Seances Acad. Sci., 1958,
Constit. of Atractylodes japonica. Antiinflammatory. 246, 1874 (struct)
Cryst. or oil. Mp 109-110.SO. [oc]i? +222° (c, O.Ql in Ukita, T. et a/, J. Am. Chern. Soc., 1960, 82, 2224
MeOH). (Dihydroisoalantolac tone)
Bunesova, V. eta/, Collect. Czech. Chern. Commun., 1961, 26, 135,
Endo, K. et a/, Chern. Pharm. Bull., 1979, 27, 2954 (isol)
2916 (Isotelekin)
Bohlmann, F. et at, Phytochemistry, 1980, 19, 433 (isol)
Marshall, J.A. et al, J. Org. Chern., 1964, 29, 3727 (pmr, struct)
Bokel, H.H. eta/, Justus Liebigs Ann. Chern., 1982, 73 (synth)
Miller, R.B. et al, Tetrahedron, 1974, 30, 2961 (synth)
Tada, M., Chern. Lett., 1982, 441 (synth)
4(15),7-Eudesmadien-12,8-olide Sq-01062 Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1445 (derivs)
4( 15), 7-Se/inadien-12 ,8-o/ide Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3551 (epo:cides)

[l'y~)=o 5,7(11 )-Eudesmadien-12,8-olide Sq-01064

~
11a.-form

C 15H 200 1 M 232.322

llrz-form [74634-80-3]
C 15H 200 1 M 232.322
Constit. of Aster umbellatus. Oil.
8/J-form [66397-38-4] Neoalllntolactone
llfJ-form [74634-79-0]
Constit. of Inula racemosa. Cryst. (MeOH). Mp 110°.
Constit. of A. umbellatus. Oil.
[oc]n - O.Ql 0 (CHC13).
Bohlmann, F. et at, Phytochemistry, 1980, 19, 433.
Ravindranath, K.R. et al, Indian J. Chern., Sect. B, 1978, 16, 27.

344
5,11(13)-Eudesmadien-12,8-olide - Furanoeudesma-1,4-dien-6-one Sq-01065 - Sq-01072

5,11(13)-Eudesmadien-12,8-olide Sq-01065 3,5,11(13)-Eudesmatrien-12,8-olide Sq-01068

(X):?o
C 15H 200 2 M 232.322
8ft-form [546-43-0) Alantolactone. Helenine. A/antic anhydride ClsH!aOz M 230.306
Constit. of Inula helenium, I. racemosa and I. grandis. BP-form
Cryst. (pentane). Mp 78-80°. [1X)n + 175° (CHCI 3). Isoalantodiene
Constit. of Inula racemosa. Cryst. Mp 82°.
1P-Hydroxy: [68776-47-6]. 1P-Hydroxy-5,11(13)-
eudestnadien-12,8P-olide. 1ft-Hydroxyalantolactone Kalsi, P.S. eta/, Phytochemistry, 1989, 28, 2093 (iso/, pmr)
C 15H 20 0 3 M 248.321
From I. helenium. 4,6,11(13)-Eudesmatrien-12,8-olide Sq-01069
21X-Hydroxy: [68776-45-4]. 21X-Hydroxy-5,11(13)-

~0
eudesmadien-12,8P-olide. 2rx.-Hydroxyalantolactone
C 15H 200 3 M 248.321
Constit. of I. spp. and Francoeuria crispa. Cryst. (pet.
ether). Mp 104°. [1X)n + 156.3° (c, 1 in CHCI 3).
2-0xo: [68776-46-5]. 2-0xo-5,11(13)-eudesmadien-12,8P-
CisHI80z M 230.306
olide. 2-0xoa/antolactone
C1sH 180 3 M 246.305 8ft-form
From I. helenium. Cryst. (EtzO). Mp 152-153°. [1X)~4 Alantodiene
+ 301.3° (c, 1.3 in CHCI 3). Constit. of Inula racemosa. Oil.
Tsuda, K. eta/, J. Am. Chern. Soc., 1957, 79, 5721 (struct) Kalsi, P.S. eta/, Phytochemistry, 1989, 28, 2093 (iso/, pmr)
Marshall, J.A. et a/, J. Org. Chern., 1964, 29, 3727 (pmr, struct)
Marshall, J.A. eta/, J. Am. Chern. Soc., 1966, 88, 3408 (synth) Fruticolide Sq-01070
Khvorost, P.P. et a/, Khim. Prir. Soedin., 1976, 12, 820 (isol)
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1165 (derivs) [115334-55-9)
Al-Yahya, M.A. eta/, J. Nat. Prod. (Lloydia), 1984, 47, 1013
(deriv)
Milman, I.A., Khim. Prir. Soedin., 1990, 26, 307; Chern. Nat.
Compd. (Engl. Trans/.), 251 (rev)

1,4(15),7(11)-Eudesmatrien-12,8-olide Sq-01066

Q:Yo
C 15H 180 2 M 230.306
8rx.-form [20267-90-7] Lindestrenolide C 30H 3z06 M 488.579
Constit. of Lindera strychnifolia. Oil. Bp0 _2 100-105° Constit. of Ferreyranthus fruticosus. Oil.
(bath). [IX)~ + 189° (c, 1.1 in dioxan). Jakupovic, J. eta/, Phytochemistry, 1988, 27, II 13.
8,9-Didehydro: [32810-35-8). 1,4(15), 7(11),8-
Eudesmatetraen-12 ,81X-olide. Dehydrolindestrenolide Furanoeudesma-1,3-diene Sq-01 071
From L. strychnifolia. Cryst. (EtzOjpet. ether). Mp lll-
1130. [IX)~ + 180.4° (c, 1 in EtOH).
Takeda, K. eta/, J. Chern. Soc. C, 1968, 569.
Tada, H. et a/, J. Chern. Soc. C, 1971, 1070.

1,4(15),11(13)-Eudesmatrien-12,8-olide Sq-01067 ClsH180 M 214.307

Constit. of oil of myrrh. Liq. [1X)i? + 59° (c, 0.82 in
CHCI 3).
Brieskorn, C.H. et a/, Phytochemistry, 1983, 22, 187.

Furanoeudesma-1,4-dien-6-one Sq-01072
C 15H 180 2 M 230.306
(5p,7p,ap,10rx.)-form [97456-59-2]1,2,4,15-Tetradehydro-4,5-
dihydrosteiractinolide
Constit. of Spilanthes leiocarpa. Oil.
Bohlmann, F., Phytochemistry, 1985, 24, 1100.
C!sHI,02 M 228.290
Constit. of oil of myrrh. Liq.
Brieskorn, C.H. et a/, Phytochemistry, 1983, 22, 187.

345
Furanoeudesmane-3,4-diol - 7-Hydroperoxy-4(15)-eudesmen-12,8-... Sq-01073 - Sq-01079

Furanoeudesmane-3,4-diol Sq-01073 Heleniumlactone 1 Sq-01076

[125164-74-1]

CtsH 220 3
HO'g:qHO
M 250.337
(Ja.,4a.)-form
3a-Hydroxyfuroepaltol
Constit. of Epaltes gariepina. Oil. [a]i;' + 73° (c, 0.2 in
CHC1 3).
3-(2,3-Epoxy-2-methylbutanoyl): [125164-75-2].
C 20 H 28 0 5 M 348.438 C30H 420 3 M 450.660
Constit. of E. gariepina. Oil. Constit. of Helenium autumnale. Cryst. Mp 80°.
3-(3-Methylbutanoyl): [125164-76-3]. 5,6-Dihydro, 4,15-didehydro: Heleniumlactone 2
C20H 300 4 M 334.455 C30H 420 3 M 450.660
Constit. of E. gariepina. Oil. Constit. of H. autumnale. Oil.
3-Angeloyl: [125164-77-4]. Matusch, R. eta/, Helv. Chim. Acta, 1987, 70, 342.
C 20 H 280 4 M 332.439
Constit. of E. gariepina. Oil. [a]~ + 23° (c, 0.44 in Heleniumlactone 3 Sq-01 077
CHCI 3).
Zdero, C. eta/, Phytochemistry, 1989, 28, 3097 (isol, pmr)

Furanoeudesmane-3,4,6-triol Sq-01074

C1sH2204
HO'W?HO
M 266.336
OH

(Ja.,4a.,6fl)-form
3-(2,3-Epoxy-2-methylbutanoyl): [125164-78-5].
C 20 H 280 6 M 364.438
Isol. from Epaltes gariepina. Oil.
Zdero, C. et a/, Phytochemistry, 1989; 28, 3097 (isol, pmr)
Furanoeudesman-1-ol
8,12-Epoxy-3,7,11-eudesmatrien-1-o/
C 30 H 420 3 M 450.660
Constit. of Helenium autumnale. Oil.
Matusch, R. eta/, Helv. Chim. Acta, 1987, 70, 342.
4-Hydroperoxy-2,11(13)-eudesmadien- Sq-01078
Sq-01075 12,8-olide
4-Peroxy-2,11 (13)-eudesmadien-12 ,8-o/ide

HO
ffTY 'Fo 0

C1sH2002
~
M 232.322
C1sH 2004
(4a.,8fl)-form
~
M 264.321

Constit. of Artemisia iwayomogi. Oil. [aln + 24'' (c, 0.46

lP-form in CHC1 3).
Ac: [108044-18-4].
Greger, H. et a/, Phytochemistry, 1986, 25, 891.
C 17H 220 3 M 274.359
Constit. of Smyrnium galaticum. Amorph.
7-Hydroperoxy-4(15)-eudesmen-12,8-olide Sq-01 079

yj:?a
U1ubelen, A. eta/, J. Nat. Prod. (Lloydia), 1986, 49, 1104.

CtsHn04 M 266.336
(7a.,8fl)-form [129385-70-2]
Constit. of lnula racemosa. Yellow gum.
Goyal, R. et a/, Phytochemistry, 1990, 29, 2341 (isol, ms, ir, pmr)

346
1-Hydroxy-3,11(13)-eudesmadien-12,8-... - 3-Hydroxy-4,11(13)-eudesmadien-12,8-Sq-01080- Sq-01085

1-Hydroxy-3,11(13)-eudesmadien-12,8- Sq-01080 Constit. of Commiphora myrrh.

oUde Ac: Cryst. Mp 170°.

¢:x?o
Mincione, E. et al, Chim. Ind. (Milan), 1972, 54, 525.

2-Iiydroxy-4(15),11(13)-eudesmadien- Sq-01 084

HQy:x;ro
12,8-oUde

C 15H 280 3 M 248.321

(JP,Brz)-form
1-(2-M ethylpropanvyl): [111625-65-1 ]. Subcordatolide E
C1,H160 4 M 318.412 C 15H:11.03 M 248.321
Constit. of Ca/ea subcordata. Gum. (lrz,B/1)-form [5938-03-4] Iva/in
Ober, A.G. et al, J. Nat. Prod. (Lloydia), 1987, 50, 604. Constit. of Iva microcephala and /. imbriata. Cryst.
(C6H 6/pet. ether). Mp 130-132°. [ex]~ + 142° (c, 1.03 in
CHC13).
1-Hydroxy-4,11(13)-eudesmadien-12,8- Sq-01081 Herz, W. et al, J. Org. Chern., 1962, 27, 905.
oUde Tomioka, K. eta/, Tetrahedron Lett., 1984, 25, 333 (synth)

~q''=O 3-Hydroxy-4,11(13)-eudesmadien-12,8-
olide
Sq-01085

~
C 15H 280 3 M 248.321
(lp,B/1)-form [14164-59-1] lv1111gustin
H0'~0 (3a,8~)-fonn
lsol. from Iva angustifolia. Cryst. (CHC1 3jpet. ether). C1sH2003 M 248.321
Mp 120-122°. [cx]i; +85° (c, 1.05 in CHC1 3). (Jrz,B/1)-form
0-(2- M ethylbutanoyl): Constit. of Artemisia iwayomogi. Oil.
CzoH 280 4 M 332.439 3-Hydroperoxide: 3rz-Hydroperoxy-4,11(13)-eudesmadien-
Constit. of Wunderlichia mirabi/is. Oil. [cx]~4 +46° (c, 0.5 l1,8fl-olide. 3cx-Peroxy-4, II (13)-eudesmadien-12,8P-olide
in CHC13). C1sH2004 M 264.321
Herz, W. et al, J. Org. Chern., 1967, 32, 3658 (isol) From A. iwayomogi. Oil.
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 228 (derivs) 4cx,5cx- Epoxide: 4rz,5rz-Epoxy-3rz-hydroxy-11(13)-eudesmen-
Marco, J.A. eta/, Can. J. Chern., 1987, 65, 630 (synth)
11,BfJ-olide
C 15H 200 4 M 264.321
2-Hydroxy-3,11(13)-eudesmadien-12,8- Sq-01082 Constit. of A. iwayomogi. Oil. [cxJn + 140° (c, 0.18 in
oUde CHC1 3).
11 cx,13-Dihydro: 3rz-Hydroxy-4-eudesmen-11,8fJ-olide
HO,~O C 15H 220 3 M 250.337
Constit. of Ondetia linearis. Cryst. Mp 123°. [cx]i;' +99°
(c, 0.54 in CHC1 3).
(Jp,B/1)-form
C 15H 280 3 M 248.321 Ac: 3fJ-Acetoxy-4,11(13)-eudesmadien-11,8fJ-olide
(2«,8/1)-form C17H 210 4 M 290.358
Constit. of Ondetia linearis. Constit. of Calea szyszy/owiczii. Oil. [cxJn -25° (c, 0.11
Ac: Cryst. Mp 153°. [cx]i;' +71° (c, 0.27 in CHC1 3). in CHC1 3).
2-Ketone: [35730-85-9]. 2-0xo-3,11(13)eudesmadien-12,8P- 4cx,5cx-Epoxide: 4rz,5rz-Epoxy-3fJ-hydroxy-11(13)-eudesmen-
o/ide. Pinnatifidin 11,8fJ-olide
CtsHta03 M 246.305 C1sH2004 M 264.321
Constit. of Helenium pinn(ltijidum. Cryst. (C 6H 6/pet. From A. iwayomogi. Oil. [cx]n +250° (c, 0.05 in CDC13).
ether). Mp 164-165°. [cx]n +302.2° (c, 0.75 in EtOH). 11P,13-Dihydro: 3fJ-Hydroxy-4-eudesmen-11,8fJ-olide
Herz, W. et al, J. Org. Chern., 1962, 27, 4041 (Pinnatijidin) C 15H 210 3 M 250.337
Zdero, C. eta/, Phytochemistry, 1989, 28, 1653. Constit. of 0. linearis. Gum. [cx]i;' + 145° (c, 0.12 in
CHC1 3).
2-Hydroxy-4(15),7(11)-eudesmadien-12,8- Sq-01083 Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227 (isol)
Greger, H. eta/, Phytochemistry, 1986, 25, 891 (isol)
oUde Zdero, C. et al, Phytochemistry, 1989, 28, 1653.

HOWtO

C 15H 280 3 M 248.321

(2~,81;,10~)-form [39007-92-6) Commiferin

347
3-Hydroxy-4(15),11(13)-eudesmadien-... - 7-Hydroxy-4(15),11(13)-eudesmadien-... Sq-01086 - Sq-01091

3-Hydroxy-4(15), 11(13)-eudesmadien- Sq-01086 5-Hydroxy-4(15),11(13)-eudesmadien- Sq-01089

12,8-olide 12,8-olide

C 15H 200 3 M 248.321 C 15H 200 3

CJ:Vo
M 248.321
(31¥.,51¥.,8/1)-form [11322-82-6]/sote/ekin (51¥.,8/1)-form [6752-90-5] Te/ekin
Constit. of Te/ekia speciosa. Cryst. (Et20jpet. ether). Constit. of Telekia speciosa. Cryst. (EtOAcjheptane).
Mp 144-145°. [1X]i,I + 100.5° (c, 4.6 in CHC1 3). Mp 159.5-160°. [1X]i,I +234° (c, 4.56 in CHC13).
3-Hydroperoxide: 31X-Hydroperoxy-4(15), 11(13)- 5-Hydroperoxide: [89900-44-7]. 51X.-Hydroperoxy-
eudesmadien-12,8P-olide. 31¥.-Peroxyisoalantolactone 4(15),11(13)-eudesmadien-12,8P-olide
C 15H 200 4 M 264.321 C1 5H 200 4 M 264.321
lsol. from Artemisia iwayomogi. Cryst. Mp 148°. [1X]n Constit. of Calea szyszylowiczii. Oil. [IX]~ + 125° (c, 3.95
+93° (c, 0.48 in CHC1 3). in CHC1 3).
41X,15-Epoxide: 41X, 15-Epoxy-3-hydroxy-11 ( l3)-eudesmen- 41X,15-Epoxide: 4a., 15-Epoxy-SIX-hydroxy-11 (13)-eudesmen-
12,8P-olide. 41¥.,15-Epoxyisote/ekin 12,8P-olide. 4~¥.,15-Epoxyte/ekin
C 15H 200 4 M 264.321 C 15H 200 4 M 264.321
Constit. of Inula racemosa. Cryst. Mp 180°. Constit. of Inula racemosa. Cryst. Mp 164°.
(3P,51X.,8/1)-form (5p,8fJ)-form [89921-57-3]
Constit. of Gaillardia aristata. Mp 176-177°. [1X]i,6 C 15H200 3 M 248.321
+ 156.6° (c, 2.0 in CHC1 3). Constit. of C. szyszylowiczii. Cryst. (Et 20jpet. ether).
Benesova, V. eta/, Collect. Czech. Chern. Commun., 1961, 26, 1350 Mp 123°.
(isol, struct) 5-Hydroperoxide: [89921-56-2].
Herz, W. et al, J. Org. Chern., 1968, 33, 3743 (isol) C 15H 200 4 M 264.321
Miller, R.B. et al, J. Am. Chern. Soc., 1974, %, 8102 (synth)
Greger, H. et al, Phytochemistry, 1986, 25, 891 (hydroperoxide)
Constit. of C. szyszylowiczii. Cryst. (Etpjpet. ether).
Goyal, R. et al, Phytochemistry, 1990, 29, 2341 (epoxide) Mp 225°. [1X]~ -32° (c, 0.32 in CHC1 3).
Benesova, V. eta/, Collect. Czech. Chern. Commun., 1961, 26,
13'50; 1962, 27, 498 (isol, struct)
4-Hydroxy-5,11(13)-eudesmadien-12,8- Sq-01087 Marshall, J.A. eta/, J. Am. Chern. Soc., 1966, 88, 3408 (synth)
olide Bohlmann, F. eta/, Justus Lieblgs Ann. Chern., 1983, 2227.
Goyal, R. et al, Phytochemistry, 1990, 29, 2341 (isol, pmr)

~o)=o 7-Hydroxy-3,11(13)-eudesmadien-12,8- Sq-01090

H~ (41X,8~}form olide
I
C 15H 200 3 M 248.321
(41¥.,8/1)-form
4-Hydroperoxide: 4-Hydroperoxy-5,11(1 3)-eudesmadien-
12,8-o/ide
~~{o
C 15H 200 4 M 264.321 C15H200 3 M 248.321
Constit. of Calea szyszylowiczii. (5P,7P,8~X.,101X.)-form[72703-94-7] ent-71¥.-
(4p,8fJ)-form Hydroxydiplophyllo/ide
Constit. of C. szyszylowiczii. Oil. Constit. of Chi/oscyphus polyanthus. Cryst. (hexane). Mp
4-Hydroperoxide: Constit. of C. szyszylowiczii. 72-74°. [1X]n -36.1° (c, 1 in CHC1 3). Formerly thought
51X,6-Dihydro: 4-Hydroxy-11(13)-eudesmen-12,8fi-olide. to be SIX-hydroxy.
Septuplinolide Asakawa, Y. eta/, Phytochemistry, 1979, 18, 1007 (isol)
Constit. of C. septuplinervia. Cryst. Mp 171-172°. Asakawa, Y. et al, Phytochemistry, 1983, 22, 961 (struct)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2227.
Ober, A.G. eta/, Phytochemistry, 1987, 26, 848 (Septuplinolide) 7-Hydroxy-4(15),11(13)-eudesmadien- Sq-01091

Y=f?o
Tada, M. eta/, Chern. Lett., 1989, 1085 (synth) 12,8-olide

c:cq=o
4-Hydroxy-7(11),8-eudesmadien-12,8-olide Sq-01 088

HO C20 H 300 3 M 318.455

(71X.OH,8fJ)-form
C 15H 200 3 M 248.321
7~¥.-Hydroxyisoalantolactone
4~¥.-form [90332-92-6] Shizukolidol Constit. of Apa/ochlamys spectabilis.
Consit. of Chloranthus japonicus. Needles. Mp 194-195°.
Zdero, C. eta/, Phytochemistry, 1990, 29, 3201 (isol)
[1X]i,? -64° (c, O.o3 in CHC13).
Kawabata, J. et al, Agric. Bioi. Chern., 1984, 48, 713.

348
8-Hydroxy-4(15),7(11)-eudesmadien-... - 1-Hydroxy-3,7(11),8-eudesmatrien-... Sq-01092 - Sq-01098

8-Hydroxy-4(15),7(11)-eudesmadien-12,8- Sq-01 092 15-Hydroxy-4, 11(13)-eudesmadien-12,8- Sq-01095

olide olide

yj:(o C 15H 200 3

HOg::c{O

M 248.321
C 15Hll,0 3 M 248.321
BP-form [108560-05-0]
BP-form [73030-71-4] Atractylenolide Ill. 8-Hydroxyastero/ide Constit. of Inula racemosa. Cryst. Mp 217°.
Constit. of Aster umbellatus, Cryst. (Btpjpet. ether).
Mp 200-201° (192-193° ). [cx]i;' + 185.2° (c, 0.3 in 15-0-(6-Acetyl-P-v-glucopyranoside): [108544-68-9].
CHC1 3). A.bsinthifolide
C23 H 320 9 M 452.500
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 433. Constit. of Bahia absinthifolia. Yellow gum. [cx] 0
Uchida, M. et al, Chern. Pharm. Bull., 1980, 28, 92.
- 18.27° (c, 0.208 in CHC1 3).
15-Aldehyde: [116965-35-6]. 15-0xo-4,11(13)-eudesmadien-
9-Hydroxy-4,11(13)-eudesmadien-12,8- Sq-01093 12,8-o/ide. /soinunal
olide C,sH,80 3 M 246.305
Constit. of I. racemosa. Plant growth regulator. Cryst.
Mp 150°.
Perez, C.A.L. et a/, Phytochemistry, 1987, 26, 765 (Absinthifolide)
Kalsi, P.S. et a/, Phytochemistry, 1988, 27, 2079 (isol)

3-Hydroxy-12,8-eudesmanolide Sq-01096
C 15H 200 3 M 248.321

HO'~O
(7«,8«,9«,10«)-form
Ac: [64340-35-8]. 9-A.cetoxydiplophyllin
C 17H 220 4 M 290.358
Constit. of Diplophyllum albicans and D. taxifolium.
Cryst. Mp 92-95°. [cx] 0 -132° (pentane). C 15H 240 3 M 252.353
Ohta, Y. et al, Tetrahedron, 1977, 33, 617. (3«,4P,BP,11 «)-form [100045-43-0]
Constit. of Stevia achalensis. Oil.
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1986, 799.
15-Hydroxy-3, 11(13)-eudesmadien-12,8- Sq-01094
olide
1-Hydroxy-2,4(15), 11(13)-eudesmatrien- Sq-01097
12,8-olide

CH2 0H
C 15H 200 3 M 248.321
BP-form [119285-33-5]15-Hydroxyisoalloa/antolactone
Constit. of Ambrosia artemisioides. Oil.
C 15H 180 3 M 246.305
15-Ac: [119285-34-6]. 15-Acetoxyisoalloa/antolactone
C17H 22 0 4 M 290.358 (1«,8p)-form
Constit. of A. artemisioides. Oil. Constit. of Ferreyranthus fruticosus. Oil.
15-Cinnamoy/ (E-): [119285-35-7]. 15- Jakupovic, J. et al, Phytochemistry, 1988, 27, 1113.
CinnamoyloxyisoaUoalantolactone
C24H 260 4 M 378.467 1-Hydroxy-3,7(11),8-eudesmatrien-12,8- Sq-01098
Constit. of A. artemisioides. Oil. olide
15-Cinnamoyl (Z-): [119285-36-8].
Cl4Hl604 M 378.467
Constit. of A. artemisioides. Oil.
15-Aldehyde: [99103-26-1]. 15-0xo-3,11(13)-eudesmadien-
12,8P-olide. lnunal
C,sH 180 3 M 246.305
Constit. of Inula racemosa. Cryst. Mp 160°.
Kaur, B. et al, Phytochemistry, 1985, 24, 2007 (isol)
c,sH,ao3 M 246.305
Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551 (derivs) 1P-form
Ac: 1P-Acetoxy- 3, 7(11 ),8-eudesmatrien-12,8-o/ide
C 17H 200 4 M 288.343
Constit. of Smyrnium perfoliatum. Amorph.
Goren, N. eta(, Phytochemistry, 1987, 26, 2585.

349
1-Hydroxy-4(15),7(11),8-... - Lindestrene Sq-01099 - Sq-01106

1-Hydroxy-4(15),7(11),8-eudesmatrien- Sq-01099 2-Hydroxy-5-eudesmen-12,8-olide Sq-01103

12,8-olide

~0 C 15Hn03 M 250.337
(211.,8P,l111.H)-form
21X-Hydroxy-111X, 13-dihydroa/anto/actone
CtsHtsOJ M 246.305 Constit. of Ondetia linearis. Cryst. Mp 147°.
lP-forln II IX-Hydroxy: 21X, 111X-Dihydroxy-5-eudesmen-12,8/J-olide.
Ac: 1P-Acetoxy-4(15), 7(11 ),8-eudesmatrien-12,8-olide 21X, 111X- Dihydroxy-11, 13-dihydroa/anto/actone
C 17H 200 3 M 272.343 C 15H 1z04 M 266.336
Constit. of Smyrnium perfoliatum. Amorph. Constit. of 0. linearis. Cryst. Mp 186°. (1X]~4 -26° (c,
Goren, N. et a/, Phytochemistry, 1987, 26, 2585. 0.16 in CHC1 3).
(211.,8P,Jl PH)-form
3-Hydroxy-1,4(15),11(13)-eudesmatrien- Sq-01100 21X-Hydroxy-11p, 13-dihydroalt,mto/actone
12,8-olide Constit. of 0. linearis. Cryst. Mp 134°. [1X]i;' + 9° (c, 0.18
in CHC1 3).

~0'>= Zdero, C. eta/, Phytochemistry, 1989, 28, 1653.

HO~ O 4-Hydroxy-1-oxo-2,11(13)-eudesmadien- Sq-01104

12,8-olide
CtsHt 803 M 246.305

AT~0'-=o
(3p,8f/)-form [73723-60-1]
Constit. of Baltimora recta. Cryst. (CHC1 3 jhexane). Mp
146-147°. [1X]n + 160° (c, 2.5 in CHC1 3).
Ac: [73723-61-2].
C 17H 100 4 M 288.343
Constit. of B. recta. Cryst. (CHC1 3 jhexane). Mp 166-
C 15H 180 4
~
M 262.305
1670. [1X]n + 120° (c, 1.5 in CHC1 3).
(411.,811.)-form [92609-71-7] Subcordatolide B
Herz, W. eta/, Phytochemistry, 1979, 18, 1743.
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113. Constit. of Ca/ea subcordata. Cryst. (CHC1 3). Mp 188.5-
1890.
(4~~.,8/1)-form
5-Hydroxy-4(15),7(11 ),8-eudesmatrien- Sq-01101
Constit. of Ferreyranthus fruticosus. Cryst. Mp 117°.
12,8-olide
Ober, A.G. eta/, J. Nat. Prod. (Lioydia), 1984, 47, 626
(Subcordatolide B)
fryo'>= Jacupovic, J. eta/, Phytochemistry, 1988, 27, 1113 (isol)

~0 11-Hydroxy-3-oxo-1,4(15)-eudesmadien- Sq-01105
12,8-olide
CtsH 180 3 M 246.305
511.-form ~oh
o~~-i;-{ 0~
Constit. of Lophocolea heterophylla. Oil. [1X]n -149.3°
(c, 0.89 in CHC1 3).
Toyota, M. eta/, Phytochemistry, 1990, 29, 2334 (iso/, pmr, cmr)
CtsH 180 4 M 262.305
8-Hydroxy-1,4(15),7(11)-eudesmatrien- Sq-01102 (8P,ll11.)-form [33299-79-5] Farinosin
Constit. of Encelia farinosa and E. virginensis. Cryst.
12,8-olide

00
(CHC1 3 jhexane). Mp 200-201°. [1X]~4 -111° (c, 2.3 in
OH CHC1 3).
Herz, W. eta/, J. Org. Chern., 1968, 33, 3743.

Lindestrene Sq-01106
Furanoeudesma-1 ,4( 15)-diene
CtsH 180 3 M 246.305 [2221-88-7]
BP-form (20267-92-9] Hydroxylindestrenolide
Constit. of Lindera strychnifolia. Cryst. (EtOAc). Mp
220-221°. (IX]~ +209.8° (c, 1 in dioxan).
Takeda, K. eta/, J. Chern. Soc. C, 1968, 569.

CtsH 180 M 214.307

Constit. of Lindera strychnifolia. Bp2 100-102°. [1X)1~ -63.4°
(c, 0.8 in dioxan).

350
Mikacynancholide - 3-0xo-1,4(15),11(13)-eudesmatrien-... Sq-01107 - Sq-01112

1,2-Dihydro: [6989-21-5]. Atractylon. Furanoeudesm-4(15)- (7p,Bp,JO/l)-form

ene Isol. from Eupatorium quadrangulare and Artemisia
C 15H 200 M 216.322 iwayomogi. Ant repellant substance. Cryst. Mp 145-147°,
Constit. of Atractylis ovata and Atractylodes japonica. Mp 170°. [1X]i,' +161°.
Cryst. Mp 38°. [1X]n +40° (c, 10 in CHC1 3). Asakawa, Y. eta/, Phytochemistry, !979, 18, 1007 (isol)
Hikino, H. et a/, Chern. Pharm. Bull., 1962, 10, 641 (struct) Bohlmann, F. eta/, Phytochemistry, 1983, 23, 1185 (isol)
Minato, H. et a/, J. Chern. Soc. C, 1966, 1866; 1968, 621 (synth) Okunade, A.E. eta/, Phytochemistry, 1985, 24, 1199 (isol)
Takeda, K. eta/, J. Chern. Soc. C, 1969, 1920 (struct)
Miller, R.B. eta/, J. Org. Chern., 1973, 38,.4424 (synth)
3-0xo-1,4,11(13)-eudesmatrien-12,8-olide Sq-01111

~ikacynancholide Sq-01107
[92631-94-2]

~0 C 15H 160 3 M 244.290

BP-form [10067-18-2] Yomogin
Constit. of Artemisia princeps. Cryst. (EtOAc). Mp 201-
2020. [1X]~ -88° (c, 0.11 in CHC1 3).
0
lliX,JJ-Dihydro: 3-0xo-1,4-eudesmadien-12,8P-olide. llrx,JJ-
C 15H 140 5 M 274.273 Dihydroyomogin
Constit. of Mikania cynanchifolia. Gum. C15H 180 3 M 246.305
Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1099. Constit. of Ferreyranthus fruticosus. Cryst. Mp 167°.
11X,21X- Epoxide: 11X,21X- Epoxy-4, 11 (13)-eudesmadien-12,8P-
Nehipediol Sq-01108 olide. lrx,2rx-Epoxyyomogin
IP,51X-Dihydroxyfuranoeudesman-6-one C 15H 160 4 M 260.289
[62433-66-3] Constit. of F. fruticosus. Cryst. Mp 176°.
11X,21X-Epoxide, 4P,51X-dihydro: see 3-0xo-1 ,4(15), 11 (13)-
OH eudesmatrien-12,8-olide, Sq-01112

~0\
Geissman, T.A., J. Org. Chern., 1966, 31, 2523 (isol, struct)
Caine, D. et a/, Tetrahedron Lett., 1975, 743 (synth)
Marco, J.A. eta/, Can. J. Chern., 1987, 65, 630 (synth)

~
OH
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113 (derivs)

3-0xo-1,4(15),11(13)-eudesmatrien-12,8- Sq-01112
C 15H 200 4 M 264.321 olide
Constit. of Nepeta hindostana. Cryst. (MeOH). Mp 150-
1520.
St. Pyrek, J. eta/, Pol. J. Chern. (Rocz. Chern.), 1976, 50, 1931.

Nehipetol Sq-01109
I IX- Hydroxyfuranoeudesm-4-en-6-one. Curcolone C 15H 160 3 M 244.290
[17015-43-9] BP-form [15569-50-3] Encelin. Dehydrofarinosin
Constit. of stems of Encelia farinosa. Cryst.
OH (EtOAcjhexane). Mp 195-196°. [IX]~ -16.SO (c, 3.67 in

M
I
CHC1 3).
41X,l5-Dihydro: [92592-61-5]. 3-0xo-1,11(13)-eudesmadien-
12 ,8P-olide. 4rx,15-Dihydroencelin
C 15H 180 3 M 246.305
0 Constit. of Perymenium featherstonei. Cryst. (Et 20). Mp
C 15H 180 3 M 246.305 175°. [1X]i;' +14° (c, 0.1 in CHC1 3).
Constit. of Nepeta hindostana. Cryst. (MeOH). Mp 152- lliX,13-Dihydro: [36170-17-9]. 3-0xo-1 ,4(1 5)-eudesmadien-
1540. [1X]n + 13.7° (c, 3.8 in CHC1 3). 12,8P-olide. Virginin. Dihydroencelin
Hikino, H. eta/, Chern. Pharm. Bull., 1968, 16, 827 (isol, struct) C 15H 180 3 M 246.305
St. Pyrek, J. eta/, Pol. J. Chern. (Rocz. Chern.), 1976, 50, 1931. Constit. of E. virginensis. Cryst. (Et20). Mp 241-242°.
[1X]~4 -128° (c, 0.14 in CHC1 3).
3-0xo-4,11(13)-eudesmadien-12,8-olide Sq-01110 41X,l5-Dihydro, 11X,21X-epoxide: [90746-98-8]. 11X,21X- Epoxy- 3-
oxo-11 (13)-eudesmen-12,8P-olide. Himeyoshin
C,sH 180 4 M 262.305
Constit. of Artemisia feddei. Mp 214-215°.
(7 et,8et, 1Oet )-form 4P,J5-Dihydro, 11X,21X-epoxide: lrx,1rx-Epoxy-4p,5-
dihydroroyomogin
c,5H 180 4 M 262.305
C, 5H, 80 3 M 246.305 Constit. of Ferreyranthus fruticosus. Cryst. Mp 185°.
(7rx,Brx,10rx)-form [72747-95-6] 3-0xodip/ophy//in Geissman, T.A. et a/, J. Org. Chern., 1968, 33, 656 (Encelin)
Constit. of Chiloscyphus polyanthus. Cryst. Mp 170-171°. Sims, J .J. et al, Phytochemistry, 1972, 11, 444 ( Virginin)
[1X]n -40.2° (c, 0.4 in CHC1 3). Bohlmann, F. et al, Phytochemistry, 1983, 23, 1185 (4,15·
Dihydroencelin)

351
1-0xo-7(11)-eudesmen-12,8-olide - 1,3,6-Trihydroxy-4,11(13)-... Sq-01113 - Sq-01119

Nagaki, M., Phytochemistry, 1984, 23, 462 (Himeyoshin) Stylotellin Sq-01117

Jakupovic, J. et al, Phytochemistry, 1988, 27, 1113 (1,2-Epoxy-4,5-
dihydroroyomogin) [108648-45-9]
Milman, I.A. et al, Khim. Prir. Soedin., 1990, 26, 307; Chern. Nat.
Compd. (Engl. Trans/.), 251 (rev)

1-0xo-7(11)-eudesmen-12,8-olide Sq-01113

C16H 25N M 231.380

Constit. of sponge Stylotella sp. Oil. [ex] 0 -47° (c, 1.7 in
CHC13).
Pais, M. et al, Tetrahedron Lett., 1987, 28, 1409.

C 15H 200 3 M 248.321 1,4,6,9-Tetrahydroxy-11(13)-eudesmen- Sq-01118

8rx.-form [108044-20-8] 12,8-olide
Constit. of Smyrnium galaticum. Amorph.
Ulubelen, A. et al, J. Nat. Prod. (Lloydia), 1986, 49, 1104. HO OH

3-0xo-11(13)-eudesmen-12,8-olide Sq-01114
H~o
~0 C 15H 220 6 M 298.335
(lfl,4rx.,6fl,8Jl,9fl)-form
1,9-Di-Ac: Trilobolidet
C 15H 200 3 M 248.321 C19H 260 8 M 382.410
(4f.,5f.,7fl,8fl,l0f.)-form [50334-39-9] Graveolide 6-(Methy/propanoyl), 1,9-di-Ac:
Constit. of lnula graveo/ens. Cryst. Mp 153-154°. (ex]~ C23H 320 9 M 452.500
+ 157.6° (c, 5 in CHC1 3). Constit. of Wedelia trilobata. Cryst. (Etp). Mp 230-
d'A1contres, G.S. et al, Gazz. Chim. !tal., 1973, 103, 239. 2310. (ex]i;' +30.8° (c, 0.7 in CHC1 3).
6-Ange/oy/, 1,9-di-Ac:
Rudbeckiolide Sq-01115 C24H 320 9 M 464.511
[1 02260-72-0] Constit. of W. trilobata. Cryst. (Etp). Mp 180-186°.
(ex]i;' + 12.8° (c, 0.6 in CHC1 3).
6-(Methy/propenoyl), 1,9-di-Ac:
C23H 300 9 M 450.485
Constit. of W. trilobata. Gum.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 751.

,,
1,3,6-Trihydroxy-4,11(13)-eudesmadien- Sq-01119

M
0 12,8-olide
HO
C30H 360 4 M 460.612
Constit. of roots of Rudbeckia /aciniata. Oil.
0
Jakupovic, J. et al, Justus Liebigs Ann. Chern., 1986, 1474.
H
Shizukafuranol Sq-01116 OH
Furanoeudesman-4-o/. Furoepaltol C 15H 200 5 M 280.320
[90332-93-7] Named as derivatives of Steiractino1ide which is unknown.
(lrx.,3fl,6rx.,8f/)-form

HO
Q)Q 6-Tigloy/, 3-Ac: (86918-90-3].
C22 H 280 7

CHC1 3).
M 404.459
Constit. of Steiractinia mol/is. Oil. [ex]i;' +48° (c, 0.27 in

C 15H 22 0 2 M 234.338 6-Tig/oy/, l-Ac: (86918-91-4].

Constit. of Ch/oranthus japonicus. Cryst. M p 69-70°. [ex]~ C22 H 280 7 M 404.459
-67.1° (c, 0.16 in CHC1 3). Constit. of S. mol/is. Oil. [ex]i;' + 50° (c, 0.22 in CHC1 3).
Kawabata, J. et al, Agric. Bioi. Chern., 1984, 48, 713. 6-Tigloy/, 1,3-di-Ac: [86918-92-5].
C24H 300 8 M 446.496
Constit. of S. mol/is. Oil. [ex]~4 +65° (c, 0.72 in CHC13).
6-(2-Methylpropenoyl), 3-(2-methy/propanoyl), l-Ac: [86918-
94-7].
C25H 320 8 M 460.523
Constit. of Aspilia pluriseta. (ex]i;' +49° (c, 0.36 in
CHC1 3).

352
1,4,6-Trihydroxy-11(13)-eudesmen-... - Decipienin B Sq-01120- Sq-01124

6-(2-Methylpropenoyl), 1,3-di-Ac: [86918-95-8].

12,6-Eudesmanolides
C23H:zs08 M 432.469
Constit. of A. pluriseta. Cryst. (Etp). Mp 123-124°. [ocJi:
+ 70° (c, 0.39 in CHC1 3).
[86918-88-9)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 962 (cryst
struct)
Cyclocratystyolide Sq-01122
1,4,6-Trihydroxy-11(13)-eudesmen-12,8- Sq-01120 [114916-02-8]
olide

C 15H 22 0 5
m
Hci
M 282.336
(1 p,4rz,6rz,8rz )-form
lm \
0

C20H 260 7 M 378.421

1,6-Di-Ac: 1fi,6oc-Diacetoxy-4oc-hydroxy-11-eudesmen-12,8oc- Constit. of Cratystylis conocephala. Oil.
olide
Zdero, C. et a/, Phytochemistry, 1988, 27, 865.
Ct9H260 7 M 366.410
Constit. of Gnephosis arachnoidea. Gum. [oc]i;4 -7° (c,
0.25 in CHC1 3). (X-Cyclohallerin Sq-01123
(1P,4f.,6rz,8rz)-form
6-Angeloyl: [60323-90-2]. Tanapsin
C20H:zs06 M 364.438
Constit. of Tanacetum pseudoachillea. Cryst. Mp 191-
1920. [oc]i;4 -139° (c, 1.38 in MeOH).
Yunusov, A.l. et a/, Khim. Prir. Soedin., 1976, 309.
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3181.
C20 H:14P 4 M 334.455
Tubipofuran Sq-01121 Constit. of Laserpitium halleri as a mixt. of 12-epimers.
Furanoeudesma-1 ,3-diene Me ether (12/f): Methyl-oc-cyclohallerin
Gum. [oc]i; -140° (c, 0.51 in CHC1 3).
!14•15 -Isomer: P-Cyclohallerin
C20 H 300 4 M 334.455
Constit. of L. halleri as a mixt. of 12-epimers.
!14 •15 -Isomer, Me ether (12/f): Methyl-p-cyclohallerin
Oil. [oc]i; + 8° (c, 0.6 in CHC1 3).
C 15H 180 M 214.307
Appendino, G. eta/, Phytochemistry, 1987, 26, 1755.
lsol. from Tubipora musica. Shows cytotoxic and
ichthyotoxic props. Oil. [ocln + 5. 7° (c, 0.6 in CHC1 3).
15-Acetoxy: 15-Acetoxytubipofuran Decipienin B Sq-01124
C17H 200 3 M 272.343 [51943-81-8]
From T. musica. Shows cytotoxic and ichthyotoxic
props. Oil. [ocln + 10.7° (c, 0.5 in CHC1 3).
Iguchi, R. eta/, Chern. Lett., 1986, 1789 (isol)

C20 H 260 6 M 362.422

Constit. of Melanoselinum decipiens. Cryst. (C6H 6 jpet.
ether). Mp 160-162°. [ocJn +44° (c, 3 in EtOH).
Gonzalez, A.G. eta/, An. Quim., 1973, 69, 1339.

353
1,3-Dihydroxy-4,11(13)-eudesmadien-... - 1,5-Dihydroxy-4(15),11(13)-... Sq-01125 - Sq-01127

1,3-Dihydroxy-4,11(13)-eudesmadien-12,6- Sq-01125 Irwin, M.A. eta/, Phytochemistry, 1973, 12, 871 (Ridentin B)
Samek, Z. et a/, Collect. Czech. Chern. Commun., 1975, 40, 2676
olide (Erivanin)
Arias, J.M. eta/, J. Chern. Soc., Perkin Trans. I, 1987, 471 (synth)
HOI Harapanhalli, R.S. eta/, J. Chern. Soc., Perkin Trans. I, 1988,
2633 (synth)
(1 a.,3a.,6a.)-form Bruno, M. et a/, Phytochemistry, 1988, 27, 1201 (1-Epierivanin)
Sanz, J.F. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 940 (3-
HO' Epierivanin)
I

0 1,5-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01127
C15H2004 M 264.321 12,6-olide
(1rx..Jrx.,6rx.)-form
1rx..Jrx.-Dihydroxyarbusculin B HO

M
Constit. of Schistostephium hepatolobum. Gum. [IX]~
+ 18° (c, 0.1 in CHC1 3).
(lp.Jrx.,6rx.)-form [94529-67-6] Armefolin
Constit. of Artemisia mexicana. Cryst. Mp 175°. [1X]n
+ 105.5° (c, 2 in CHC1 3).
ITiiiQ= 0
(tp,5a,6a)-fo'm

(lp.Jp,6rx.)-form
C15H2004 M 264.321
3-Ac: [72635-13-3]. Montathanolide
(lp,5rx.,6rx.)-form [1401-54-3] Tanacetin
C17H2205 M 306.358 Constit. of Tanacetum vulgare. Cryst. (CHClJMe 2CO).
Constit. of Athanasia dregeana. Oil.
Mp 205-206°. [1X]i;5 + 154° (c, 0.15 in EtOH).
3-Ketone: see 1-Hydroxy-3-oxo-4,11(13)-eudesmadien-12,6-
111X,l3-Dihydro: [36312-98-8]. Arsubin
o/ide, Sq-01181
C15H2204 M 266.336
(1 rx..Jrx.,6f/)-form lsol. from Artemisia fragrans and A. transiliensis. Cryst.
Di-Ac: [41929-27-5]. Armexin (EtOH). Mp 233-234°. [rx.Ji? +217.2° (c, 1 in EtOH).
C 19H 140 6 M 348.395 np,JJ-Dihydro: [22149-38-8]. IP,51X-Dihydroxy-4(15)-
lsol. from A. mexicana.
eudesmen-12,61X-Oiide. Artemin
Romo, J. eta/, Rev. Latinoam. Quim., 1972, 3, 122; CA, 78, C15H2204 M 266.336
121339m (Armexin) Constit. of Artemisia spp. Cryst. (EtOAcjpet. ether).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 995; 1983, 23, 1665.
Mp 238-240°. [1X]n + 167° (c, 0.5 in CHCl 3).
Mata, R. et a/, Phytochemistry, 1984, 23, 1665 (Armefolin)
11P,13-Dihydro, l-Ac:
C17H1405 M 308.374
1,3-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01126 lsol. from A. herba-alba. Gum.
12,6-olide (lp,5p,6rx.)-form
11 p,JJ-Dihydro: [129138-11-0]. lsogaUicadiol
C15H2204 M 266.336
Isol. from A. maritima. Cryst. (CH 2C12 jhexa111e). Mp
187-189°. [1X]n -94.2° (c, 0.2 in CHC1 3).
(1 rx.,5rx.,6rx. )-form
11P,J3-Dihydro: 1-Epiartemin
C 15H 200 4 M 264.321
C15H2004 M 264.321 lsol. from A. diffusa. Cryst. Mp 188°.
(lrx..Jrx.,6rx.)-form [27740-14-3] Ludovicin B Tarasov, V.A. eta/, Khim. Prir. Soedin., 1971, 7, 480; 1973, 9, 745;
Constit. of Artemisia ludoviciana. Cryst. Chern. Nat. Compd. (Engl. Trans/.), 722, 649 (Arsubin)
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1973, 38, 1971
(CHP2/Et0Ac). Mp 152°. [1X]i;5 + 138°. (iso/, struct)
11 p,J3-Dihydro: [25645-08-3]. 11X,31X•Dihydroxy-4(15)- Gonzalez, A.G. eta/, Phytochemistry, 1977, 16, 1836 (Artemin,
eudesmen-12,61X-olide. Erivanin Arsubin)
CI5H2204 M 266.336 El-Feraly, F.S. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 355
Constit. of A. fragrans. Cryst. Mp 203-205°. [1X]i? + 112° (synth)
(c, 3.9 in EtOH). Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 2723 (1-Epiartemin)
Gonzalez, A.G. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 462
(1rx..JP,6rx.)-form (lsogallicadiol)
11P,l3-Dihydro: 3-Epierivanin Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3661 (deriv)
C15H220 4 M 266.336
Constit. of A. herba-a/ba. Gum. [IX]~ + 124° (c, 0.7 in
CHCl 3).
(1 P.Jrx.,6rx. )-form
11 p,JJ-Dihydro: [32203-46-6]. 1p,31X-Dihydroxy-4( 15)-
eudesmen-12,61X-olide. 1-Epierivanin
C 15H 220 4 M 266.336
Constit. of Picris acu/eata. Gum.
(lp.Jp,6rx.)-form [41653-78-5] Ridentin B
Constit. of A. tripartita. Cryst. (EtOAc). Mp 188-190°.
Lee, K.H. eta/, Phytochemistry, 1970, 9, 403 (Ludovicin B)

354
1,7-Dihydroxy-3,11(13)-eudesmadien-... - 1,8-Dihydroxy-4,11(13)-eudesmadien-... Sq-01128 - Sq-01131

1,7-Dihydroxy-3,11(13)-eudesmadien-12,6- Sq-01128 11 p,l3-Dihydro: 81¥.-Hydroxy-IIP,l3-dihydrobalchanin

olide C15H 2204 M 266.336
lsol. from L. serotina. Oil.

9?;
HO (1 p,6~¥.,8/l)-form
Sfi-Hydroxybalchanin
8-Ac: [56064-70-1]. 11.-Liriodenolide
Ct,H220 5 M 306.358
Constit. of Liriodendron tulipifera. Cryst.
(Et20/diisopropyl ether). Mp 72-73°.
0 8-Angeloyl:
C15H:1004 M 264.321 C20 H 260 5 M 346.422
(lft,61¥.,71¥.)-form Constit. of Tithonia rotundifolia. Gum. [1X]i;' + 58° (c,
7-Hydroxysantamarine 0.05 in CHC1 3).
Constit. of Decachaeta ovalifolia. Cryst. (as l-Ac). Mp 8-(3-Hydroxy-2-methylenebutanoyl): [92356-87-1].
210° dec. (l-Ac). Tirotundifolin C
De Luengo, D.H. et a/, Phytochemistry, 1986, 25, 1917. C20H 260 6 M 362.422
Constit. of Tithonia rotundifolia. Cryst.
(Me2CO/hexane). Mp 168-170°. [1X] 0 +30.8° (c, 0.2 in
1,7-Dihydroxy-4(15), 11 (13)-eudesmadien- Sq-01129 MeOH).
12,6-olide
8-(2-Hydroxymethyl-2-propenoyl)(Z-): [92356-86-0].
7-Hydroxyreynosin
Tirotundifolin D
C20H 260 6 M 362.422
Constit. ofT. rotundifolia. Cryst. (Me 2CO/hexane). Mp
163-165°.
8-(2,3-Epoxy-2-methylbutanoyl):
C20 H 260 6 M 362.422
Constit. of T. rotundifolia. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 267; 1982, 21, 1343
C 15H 200 4 M 264.321 (is of)
Holub, M. eta/, Collect. Czech. Chern. Commun., 1982, 47, 2927
(lft,61¥.,71¥.)-form (8- Hydroxybalchanin)
Constit. of Decachaeta ovatifolia. Doskotch, R.W. eta/, J. Nat. Prod. (Lloydia), 1983, 46, 923 (1¥.-
l-Ac: Cryst. Mp 199° dec. Liriodenolide)
Serkerov, S.V. et a/, Khim. Prir. Soedin., 1983, 19, 578 (Artapshin)
De Luengo, D.H. eta/, Phytochemistry, 1986, 25, 1917. Perez, A.L. et a/, Phytochemistry, 1984, 23, 823 (Tirotundifolins)
Mata, R. eta/, Phytochemistry, 1984, 23, 1665 (Epoxyludalbin)
1,8-Dihydroxy-3,11(13)-eudesmadien-12,6- Sq-01130 Fernandez, J. eta/, Tetrahedron, 1987, 43, 805 (synth, Artapshin)
olide
1,8-Dihydroxy-4,11(13)-eudesmadien-12,6- Sq-01131
HOI olide

?rro"
~ (1~.6a,8a)-fo~

Ct5H2004 M 264.321
0
[36204-28-1] Dimerostemmabrasiolide
(1~¥.,611.,81¥. )-form
l-Ac: [36437-92-0]. lsoludalbin Ct5H2004 M 264.321
C17H 22 0 5 M 306.358 (1 p,6~~.,8~~. )-form
Constit. of Artemisia ludoviciana. Cryst. (EtOAcjpet. 8-Ac: [41059-81-8]. y-Liriodenolide
ether). Mp 174-175°. Ct,H 220 5 M 306.358
8-Ac: [36437-90-8]. Ludalbin Constit. of Liriodendron tulipifera. Cryst. (Etpjhexane).
C17H 220 5 M 306.358 Mp 179-180°. [1X]~ -4° (c, 0.25 in MeOH).
Constit. of A. ludoviciana and A. mexicana. Cryst. 8-Angeloyl: Chapinolin
(Etpjpet. ether). Mp 169-171°. [iX]iJ +227.6° (c, 1 in C:10H 260 5 M 346.422
CHC1 3). Constit. of Squamopappus skutchii. Gum.
1-0-(2-Hydroxymethylpropenoyl): 11P,J3-Dihydro: [125675-23-2]. Ip,8~~.-Dihydroxy-4-
C19H 2406 M 348.395 eudesmen-12,61¥.-olide
Constit. of Dimerostemma brasilianum. Gum. C15H 2204 M 266.336
61X,71X-Epoxide, 8-Ac: 11.-Epoxyludalbin lsol. from Artemisia herba-a/ba. Needles
C17H 220 6 M 322.357 (EtOAcjhexane). Mp 92-94°.
Constit. of A. mexicana. Cryst. Mp 185°. (lft,61¥.,8fl)-form
(lft,61¥.,81¥.)-form [84305-05-5] 811.-Hydroxybalchanin 8-Ange/oyl:
Constit. of Leucanthemella serotina. Cryst. C:10H260 5 M 346.422
(CHC1 3/Et20). Mp 80-82°. [1X]i,O + 150.6° (c, 0.29 in Constit. of Tithonia rotundifolia. Gum.
CHC1 3). 8-(2,3-Epoxy-2-methy/butanoyl):

355
1,8-Dihydroxy-4(15),11(13)-... - 1,9-Dihydroxy-4(15),11(13)-... Sq-01132 - Sq-01134

C20H 260 6 M 362.422 Constit. of Tithonia rotundifolia. Cryst.

Constit. of T. rotundifolia. (Me 2C0jhexane). Mp 90-92°. [1X]n + 56.9° (c, 0.23 in
8-(3-Hydroxy-2-methy/enebutanoyl): CHC1 3).
C20H 260 6 M 362.422 8-(2,3-Dihydroxy-2-methy/butanoyl): [92356-85-91.
Constit. ofT. rotundifolia. Cryst. (Me 2COjhexane). Mp Tirotundifolin E
163-165°. [1X]n -12.2° (c, 0.212 in MeOH). C20 H 280 7 M 380.437
lliX,l3-Dihydro, 8-Ac: [128502-76-1]. BP-Acetoxy-lP- Constit. ofT. rotundifolia. Cryst. (Me 2C0jhexane). Mp
hydroxy-4-eudesmen-12 ,6rz-olide 213-215°. [1X]n +9.3° (c, 0.224 in MeOH).
C 17H 240 5 M 308.374 8-(3-Hydroxy-2-methylenebutanoyl): [94190-29-1].
lsol. from Stevia aff. tomentosum. Cryst. Mp 162-164°. Trichomatolide D
(6p,8rz )-form C20 H 2P 6 M 362.422
]-Ketone: see 8-Hydroxy-1-oxo-4-eudesmen-12,6-o/ide, Sq- Constit. of Calea trichomata. Gum.
01190 8-(2-Hydroxymethy/-2-butenoyl)(E-): [94190-28-0].
[125761-13-9] Trichomatolide E
Doskotch, R.W. et a/, Phytochemistry, 1975, 14, 769 (y- C20 H 260 6 M 362.422
Liriodenolide) Constit. of C. trichomata. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 267. (lp,sp,6p,ap,JOrz)-form
Perez, C.A.L. eta/, Phytochemistry, 1984, 23, 823 (Tirotundifolin Constit. of Pegolettia oxydonta. Gum.
B)
Vargas, D. eta/, Phytochemistry, 1988, 27, 1413 (Chapinolin) Bohlmann, F. eta/, Chern. Ber., 1978, 111, 843; 1980, 1113, 2410.
Marco, J.A., Phytochemistry, 1989, 28, 3121 (isol, deriv) Hoeneisen, M. et a/, Phytochemistry, 1980, 19, 2765 (Arturin)
Martinez-Vazquez, M. et a/, Phytochemistry, 1990, 29, 1689 (deriv) Doskotch, R.W. eta/, J. Nat. Prod. (Lloydia), 1983, 46, 923 (/J-
Liriodenolide)
Perez, A.L. et a/, Phytochemistry, 1984, 23, 823 (Tirotundifolins)
1,8-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01132 Ober, A.G. eta/, Phytochemistry, 1984, 23, 1439 (Trichomatolides)
12,6-olide Fernandez, I. et a/, Tetrahedron, 1987, 43, 805 (synth)
Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 1535.
1,8-Dihydroxy-ft-cyclocostunolide
Bohlmann, F. eta/, Phytochemistry, 1989, 28, 1949.
HOI
1,9-Dihydroxy-3,11(13)-eudesmadien-12,6- Sq-01133
olide
(1 a,6a,8a)-:form HOI OH
I

C 15H 200 4 M 264.321

(lrz,6rz,8rz)-form [66656-17-5]
Constit. of Zexmenia phyllocephala. Cryst. Mp 202-204°.
1-(Methy/propanoyl):
C 19H 260 5 M 334.411 C 15H 200 4
~
M 264.321
0

Constit. of Z. gnaphaloides. Oil. [1X]~4 + 136° (c, 0.15 in (lrz,6rz,9rz)-form [100343-65-5]1rz,9rz-Dihydroxy-rz-

CHC1 3). cyclocostunolide
11 p,J3-Dihydro, 1-(methy/propanoyl): Constit. of Pluchea dioscoridis. Oil. [1X]i,S + 135° (c, 0.1 in
CHC1 3).
CI9H280s M 336.427
Constit. of Z. gnaphaloides. Oil. [1X]i;' + 142° (c, 0.35 in (lp,6rz,9rz)-form
CHC1 3). 9rz-Hydroxysantamarine
llft,13-Dihydro, 1-(2-hydroxymethylpropanoyl): Constit. of P. dioscoridis. Cryst. Mp 149°. [1X]i;' +56.7°
(c, 0.2 in CHC1 3).
CI9H280 6 M 352.427
Constit. of Z. gnaphaloides. Oil. [1X]~4 + 161° (c, 0.78 in Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1975 (9a:-
CHC1 3). Hydroxysantamarine)
Dawidar, A.-A. et a/, Chern. Pharm. Bull., 1985, 33, 506B
(lft,6rz,8rz)-form (Dihydroxy-a:-cyclocostunolide)
lliX,l3-Dihydro: Desacetyldihydro-p-cycloisopyrethrosin
C!sHzz04 M 266.336 1,9-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01134
Isol. from Chrysanthemum cinerariaefolium. Cryst. +!
EtOAc. Mp 196-197° (softens at 112°). [1X]~4 + 184° (c, 12,6-olide
0.125 in MeOH).

~
(1P,6rz,8/l)-form
8-Ac: [69845-02-9]. P-Liriodenolide
C 17H 2z0 5 M 306.358
Constit. of Liriodendron tulipifera. Cryst.
(Et20jdiisopropy1 ether). Mp 119-120°.
8-Ange/oyl: [78012-26-7]. Arturin 0
C20 H 26 0 5 M 346.422
C 15H 200 4 M 264.321
Constit. of Podanthus mitiqui. Oil.
(lp,5rz,6rz,9/l)-form [83117-69-5] 9p-Hydroxyreynosin
8-(2,3-Epoxy-2-methy/butanoyl): [92356-89-3]. Tirotundifolin
Constit. of lnula heterolepsis. Gum. [1X]i;' + 19° (·~. 0.1 in
A
CHC1 3).
M 362.422

356
2,5-Dibydroxy-4(15),11(13)-... - 1,4-Dibydroxy-12,6-eudesmanolide Sq-01135 - Sq-01140

11 p,13-Dihydro: 1p,9P-Dihydroxy-4(15)-eudesmen-12,6a- (4«,6«)-form [41988-88-9] Arbusculill D

olide. 9/J-Hydroxy-11 ,13-diltydroreynosin Constit. of Artemisia arbuscu/a. Cryst. (EtOAc). Mp
C15Hn04 M 266.336 170-172°.
lsol. from Artemisia herba-a/ba. Gum. Irwin, M.A. eta/, Phytochemistry, 1973, 12, 853.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1166 (9-
Hydroxyreynosin)
Ahmed, A.A. eta/, Phytochemistry, !990, 29, 3661 (9-Hydroxy-
5,8-Dihydroxy-4(15), 11(13)-eudesmadien- Sq-01138
!!, 13-dihydroreynosin) 12,6-olide

2,5-Dihydroxy-4(15),11(13)-eudesmadien- Sq-01135
12,6-olide

C15H100 4 M 264.321
(5«,6«,8«)-form [33530-73-3] Rot/tin B
Constit. of Artemisia rothrockii. Cryst. (EtOAc). Mp
254-256°. [a]i; +242° (c, 1.45 in MeOH).
C,sH100 4 M 264.321 (51; ,61; ,81;)-form
(2«,5«,6/1)-form 11,,13-Dihydro, 8-Ac: [107195-85-7]. Nitrosin
2-Ac: [128988-29-4]. 2«-Acetoxy-5«- C17H 1•.05 M 308.374
ltydroxyisosplrllerfllltltolide Constit. of A. nitrosa. Cryst. (Etpjhexane). Mp 187-
C 17H 220 5 M 306.358 1880. [a]!: + 37.7° (c, 1.2 in EtOH) .
. Constit. of Sphaeranthus suaveolens. Gum. Irwin, M.A. eta/, Phytochemistry, 1971, 10, 637 (isol, struct)
5-Hydroperoxide, 2-Ac: [128988-30-7]. 2«-Acetoxy-5«- Carda, M. et a/, Tetrahedron, 1986, 42, 3655 (synth)
ltydroperoxyisosphaerfllltltolide Adekenov, S.M. eta/, Khim. Prir. Soedin., 1986, 22, 608 (Nitrosin)
C 17Hn06 M 322.357
Constit. of S. suaveolens. Gum. 1,3-Dihydroxy-12,6-eudesmanolide Sq-01139
Jakupovic, J. eta/, Phytochemistry, 1990, 29, 1213 (isol, pmr)

2,7-Dihydroxy-4,11(13)-eudesmadien-12,6- Sq-01136
olide
HO~H~ '
0
II
--

0
C,sH240 4 M 268.352
(JP,JP,4P,6«,11«)-form
4,11,13,15- Tetraltydroridentin B
C 15H100 4 M 264.321 Constit. of Taraxacum officina/e. Cryst. (Et20jpet.
ether). Mp 141-142°.
(2«,6P,7«)-form [128988-26-1]
2a, 7a-Dihydrosphaerantholide Hansel, R. et a/, Phytochemistry, 1980, 19, 837.
Constit. of Sphaeranthus suaveolens. Cryst. Mp 176°.
[a]i; -32° (c, 0.62 in MeOH). 1,4-Dihydroxy-12,6-eudesmanolide Sq-01140
2-Ac: [128988-27-2].
C 17H 220 5 M 306.358
Constit. of S. suaveolens. Cryst. Mp 167°. [a]i;' -91° (c,
2.88 in CHC1 3).
11a,J3-Dihydro: [128988-28-3]. 2«,7«-Dihydroxy-4-
eudesmen-12,6/J-olide
C 15H 220 4 M 266.336
Constit. of S. suaveolens. Cryst. Mp 229°. [a]i; -18° (c,
0.67 in MeOH). C,sH240 4 M 268.352
Jakupovic, J. et al, Phytochemistry, !990, 29, 1213 (isol, pmr) (JP,4«,6«,11PH)-form [66428-35-1]
1P-Hydroxyarbuscalin A
4,13-Dihydroxy-7(11)-eudesmadien-12,6- Sq-01137 Constit. of Vladimiria souliei and Tanacetum vulgare.
olide Prisms (EtOH). Mp 200-201 o (194-196°).
(1P,4«,6P,11«H)-form
11P-Hydroxy-11-epicolartin
Isol. from Artemisia herba-alba. Cubes (EtOAc). Mp
250-251°.
(1 p,4P,6P,11«H)-form
11P-Hydroxy-4,11-diepicolartin
Isol. from A. herba-alba. Cubes (EtOAc). Mp 198-200°.
M 266.336

357
1,2-Dihydroxy-4(15)-eudesmen-12,6-... - 1,5-Dihydroxy-3-eudesmen-12,6-olide Sq-01141 - Sq-01144

Samek, E. et al, Collect. Czech. Chern. Commun., 1973, 38, 1971 Rustaiyan, A. et al, Phytochemistry, 1989, 28, 2723 (!·
(isol, pmr, ir, ms, cd) Epidehydroisoerivanin)
Ando, M. et al, Tetrahedron, 1977, 33, 2785 (synth, ir, pmr) Sanz, J.F. et al, J. Nat. Prod. (Lloydia), 1990, 53, 940 (deriv)
Gonzalez, A. G. et al, Tetrahedron, 1980, 36, 2015 (synth, pmr, ir)
Sanz, J.F. et al, Phytochemistry, 1990, 29, 541 (isol, pmr, cmr, ir,
ms) 1,4-Dihydroxy-11(13)-eudesmen-12,6-olide Sq-01143
Tan, R.X. et al, Phytochemistry, 1990, 29, 1209 (isol, pmr)
HO
I

1,2-Dihydroxy-4(15)-eudesmen-ll,(H)Iide Sq-01141

H0,~--
(lcx,4POH,6cx}:lorm

0
C15H110 4 M 266.336
(1~,4POH,6~)-form [50301-94-5]1~-Hydroxyarbusculin A
0 Isol. from Tanacetum vulgare. Cryst. Mp 194-196°.
C 15H 110 4 M 266.336 (lp,4~0H,6~)-form

(1P,2~,6~,11 PH)-form [128722-93-0] 111X,13-Dihydro: lfi,41X-Hydroxy-12,61X-eudesmanolide. 1P-

Constit. of V/adimiria souliei. Hydroxy-11-epicolartin
Tan, R.X. et al, Phytochemistry, 1990, 29, 1209 (isol, pmr) C15H 2404 M 268.352
lsol. from Artemisia herba-alba. Cubes (EtOAc). Mp
250-251°.
1,3-Dihydroxy-4-eudesmen-12,6-olide Sq-01142 llfi,13-Dihydro: 1P·Hydroxycolartin
HO C 15H 240 4 M 268.352
I lsol. from A. herba-a/ba. Needles (EtOH). Mp 185-190°.

HO'~-
[1X]~4 + 7° (c, 0.2 in CHC1 3).
(1P,4POH,6~)-form
(la,3a,6a,lla),{o'm llfi,13-Dihydro: Dendroserin
C15H240 4 M 268.352
Constit. of Dendroseris neriifolia. Needles (MeOH). Mp
0
178-182°.
C 15H 110 4 M 266.336 lltX,13-Dihydro: 1P-Hydroxy-4,11-diepicolartin
(1~,3~,6~,11~)-form [71241-93-5] Alklumol. Isoerivanin C15H240 4 M 268.352
Constit. of Artemisia fragrans and Balsamita major. Isol. from A. herba-a/ba. Cubes (EtOAc). Mp 198-200°.
Cryst. Mp 179-181° (172-174°). Samek, Z. et al, Collect. Czech. Chern. Commun., 1973, 38, 1971
3-Ketone: see 1-Hydroxy-3-oxo-4,11(13)-eudesmadien-12,6- (Hydroxyarbusculin A)
olitle, Sq-01181 Ando, M. et al, Tetrahedron, 1977, 33, 2785 (synth)
(1~,3p,6~,11~)-form Campos, V. et al, Heterocycles, 1989, 28, 779 (Dendroserin)
Sanz, J.F. et al, J. Nat. Prod. (Lloydia), 1990, 53, 940 (l-
3-Propanoy/:
Hydroxycolartin)
C 18H 21,05 M 322.400 Sanz, J.F. et al, Phytochemistry, 1990, 29, 541 (1-Hydroxy-II-
Constit. of A. herba-alba. Gum. [1X]~4 -25° (c, 0.3 in epicolartin, I-Hydroxydiepicolartin)
CHC1 3).
(1P,3~,6~,11~)-form [85847-69-4]1-Epialklumol. 1-
1,5-Dihydroxy-3-eudesmen-12,6-olide Sq-01144
Epiisoerivanin

%--
Constit. of Picris aculeata and A. judaica. Gum or oil.
[1X]i: + 39° (c, 0.93 in CHC13).
3-Ketone: Jfi-Hydroxy-3-oxo-4-eudesmen-12,6-o/ide. 1-
Epidelrydroisoerivanin
C15H 200 4 M 264.321
lsol. from A. dijfusa. Cryst. Mp 139°. (1X]i: +43° (c, 0.2
in CHC1 3). 0
(1 p,3p,6~,11 ~)-form C 15H 220 4 M 266.336
3-Ac: [73483-51-9]. Torrentin (1P,5~,6~,11~)-form [119143-96-3] Gallicadiol
C 17H 2P 5 M 308.374 Constit. of Artemisia maritima gal/ica. Cryst.
lsol. from A. herba-a/ba. Cryst. (Et20jhexane). Mp 157- (CH 2Cl 2/hexane). Mp 219-221°. [1X]n -11.7° (c. 0.2 in
1590 (150-151°). Struct. revised in 1989. CHC1 3). Rare cis-eudesmanolide.
3-Propanoy/: Gonzalez, A.G. et al, Tetrahedron, 1988, 44, 6750.
C 18H 21;05 M 322.400
Consit. of A. herba-a/ba. Cryst. (EtOAcjpentane). Mp
151-152°. [1X]i: + 18° (c, 0.62 in CHC1 3).
Samek, Z. et al, Collect. Czech. Chern. Commun., 1979, 44, 1468
(isol, struct)
Serkerov, S.V., Khim. Prir. Soedin., 1979, 15, 282, 424 (isol, struct)
Khafagy, S.M. et al, Phytochemistry, 1988, 23, 1125.
Bruno, M. et al, Phytochemistry, 1988, 27, 1201 (isol)
Marco, J.A. et al, Phytochemistry, 1989, 28, 2505 (Torrentin)

358
1,8-Dihydroxy-3-eudesmen-12,6-olide- 1,15-Dihydroxy-11(13)-eudesmen-12,6-... Sq-01145- Sq-01150

1,8-Dihydroxy-3-eudesmen-12,6-olide Sq-01145 1,11-Dihydroxy-3-eudesmen-12,6-olide Sq-01148

m
HO

ltl'f;B{oH
0
CISHll04 M 266.336 CISH2204 M 266.336
(1 p,6«,8P,ll «H)-form (1«,5P,6P,7«,10«,11«)-form
8-Ac: [128502-78-3]. 8fi-Acetoxy-1fi-hydroxy-111XH-eudesm- 11-Angeloyl: [93414-12-1]. Isolasolide
3-en-12,61X-olide C20H 280 5 M 348.438
C 17H 240 5 M 308.374 Constit. of roots of Laser trilobum. Cryst. Mp 120-121°.
Constit. of Stevia aff. tomentosum. Gum. [1X]i? -62.3°.
Martinez-Vazquez, M. et al, Phytochemistry, 1990, 29, 1689 (isol, (Ip,sp,6p,7p,I0«,11«)-form
pmr, cmr) 11-Angeloyl, l-Ac: [85643-91-0]. /sosilerolide
C22H 300 6 M 390.475
1,8-Dihydroxy-4(15)-eudesmen-12,6-olide Sq-01146 Constit. of Laserpitium siler. Cryst. Mp 141-143°. [1X]i?
-138.9°.
11-(3-Methyl-2-butenoyl), l-Ac: [50938-18-6]. Silerolide
C22 H 300 6 M 390.475
lsol. from L. siler. Noncryst.
Holub, M. eta/, Collect. Czech. Chern. Commun., 1970, 35, 3296;
1973, 38, 1804 (isol, struct)
Holub, M. et al, Tetrahedron, 1982, 23, 4853 (cryst struct)
Holub, M. et al, Tetrahedron Lett., 1984, 25, 3755.
Smitalova, Z. et a/, Collect. Czech. Chern. Commun., 1986, 51,
C1 5H120 4 M 266.336 1323.
(JP,6«,8«)-form [80377-69-1] Artapshin
Constit. of Artemisia fragrans and Lasiolaena santosii.
Oil. [1X]i;' +20° (c, 0.32 in CHC1 3).
1,11-Dihydroxy-4(15)-eudesmen-12,6-olide Sq-01149
Serkerov, S.V. et al, Khim. Prir. Soedin., 1983, 19, 578; Chern. Nat. HO
I I
Compd. (Engl. Trans/.), 543 (iso[)

~-OH
Fernandez, J. et al, Tetrahedron, 1987, 43, 805 (synth)

1,9-Dihydroxy-3-eudesmen-12,6-olide Sq-01147

"9 OH H
0
(1«,5P,6P,7P,10«,11at:)-form
11-Angeloyl: [50657-06-2]. Lasolide
::::::,.. (1cr,5M~,9~,11crH)-form
C20 H 280s M 348.438
H
0 Constit. of Laser trilobum. Cryst. (EtOHfpet. ether).
0 Mp 149-151°.
Holub, M. et al, Collect. Czech. Chern. Commun., 1973, 38, 1428
C1sH 220 4 M 266.336
(iso[)
(1«,5P,6P,9P,ll«H)-form Holub, M. et a/, Tetrahedron Lett., 1984, 25, 3755 (isol)
1-Angeloyl, 9-Ac: [79306-89-1]. lnucrithmolide
C22H 300 6 M 390.475 1,15-Dihydroxy-11(13)-eudesmen-12,6- Sq-01150
Constit. of Inula crithmoides. Cryst. Mp 162-164°. [1X]i;'
olide
- 122° (c, 0.4 in CHC1 3).
(1 P,5«,6«,9«,11 PH)-form HO
9«-Hydroxy-11 p,/3-dihydrosantamarine
Constit. of Pluchea dioscoridis. Oil. [1X]~4 +20° (c, 0.5 in
CHC1 3).
Mahmoud, Z.F. et al, Phytochemistry, 1981, 20, 735
(lnucrithmolide)
Bohlmann, "F. et al, Phytochemistry, 1984, 23, 1975 (iso[)

C 15H 220 4 M 266.336

(JP,6«)-form [92632-21-8]
15-Hydroxy-4p, 15-dihydroreynosin
Constit. of Sonchus macrocarpus. Oil.
1-0-P-n-Glucopyranoside: [126585-71-5]. Sonchuside F
C21 H 320 9 M 428.478
Constit. of S. asper. Amorph. powder. [1X]i,3 -5.6° (c,
0.63 in MeOH).

359
3,4-Dihydroxy-7-eudesmen-12,6-olide - 1,8-Dihydroxy-3-oxo-4,11(13)-... Sq-01151 - Sq-01155

11P,J3-Dihydro: 1,15-Dihydroxy-12,6-eudesmanolide !sol. from Sphaeranthus indicus. Shows immune-

CtsH 240 4 M 268.352 stimulating activity. Cryst. (MeOH). Mp 54.5-55°. [IX]~
Constit. of S. macrocarpus. Oil. -13.25°.
11P,13-Dihydro, 1-0-P-v-glucopyranoside: [126585-73-7]. Ruangrungsi, N. eta/, J. Nat. Prod. (Lloydia), 1989, ~12, 130
Sonchuside H (Grangolide)
C21 H 340 9 M 430.494 Shekhani, M.S. eta/, Phytochemistry, 1990, 29, 2573
Constit. of S. asper. Amorph. powder. [IX]~ -38.1° (c, (Sphaeranthanolide)
0.21 in MeOH).
11P,J3-Dihydro, 15-0-P-v-glucopyranoside: [126585-74-8]. 3,9-Dihydroxy-4-eudesmen-12,6-olide Sq-01153
Sonchuside I
Constit. of S. asper. Amorph. powder. HO

H<Y~--
15-Aldehyde: 1P-Hydroxy-15-oxo-11(13)-eudesmen-12,61X-
olide. Sonchucarpolide
CtsH200 4 M 264.321
Constit. of Sonchus macrocarpus. Gum. Occurs in mixt.
with dihydro deriv. 0
15-Aldehyde, 1-0-P-v-glucopyranoside: Sonchuside E
C21 H 34P 9 M 426.463 CtsH22 0 4 M 266.336
Constit. of S. asper. Amorph. powder. [1X]i? -27.6° (c, (3rx.,6rx.,9p,1lrx.)-form [95262-46-7] Herbolide E
0.49 in Hp). Constit. of Artemisia herba-alba. Cryst. (Me2CO). Mp
15-Aldehyde, 11P,13-dihydro: IP-Hydroxy-15-oxo-12,6rx.- 162-164°. [1X]i? + 154° (c, 0.2 in CHC13).
eudesmanolide Segal, R. et a/, Phytochemistry, 1984, 23, 2954.
CtsHz20 4 M 266.336
Isol. from S. macrocarpus. Gum. 5,9-Dihydroxy-4(15)-eudesmen-12,6-olide Sq-01154

%--
15-Aldehyde, 11 p,13-dihydro, 1-0-P-v-glucopyranoside:
Sonchuside G OH
C21 H 320 9 M 428.478
Constit. of S. asper. Amorph. powder. [1X]i? -37.9° (c,
1.82 in H 20).
Mahmoud, Z. eta/, Phytochemistry, 1983, 22, 1290; 1984, 23, 1105
(isol, pmr)
Shimizu, Z. eta/, Phytochemistry, 1989, 28, 3399 (isol, pmr, cmr) 0
CtsHn04 M 266.336
3,4-Dihydroxy-7-eudesmen-12,6-olide Sq-01151 (5rx.,6rx.,9P,Ilrx.)-form [97649-06-4] Herbolide I
Constit. of Artemisia herba-alba. Cryst. (Etp). Mp 213-
2150. [1X]i? + 170° (c, 0.11 in CHC1 3).
Segal, R. et a/, Phytochemistry, 1985, 24, 1381.
HOcn --
~:f\iJ6)_ 1,8-Dihydroxy-3-oxo-4,11(13)- Sq-01155
0 eudesmadien-12,6-olide

111-0H
C 15H 220 4 M 266.336
(3~,4~,6rx.,llrx.)-form
Mibulactone
Constit. of Artemisia monogyna. Cryst. Mp 228°. [IX])?
+ 156.4°.
Karyone, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1949, 0~
69, 310; CA, 1937, 44 (isol)
Fukui, T., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1958, 78, 712
0
(struct) Ct 5Hta05 M 278.304
(Ip,6rx.,Brx.)-form
3,7-Dihydroxy-4-eudesmen-12,6-olide Sq-01152 8-Ac: 8rx.-Acetoxyarmexifolin
C 17H 200 6 M 320.341

{i1/oH lsol. from Artemisia mexicana. Cryst. Mp 215°. [1X]n

+ 147° (c, 1.33 in CHCI 3).
Mata, R. et a/, Phytochemistry, 1984, 23, 1665.
HO/~~-r
0
C 15H 220 4 M 266.336
(3rx.,6P,7P,11fl)-form [120396-56-7] Grangolide
Constit. of Grangea maderaspatana. Cryst. Mp 135-139°.
[1X]i;' + 12° (c, 2.76 in CHC1 3).
3-0-P-v-Glucopyranoside: [129885-23-0]. Sphaeranthanolide
C21 H 320 9 M 428.478

360
4,8-Dihydroxy-1-oxo-2-eudesmen-... - 3,4-Epoxy-1-hydroxy-1(13)-eudesmen-... Sq-01156 - Sq-01159

4,8-Dihydroxy-1-oxo-2-eudesmen-12,6- Sq-01156 (1 «,4«.,6«.,8«. )-form

olide 1-(2-Methylpropenoyl):
C 19H 140 6 M 348.395
Constit. of D. brasilianum. Gum.
1-(2-Hydroxymethylpropenoyl):
C 19H 140 7 M 364.394
Constit. of D. brasilianum. Gum. [1X]~4 -109° (c, 0.3 in
CHCI 3).
1-(2,3-Epoxy-2-methylpropanoyl):
C19H140 7 M 364.394
C 15H100 5 M 280.320 Constit. of D. brasi/ianum. Gum.
(4«.,6«.,8«.,11«.)-form [50657-15-3] Tabarin 1-Tigloy/:
Constit. of Artemisia canariensis. Cryst. (EtOAc). Mp C10H160 6 M 362.422
213-215°. [1X]n + 10°. Constit. of D. brasilianum. Gum.
11 ,13-Didehydro, 8-Ac: [65017-99-4]. Artemexifolin 1-(4-Acetoxy-2Z-butenoyl):
C 17H100 6 M 320.341 Cz2H 280 8 M 420.458
Constit. of A. mexicana. Cryst. (Me 2COfdiisopropy1 Constit. of D. brasi/ianum. Gum.
ether). Mp 260°. 1-(2-Ace toxymethyl-2Z-butenoyl):
Gonzalez, A.G. eta/, An. Quim., 1973, 69, 667; CA, 79, 92415w CzzH280 8 M 420.458
(Tabarin) Constit. of D. brasilianum. Gum.
Mata, R. eta/, Phytochemistry, 1984, 23, 1665 (Artemexifolin)
1-(2-Hydroxymethyl- 2Z-butenoyl):
C10H 160 7 M 378.421
4,15--Epoxy-1,8-dihydroxy-11(13)- Sq-01157 Constit. of D. asperatum. Gum. [1X]i: + 85° (c, 0.23 in
eudesmen-12,6-olide CHCI 3).
HOI Bohlmann, F. eta/, Phytochemistry, 1981, 20, 838, 1335; 1982, 21,
1343.

2,3-Epoxy-1-hydroxy-4(15),11(13)- Sq-01158
(1 tx,4~,6tx,8tx )-form eudesmadien-12,6-olide

C15H100 5 M 280.320
(1«,4P,6«.,8«.)-form [79405-88-2] Dimerostemmolide
0<RrOH
1-(2-Hydroxymethylpropenoyl): H I -
C19H140 7 M 364.394 0
Constit. of Dimerostemma brasilianum. Gum. 0
1-Angeloy/: C15H 1804 M 262.305
C10H160 6 M 362.422 (1~,2~,3~,5«.,6«.)-form
Constit. of D. lippioides. Gum. [1X]i: + 10° (c, 0.12 in Angeloyl: [37905-05-8]. Badkhysinin
CHC1 3).
C10H140 5 M 344.407
1-(2,3-Epoxy-2-methy/butanoyl): Constit. of Ferula oopoda and F. badhysi. Cryst. Mp
C10H 160 7 M 378.421 104-105°. [1X]n -212° (CHCI 3).
Constit. of D. asperatum. Gum. [1X]i: -42° (c,. 1.3 in
111;,,13-Dihydro, angeloy/: [37551-59-0]. Badkhysidin
CHCI 3).
C10H 160 5 M 346.422
1-(2-Hydroxymethyl-2Z-butenoyl): Constit. of F. oopoda and F. badhysi. Cryst. Mp 117-
CzoH160 7 M 378.421 ll80.
Constit. of D. asperatum. Gum. [1X]i: -31° (c, 0.6 in
Serkerov, S.V., Khim. Prir. Soedin., 1971, 7, 590; 1972, 8, 176;
CHC1 3). 1976, 12, 393 (isol, struct)
1-(4-Acetoxy-2-methy/-2E-butenoyl):
CzzH 280 8 M 420.458
Constit. of D. brasilianum. Gum. 3,4-Epoxy-1-hydroxy-1 (13)-eudesmen- Sq-01159
1-(4-Acetoxy-2-methy/-2Z-butenoyl):
12,6-olide
CzzH280 8 M 420.458 HO
Constit. of D. brasi/ianum. Gum. I

1-(2-Hydroxymethylpropenoyl), 8-(2-methy/propanoyl):
C23 H 320 8 M 436.501 (1)
Constit. of D. brasi/ianum. Gum. [1X]~4
CHCI 3).
8-Angeloyl, 1-(2-hydroxymethyl-2Z-butenoyl):
+ 135° (c, 0.4 in
bYhb:r
0
C25 H 320 8 M 460.523
Constit. of D. lippioides. Gum. C 15H100 4 M 264.321
1-(2-Hydroxymethyl-2Z-butenoyl), 8-(2-methylbutanoyl): (1«.,3«.,4«.,6«.)-form [27740-13-2] Ludovicin A
C25H 340 8 M 462.539 Constit. of Artemisia ludoviciana. Cryst. (Et20/CH 2Cl2).
Constit. of D. lippioides. Gum. Mp 215°. [IX]~ + 128° (CHCI 3).
(1 P,3«,4«.,6«. )-form [3668-04-0] «.-Epoxysantamarine

361
4,5-Epoxy-1-oxo-12,6-eudesmanolide - 1,3,11(13)-Eudesmatrien-..1.2,6-olide Sq-01160 - Sq-01165

Constit. of Ambrosia confertifiora. Cryst. (EtOAc). Mp (5fJ,7fJ,10/I)-form [27579-97-1] (- )-FruUanolide

243-243.SO. [a]~ + 87.SO (c, 0.096 in EtOH). Constit. of F. tamarisci. Cryst. (hexane). Mp 76.5-77°.
Lee, K.H. et al, Phytochemistry, 1970, 9, 403 (Ludovicin A) [1X]n -113° (c, 0.22 in CHC1 3).
Yoshioka, H. et al, Phytochemistry, 1970, 9, 823 (IX- t> Potent allergen.
Epoxysantamarine) (6rx.,7fJ,1 0/1)-form
Ando, M. et al, Tetrahedron, 1977, 33, 2785 (synth) Arbuscu/in B
Constit. of Artemisia arbuscula and F. tamarisci. Cryst.
4,5-Epoxy-1-oxo-12,6-eudesmanolide Sq-01160 (Et20jpet. ether). Mp 86.5-88°. [1X]~4 +47.3° (c, 3 in
CHCl 3).
0 Irwin, M.A. et al, Phytochemistry, 1969, 8, 24121 (isol. struct)

~--
Perold, G.W. et al, Tetrahedron, 1972, 5797 (isol)
Connolly, J.D. et al, Phytochemistry, 1973, 12, 631 (isol)
Green, A.E. et al, J. Org. Chem., 1974, 39, 186, 948 (5ynth)
Asakawa, Y. et al, Bull. Soc. Chim. Fr., 1976, 1465 (isol, tox)
Yamakawa, K. et al, Heterocycles, 1977, 8, 103 (synth)
0 Still, W.C. et al, J. Am. Chem. Soc., 1977, 99, 948 (synth)
Kido, F. et al, J. Am. Chem. Soc., 1979, 101, 6420 (synth)
C 15H 200 4 M 264.321 Semmelhack, M.F. et al, J. Am. Chem. Soc., 1981, 10~1. 3945
(4rx..Srx.,6«.,11fJH)-form (81241-39-6] Maritimin (synth)
Constit. of Artemisia maritima gallica. Cryst. Minami, T. et al, J. Chem. Soc., Perkin Trans. I, 1990. 2385
(EtOAcjpet. ether). Mp 176-178°. [a]n -42° (c, 0.3 in (synth)
Clive, D.L.J. et al, J. Org. Chem., 1990, 55, 1096 (synth)
CHC1 3).
Gonzalez, A.G. et al, Phytochemistry, 1981, 20, 2367.
4(15), 11(13)-Eudesmadien-12,6-olide Sq-01164
1,3-Eudesmadien-12,6-olide Sq-01161

0 (5cx,6cx,7~,10~)-:form

C,sH2001 M 232.322
C15H 200 1 M 232.322 (5«.,6«.,7/l,l 0/1)-form [2221-82-1] fJ-Cyclocostunolide
Constit. of Saussurea lappa. Cryst. (Etp). Mp 66.5-67°.
(6«.,7«.,11~)-form [37905-06-9] Feropodin
[IX]~ + 179° (CHC1 3).
Constit. of Ferula oopoda. Cryst. (EtOH aq.). Mp 140-
1410. 111X,l3-Dihydro: 11«.,13-Dihydro-fJ-cyclocostuno/ide
C,sH120 2 M 234.338
Serkerov, S.V., Khim. Prir. Soedin., 1969, 5, 245; CA, 72, 63618q.
Serkerov, S.V., Khim. Prir. Soedin., 1971, 7, 667; CA, 77, 5623e.
Constit. of Artemisia herba-alba. Needles (Et20jhexane).
Mp 113-IW. [IX]~ +198° (c, 0.4 in CHC1 3).
(5rx.,6fJ,7rx.,lOrx.)-form [62870-72-8] ent-cis-fJ-Cyclocostunolide
3, 11(13)-Eudesmadien-12,6-olide Sq-01162 Isol. from Frullania dilatata. Cryst. (hexane). Mp 75-76°.
[1X]D + 38o.

C11 (5«.,6«.,7«.,10/1)-form [62487-25-6] Critonilide

lil6-Y 0
C 15H 200 1 M 232.322
(5«.,61X)-form [2221-81-0] «.-Cyclocostunolide
Constit. of Moquinea velutina. Cryst. (MeOH/Etp).
Mp 80-82°. [a]i; + 116° (CHC1 3).
Tomassini, T.C.B. et al, Phytochemistry, 1972, 11, 1177 (isol)
Jain, T.C. et al, Tetrahedron, 1975, 31, 2211 (synth)
da Silva, A.J.R. et al, Org. Magn. Reson., 1981, 16, 234 (cmr)
Constit. of Critonia morifolia. Cryst. (Et20jpet. ether).
Mp 73.SO. [1X]i; + 140.3° (c, 2.05 in CHC1 3).
(5fJ,6«.,7«.,10rx.)-form [74006-29-4] fJ-Frullanolide
Constit. of Frullania brotheri. Cryst. (EtOAcjhexane).
Mp 165-167°. [1X]n +178° (c, 1.17 in CHC1 3).
(5«.,6«.,7fJ,JO«.)-form [97916-07-9] Morifolin B
Constit. of C. morifolia. Oil.
Jain, T.C. eta/, Tetrahedron, 1975, 31, 2211 (synth)
Asakawa, Y. eta/, Bull. Soc. Chim. Fr., 1976, 1465 (iso·~
Bohlmann, F. eta/, Chem. Ber., 1977, 110, 301 (Critoni.lide)
Govindan, S.V. et a/, Indian J. Chem., Sect. B, 1977, 15, 956 (isol)
Takeda, R. et al, Bull. Chem. Soc. Jpn., 1983, 56, 1120 (/1-
Frullano/ide)

W-r
4,11(13)-Eudesmadien-12,6-olide Sq-01163 Gonzalez, A.G. et al, Heterocycles, 1985, 23, 1601 (Morifolin B)
Sanz, J.F. et al, Phytochemistry, 1990, 29, 541 (iso/, cmr, pmr)
I

1,3,11(13)-Eudesmatrien-12,6-olide Sq-01165
(6a,1a,IO.}fo"" 1,3,11(13)-Selinatrien-12,6-olide

~
0
C,sH2001 M 232.322
(6«.,71X,l0rx.)-form [40776-40-7] ( + )-FruUanolide
Constit. of Frullania dilatata. Cryst. (hexane). Mp 76.5- 0
770. (a)n + 114° (c, 0.25 in CHC1 3).
t> Potent allergen. M 230.306

362
1-Hydroxy-3,11(13)-eudesmadien-... - 2-Hydroxy-4,11(13)-eudesmadien-... Sq-01166 - Sq-01169

6«-form [71609-02-41 Gaz.aniolide El-Feraly, F.S. eta/, Phytochemistry, 1979, 18, 881 (Magnolia/ide)
Constit. of Gazania krebsiana. Oil. Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (1-
Hydroxysteiractinadieno/ide)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 332.

1-Hydroxy-4(15),11(13)-eudesmadien- Sq-01168
1-Hydroxy-3,11(13)-eudesmadien-12,6- Sq-01166
12,6-olide
olide

C1sH:zo03
~
M 248.321
0
(1 «,6« )-form
(1P,6«)-form [4290-13-51 Santamarine. Balchanin
Constit. of Artemisia balchanorum and Chrysanthemum
parthenium. Cryst. (diisopropyl etherjMe2 CO). Mp 142°
(134-136°). [ali? +96.6° (CHC1 3). (1P,6«)-form [28254-53-7] Reynosin
11P,J3-Dihydro: IP-Hydroxy-3-eudesmen-12,6a-olide.
llp,I3-Dihydrosantamarine. IP-Hydroxy-3-santen-12,6-
o/ide (obso/.)
C1sHu03 M 250.337
Constit. of A. canariensis and A. tridentata ssp.
wyomingensis. Cryst. Mp 132-133°. [aln +71° (c, 1.0 in
CHC1 3). Also see 1-Hydroxy-3-eudesmen-12,6-olide, Sq-
01175.
lla,l3-Dihydro: 11«,13-Dihydrosantamarin
C1sHu03 M 250.337
Constit. of A. herba-alba. Cryst. (EtzO/hexane). Mp 92-
950. [alii +93° (c, 0.9 in CHC1 3). Also see 1-Hydroxy-3-
eudesmen-12,6-olide, Sq-01175.
(ent-1p,6« )-form
la-Hydroxy-3, 11 (13)-steiractinadien-12,6P-olide
lsol. from Geigeria rigida. Gum.
Suchy; M. eta/, Collect. Czech. Chern. Commun., 1962, 27, 2925
(is of)
Romo de Vivar, A. eta/, Tetrahedron, 1965, 21, 1741 (isol, struct)
Pathak, S.P. eta/, Chern. Ind. (London), 1970, 1147 (struct)
Shafizadeh, F. eta/, Phytochemistry, 1971, 10, 2745 (isol)
Yamakawa, K. eta/, Heterocycles, 1977, 8, 103 (synth)
Ando, M. eta/, Tetrahedron, 1977, 33, 2785 (synth) 2-Hydroxy-4,11(13)-eudesmadien-12,6-
Rodrigues, A.A.S. et a/, Phytochemistry, 1978, 17, 953 (synth)
Holub, M. eta/, Collect. Czech. Chern. Commun., 1982, 47, 2927
(deriv)
Gonzalez, A.G. eta/, Phytochemistry, 1983, 22, 1509 (isol)
Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (iso/, pmr, cd)
Sanz, J.F. eta/, Phytochemistry, 1990, 29, 541 (deriv, pmr, cmr)
C1sH:zo03
M 248.321
Constit. of Schistostephium rotundifolium. Gum. [ali:
+ 132° (c, 0.75 in CHCI 3).
Constit. of Ambrosia corifertiflora. Cryst.
(C 6H 6 jcyclohexane). Mp 145-146°. [ali; + 180° (c, 0.12
in EtOH).
lla,J3-Dihydro: [32223-12-41. Dihydroreynosin
C1sH 2z03 M 250.337
Constit. of Artemisia canariensis and Michelia
compressa. Cryst. (hexane). Mp 136-137°. Struct. revised
in 1990.
11P,13-Dihydro: 11-Epidihydroreynosin
Ct5Hu03 M 250.337
Constit. of A. herba-alba and Centaurea ornata. Needles
(Et20jhexane). Mp 142-145°. [ali: + 1.8° (c, 0.9 in
CHCI 3).
Yoshioko, H. eta/, Phytochemistry, 1970, 9, 823 (iso/, struct)
Ando, M. eta/, Tetrahedron, 1977, 33, 2785 (synth)
Rodrigues, A.A.S. et a/, Phytochemistry, 1978, 17, 953 (synth)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1666; 1983, 22, 1623
(isol, struct)
Gonzalez, A.G. eta/, Phytochemistry, 1983, 22, 1509 (isol)
Navarro, J.J. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 573 (isol,
pmr, cmr, struct)
Sq-01169
olide

1-Hydroxy-4, 11(13)-eudesmadien-12,6- Sq-01167

olide Ct5H:zo03 M 248.321
(2«,6p)-form [128988-24-91 2«-Hydroxysphaerantholide

~
Constit. of Sphaeranthus suaveolens. Cryst. Mp 80°. [ali:
-60° (c, 0.36 in CHCI 3).
Ac: [128988-25-0l. 2«-Acetoxysphaerantholide
(1~,6cx}jorm C 17Hu04 M 290.358
Constit. of S. suaveolens. Cryst. Mp 131°. [a]~4 -99° (c,
0 0.57 in CHCI 3).
Jakupovic, J. eta/, Phytochemistry, 1990, 29, 1213 (isol, pmr)
C1sH:zo03 M 248.321
(1P,6«)-form [72145-13-21 Magnolia/ide
Constit. of Magnolia grandiflora. Cryst. (hexanejEtzO).
Mp 152-153°. [ali; +74° (c, 0.23 in EtOH).
(ent-1P,6«)-form [125356-46-91
la-Hydroxy-4, 11 (13)-steiractinadien-12,6P-olide
Isol. from Geigeria rigida. Gum.

363
5-Hydroxy-4(15),11(13)-eudesmadien-... - 1-Hydroxy-3-eudesmen-12,6-olide Sq-01170 -- Sq-01175

5-Hydroxy-4(15),11(13)-eudesmadien- Sq-01170 C 17H 2z04 M 290.358

12,6-olide From A. tournefortiana. Oil. [rx.]i;' + 14° (c, 0.2 in
CHC1 3).

~
9-Ketone: [111420-61-2]. 9-0xo-4,11(13)-eudesrnadien-12,6P-
olide. 9-0xotournefortiolide
C,sH 180 3 M 246.305
From A. tournefortiana. Cryst. Mp 165°. [rx.J~: +44° (c,
2.2 in CHC1 3).
0
Rustaiyan, A. et a/, Phytochemistry, 1987, 26, 2307.
C 15H 200 3 M 248.321
(5rx.,6rx.,7p,JOf/)-form [33530-71-1] Arbusculin C 3-Hydroxy-1,4(15),11(13)-eudesmatrien- Sq-01173
Constit. of Artemisia spp. Cryst. (EtzO/EtOAc). Mp
12,6-olide
150-151°. [rx.]i;l + 113° (c, 3 in CHC1 3).
(5p,6rx.,7rx.,10rx.)-form [62870-71-7]

HO'~
ent-5rx.-Hydroxy-4(15), 11 (13)-eudesmadien-12,6P-olide.
Oxyfrullanolide
Constit. of Frullania dilatata. Cryst. (hexane). Mp 179-
1800. [1X]D + 71°.
0
Irwin, M.A. eta/, Phytochemistry, 1971, 10, 637 (struct)
Asakawa, Y. et a/, Bull. Soc. Chim. Fr., 1976, 1665 C,sH,80 3 M 246.305
(Oxyfrullanolide) (3rx.,6rx.)-form [82461-09-4] Brachylaenolide
Yamakawa, K. eta/, Heterocycles, 1977, 8, 103 (synth) Constit. of Brachylaena transvaalensis. Cryst. (Et20jpet.
El-Feraly, F.S. et a/, J. Chern. Soc., Perkin Trans. I, 1983, 355
ether). Mp 138°. [rx.]i;' + 150° (c, 0.04 in CHCI 3).
(synth)
Ac:
C 17H 200 4 M 288.343
7-Hydroxy-4,11(13)-eudesmadien-12,6- Sq-01171 Constit. of Dicoma capensis. Cryst. Mp 139°.
olide 3-Ketone: 3-0xo-1,4(15),JJ(J3)-eudesmatrien-12,6rx.-olide.
Dehydrobrachylaenolide
C,sH 160 3 M 244.290
Constit. of B. transvaalensis. Cryst. (2-propanol). Mp
(6J3,7a)-form 225°. [rx.]i;' +67° (c, 0.16 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 647.
Zdero, C. et a/, Phytochemistry, 1990, 29, 183 (isol, pmr)
C 15H 200 3 M 248.321
(6p,7rx.)-form 8-Hydroxy-1,3,11(13)-eudesmatrien-12,6- Sq-01174
7rx.-Hydroxyfrullanolide olide
Constit. of Sphaeranthus indicus. Cryst.
(EtOAcjpentane). Mp 62-63°. [rx.Ji: -44.21° (c, 2.09 in
CHC1 3).
(6p,7fl)-form
7P-Hydroxyfrullanolide
From S. indicus. Mp 72-73°. [rx.Ji: -63.16° (c, 3.07 in
CHC1 3).
C 15H 180 3 M 246.305
Jlrx.,l3-Dihydro: 7P-Hydroxy-4-eudesmen-12,6P-olide
C 15H 22 0 3 M 250.337 (6rx.,8rx.)-form
From S. indicus. Cryst. (EtOAcfhexane). Mp 81-82°. 8-Hydroxygazaniolide
[rx.Ji: -61.8° (CHC1 3). 8-(3-Methy/butanoyl): [71608-92-9].
Gogte, M.E. et a/, Indian J. Chern., Sect. B, 1986, 25, 233 (isol) C20H 260 4 M 330.423
Sohoni, J.S. eta/, J. Chern. Soc., Perkin Trans. I, 1988, !57 (isol) Constit. of Gazania krebsiana. Oil.
Atta-ur-Rahman, J. Chern. Res. (S), 1989, 68 (isol) Bohlmann, F. eta/, Phytochemistry, 1979, 18, 332.

9-Hydroxy-4,11(13)-eudesmadien-12,6- Sq-01172 1-Hydroxy-3-eudesmen-12,6-olide Sq-01175

olide
HO
I

C 15H 200 3
~
M 248.321
0

(6P,9fl)-form [111394-33-3] 9P-Hydroxytournefortiolide

C 15H 22 0 3
(lrx.,6rx.)-form
~--
M 250.337
0

Ac: [125675-22-1]. Ja.-Acetoxy-3-eudesmen-12,6rx... o/ide

Constit. of Artemisia tournefortiana. Oil. [rx.]i;l -12° (c, C 17H 240 4 M 292.374
0.6 in CHC1 3).
Ac: [111394-34-4]. 9P-Acetoxytournefortiolide

364
1-Hydroxy-4-eudesmen-12,6-olide - 1-Hydroxy-3-oxo-4,11(13)-... Sq-01176 - Sq-01181

Constit. of Artemisia herba-alba. Gum. [oc]i;l + 154° (c, 8-Hydroxy-4-eudesmen-12,6-olide Sq-01178

0.1 in CHC1 3).
(lp,6rx.)-form
1P-Hydroxy- 3-eudesmen-12,6P-olide
Cryst. (Et20/hexane). Mp 130-132°. [ocln +62° (c, 0.28
in CHCI 3).
Gonzalez, A.G. eta/, J. Chern. Soc., Perkin Trans. I, 1978, 1243
(synth, ir, uv, pmr)
Marco, J.A. eta/, Phytochemistry, 1989, 28, 3121 (isol, pmr, cmr) C1sH2003 M 248.321
(6rx.,8rx.)-form [33530-72-2] Rothin A
1-Hydroxy-4-eudesmen-12,6-olide Sq-01176 Constit. of Artemisia rothrockii. Cryst. (Et20/Et0Ac).

1h
Mp 133-134°.
Irwin, M.A. eta/, Phytochemistry, 1971, 10, 637 (isol, struct)
Carda, M. eta/, Tetrahedron, 1986, 42, 3655 (synth)
(IP,6a,ll PH)-[D'm

Y"Q-- 8-Hydroxy-4(15)-eudesmen-12,6-olide Sq-01179

0
C1sH2203 M 250.337
(Jp,6rx.,JIPH)-form [41410-55-3] Artesin
Constit. of Artemisia santo/ina, A. granatensis and
others. Cryst. (EtOAcjC 6H 6). Mp 177° (172°). [ocln
C1sH2003 M 248.321
+49°. Data on 11-config. confused until 1989; see
Marco for summary. (6«,8« )-form
Constit. of Perymenium mendezii. Gum.
(1 p,6rx.,ll rx.H)-form
11-Epiartesin. 11-epi-Artesin Ac: [24164-16-7]. P-Cyclotulipinolide
Isol. from A. herba-alba. Needles (Et20jpentane). [oc]i;l C1 7 H 220 4 M 290.358
+ 82° (c, 0.6 in CHCI 3). Cryst. (EtOAcjhexane). Mp 135-136°.
Gonzalez, A.G. eta/, J. Chern. Soc., Perkin Trans. I, 1978, 1243 Maldonado, E. eta/, Phytochemistry, 1984, 23, 813.
(isol)
Villar, A. eta/, Phytochemistry, 1983, 22, 777 (isol) 9-Hydroxy-3-eudesmen-12,6-olide Sq-01180
Marco, J.A., Phytochemistry, 1989, 28, 3121 (bib/)

%--
4-Hydroxy-11(13)-eudesmen-12,6-olide Sq-01177

C1sH2203
HSJQ
M 250.337
0 C1sH2203 M 250.337
0

(6rx.,9p,llrx.)-form [97669-46-0] Herbolide G

Constit. of Artemisia herba-alba. Cryst. (Etp). Mp 126-
(4rx.,6rx.)-form [27652-22-8] Arbusculin A 1280. [oc]i; +1U0 (c, 0.7 in CHCI 3).
Constit. of Artemisia arbuscula and Mochina vellutina.
Cryst. (Etpjpet. ether). Mp 76.5-77.7°. [ocJ;4 +25.8° (c, Segal, R. et a/, Phytochemistry, 1985, 24, 1381.
4.2 in CHCI 3).
IIP,J3-Dihydro: [24493-40-1]. 4oc-Hydroxyeudesman-12,6oc- 1-Hydroxy-3-oxo-4,11(13)-eudesmadien- Sq-01181
olide. Colartin 12,6-olide
ClsH 240 3 M 252.353
Constit. of A. tripartita. Cryst. (Etpjpet. ether). Mp
107-108°. [oc]i;l + 11.4° (c, 3.67 in CHCI 3).
lloc,J3-Dihydro: 11-Epicolartin
C 15H 240 3 M 252.353
Isol. from A. herba-alba. Cryst. (EtOAcjhexane). Mp
122-123°. [oc]i;l +68° (c, 2.24 in CHC1 3).
Irwin, M.A. eta/, Phytochemistry, 1969, 8, 2411 (Co/arlin,
Arbusculin A) C!sH!s04 M 262.305
Yamakawa, K. eta/, Heterocycles, 1977, 8, 103 (synth) (lrx.,6rx.)-form [27740-15-4] Ludovicin C
Sanz, J.F. eta/, Phytochemistry, 1990, 29, 541 (11-Epico/artin) Constit. of Artemisia ludoviciana. Cryst. (Et20/CH 2Cl 2).
Mp 193-195°. [oc]i; +95° (CHC1 3).
lloc,J3-Dihydro, Ac: [104720-09-4]. ArtegaUin
C 17H 220 5 M 306.358
Constit. of A. caerulescens spp. gallica. Oil. [ocln + 14.1°
(c, 0.66 in CHCI 3).

365
4-Hydroxy-1-oxo-2,11(13)-... - 8-Hydroxy-3-oxo-12,6-eudesmanolide Sq-01182 -· Sq-01186

11fi,13-Dihydro: [71327-31-6]. 11X-Hydroxy-3-oxo-4- (6p,]J~)-form

eudesmen-12,61X-olide. Dehydroisoerivanin. Alkhanin. Angeloyl: [51848-01-2). Decipienin A
Alkanin C20 H 240 5 M 344.407
C 15H 100 4 M 264.321 Constit. of Melanoselinum decipiens. Cryst. (C6H 6 /pet.
Constit. of Balsamita major and A. fragrans. Cryst. Mp ether). Mp 185-186°. [1X]n + 54.9° (c, 3.2 in EtOH).
201-203°. Pinhey, J.T. et a/, Aust. J. Chem., 1965, 18, 543 (ot-
(1P,61X)-form [64929-15-3] Armexifolin. 1-Epiludovicin C Hydroxysantonin)
Isol. from Tanacetum vulgare and A. mexicana. Cryst. Gonzalez, A.G. eta/, Ann. Quim., 1973, 69, 1339; 1974, 70, 1028
Mp 201-203°. (Decipienin A)
Lee, K.H. eta/, Phytochemistry, 1970, 9, 403 (iso/)
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1979, 44, 1468 1-Hydroxy-3-oxo-12,6-eudesmanolide Sq-01185
(Dihydroisoerivanin)
Serkerov, S., Khim. Prir. Soedin., 1979, 44, 488. HO
I
Ognyanov, I. et a/, Planta Med., 1983, 48, 181 (iso/)
Mata, R. et a/, Phytochemistry, 1984, 23, 1665 (isol)
Feliciano, A.S. eta/, Phytochemistry, 1986, 25, 1757 (Artegallin)
0 __ 13 (lcx,4cx,6cx,11cx)form
4-Hydroxy-1-oxo-2,11(13)-eudesmadien- Sq-01182
12,6-olide
0 C 15H 220 4 M 266.336
(lrx,4rx,6rx,llrx)-form [41787-77-3] Arsantin
Constit. of Artemisia santo/ina. Cryst. Mp 168°. [1X]n
+31°.
(Jp,4rx,6rx,llrx)-form [41135-04-0) Arsanin. Taraxacolide B
Constit. of A. santo/ina. Cryst. (EtOH). Mp 193-194°.
[1X]D +26o.
C,sH1804 M 262.305 1-0-P-v-Glucopyranoside:
(4rx,6rx)-form [16981-97-8] Arglanine C1 ,H310 9 M 428.478
Constit. of Artemisia douglasiana and A. mexicana. Constit. of Taraxacum officina/e. Amorph., cryst. (as
Cryst. Mp 185-187° (207°). [1X]i;' +111°. tetra-Ac). Mp 192° (tetra-Ac).
11 ,13-Dihydro: see 4-Hydroxy-1-oxo-2-eudesmen-12,6-olide, 11,13-Didehydro: [24778-20-9]. 1fi-Hydroxy-3-oxo-11(13)-
Sq-01189 eudesmen-12,61X-olide. Artecalin. Dehydroarsanin
Matsueda, S. et a/, Tetrahedron Lett., 1967, 2017 (isol, struct) C 15H 200 4 M 264.321
Yamakawa, K. eta/, Tetrahedron Lett., 1975, 4137 (synth) Isol. from A. californica, A. tripartita and many other
Mata, R. eta/, Phytochemistry, 1984, 23, 1665 (iso/) plants. Cryst. (EtOAc). Mp 225-227°. [1X]i;' +45° (c, 0.01
in CHC1 3).
8-Hydroxy-3-oxo-1,4-eudesmadien-12,6- Sq-01183 Geissman, T.A. eta/, Phytochemistry, 1969, 8, 1297 (Artecalin)
Akeyev, B. eta/, Khim. Prir. Soedin., 1971, 7, 531; CA. 75,
olide 14850lh (iso/)
Moiseeva, G.P. eta/, Khim. Prir. Soedin., 1973, 9, 167; CA, 79,
5470u (struct)
Yamakawa, K. eta/, Chem. Pharm. Bull., 1976, 24, 2810 (synth)
Abduazimov, B.K. et al, Khim. Prir. Soedin., 1980, 633 (Artecalin)
Hansel, R. eta/, Phytochemistry, 1980, 19, 837.
Yunusov, A.l. eta/, Khim. Prir. Soedin., 1983, 532 (Ar1eca/in)

C 15H 180 4 M 262.305 8-Hydroxy-3-oxo-12,6-eudesmanolide Sq-01186

(6rx,8rx,llrx)-form [481-05-0] Artemisin
Constit. of Artemisia maritima and A. cina. Cryst.
(Hp). Mp 202-203°. [1X)n -84.3° (EtOH).
Bolt, A.J.N. eta/, J. Chern. Soc., 1963, 5235 (struct)
Nakazaki, M. eta/, Bull. Chern. Soc. Jpn., 1969, 42, 3366 (synth)

11-Hydroxy-3-oxo-1,4-eudesmadien-12,6- Sq-01184 C 15H2204 M 266.336

olide (4P,6rx,8rx,llrx )-form [38412-44-1] Arabsin
Constit. of Artemisia absinthium. Cryst. (C 6H 6). Mp 188-

O~h-
1890. [1X]i;' +89° (c, 2.71 in EtOH).
Akhadov, I.S. et a/, Khim. Prir. Soedin., 1972, 245.
, OH
I H ....
0
0
C,sH 180 4 M 262.305
(6rx,llp)-form
11-Hydroxysantonin. IX-Hydroxysantonin
!sol. from dog urine after ingestion of Santonin. Cryst.
(EtOH). Mp 295° subl.

366
8-Hydroxy-3-oxo-1,4(15),11(13)-... - 1-0xo-2,4-eudesmadien-12,6-olide Sq-01187- Sq-01191

w;
8-Hydroxy-3-oxo-1,4(15),11(13)- Sq-01187 Gonzalez, G. et al, J. Chern. Soc., Perkin Trans. I, 1978, 1243
(synth)
eudesmatrien-12,6-olide Ando, M. et al, Bull. Chern. Soc. Jpn., 1979, 52, 2737 (synth)
H Gonzalez, A.G. eta/, Phytochemistry, 1983, 22, 1509 (isol)
Metwally, M.A. et al, Phytochemistry, 1985, 24, 1103 (derivs)
Abagaz, B. eta/, Tetrahedron, 1986, 42, 6003 (cryst struct)
0 7 Arias, J.M. et al, J. Chern. Soc., Perkin Trans. I, 1987, 471 (synth)
Al-Said, M.S. et al, Phytochemistry, 1989, 28, 107 (synth)
0
0
8-Hyd.roxy-1-oxo-4-eudesmen-12,6-olide Sq-01190
C 15H 160 4 M 260.289
(6«,8rx.)-form
O OH
Ac: [84743-54-4]. ·lraZiliiOiide
C 17H 180 5 M 302.326 H
Constit. of Hieracium irazuensis. Cryst. (EtOAc). Mp
202-204°.
-- (6cx,8cx, llcx)-form

Hasbun, C. et al, J. Nat. Prod. (Lloydia), 1982, 45, 749.

0
C 15Hzo04 M 264.321
9-Hyd.roxy-3-oxo-1,4(15),11(13)- Sq-01188
(6rx.,8«,11«)-form
eudesmatrien-12,6-olide
8rz.-Hydroxytaurin
OH Constit. of Artemisia santonicum. Cryst. Mp 150-152°.
[1X] 0 -10° (c, 0.63 in CHCI 3).

0~
Ac: 8«-Acetoxytaurin
Ct,Hn0 5 M 306.358
Constit. of A. santonicum. Oil.
Propanoy/: 8«-Propanoyloxytaurin
0 CtaH240s M 320.385
C 15H 160 4 M 260.289 Constit. of A. santonicum. Oil.
(6rx.,9fl)-form 2-Methylpropanoy/: 8«-lsobutyroxytaurin
C 19H 160 5 M 334.411
Ac: [112356-36-2]. 9P-Acetoxy-3-oxo-1,4(15),11(13)-
Constit. of A. santonicum. Oil.
eudesmatrien-12,6-olide. Gutenbergin
Ct,H 180 5 M 302.326 Tigloyl: 8rz.-Tigloyloxytaurin
Constit. of Gutenbergia cordifo/ia. Cryst. (MeOH). Mp CzoH160 5 M 346.422
189-191°. [1X]i,S +87° (c, 0.23 in MeOH). Constit. of A. santonicum. Oil.
Fujimoto, Y. eta/, Phytochemistry, 1987, 26, 2593. 41X,51X-Epoxide: 4,5-Epoxy-8-hydroxy-1-oxo-12,6-
eudesmano/ide. 4rz.,5rx.-Epoxy-8rz.-hydroxytaurin
C 15Hzo05 M 280.320
4-Hyd.roxy-1-oxo-2-eudesmen-12,6-olide Sq-01189 Constit. of A. santonicum. Cryst. Mp 256-258°.
(6/l,B«,llfl)-form [474-05-5] lfi·Santonin. Pseudosantonin

ffi__,H
0
lsol. from A. spp. Cryst. (EtOH). Mp 182.8° (185-188°).
[IX]~ -169° (CHC1 3).
Clemo, G.R. et al, J. Chern. Soc., 1946, 30 (isol)
H~-- Absolute Pinhey, J.T. et al, Aust. J. Chern., 1965, 18, 543 (pmr)
Moss, G.P. et al, J. Chern. Soc., Perkin Trans. I, 1974, 1525 (cmr,
configuration
stereochem)
0
Meri~;li, A.H. et al, Planta Med., 1988, 54, 447 (iso/, pmr)
C 15Hzo04 M 264.321
(4rx.,6rx.,llrx.)-form [3162-56-9] Vulgarin. Barre/in. Judaicin. 1-0xo-2,4-eudesmadien-12,6-olide Sq-01191
Tauremisin A
Constit. of Artemisia vulgaris, A. judaica and A. taurica.

~OH
Oral hypoglycemic agent. Cryst. (EtOH). Mp 174-175°.
[1X]~ +48.7° (c, 3.86 in CHC13).
I> LE3170000.
4-Hydroperoxide: [72505-77-2]. 4rx.-
Hydroperoxydesoxy,ulgarin. Peroxyvulgarin
C 15Hzo05 M 280.320 0
From A. judaica. Gum, needles (Me2CO/Et20). Mp 170- C 15H 180 4 M 262.305
1710. [1X] 0 -44° (c, 0.1 in MeOH).
Angeloyl: [60461-01-0]. Semopodin
11,13-Didehydro: see 4-Hydroxy-1-oxo-2,11(13)- CzoH240 5 M 344.407
eudesmadien-12,6-o/ide, Sq-01182 Constit. of the seeds of Feru/a oopoda. Cryst. Mp 177-
(4fl,6rx.,ll«)-form [66289-87-0] 4-EpiPulgarin 1780.
From A. judaica and A. canariensis. Cryst.
Serkerov, S.V. et a/, Khim. Prir. Soedin., 1976, 392; CA, 85,
(C 6H 6fhexane)(also descr. as gum). Mp 192-194°. [1X] 0 124181j.
+77.5° (c, 5.7 in CHC1 3).
[5091-07-6, 66289-87·0]
Geissman, T.A. eta/, J. Org. Chern., 1962, 27, 1855 (iso/, struct)

367
3-0xo-1,4-eudesmadien-12,6-olide - 3-0xoeudesman-12,6-olide Sq-01192 - Sq-01197

3-0xo-1,4-eudesmadien-12,6-olide Sq-01192 3-0xo-1,7(11)-eudesmadien-12,6-olide Sq-01195

od2i--
CtsH 180 3 M 246.305
o
(6cx, 11 ~H)-form

CtsH180 3
0~~ 1H
I

M 246.305
0
0

(4rr.,5fl,6fl,JO/l)-form [17335-57-8]
t> LE3150000.
y- M etasantonin
(6rr.,llfJH)-form [481-06-1] «-Santonin. Santonin Formed by acid-catalysed rearrangement of Santonic
Occurs widely in plants, especially Artemisia spp. Used acid. Cryst. (EtOAcjpet. ether). Mp 134°. [1X)i~ -225.6°
in treatment of nervous complaints and as anthelmintic. (c, 0.13 in CHCl 3).
Cryst. (Hp, EtOH or Et20). Mp 174-176°. [1X]~ -173°
Hartmann, A.G. et a/, J. Org. Chern., 1968, 33, 3988 (struct)
(EtOH). Chemistry, esp. photochemistry, extensively McMurry, T.B.H. eta/, J. Chern. Soc. C, 1970, 2012 (synth)
investigated.
(6rr.,llrr.H)-form [481-07-2] Jl-Santonin
C15H 180 3 M 246.305 3-0xo-1,11(13)-eudesmadien-12,6-olide Sq-01196
Constit. of A. spp. Cryst. (EtOH). Mp 216-218°. [1X]~
-137.2° (CHC1 3).
Pinhey, J.T. eta/, Aust. J. Chern., 1965, 18, 543 (pmr) 0
Asher, J.D.M. eta/, J. Chern. Soc., 1965, 6041 (cryst struct) I
Boocock, D.G.B. eta/, J. Chern. Soc., Chern. Commun., 1966, 90
(ms) 0
Coggan, P. et a/, J. Chern. Soc. B, 1969, 237 (cryst struct)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen C15H 180 3 M 246.305
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, (4rr.,6rr.)-form [18375-00-3] Tuberiferine
no. 1903 (occur) Constit. of roots of Sonchus tubifer. Cryst. Mp 160-162°.
Heathcock, C.H., The Total Synthesis of Natural Products, [1X]i,O + 9.2°.
(ApSimon, J.W., Ed.), Wiley, N.Y., 1973, 2, 315 (rev)
Marshall, J.A. eta/, J. Org. Chern., 1978, 43, 1086 (synth)
11 IX,13-Dihydro: 3-0xo-1-eudesmen-12 ,6-o/ide
El-Feraly, F.S. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 355 C15H100 3 M 248.321
(synth) Constit. of Dicoma anomala. Gum. [1X]n +30° (c, 0.15 in
Kutney, J.P. eta/, Can. J. Chern., 1984, 62, 2813 (synth) CHCl 3).
11fi,13-Dihydro:
3-0xo-1,4(15)-eudesmadien-12,6-olide Sq-01193 C15H100 3 M 248.321
Constit. of Brachylaena transvaa/ensis. Cryst. (Etpjpet.
ether). Mp 136°. [IX]~ +27° (c, 0.03 in CHCl3).

0~--
Barrera, J.B. eta/, Tetrahedron Lett., 1967, 3475 (isol, struct)
Yamakawa, K. eta/, Tetrahedron Lett., 1975, 2829 (synth)
Grieco, P.A. et a/, J. Chern. Soc., Chern. Commun., 1976, 582
(synth)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 647, 2029 (isol)
0
Ando, M. eta/, J. Org. Chern., 1987, 52, 4792 (synth)
CtsHt803 M 246.305
(6rr.,ll fJH)-form [7 5683-62-4] 3-0xo-12,6-eudesmanolide Sq-01197
Constit. of Arctotheca calendula. Santonan
Inayama, S. et a/, J. Chern. Soc., Chern. Commun., 1980, 445

ortl _-
(synth)
Tsichritzis, F. eta/, Phytochemistry, !990, 29, 195 (isol, pmr, cmr)

3-0xo-1,5-eudesmadien-12,6-olide Sq-01194 -T b~ i (4cx,5cx,6cx,11cx)-:ft~rm

0

o~-
C15H 120 3 M 250.337
(4rr.,5rr.,6rr.,llrr.)-form [13902-54-0] Artepaulin. IX-
Tetrahydrosantonin
lsol. from flowers of Artemisia pauciflora. Cryst.
o (EtOH). Mp 158°. [1X]~ +17.8° (MeOH).
C15H 180 3 M 246.305 (4fl,5fl,6rr.,llrr.)-form [17956-11-5]
(4/l,llrr.)-form [23811-05-4] P- Tetrahydrosantonin
Pyrosantonin Cryst. (Et20). Mp 105°. [IX]~ +9.3° (MeOH).
Prod. from the pyrolysis of Santonin. Cryst. (MeOH). (4fl,5rr.,6rr.,llrr.)-form [14804-46-7]
Mp 121-123°. [IX]~ -144° (c, 0.14 in CHCl3). y- Tetrahydrosantonin
McMurry, T.B.H. eta/, J. Chern. Soc. C, 1971, 1389. Cryst. (EtOH). Mp 96-97°. [1X]i:' + 7.3°.
Banerji, J.C. eta/, J. Chern. Soc., 1957, 5041 (synth)
Hendrickson, J.B. eta/, J. Chern. Soc., 1962, 1678 (synth)
Narayanan, C.R. eta/, J. Org. Chern., 1968, 33, 3156 (struct)
Adekenov, S.M. eta/, Khim. Prir. Soedin., 1983, 238 (isol)

368
1-0xo-4-eudesmen-12,6-olide - 1,3,8-Trihydroxy-4(15),11(13)-... Sq-01198 - Sq-01203

1-0xo-4-eudesmen-12,6-olide Sq-01198 1,3,4,13-Tetrahydroxy-7(11 )-eudesmen- Sq-01201

12,6-olide

(n --
~ 0
(6a,11a)-form

CtsH2003 M 248.321
(6rz,llrz.)-form [23522-05-6] Taurin CtsH 220 6 M 298.335
Constit. of Artemisia granatensis, A. taurica and A. (1P,3P,4rz,6rz)-form
hanseniana. Cryst. (EtOH). Mp 118-119° (109-110°). [IX]~
- 120° (c, 5 in EtOH). 3-Ac: [126005-61-6]. 3P-Acetoxy-1p,41X,13-trihydroxy-7(11)-
eudesmen-I2,61X-olide
(6rz,ll /I)-form Ct,H2407 M 340.372
11-Epitaurin. 11-epi-Taurin Constit. of Achillea fragrantissima. Oil.
Constit. of A. herba-alba. Oil. [IX]~ -45° (c, 0.9 in
CHC1 3). 3,13-Di-Ac: [126005-62-7]. 3p, 13-Diacetoxy-1P,41X-
dihydroxy- 7( 11 )-eudesmen-12,61X-olide
(6p,llrz.)-form [54192-33-5] Finitin C 19H 260 8 M 382.410
Constit. of A. spp. Mp 153-155°. [1X]n -167.7° (c, 1.7 in Constit. of A. fragrantissima. Oil.
CHCI 3).
Abdel-Mogib, M. eta/, Phytochemistry, 1989, 28, 3528 (isol, pmr)
(6p,llfl)-form
Deoxy-1{1-santonin. Deoxypseudosantonin
Isol. from A. spp. Mp 101-102°. [1X]i;l -207° (EtOH). 1,2,8-Trihydroxy-3,11(13)-eudesmadien- Sq-01202
[52918-33-9] 12,6-olide
Dauben, W. eta/, J. Am. Chern. Soc., 1960, 82, 2239 (Finitin)
Kechatova, N.A. eta/, Khim. Prir. Soedin., 1968, 205 (Taurin)
Gonzalez, A.G. eta/, An. Quim., 1974, 70, 231; 1975, 71, 437 (isol,
pmr)
Serkerov, S.V. eta/, Khim. Prir. Soedin., 1976, 665 (Taurin)
Calleri, M. eta/, Acta Crystal/ogr., Sect. C, 1983, 39, 1115 (cryst
struct, 11-Epitaurin)
Sanz, J.F. eta/, Phytochemistry, 1990, 29, 541 (11-Epitaurin)
Ct5H 200 5 M 280.320
3-0xo-7-eudesmen-12,6-olide Sq-01199 (lrz,2P,6rz,Brz)-form
Monogynin
1-(2-Hydroxymethylpropenoyl):
C19H 240 7 M 364.394

~
Constit. of Dimerostemma brasilianum. Gum. [1X]i;
-188° (c, 0.13 in MeOH).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1343.

0 1,3,8-Trihydroxy-4(15),11(13)- Sq-01203
C1sH2003 M 248.321 eudesmadien-12,6-olide
Tentative struct. lsol. from Artemisia monogyna (A.
maritima). Scales (C 6H 6jMe2CO). Mp 138°. [1XjJ;· 5
-164.3° (CHCI 3).
Fukui, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1948, 68,
269; 1958, 78, 710 (isol) HO ~
Geissman, T.A. et a/, Pure Appl. Chern., 1970, 21, 167 (bib/)

Shonachalin B Sq-01200
C1sH200s M 280.320
[101540-24-3]
(1 P,3rz,6rz,Bf/)-form
8-Tigloyl: [94190-31-5]. Trichomatolide B
C 20 H 260 6 M 362.422
Constit. of Calea trichomata. Gum.
!:J.4•5-Isomer, 8-tig/oyl: [94190-30-4]. Trichomatolide C
C 20 H 260 6 M 362.422
From C. trichomata. Gum.
C 15H 22 0 4 M 266.336 Ober, A.G. et a/, Phytochemistry, 1984, 23, 1439.
Struct. revised in 1990. Constit. of Artemisia fragrans.
Cryst. (Et 20jhexane). Mp 127-129°.
Serkerov, S.V. eta/, Khim. Prir. Soedin., 1985, 21, 597 (isol)
Sanz, J.F. eta/, Phytochemistry, 1990, 29, 2913 (isol, struct, pmr,
cmr)

369
1,3,9-Trihydroxy-4(15),11(13)-... - 1,4,15-Trihydroxy-11(13)eudesmen-... Sq-01204 - Sq-01210

1,3,9-Trihydroxy-4(15),11(13)- Sq-01204 1,3,4-Trihydroxy-12,6-eudesmanolide Sq-01207

eudesmadien-12,6-olide
HO

HO~':
HO HO
I I

H<Y(t) --

lib-{ HO \ ' I
I
0 0
0 C 15H 240 5 M 284.352
C15H 200 5 M 280.320 (1 rx.,JP,4P,6rx.,l Orx.,IlPH)-form [120 163-09-9]
Constit. of Pyrethrum santalinoides. Gum. [a:]i;' + 10° (c,
(1 rx.,3rx.,6rx.,9rx. )-form 0.33 in CHC1 3).
Cratystyolide
Abdel-Mogib, M. eta/, Phytochemistry, 1989, 28, 268
3-Ac:
C 17H:zz06 M 322.357
Constit. of Cratystylis conocephala. Cryst. Mp 222-223°. 1,2,11-Trihydroxy-4-eudesmen-12,6-olide Sq-01208
[a:]i;' + 133° (c, 0.25 in CHC1 3).
OH
1,9-Di-Ac:
C19H 240 7 M 364.394
Constit. of C. conocephala. Cryst. Mp 236°. H O ¢ ?,.H
;
Tri-Ac: ~ '
C 21 H 260 8 M 406.432
b 11 'oH
Constit. of C. conocephala. Cryst. Mp 196-198°. [a:]i;' 0
+ 112° (c, 0. 73 in CHC13).
Ct5H:zz05 M 282.336
Zdero, C. et al, Phytochemistry, 1988, 27, 865.
(lp,2p,6rx.,ll/l)-form [59481-62-8] Decipienin H
Constit. of Melanoselinum decipiens.
1,3,13-Trihydroxy-4(15),7(11 )- Sq-01205
11-Angeloyl: [59481-61-7]. Decipienin G
eudesmadien-12,6-olide C20H 280 6 M 364.438
From M. decipiens.
Gonzalez, A.G. eta/, Rev. Latinoam. Quim., 1976, 7, 37.

1,4,11-Trihydroxy-2-eudesmen-12,6-olide Sq-01209
OH

Ct5Hzo05 M 280.320
(lp,Jp,6rx.)-form
3-Ac: [115338-1 0-8]. 13-Desacetyleudesmaafraglaucolide
C 17H 220 6 M 322.357
Constit. of Artemisia judaica. Oil. [a:Ji;' + 82° (c, 0.88 in
Ct5Hzz05 M 282.336
CHC1 3).
(1 rx.,4rx.,6rx.,ll /I)-form
3,13-Di-Ac: [115346-36-6]. Eudesmaafrag/aucolide
Ct9H2407 M 364.394 11-Angeloyl: [57129-58-5]. Decipienin F
Constit. of A. afra. Oil. C20H 280 6 M 364.438
From Melanoselinum decipiens. Oil. [a:] 0 -57° (c, 1 in
Jakupovic, J. et al, Phytochemistry, 1988, 27, 1129 (isol)
.Khafagy, S.M. et a/, Phytochemistry, 1988, 27, 1125 (isol)
EtOH) .
(lrx.,4p,6rx.,IJJI)-form [57082-64-1] Decipienin E
Constit. of M. decipiens. Oil.
1,8,13-Trihydroxy-4(15),7(11)- Sq-01206
11-Angeloyl: [57082-63-0]. Decipienin D
eudesmadien-12,6-olide C 20H 280 6 M 364.438
From M. decipiens. Oil.
Gonzalez, A.G. eta/, An. Quim., 1974, 70, 1028.

1,4,15-Trihydroxy-11(13)eudesmen-12,6- Sq-01210
olide

(1 p,6rx.,8/l)-form
8-Tigloyl: [92484-28-1]. Trichomatolide A
C 20H 260 6 M 362.422
Constit. of Calea trichomata. Gum.
Ober, A.G. eta/, Phytochemistry, 1984, 23, 910.

M 282.336

370
Vernodesmine- Alatusamine Sq-01211 - Sq-01214

15-(2-Methylpropenoyl): [54278-81-8]. Vahlenin Constit. of Agar wood oil (from fungus infected Aquilaria
CI,Hl606 M 350.411 agallocha). Oil. Bp6 134°. [ocln +37.1° (c, 6.1 in CHC1 3).
Constit. of Centaurea hyssopifolia. Cryst. Mp 200° 3oc,4oc-Epoxide: [73465-83-5].
(sinters). [ocln + 17° (c, 1.68 in MeOH). CisH 240 1 M 236.353
Gonzalez, A.G. et al, Phytochemistry, 1974, 13, 1193. Constit. of Alpinia japonica. Oil. [oc]i,S -20.8° (c, 0.4 in
EtOH).
Vernodesmine Sq-01211 3P,4P-Epoxide: [60064-95-1].
[58870-21-6] CisH 240 1 M 236.353
Constit. of A.japoni~a. Needles. Mp 90-91°. [ocln -48.2°
(c, 0.36 in CHC13).

~:'{;-ooc'( 3,4P-Dihydro: [5956-09-2]. Dihydroagarofuran

C 15H 260 M 222.370
Constit. of A. japonica and Feru/a spp. Oil. Bp0.8 82°.

~
[oc]n -79.4° (c, 0.75 in CHC1 3).
3,4-Dihydro, 4oc-hydroxy: [15052-76-3]. 4rx.-
0 Hydroxydihydroagarofuran
C 15H 260 1 M 238.369
~zsHuP 7 M 440.492
Constit. of Vernonia pectoralis. Cryst. Mp 190-194°. [ocln Constit. of A. japonica. Needles (hexane). Mp 128-
+27° (c, 0.58 in Me 2CO). 129.SO. [ocJn -71.6° (c, 0.16 in EtOH).
tl4•15 -Jsomer: P-Agarofuran
McPhail, A.T. et a/, Tetrahedron Lett., 1975, 3675 (isol, cryst
struct) C1sH240 M 220.354
Constit. of Agar wood oil (A. agallocha). Oil. Bp8 130°.
[oc]~ -127.1° (c, 8.3 in CHC1 3). n~ 1.4973.
Maheshwari, M.L. et a/, Tetrahedron, 1963, 19, 1077 (isol)
Barrett, H.C. eta/, J. Am. Chern. Soc., 1967, 89, 5665 (struct)
Marshall, J.A. eta/, J. Org. Chern., 1968, 33, 435 (synth)
Agarofuran eudesmanes Huffmann, J.W. et a/, J. Org. Chern., 1976, 41, 3705 (synth)
Thomas, A.F., Tetrahedron Lett., 1976, 1717 (isol)
Biichi, G. eta/, J. Org. Chern., 1979, 44, 54 (synth)
Itokawa, H. eta/, Chern. Pharm. Bull., 1980, 28, 681 (isol)
Huffman, J.W. eta/, J. Org. Chern., 1982, 47, 3254 (synth)
ltokawa, H. et a/, Chern. Pharm. Bull., 1985, 33, 1148 (derivs, cryst
Acanthothamine Sq-01212 struct)
[107651-98-9]
Alatusamine Sq-01214
CH2 0Ac (8oc)-8-(Acetyloxy)-8-deoxo-4-deoxyevonimine, 9Cl
AcO i
OAc [89945-80-2]

A,:~rt"
0 ~~~rft
0 '
l0

C34H 43N0 16 M 721.711 C38 H 47N0 17 M 789.786

Alkaloid from the stems of Acanthothamnus aphyllus
(Celastraceae). Cryst. (CH 2Cl 2). Mp 287-290°.
Di-0-Ac: Mp 145-148°. [oc]i? +43.25° (c, 0.004 in CHC1 3).
Soriano-Garcia, M. eta/, J. Crystallogr. Spectrosc. Res., 1986, 16,
507; CA, 106, 156742m (cryst struct)
Sanchez, A.A. et a/, Phytochemistry, 1986, 25, 2647 (iso/, ir, pmr,
cmr, struct)
IX-Agarofuran Sq-01213
[5956-12-7]
Alkaloid from the fruits of Euonymus alatus forma striatus
(Celastraceae). Amorph. solid. [oc]~ -ll 0 (c, 3.0 in
CHC1 3).
Picrate: Mp 138-144°.
4P,26-Dihydroxy: [89945-79-9]. Alatusinine. (81X)-8-
(Acetyloxy)-8-deoxo-26-hydroxyevonimine, 9CI
C38 H47N0 19 M 821.785
Alkaloid from the fruits of E. alatus forma striatus
(Celastraceae). Amorph. solid. [oc]~ -16° (c, 0.6 in
CHC13).
Ishiwata, H. eta/, Phytochemistry, 1983, 22, 2839 (isol, uv, ir, pmr,
struct, synth)

M 220.354

371
Cassinine - Cathedulin K2 Sq-01215 - Sq-01220

Cassinine Sq-01215 Cathedulin E5 Sq-01217

[62948-58-7] [61230-24-8]
CH20Ac CH20R3
AcO
I
i
1
OAc
I
R 20I iI OR4
1
AcO, : ~OAc
Absolute
configuration

0 0 I 0 \
\ I /
) I - 0
0 I

~ J
R 1 = R 6 = Ac,R2 = PhCO-,R3 = Nicotinoyl,
R 5 = 3,4 ,5-Trimethoxybenzoyl,
C44H51 N0 17 M 865.883
R4 = -COC(CH3)20Ac
Alkaloid from the root bark of Cassine metabelica
(Celastraceae). Mp 295-298°. Opt. rotn. not reported. C59H64N 20 23 M 1169.154
Wagner, H. et al, Tetrahedron Lett., I977, I25 (prnr, crnr, cryst Alkaloid from Catha edulis (Celastraceae). Amorph. solid.
struct) Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965,
2982 (isol, struct)
Cathedulin E3 Sq-01216
Cathedulin Kll Cathedulin E6 Sq-01218
[61230-22-6] [61230-23-7]

'
As Cathedulin E5, Sq-01217 with
~ R = Ac, R 2 = PhCO-, R 3 = Nicotinoyl, R 4 =
1

-COC(CH 3)pAc, R 5 = 3,4,5-Trimethoxybenzoyl, R 6 =

H

Ac<;>C(H2
'o ,0 : :,. I C57 H 62N 20 22 M 1127.117
Alkaloid from Catha edulis (Celastraceae). Amorph. solid.
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965,
2982 (isol, uv, ir, prnr, crnr, struct)
AcOh
\ Q ; ____
. Q 0
Cathedulin Kl Sq-01219
~ 'H Cathedulin Yl
OH OAc
[68423-03-0]
o o 'cH2
I As Cathedulin E5, Sq-01217 with
0 0 R1 = R2 = R 3 = R 5 = R6 = Ac, R 4 =
'
'
-COC(CH 3)pAc
C42H 53N0 20 M 891.875
Alkaloid from Catha edulis (Celastraceae). Mp 165-168°.
C 54H 68Nz023 M 1105.068 Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965 (isol,
Alkaloid from Catha edulis (Celastraceae). Cryst. uv, ir, prnr, rns, struct)
(Etpjpet. ether). Mp 245-248°. [1X]i,O -44.8° (c, 0.27 in Crombie, L. et al, J. Chern. Soc., Perkin Trans. 1, 1979, 2976
CHC13). (struct)
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965,
2982 (isol, ir, uv, prnr, ms, struct) Cathedulin K2 Sq-01220
[68419-27-2]
As Cathedulin E5, Sq-01217 with
R = H, R 2 = R3 = R 5 = R 6 = Ac, R4 =
1

-COC(CH 3)pAc
C40 H51 N0 19 M 849.838
Major alkaloid from Catha edu/is(Celastraceae). Needles
(Etpjhexane). Mp 181-184°. [1X]i,O -17.8° (c, 1.9 in
CHC1 3).
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. 1, 1979, 2965 (isol,
uv, ir, pmr, ms, cmr, struct)
Crombie, L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2976 (prnr,
crnr, struct)

372
Cathedulin K6 - 1,9-Dihydroxydihydro-P-agarofuran Sq-01221 - Sq-01227

Cathedulin K6 Sq-01221 Cathedulin K19 Sq-01225

[68419-28-3] [106999-79-5]
As Cathedulin E5, Sq-01217 with

Oco
N
R1 = R 3 = H, R 2 = R 5 = R 6 = Ac, R4 =
-COC(CH 3h0Ac
C38H 49N018 M 807.801 / C H2 \
Alkaloid from Catha edulis (Celastraceae). Mp 176-180°.
ifoMe OAc o
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965 (isol,
uv,c ir, prnr, ms, struct)
Crombie, L. et al, J. Chern. Soc., Perkin Trans. J, I979, 2976
MeoQh
~ 11
+I COO CH OAc
(struct) COO 2 OAc

Cathedulin K12 Sq-01222

[68419-29-4]
As Cathedulin E5, Sq-01217 with 0

R 1 = R 2 = R 6 = Ac, R 3 = l'llll;otinoyl, R4 =
-COC(CH 3) 20Ac, R 5 = 3,4,5-trimethoxybenzoyl
C54H 62N 20 23 M ll07.083 C54H 58N 20 23 M ll03.052
Alkaloid from Catha edulis (Celastraceae). Cryst. (Et20). Alkaloid from fresh young leaves and stems ofCatha edulis
Mp 268-272°. (Celestraceae). Cryst. (MeOH). Mp 249-251°.
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965,
Crombie, L. eta/, J. Chern. Soc., Perkin Trans. I, I986, 53 I (iso/,
2982 (isol, uv, ir, prnr, ms, struct)
prnr, crnr, struct)

Cathedulin Kl5 Sq-01223 Cathedulin K20 Sq-01226

[68419-30-7] [106982-89-2]
As Cathedulin E6, Sq-01218 with
R1 = R 3 = H, R 2 = R 5 = R 6 = Ac, R4 =
-COC(CH 3) 20H
C36H 47N017 M 765.764
Alkaloid from Catha edulis (Celastraceae). Cryst.
(Et20/hexane). Mp 191-194°.
Baxter, R.L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2965 (isol,
uv, ir, prnr, ms, struct)
Crombie, L. et al, J. Chern. Soc., Perkin Trans. I, I979, 2976
(struct)

Cathedulin K17 Sq-01224

[106999-78-4]

Ac~ oocO
C59H 62N 20 23 M 1167.138
MeO_ COO ~H OAc Alkaloid from fresh young leaves and stems ofCatha edulis
MeoQcoo 2 OOCPh (Celestraceae).
Crombie, L. eta/, J. Chern. Soc., Perkin Trans. I, I986, 53 I (iso/,
MeO H prnr, crnr, struct)

1,9-Dihydroxydihydro-IJ-agarofuran Sq-01227
H? OH
9

C59H 62 N 20 23 M ll67.138
Alkaloid from fresh young leaves and stems ofCatha edulis
(Celestraceae). Cryst. solid. 0
Crombie, L. et al, J. Chern. Soc., Perkin Trans. I, I986, 53 I (iso/,
prnr, struct) C 15H 260 3 M 254.369
(la.,9/f)-form
9-(2,3-Epoxycinnamoyl), l-Ac:
C26 H 340 6 M 442.551

373
9-Eremophilene-11,12-diol- Evonine Sq-01228 - Sq-01230

Isol. from Celastrus gemmatus. Cryst. (MeOH). Mp 128- Sugiura, K. et a/, Tetrahedron Lett., 1973, 113 (uv, ir, pmr, struct,
1290. [ex]~ -59.67° (c, 0.553 in CHC1 3). Defectively Evonimine, Euonine)
named, shown in nonstandard orientation and descr. as Yamada, K. et al, Tetrahedron, 1978, 34, 1915 (isol, uv, ir, pmr,
(lp,9ex). struct, Alatamine)

Yongqiang, T. eta/, Phytochemistry, 1990, 29, 2923 (isol, uv, cmr,

ms) Evonine, 9CI Sq-01230
[33458-64-9]
9-Eremophilene-11,12-diol Sq-01228 CH20Ac
AcO OAc!
(4o,5~. 7~,11R}-/o~
AcO, ' : ' 0
Wf'CH,OH
I

C 15H 260 1 M 238.369

(4r~.,5p,7p,JJR)-form[99694-82-3] Debneyol
Phytoalexin from Nicotiana debneyi and N. tabacum.
Ip-Hydroxy: Ip-Hydroxy-9-eremophi/ene-11 ,12-diol. 1-
Hydroxydebneyol
C 15H 260 3 M 254.369
C 36H 43N0 17 M 761.732
Constit. of N. tabacum.
Alkaloid from Euonymus alatus, E. europaeus and E.
8P-Hydroxy: 8P-Hydroxy-9-eremophi/ene-11, 12-diol. 8- sieboldiana (Celastraceae). Cryst. (EtOH or pet.
Hydroxydebneyol ether/Me 2CO). Mp 184-190°. [exJn +8.4° (c, l .5 in
C 15H 260 3 M 254.369 CHC1 3); +21.1° (c, 1.46 in EtOH).
Constit. of N. tabacum.
0 2-De-Ac: [36017-57-9]. ()2-Deacetylevonine
(4«,5P,7«,11R)-form C 34H 41 N0 16 M 719.695
7-Epidebneyol Minor alkaloid from the seeds of E. europaeus
Burden, R.S. et al, Phytochemistry, 1985, 24, 2191 (isol) (Celastraceae). Cryst. (EtOH). Mp 135°.
Watson, D.G. et al, Phytochemistry, 1985, 24, 2195 (isol) 0 6-De-Ac: [33540-08-8]. Evorine. Neoevonine
Brooks, C.J.W. et al, Phytochemistry, 1987, 26, 2243 (biosynth)
Whitehead, I.M. et al, Phytochemistry, 1988, 27, 1365 (isol,- derivs) C 34 H 41 N0 16 M 719.695
Whitehead, I.M. et al, Phytochemistry, 1989, 28, 775 (biosynth) Alkaloid from E. alatus, the fruits of E. sieboldiana and
the seeds of E. europaeus (Celastraceae). Cryst. (MeOH,
Et20jpet. ether or pet. etherjMe2CO). Mp 266-268°
Evonimine, 9CI Sq-01229 (257-259°). [ex]~ +20° (c, 1.11 in CHC1 3); +41° (c, 1.13
/soevonine in MeOH).
[41758-54-7] 02,06-Di-de-Ac: [36072-68-1). ()2,£r-Dideacetylevonine
CH20Ac C31 H 39N0 15 M 677.658
AcO : OAc Minor alkaloid from the seeds of E. europaeus
(Celastraceae). Cryst. (EtOH). Mp 141°.
1
Ac0~! 0 2
1
8
0 6,09-Di-de-Ac: [35721-62-1]. Evozine
C31 H 39N0 15 M 677.658
a ~ Alkaloid from the seeds of E. europaeus (Celastraceae).
H. Ac Cryst. (Me0H/Et20). Mp 288-290°. [ex]~ + 13° (c, 0.92
0 in CHC1 3).
6 0 :
4-Deoxy: [36017-50-2). Evonoline. 4-Desoxyevonine
o/ C36H 43N0 16 M 745.733
Alkaloid from the seeds of E. europaeus (Celastraceae).
N'I ' Cryst. (pet. etherjMe 2CO). Mp 150-158°. [ex]i? +6.0° (c,
3.2 in CHC1 3).
C 36H 43N017 M 761.732 8ex-Alcohol, 8-Ac: [33458-82-1]. Euonymine
Alkaloid from the seeds of Euonymus europaeus and E. C38 H 47 N0 18 M 805.785
sieboldiana (Celastraceae). Amorph. [exJn +21° (c, 1.5 in Alkaloid from E. alatus and the fruits of E. sieboldiana
CHC1 3); + 30.5° (c, 0.9 in EtOH). (Celastraceae). Amorph.
8ex-Alcohol, 8-Ac: [41758-69-4]. Euonine 8ex-Acetoxy, 8-deoxo, picrate: Cryst. (C 6H 6). Mp 140-146°.
C 38H 47 N018 M 805.785 [exJn -20° (c, 0.32 in CHC1 3).
Minor alkaloid from the seeds of E. sieboldiana
(Celastraceae). Mp 149-153°. [exJn - 2.SO (c, 6.4 in 8-ex-Alcohol, 8-Ac, 6-de-Ac: [33510-25-7]. Neoeuonymine
CHCl 3). C 36 H 45N0 17 M 763.748
Alkaloid from E. sieboldiana (Celastraceae). Cryst.
02-De-Ac, 0 2-benzoyl, 26-hydroxy: [41855-33-8]. Alatamine (MeOH). Mp 259-262°. [exJi? - UO (c, 0.49 in CHC1 3).
C41 H 45 N0 18 M 839.802
Alkaloid from E. alatus (Celastraceae). Cryst. (MeOH). Klasek, A. et al, Helv.'Cmm. Acta, 1971, 54, 2144 (isol, uv, ir, ms)
Pai1er, M. et al, Monatsh. Chern., 1971, 102, 1873 (O'-
Mp 185-193°. [ex)~ +44° (c, 1.08 in CHC1 3). Deacety1evonine, Dideacety1evnone,synth; Evonoline,)
0 2-De-Ac, 0 2-benzoyl, 0 26-acetoxy: Mp 183-189°. Sugiura, K. et al, Tetrahedron Lett., 1971, 2733 (Euonymine, isol,
Dubravkova, L. et al, Phytochemistry, 1973, 12, 944; Collect. uv, ir, struct)
Czech. Chern. Commun., 1973, 38, 2132 (iso/, uv, ord, ir, pmr, Wada, H. et al, Tetrahedron Lett., 1971, 3131 (stereochem)
ms, struct) Sasaki, K. et al, J. Chern. Soc., Perkin Trans. 2, 1972, 1268
(Evonine, Evorine, cryst struct, abs con.fig)

374
1,2,3,4,6,9,14-Heptahydroxydihydro-... - 1,2,3,4,9,14-Hexahydroxydihydro-p-... Sq-01231 - Sq-01234

Khisek, A. eta/, Tetrahedron Lett., 1972, 941 (Evorine, 1,2,4,6,8,9,14-Heptahydroxydihydro-JJ- Sq-01233

Dideacetylevonine, pmr, struct)
Budzikiewicz, H. et at, Z. Naturforsch., B, 1972, 27, 800 (Evonine,
agarofuran
Evonoline, Evorine, isol, uv, ir, pmr,ms, struct) 14
Dubravkova, L. eta/, Collect. Czech. Chern. Commun., 1973, 38, CHpH
2132 (Evonine, Evonoline, isol, uv, ord, ir, pmr, ms) HO: OH
Crombie, L. eta/, Phytochemistry, 1973, 12, 703 (Evonine, I :
I
I

Dideacetylevonine, 0 2- Deacetylevonine) I

Shizuri, Y. et at, Tetrahedron, 19.73, 29, 1773 (Evonine, Evorine,

isol, uv, ir, pmr, struct) (1 cx,2cx,6~,8cx,9cx )-form
Sugiura, K. et at, Chern. Lett., 1975, 579 (synth)
Yamada, K. eta/, Tetrahedron, 1977, 33, 1725; 1978, 34, 1915
(Euonymine, Neoeuonymine, isol, uv, ir, pmr,struct, synth)

1,2,3,4,6,9,14-Heptahydroxydihydro-JJ- Sq-01231 C1sH 260 8 M 334.366

agarofuran (1 rx.,2rx.,6P,Brx.,9rx. )-form
9-Benzoy/, 1,2,6,8,14-penta-Ac: [116159-73-0]. Celangulin
14
CHPH C 31 H~.0 14 M 648.660
HOI ! OH Constit. of Celastrus angu/atus. Insect antifeedant.
I I
I Amorph. powder.
I
1,9-Dibenzoy/, 2,6,8,14-tetra-Ac: 2rx.,6P,Brx.,14-Tetraacetoxy-
lrx.,9rx.-dibenzoyloxy-4p-hydroxydihydro-p-agarofuran
C37 H 4z0 14 M 710.730
Constit. of Maytenus canariensis. Amorph. solid. Mp
50-52°.
(1 rx.,2rx.,6P,Brx.,9fl)-form
Ct 5Hu08 M 334.366 2,8,9-Tribenzoy/, 1,6,14-tri-Ac: [111950-73-3]. Brx.-
(lrx.,2rx.,1P,4POH,9fl)-form Benzoyloxyacetylpringleine
9-(3-Pyridinecarbonyl), 1,2,6,14-tetra-Ac: (31146-55-1]. C4zH440 14 M 772.801
Maytoline !sol. from C. pringlei. Amorph. powder. Mp 98°.
C19H 37N0 13 M 607.610 Sanchez, A.A. et at, Phytochemistry, 1987, 26, 2631
Alkaloid from the fruit of Maytenus serrata (M. ovatus) (Benzoyloxyacetylpringeleine)
(Celastraceae). Noncryst. [rx.]i,S +0.3° (c, 0.75 in CHC1 3). Wakabayashi, N. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 537
(Celangulin)
9-(3-Pyridinecarbonyl), 1,2,6,14-tetra-Ac; B,Mel: [31146-59- Gonzalez, A.G. et at, Phytochemistry, 1989, 28, 173.
5].
Cryst. (MeOH/EtzO). Cryst. unstable in air and rapidly
lose solvent of crystallization to give a powder. Mp 190- 1,2,3,4,9,14-Hexahydroxydihydro-P- Sq-01234
1930 dec. agarofuran
9-(3-Pyridinecarbonyl), 6-benzoy/, 1,2,3,14-tetra-Ac: (60512-
69-8]. Maytolidine
C36H 41 N0 14 M 711.718
Alkaloid from the fruit of M. serrata (Celastraceae).
Cryst. (EtOAcjEtzO). Mp 128-132°.
Bryan, R.F. eta/, J. Chern. Soc. B, 1971, 2159 (cryst struct)
Kupchan, S.M. eta/, J. Org. Chern., 1977, 42, 115 (isol, uv, ir,
pmr, ms, struct)

1,2,3,6,8,9,14-Heptahydroxydihydro-JJ- Sq-01232 CtsHu07 M 318.366

agarofuran (lrx.,2rx.,3P,4POH,9fl)-form
CtsHu08 M 334.366 9-(3-Pyridinecarbonyl), 2-benzoy/, 1,14-di-Ac: [58546-13-7].
(lrx.,2rx.,Jp,6p,Brx.,9rx.)-form Cathidine D
8-Benzoy/, 1,2,3,6,9,14-hexa-Ac: Ejap 6 C31 H 37N0 11 M 611.644
C34H410ts M 690.697 Alkaloid from Catha edulis (Celastraceae). Cryst.
!sol. from Euonymus japonicus. Cryst. (MeOH). Mp 140- (MeOH). Mp 219.5-222°. [rx.Jn + 74o (c, 0.5 in CHC1 3).
1420. Cais, M. et at, Tetrahedron, 1975, 31, 2727 (isol, uv, ir, pmr, struct)
Rozsa, Z. eta/, J. Chern. Soc., Perkin Trans. I, 1989, 1079.

375
1,2,4,6,8,9-Hexahydroxydihydro-P-... - 1,2,6,8,9,14-Hexahydroxydihydro-P-... Sq-01235 - Sq-01237

1,2,4,6,8,9-Hexahydroxydihydro-P- Sq-01235 C36 H 54Pu M 674.784

agarofuran lsol. from E. europaeus. Complete struct. unknown.
3-Furoy/, bis(2-methylbutanoyl), di-Ac: Eur 9
HO OH C34H 480u M 648.746
I I
lsol. from E. europaeus. Complete struct. unknown.
9-(3-Pyridinecarbonyl), 1,2,6,14-tetra-Ac: [31146-56-2].
Maytine
C29H 37NOu M 591.611
Alkaloid from the fruits of Maytenus serrata
(Celastraceae). Noncryst.
1,2,9-Trifuroyl, 6,12-di-Ac: 6p,I2-Diacetoxy-Irx.,2rx.,9fJ-tri(2-
C 15H 260 7 M 318.366 furancarbonyloxy)-4fJ-hydroxydihydro-fJ-agarofuran
(Irx.,2rx.,6p,ap,9fl)-form C34H 360 15 M 684.649
8,9-Di/Jenzoy/, 1,6-di-Ac: [111514-63-7]. Triptofordin C2 Constit. of Euonymus bungeanus. Amorph. powder. [ex]i:
C33H 380n M 610.657 + 83.94° (c, 0.554 in CHCI3).
Constit. of Tripterygium wilfordii var. regelii. Amorph. 1,9-Difuroy/, 2-(2-methylbutanoyl), 6,12-di-Ac: 6P,I2-
powder. Mp 128-131°. [ex]i;1 -44.7° (c. 0.27 in MeOH). Diacetoxy-Irx.,9fJ-di(2-furancarbonyloxy)-2rx.-(2-
MF incorrectly given as C33 H340u. methylbutanoyloxy)-4fJ-hydroxydihydro-fJ-agart~furan
2-Ketone, 8,9-dibenzoy/, 1,6-di-Ac: [111514-62-6]. C34H 420 14 M 674.697
Triptofordin CI Constit. of E. bungeanus. Cryst. (EtOAcfpet. ether). Mp
C33H360n M 608.641 145-146°. [ex]~ +43.07° (c, 0.534 in CHCI 3).
From T. wilfordii var. rege/ii. Cryst. (MeOH). Mp 249- 2,9-Difuroyl, 1-(2-methy/butanoyl), 6,12-di-Ac: 6P,l2-
2510. [ex]i,S -22.6° (c, 0.22 in MeOH). Diacetoxy-2rx.,9fJ-di(2-furancarbonyl)-Irx.-(2-
Takaishi, Y. eta/, Phytochemistry, 1987, 26, 2325. methylbutanoyloxy)-4fJ-hydroxydihydro-fJ-agart~furan
Constit. of E. bungeanus. Amorph. powder. [ex]~
+ 70.85° (c, 0.494 in CHCI3).
1,2,4,6,9,14-Hexahydroxydihydro-IJ- Sq-01236
Sugiura, K. et a/, Chern. Lett., 1975, 471 (Euolalin)
agarofuran Kupchan, S.M. eta/, J. Org. Chern., 1977, 42, 115 (Maytine)
Sanchez, A.-A. et al, Phytochemistry, 1987, 26, 2631.
Rozsa, Z. et al, J. Chern. Soc., Perkin Trans. I, 1989, 1089.
Tu, Y.Q. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 603.

1,2,6,8,9,14-Hexahydroxydihydro-P- Sq-01237
agarofuran

Ct5H:u;07 M 318.366
(lrx.,2rx.,6P,9fl)-form (lcr,2cr,6j3,8cr,9cr)-form
2,9-Dibenzoy/, 6,14-di-Ac: [111950-80-2]. Pringleine
C33H380n M 610.657
Constit. of Celastrus pringlei. Amorph. powder. Mp
128°.
2,9-Dibenzoy/, 1,6,14-tri-Ac: [111950-72-2]. Acetylpringleine
C15H 260 7 M 318.366
C35H 400u M 652.694 (Irx.,2rx.,6P,8rx.,9rx.)-form [57461-75-3] Alatoft
From C. pringlei. Amorph. powder. Mp 118°. Constit. of Alatus striatus. Amorph. Ever-2, Ever-6 and
Ever-7 are esters isol. from Euonymus verrucosus.
1,2-Dibenzoy/, 9-(2-methy/butanoyl), 6,14-di-Ac: [56691-82-
8]. Euolalin Hexa-Ac: Cryst. Mp 205-207°.
C38H 460u M 694.774 6,9,14- Tri-Ac, 1,2,8-tribenzoy/: [60389-86-8]. Alatolin
Constit. of Euonymus a/atus. Cryst. Mp 219-221°. [ex]~ C42H440 13 M 756.802
+88.SO (c, 2.3 in CHC1 3). lsol. from Euonymus a/atus and E. europaeus. Amorph.
Tris(3-furoyl), di-Ac: Eur I powder. [ex]~ + 14.0° (c, 2.3 in CHC13).
C34H 360 15 M 684.649 Tri-Ac, tribenzoy/: [57651-32-8]. Polyester AI
lsol. from E. europaeus. Posn. of ester groups C42H440 13 M 756.802
undetermined. lsol. from seeds of E. europaeus. Mp 95-100°. Posn. of
Dibenzoyl, tri-Ac: Eur 3 ester groups unknown. It has been impossible to
C35H400 12 M 652.694 determine whether Alatolin and polyester AI are
Isol. from E. europaeus. Posn. of ester groups identical or different.
undetermined. Tetra-Ac, dibenzoyl: [57651-33-9]. Polyester A2
Tris(3-furoyl), 2-methylbutanoy/, di-Ac(J): Eur 6 C37 H420 13 M 694.731
C39H 440 16 M 768.767 From E. europaeus. Cryst. (diisopropyl ether). Mp 188-
Isol. from E. europaeus. Complete struct. unknown. 1920. Posn. of ester groups unknown.
Tris(3-furoyl), 2-methylbutanoyl, di-Ac(2): Eur I5 Tri-Ac, dibenzoyl: [57636-54-1]. Polyester A3
C39H 440 16 M 768.767 C35H 400 12 M 652.694
lsol. from E. europaeus. Complete struct. unknown. From E. europaeus. Mp 85-90°.
Benzoyl, bis(2-methylbutanoyl), di-Ac: Eur 7 2,8-Dibenzoy/, 6,9,14-tri-Ac: Eur 14

376
1,2,6,8,9,15-Hexahydroxydihydro-P.... - 1,4,6,8,9,14-Hexahydroxydihydro-p.... Sq-01238 - Sq-01239

C 35H 400 11 M 652.694 Constit. of M. chubutensis. Oil.

lsol. from E. europaeus and E. /atifo/ius. 1,2,6,8,15-Penta-Ac, 9-benzoy/: 1«.,2«.,6P,B«.,l5-
8-Benzoy/, 1,2,6,9,14-penta-Ac: Ejap 5. Elat 4 Pentaacetoxy-9P-benzoyloxydihydro-P-agarofuran
C32H400 13 M 632.660 C 32 H 400 13 M 632.660
lsol. from E. japonicus E. europaeus and E. latifolius. Constit. of M. chubutensis. Cryst. (EtOAc). Mp 135-
Cryst. (cyclohexanefEtOAc). Mp 245-247°. Ejap 5 and 1400. [a]~ + 7.7° (c, 0.52 in CHC1 3).
Elat 4 appear to be identical although this is not stated. 8-Ketone, 1,2,6-tri-Ac, 9-benzoyl: 11Z,2«.,6P-Triacetoxy-9P-
8-Benzoy/, 2,6,9,14-tetra-Ac: Ejap 12 benz.oyloxy-15-hydroxy-8-oxodihydro-p.agarofuran
C 30H 380 11 M 590.623 C 28 H 340 11 M 546.570
I sol. from E. japonicus. Cryst. (MeOH). Mp 134-135°. Constit. of M. chubutensis. Oil. [ex]~ + 10° (c, 0.27 in
1,8-Dibenzoy/, 2,6,9,14-tetra-Ac: Eur 2. Elat 6. A2 CHC1 3).
C 37 H 420 13 M 694.731 8-Ketone, 1,2,6,15-tetra-Ac, 9-benzoyl: 1«.,2«.,6P,l5-
lsol. from E. europaeus and E. latifolius. Tetraacetoxy-9P-benz.oyloxy-8-oxodihydro-P-agarofuran
1,8-Dibenzoy/, 2,9,14-tri-Ac: Eur 21 Constit. of M. chubutensis. Oil. [a]~ + 174° (c, 0.46 in
C 35H 40 0 11 M 652.694 CHC1 3).
lsol. from E. europaeus. [128397-66-0, 128443-60-7]
(1 «.,2«.,6P,8«.,9fl)-form Gonzalez, A.G. eta/, Heterocycles, 1989, 29, 2287 (isol, prnr)
8,9-Dibenzoy/, 1,2,6,14-tetra-Ac: Elat 5 Gonzalez, A.G. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 474 (isol,
C 37H 420 13 M 694.731 prnr)
lsol. from E. latifolius.
9-Benzoy/, 1,2,6,8,14-penta-Ac: Ejap 4 1,4,6,8,9,14-Hexahydroxydihydro-~ Sq-01239
C32H400 13 M 632.660 agarofuran
lsol. from E. japonicus. Cryst. (cyclohexanefEtOAc). 14
Mp 245-247°. CH2 0H
Budzikiewicz, H. et a/, Tetrahedron, 1975, 31, 1701, 2638 HO:
I I
OH
I
(polyesters) : ,OH
Romer, A. et al, Z. Naturforsch., B, 1976, 31, 607 (Alatolin)
Sugiura, K. eta/, Tetrahedron, 1982, 38, 3465 (iso/, struct) (1 a,6~,8a,9a }form
Begley, M.J. eta/, J. Chern. Soc., Perkin Trans. 1, 1986, 535 (isol)
Rozsa, M.J. et al, J. Chern. Soc., Perkin Trans. 1, 1989, 1079, 1089
(isol, struct)

1,2,6,8,9,15-Hexahydroxydihydro-~­ Sq-01238 C 15H 260 7 M 318.366

agarofuran (1«.,6P,8«.,9«.)-form
ent-5ex, 11-Epoxy-1p,4a,6a,8P,9P, 14-eudesmanehexo/
1,9-Dibenzoyl, 6,8,14- Tri-Ac: 6P,8«.,14- Triacetoxy-1 «.,91X.-
dibenz.oyloxy-4p.hydroxydihydro-p.agarofuran
C 35 H 400 11 M 652.694
Constit. of Maytenus canariensis. Cryst. Mp 212-213°.
1-Cinnamoyl, 9-benzoy/, 6,8,14-tri-Ac: [112018-96-9].
Triptofordin D2
C37H 420 11 M 678.732
Constit. of Tripterygium wilfordii. Needles (MeOH). Mp
103-109°. [a)i; -3.5° (c, 0.28 in MeOH).
C 15H 260 7 M 318.366
1-(E-Cinnamoyl), 8-(3-pyridinecarbonyl), 9-benzoyl, 6,14-di-
(1 «.,2«.,6P,8«.,9«. )-form
Ac: [112494-33-4]. Triptofordinine AI
1,2 ,6-Tri-Ac, 9-benzoy/: [128397 -64-8]. 1«.,2«,6P-Triacetoxy- C41 H 43N0 11 M 741.790
9«.-benz.oyloxy-8«.,15-dihydroxydihydro-p.agarofuran Alkaloid from leaves of Tripterygium wilfordii var.
C 28 H 360 11 M 548.586 regelii (Celastraceae). Mp 193-194°. [1X]n -81.4°
Constit. of Maytenus chubutensis. Oil. [ex]~ - 11.2° (c, (MeOH).
0.83 in CHC1 3).
1-(Z-Cinnamoyl), 8-(3-pyridinecarbonyl), 9-benzoy/, 6,14-di-
1,2,6,8- Tetra-Ac, 9-benzoy/: [128397-65-9]. 1«.,2«.,6P,B«.- Ac: [112571-89-8). Triptofordinine A2
Tetraacetoxy-9«.-benz.oyloxy-15-hydroxydihydro-P- C41H 43N0 11 M 741.790
agarofuran Alkaloid from T. wilfordii var. regelii. Mp 93-94°. [1X]n
C30H 38 0 11 M 590.623 -101.0° (MeOH).
Constit. of M. chubutensis. Oil.
9-Benzoyl, 8-(2-methylbutanoyl), 1,6,14-tri-Ac: 1«.,6P,l5-
(1 «.,2«.,6P,8«.,9fl)-form Triacetoxy-9«.-benzoyloxy-4P-hydroxy-8«.-(2-
1,2,6-Tri-Ac, 9-benzoy/: 1«.,2«.,6P-Triacetoxy-9P-benz.oyloxy- methylbutanoyloxy )dihydro-p.agarofuran
8«.,15-dihydroxydihydro-p-agarofuran C33H 440 11 M 632.703
Constit. of M. chubutensis. Oil. [ex]~0 + 17.2° (c, 0.53 in Constit. of Maytenus canariensis. Amorph. solid. Mp
CHC1 3). 57°.
1,2,6,8- Tetra-Ac, 9-benzoyl: 1«.,2«.,6P,B«.-Tetraacetoxy-9P- 1,9-Dibenzoyl, 8-(2-methylbutanoyl), 6,15-di-Ac: 6p,l5-
benz.oyloxy-15-hydroxydihydro-p.agarofuran Diacetoxy-l «.,9«.-dibenz.oyloxy-4p.hydroxy-8«.-(2-
Constit. of M. chubutensis. Oil. [a]~ -20.6° (c, 1.79 in methylbutanoyloxy )dihydro-p.agarofuran
CHC1 3). C36 H 420 10 M 634.722
1,2,6,15- Tetra-Ac, 9-benzoyl: 1«.,2«.,6P,l5-Tetraacetoxy-9p- Constit. of M. canariensis. Amorph. solid. Mp 62°.
benzoyloxy-81X.-hydroxydihydro-P-agarofuran (11Z,4P,6P,BP,9«)-form

377
Horridine- 1,2,4,6,9-Pentahydroxydihydro-IJ-... Sq-01240 - Sq-01243

ent-5oc,ll-Epoxy-lp,4oc,6rx.,8rx.,9p, 14-eudesmanehexol Mayteine Sq-01241

1-Benzoyl, 9,14-di-Ac: [107602-75-5]. 9rx.,l4-Diacetoxy-lrx.- [1 04736-05-2]
benzoyloxy-4p,6p,8p-trihydroxydihydro-P-agarofuran
C26H 340 10 M 506.549
Constit. of Rzedowskia tolantonguensis. Cryst.
(EtOAcjhexane). Mp 278-281°.
1-Benzoyl, 6,9,14-tri-Ac: [107602-77-7]. 6P,9rx.,l4-
Triacetoxy-1 rx-benzoyloxy-4P,8P-dihydroxydihydro-P-
agarofuran
C28H 360 11 M 548.586
From R. tolantonguensis. Cryst. (EtOAcjhexane). Mp
142-145°.
1-Benzoy/, 6,8,9,14-tetra-Ac: [107602-74-4]. 6P,8P,9rx,l4-
Tetraacetoxy-l rx-benzoy/oxy-4p-hydroxydihydro-P-
agarofuran
C30H 380 12 M 590.623
From R. tolantonguensis. Cryst. (EtOAcjhexane). Mp C43H 49N0 18 M 867.856
210-212°. Alkaloid from the roots of Maytenus guianensis
1,8-Dibenzoy/, 9,14-di-Ac: [107602-78-8]. 9rx,l4-Diacetoxy- (Celastraceae). Amorph. solid. Mp 172-175°. [rx]~
loc,8P-dibenzoyloxy-4p,8p-dihydroxydihydro-P-agarofuran -9.36° (c, 0.47 in CHC1 3).
C33H 380 11 M 610.657 De Sousa, J.R. eta/, Phytochemistry, 1986, 25, 1776 (twl, uv, ir,
From R. tolantonguensis. Cryst. (Et0Ac/C 6H 6). Mp 202- pmr, ms, struct)
2040.
8-Ketone, 1-benzoy/, 6,9,14-tri-Ac: [107602-76-6]. 6P,9rx,l4- Neoalatamine Sq-01242
Triacetoxy-l rx-benzoy/oxy-4p-hydroxy-8-oxodihydro-P-
0 2,06-Dideacety/-02-benzoy/-26-hydroxyevonimine, 9CI
agarofuran
C28H 340 11 M 546.570 [89945-78-8]
From R. tolantonguensis. Cryst. (EtOAcjhexane). Mp CHpAc
224-226°. AcO :I OAc
I 1
8-Ketone, 1-cinnamoy/, 9-benzoy/, 6,14-di-Ac: [111950-42-6].
Triptofordin Dl Ph~,(Ylo
C35H 380 11 M 634.679

~
Constit. ofT. wilfordii. Needles (MeOH). Mp 224-226°.
[rx]i,? +56.1° (c, 0.25 in MeOH).
Gonzalez, A.G. eta/, Heterocycles, 1986, 24, 3379. 0 '
Takaishi, Y. eta/, Chern. Pharm. Bull., 1987, 35, 3534 0/
(Trlptofordinins)
Takaishi, Y. eta/, Phytochemistry, 1987, 26, 2581 (Triptofordins)
Gonzalez, A.G. eta/, Phytochemistry, 1989, 28, 173; 1990, 29,
2577. C39H 43N0 17 M 797.765
Alkaloid from the fruits of Euonymus a/atus forma striatus
Horridine Sq-01240 (Celastraceae). Amorph. solid. [rx]~ +42° (c, 1.1 in
CHC1 3).
[102865-30-5]
Ishiwata, H. et a/, Phytochemistry, 1983, 22, 2839 (isol, uv, ir, pmr,
CH2 0Ac struct)
AcO ! OOCPh
1 1,2,4,6,9-Pentahydroxydihydro-p- Sq-01243
Ac0: m
I OAc
agarofuran
-H
COO/ OA
HOo c,

'6

C15H 260 6 M 302.367

C43H 49N0 18 M 867.856 (1 rx.,2p,6p,9fl)-form
Alkaloid from the root bark of Maytenus horrida
1-Cinnamoy/, 6-(3-pyridinecarbonyl), 9-Ac: [117677-26-6].
(Celastraceae). Amorph. powder.
9P-Acetoxy-lrx.-cinnamoyloxy-2p,4P-dihydroxy-6P-
Gonzalez, A.G. eta/, Heterocycles, 1986, 24, 1295 (isol, uv, ir, nicotinoyloxydihydro-fl-agarofuran. 1rx-Cinnamoyloxy-6P-
pmr, cmr, ms, struct) nicotinoy/oxy-9P-acetoxy-2P,4P-dihydroxydihydro-P-
agarofuran
C32 H 37N09 M 579.646
Alkaloid from the aerial parts of Orthosphenia mexicana
(Celastraceae). Amorph. solid.

378
1,2,6,9,14-Pentahydroxydihydro-P-... - 1,2,6,9,15-Pentahydroxydihydro-P-... Sq-01244 - Sq-01246

6,9-Di-Ac, 1-cinnamoy/: 6P,9P-Diacetoxy-1 rx-cinnamoyloxy- 1,2,6,9,14-Pentahydroxydihydro- JJ- Sq-01245

2P,4P-hydroxydihydro-P-agarofuran agarofuran
C28 H 360 9 M 516.587
Constit. of Orthosphenia mexicana. CHPH
1-(2,3-Epoxycinnamoyl), 2,9-di-Ac: [117610-40-9]. HOi OH
I :
Rzedowskin A I
l 9
C28H 360 10 M 532.586 I

Constit. of Rzedowskia tolantonguensis. Cryst.

(Me 2COjhexane). Mp 210°. Rzedowskin Band
Rzedowskin C are mixts. of related esters isol. from the
same source.
(1 rx.,2rx.,9f/)-form
6-Ketone, 1,9-dibenzoy/, 2-Ac: [83790-33-4]. Mortonol B C 15H 260 6 M 302.367
C31H 340 9 M 550.604 (1 rx.,2rx.,6p,9rx. )-form
Constit. of Mortonia greggii. Cryst. (Me2CO/diisopropyl
0-(2-Methy/butanoyl), bis(3-furoyl), di-Ac: [57651-30-6].
ether). Mp 216-218°. [rxln +23.45° (CHC1 3).
Polyester B1
Martinez, M. et al, Phytochemistry, 1982, 21, 1335 (Martino/ B) C34H42014 M 674.697
Gonzalez, A.G. et al; Phytochemistry, 1987, 26, 2133; 1988, 27,
lsol. from seeds of Euonymus verrucosus. Mp 112-120°.
473 (isol, ir, pmr, ms, struct)
Jimenez, M. et al, Phytochemistry, 1988, 27, 2213 (Rzedowskins) Posn. of ester groups unknown.
Tris(3-furoyl), di-Ac: [57636-55-2]. Polyester B4
C34 H 360 15 M 684.649
1,2,6,9,14-Pentahydroxydihydro-1}- Sq-01244
lsol. from seeds of E. europaeus. Mp 106-ll0°. Posn. of
agarofuran ester groups unknown.
9-Benzoy/, 1,2,6,14-tetra-Ac: Eur 8. Elat 2
C30H 380 11 M 574.624
Isol. from E. europaeus and E. latifolius.
2,9-Dibenzoy/, 1,6,14-tri-Ac: Elat 1
C3sH400 11 M 636.694
Isol. from E. Iatifa/ius.
Budzikiewicz, H. eta/, Tetrahedron, 1975, 31, 1701, 2638.
Rozsa, Z. et al, J. Chern. Soc., Perkin Trans. I, 1989, 1089.

CtsH:u,06 M 302.367 1,2,6,9,15-Pentahydroxydihydro-P- Sq-01246

(1rx.,2rx.,6P,9fl)-form agarofuran
9-(3-Pyridinecarbonyl), 2-benzoy/, 1,6-di-Ac: [93772-06-6].
Maymyrsine HO CHPH
C32H 37N0 10 M 595.645 I
I I
OHi
Alkaloid from the fruits of Maytenus myrsinoides HO, I

(Celastraceae). Prisms (EtOH). Mp 185-187°. [rxln +93°

(c, 1 in CHC1 3).
9-(3-Pyridinecarbonyl), 2-benzoy/, 1,6,14-tri-Ac: [93772-07-
7]. Acetylmaymyrsine
C34H 39N0 11 M 637.682
Alkaloid from the fruits of M. myrsinoides
(Celastraceae). Amorph. solid. [rx]~ +92° (c, 1 in C15H 260 6 M 302.367
CHC1 3). (1 rx.,2rx.,6P,9fl)-form
9-(3-Pyridinecarbonyl), 1-(S-2-methy/butanoyl), 2,6,14-tri- 1,2,6-Tri-Ac, 9-benzoy/: [128397-60-4]. 1rx.,2rx.,6P-Triacetoxy-
Ac: E11er 1 9P-benzoyloxy-15-hydroxydihydro-P-agarofuran
C32 H43N0 11 M 617.692 C28 H 360 10 M 532.586
Alkaloid from Euonymus verrucosus (Celastraceae). Constit. of Maytensis chubutensis. Gum. [rx]~ +29.2° (c,
Cryst. (MeOH aq.). Mp 189-192°. 2.24 in CHC1 3).
Baudouin, G. et al, Heterocycles, 1984, 22, 2221 (uv, ir, pmr, ms, 1,2,6,15-Tetra-Ac, 9-benzoy/: [122475-45-0]. 1rx.,2rx.,6P,15-
cryst struct, deriv) Tetraacetoxy-9P-benzoyloxydihydro-P-agarofuran
Begley, M.J. et al, J. Chern. Soc., Perkin Trans. I, 1986, 535 (cryst C30H 380 11 M 574.624
struct, Ever I) Constit. of M. chubutensis, Euonymus latifolius and E.
europaeus. Oil. [rx]~ + 38.SO (c, 1.16 in CHC1 3).
Rozsa, Z. eta/, J. Chern. Soc., Perkin Trans. I, 1989, 1089 (deriv)
Gonzalez, A.G. eta/, J. Nat. Prod. (Lloydia), 1990,.53, 474 (isol,
pmr, cmr)

379
1,2,8,9,14-Pentahydroxydihydro-p-... - 1,6,8,9,14-Pentahydroxydihydro-p-... Sq-01247 - Sq-01250

1,2,8,9,14-Pentahydroxydihydro- Jl- Sq-01247 Constit. of 0. mexicana. Cryst. Mp 76-80°.

agarofuran (1~:~.,6p,Bp,9fl)-form

14 1-Benzoyl, 6/3-(3-pyridinecarbonyl), 9-Ac: 9ft-Acetoxy-l~:~.­

CH20H benzoyloxy-4ft-hydroxy-6ft-nicotinoy/oxydihydro-p-
HOI
I
i OH agarofuran. loe-Benzoyloxy-6f3-nicotinoyloxy-9f3-acetoxy-
HO, : /OH 4f3-hydroxydihydro-f3-agarofuran
C30 H 35N0 8 M 537.608
Alkaloid from the aerial parts of 0. mexicana and the
root bark of R. tolantonguensis (Ce1astraceae). Mp 139-
1480.
(1~:~.,6p,8~:~.,9fl)-form
C 15H 260 6 M 302.367 6,9-Bis(3-furoyl), 1,8-di-Ac: [112592-79-7].
(1~:~.,2~:~.,8~:~.,9/1)-form Acetoxyeumaiteno/
14-(3-Pyridinecarbonyl), 9-benzoyl, 1,2-di-Ac: [61166-34-5]. CzgH340 12 M 574.580
Cathedulin EB. Cathedu/in Y8 Constit. of Maytenus boaria. Cryst. (EtzOjpet ether).
C 32H 37N0 10 M 595.645 Mp 95-97°.
Alkaloid from Catha edu/is (Celastraceae). Gum. May Gonzalez, A.G. eta/, Phytochemistry, 1987, 26, 2133; 1988, 27,
be an artifact of isol. since the 4-nicotinoyl group of 473 (isol, ir, uv, pmr, ms, struct)
Cathedulin E2 is labile. Becerra, J. et a/, Phytochemistry, 1987, 26, 3073
(Acetoxyeumaitenol)
8,14-Bis(3-pyridinecarbonyl), 9-benzoyl, 1,2-di-Ac: [61231-
06-9]. Cathedulin E2. 0 4 -Nicotinoylcathedu/in E8.
Cathedu/in 2 1,4,6,9 ,14- Pentahydroxydihydro-~­ Sq-01249
C 38H 40Nz0 11 M 700.741 agarofuran
Alkaloid from C. edulis (Celastraceae). Cryst. (EtzOjpet.
ether). Mp 149-151° (transition at 137-140°). [oe]~ -74°
(c, 0.22 in CHC1 3).
Baxter, R.L. eta/, J. Chern. Soc., Perkin Trans. I, 1979, 2965,
2972 (isol, uv, ir, pmr, cmr, ms, struct)

1,4,6,8,9-Pentahydroxydihydro- ~­ Sq-01248
agarofuran
HO OH CtsHz606 M 302.367
I I
(1~:~.,6ft,9fl)-form
6,9,14- Tri-Ac, ]-benzoyl.· [107602-73-3]. 6ft,9ft,l4··
Triacetoxy-1~:~.-benzoyloxy-4p-hydroxydihydro-P­
agarofuran
( 10!,6~,8 ~,90! )-form
C28 H 360 10 M 532.586
Constit. of Orthosphenia mexicana. Cryst. Mp 188-190°.
Called 6,9,15-Trihydroxy in the ref.
C 15H 260 6 M 302.367 9-Cinnamoyl, 1,6-di-Ac: Vaalens 5
(1~:~.,6ft,8ft,9~:~.)-form C28H 360 9 M 516.587
Constit. of Catha transvaalensis. Mp 195-197°.
1-Benzoyl, 6-(3-pyridinecarbonyl), 9-Ac: [110559-19-8]. 9~:~.­
Acetoxy-l~:~.-benzoyloxy-4ft,8P-dihydroxy-6ft­ Gonzalez, A.G. eta/, Phytochemistry, 1988, 27, 473.
nicotinoyloxydihydro-ft-agarofuran. Joe-Benzoyloxy-6f3- Crombie, L. eta/, J. Chern. Soc., Perkin Trans. 1, 1989, 1700.
nicotinoyloxy-9oe-acetoxy-4f3,8f3-dihydroxydihydro-f3-
agarofuran 1,6,8,9,14-Pentahydroxydihydro- ~­ Sq-01250
C 30 H 35N09 M 553.608 agarofuran
Alkaloid from the aerial parts of Orthosphenia mexicana
CtsHz606 M 302.367
(Celastraceae). Mp 184-186°.
(1~:~.,6ft,8~:~.,9~:~. )-form
1-Benzoyl, 6-(3-pyridinecarbonyl), 8,9-Di-Ac: [11 0559-18-7].
8p,9~:~.-Diacetoxy-1~:~.-benzoy/oxy-4ft-hydroxy-6p­
3-Pyridinecarbonyl, benzoyl, tri-Ac: Ejap 13
nicotinoyloxydihydro-P-agarofuran. Joe-Benzoyloxy-6f3- C 34H 39N0 11 M 637.682
nicotinoyloxy-8f3,9oe-diacetoxy-4f3-hydroxydihydro-P- Isol. from Euonymus japonicus. Amorph. Posn. of ester
agarofuran groups not detd.
C 32 H 37N0 10 M 595.645 (1~:~.,6ft,8~:~.,9fl)-form
Alkaloid from the root bark of Rzedowskia 9-Benzoyl, 1,6,8,14-tetra-Ac: Ejap 3
tolantonguensis (Celastraceae). Mp 114-116°. Rzedowskia C 30 H 380 11 M 574.624
is not a generally recognised genus. Isol. from E. japonicus. Cryst. (cyclohexanejEtOAc).
6,9-Di-Ac, ]-benzoyl.· [114226-33-4]. 6f3,9oe-Diacetoxy-1oe- Mp 118°.
benzoyloxy-4f3,8f3-dihydroxydihydro-f3-agarofuran 9-(3-Pyridinecarbonyl), 1,6,8,14-tetra-Ac: Ejap 14
Cz6H3409 M 490.549 C 29H 37N0 11 M 575.611
Constit. of Orthosphenia mexicana. Cryst. Mp 194-198°. Isol. from E. japonicus. Amorph.
6,8 ,9- Tri-Ac, ]-benzoyl.· [114226-31-2]. 6f3,8f3,9oe- Triacetoxy- 9-Benzoyl, 1,6,14-tri-Ac: Ejap 10
1oe-benzoyloxy-4f3-hydroxydihydro-f3-agarofuran
C 28H 360 10 M 532.586

380
1,4,6,9-Tetrahydroxydihydro- p..... - 1,2,9-Trihydroxydihydro- p..... Sq-01251 - Sq-01255

C28 H360 10 M 532.586 Alkaloid from Celastrus paniculatus (Celastraceae).

Isol. from E. japonicus. Cryst. (MeOH). Mp 203-205°. Cryst. (MeOH). Mp 245-249°. [rx]~ -64.7° (c, 0.46 in
Rozsa, Z. et al, J. Chern. Soc., Perkin Trans. 1, 1989, 1079. CHC1 3). 4-Config. not certain.
9-(3-Pyridinecarbonyl), 6-benzoyl, l-Ac: (58074-71-8).
1,4,6,9-Tetrahydroxydihydro-IJ-agarofuran Sq-01251 Celapagine
C30 H 35N0 8 M 537.608
Alkaloid from C. paniculatus (Celastraceae). Cryst.
(MeOH). Mp 275-283°.
Wagner, H. et al, Tetrahedron, 1975, 31, 1949 (Celapanine)
Becerra, J. et al, Phytochemistry, 1987, 26, 3073 (Eumaitenin)

1,6,9,14-Tetrahydroxydihydro-P- Sq-01253
agarofuran
C15H 160 5 M 286.367 CtsH160 5 M 286.367
(lrx,6p,9fl)-form (lrx,6p,9fl)-form
9-Ac,l-benzoy/: 9P-Acetoxy-1rx-benzoy/oxy-4P,6P- 9-Benzoyl, 1,6,14-tri-Ac: Ejap 2
dihydroxydihydro-P-agarofuran C28H 360 9 M 516.587
C24H 320 7 M 432.513 Isol. from Euonymus japonicus. Cryst.
Constit. of Orthosphenia mexicana. (cyclohexanejEtOAc). Mp 149-150°.
6,9-Di-Ac,l-benzoyl: 6P,9P-Diacetoxy-1 rx-benzoyloxy-4P- 9-(3-Pyridinecarbonyl), 1,6,14-tri-Ac: Ejap 7
hydroxydihydro-P-agarofuran C27 H 35N09 M 517.575
C16H 340 8 M 474.550 Isol. from E. japonicus. Amorph.
Constit. of 0. mexicana. Cryst. Mp 202°. Rozsa, Z. et al, J. Chern. Soc., Perkin Trans. 1, 1989, 1079.
1,9-Dibenzoy/: [81531-41-1). Triptofordin B
C29H 340 7 M 494.583 1,8,9,14-Tetrahydroxydihydro-P- Sq-01254
Constit. of Tripterygium wilfordii var. regelii. Cryst. agarofuran
(MeOH). Mp 193-195°. [rx]i,' +75.6° (c, 0.23 in MeOH).
6,9-Bis(3-furoyl), l-Ac: [112569-60-5]. Eumaitenol
C27H320 10 M 516.544
Constit. of Maytenus boaria. Cryst. (Etpjpet. ether).
Mp 208-2WO.
6-Ketone, 1,9-dibenzoy/: [81531-21-7]. Mortonol A
C29H 320 7 M 492.568
Constit. of Mortonia greggii. Mp 208-209°. [rx]i; + 24.6°
(CHC1 3).
Rodriguez-Hahn, L. et al, Phytochemistry, 1981, 20, 2525. C 15H160 5 M 286.367
Takaishi, Y. et al, Phytochemistry, 1987, 26, 2325. (lrx,8P,9fl)-form [42719-36-8)
Becerra, J. et al, Phytochemistry, 1987, 26, 3073 (Eumaitenol) Ma/kangunio/
Gonzalez, A.G. et al, Phytochemistry, 1988, 27, 473. CtsH160 5 M 286.367
Cryst. Mp 171-172°. [rx) 0 -32.94° (c, 3 in dioxan).
1,6,8,9-Tetrahydroxydihydro-p-agarofuran Sq-01252 9-Benzoy/, 8-Ac: [52691-06-2]. Malkangunin
C24 H 3P 7 M 432.513
HO OH Constit. of Celastrus paniculatus. Cryst. (Et20jpet.
I
ether). Mp 240-245°. [rx] 0 -58.8° (c, 1 in CHC1 3).
Wagner, H. et al, Tetrahedron, 1975, 31, 1949 (isol)
Lotter, H. et al, Tetrahedron Lett., 1978, 3243 (abs config)

1,2,9-Trihydroxydihydro-p-agarofuran Sq-01255
OH OH
C 15H 160 5 M 286.367
(Irx,6p,8rx,9fl)-form HO,~

IE+
9-(3-Furoyl), 1,8-di-Ac: [112516-44-6]. Eumaitenin
C16H 340 10 M 506.549
Constit. of Maytenus boaria. Cryst. (EtOAcjpet. ether).
Mp 183-185°.
Ct5H160 4 M 270.368
9-(3-Pyridinecarbonyl), 6-benzoyl, 1,8-di-Ac: [52691-07-3].
Ceillpanigine (lrx,2rx,9fl)-form [59812-47-4]/socelorbicol
C32H37N09 M 579.646 C 15H160 4 M 270.368
Alkaloid from Celastrus paniculatus (Celastraceae). Parent alcohol from esters isol. from the seed oil of
Cryst. (EtOH). Mp 184-185°. Celastrus orbicu/atus. Cryst. (CHC1 3 jMe2CO). Mp 240-
2410. [rx)~ -8° (c, 0.3 in CHC1 3).
(lrx,6P,8P,9rx )-form
1-E-Cinnamoy/, 2,9-di-Ac: [59812-48-5].
9-(3-Pyridinecarbonyl), 6-(3-furoyl), 1,8-di-Ac: [52658-32-9).
C28H 360 7 M 484.588
Celapanine
Constit. of C. orbicu/atus. Amorph. solid.
C30 H35N0 10 M 569.607
9-(2,3-Epoxycinnamoy/), 1,2-di-Ac:

381
1,4,9-Trihydroxydihydro-p.... - Wilforgine Sq-01256 - Sq-01259

C:zaH360 8 M 500.588 Wilfordine Sq-01258

Isol. from C. gemmatus. Cryst. (MeOH). Mp 173-174°. 8-(Acetyloxy)-02-benzoyl-02-deacetyl-8-deoxo-26·-
[at:]~ -7.87° (c, 0.508 in CH03). Defectively named, hydroxyevonimine, 9CI
shown in nonstandard orientation and descr. as [37239-51-3]
(lf/,2f/,9ot).
9-(2,3-Epoxycinnamoyl), 2-benzoyl, l-Ac:
C33H 380 8 M 562.658
Isol. from C. gemmatus. Amorph. powder. (at:]~ +45.37°
(CHC13). Defectively named.
9-(2,3-Epoxycinnamoyl); 2-butanoyl, l-Ac:
CJI400 8 · M 528.641
Isol. from C. gemmatus. Amorph. powder.
Smith, C.R. et al, J. Org. Chem., 1976, 41, 3264 (isol)
Huffman, J.W. eta/, Tetrahedron, 1987, 43, 5551 (synth)
Yongqiang, T. eta/, Phytochemistry, 1990, 29, 2924 (isol) R =OH

1,4,9-Trihydroxydihydro-IJ-agarofuran Sq-01256 C 43H..,N019 M 883.855

M
Alkaloid from Tripterygium wilfordii andEuonymus alatus
(Celestraceae). Shows insecticidal properties. Cryst.
(Me2COjMeOH). Mp 170-176°. [at:]~ +5o (c, 5.0 in

~
CHC13).
Beroza, M., J. Am. Chem. Soc., 1951, 73, 3656 (isol)
Shizuri, Y. et al, Tetrahedron Lett., 1973, 741 (pmr, struct)
Yantada, K. et at, Tetrahedron, 1978, 34, 1915 (isol, ur•, ir, pmr,
struct)
C 15H:u;04 M 270.368
(lot,9f/)-form
Wilforgine Sq-01259
]-Benzoyl, 9-cinnamoyl: [111514-61-5]. Triptofordin A
C31H 360 6 M 504.622 [37239-47-7]
Constit. of Tripterygium wilfordii var. regelii. Cryst. CH2 0Ac
(MeOH). Mp 220-221°. (at:]~ + 191.7° (c, 0.23 in
MeOH).
AcO
I
lI OAc
I
: . . OAc
Takaishi, Y. eta/, Phytochemistry, 1987, 26, 2325.

1,6,9-Trihydroxydihydro-IJ-agarofuran Sq-01257
OH

C41 H47N0 19 M 857.818

C 15H:u,04 M 270.368 Alkaloid from the roots of Tripterygium hypoglaucum
(Celastraceae). Shows insecticidal properties. Plates
(lot,6fl,9f/)-form [59812-41-8] Celorbicol
(Me2CO/MeOH). Mp 2UO. [at:]~ +25° (Me 2CO).
C 15H:u,04 M 270.368
Parent alcohol of esters from the seed oil of Celastrus Beroza, M., J. Am. Chem. Soc., 1952, 74, 1585 (isol, uv, ir)
Zhang, Z. eta/, Jiegou Huaxue, 1986, S, 83; CA, 107, 237078x.
orbiculatus. Cryst. (CHC1 3/Me2CO). Mp 222-223°. (at:]~
-24° (c, 0.5 in CHC1 3).
Smith, C.R. eta/, J. Org. Chem., 1976, 41, 3264.

382
Wilforidine - Mortonin A Sq-01260 - Sq-01264

Wilforidine Sq-01260

Secoeudesmanes
[98618-76-9]
CH 20Ac
:I OAc
I
: ;OAc

1-Hydroxy-5,10-dioxo-1,10:5,10-diseco- Sq-01262
11(13)-eudesmen-12,8-olide

HOH2C ~O)=o
~
C15H 220 5 M 282.336
BP-form [73971-68-3]
C36H45N0 18 M 779.747
Alkaloid from Tripterygium wilfordii (Celastraceae). Oil.
0-(6-0-Acetyi-P-D-glucopyranoside): [73971-66-1].
He, Z. et al, Huaxue Xuebao, 1985, 43, 593; CA, 103, 157321y.
C23H340 11 M 486.515
Constit. of Picradeniopsis woodhousei. Unstable oil.
Wilforine Sq-01261 Herz, W. et al, J. Org. Chern., 1980, 45, 3163.
As Wilfordine, Sq-01258 with
R=H 1-Hydroxy-1,10-seco-5(10),11(13)- Sq-01263
eudesmadien-12,8-olide
C43H49N0 18 M 867.856 1-Hydroxyeriolanolide
Alkaloid from Tripterygium wilfordii and Maytenus
senegalensis (Celestraceae). Shows insecticidal properties.
Plates (Me 2CO/MeOH). Mp 169-170°. [cx]i;' +30°
(Me 2CO).
De-Ac: Wi/forzine
HOH,C~ 0
C41H47NOt7 M 825.819 CISH2203 M 250.337
Alkaloid from the roots ofT. wi/fordii(Celestraceae).
1-0-(6-0-Acetyi-P-D-glucopyranoside): [73971-69-4].
Needles (Me 2CO/MeOH). Mp 177-178°. [cx]i;' +6°
C23H340 9 M 454.516
(Me 2CO). Prob. the 2- or 6-deacetyl deriv. of Wilforine.
Constit. of Picradeniopsis woodhousei. Oil. [cxln -26.5°
Has been shown not to be an artefact.
(c, 0.9 in CHC13).
Beroza, M., J. Am. Chern. Soc., 1951, 73, 3656 (isol)
Beroza, M., J. Am. Chern. Soc., 1953, 75, 2136 (isol, uv,
]-Carboxylic acid: [73971-64-9]. lvangulic acid. Ivangulinic
Wilforzine) acid
Tin-Wa, M. et al, J. Nat. Prod. (Lloydia), 1971, 34, 79 (isol) CISH2004 M 264.321
Constit. of Gnephosis arachnoidea. Gum.
]-Carboxylic acid, Me ester: [14271-37-5]. lvangulin
Ct,Hn04 M 278.347
Constit. of Iva angustifo/ia. Cryst. (C6H 6 /Etp). Mp 84-
850. [cx]i,1 + 109° (CHC1 3).
Herz, W. et al, J. Org. Chern., 1967, 32, 3658; 1980, 45, 3163 (isol,
struct)
Grieco, P.A., J. Org. Chern., 1977, 42, 4113 (synth)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3181 (Ivangulic acid)

Mortonin A Sq-01264
Mortonin
[38344-03-5]
PhCOO

~
~~
CuH 260 6 M 386.444
Constit. of Mortonia greggii and M. hidalgensis. Cryst. Mp
195-196°.
2cx-Acetoxy: [67991-39-3]. Mortonin B
C14H 280 8 M 444.480
Constit. of M. greggii.
Rodriguez-Hahn, L. et al, Tetrahedron, 1977, 33, 657 (isol)
Martinez, M. et al, Phytochemistry, 1982, 21, 1335 (isol, struct)

383
Mortonin C- 1,6,14-Trihydroxy-1,10-seco-5(10)... Sq-01265 - Sq-01272

Mortonin C Sq-01265 Secoisoerivanin pseudoacid Sq-01269

[67991-38-2]

Ph~h

~<41
O~---~H~--
0 0
C~32os M 508.567 C1sH2005 M 280.320
Constit. of Mortonia greggii and M. hidalgensis. Cryst. Mp Constit. of Artemisia judaica. Oil.
202-204°. Khafagy, S.M. eta/, Phytochemistry, 1988, 27, 1125.
Romo de Vivar, A. eta/, Rev. Latinoam. Quim., 1972, 3, 1 (isol)
Rodriguez-Hahn, L. eta/, Rev. Latinoam. Quim., 1977, 8, 161
(struct) Senoxepin Sq-01270
Martinez, M. eta/, Phytochemistry, 1982, 21, 1335 (struct) [64197-44-0]

Q?r
Rodriguez-Hahn, L. eta/, Tetrahedron, 1984, 40, 1743 (cryst
struct)

Mortonin D Sq-01266
[67991-42-8]
0

Ph~-- C14H1403 M 230.263

Constit. of Senecio spp. Yellow oil. [1X]i: - 126.SO (c, 0.9 in
CHCI 3).
H~~w Bohlmann, F. eta/, Phytochemistry, 1977, 16, 965.

c~ 3 20s M 508.567 Smyrnicordiolide Sq-01271

Constit. of Mortonia greggii. [97983-42-1]
Rodriguez-Hahn, L. et a/, Rev. Latinoam. Quim., 1977, 8, 161
(struct)

Phytuberol Sq-01267
[56857-64-8]
CtsHtsOJ M 246.305
Constit. of Smyrnium cordifolium. Amorph.
8P-Hydroxy: [97941-57-6]. BP-Hydroxysmyrnicordiolide
CtsHts04 M 262.305
From S. cordifolium. Cryst. Mp 215°. [1X]i: +253.1°
(CHCI 3).
C 15H 240 3 M 252.353
Constit. of Nicotiana tabacum. Oil. 8,9-Didehydro: [100668-33-5]. Smyrnicordi-8-enolide
CtsHt603 M 244.290
Ac: [37209-50-0]. Phytuberin Constit. of S. rotundifolium. Amorph.
Ct,H 260 4 M 294.390
Phytoalexin of potato tubers infected with Erwinia Stereoisomer: [100761-29-3). /sosmyrnicordiolide
carotovora. Oil. [1X]n -35.9° (c, 1.34 in CHCI 3). C 15Ht80 3 M 246.305
Constit. of S. rotundifolium. Amorph. No info. on
Coxon, D.T. eta/, J. Chern. Soc., Perkin Trans. I, 1977, 53. stereochem.
Takagi, Y. et a/, Agric. Bioi. Chern., 1979, 43, 2395.
Caine, D. et al, J. Am. Chern. Soc., 1980, 102, 7568 (synth) Ulubelen, A. eta/, Phytochemistry, 1985, 24, 1305.
Findlay, J.A. eta/, Can. J. Chern., 1980, 58, 2827 (synth) Goren, N. eta/, Phytochemistry, 1985, 24, 3051.
Murai, A. et al, Bull. Chern. Soc. Jpn., 1982, 55, 1202 (synth)
1,6,14-Trihydroxy-1,10-seco-5(10),11(13)- Sq-01272
Secocrispiolide Sq-01268 eudesmadien-12,8-olide
[72776-46-6] 1,6,14-Trihydroxyeriolanolide

C15H 180 2 M 230.306

Constit. of Pulicaria crispa. Oil. [1X]~4 + 5.4° (c, 0.5 in C 15H 220 5 M 282.336
CHCI 3). 6«-form
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1231. 14-(Methylpropanoyl):
C 19H 280 6 M 352.427
Constit. of Eriophyllum /anatum. Gum.
14-(Methy/propanoyl), 6-Ac:
C 21 H 300 7 M 394.464
384
Umbellifolide - Zinaflorin IV Sq-01273 - Sq-01274

Constit. of E. lanatum. Gum. [a]i;l -16° (c, 1 in CHC1 3). Zinaflorin IV Sq-01274
14-(Methylpropanoyl), l-Ac: [88930-59-0]
C21 H 300 7 M 394.464
Constit. of E. lanatum. Cryst. (Etpjpet. ether). Mp 94°.
[a]i;l + 85° (c, 0.53 in CHC1 3).
14-(Methy/propanoyl), 1,6-di-Ac:
C13H 310 8 M 436.501
Constit. of E. lanatum: Gum.
14-(2-Methylpropenoyl):
C 19Hu;06 M 350.411
Constit. of E. lanatum. Gum.
14-(2-Methylpropenoyl), 6-Ac: C10H 140 7 M 376.405
C11 H180 7 M 392.448 Also represented in the ring opened form with epoxide and
Constit. of E. lanatum. Gum. -CHO functions in ring A. Constit. of Zinnia
14-(2-Methylpropenoyl), l-Ac: peruviana. Cryst. Mp 194-196°. [aln + 137.5° (c, 0.145 in
C11 H180 7 M 392.448 CHC1 3), [1X]n + 96.2° (c, 5.1 in EtOH).
Constit. of E. lanatum. Gum. 0 6-Deacyl, 0 6-tig/oy/:
14-(2-Methylpropenoyl), 1,6-di-Ac: CzoH140 7 M 376.405
C13H 300 8 M 434.485 Constit. of Z. peruviana.
Constit. of E. lanatum. Gum. 0 6-Deacy/, 0 6-(2-methy/propenoyl): [88930-72-7].
6-Angeloyl: [52617-35-3]. Eriolangin Ct9Hz207 M 362.379
C10H180 6 M 364.438 Constit. of Z. peruviana.
Constit. of E. lanatum. Antitumour and antileukaemic Herz, W. eta/, Phytochemistry, 1981, 21, 2229 (isol)
agent. Cryst. (CHC1 3). Mp 94-96°. [a]i;l -91° (CHC1 3). Ortega, A. eta/, Chern. Lett., 1983, 1607 (cryst struct)
6-(2-Methylpropenoyl): [52617-36-4]. Eriolanin Mirand, R. et a/, J. Nat. Prod. (Lloydia), 1989, 52, 1128 (isol, pmr)
C19H160 6 M 350.411
Constit. of E. lanatum. Antileukaemic. Cryst.
(CHC1 3jpet. ether). Mp 126.5-128°. [a]i;l -93° (CHC1 3).
Kupchan, S.M. et a/, J. Chern. Soc., Chern. Commun., 1973, 842
(Eriolanin, Eriolangin)
Grieco, P.A. eta/, J. Am. Chern. Soc., 1980, 102, 5886 (synth)
Roberts, M.R. et a/, J. Am. Chern. Soc., 1981, 103, 724 (synth)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2239.

U mbellifolide Sq-01273
Tetrahydro-6-methyl-3-methylene-6-(4-oxopentyl)-2,5-
(3H,4H)-benzofurandione, 9CI. 4,5-Dioxo-4,5-seco-11(13)-
eudesmen-12 ,8P-olide
[89026-40-4]

~0
C 15H:w04 M 264.321
Constit. of Artemisia umbelliformis and Calea
szyszylowiczii. Cryst. (Et0Ac/Et 20). Mp 113°. [a]i;l
+60.8° (c, 0.5 in CHC1 3).
Appendino, G. eta/, J. Chern. Soc., Perkin Trans. l, 1983, 2705
(isol, cryst struct)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2227 (isol)
Marco, J.A. et a/, Tetrahedron, 1987, 43, 2523 (synth)

385
Alhanol - Cybullol Sq-01275 - Sq-01286

Chamaecynone Sq-01283
7- Ethynyl-4a,5 ,6, 7,8,8a-hexahydro-1 ,4a-dimethyl-2(1H)-
Noreudesmanes naphtha/enone, 9CI
[10208-54-5]

Alhanol Sq-01275
1cx,3cx-Dihydroxy-4-eudesmen-12 ,6cx-olide. 1soerivanin
0~~ ,H
C14H180 M 202.296
Constit. of Chamaecyparis formosensis. Cryst. Mp 92°. [cxln
-93.3° (MeOH).
4-Epimer: [10208-55-6]. lsochamaecynone
Ct4H180 M 202.296
lsol. from C. formosensis. Oil.
4-Epimer, 4cx-hydroxy: [26607-26-1]. 4-
Hydroxyisochamaecynone
C15H2204 M 266.336 c14H 180 2 M 218.295
Constit. of Balsamita major and Artemisia fragrans. Cryst. Isol. from C. formosensis. Cryst. Mp 162°. [cx]i? -39.2°
M p 179-181 o ( 172-177°). (EtOH).
3-Ketone: Alhanin. Dehydroisoerivanin Nozoe, T. et al, Tetrahedron Lett., 1966, 3663; 1967, 2821 (isol,
C15H 200 5 M 280.320 struct, synth)
Constit. of B. major. Cryst. Mp 201-203° (189-191°). Ando, M. eta/, Tetrahedron Lett., 1969, 4689 (4-
Hydroxyisochamaecyn~?ne)
1-Epimer: 1P,3cx-Dihydroxy-4-eudesmen-12,6cx-olide. 1-
Harayama, T. et a/, Tetr1;1hedron Lett., 1977, 3273 (synth)
Epiisoerivanin Mizuno, Y. et al, J. Che1n. Soc., Perkin Trans. I, 1982, 2849
c1sH220 4 M 266.336 (synth)
Constit. of Artemisia judaica. Oil. [cx]i;' + 39° (c. 0.93 in
CHC1 3).
Cogeijerene Sq-01285
Serekov, S.V. eta/, Khim. Prir. Soedin., 1978, 75; 1979, 326.
1,2,3, 7,8,8a-Octahydro-4,8a-dimethylnaphthalene
Samek, Z. et al, Collect. Czech. Chern. Commun., 1979, 44, 1468
(isol, struct)
Khafagy, S.M. et al, Phytochemistry, 1988, 27, 1125 (epimer)

Chamaecynenol Sq-01282
Chamecynenol
[22387-90-2] C 12H 18 M 162.274
Constit. of Geijera parviflora. Liq. Bp 10 97°. [cxln +0.70°.

~
Gough, J. et al, Tetrahedron Lett., 1961, 763.

Cybullol Sq-01286
HOH2C15 Octahydro-5,8a-dimethy/-2,4a(2H)-naphthalenediol, 9CI. 5,9-
Dimethy/-2,10-decalindiol
C 14H200 M 204.311 [60433-05-8]
Constit. of Chamaecyparisformosensis. Oil. Bp 2 116-118°.
[cx]i;· 5 + 9.3°.
Ac:
~OH
cl6H220 2 M 246.349
Constit. of C.formosensis. Oil. Bp 2 116-118°. ~
p-Nitrobenzoyl: Cryst. Mp 100-101°. C 12H 220 2 M 198.305
3,4-Didehydro: [20489-25-2]. Dehydrochamaecynenol Metab. of Cyathus bulleri. Cryst. Mp 125-126° [cxlii -16°
C 14H 180 M 202.296 (c, 0.4 in MeOH).
Constit. of C.formosensis. Oil. Bp1. 8 113-116°. [cx]~.4 Ayer, W.A. eta/, Can. J. Chern., 1976, 54, 910, 3276 (isol, struct,
-193.1° (c, 0.7 in MeOH). synth)
3,4-Didehydro,15-aldehyde: [20489-26-3].
Dehydrochamaecynenal
Ct4Ht60 M 200.280
Constit. of C. formosensis. Oil. Bp1. 8 113-116°.
Takase, K. et a/, Chern. Ind. (London), 1968, 1638.
Asao, T. et al, Tetrahedron Lett., 1968, 3639
(Dehydrochamaecynenol, Dehydrochamaecynal)
Shimanouchi, H. eta/, Bull. Chern. Soc. Jpn., 1969, 42, 334.

386
3,4-Dihydroxy-11,12,13-trinor-8-... Sq-01289 - Sq-01296

3,4-Dihydroxy-11,12,13-trinor-8- Sq-01289 Odorous substance produced by Streptomyces spp. and

eudesmanone blue-green algae. Oil with characteristic penetrating
earthy odour. [ex]~ ca. -140° (MeOH), (ex] 0 -16.5°
(CHC1 3). Stereoisomers known synthetically.

Hif~tt HO '
6,7-Didehydro: 1,2,3,4,4a,5,8,8a-Octahydro-4,8a-
dimethylnaphthalen-4a-ol. Dehydrogeosmin
CuH100 M 180.289
Constit. of various cactus spp. flower scent. Oil.
CuH100 3 M 212.288 (±)-form [16423-19-l]
(3Jl,4JI)-form [125411-05-4] Oil, cryst. on standing. Mp 78-82°.
ll, 12,13- Trinor- 3,4-diepicuauhtemone [5173-69-3, 5173-70-6, 16452-32-7, 23333-91-7, 62823-65-8, 73428-
Constit. of P/uchea arguta. Cryst. (MeOH). Mp 180°. 92-09]
(ex] 0 + 142.9° (c, 0.014 in MeOH). Marshall, J.A. et al, J. Org. Chern., 1966, 31, 1020; 1968, 33, 2593
Ahmad, V.U. eta/, Phytochemistry, 1989, 28, 3081 (isol, pmr, cmr) (synth)
Gerber, N.N. et al, Tetrahedron Lett., 1968, 2971 (isol, struct)
Ayer, W.A. et al, Can. J. Chern., 1976, 54, 3276 (isol, struct, synth,
Douglanine Sq-01290 abs con.fig)
[16886-36-5] Kaiser, R. eta/, Helv. Chim. Acta, 1990, 73, 133 (isol, synth, ms,
pmr, cmr)
HOI

oq:y
Glutinosone Sq-01295

~
[55051-94-0]

0 HO I ,?
ClsH100 3 M 248.321 IH
Constit. of Artemisia douglasiana. Cryst. Mp 115-117°. [ex]i:
+ 133°. C14H100 2 M 220.311
Phytoalexin formed in the leaves of Nicotiana g/utinosa
Matsueda, S. eta/, Tetrahedron Lett., 1967, 2159 (isol) following infection with tobacco mosaic virus.
UI-Haque, M. et al, J. Chern. Soc. B, 1970, 598 (cryst struct)
Antifungal antibiotic. Oil. [ex] 0 + 57.2°.
Geosmin Sq-01294 Ac: Oil. [ex] 0 + 64.8°.
Octahydro-4,8a-dimethy/-4a(2H)-naphthaleno/, 9CI. 1,10- Murai, A. et a/, Bull. Chern. Soc. Jpn., 1980, 53, 1045 (ir, ms, pmr,
Dimethy/-9-deca/o/ cmr, abs conjig, synth, uv)
[19700-21-l]

qp
4,4a,5,6,7,8-Hexahydro-4a,8-dimethyl- Sq-01296
I
2(3H)-naphthalenone, 9CI
a
(4071-63-0]
4

H
M 182.305

CuH 180 M 178.274

(4aS,8S)-form [39850-89-0]
Constit. of the oil of Vetiveria zizanioides. Oil. Bp0 .05
70°. [ex]~ +201.7° (c, 2 in CHC1 3).
[58407-30-0, 60102-91-2, 64281-61-4, 69460-62-4]
Maurer, B. eta/, Helv. Chim. Acta, 1972, 55, 2371.

387
6-Hydroxy-12,13-dinor-3-oxo-4-eudesmen-... Sq-01297 - Sq-01302

6-Hydroxy-12,13-dinor-3-oxo-4-eudesmen- Sq-01297 Lacinilene D Sq-01301

11-oic acid 1,4-Dihydroxy-1-methyl-7-(1-methylethyl)-2( JH)-
naphthalenone, 9Cl. 1,4-Dihydroxy-7-isopropyf-J. methyl-

WCOOH
2(JH)-naphthalenone

m
[41743-45-7]

OH
CI3HI804 M 238.283
6fl-form 0~
OH
Me ester: Jasomontanone
Ct4H:zo04 M 252.310 Ct4Ht603 M 232.279
Constit. of Jasonia montana. Oil. Constit. of the heartwood of Ulmus laciniata. Yellow
needles (Et0Ac/C6H 6). Mp 181-182.SO.
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3658 (isol, pmr, cmr)
Nishikawa, K. eta/, Mokuzai Gakkaishi, 1972, 18, 62:1; CA, 78,
108241.
11-Hydroxy-13-nor-3-oxo-1,7(11)- Sq-01298
eudesmadien-12,6-olide Liguhodgsonal Sq-01302
5,6,7,8-Tetrahydro-3-hydroxy-7-(1-methylethenyl)-1-

O~OH
naphthalenecarboxaldehyde, 9CI. 5,6,7,8- Tetrahydro-3-
hydroxy-7-isopropenyl-1-naphtha/dehyde
' i '1~ H2 OI Q ) y
0
~
Ct4Ht,04 M 248.278 CHO
6«-form
Found in Crepis pygmaea. Cryst. (MeOH). Mp 178- Ct4Ht602 M 216.279
1800. [alii + 104° (c, 0.15 in CHC1 3). (R)-form [64185-18-8]
Casinovi, C.G. et a/, P/anta Med., 1982, 44, 186. Constit. of Ligularia spp. Oil. [1X]~4 + 104° (c, 0.5 in
CHC1 3).
Deoxy: 5,6,7,8- Tetrahydro-7-(1-methylethenyl)-1-
11-Hydroxy-3-oxo-13-nor-7(11)- Sq-01299 naphtha/enecarboxa/dehyde, 9Cl. 5,6, 7,8- Tetrahydro-7-
eudesmen-12,6-olide isopropeny/-1-naphtha/dehyde. 2-Deoxyliguhodgsonal
Ct4Ht60 M 200.280

O~~OH
Constit. of Senecio nebrodensis.
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 2640 (iso/, struct)
I H \ Bohlmann, F. eta/, Phytochemistry, 1981, 20, 467.
I 0
0
Ct4Hta04 M 250.294
Constit. of Crepis pygmaea. Cubes (Et20). Mp 179-180°.
[1X]n +25.7° (c, 2.9 in CHC1 3).
Rossi, C. eta/, J. Chern. Res. (S), 1985, 160 (synth)
Rossi, C. eta/, Phytochemistry, 1985, 24, 603 (isol)

388
Ligujapone - Platyphyllide Sq-01303 - Sq-01309

Ligujapone Sq-01303 Oxyglutinosone Sq-01308

3,4-Dihydro-6-hydroxy-3-(J~methylethenyl)-1(2H)­ [69297-50-3]
naphthalenone, 9CI. 6-Hydroxy-3-isopropeny/-5-methy/-2-
tetra/one

HO
0~
: I
: OH
C14H20 0 3 M 236.310
Constit. of Nicotiana g/utinosa. Oil. [1X] 0 + 130°.
Murai, A. et al, Bull. Chern. Soc. Jpn., 1980, 53, 1045.
C14H 160 2 M 216.279
(S)-form [64185-24-6] Platyphyllide Sq-01309
Constit. of Ligularia spp. Oil. A.max 220 Oog e 4.24) and
272(2.34) (Et 20). [64185-74-6]

J_[ l-..
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 2640 (isol, struct)

14-Norfuranoeudesm-5(10)-ene-6,9-dione
5,6,7,8-Tetrahydro-3,5-dimethylnaphtho[2,3-blfuran-4,9-
Sq-01306 ~
dione, 9CI

M
0 c.4HI4ol
C 14H 140 3 M 230.263
4rx.-form [24393-84-8] Tetrahydromaturinone
Constit. of Cacalia de/phiniifolia. Yellow needles. Mp
88-88.SO. [1X] 0 +34.7° (c, lin CHC1 3).
Naya, K. eta/, Chern. Lett., 1976, 73 (isol, struct, synth)
15-Nor-4-oxo-11(13)-eudesmen-12-oic acid Sq-01307
15-Nor-4-oxocostic acid
M 214.263
Constit. of Senecio spp. Oil. [1X]i; -17.8° (c, 3.1 in CHC1 3).
]-Hydroxy: 1-Hydroxyplatyphyl/ide
C14H140 3 M 230.263
Constit. of S. gilliesiano. Cryst. (cyclohexane/C 6 H 6). Mp
118-120°. [1X]i:' +42.7° (c, 6.38 in MeOH).
2-Hydroxy: [72145-19-8]. 2-Hydroxyplatyphyllide
Ct4Ht40 3 M 230.263
Constit. of Ligularia intermedia. Oil. [1X]~4 -9° (c, 0.3 in
CHCI 3) (as acetate).
Bohlmann, F. et al, Phytochemistry, 1977, 16, 965; 1979, 18, 877
(isol, struct)
Bohlmann, F. et al, Chern. Ber., 1979, 112, 2811 (synth)
Guidugli, F.H. eta/, Phytochemistry, 1986, 25, 1923 (isol)

9=\~H
C 14H 200 3 M 236.310
Constit. of Apalochlamys spectabilis. Oil (as Me ester). [1X]i;
-9° (c, 3.79 in CHC1 3)(Me ester).
Zdero, C. et al, Phytochemistry, 1990, 29, 3201 (isol)

389
Rishitin - 1,2,3,4-Tetrahydro-2-isopropenly-8-... Sq-01310 - Sq-01314

Rishitin Sq-01310 1,2,3,4-Tetrahydro-2-isopropenyl-8- Sq-01314

[18178-54-6] methyl-1-naphthol
1,2,3,4-Tetrahydro-8-methyl-2-(1-methylethenyl)-1-
naphthalenol, 9CI
HO:((\'

wY
HO
: I
C14H 220 2 M 222.327
Constit. of the tubers of white potatoes (Solanum spp.) OH
infected by Phytophthora infestans. Cryst. Mp 65-67°. C,4H 180 M 202.296
[1X]i:' -8.7° (CHC1 3). 6P-form
3-0-[IX-L-Rhamnopyranosyl-(1->4)-P-n-glucopyranosyl- cis-form
(1 ->4)-P-n-glycopyranoside]: Norsesquiterpenoid constit. of Virginia tobacco
C32H 520 16 M 692.753 condensate. Abs. config not proved.
From tobacco. Cryst. Mp 208-212.5°. [1X] 0 -44.6° (c, [67494-23-9, 67494-24-0)
0.33 in EtOH).
Demole, E. eta/, Helv. Chim. Acta, 1978, 61, 1335 (isol, synth, ir,
Bukhari, S.T.K. eta/, J. Chern. Soc. C, 1969, 1073 (struct) ms)
Murai, A. eta/, Bull. Chern. Soc. Jpn., 1977, SO, 1206 (synth)
Stoessl, A. eta/, Can. J. Chern., 1983, 61, 1766 (biosynth)
Kodama, H. eta/, Agric. Bioi. Chern., 1985, 49, 2537 (deriv)
Brindle, P.A. et a/, Phytochemistry, 1985, 24, 1219 (biosynth)

Rishitin Ml Sq-01311
[65513-76-0]

HO~
I CH20H 11
HO I I
I 13

C 14H 220 3 M 238.326

Metab. of Rishitin from Solanum tuberosum. Oil. [1X] 0
-33.2° (EtOH).
JJR,l3-Dihydro: [66113-29-9]. Rishitin M2
C14H 240 3 M 240.342
Metab. of Rishitin from S. tuberosum. Oil. [1X] 0 -17.7°
(EtOH).
Murai, A. et a/, J. Chern. Soc., Chern. Commun., 1977, 670; 1986,
891 (isol, struct, biosynth)

390
Tirotundifolin C - Emmotin A Sq-01315 - Sq-01320

Tirotundifolin C Sq-01315
OH
Emmotin group

10-Desmethyl-1-methyl-1,3,5(10),11(13)- Sq-01318
0
eudesmatetraen-12,8-olide

R=-ocYy OH
C:zoH 260 6 M 362.422
Constit. of Tithonia rotundifolia. Cryst. (Me 2CO/hexane).
Mp 168-170°. [aJn +30.8° (c, 0.2 in MeOH). C13H 160 2 M 228.290
/!;. 4 •5-Isomer: Tirotundifolin B ap-form
C2oH 260 6 M 362.422 Constit. of Ferreyranthus fruticosus. Cryst. Mp 122°.
Constit. ofT. rotundifolia. Cryst. (Me 2COfhexane). Mp Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113.
163-165°. [cxln -12.2° (c, 0.212 in MeOH).
Perez C., A.L. eta/, Phytochemistry, 1984, 23, 823.
Desmotroposantonin Sq-01319
Tirotundifolin D Sq-01316
As Tirotundifolin C, Sq-01315 with
II ~(H)-form
R = H 3CCH=C(CHpH)CO- Absolute
C:wH2606 M 362.422 configuration
Constit. of Tithonia rotundifolia. Cryst. (Me 2COjhexane).
Mp 163-165°. C13H 180 3 M 246.305
Perez C., A.L. eta/, Phytochemistry, 1984, 23, 823. Prod. from Santonin by acid treatment.
(llPII)-form [5951-46-2]r~.-Desmotroposantonin
Tirotundifolin E Sq-01317 Cryst. (EtOH). M"p 194-195°. [cxJn -140°.
As Tirotundifolin C, Sq-01315 with (ll«ll)-form [5951-45-1] P-Desmotroposantonin
Cryst. (MeOH). Mp 255°. [a]~ -107.7° (c, 0.35 in
R = -OCC(OH)(CH 3)CH(OH)CH 3 CHC1 3).
C:wH280 7 M 380.437 McPhail, A.T. eta/, J. Chern. Soc. B, 1967, 101 (cryst struct)
Constit. of Tithonia rotundifolia. Cryst. (Me2COfhexane). McPhail, A.T: eta/, J. Chern. Soc. C, 1967, 201 (synth)
Mp 213-215°. [cxJn +9.3° (c, 0.224 in MeOH). Wasada, N. eta/, Tetrahedron, 1967, 23, 4623 (ms)
Edward, J.T. eta/, J. Org. Chern., 1978, 43, 536 (synth)
Perez C., A.L. eta/, Phytochemistry, 1984, 23, 823.

Emmotin A Sq-01320
[53915-44-9]
0

CJJ_
MeO~OH

H~1s --~H
Il
Ct6Hn04 M 278.347
Constit. of trunk wood of Emmotum nitens. Cryst.
(Etpjpet. ether). Mp 79°.
Di-Ac: Cryst. (Etpjpet. ether). Mp 98-99°.
15-Hydroxy: [53915-45-0]. Emmotin B
Ct6H 220 3 M 294.347
Constit. of E. nitens. Cryst. (EtOH). Mp 138-140°.
15-Hydroxy, tri-Ac: Cryst. (EtOH). Mp 125-126°.
de Oliveira, A.B. eta/, Phytochemistry, 1974, 13, 1199 (isol)
de Oliveira, A.B. eta/, Phytochemistry, 1976, IS, 1267 (ahs config)

391
Emmotin C - Rishitinol Sq-01321 - Sq-01327

Emmotin C Sq-01321 Emmotin H Sq-01325

7,8-Dihydroxy-4-methy/-6-( 1-methy/ethyl)-1- 3-(1-Hydroxy-1-methy/ethyl)-5,8-dimethyl-1,2-
naphtha/enecarboxa/dehyde, 9CI. 7,8-Dihydroxy-6-isopropy/- naphthoquinone
4-methy/-1-naphtha/dehyde [61263-74-9]

(?;o
[53915-46-1)

ffioH
·~ ~OH
C 15H 1,03 M 244.290
c.sH 1,03 M 244.290 Constit. of Emmotum nitens. Red cryst. (hexane/Et 20).
Constit. of trunk wood of Emmotum nitens. Cryst. Mp 178-180°.
(Et20/pet. ether). Mp 121-124°.
de Oliveira, A.B. eta/, Phytochemistry, 1976, 15, 1267 (isol)
de Oliviera, A.B. eta/, Phytochemistry, 1974, 13, 1199. Reddy, P.A. et al, J. Chern. Soc., Perkin Trans. I, 1979, 237
(synth)
Emmotin D Sq-01322 Veluchamy, T.P. et al, Indian J. Chern., Sect. B, 1986, 25, 1247
(synth)
[53915-47-2]
Occidol Sq-01326
1,2,3 ,4-Tetrahydro-rx.,a.,5 ,8-tetramethy/-2-
naphtha/enemethano/, 9CI

C1sH1404 M 258.273
Constit. of trunk wood of Emmotum nitens. Cryst. (EtOH).
Mp 209~210°. C 15H 220 M 218.338
de Oliveira, A.B. eta/, Phytochemistry, 1974, 13, 1199. (R)-form [5986-36-7]
Constit. of Thuja occidentalis. Cryst. Mp 69-70°. [a.]n
+ 163.7° (c, 1.2 in CHC1 3).
Emmotin F Sq-01323
Nakazaki, M. et al, Bull. Chern. Soc. Jpn., 1962, 35, 1387 (ahs,
[61263-72-7] config)
Ho, T.-L., J. Chern. Soc., Perkin Trans. I, 1973, 2579.
Reddy, P.A. et al, Indian J. Chern., Sect. B, 1980, 19, 753 (synth)

Rishitinol Sq-01327
(31316-42-4]
C 15H 100 3 M 248.321
Constit. of trunk wood of Emmotum nitens. Cryst. (EtOH). ~OH
Mp 100-102°.
de Oliveira, A.B. et al, Phytochemistry, 1976, 15, 1267 (struct, ahs
config)
~OH
C15H 220 2 M 234.338
Emmotin G Sq-01324 Phytoa1exein of tubers of white potatoes (Solanum
tuberosum and S. demissum) infected by Phytophthora
3-Hydroxy-a.,a.,5,8-tetramethyl-2-naphthalenemethanol, 9CI
infestans. Cryst. (hexane). Mp 127-129°. [a.]n +47°
[61263-73-8] (CHC1 3).
Schwochau, M. et al, Arch. Biochem. Biophys., 1969, 134, 34.
Katsui, N. et al, Bull. Chern. Soc. Jpn., 1972, 45, 2871.

C 15H 180 2 M 230.306

Constit. of the trunk wood of Emmotum nitens. Cryst.
(EtOH). Mp 112-115°.
de Oliveira, A.B. et al, Phytochemistry, 1976, 15, 1267 (isol, struct)
Velusamy, T.P. et al, Indian J. Chern., Sect. B, 1981, 20, 351
(synth)

392
Axamide 1 - Uvarisesquiterpene C Sq-01328 - Sq-01332

7,11-Dihydro, 7-methoxy: [87425-40-9]. 7~-Methoxy-4(14)­

oppositen-1P-ol
Oppositanes Ct6H 280 2 M 252.396
Constit. ofT. japonica. Amorph. [1X] 0 + 29.8°.
Niwa, M. eta/, Tetrahedron Lett., 1978, 4043 (synth)
Itokawa, H. et a/, Chern. Lett., 1983, 1253 (isol)

Axamide 1 Sq-01328 1,4,11-0ppositanetriol Sq-01330

[56012-88-5] OH

lh QJ~
YAM~ I
I roH
NHCHO (1p,4fl)-form [99933-32-1] Bullatantriol
C 16H 27NO M 249.395 C1sH280 3 M 256.384
Constit. of Axinella cannabina. Oil. [1X] 0 + 10° (c, 1.2 in Constit. of Annona bullata. Cryst. (MeOH/Et20). Mp
CHC1 3). 179.5-181.SO. [1X]i? +45.3° (c, O.oi in MeOH).
7,11-Didehydro: [62078-09-5]. Axamide 4 Kutschabsky, L. eta/, Phytochemistry, 1985, 24, 2724.
C16H 25NO M 247.380
Constit. of A. cannabina. Cryst. Mp 81-84°. [1X] 0 +63.3°. Oppositol Sq-01331
/sothiocyanate: [53822-97-2]. Axisothiocyanate 1 [50906-52-0]
Ct6H 25NS M 263.446
lsol. from A. cannabina. Oil. [1X] 0 + 5.9° {c, 2.5 in
CHC1 3). Has - NCS replacing - NHCHO.
Isocyanide: [53822-96-1]. Axisonitrile 1 Absolute
Ct6H25N M 231.380 configuration
From A. cannabina. Cryst. Mp 43-45°. [1X] 0 +22.6° (c, l
in CHC1 3). Has - NC replacing - NHCHO.
7,11-Didehydro, isocyanide: [62078-10-8]. Axisonitrile 4
C 1 ~ 23 N M 229.364 C1sH25Br0 M 301.266
lsol. from A. cannabina. Cryst. Mp 56-58°. [1X] 0 + 51.4° Constit. of Laurencia subopposita. Mp 54-55°. [1X]ii -232°
(c, 1 it} CHC1 3). (c, 0.2 in EtOH).
7,11-Didehydro, isothiocyanate,· [62078-11-9]. Hall, S.S. eta/, J. Am. Chern. Soc., 1973, 95, 7187.
Axisothiocyanate 4
C 16H 23NS M 261.430
Isol. from A. cannabina. Oil. [1X] 0 -35.9° (c, 1.2 in
Uvarisesquiterpene C Sq-01332
CHC1 3). [117176-80-4]
Cafieri, F. eta/, Tetrahedron, 1973, 29, 4259 (isol)
Fattorusso, E. eta/, Tetrahedron, 1975, 31, 269 (isol)
Iengo, A. eta/, Experientia, 1977, 33, II; 1979, 35, 10 (isol, struct)
Adinolfi, M. eta/, Tetrahedron Lett., 1977, 2815 (struct)
Piers, E. eta/, Can. J. Chern., 1986, 64, 2475 (synth)
Piers, E. eta/, Tetrahedron, 1987, 43, 5521 (synth)

4(14),7(11)-Oppositadien-1-ol Sq-01329
Octahydro-3a-methyl-7-methylene-1-(2-methyl-1-propenyl)- CzzH320 2 M 328.494
JH-inden-4-ol, 9CI. 1-Hydroxy-4(14),7(1 1)-oppositadiene Cons tit. of Uvaria angolensis. Amorph.
Muhammad, I. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 719.

Absolute
configuration

C1sH240 M 220.354
1/J-form [70389-95-6]
Constit. of fruit of Tori/is japonica. Oil. [1X] 0 +29.3°.
1!. 11 -isomer: [70389-96-7]. 4(14),11-0ppositadien-1/J-ol
CISH240 M 220.354
Constit. ofT. japonica. Oil. [1X] 0 +40.3°.
7,11-Dihydro, ]/-hydroxy: 4(14)-0ppositene-1P,/1-diol
CISH2602 M 238.369
Constit. of T. japonica. Oil.

393
Farfugin A - Crispatanolide Sq-01333 - Sq-01338

Farfugin group Cycloeudesmanes

Farfugin A Sq-01333 Brothenolide Sq-01335

m
[36061-18-4] [76045-51-7]

~ W-~ I 0-.{
0
C 15H 180 M 214.307
Constit. of Farfugium japonicum. Cryst. (EtOH). Mp 80.5- C 15H 200 2 M 232.322
82.SO. [ex]~ + 39° (c, 0.3 in EtOH). Constit. of Frullania brotheri. Cryst. Mp 113-114°. [cx]n
+ 153° (c, 1.14 in CHC1 3).
Tada, M. et a/, Bull. Chern. Soc. Jpn., 1977, 50, 463.
Takeda, R. eta/, Bull. Chern. Soc. Jpn., 1983, 56, ll20.

Farfugin B Sq-01334
Chloranthalactone C Sq-01336

m
[36061-19-5]
[73215-91-5]

~0
~~ CH20Ac
C 15H 180 M 214.307 C17H 200 4 M 288.343
Constit. of Farfugium japonicum. Liq. Constit. of Ch/oranthus japonicus. Cryst. (Me 2CO). Mp
Tada, M. et al, Bull. Chern. Soc. Jpn., 1977, 50, 463. 159-160°.
Uchida, M. et a/, Chern. Pharrn. Bull., 1980, 28, 92.

Chloranthalactone D Sq-01337
[73306-74-8]
OH

~0
C 15H 180 3 M 246.305
Constit. of Chloranthus japonicus. Cryst. (EtOAc). Mp
153-154°. [cxH& +351.4° (c, 0.1 in MeOH).
9cx-Hydroxy: Chlorantha/actone E
C15H 180 4 M 262.305
Constit. of C.japonicus. Cryst. (EtOAc). Mp 162-163°.
Uchida, M. eta/, Chern. Pharrn. Bull., 1980, 28, 92.

Crispatanolide Sq-01338
[76190-55-1]

C 15H:u02 M 234.338
Constit. of Makinoa crispata. Cryst. Mp 109-110°. [cx]n
+68.7° (c, 0.8 in CHC1 3).
Asakawa, Y. eta/, J. Chern. Soc., Chern. Cornrnun., 1980, 1232.

394
6,8-Cyclo-4(14)-eudesmen-1-ol- Lindenene Sq-01339 - Sq-01345

6,8-Cyclo-4(14)-eudesmen-1-ol Sq-01339 Metab. of the sponge Epipolasis kushirnotoensis. Cryst.

1-Hydroxy-6,8-cyclo-4( 14)-eudesrnene [rxln + 7.6° (c, 1.0 in CHC1 3).
(-)-form
HO Metab. of the sponge Acanthella pulcherrirna. Oil. [rxln

~
-8.0° (c, 1.3 in CHC1 3).
Absolute [83631-19-0]
configuration Tada, H. eta/, Chern. Pharm. Bull., 1985, 33, 1941.,
Capon, R.J. eta/, Aust. J. Chern., 1988, 41, 979 (isol)
C 15H 2•.0 M 220.354
lfl-form [84071-85-2] Epipolasinthiourea A Sq-01343
Constit. of Tori/is japonica. Oil. [rxln + 12.4°. [97915-89-4]
Yamamura, S. eta/, Chern. Lett., 1982, 1681 (synth) As Epipolasin A, Sq-01342 with
Itokawa, H. eta/, Chern. Lett., 1983, 1253 (isol)
X= -NHCSNHCH 2 CH 2Ph
Cycloeudesmol Sq-01340 C14H 36N 2S M 384.628
Jsocycloeudesrnol Metab. of sponge Epipolasis kushirnotoensis. Oil.
[75744-72-8] Tada, H. eta/, Chern. Pharm. Bull., 1985, 33, 1941.

ill Geigeranolide
[84093-48-1]
Sq-01344

~H
C 15H 21;0 M 222.370
Isol. from Laurencia nipponica and Chondria oppositiclada.
Shows antibiotic props. Cryst. (hexane/isopropyl ether).
Mp 99.5-100.5°. [rxln +21.5° (c, 2.1 in CHC1 3).
Suzuki, T. eta/, Chern. Lett., 1980, 1267 (isol, struct) C 15H 200 2 M 232.322
Suzuki, T. eta/, Tetrahedron Lett., 1981, 22, 3423 (cryst struct, abs Constit. of Geigeria spp. Cryst. (pet. ether). Mp 92°. [rx]~4
config) + 59° (c, 3 in CHC1 3).
Chen, E.Y., Tetrahedron Lett., 1982, 23, 4769 (synth)
Chen, E.Y., J. Org. Chern., 1984, 49, 3245 (synth)
11P,13-Dihydro: [84093-49-2]. 11P,13-Dihydrogeigeranolide
Ando, M. eta/, J. Org. Chern., 1985, 50, 251 (struct) C 15H 2z02 M 234.338
Ando, M. et a/, Tetrahedron Lett., 1985, 26, 235 (synth) Constit. of G. spp. Gum. [oc]~ + 10° (c, 0.09 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679.
13-Deoxyisoonoceriolide Sq-01341
[90081-38-2] Lindenene Sq-01345
[24173-83-9]

~0}

C 15H 180 2 M 230.306

~3
C 15H 180 M 214.307
Stereochem. of these compds. revised in 1984. Constit. of Constit. of Lindera strychnifolia. Oil. [rxln -50.1 o (c, 1.6 in
Wunderlichia rnirabilis. Cryst. (pet. ether). Mp 84°. [rx]~ CHC1 3).
-140° (c, 0.11 in CHC1 3).
6rx-Hydroxy: [26146-27-0]. Lindenenol. !Linderene
6rx-Hydroxy: [80368-27-0].
CtsH 180 2 M 230.306
CtsH 180 3 M 246.305 Constit. of L. strychnifolia. Cryst. Mp 145°. [rxln + 15.1°
Constit. of W. rnirabilis. Gum. (CHC1 3).
6rx-Acetoxy: [90081-39-3]. 6rx-Acetoxy:
Cryst. (Et20jpet. ether). Mp 192°. [oc]~4 -286° (c, 0.19 C 17H 200 3 M 272.343
in CHC1 3). lsol. from L. strychnifolia. Prisms (pet. ether). Mp 79-
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 10, 228, 820. [oc]i;'· 5 +25.7° (c, 1.168 in EtOH).
1631.
6-0xo: [26379-19-1]. Lindenenone
CtsH 160 2 M 228.290
Epipolasin A Sq-01342 Constit. of L. strychnifolia. Cryst. (pet. ether). Mp
I
107.5-108.5°. [rxln -333° (c, 0.2 in dioxan).
13-Methoxy: [17910-10-0]. Linderoxide

~ (+)of~m C 16H 200 2 M 244.333

Constit. of L. strychnifolia. Oil. [rx]i,l - 52.SO (c, 0.8 in
CHC1 3).
!J.4•5-Jsorner, 13-rnethoxy: [15004-40-7]. Jsolinderoxide
X= -NCS Ct6Hzo0z M 244.333
C 16H 25NS M 263.446 Constit. of L. strychnifolia roots. Oil. Bp0 _3 97-100°. [rx]i;'
-238° (c, 1.5 in dioxane).
(+)-form [97950-05-5]

395
Lumiyomogin - Shizukaol A Sq-01346 - Sq-01352

Takeda, K. eta/, Tetrahedron, 1964, 20, 2655, 2991 (Lindenenol) Ratibinolide Sq-01350
Takeda, K. eta/, J. Chern. Soc. C, 1967, 631; 1969, 1920, 2786
(lsolinderoxide, Linderene, Lindenenone) [130 170-06-8]
Ishii, H. et a/, Tetrahedron, 1968, 24, 625 (Linderoxide)

l~
Tori, K. eta/, Tetrahedron Lett., 1975, 4583 (cmr)

Lumiyomogin Sq-01346
[115334-56-0]

0
CisHI80 3 M 246.305
Constit. of Ratibida latipalearis. Cryst. Mp 142-144°. [1X]i,S
+94° (CHC1 3).
Mata, R. eta/, Heterocycles, 1990, 31, II II (isol, pmr, cmr, cryst
CisHI603 M 244.290 struct)
Constit. of Ferreyranthus fruticosus. Cryst. Mp 94°.
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113. Shizukanolide Sq-01351
Ch/oranthalactone A
5-Maalianol Sq-01347 [70578-36-8]

C 15H 260 M 222.370 C15H 180 1 M 230.306

Sterochem. of compds. descr. under 13-
51X.-form [72236-31-8]
Deoxyisoonoceriolide, Sq-01341 was revised in 1984.
Constit. of Plagiochila ovalifolia. Oil. [1X]n + 106° (c, 2.5 Not clear whether compds. covered by this entry are
in CHC1 3). affected by the revision. Constit. of Chloranthus
Matsuo, A. eta/, Experientia, 1979, 35, 1279. japonicus and C. g/aber. Cryst. (also descr. as oil). Mp
95-96.SO. [IX]~ +200° (c, 2.1 in CHC1 3).
y-Maaliene Sq-01348 8,9-Didehydro: [66395-02-6]. Dehydroshizukanolide
[20071-49-2] clsH 160 1 M 228.290
Constit. of C. japonicus. Cryst. or oiL Mp 64-65.SO. [IX]~
+59.8° (c, 1 in CHC1 3).
81X,91X-Epoxide: [66395-03-7]. Ch/orantluzlactone B
CisH 180 3 M 246.305
Constit. of C. japonicus and C. glaber. Cryst. (Me 2CO).
Mp 145-146°. [IX]~ -1303° (c, 0.1 in MeOH).
C 15H 14 M 204.355 13-Hydroxy: 8,9-Dihydroonoseriolide
Constit. of Pseudopterogorgia americana. Oil. [1X]i,S + 10.9°
CisH 180 3 M 246.305
(c, 1.2 in hexane). Isol. from Actinoseris polymorpha. Cryst. (Etpjpet.
Weinheimer, A.J. eta/, J. Chern. Soc., Chern. Commun., 1968, ether). Mp 174°. [1X]i;' -203° (c, 0.31 in CHC1 3).
1070.
8,9-Didehydro, 13-hydroxy: [76015-58-2]. Onoseriolide
Constit. of Onoseris albicans. Oil. Mp 93° (as acetate).
Maaliol Sq-01349 [1X]i;' -18.3° (c, 0.06 in CHC1 3) (acetate).
Maa/ialcohol Kawabata, J. eta/, Agric. Bioi. Chern., 1979, 43, 885; 1981, 45,
[527-90-2] 1447.
I
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 689; 1981, 20, 1631.

H~
Shizukaol A Sq-01352

C 15H 260 M 222.370

Constit. of Nardostachys jatamansi, Valeriana officina/is, V.
wallichii, Eriostemon myoporoides, Prostanthera
prunelloides, Canarium samoense and others. Cryst.
(EtOH). Mp 103.5-105°. [1X]n + 18.4° (c, 1.1 in EtOH).
Biichi, G. et a/, J. Am. Chern. Soc., 1959, 81, 1968 (struct)
Bates, R.B. et a/, J. Am. Chern. Soc., 1960, 82, 2327 (synth)
Biichi, G. et a/, Tetrahedron Lett., 1962, 827 (abs config)
C31H3406 M 502.606
Constit. of Chloranthus japonicus. Needles. Mp 85-88°. [1X]i,3
-216° (c, 0.54 in CHC1 3).

396
P-Gorgonene - Eremofortin B Sq-01353 - Sq-01358

Kawabata, J. et al, Phytochemistry, 1990, 29, 2332 (isol, pmr, cmr,

ir, uv, ms)

Simple eremophilanes
Gorgonanes

IJ-Gorgonene Sq-01353

c;pA
[20071-48-1]
C 1 ~H 12 0 3 M 250.337
3rr.-form [19887-91-3] Petasitol
Cryst. (EtOAcjpet. ether). Mp 110-113°. [IX]~ -1.2° (c,
Absolute 1.1 in CHCI 3).
configuration 3-Ange/oy/: [19887-90-2].
C20H 280 4 M 332.439
C 1 ~H 24 M 204.355 Constit. of Petasites japonicus. Oil. [1X]it -26°.
Constit. of Pseudopterogorgia americana. Oil. [1X]i,S + 13.9° Takagi, I. et al, Bull. Chem. Soc. Jpn., 1977, 50, 3320.
(neat).
AgN0 3 complex: Cryst. (Me2COjhexane). Mp 132.5- 1,10-Epoxy-11(13)-eremophilen-12-oic Sq-01356
133.SO. acid ·
Bilayet Hossain, M. et al, J. Am. Chem. Soc., 1968, 90, 6607
(struct)
Boeckman, R.K. et al, J. Org. Chem., 1975, 40, 1755 (synth)

Maalioxide Sq-01354

C 1 ~H 12 0 3 M 250.337
(Jp,J0/1)-form [122769-19-1]
(-)-form Constit. of Ondetia linearis. Oil.
Zdero, C. et al, Phytochemistry, 1989, 28, 1653.

C 1 ~H 16 0 M 222.370
1,10-Epoxyfuranoeremophilan-6-one Sq-01357
(+)-form

(yQ
Constit. of Va/eriana wallichi. Cryst. by subl. Mp 66°. 0
[1X]n +33.3° (c, 4 in CHC1 3).
(-)-form [53625-18-6]
Constit. of Plagiochila acanthophylla. Cryst. by subl. Mp
66°. [1X]n -34.SO (c, 1 in CHCI 3).
Narayanan, C.S. et al, Tetrahedron, 1964, 20, 963. Ct~H 180 3 M 246.305
Matsuo, A. et al, Experientia, 1974, 30, 321. (lp,J0/1)-form [59742-12-0]
Constit. of Senecio salignus and otherS. spp. Cryst. (pet.
ether). Mp 105.SO. [1X]~4 -62.0° (c, 1.56 in CHCI 3).
Bohlmann, F. et al, Chem. Ber., 1976, 109, 819.

Eremofortin B Sq-01358
[60048-73-9]

~0
HO~'-(
C 1 ~H 20 0 3 M 248.321
Constit. of Penicillium roqueforti. Nontoxic. Cryst. (Et20).
Mp 121-123°. [1X]n + 115° (c, 0.9 in CHCI 3).
Moreau, S. et al, Tetrahedron, 1980, 36, 2989 (isol)
Yamakawa, K. et al, Chem. Lett., 1981, 929 (synth)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 874.

397
Eremofortin C- 9,11-Eremophiladiene-1,3-diol Sq-01359 - Sq-01364

Eremofortin C Sq-01359 3,11-Eremophiladiene Sq-01362

[62375-74-0] [3242-04-4]

Y=Y
H

~~u
AcO~t-CH2 0H
C 17Hn06 M 322.357 C~~H 14 M 204.355
Constit. of Penicillium roqueforti. Cryst. (Et2 0). Mp 122- Oil. Bp0 . 38 85-88° (bath).
1260.
Piers, E. eta/, Can. J. Chern., 1969, 47, 137.
12-Deoxy: [62445-06-1). Eremofortin A
C 17 Hn0~ M 306.358
Constit. of P. roqueforti. Cryst. (Et20). Mp 159-161°.
9,11-Eremophiladiene Sq-01363
Aristolochene
[a] 0 +205° (c, 0.9 in CHC1 3). Nontoxic.
12-Carboxamide: [77732-43-5]. Eremofortin E
CI,H11 N06 M 335.356
Prod. by P. roqueforti. Toxin. Involved in the biosynth. ~ (4a,5tt.1P)-fo""
of PR Toxin, Sq-01405. Mp 240° dec. [a] 0 +227° (c,
5.4 in CHCl 3).
C 1 ~H 14 M 204.355
Moreau, S. eta/, J. Org. Chern., 1977, 42, 2632.
Moreau, S. eta/, Tetrahedron, 1980, 36, 2989. (4rx..Srx.,7f/)-form [26620-71-3]
Cole, R.J. eta/, Handbook of Toxic Fungal Metabolites, Academic Constit. of Aristolochia indica. Oil. [a]i,S -76.5° (neat).
Press, N.Y., 1981, 873, 875. (4P.SP,7rx.)-form
Metab. of Aspergillus terreus. Oil. [a] 0 + 79.4° (c, 0.0176
1(10),7(11)-Eremophiladiene Sq-01360 in hexane).
lsoeremophilene Govindachari, T.R. et a/, Tetrahedron, 1970, 26, 619 1isol)
[54911-12-5] Piers, E. eta/, Can. J. Chern., 1973, 51, 2166 (synth)
Cane, D.E. eta/, J. Antibiot., 1987, 40, 1331 (isol, struct)
Cane, D.E. et a/, Tetrahedron Lett., 1990, 31, 1943 (aiJs config)
Whitehead, I.M. et a/, Phytochemistry, 1990, 29, 479 (synth)

9,11-Eremophiladiene-1,3-diol Sq-01364
C 1 ~H 14 ,M 204.355

oo·~
Constit. of Othonna spp. Oil. Bp0 . 1 85°.
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 3928 (iso/, struct)

1(1 0),11-Eremophiladiene Sq-01361

C 1 ~H 140 1 M 236.353
(lp,3rx.,4rx..Sfl)-form [37208-05-2] Capsidiol
Phytoalexin of infected sweet peppers (Capsicum
annuum). Antifungal agent. Cryst. (Et2 0). Mp 152-153°.
C 1 ~H 14 M 204.355 [cx]i;1 + 21° (c, 2.1 in CHCl 3).
(4rx..Srx.,7f/)-form [4630-07-3] Valencene 1-Ketone: [41720-93-8). 3-Hydroxy-9,11-eremophi/adien-1-
Constit. of orange oil. Oil. Bp 11 123°. [a] 0 + 79.2°. one. Capsenone
(4P.SP,7fl)-form [10219-75-7] Eremophilene C 1 ~Hn0z M 234.338
Constit. of essential oil of Petasites spp. Oil. Bp 13 Prod. from Capsidiol by Botrytis cinerea and Fusarium
129.SO. [a]i;' -142.SO. oxysporum.
Ki'epinsky, J. eta/, Tetrahedron Lett., 1968, 3315 (isol) 1-Ketone, 9,10fi-dihydro: [109986-01-8]. 3-Hydroxy-11-
Coates, R.M. eta/, J. Org. Chern., 1970, 35, 2597 (synth) eremophi/en-1-one. Dihydrocapsenone
Ishida, T. eta/, Chern. Ind. (London), 1970, 312 (isol, struct) C 1 ~H 140 1 M 236.353
McGuire, H.M. eta/, J. Chern. Soc., Perkin Trans. I, 1974, 1879 Constit. of C. annuum.
(synth) [1 09986-02-9]
Miller, C.A. eta/, J. Chern. Soc., Chern. Commun., 1977, 230
{biosynth) Ward, G.W.B. eta/, Phytopathology, 1972, 62, 1186 iCapsenone)
Naf, F. eta/, Helv. Chim. Acta, 1982, 65, 2212 (synth) Gordon, M. eta/, Can. J. Chern., 1973, Sl, 748 (struct)
Torii, S. et a/, Bull. Chern. Soc. Jpn., 1982, 55, 887 (synth) Baker, F.C. eta/, Phytochemistry, 1976, 15, 689 (biosynth)
Majetich, G. eta/, J. Org. Chern., 1985, SO, 3615 (synth) Hoyano, Y. et a/, Can. J. Chern., 1980, 58, 1894 (biosynth)
Stillman, M.J., eta/, Can. J. Chern., 1981, 59, 2303 (abs con.fig)
Whitehead, I.M. eta/, Phytochemistry, 1987, 26, 1367
(Dihydrocapsenone)
Whitehead, I.M. et a/, Phytochemistry, 1989, 28, 775 (biosynth)

398
1(10),7(11)-Eremophiladien-12-... - 1(10),11-Eremophiladien-2-one Sq-01365 - Sq-01371

1(10),7(11)-Eremophiladien-12-oic acid Sq-01365 Constit. of Vetiveria zizanioides. Cryst. (pet. ether). Mp 89-
lsovalencenic acid 900. [a]~ + 162.8° (c, 2.8 in CHC1 3).
[22387-68-4] Karkhanis, D.W. eta/, Indian J. Chern., Sect. B, I978, 16, 260.

Q:\=>H I
1(10),11(13)-Eremophiladien-12-ol
12-Hydroxyeremophilene
Sq-01369

C15H 22 0 1 M 234.338
Minor constit. of vetiver oil. Cryst. Mp 135-137°.
Hanayama, N. eta/, Tetrahedron Lett., I968, 6099 (isol, struct)
Pinder, A.R., J. Chern. Soc., Perkin Trans. I, I980, I752 (synth)
C15H 140 M 220.354
1(10),11(13)-Eremophiladien-12-oic acid Sq-01366 Ac: [64166-15-0]. 12-Acetoxyeremophi/ene
Eremophi/en-12-oic acid C 17H160 1 M 262.391
Constit. of Tessaria absynthioides. Oil. [a]~4 -67°
(CHCI 3).
Bohlmann, F. eta/, Phytochemistry, I977, 16, 1302.

1(1 0),7(11 )-Eremophiladien-2-one Sq-01370

C 15H 22 0 1 M 234.338 IX- Vetivone. lsonootkatone. a- Vetiverone
Me ester: [62458-45-1]. [15764-04-2]
C16H140 1 M 248.364
Constit. of Tessaria absynthioides. Oil. [a]i;' -91° (c, 2.6
in CHCI 3). 0~ Absolute
configuration
Bohlmann, F. eta/, Phytochemistry, I977, 16, 1302.

CtsHllO M 218.338
9,11(13)-Eremophiladien-12-oic acid Sq-01367 Constit. of vetiver oil. Solid. Mp 51-5l.SO. Bp4 152-153°.
[69905-01-7] [a]i,O + 225° (c, 7.2 in EtOH).
Semicarbazone: Cryst. Mp 222-223°. [aln +334.2° (c, 4 in
AcOH).
Endo, K. eta/, J. Chern. Soc., Chern. Commun., 1967, 89 (struct)
Marshall, J.A. eta/, J. Org. Chern., I97I, 36, I78 (synth)
Dastur, K.P., J. Am. Chern. Soc., I974, 96, 2605 (synth)
C15H110 1 M 234.338
Constit. of Athanasia thodei. Oil (as Me ester) . .[a]n -0.9° 1(1 0),11-Eremophiladien-2-one Sq-01371
(c, 1.74 in CHCI 3) (Me ester). Nootkatone
2P-Hydroxy: [100045-53-2]. 2P-Hydroxy-9,11(13)- [4674-50-4]
eremophiladien-12-oic acid
C15H110 3 M 250.337
Constit. of Stevia achalensis. Oil. [a]i;' -16° (c, 0.25 in 0~
CHCI 3).
3P-Hydroxy: [100045-54-3]. 3P-Hydroxy-9,11(13)-
eremophiladien-12-oic acid
~
CtsH110 3 M 250.337 Ct5H110 M 218.338
Constit. of S. achalensis. Oil. [a]i;' + 13° (c, 1.41 in Constit. of Chamaecyparis nootkatensis, grapefruit oil and
CHCI 3). juice. Flavouring ingredient. Cryst. (pet. ether). Mp 36-
370. [aJn + 195.SO (c, 1.5 in CHCI 3).
3-0xo: [100045-55-4]. 3-0xo-9,11(13)-eremophiladien-12-oic
acid Semicarbazone: Cryst. Mp 195-197° dec. [1X]n + 384° (c, 0.5
CtsH100 3 M 248.321 in CHCI 3).
Constit. of S. achalensis. Oil. MacLeod, W.D. eta/, Tetrahedron Lett., I965, 4779 (struct)
McGuire, H.M. et a/, J. Chern. Soc., Perkin Trans. I, I974, I879
Bohlmann, F. eta/, Phytochemistry, I978, 17, I595. (synth)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., I986, 799. Takagi, Y. eta/, Tetrahedron, I978, 34, 5I7 (synth)
Hiyama, T. eta/, Tetrahedron Lett., I979, 3529 (synth)
1(1 0),7(11 )-Eremophiladien-12-ol Sq-01368 Yanami, T. eta/, J. Org. Chern., I980, 45, 607 (synth)
lsovalencenol Inokuchi, T. eta/, J. Org. Chern., 1982, 47, 4622 (synth)
Torii, S. eta/, Bull. Chern. Soc. Jpn., I982, SS, 887 (synth)
[22387-74-2] Majetich, G. eta/, J. Org. Chern., I985, SO, 36I5 (synth)

~ CH2 0H
~ I

M 220.354

399
1(10),11-Eremophiladien-8-one - 9-Eremophilene-1,6-diol Sq-01372 - Sq-01380

1(10),11-Eremophiladien-8-one Sq-01372 1,7(11 ),9-Eremophilatriene Sq-01376

lsofukinone fJ- VetiJ/enene
[77820-40-7] [27840-40-0]

C 15H 220 M 218.338 C15H22 M 202.339

Constit. of Ligularia speciosa. Oil. [1X] 0 + 102° (c, 1.4 in Constit. of vetiver oil. Oil. [1X] 0 -160°.
CHC1 3).
Andersen, N.H. eta/, Tetrahedron Lett., 1970, 1754.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2471.
1,9,11-Eremophilatriene Sq-01377
1(1 0), 11-Eremophiladien-9-one Sq-01373
Eremophilone
[562-23-2]
(Y1
~ I

C 15H 22 M 202.339
(4«,5«,7/1)-form [5090-61-9] Nootkatene
Constit. of Chamaecyparis nootkatensis. Bp 11 134°. [1X] 0
-177° (c, 2 in CHC1 3).
C 15H 22 0 M 218.338 MacLeod, W.D. eta/, Tetrahedron Lett., 1965, 4779.
Constit. of the oil from wood of Eremophi/a mitchelli and
from rhizomes of Petasites spurius. Cryst. (MeOH). Mp 6,9,11-Eremophilatriene Sq-01378
41-42°. Bp 15 171°. [1X] 46 -207° (MeOH). )'- Vetivenene
Zalkow, L.H. et a/, J. Am. Chern. Soc., 1960, 82, 6354 (abs config) [28908-26-1]
Novotny, L. eta/, Collect. Czech. Chern. Commun., 1962, 27, 2459
(isof)
McMurry, J.E. et a/, J. Org. Chern., 1975, 40, 1829 (synth)
Ziegler, F.E. eta/, J. Org. Chern., 1977, 42, 1991 (synth)
Ficini, J. eta/, Tetrahedron Lett., 1977, 1081 (synth)

1,11-Eremophiladien-9-one Sq-01374 C 15H 22 M 202.339

Constit. of vetiver oil. Oil.
[22489-11-8]
Andersen, N.H. eta/, Tetrahedron Lett., 1970, 1759.

1,7(11),9-Eremophilatriene-3,8-dione Sq-01379
Warburgiadione
[13855-36-2]

C 15H 110 M 218.338 ~0 Absolute

Constit. of the oil of Eremophila mitchelli. Cryst. Mp 43-
440. [1X] 0 +214° (c, 0.09 in MeOH). 0~ configuration

Chetty, G.L. eta/, Tetrahedron Lett., 1969, 307 (iso/, struct)

Zalkow, L.H. eta/, J. Org. Chern., 1975, 40, 1833 (synth) ctsH180 1 M 230.306
Constit. of the heartwood of Warburgia ugandensis. Yellow
cryst. (MeOH). Mp 127-128°. [1X] 0 +25° (CHC1 3).
9,11-Eremophiladien-8-one Sq-01375 Brooks, C.J.W. et a/, Tetrahedron, 1969, 25, 2865 (isol, struct)
Alloeremophilone. allo-Eremophilone. Neopetasan Yamakawa, K. eta/, Chern. Pharm. Bull., 1979, 27, 331 (synth)
[13902-42-6]
9-Eremophilene-1,6-diol Sq-01380

C 15H 110 M 218.338

Constit. of the essential oil of Eremophila mitchel/i and
Petasites hybridus. Oil. [1X] 0 + 102°.
Bates, R.B., Chern. Ind. (London), 1966, 2170.
Neuenschwander, M. eta/, Helv. Chim. Acta, 1979, 62, 609 (iso[)
C 15H260 2
(1 p,6fl)-form
~
M 238.369

6-Cinnamoy/: [126394-63-6]. Wrightol

C14H 320 3 M 368.515

400
11-Eremophilene-2,9-dione - 7(11)-Eremophilen-8-one Sq-01381 - Sq-01386

Constit. of Solidago wrightii. Foam. 1(10)-Eremopbilen-11-ol Sq-01384

Jolad, S.D. et a/, Phytochemistry, 1989, 28, 3229 (isol, pmr, cmr,

~OH
ms)

11-Eremophilene-2,9-dione Sq-01381 (4a,5a, 7~)-form

0
0Q:\H 10
C 15H 260 M 222.370
(4rz,5rz,7fJ)-form [20489-45-61 Valeriano/
Constit. of the root of Valeriana officina/is. Oil. Bp0. 01
.0 120°. [ali? + 134° (CHC1 3) .
I
I
I
I 3,5-Dinitrobenzoyl: Cryst. (hexane). Mp 148°.
(4p,sp,7fJ)-form [10219-71-31 Eremoligenol
C 15Hzz02 M 234.338
Constit. of the root of Ligularia fischeri. Oil. Bp 2 120°.
(4rz,5rz)-form [ali; -93.SO (c, 0.675 in CHC13).
Constit. of grapefruit, Citrus paradisi. Cryst.
Ishii, H. et a/, J. Chern. Soc. C, 1966, 1545 (isol, struct)
(Et20jpentane). Mp 60-61°. [ali? +30.6° (c, 0.75 in
Jommi, G. eta/, Tetrahedron Lett., 1967, 677 (isol, struct)
CHC1 3). Coates, R.M. eta/, J. Org. Chern., 1970, 35, 2597 (synth)
1,10-Didehydro: 1(10),11-Eremophiladiene-2,9-dione Odom, H.C. eta/, J. Chern. Soc., Perkin Trans. 1, 1972, 2193
C1sH 20 0 2 M 232.322 (synth)
Constit. of C. paradisi. Cryst. (pentane). Mp 71-72.SO. Naf, F. eta/, Helv. Chim. Acta, 1982, 65, 2212 (synth)
[ali? +45.7° (c, 1.29 in CHC13).
Demole, E. eta/, Helv. Chim. Acta, 1983, 66, 1381. 9-Eremophilen-11-ol Sq-01385

11-Eremophilene-2,8,9-triol Sq-01382
Decahydro-4a,5-dimethyl-3-(1-methylethenyl)-1 ,2, 7- (4cx,5cx, 7P}:form
naphthalenetriol, 9CI

OH C1 5H 260 M 222.370
HI
(4rz,5rz,7fJ)-form [86747-08-21 Jinkoheremol
HO,~ (2cx,8cx,9cx, 1OcxH)-form Constit. of Agarwood. Oil. [al 0 -66° (c, 0.13 in
CHC1 3).
(4P,5P,7fJ)-form [54832-19-81
Constit. of Alpinia japonica. Plates by subl. Mp 64-66°.
CtsH2603 M 254.369 [al 0 -14.9° (c, 0.45 in-CHC1 3).
(2rz,8rz,9rz,lOrzH)-form [53820-53-41 Laterijlorol Nakanishi, T. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 601.
Occurs as mixt. of esters in Euryops lateriiflorus and E. ltokawa, H. eta/, Chern. Pharm. Bull., 1985, 33, 1148.
imbricatus. Cryst. (EtzOjpet. ether). Mp 158°.
(8rz,9rz,l OPH)-form 7(11 )-Eremophilen-8-one Sq-01386
2-Ketone: 8a,9a-Dihydroxy-IOPH-eremophil-II-en-2-one
CtsH240 3 M 252.353
Occurs as mixt. of esters in E. spp. Oil.
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 2730 (isol, struct)
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1135 (iso/, struct)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 1785 (synth,
struct) C 15H 240 M 220.354
(4p,sp,JOfJ)-form [19593-06-71 Fukinone
1(10)-Eremophilen-7-ol Sq-01383 Constit. of Petasites japonicus. Oil. Bp0 . 8 97°. [a]~4
1(10)- Valencen-7-o/ +67.5° (c, 1 in MeOH).
[117005-44-41 9,10-Didehydro: [ 19598-45-91. 7(1 1),9-Eremophi/adien-8-one.
lsopetasan. Dehydrofukinone
Constit. of Cacalia hastata and P. hybridus. Oil. [a] 0

~H + 162° (c, 1.9 in MeOH).

Naya, K. eta/, Tetrahedron, 1968, 24, 5871 (isol)
Piers, E. eta/, J. Org. Chern., 1970, 35, 3997 (synth)
Pinder, A.R. eta/, J. Chern. Soc. C, 1971, 3410 (synth)
C 15H 26 0 M 222.370 Hayashi, K. eta/, Phytochemistry, 1973, 12, 2931 (isol)
(al 0 + 75° (c, 0.36 in CHC1 3). Sato, T. eta/, Chern. Lett., 1977, 10, 1191 (struct)
(4rz,5rz,7rz )-form Torii, S. eta/, Bull. Chern. Soc. Jpn., 1979, 52, 2640 (synth)
Constit. of Bazzania fauriana. Oil. [al 0 + 75° (c, 0.36 in Neuenschwander, M. eta/, Helv. Chim. Acta, 1979, 62, 609 (isol)
CHC1 3).
Toyota, M. eta/, Phytochemistry, 1988, 27, 2155 (isol, struct)
Tori, M. eta/, J. Chern. Res. (S), 1990, 164 (synth, abs config)

401
11-Eremophilen-1-one- 9-Hydroxy-1(10),7(11)-... Sq-01387 - Sq-01392

11-Eremopbilen-1-one Sq-01387 Isol. from roots of P. hybridus. Mp 65-68°. [exln +49°

Er;emofflkinone (CHC1 3).
[35943-99-8] 0-(3-Methylthio-2Z-propenoyl): [70238-51-6]. S-Petasin
C 19H 260 3S M 334.479
From P.fragrans. Cryst. Mp 123-125°. [exln +51 ° (c, 1
in CHC1 3).
3-0-(5-Acetoxy-4-methyl-2Z-pentenoyl): [69734-54-9].
Senescaposone
C23 H 320 5 M 388.503
Constit. of Senecio scaposus. [ex]i;' -61.6° (c, 4.9 in
C 15H 240 M 220.354 CHC13).
Constit. of rhizomes of wild Petasites japonicus. Fragrance.
(3rz,7f/)-form
Oil. Bp0 _15 75-100° (bath). [ex]i;' + 24.6° (c, 1.1 in CHC1 3).
0-(3-Methythio-2Z-propenoyl): [87984-58-5]. Neo-S-petasin
Naya, K. et al, Chern. Lett., 1972, 241.
C19H 260 3S M 334.479
From P.fragrans. Cryst. Mp 83-84°. [exln -105° (c, 0.94
Furanoeremophilail-14,6-olide Sq-01388 in CHC13).
[23849-98-1] Herbst, D. et al, J. Am. Chern. Soc., 1960, 82, 4337 (Petasin)
Brooks, C.J.W. et al, Phytochemistry, 1972, 11, 3235 (l>iosynth)

ffi) Bohlmann, F. et al, Phytochemistry, 1978, 17, 1337

(Senescaposone)
Sugama, K. et al, Phytochemistry, 1983, 22, 1619 (S-Petasin, Neo-

}:7 CH3
S-petasin)

0 8-Hydroxy-1,11-eremopbiladien-9-one Sq-01391
C 15H 180 2 M 230.306
6rz-form
Constit. of Ligularia hodgsoni. Cryst. Mp 136-138°. [exln
-47° (dioxan).
Ishizaki, Y. et al, J. Chern. Soc., Chern. Commun., 1969, 551.
C 15H 220 2 M 234.338
3-Hydroxy-7(11 ),9-eremophiladien-8-one Sq-01389 Brz-form

f('yo Constit. of Eremophila mitchelli. Cryst. (pet. ether). Mp

HO'~
C 15H 22 0 2 M 234.338
Jrz-form [469-67-0] Isopetasol
Constit. of Petasites fragrans. Cryst. (EtOAc/Etp). Mp
126-127° (123.5-125°). [ex]n + 113° (c, 0.9 in CHC1 3).
3-(5-Acetoxy-4-methyl-2Z-pentenoyl): [69734-55-0].
Isosenescaposone
C23H 32 0 5 M 388.503
Constit. of Senecio scaposus. Oil. [ex]i;' -2.0° (c, 3.6 in
CHC1 3).
3-Ketone: 7(11),9-Eremophi/adien-8-one. Isopetasone
Cryst. (MeOH). Mp 113-115°. [ex]n +31° (CHC1 3).
Brooks, C.J.W. et al, Tetrahedron, 1969, 25, 2865 (synth)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1337
103°. [ex]~ + 59.3° (c, 1.1 in CHCI 3).
6 1•10-Isomer: 8-Hydroxy-1(10),11-eremophiladien-9-one
C15H 220 2 M 234.338
Constit. of E. mitchelli. Oil. Bp0_0003 50°. [ex]~ -33.6° (c,
0.8 in MeOH).
1,2-Dihydro: 8-Hydroxy-11-eremophi/en-9-one.
Hydroxydihydroeremophilone. Santa/camphor
C15H 240 2 M 236.353
Isol. from E. mitchelli and Santa/urn preissian.um. Prisms
(MeOH). Mp 102-103°. [ex]n +90.6° (CHC1 3).
Grant, D.F. et al, Chern. Ind. (London), 1956, 278.
Zalkow, L.H. et al, J. Am. Chern. Soc., 1960, 82, 6354 (abs config)
Massy-Westropp, R.A. et al, Aust. J. Chern., 1966, 19, 303.
9-Hydroxy-1(10),7(11)-eremophiladien-8- Sq-01392
one

eM
(lsosenescaposone) OH
Sugama, K. et al, Phytochemistry, 1983, 22, 1619 (Isopetasol)

3-Hydroxy-9,11-eremophiladien-8-one Sq-01390

1('10 CISH2202 M 234.338

(3a, 7a )-form
HO"~'( 9P-form
Ac: [55050-19-6]. 9-Acetoxy-1,10-didehydrofukinone
C 17H 240 3 M 276.375
C 15H 220 2 M 234.338
Constit. of Senecio elegans. Oil. Bp0 _1 120°. [cx]i;' - 52.7°
(3rz,7rz)-form [64236-38-0] Petasol (c, 3.4 in CHC1 3).
Constit. of Petasites fragrans. Viscous yellow oil. [exln
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2912 (isol)
+ 124° (c, 0.74 in CHC1 3).
0-Ange/oy/: [26577-85-5]. Petasin
C20H 280 3 M 316.439

402
9-Hydroxy-7(11),9-eremophiladien-8-... - 3-Hydroxyfuranoeremophilane Sq-01393- Sq-01400

om
9-Hydroxy-7(11 ),9-eremopbilad.ien-8-one Sq-01393 4-Hydroxy-1(10)-eremopbilen-2-one Sq-01397
2-Hydroxyeremophilone
[4895-42-5]

H~
C 15H 240 2 M 236.353
4/l-form
C15H:n02 M 234.338 4-Hydroxy-2-oxovalencene
Constit. of Eremophila mitchelli. Cryst. (MeOH). Mp 66- Constit. of Geigeria ornativa. Oil. [1X]i.4 +46° (c, 0.41 in
670. [1X]n + 131° (MeOH). CHC1 3).
Zalkow, L.H. et al, Tetrahedron, 1966, 22, 337. [125289-80-7]
Pinder, A.R. eta/, J. Chern. Soc. C, 1971, 3410. Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr)

2-Hydroxy-7(11)-eremopbilen-8-one Sq-01394 11-Hydroxy-1(10)-eremopbilen-2-one Sq-01398

om
11-Hydroxy-1(10)-valencen-2-one
H
HO~
Cryst. ~H
(2P,4P,5P,JOPII)-form C15H 240 2 M 236.353
0-(3-Methylthio-2Z-propenoyl): [36031-35-3]. S-Japonin (4«,5«,71)-form
C 1,H:11P 3S M 336.494 Constit. of Teucrium carolipaui. Thick oil. [IX]~ + 131.2°
Constit. of leaves of Petasites japonicus. Mp 116.5-117°. (c, 0.188 in EtOH).
[1X]i;4 + 7.0° (c, 1.01 in CHC1 3). Savona, G. et al, Phytochemistry, 1987, 26, 571.
Naya, K. et al, Chern. Lett., 1972, 241.
11-Hydroxy-6-eremopbilen-8-one Sq-01399
2-Hydroxy-11-eremopbilen-9-one Sq-01395 Petasitolone
[35124-22-2]

HO,~O
w;OH
H

I ~
I I
I

C 15H 240 2 M 236.353 CtsH240 2 M 236.353

(2«,4«,5«,7P,10p)-form [74299-59-5] Rishitinone Constit. of Petasites japonicus. Oil. Bp0_15 92°. [1X)i;4 + 16.7°
Constit. of diseased potato tubers. Cryst. Mp 72-75°. (c, 0.99 in MeOH).
[«Jn +10.lo. Naya, K. et al, Bull. Chern. Soc. Jpn., 1971, 44, 3165.
Katsui, N. et al, Bull. Chern. Soc. Jpn., 1982, 55, 2478 (isol, struct) Liu, H.-J. eta/, Can. J. Chern., 1984, 62, 2676 (synth)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2042 (synth)
3-Hydroxyfuranoeremopbilane Sq-01400
3-Hydroxy-11(13)-eremopbilen-9-one Sq-01396
[126199-39-1]

C15H:n02 M 234.338
(3«,10«H)-form
3-Methyl-2-pentenoyl: Constit. of Senecio praecox. Oil.
C15H 240 2 M 236.353 Bohlmann, F. et al, Chern. Ber., 1976, 109, 819.
(3«,10p)-form
Constit. of Senecio glutinosus. Oil.
Zdero, C. eta/, Phytochemistry, 1989, 28, 3532 (isol, pmr)

403
9-0xo-1(10),11(13)-eremophiladien-... - 3,7,13-Trihydroxy-1,9,11-... Sq-01401- Sq-01406

9-0xo-1(10),11(13)-eremophiladien-12-al Sq-01401 Constit. of Hansfordia pulvinata and Asper!{illus oryzae.

[99305-20-1] Phytotoxin and sporogenic agent. Cryst. Mp 104-105°.
[rx]i? + 236° (c, 0.5 in MeOH).
0 11,12-Epoxy: [85431-61-4]. Phaseolinone

~0
C 15H 200 5 M 280.320
Constit. of Macrophomina phaseolina. Seed germination
inhibitor for Phaseo/us mungo. Cryst. Mp 126-128°. [rx] 0
+94.SO (c, 0.8 in EtOH).
Riche, C. eta/, Tetrahedron Lett., 1974, 2765 (isol, struct)
C 15H 200 1 M 232.322 Riche, C. et a/, Acta Crystallogr., Sect. B, 1975, 31, 1476 (cryst
Constit. of Eremophila rotundifolia. Oil. Bp0 . 002 95-105°. struct)
Yamakawa, K. et al, Chern. Pharm. Bull., 1980, 28, 3265 (synth)
Abell, A.D. et al, Aust. J. Chern., 1985, 38, 1263.
Dhar, T.K. eta/, Tetrahedron Lett., 1982, 23, 5459 (Phaseolinone)
Tirilly, Y. et al, Phytochemistry, 1983, 22, 2082 (deril')
2-0xo-1(1 0), 11(13)-eremophiladien-12-oic Sq-01402 Tanaka, S. et al, Agric. Bioi. Chern., 1984, 48, 3189 1deriv)
acid Mori, K. et al, Justus Liebigs Ann. Chern., 1988, 97 (.1ynth)
Kitahara, T. et al, Tetrahedron, 1988, 44, 4339 (synthi
1,2 ,3 ,4,6, 7,8,8a-Octahydro-8,8a-dimethyl-rx-methylene-6-oxo-
2-naphthaleneaceticacid, 9CI. Tessaric acid
[58142-10-2] PR Toxin Sq-01405
[56299-00-4]
0~
~COOH ~<:
C 15H 200 3 M 248.321 A cO~
Constit. of Tessaria absynthioides. Cryst. Mp 154-155°. CHO
[rx]i;1 -143.4°. C 17H 200 6 M 320.341
llrx,13-Dihydro: [83016-43-7]. 2-0xo-1(10)-eremophilen-12- Toxin from Penicillium roqueforti. Inhibits microsomal
oic acid. 11S,13-Dihydrotessaric acid protein synth. Cryst. Mp 155-157°. [rx]i;' +290° (c, 1.34
CtsHu03 M 250.337 in CHC1 3).
Constit. of Pluchea sericea. Cryst. (Me 2CO/diisopropyl t> Possible carcinogen. WH1316970.
ether). Mp 156-157°. [rx]i? -190.43° (c, 0.209 in CHC1 3). Wei, R. et al, Appl. Microbial., 1973, 25, Ill (isol)
Giordano, O.S. eta/, CA, 1976, 84, 56487r. Wei, R. et al, Tetrahedron, 1975, 31, 109 (struct, pmr, ms)
Romo de Vivar, A. et al, Chern. Lett., 1982, 957 (cryst struct) Ueno, Y. et al, Cancer Res., 1976, 36, 445 (tox)
Baert, F. et al, Acta Crystallogr., Sect. B, 1980, 36, 402 (cryst
struct, abs config)
9-0xo-11(13)-eremophilen-12-oic acid Sq-01403 Chalmers, A.A. et al, J. Chern. Soc., Perkin Trans. 1, 1981, 2899
Flourensic acid (biosynth)
[33596-80-4] Moreau, S. et al, Phytochemistry, 1981, 20, 2339 (biosynth)
Gorst-Allman, C.P. eta/, Tetrahedron Lett., 1982, 23, 5359

(1\COOH
(biosynth)
Cole, R.J. et al, Handbook of Toxic Fungal Metabolites, Academic
Press, N.Y., 1981, 870.

3,7,13-Trihydroxy-1,9,11-eremophilatrien- Sq-01406
8-one
C 15Hu03 M 250.337
Constit. of Flourensia cernua. Cryst. (CHC1 3/Et20). Mp
160-161°. [rx]i;' +60.4° (c, 1.1 in MeOH).
Kingston, D.G.I., Phytochemistry, 1975, 14, 2033 (isol, struct)
Herron, J.N. eta/, J. Chern. Soc., Perkin Trans. 1, 1983, 161
(synth)
(3p,7fl)-form
Phomenone Sq-01404 3-0-(5S-Methyi-2E,4E-octadienyl): [121661-42-5].
6rx,7rx-Epoxy-3rx,13-dihydroxy-9,12-eremophiladien-9-one Dendryphiellin E
C24 H 310 5 M 400.514
[55785-58-5] Meta b. of Dendryphiella salina. Oil. [rx]i? + 166.7° (c,
0.22 in EtOH). Treatment with acidic ethanol gives an
artefact Dendryphiellin F.
3-Ketone: [121661-44-7]. 7,13-Dihydroxy-1,9,11-
eremophilatriene-3,8-dione. Dendryphiellin G
Metab. of D, salina. Oil. [rx]i? - 11.2° (c, 0.12 in EtOH).
C 15H 200 4 M 264.321 Guerriero, A. et al, Helv. Chim. Acta, 1989, 72, 438 (isol, pmr,
Phytotoxin of Phoma exigua. Cryst. (EtOAc). Mp 148- cmr)
1490. [rx) 0 +225°.
13-Deoxy: [88418-12-6]. 13-Desoxyphomenone. Sporogen
A.O I
M 248.321

404
12,12'-Bifuranoeremophila-7,11-dien-... - 1,8-Dihydroxy-7(11)-eremophilen-... Sq-01407 - Sq-01413

1,8-Dihydroxy-4(15),7(11)-eremophiladien- Sq-01411
12,8-olide
Eremophilanolides and
furanoeremophilanes ~0
C15H 100 4 M 264.321
12,12'-Bifuranoeremophila-7,11-dien-3-ol Sq-01407 (lf.,8~,JOPH)-form [84807-45-4] /stanbulin D
Constit. of Smyrnium creticum. Cryst. (EtOH). Mp 204-
H 2060.
OH
Ulubelen, A. eta/, Phytochemistry, 1982, 21, 2128.

H 6,10-Dihydroxy-7(11 ),8-eremophiladien- Sq-01412

C.lOH4z04 M 466.659 12,8-olide
(3P,J' /1)-form
Di-0-angeloyl: 12,12' -Bz13-angelyloxyfuranoeremophila-
7,11-diene]
C 40Hs.06 M 630.863
fPyo\:::o
Constit. of Farfugium japonicum. Cryst. Mp 76-78°. [a]~1
+80.6° (c, 0.62 in CHC1 3).
~OH
Kurihara, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1981, (6p,JO/l)-form
101, 35. 6-Me ether: [62078-12-0]. Ligolide
Ct,H1z04 M 278.347
Cyclodebneyol Sq-01408 Constit. of Ligularia macrophylla.
[104777-67-5] Nitonova, L.P. et a/, Khim. Prir. Soedin., 1976, 742; CA, 86,
103055b.

cr=Q
: H OH
1,8-Dihydroxy-7(11)-eremophilen-12,8-
olide
Sq-01413

C 15H 140 1 M 236.353

Constit. of Nicotiana debneyi. Oil.
Burden, R.S. eta/, Phytochemistry, 1986, 25, 1607.
(l~,8(J(OH)-form
7P,8P:8tx,12-Diepoxy-11 (13)-eremophilene Sq-01409
7P,8P:8a,J2-Bisepoxy-11(13)-eremophilene C 15H 110 4 M 266.336
[97456-95-6] (lp,81T.OH)-form
l-Ac: [128255-37-8]. Palmosalide B
C1 7H 140 5 M 308.374
Constit. of Coelogorgia palmosa. Oil. [aln +52.8° (c, l.5
in CHC1 3).
(41T.,51T.,8POH,l0fl)-form
C 15H 110 1 M 234.338 1-Ketone: [35481-83-5]. ent-8cx-Hydroxy-1-oxo-7(11)-
Constit. of a Blumea sp. Oil. eremophilen-12,8-olide. lstanbulin A
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 505. C 15H 100 4 M 264.321
Isol. from Smyrnium olusatrum. Cryst. Mp 246°. [a]i,O
+81.SO (MeOH).
1,8-Dihydroxy-3,7(11)-eremophiladien- Sq-01410
U1ubelen, A. eta/, Tetrahedron Lett., 1971, 4455 (lstanbulin A)
12,8-olide Budesinsky, M. eta/, Collect. Czech. Chern. Commun., 1984, 49,
1311 (abs config, Istanbulin A)

~0
Weimer, D.F. et a/, Tetrahedron Lett., 1990, 31, 1973 (Palmosalide
B)

C 15H 100 4 M 264.321

[111950-79-9] /stanbulin F
'(JP,B~,J0/1)-form
Constit. of Smyrnium connatum. Amorph.
Goren, N. eta/, Phytochemistry, 1987, 26, 2633.

405
1,10-Dihydroxy-11(13)-eremophilen-... - 3,6-Dihydroxyfuranoeremophil-1(10)-... Sq-01414- Sq-01419

1,10-Dihydroxy-11(13)-eremophilen-12,8- Sq-01414 (lrr.,6P,10rr.H)-form

olide 6-(Methylpropanoyl): [55050-48-1].
C1,H11;05 M 334.411
Constit. of Senecio umbellatus. Cryst. (EtzO/pet. ether).
Mp 110-112°. [oc]i;l -30.2° (c, 1.2 in CHC1 3 ).
6- Tigloyl: [55058-60-1].
C20H 21;05 M 346.422
Constit. of S. umbellatus. Oil.
6-Angeloyl: [55658-63-4].
C1sH2204 M 266.336 C20H 21;05 M 346.422
(Jp,ap,IOrr.)-form Constit. of S. rigidus. Oil.
Constit. of Ondetia linearis. Oil. [oc]i;l +43° (c, 1.14 in 6-Angeloyl, l-Ac: [55658-64-5].
CHC1 3). C22 H280 6 M 388.460
11 p,J3-Dihydro: IP,IOrr.-Dihydroxy-llfJH-eremophillln- Constit. of S. rigidus. Oil.
12,8P-olide 1-(3-Methylbutanoyl), 6-(methylpropanoyl):
C 1sH240 4 M 268.352 C24 H 340 6 M 418.529
Constit. of 0. linearis. Gum. From S. panduriformis. Cryst. (Et20jpet. ether). Mp
10-Deoxy, JOoc-chloro: lOrr.-Chloro-lP-hydroxy-11(13)- 128°. [oc]i;l -103° (c, 0.53 in CHC1 3).
eremophilen-12 ,8P-olide Bohlmann, F. et a/, Chern. Ber., 1974, 107, 2912; 1977, 110, 474.
C15H 21 C103 M 284.782
Constit. of 0. linearis. Cryst. Mp 203°. [oc]i;l +41° (c,
0.46 in CHC1 3). 4,6-Dihydroxyfuranoeremophilan-9-one Sq-01418
4,6-Dihydroxy-9-oxofuranoeremophilane
Zdero, C. et a/, Phytochemistry, 1989, 28, 1653.

6,8-Dihydroxy-7(11)-eremophilen-12,8- Sq-01415
olide

~o'>=o C 15H 200 4 M 264.321

~
OH
(4rr.,6p,JOrr.H)-form
6-(Methylpropanoyl): [53820-31-8].
C 15H 220 4 M 266.336 C19H 260 5 M 334.411
(6p,apOH)-form [58848-38-7] Constit. of Euryops hebecarpus. Cryst. (Etpjpet. ether).
Constit. of Ligularia fauriei and Petasites japonicus. Mp 208°.
Cryst. (CHC1 3/C 6H 6). Mp 217-218°. [oc] 0 +82° (c, 1 in 6-Tigloyl: [53820-42-1].
EtOH). C20H 260 5 M 346.422
[65349-94-2] Constit. of E. virgineus. Cryst. Mp 242°.
Moriyama, Y. eta/, Bull. Chern. Soc. Jpn., 1976, 3196. 6-Angeloyl: [53820-27-2].
C20 H 260 5 M 346.422
3,6-Dihydroxyfuranoeremophilan-15-oic Sq-01416 Constit. of E. hebecarpus. Cryst. (Et20/pet. ether). Mp
acid 214°. [ocJi: -9.8° (c, 0.1 in CHCI 3).
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730.

~0)> 3,6-Dihydroxyfuranoeremophil-1 (1 0)-en-9- Sq-01419

one
HO~ 3,6-Dihydroxy-9-oxoeuryopsin
HOOC OH
CisH 200 5 M 280.320
(3p,6fl)-form
3,6-Diangeloyl: [54878-43-2].
C25H 320 7 M 444.524
Constit. of Othonna spp. Viscous oil.
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 3928.
C 15H 180 4 M 262.305
(3p,6fl)-form
1,6-Dihydroxyfuranoeremophilan-9-one Sq-01417
6-(Methylpropenoyl): [53987-94-3].
1,6-Dihydroxy-9-oxofuranoeremophilane
C19H 220 5 M 330.380
From Euryops spathaceus. Cryst. (Etpjpet. ether). Mp
145.5°.
6-Angeloyl: [53820-51-2].
C20H 240 5 M 344.407
Constit. of E. spathaceus. Cryst. (Etpjpet. ether). Mp
151°.
M 264.321 3,6-Bis(methylpropenoyl): [53820-70-5].

406
1,10-Epoxy-4,6-dihydroxyfurahoeremop ... - 1,10-Epoxyfuranoeremophilan-6-ol Sq-01420- Sq-01424

C23H:uP6 M 398.455 (l1X.,101X.)-fornt [35470-54-3]

Co11$tit. of E. spathaceus. Oil.
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730.
1,10-Epoxy-4,6-
dihydroxyfuranoeremophilan-9-one
8,8a- Epoxyfuranoligularan
Constit. of S. silvaticus. Viscous liq. Bp 242°. [ex]~
-22.6° (EtOH).
Sq-01420 Schild, W., Tetrahedron, 1971, 27, 5735.
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2912.

@
1,10-Epoxyfuranoeremophilane-3,6-diol Sq-01423

bH~H
C15H 180 5 M 278.304
(4rx.,6P,JO/I)-form C 15H 200 4 M 264.321
6-(2-Methy/propanoyl): [59742-13-1). 1,10-Epoxy-4- 6-Tigloyl: [41929-06-0]. Nemosenin A
hydroxy-6-isobutyryloxyfuranoeremophilan-9-one C~~ 260 5 o M 34~.422
C1,H240 6 M 348.395 [ex] 0 -35.3 (c, 0.4 m CHC1 3).
Constit. of Senecio salignus. Cryst. (Etp). Mp 155°. 6-(l-Methylbutanoyl): [41929-07-1]. Nemosenin B
Bohlmann, F. et al, Chern. Ber., 1976, 109, 819. C20 H 280 5 M 348.438
[ex]~ -19° (c, 0.3 in CHC1 3).
1,10-Epoxy-11(13)-eremophilen-12,8-olide Sq-01421 6-(l-Methylpropanoyl): [41929-08-2). Nemosenin C

(tx?o
C19H 260 5 M 334.411
0 [ex]~ -34.4° (c, 0.5 in CHC1 3).
6-(l-Methylpropanoyl), 3-Ac: [41983-88-4]. Nemosenin D
C21H 280 6 M 376.449
Cryst. Mp 134-135°. [ex]~ -27.SO (c, 0.1 in CHC1 3).
Novotny, L. et al, Collect. Czech. Chern. Commun., 1973, 38, 739.
C 15 H~,0 3 M 248.321
(Jp,ap,J0/1)-form 1,10-Epoxyfuranoeremophilan-6-ol Sq-01424
Constit. of Ondetia linearis. [ex]i: -17° (c, 3.68 in
CHC1 3). 0

~
11 cx,13-Dihydro: Jp,JOP-Epoxy-llrx.H-eremophi/en-12,8P-
olide
C15H 22 0 3 M 250.337
Constit. of 0. linearis. Cryst. Mp 98°.
OH
lex-Hydroxy: Jp,JOP-Epoxy-2rx.-hydroxy-11(13)-eremophi/en-
12,8P-olide C 15H 200 3 M 248.321
CtsHzo04 M 264.321 (lp,6p,JO/I)-form [41702-76-5]
Constit. of 0. linearis. Gum. Constit. of Ligularia spp. Oil. [ex] 0 -45° (c, 0.11 in
lex-Hydroxy, 11ex,13-dihydro: lp,JOP-Epoxy-2~X.-hydroxy­ EtOH).
ll1X.H-eremophi/en-12,8P-olide 0-(l-Methylpropenoyl): [55050-49-2). 1p, 1OP-Epoxy-6p-(2-
C 15H 220 4 M 266.336 methylacryloyloxy)furanoeremophilane
Constit. of 0. linearis. Cryst. Mp 145°. [ex)i: -74° (c, 0.4 C19H 240 4 M 316.396
in CHC1 3). Constit. of Senecio rigidus. Oil.
lex-Hydroxy, 11P,13-dihydro: 1P,10P-Epoxy-1rx.-hydroxy- 0-(3-Methyl-l-butenoyl): [55050-50-5]. 1P,10P-Epoxy-6P-
11PH-eremophi/en-11,8P-olide senecionyloxyfuranoeremophilane
C1sH 220 4 M 266.336 C20 H 260 4 M 330.423
Constit. of 0. linearis. Gum. Constit. of S. rigidus. Oil.
lex-Hydroxy, 11P,13-dihydro: Jp,JOP-Epoxy-3rx.-hydroxy- 0-(4-Hydroxy-l-methyl-l-butenoyl): [63366-01-8). 1,JOp-
11PH-eremophi/en-11,8P-olide Epoxy-6p-(y-hydroxyangeloyloxy)furanoelemophilane
C15H 220 4 M 266.336 C20 H 260 5 M 346.422
Constit. of 0. linearis. Gum. Constit. of Ligularia vorobierii.
Zdero, C. et al, Phytochemistry, 1989, 28, 1653. 6-Ketone: 1,10-Epoxyfuranoeremophilan-6-one
CtsH 180 3 M 246.305
1,10-Epoxyfuranoeremophilane Sq-01422 Constit. of S. salignus and other S. spp. Cryst. (pet.
ether). Mp 105.SO. [ex]i: -62.0° (c, 1.56 in CHCI 3).
Sato, T. et al, Chern. Lett., 1972, 637 (iso[)
Novotny, L. et al, Collect. Czech. Chern. Commun., 1973, 38, 739
(struct)
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2912; 1976, 109, 819;
1977, 110, 1759 (iso[)
Sato, T. et al, Bull. Chern. Soc. Jpn., 1975, 48, 112 (isol, nmr)
CtsHzo0 2 M 232.322
(lp,J0/1)-form [55102-21-1]
Constit. of Senecio glastifolius. Oil. Bp0 . 1 120°. [ex]i:
-24.3° (c, 0.85 in CHC1 3).

407
1,10-Epoxyfuranoeremophil-1(10)-ene-... - 1(10),7(11),8-Eremophilatrien-12,8-... Sq-01425 - Sq-01430

1,1~Epoxyfuranoeremophil-1(10)-ene-6,9- Sq-01425 3fl-Hydroxy: [100045-48-5]. 3P-Hydroxy-1(10),1 I(I3)-

dione eremophiladien-12,8P-olide. 3P-HydroxyxtmtluModiene
C15H 100 3 M 248.321
oo

cHQ
Constit. of S. achalensis. Oil.
3-0xo: [100045-49-6]. 3-0xo-1(10),11(13)-eremophiladien-
12,8P-olide. 3-0xoxtmt/uuwdiene
C 15H 180 3 M 246.305
Constit. of S. achalensis. Cryst. (Et20/pet. ether). Mp
126°. [oc]~4 -72° (c, 0.17 in CHC1 3).
C 15H 160 4 M 260.289 11 p,13-Dihydro: [60362-07-4]. (1 1R)-Eremophi/-1 ( 1O)-en-
(lfl)Of/)-form 12P,8P-olide. Xantluurene
Constit. of Senecio smithii. Cryst. (Et20jpet. ether). Mp C 15H 220 2 M 234.338
104°. [oc]~ -26.7° (c, 0.12 in CHC13). Constit. of Xanthium canadense. Oil. [oc]~ -32.2° (c, 1.8
in MeOH).
Bohlmann, F. et al, Phytochemistry, 1981, :ZO, 2389.
Bohlmann, F. et al, Chern. Ber., 1976, 109, 2651 (Dugesialactone)
Tanaka, N. et al, Chern. Pharm. Bull., 1976, 24, 1419
1,1~Epoxy-13-bydroxy-7(11)­ Sq-01426 (Xanthanodiene, Xanthanene)
eremophilen-12,8-olide Bohlmann, F. et al, Justus Liebigs Ann. Chem., 1986, 799 (derivs)

c;tc(:H
9,11(13)-Eremophiladien-12,8-olide Sq-01429

~:-~o (1o,8a)-f•~
C 15H 100 4 M 264.321
CtsH21,0z M 232.322
(lfl,Bfl)0/1)-form [122769-17-9]
Constit. of Ondetia linearis. Cryst. Mp 129°. [oc]~ -75° (7rz,Brz)-form [62870-69-3] Eremofrlll/Juwlide
(c, 0.2 in CHC1 3). Constit. of Frullania dilatata. Cryst. (hexane). Mp 82-
82.50. [oc]n +9°.
Zdero, C. et al, Phytochemistry, 1989, 28, 1653.
(7p,BJI)-form
Constit. of Artemisia pectinata. Oil. Bp0 _1 150°. [oc]~
Eremofortin D Sq-01427 +47.9° (c, 0.3 in CHC1 3).
[60048-74-0] 3P-Hydroxy: [100045-50-9]. 3P-Hydroxy-9,11(13)-
eremophiladien-l2,8P-olide

~o\ . C15H.03 M 248.321

Constit. of Stevia achalensis. Oil. [oc]~ +46° (c, 0.20 in
CHC1 3).
A cO~ 3-0xo: [100045-51-0]. 3-0xo-9,1 1(13)-eremophiladien-12,8P-
olide
C 17H 140 6 M 324.373
Sesquiterpene antibiotic. Prod. of Penicillium roqueforti. C 15H 180 3 M 246.305
Constit. of S. acha/ensis. Oil. [oc]~ + 21° (c, 0.20 in
Toxin. Involved in the biosynth. of PR Toxin, Sq-
01405. Cryst. (EtOAc). Mp 209-211°. [oc]n +91° (c, 1.2 CHCIJ.
in CH03). Asakawa, Y. et al, Bull. Soc. Chim. Fr., 1976, 1465.
Bohlmann, F. et al, Phytochemistry, 1985, 24, 995.
Amoux, B. eta/, Acta Crystallogr., Sect. B, 1977, 33, 2930 (cryst Bohlmann, F. eta/, Justus Liebigs Ann. Chem., 1986, 799.
struct)
Moreau, S. et al, Tetrahedron, 1980, 36, 2989 (isol, stereochem,
spectra, struct) 1(10),7(11),8-Eremophilatrien-12,8-olide Sq-01430
Ugulare110/ide
1(10),11(13)-Eremophiladien-12;8-olide Sq-81428 [20489-24-1]

s
~o

--
to
11
~ 13 (7r:J.,8r:J.)-jorm
c;cc?o
C15H 180 2 M 230.306
C 1Jl.02 M 232.322
Constit. of Ligularia sibirica. Yellow cryst. (Etp or pet.
(7rz,Brz)-form [60857-75-2] D11gesialtu:tone ether). Mp 134.5-135°. [oc]n -332° (MeOH).
Constit. of Dugesia mexicana. Oil.
Ishizaki, Y. et al, Tetrahedron, 1970, 26, 5387.
(7/l,Bf/)-form [60362-06-3] Xtmtluutodiene Yamakawa, K. eta/, Chem. Pharm. Bull., 1980, 28, 3265 (synth)
Constit. of roots of Xanthium canadense. Syrup. [oc]i:
-42.9° (c, 2.3 in CHC1 3).
lac-Hydroxy: [100045-47-4]. 2ac-Hydroxy-I(IO),II(I3)-
eremophiladien-12,8fl-olide. 2rz-Hydroxyxantluuwdiene
C 15H 100 3 M 248.321
Constit. of Stevia achalensis. Oil. [oc]~ -31° (c, 0.43 in
CHC1 3).

408
7(11)-Eremophilene-12,8:14,6-... - Furanoeremophilane-2,3-diol Sq-01431 - Sq-01436

7(11 )-Eremophilene-12,8: 14,6-diolide CtsH200 M 216.322

Po
Sq-01431
Constit. of Senecio spp. Oil. Bp0.1 130°. [IX]~ + 145° (c,
H 1.2 in CHC1 3).
Novotny, L. eta/, Collect. Czech. Chern. Commun., 1962, 27, 1400,
2462; 1965, 30, 3579 (iso/, struct)
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1767 (synth)
Nayakura, I. eta/, Chern. Lett., 1975, 1143 (synth)
Bohlmann, F. eta/, Phytochemistry, 1977, 16, 135 (iso[)

CtsHts04 M 262.305 Furanoeremophilane-1,3-diol Sq-01435

(6a.,8a. )-form [58947-65-2] 1,3-Dihydroxyfuranoeremophi/ane
Constit. of Ligularia fauriei. Cryst. (Et20). Mp 186-
186.SO dec. [1X]n + 93° (c, 0.91 in CHC1 3).
Moriyama, Y. eta/, Bull. Chern. Soc. Jpn., 1976, 49, 3196.

7(11 )-Eremophilen-12,8-olide Sq-01432

~-0~
CtsH220 3 M 250.337
(1«,3«,1 O«H)-form
~0 11X-Hydroxyeuryopsonol
3-(3-Methy/-2-butenoyl):
C 15H 220 2 M 234.338 C20H 280 4 M 332.439
(8a.,10PH)-form [4871-90-3] Eremophilenolide Constit. of Senecio smithii. Cryst. (Etp). Mp 194°.
[1X]~+ oo (c, 0.35 in CHC1 3).
Constit. of Petasites officianalis. Cryst. (Et20). Mp 125°.
[IX)~ -16.6°. 3-Ange/oyl:
9,10-Didehydro: 7(11),9-Eremophi/adien-12,81X•olide
C20H 280 4 M 332.439
Constit. of S. smithii. Cryst. (Et20jpet. ether). Mp 150°.
C1sH2002 M 232.322
[1X]~ -0.8° (c, 0.95 in CHC1 3).
Constit. of Senecio hieracioides. Oil. [IX]~ -10° (c, 0.92
in CHC1 3). 3-(2-M ethylpropanoyl):
9,10-Didehydro, 8P-hydroxy: 8P-Hydroxy-7(11),9- C19H 2804 M 320.428
eremophiladien-12,81X-olide Constit. of S. smithii. Gum.
CtsH 200 3 M 248.321 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2389
Constit. of S. hieracioides. Oil.
(8p,JOa.H)-form [29395-64-0] Tetrahydroligularenolide Furanoeremophilane-2,3-diol Sq-01436
Constit. of S. aureus. Cryst. Mp 91-92°. 2,3-Dihydroxyfuranoeremophi/ane
Piers, E. eta/, Can. J. Chern., 1973, 51, 2166 (synth)
Nayakura, I. et a/, Chern. Lett., 1975, 1143 (synth)
Horii, Z. eta/, Chern. Pharm. Bull., 1977, 25, 2782 (synth) HO~o)>
Pennanen, S.l., Acta Chern. Scand., Ser. B, 1981, 35, 555 (synth)
Nachman, R.J., Phytochemistry, 1983, 22, 780 HO~ (2P,3P}:form
( Tetrahydroligularenolide)
Bohlmann, F. eta/, J. Nat. Prod. (Lioydia), 1984, 47, 718 (derivs) CtsH 220 3 M 250.337
(2p,3p)-form [54879-03-7]
9-Eremophilen-12,8-olide Sq-01433 Oil.

Q:W=o
2-Ac, 3-ange/oy/: [54878-86-3].
C22 H 300 5 M 374.476
Constit. of Orthonna spp. Oil.
2,3-Diangeloyl: [54878-87-4].
C25 H 340 5 M 414.541
C 15H 220 2 M 234.338 Constit. of 0. spp. Oil.
(8«,ll«H)-form [62870-78-4] DihydroeremofruUanolide
(2p,3a.,10a.H)-form [54878-93-2]
Constit. of Frullania dilatata. Cryst. (hexane). Mp 70- Cryst. (Et20). Mp 111.5°.
710. [1X]n + 108°.
3-Ac, 2-ange/oy/: [54878-89-6].
Asakawa, Y. eta/, Bull. Soc. Chim. Fr., 1976, 1465.
C22H300 5 M 374.476
Constit. of 0. spp. Oil.
Furanoeremophilane Sq-01434 3-Ac, 2-(3-methy/-2-butenoyl): [54878-90-9].
[6750-13-6] C22H3005 M 374.476
Constit. of 0. spp. Cryst. (pet. ether). Mp 114.SO. [1X]~4

W<
H -15.3° (c, 2.8 in CHCI 3).
2-Ange/oy/, 3-(3-methy/-2-butenoyl): [54878-88-5].
C25 H 340 5 M 414.541
Constit. of 0. spp. Oil.
CtsH220 M 218.338 2,3-Diange/oy/: [54911-15-8].
Constit. of Petasites a/bus, P. spurius, P. japonicus and C25H 340 2 M 366.542
Ligularia fischeri. Oil. Bp 16 148°. [1X]n - 8.4°. n~ 1.5172. Constit. of 0. spp. Oil.
9,10-Didehydro: [62787-33-1]. Furanoeremophil-9-ene Bohlmann, F. et a/, Chern. Ber., 1974, 107, 3928.

409
Furanoeremophilane-2,9-diol - Furanoeremophilane-6,10-diol Sq-01437 - Sq-01442

Furanoeremophilane-2,9-diol Sq-01437 Constit. of P. japonicus. Cryst. Mp 107-10H'. [1X]n

2,9-Dihydroxyfuranoeremophilane -60.5°.
(3p,6f,)-form [20016-50-6]
OH Japonicin
HO~o\ Cryst. Mp 196°. May be identical with Fur.mofukinol.

~
3-0-Ange/oy/: Angeloyljaponicin. Angelyljaponicin
C20H 280 4 M 332.439
Isol. from P. paradoxus. Noncryst.
C 15H 220 3 M 250.337 Novotny, L. eta/, Phytochemistry, 1968, 7, 1349 (Japonicin)
Nagano, H. eta/, Bull. Chern. Soc. Jpn., 1972, 45, 1935 (isol)
(2p,9fl)-form Bohlmann, F. eta/, Chern. Ber., 1974, 107, 3928 (iso[)
Furanopetasol Naya, K. eta/, Chern. Lett., 1978, 301 (struct)
2-Ange/oy/: [6902-62-1]. Furanopetasin Yamakawa, T. eta/, Chern. Pharm. Bull., 1979, 27, 1747 (synth)
C20H 280 4 M 332.439
Constit. of Petasites officianalis. Cryst. Mp 105-106°. Furanoeremophilane-3,9-diol Sq-01440
Novotny, L. eta/, Collect. Czech. Chern. Commun., 1964, 29, 1922; 3,9-Dihydroxyfuranoeremophi/ane
1987, 52, 1786 (isol, struct, cd)

Furanoeremophilane-2,1 0-diol
2,10-Dihydroxyfuranoeremophilane
Sq-01438
~0\
HO~
WQ
HO HO
C15H 220 3 M 250.337
(3p,9f/)-form [51117-10-3]
Cryst. Mp 187° dec. [1X]i,9 -24° (c, 0.5 in EtOH).
C15H2P 3 M 250.337
3-Ange/oy/: [51117-16-9].
(2p,IOf/)-form C20H 280 4 M 332.439
2-(Methylpropenoy/): [53820-40-9]. Constit. of Farfugium japonicum. Oil. [1X]ji -11 o (c, 0.8
C 1,H 260 4 M 318.412 in MeOH).
Constit. of Euryops abrotanifolius. Oil. 3-Ange/oy/, 9-(3-methy/-2-butenoyl): [51117-15-8].
10-Ange/oy/: [53820-35-2]. C 25H 340 5 M 414.541
C 20H 28 0 4 M 332.439 Constit. of F. japonicum. Oil. [IX]:,? + 17° (c, 1.5 in
Constit. of E. chrysanthemoides. Oil. MeOH).
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 2730. Nagana, H. eta/, Bull. Chern. Soc. Jpn., 1973, 46, 2840

Furanoeremophilane-3,6-diol Sq-01439 Furanoeremophilane-3,15-diol Sq-01441

3,15-Dihydroxyfuranoeremophi/ane

C15Hzz0 3 M 250.337
H~ CHpH
(3p,6f/)-form C 15H 2P 3 M 250.337
Furanofukinol 3P-form
Constit. of Petasitesjaponicus. Cryst. Mp 178-180°.
3,15-Diange/oy/: [54878-39-6].
6-Ac: [34335-95-0]. C 25H 340 5 M 414.541
C 17H 240 4 M 292.374 Constit. of Orthonna spp. Oil.
Constit. of P. japonicus. Viscous oil.
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 3928.
3-0-Ange/oy/:
C 20H 280 4 M 332.439
Constit. of Othonna spp. Oil. Furanoeremophilane-6,1 0-diol Sq-01442
6,10-Dihydroxyfuranoeremophi/ane
6-0-Ange/oyl:
C 20H 280 4 M 332.439

c;t2Q
OH
Constit. of P. japonicus. Viscous oil.
3-Ac, 6-0-ange/oy/: [38927-57-0].
C 22H 300 5 M 374.476
Constit. of Farfugium hiberniflorum. Viscous oil.
6-Ac, 3-0-ange/oy/: [54911-13-6]. OH
CzzH 300 5 M 374.476 C 15H 220 3 M 250.337
Constit. of 0. spp. Oil. (6p,JOf/)-form [35101-40-7]
6-0-Ange/oy/, 3-(3-methylthio-2Z-propenoyl): [34335-97-2]. Constit. of Ligularia japonica. Cryst. Mp 120-122". [1X]n
S-Furanopetasitin + 58° (EtOH).
C 1,H260 4S M 350.478 6-(2-Methy/propanoy/): [60410-89-1].

410
Furanoeremophilane-1,6,10-triol - Furanoeremophilan-6-ol Sq-01443 - Sq-01447

C 19H 280 4 M 320.428 Furanoeremophilan-2-ol Sq-01445

Constit. of Tetradymia glabrata. Cryst. (pet. ether). Mp 2-Hydroxyfuranoeremophilane
100-100.SO. [1X]n -56.1° (MeOH).
6-Angeloyl: [54878-42-1].
C 20H 28 0 4 M 332.439 HO~o)>
Constit. of Othonna spp. Cryst. (Et20jpet. ether). Mp
112°. [IX]~ -114.4° (c, 4.7 in CHC1 3).
6-(3-Methyl-2-butenoyl): [54878-41-0].
C 15H 220 2 M 234.338
~
C 20H 280 4 M 332.439
Constit. of Farfugium japonicum. Cryst. (pet. ether). Mp Angeloyl: [34335-98-3]. Furanojaponin
82-84°. [IX]~ -68° (c, 0.84 in MeOH). C20 H 280 3 M 316.439
Constit. of Petasites japonicus. Oil. Bp0 _00005 110-130°.
6-(3-Methyl-2-pentenoyl): [59806-64-3].
CltHJ004 M 346.466 Naya, K. eta/, Tetrahedron Lett., 1971, 2961.
Constit. of 0. heterophylla. Oil.
6-Me ether: [40267-27-4]. 6P-Methoxyfuranoeremophilan- Furanoeremophilan-3-ol Sq-01446
10P-ol 3-Hydroxyfuranoermophilane
C 16H 240 3 M 264.364
Constit. of L. japonica. Cryst. Mp 82-84°. [1Xln +5° (c, 2
in EtOH). r('yo)> (31X, 1OiXH)-form
Nagano, H. eta/, Bull. Chern. Soc. Jpn., 1973, 46, 2840 (isol)
Bohlmann, F. et a/, Chern. Ber., 1974, 107, 3928 (isol) HO'~
Tada, M. et a/, Bull. Chern. Soc. Jpn., 1974, 47, 1999 (isol)
C15H 220 2 M 234.338
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 1230 (isol)
Jennings, P.W. et a/, J. Org. Chern., 1976, 41, 4078 (isol) (3rx.,10rx.H)-form
3-Methyl-2-pentenoyl: [59742-05-1].
Furanoeremophilane-1,6,10-triol Sq-01443 C 21 H 300 3 M 330.466
Constit. of Senecio praecox.
HO

(f;Q
(3ft,JOPH)-form [51117-14-7]
Cryst. (pet. ether). Mp 79-80°. [1X]i;5 + 67° (c, 0. 7 in
MeOH).
2-Methylpropenoyl: [59806-17-6].
C 19H 260 3 M 302.413
OH Constit. of Othonna macrophylla. Oil.
C 15H 220 4 M 266.336 Angeloyl: [51117-17-0].
(lrx.,6P,JOfJ)-form [25274-06-0] Euryopsol C20H 280 3 M 316.439
Constit. of Euryops floribundus. Cryst. (EtOH). Mp 173- Constit. of Farfugium japonicum and 0. spp. Oil. [IX]~
1740. [1X]:J + W (c, 1.1 in EtOH). -38° (c, 1.3 in MeOH).
Rivett, D.E.A. et al, Tetrahedron, 1967, 23, 2431 (isol) Nagano, H. et al, Bull. Chern. Soc. Jpn., 1973, 46, 2840 (isol)
Eagle, G.A. et al, Tetrahedron, 1969, 25, 5227 (struct) Bohlmann, F. et al, Chern. Ber., 1974, 104, 3928; 1976, 109, 819,
Chalmers, A.A. et al, S. Afr. J. Chern., 1980, 33, I (crnr) 1230 (isol)

Furanoeremophilane-3,6,9-triol Sq-01444 Furanoeremophilan-6-ol Sq-01447

6-Hydroxyfuranoeremophilane
OH

H$
H

OH
Q)Q OH
C 25H 220 4 M 386.446 C 15Hu02 M 234.338
(3p,6rx.,9«,10PH)-form 6fl-form [4176-11-8] Petasalbin. Ligularol
6,9-Diangeloyl: [18142-27-3]. Kablicin Constit. of coltsfoot, Petasites a/bus and Ligularia
C25H 340 6 M 430.540 sibirica. Also P. spurius, P. japonicus and L. fischeri.
Constit. of Petasites kablikianus and P. paradoxus. Cryst. Mp 81-82°. [1X]n -11.2°.
Cryst. Mp 72°. [1X]i? -18.4°. Ac: [4467-60-1].
(3«,6/l)-form Ct 7H 240 3 M 276.375
Constit. of Lopholaena dregeana. Oil.
9-Ketone, 3-angeloyl, 6-(3-methyl-2-butenoyl):
C25H 320 6 M 428.524 Angeloyl: Albopetasin
Constit. of Senecio andreuscii. Needles. Mp 213-215°. C20H 300 2 M 302.456
[1X]i;5 -113.8° (CHC1 3). Constit. of P. a/bus and P. spurius. Cryst. Mp 106-107°.
[1X]D + oo.
Novotny, L. eta/, Tetrahedron Lett., 1968, 1041, 2281 (facing)
Reyes, B. eta/, Heterocycles, 1990, 31, 1405. 0-(3-Methyl-2-butenoyl):
C20H 280 3 M 316.439
Constit. of Farfugium japonicum. Oil.
Me ether: [34335-93-8]. 6fl-Metlwxyfuranoeremophilllne
C 16H 240 2 M 248.364

411
Furanoeremophilan-10-ol - Furanoeremophil-1(10)-ene-4,6-diol Sq-01448 - Sq-01453

Constit. of P. japonicus. Oil. Bp0.0004 90-100°. [ex]n Furanoeremophilan-9-one Sq-01451

-52.5°. Furanoeremophilone
6-Ketone: [4234-94-0]. Furanoeremophilan-6-one. Ligultuone
C 15H 11,01 M 232.322
Constit. of Ligularia sibirica and L. fischeri. Mp 64-65°.
[ex]~ -57.7° (c, 1 in CHC1 3).
Novotny, L. et al, Collect. Czech. Chern. Commun., 1964, 29, 2189
(struct)
Ishii, H. et al, Tetrahedron, 1965, 21, 2605 (isol, uv, ir, pmr, struct, C15H 100 1 M 232.322
synth)
Novotny, L. et al, Phytochemistry, 1966, 5, 1281 (occur)
lOrzH-form [6902-61-0]
Naya, K. et al, Tetrahedron Lett., 1971, 2961 (isol, ether) Constit. of Senecio aureus and Petasites hybridus. Cryst.
Nagaro, H. et pi, Bull. Chern. Soc. Jpn., 1973, 46, 4840 (isol) (C 6H 6 /hexane). Mp 150°. [oc)n + 0°.
Bohlmann, F. et al, Phytochemistry, 1977, 16, 1769 (isol) Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1976, 1487.
Sato, T. et al, Tetrahedron Lett., 1977, 3895 (cmr) YaJ;Dakawa, K. et al, Chern. Pharm. Bull., 1978, 26, 3704.
Tada, M. et al, Chern. Lett., 1979, 1441 (synth) Zalkow, L.H. et al, J. Chern. Soc., Perkin Trans. 1, 1979, 1542.
Yamakawa, K., Chern. Pharm. Bull., 1979, 27, 1747 (synth)
Miyashita, M. et al, J. Org. Chern., 1980, 45, 2945 (synth)
Jacobi, P.A. et al, J. Am. Chern. Soc., 1981, 103, 4611 (synth) Furanoeremophil-1(10)-ene-3,6-diol Sq-01452
3,6-Dihydroxyfuranoeremophil-1( 10)-ene
Furanoeremophilan-10-ol Sq-01448
10-Hydroxyfuranoeremophilane ~0~

q::q OH HO'~
OH
C 15Hzc,03 M 248.321
(3rz,6fl)-form [68773-29-5]
C 15Hn03 M 250.337 3oc,6P- Dihydroxyeuryopsin
Oil.
lOP-form [52279-13-7] Tetradymol
Toxic constit. of Tetradymia glabrata. Cryst. Mp 92- 1P,10P-Epoxide, 3-0-ange/oy/: [63366-05-2].
92.SO. [ex]~ + 56°. C10H 160 5 M 346.422
Constit. of Ligularia vorobierii. Oil.
Jennings, P.W. et al, J. Org. Chern., 1974, 39, 3392.
1P,10P-Epoxide, 3-0-ange/oy/, 6-0-Ac: [63366-03-0].
C11H 180 6 M 388.460
Furanoeremophilan-15,6-olide Sq-01449 Constit. of L. vorobierii. Oil. [ex]~ -19° (c, 1 in CHC1 3).

cbo
1P,10P-Epoxide, 3-(2-methy/-2-propenoyl): [63366-04-1 ).
C 1,H1.,05 M 332.3fJ6
Constit. of L. vorobierii. Oil. [ex]~ -4° (c, 0.02 in

fci \ CHC1 3).

1P,10P-Epoxide, 3-(2-methy/-2-propenoyl), 6-Ac: [63366-02-
9].
CnH160 6 M 374.433
C 15H 180 3 M 246.305 Constit. of L. vorobitrii. Oil.
6rz-form [70614-96-9] Bohlmann, F. eta/, Chern. Ber., 1977, 110, 1759 (isol)
Constit. of Ligularia hodgsoni. Cryst. (EtOAc). Mp 136- Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1135 (syntJI)
1380. [exJn -45° (c, 0.45 in dioxan).
[23849-98-1] Furanoeremophil-1(1 0)-ene-4,6-diol Sq-01453
Ishizaki, Y. et al, Bull. Chern. Soc. Jpn., 1979, 52, 1182. 4,6-Dihydroxyfuranoeremophil-1(10)-ene

Furanoeremophilan-1-one Sq-01450
~)
~0\ H~
~
C 15H 100 3 M 248.321
(4«,6/1)-form
C 15H 100 2 M 232.322 4ex,6P-Dihydroxyeuryopsin
lOrzH-form [52061-43-5] 6-(2-Methy/propanoyl): [53820-29-4].
Constit. of Smyrnium o/usatrum. Cryst. (pet. ether). Mp C 19H 160 3 M 302.413
72-73°. [ex]~ -51.5° (c, 2.8 in CHC13). From Euryops hebecarpus. Oil.
9,10-Didehydro: [62787-34-2]. Furanoeremophil-9-en-1-one 6-(2-Methy/butanoyl): [55050-45-8].
C15H 180 1 M 230.306 C:zoH180 3 M 316.439
Constit. of Senecio spp. Yellow oil. lsol. from Senecio e/egans. Oil.
Bohlmann, F. et a/, Chern. Ber., 1973, 106, 3614 (isol) 6-(3- M ethylbutanoyl): [53820-25-0].
Bohlmann, F. et al, Phytochemistry, 1977, 16, 135 (deriv) C10H 180 3 M 316.439
From E. hebecarpus. Oil.
6-(3-Methy/-2-butenoyl): [55050-46-9].

412
Furanoeremophil-1(10)-ene-2,9-dione- 10-Hydroxy-1,11(13)-eremophiladien-... Sq-01454- Sq-01459

C:zoll:u;03 M 314.424 Furanoeremophil-1-en-3-one Sq-01456

From S. elegans. Oil.
H

oW{
6-Tigloyl: [53820-41-0].
C 20H 260 3 M 314.424
From E. virgineus and S. elegans. Oil.
6-Angeloyl:
C20H 260 3 M 314.424
Constit. of E. hebecarpus. Oil. [IX]~ + 50.4° (c, 10 in CtsH 180 2 M 230.306
CHC1 3). lOtz.-form [16148-24-6] Furanoligularenone
IP,JOP-Epoxide, 6-(2-methylpropanoyl): [53820-30-7]. Constit. of Ligularia sp. and Senecio nemorensis. Cryst.
C 1,H260 4 M 318.412 Mp 95°. [1X]n + 3°.
Constit. of E. hebecarpus. Oil. Patil, F. et al, Bull. Soc. Chim. Fr., 1965, 3085 (iso{)
1,10-Epoxide, 6-(3-methylbutanoyl): [53859-44-2]. Jizba, J. et al, Collect. Czech. Chern. Commun., 1978, 43, 1113
C 20H 280 4 M 332.439 (isol, struct)
Constit. of E. abrotanifolius. Oil. Yamakawa, K. et al, Chern. Pharm. Bull., 1980, 28, 3265 (synth)
1,10-Epoxide, 6-angeloyl: [53820-36-3].
C 20H 260 4 M 330.423 Furanoeremophil-1(1 0)-en-9-one Sq-01457
Constit. of E. abrotanifolius. Oil. 9-0xoeuryopsin
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730, 2912 (iso{) [53820-68-1]

Furanoeremophil-1(1 0)-ene-2,9-dione
2,9-Dioxoeuryopsin
Sq-01454
~0\
[53820-34-1]
~
o~o, CtsHts02 M 230.306
Constit. of Euroyops hebecarpus. Cryst. (pet. ether). Mp

~
119-120°. [1X]~4 +0.35° (c, 1.3 in CHC1 3).
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730.

ctsH 1,03 M 244.290

Constit. of Euryops chrysanthemoides. Cryst. (Et20). Mp 8-Hydroxy-1(10),7(11)-eremophiladien- Sq-01458
198°. 12,8-olide
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730 (iso{)
OH
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1135 (iso{)

Furanoeremophil-1(10)-en-6-ol
6-Hydroxy-l ( 10)-furanoeremophilene
Sq-01455 ~0
C 15H 200 3 M 248.321
8tz.OH-form [128255-36-7] Palmosalide A
Constit. of Coelogorgia palmosa. Cryst. Mp 172-174°.
[1X]n + 155° (c, L1 in CHC1 3).
Weimer, D.F. et al, Tetrahedron Lett., 1990, 31, 1973 (isol, struct)
C 15H 200 2 M 232.322
6/l-form [65563-80-6]
10-Hydroxy-1,11(13)-eremophiladien-12,8- Sq-01459
6-Angeloyl: [40072-63-7]. 6P-Angeloyloxyeuryopsin
C:zoll 280 2 M 300.440 olide
Constit. of Euryops spp. Oil. [IX]~ +4.2° (c, 0.7 in
CHC1 3).
liX,lOIX-Epoxide, 6-Ac: [40072-65-9]. 6P-Acetoxy-11X,IOIX-
epoxyeuryopsin
Ct,H 220 4 M 290.358
Constit. of E. spp. Oil.
C 15H 200 3 M 248.321
liX,IOIX-Epoxide, 6-ange/oy/: [40072-64-8].
C 15H 200 3 M 248.321 (Bp,JOtz.)-form [122769-15-7]
Constit. of E. spp. Oil. [IX]~ -17.SO (c, 3.4 in CHC1 3). Constit. of Ondetia linear is. Oil.
IP,JOP-Epoxide, 6-angeloyl: [41929-09-3]. Senemorin 11X,21X-Epoxide: [122769-16-8]. ltz.,2tz.-Epoxy-10tz.-hydroxy-
Constit. of Senecio spp. Oil. [IX]~ -70.2° (c, 0.2 in 11(13)-eremophilen-12,8fl-olide
CHC1 3). C 15H 200 4 M 264.321
Constit. of 0. linearis. Oil.
Bohlmann, F. et al, Chern. Ber., 1972, 105, 3523 (iso{)
Novotny, L. et al, Collect. Czech. Chern. Commun., 1973, 38, 739 Zdero, C. et al, Phytochemistry, 1989, 28, 1653.
(iso{)
Bohlmann, F. et al, Chern. Ber., 1976, 109, 819 (iso{)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1135 (iso{)

413
8-Hydroxy-7(11)-eremophilene-... - 9-Hydroxyfuranoeremophilan-15,6-... Sq-01460 - Sq-01466

8-Hydroxy-7(11)-eremopbilene-12,8:14,• Sq-01460 8-Hydroxy-7(11 )eremopbilen-12,8-olide Sq-01463

s;r<o
diolide

Q:r{o
H OH
H HO

C15H 220 3 M 250.337

0 (BR,JOocH)-form
C15H 180 5 M 278.304 8-Et ether: [71973-20-1]. 8a-Ethoxy-7(ll)-eremophilen-
(6«,8/1)-form [58947-64-1] 12,8P-olide
Constit. of Ligu/aria fauriei. Cryst. (CHCI 3/C6H 6). Mp Ct,H160 3 M 278.391
253.5-254°. [ocJn +94° (c, 0.9 in CHCl 3). Constit. of Senecio aureus. Cryst. Mp 77-80°. Bp0 _3 185°.
Zalkow, L.H. et al, J. Chem. Soc., Perkin Trans. 1, 1979, 1542.
Moriyama, Y. et al, Bull. Chem. Soc. Jpn., 1976, 49, 3196.

2-Hydroxy-7(11)-eremopbilen-12,8-olide Sq-01461 10-Hydroxy-7(11)-eremopbilen-12,8-olide Sq-01464

HO'(t»o H

C 15H 220 3 M 250.337 C15H 110 3 M 250.337

2fl-form (Boc,JO/l)-form [130395-65-2]
Cryst. Mp 63°. [a]~ + 124.6° (c, 0.4 in CHC1 3). Constit. of Hertia cheirifolia. Cryst. (EtpfMeOH). Mp
Ange/oy/: Petasitolide A 164-165°. [ocJn -169° (c, 0.47 in CHCl 3).
C20H 280 4 M 332.439 Massiot, G. et al, Phytochemistry, 1990, 29, 2207 (isol, pmr, cmr)
Constit. of Petasites officina/is. Cryst. Mp 147°. [ocln
+48°.
3-Hydroxyfuranoeremopbilan-15-oic acid Sq-01465
Tigloy/: Petasitolide B
c~ 280 4 M 332.439
Constit. of P. officina/is. Cryst. Mp 146°. [ocln +31.8°.
0-(3-Methylthio-2E-propenoyl): S-Petasitolide A
C19H 21;04 S M 350.478
Constit. of P. officina/is. Cryst. Mp 199-200°. [ocln
-32.9°. C15H 200 4 M 264.321
0-(3-Methylthio-2Z-propenoyl): S-Petasitolide B 3fl-form
C 1,H160 4S M 350.478
Constit. of P. officina/is. Mp 201-202°. [ocln -15.3°. 3-Ange/oy/: [54878-37-4].
C20H 160 5 M 346.422
Novotny, L. et al, Tetrahedron Lett., 1961, 697 (isol) Constit. of Othonna spp. Amorph. solid.
Novotny, L. et al, Collect. Czech. Chem. Commun., 1964, 29, 2182
(is of) Bohlmann, F. et al, Chem. Ber., 1974, 107, 3928.
Kitahara, Y. et al, Chem. Lett., 1977, 1031 (struct)
9-Hydroxyfuranoeremopbilan-15,.olide Sq-01466
•Hydroxy-7(11)-eremopbilen-12,8-olide Sq-01462
6-Hydroxyeremophileno/ide OH

C15H 220 3 M 250.337 C15H 180 4

~
0
M 262.305
(6P,8«)-form [10250-03-0] (6«,9/l)-form
Constit. of Petasites a/bus, P. japonicus and Ligularia Ange/oyl: [64185-26-8]. Ligucahhaefolin
fischeri. Cryst. (Et 20). Mp 208°. [ocln + 205.8° (c, l in C20H 240 5 M 344.407
CHCl 3). Constit. of Ligularia calthaefolia. Oil.
Moriyama, Y. et al, Bull. Chem. Soc. Jpn., 1976, 49, 3196. Bohlmann, F. et al, Chem. Ber., 1977, 110, 2640.

414
2-Hydroxyfuranoeremophilan-9-one- 6-Hydroxyfuranoeremophil-1(10)-en-9-... Sq-01467- Sq-01471

2-Hydroxyfuranoeremophilan-9-one Sq-01467 C20H 260 4 M 330.423

2-Hydroxy-9-oxofuranoeremophilane Constit. of Senecio umbellatus. Oil.
3-Methylbutanoyl: [55050-52-7].
Ho C20H 280 4 M 332.439
HO~o\ Constit. of S. umbellatus. Oil.

~
3-Methylpentanoyl: [59742-00-6].
C21 H 300 4 M 346.466
Constit. of S. praecox. Oil.
C 15H 200 3 M 248.321 3-Methyl-2-pentenoyl: [59742-01-7].
(2rx.,10rx.H)-form C21 H 280 4 M 344.450
Angeloyl: [38836-41-8]. Constit. of S. praecox. Oil.
C20H 260 4 M 330.423 Methylpropenoyl: [24405-84-3].
Constit. of Petasites hybridus. Cryst. Mp 119-120°. C,9H240 4 M 316.396
Novotny, L. eta/, Phytochemistry, 1972, 11, 2795. Constit. of S. umbellatus. Cryst. (EtzO/pet. ether). Mp
95°.
3-Hydroxyfuranoeremophilan-9-one Sq-01468 3-Methyl-2-butenoyl: [59742-08-4].
C20 H 260 4 M 330.423
Constit. of S. praecox. Oil.

~0\ (6p,JOPH)-form [24405-68-3]

Cryst. (Etz0/C 6H 6). Mp 164-167°.
HO~~ 0-Methylpropenoyl: [53820-45-4].
Constit. of E. spathaceus. Cryst. (Et20jpet. ether). Mp
C,5H 200 3 M 248.321 109.5°.
(3rx.,l0rx.H)-form [15401-89-5] Euryopsonol 6-Ketone: [18452-51-2]. Furanoeremophilane-6,9-dione
Constit. of Euryops fioribundus. Cryst. (EtOH). Mp 230- C,5H 180 3 M 246.305
231°. [ex]!; -36° (c, 1.2 in CHC1 3). Constit. of S. lanceus. Oil. Bp 0 . 1 140°. [ex]i;' + 10° (c, 0.7
Ac: Cryst. (EtOH). Mp 197-198°. in CHC1 3).
2-Methylpropanoyl: Samek, Z. eta/, Collect. Czech. Chern. Commun., 1969, 34, 2792
C 19H 260 4 M 318.412 (struct)
Bohlmann, F. eta/, Chern. Ber., 1972, lOS, 3523; 1974, 107, 2912;
Constit. of E. spp. Cryst. (pet. ether). Mp 111°. 1976, 109, 819 (isol)
2-Methylpropenoyl: Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1976, 1487 (synth)
C 19H 240 4 M 316.396 Yamakawa, K. eta/, Chern. Pharm. Bull., 1981, 29, 3474 (synth)
Constit. of E. linifolius. Mp 144°.
3-Methylbutanoyl: 6-Hydroxyfuranoeremophil-1-en-9-one Sq-01470
C20H 280 4 M 332.439
Constit. of E. spp. Cryst. (pet. ether). Mp 111°. [ex]~4
-49.SO (c, 1.72 in CHC1 3).
Angeloyl: [53820-26-1]. ~0\
C20H 260 4 M 330.423
From E. hebecarpus. Cryst. (pet. ether). Mp 161-162°. ~
OH
3-Methyl-2-butenoyl:
C20H 260 4 M 330.423 C,sH180 3 M 246.305
Constit. of Senecio smithii. Cryst. (EtzO). Mp 195°. [ex]i;' (6P,l OPH)-form
-61.8° (c, 0.6 in CHC1 3). 0-(2-Methylpropanoyl): [18883-10-8]. lsoadenostylone
Rivett, D.E.A. eta/, Tetrahedron, 1967, 23, 2431 (struct) C 19H 240 4 M 316.396
Bohlmann, F. et a/, Chern. Ber., 1974, 107, 2730 (isol) Constit. of Adenostyles alliariae. Cryst. Mp 92-94°.
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1976, 1487 (synth) [exJn+ oo.
Pinder, A.R., Prog. Chern. Org. Nat. Prod., 1977, 34, 132 (rev) Samek, Z. et a/, Collect. Czech. Chern. Commun., 1969, 32, 2292.
Chalmers, A.A. et a/, S. Afr. J. Chern., 1980, 33, I (cmr)
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 2389 (isol)
6-Hydroxyfuranoeremophil-1(10)-en-9-one Sq-01471
6-Hydroxyfuranoeremophilan-9-one 6-Hydroxy-9-oxoeuryopsin
Sq-01469
6- Hydroxy-9-oxofuranoeremophilane

C 15H 200 3
~
M 248.321
OH C,sH 180 3 M 246.305
6p-form [62742-87-4]
(6p,JOrx.H)-form Constit. of Senecio lanceus. Oil. [ex]~4 -65° (c, l.l in
CHC1 3).
Ac: [24405-85-4]. Dihydrodecompositin
Ac: [24405-79-6]. Decompostin
C 17H 22 0 4 M 290.358
Constit. of Euryops spp. Oil. C,7H 200 4 M 288.343
Constit. of roots of Cacalia decomposita. Yellow cryst.
Angeloyl: [24405-77-4]. (Me 2C0jhexane). Mp 183-184°. [ex]~ +60° (CHC1 3).

415
6-Hydroxyfuranoeremophil-9-en-1-one - 2-0xo-1(10),11(13)-eremophiladien-... Sq-01472 - Sq-01475

Propanoyl: 6-Hydroxyfuranoeremophil-9-en-1-one Sq-01472

CtsH210 4 M 302.369 9,10-Dehydro-6-hydroxy-1-furanoeremophilanont'
Constit. of S. lanceus. Cryst. (Et20jpet. ether). Mp 96°.
[1X]i;l -67° (c, 0.4 in CHC1 3).
0-(2-Methylpropanoyl): [18883-09-5]. Adenostylone
C 19H 240 4 M 316.396
Constit. of Adenostyles alliariae.
0-(3-Methylbutanoyl): [59742-02-8].
C 20H 21;04 M 330.423
C 1sHts0 3 M 246.305
Constit. of S. praecox. Oil.
6ft-form [61520-27-2]
0-(3-M ethylpentanoyl):
Constit. of Senecio spp. Unstable yellow oil. [1X]~4 +93°
C 11H 280 4 M 344.450
(c, 3.2 in CHC1 3).
Constit.of S. praecox. Oil.
(2-Methylpropanoyl): [61520-28-3].
0-(2-Methyl-2-propenoyl): [53820-46-5].
C 19H 240 4 M 316.396
C 19H 21 0 4 M 314.380
Constit. of S. spp. Unstable yellow oil. [1X]i;l --52° (c, 1.3
Constit. of Euryops spathaceus. Oil.
in CHC1 3).
0-(3-Methyl-2-butenoyl): Angeloyl: [61520-29-4].
C 20H 24 0 4 M 328.407
C20H 240 4 M 328.407
From S. lanceus. Oil. Constit. of S. spp. Unstable yellow oil. [1X]i;l - 107° (c,
0-(3-Methyl-2-pentenoyl): [59742-04-0]. 3.9 in CHC1 3).
C 11 H 21;04 M 342.434
Bohlmann, F. et a/, Chern. Ber., 1976, 109, 3570.
Constit. of S. praecox. Oil.
0-(2,3-Epoxy-3-methylbutanoyl): [53820-37-4].
C 20H 240 5 M 344.407 8-Hydroxy-1-oxo-3,7(11 ),9- Sq-01473
Constit. of E. abrotanifolius. Cryst. (EtpjCHCl 3). Mp eremophilatrien-12,8-olide
194°. [1X]~4 -43.0° (c, 1.36 in CHC1 3).

~o'\::o
1p,1 op-Epoxide: 1p,1Ofl-Epoxy-6-hydroxyfuranoeremophil-
1(10)-en-9-one
Ct5H 180 4 M 262.305
Constit. of S. smithii. Cryst. (Etpjpet. ether). Mp 183°.
11X,l01X-Epoxide, Ac: [40072-67-l]. 11X,101X- ~
Epoxydecompositin . C 15H 160 4 M 260.289
C 17H 200 5 M 304.342 81;-form [84807-44-3]/stanbulin E
Constit. of E. spp. Cryst. (Et 20jpet. ether). Mp 185°. Constit. of Smyrnium creticum. Cryst. (EtOH). Mp 246-
[1X]i;l +OS (c, 1.2 in CHC1 3). 2480.
lfi,JOfi-Epoxide, 0-tigloyl: [55102-26-6]. Ulubelen, A. et a/, Phytochemistry, 1982, 21, 2128.
C 20H 240 5 M 344.407
Constit. of S. rigidus. Cryst. (Etpjpet. ether). Mp 103-
1050. 1-0xo-4(15),7(11)-eremophiladien-12,8- Sq-01474

<txro
lfi,JOP-Epoxide, 0-(3-methylpentanoyl): [59742-09-5].
olide
C 21 H 280 5 M 360.449
OH
Constit. of S. praecox. Oil.
1fi,10fi-Epoxide, 0-(3-methyl-2-butenoyl): (55050-51-6].
C 20H 240 5 M 344.407
Constit. of S. glastifolius. Cryst. (Etpjpet. ether). Mp
138-140°.
1fi,JOP-Epoxide, 0-(3-methyl-2-pentenoyl): [59742-1 0-8]. C 15H 180 3 M 246.305
C 11H 260 5 M 358.433 (8/;,lO«H)-form [71609-00-2]/stanbulin C
Constit. of S. praecox. Oil. Constit. of Smyrnium connatum. Cryst. Mp 178-180°.
Haqnatha, J. eta/, Collect. Czech. Chern. Commun., 1969, 34, 1739 Ulubelen, A. et a/, Phytochemistry, 1979, 18, 338.
(struct)
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1969, 34, 2792
2-0xo-1(10),11(13)-eremophiladien-12,8- Sq-01475
(abs config)
Bohlmann, F. eta/, Chern. Ber., 1972, 105, 3523; 1974, 107, 2730, olide
2912; 1976, 109, 819, 3570; 1977, 110, 474 (isol)
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1135 (synth)
Yamakawa, K. eta/, Chern. Pharm. Bull., 1981, 29, 3474; 1984, 32,
3396 (synth)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2389 (isol)

C 1sHts03 M 246.305
8ft-form [122769-14-6]
Constit. of Ondetia linearis. Oil.
Zdero, C. eta/, Phytochemistry, 1989, 28, 1653.

416
1-0xo-7(11)-eremophilen-12,8-olide- Warburgin Sq-01476 - Sq-01481

1-0xo-7(11 )-eremophilen-12,8-olide Sq-01476 Isol. from Hertia cheirifolia. Cryst. Mp 175-176°. [1X]n
-158° (c, 1.9 in CHC1 3).

/h~o'=o
Massiot, G. et a/, Phytochemistry, 1990, 29, 2207 (iso/, pmr, cmr)

1,2,6-Trihydroxyfuranoeremophilan-9-one Sq-01480
~ I HO H 0

H~
C 1 ~H 10 0 3 M 248.321
(4«.,5«.,8«.,JOPH)-form [12656-97-2]/stanbulin B
Constit. of Smyrnium olusatrum. Cryst. Mp 167°. [IX]~
+ 120.6° (M~OH).
Cox, P.J. eta/, Tetrahedron, 1980, 36, 3437 (cryst struct) C 1 ~H 10 0~ M 280.320
Budesinsky, M. et a/, Collect. Czech. Chern. Commun., 1984, 49,
1311 (abs config) (1 «.,1«.,6P,l O«.H)-form
1-(3-M ethyl-2-butenoyl), 6-(methylpropanoyl): [62706-48-3].
3,6,8,1 0-Tetrahydroxy-7(11 )-eremophilen- Sq-01477 C24H 320 7 M 432.513
Constit. of Senecio panduriformis. Cryst. (Et20jpet.
12,8-olide ether). Mp 90°. [1X]~4 -92° (c, 0.94 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 474.

Warburgin Sq-01481
[10208-62-5]

C 1 ~H 21 0 6 M 298.335 ('Ylr-)
(3fJ,6p,8r~.OH,IOfl)-form
0~00Me
8-Me ether, 3-angeloyl: [130395-62-9]. 3P-Angeloyloxy-
6P,l OP-dihydroxy-8«.-methoxy-7(11)-eremophilen-12,8P- Ct6H 160 4 M 272.300
olide Constit. of heartwood of Warburgia ugandensis. Yellow
C21H300 7 M 394.464 cryst. by subl., unstable towards air and light. Mp 159-
lsol. from Hertia cheirifolia. Cryst. Mp 199-200°. [1X]n 1610. [1X]n + 120° (CHCI 3).
-126° (c, 0.5 in CHC1 3). Brooks, C.J.W. et a/, Tetrahedron, 1969, 25, 2865.
Massiot, G. eta/, Phytochemistry, 1990, 29, 2207 (iso/, pmr, cmr)

3,8, 10-Trihydroxy-7(11 )-eremophilen-12,8- Sq-01478

olide

C 1 ~H 21 0~ M 282.336
(3P,8«.0H,10fl)-form
8-Me ether, 3-angeloyl: [130395-61-8]. 3P-Angeloyloxy-10P-
hydroxy-8«.-methoxy-7(11)-eremophilen-12,8P-olide
C21H 300 6 M 378.464
lsol. from Hertia cheirifolia. [1X]n -33° (c, 0.4 in
CHCI 3).
Massiot, G. eta/, Phytochemistry, 1990, 29, 2207 (isol, pmr, cmr)

6,8,10-Trihydroxy-7(11)-eremophilen-12,8- Sq-01479
olide

C 1 ~H 21 0~ M 282.336
(6P.SPOH,l Ofl)-form
8-Me ether: [130395-63-0]. 6p,JOP-Dihydroxy-8P-methoxy-
7(11)-eremophilen-12,8«.-olide
C 16 H 24 0~ M 296.363

417
4,5-Didebydro-6-hydroxy-5,6-... - Senglutinosin Sq-01482 - Sq-01488

8-Epimer, 6-0-tigloyl:
C20H 260 6 M 362.422
Seco- and Constit. of S. macrotia. Gum (as acetate).
6-(3-Methylbutanoyl):
C20H 280 6 M 364.438
abeoeremophilanes Constit. of S. macrotis. Gum (as acetate). [cx]i;' +46° (c,
0.1 in CHC1 3) (as acetate).
8-Epimer, 6-(3-methylbutanoyl):
C20H 280 6 M 364.438
Constit. of S. macrotis. Gum (as acetate).
4,5-Didehydro-6-hydroxy-5,6- Sq-01482 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1155.
secoeuryopsin
Norsecoglutinosone Sq-01485
[126199-40-4]

C1sH200 2 M 232.322
A secofuranoeremophiladiene.
Angeloyl: [53820-28-3]. 6-Angeloyloxy-4,5-didehydro-5,6-
secoeuryopsin
;.D:rn,
0
C20H:u;03 M 314.424 Ct4H 180 4 M 250.294
Constit. of Euryops hebecarpus. Unstable oil. Constit. of Senecio glutinosus. Oil.
Bohlmann, F. eta/, Chem. Ber., 1974, 107, 2730. Zdero, C. eta/, Phytochemistry, 1989, 28, 3532 (isol, pmr)

8-Hydroxy-6-methoxy-3,4,5- Sq-01483 Secoeurabicanal Sq-01486

trimethylnaphtho[2,3-b]furan-9(4H)-one y,3,5- Trimethylbenzofuranbutanal, 9CI
[125363-01-1] [121817-55-8]

/yy)
OH~H3CVL-(
CtsH180 2 M 230.306
C16H 160 4 M 272.300 Constit. of Euryops arabicus.
Constit. of Senecio linifolius. Orange cryst. Hafez, S. eta/, Phytochemistry, 1989, 28, 843.
(EtOAcjhexane). Mp 129°. [cxln + 53° (c, 0.2 in CHC1 3).
4-Hydroxy: [125340-15-0]. 4,8-Dihydroxy-6-methoxy-3,4,5- Secoeurabicol Sq-01487
trimethylnaphtho[2,3-blfuran-9(4H)-one cx-2-Butenyl-3,5-dimethyl-6-benzofuranmethanol, 9CI
C 16H 160s M 288.299 [121817-54-7]
Constit. of S. linifolius. Yellow cryst. (EtOAc/hexane).
Mp 208°. [cxln + 17° (c, 0.5 in CHC1 3). OH
Torres, P. eta/, Phytochemistry, 1989, 28, 3093 (isol, pmr)

6-Hydroxysecomacrolide Sq-01484

r l H O H}-o\._ C1sH 180 2 M 230.306

Constit. of Euryops arabicus. A seco-furoeremophilane.
~0 Hafez, S. eta/, Phytochemistry, 1989, 28, 843.
OH
C 1sH:zoOs M 280.320 Senglutinosin Sq-01488
6P-form [126199-38-0]
6-0-Angeloyl:
C:zoH 260 6 M 362.422
Constit. of Senecio macrotis. Gum (as acetate). [cx]i;'
+ 110.6° (c, 0.3 in CHC1 3) (acetate).

r
8-Epimer, 6-0-angeloyl:
C20H 260 6 M 362.422
ooc
Constit. of S. macrotis. Gum (as acetate).
6-0- Tigloyl: C20H 240 3 M 312.408
C:zoH 260 6 M 362.422 Constit. of Senecio glutinosus. Oil.
Constit. of S. macrotis. Gum (as acetate). [cx]i;' + 130° (c,
0.2 in CHC1 3) (acetate). Zdero, C. eta/, Phytochemistry, 1989, 28, 3532 (iso/, pmr)

418
5,6,9,10-Tetradehydro-1,4:3,14-... - 14-Nordehydrocalohastine Sq-01489 - Sq-01495

5,6,9~1 0-Tetradehydro-1,4:3, 14-diepoxy-4- Sq-01489 8-Hydroxy-6-methoxy-3,5- Sq-01492

hydroxy-4,5-secofuranoeremophilane dimethylnaphtho(2,3-b]furan-4,9-dione
5,7,8,10-Tetrahydro-3,8-dirnethyl-7,10-rnethanofuro[2,3- [125340-16-1]
i][2,5]benzodioxocin-8-ol, 9CI
[53820-32-9]

C 15H 120 5 M 272.257

Constit. of Senecio linifolius. Red needles (Me 2CO). Mp
CISHI604 M 260.289
260°.
Constit. of Euryops hebecarpus. Oil. }.max 250, 275, 281 nm.
Torres, P. et al, Phytochemistry, 1989, 28, 3093 (isol, pmr)
Bohlmann, F. et al, Chern. Ber., 1974, 107, 2730.

6-Hydroxy-11,12,13-trinor-1(10),7- Sq-01493
eremophiladiene-2,9-dione

ow
4,4a,5,6- Tetrahydro-4-hydroxy-4a,5-dirnethyl-1 ,7-

Noreremophilanes naphthelenedione, 9CI

Dendryphiellin A Sq-01490
I OH
[113592-81-7]
C 12H 140 3 M 206.241
(4rx.,5rx.,6if>-form [38226-98-1] Narchinol A
Constit. of Nardostachys chinensis. Yellow cryst.
(EtOAc). Mp 146-148°.
Ac: [38236-33-8].
Yellow needles (EtOAc). Mp 96.5-98°.
C 21 H 280 5 M 360.449 Hikino, H. et al, Phytochemistry, 1972, 11, 2097 (isol, uv, derivs)
Meta b. of Dendryphiella salina. Oil. [1X]i? + 571.1° (c, 0.31
in EtOH).
1-Hydroxy-11,12,13-trinor-9- Sq-01494
6'-Hydroxy, 8'-deoxy: [121678-86-2]. Dendryphiellin B eremophilen-8-one
C 21 H 280 5 M 360.449
4,4a,5,6,7,8-Hexahydro-8-hydroxy-4a,5-dirnethyl-2(3H)-
Metab. of D. salina. Oil. [1X]i? +280° (c, 0.05 in EtOH).
naphthalenone, 9CI. 1-Hydroxyisoondetianone
8'-Deoxy: [121661-41-4]. Dendryphiellin C
C 21 H 28 0 4 M 344.450
Metab. of D. salina. Oil. [1X]i? + 506.9° (c, 0.41 in
MeOH). Has (6' S)-config.
9' -Hydroxy, 8' -deoxy: [121678-87-3]. Dendryphiellin D
C21H280S M 360.449
Metab. of D. salina. Oil. [1X]i? +349.1° (c, 0.092 in
EtOH). C 12H 180 2 M 194.273
Guerriero, A. et al, Helv. Chim. Acta, 1988, 71, 57; 1989, 72, 438 1«-form [122872-02-0]
(isol, pmr, cmr, uv, cd) Constit. of Ondetia linearis. Oil. [1X]i;' + 140° (c, 0.27 in
CHC1 3).
2,10-Dihydroxy-11,12,13-trinor-6- Sq-01491 Zdero, C. et al, Phytochemistry, 1989, 28, 1653.
eremophilen-8-one
4a,5,6,7,8,8a-Hexahydro-7,8a-dihydroxy-4a,5-dirnethyl- 14-Nordehydrocalohastine Sq-01495

HO,Wo
2( 1H)-naphthalenone, 9CI. 2,10-Dihydroxyondetianone 9-Methoxy-3,5-dirnethylnaphtho[2,3-blfuran. 9-Methoxy-14-
norfuranoerernophilane
OH [125340-14-9]

C 12H 180 3 M 210.272

(1«,10/1)-form [122769-18-0]
Constit. of Ondetia linearis. Cryst. Mp 148°. [1X]~4 +27° CISHI402 M 226.274
(c, 0.23 in CHC1 3). Cons tit. of Senecio linifolius. Oil.
Zdero, C. et al, Phytochemistry, 1989, 28, 1653. Torres, P. et al, Phytochemistry, 1989, 28, 3093 (isol, pmr)

419
11,12,13-Trinor-1(10)-eremophilen-7-... - 1(10),8-Aristoladien-2-one Sq-01496 - Sq-01501

11,12,13-Trinor-1(10)-eremophilen-7-one Sq-01496 Struct. revised in 1982, formerly thought to be a

3,4,6,7,8,8a-Hexahydro-8,8a-dimethyl-2(1H)-naphthalenone, Muurolene (decalin) deriv. Constit. of Chiloscyphus
9CJ pa/lescens and C. potydnthus. Oil. Bp 2 121-122°. [ex]i;"
-45.7° (c, 1 in dioxan).
2,4-Dinitropheny/hydrazone: Cryst. Mp 174-175°.
Matsuo, A., Tetrahedron, 1972, 28, 1203 (isol)
Gras, J.-L., J. Org. Chern., 1981, 4Ci, 3738 (synth)
Connolly, J.D. et al, J. Chern. Soc., Chern. Commun., 1982, 1236
(struct)
C 12H 180 M 178.274 Gerling, K.-G. et a/, Tetrahedron Lett., 1985, 26,. 1293 (synth)
(4«.5«)-form [39850-88-9] Tori, M. et al, J. Chern. Soc., Perkin Trans. 1, 1989, 1552 (abs
Constit. of the oil of Vetiveria zizanioides. Oil, cryst. on config)
standing. Mp 27.SO. [ex]~ + 101.2° (c, 1.2 in CHC1 3). Tori, M. eta/, Bull. Chern. Soc. Jpn., 1990, 63, 1706 (synth)
Semicarbazone: Mp 210-210.5°.
[51608-12-9, 55102-28-8]
Maurer, B. et al, Helv. Chim. Acta, 1972, 55, 2371.

11,12,13-Trinor-6,9-eremophiladien-8-one Sq-01497
5,6,7,8-Tetrahydro-4,4a-dimethyl-2(4aH)-naphthalenone, 9CI
Aristolanes
[74410-98-3]

1,9-Aristoladiene Sq-01500
[34143-96-9]

C 12H 160 M 176.258

Constit. of Senecio humillimus. Oil. [ex]~4 -12.4° (c, 1 in
CHCl 3). .

Bohlmann, F. et a/, Phytochemistry, 1981, 20, 1739.

CuH22 M 202.339
Constit. of Nardostachys chinensis. Oil.
Riicker, G. et al,Justus Liebigs Ann. Chern., 1971, 748, 214.

Chiloscyphane group 1(10),8-Aristoladien-2-one

[22391-34-0]
Sq-01501

L;Q
OH

Chiloscypholone Sq-01498
[84507-58-4]

C1 5H 200 M 216.322
Constit. of Nardostachys chinensis. Oil. [ex]~ +23° (c, 4.3
in CHCl 3).
8,9-Dihydro, 9<;-hydroxy: [26808-51-5]. 9-Hydroxy-1(10)-
aristo/en-2-one. Debilone
C 15H 140 2 M 236.353 C15H220 2 M 234.338
Constit. of Chiloscyphus pallescens. Cryst. Mp 93-94°. [exln Constit. of Aristolochia debilis. Cryst. (2-propanol). Mp
+53.9° (c, 0.86 in CHCl 3). 135°.
Connolly, J.D. et al, J. Chern. Soc., Chern. Commun., 1982, 1236 8,9-Dihydro, 9ex-hydroperoxy: 9«.-Hydroperoxy-1(10)-
(isol, struct) aristolen-2-one
Tori, M. eta/, J. Chern. Soc., Perkin Trans. 1, 1989, 1552 (abs C15H220 3 M 250.337
config) Constit. of A.debilis. Cryst. (Et20). Mp 140°.
Riicker, G. eta/, Justus Liebigs Ann. Chern., 1968, 717, 221; 1971,
Chiloscyphone Sq-01499 748, 211.
[23538-45-6] Riicker, G. et al, Phytochemistry, 1984, 23, 1647.

M 218.338

420
1(10)-Aristolen-12-al- 1,10-Epoxy-8,9-aristolanedione Sq-01502 - Sq-01509

1(10)-Aristolen-12-al Sq-01502 9-Aristolen-8-one Sq-01507

[94271-19-9] Aristolone
[25274-27-5]

C13H 22 0 M 218.338
Constit. of Aristolochia debilis. Cryst. (Etp). Mp 65°. C13H220 M 218.338
Rucker, G. eta/, Phytochemistry, 1984, 23, 1647. Constit. of Aristolochia debilis. Cryst. Mp 100-101°. [IX]~
-339.4°.
1(10)- Aristolene Sq-01503 liX-Hydroxy: liT.-Hydroxy-9-aristolen-8-one
P-Gurjunene CtsH2202 M 234.338
Constit. of A.debilis. Cryst. (Et 20fpentane). Mp 134°.
[17334-55-3]
Buchi, G. eta/, Tetrahedron Lett., 1962, 827 (pmr, abs con.fig)
Piers, E. et at, Can. J. Chern., 1969, 47, 4307 (synth)
Allen, F.H. eta/, Acta Crystallogr., Sect. B, 1973, 29, 1451 (cryst
struct)
Absolute Rucker, G. et a/, Phytochemistry, 1984, 23, 1647 (deriv)
configuration

C13H24 M 204.355
1,10-Epoxy~aristolane Sq-01508
Constit. of, inter alia, gurjun balsam. Oil. Bp 13 120-123°. [87332-34-1]
[1X]i,O +81.8°.
Coates, R.M. eta/, J. Chern. Soc., Chern. Commun., 1968, 515
(synth, bib[)

9-Aristolene Sq-01504
C13H 24 M 204.355
CtsH240 M 220.354
(+)-form [27862-07-3]
Constit. of the sea pen Scytalium splendens. Oil. [1X]i;
ent-9-Aristolene. 11.-Ferulene
-24.1 o (c, 0.332 in CHC1 3).
Constit. of Ferula communis. Oil. Bp8 110°. [1X]n +68°
(neat). Do, M.N. et at, J. Org. Chern., 1983, 48, 4410.
(-)-form [6831-16-9] Aristolene
Constit. of calarene from sweet flag oil and essence of 1,10-Epoxy-8,9-aristolanedione Sq-01509
nard (Nardostachys jatamansi). Oil. [1X]n -98.7° (neat).
Pesnelle, P. et a/, Bull. Soc. Chim. Fr., 1963, 912 (isol)
Carboni, S. eta/, Tetrahedron Lett., 1965, 3017 (isol)
Weinheimer, A.J., J. Chern. Soc., Chern. Commun., 1968, 1070
(is of)

9-Aristolen-1-ol Sq-01505
C13H 240 M 220.354 C13H 200 3 M 248.321
liZ-form [26128-14-3] (JIT.,l01Z)-form [117634-64-7] Kanshone C
Constit. of Nardostachys chinensis. Cryst. Mp 85°. [1X]i; Constit. of Nardostachys chinensis. Yellow needles. Mp
+ 35.9° (c, 5.3 in CHC1 3). 136-137°. [1X]n -13.4° (c, 0.4 in CHC13).
Teisseire, P. et at, Recherches, 1969, 17, 121 (synth) Bagchi, A. eta/, Phytochemistry, 1988, 27, 2877.
Rucker, G. et at, Justus Liebigs Ann. Chern., 1971, 748, 214 (isol)

1(10)-Aristolen-9-one Sq-01506
Gansongone
[114339-93-4]

C13H 22 0 M 218.338
Constit. of Nardostachys chinensis. Oil. [1X]i,O +20° (c, 2.0
in CHC1 3).
Shide, L. et a/, Planta Med., 1987, 53, 556.

421
11,12-Epoxy-1(10)-nardosinene- Lemnalactone Sq-01510 - Sq-01515

Constit. of N. chinensis. Gum. [1X]n -42.2° (c, 1.29 in

CHC1 3).
Nardosinanes Deoxy: [27062-01-7]. Isonardosinone
Ct5H 120 3 M 250.337
Constit. of N. chinensis, Cryst. [a]i,O + 13.2° (c, 0.85 in
CHC1 3).
[50340-19-7]
11,12-Epoxy-1(10)-nardosinene Sq-01510 Riicker, G. et al, Justus Liebigs Ann. Chern., 1970, 733, 152
(Isonardosinone)
Riicker, G. et al, Phytochemistry, 1974, 13, 1907 (con.fig,
lsonardosinone)
Bagchi, A. et al, Phytochemistry, 1988, 27, 3667 (Kanshones)

Lemnacarnol Sq-01514
C 15Hz..0 M 220.354 [55890-26-1]
Constit. of Phyllogorgia dilatata. Oil. [aln -62° (c, 1 in
CHC1 3).
Kelecom, A. et al, J. Nat. Prod. (Lloydia), 1990, 53, 750 (isol)

Kanshone A Sq-01511
[115356-18-8]
C 15H 240 3 M 252.353

9i
Constit. of Lemnalia carnosa. Cryst. (EtzO). Mp 160-163°.
2-Ketone: 2-0xolemnacarnol
Ct 5H 120 3 M 250.337
Constit. of P.fu/vum. Oil. [1X]n +9° (c, 0.26 in MeOH).
2-Deoxy: [63043-65-2]. 2-Deoxylemnacarnol
Ct 5H 240 1 M 236.353
OH Constit. of L. africana and Paralemnalia thyrsoides.
Cryst. Mp 101-103°. [1X]n -165° (c, 0.1 in CHC1 3).
C 15H 120 1 M 234.338
Constit. of Nardostachys chinensis. Oil. [1X]n -147.8° (c, 2-Deoxy, 12-oxo: [63043-66-3]. 2-Deoxy-12-oxolemnacarnol
0.35 in CHC1 3). Constit. of P. thyrsoides. Cryst. (1X]n -20° (CHC1 3).
Bagchi, A. et a[, Phytochemistry, 1988, 27, 1199. Tursch, B. eta[, Bull. Soc. Chim. Be/g., 1975, 84, 81 (isol)
Karlsson, R. et al, Acta Crystallogr., Sect. B, 1976, 32, 1614 (abs
con.fig)
Kanshone B Sq-01512 Losman, D. eta[, Acta Crystallogr., Sect. B, 1977, 33, 1959 (cryst
[115370-61-1] struct, deriv)
Daloze, D. et al, Bull. Soc. Chim. Belg., 1977, 86, 47 (2-
Deoxylemnacarnol, 2- Deoxy-12-oxolemnacarnol)

HO~O
Bowden, B.F. eta[, Tetrahedron Lett., 1980, 3105 (isol)

Lemnalactone Sq-01515
I 0 [63043-49-2]
I I
0
C 15H 120 4 M 266.336
Constit. of Nordostachys chinensis. Needles. Mp 137-138°.
[1X]n + 133.8° (c, 1.1 in CHC1 3).
Bagchi, A. et al, Phytochemistry, 1988, 27, 1199.
C 15H 1z01 M 234.338
Kanshone D Sq-01513 Constit. of Paralemnalia digitiformis. Cryst. Mp 105-106°.
[119403-26-8] [aJn -240° (c, 0.3 Jn CHC1 3).
7-Epimer: [72541-01-6]. 7-Epilemnalactone
Constit. of P. digitiformis. Cryst. Mp < 30°. [1X]n -84°
(c, 0.6 in CHC1 3).
HO2 Y : ? O0
Ahond, A. et al, Bull. Soc. Chim. Belg., 1979, 313.
I Ahond, A. et al, Tetrahedron Lett., 1979, 1879.
I

OH
C 15H 120 4 M 266.336
Constit. of Nardostachys chinensis. Needles. Mp 152-153°.
[1X]n + 57.9° {c, 0.52 in CHC1 3).
2-Ketone: [119403-27-9]. Kanshone E
CtsH 200 4 M 264.321

422
Lemnaliadione- 2,5-Epoxy-1(6)-brasilen-9-ol Sq-01516 - Sq-01521

Lemnaliadione Sq-01516

Brasilanes

1(6)-Brasilen-2-ol Sq-01519
C 14H 21,03 M 236.310
Constit. of Paralemnalia thyrsoides and Lemnalia africana. OH

60-(2a,9~),(o'm
Cryst. Mp 87-89°. [exJn -298° (c, 1.0 in CHCl 3).
Izac, R.R. eta/, Tetrahedron Lett., 1982, 23, 817.

Nardonoxide Sq-01517 I

[111514-48-8] ~
C 15H 21;0 M 222.370
(2rx.,9fl)-form [70000-41-8] 2-Epibrasilenol. 2-epi-Brasilenol
C15H 160 . M 222.370
From Aplysia brasiliana. Oil. [ex]i,l +96° (c, 1.05 in
CHCl 3).
(2p,9fl)-form [70000-39-4] Brasilenol
Constit. of A. brasiliana. Cryst. Mp 55-56°. [ex]i,l +33.4°
(c, 1.6 in CHCl 3).
CISHlOOl M 232.322
Constit. of Nordostachys chinensis. Cryst. (MeOH). Mp 62- Ac:
640. [ex]~ -85° (c, 0.65 in CHCl 3). C17H 180 1 M 264.407
Constit. of A. brasi/iana. Oil.
Shide, L. et a/, Planta Med., 1987, 53, 332.
Stallard, M.O. et a/, Tetrahedron, 1978, 34, 2077 (isol, struct)
Greene, A.E. eta/, J. Org. Chern., 1986, 51, 4250; 1987, 52, 1169
Nardosinone Sq-01518 (synth, abs config)
[23720-80-1]
5,9-Dihydroxy-1(6)-brasilen-7-one Sq-01520

HO~

~H
Absolute
configuration

C 15Hzz03 M 250.337 ~
Constit. of Nardostachys chinensis. Cryst. Mp 108-110°. C 15Hzz01 M 234.338
[ex]~ + 103° (c, 3.02 in CHCl 3). (5ft,9rx.)-form
Riicker, G. eta/, Arch. Pharrn. (Weinheirn, Ger.), 1975, 308, 858 Metab. of Laurencia obtusa. Cryst. (Etpjcyclohexane).
(conforrnn) Mp 126-128°. [ex]i; +7.1° (c, 3 in EtOH).
Riicker, G., Justus Liebigs Ann. Chern., 1975, 311 (struct, abs Caccamese, S. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 1287 (isol,
conjig) prnr, crnr, cryst struct)
Friemann, J. eta/, Justus Liebigs Ann. Chern., 1981, 2057 (cryst
struct, abs conjig)
2,5-Epoxy-1(6)-brasilen-9-ol Sq-01521

C 15H 140 1 M 236.353

(2P,5P,9fl)-form
Metab. of Laurencia obtusa. Cryst. (Etpjcyclohexane).
Mp 121-123°. [ex]i; +5.0° (c, 2.5 in EtOH).
Caccmese, S. eta/, J. Nat. Prod. (Lioydia), 1990, 53, 1287 (isol,
prnr, crnr)

423
Adenostin A - Cacalone Sq-01522 - Sq-01527

Cacalol Sq-01525

Cacalol group
[24393-79-1]

~0)
Adenostin A Sq-01522
~ 14 13

(100853-39-2] CtsH180 1 M 230.306

Constit. of Cacalia decomposita. Cryst. (Et20/pentane).
Mp 92-94°. [ex]~ + WO (CHC1 3).
Ac:
C 17H 100 3 M 272.343
Constit. of C. spp. Cryst. (Me 2COfhexane). Mp 103.5-
104.50. (ex] 0 -96.SO (c, 1 in CHC1 3).
3-Methy/-2-butenoy/:
C 10H 260 3 M 314.424
lsol. from C. spp. [cx]n + 17° (c, l in CHC1 3).
13-Acetoxy: (100853-40-5]. Adenostylol
c~ 3404 M 458.596 C 17H 100 4 M 288.343
Constit. of Cacalia adenostyloides. Needles Constit. of C. adenostyloides. Oil. (ex]~ +33.3° (c, 0.12 in
(CHC1 3fhexane). Mp 186-188°. [ex)~ -2.4° (c, 0.5 in CHC1 3).
CHC1 3). Deoxy, 1-oxo: [71047-11-5]. 1-0xo-9-deoxycacalol
Kuroyanagi, M. et al, Chem. Pharm. Bull., 1985, 33, 4792. C1 5HI,o1 M 228.290
Constit. of Senecio serratifolius. Oil.
Adenostin B Sq-01523 14-0xo: [65080-19-5]. Cacalal
CtsHt,03 M 244.290
[100853-41-6]
Constit. of C. delphiniifolia. Cryst. Mp 155-156°. [a:]n
+ 136° (c, 0.92 in CHC1 3).
2,14-Dihydroxy: see 2,14-Dihydroxycaca/o/, Sq-01532
3,14-Dihydroxy: see 3,14-Dihydroxycaca/ol, Sq-01533
1,2-Didehydro: see Demethylcacalohastine, Sq-01531
1,13-Dioxo: see Viteralone, Sq-01534
Naya, K. et al, Chem. Lett., 1976, 73; 1977, 1179 (isol)
Inouye, Y. et al, Bull. Chem. Soc. Jpn., 1977, 50, 961 (synth)
Terabe, M. et al, Bull. Chem. Soc. Jpn., 1978, 51, 661 (abs config)
Huffman, J.W. et al, J. Org. Chem., 1979, 44, 1851 (synth)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 125 (1-0xo-9-
deoxycacalol)
Kuroyanagi, M. et al, Chem. Pharm. Bull., 1985, 33, 4792
(Adenostylol)
Hafez, S. et al, Phytochemistry, 1989, 28, 843
C311H 340 4 M 458.596 (Didehydrodesoxycacalohastine)
Constit. of Cacalia adenostyloides. Cryst. (hexane). Mp
202-205°. [cx]~ -158.3° (c, 1.0 in CHC1 3).
Cacalolide Sq-01526
Kuroyanagi, M. et al, Chem. Pharm. Bull., 1985, 33, 4792.
[58879-96-2]
Adenostylide Sq-01524

W
[100853-42-7]
OH 0
0
:::::,... C 15H 180 3 M 246.305
Constit. of Cacalia spp. Yellow prisms. Mp 158-159.SO.
OH (a:)n + 18° (c, 1.03 in MeOH).
C 15H 180 4 M 262.305 Naya, K. et al, Chem. Lett., 1976, 73; 1977, 1179 (isol, struct)
Constit. of Cacalia adenostyloides. Amorph. powder. Mixt.
of epimers at C-6. Cacalone Sq-01527
Di-Ac: Cryst. (MeOH). Mp 155-156°. [ex]~ + 19.2° (c, 1.3 5,6,7,8-Tetrahydro-4-hydroxy-3,4,5-trimethylnaphtho[2,3-
in MeOH). b)furan-9(4H)-one, 9CI
Kuroyanagi, M. et al, Chem. Pharm. Bull., 1985, 33, 4792. (26294-92-8]

424
Cacalonol- 2,14-Dihydroxycacalol Sq-01528 - Sq-01532

C15H 180 3 M 246.305 Demethylcacalohastine Sq-01531

Constit. of Cacalia decomposita. Cryst. (Me 2CO/hexane). 1,2-Didehydrocaca/o/
Mp 120-121°. [1X]n +84o (CHC1 3).
6-Epimer: [60428-00-4]. Epicacalone
C 15H 180 3 M 246.305
Constit. of C. spp. Cryst. (diisopropyl etherjMe 2CO).
Mp 129.5-131°. [IX]~ +95° (c, 0.98 in CHC1 3).
Yuste, F. eta/, J. Org. Chern., 1976, 41, 4103 (struct)
Casares, A. eta/, Tetrahedron Lett., 1976, 2485 (struct)
C 15Ht 60 2 M 228.290
Omura, K. eta/, Chern. Lett., 1978, 1257 (isol) Me ether: [52078-95-2]. Caca/ohastine
Kuroyanagi, M. eta/, Chern. Pharm. Bull., 1985, 33, 4792 (isol) C 16H 180 2 M 242.317
Soriano-Garcia, M. eta/, Acta Crystallogr., Sect. C, 1988, 44, Constit. of Cacalia hastata. Cryst. Mp 84-85.5°. [1X]n
1092 (cryst struct) +90.SO (c, 0.54 in MeOH).
14-Hydroxy: 14-Hydroxydemethy/cacalohastine. 14-
Cacalonol Sq-01528 Hydroxycaca/ohastine
4-Hydroxy-3,4,5-trimethylnaphtho(2,3-blfuran-9(4H)one, 9CI C15H 1603 M 244.290
[54 707-45-8] Occurs in the form of esters in Senecio lydenburgensis
and S. coronatus. The name 14-Hydroxycacalohastine as
used by the authors is misleading.
3P,14-Dihydroxy: 3P,14-Dihydroxydemethylcaca/ohastine.
3p, 14-Dihydroxycacalohastine
C15H 160 4 M 260.289
Occurs as esters in S. lydenburgensis. Inconsistent
nomenclature.
C 15H 140 3 M 242.274 3,4-Didehydro, Me ether: Dehydrocaca/ohastine
Constit. of Caca/ia auriculata. Cryst. Mp 201-203°. C 16H 160 2 M 240.301
3-Methoxy: [58880-00-5]. 3-Methoxycaca/ono/. 6- Constit. of the roots of C. hastata. Needles (MeOH aq.).
Methoxycaca/ono/ Mp 7l-77.SO.
ci6H 160 4 M 272.300 14-Acetoxy, 0-propanoy/: 14-Acetoxycaca/ohastine
Constit. of C. delphiniifolia. Yellow prisms. Mp 94-95°. propionate (incorr.)
6-Hydroperoxide: [58879-98-4]. Peroxycaca/onol C20 H 220 5 M 342.391
C15H 140 4 M 258.273 From S. spp.
Constit. of C. spp. Pale yellow plates. Mp 204-205°. 14-Propanoy/oxy, 0-propanoy/: 14-
Naya, K. et a/, Chern. Lett., 1976, 73. Propiony/oxycaca/ohastine propionate (incorr.)
C21 H 240 5 M 356.418
Cinalbicol Sq-01529 From S. lydenburgensis. Gum.
3P-Hydroxy, 14-ange/oy/oxy, 0-propanoy/: 14-Ange/oy/oxy-
[69904-85-4]
3P-hydroxycaca/ohastine propionate (incorr.)
C23 H 280 6 M 400.471
From S. lydenburgensis. Gum.
Deoxy: 1,2-Dehydrodesoxycaca/o/
C15H 160 M 212.291
Cons tit. of Euryops arabicus.
C 15H 200 M 216.322 3P-Acetoxy, Me ether: [62706-45-0]. 3P-
Constit. of Cineraria spp. Oil. [1X]i;l + 14.4° (c, 0.43 in Acetoxycacalohastine
CHC1 3). CtsH 200 4 M 300.354
Bohlmann, F. et a/, Phytochemistry, 1978, 17, 1629. Constit. of S. panduriformis. Oil. [1X]i;l +49.SO (c, 3.5 in
CHC1 3).
Hayashi, K. eta/, Phytochemistry, 1973, 12, 2931 (isol)
Cinariolide Sq-01530 Bohlmann, F. eta/, Chern. Ber., 1977, 110, 474 (3-
[69904-88-7] Acetoxycaca/ohastine)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 681 (derivs)
0

c;Q-< 2,14-Dihydroxycacalol

HO,~o~
OH
Sq-01532

C 15H 180 2 M 230.306

Constit. of Cineraria spp. Oil. [1X]i;l -13.7° (c, 14.5 in
CHC1 3).
~ f_fH2 0H
2a.-form

Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1629. M 262.305

CI5HI804
2rt-form
9-0-Propanoy/, 2,14-di-Ac:
C22H260 7 M 402.443
Constit. of Senecio lydenburgensis. Gum.
2-0-(3-Methy/butanoy/), 9-0-propanoy/, 14-Ac:

425
3,14-Dihydroxycacalol- Kanokonol Sq-01533 - Sq-01537

C:zsH32 0 7 M 444.524
Constit. of S. lydenburgensis. Gum.
9-0-Propanoyl, 14-Ac:
C20 H 240 6 M 360.406
Valeranes
Cons tit. of S. lydenburgensis. Gum.
14-0-(2-M ethylpropanoyl), 9-0-propanoyl:
C22 H 280 6 M 388.460
(jatamansanes)
Constit. of S. lydenburgensis. Gum.
2P-form
9-0-Propanoyl, 2,14-di-Ac: From S. lydenburgensis. Gum.
Cryptofauronol Sq-01535
Bohlmann, F. eta/, Phytochemistry, I982, 21, 681.
[2212-90-0]
3,14-Dihydroxycacalol Sq-01533 I

CtsH 180 4
3P-form
M 262.305
~ Absolute
3-Ac, 9-propanoy/,14-angeloyl:
~configuration
HO
C:zsH320 7 M 444.524
Constit. of Senecio lydenburgensis. Gum. C 15H 260 2 M 238.369
Bohlmann, F. eta/, Phytochemistry, I982, 21, 681. Constit. of Japanese valerian. Prisms (pet. ether). Mp 90-
910. [1X] 0 -7.4° (c, 7 in CHC1 3).
Hikino, H. eta/, Chern. Pharm. Bull., I966, 14, 735 (iso/, abs
Viteralone Sq-01534 config)
5 ,6, 7,8- Tetrahydro-4,5-dimethyl-8-oxonaphtho(2,3- blfuran-3- Sammes, P.G. eta/, J. Chern. Soc., Chern. Commun., I983, 666
carboxaldehyde, 9Cl. 3-Formyl-4,5-dimethyl-8-oxo-6,7- (synth)
dihydro-5H-naphtho(2,3-blfuran Sammes, P.G. eta/, J. Chern. Soc., Perkin Trans. I, I986, 28I
(synth)

Fauronol Sq-01536
[25146-17-2]

CtsHt40J M 242.274
(R)-form [93290-66-5]
Constit. of Vitex rotundifolia. Cryst. Mp 153-154°. [1X] 0
-3.4° (c, 0.4 in CHC1 3). C 15H 260 2
0~
M 238.369
(S)-form Ac: [2658-82-4]. Fauronyl acetate
Constit. of V. negundo. Cryst. Mp 145°. [1X]i? +6.4° (c, C 17H 280 3 M 280.406
1.07 in CHC1 3). Constit. of root of Valeriana officina/is var. latifolia. Mp
Vishnoi, S.P. eta/, Phytochemistry, I983, 12, 597. 85-86°. [1X] 0 -77.6°.
Tada, H. eta/, Heterocycles, I984, 22, 2203. Ac, semicarbazone: Mp 218.5-220°.
Hikino, H. eta/, Chern. Pharm. Bull., I965, 13, 63I; I966, 14, 735
(isol, struct, abs corifig)
Sammes, P.G. eta/, J. Chern. Soc., Perkin Trans. I, I986, 28I
(synth)

Kanokonol Sq-01537
14-Hydroxyvaleranone
[2649-70-9]

C 15H 260 2 M 238.369

Constit. of valerian root oil (Valeriana wallichi). Cryst. Mp
53-54°. [1X] 0 -72° (c, 5.8 in CHC1 3).
Ac: Kanokonyl acetate. Acetoxyvaleranone
Ct6H280 2 M 252.396
Constit. of valerian roots. Bp0 _3 I80-185° (bath). [1X] 0
-55.5° (c, 1.18 in CHC1 3).
Semicarbazone: Cryst. Mp 192-193°.

426
Valeranone - Manicol Sq-01538 - Sq-01544

Hikino, H. eta/, Chern. Pharm. Bull., 1963, 11, 1210 (isol) lsooccidol 1 Sq-01541
Kulkarni, K.S. et a/, Tetrahedron, 1964, 20, 1289 (struct) 1,2 ,3,4-Tetrahydro-IX,IX,7,8-tetramethyl-2-
Hikino, H. et al, Chern. Pharm. Bull., 1965, 13, 626 (conformn)
naphthalenemethanol

Valeranone Sq-01538
Jatamansone

(-)-form
Absolute C 15H 220 M 218.338
configuration (R)-form [87797-88-4]
Stress compd. from Nicotiana rustica.
C 15H:u.0 M 222.370 Uegaki, R. et al, Phytochemistry, 1983, 22, 1193.
(+)-form [1803-39-0]
Oil. Bp0. 1 95-98°. [1X]n + 76° (CHC1 3). Isooccidol 2
t> QK5075000. Sq-01542
1,2 ,3,4- Tetrahydro-IX,IX,5 ,6-tetramethy/-2-
(-)-form [5090-54-0] naphtha/enemethano/
Constit. of the roots of Valeriana officina/is and
Nardostachys jat amansi. Oil. [IX]~ -51.9° (c, 0.3 in

~OH
CHC1 3).
Klyne, W. et al, Tetrahedron Lett., 1964, 1443 (abs corifig)
Marshall, J.A. et al, Tetrahedron Lett., 1965, 4807 (synth)
Banerjee, D.K., J. Indian Chern. Soc., 1972, 49, I (rev)
Talvitie, A. eta/, Finn. Chern. Lett., 1977, 197 (pmr)
Wenkert, E. et al, J. Am. Chern. Soc., 1978, 100, 1263 (synth) C15H 220 M 218.338
Sammes, P.G. eta/, J. Chern. Soc., Chern. Commun., 1983, 666 (R)-form [87797-89-5]
(synth) Stress compd. from Nicotiana rustica.
Sammes, P.G. et a/, J. Chern. Soc., Perkin Trans. I, 1986, 281
. (synth) Uegaki, R. eta/, Phytochemistry, 1983, 22, 1193 .
Vite, G.D. eta/, J. Org. Chern., 1988, 53, 2560 (synth)
Lacinilene B Sq-01543
3,4-Dihydroxy-4,7-dimethyl-6-(1-methylethyl)-1(4H)-
naphthalenone, 9CI
[34069-05-1]
Miscellaneous
rearranged eudesmanes
CtsH 180 3 M 246.305
Helicquinone Sq-01539 Constit. of the heartwood of Ulnus laciniata. Mp 180-182°.
Di-Ac: Mp 138-141°.
[1 09028-48-0]
Suzuki, H. et al, Mokuzai Gakkaishi, 1971, 17, 221 (uv)
Suzuki, H. et al, Mokuzai Gakkaishi, 1972, 18, 617; CA, 78,
108174 (struct)

Manicol Sq-01544
[76235-60-4]

CtsHt 40 4 M 258.273
Constit. of Helicteres angustifolia. Red cryst. Mp 360°.
Wang, M. et al, Phytochemistry, 1987, 26, 578.

4-Hydroxy-2-isopropyl-4,7-dimethyl- Sq-01540
HOY=\
0 OH

1(4H)-naphthalenone CtsH180 3 M 246.305

[60263-15-2] Constit. of Dulacia guianensis. Pale-yellow cryst. (EtOAc).
Mp 139-140°. [IX]~ +90.6° (c, 0.94 in CHC1 3). Revised
struct.
Polonsky, J. et al, Tetrahedron, 1983, 39, 2647 (cryst struct)

CtsH 180 2 M 230.306

Constit. of Heterotheca inuloides. Oil.
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 2021.

427
1,2,3,4,4a,5,6,7-0ctahydro-4a,5-... - Benghalensitriol Sq-01545 - Sq-01550

1,2,3,4,4a,5,6,7-0ctahydro-4a,5-dimethyl- Sq-01545 lsol. from Artemisia annua. Shows antibacterial activity.

2-(1-methylethenyl)naphthalene Cubes (pet. ether). Mp 131°. [cx] 0 +36° (c, O.Dl in
CHC1 3).
6,7-Didehydro: 4,6,11(13)-Cadinatrien-12-oic acid. 6,7-
Dehydroartemisinic acid
CisH200 2 M 232.322
Constit. of A. annua. Cryst. (Et20jhexane). Mp 129-
1300. [cx] 0 +317° (c,0.05 in MeOH).
Tu, Y.Y. et al, Planta Med., 1982, 44, 143 (isol)
C15H24 M 204.355 Zhou, W. eta/, CA, 1985, 103, 160709 (config)
Constit. of Helichrysum davyi. Oil. [cx]i;' -20° (c, 0.05 in Roth, R.J. et al, Planta Med., 1987, 53, 501 (isol)
CHC1 3). EI-Feraly, F.S. et al, J. Nat. Prod. (Lloydia), 1989, 52, 196 (isol,
Jakupovic, J. et al, Phytochemistry, 1987, 26, 1841. deriv, pmr, cmr)
Akhila, A. et al, Phytochemistry, 1990, 29, 2129 (biosynth)

Arteannuin B Sq-01549
[50906-56-4]
Cadinane group

1-Acetoxydihydroisochromolaenin Sq-01546
[62502-11-8]

mo
C15H 200 3 M 248.321
AcO ,
Constit. of Artemisia annua. Cryst. Mp 152°. [cx]i:' -6°.
4,5-Diepimer: [107172-37-2]. Arteannuin C
CisH 200 3 M 248.321
Constit. of A. annua. Cryst. Mp 128°. [cxli:' -26° (c, 0.53

C 17H 200 3
~
M 272.343
in MeOH).
Jeremic, D. et al, Tetrahedron Lett., 1973, 3039 (isol)
Uskokovic, M.R. et a/, Helv. Chim. Acta, 1974, 57, 600 (struct)
The trivial name is misleading since this is not the acetoxy Leppard, D.G. eta/, Helv. Chim. Acta, 1974, 57, 602 (cryst struct)
deriv. of dihydroisochromolaenin (see Chromolaenin, Goldberg, 0. et al, Helv. ·chim. Acta, 1980, 63, 2455 (synth)
Yusupova, I.M. et al, Khim. Prir. Soedin., 1986, 22, 733 (cryst
Sq-01597). Constit. of Chromolaena spp. Cryst. struct)
(Etpjpet. ether). Mp 113-lW. [cx]i;' -147° (c, 0.1 in Misra, L.N. et al, Phytochemistry, 1986, 25, 2892 (Arteannuin C)
CHC1 3). Lansbury, P. et al, Tetrahedron Lett., 1986, 27, 3967 (synth)
Bohlmann, F. et al, Chern. Ber., 1977, 110, 487. Jung, M. et al, J. Nat. Prod. (Lloydia), 1987, 50, 972 (synth)
Akhida, A. eta/, Phytochemistry, 1987, 26, 1927 (biosynth)
4,11-Amorphadiene Sq-01547
4,11-Cadinadiene (incorr.) Benghalensitriol Sq-01550
[87174-93-4]

HO-MH
C•sH24 M 204.355
Relative config. only detd. Constit. of Viguiera C 15H 260 4
HOUX
M 270.368
oblongifo/ia. Oil. [cx]i;' -8° (c, 0.4 in CHC1 3). Constit. of Meriandra benghalensis. Cryst. (EtOAc). Mp
Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1183. 218°. [cx]i;1 +7.9° (c, 0.126 in Py).
Perales, A. eta/, J. Org. Chern., 1983, 48, 5318.
4,11(13)-Amorphadien-12-oic acid Sq-01548
Artemisinic acid. Artemisic acid. Qing Hau acid. Arteannuic
acid
[80286-58-4]

M 234.338

428
Bicadinane - 15-Cadalenal Sq-01551 - Sq-01558

Bicadinane Sq-01551 fl. 10<14'-Isomer: [68000-46-4]. 4,10(14)-Bulgaradiene. y-

Bulgarene
C 15H 24 M 204.355
Constit. of J. oxycedrus. Oil.
De Pascual Teresa, J. et al, An. Quim., 1977, 23, 1527.

4(15),5-Bulgaradiene Sq-01555
Nephthene

C 30H 52 M 412.741
Found in crude oil.
Cox, H.C. et al, Nature (London), 1986, 319, 316 (isol)
van Aarssen, B.G.K. et al, Tetrahedron Lett., 1990, 31, 4645 (isol)

Bicalamenene Sq-01552 CtsH 24 M 204.355

[96622-98-9] Constit. of coral Nephthea sp. Oil. [1X]i? -9° (c, 5.3 in
CHCI 3).
Kitagawa, I. et al, Chern. Pharm. Bull., 1987, 35, 124.

4(15),10(14)-Bulgaradiene Sq-01556
e-Bulgarene
[15890-31-0]
I

~
C 30H 42 0 2 M 434.661
Constit. of Dysoxylum alliaceum. Pale-yellow syrup. [1X]i;
+32.4° (c, 1.55 in CHC1 3).
Nishizawa, M. et al, Tetrahedron Lett., 1985, 26, 1535 (struct,
synth) CtsH24 M 204.355
Constit. of the oil of Mentha piperita. Bp4_5 107-115°. [1X]i?
8,8' -Bis(7-hydroxycalamenene) Sq-01553 -17.1°.
Linek, A. et al, Tetrahedron Lett., 1968, 23 (isol, struct)
"-y/ Koster, F.-H. et al, Justus Liebigs Ann. Chern., 1986, 78 (synth,
I
I cmr)

Bulgarene dihydrobromide Sq-01557

[13833-16-4]

CJJI 42 0 2 M 434.661
Constit. of Heritiera ornithocephala. Oil. [1X]i; -288° (c,
C15H 26 Br2 M 366.178
·42
Cryst. (EtOAc). Mp 116-117°.
CHCI 3).
[1X]~ +61.4° (c, 0.1 in
0.32 in CHC1 3).
V1ahov, R. et al, Collect. Czech. Chern. Commun., 1967, 32, 822
Cambie, R.C. eta/, Phytochemistry, 1990, 29, 2329 (isol, pmr, cmr) (synth)
Linek, A. et al, Tetrahedron Lett., 1968, 23 (cryst struct)
4,9-Bulgaradiene Sq-01554
P1-Bulgarene 15-Cadalenal Sq-01558
[68000-45-3] 5-Methyl-8-(1-methylethyl)-2-naphthalenecarboxaldehyde. 8-
lsopropyl-5-methyl-2-naphthalenecarboxaldehyde
14

~ HI OHC~
M
~
C 15H 24 M 204.355 CtsH 160 M 212.291
Constit. of berries of Juniperus oxycedrus. Oil. [1X]n -98.5° Cadalane numbering shown. Constit. of Calocedrus
(c, 0.76 in CHC1 3). formosana.

429
3,8-Cadalenediol - 1(10),3-Cadinadiene Sq-01559 - Sq-01564

2,3-Dihydro: 3,4-Dihydro-8-isopropyl-5-methyl-2- 3-Cadalenol Sq-01561

naphthalenecarboxaldehyde. 2,3-Dihydro-15-cadalenal 3,8-Dimethyl-5-(1-methylethyl)-2-naphthalenol, 9CI. 5-
CtsHt80 M 214.307 /sopropyl-3,8-dimethyl-2-naphthol. 3-Hydroxycadalene. 7-
From C. formosana. Hydroxycadalene
Carboxylic acid, Me ester: Methyl 8-isopropyl-5-methyl-2- [2102-75-2]
naphthalenecarboxylate. Methyl 15-cadalenoate
C 16H 180 2 M 242.317
Constit. of C. formosana.
Carboxylic acid, 2,3-dihydro, Me ester: Methyl 3,4-dihydro-
8-isopropyl-5-methyl-2-naphthalenecarboxylate. Methyl
2,3-dihydro-15-cadalenoate
C 16H 2(.02 M 244.333
From C. formosana. C 15H 180 M 214.307
Fang, J.-M. et al, Phytochemistry, 1987, 26, 853. Constit. of various heartwoods. Cryst. (pet. ether). Mp
118-119.SO.
3,8-Cadalenediol Sq-01559 Picrate: Reddish-brown needles. Mp 138.5-139.SO.
4, 7- Dimethyl-1-( 1-methylethyl)-2 ,6-naphthalenediol. 1- Briggs, L.H. et al, J. Chern. Soc., 1949, 1098 (synth)
1sopropyl-4, 7-dimethyl-2 ,6-naphthalenediol. 3, 7-Calalenediol Gallagher, M.J. et al, Aust. J. Chern., 1965, 18, 1111 (synth, uv)
Alexander, J. et al, Tetrahedron, 1971, 27, 645 (synth, ir, uv)

5-Cadalenol Sq-01562
2,5-Dimethyl-8-(1-methylethyl)-1-naphthalenol, 9CI. 8-
/sopropyl-2 ,5-dimethyl-1-naphthol. 5-Hydroxycadalene

C 15H 180 2 M 230.306

8-Me ether: 5-1sopropyl-6-methoxy-3,8-dimethyl-2-naphthol.
8-Methoxy-3-cadalenol
C 16H 200 2 M 244.333
Cons tit. of Zelkova serrata. Mp 110-111 o.
Hayashi, Y. et al, Mokuzai Gakkaishi, 1972, 18, 41; CA, 76,
C 15H 180 M 214.307
138179v. Oil. Bp 0 .2 112-114°.
Picrate: Brownish-red needles (EtOH). Mp 135-136°.
3,9-Cadalenediol Sq-01560 Plattner, P.A. et al, Helv. Chim. Acta, 1941, 24, 1163 (synth)
1,6-Dimethyl-4-(1 -methylethyl)-2, 7-naphthalenediol. 1,6- Takeda, K. et al, Tetrahedron, 1961, 13, 308 (synth, ir, uv)
Dimethyl-4-isopropyl-2,7-naphthalenediol. 2,7-Cadalenediol
[77401-25-3] 9-Cadalenol Sq-01563
1,6-Dimethyl-4-(1-methylethyl)-2-naphthalenol, 9CI. 4-
Isopropyl-1 ,6-dimethyl-2-naphthol. 3-Hydroxycadalene. 2-
Hydroxycadalene

MoH
~
CtsHts02 M 230.306
Constit. of Gossypium spp. Oil.
Bis(3,5-dinitrobenzoyl): Cryst. Mp 212-213°.
3-Me ether: [68233-94-3]. 9-Hydroxy-3-methoxycadalene
C 15H 180 M 214.307
Needles (pet. ether). Mp 76.5-77.SO.
C 16H 200 2 M 244.333
Isol. from G. sp. Oil. Mp 217-217.5° (as 3,5- Picrate: Mp 141-142°.
dinitrobenzoyl). Gallagher, M.J. et al, Aust. J. Chern., 1965, 18, 1111 (synth, uv)
Stipanovic, R.D. et al, Phytochemistry, 1981, 20, 729 (isol)
McCormick, J.P. et al, J. Org. Chern., 1984, 49, 34 (synth) 1(10),3-Cadinadiene Sq-01564
Essenberg, M. et al, J. Chern. Soc., Chern. Commun., 1985, 556 w-Cadinene
(biosynth)

C 15H24 M 204.355
Constit. of Mentha piperata. Oil. Bp4 . 5 115-128°. [a]i;>
+ 92°. Originally named J-Cadinene, which led to
confusion with 1(10),4-Cadinadiene, Sq-01565.
Connell, D.W. et al, Tetrahedron Lett., 1968, 519.

430
1(10),4-Cadinadiene - 4(15),9-Cadinadiene Sq-01565 - Sq-01571

1(10),4-Cadinadiene Sq-01565 (-)-form

0-Cadinene Constit. of Dictyopteris zonaroides. Oil. [exln -217.8° (c,
0.46 in cyclohexane).
(+)-form
12-Hydroxy: 12-Hydroxyzonarene
CISH240 M 220.354
Constit. of Lemnalia cervicornis. [exln +227.6° (c, 0.14 in
CHCI 3).
12-Acetoxy: 12-Acetoxyzonarene
CISH24 M 204.355 C 17H160 2 M 262.391
(+)·form [483-76-1] From L. cervicornis. Oil. [exln +241.8° (c, 0.75 in
Constit. of inter alia the essential oils of y1ang-ylang, CHC13).
citronella, cubebs, sweetfiagand cade. Oil. Bp 10 133-134°.
Fenica1, W. et al, Phytochemistry, 1972, 11, 1161 (iso/, struct)
Bisepoxide: Cryst. Mp 86-87°. [exln +23° (c, 6.7 in CHCI 3). Andersen, N.H. et al, Phytochemistry, 1973, 12, 827 (stereoisomers)
(±)-form Iguchi, M. et al, Bull. Chern. Soc. Jpn., 1973, 46, 2920 (synth, abs
Dysoxylonene config)
Constit. of Dysoxylumfraseranum. Bp 10 133°. Williams, J.R. et al, J. Org. Chern., 1983, 48, 3162 (synth)
Bowden, B.F. et al, Aust. J. Chern., 1986, 39, 103 (derivs)
Herout, V. eta/, Collect. Czech. Chern. Commun., 1954, 19, 118
(struct)
Nagasampagi, B.A. eta/, Tetrahedron Lett., 1968, 1913 (struct) 4,9-Cadinadiene Sq-01569
Nishimura, H. et al, Agric. Bioi. Chern., 1981, 45, 1861 (synth) rx.-Cadinene
[24406-05-1]
1(10),11-Cadinadiene Sq-01566
fl-Metrosiderene

CISH24 M 204.355
Constit. of Humulus lupulus. Oil. [ex]~4 -62.4° (c, 0.808 in
CISH24 M 204.355 CHCI3).
Constit. of Metrosideros umbel/ata. Oil. Obt. only as a Naya, Y. et al, Bull. Chern. Soc. Jpn., 1969, 42, 1468 (isol, struct)
mixt. with ex-Metrosi4erene. Vig, O.P. et al, Indian J. Chern., Sect. B, 1982, 21, 145 (synth)
1!. 7•11 - Isomer: 1(10), 7(1 1)-Cadinadiene. rx.-Metrosiderene
CISH24 M 204.355 4,10(15)-Cadinadiene Sq-01570
Constit. of M. umbe/lata. y-Cadinene
Corbett, R.E. et al, J. Chern. Soc., 1954, 1179. [1460-97-5]

3,10(14)-Cadinadiene Sq-01567
y2-Cadinene

m
[5957-56-2]

C 15H 24 M 204.355
Constit. of the oil of citronella. Oil. Bp5 110-115°. [ex]~
H' + 148°.
A Vig, O.P. et al, Indian J. Chern., 1970, 8, 29 (isol, struct)
Sakurai, H. et al, Tetrahedron, 1983, 39, 883 (synth)
CISH24 M 204.355
Constit. of Vetiveria zizanioides. Oil. Bp 3 115°. [ex]~ -4.9°
(CHCI 3). 4(15),9-Cadinadiene Sq-01571
y1-Cadinene
Burk, L.A. et al, Tetrahedron, 1976, 32, 2083.
Vig, O.P. et al, Indian J. Chern., Sect. B, 1981, 20, 972 (synth) [66141-11-5]

4,6-Cadinadiene Sq-01568
Zonarene
[41929-05-9]

~
C15H 24 M 204.355
Constit. of Malabar lemon grass oil (Cymbopogon nardus),
Hardwickia pinnata and Dictyopteris divaricata. Bp9 120-
(-)-form
121°. [exln - J90. ni:·
5 1.5155.
12
Dev, S. et al, J. Indian Chern. Soc., 1949, 26, 263 (isol)
M 204.355

431
4(15),10(14)-Cadinadiene - 4,10(15)-Cadinadien-2-ol Sq-01572 - Sq-01578

Irie, T. et al, Bull. Chern. Soc. Jpn., 1964, 37, 1053 (isol) 1(10),4-Cadinadien-9-ol Sq-01576
Andersen, N.H. et al, Phytochemistry, 1977, 16, 1731 (struct) o-Cadinen-9-o/
Vig, O.P. et al, Indian J. Chern., Sect. B, 1979, 17, 552 (synth)

4(15},10(14)-Cadinadiene Sq-01572
Decahydro-1 ,6-bis(methy/ene)-4-(1-methy/ethy/)naphtha/ene,
9CI. Decahydro-4-isopropy/-1 ,6-dimethy/enenaphtha/ene. e-
Ctulinene
[25548-04-3]
C 15H 240 M 220.354
H 'h.-form
I

Ange/oyl: [72943-93-2].
C 20H 320 2 M 304.472
Absolute Constit. of Heterotheca subaxillaris. Oil.
configuration Ketone: [73484-15-8]. 1(10),4-Cadinadien-9-one. o-Cadinen-
9-one
C 15H 24 M 204.355
C 15H 220 M 218.338
Constit. of Mentha arvensis and Juniperus communis. Oil.
Constit. of H. grandiflora. Oil.
Bp2 99-100°. [1X]i; +50.7° (c, 1.5 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1185, 1675.
[1080-67-7, 27542-04-7]
Burk, L.A. et al, Tetrahedron, 1976, 32, 2083 (bib{)
Koster, F.-H. et al, Justus Liebigs Ann. Chern., 1986, 78 (synth, 4,10(14)-Cadinadien-12-ol Sq-01577
cmr) Khusol
Hagiwara, H. et al, J. Chern. Soc., Chern. Commun., 1987, 1333 [18045-73-3]
(synth)

1(10),4-Cadinadiene-3,9-diol Sq-01573
3,9•Dihydroxy-o-cadinene

HO,~_,.OH

~HI
C 15H 240 M 220.354
Constit. of oil of Vetiveria zizanioides. Cryst. (pet. ether).
A Mp 101-102°. [1X]i; -137° (c, 2.9 in CHC1 3).
Ac: Oil. Bp0 . 7 155°. [1X]i;' -115° (c, 2 in CHCI 3).
CtsH:z.c02 M 236.353
Ka1si, P.S. et al, Tetrahedron, 1963, 19, 1073.
(3«,9«)-form
Constit. of Helichrysum dasyanthum. Gum.
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1119.
4,10(14)-Cadinadien-2-ol Sq-01578

4,1 0(14)-Cadinadiene-2,9-diol Sq-01574

HO
OH

::::-.... I
HI C 15H 240 M 220.354
_,.).._..__ 2«-form [41678-93-7] Epikhusinol
Constit. of vetiver oil. Oil. Bp1. 5 150° (bath). [IX]~ -20°
C 15H 240 2 M 236.353 (c, 0.4 in CHCl 3).
(2P,9fl)-form 2fJ-form [24268-34-6] Khusinol
Vetidiol Constit. of Vetiveria zizanioides. Cryst. (pet. ether). Mp
Constit. of vetiver oil. Cryst. Mp 170°. [IX]~ -140°. 87°. (1X]n + 174.4° (c, 5 in CHCl 3).
Ka1si, P.S. et al, Tetrahedron, 1987, 43, 2985. JOP,15-Epoxide: [3484-48-8]. wp, 15-Epoxy-4-cadinen-2-o/.
10p,15-Epoxykhusinol. Khusinoloxide
1(10),4-Cadinadien-14-oic acid Sq-01575 CtsH 240 2 M 236.353
Cadinen-14-oic acid Constit. of V. zizanioides. Cryst. (pet. ether). Mp 113°.
[1X]~ -24.9° (c, 1.9 in CHCI 3).

~H
4P,5P-Epoxide: [73650-15-4]. 4P,5P-Epoxy-! 0( 14)-cadinen- 2-
o/. lsokhusinoloxide
CtsH 240 2 M 236.353
Constit. of vetiver oil (V. zizanioides). Cryst. (pet. ether).
Mp 82°.
Seshadri, R. et al, Tetrahedron, 1967, 23, 1267 (isol)
C 15H 220 2 M 234.338 Tirodkar, S.V. et al, Sci. Cult., 1969, 35, 27 (struct)
Constit. of Heterotheca grandiflora. Cryst. Mp 104°. Kelly, R.B. et at, Can. J. Chern., 1972, 50, 3272 (struct)
Ka1si, P.S. et a/, Indian J. Chern., 1972, 10, 1127 (iso/, struct)
E1-Dahmy, S. et al, Phytochemistry, 1986, 25, 1474.

432
1,9-Cadinadien-3-one - 4-Cadinen-1-ol Sq-01579 - Sq-01586

Agrawal, R.C., Indian J. Chern., 1975, 13, 376 (synth) Cadinene dibydrochloride Sq-01583
Kalsi, P.S. et al, Bull. Soc. Chim. Fr., Part II, 1979, 599
(lsokhusinoloxide) As Cadinene dihydrobromide, Sq-01582 with
R = Cl
1,9-Cadinadien-3-one Sq-01579
C 15Hu;C12 M 277.276
(-)-form [16641-30-8]
Cryst. (pet. ether). Mp 117-llS.SO. [«Ji? -37° (CHC1 3).
(+)-form [3038-33-3)
Cryst. (pet. ether). Mp 117°. [«Jn +37.5° (CHC1 3).
Burk, L.A. et al, Tetrahedron Lett., 1971, 4367 (synth)
Pier, E. et al, Can. J. Chern., 1975, 53, 1281 (synth)
C15H:z:z0 M 218.338
Constit. of Helichrysum petio/are. Oil. 4-Cadinene-1 0,14-diol Sq-01584
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1119. 14-Hydroxy- r-cadinol

1,4,9-Cadinatriene Sq-01580 HO CHzOH

~
1,4,9-Cada/atriene
[71609-04-6]

C 15H 260 2 M 238.369

Constit. of Pulicaria pa/udosa. Oil. [«Ji: + 3.2° (CHC1 3).
San Feliciano, A. et al, Phytochemistry, 1989, 28, 2717 (isol, pmr,
cmr)
C 15H 22 M 202.339
Constit. of Acorus calamus. Oil. Bp0 _01 80°. [a]i;1 -156.4°
(c, 1 in CHC13). 4(15)-Cadinene-6,10-diol Sq-01585
Rohr, M. et al, Phytochemistry, 1979, 18, 328.

4(15),5,11-Cadinatriene
1-Epibicyc/osesquiphe/landrene. 1-epi-
Bicyc/osesquiphel/andrene
[54274-73-6]
Sq-01581

C15Hu;02
~H (6~,10.)-fo~
M 238.369
(6p,10rr.)-form [25330-21-6] /socalamendio/
Constit. of the rhizomes of Acorus calamus. Cryst.
(EtzO/hexane). Mp 72.5-73.SO.
(6p,10p)-form (30167-28-3] Ca/amendiol. Ca/ameone
Constit. of sweetfiag essential oil. Cryst. (Etpjhexane).
Mp 170-17l.SO. [«]~ -4.4° (EtOH).
C15H 24 M 204.355
Constit. of Ocimum basi/icum. Oil. Yamamura, S. et al, Tetrahedron, 1971, 27, 5419 (isol, struct)
Niwa, M. et al, Bull. Chern. Soc. Jpn., 1976, 49, 3148 (synth)
Terhune, S.J. eta/, Phytochemistry, 1974, 13, 1183 (isol, struct) Williams, J.R. et al, J. Org. Chern., 1980, 45, 4479 (synth)
Vig, O.P. et al, J. Indian Chern. Soc., 1976, 53, 593 (synth)
4-Cadinen-1-ol Sq-01586
Cadinene dihydrobromide Sq-01582 Cubeno/
[21284-22-0]

Absolute
configuration

R=Br
C 15Hu;Br2 M 366.178 C 15Hu;O M 222.370
Cryst. prod. obt. from Cadinene. Cryst. Mp 124-125°. [«ln Constit. of oil of cubeb. Oil. Bp2_5 170-180° (bath). [«]~
-36.13°. -30.6°.
Hanic, F., Chern. Listy, 1958, 52, 165 (cryst struct) Ohta, Y. eta/, Tetrahedron Lett., 1967, 2073 (isol, struct)
Sykora, V. et al, Collect. Czech. Chern. Commun., 1958, 23, 2181 Adams, D.R. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1502
(abs cmifig) (isol)

433
4-Cadinen-10-ol- Calamenene Sq-01587 - Sq-01591

4-Cadinen-1 0-ol Sq-01587 Bohlmann, F. et al, Chern. Ber., 1976, 109, 2021 (3-Hydroxy-rx-
calacorene)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1675 (3-Hydroxy-P-
~H calacorene)

y-Calacorene Sq-01590
~ lOcx-form 1,2-Dihydro-1 ,6-dimethyl-4-(1-methylethyl)naphthalene, 9Cl.
1,3,5,7-Cadinatetraene, 8Cl. 1,2-Dihydro-4-isopropyl-1 ,6-
C 15Hu;0 M 222.370 dimethylnaphthalene. 9,10-Dihydrocadalene. 1,2-
10rz-form [481-34-5] rz-Cadinol Dihydocadalene
Constit. of Chamaecyparis lawsoniana and Juniperus [24048-45-1]
communis. Also from C. obtusa, C. pisifera, J.
horizontalis, J. scopulorum, Athrotaxis spp. and
Neocallitropsis araucaroides. Cryst. Mp 74.5-75°. [cx] 0
-47° ( -38.5°).
10fJ-form [5937-11-1] T-Cadinol
Constit. of Taiwania cryptomeroides and Arthrotaxis
selaginoides. Mp 64-64.5°. [cx] 0 + 3.4° (c, 1.2 in CHC1 3).
Nagasampagi, B.A. et al, Tetrahedron Lett., 1968, 1913 (isol) C 15H 20 M 200.323
Caine, D. eta/, Tetrahedron Lett., 1977, 3107 (synth) The (S)-Config is given in CA but does not appear to be
Borg-Karlson, A.-K. et a/, Tetrahedron, 1981, 37, 425 (sterochem) clearly stated in the lit.
Bottini, A.T. et al, J. Nat. Prod. (Lloydia), 1987, 50, 732 (cmr) (S)-form
Constit. of Juniperus rigida and Humulus lupulus. Oil.
10(15)-Cadinen-11-ol Sq-01588 3-Methoxy: 3-Methoxy-9,10-dihydrocadalene
Veticadinol C 16H 220 M 230.349
[14107-43-8] Isol. from Lemnalia cervicornis. Oil. [cx] 0 -54.9° (c, 0.69
in CHC1 3).

--eli
(±)-form
Bp9 125-126°.
Naya, Y. et al, Bull. Chern. Soc. Jpn., 1969, 42, 2088.
Adachi, K. et al, Bull. Chern. Soc. Jpn., 1983, 56, 651 (synth)
Bowden, B.F. et al, Aust. J. Chern., 1986, 39, 103 (deriv)
OH
Calamenene Sq-01591
C 15H 260 M 222.370 1,2,3,4-Tetrahydro-1 ,6-dimethyl-4-(1-
Constit. of vetiver oil. Oil. Bp 10 100-105°.
methylethyl)naphthalene, 9Cl. 1,2,3,4- Tetrahydro-4-
Chiurdoglu, G. et al, Bull. Soc. Chim. Be/g., 1961, 70, 5 (isol) isopropyl-1 ,6-dimethylnaphthalene. 4-/sopropyl-1 ,6-
Vig, O.P. et al, Indian J. Chern., 1969, 7, 434 (synth) dimethyltetralin. 7,8,9,10- Tetrahydrocadalane

ot-Calacorene Sq-01589
1,2-Dihydro-4, 7-dimethyl- I-( 1-methylethyl)naphthalene, 9Cl.
1,2-Dihydro-1-isopropyl-4,7-dimethylnaphthalene. 7,8-
Dihydrocadalene. 3,4-Dihydrocadalene
[21391-99-1] A I
(7R,10R)-form

C 15H 22 M 202.339
Two numbering systems have been used for ca1amenes.
(7R,10R)-form [22339-23-7]
Constit. of Eremophila drummondii. Oil. [cx] 0 +41.3° (c,
1.2 in CHC1 3).
3-Hydroxy: 5,6, 7,8- Tetrahydro-5-isopropyl-3 ,8-dimethyl-2-
C 15H 20 M 200.323 naphthol. 3-Hydroxy-10-epicaltunenene. 2-Hydroxy-9-
Constit. of hop, pine, vetiver, sweettlag, Juniperus and epicalamenene
other oils. Oil. [cx]i,O + 52.1°. C 15H 220 M 218.338
3-Hydroxy: [60263-12-9]. 3-Hydroxy-rz-calacorene. 5,6- Constit. of Osteospermum barberiae and E. drummondii.
Dihydro-5-isopropyl-3,8-dimethyl-2-naphthol (cx] 0 +27°.
C 15H 200 M 216.322 5- Hydroxy: 5,6, 7,8- Tetrahydro-8-isopropyl-2,5-dimethyl-1-
Constit. of Heterotheca inuloides. Cryst. (pet. ether). Mp naphthol. 5-Hydroxycalamenene. 4-Hydroxycalamenene
103.5". C 15H 220 M 218.338
11.1°· 14-/somer, 3-hydroxy: [73484-09-0]. 3-Hydroxy-fJ- Constit. of Bazzania tricrenata. Oil. Isol. in small amt.
calacorene only.
C 15H 200 M 216.322 (7S,10S)-form [483-77-2]
lsol. from H. grandiflora. Oil (as acetate). Constit. of Ulmus thomasii. Oil. Bp 13 126°. [cx] 0 -47°
Heymes, A. eta/, Recherches, 1974, 19, 214 (synth) (CHC1 3).
3-Hydroxy: 3-Hydroxycalamenene
Constit. of U. thomasii. Cryst. [cx] 0 -30° (c, 1 in
CHC1 3).

434
3,7-Calamenenediol - 3,9-Calamenenediol Sq-01592 - Sq-01594

2-Hydroxy, 3-acetoxy: 3-Acetoxy-2-hydroxycalamenene 3,8-Calamenenediol Sq-01593

C 17H 240 3 M 276.375 3, 7-Calamenenediol
Isol. from the liverwort Lophocolea heterophylla. Oil.
(7R,JOS)-form
Oil. [IX]D + 82°.
2-Hydroxy: 5 ,6,7,8-Tetrahydro-5-isopropyl-3,8-dimethyl-1-
naphthol. 2-Hydroxycalamenene
C 15H 22 0 M 218.338
Isol. from dried seeds of Dysoxylum acutangulum and D.
C 15H 220 2 M 234.338
alliaceum. Fish-poison also showing antibacterial
Two numbering systems are used for calamenenes.
activity. Liq. Bp0_1 150-155°. [IX]); +38.0° (CHC1 3).
(7rx.,8fl,l0fl)-form
2-Methoxy: [71306-08-6]. 2-Methoxycalamenene
Constit. of Lemnalia cervicornis. Oil. [1X]n +23.3° (c, 0.3
Ct6H240 M 232.365 in CHC1 3).
Constit. of the horny coral Subergorgia hicksonii. Oil.
Bp0_1 lWO. [1X]i;5 +30° (c, 0.1 in CHC1 3). 3-Me ether: 3-Methoxy-8-calamenenol. 7-Methoxy-3-
calamenenol
5-Hydroxy, 8-methoxy: [71306-09-7]. 5-Hydroxy-8-
methoxyca/amenene
Ct6H2402 M 248.364
From L. cervicornis. Oil. (1X]n + 22° (c, 0.25 in CHC1 3).
Ct6H 240 2 M 248.364
Constit. of S. hicksonii. Cryst by sub!. Mp 84°. (1X]i;5 3-Me ether, 8-Ac: 8-Acetoxy-3-methoxyca/amenene. 3-
+58° (c, 0.1 in CHC1 3). Acetoxy-7-methoxycalamenene
CtsH260 3 M 290.402
3-Hydroxy: 3-Hydroxycalamenene. 2-Hydroxycalamenene
From roots of 0. spp. From L. cervicornis. Oil. [1X]n +22.3° (c, 0.57 in CHC1 3).
8-Ketone: 3-Hydroxy-8-calamenenone. 7-Hydroxy-3-
(7S,JOR)-form
calamenenone
From Cedrela toona. Oil. [1X]n -80°.
CtsH 200 2 M 232.322
Sangaiah, R. eta/, Indian J. Chern., Sect. B, 21, 13 (synth) From L. cervicornis. Cryst. (MeCN). Mp 121-123°. [1X]n
Plattier, M. et al, Recherches, 1974, 19, 214 (synth) + 178.1 o (c, 0.18 in CHC1 3).
Andersen, N.H. et al, Phytochemistry, 1977, 16, 1731 (isol, deriv)
Croft, K.D. eta/, J. Chern. Soc., Perkin Trans. I, 1978, 1267 (isol, 8-Ketone, 3-Ac: 3-Acetoxy-8-ca/amenenone. 7-Acetoxy-3-
cryst struct) calamenenone
Kashman, Y., Tetrahedron, 1979, 35, 263 (derivs) Ct 7H 220 2 M 258.360
Bunko, J.D. et al, Aust. J. Chern., 1981, 34, 2237 (synth, struct, abs From L. cervicornis. Oil. [1X]n + 173.6° (c, 1.24 in
conjig) CHC1 3).
Adachi, K. et al, Bull. Chern. Soc. Jpn., 1983, 56, 651 (synth)
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1645 (derivs) 8-Ketone, 3-Me ether: 3-Methoxy-8-calamenenone. 7-
Nishigawa, M. et al, Phytochemistry, 1983, 22, 2083 (derivs) M ethoxy-3-calamenenone
Vig, O.P. et at, Indian J. Chern., Sect. B, 1984, 23, 992 (synth) Ct6H240z M 248.364
Uemura, M. eta[, Tetrahedron, 1985, 41, 5771; Chern. Lett., 1985, From L. cervicornis. Oil. [1X]n + 136.6° (c, 0.2 in CHCI 3).
91 (synth, derivs) Bowden, B.F. et a/, Aust. J. Chern., 1986, 39, 103.
Tanaka, J. et al, Bull. Chern. Soc. Jpn., 1990, 63, 272 (5-
hydroxycalamenene, synth, struct)
Toyota, M. et al, Phytochemistry, 1990, 29, 2334 (3-Acetoxy-2- 3,9-Calamenenediol Sq-01594
hydroxycalamenene)

3,7-Calamenenediol Sq-01592
4, 7-Calamenenediol

CtsH22 0z M 234.338
(7cx( OH),10f3)-form 9rx.-form
9-Angeloyl: [72943-95-4].
C20H 280 3 M 316.439
CtsHnOz M 234.338 Constit. of Heterotheca subaxillaris. Oil. (1X]i; +21.7° (c,
Two numbering systems are used for calamenenes. 4.4 in CHCI 3).
(7rx.(OH),10fl)-form 9-Angeloyl, 3-Me ether: (72943-96-5).
3-Me ether: 3-Methoxy-7-calamenenol. 7-Methoxy-4- C11H 300 3 M 330.466
calamenenol Constit. of H. subaxillaris. Oil.
Ct6H24 0 2 M 248.364 Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1185.
Constit. of Lemnalia cervicornis. Oil. [1X]n - 1.2° (c, 2.26
in CHC1 3).
(7/l(OH),l0/1)-form
3-Me ether: From L. cervicornis. Oil. [1X]n +33.5° (c, 0.33
in CHC1 3).
Bowden, B.F. et at, Aust. J. Chern., 1986, 39, 103.

435
3,14-Calamenenediol - 3,4-Dihydro-6-hydroxy-4,7-dimethyl-... Sq-01595 - Sq-01601

3,14-Calamenenediol Sq-01595 Bohlmann, F. et al, Chern. Ber., 1977, 110, 487 (Chromolaenin)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1177 (iso[)
[7 3484-06-7] Juo, R.-R. et al, J. Org. Chern., 1985, 50, 700 (synth)
Misra, L.N. et a/, Tetrahedron, 1985, 41, 5353 (synth)

ot-Corocalene Sq-01598
1,2-Dihydro-3 ,8-dimethyl-5-(1-methylethyl)naphthalene. 1,2-
Dihydro-5-isopropyl-3,8-dimethylnaphthalene
[20 129-39-9]

C 15H 22 0 2 M 234.338
Constit. of Heterotheca grandiflora. Oil.
14-Ac: 14-Acetoxy-3-calamenenol
Ct,H 240 3 M 276.375
Constit. of Senecio tomentosus. Oil.
14-Carboxylic acid: [73484-07-8]. 3-Hydroxy-14-calamenoic C 15H 20 M 200.323
acid Constit. of the oil of hops (Humulus lupulus). Oil.
C 15H 200 3 M 248.321 Naya, Y. et al, Bull. Chern. Soc. Jpn., 1969, 42, 2088.
Constit. of H. grandiflora. Oil.
14-Carboxylic acid, Me ether: [73484-01-2]. 3-Methoxy-14-
calamenoic acid
Curzeone Sq-01599
7,8-Dihydro-1,5,8-trimethylnaphtho[2,1-blfuran-9(6H)one,
Ct6Hn03 M 262.348
Constit. of H. grandiflora. Cryst. (pet. ether). Mp 98°. 9Cl
[1X]~ +6.9° (c, 2 in CHC1 3). [104068-56-6]
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1675 (isol, struct)
Mericli, A.H. eta/, Phytochemistry, 1989, 28, 1149 (14-Acetoxy-3-
calameneno[)

3,7,8-Calamenenetriol Sq-01596
3,4,7-Calamenenetriol
C 15H 160 2 M 228.290
Constit. of Curcuma zedoaria. Cryst. Mp 72-74°. [IX]~
(7t1( OH),8~,10~):form + 24° (c, 2 in CHC1 3).
OH Shiobara, Y. eta/, Phytochemistry, 1986, 25, 1351.

Deoxyhemigossypol Sq-01600
C 15H 22 0 3 M 250.337 5-Isopropyl-7-methyl- 2H -naphtha[1,8- belfuran-3 ,4-diol
(7u.(OH),8p,J0/1)-form [57765-65-8]
lsol. from Lemnalia cervicornis. Cryst. (CHC1 3). Mp 160-
1620. [1X] 0 +21.6° (c, 0.21 in MeOH).
(7p(OH),8p,J0/1)-form
From L. cervicornis. Cryst. (CHC1 3). Mp 162-164°. [1X] 0
+89.3° (c, 0.1 in MeOH).
Bowden, B.F. et al, Aust. J. Chern., 1986, 39, 103.

Chromolaenin Sq-01597 C 15H 160 3 M 244.290

Laevigatin Cadalane numbering shown. Constit. of tissues of
Gossypium barbadense infected with Verticillium dahliae.
[62502-10-7]
Pale-yellow cryst. (C 6H 6 jhexane). Mp 134-138°.
9-Me ether: [40817-06-9]. Vergosin
C 16H 180 3 M 258.316
Constit. of G. barbadense. Pale-yellow cryst.
(C 6H 6 /hexane). Mp 121.5-123°.
Stipanovic, R.D. eta/, Phytochemistry, 1975, 14, 1809.

C 15H 160 M 212.291 3,4-Dihydro-6-hydroxy-4,7-dimethyl-2H-1- Sq-01601

Constit. of Chromolaena spp. and of Eupatorium benzopyran-2-one
laevigatum. Cryst. (pet. ether). Mp 74° (65-66°). Bp0. 1
120°. [1X]14 +76S (c, 1.7 in CHC1 3), +88°.

=-~o6o
9,10-Didehydro: [72943-86-3]. Dehydrochromolaenin
C 15H 140 M 210.275
Constit. of C. laevigata. Oil.
11X,2-Dihydro: [72943-87-4]. Dihydroisochromolaenin
M 192.214
C 15H 180 M 214.307
Constit. of C. arnottiana. Oil.

436
7,12-Dihydroxy-4-amorphen-3-one - 1,4-Epoxycadinane Sq-01602 - Sq-01607

Constit. of Heritiera ornithocephala. Oil. [oc]~ -4° (c, 0.3 3,10-Dihydroxy-4,11(13)-muuroladien-12- Sq-01605
in CHC13). Probably a degraded cadinane. oic acid
Cambie, R.C. et a/, Phytochemistry, 1990, 29, 2329 (isol, pmr, cmr)

7,12-Dihydroxy-4-amorphen-3-one Sq-01602 no~"

X@ ~
l;l:

H
8

'OH
C15H 220 4 M 266.336
~OOH
Compounds renumbered using normal numbering system.
12CH2 0H (3P,JO/I)-form
C 1sH240 3 M 252.353 Epizafronic acid
Rei. configs. only of these compds. detd. Constit. of Constit. of Leucanthemopsis pu/veru/enta. Cryst. (as Me
Chromelaena pseudoinsignis. Gum. ester). Mp 175-178° (Me ester). [ocln -180° (c, 2.0 in
EtOH) (Me ester).
12-Deoxy, 8-oxo: 7-Hydroxy-4-amorphene-3,8-dione. 7-
Hydroxy-8-oxoagerap/wrone 3-Ac: 3ft-Acetoxy-10P-hydroxy-4,11(13)-muuroladien-12-oic
acid. Acetylepizafronic acid
C1sH 220 3 M 250.337
Constit. of Ageratina adenophora. Oil. C17H 240 5 M 308.374
Constit. of L. pulveru/enta. Cryst. (as Me ester). Mp 99-
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1432; 1982, 21, 371. 1010 (Me ester). [ocln -ll3° (c, 2.1 in CHC1 3) (Me ester).
[91896-96-7, 91896-97-8)
9,15-Dihydroxy-4,10(14)-cadinadien-3-one Sq-01603 De Pascual Teresa, J.·et al, Tetrahedron, 1984, 40, 2189.

HOH2 Cw
O~OH
H•
/'-..
2,5-Dimethyl-8-isopropyl-1,4-
naphthoquinone
2,5-Dimethy/-8-(1-methy/ethyl)-1,4-naphtha/enedione. 3,7,9-
Cada/atriene-2,5-dione. Cadlllenequinone. Stahlianthusone
[87018-26-6]
Sq-01606

C15H 220 3 M 250.337

9/J-form
9-HydroxyschizandroMI
Metab. of the bird's nest fungus Cyathus striatus. Cryst.
(EtOAc). Mp 151-154°. [oc]i;4 -26° (c, 0.029 in CHC1 3).
Ayer, W.A. eta/, Tetrahedron, 1982, 38, 1409.

8,9-Dihydroxy-1,3,5,7,9-cadinapentaen- Sq-01604 c,sH,60z M 228.290

14,2-olide Cadalene numbering shown. Isol. from seed oil of
3,4-Dihydroxy-5-isopropy/-7-methyl-2H -naphtho[ 1,8- Stahlianthus campanu/atus and essential oil of S.
bclfuran-2-one. 8,9-Dihydroxy-14,2-cada/eno/ide invo/ucratus. Yellow cryst. Mp 58.5-59.0°.
t> Causes intense skin allergy (generalized eczema).
0
3,4-Dihydro: [870 18-25-5]. 2,5-Dihydro-8-isopropy/-1 ,4-
deca/indione. Dilrydrocadslenequinone
C,sH 180 1 M 230.306
Isol. from seeds of S. campanulatus. Cryst. Mp 65-66°.
Opt. inactive.
Ruzicka, L. et al, Helv. Chim. Acta, 1922, S, 345 (synth)
Le Thi Ngoc, L. eta/, Bull. Soc. Chim. Fr., Part II, 1983, 112 (isol)
C15H 140 4 M 258.273
9-Me ether: [61470-49-3]. 8-Hydroxy-9-met/roxy-1.],5,7,9- 1,4-Epoxycadinane Sq-01607
cadbuzpentaen-14,2-olide [73772-79-9]
C16H 160 4 M 272.300 I
Constit. of Sa/mafia malbarica. Cryst. (C 6H6). Mp 206°.

~
Sood, R.P. et al, Phytochemistry, 1982, 21, 2125.

C15H160 M 222.370
Constit. of Dilophus fasciola. Cryst. Mp 54-55°. [ocln
-46.6° (c, 1 in CHC1 3).
Fattorusso, E. et al, Gazz. Chim. /tal., 1979, 109, 589.

437
5,8-Epoxy-4-hydroxy-3-amorphanone - Hibiscone D Sq-01608 - Sq-01614

5,8-Epoxy-4-hydroxy-3-amorphanone Sq-01608 Heritonin Sq-01612

5,8-Epoxy-4-hydroxy-3-cadinanone (incorr.) 4,5-Dihydro-7-methoxy-1 ,5,8-trimethylnaphtho[2,1-b]furan-
[89155-79-3] 2(3aH)-one, 9CI

ofi)
[123514-48-7]

,0,
HO- , '
HI
/---...
C15H140 3 M 252.353
Constit. of Eupatorium adenophorum. Oil. [ex]~ + 30° (c,
0.33 in CC14).
C16H 180 3 M 258.316
Shukla, V.S. et al, Chern. Ind. (London), 1983, 863. lsol. from Heritiera littoralis. Piscicide. Cryst.
(C6H 6 /Etp). Mp 115-116°.
4,10-Epoxymuurolane Sq-01609 Miles, P.lf. et al, J. Nat. Prod. (Lloydia), 1989, 52, 896 (isol, pmr)
[70470-08-5]
Hibiscone A Sq-01613
[74636-00-3]

C15H:u,O M 222.370
Constit. of Dilophus fasciola. Oil. [exln + 15.4° (c, 1 in
EtOH).
Amico, V. eta/, Experientia, 1979, 35, 450. CtsHllpl M 232.322
Constit. of Hibiscus e/atus. Cryst. (CHC1 3 jpet. ether). Mp
9,10-Epoxy-4-muurolene Sq-01610 94-95°. [ex]~ +40° (c, 0.74 in CHC1 3).

ill
9ex-Hydroxy: [74635-99-7]. Hibiscone B
C15H 200 3 M 248.321
I
Constit. of H. e/atus. Cryst. (Etpjpet. ether). Mp 123°.
[exm.s + 3° (c, 1.1 in CHC1 3).
I 9-0xo: [70863-78-4]. Gmelofuran. Hibiscone C
H: C1sH1803 M 246.305
~ Constit. of Gmelia arborea and H. elatus. Cryst. Mp
C15H140 M 220.354 122-123°. [ex]~ -900° (CHC1 3).
(9a.,l Oa. )-form 9-0xo, 3ex-alchohol: [5956-13-8]. Agarol
Constit. of Xenia spp. Cryst. (Et 20jpet. ether). Mp 47- CtsH 200 3 M 248.321
500. [exln + 146° (c, 0.1 in CHC13). Constit. of Aquilaria agallocha. Oil. The registry no. for
this compd. was originally assigned to a C 15H 260
Bowden, B.F. et al, Aust. J. Chern., 1986, 39, 1717. compd. ofunre1ated struct.
Joshi, K.C. et al, Tetrahedron Lett., 1978, 4719 (Gmelofuran)
Heritol Sq-01611 Ferreira, M.A. et al, J. Chern. Soc., Perkin Trans. 1, 1980, 249
[108295-47-2] (Hibiscones, cryst struct, Gmelofuran)
Pant, P. et al, Phytochemistry, 1980, 19, 1869 (Agarol)
Koft, E.R. et al, J. Am. Chern. Soc., 1982, 104, 5568; 1984, 106,
2115 (synth)

Hibiscone D Sq-01614
[74635-98-6]

C15H 160 3 M 244.290

Constit. of Heritiera littoralis. lchthyotoxin. Needles
(MeOH). Mp 271-272°. [ex]~ +261.3°.
Miles, D.H. et al, J. Org. Chern., 1987, 52, 2930 (isol, cryst struct)

C15H.,03 M 244.290
Constit. of Hibiscus e/atus. Cryst. (CHC1 3). Mp 140°. [ex]~
+ 37° (c, 0.97 in CHC1 3).
Ferreira, M.A. et al, J. Chern. Soc., Perkin Trans. J, 1980, 249.

438
Hibiscoquinone A- 10-Hydroxy-4,11-cadinadien-15-... Sq-01615 - Sq-01621

Hibiscoquinone A Sq-01615 Constit. of A. adenophora. Oil. [1X]i;' + 50° (c, 0.1 in

[74635-96-4] CHC1 3).
8-Ketone, 7,11-didehydro: 4,7(1 1)-Amorphadiene-3,8-dione.
7,11-Dehydro-8-oxoageraphorone

~OH ClsH21,02 M 232.322

Constit. of A. adenophora. Oil. [1X]i;' + 297° (c, 0.1 in

~
CHC1 3).
8-Ketone, 7,11-didehydro, 12-hydroxy: 12-Hydroxy-
4, 7(1 1)amorphadiene-3 ,8-dione. 7,11-Dehydro-12-hydroxy-
R =CHO 8-oxoageraphorone
C 15H 200 3 M 248.321
C 15H 140 4 M 258.273 Constit. of A. adenophora. Oil. [1X]i;' +40° (c, 0.8 in
Constit. of Hibiscus elatus and H. tiliaceus. Purple-brown
CHC1 3).
needles (Et 20). Mp 145°. Rapidly decolourized by light
in soln., slowly in solid state. Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1432.
Ferreira, M.A. et at, J. Chern. Soc., Perkin Trans. I, 1980, 249
(isol, struct) 3-Hydroxy-15-cadalenoic acid Sq-01619
Ali, S. et at, J. Chern. Soc., Perkin Trans. I, 1980, 257 (isol) 3-Hydroxy-5-methyl-8-( 1-methylethyl)-2-
naphthalenecarboxylic acid, 9C1. 3-Hydroxy-8-isopropyl-5-
Hibiscoquinone B Sq-01616 methyl-2-naphthoic acid. 7-Hydroxy-15-cadalenoic acid

HOm
[74635-95-3] [51769-00-7]
As Hibiscoquinone A, Sq-01615 with
R = OH
C 14H 140 4 M 246.262
Constit. of Hibiscus elatus and H. tiliaceus, also found in HOOC~
heartwood of Kydia calycina. Purple-brown cryst.
(C6H 6). Mp 169°.
C15H1 60 3 M 244.290
10-Deoxy: [74635-94-2]. Hibiscoquinone C Constit. of Ulmus parvifolia.
C14H1403 M 230.263 Yasuda, S. eta/, CA, 1974, 80, 83284 (isol, ir, pmr)
Constit. of H. elatus. Brown-red cryst. (MeOH). Mp
225° dec.
Ferreira, M.A. eta/, J. Chern. Soc., Perkin Trans. I, 1980, 249 3-Hydroxy-1(10),4-cadinadien-15-oic acid Sq-01620
(iso/, struct) 3-Hydroxy-o-cadinen-15-oic acid
Ali, S. eta/, J. Chern. Soc., Perkin Trans. I, 1980, 257 (isol)
Joshi, K.C. eta/, Planta Med., 1983, 49, 127 (isol)
HOY'A
Hibiscoquinone D
[74635-93-l]
Sq-01617
HOOC~
12

clsHuOJ M 250.337
Ac:
C17H 240 4 M 292.374
Constit. of Heterotheca latifolia. Oil (as Me ester). [1X]~4
-16° (c, 1.4 in CHC1 3) (Me ester).
Bohlmann, F. et at, Phytochemistry, 1982, 21, 2982.
C 15H 120 5 M 272.257
Constit. of Hibiscus elatus. Dark-brown cryst. (CHC1 3).
Mp 350° dec. 10-Hydroxy-4,11-cadinadien-15-oic acid Sq-01621

H£P
Ferreira, M.A. eta/, J. Chern. Soc., Perkin Trans. I, 1980, 249.
H' OH

8-Hydroxy-4-amorphen-3-one Sq-01618
8-Hydroxyageraphorone
HI
~
ClsH 220 3 M 250.337
Constit. of Eremophila interstans.
Ghisalberti, E.L. et at, Phytochemistry, 1990, 29, 2700 (isol, pmr,
cmr)
C 15H 240 2 M 236.353
Abs. configs. unknown. Constit. of Ageratina adenophora.
Oil. [1X]~4 +44° (c, 0.5 in CHC1 3).
8-Ketone: 4-Amorphene-3,8-dione. 8-0xoageraphorone
ClsHuOz M 234.338

439
12-Hydroxy-1(10),4-cadinadien-15-... - 3-Hydroxy-4,9,11(13)-cadinatrien-12-... Sq-01622 - Sq-01627

12-Hydroxy-1(10),4-cadinadien-15-oic Sq-01622 C20H 280 3 M 316.439

acid Constit. of Heterotheca grandiflora. Oil. [ali: + 51.4° (c,
0.6 in CHCl 3).
Deoxy: 1(10),4-Cadinadien-3-one. Cadinen-2-one (incorr.)
C•sHzP M 218.338
Constit. of H. grandiflora. Oil.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1675; 1986, 25,
1474.

C 15H 22 0 3 M 250.337 15-Hydroxy-4,10(14)-cadinadien-3-one Sq-01626

Constit. of Heterotheca latifolia. Oil (as Me ester). [ali: Schizandronol

d5
-116° (c, 0.3 in CHCl 3) (Me ester). [61206-02-81
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2982. 14

0
12-Hydroxy-4,11(13)-cadinadien-15-oic Sq-01623
acid HOH2C
HI

H~
~
Absolute C 15H 220 2 M 234.338
configuration Constit. of the wood of Schizandra nigra and metab. of
HI birds nest fungus Cyathus striatus. Cryst. (Etpjpet.
...l 12 ether). Mp 110°.
~i'CHPH
13 Ac: Cryst. (MeOH aq.). Mp 77-78°.
CisHn03 M 250.337 10,14P-Epoxide: [834 74-53-71. 10, 14P-Epoxy-15-hydroxy-4-
Constit. of Eremophila virgata. New stereochemical class in cadinen-3-one. Schizandronol 8,13P-oxide
the cadinane series. CisH 220 3 M 250.337
11,13-Epoxy, 12-deoxy: 11,13-Epoxy-4-cadinen-15-oic acid From C. striatus. [ali: -5° (c, O.Ql5 in CHCl 3).
C15H 220 3 M 250.337 Takahashi, K. eta/, Chern. Pharm. Bull., 1976, 24, 2000.
Constit. of E. virgata. Needles (Etp). Mp 180-181°. [aln Ayer, W.A. et al, Tetrahedron, 1982, 38, 1409 (isol)
+ 117° (c, 0.9 in CHCl 3).
11R,J3-Dihydro: 12-Hydroxy-4-cadinen-15-oic acid 3-Hydroxy-4,9,11(13)-cadinatrien-12-oic Sq-01627
CisH240 3 M 252.353 acid
Constit. of E. virgata.
6,7-Diepimer: 12-Hydroxy-4,11(13)-muuroladien-15-oic acid
C 15H 220 3 M 250.337
Constit. of E. virgata.
Ghisalberti, E.L. et al, Tetrahedron, 1989, 45, 6297 (cryst struct)

4-Hydroxy-1,9-cadinadien-3-one Sq-01624
C1sH2003 M 248.321
Compounds renumbered from the lit. using normal

H~
cadinane numbering system.
3ft-form
Ledesmic acid
Constit. of Leucanthemopsis pulverulenta. Oil (as Me
ester). [aln + 7.4° (c, 0.80 in CHCl 3) (Me ester).
C 15H 220 2 M 234.338
Ac: 3P-Acetoxy-4,9,11(13)-cadinatrien-12-oic acid.
Me ether: 4-Methoxy-1,9-cadinadien-3-one AcetyUedesmic acid
C16H 240 2 M 248.364 C 17H 2P 4 M 290.358
Constit. of Senecio tomentosus. Oil. [ali: +28° (c, 0.36 Constit. of L. pu/verulenta. Oil (as Me ester). [aln
in CHCl 3). - 11. 7o (c, 5.6 in CHCl 3).
Mericli, A.H. eta/, Phytochemistry, 1989, 28, 1149. (91896-94-5, 91896-95-6)
De Pascual Teresa, J. eta/, Tetrahedron, 1984, 40, 2189.
8-Hydroxy-1(10),4-cadinadien-3-one Sq-01625
8-Hydroxy-J-cadinen-3-one

0~
~'OH
C 15H 220 2 M 234.338
8-Ange/oy/: [73484-10-31.

440
10-Hydroxy-4-cadinen-3-one - 4-lsopropyl-1,6-dimethylnaphthalene ... Sq-01628 - Sq-01634

Xii
10-Hydroxy-4-cadinen-3-one Sq-01628 3-Hydroxy-4,9,11(13)-muurolatrien-12-oic Sq-01632
acid
1
pH
3 I 0
~0~
"""'-
H
6 7

C 15H 240 2 M 236.353

10«-form [20085-91-0] C 15H 200 3
~DOH
M 248.321
Constit. of Taiwania cryptomeroides . Cryst. (hexane). Compounds renumbered from the lit. using normal
Mp 111-111S. [cx]i!· 5 -123.2° (c, 1.2 in CHC1 3). numbering system.
Lin, Y.T. eta/, Tetrahedron Lett., 1968, 3881. 3fl-form
Epiledesmic acid
10-Hydroxy-15-calamenenoic acid Sq-01629 Constit. of Leucanthemopsis pulverulenta. Oil (as Me
ester). [cxln -84.9° (c, 0.83 in CHC1 3) (Me ester).
OH Ac: 3P-Acetoxy-4,9,11(13)-muurolatrien-12-oic acid

~02
C 17H 220 4 M 290.358
Constit. of L. pulverulenta. Oil (as Me ester). [cxln
-70.5° (c, 1.9 in CHC1 3) (Me ester).
[91896-98-9]
De Pascual Teresa, J. et a/, Tetrahedron, 1984, 40, 2189.
C15H 200 3 M 248.321
10«-form Isohemigossypolone Sq-01633
Constit. of Heterotheca latifolia. 5,8-Dihydro-2,7-dihydroxy-6-methyl-4-(1-methylethyl)-5,8-
Me ester: Oil. [cxln +65° (c, 0.1 in CHC1 3). dioxo-1-naphthalenecarboxaldehyde. 5-Formyl-3-hydroxy-8-
10fl-form isopropyl-2-methyl-1,4-naphthoquinone. 3-Hydroxy-2,5-

W
Constit. of H. latifolia. dioxo-1(6),3,7,9-cadalatetraen-14-al
Me ester: Oil. [69688-68-2]
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2982.
O CHO
H
2-Hydroxy-8,12-dioxo-4,11(13)- Sq-01630 I
bulgaradien-15-oic acid #
Panal
0
[115374-28-2]
C 15H 140 5 M 274.273

~
Probably occurs in Bombax malabaricum. Orange cryst.
Incorrectly considered to be Hemigossypolone; not
identical with authentic Hernigossypolone.
HOOC~o 3-Me ether: [74636-01-4]. 8-Formyl-7-hydroxy-5-isopropyl-
HI 2-methoxy-3-methyl-1 ,4-naphthoquinone.
~CHO lsohemigossypolone methyl ether
CI,H160s M 288.299
CJsHJaOs M 278.304 Isol. from root bark of B. malabaricum. Yellow cryst.
Constit. of luminous mushroom Panel/us stipticus. (MeOH). Mp 82°.
Amorph. solid. [cxln - 17° (c, 0.9 in MeOH).
Seshadri, V. et at, Curr. Sci., 1971, 40, 630 (isol)
Nakamura, H. et al, Tetrahedron, 1988, 44, 1597 (isol) Sankaram, A.V.B. eta/, Phytochemistry, 1981, 20, 1877 (isol, uv,
ir,pmr, ms)
3-Hydroxy-4,7(11 )-muuroladien-8-one Sq-01631
4-lsopropyl-1,6-dimethylnaphthalene, SCI Sq-01634
HXb:oH 1,6-Dimethyl-4-(1-methylethyl)naphthalene, 9CI. Cadalene
[483-78-3]
"""'- 0
HI
C 15H 22 0 2 M 234.338
3«-form
Ac: [62458-51-9]. 3-Acetoxy-4,7(11)-muuroladien-8-one. 3cx-
Acetoxy-6fJH-cadina-4, 7(11 )-dien-8-one
C1,H 240 3 M 276.375 C1sH1a M 198.307
Cons tit. of Ageratina petiolaris. Oil. Occurs in various plants, e.g. Abies sibirica resin and
Dictyopteris divaricata. di9 0.979. Bp720 291-292°, Bp3
Bohlmann, F. et at, Chern. Ber., 1977, 110, 301. 106°. n~ 1.5851.
Picrate: Orange needles (EtOH). Mp 115°.

441
2-Isopropyl-4,7-dimethyl-1-naphthol- Mansonone C Sq-01635 - Sq-01641

Ruzicka, L. et al, Helv. Chim. Acta, 1922, 5, 369 (synth)
Barnett, E. de B. et al, J. Chern. Soc., 1933, 22 (synth)
Johnson, W.S. et al, J. Am. Chern. Soc., 1941, 69, 792 (synth)
Nagasampagi, B.A. et al, Tetrahedron, 1966, 22, 1949 (uv, ir)
Kohli, J.C. et al, Experientia, 1912, 28, 131 (synth)
Takahashi, K. et al, Chern. Pharm. Bull., 1916, 24, 2000 (cmr)
2-Isopropyl-4,7-dimethyl-1-napbthol Sq-01635
4-Hydroxyisocadalene
Isol. from Gossypium hirsutum bracts. Mp 62-63°. The abs.
config. has been detd.; the (R)-enantiomer is
dextrorotatory but there is no indication in the literature
as to which enantiomer occurs naturally.
Me ether: [72843-51-7].
C 16H 200 3 M 260.332
From G. hirsutum. Cryst. (CClJ, also descr. as yellow
oil. Mp 100-102°. One natural sample is definitely
racemic. Posn. of methylation not indicated.
Jeffs, P.W. et al, J. Org. Chern., 1915, 40, 2958.
Stipanovic, R.D. et al, Phytochemistry, 1915, 14, 1041 (ms, ir, uv,
struct)
McCormick, J.P. et al, J. Org. Chern., 1984, 49, 34 (synth)
Stipanovic, R.D. et al, J. Org. Chern., 1986, 51, 2500 (abs config)

C 15H 180 M 214.307 Mansonone A Sq-01639

Constit. of Heterotheca inu/oides. Oil. 5 ,6, 7,8- Tetrahydro-3,8-dimethy/-5-( 1-methy/ethyl)-1 ,2-
Me ether: naphtha/enedione, 9Cl. 5,6,7,8- Tetrahydro-5-isopropy/-3,8-
C 16H 14,0 M 228.333 dimethy/-1 ,2-naphthoquinone
Constit. of H. inuloides. Oil. [7715-94-8]
Bohlmann, F. et al, Chern. Ber., 1916, 109, 2021.

4-lsopropyl-7-methyl-1- Sq-01636
naphtbalenecarboxaldehyde
7- M ethy/-4-( 1-methy/ethyl)-1-naphtha/enecarboxa/dehyde.
14-Cadll/enal

C 15H 200 1 M 232.322

Constit. of Mansonia a/tissima heartwood. Red cryst.
(cyclohexane). Mp 117-118°. [ocln + 680° (c, 0.2 in
CHC1 3). ).max 209 (log e 4.32) and 430 nm (2.93) (EtOH).
Marini Betto1o, G.B. et al, Tetrahedron Lett., 1965, 4857 (isol, uv,
pmr)
C 15H 160 M 212.291 Tanaka, N. et al, Tetrahedron Lett., 1966, 2767 (isol, uv)
Constit. of Helichrysum ambiguum. Oil. Dumas, M.T. et al, Experientia, 1983, 39, 1089 (isol)
Jakupovic, J. et al, Phytochemistry, 1989, 28, 543. Murali, D. et al, Indian J. Chern., Sect. B, 1987, 26, 668 (synth)

1-lsothiocyanato-4-muurolene Sq-01637 Mansonone B Sq-01640

4-Muuro/ene-1-isothiocyanate
[117605-65-9]
H:¢20I I
0

C15H2003 M 248.321
Tautomeric with the 1,2-naphthoquinone struct. Constit.
C 16H 25NS M 263.446 of Mansonia altissima heartwood. Gold-yellow cryst.
Metab. of the sponge Acanthella pulcherrima. (hexane). Mp 68-69°. ).max 226 (loge 3.68), 272(3.69) and
408 nm (2.40) (EtOH).
Capon, R.J. et al, Aust. J. Chern., 1988, 41, 979.
Marini Bettolo, G.B. et al, Tetrahedron Lett., 1965, 4857 (isol, uv,
pmr)
Lacinilene C Sq-01638
1, 7- Dihydroxy-1,6-dimethy/-4-(1-methy/ethyl)-2(1H)-
naphtha/enone, 9Cl. 1,7-Dihydroxy-4-isopropy/-1 ,6-dimethy/- Mansonone C Sq-01641
3,8-Dimethy/-5-(1-methy/ethyl)-1 ,2-naphtha/enedione, 9Cl.
2(1H)-naphthalenone
Cada/ene-2 ,3-quinone. Cada/ene-7,8-quinone (inc orr.)
[41653-72-9]
[5574-34-5]

(R)-form

M 246.305
M 228.290

442
Mansonone D - Mansonone I Sq-01642 - Sq-01646

Constit. of Mansonia altissima and Ulmus laciniata Mansonone G Sq-01644

heartwoods. Orange cryst. (hexane). Mp 134-138°.
Marini Bettolo, G.B. et al, Tetrahedron Lett., 1965, 4857 (isol, uv,
pmr)
Oliver, R.W.A. et al, J. Chern. Soc. B, 1971, 341 (ms)
Krishnamoorthy, V. et al, Phytochemistry, 1971, 10, 1669 (synth)
Strunz, G.M. et al, Phytochemistry, 1989, 28, 2861 (synth)
6-Hydroxy-3,8-dimethyl-5-( 1-methylethyl)-1 ,2-
naphthalenedione, 9Cl. 6-Hydroxy-5-isopropyl-3,8-dimethyl-
1,2-naphthoquinone, 8Cl. 8-Hydroxy-1(6),4,7,9-
cadalatetraene-2,3-dione
[7715-96-0]

Mansonone D Sq-01642
1,2-Dihydro-1,5,8-trimethylnaphtho[2,1-blfuran-6,7-dione,
9C/
[5090-86-8]

CtsHt603 M 244.290
Constit. of Mansonia altissima heartwood. Orange cryst.
Mp 210-213°.
Me ether: [36150-18-2]. 6-Methoxy-3,8-dimethyl-5-(1-
methylethyl)-1 ,2-naphthalenedione, 9CI
Ct,H 180 3 M 258.316
CtsH 140 3 M 242:274 Constit. of Zelkova serrata heartwood. Orange cryst.
Constit. of Mansonia altissima. Orange cryst. Mp 163.5-164.SO.
(cyclohexanejC 6H 6). Mp 73-75°. Tanaka, N. et al, Tetrahedron Lett., 1966, 2767 (isol, ir)
Vishwanatha, V. et al, Indian J. Chern., 1973, 11, 974 (synth, ir,
Marini Bettelo, G.B. et a/, Tetrahedron Lett., 1965, 4857 (isol, uv,
pmr)
pmr)
Viswanatha, V. et al, Tetrahedron Lett., 1974, 247 (synth, uv, ir,
pmr) Mansonone H Sq-01645
2,3-Dihydro-4-hydroxy-3,6,9-trimethylnaphtho[ 1,8- be ]pyran-
Mansonone F Sq-01643 7,8-dione, 9C/, 8CI
3,6,9-Trimethylnaphtho[1,8-bc]pyran-7,8-dione, 9C/, 8CI [13383-59-0]
[5090-88-0]

CtsH 1404 M 258.273

C 15H 120 3 M 240.258 Constit. of Mansonia altissima heartwood. Red cryst. Mp
Cadalane numbering shown. Constit. of Mansonia 320°.
altissima and Ulmus laciniata heartwoods. Violet cryst. Me ether: [7715-98-2]. Mansonone M
(C 6H 6). Mp 214-215°. Amax 234 and 555 nm (EtOH). C 16H 160 4 M 272.300
11,12-Dihydro: [5090-87-9]. Mansonone E Constit. of Helicteres angustifolia. Orange-red needles
CtsHt403 M 242.274 (MeOH). Mp 208-209°. [1X]i; +28.3° (c, 3.1 in CHCI3).
Constit. of M. altissima, U. laciniata and U. parvijlora. Tanaka, N. et al, Tetrahedron Lett., 1966, 2767 (isol, ir)
Orange-yellow cryst. (cyclohexane). Mp 148-149°. [IX]~ Oliver, R.W.A. et al, J. Chern. Soc. B, 1971, 341 (ms)
+82°. Abs. config. unknown. Chen, C.-M. eta/, Phytochemistry, 1990, 29, 980 (isol, pmr, cmr)
14-Hydroxy: [24562-65-0]. Mansonone L
CtsH 120 4 M 256.257 Mansonone I Sq-01646
Constit. of M. altissima heartwood. Violet cryst. [26511-91-1]
(EtOAc). Mp 165-167°.

0~
~ I ~
0
Marini Bettolo, G.B. et al, Tetrahedron Lett., 1965, 4857 (isol, uv,
pmr)
Tanaka, N. et al, Tetrahedron Lett., 1966, 2767 (isol, pmr, deriv)
Galeffi, C. et al, Tetrahedron Lett., 1969, 3583 (Mansonone L) #
Oliver, R.W.A. eta/, J. Chern. Soc. B, 1971, 341 (ms)
Best, W.M. et al, Aust. J. Chern., 1986, 39, 647 (synth) 0
Chen, C.-M. et al, Phytochemistry, 1990, 29, 980 (isol, pmr, cmr)
OH
CtsHt404 M 258.273
Constit. of Mansonia altissima. Cryst. Mp 213-214°.
Shimoda, K. et al, Mokuzai Gakkaishi, 1967, 13, 126 (isol, struct)
Best, W.M. et al, Aust. J. Chern., 1986, 39, 647 (synth)

443
4,9-Muuroladien-14-al- 4,10(14)-Muuroladien-15-oic acid Sq-01647 - Sq-01653

mo
4,9-Muuroladien-14-al Sq-01647 4,7(11 )-Muuroladiene-8,9-diol Sq-01650
Sclerosporal

(-)-form
HI
~ CISHl40l M 236.353
C 15H 120 M 218.338 (8rx.,9rx.)-form
(-)-form [69394-04-3] 9-Ac: [67604-10-8]. 8-Acetoxy-9-hydroxyverboccidentene
Constit. of Sclerotinia fruticola. Sporogenic agent. Oil. C17H160 3 M 278.391
[1X]i,<' -33.3° (c, 0.62 in CHC1 3). Constit. of Verbesina occidentalis. Oil.
14-Carboxylic acid: [66419-03-2]. 4,9-Muuroladien-14-oic Bohlmann, F. et al, Phytochemistry, 1978, 17, 453.
acid. Sclerosporin
C15H 120 1 M 234.338 4,9-Muuroladiene-1,8-diol Sq-01651
Constit. of S. fruticola. Sporogenic antifungal agent. rx.-Muurolene-1 ,8-dio/
Cryst. (pet. ether). Mp 159-160°. [1X)i,<' +11.1° (c, O.Q35
in MeOH).

~-oH
(+)-form [97286-74-3)
Oil. Bpu 110°. [IX]~ +35.3° (c, 0.69 in CHC13).
14-Carboxylic acid: [97286-73-2]. (- )-Sclerosporin
C15H120 1 M 234.338
From Diplocarpon mali. Shows antifungal props. Cryst.
(pet. ether). Mp 163°. [IX]~ -17° (c, 3.7 in CHC1 3). CISHl40l M 236.353
Katayama, M. et a/, Tetrahedron Lett., 1979, 1773; 1983, 24, 1703; 8rx.-form
1984, 25, 4685 (isol, synth, struct, abs config) 8-Angeloyl: [73484-13-6].
Kitahara, T. et al, Tetrahedron, 1985, 41, 5475 (synth) C10H300 3 M 318.455
Sawai, K. et al, Agric. Bioi. Chern., 1985, 49, 2501 (isol) Constit. of Heterotheca grandifiora. Oil. [1X]i;l -62° (c,
2.4 in CHC1 3).
4,1 0(14)-Muuroladiene Sq-01648 Bohlmann, F. et al, Phytochemistry, 1979, 18, 1675.
1-Muurolene. y-Amorphene
[24268-39-1] 4,10(14)-Muuroladiene-1,3,9-triol Sq-01652
1,3 ,9-Trihydroxymuurolene

CISHl4 M 204.355
Constit. of Pinus sylvestris, Amorpha fruticosa and Agathis
CISHl403 M 252.353
australis. Oil. [1X]n -1.8°.
(1rx.,3rx.,9rx.)-form
Briggs, L.H. et al, Aust. J. Chern., 1973, 26, 2229.
Constit. of Helichrysum dasyanthum. Gum.
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1119.
4(15),10(14)-Muuroladiene Sq-01649
e-Muurolene

m
4,10(14)-Muuroladien-15-oic acid Sq-01653
[1136-29-4] y-Muurolen-15-oic acid

~
HOOC~
C15H 14 M 204.355
~ H•
~
I

C15H 120 1 M 234.338

Constit. of ylang-ylang oil and Swedish turpentine. Oil.
Constit. of Trichogonia grazielae. Oil. [1X)~4 + 28.1° (c, 8.2
[IX)~ + 50.7° (c, 2.2 in CHC1 3).
in CHC1 3) (as Me ester).
Burk, L.A. et al, Tetrahedron, 1976, 32, 2083 (isol)
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1323.
Koster, F.-H. et al, Justus Liebigs Ann. Chern., 1986, 78 (synth,
cmr)

444
4,9-Muuroladien-14-ol- 4-Muurolen-1-ol Sq-01654 - Sq-01660

4,9-Muuroladien-14-ol Sq-01654 (3p,JO/I)-form [23971-80-4]

From T. cryptomeroides. Cryst. (EtOAc). Mp 168-170°.
[1X]i: -1 UO (c, 1 in MeOH).
Kuo, Y.H. eta/, Tetrahedron Lett., 1969, 2375 (isol)
Ohloff, G. eta/, Helv. Chim. Acta, 1970, 53, 245 (synth)

4-Muurolene-7, 15-diol Sq-01658

Pernetol
C 15H 240 M 220.354
[99957-16-1]

CQ
Constit. of Xenia spp. Oil. [1X]n +67° (c, 0.25 in CHCI 3).
41X,51X-Epoxide, 15-Ac: 15-Acetoxy-4rx.,5rx.-epoxy-9-muurolene H:
C 17H 260 3 M 278.391
From X. spp. Oil. [1X]n -19° (c, 0.3 in CHC1 3). 15
14-Aldehyde: see 4,9-Muuroladien-!4-al, Sq-01647 HOCH2
Bowden, B.F. eta/, Aust. J. Chern., 1986, 39, 1717. HI OH
~
4(15),5,11-Muurolatriene Sq-01655 C 15H 260 2 M 238.369
BicyclosesquipheUandrene 7p-form
[54324-03-7] Constit. of Pernettya furens. Amorph. powder. [1X]n
+ 14.09° (c, 0.908 in CHC1 3).
15-Aldehyde: [99957 -17-2]. 7- Hydroxy-4-muurolen-15-al.
Pernetal
CtsH 240 2 M 236.353
From P. furens. Gum. [1X]n + 17.8° (c, 1.06 in CHCI 3).
15-Carboxylic acid: [99957-13-8]. 7-Hydroxy-4-muurolen-
15-oic acid. Pernetic acid A
C 15H 24 M 204.355 C 15H 240 3 M 252.353
Constit. of Piper cubeba. Oil. From P. furens. Cryst. (MeCN aq.). Mp 143-144°. [1X]n
Terhune, S.J. et a/, Phytochemistry, 1974, 13, 1183 (iso/, struct) +2.7° (c, 1.64 in CHCI 3).
Vig, O.P. et a/, J. Indian Chern. Soc., 1976, 53, 593 (synth) 15-Carboxylic acid, Me ester: [99957-18-3].
Ct6HuOJ M 266.380
Muurolene dihydrochloride Sq-01656 From P. furens. Cryst. (EtOAcjpet. ether). Mp 96-97°.
[10207-94-0] [1X]n +2.9° (c, 2.17 in CHC1 3).
Hosozawa, S. eta/, Phytochemistry, 1985, 24, 2317 .

. ~ 3-Muurolen-1-ol
lsoepicubenol
Sq-01659

~
I

~
C 15H 26Cl2 M 277.276
Prod. of HCI addn. to sesquiterpenes used as
characterising deriv. Plates. Mp 86-87°. [1X]i? -12° (c,
0.107 in CHCI 3).
Gati1ov, Y.V. eta/, Khim. Prir. Soedin., 1981, 1, 52 (cryst struct) C 15H 260 M 222.370
Borg-Karlson, A.K. eta/, Acta Chern. Scand., Ser. B, 1982, 36, (lp,JOrx.)-form [73484-14-7]
137 (cryst struct) Constit. of Heterotheca grandijlora. Oil.
Soffer, M.D. eta/, Tetrahedron Lett., 1983, 24, 1455 (cryst struct,
abs config) Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1675 (isol)
Bohlmann, F. et al, Tetrahedron, 1983, 39, 443 (synth)

4-Muurolene-3,10-diol Sq-01657
4-Muurolen-1-ol Sq-01660

HO,rKH

C 15H 260 2
~ (3o,!O~)·fo'm
M 238.369
(-)-form

(3rx.,10f/)-form [23971-79-1] C 15H 260 M 222.370

Constit. of Taiwania cryptomeroides. Cryst. (EtOAc). (-)-form
Mp 206-207°. [1X]i,7 -47.7° (c, I in EtOH). Epicubenol. epi-Cubenol
3-Ketone: [23971-78-0]. 10-Hydroxy-4-muurolen-3-one Constit. of cubeb oil and of Cedrus atlantica. Oil. Bp2. 5
C 15H 240 2 M 236.353 170-180° (bath). [1X]~ -100.6° (CHC1 3).
Constit. of T. cryptomeroides. Cryst. (hexane). Mp 126- (+)-form
1270. [1X]i,7 -104° (c, 1 in EtOH). ent-Epicubenol

445
4-Muurolen-10-ol - 1,2,8,8a-Tetrahydro-1-isopropyl-4,6-... Sq-01661 - Sq-01666

Constit. of Scapania undulata. Oil. [1X]i;' + 111.6° (c, 4. 7 FJrocurzerenone Sq-01663

in CHC1 3). 6,7-Dihydro-1,5,8-trimethylnaphtho[2,1-b}furan, 9CI
Ohta, Y. eta/, Tetrahedron Lett., 1967, 2073 (isol, struct) [20013-75-6]
Gerber, N.N., Phytochemistry, 1971, 10, 185 (isol)
Connolly, J.D. et al, Phytochemistry, 1982, 21, 233 (isol, struct)

4-Muurolen-10-ol

H pH
Sq-01661

~0
~(1~,5~,6~,10.)-fo~ C1sH 160 M 212.291
Constit. of the rhizomes of Curcuma zedoaria. Cryst. (pet.
ether). Mp 76.5-77.SO.
4,5-Dihydro: [59462-26-9]. Dihydropyrocurzerenone
C1sH11;0 M 222.370 C 15H 180 M 214.307
(JP.5P,6P,101X)-form [36564-42-8] Torreyol. t5-Cadinol. Constit. of Chloranthus serratus. Cryst. (pet. ether). Mp
Sesquigoyol 65-66°. [IX]~ -28° {c, 0.84 in CHC1 3).
Constit. of Pinus parviflora, P. formosana, Siberian cedar Viswanatha, V. eta/, J. Chern. Soc., Perkin Trans. 1, 1974, 450
and other spp. Cryst. Mp 139-140°. [1X]i? + 102° (c, 3.2 (synth)
in EtOH). First thought to be a cadinene and therefore Hikino, H. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 478 (isol,
appropriately named but since shown to be a struct)
Takemoto, T. eta/, Chern. Pharm. Bull., 1976, 24, 531 (deriv)
muurolane. Miyashita, M. eta/, J. Org. Chern., 1984, 49, 3728 (synth)
(I1X.51X,61X,l Op)-form
Cedrelllnol. Brown-algae cadinol. Pilgerol
Constit. of P. a/bicaulis, P. armandi, Juniperus communis Ryomenin Sq-01664

ro
and Pilgerodendron uniferum. Also from Cedrela [72896-75-4]
odorata, Chamaecyparis lawsoniana, Athrotaxis

Hooey
selaginoides, Cryptomeria japonica, Dictyopteris
divaricata and others (some earlier identifications prob.
erroneous in view of uncertainty over struct.). Mp 139-
1400. [1X]i? -102° (c, 3.2 in EtOH).
(1 P.5P,6P,J Op)-form [19912-62-0]
T-Muurolol .
Constit. of Taiwania cryptomeroides, Arthrotaxis CISHI803 M 246.305
selaginoides and Cedrela toona. Cryst. Mp 80.5-81.5°.
Constit. of Arachniodes standishii. Cryst. (C6H 6 /hexane).
Mp 204-207°. [1X]~ -2W (c, 0.14 in MeOH).
[IX]~ -1 W (c, 1 in CHC1 3).
Tanaka, N. et a/, Chern. Pharm. Bull., 1980, 29, 3070.
Cheng, Y.S. eta/, J. Chern. Soc., Chern. Commun., 1967, 565 (isol)
Nagasampagi, B.A. eta/, Tetrahedron Lett., 1968, 1913 (synth)
Vig, O.P. et a/, Indian J. Chern., Sect. B, 1979, 17, 552 (synth) 5,5a,6, 7-Tetrahydro-1,5-
Borg-Karlson, A.-K. et a/, Tetrahedron, 1981, 37, 425 (struct, dimethylnaphtho[2,1-b)furan-8(4H)-one,
config)
Rodriguez-Avial Franke, L.R. eta/, Tetrahedron, 1984, 40, 3491 9CI Sq-01665
(synth) I ,2,3 ,4-Tetrahydro-15-nor-4-oxochromolaenin
(107390-17-0]
Pernetic acid B Sq-01662
4,11-Amorphadien-15-oic acid
[99957-14-9]
H:

~~ Ct4Ht,02 M 216.279
Constit. of Baccharis ulicina. Cryst. Mp 125°.
Zdero, C. eta/, Phytochemistry, 1986, 25, 2841.
CISH2202 M 234.338
Probable abs. config. indicated. Constit. of Pernettya 1,2,8,8a-Tetrahydro-1-isopropyl-4,6- Sq-01666
furens. Cryst. (MeCN aq.). Mp 147-149°. [1X]n -31.7° (c, dimethyl-2-naphthol
0.51 in CHC1 3). [60263-13-0]
6-Epimer: [100019-20-3]. 4,11-Cadinadien-15-oic acid.
Pernetic acid C
CISH2202 M 234.338
From P.furens. Cryst. (MeCN aq.). Mp 158-160°. [1X]n ~
+ 32.9° (c, 0.42 in CHC13). ~-oH
Hosozawa, S. eta/, Phytochemistry, 1985, 24, 2317.

446
Thespesone - Gliocladic acid Sq-01667 - Sq-01673

C 15H120 M 218.338
Constit. of Heterotheca inuloides. Oil.
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 2021.
Nor- and secocadinanes
Thespesone Sq-01667
[85889-26-5]
Calacone Sq-01670

Absolute
configuration
CtsHt404 M 258.273
Constit. of Thespesia populnea. Yellow needles C 15H 240 M 220.354
(CHC1 3fC 6HJ. Mp 156-157°. [IX]~ -336° (c, O.Dl in Constit. of Acarus calamus. Oil. [IX]~ +0.9° (pet. ether).
CHC1 3). Vrkoc, J. eta/, Collect. Czech. Chern. Commun., 1961, 26, 1021,
Nee1akantan, S. et a/, Indian J. Chern., Sect. B, 1983, 22, 95. 1343.

Thespone Sq-01668 Chromoamottione Sq-01671

1,5,8-Trimethylnaphtho[2,1-blfuran-6,7-dione [72943-97-6]
[85889-25-4] I
H•

~0
Ct4H1a02 M 218.295
Constit. of Chromo/aena arnottiana. Oil. [1X]i;l + 151° (c, 0.5
C1sH 120 3 M 240.258
in CHCI 3).
Constit. of Thespesia populnea. Red needles (CHC1 3/C6H 6).
Mp 196-197°. Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1177 (iso/, struct)
Nee1akantan, S. eta/, Indian J. Chern., Sect. B, 1983, 22, 95.
3,5-Dihydro-8-hydroxy-5-isopropyl-2,7- Sq-01672
Verboccidentafuran Sq-01669 dimethyl-1-benzoxepin-4(2H)-one
[67604-03-9]

C 15H 100 M 216.322

~0 C 15H 100 3 M 248.321
Constit. of Heritiera ornithocephala. Amorph. solid. Mp
100-105°. [IX]~ -25° (c, 0.3 in CHC1 3).
Constit. of Verbesina occidentalis. Oil. [IX]~ + 54.8° (c, 1 in
CHC1 3). Cambie, R.C. et al, Phytochemistry, 1990, 29, 2329 (isol, pmr, cmr)
41X,51X-Epoxide: Verboccidentafuran 4rx.,5rx.-epoxide
C 15H100 2 M 232.322 Gliocladic acid Sq-01673
Constit. of Baccharis sa/ificifolia. [IX]~ + 24° (c, 0.25 in [82425-48-7]
CHC1 3).
2-0xo: 2-0xoverboccidentafuran
CtsH 1802 M 230.306
Constit. of Smallanthus uvedalia. Oil.
1-Hydroxy: [67604-05-1]. IP-Hydroxyverboccidentafuran
C 15H100 2 M 232.322 I
Constit. of V. occidentalis. Oil. [1X]i;l +63.4°. ~
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 453 (isol) C14H2P4 M 254.325
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 1689 (synth, Antitumour antibiotic. Isol. from G/iocladium virens.
struct)
Zdero, C. eta/, Phytochemistry, 1986, 25, 2841 (epoxide)
Active against Bacteroides.
Dominguez, X.A. eta/, Phytochemistry, 1988, 27, 1863 ltoh, Y. eta/, J. Antibiot., 1980, 33, 468 (isol)
(Oxoverboccidentafuran) ltoh, Y. et a/, J. Antibiot., 1982, 35, 541 (struct)

447
Heptelidic acid - Khusitene Sq-01674- Sq-01680

Heptelidic acid Sq-01674 5-lsopropyl-8-methyl-2-naphthol Sq-01678

Avocettin 8-Methyi-5-(J-methy/ethyl)-2-naphthaleno/, 9CI. Lacinilene
[7431 0-84-2] A. 15-Nor-3-cada/eno/
[40525-06-2]

C 15H 200 5 M 280.320

Metab. of Glioc/adium virens, Anthostoma avocetta, C14H 1,o M 200.280
Trichoderma viride and Chaetomium g/obosum. Constit. of the heartwood of Ulmus /aciniata. Mp 101-
Antibiotic. Needles (CH 2Cl2jcyclohexane). Mp 62-65°. 1020.
[rx] 0 + 7.4° (c, 1.0 in CHC1 3). Ac: Mp 94-96°.
Arigoni, D., Pure Appl. Chern., 1975, 41, 219 (struct, biosynth) Suzuki, H. eta/, Mokuzai Gakkaishi, 1971, 17, 221; 1972, 18, 37;
ltoh, Y. eta/, J. Antibiot., 1980, 33, 468, 525 (struct) CA, 76, 150983 (uv)
Stipanovic, R.D. eta/, Tetrahedron, 1983, 39, 1103 (cryst struct) Nishikawa, K. eta/, Mokuzai Gakkaishi, 1972, 18, 471; CA, 77,
149681.
Nagaoka, M. eta/, Mokuzai Gakkaishi, 1972, 18, 509; CA, 78,
1-Isopropyl-4-methylnaphtbalene Sq-01675 15872 (struct)
1-Methy/-4-( 1-methy/ethyl)naphtha/ene, 9CI
[1680-53-1] Khusilal Sq-01679
[2221-68-3]

~
Ct4Ht, M 184.280 OHC~
dl4·5 0.993. Bp 12 145-148°. nJ:· 5 1.5907. HI
Picrate: Orange-yellow needles (EtOH). Mp 99-100°. ~
Rapson, W.S. eta/, J. Chern. Soc., 1933, 128. C 14H 180 M 202.296
Constit. of vetiver oil (Vetiveria zizanioides). Bp0 _3 115°
(bath). [rx]~ -261° (c, 9.7 in CHC1 3).
1-Isopropyl-7-methylnaphtbalene Sq-01676
Apocada/ene Oxime: Plates (pet. ether). Mp 101-102°.
C14H 16 M 184.280 Kalsi, P.S. eta/, Tetrahedron, 1964, 20, 2617 (isol)
Gill, H.S. eta/, Chern. Ind. (London), 1969, 1779 (struct)
d~00.983. Bp 282°, Bp 12 139-141°. ni,U 1.5884. Hagiwara, H. et a/, Chern. Lett., 1990, 2067 (synth)
Picrate: Orange-yellow needles (EtOH). Mp 166° (163-
1640).
Khusitene Sq-01680
Ruzicka, L. eta/, Helv. Chim. Acta, 1922, S, 710.
Barnett, E. de B. eta/, J. Chern. Soc., 1933, 437.

5-lsopropyl-3-metbyl-2-naphthol Sq-01677
14-Nor-3-cada/eno/ (+)-form

Ct4Hn M 190.328
(+)-form [35043-54-0]
Constit. of vetiver oil. Oil. Bp 2 115° (bath). [rx]~ + 124°
(c, 3 in CHC1 3).
C 14H 160 M 200.280 (-)-form
Me ether: [73484-08-9]. 1-/sopropy/-6-methoxy-7- Bp 2 110° (bath). [rx]i? -118° (c, 1.4 in CHC1 3).
methy/naphtha/ene. 3-Methoxy-14-norcada/ene 11-0xo: [2221-76-3]. Khusitone
C 15H 180 M 214.307 Ct4H200 M 204.311
Constit. of Heterotheca grandijlora. Oil. Minor constit. of oil of Vetiveria zizanioides. Bp 0 _35 118°
Bohlmann, F. et a/, Phytochemistry, 1979, 18, 1675. (bath). [rx]~ - 134.8° (c, 0.59 in CHC1 3).
11-0xo, semicarbazone: Cryst. (EtOH). Mp 183-184°. [rx] 0
-65.4° (c, 1.22 in CHC1 3).
Trivedi, G.K. eta/, Tetrahedron, 1964, 20, 2631 (abs config)
Raj, B. et a/, Indian J. Chern., 1971, 9, 1047 (isol, struct)
Vig, O.P. et a/, Indian J. Chern., 1974, 12, 1050 (synth)

448
Norkhusinol oxide - 5,6,7,8-Tetrahydro-5-isopropyl-3-... Sq-01681 - Sq-01686

Norkhusinol oxide Sq-01681 Luo, X. eta/, Helv. Chim. Acta, 1984, 67, 1515
(Dihydroguinghaosu)
[1 02818-86-0] Zhongshan, W. eta/, Can. J. Chern., 1985, 63, 3070 (pmr, cmr)
Acton, N. eta/, Planta Med., 1985, 441 (Artemistene)
Klayman, D.L., Science (Washington, D.C.), 1985, 228, 1049 (rev,
pharmacal)
El-Feraly, F.S. eta/, Phytochemistry, 1986, 25, 2777 (biosynth)
Zhou, W.-S., Pure Appl. Chern., 1986, 58, 817 (synth)
Gu, H. eta/, Int. Congr. Ser.-Excerpta Med., 1987, 750, 657 (rev,
pharmacol)
Luo, X.D. et a/, Med. Res. Rev., 1987, 7, 29 (rev, synth, struct,
CI4Hl202 M 222.327 pharmacal)
Constit. of oil of Vetiveria zizanioides. Plant growth factor. Akhila, A. et a/, Phytochemistry, 1987, 26, 1927 (biosynth)
Blasko, G. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 1273 (pmr, cmr)
Cryst. Mp 76°. [ex]i? -120°.
Roth, R.J. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 1183 (synth)
Kalsi, P.S. eta/, Tetrahedron, 1985, 41, 3387. Ye, B. eta/, J. Chern. Soc., Chern. Commun., 1990, 726 (syn.th)
El-Feraly, F.S. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 66 (synth,
Artemisitene)
Pernetic acid D Sq-01682 Ravindranathan, T. eta/, Tetrahedron Lett., 1990, 31, 755 (synth)
[999 57-15-0]
Secofloribundione Sq-01684
[116374-12-0]

C1sH2204 M 266.336
Constit. of Pernettya furens. Cryst. (EtOAcfpet. ether).
Mp 134.5-135.SO. [ex]D -21.7° (c, 0.94 in CHC1 3).
8-Epimer: [100019-21-4]. Pernetic acid E
CisH120 4 M 266.336 C15H2404
~
M 268.352
Constit. of Liabum jloribundum. Oil.
OCHO

From P. furens. Cryst. (EtOAc/pet. ether). Mp 134.5-

1360. [ex]D -128.5° (c, 0.85 in CHC1 3). Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1771.
Hosozawa, S. eta/, Phytochemistry, 1985, 24, 2317.
Tetradehydrochromoamottione Sq-01685
Qinghaosu Sq-01683 1-Acetyl-4, 7-dimethyl-2-naphthol. 8-Hydroxy-12-norcadalen-
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1 ,2- 11-one

M
benzodioxepin-10(3H)-one, 9CI. Arteannuin. Artemisinin,
INN. Qing Hau Sau. QHS
[63968-64-9]

~OH
C14H 140 2 M 214.263
Constit. of Chromolaena laevigata. Oil.
Misra, L.N. et a/, Tetrahedron, 1985, 41, 5353.

C1sH220 5 M 282.336 5,6,7,8-Tetrahydro-5-isopropyl-3-methyl-2- Sq-01686

Constit. of Artemisia annua (Qinghaosu). Antimalarial. naphthol
Needles. Mp 156-157°. [ex]~ +66.3°. 3-Hydroxy-14-norcalamenene
I> KD4170000. [73484-02-3]
12P-Alcohol: Dihydroqinghaosu
CisH 24 0 5 M 284.352
I sol. from qainghaosu. Antimalarial. Cryst. (diisopropyl
ether). Mp 152-154°. [ex]i; + 129° (c, 0.92 in CHC1 3).
12P-Alcohol, Me ether: Artemether
CI,HuOs M 298.378 C14H 200 M 204.311
Antimalarial. Cryst. (hexane). Mp 86-87°. [ex]~ + 163° Constit. of Heterotheca grandiflora. Oil.
(c, 2.58 in CHC1 3).
Me ether: [73484-03-4]. 3-Methoxy-14-norcalamenene
11 ,13-Didehydro: [10 1020-89-7]. Artemisitene C15H 120 M 218.338
CisH 20 0 5 M 280.320 Constit. of H. grandiflora. Oil. [ex]~ + 53.9° (c, 1.3 in
Constit. of A. annua. Cryst. Mp 161-162°. [ex]~ + 134° CHC1 3).
(c, 0.455 in CHC1 3).
1-0xo: [73484-04-5]. 3-Hydroxy-14-nor- 10-calamenenone
Martindale, The Extra Pharmacopoeia, 28th/29th Ed., C14H 180 2 M 218.295
Pharmaceutical Press, London, 1982/1989, 12023.
Constit. of H. grandiflora. Oil.
Schmid, G. eta/, J. Am. Chern. Soc., 1983, 105, 624 (synth)

449
11,12,13-Trinor-4-amorphene-3,8-... - Primnatrienone Sq-01687 - Sq-01690

1-0xo, Me ether: [73484-05-6]. 3-Methoxy-14-nor-10- 12-Noralliacolide Sq-01689

calamenenone [79232-31-8]
C 15H 200 2 M 232.322
Constit. of H. grandijlora. Oil.
Bohlmann, F. et at, Phytochemistry, 1979, 18, 1675.

11,12,13-Trinor-4-amorphene-3,8-dione Sq-01687
1,3 ,4,4a,5,8a- Hexahydro-4, 7-dimethyl-2 ,6-naphthalenedione,
9CI. 11,12,13- Trinor-4-cadinene-3,8-dione (incorr.)
[89155-80-6] Ct4H200 4 M 252.310

xbo
Constit. of Marasmius alliaceus. Cryst. Mp 198°.
Farrell, I.W. eta/, J. Chern. Soc., Perkin Trans. I, 1981, 1790.

H
Primnatrienone Sq-01690
CuH160 2 M 192.257
Constit. of Eupatorium adenophorum. Oil. [IX]~ +49.6° (c,
2.5 in CC14).
Shukla, V.S. et al, Chern. Ind. (London), 1983, 863.

C 15H 200 M 216.322

6-Hydroxy: [116173-40-1]. 6-Hydroxyprimnatrienone
Alliacanes C15H 200 2 M 232.322
Constit. of a Primnoeides sp. Cryst. (CH 2Cl 2jhexane).
Mp 137-138°.
6-Methoxy: [116173-41-2]. 6-Methoxyprimnatrienone
Ct6H 2P 2 M 246.349
Alliacolide Sq-01688 Constit. of a P. sp. Oil.
[66389-08-0] 6-Methoxy, 3-hydroxy: [116173-38-7]. 3-Hydroxy-6-
methoxyprimnatrienone
C16H 220 3 M 262.348
Constit. of P. sp. Cryst. (EtOAcjhexane). Mp 122-124°.
6-Methoxy, 3-acetoxy: [116173-39-8]. 3-Acetoxy-6-
methoxyprimnatrienone
CtsHzP4 M 304.385
Constit. of a P. sp. Oil. [ali? + 1.5° (c, 0.3 in CHCI 3).
6-Methoxy, 3-oxo: [116173-37-6]. 6-Methoxy-1,3-
C 15H 220 4 M 266.336 primnatrienedione
Metab. of Marasmius alliaceus. Cryst. (EtOAcjpet. ether). C 16H 200 3 M 260.332
Mp 192-194°. [a]i? -35° (c, 0.1 in CHC1 3). Pale yellow microcryst. Mp 92-93°.
]a-Hydroxy: [101043-01-0]. 11%-Hydroxyalliacolide Cambie, R.C. eta/, Aust. J. Chern., 1988, 41, 365.
C 15H 220 5 M 282.336
Constit. of M. alliaceus. Cryst. (EtOAc). Mp 164-166°.
[a]i,3 +4.6° (c, 1 in CHC1 3).
lla-Hydroxy: [79232-30-7]. 11-Hydroxyalliacolide
C 15H 220 5 M 282.336
Constit. of M. alliaceus. Mp 199-20l.SO, Mp 228-229°
(double Mp). [1X] 0 -8.6° (c, 0.56 in CHC1 3).
12-Hydroxy: [79232-32-9]. 12-Hydroxyalliacolide
C 15H 220 5 M 282.336
Constit. of M. alliaceus. Cryst. (Etpjpet. ether). Mp
191-193°. [1X] 0 -32° (c, 0.47 in CHC1 3).
Deoxy: [79232-28-3]. Alliacide
C 15H 220 3 M 250.337
Constit. of M. alliaceus. Cryst. (pet. ether). Mp 168-
1710.
King, T.J. eta/, J. Chern. Soc., Chern. Commun., 1977, 727 (isol)
Farrell, I.W. et al, J. Chern. Soc., Perkin Trans. I, 1981, 1790 (11-
Hydroxyalliacolide, 12-Hydroxyalliacolide, Alliacide)
Bradshaw, A.P.W. et at, J. Chern. Soc., Perkin Trans. I, 1981,
1794; 1982, 2787 (ahs conjig, biosynth)
Avent, A.G. et at, J. Chern. Soc., Perkin Trans. I, 1985, 2749 (1-
H ydroxyalliacolide)
Ladlaw, M. eta/, J. Chern. Soc., Perkin Trans. I, 1988, 1107
(synth)

450
Abrotanifolone- 2-Hydroxy-1(10)-oplopene-4,9-dione Sq-01691 - Sq-01697

Constit. of Notonia petraea. Oil. [rx]i)4 -14.3° (c, 2 in

CHC13).
Oplopanes Bohlmann, F. et at, Phytochemistry, 1979, 18, 1063.

4,9-Dihydroxy-1 0(14)-oplopen-4-one Sq-01695

Abrotanifolone
[60263-03-8]
Sq-01691
~OH
0 ~ooc~ OH
~ooc
'H' "=/
C 15H140 3 M 252.353
AcO~ ~ ~ (4S,9fl)-form
0 Di-Ac: [125988-76-3]. Petasipaline A
C19H 280 5 M 336.427
C28H 44,08 M 504.619 Constit. of Petasites palmatus. Needles (hexane). Mp
Constit. of Senecio abrotanifolius. Cryst. (Et20jpet. ether). 101-103°. [rxJn -51.6° (c, 0.38 in CHC1 3).
Mp 133°.
Hayashi, K. eta/, Phytochemistry, 1989, 28, 3373 (isol, pmr, cmr)
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 2014.

10-Hydroxy-4-oplopanone Sq-01696
3,10-Dihydroxy-4-oplopanone Sq-01692
3-Hydroxyoplopanone

.-<::('
PH
moHH,
Hfonn

CisH 260 2 M 238.369

Cadinane numbering system.
C 15H 260 3 M 254.369 (+)-form
Constit. of Pallenis spinosa. Gum. Constit. of soft coral Nephthea sp. Needles (pet. ether).
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3355 (isol, pmr, cmr) Mp 83-84°. [rx]i,2 + 19° (c, 0.8 in dioxan).
(-)-form [1911-78-0]
10,15-Dihydroxy-4-oplopanone Sq-01693 Constit. of Oplopanax japonicus. Cryst. (Et20jpet.
ether). Mp 96-97°. [rx]~ -20° (c, 0.6 in dioxan).
15
Takeda, K. et at, Tetrahedron, Suppl., 1966, 7, 219 (isol, ir, pmr,

~H
ord, struct)
Caine, D. eta/, J. Org. Chern., 1973, 38, 3663 (synth)
Wratten, S.J. et a/, J. Org. Chern., 1977, 42, 3343 (iso[)
Taber, D.F. eta/, J. Org. Chern., 1978, 43, 4925 (synth)
Koster, F.-H. et at, Tetrahedron Lett., 1981, 22, 3937 (synth)
Piers, E. eta/, J. Org. Chern., 1990, 55, 2380 (synth)

C 15H 260 3 M 254.369

2-Hydroxy-1(1 0)-oplopene-4,9-dione Sq-01697

HM
Biogenetic numbering (of cadinanes).

J:Xo
15-Angeloyl: 15-Angeloyloxy-10-hydroxy-4-op/opanone
C28H 310 4 M 336.470
Constit. of Senecio mexicanus. Oil. [rxln - 22° (c, 0.17 in
CHCI 3).
Joseph-Nathan, P. eta/, Phytochemistry, 1989, 28, 2397 (isol, pmr,
ms)

4,9-Dihydroxy-1 0(14)-oplopen-3-one C,sH140 3 M 252.353

Sq-01694
2«-form

O=<f:t"
0-Cinnamoy/: [119285-30-2]. 2rx-Cinnamoy/oxy-9-
oxoisoanhydrooplopanone. lrx-Cinnamoy/oxy-7-
oxoisoanhydroop/opanone (incorr.)
C14H180 4 M 380.483
I HI Constit. of Ambrosia artemisioides. Oil.
HO~ /-....
0-(4-Methoxybenzoyl): [119285-31-3]. 2rx-Anisoy/oxy-9-
C 15H 140 3 M 252.353 oxoisoanhydroop/opanone. l rx-Anisoy/oxy- 7-
(ent-4~ ,9«)-form oxoisoanhydrooplopanone (inc orr.)
9-(3-Methy/butanoyl), 4-Ac: [72247-71-3]. Notonipetrone C23H 280 5 M 384.471
C12H 340 5 M 378.508 Constit. of A. artemisioides. Oil.

451
4-Hydroxy-10(14)-oplopen-3-one - 10(14)-0plopen-4-one Sq-01698 - Sq-01703

0-Ange/oy/: [119285-29-9]. 2rx-Angeloyloxy-9- Constit. of S. mexicanus. Cryst. Mp 51-53°. [rx]n -194°

oxoisoanhydrooplopanone. 1rx-Angeloy/oxy-7- (c, 2 in CHCI 3).
oxoisoanhydroop/opanone (incorr.) Joseph-Nathan, P. et al, Phytochemistry, 1989, 28, 1207, 2397 (isol,
Czoll 280 4 M 332.439 pmr, cmr, cryst struct)
Constit. of A. artemisioides. Oil.
2-Deoxy: [119285-28-8]. 1(10)-0p/opene-4,9-dione. 1- 9-0plopen-4-one Sq-01701
0xoisoanhydroop/opanone (incorr.) rx.-Oplopenone
C15H 220 1 M 234.338
Constit. of A. artemisioides. Oil. [79560-34-2]
Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551.

4-Hydroxy-10(14)-oplopen-3-one Sq-01698

C15H 140 M 220.354

Constit. of the oil from Santo/ina oblongifo/ia. Oil. [rx]n
-14.SO (c, 0.8 in CHCI 3).
de Pascual-Teresa, J. et al, Phytochemistry, 1983, 22, 2235 (isol,
C15H140 1 M 236.353 struct, synth)
Cadinane numbering shown. Constit. of Senecio
mexicanus. Cryst. Mp 100-102°. [rx]n -108° (c, 0.14 in
CHCI 3).
10(14)-0plopen-3-one Sq-01702
Ac: [125988-77-4]. Petasipaline B
[127486-56-0]
C 17H 160 3 M 278.391

0~
Isol. from Petasites pa/matus. Plates (MeOH). Mp 88-
90.50. (rx]n -56.3° (c, 0.46 in CHCI 3).
Joseph-Nathan, P. et al, Phytochemistry, 1989, 28, 2347 (isol, pmr,
cmr, cryst struct)
Hayashi, K. et al, Phytochemistry, 1989, 28, 3373 (Petasipaline B) ~rtt
lmplexin Sq-01699 C15H 140 M 220.354
Constit. of Senecio mexicanus. Cryst. Mp 54-56°. [rxln
-108° (c, 0.13 in CHC1 3).

f~w~
I ooc)--\
ooc
(4E)-form
[127486-59-3]
Joseph-Nathan, P. et al, Phytochemistry, 1990, 29, 977 (isol, pmr,

"==\
4 cmr, cryst struct)
5r
<t---
I

14 10(14)-0plopen-4-one Sq-01703
o Oplopenone. Anhydrooplopanone
C31 H 440 8 M 544.684 (28305-60-4]
(4E)-form (79383-69-0]
Constit. of Senecio implexus. Gum. [rx]i;' -58.9° (c, 0.37
in CHCI 3).
(4Z)-form
Constit. of S. implexus. Gum.
4P,5-Dihydro, 5-acetoxy:
C33H 480 10 M 604.736
Constit. of S. implexus. Gum. [rx]i;' -15.6° (c, 0.43 in C 15H 140 M 220.354
CHCI3). Different numbering system used in references. Cadinane
Bohlmann, F. et al, Phytochemistry, 1981, 20, 251.
system used here. Constit. of Euryops pedunculatus.
Cryst. (pet. ether). Mp 68°. [rx]i;' -15.2° (c, 0.4 in
CHC1 3).
4,10(14)-0plopadien-3-ol Sq-01700
2rx-Ange/oyloxy: (119285-27-7]. 2rx-
Ange/oxyanhydrooplopanone. 1rx-
Ange/oxyanhydrooplopanone (incorr.)
C10H 300 3 M 318.455
Constit. of Ambrosia artemisioides. Oil.
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1135 (isol)
Jakupovic, J. et al, Phytochemistry, 1988, 27, 3551 (deriv)

C15H1P M 220.354
Biogenetic numbering (cf. cadinanes). Constit. of Senecio
mexicanus. Cryst. Mp 54-56°. [rx]n +29° (c, 0.1 in
CHCI 3).
3-Ketone: 4,1 0(14)-0plopadien-3-one

452
Jungianol- Cryptoporic acid E Sq-01704 - Sq-01707

Mutisianthol group Drimanes

Jungianol Sq-01704 11,12-Bis(7-drimen-11-oxy)-11,12-epoxy- Sq-01706

[62885-78-3] 7-drimene
[62754-34-1]

C 15H 200 M 216.322

Constit. of Jungia malvaefolia. Oil. Bp0 . 1 130° (bath).
Bohlmann, F. eta/, Phytochemistry, 1977, 16, 239.
~ 0

Mutisianthol Sq-01705
[70855-59-3]

C45H 720 3 M 661.062

Constit. of Drimys winteri. Cryst. (MeOHfdioxan). Mp
128-131°. [cxln -24° (c, 1 in C6H6).
CISH200 M 216.322
Constit. of Mutisia homoeantha. Oil. [cx]i;' +94° (c, 0.11 in Aasen, A.J. eta/, Acta Chern. Scand., Ser. B, 1977, 31, 51.
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 99. Cryptoporic acid E Sq-01707
[120001-10-7]
MeOOC\ I
r-COOH

CH,O~

HOH2
w:QS#
£
pHP
0

MeOOC .,
I
HOOC~OH2 C
I
~OOMe

C4SH6801S M 849.023
Metab. of Cryptoporus volvatus.
15-Deoxy: [119979-94-1]. Cryptoporic acid C
C45H680 14 M 833.024
Metab. of C. volvatus. [cxJn +61.2°.
5"'-+ 15 Lactone: [119979-95-2]. Cryptoporic acid D
C44H640 14 M 816.981
Metab. of C. volvatus.
Hashimoto, T. eta/, J. Chern. Soc., Chern. Commun., 1989, 258
(isol, cryst struct)

453
6,7-Dihydroxy-11,12-drimanolide - 3,11-Dihydroxy-7-drimen-6-one Sq-01708- Sq-01713

6,7-Dihydroxy-11,12-drimanolide Sq-01708 3,9-Dihydroxy-7-drimen-12, 11-olide Sq-01711

~0
HO~
C15H 210 4 M 266.336
C 15H 240 4 M 268.352 (3P,9rz.)-form
(6«,7/1)-form [65883-00-3] 6«,7/J-Dihydroxydihydrodrimenin 3P,9rz.-Dihydroxycinnamolide
Metab. of Mycocalia reticulata. Cryst. Mp 43-45°. Constit. of Cane/la winterana. Arnorph. [ex] 0 -14° (c,
0.01 in MeOH).
6-Deoxy: [65882-99-7]. 7P-Hydroxy-ll,l2-drimanolide. 7/J-
Hydroxydihydrodrimenin Kioy, D. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1372 (isol, pmr)
C 15H 240 3 M 252.353
Metab. of M. reticulata. Cryst. (C 6H 6jpentane). Mp 3,13-Dihydroxy-7-drimen-12,11-olide Sq-01712
157-158°. [ex]~ -65° (c, 0.0024 in C6HJ.

~0
6-Deoxy, 7-Ketone: [24034-38-6]. 7-0xo-11,12-drimanolide.
7-0xodihydrodrimenin 0
C 15H 120 3 M 250.337
Metab. of M. reticulata. Cryst. Mp 120-122°. [ex]~
HO~
-118° (c, 0.002 in C6H 6). H
Ayer, W.A. et al, Tetrahedron, 1977, 33, 2771. HOH2 C
C 15H 120 4 M 266.336

w:H
7,11-Dihydroxy-~anone Sq-01709 (3P,5P,9rz.,10rz.)-form
/resin
Constit. of lresine ce/osioides. Cryst. (Me2COfhexane).
Mp 140-142°. [ex]~ +21° (CHC1 3).
Absolute 7,8P-Dihydro: 3,13-Dihydroxy-12,11-drimenolide.
configuration Dihydroiresin
C 15H 240 4 M 268.352
0
Minor constit. of I. celosioides. Mp 212-213° (as
C 15H 21P 3 M 254.369 diacetate).
(5«,7P,8P,9P,10f/)-form [82526-31-6] Uvidin D 1:18•9-Isomer: [561-89-7]. 3,13-Dihydroxy-8-drimen-12,11-
Constit. of Lactarius uvidus. Needles (CHCl 3). Mp 152- olide. lsoiresin
1540. C 15H 1P 4 M 266.336
de Bernardi, M. et al, J. Chern. Soc., Perkin Trans. I, 1983, 2739. Constit. of I. ce/osioides. Oil. Mp 166-168° (as
diacetate). [ex]0 -73.0° (CHC1 3) (diacetate).
6,9-Dihydroxy-7-drimene-11,12-dial Sq-0171 0 7,8P-Dihydro, 3-ketone: 13-Hydroxy-3-oxo-12,11-
drimano/ide. Dihydroiresone
OHC OH ClsH 2z04 M 266.336

~.''CHO
Isol. from /. ce/osioides. Needles (C 6H 6/MeOH). Mp
215-2W.
~ (6a.,9r:x)-form Crabbe, P. et al, Bull. Soc. Chim .. Belg., 1958, 67, 632 (derivs)
Djerassi, C. et al, J. Am. Chern. Soc., 1958, 80, 2593 (struct)
OH Rossmann, H.G. et al, Tetrahedron, 1958, 4, 275 (cryst struct)
C 15H 210 4 M 266.336 Pelletier, S.W. et al, J. Am. Chern. Soc., 1968, 90, 5318 (synth)
(6rz.,9«)-form [87420-14-2] Muk1111dial
Constit. of Warburgia stuhlmannii and W. ugandensis 3,11-Dihydroxy-7-drimen-6-one Sq-01713
and Canella winterana. Shows molluscicidal activity.
Cryst. Mp 173°.
(6P,9rz.)-form
6-Ac: [23599-45-3]. Cinnamodial. Ugandensidial.
Agandencidial
C 17H 240 5 M 308.374
Constit. of Cinnamosmafragrans. Cryst. Mp 141-143°.
[ex]~ -42l.SO (c, l in CHCI 3). C 15H 240 3 M 252.353
Brooks, C.J.W. et al, Tetrahedron, 1969, 25, 2887 (struct) (3P,5rz.,9P,10fl)-form
Canonica, L. et al, Tetrahedron, 1969, 25, 3895 (struct) Deoxyuvidin B
Burton, L.P.J. et al, J. Appl. Chern., 1981, 103, 3226 (synth) Metab. of Alternaria brassicae. Powder.
Kubo, J. et al, Chern. Lett., 1983, 979 (isol) 7P,8P-Epoxy: [74636-05-8]. 7P,8P-Epoxy-3p,Il-dihydroxy-6-
White, J.D. et al, J. Org. Chern., 1985, 50, 357 (synth) drimanone. Uvidin B
Kioy, D. et al, J. Nat. Prod. (Lloydia), 1989, 52, 174 (isol, pmr,
C 15H 240 4 M 268.352
cmr)
Cortes, M. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1369 (synth) Metab. of Lactarius uvidus. Cryst. (EtOAc). Mp 180-
1810. [ex]~ + mo (Me2CO).
3-Deoxy, 7P,8P-epoxy: [74636-06-9]. 7P,8P-Epoxy-ll-
hydroxy-6-drimanone. Uvidin A
454
5,11-Dihydroxy-7-drimen-6-one - 7-Drimene-11,12-dial Sq-01714 - Sq-01720

ClsH240 3 M 252.353 Metab. of Fornes annosus. Cryst. (C 6H 6/Me 2CO). Mp

Metab. of L. uvidus. Cryst. (Etpjpentane). Mp 123- 152-155°. [aln -25.3° (c, 0.08 in CHC1 3).
1240. [a]~ + 151.1° (CHC1 3). Donnelly, D.M.X. eta/, J. Chern. Soc., Perkin Trans. 1, 1980,
3-Deoxy, 7fi,8fi-epoxy, 6P-alcoho/: [74635-85-1]. 7fi,8P- 2196.
Epoxy-6p, 11-drimanedio/. Uvidin C

w-OH
ClsH260 3 M 254.369 8-Drimanol Sq-01718
Constit. of L. uvidus. Plates (hexane). Mp 110-112°.
de Bernardi, M. et a/, J. Chern. Soc., Perkin Trans. 1, 1980, 221
(Uvidins)
Ayer, W.A. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 408
(Deoxyuvidin B)

5,11-Dihydroxy-7 -drimen-6-one Sq-01714 C15H 280 M 224.386

w
(5«,8«,9P,lOfJ)-form [53163-43-2]
CH2 0H Constit. of Greek tobacco. Cryst. Mp 73-75°.
Hlubucek, J.R. eta/, Acta Chern. Scand., Ser. B, 1974, 28, 289.

11-Drimanol Sq-01719
HO
C15H2403 M 252.353
(5«,9P,l0fl)-form [82526-30-5] Uvidin E
Constit. of Lactarius uvidus. Needles (Etpjhexane). Mp
127-129°. [a]i; +6.4° (c, 0.4 in CHC1 3).
de Bernardi, M. eta/, J. Chern. Soc., Perkin Trans. 1, 1983, 2739. C 15H 280 M 224.386
(5«,8«,9P,l 0/1)-form [510-98-5]
Drimane Sq-01715 Cryst. Mp 110-111°. [aln +9°.
Decahydro-1 ,1 ,4a,5,6-pentamethylnaphthalene, 9CI (5«,8P,9P,lOfJ)-form [33762-81-1]
Constit. of Bazzania trilobata. Cryst. Mp 110-111°. [aln
+34°.
Appel, H.H. eta/, J. Chern. Soc., 1959, 3322 (struct)
Carman, R.M. et a/, Aust. J. Chern., 1966, 19, 629 (struct)
Huneck, S., Z. Naturforsch., B, 1967, 22, 462 (isol)

C 15H 28 M 208.386
7-Drimene-11,12-dial Sq-01720
(5«,8«,9P,l0fl)-form [5951-58-6]

Q:JCHO
Constit. of petroleum. 11
CHO
Alexander, R. eta/, J. Chern. Soc., Chern. Cornrnun., 1983, 226.

8,11-Drimanediol Sq-01716
H
ClsH120 1 M 234.338
(5«,9P,l0fl)-form [6754-20-7] Polygodial. Tadenonal
Isol. from Polygonum hydropiper and Drimys lanceolata.
Insect growth regulator. Shows antibacterial and
antifungal activity. Plant growth regulator (inhibits rice
C 15H 280 1 M 240.385
husk germination, promotes root elongation in rice).
(5«,8«,9P,lOfJ)-form [52617-99-9] Needles (pet. ether). Mp 57° (50°). Bp0.8 138-140°. [aln
Constit. of Greek tobacco. Cryst. (Et 20/hexane). Mp -2W (90% EtOH).
119-120°. [a]~ + 1.6° (c, 0.63 in CHC1 3). I> Skin irritant.
Hlubucek, J.R. et a/, Acta Chern. Scand., Ser. B, 1974, 28, 289 11-Carboxy/ic acid: [98204-84-3]. 12-0xo-7-drimen-11-oic
(isol) acid. Polygonic acid
Pelletier, S.W. et a/, J. Org. Chern., 1975, 40, 1607 (synth)
Nishizawa, M. eta/, Tetrahedron Lett., 1983, 24, 2581 (synth) cl5Hllo3 M 250.337
Constit. of P. hydropiper. Cryst. Mp 96-<no. [a]i; -31°
(c, 1.06 in CHC1 3).
7 ,8, 11-Drimanetriol Sq-01717 3fi-Acetoxy: 3P-Acetoxypolygodial
C17H 240 4 M 292.374
Constit. of Canella winterana. Cryst. Mp 131-132°. [a]i,S
-58° (c, 0.05 in CHC1 3).
Loder, J.W. et a/, Aust. J. Chern., 1962, 15, 322, 389 (isol, uv, ir,
prnr)
Kubo, I. eta/, J. Chern. Soc., Chern. Cornrnun., 1976, 1013 (iso/,
C 15H 280 3 M 256.384 struct)
Jalali-Naini, M. eta/, Tetrahedron, 1983, 39, 749 (synth)
(5«,7«,8P,9P,l0fJ)-form [76163-71-8] Cortes, M.J. eta/, Chern. Ind. (London), 1985, 735 (synth)

455
7-Drimene-3,11-diol- 8(12)-Drimen-11-ol Sq-01721 - Sq-01727

Fukuyama, Y. eta/, Phytochemistry, 1985, 24, 1521 (Polygonic 7-Drimene-11,12,14-triol Sq-01725

acid)
Mori, K. et a/, Tetrahedron, 1986, 42, 273 (synth) [124869-11-0]
Caprioli, V. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 146 (synth)

~~,OH
Jansen, B.J.M. eta/, J. Org. Chern., 1988, 53, 855 (synth)
Banthorpe, D.V. eta/, Phytochemistry, 1989, 28, 1631 (biosynth)
Al-Said, M.S. eta/, Phytochemistry, 1990, 29, 975 (iso/, pmr, cmr)

7-Drimene-3,11-diol
[124987-04-8]
Sq-01721
HOH~
C 15H 160 3 M 254.369
Metab. of Marasmius oreades. Cryst. (EtOAc). Mp 178-
1800. [oc]~ -10.7° (c, 0.15 in MeOH).
Ayer, W.A. eta/, Can. J. Chern., 1989, 67, 1371 (isol, pmr, cmr)

7-Drimen-11-ol Sq-01726
CtsH160 1 M 238.369
JP-form
Constit. of Marasmius oreades. Oil.
Ayer, W.A. et a/, Can. J. Chern., 1989, 67, 1371 (isol, pmr, cmr)

6-Drimene-8,9,11-triol Sq-01722
C 15H 21;0 M 222.370
(5«.,9P,JOfJ)-form [468-68-8] Drimenol
Constit. of Drimys winteri and Warburgia ugandensis.
Plant growth regulator (inhibits cress root growth,
promotes wheat seed germination). Cryst. (C 6H6). Mp
97.8°. Bp 3_5 150.5-151°. [ocJ::i -19.1° (C 6H 6).
CtsH160 3 M 254.369 Appel, H.H. eta/, J. Chern. Soc., 1959, 3322 (isol, struct)
Wenker!, E. eta/, J. Am. Chern. Soc., 1964, 86, 2044 (synth)
(5«.,8P,9«.,10f/)-form [110538-22-2]1soalbrassitriol Huneck, S. eta/, Phytochemistry, 1972, 11, 2429.
Metab. of Alternaria brassicae. Oil. Pelletier, S.W. eta/, J. Org. Chern., 1975, 40, 1607 (synth)
Ayer, W.A. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 408. Nishizawa, M. et a/, Tetrahedron Lett., 1983, 24, 2581 (synth)

7-Drimene-3,11,12-triol Sq-01723 8(12)-Drimen-11-ol Sq-01727

C 15H 260 M 222.370

CtsH160 3 M 254.369
(5«.,9P,JOfJ)-form [54632-04-1] Albicanol
3P-form [101470-79-5]
Constit. of Diplophyllum albicans and D. taxifolium. Oil.
Constit. of Marasmius oreades. Cryst. (EtOAc). Mp 165-
1660. [oc]i? -10.9° (c, 1.1 in MeOH). 3,4-Dihydroxycinnamoy/: [80357-99-9].
C24H3z04 M 384.514
Sierra, J.R. eta/, Phytochemistry, 1986, 25, 253 (synth)
Ayer, W.A. eta/, Can. J. Chern., 1989, 67, 1371 (isol, pmr, cmr)
Constit. of Bazzania spp. Cryst. Mp 179-180°. [oc] 0
-18.3° (c, 3.2 in MeOH).
2,4-Dihydroxycinnamoy/: [80358-00-5].
7-Drimene-6,9,11-triol Sq-01724
C24H320 4 M 384.514
6,9,11- Trihydroxy-7-drimene Constit. of B. spp. Oil.
Ohta, Y. et a/, Tetrahedron, 1977, 33, 617 (isol)
Toyata, M. eta/, Phytochemistry, 1981, 20, 2359 (isol)
Armstrong, R.J. eta/, Can. J. Chern., 1986, 64, 1002 (synth)
Ragoussis, V. eta/, J. Chern. Soc., Perkin Trans. I, 1987, 987
(synth)
Shishido, K. et a/, J. Chern. Soc., Chern. Commun., 1989, 1093
(synth)
C 15H 21;03 M 254.369
(5«.,6«.,9«.,10/1)-form [110557-39-6] Albrassitriol
Metab. of Alternaria brassicae. Amorph. powder. Mp
100-104°.
Ayer, W.A. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 408.

456
9(11)-Drim.en-8-ol - 8-Drimen-12,11-olide Sq-01728 - Sq-01731

9(11)-Drimen-8-ol Sq-01728 9a-Hydroxy: 9-Hydroxy-7-drimen-12,11-o/ide. 9«.-

Decahydro-2,5,5,8a-tetramethy/-1-methy/ene-2-naphtha/eno/, HydroxydllllllmOiide
9Cl C15H 220 3 M 250.337
Constit. of Cane//a winterana. Cryst. Mp 150-155°. [1X]n
-10° (c, 0.44 in CHC1 3).
~
~-ou
11rx.-Ethoxy: 11a-Ethoxy-1-drimen-l2,1l-o/ide. 11«.-
Etlwxycinnamolide
C17H 260 3 M 278.391
Constit. of Polygonum hydropiper. Cryst. Mp 45-47°.
CtsH 260 M 222.370 6P-Acetoxy: [24173-64-6]. 6P-Acetoxy-1-drimen-l2,ll-o/ide.
(5P,8«)0rx.)-form [86546-84-1] Bemtll'ivolide
Metab. of Aspergillus oryzae. Oil. [a]~ -132° (c, 0.08 in C17H 140 4 M 292.374
CHC1 3). Constit. of Cinnamosma fragrans. Cryst. (diisopropyl
(5P,BP.IOrx.)-form [86546-83-0] ether). Mp 137-138°. [1X]n -258° (CHC13).
Metab. of A. oryzae. Oil. [a]~ +4.4° (c, 0.14 in CHC1 3). 6P,9a-Dihydroxy: [16772-63-7]. 6P,9a-Dihydroxy-7-drimen-
Wada, K. eta/, Agric. Bioi. Chern., 1983, 47, 1075 (isol) l2,ll-o/ide. Pereniporin B
Leite, M.A.F. eta/, J. Org. Chern., 1986, Sl, 5409 (synth, abs C15H 220 4 M 266.336
config) lsol. from Perenniporia medu//aepanis. Active against
gram-positive bacteria and leukaemia. Powder. Mp 181-
1830. [rx.]~4 -208° (c, 0.05 in MeOH).
7-Drimen-11,12-olide Sq-01729
Drimenin 6P-Acetoxy, 9a-hydroxy: [23599-46-4]. 6P-Acetoxy-9a-
hydroxy-1-drimen-l2, 11-o/ide. Cinnamosmolide
[2326-89-8] C17H140 5 M 308.374
Constit. of C. fragrans. Cryst. Mp 204°. [ali:' -332.4°
(c, I in CHCI 3).
3P-Hydroxy: 3/J.-Hydroxycinnamolide. Cinnamo/ide-3P-ol
C1sH220 3 M 250.337
Constit. of Marasmius oreades and Warburgia
stuh/mannii. Oil or amorph. solid. [1X]n +37° (c, 0.5 in
MeOH).
C 15H 220 1 M 234.338 3P-Acetoxy:
Constit. of Drimys winteri. Cryst. (MeOH). Mp 133°. [1X]n C17H 140 4 M 292.374
-42° (c, 0.76 in C6H 6). lsol. from W. ugandensis. Prisms (EtOAcfpet. ether).
3P-Acetoxy: 3fJ.-Acetoxydrimenin Mp 153-155°. [1X]n +7° (c, 3 in CHC13).
C17H 140 4 M 292.374 Canonica, L. eta/, Tetrahedron, 1969, 25, 631, 3903 (Bemarivo/ide)
Constit. of D. winteri. Cryst. (EtOAcfhexane). Mp 173- Suzuki, T. eta/, Bull. Chern. Soc. Jpn., 1970, 43, 1268 (synth)
1740. [ali:' -7° (c, 0.9 in CHC13). Yamagawa, H. eta/, Synthesis, 1970, 257 (Cinnamosmolide)
Nakanishi, K. eta/, lsr. J. Chern., 1977, 16, 28 (isol)
11a-A/coho/: [72581-69-2]. 11 ,12-Epoxy-7-drimen-11a-o/. Fukuyama, T. eta/, Phytochemistry, 1985, 24, 1521 (11-
lsodrimeninol Ethoxycinnomo/ide)
C15H140 1 M 236.353 K.ida, T. eta/, J. Antibiot., 1986, 39, 615 (Pereniporin B)
Constit. of Polygonum hydropiper. Oil. [1X]n -37° (c, 1.5 Ayer, W.A. eta/, Can. J. Chern., 1989, 67, 1371 (iso/, pmr, cmr)
in CHC1 3). Mori, K. eta/, Justus Liebigs Ann. Chern., 1989, 939 (synth)
Appel, H.H. eta/, J. Chern. Soc., 1960, 4685 (isol) K.ioy, D. eta/, Phytochemistry, 1990, 19, 3535 (3P-
Hydroxycinnamo/ide)
K.itahara, Y. eta/, J. Chern. Soc., Chern. Commun., 1969, 342
(synth)
Yanagawa, H. et a/, Synthesis, 1970, 257 (synth) 8-Drimen-12,11-olide Sq-01731
Asakawa, Y. et a/, Experientia, 1979, 35, 1420 (lsodrimeninol) Confertifolin
Jalali-Naini, M. eta/, Tetrahedron, 1983, 39, 749 (synth)
Liapis, M. eta/, J. Chern. Soc., Perkin Trans. 1, 1985, 815 (synth) [1811-23-0]
Sierra, J.R. eta/, Phytochemistry, 1986, 25, 253 (Acetoxydrimenin)

~O
Ragoussis, V. eta/, J. Chern. Soc., Perkin Trans. 1, 1987, 987
(synth)

7-Drimen-12,11-olide
CiiUfllmolide
Sq-01730 W J\boolut<
configuration
[23599-47-5] C15H 220 1 M 234.338
Constit. of the bark of Drimys winteri. Cryst. (pet. ether).

~0
Mp 152°. [1X]n + 72° (c, 2 in CHC13).
11a-Hydroxy: [24173-70-4]. 11a-Hydroxy-8-drimen-l2,11-
o/ide. Va/diviolide

C15H 220 1
~
M 234.338
C15H 220 3 M 250.337
Isol. from bark of D. winteri. Cryst. (C6H 6). Mp 177-
1780. [1X]n + l U0 (c, l.l8 in CHC13).
Constit. of Cinnamosma fragrans. Shows antifungal 6-0xo: [24179-85-9]. 6-0xo-8-drimen-12,11-o/ide. Fragrolide
activity. Cryst. Mp 125-126°. [ali:' -29.4° (c, I in CtsHzo03 M 248.321
CHC1 3). Constit. of Cinnamosma fragrans. Cryst. (diisopropyl
ether). Mp 165-166°. [ali:' + 149° (CHCI 3).

457
8-Drimen-7-one- Isodrimenin Sq-01732 - Sq-01736

7C,,11C,-Dihydroxy: 7C,,llt,-Dihydroxy-8-drimen-l2,ll-olide. 3P-Chloro, Me ester: [92675-15-5].

7t,, ll t,-Dihydroxyconfertifolin. Fuegin Mp 138-139°. [ex]i? -24.13° (c, 1.73 in CHC1 3).
Constit. of D. winteri. Cryst. (CH 2Cl 2 jpet. ether). Mp lchihara, A. eta/, Tetrahedron Lett., 1984, 3209 (iso/, ir, pmr, cmr)
170-172°. [exJn +76° (c, 1.12 in CHC1 3).
6,7-Didehydro: [24173-65-7]. 6,8-Drimadien-12,11-olide. Euryfuran Sq-01734
Benuulienolide 11,12-Epoxy-8(1 2),9(1 1)-drimadiene
CtsH 200 2 M 232.322
Constit. of Cinnamosma fragrans. Cryst. (diisopropyl [79895-94-6]
ether). Mp 124-125°. [ex]i? +72o (CHC1 3).
7ex-Chloro, 6P-hydroxy: 7«-Chloro-6/J-hydroxyconfertifolin
CtsH 21 0 3 M 249.329
Constit. of Makinoa crispata. Plates (EtOAcjhexane).
Mp 194.5-196°. [exln +36° (c, 0.88 in Me2CO).
6p,7ex-Dihydroxy: 6P,7«-Dihydroxyconfertifolin
CtsH2204 M 266.336 CtsH220 M 218.338
Constit. of M. crispata. Needles (EtOAcjhexane). Mp Constit. of the nudibranch Hypselodoris spp. and Dysidea
212-215°. [ex]b +47.9° (c, 0.73 in Me2CO). herbacea. Oil. [ex]~ + 15.3° (c, 0.4 in CC14), [exln -24° (c,
6p, 7P-Epoxy: 6P,7fJ-Epoxyconfertifolin 0.5 in CHC1 3).
CtsH200 3 M 248.321 Dunlop, R.W. eta/, Aust. J. Chern., 1982, 35, 95 (isol)
Constit. of M. crispata. Needles (Etp). Mp 138-140°. Hochlowski, J.E. eta/, J. Org. Chern., 1982, 47, 88 (iso/, struct)
[exln + 16.7° (c, 0.65 in Me2CO). Ley, S.V. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 1379 (synth)
Nakano, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1987, 2137
Appel, H.H. eta/, J. Chern. Soc., 1960, 4685 (iso/, struct) (synth)
Appel, H.H. et a/, Tetrahedron, 1963, 19, 635 (Valdiviolide, Fuegin)
Wenkert, E. eta/, J. Am. Chern. Soc., 1964, 86, 2044 (synth)
Canonica, L. et a/, Tetrahedron, 1969, 25, 3903 (Fragro/ide, 9-Hydroxy-7-drimene-11,12-dial Sq-01735
Bemadienolide)
Akita, H. et al, Chern. Pharm. Bull., 1980, 29, 2166 (synth)
Ley, S.V. eta/, J. Chern. Soc., Perkin Trans. I, 1983, 1379 (synth)
White, J.D. eta/, J. Org. Chern., 1985, SO, 357 (synth, Fragrolide)
Hashimoto, T. eta/, Phytochemistry, 1989, 28, 3377 (derivs)

8-Drimen-7-one Sq-01732
[55733-01-2] CtsH2203 M 250.337
9«-form [62994-47-2] Warburgfllllll
Ct 5H 220 3 M 250.337
lsol. from Warburgia spp. Antifeeding compd. Cryst.
(hexane). Mp 106-107°. [ex]~ +260° (c, 0.45 in CHC1 3).
Kubo, I. eta/, J. Chern. Soc., Chern. Commun., 1976, 1013 (isol,
C 15H240 M 220.354 struct)
Nakanishi, K. et a/, Jsr. J. Chern., 1977, 16, 28 (iso/, struct)
Constit. of Nicotiana tabacum. Cryst. Mp 52-53°. [ex]i? Hollinshead, D.M. eta/, J. Chern. Soc., Perkin Trans. 1, 1983,
+ 58.7° (c, 0.2 in CHC1 3). 1579 (synth, bib[)
Aasen, A.J. eta/, Acta Chern. Scand., Ser. B, 1975, 29, 51. Razmilic, I. et a/, Chern. Lett., 1985, 1113 (synth)
Manna, S. eta/, J. Chern. Soc., Chern. Commun., 1987, 1324
(synth)
5,6-Epoxy-8-hydroxy-11-drimanoic acid Sq-01733 Nakano, T. eta/, J. Chern. Soc., Perkin Trans. 1, 1987, 2137
(synth)
Ayer, W.A. eta/, Can. J. Chern., 1988, 66, 1675 (synth)
Jansen, B.J.M. et a/, J. Org. Chern., 1988, 53, 855 (synth)

lsodrimenin Sq-01736
8-Drimen-11 ,12-olide
C 15H2404 M 268.352 [36506-91-9]
(5«,6«,8«,9P,JOfl)-form [92675-ll-l]
Altiloxin A
lsol. from Phoma asparagi. Phytotoxic. Inhibits root
growth. Acidic cryst. Mp 136-137°. [ex]~ -16.9° (c, 0.7
in CHC1 3).
Me ester: [92675-12-2].
Mp l20-l2l 0 • [ex]i? -24.73° (c, 1.65 in CHC1 3).
CtsH220 2 M 234.338
3P-Chloro: [92675-14-4]. 3-Chloro-5,6-epoxy-8-hydroxy-11-
From the bark of Drimys winteri. Cryst. (hexane) or by
drimanoic acid. Altiloxin B
subl. Mp 131-132°. [exJn +87° (c, 2.02 in CHC1 3).
C15H 23Cl04 M 302.797
From P. asparagi. Phytotoxic inhibitor of plant growth. 6P-Hydroxy: [75320-93-3]. 6P-Hydroxy-8-drimen-l1, 12-
Acidic cryst. Mp 145-148°. [ex]i? -10.9° (c, 0.88 in olide. 6/J-Hydroxyisodrimenin
CHC1 3). CtsH220 3 M 250.337
Constit. of Protowoodsia machuriensis. Cryst.
(CHC1 3jhexane). Mp 256-258°. [ex]i;' +9.7° (c, 0.2 in
MeOH).

458
Marasmal - Officinalic acid Sq-01737 - Sq-01740

7rx-Hydroxy: [41060-24-6]. 7rx-Hydroxy-8-drimen-11,12- 14-Hydroxy: [124987-02-6]. 14-Hydroxymarasmene

olide. 7rx-Hydroxyisodrimenin. Futronolide C 13H 220 3 M 250.337
C 13H:zz0 3 M 250.337 Metab. of M. oreades. Prisms (CH 2Cl2 jhexane). Mp
Constit. of D. winteri. Cryst. (CH 2Cl2 /C 6H 6). Mp 215- 162.5-163°. [rx]i;' +23.8° (c, 0.32 in MeOH).
2170. 1rx,15-Dihydroxy: [124869-04-1]. 1rx.,15-
6fi, 7rx-Dihydroxy: 6p, 7 rx-Dihydroxy-8-drimen-11, 12-o/ide. Dihydroxymarasmene
Deacetylugandensolide C13H 220 4 M 266.336
C 13Hu04 M 266.336 Metab. of M. oreades. Cryst. (EtOAcjhexane). Mp 152-
Constit. of Warburgia ugandensis and W. stuhlmannii. 1550.
Needles (EtOAcjMeOH). Mp 260-265°. [rx]n + 70° (c, 1 3rx,15-Dihydroxy: [124869-03-0]. 3rx.,15-
in MeOH). Dihydroxymarasmene
6fi-Acetoxy, 7rx-hydroxy: [24034-31-9]. 6fi-Acetoxy-7rx- C 13H:zz04 M 266.336
hydroxy-8-drimen-11, 12-o/ide. Ugandensolide Metab. of M. oreades. Cryst. (EtOAcjhexane). Mp 146-
C 17H 240 3 M 308.374 1470.
Constit. of W. ugandensis. Cryst. (EtOH). Mp 218°. [rxln 3-0xo: [124894-87-7]. Marasmen-3-one
+ 23° (CHC1 3). C13H 200 3 M 248.321
Appel, H.H. et a/, J. Chern. Soc., 1960, 4685 (isol, struct) Metab. of M. oreades. Cryst. (CH 2Cl2 jhexane). Mp 135-
Wenkert, E. eta/, J. Am. Chern. Soc., 1964, 86, 2044 (synth) 1380. [rx]i;' -1.6° (c, 1 in MeOH).
Brooks, C.J.W. eta/, Tetrahedron, 1969, 25, 2887 (Ugandensolide) 15-Hydroxy, 3-oxo: [124894-86-6]. 15-Hydroxymarasmen-3-
Kato, T. eta/, Tetrahedron Lett., 1972, 4257 (Futronolide)
Tanaka, N. et al, Chern. Pharm. Bull., 1980, 28, 2185 (6P-
one
Hydroxyisodrimenin) C 13H 200 4 M 264.321
Akita, H. et al, Chern. Pharm. Bull., 1980, 29, 2166 (synth) Metab. of M. oreades. Oil.
Nakano, T. et al, J. Chern. Soc., Perkin Trans. 1, 1982, 1163 15-0xo: see Marasmone, Sq-01739
(synth) Ayer, W.A. eta/, Can. J. Chern., 1989, 67, 1371 (isol, pmr, cmr)
Armstrong, R.J. eta/, Can. J. Chern., 1986, 64, 1002 (synth)
Ragoussis, V. eta/, J. Chern. Soc., Perkin Trans. 1, 1987, 987
(synth) Marasmone Sq-01739
Kioy, D. eta/, Phytochemistry, 1990, 29, 3335 [122458-04-2]
(Deacetylugandensolide)

Marasmal Sq-01737
[124869-10-9]

C13H 180 3 M 278.304

Constit. of Marasmius oreades. Foam. [rx]i;' + 74.6° (c, 1.44
in MeOH).
3-Deoxy, 2,3-didehydro: [122458-06-4]. Anhydromarasmone
C 13H 200 6 M 296.319 C 13H 160 4 M 260.289
Metab. of Marasmius oreades. Cryst. (CHC1 3). Mp 195- Constit. of M. oreades. Cryst. (CH 2Cl 2jhexane). Mp
2000. [rx]i;' -73.1° (c, 0.32 in MeOH). 194-196°. [1X]i;' -59.8° (c, 0.4 in MeOH).
Ayer, W.A. eta/, Can. J. Chern., 1989, 67, 1371 (isol, pmr, cmr) 11X-Alcohol: [122458-07-5]. Dihydromarasmone
C 13H 200 3 M 280.320
Constit. of M. oreades. Prisms (EtOAcjCH 2Cl2jhexane).
Marasmene Sq-01738
Mp 164-165°. [1X]i;' +28° (c, 0.5 in MeOH).
[124869-12-1]
11X-Alcohol, 3-ketone: [122458-05-3]. 1somarasmone
H C 13H 180 3 M 278.304
I Constit. of M. oreades. Prisms (CHC1 3). Mp 247-250°.
Ayer, W.A. et al, Can. J. Chern., 1989, 67, 773 (isol, pmr, cmr,
cryst struct)

Officinalic acid Sq-01740

14 [23983-77 -9]
C 13H:zz02 M 234.338
Metab. of Marasmius oreades. Needles. Mp 70-74°. [rx]i;'
+ 57° {c, 0,07 in MeOH).
3P-Hydroxy: [124869-08-5]. 3fJ-Hydroxy11Ull'asmene
C 13Hu03 M 250.337
Metab. of M. oreades. Microcryst. solid. Mp 129-133°.
[rx]~4 + 34° (c, 1.05 in MeOH).
13-Hydroxy: [124869-09-6]. 13-Hydroxymarasmene
C 13H:zz03 M 250.337
Metab. of M. oreades. Microcryst. Mp 147-150°. [rx]i;'
+3.7° {C, 0.2 in MeOH). M 500.674

459
Olepupuane- 1,6,13-Trihydroxy-12,11-drimanolide Sq-01741- Sq-01746

Constit. of Fornes officina/is. Cryst. Mp 272°. [<Xln -60° (c, Terpene antibiotic. Prod. by Perenniporia medullaepanis.
0.5 in dioxan). Active against gram-positive bacteria and leukaemia
Epstein, W.W. eta/, J. Am. Chern. Soc., 1979, 101, 2748 (isol) cells. Powder. Mp 164-166°. [<X]i;' -181° (c, 0.25 in
Erb, B. eta/, Croat. Chim. Acta, 1985, 58, 653 (synth) MeOH).
Kida, T. eta/, J. Antibiot., 1986, 39, 615 (isol, struct, pmr, props)
Olepupuane Sq-01741 Mori, K. et a/, Justus Liebigs Ann. Chern., 1989, 939 (synth)
[85356-02-1]
Polygodial acetal Sq-01744

::0
[98204-88-7]

yv'OAc

C 19H 280 5 M 336.427

Constit. of Dendrodoris spp. and Doriopsilla spp. Oil. [<X]n
-83.3° (c, 0.54 in CHCI 3). Ct,H 280 3 M 280.406
6P-Acetoxy: [97530-61-5]. From Polygonum hydropiper. Yellow oil.
C 21 H 300 7 M 394.464 Fukuyama, Y. eta/, Phytochemistry, 1985, 24, 1521.
Constit. of nudibranch Dendrodoris grandifiora. [<Xln
-118.7° (c, 1.3 in CHC1 3). Purpuride Sq-01745
Okuda, R.K. et a/, J. Org. Chern., 1983, 48, 1866 (isol) [41411-07-8]
Cimino, G. eta/, Tetrahedron, 1985, 41, 1093 (isol)
Cimino, G. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 1010 (isol, pmr)

Oreadone Sq-01742

C 22 H 33N0 5 M 391.506
Metab. of Penicillium purpurogenum. Cryst. (EtOAc). Mp
C 14Hzo03 M 236.310 200-201°.
Formyl: 0-Formyloreadone King, T.J. eta/, J. Chern. Soc., Perkin Trans. 1, 1973, 78.
C 1sH 200 4 M 264.321
Metab. of Marasmius oreades. Glass. [,:x]i;' +278° (c, 1,6,13-Trihydroxy-12,11-drimanolide Sq-01746

w
O.o? in MeOH).
3<X-Hydroxy: [124869-06-3]. 3rx-Hydroxyoreadone
C 14H 200 4 M 252.310
Metab. of M. oreades. Prisms (CH 2Cl2 jhexane). Mp
103-108°. [<X]i;' + 130.2° (c, 1 in MeOH).
2,3-Didehydro: [124869-07-4]. Dehydrooreadone HOH,c' OH O
ci4HI 80 3 M 234.294
Metab. of M. oreades. Solid. C15H 240 5 M 284.352
Ayer, W.A. et a/, Can. J. Chern., 1989, 67, 1371 (iso/, prnr, cmr, (Jp,6fl)-form
struct)
6-Benzoyl: Deacetylpebrolide
C22H 280 6 M 388.460
Pereniporin A Sq-01743 Constit. of Pencicillium brevicompactum. Cryst.
JJ,x,J2-Epoxy-7-drimene-6P,ll<X-diol (CHC1 3jpet. ether). Mp 252-255°. [<X]n -25° (CHC1 3).
[1 03244-42-4] 6-Benzoyl, 13-Ac: [79236-15-0]. Pebrolide
C24H 300 7 M 430.497

~
Constit. of P. brevicompactum. Cryst. (CHC1 3 jpet.
ether). Mp 167-170°. [<X]n -41° (CHC1 3).
1-Deoxy, 6-benzoyl, 13-Ac: 1-Deoxypebrolide
C24H 300 6 M 414.497

M 268.352
~ Constit. of P. brevicompactum. Cryst. (Et 2CO). Mp 171-
1730.
McCorkindale, N.J. eta/, Tetrahedron, 1981, 37, 649, 1991 (isol,
biosynth)

460
6,14,15-Trihydroxy-8-drimen-12,11-... - Muzigadial Sq-01747 - Sq-01751

6,14,15-Trihydroxy-8-drimen-12,11-olide Sq-01747
0
0
Coloratanes

4(13),8-Coloratadienolide Sq-01749
6p-form [60114-23-0]
6-Benzoy/,14,15-Di-Ac: [55778-98-8]. Astellolide A.
Parasiticolide A
C26H 300 8 M 470.518
Constit. of Aspergillus variecolor, A. parasiticus and
Eurotium chevalieri. Cryst. (EtOAc). Mp 214-216°. [1X]i;1
-13° (c, 1.13 in CHC1 3).
6-(4-Hydroxybenzoyl), 14,15-Di-Ac: [78834-89-6].
AsteUolide B C1sH 200 2 M 232.322
C26H 300 9 M 486.518 Constit. of Pseudowintera colorata. Cryst. (EtOH). Mp
From A. variecolor. Cryst. (EtOAc). Mp 251-253°. 132-133°. [1X]i,'l +292.1° (c, 0.47 in CHC1 3).
Fukugama, K. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 2949 (cryst Corbett, R.E. eta/, J. Chern. Soc., Perkin Trans. J, 1976, 850 (isol)
struct) Groot, A. de. eta/, Tetrahedron Lett., 1982, 23, 4831 (synth)
Hamasaki, T. et a/, Agric. Bioi. Chern., 1975, 39, 749 (isol, struct)
Gould, R.O. eta/, Tetrahedron Lett., 1981, 1047 (cryst struct)
9-Hydroxy-4(13),7-coloratadien-12,11- Sq-01750
olide
Winterin Sq-01748
[6754-56-9]

Absolute
configuration
C1sH 200 3 M 248.321
(3«.H,9«.)-form
C1sH20 0 3 M 248.321
Muzigadiolide
Constit. of the bark of Drimys winteri. Cryst. (EtzO). Mp
Constit. of Warburgia stuhlmannii. Needles (CHC1 3). Mp
158°. [1X]n + 109° (c, 2.52 in CHC1 3).
140-145°. [1X]n +380° (c, 0.6 in MeOH).
Appel, H.H. et at, Tetrahedron, 1963, 19, 635 (isol, struct)
Pelletier, S.W. et a/, Tetrahedron, 1977, 33, 1021 (synth, abs config) Kioy, D. et at, Phytochemistry, 1990, 29, 3535 (isol, pmr)

Muzigadial Sq-01751
Canellal
[66550-09-2]

~~HO
~
C1sH200 3 M 248.321
lsol. from Warburgia ugandensis and Canella winterana.
Antifeedant. Cryst. Mp 127-128°. [Ot:]i; -193° (c, 0.2 in
CHC1 3).
41X,l3-Epoxide: 4«.,13-Epoxymuzigadial
C1sH200 4 M 264.321
Constit. of C. winterana. Cryst. (Me 2CO/Et20). Mp
140-142°. [1X]n -240° (c, 0.5 in CHC1 3).
9-Deoxy: 9-Deoxymuzigadial
C1sH 200 2 M 232.322
Constit. of C. winterana. Cryst. Mp 74-76°. [Ot:]i; -99°
(c, 0.05 in CHC1 3).
9-Deoxy, 1!3-isomer: 9-Deoxyisomuzigadial
C1sH 200 2 M 232.322
Constit. of C. winterana. Cryst. Mp 96-98°. [Ot:]i; -381°
(c, 0.05 in CHC1 3).
Kubo, I. eta/, Tetrahedron Lett., 1977, 4553 (isol)

461
0-Ambrinol - 8,9-Seco-9(11)-drimen-8-one Sq-01752- Sq-01757

E1-Feraly, F.S. et al, J. Chern. Soc., Chern. Commun., 1978, 75 Constit. of tobacco. Oil.
(isol, cryst struct) Oh1off, G. et al, Helv. Chim. Acta, 1973, 56, 1414 (synth)
Bosch, M.P. et al, J. Org. Chern., 1986, 51, 773 (synth) Hlubucek, J.R. et al, Acta Chern. Scand., Ser. B, 1974, 28, 18 (isol)
Jansen, B.J.M. et al, J. Org. Chern., 1988, 53, 855 (synth)
Al-Said, M.S. et al, Phytochemistry, 1989, 28, 297; 1990, 29, 975
(derivs) 7-Oxo-11-nor-8-drimen-12-oic acid Sq-01755
3,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethyl-3-oxo-2-
naphthalenecarboxylic acid, 9CI

Nor- and secodrimanes (~t:Co"

C 14H 200 3 M 236.310
Me ester: [112358-43-7].
C 13H 120 3 M 250.337
0-Ambrinol Sq-01752 Constit. of fungus Lepista g/aucocana. Oil. [oc]i? +28.2°

W"
1,2,3,4,4a,5,6,8a-Octahydro-2,5,5-trimethyl-2-naphthalenol
(c, 0.90 in CHCl 3).
Errington, S.G. et al, J. Chern. Res. (S), 1987, 47.
Janaki, S. et al, Indian J. Chern., Sect. B, 1988, 27, 505 (synth)

(2R•,4aR•.&R+fo'm Polygonal Sq-01756

7oc-Hydroxy-11-nor-8-drimen-12-a/
C 13H 120 M 194.316 [72537-20-3]
Compounds related to ambergris constituents with weak
woody odours. ~CHO
(2R*;4aR* ,BaR*)-form [83153-02-0]
Cryst. (hexane). Mp 82-83°. ~'OH
(2R* ,4aS* ,BaR*)-form [83153-00-8]
Oil. Bp0 _1 90-91°. C 14H 120 2 M 222.327
(2R* ,4aS* ,BaS*)-form [83152-99-2] Constit. of Polygonum hydropiper. Cryst. Mp ll6-ll7°.
Cryst. (hexane). Mp 43-45°. (ocJn -7.3° (c, 7.4 in CHCl3).
(2R*,4aR* ,BaS*)-form (83153-01-9] 7-Epimer: [98204-83-2]. lsopolygonal
Cryst. (hexane). Mp 101-102°. C 14H 120 2 M 222.327
Constit. of P. hydropiper. Oil. [oc]i;' + 73° (c, 1.88 in
Christenson, P.A. et al, J. Org. Chern., 1982, 47, 4786 (synth)
CHCl 3).
7-Ketone: [72581-67-0]. 7-0xo-11-nor-8-drimen-12-a/.
11-Nor-8,9-drimanediol Sq-01753 Polygonone
Decahydro-2,5,5,8a-tetramethyl-1 ,2-naphtha/enedio/, 9CI C 14H 200 2 M 220.311

cP-OH
From P. hydropiper. Oil.
Asakawa, Y. et al, Experientia, 1979, 35, 1420 (Polygonal)
Fukuyama, Y. et al, Phytochemistry, 1985, 24, 1521 (Isopolygonal,
Polygonone)

8,9-Seco-9(11 )-drimen-8-one Sq-01757

C 14H:u;02 M 226.358 4-(2,2,6- Trimethy/-6-viny/cyc/ohexyl)-2-butanone
(8«,9fl)-form [79886-54-7] [52690-42-3]
Constit. of Greek tobacco. Cryst. Mp 153-154°. [ocJn

Q:y
-15° (c, 0.06 in CHCl 3).
9-Deoxy: [79951-97-6]. 11-Nor-8«-drimanol
C 14H:u;0 M 210.359
Constit. of Greek tobacco. Oil. [ocJn -10° (c, 0.03 in 0
CHCl 3).
C 13H 260 M 222.370
Ohloff, G. et al, Helv. Chim. Acta, 1973, 56, 1414. Constit. of tobacco. [oc]i? -0.5° (c, 0.2 in CHCl 3).
Wahlberg, I. eta/, Acta Chern. Scand., Ser. B, 1981, 35, 307.
H1ubucek, J.R. eta/, Acta Chern. Scand., 1974, 288, 18.

11-Nor-8-drimen-7-one Sq-01754
1sonordrimenone
[51020-10-l]

M 206.327

462
 2,4-Dihydroxy-1(5),11(13)-... - Echinaxanthol Sq-01758 - Sq-01761

Winters, T.E. eta/, J. Org. Chem., 1969, 34, 153 (Xanthanol,

Isoxanthanol)

Xanthanes Bohlmann, F. eta/, Chem. Ber., 1977, 110, 1330 (2-

Deacetoxyxanthinin)
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 885; 1981, 20, 2429;
1982, 21, 1441.
Omar, A.A. eta/, Phytochemistry, 1984, 23, 915 (isol)

2,4-Dibydroxy-1(5),11(13)-xantbadien- Sq-01758 4,9-Dibydroxy-1(5),11(13)-xantbadien- Sq-01759

12,8-olide 12,6-olide

HO (21;,4~,8cx):form
0

CtsHn04 M 266.336
(2~,4~,81¥.)-form
Deacetylxantlumol C15H 210 4 M 266.336
Constit. of Xanthium strumarium. Cryst. Mp 160-161°. [94662-97-2] Dicorin
(4~,6P,91X.,10f/)-form
[ex]i; -50° (c, 0.3 in CHCI 3). Constit. of Dicoria canescens. Syrup. [ex]~4 -117° (c, 1.3
2-Ac: Xanthanol in CHC1 3).
Ct 7H 240 5 M 308.374 Di-Ac: Cryst. (Et20jpet. ether). Mp ll8-l20°. [ex]i; -100°
From X. spinosum. Cryst. Mp 78-79°. [ex]i; -50° (c, 0.3 (c, 0.77 in CHC13).
in CHCl 3). 11P,13-Dihydro: 4,9-Dihydroxy-1(5)-xanthen-12,6-olide.
4-Ac: [28582-79-8]. lsoxanthanol Dihydrodicorin
Ct,H240s M 308.374 C15H 240 4 M 268.352
Constit. of X. strumarium. Cryst. (Et20jhexane). Mp Isol. from D. canescens. Cryst. (Etpjpet. ether) (as di-
101-102°. [ex]~ -27.9° (c, l in CHCI 3). Ac). Mp 140-141° (di-Ac). [ex]~4 -95° (c, 0.49 in CHC1 3)
Di-Ac: Cryst. (Et20jhexane). Mp 69-70°. [ex]~ -30.0° (c, (di-Ac).
0.99 in CHCl 3). Fang, S.D. eta/, Phytochemistry, 1984, 23, 2553.
2-Epimer, 2-Ac: 2-Epixanthanol
C17H 240 5 M 308.374 4,5-Dioxo-1(10)-xaritben-12,8-olide Sq-01760
Constit. of X. orientale. Gum.
4-Ketone, 2-Ac: [580-49-4]. Xanthinin
C17H 22 0 5 M 306.358
Constit. of X. pensy/vanium and X. italicum. Cryst.
(Et20). [exJn -53° (c, 2.4 in CHC1 3).
2-Deoxy, 4-ketone: 2-Deacetoxyxanthinin
C15H11P 5 '
M 280.320 ''
lsol. from Inula viscosa. Oil. [ex]i; + 14.1° (c, 1.5 in CtsH 200 4 M 264.321
CHCI 3). (8p,ll PH)-form
2-Deoxy, 11P,13-dihydro: [72145-31-4]. 4-0xo-1(5)-xanthen- Constit. of Dittrichia graveo/ens. Oil. [ex]~4 + 15° (c, 0.1
12,8ex-olide. 2-Deacetoxy-11p,13-dihydroxanthinin in CHCl 3).
C15H 220 3 M 250.337
Rustaiyan, A. eta/, Phytochemistry, 1987, 26, 2603.
Constit. of Helichrysum splendidum.
(2~¥.,8/I)-form
Ecbinaxantbol Sq-01761
4-Ketone, 2-Ac: [26791-72-0]. Xanthumin
C17H 220 5 M 306.358 [102341-43-5]
Constit. of X. spp. Cryst. (Et20/CHCI 3). Mp 100.5-101°.

~H
[ex]i;1 -48.2° (c, l in dioxan).
(2ft,8f/)-form
4-Ketone, 2-Ac: 2-Epixanthinin
C17H 210 5 M 306.358
Constit. of X. indicum. Cryst. [ex]~4 + 10° (c, 0.05 in
CHCI 3).
C15H 11,03 M 254.369
(2~,4~ ,8/I):form
A 5,10-cycloxanthane. Oil.
4-Ac: [18665-84-4]. Gafrinin
8-Cinnamoy/: [102273-87-0]. Cinnamoylechinaxanthol
C17H 240 5 M 308.374
C24H 310 4 M 384.514
Constit. of Geigeria africana and/. grandis. Cryst. Mp
Constit. of Echinacea purpurea. Oil.
ll0°. [ex]~ -16.1° (c, 5.2 in EtOH).
Bauer, R.F.X. eta/, Helv. Chim. Acta, 1985, 68, 2355.
Geissman, T. eta/, J. Org. Chem., 1962, 27, 2692 (Xanthinin)
Minato, H. eta/, J. Chem. Soc., 1965, 7009.
Anderson, L.A.D. eta/, Tetrahedron, 1968, 24, 1687 (Gafrinin)

463
Griesenin - 4-0xo-1(5),2,11(13)-xanthatrien-... Sq-01762 - Sq-01765

Griesenin Sq-01762 4-0xo-1(5),2,11(13)-xanthatrien-12,8-olide Sq-01765

[20087-04-1]
0

C15H 180 3 M 246.305

(8«,10/1)-form [26791-73-1] Xanthatin
C15H 160 4 M 260.289 Constit. of Xanthium spp. Cryst. (EtOH aq.). Mp 114-
Constit. of Geigeria africana. Cryst. (CHC1 3/Etp). Mp 1150. [oc] 0 -20°.
196-197.SO. [oc] 0 +284° (c, 0.6 in EtOH). 1oc,5oc-Epoxide: 1,5-Epoxy-4-oxo-2,11(1 3)-xanthadien-12,8oc-
2,3-Dihydro: [20087-05-2]. Dihydrogriesenin olide. 1«,5«-Epoxyxanthatin
C1sH180 4 M 262.305 C1sH1804 M 262.305
Constit. of G. africana. Cryst. (CHC1 3/Et 20). Mp 139.5- Constit. of X. spinosum. Oil.
140.50. [oc] 0 +92° (c, 0.72 in EtOH). 1P,5P-Epoxide: 1P,5P-Epoxyxanthatin
de Kock, W.T. et a/, Tetrahedron, 1968, 24, 6037, 6045 (isol, pmr) c1sH1804 M 262.305
From X. spinosum. Oil.
2-Hydroxy-4-oxo-1(5),11(13)-xanthadien- Sq-01763 (8P,10/I)-form
12,tH.Iide 1P,5P-Epoxide: 8-Epixanthatin 1P,5ft-epoxide
C1sH1 804 M 262.305
lsol. from X. spp. Gum. [oc]i: + 29° (c, 0.4 in CHC1 3).
1P,5P-Epoxide, 11oc,13-dihydro: 1P,5P-Epoxy-4-oxo-2-
xanthen-12,8ft-olide. 1P,5P-Epoxy-11oc,13-
dihydrotomentosin (incorr.)
CtsH1004 M 264.321
Constit. of X. pungens. Gum.
2,3-Dihydro: [33649-15-9]. 4-0xo-1(5),11(13)-xanthadien-
12,8P-olide. Tomentosint
C 15H 200 4 M 264.321 C15H100 3 M 248.321
(2S,6ft,10f/)-form [23264-32-6] Parthemollin lsol. from Parthenium tomentosum and Inula spp. Oil.
Constit. of Parthenice mol/is. Cryst. (EtOAc). Mp 116- Deuel, P.G. et a/, J. Am. Chern. Soc., 1957, 79, 3778 (isol)
1180. [oc]i: -130° (c, 4.28 in CHC1 3). Rodriguez, E.H. eta/, Phytochemistry, 1971, 10, 1145 (Tomentosin)
Herz, W. eta/, J. Org. Chern., 1970, 35, lllO (isol) Bohlmann, F. et al, Phytochemistry, 1982, 21, 1441 (isol)
Sundararaman, P. eta/, Tetrahedron Lett., 1973, 3809 (struct) Omar, A.A. et a/, Phytochemistry, 1984, 23, 915 (isol)
Sundararaman, P. eta/, J. Chern. Soc., Perkin Trans. 2, 1975, 440 Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 22ll (isol, pmr)
(cryst struct)

6-Hydroxy-4-oxo-1(5),11(13)-xanthadien- Sq-01764
12,8-olide

(6ft,8P,J 01;)-form
Ac: [79383-84-9]. lnuchinenolide A
C17Hu0s M 306.358
Constit. of Inula britannica. Oil. [ocli:' -54.6° (c, 0.5 in
CHC1 3).
Ito, K. et a/, Phytochemistry, 1981, 20, 271.

464
Carabrone - Curcumol Sq-01766 - Sq-01771

Carabranes Simple guaianes

Carabrone Sq-01766 Alismoxide Sq-01768

[1748-81-8] [8770 1-68-6]

C 15H 200 3 M 248.321 C15Hz.c0 M 220.354

Constit. of the fruits of Carpesium abrotanoides. Cryst. Constit. of Alisma p/antago-aquatica. Oil. [txln +3.1° (c,
(Et20jpet. ether). Mp 90-91°. [oc]n + 116.9° (c, 1 in 0.63 in CHC13).
EtOH). Oshima, Y. eta/, Phytochemistry, 1983, 22, 183.
4(.-A/coho/: [68776-20-5]. C•abrol
C 15H 220 3 M 250.337 3-Chloro-2-oxo-1(10),3,7(11),8- Sq-01769
Constit. of C. abrotanoides. Oil. Bp0 _2 110°. guiatetraen-12,6-olide
Minato, H. eta/, J. Chem. Soc. C, 1968, 2131 (Carabrone) [125280-53-7]
Maruyama, M. eta/, Phytochemistry, 1983, 22, 2773 (Carabrol)

Precarabrone Sq-01767
[74513-23-8]

Ct5H 13C103 M 276.719

Constit. of Stevia sanguinea. Yellowish solid.
M 220.354 Gil, R.R. eta/, Phytochemistry, 1989, 28, 2841 (isol, pmr)
C 15Hz.c0
Constit. of Silphium perfo/iatum. Oil. BPo.s 68°.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1987 (isol) Curcumenol Sq-01770
Bohlmann, F. et a/, Justus Liebigs Ann. Chern., 1982, 1211 (synth) [19431-84-6]

C 15H 220 2 M 234.338

Constit. of Curcuma zedoaria. Cryst. (EtOAc). Mp 118.5-
119.50. [txln +397° (c, 5.1 in CHC1J.
A. 1004l.Jsomer: [24063-71-6]. Isocfll'cllmeiiOI
C 15H 220 2 M 234.338
Constit. of C. zedoaria. Cryst. (EtOAc). Mp 139-141°.
[tx]n + 34° (c, 1.0 in CHC13).
Hikino, H. et a/, Chern. Pharm. Bull., 1968, 16, 39;. 1969, 17, 959.

Curcumol Sq-01771
[4871-97-0]

~
~-OH

r
M 236.353

465
Cyclokessol- 1,4-Dimethyl-7-(1-methylethenyl)... Sq-01772 - Sq-01779

Constit. of Curcuma wenyujin and C. zedoaria. Cryst. Mp
141-142°. [1X] 0 -32.26° (c, 2.127 in CHC1 3).
Hikino, H. eta/, Chern. Pharm. Bull., 1966, 14, 1241 (isol)
Inayama, S. eta/, Chern. Pharm. Bull., 1984, 32, 3783 (cryst struct,
abs conjig)
Constit. of C. aromatica. Needles (hexane). Mp 83-85°.
[1X]~ -43.1° (c, 0.2 in MeOH).
Kouno, I. eta/, Phytochemistry, 1985, 24, 1845 (isol)
Kuroyanagi, M. et al, Chern. Pharm. Bull., 1987, 35, 53 (cryst
struct)

Cyclokessol Sq-01772 8,11-Dihydroxy-4-guaien-3-one Sq-01776

H~
/ H
O~H
OH
CisH 240 2 M 236.353
C15H 240 3 M 252.353
Ac: [103223-36-5]. Cyclokessyl acetate
(lfJ,BfJ,J0/1)-form
C 17H:11;03 M 278.391
Constit. of essential oil of Valeriano fauriei. Cryst. Mp 8-Angeloyl, 11-Ac: [13018-10-5]. Tori/in
84-85.SO. [1X] 0 -46.4° (c, 0.40 in CHC1 3). C 22 H 3z0 5 M 376.492
Constit. of seeds of Tori/is japonica. Cryst. (pet. ether).
Oshima, Y. et al, Tetrahedron Lett., 1986, 27, 1829.
Mp 77-78°. [1X]b4 -45.3° (c, 0.85 in EtOH).
Chikamatsu, H. et al, Tetrahedron, 1969, 25, 4751.
1,6-Dihydroxy-4,11-guaiadien-3-one Sq-01773
1-(Dimethylaminomethyl)-S-isopropyl-3,8- Sq-01777
dimethylazulene
N,N,3,8-Tetramethyl-5-(1-methylethyl)-1-
azulenemethanamine, 9CI. N,N-Dimethylamino-3-
guaiazulenylmethane
[88141-88-2]
C 15H 22 0 3 M 250.337
6-Ac: [116085-10-0]. 6P-Acetoxy-lP-hydroxy-4, ll-guaiadien-
3-one
C 17H 240 4 M 292.374
Constit. of Pleocarphus revolutus.
Zdero, C. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 509.
C18H 25N M 255.402
4,5-Dihydroxy-7(11),9-guaiadien-8-one Sq-01774 Constit. of blue gorgonian (family Paramuriceidae).
Viscous blue oil.
[93801-01-5]
Li, M.K.W. eta/, Tetrahedron Lett., 1984, 25, 4707.

2,4-Dimethyl-7-ethylazulene Sq-01778
Se-Chamazulene
[490-88-0]
C1sH 220 3 M 250.337
C14H16 M 184.280
(4fJ.SfJ)-form [129673-90-1] Procurcumadiol Dehydrogenation prod. of natural compds. Blue oil.
Constit. of Curcuma tonga. Needles (C6H 6). Mp 150-
1,3,5-Trinitrobenzene complex: Violet cryst. (EtOH). Mp
150.SO.
112°.
Ohshiro, M. et al, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr)
Mangoni, L. et al, Gazz. Chim. /tal., 1962, 92, 286.

4,10-Dihydroxy-7(11)-guaien-8-one Sq-01775
1,4-Dimethyl-7-(1-methylethenyl)azulene, Sq-01779
9CI

~. 7-lsopropenyl-1 ,4-dimethylazulene. Lactarazulene

[489-85-0]

HO~O
CisH240 3 M 252.353
(la.,4fJ,5fJ,JOfJ)-form [98644-24-7] Zedoarondiol
Constit. of Curcuma zedoaria and C. aromatica. Needles
(CHC1 3). Mp 133-134°. [1X]~ -44.0° (c, 1.0 in MeOH). ClsH16 M 196.291
10-Me ether: Methylzedoarondiol Constit. of Lactarius deliciosus. Blue liq. Bp0.01 85-90°.
C 16H 260 3 M 266.380 Sorm, F. et a/, Collect. Czech. Chern. Commun., 1954, 19, 357.

466
5,11-Epoxyguaiane - 1(5),6-Guaiadiene Sq-01780 - Sq-01784

5,11-Epoxyguaiane Sq-01780 11,12-Epoxy-10(14)-guaien-4-ol Sq-01782

~ (lo,4a,5~,7~,10.),{onn
I
I

C 15H 160 M 222.370

(lrx.,4rx..Sft,7p,10rx.)-form
Constit. of Ligularia sp. Oil. [1X] 0 -45° (c, 2 in CHC1 3). C 15H 240 2 M 236.353
(Ift,4rx..SP,7P,l0f/)-form [21764-22-7] Liguloxide (lrx.,4rx..Srx.)-form
Constit. of L.fischeri. Cryst. Mp 36°. [IX]~ -58.2° (c, 1 Constit. of Pleocarphus revolutus. Oil. [1X]i;' +5° (c, 0.89
in CHC1 3). in CHC1 3).
9P-Hydroxy: [21764-23-8). Liguloxidol Zdero, C. et a/, J. Nat. Prod. (Lloydia), 1988, Sl, 509.
C 15H 160 2 M: 238.369
Constit. of L. fischeri. Oil. [IX]~ -36.8° (c, 1 in CHC1 3). Furopelargone Sq-01783
9P-Acetoxy: (18680-79-0]. Liguloxidol acetate
C 17H 280 3 M 280.406
Constit. of L. fischeri. Cryst. Mp 85°. [1X] 0 -52°.
3P-Hydroxy: 5,11-Epoxy-3p-guaianol. 3ft-Hydroxyliguloxide (1R)-form
C 15H 160 2 M 238.369
Constit. of Pulicaria paludosa. Oil. [IX]~ -22.2° (CHC1 3).
(lft,4P.SP,7P,l0fl)-form (20149-50-2] Guaioxide
Constit. of guaiac wood oil (Bulnesia sarmienti). Oil. C 15H 220 2 M 234.338
[IX)~ -40° (c, 1 in CHC1 3). (IR)-form [1143-45-9] Furopelargone A. Pelargone A.
Ishii, H. eta/, Tetrahedron, 1970, 26, 2751, 2911. Pelargone
Hirota, H. eta/, Bull. Chern. Soc. Jpn., 1980, 53, 785. Constit. of Pelargonium roseum. Oil. d~0 0.986. Bp0 .05 60-
San Feliciano, A. eta/, Phytochemistry, 1989, 28, 2717 (3P- 620. [1X]i,U -124.2° (neat). ni,U 1.4840.
Hydroxyliguloxide)
Semicarbazone: Cryst. (MeOH). Mp 152-153°. [IX)~ -170°
(c, 2 in CHC1 3).
3,4-Epoxy-8,1 0-guaianediol Sq-01781 (JS)-form [1143-46-0) Furopelargone B. Pelargone B
Constit. of P. roseum. Oil. Bp0 _1 81-83°. [1X)~4 +49° (c,

O~OH
1.5 in CHC1 3).
Semicarbazone: Cryst. (MeOH). Mp 160-164°.
1,2-Didehydro: [18492-61-0). Furopelllrgone C
CtsH 180 2 M 230.306
Constit. of P. roseum. Oil. Bp0_1 75°. [1X]i,U + 159° (c, 0.44
in CHC1 3).
CtsH160 3 M 254.369
2,3-Didehydro: [18492-62-1]. Furopelllrgone D
8-(4-Hydroxybenzoyl): (66559-24-8). Tenuferidin C15H 180 2 M 230.306
C 22H:31,05 M 374.476 Constit. of P. roseum. Oil. Bp0 _1 75-80°. [1X]i,U -57° (c,
lsol. from Ferula tenuisecta. Cryst. (Etp). Mp 164-165°. 0.33 in CHC1 3).
[1X] 0 + 75.0° (c, 1.2 in CHC1 3).
Lukas, G. eta/, Tetrahedron, 1964, 20, 1789 (iso/, uv, ir, pmr, ms,
8-(3-Hydroxy-4-methoxybenzoyl): [66559-22-6]. Tenuferin ord)
C 23H 320 6 M 404.502 Biichi, G. eta/, J. Am. Chern. Soc., 1965, ff7, 1589 (synth)
Isol. from F. tenuisecta. Cryst. (Etp). Mp 176-178°. [1X] 0 Biichi, G. et a/, Tetrahedron, 1968, 24, 2049 (synth)
+ 134.6° (c, 0.49 in MeOH). Giannotti, C. et a/, Tetrahedron, 1968, 24, 2055 (isol)
8-(4-Hydroxy-3-methoxybenzoyl): [66559-23-7]. Tenuferinin Takeda, A. eta/, J. Org. Chern., 1980, 45, 3125 (synth)
C 23 H320 6 M 404.502
lsol. from F. tenuisecta. Cryst. (Etp). Mp 102-103°. [1X] 0 1(5),6-Guaiadiene Sq-01784
+ 106.8° (c, 0.6 in MeOH). 1,2,3,4,5,6-Hexahydro-1,4-dimethyl-7-(1-
8-(3,4-Dimethoxybenzoyl): [66569-59-3]. Akiferinin methylethyl)azulene, 9CI. 1,2,3,4,5,6-Hexahydro-7-isopropyl-
C 24H 340 6 M 418.529 1,4-dimethylazulene
Constit. of F. akitschkensis. Mp 176-177°. [1X]i,U +73.1°
(c, 0.82 in CHC1 3).
Saidkhodzhaev, A.l. eta/, Khim. Prir. Soedin., 1978, 70, 137; (4cx,10cx)-form
Chern. Nat. Compd. (Engl. Trans/.), 55, 112.

C15H 24 M 204.355
(4rx.,l0rx.)-form [111900-51-7]
Constit. of Tolu balsam (from Balsamum tolutanum).
Oil. [1X]i;5 + 80° (c, 0.25 in CHC1 3).
(4P,10rx.)-form [111900-50-6]

467
1(5),7(11)-Guaiadiene- 4,6-Guaiadiene Sq-01785- Sq-01790

Constit. of Tolu balsam (B. tolutanum). Oil. [1X]i;5 + 36.2° 1(10),11-Guaiadiene Sq-01788
(c, 0.16 in CHC1 3).
Friedel, H.D. et al, Helv. Chim. Acta, 1987, 70, 1616.

1(5),7(11)-Guaiadiene Sq-01785
fl-Guaiene
[88-84-6]
C 15H 24 M 204.355
(4P,5rz,l0f/)-form [3691-11-0]rz-Bulnesene. t5-Guaiene
Constit. of guaiac wood oil (Bulnesia sarmienti). Also
from Pogostemon patchouli and Gossypium sp. Oil. Bp8
118°. [1X]n +8.28°. n~ 1.5046.
(4f.,5f.,l0f.)-form
rz-Chigadmtuene
C15H 24 M 204.355 Constit. of oil of Lansium anamalayanum. Oil. Bp9 117-
Constit. of sweet-flag oil. Oil. Bp 15 .5 137-139°. [IX]~ + 13°. 1180. [IX]~ -150° (CHC13).
I> ME6344000. Somasekar, A. et al, J. Indian Chern. Soc., 1952, 29, 604, 620 (a·
Takeda, K. et al, Tetrahedron, 1961, 13, 308 (synth) Chigadmarene)
Bates, R.B. et al, J. Am. Chern. Soc., 1962, 84, 1307 (struct) Bates, R.B. et al, J. Am. Chern. Soc., 1962, 84, 1307 (struct)
Minyard, J.B. et al, J. Agric. Food Chern., 1966, 14, 332 (isol)
Francis, N.J.O., Planta Med., 1972, 22, 201 (biosynth)
1(5),11-Guaiadiene Sq-01786 Mehta, G. et al, Tetrahedron Lett., 1975, 4495 (synth)
rz-Guaiene
[3691-12-l] 3,1 0(14)-Guaiadiene Sq-01789
Sc/erosporene
[69394-03-2]

C15H 24 M 204.355
Constit. of guaiac wood oil (Bulnesia sarmientl) and
patchouli oil (Postegmon patchouli). Oil. Bp 2.5 78-79°.
[IX]~ -64.5° (c, 3.6 in dioxan).
CtsHu M 204.355
lrx,51X-Epoxide: [10410-05-6]. 11X,51X-Epoxy-11-guaiene. Metab. of Sc/erotinia frutico/a.
Epoxyguaiene Katayama, M. et al, Tetrahedron Lett., 1979, 1773.
C 15H 240 M 220.354
Constit. of the essential oil of Cyperus rotundus. Oil. Bp 1
102-104°. [1X]n + 11.0°. 4,6-Guaiadiene Sq-01790
Takeda, K. et al, Tetrahedron, 1961, 13 (isol, struct)
Kapadia, V.H. et al, Tetrahedron Lett., 1967, 4661.

1(10),7(11)-Guaiadiene Sq-01787

C 15H 24 M 204.355
(la,J0/1)-form
lsoguaiaene. Isoguajen
Constit. of Ambrosia cumanensis and Parthenium
hysterophorus. Oil. Bp0.1 110° (bath). [1X]i;' + 36° (c, 1.7
C15H 24 M 204.355 in CHC1 3).
(4P,5rz)-form [3772-93-8] fl-Bulnesene (lf.,JOf.)-form [72646-95-8]
Constit. of guaiac wood oil (Bulnesia sarmientl) and Constit. of Athanasia dregeana. Oil. [1X]i;' -27.5° (c, 2 in
patchouli oil (Postegmon patchoulz). CHC1 3).
Heathcock, C.H. et al, J. Am. Chern. Soc., 1971, 93, 1746 (isol) Bohlmann, F. et al, Phytochemistry, 1977, 16, 575; 1979, 18, 995.
Oppolzer, W. et al, Helv. Chim. Acta, 1980, 63, 1198 (synth)
Sammes, P.G. et al, J. Chern. Soc., Chern. Commun., 1983, 666
(synth)
Bromidge, S.M. et al, J. Chern. Soc., Perkin Trans. 1, 1985, 1725
(synth)

468
5,11-Guaiadiene- 4,6-Guaiadien-11-ol Sq-01791 - Sq-01798

5,11-Guaiadiene Sq-01791 4,11(13)-Guaiadien-12-oic acid Sq-01795

~r COOH

C 15H 14 M 204.355 C15H 220 1 M 234.338

(lfJ,4rx.,7fJ,JOrx.)-form [22567-17-5] -y-Gurjunene (lrx.,7rx.,JOfJ)-form [57110-46-0] Aciphy/Jaic acid
Constit. of Dipterocarpus dyeri. [a:ln + 147°. Constit. of Anthemis spp. Oil. Bp0 . 1 150°.
Ehret, C. eta/, Tetrahedron, 1969, 25, 1785. Bohlmann, F. eta/, Chern. Ber., 1975, 108, 1902.

6,9-Guaiadiene Sq-01792 1(10),3-Guaiadien-8-ol Sq-01796

[36577-33-0]

~H
CtsH140 M 220.354
C 15H 14 M 204.355 8rx.-form
Constit. of the essential oil of geranium bourbon. Oil. Bp 7
110°. [a:]n -50.9° (c, 1.5 in EtOH). 0-(4-Hydroxybenzoyl): [69219-45-0]. Microferin
C22H 280 3 M 340.461
Nagahama, Y. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 3706.
Constit. of Ferula microcarpa. Cryst. (hexane). Mp 144-
1450. [a:]~ + 122.9° (c, 0.8 in CHC1 3).
9,11-Guaiadiene-3,4-diol Sq-01793 0-(4-Hydroxy-3-methoxybenzoyl): [69219-46-1].
Microferinin
C23H 300 4 M 370.488
From F. microcarpa. Cryst. (hexane). Mp 152-154°. [a:]i;'
+89.3° (c, 0.9 in CHC1 3).
Golovina, L.A. et a/, Khim. Prir. Soedin., 1978, 566.

1(1 0),7(11 )-Guaiadien-4-ol Sq-01797

C15H 140 1 M 236.353
(lfJ,3fJ,4rx..Srx.,7fJ)-form [107196-11-2] Dolich/asin
Constit. of Dolich/asium /agascae. Oil. [a:]i;' -16° (c, 3.96
in CHC1 3).
8a:-Hydroxy: 9,11-Guaiadiene-3,4,8-trio/. 8«.-
Hydroxydolichlllsin
CtsH140 3 M 252.353
From D. /agascae. Cryst. Mp 75°. [a:]i;' + 12° (c, 0.33 in
CHC1 3). C15H 140 M 220.354
8a:-Acetoxy: 8rx.-Acetoxydolichlasin (4rx..Srx.)-form [54750-42-4] 4-Hydroxy-fl-bulnesene
C 17H:11;04 M 294.390 Constit. of Asarum cau/escens. Oil.
From D. /agascae. Oil. [a:]i;' -9° (c, 0.72 in CHC13). Endo, J. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1974, 94,
1574.
Zdero, C. eta/, Phytochemistry, 1986, 25, 2873.

1,3-Guaiadien-15-oic acid Sq-01794

4,6-Guaiadien-11-ol Sq-01798

C 15Hzz01 M 234.338
C 15H 140
(1 rx.,lOfl)-form
~H
M 220.354
(7fJ,JOfJ)-form [54928-04-0] Jatamansic acid
11-Hydroxyguaiene
Constit. of Nardostachys jatamansi. Cryst. (EtOH). Mp
Constit. of Ambrosia cumanensis and Parthenium
123°. [a:]n -394° (CHC1 3).
hysterophorus. Oil. [a:]i;' +34° (c, 2.5 in CHC1 3).
Rucker, G. eta/, Arch. Pharm. (Weinheim, Ger.), 1974, 307, 791.
Bohlmann, F. eta/, Phytochemistry, 1977, 16, 575.

469
6,10(14)-Guaiadien-4-ol - 1,3,5,7,9-Guaiapentaene Sq-01799 - Sq-01805

6,10(14)-Guaiadien-4-ol Sq-01799 4,11-Guaiadien-3-one Sq-01803

rf\ (1 ex, 7~, I 0~)-form

HO~
C 15H 2•.0 M 220.354 C 15H 220 M 218.338
(IP,4«,5fl)-form [87827-55-2] Alismol (1«,7P,10fl)-form
Constit. of Alisma plantago-aquatica. Oil. [1X]n + 8. 7° (c, Constit. of Baccharis boliviensis. Oil. [1X]i," + 63° (c, 0.23
0.24 in CHC1 3). in CHC1 3).
(1!,4«,5«)-form [72646-96-9] (Ip,7p,l0«)-form [7764-53-6]
Constit. of Athanasia dregeana. Oil. [1X]i," -27.SO (c, 2 in Constit. of Pleocarphus revolutus. Oil. [1X]i," -63° (c, 0.75
CHC1 3). in CHCI 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 995. Buehl, G. et al, Proc. Chern. Soc., London, 1962, 280 (synth)
Oshima, Y. et al, Phytochemistry, 1983, 22, 183. Zdero, C. et al, Phytochemistry, 1989, 28, 531 (iso[)

1(5),7(11)-Guaiadien-8-one Sq-01800 1,3,5,7(11),9-Guaiapentaen-15-al Sq-01804

Calamusenone
[71305-96-9]

0~
I

~0
~ C15H 160 M 212.291
Constit. of Lactarius sanguifluus. Blood-red oil.
C15H:z:z0 M 218.338 De Rosa, S. eta/, Phytochemistry, 1987, 26, 2007.
Constit. of Acarus calamus. Oil. Bp0_01 90°. [IX]~ + 137° (c,
0.83 in CHCI 3).
1,3,5,7 ,9-Guaiapentaene Sq-01805
Rohr, M. eta/, Phytochemistry, 1979, 18, 279.
1,4-Dimethyl-7-(1-methylethyl)azulene, 9CI. 7-Isopropyl-1 ,4-
dimethylazulene. Guaiazulene. S-Guaiazulene. Kessazulene.
1(5),11-Guaiadien-2-one Sq-01801 Azulon. Eucazu/ene. Other proprietary names
[489-84-9]

~
C 15H:z:z0 M 218.338 ~2
(4p,7p,JOfl)-form [18374-76-0] Rotundone
Constit. of the essential oil of Cyperus rotundus. Oil. Bp 1 C 15H 18 M 198.307 .
128-129°. [1X]n -92.7°. Obt. from essential oils, e.g. chamomile oil. Found also m
marine red algae and the gorgonian Euplexaura erecta.
Kapadia, V.H. et al, Tetrahedron Lett., 1967, 4661. Used to treat gastrointestinal disorders. Blue-violet
Paknikar, S.K. et al, Indian J. Chern., Sect. B, 1983, 22, 1060
(synth) plates (EtOH) or blue oil. Mp 31.SO. Bp 12 167-168°. A.max
556, 581, 603, 632 and 662 nm(Et20).
I> C04790000.
4,7(11 )-Guaiadien-8-one Sq-01802
1,3,5-Trinitrobenzene complex: [4968-29-0].
Black needles (EtOH). Mp 151-151.5°.
Picrate: Black needles (EtOH). Mp 122-l22.SO.
2-Bromo: [90052-61-2]. 2-Bromo-1,3,5,7,9-guaiapentaene. 3-
Bromo-7-isopropyl-1 ,4-dimethylazulene. 3-
Bromoguaiazulene
C 15H 17Br M 277.203
C 15H 22 0 M 218.338 Constit. of a gorgonian of the Paramuriceidae family.
Constit. of Acarus calamus. Oil. Bp0_01 90°. [IX]~ -178° (c, Oil.
1 in CHC1 3). 2-Chloro: [90052-60-1]. 2-Chloro-1 ,3,5,7,9-guaiapentaene. 3-
Rohr, M. et al, Phytochemistry, 1979, 18, 279. Chloro-7-isopropyl-1 ,4-dimethylazulene. 3-
Chloroguaiazulene
C15H 17Cl M 232.752 . . .
Constit. of a gorgonian of the Paramunce1dae family.
12-Bromo: [90052-62-3]. 12-Bromo-1,3,5,7,9-guaiapentaene.
7-(2-Bromo-1-methylethyl)- I ,4-dimethylazulene, 9CI.
Ehuazu/ene
470
1,3,5,7(11),9-Guaiapentaen-15-ol- 1(5)-Guaien-11-ol Sq-01806 - Sq-01812

C 15H 17Br M 277.203 6-Guaiene-4,1 0-diol Sq-01809

Constit. of a gorgonian of the Paramuriceidae family. [74 513-46-5]
Oil. [aln + 2° (hexane).
Plattner, P.A. et a/, Helv. Chim. Acta, 1949, 32, 2137, 2452 (synth)
Sorm, F. eta/, Collect. Czech. Chern. Commun., 1951, 16, 168, 626
(iso/, synth)
Caujolle, F. eta/, Ann. Pharm. Fr., 1952, 10, 412 (pharmacal)
Herz, A., Arzneim.-Forsch., 1953, 3, 253 (pharmacal)
Jacob, T.M. eta/, Tetrahedron, 1964, 20, 2821 (uv, synth)
Llinas, J.R. et a/, Can. J. Chern., 1975, 53, 2911 (pmr, cmr)
Hoffmann, W. eta/, Tetrahedron Lett., 1975, 533 (synth) C 15H160 1 M 238.369
Mukherjee, D. et a/, J. Am. Chern. Soc., 1979, 101, 251 (synth)
Fusetani, N. et a/, Experientia, 1981, 37, 680 (isol) (4rt.,5rt.,10rt.)-form
Martindale, The Extra Pharmacopoeia, 28th/29th Ed., Constit. of Silphium perfoliatum. Cryst. (EtzO/pet.
Pharmaceutical Press, London, 1982/1989, 1611. ether). Mp 144°. [a]~4 -1.1° (c, 0.9 in CHC1 3).
Li, M.K.W. et a/, Tetrahedron Lett., 1984, 25, 587 (derivs) (4rt.,5fl,l0rt.)-form
Constit. of S. perfoliatum. Cryst. (EtzOjpet. ether). Mp
1,3,5,7(11),9-Guaiapentaen-15-ol Sq-01806 111.SO. [aln + 0°.
Sangol Bohlmann, F. et al, Phytochemistry, 1979, 18, 1987.
[130177-42-3]
10(14)-Guaiene-4,11-diol Sq-01810

C 15H 180 M 214.307

H~
y~H
Constit. of Lactarius sanguifluus. Dark red oil. CtsHu01 M 238.369
Sterner, 0. eta/, Phytochemistry, 1989, 28, 2501 (iso/, pmr) (lrt.,4rt.,5rt.)-form [65647-30-5]
Constit. of Chenopodium botrys. Cryst. (Et20). Mp 117°.
[aln -35° (c, 1.2 in MeOH).
4(15),10(14),11(13)-Guaiatriene-6,12-diol Sq-01807
11-Ac: [74799-29-4]. 11-Acetoxy-10(14)-guaien-4a-ol
C1 7H180 3 M 280.406
Constit. of C. botrys. Oil. [aln +20° (c, 0.9 in CHC1 3).
de Pascual, T.-J. eta/, Tetrahedron, 1980, 36, 371.

10(14)-Guaiene-4,6,8-triol Sq-01811

C 15H 110 1 M 234.338

(lrt.,4rt.,5rt.,7f/)-form [90548-06-4] Watsonol A
Constit. of Magnolia watsonii. Cryst. Mp 65-67°.
12-Ac: [90548-07-5]. Watsonol B
-~-'
H H
HO
1
• OH

C 17H140 3 M 276.375
From M. watsonii. Oil. C 15H 160 3 M 254.369
Ito, K. et a/, Phytochemistry, 1984, 23, 188. (lrt.,4/l,5P,6P,7fl,8f/)-form [1 02273-88-1]
Dihydroxynardol
1(5),6,9-Guaiatrien-8-one Sq-01808 Oil.
Orobanone 8-Cinnamoyl: Cinnamoyldihydroxynardol
[78916-35-5] C14H 310 4 M 384.514
Constit. of Echinacea purpurea. Oil.
Bauer, R.F.X. et al, Helv. Chim. Acta, 1985, 68, 2355.

1(5)-Guaien-11-ol Sq-01812

~H
C15H100 M 216.322
Constit. of Orobanche rapu-genistae. Oil.
Fruchier, A. et a/, Phytochemistry, 1981, 20, 777.

C 15H 160 M 222.370

(4fl,7fl,l0f/)-form [489-86-1] Guaiol. Champacol

471
1(10)-Guaien-11-ol - 7-Guiaene-4,10-diol Sq-01813 - Sq-01819

Constit. of guaiacum resin. Also occurs in Callitris 6-Guaien-4-ol Sq-01816

intratropica, Eucalyptus maculate, Drimys lanceolata and
others. Simple esters, esp. the acetate used in perfumery
industry. Cryst. (Me 2CO at -15°). Mp 89-90°. [cxln
-41 o (c, 3.5 in CHCl 3).
Minato, H. eta/, Tetrahedron, 1961, 13, 308 (struct)
Marshall, J.A. eta/, J. Org. Chem., 1972, 37, 982 (synth)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, C15H160 M 222.370
no. 1916 (occur)
Buchanan, G.L. eta/, J. Chem. Soc., Perkin Trans. I, 1973, 2404 (1«,4«,5P)OI;.)-form [74513-47-6]
(synth) Constit. of Silphium perfoliatum. Oil.
Andersen, N.H. eta/, Tetrahedron Lett., 1973, 2079 (synth) Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1987.

1(10)-Guaien-11-ol Sq-01813 10(14)-Guaien-4-ol Sq-01817

Nardo/

~H
[6090-27-3]

C15H 160 M 222.370

(4P,5«,7f/)-form [22451-73-6] Bulnesol
Constit. of guaiac wood oil (Bulnesia sarmientt). Also
C15H 160
H0«1
M 222.370
Constit. of Nardostachys jatamansi and Japanese valenan
.
from Ferula spp. Cryst. Mp 69-70°. Bp4 136-138°. [cxln (Valeriana sp.). Bp0 _5 120-125° (bath). [cx]i,? -10.17° (c,
+ 3.8° (EtOH). 2.36 in CHCl 3), [cxJn + 5.4°.
Heathcock, C.H. eta/, J. Am. Chem. Soc., 1971, 93, 1746 (synth) Sastry, S.D. eta/, Tetrahedron Lett., 1966, 1035 (isol, struct)
Andersen, N.H. eta/, Synth. Commun., 1973, 3, 115 (synth) Hikino, H. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1974, 95,
Teisseire, P. eta/, Recherches, 1974, 19, 8 (isol) 243 (isol)

2-Guaien-1 0-ol Sq-01814 11-Guaien-10-ol Sq-01818

Karatavin Pogostol
[69219-47-2] [21698-41-9]
OH

C 15H160 M 222.370
Constit. of Ferula karatavica. Cryst. (pet. ether). Mp 136-
C15H 160 M 222.370
~ .
Constit. of patchouli oil from Pogostemon cab/in. 011. [cxln
1370.
-20.2° (c, 8.7 in CHC1 3).
Bagirov, V.Yu., Khim. Prir. Soedin., 1978, 655. Hikino, H. eta/, Chem. Pharm. Bull., 1968, 16, 1608 (isol)
Bruns, K., Parfuem. Kosmet., 1978, 59, 109 (isol)
5-Guaien-11-ol Sq-01815
7-Guiaene-4,1 0-diol Sq-01819

~H
Curcumadiol
[31946-48-2]
OH

C15H160 M 222.370
(JP,4«,7P)0«)-form [68349-52-0]
Constit. of Dipterocarpus spp. Oil. [ex]~
CHCl 3).
+ 75° (c, 1.4 in
C15H160 2
HO~
M 238.369
Constit. of Curcuma zedoaria. Cryst. (EtOAc). Mp 145-
Riicker, G. eta/, Phytochemistry, 1978, 17, 809.
145.SO. [cxJn -11.6° (c, 1.7 in EtOH).
Hinkino, H. eta/, Chem. Pharm. Bull., 1971, 19, 93.

472
Hanalpinol- 11-Hydroxy-4-guaien-3-one Sq-01820 - Sq-01827

Hanalpinol Sq-01820 4-Hydroxy-7(11),9-guaiadien-8-one Sq-01824

[94388-64-4]

ih-f"
~ C 15H 110 1 M 234.338
(11X,4P,5fl)-form [21698-40-8] Procurcumenol
C 15H 240 3 M 252.353
Constit. of rhizomes of Alpinia japonica. Oil. [1X]i,S + 167.8° Constit. of the dried rhizomes of Curcuma zedoaria and
(c, 0.42 in EtOH). C. longa. Oil. [1X]n + 140.9° (c, 10.5 in CHCl3). Struct.
Ketone: [96030-75-0]. revise<I,in 1986.
Plates (pentane). Mp 80.5-82°. Hikino, H. eta/, Chern. Pharm. Bull., 1968, 16, 1605; 1977, 25, 6
Itokawa, H. eta/, Chern. Pharm. Bull., 1985, 33, 2023 (cryst struct) (isol)
Yoshihara, M. et al, Chern. Pharm. Bull., 1986, 34, 434 (struct)
Ohshiro, M. et al, Phytochemistry, 1990, 29, 2201 (isol, pmr, cmr)
Hanamyol Sq-01821
[94388-63-3] 4-Hydroxy-7(11 ),10(14)-guaiadien-8-one Sq-01825

C 15H 21,01
~
M 238.369
H

Constit. of rhizomes of Alpinia japonica. Needles. Mp 90-

930. [1X]); -18.0° (c, 0.1 in CHCl 3). C15H 110 1 M 234.338
Itokawa, H. eta/, Chern. Lett., 1984, 1687 (cryst struct) (11X,4P,5fl)-form
Minor constit. of essential oil of Zedorariae Rhizoma.
Needles (Etpjhexane). Mp 96-98°. [IX]~ -44° (CHCl 3).
2-Hydroxy-12,6-furano-9-guaien-8-one Sq-01822
Yoshihara, M. et al, Chern. Pharm. Bull., 1986, 34, 434 (cryst
struct)

12-Hydroxy-4,11(13)-guaiadien-3-one Sq-01826
I
H'

ClsHls03 M 246.305
Me ether: 2-Methoxyfurano-9-guaien-8-one
C 16H 100 3 M 260.332
Constit. of essential oil of myrrh. Oil.
Brieskom, C.H. eta/, Phytochemistry, 1983, 22, 1207. C 15H 110 1
~~OH
M 234.338
(Jp,JOiX)-form
1-Hydroxy-4,11-guaiadien-3-one Sq-01823 Ac:
C1,H240 3 M 276.375
Constit. of Jungia stuebelii. Gum. [1X]i: -36° (c, 0.28 in
CHC1 3).
(2-Hydroxy-2-methylbutanoyl):
C10H 300 4 M 334.455
Constit. of Moscharia pinnatifida. Oil.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1201 (isol)
Singh, P. et al, Phytochemistry, 1990, 29, 3944 (isol)
C 15H 110 1 M 234.338
(lp,7p,JOiX)-form
Constit. of Jungia stuebelii. Gum. [1X]i;l -29° (c, 0.14 in 11-Hydroxy-4-guaien-3-one Sq-01827
CHCl 3).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1201.

C1sH2401 M 236.353
(11X,7P,10f/)-form [20482-28-4]

473
5-Hydroxy-2-oxo-1(10),3,11(13)-... - P-Kessyl al(:ohol Sq-01828 - Sq-01833

Constit. of Euryops pedunculatus. Oil. [a]i;' + 18° (c, 0.2 7-Isopropenyl-4-methyl-1- Sq-01830
in CHC1 3). azulenecarboxaldehyde
Jakupovic, J. et al, Phytochemistry, 1987, 26, 1049. 1-Formy/-7-isopropenyl-4-methy/azulene. Lactaroviolin
[85-33-6]
5-Hydroxy-2-oxo-1(10),3,11(13)- Sq-01828
guaiatrien-12-oic acid
0 14

C15H 180 4
~'
M 262.305
HOOC
C 15H 140 M 210.275
Constit. of Lactarius deliciosus. Antibiotic active
principally against Mycobacterium tuberculosis. Violet-
red cryst. (pet. ether). Mp 58°.
SP-form 11,12-Dihydro: [24687-70-5]. 11,11-Dihydrolactaroviolin. 1-
Hypocretenoic acid Formyl-7-isopropy/-4-methy/azu/ene
Me ester: [84813-80-9]. C 15H 160 M 212.291
C16H 200 4 M 276.332 Constit. of L. deterrimus. Cryst. Mp 59-60°.
Constit. of Hypochoeris cretensis. Gum. [ali;' + 35° (c, Schmid, R. et al, Helv. Chim. Acta, 1954, 37, 2018 (struct)
0.1 in CHC1 3). Sorm, F. et a/, Collect. Czech. Chern. Commun., 1955, 20, 227
Lactone: [84813-70-7]. Hypocretenolide (struct)
C15H 160 3 M 244.290 Meache, D. eta/, Helv. Chim. Acta, 1967, 50, 1178 (pmr)
Constit. of H. cretensis. Gum. Kou1, S.K. et al, Phytochemistry, 1985, 24, 181 (deriv)
Lactone, 14-hydroxy: 14-Hydroxyhypocretenolide
C 15H 160 4 M 260.289 7-Isopropyl-2,4-dimethylazulene Sq-01831
Constit. of Hedypnois cretica. Oil. 2,4-Dimethyl-7-(1-methylethyl)azu/ene, 9CI. Se-Guaiazulene
Lactone, 14-P-n-G/ucopyranosy/oxy: [492-45-5]
C21 Hu,09 M 422.431
Constit. of H. cretica.
Lactone, Jla,13-Dihydro, 14-hydroxy: 14-Hydroxy-11,13-
dihydrohypocretenolide
C 15H 180 4 M 262.305
Constit. of H. cretica. Oil.
Lactone, 11 a,13-Dihydro, 14-P-n-g/ucopyranosy/oxy:
C 11 H:~~~09 M 424.447 C 15H 18 M 198.307
Constit. of H. cretica. Found in essential oils. d~g 0.985. Bp3 138-140°.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2119 (isol, struct) 1,3,5-Trinitrobenzene complex: [40980-27-6].
Harraz, F.M. et al, Phytochemistry, 1988, 27, 1866 (derivs) Dark-red-brown needles (EtOH). Mp 152°.
Picrate: Mp 113°.
10-Isocyano-6-guaiene Sq-01829 Sorm, F. et al, Collect. Czech. Chern. Commun., 1951, 16, 184.
6-Guaiene- 10-isocyanate Jacob, T.M. et al, Tetrahedron, 1964, 20, 2821.

rn
Hoffmann, W. et al, Tetrahedron Lett., 1975, 533.
[114944-03-5]

8-Isopropyl-2,4-dimethylazulene Sq-01832
Zierazulene
C 15H 18 M 198.307
A.max 546 nm.

~ 1,3,5-Trinitrobenzene complex: Mp 122.5°.

Picrate: Mp 119°.
C16H15N M 23 1.380 Birch, A.J. eta/, Chern. Ind. (London), 1955, 1773.
Constit. of an unidentified sponge. Cryst. Mp 57-59°. [aln
-60.1° (c, 0.4 in CHC1 3).
P-Kessyl alcohol Sq-01833
Tada, H. et a/, J. Org. Chern., 1988, 53, 3366 (iso/, pmr, cryst
struct) [3466-70-4]
HO HI

C15H160 1 M 238.369
~(
Cryst. (EtOH or pet. ether). Mp 150.5-151°. [aln -15.1°
(c, 5.3 in CHC1 3).
2-Ketone: [3466-16-8]. P-Kessyl ketone

474
Kessyl glycol- 2-0xo-1(10),3,5-guaiatrien-2-... Sq-01834 - Sq-01839

Cryst. (EtOH). Mp 109-110°. [1X]n -182.7° (c, 5.0 in Pigment of the sea gorgonian Paramuricea chamaeleon.
CHC1 3). Dehydrogenation prod. of sesquiterpenoids. Lustrous
Hikino, H. eta/, Chern. Pharm. Bull., 1967, 15, 485. violet-black plates (2-propanol). Mp 106-107°.
2,3-Dihydro: [110207-64-2]. 2,3-Dihydro/inderazulene. /1,11-
Kessyl glycol Sq-01834 Dihydrolinderazulene
Kessoglyco/
C15H 160 M 212.291
Constit. of an Acalycigorgia sp. Purple oil. [1X]n +800°
[6894-57-1] (c, 0.05 in CHC1 3).

\-W-aH
Takeda, K. et al, J. Chern. Soc., 1964, 2591 (synth, bib[)
H~ Imre, S. eta/, Experientia, 1981, 37, 442 (isol)
Sakemi, S. eta/, Experientia, 1987, 43, 624 (deriv)

3-0xo-4,11(13)-guaiadien-12-oic acid Sq-01838

/ H
C,5H 21;03 M 254.369
Constit. of the rhizome of Valeriana officina/is. Cryst. Mp
128°. Bp4 130-135°. [1X]n -19.3° (c, 3.4 in CHC1 3).
Di-Ac: Cryst. (pet. ether). Mp 117°. [1X]n -78.SO (c, 10.4 in
CHC1 3).
8-Deoxy: [3321-65-1]. rz-Kessyl alcohol
C 15H 160 1 M 238.369 C,5H 200 3 M 248.321
Constit. of V. officina/is and other spp. Cryst. (EtOH or (lrz,7P,10fl)-form [83161-56-2] Pechueloic acid
pet. ether). Mp 85-86°. [1X]n -38.4° (c, 10.1 in CHC1 3). Constit. of Decachaeta scabre/la. Gum.
8-Deoxy, 2-ketone: [7637-95-8]. IX-Kessyl ketone Me ester: Methyl pechueloate
Cryst. (EtOH). Mp 105°. [IX]~ + 239° (c, 10.0 in CHC1 3). C 16Hzz0 3 M 262.348
8-Deoxy, I-epimer: /sokessyl alcohol Constit. of Pechuel-Loeschea leibnitziae. Gum. [1X]i;'
Cryst. (EtOH). Mp 118-119°. +24° (c, 0.4 in CHC1 3).
8-Deoxy, I-epimer, 2-ketone: [7663-37-8]. lsokessyl ketone ll,I3-Dihydro: 3-0xo-4-guaien-I2-oic acid. /1,13-
Cryst. (EtOH). Mp 56°. [1X]n -133.5°. Dihydropechueloic acid
2,8-Dideoxy: [3321-66-2]. Kessane C 15H 110 3 M 250.337
C 15H160 M 222.370 From D. scabre/la. Gum.
Constit. of V. officina/is. Liq. Bp6 110-112°. [1X]n - 7.2° Bohlmann, F. et a/, Phytochemistry, 1982, 21, 1160.
(c, 10.0 in CHC1 3). Miski, M. eta/, Phytochemistry, 1987, 26, 199.
Hikino, H. et a/, Chern. Pharm. Bull., 1963, 11, 547 (Kessane)
Ito, S. eta/, Tetrahedron, 1967, 23, 553 (struct) 2-0xo-1(10),3,5-guaiatrien-2-oic acid Sq-01839
Hikino, H. et a/, Tetrahedron, 1968, 24, 3147 (synth)
Kato, M. eta/, J. Chern. Soc., Chern. Commun., 1970, 937 (synth) Parishin B
[23554-79-2]
Lactarofulvene Sq-01835
I ,6-Dihydro-7-isopropenyl-4-methyl-I-methy/eneazu/ene, 8CI.
I ,6-Dihydro-4-methyl-I-methylene-7-(I-
methylethenyl)azulene
[18454-60-9]

C15H 180 3 M 246.305

Isol. from Artemisia tridentata ssp. tridentata f. parishii.
Mp 221-223°. [1X]D + 153°.
Irwin, M.A., Ph. D., Thesis Univ. of California at Los Angeles
(isol)
C 15H 16 M 196.291 Marx, J.N. et a/, Tetrahedron, 1969, 25, 2117 (synth)
Constit. of Lactarius de/iciosus. Unstable orange liq.
Betelli, D.J. et a/, Tetrahedron, 1968, 24, 2079.

Linderazulene Sq-01836
3,5,8-Trimethylazuleno[6,5-b]furan, 9CI
[489-79-2]

~
M 210.275

475
Oxycurcumenol - 1-Chloro-3,4-epoxy-2,10-dihydroxy-... Sq-01840 - Sq-01844

Oxycurcumenol Sq-01840
[119205-46-8]
12,6-Guaianolides

Bishopantholide Sq-01842
[99305-09-6]
C 15H120 3 M 250.337
Constit. of Curcuma heyneana. Prisms (MeOH). Mp 114-
1W. [1X)i:' -133° (c, 0.1 in CHC1 3).
Firman, K. eta/, Phytochemistry, 1988, 27, 3887.

Zedoarol Sq-01841
[103994-22-5]
0
C 17H 200 8 M 352.340
Constit. of Bishopanthus soliceps. Oil. [1X)n +28° (c, 0.19 in
CHC1 3).
2P,3P-Epoxide: 2P,3fJ-Epoxybishopantholide
C 17H 200 9 M 368.340
From B. soliceps. Oil. [1X)n +44° (c, 0.3 in CHC13).
C 15H 180 3 M 246.305 Singh, P. et a/, Phytochemistry, 1985, 24, 2110.
Constit. of Curcuma zedoaria. Oil. [IX)~ + 11.6° (c, 2.0 in
CHC1 3).
3-Chloro-8,9-dihydroxy-2-oxo- Sq-01843
Shiobara, Y. et a/, Phytochemistry, 1986, 25, 1351.
1(10),3,11(13)-guaiatrien-12,6-olide
0

0
C 15H 15Cl0 5 M 310.733
(1 rx,6rx,Bp,9fJ)-form
3-Ch/oro-8,9-dihydroxydehydroleucodin
8-(2-Acetoxymethyl-2E-butenoyl):
C12H 23C10 8 M 450.872
Constit. of Lasiolaena santosii. Gum. [1X)i;l -60° (c, 0.4
in CHC1 3).
8-(2-Acetoxymethyl-2E-butenoyl), 9-Ac:
C24 H 25C108 M 476.909
Constit. of L. santosii. Gum.
9-Deoxy, 8-0-(2-Acetoxymethyl-2E-butenoyl):
CuH 23Cl0 7 M 434.872
Constit. of L. santosii. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.

1-Chloro-3,4-epoxy-2,1 0-dihydroxy- Sq-01844

11(13)-guaien-12,6-olide

0
C 15H 19C10 5 M 314.765
(lrx,2P,3P,4P,5rx,6rx,10rx)-form [98259-96-2) Ch/oroklozchin

476
4-Chloro-1,2-epoxy-3,10-dihydroxy•.•. - 14-Chloro-2,8,10-trihydroxy-3,11(13)... Sq-01845- Sq-01850

Constit. of Artemisia klotzchiana. Cryst. 14-Chloro-2,5,8,10-tetrahydroxy-3,11(13)- Sq-01848

(Me 2COfdiisopropyl ether). Mp 230°. [ocln -ll9.SO. guaiad.ien-12,6-olide
Mata, R. et al, Phytochemistry, 1985, 24, 1515.
HOHq CH2 Cl
4-Chloro-1,2-epoxy-3,10-dihydroxy- Sq-01845 H'
I

11(13)-guaien-12,6-olide

0
C15H 19Cl0 6 M 330.764
(lrz,2fl,5rx,6rz,8fl,l0rz)-form
8-Angeloy/: [20071-50-5]. Eupachlorin
C20H 25CI07 M 412.866
CtsH 19CI05 M 314.765 Constit. of Eupatorium rotundifolium. Tumour inhibitor.
(1«,2«.3rx,4fl,5rx,6rx,l0ri)-form [117255-08-0] Andalucin Cryst. (MeOH). Mp 219-221° dec. [oc]i; -ll0° (c, 0.35
Constit of Artemisia lanata. Gum. in EtOH).
Aguilar, J.M. eta/, Phytochemistry, 1988, 27, 2229. 8-Ange/oy/, 2-Ac: [20501-52-4]. Eupachlorin acetate
C22H 27CI08 M 454.903
14-Chloro-3,4-epoxy-2,5,8,1 0- Sq-01846 Constit. of E. rotundifolium. Tumour inhibitor. Cryst.
(C6H6). Mp 161-164° dec. (in vacuo). [01:]~ -192° (c, 0.63
tetrahydroxy-11(13)-guaien-12,6-olide in MeOH).
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3876.

15-Chloro-2,3,4,8-tetrahydroxy- Sq-01849
10(14),11 (13)-guaiad.ien-12,6-olide

C,sH19Cl07 M 346.764
(1 «,2fl.3rx,4rx,5rx,6rx,8fl,l Orx )-form
8-Ange/oy/: [20071-52-7]. Eupachloroxin
C20H25Cl08 M 428.865 0
Constit. of Eupatorium rotundifolium. Tumour inhibitor. CtsH,9Cl06 M 330.764
Amorph. Chromatography on acid-washed alumina (lrz,2rz.3/l,4rz,5rz,6rz,8rz)-form
gives Eupatoroxin. 8-(2-Methy/propenoyl): [I 06566-98-7]. Chlororepdiolide
5-Deoxy, 8-0-(4-Acetoxy-2Z-butenoyl): [53142-40-8]. Ct9H23CI0 7 M 398.839
Graminichlorin Constit. of Centaurea repens. Cryst. Mp 207-208°. [01:]~
CuH 27 Cl09 M 470.903 +80.2° (c, 0.109 in CHCI3).
Constit. of Liatris spp. Gum. [oc]i; -36° (c, 1.25 in (lrz,2fl.3fl,4rz,5rz,6rz,8rz)-form
CHCI 3).
8-(2-Methy/propenoyl): [106310-35-4]. Repensolide
Kupchan, S.M. et al, J. Org. Chern., 1969, 34, 3876 Ct9H23Cl0 7 M 398.839
(Eupachloroxin)
Herz, W. eta/, J. Org. Chern., 1975, 40, 199 (Graminich/orin) Constit. of C. spp. Oil.
Stevens, K.L. eta/, J. Nat. Prod. (Lioydia), 1986, 49, 833.
Jakupovic, J. eta/, Planta Med., 1986, 398.
3-Chloro-1,2-epoxy-4,8,10-trihydroxy- Sq-01847
11(13)-guaien-12,6-olide
14-Chloro-2,8,10-trihydroxy-3,11(13)- Sq-01850
guaiad.ien-12,6-olide
[72947-97-8]

C15H 19Cl06 M 330.764

[72971-52-9] Bibsanin.
(1~,2~.3~,4~,5rx,6rx,8rx,JO~)-form
Biebsanin
Constit. of Achillea biebersteinii and A. santo/ina. Cryst. CtsH,9CI05 M 314.765
(EtOAc). Mp 258-259°. [oc]i? -34° (c, I in Py). (lrz,2fl,5rz,6rz,8fl,l0rz)-form
Yusupov, M.l. eta/, Khim. Prir. Soedin., 1979, 580. 8-(4-Hydroxy-2-methyl-2Z-butenoy[) 2-Ac: Eupachifolin D
C 22 H 27Cl08 M 454.903

477
15-Chloro-3,4,8-trihydroxy-10(15)... - 1,2:3,4-Diepoxy-8,10-dihydroxy-12,6-... Sq-01851 - Sq-01854

Constit. of Eupatorium chinense. Cryst. Mp 247-250°. C 1 ~H 18 0~ M 278.304

[a)~ -92.6° (c, 0.22 in CHC1 3).
Ito, K. eta/, Chern. Lett., 1979, 1473.
15-Chloro-3,4,8-tribydroxy-1 0(15),11(13)-
guaiadien-12,6-olide
There is considerable confusion in the literature concerning
the structure of this compound. Constit. of
Chrysanthemum parthenium, C. morifolium, Artemisia
mexicana, A. k/otzchianaand Tanacetum parthenium.
Sq-01851 Cryst. (Me2CO). Mp 250°. [a]~ -13.4° (c, 0.35 in
CHC1 3). The structs. of closely related compds.
Chrysartemin B and Artecanin require clarification at
present.
[29431-83-2, 29431-84-3)
Begley, M.J. eta/, Phytochemistry, 1989, 28, 940 (isol, cryst struct,
bib/)

0 Crepiside C Sq-01853
C 1 ~H 19 Cl0~ M 314.765 [100228-51-l)
The publ. stereochem. info. on the compds. covered by
this entry appears to be incomplete but they are prob.
stereochernically homogeneous as given here.
(1«,3P,4«,5«,6«,8«)-form [38290-03-8] Chlorohyssopifolin B
Constit. of Centaurea hyssopifolia. Cryst. Mp 192-194°.
[aJn +67° (c, 0.3 in CHC13).
8-0-(2,3-Dihydroxy-2-methy/butanoyl): [54278-80-7].
Chlorohyssopifolin E
C19H 25Cl08 M 416.854 C21 H 280 9 M 424.447
Constit. of C. hyssopifolia. Cryst. Mp 118-119°. [aJn Constit. of Crepis japonica. Needles (MeOH). Mp 213-
+91° (c, l.l in MeOH). 2160. [a]~ + 24.0° (c, 1.56 in MeOH).
8-0-(2-Ethoxy-3-hydroxy-2-methy/propanoyl): [54278-79-4). 8-Epimer: [100187-62-0]. Crepiside D
Chlorohyssopifolin D C21 H 280 9 M 424.447
C21 H 29Cl08 M 444.908 Constit. of C.japonica. Amorph. powder. [a]~ +5l.SO
Constit. of C. hyssopifolia. Cryst. Mp 186-188°. [aJn (c, 0.68 in MeOH).
+89° (c, 1.3 in MeOH). 8-Epimer, 8-0-(p-hydroxypheny/acetyl): [I 00187-61-9].
8-0-(2-Methy/propenoyl): [62462-98-0]. Linichlorin A Crepiside F ·
C1,H 23Cl0 6 M 382.840 C29H340 11 M 558.581
Constit. of C. linifolia. Cryst. (CHC1 3/diisopropyl ether). Constit. of C. japonica. Amorph. powder. [1X]n + 68.3°
Mp 153-155°. [aJn +89° (c, 0.6 in CHC13). (c, 0.41 in MeOH).
8-0-(3-Ch/oro-2-hydroxy-2-methy/propanoyl): [37006-36-3). Miyase, T. eta/, Chern. Pharm. Bull., 1985, 33, 4451.
Centaurepensin. Chlorohyssopifolin A
C1,H%4Cl20 7 M 435.300 1,2:3,4-Diepoxy-8,10-dihydroxy-12,6- Sq-01854
Constit. of C. repens. Cryst. Mp 214-215°. [a]~4 + 107.2°
(c, l.l in THF). guaianolide
8-(2,3-Epoxy-2-methy/butanoyl)(R-): [95602-93-0).
Solstitiolide. Repin 4,5-ch/orohydrin
C19H 23Cl07 M 398.839
Isol. from Centaurea so/stitialis. Oil. Mixt. with -OH
Episolstitiolide.
8-(2,3-Epoxy-2-methy/butanoyl)(S-): [95602-95-2].
Episolstitiolide. Subluteolide 4,5-ch/orohydrin
C1,H23Cl07 M 398.839 0
From C. so/stitialis. Oil.
C 1 ~H 20 0 6 M 296.319
Gonzales, A.G. eta/, J. Chern. Soc., Perkin Trans. I, 1976, 1663.
Gonzalez, A.G. eta/, Can. J. Chern., 1978, 56, 491.
(IP.2P,3P,4P,6«,8«,10rx.,Ilrx.)-form
Merill, G.B. eta/, Phytochemistry, 1985, 24, 2013 (Solstitiolide, 8-Ac: Ezoartemin
Episo/stitiolide) C17H 220 7 M 338.357
Constit. of Artemisia montana. Cryst. Mp 266-267°.
Chrysartemin A Sq-01852 Nagaki, M. eta/, Phytochemistry, 1989, 28, 2731 (iso/)
Canin
[24959-84-0]

478
1,2:3,4-Diepoxy-8,10-dihydroxy-... - 1,2:3,4-Diepoxy-10-hydroxy-11(13)-... Sq-01855 - Sq-01859

1,2:3,4-Diepoxy-8,10-dihydroxy-11(13)- Sq-01855 Constit. of Liatris pycnostachya. Gum. [ex]~ -80° (c,

guaien-12,6-olide 0.20 in CHC1 3). Struct. given here has been revised
following on from the revised struct. given to Spicatin
(see 10,14-Epoxy-2,8-dihydroxy-3,11(13)-guaiadien-12,6-
olide, Sq-01912).
8-0-(4-Acetoxy-2-methyl-2Z-butenoyl): [53142-34-0].
Graminiliatrin
CzzH160 9 M 434.442
Constit. of L. spp. [cxln -48.6° (c, 1 in CHC1 3).
8-Tigloyl: [72947-98-9]. Eupachifolin E
C 20 H 240 7 M 376.405
C 15H 180 6 M 294.304 Constit. of Eupatorium chinense. Cryst. Mp 262-264°.
(1 «.,2«.,3«.,4«..5«.,6«.,8«.,1 0«. )-form [41653-84-3] [cx]i? -55.7° (c, 0.2 in Py).
Rupin A Herz, W. et al, J. Org. Chern., 1975, 40, 199 (Epoxyspicatin,
Constit. of Artemisia tripartita. Cryst. (EtOH). Mp 260- Gramini/iatrin)
3000 dec. Ito, K. et al, Chern. Lett., 1979, 1473 (Eupachifolin E)
8-Ac: [41653-85-4]. Rupin B Herz, W. et al, Phytochemistry, 1979, 18, 1337.
C 17H 200 7 M 336.341
Constit. of A. tripartita. Cryst. (EtOAc). Mp 235-245° 1,10:3,4-Diepoxy-11(13)-guaien-12,6-olide Sq-01857
dec. 1,10:3,4-Bisepoxy-11(13)-guaien-12,6-olide
(1 «.,2«.,3«.,4«..5«.,6«.,8p,1 0«. )-form
8- Tigloyl: [99956-50-0]. Solidaginolifk A
C 20H 1,p7 M 376.405
lsol. from Calea solidaginea. Gum.
8-(3-Acetoxy-2-methyl-2E-butenoyl): [102907-29-9].
Jamaicolide B
CnH160 9 M 434.442
Constit. of C. jamaicensis. Gum.
(1 P.2P,3P,4P.5«,6«,8«,1 0« )-form C 15H 180 4 M 262.305
8-Ac: [69684-72-6]. Yomogiartemin (1~,3~,4~,5«.,6«.,10~)-form [36416-50-9] 1soepoxyestafiatin
C 17H 200 7 M 336.341 Constit. of Lidbeckia pectinata and Pentzia elegans.
Constit. of Artemisia feddei. Cryst. (EtOAc). Mp 240- Cryst. (EtzOjpet. ether). Mp 168°.
2420. Bohlmann, F. et al, Tetrahedron Lett., 1972, 621.
11P,l3-Dihydro, 8-Ac: [92678-98-3]. Yamayomoginin
C 17Hzz07 M 338.357 1,2:3,4-Diepoxy-8-hydroxy-9,11(13)- Sq-01858
Constit. of A. montana. Cryst. Mp 261-262°.
guaiadien-12,6-olide
Irwin, M.A. et al, Phytochemistry, 1973, 12, 863 (Rupins)
Koreeda, M. et al, Chern. Lett., 1979, 81 (Yomogiartemin)
Matsueda, S. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1984,
104, 753 (Yamayomoginin)
Ober, A.G. et al, Phytochemistry, 1985, 24, 2728; 1986, 25, 877
(Solidaginolide, Jamaicolide)

3,4:10,14-Diepoxy-2,8-dihydroxy-11(13)- Sq-01856
guaien-12,6-olide
C 15H 160 5 M 276.288
(1«.,2«,3«.,4«.5«,6«.,8/1)-form
Tigloyl: [99956-51-1]. Solidaginolifk B
C20 H 110 6 M 358.390
Constit. of Calea solidaginea. Gum.
Ober, A.G. et al, Phytochemistry, 1985, 24, 2728.

0 1,2:3,4-Diepoxy-1 0-hydroxy-11 (13)- Sq-01859

C 15H 180 6 M 294.304 guaien-12,6-olide
(1«,2P,3«,4«.5«,6«,8P,10«.)-form
8-(2-Methylbutanoyl):
C20H 160 7 M 378.421
Constit. of Eupatorium anomalum. Gum.
8-(3-Methylbutanoyl):
C 20H 160 7 M 378.421
Constit. of E. anomalum. Gum.
8-0-[2-[(2-Hydroxymethyl-2E-butenoyloxy)methyl]-2E- 0
butenoyl], 2-Ac: [53177-31-4]. Epoxyspicatin C15H 180 5 M 278.304
C17H 310u M 532.543
(lp,2p,3p,4p,5«.,6«.,10P(OII))-form [83059-05-6]
lsochrysartemin

479
3,4:10,14-Diepoxy-2,5,8-trihydroxy-... - 3,8-Dihydroxy-4(15),10(14)-... Sq-01860 - Sq-01863

Constit. of Ajania fastigiata. Cryst. Mp 237-238°. [IX]~ 3,4-Dihydroxy-10(14),11(13)-guaiadien- Sq-01862

+44° (c, 2.14 in CHC1 3). 12,6-olide
Yusupov, M.l. eta/, Khim. Prir. Soedin., 1982, 18, 200.

3,4:10,14-Diepoxy-2,5,8-trihydroxy- Sq-01860
11(13)-guaien-12,6-olide

CtsH2004 M 264.321
(3p,4rx.,6rx.)-form
3-0-P-D-Glucopyranoside: [109605-94-9]. Diaspanoside C
0 C21H3009 M 426.463
CtsH180 7 M 310.303 Constit. of Diaspananthus unifiora. Amorph. powder.
[IX]~ -22.1° (c, 0.34 in MeOH).
(lrx.,2P,Jrx.,4rx.,5rx.,6rx.,8P,JOrx.)-form
8-Angeloyl: [20071-51-6]. Eupatoroxin Adegawa, S. et al, Chern. Pharm. Bull., 1987, 35, 1479 (isol, pmr,
cmr, ir)
C20H 240 8 M 392.405
Constit. of Eupatorium rotundifolium. Tumour inhibitor.
Cryst. (Me2C0jpet. ether). Mp 197-200°. [IX]~ -98° (c, 3,8-Dihydroxy-4(15),1 0(14)-guaiadien- Sq-01863
1.08 in MeOH). 12,6-olide
(lrx.,2P,Jrx.,4rx.,5rx.,6rx.,8p,l0p)-form
8-Angeloyl: [20071-54-9]. 10-Epieupatoroxin
C20H 240 8 M 392.405
Isol. from E. rotundifolium. Tumour inhibitor. Mp 230- HO- -OH
(lcx,3cx,5cx,6cx,8cx,ll ~H)-form
2320. [1X]~ -109° (c, 0.33 in MeOH).
Kupchan, S.M. et al, J. Org. Chern., 1969, 34, 3876.

2~,14:3~X,4~X-Diepoxy-211,8~,1 O~X­ 0
trihydroxy-1~X,5~X-guai-11(13)-en-12,6~X- CtsH200 4 M 264.321
olide Sq-01861 (1«,3rx.,5rx.,6rx.,8rx.,ll PH)-form [99305-0 1-8]
3-Epi-11, 13-dihydrodeacylcynaropicrin
Constit. of Saussurea involucrata and Centaurea
canariensis. Needles. Mp 157-158°. [IX]~ +64.2° (c, 0.112
in MeOH).
8-0-P-D-Glucopyranoside: [126254-85-1].
C21H300 9 M 426.463
Constit. of S. involucrata. Needles. Mp 244-245°.
0 (1 rx.,JP,5rx.,6«,8rx.,ll PH)-form
CtsH 180, M 310.303 3-0-P-D-Glucopyranoside: 11P,13-Dihydro-8rx.-
8-(2-Methy/butanoyl): [73021-00-8]. Anomalide hydroxyglucozaluzanin C
C20H 260 8 M 394.421 C21 H 300 9 M 426.463
Constit. of Eupatorium anomalum and E. mohrii. Cryst. Constit. of Brachylaena nereiifolia. Cryst. (as penta-Ac).
(MeOH/EtOAc). Mp 158-159°. [1X]n +3.2° (c, 0.005 in Mp 130° (penta-Ac).
CHC1 3). Also occurs as mixt. (Mp 152-153°) with the (1 rx.,Jp,5rx.,6rx.,8rx.,ll rx.H)-form
corresponding 3-methylbutanoate in E. anoma/um. Brx.-Hydroxy-11 rx.,13-dihydroza/uzanin C
Cryst. struct. analysis was done on the mixt. Constit. of Ainsliaea fragrans.
8-(3-M ethy/butanoyl): [73021-0 1-9]. (lrx.,5rx.,6rx.,8p)-form
C20H 260 8 M 394.421 11 ,13-Didehydro, 3-ketone: 8fi-Hydroxy-3-oxo-
Constit. of E. anomalum. Not obt. pure. 4(15), 10(14),11(13)-guaiatrien-12,61X-olide. BP-
[73543-78-9] Hydroxydehydrozaluzanin C
Herz, W. et a/, Phytochemistry, 1979, 18, 1337 (iso[) CtsHt604 M 260.289
Cox, P.J. et a/, Tetrahedron Lett., 1979, 3509 (isol, cryst struct) Constit. of Andryala pinnatifida. Gum. [1X]~4 + 10° (c, 0.1
in CHC1 3).
Collado, l.G. et a/, Phytochemistry, 1985, 24, 2107 (isol, ms, pmr,
ir)
Li, Y. eta/, Phytochemistry, 1989, 28, 3395 (isol, pmr, cmr, cryst
struct)

480
3,10-Dihydroxy-4(15),11(13)-... - 4,10-Dihydroxy-2,11(13)-guaiadien-••• Sq-01864 - Sq-01868

3,10-Dihydroxy-4(15),11(13)-guaiadien- Sq-01864 (4«,5«,6«,8«,11 /I)-form

12,6-olide 8-Ac: 8«-Acetoxytannunolide
C 17H 120 5 M 306.358
Constit. of Tanacetum annuum. Cryst. (Et20). Mp 159-
1600. [cxJn + 10.7° (c, l in CHC1 3).
HO (4«,5«,6«,8P,Ilf/)-form
8-Ac: Steviserrolide A
C 17H 220 5 M 306.358
Constit. of Stevia serrata. Oil.
(4P,5«,6«,8«,11 «)-form
C 15H:u.04 M 264.321 8-Ac: 4-Epimatricin
(1«)P,5«,6«,10«)-form C17H 120 5 M 306.358
3-0-P-D-Glucopyranoside: [93236-44-3]. Ixerin D Constit. of A. arborescens. Cryst. (EtOAc). Mp 147°.
C11H 300 9 M 426.463 [cx]i; -80° (c, 0.52 in CHC1 3).
Constit. of Ixeris tamagawaensis. Needles (MeOH). Mp (4P,5«,6«,8P,I1/I)-form
230-231°. [ex)~ -32.7° (c, 0.51 in MeOH). 8-Ac: Steviserrolide B
11P,l3-Dihydro, 3-0-P-D-glucopyranoside: [93236-45-4]. C 17H 120 5 M 306.358
Ixerin E Constit. of S. serrata. Oil.
C11H 310 9 M 428.478 Cekan, Z. et a/, Collect. Czech. Chem. Commun., 1954, 19, 798;
Constit. of I. tamagawaensis. Needles (MeOH/C6H 6). 1957, 22, 1921 (isol)
Mp 214.5-2W. [ex]~ -12.3° (c, 0.16 in MeOH). Appendino, G. eta/, Phytochemistry, 1982, 21, 2555 (isol, struct)
Calderon, J.S. eta/, Phytochemistry, 1989, 28, 3526 (isol, pmr)
(1 ~)P,5«,6«,10~)-form [1 01221-74-3] Isopyrethroidinin Barrero, A. F. eta/, Phytochemistry, 1990, 29, 3575 (isol, pmr, cmr)
Constit. of Pyrethrum pyrethroides. Cryst.
(EtOAcjhexane). Mp 143-145°. [ex]~ -69.SO (c, 0.27 in
EtOH). 4,8-Dihydroxy-1 0(14), 11(13)-guaiadien- Sq-01867
Asada, H. eta/, Chem. Pharm. Bull., 1984, 32, 3036 (Ixerins) 12,6-olide
Abduazimov, B.Kh. eta/, Khim. Prir. Soedin., 1985, 21, 543
(Isopyrethroidinin)

3,11-Dihydroxy-4(15),10(14)-guaiadien- Sq-01865
12,6-olide (lcx,4cx,5cx,6cx,8cx)-form

c 15H 100 4 M 264.321

Mp 194°.
(1 «,4«,5«,6«,8« )-form
8-Ac: [82461-08-3]. Michefuscalide. P-Cyclolipiferolide
C 17H 120 5 M 306.358
Constit. of Michelia fuscata and Liriodendron tulipifera.
C 15H 100 4 M 264.321 Cryst. (EtzO) (also descr. as oil). Mp 161-162°. [cx]i;'
(l«)P,5«,6«,11f/)-form -101.4° (c, 0.5 in MeOH).
3-0-P-D-Glucopyranoside: Ixerisoside C (1«,4«,5«,6«,8/1)-form [97108-36-6] Vestenolide
C11 H 300 9 M 426.463 Constit. of Vicoa vestita. Cryst. [cxJn -103.23° (c, 0.5 in
Constit. of Ixeris repens. Amorph. powder. [ex]i; + 32.2° MeOH).
(c, l.17 in MeOH). Iida, T. et al, Phytochemistry, 1982, 21, 701 (Michefuscalide)
Warashina, T. eta/, Phytochemistry, 1990, 29, 3217 (isol) Doskotch, R.W. eta/, J. Nat. Prod. (Lloydia), 1983, 46, 923 (/J-
Cyclolipiferolide)
Sachdev, K. eta/, J. Nat. Prod. (Lloydia), 1985, 48, 249
4,8-Dihydroxy-1(10),2-guaiadien-12,6- Sq-01866 ( Vestenolide)
olide
4,10-Dihydroxy-2,11(13)-guaiadien-12,6- Sq-01868
olide
(4cx,5cx,6cx,8cx,llcx)-form

C 15H 100 4 M 264.321

(4«,5«,6«,8«,11 «)-form
0
8-Ac: [29041-35-8]. Matricin. Prochamazulene
C 17H 120 5 M 306.358 C15H 100 4 M 264.321
Constit. of Artemisia arborescens, A. carruthii and (1«,4«,5«,6«,10r!.)-form
Matricaria chamomilla. Cryst. Mp 158-160°. [cxJi? -131 o Constit. of Eriocephalus giessii. Oil.
(c, 1.96 in CHC1 3).

481
8,10-Dihydroxy-1,4-guaiadien-12,6-... - 8,14-Dihydroxy-3,11(13)-guaiadien-... Sq-01869 - Sq-01871

2,3-Dihydro: [92618-98-9]. 4,10-Dihydroxy-II(I 3)-guaien- Constit. of Chrysanthemum ornatum. Antimicrobial. Oil.

I2,6-olide. MagMgrtu~diolide
C 15H 120 4 M 266.336
Constit. of Magnolia grandiflora. Prisms. Mp 176-177°.
(111.,4,,511.,611.,10')-form [97534-13-9] Pyrethroidin
Constit. of Pyrethrum pyrethroides. Cryst.
(EtOAcjhexane). Mp 180-182°. [a]i;1 -105° (c, 0.33 in
MeOH).
Halim, A.F. et al, Phytochemistry, 1984, 23, 914
(Magnograndiolide)
Abduazimov, B.K.L. et al, Khim. Prir. Soedin., 1985, 199
(Pyrethroidin)
Zdero, C. et al, Phytochemistry, 1987, 26, 2763 (isol)
8,10-Dihydroxy-1,4-guaiadien-12,6-olide
OH
[a]~ + 100° (c, 0.2 in MeOH).
II p,I3-Dihydro: 8,10-Dihydroxy-3-guaien-I2 ,6-o/ide.
II p, 13-Dihydroepiligustrin (incorr.)
Constit. of Eriocephalus giessii. Cryst. Mp 67°.
II p,I3-Dihydro, 8-Ac: Dihydrocumambrin A
C 17H:u05 M 308.374
From C. coronarium. Cryst. Mp 174°. [a]i;' +44° (c, 0.08
in CHCI 3).
(111.,511.,611.,8P,1011.)-form
Cryst. (MeOH). Mp 91-92°.
8-Angeloyl: Constit. of Helianthus maximiliani. Cryst.
(EtOAc). Mp 160-161°.
Sq-01869 8-(3-Hydroxy-2-methylenebutanoyl):
C20H 260 6 M 362.422
From H. maximiliani. Oil.

d\-oH 8-(2-Hydroxymethyl-2Z-butenoyl): [89908-04-3]. 1,10-

Hydrobahia 111

'Q---
C20H 260 6 M 362.422

r From H. maximiliani and Bahia oppositifolia. Cryst.

(diisopropyl etherjMeOH). Mp 129-130°.
8-(2 ,3-Epoxy-2-methylbutanoyl):
o C20 H 260 6 M 362.422
(611.,811.,1011.,1111.)-form From H. maximiliani. Oil.
8-Ac: .[71616-00-7). Achillicin Romo, J. et al, Tetrahedron, 1968, 24, 5625 (Cumambrins)
C 17H 120 5 M 306.358 Irwin, M.A. et al, Phytochemistry, 1969, 8, 305 (Cumambrins)
Constit. of Achillea millefolium. Cryst. Bohlmann, F.B. et al, Phytochemistry, 1980, 19, 2663, 2669 (derivs)
Haruna, M. et al, Phytochemistry, 1981, 20, 2583 (derivs)
Banh-Nhu, C. et al, Phytochemistry, 1979, 18, 331. Watson, W.H. et al, Acta Crystallogr., Sect. B, 1982, 38, 1608
(cryst struct)
8,10-Dihydroxy-3,11(13)-guaiadien-12,6- Sq-01870 Nelson, P. et al, Phytochemistry, 1983, 22, 2755.
Gershenzon, J. et al, Phytochemistry, 1984, 23, 1959 (derivs)
olide EI-Nasry, S. et al, Phytochemistry, 1984, 23, 2953
(Dihydrocumambrin A)
Zdero, C. et al, Phytochemistry, 1987, 26, 2763 (isol)

( 1cx,5cx,6cx,8cx, 1Ocx )-form 8,14-Dihydroxy-3,11(13)-guaiadien-12,6- Sq-01871

olide

0
C 15H 200 4 M 264.321
(111.,$11.,611.,811.,1011.)-/orm [21982-83-2] Cumambrin B. 8-
Hydroxycumambrano/ide
Constit. of Artemisia nova, A. tripartita ssp. rupicola,
Ambrosia cumanensis and A. acanthicarpa. Cryst.
(EtOAcjEtp). Mp 178-180°. [a]n +92.5° (c, 5.58 in C 15H 200 4 M 264.321
CHC1 3).
(111.,511.,611.,8P,l0f/)-form
8-Ac: [20482-33-1]. Cumambrin A
8-(4-Hydroxy-2-methyl-2E-butenoyl): [103974-70-5].
C 17H120 5 M 306.358
Constit. of Artemisia nova, A. tripartita ssp. rupicola, Breviarolide
Ambrosia cumanensis and A. acanthicarpa. Cryst. Mp C20 H 260 6 M 362.422
Constit. of Stevia breviarietata. Cryst. (C6H 6 /CHCI 3).
188-190°. [a)n + 103° (c, 2.79 in CHCI 3).
Mp 83-85°.
8-(2-M ethylpropanoyl):
Oberti, J.C. et al, Phytochemistry, 1986, 25, 1479.
C1,H 260 5 M 334.411
Constit. of Eremanthus incanus. Cryst. (Etpjpet. ether).
Mp 130°.[a]i;' +84.1° (c, 0.22 in CHCI 3).
8-(2-Methylpropenoyl):
C1,H:u05 M 332.396
Constit. of Lychnophora blanchetii. Gull)..
8-Tigloyl:
CzoH 260 5 M 346.422
Constit. of L. blanchetii. Gum.
8-Angeloyl:
CzoH 260 5 M 346.422

482
9,10-Dihydroxy-3,11(13)-guaiadien-.•• - 1,8-Dihydroxy-3,10(14),11(13)-••• Sq-01872 - Sq-01876

9,10-Dihydroxy-3, 11(13)-guaiadien-12,6- Sq-01872 1,8-Dihydroxy-3,9,11(13)-guaiatrien-12,6- Sq-01875

olide olide

CtsH 1804 M 262.305

CtsH 200 4 M 264.321
(lrz.,5rz.,6rz.,Brz.)-form [41653-82-1] Rupicolin A
(6«,9rz.JOrz.)-form [128366-54-1]
Constit. of Artemisia tripartita. Cryst.
Constit. of Ajania achilleoides. Cryst. Mp 139°. [1X]~4
(EtOAcjEtOHjEtzO). Mp 155-156°.
+50° (c, 0.6 in CHC1 3).
(1rz.,5rz.,6rz.,8f/)-form
9-Propanoyl: [128366-55-2].
C18H:w05 M 320.385 8-(2-Methylpropanoyl): 8-Epiisobutyrylrupico/in A
Constit. of A. achilleoides. Gum. C 19H:w05 M 332.396
Constit. of Calea subcordata. Gum.
9-Ketone: [128366-56-3]. 101X-Hydroxy-9-oxo-3,11(13)-
guaiadien-12,61X-olide 8-(4-Hydroxy-2-hydroxymethyl-2E-butenoyl): [82433-03-2].
C 15H 180 4 M 262.305 Eupahakonin A
Constit. of A. achilleoides. Gum. C20 H:w07 M 376.405
Constit. of Eupatorium chinense var. hakonense. Oil. [IX]~
Zdero, C. eta/, Phytochemistry, 1990, 29, 1585 (isol, pmr)
-146° (c, 0.2 in MeOH).
1-Hydroperoxide: [82425-23-8]. Peroxyeupahakonin A.
4,8-Dihydroxy-1,9-guaianadien-12,6-olide Sq-01873 Peroxyeuphakonin A (incorr.)
C20H:w08 M 392.405
Constit. of E. chinense. Amorph. Mp 143-146°. [IX]~
-165° (c, 0.21 in MeOH).
Irwin, M.A. eta/, Phytochemistry, 1913, 12, 863 (Rupicolin A)
Ito, K. et al, Phytochemistry, 1982, 21, 715 (Eupahakonin,
Peroxyeupahakonin)
Ober, A.G. et al, Phytochemistry, 1984, 23, 1289 (8-
Epiisobutyrylrupicolin A)

C 15H 200 4 M 264.321

1,8-Dihydroxy-3,10(14),11(13)-guaiatrien- Sq-01876
8-Ac: Sieversin
12,6-olide
C17H 220 5 M 306.358
lsol. from Artemisia sieversiana. Mp 128-131°.
Nazarenko, M.V., Zh. Prikl. Khim. (Leningrad), 1961, 34, 1633;
1965, 38, 2372.
Geissman, T.A. et al, JPAC, 1910, 21, 167. (1cx,5cx,6cx,8cx)-form

8,9-Dihydroxy-1(10),2,4(15),11(13)- Sq-01874
guaiatetraen-12,6-olide 0
C 15H 180 4 M 262.305
(lrz.,5rz.,6rz.,Brz.)-form [41653-83-2] Rupicolin B
Constit. of Artemisia tripartita. Granules (EtOAcjEt 20).
Mp 142-144°.
3,;,4,;-Epoxide: 3,4-Epoxy-1,8-dihydroxy-10(14),11(13)-
guaiatri_en-12,6-o/ide. !Rupicolin B oxide
C 15H 180 5 M 278.304
Constit. of Ajania fastigiata. Cryst. (C 6H 6 /Me2CO). Mp
CtsH 160 4 M 260.289 191-192°. [1X]i? + 149° (c, 2.54 in CHC1 3).
(5rz.,6rz,Brz.,9rz.)-form (1rz.,5rz.,6rz.,Bf/)-form
Di-Ac: [72635-14-4]. 8-Acetoxy-4-anhydroat/uurwntanolide 8-(4-Hydroxy-2-hydroxymethyl-2E-butenoyl): [82598-57 -0].
C1,H200 6 M 344.363 Eupahakonin B
Constit. of Athanasia montana. Cryst. (Et20). Mp 193°. CmH:w07 M 376.405
[IX]~ +225.6° (c, 0.5 in CHC1 3).
Constit. of Eupatorium chinense var. hakonense. Oil. [IX]~
8-(Methylpropanoyl), 9-Ac: [72635-04-2]. +65.3° (c, 0.2in MeOH).
C11H:w06 M 372.417 1-Hydroperoxide, 8-(4-hydroxy-2-hydroxymethyl- 2E-
Constit. of A. montana. Oil. butenoyl): [82425-22-7]. Peroxyeupahakonin B
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 995. C20H:w08 M 392.405
Constit. of E. chinense. Cryst. (Me2CO). Mp 147-148°.
[1X]~ +35.4° (c, 0.18 in MeOH).
8-(2-Methylpropanoyl): 8-Epiisobutyrylrupicolin B

483
2,8-Dihydroxy-3,10(14),11(13)-..• - 3,8-Dihydroxy-4(15),10(14),11(13)-•.. Sq-01877 - Sq-01879

C19H 240 5 M 332.396 2,8-Dibydroxy-4(15),10(14),11(13)- Sq-01878

Constit. of Ca/ea subcordata. Gum. guaiatrien-12,6-olide
Yusupov, M.l. et al, Khim. Prir. Soedin., 1982, 18, 260; Chern.
Nat. Compd. (Engl. Trans/.), 243 (Rupicolin B oxide)
Ito, K. eta/, Phytochemistry, 1982, 21, 715 (Eupahakonin B,
Peroxyeupahakonin B)
Ober, A.G. eta/, Phytochemistry, 1984, 23, 1289 (8-
Epiisobutyrylrupicolin B)

2,8-Dibydroxy-3,10(14),11(13)-guaiatrien- Sq-01877
12~olide
Ct 5Ht80 4 M 262.305

H~\,
~~
(11;,2fJ.S1;,6r~.,8r~.)-form
8-0-(2-Hydroxymethylpropenoyl): [85011-56-9]. Acroptin
OH C19Hn06 M 346.379
(1 cx,2~,5cx,6~, 7cx,8~)-form Constit. of Acroptilon repens. Cryst. (C 6H 6). Mp 199-
H ' 2010.

~
0
Serkerov, S.V. et al, Khim. Prir. Soedin., 1982, 18, 112; Chern. Nat.
Compd. (Engl. Trans/.), 614.

CtsHt80 4 M 262.305
3,8-Dibydroxy-4(15),10(14),11(13)- Sq-01879
(lr~.,2fJ.S«,6fJ,7r~.,8/l)-form[111576-37-5]
Constit. of Hymenothrix wislizenii. Oil. guaiatrien-12,6-olide
(I r~.,2P.S«,6fl,7fl,B/1)-form
2ft-Hydroxyligustrin
8-0-(2,3-Epoxy-2-methy/butanoyl):
C~ 24 06 M 360.406 (I cx,3~,5cx,6cx,8cx)-form
Constit. of Trichogonia santosii. Oil. [a]i;' -31° (c, 0.52
in CHC13). Diastereoisomeric epoxide also isolated.
2-Ketone, 8-0-(2,3-epoxy-2-methylbutanoyl):
C20Hn06 M 358.390 0
Constit. ofT. santosii. Oil. [a]i;' +41 ° (c, 0.65 in Ct 5H 180 4 M 262.305
CHC1 3). (lr~.,3fl.S«,6«,8«)-form [3!565-50-!]8-Hydroxyzaluzanin C
8-0-[[(2E-Hydroxymethyl-2-butenoyl)oxy]-2E-butenoylj: Constit. of Amberboa muricata. Cryst. Mp 150-151.5°.
[100015-12-1]. Prespicatin [1X]i? +119.7°.
C25H.34P 8 M 458.507 8-(3-Methyl-2-butenoyl):
Constit. of Liatris spicata. Oil. C10H 240 5 M 344.407
8-0-(4-Hydroxy-2-methyl-2Z-butenoyl), 2-Ac: [72947-96-7]. Constit. of Pseudostiffia kingii. Gum. [a]~4 + 32° (c, 0.2
Eupachifolin C in CHC1 3).
CnH260 7 M 402.443 8-(4-Hydroxy-3-methyl-2-butenoyl):
Constit. of Eupatorium chinense. Oil. [ali? -37.9° (c, C10H 240 6 M 360.406
0.21 in CHCI 3). Constit. of P. kingii. Gum. [1X]i;' + 22° (c, 0.25 in
10a,l4-Epoxide, 8-0-(4-Hydroxy-2-methyl-2Z-butenoyl), 2- CHCI 3).
Ac: [72947-95-6). Eupachifolin B 8-(2-Hydroxymethylpropenoyl): [35730-78-0]. Cynaropicrin
CnH11,08 M 418.443 C19Hn0 6 M 346.379
Constit. of E. chinense. Oil. [a]);~ - 111.6° (c, 0.2 in Constit. of Cynara scolymus. Noncryst. [1X]i? + 108.6°.
MeOH). 8-(3-Ch/oro-2-hydroxy-2-methylpropanoyl): [66761-09-9].
(lfJ,2fJ.Sr~.,6r~.,7fJ,8«)-form Linichlorin B
Jlf,,13-Dihydro: 2,8-Dihydroxy-3,10(14)-guaiadien-12,6- C19H 13CI06 M 382.840
olide. Dzheiranbatanolide Constit. of Centaurea linifolia. Cryst. (EtOAcjpet.
C 15H 200 4 M 264.321 ether). Mp 144-146°. [1X] 0 +95° (c, 9.5 in CHC1 3).
Constit. of Artemesia fragrans. Cryst. (C6H 6). Mp 186- Di-Ac: [71305-80-1]. 8r~.-Acetoxyzaluzanin D
1880. C 19Hn06 M 346.379
(lr~.,2fJ.S«,6r~.,7fJ,8/I)-form Constit. of C. conicum. Oil. [1X] 0 + 174° (c, 2.3 in
8-0-(4-Hydroxy-2-hydroxymethyl-2E-butenoyl), 2-Ac: CHC1 3).
[82425-20-5]. Eupahakonensin 3-0-P-v-Glucopyranoside: [100228-50-0]. Crepiside E
CnH260 8 M 418.443 . C11 H 280 9 M 424.447
Constit. of Eupatorium chinense var. hakonense. 011. [a] 0 Constit. of Crepis japonica. Amorph. powder. [a] 0
-49.SO (c, 0.2 in MeOH). + 12.9° (c, 0.62 in MeOH).
Ito, K. et al, Chern. Lett., 1919, 1473 (Eupachifolins) 8-0-(4-Hydroxyphenylacetyl), 3-0-P-v-glucopyranoside:
Ito, K. et al, Phytochemistry, 1982, 21, 115 (Eupahakonensin) [100187-60-8]. Crepiside G
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162. C19H 340 11 M 558.581
Serkerov, S.V. et al, Khim. Prir. Soedin., 1984, 20, 560 Constit. of C. japonica. Amorph. powder. [1X]i? +41.3°
(Dzheiranbatanolide)
Baruah, R.N. et al, Phytochemistry, 1985, 24, 2641 (Prespicatin)
(c, 0.40 in MeOH).
Jakupovic, J. et al, Phytochemistry, 1987, 26, 2543. 3-0-(6-0-p-Hydroxyphenylacetyl-P-v-glucopyranoside):
[100228-49-7]. Crepiside H

484
3,9-Dihydroxy-4(15),10(14),11(13)-..• - 4,5-Dihydroxy-1(10),2,11(13)-..• Sq-01880 - Sq-01881

C29H 340 11 M 558.581 Gonzalez, A.G. et al, Can. J. Chern., 1978, 56, 491 (Linichlorin B)
Constit. of C. japonica. Amorph. powder. [1X] 0 + 22.9° Bohlmann, F. et al, Phytochemistry, 1978, 17, 475; 1981, 21, 2379;
(c, 0.83 in MeOH). 1982, 21, 1171.
Gonzalez, A.G. et al, Phytochemistry, 1978, 17, 955 (Aguerins)
8-Ac: [71305-81-2]. Brx.-Acetoxyza/uzanin C Asakawa, Y. et al, Phytochemistry, 1979, 18, 285
C 17 H 20 0~ M 304.342 (Acetoxyzaluzanins)
Constit. of Conocephalum conicum. Oil. Massanet, G.M. et a/, Phytochemistry, 1984, 23, 912 (Integrifolin)
8-(2-Methy/propanoyl): [68370-46-7]. Aguerin A Rustaiyan, A. et al, Planta Med., 1984, 50, 363 (Kandavanolide)
Miyase, T. et al, Chern. Pharm. Bull., 1985, 33, 4451 (Crepisides)
C19H 24 0~ M 332.396
Kisiel, W. eta/, Phytochemistry, 1989, 28, 2403 (Tectoroside)
Constit. of Centaurea canariensis and C. linifo/ia. Oil. Warashina, T. et al, Phytochemistry, 1990, 29, 3217 (lxerisosides)
[1X] 0 +89° (c, 0.14 in CHCI3).
8-(2-Methy/propenoyl): [68370-45-6]. Aguerin B
C 1 9H 22 0~ M 330.380
3,9-Dihydroxy-4(15),10(14),11(13)- Sq-01880
Constit. of Centaurea spp. Oil. [1X] 0 +96° (c, 0.17 in guaiatrien-12,6-olide
CHCI 3).
3-Ketone: 8-Hydroxy-3-oxo-4(1 5),10(14),11(1 3)-guaiatrien-
12,6-o/ide. Brx.-Hydroxydehydrozaluzanin C
CI~H 16 0 4 M 260.289
Constit. of P. kingii, Vernonia arkansana and V.
profuga. Cryst. (MeOH). Mp 191°. [1X]~4 + 118° (c, 0.3 in
CHCI 3).
3-Ketone, 11P,J3-dihydro: 8-Hydroxy-3-oxo-4(15),10(14)- (3~,6a,9a)-form
guaiadien-12,6-o/ide
C 15H 180 4 M 262.305 C 1 ~H 18 04 M 262.305
Constit. of P. kingii and V. novebaracensis. Cryst. (3p,6rx.,9«)-form
(Etpjpet. ether). Mp 168°. [1X]~4 + 169.5° (c, 0.57 in 9rx.-Hydroxyzaluzanin B
CHCI 3). Isol. from Lactuca laciniata. Cryst. (MeOH). Mp 76-78°.
3-Ketone, 8-0-(2-hydroxymethy/propenoyl): [35821-02-4]. [IX]~ + 13.0° (c, 0.58 in MeOH).
Dehydrocyanaropicrin 11 p,13-Dihydro: 3P,91X-Dihydroxy-4(!5), 10(14)-guaiadien-
C19H2006 M 344.363 12,6-o/ide. 1lp,13-Dihydro-9rx.-hydroxyzaluzanin C
Constit. of Cynara sco/ymus. Cryst. Mp 126°. [IX]~ C 1 ~H 20 0 4 M 264.321
+60°. lsol. from L. laciniata. Amorph. [IX]~ +50.7° (c, 0.75 in
4P,llP,l3,15- Tetrahydro: see 3,8-Dihydroxy-10(14)-guaien- MeOH).
!2,6-o/ide, Sq-01888 (3P,6«,9fJ)-form [116397-93-4]
(lrx..JP,5rx.,6rx.,8fJ)-form [89647-87-0] lntegrifolin 3-0-P-D-Glucopyranoside: [I 09668-73-7]. Diaspanoside A
Constit. of Andrya/a integrifolia. Cryst. (EtOAcjpet. C21 H 280 9 M 424.447
ether). Mp 206-208°. [1X] 0 -17.5° (c, 0.2 in CHCI 3). Constit. of Diaspananthus uniflora. Amorph. powder.
3-Ac: [92484-33-8]. Kanda,anolide [1X]~ -10.9° (c, 0.32 in MeOH).
C 17 H 20 0~ M 304.342 Nishimura, K. et al, Phytochemistry, 1986, 25, 2375 (derivs)
Constit. of Centaurea kandavanensis. Cryst. Mp 142.5°. Adegawa, S. et al, Chern. Pharm. Bull., 1987, 35, 1479 (isol, pmr,
[1X]i; + 33.7° (c, 0.49 in CHCI 3). cmr, ir)
3-0-(6-0-p-Hydroxypheny/acetyl-P-D-glucopyranoside):
[100187-59-5]. Crepiside I 4,5-Dihydroxy-1 (1 0),2,11 (13)-guaiatrien- Sq-01881
C29H 340 11 M 558.581 12,6-olide
Constit. of Crepis japonica. Amorph. powder. [1X]ii
-22.6° (c, 0.31 in MeOH).
8-0-[2-Hydroxy-3-(p-hydroxyphenyl)propanoylj, 3-0-P-D-
g/ucopyranoside: Tectoroside
C30H 360 12 M 588.607
Constit. of Crepis tectorum. Oil.
3-0-P-D-Glucopyranoside, 8-(4-hydroxypheny/acetyl):
lxerisoside A 0
C29H 340 11 M 558.581
Constit. of Ixeris debilis. Amorph. powder. [1X]i,l -40.6° C 1 ~H 180 4 M 262.305
(c, 0.16 in MeOH). (4P,5rx.,6rx.)-form
9-Desacetoxy-5-hydroxyathamantholide
4P,J5-Dihydro, 3-0-P-D-glucopyranoside, 8-(2-hydroxy-3-(4-
hydroxyphenyl)propanoylj: lxerisoside B
Constit. of Ursinia nana. Gum. [1X] 0 -8° (c, 1 in
CHCI 3).
C 30H 380u M 590.623
Constit. of/. repens. Amorph. powder. [IX]~ -26.9° (c, Bohlmann, F. et al, Phytochemistry, 1982, 21, 1309.
0.46 in MeOH).
(U,..J/;,51;,61;,81;)-form
8-0-(2-Hydroxymethy/propenoyl): [35932-39-9]. Saupirin
C19H220 6 M 346.379
Constit. of the flowers of Saussurea neopulchella.
Chugunov, P.V. et al, Khim. Prir. Soedin., 1971, 7, 727 (Saupirin)
Corbella, A. et al, J. Chern. Soc., Chern. Commun., 1972, 386
( Cynaropicrin)
Gonzalez, A.G. et al, Ann. Quim., 1973, 69, 1333.

485
4,8-Dihydroxy-1(10),2,11(13)-... - 8,15-Dihydroxy-2,10(14),11(13)-... Sq-01882 - Sq-01886

4,8-Dihydroxy-1(10),2,11 (13)-guaiatrien- Sq-01882 Cz,H2406 M 372.417

12,6-olide Constit. of L. santosii. Gum.
3a,4rx-Epoxy, 8-0-(2-acetoxymethyl-2E-butenoyl):
C22 H 260 8 M 418.443
Constit. of L. santosii. Gum.
3a,4rx-Epoxy, 9-0-(2-acetoxymethyl-2E-butenoyl):
C22H 260 8 M 418.443
Constit. of L. santosii. Gum.
3a,4a-Epoxy, 9-ketone, 8-0-(2-acetoxymethyl-2E-butenoyl):
0 C22 H 240 8 M 416.427
Constit. of L. santosii. Gum. [oc]i;l -20° (c, 0.1 in
C 15H 180 4 M 262.305 CHCI 3).
(4,_,6,.,8,_ )-form Bohlmann, F. et a/, Phytochemistry, 1981, 20, 1613.
8-Ac: [73091-63-1]. 8a-Acetoxy-4a-hydroxy-1 ( 10),2, 11 (13)-
guaiatrien-12,6a-olide
8,15-Dihydroxy-1(10),3,11(13)-guaiatrien- Sq-01885
C 17H 2t,05 M 304.342
Constit. of Pentzia eenii. Cryst. Mp 170°. [oc]~4 -33° (c, 12,6-olide
0.09 in CHC1 3).
11 ,13-Dihydro: see 4,8-Dihydroxy-1(10),2-guaiadien-12,6-
olide, Sq-01866
Zdero, C. et al, Phytochemistry, 1990, 29, 189 (isol, pmr)

4,8-Dihydroxy-2,10(14),11(13)-guaiatrien- Sq-01883
12,6-olide
0
C 15H 180 4 M 262.305
(5,.,6,_,8,.)-form
15-0-(2-p-Hydroxyphenylacetyl-P-D-g/ucopyranoside):
[101921-33-9]. Crepidiaside E
C29 H 340 11 M 558.581
Constit. of Crepidiastrum keiskeanum. Amorph. powder.
[rx]i;1 -22.2° (c, 0.63 in MeOH).
C1sH180 4 M 262.305 11P,l3-Dihydro,15-0-P-D-glucopyranoside: [101921-37-3].
(1,.,4,.,5'46"-,6"-,8/1)-form Crepidiaside C
8-0-[4-Hydroxy-2-(2-hydroxymethyl-2E-butenoy/oxy)-2E- C21 H 300 9 M 426.463
butenoyl]: [92632-37-6]. Hymenopappolide Constit. of C. keiskeanum. Needles (MeOH). Mp 125-
C25H 300 9 M 474.507 1300 dec. [oc] 0 -65.1 o (c, 0.53 in MeOH).
Constit. of Hymenopappus newberryi. Gum. [oc]i;l - 124° 11 p,13-Dihydro,15-0-(2-p-hydroxyphenylacetyl-P-D-
(c, 0.18 in CHC13). glucopyranoside): [101921-34-0]. Crepidiaside D
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1055. C29H 360 11 M 560.597
Constit. of C. keiskeanum. Amorph. powder. [oc]i;1
-40.1° (c, 0.71 in MeOH).
8,9-Dihydroxy-3,10(14),11(13)-guaiatrien- Sq-01884 Adegawa, S. eta/, Chern. Pharm. Bull., 1985, 33, 4906.
12,6-olide
8,15-Dihydroxy-2,10(14),11(13)- Sq-01886
guaiatrien-12,6-olide

C,sH180 4 M 262.305
(1 ,.,s,.,6,.,8P,9fJ)-form
8,9- Dihydroxylasiolaenin 0
8-Tig/oy/: C 15H 180 4 M 262.305
C20H 240 5 M 344.407 (lp,5,.,6,.,8,.)-form
Constit. of Lasiolaena santosii. Gum. 8,15-Bis(4-hydroxy-2-methy/-2Z-butenoyl): [126616-68-0].
8-0-(2-Acetoxymethyl-2E-butenoyl): Pericomin
C21 H 240 6 M 372.417 C25H 300 8 M 458.507
Constit. of L. santosii. Gum. [oc]i;l + 15.7° (c, 0.9 in Constit. of Pericome caudata.
CHC1 3). 8-(4-Hydroxy-2-methy/enebutanoy/), 15-(4-hydroxy-2-
8-0-(2-acetoxymethyl-2E-butenoyl), 9-Ac: methy/-2Z-butenoyl): [126616-69-1]. Isopericomin
C23 H 260 7 M 414.454 C25 H 300 8 M 458.507
Constit. of Lasiolaena santosii. Gum.
9-0-(2-Acetoxymethyl-2E-butenoyl):

486
1,10-Dihydroxy-3-guaien-12,6-olide - 3,9-Dihydroxy-10(14)-guaien-12,6-... Sq-01887 - Sq-01889

Constit. of P. caudata. lsol. as a mixture with C,sH180 4 M 262.305

eupatoriopicrin (75%). Constit. of G. macrocephala and Chartolepsis intermedia.
Jolad, S.D. eta/, Phytochemistry, 1990, 29, 649 (isol, ms, pmr, cmr) Cryst. (MeOH). Mp 205°. [a]~ + 137.7° (c, 0.2 in
MeOH).
1,10-Dihydroxy-3-guaien-12,6-olide Sq-01887 Gonzalez, A.G. et al, An. Quim., 1970, 66, 799; 1973, 69, 1333
(lsolipidiol, Muricatin)
Tori, K. eta/, J. Chern. Soc. B, 1971, 1084 (pmr)
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1972, 37, 2611
(Grosheimin)
Corbella, A. eta/, J. Chern. Soc., Chern. Commun., 1972, 386
(Amberboin, Jsoamberboin)
Zakerov, S.Kh. eta/, Khim. Prir. Soedin., 1975, 11, 261; 1976, 12,
398 (Jurmolide, Maximo/ide)
Daniewski, W. eta/, Collect. Czech. Chern. Commun., 1982, 47,
3160 (Grosheiminol)
C 15Hn04 M 266.336 Miyase, T. eta/, Chern. Pharm. Bull., 1985, 33, 4445
(Macrocliniside)
(lf.,5«,6«,10f,,l1«)-form [93552-69-3] Arlatin
Constit. of Artemisia /atifolia and A. absinthium. Cryst.
(EtOH). Mp 203-205°. 3,9-Dihydroxy-1 0(14)-guaien-12,6-olide Sq-01889
Adekenov, S.M. eta/, Khim. Prir. Soedin., 1984, 20, 795 (isol)
Kasamov, Sh.Z. et a/, Khim. Prir. Soedin., 1984, 20, 794 (isol)

3,8-Dihydroxy-1 0(14)-guaien-12,6-olide Sq-01888 (1cx,3~,4cx,5cx,6cx,9~, 11 cx)-form

HO -OH 0
-H CtsHn04 M 266.336
(1 «,3P,4«,5«,6«,9P,11 «)-form [880 10-68-8] 9P-Hydroxy-
4P,11 p,13 ,15-tetrahydrozaluzanin C
0 Constit. of Liabum jloribundum and Arctotis grandis.
C 15Hn04 M 266.336 Cryst. Mp 65°. [a]~4 -25° (c, 0.26 in CHCI3).
(1 rx.,3P,4«,5«,6«,8«,11 rx. )-form [30825-68-4]/solipidiol 4,15-Didehydro: [116360-07-7]. 3,9-Dihydroxy-4(15),10(14)-
Constit. of Macroclinidium trilobum and Vernonia guaiadien-12 ,6-o/ide. 9P-Hydroxy-11p,J3-dihydrozaluzanin
profuga. Prisms (Me2CO). Mp 167-168.5". [aln +41.3°. c
3-0-P-D-Giucopyranoside: [100228-52-2]. Macrocliniside F CtsH200 4 M 264.321
C11H 310 9 M 428.478 Constit. of L. floribundum. Oil.
Constit. of M. tri/obum. Needles (MeOH) (as penta-Ac). 3-Ketone: [78012-02-9]. 9-Hydroxy-3-oxo-10(14)-guaien-
Mp 197-198° (penta-Ac). [a]~ + 16.7° (c, 1.23 in CHC1 3) 12,6-o/ide
(penta-Ac). C 15H 200 4 M 264.321
3-Ketone: [30825-69-5]. Isoamberboin. Maximo/ide Constit. of L. floribundum and A. grandis. Cryst. Mp
C 15H 11,04 M 264.321 143-144°. [1X]i;' +50° (c, 0.1 in CHCI 3). Also descr. as
Constit. of Jurinea maxima and Cynara scolymus. Cryst. oil.
(EtOAcjpet. ether). Mp 183°. [a]~ + 138° (CHC1 3). (1«,3P,4rx.,5rx.,6rx.,9P,11p)-form [116360-06-6] 9P-Hydroxy-
3-Ketone, 8-Ac: [62067-47-4]. Jurmolide 4P,11 rx.,l3,15-tetrahydrozaluzanin C
C 17H 210 5 M 306.358 Constit. of L. floribundum. Oil. [1X]i;' + 27° (c 0.57 in
Constit. of J. maxima. Cryst. (EtOH). Mp 136-137°. CHCI 3).
[aJ:::! + 102.7° (c, 0.74 in CHC1 3). 4,15-Didehydro: [116360-08-8].
11 ,13-Didehydro, 8-0-(2-hydroxymethy/propenoyl): [52597- Constit. of L. floribundum. Oil.
25-8]. Muricatin 3-Ketone: [116404-82-1].
C 1,H140 6 M 348.395 Constit. of L. jloribundum. Gum. [a]i;' + 83° (c, 0.24 in
Constit. of Amberboa muricata. Cryst. Mp 73-75°. [aln CHCI 3).
+47° (c, 0.1 in CHC1 3). (1rx.,3P,5rx.,6rx.,9rx.,l1rx.)-form
(1 rx.,3rx.,4«,5«,6«,8«,11 p)-form 4,15-Didehydro,3-0-P-D-glucopyranoside: [93236-46-5].
3-Ketone: [22339-28-2]. 8-Hydroxy-3-oxo-10(14)-guaien- Ixerin F
12,6-o/ide. Amberboin C11 H 300 9 M 426.463
C,sH 200 4 M 264.321 Constit. of lxeris tamagawaensis. Amorph. powder. [a]);
Constit. of Amberboa Iippi. Cryst. Mp 145°. [a]~ + 1.0° (c, 0.48 in MeOH).
+ 169.5" (c, 5.6 in CHCI 3). Ha1im, A.F. eta/, Phytochemistry, 1980, 19, 2767; 1983, 22, 1510.
11 ,13-Didehydro: [84305-03-3]. 3,8-Dihydroxy- Asada, H. eta/, Chern. Pharm. Bull., 1984, 32, 3036 (lxerin F)
10(14),11 (1 3)-guaiadien-12,6-o/ide. Gr:osheiminol. Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1771.
Grossheiminol
C,sH 200 4 M 264.321
Constit. of Grossheimia macrocepha/a. Oil. [a]~ + 56.4°
(c, 0.1 in Py).
3-Ketone, 11,13-didehydro: 8-Hydroxy-3-oxo-10(14),11(13)-
guaiadien-12 ,6-o/ide. Grosheimin. Grossheimin

487
10,11-Dihydroxy-3-guaien-12,6-olide - 8,11-Dihydroxy-2-oxo-1(10)-... Sq-01890 - Sq-01895

10,11-Dibydroxy-3-guaien-12,6-olide Sq-01890 5,10-Dihydroxy-2-oxo-3,11(13)-guaiadien- Sq-01893

12,6-olide

Ct5Hn04 M 266.336
(1 /1,5 fl,6fl,l 0/1,11 ri)-form C 15H.80 5 M 278.304
10,11-Diltydroxy-3-slollenolide (lrz.,5fl,6rz.,10rz.)-form
11-Ange/oy/: 5/l,lOrz.-Diltydroxy-1 rz.H-deltydroleucodin
Cwli:aPs M 348.438 Constit. of Artemisia xanthochroa. Oil.
Constit. of roots of Laser trilobum. Cryst. Mp 186-189°. Huneck, S. et al, Phytochemistry, 1986, 25, 883.
(1~,5~,6~,10~,11~)-form
11-(3-Methy/-2-butenoyl): Fegolide 8,9-Dihydroxy-2-oxo-3,11(13)-guaiadien- Sq-01894
C20H:11P 5 M 348.438 12,6-olide
Constit. of seeds of Feru/a penninervis. Cryst. Mp 165-
1660. [1X] 0 -150° (c, 0.17 in CHC1 3).
Holub, M. et a/, Tetrahedron Lett., 1984, 25, 3755 (isol)
Nurmekhamedova, M.R. eta/, Khim. Prir. Soedin., 1985, 335
(Fegolide)

10,14-Dihydroxy-4(15)-guaien-12,6-olide Sq-01891

C15H 180 5 M 278.304

(1rz.,5rz.,6«,8rz.,9fl,J Ofl)-form
9-Angeloyl: [81344-94-7]. Vicolide A
C20H1•.06 M 360.406
Constit. of Vic!Ja indica. Cryst. (Me 2C0jhexane). Mp
165°. [1X] 0 + 110° (c, 2.0 in CHC1 3).
Purushothaman, K.K. et al, J. Chern. Res. (S), 1981, 374; J. Chern.
Res. (M), 1981, 4371.
C15Hn04 M 266.336
(6rz.,JOfl,J1 «H)-form [128722-90-7]
Constit. of Vladimiria souliei.
8,11-Dihydroxy-2-oxo-1(10)-guaiadien- Sq-01895
(6rz.,JOfl,J1fJH)-form [128722-92-9]
12,6-olide
Constit. of V. souliei. Gum.
Tan, R.X. et al, Phytochemistry, 1990, 29, 1209 (isol, pmr)

3,8-Dihydroxy-2-oxo-1(1 0),3-guaiadien- Sq-01892 (50(,60(,80(,110()-form

12,6-olide

0
C 15Hts05 M 278.304
-OH
The C-11 configs. of compds. in this series do not seem
well established.
(5«,6«,8«,11«)-form
8-(2-Methylpropenoyl), 11-(2-methylpropanoyl): [58561-95-
0 8]. Oferin
C15H 180 5 M 278.304 C23H 280 7 M 416.470
(5«,6«,8«,11«)-form [66173-52-2] Artelint Constit. of Ferula olgae. Cryst. (C 6H 6jpet. ether). Mp
Constit. of Artemisia leucodes. Cryst. (EtOH). Mp 228- 214-216".
2290. 8-(3,4-Dimethoxybenzoyl), 11-(3-methyl-2-butenoyl): [68218-
Saitbaeva, I.M. et al, Khim. Prir. Soedin., 1986, 22, 112. 73-5]. MalapltyU
C29H 310 9 M 524.566
Constit. of F. malacophylla. Cryst. (EtOH). Mp 204-
2050.
(5«.,6«.,8«,11 /I)-form
8-Angeloyl, 11-Ac: [58561-94-7]. Laferin. 4-Acetoxy-10-
pruteninone (incorr.)
CnH260 7 M 402.443

488
8,15-Dihydroxy-2-oxo-3,11(13)-••• - 8,9-Dihydroxy-2-oxo-1(10),3,11(13)-••• Sq-01896 - Sq-01899

Constit. of F. olgae. Cryst. (Et20jpet. ether). Mp 142- 9,11-Dihydroxy-2-oxo-1(10),3-guaiadien- Sq-01897

1440. [1X]i? -3.1° (c, 2.97 in CHC13). 12,6-oUde
8-(2-Methylpropanoy/),11-angeloyl: Talassin B. Talasin B
C 24H 300 7 M 430.497
Constit. of Talassia transiliensis and F. olgae. Cryst. Mp
205-208°. (1X]n -72° (c, 4.16 in CHC13).
11-Angeloyl, 8-Ac: [33589-19-4]. 71%-Acetoxy-2-pruteninone
(incorr.)
C11H 260 7 M 402.443
Constit. of Laserpitium prutenicum. Cryst. (CC14 /pet.
ether). Mp 142.SO.
8,11-Diangeloyl: 71%-Angeloyloxy-2-pruteninone (incorr.) C 1 ~H 180~ M 278.304
C:zsH300 7 M 442.508 8-(3,4-Dimethoxybenzoy/),11-angeloyl: [76487-92-8].
Constit. of L. prutenicum. Cryst. (Etpjpet. ether). Mp Feguolide
194°. C19H3P 9 M 524.566
(5«,6«,8«,11 ~)-form Constit. of Ferula gigantea. Cryst. Mp 218-220°.
11-(2-Methylpropenoyl), 8-Ac: [41989-32-6]. Olgin Savina, A.A. et al, Khim. Prir. Soedin., 1979, 733.
C21 H 240 7 M 388.416
Constit. of F. olgae. Cryst. Mp 176-178°. [1X]n + 25°. 9,13-Dihydroxy-2-oxo-4(15),10(14)- Sq-01898
8,11-Diangeloyl: [41943-06-0]. Talassin A. Talasin A guaiadien-12,6-oUde
C:zsH300 7 M 442.508 Saurin
Constit. of Talassia transiliensis and F. olgae. Cryst. Mp
188-191°. (1X]n -30°. [27214-23-9]
8-Angleloyl, 11-Ac: [88108-27-4]. Ferolide
C11H 260 7 M 402.443
Constit. of F. penninervis. Cryst. Mp 178-179°. (1X]i?
-10.3° (c, 0.55 in CHC1 3).
8-Benzoyl, 11-Ac: (70476-07-2]. Malaphyllinin
C24H 240 7 M 424.449
Constit. of F. malacophylla. Cryst. (EtOH). Mp 208-
2090.
Bohlmann, F. et al, Chern. Ber., 1971, 104, 1611 (isol) C 1 ~H 18 0~ M 278.304
Konovalova, G.A. et al, Khim. Prir. Soedin., 1972, 8, 651; 1973, 9, Constit. of Saussurea pulchella. Cryst. (EtOH aq.). Mp 87-
122; 1975, 11, 590 (isol) 880. [1X]n +60.1° (c, 0.58 in dioxan).
Bagirov, V.Yu. et al, Khim. Prir. Soedin., 1978, 14, 445, 810; Kushnir, L.E. etal., Khim. Prir. Soedin., 1966, 2, 245.
Chern. Nat. Compd. (Engl. Trans/.), 377, 694 (Malaphyll,
Malaphyllinin)
Nunnukhamedova, M.R. et al, Khim. Prir. Soedin., 1983, 19, 533 8,9-Dihydroxy-2-oxo-1(10),3,11(13)- Sq-01899
(Ferolide) guaiatrien-12,6-oUde
Rychlewska, U. et al, Collect. Czech. Chern. Commun., 1985, 50,
2607 (cryst struct, Laferin)

8,15-Dihydroxy-2-oxo-3,11(13)-guaiadien- Sq-01896
12,6-oUde

0
C 1 ~H 16 0~ M 276.288
(5«,6«,8«,9/1)-form
8-(2,3-Epoxy-2-methylbutanoyl), 9-Ac: [115547-14-3].
Skutchiolide B
C 1 ~H 18 0~ M 278.304 C11H 240 8 M 416.427
(1«,5«,6«,8«,10«)-form [77353-82-3] Hyporadiolide Constit. of Squamopappus skutchii. Gum.
8-Cinnamoyl: 9-Angeloyl: Deoxypumilin
C24H 240 6 M 408.450 C10H 220 6 M 358.390
Constit. of Hypochoeris radicata. Gum. Constit. of Berlandiera latifolia. Gum.
8-(Methylpropenoyl): Singh, P. et al, Phytochemistry, 1988, 27, 609 (5-Deoxypumilin)
C1,H110 6 M 346.379 Vargas, D. eta/, Phytochemistry, 1988, 27, 1413 (Skutchiolide B)
Constit. of H. radicata. Gum.
11,13-Dihydro, 8-(methylpropenoyl):
C 1,H240 6 M 348.395
Constit. of H. radicata. Gum.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2045.

489
8,9-Dihydroxy-2-oxo-3,10(14),11(13)-... - 10,15-Dihydroxy-2-oxo-3-guaien-12,6-... Sq-01900 - Sq-01904

8,9-Dihydroxy-2-oxo-3,1 0(14), 11 (13)- Sq-01900 8-(4-Hydroxyphenylacetyl): [65725-11-3]. Lactupicrin.

guaiatrien-12,6-olide Lactucopicrin. Intybin
C23H 220 7 M 410.423
Constit. of L. serriola and L. jioridana. Also from L.
virosa, Z. scariola, L. sativa, C. intybus, C. endivia and
Sonchus palustris. Mp 132-178° dec. [cx] 0 + 73° (Py).
8-(4-Hydroxyphenylacetyl), 15-0-P-v-glucopyranoside:
Lactupicriside
C 29 H 320 12 M 572.565
0 Constit. of L. laciniata. Amorph. powder. [cx]i,S -15.3°
(c, 1.47 in MeOH).
C 15H 160 5 M 276.288
15-0-P-v-Glucopyranoside: [104778-11-2]. Picriside A
(1,.,5,.,6,.,8p,9fl)-form C 21 H 260 10 M 438.430
8,9- Dihydroxy-2-oxolasiolaenin Constit. of Picris hieracioides var. japonica. Cryst.
8-Tigloyl: (MeOH/EtOAc). Mp 248-250°. [cx] 0 -38.0° (c, 0.71 in
C 20 H 22 0 6 M 358.390 MeOH).
Constit. of Lasiolaena morii. Gum. [cx]i;l + 21° (c, 0.3 in Jlfi,13-Dihydro: [83117-63-9]. 8,15-Dihydroxy-2-oxo-
CHC1 3). 1(10),3-guaiadien-12,6-olide. 11P,13-Dihydrolactucin
3a,4a-Epoxide, 8-tigloyl: C,sH 180 5 M 278.304
C 20H 220 7 M 374.390 Constit. of L. mucronata. Cryst. Mp 91°. [cx] 0 +8.7° (c,
Constit. of L. morii. Gum. 0.63 in CHC1 3).
8-[2-(Acetoxymethyl)-2-butenoyl](E-): Jlfi,13-Dihydro, 8-Ac: [81241-46-5]. 81%-Acetoxyjaquinelin
C 22H 240 8 M 416.427 C 17H 200 6 M 320.341
Constit. of L. morii. Gum. [cx]i;l + 18° (c, 0.25 in CHC1 3). Constit. of L. jioridana. Gum.
3a,4a-Epoxide, 8-(2-acetoxymethyl-2E-butenoyl): 15-Aldehyde, 8-(methylpropenoyl): [81241-43-2].
C 22 H 24 0 9 M 432.426 C,9H 180 6 M 342.348
Constit. of L. santosii. Gum. Constit. of H. uniflora. Gum.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1613; 1982, 21, 161. Bachelor, F.W. et a/, Can. J. Chern., 1973, 51, 3626 (struct)
St. Pyrek, J. et al, Pol. J. Chern. (Rocz. Chern.), 1977, 51, 2165
(isol, derivs)
8,14-Dihydroxy-2-oxo-1(10),3,11(13)- Sq-01901 Ruban, G. et al, Acta Crystallogr., Sect. B, 1978, 34, 1163 (cryst
guaiatrien-12,6-olide struct)
Sang, T.M. et al, Phytochemistry, 1982, 21, 1163 (isol, struct,
derivs)
Nishimura, K. et al, Chern. Pharm. Bull., 1986, 34, 2518 (glucoside)
Nishimura, K. eta/, Phytochemistry, 1986, 25, 2375
(Lactupicriside)

8,9-Dihydroxy-3-oxo-10(14)-guaien-12,6- Sq-01903
olide
(51%,61%,8/1)-form
8-Tigloyl: [72782-52-6]. Eupasessifolide B
C 20H 220 6 M 358.390
Constit. of Eupatorium sessilifolium. Cryst. (CHC1 3jpet. -OH
ether). Mp 184°. [cx]i;l -30° (c, 1.6 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1401.

8,15-Dihydroxy-2-oxo-1(10),3,11(13)- Sq-01902 0
guaiatrien-12,6-olide C 15H 200 5 M 280.320
1l%,4pH,51%,6"-,8"-,9"-,11 PH-form
Constit. of Amberboa tubuliflora.
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 3946 (isol, pmr, cmr)

10,15-Dihydroxy-2-oxo-3-guaien-12,6- Sq-01904
olide
0
C 15H 160 5 M 276.288
(51%,61%,81%)-form [1891-29-8] Lactucin
Constit. of Lactuca virosa and L. serriola. Also from
Cichorium intybus. Cryst. (Me 2CO). Mp 224-228°. [cx] 0
+49° (c, 0.9 in MeOH).
8-Ac: [83117-61-7].
C 17H 180 6 M 318.326 0
Constit. of L. jioridana and L. mucronata. Gum. C 15H 200 5 M 280.320
(1 ,_,s,.,6,.,1 op,1 11% )-form [117259-18-4] Hieracin I

490
2,9-Dioxo-1(10),3,11(13)-guaiatrien-... - 3,4-Epoxy-8,9-dihydroxy-1(10),11(13) ... Sq-01905 - Sq-01908

Constit. of Picris hieracioides. Bohlmann, F. eta/, Phytochemistry, 1979, 18, 995

11 ,13-Didehydro: [117259-19-5]. 10,15-Dihydroxy-2-oxo- (Athanadregeolide)
Tsankova, E. eta/, Phytochemistry, 1981, 20, 1436 (Apressin)
3 ,11(13)-guaiadien-12,6-olide. Hieracin II Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2543 (Tanaparthin
C 15H 180 5 M 278.304 epoxides)
Constit. of P. hieracioides. Bruno, M. eta/, Phytochemistry, 1988, 27, 1871 (Isoapressin)
Kanayama, T. eta/, Bull. Chern. Soc. Jpn., 1988, 61, 2971. Begley, M.J. eta/, Phytochemistry, 1989, 28, 940 (Tanaparthin
peroxides)

2,9-Dioxo-1(10),3,11(13)-guaiatrien-12,6- Sq-01905
olide 3,4-Epoxy-1,8-dihydroxy-10(14),11(13)- Sq-01907
guaiadien-12,6-olide

(5p,6fJ)-form
C 15H 180 5 M 278.304
9-0xoisodehyd.roleucodin
C 15H 140 4 M 258.273 (1~,3~,4~,5!1.,6!1.,8!1.)-form
!sol. from Montanoa imbricata. Oil. 8-Ac: [33204-40-9]. Arteglasin B
Seaman, F.C. eta/, Phytochemistry, 1986, 25, 2663. C 17H 200 6 M 320.341
Constit. of Artemisia douglasiana. Cryst.
(Me2CO/C6H 6). Mp 192-194°. [oc]~ + 150° (c, 0.5 in
1,4-Epidioxy-9,10-dihydroxy-2,11(13)- Sq-01906 CHC1 3).
guaiadien-12,6-olide Lee, K.H. eta/, Phytochemistry, 1971, 10, 405.

3,4-Epoxy-8,9-dihydroxy-1(1 0),11(13)- Sq-01908

guaiadien-12,6-olide
( 1cx,4cx,5cx,6cx,9cx, 1Ocx )-form

(3cx,4cx,5cx,6cx,8cx,9~)-form
0
CtsHts06 M 294.304
16.
(1!1.,4!1.,5!1.,6!1.,9!1.,10!1.)-form 0
9-Ac: [79858-81-4]. Apressin C 15H 180 5 M 278.304
C 17H 200 7 M 336.341 (3!1.,4!1.,5!1.,6!1.,8!1.,9/1)-form
Constit. of Achillea depressa. Cryst. (EtOAcjpet. ether).
Mp 182-184°. [01:] 0 -46.6° (c, 0.3 in EtOH). 9-Ange/oyl: [34837-46-2]. Subacaulin
C20 H 240 6 M 360.406
10-Ac: [116384-08-8]. Isoapressin Constit. of Berlandiera subacaulis. Cryst.
C 17H 20 0 7 M 336.341 (EtOAcjhexane). Mp 160-162° dec. [oc]i? + 129.9° (c, 2.1
Constit. of A. ligustica. in CHC1 3).
9-Deoxy: [85799-10-6]. 1,4-Epidioxy-10-hydroxy-2,11(13)- 9-Tig/oy/, 8-Ac: [34829-00-0]. Berlandin
guaiadien-12,6-olide. Tanaparthin !I.-peroxide C 22 H 260 7 M 402.443
Ct 5H 180 5 M 278.304 Constit. of B. subacaulis. Cryst. (EtOAcjhexane). Mp
Constit. of Tanacetum parthenium. Cryst. Mp 95-96°. 183-185°. [oc]i? + 110.9° (c, 2.8 in CHC1 3).
[o:Ji? -32.1° (c, 0.11 in CHC1 3).
(3p,4p,5!1.,6!1.,8!1.,9/l)-form
(1 p,4P,5!1.,6!1.,9!1.,1 0!1. )-form
9-Angeloy/: Bacchariolide B
9-Ange/oy/: [72635-10-0]. Athanadregeolide C20H 240 6 M 360.406
C20H 240 7 M 376.405 Constit. of Baccharis salicina. Gum.
Constit. of Athanasia dregeana. Oil. [01:]~4 -20° (c, 2 in
CHC1 3). Herz, W. eta/, J. Org. Chern., 1972, 37, 2532 (Subacaulin,
Ber/andin)
9-Deoxy: [85758-28-7]. Tanaparthin P-peroxide Cox, P.J. eta/, J. Chern. Soc., Perkin Trans. 2, 1975, 459 (cryst
C 15H 180 5 M 278.304 struct)
Constit. of T. parthenium. Gum. Parodi, F.J. et a/, Phytochemistry, 1988, 27, 2987 (Bacchariolide B)
8oc-Hydroxy, 9-ange/oy/: 8!1.-Hyd.roxyanthad.regeolide
C 20H 240 8 M 392.405
From A. dregeana. Cryst. (Et20/pet. ether). Mp 172-
1730.
(1 p,4P,5!1.,6!1.,9!1.,1 OfJ)-form
9-Angeloy/: [72690-44-9]. 10-Epiathanad.regeolide
C 20H 240 7 M 376.405
Constit. of A. dregeana. Oil.

491
3,4-Epoxy-8,14-dihydroxy-1(10)... - 10,14-Epoxy-2,8-dihydroxy-3,11(13)-.•. Sq-01909 - Sq-01912

3,4-Epoxy-8,14-dihydroxy-1(1 0),11(13)- Sq-01909 4,15-Epoxy-3,9-dihydroxy-10(14),11(13)- Sq-01911

guaiadien-12,6-olide guaiadien-12,6-olide

C 15H 180 5 M 278.304

CtsH 180 5 M 278.304 (1fl,3Jl,4Jl,5«,6«,9«)-form
(3«,4«,5«,6«,8/1)-form 9-(3-Chloro-2-hydroxy-2-methylpropanoyl):
8-Angeloyl: [70469·59-9]. Euponin C 19H 13Cl0 7 M 398.839
Czollz.P6 M 360.406 Constit. of Acroptilon repens and Centaurea hyrcania.
Constit. of Eupatorium japonicum. Cryst. (MeOH). Mp Cryst. (EtOH). Mp 196-198°. [o:]~ +92.3° (c, 0.68 in
148-150°. [o:]~4 -69° (c, 1 in EtOH). EtOH).
Nakajima, S. et al, Agric. Bioi. Chern., 1980, 44, 2893. Evstratova, R.I. et al, Khim. Prir. Soedin., 1973, 161.

4,15-Epoxy-3,8-dihydroxy-10(14), 11(13)- Sq-01910 10,14-Epoxy-2,8-dihydroxy-3,11(13)- Sq-01912

guaiadien-12,6-olide guaiadien-12,6-olide

0
0
CtsHtaOs M 278.304
(1«,3/1,4«,5«,6«,8«)-form C 15H 180 5 M 278.304
8-(2-M ethylpropenoyl): Desoxyjanerin (1«)Jl,5«,6«,8fl,l0« )-form
C19Hll06 M 346.379 8-(4-Acetoxy-2-methyl-2Z-butenoyl): [53142-47-5].
Constit. of Pleiotaxis rugosa and Ptilostemon Deoxygraminiliatrin
diacanthum. Oil. [o:]~ + 55.7° (c, 2.0 in CHC1 3). C 15H 180 5 M 278.304
8-(2-Methylpropenoyl), 3-Ac: Cryst. (Et20fpet. ether). Mp Constit. of Liatris spp. Gum. [o:]i; -48.5° (c, 0.74 in
134-136°. CHC13).
8-(2-Hydroxymethylpropenoyl): [64205-84-1]. Janerin 8-Angeloyl: [89396-25-8]. Desoxyeuparotin
C 19Hll07 M 362.379 C10H 140 6 M 360.406
Constit. of Centaurea repens and Pleiotaxis rugosa. Oil. Constit. of Trichogonia santosii. Oil.
[o:]i; +69.SO (c, 2.14 in CHC1 3). 8-0[[2-(2-Hydroxymethyl-2E-butenoyl)oxy]-2E-butenoyl], 2-
8-(2,3-Epoxy-2-methylpropanoyl)(S-): [55399-34-3]. Ac: [53142-46-4]. Spicatint
Subluteolide C27H310 10 M 516.544
C 1,Hll07 M 362.379 Constit. of L. spicata. Resin. [o:]i; + ,Hg - 146° (c, 0.2 in
Constit. of Vernonia sublutea. Amorph. [o:Jn + 54° (c, 0.9 CHC13).
in CHC13). 2-Ketone, 8-tigloyl: [72782-53-7]. Eupasessifolide A
8-(2,3-Epoxy-2-methylpropanoyl)(R-): [11024-67-2]. Repin C 20Hll06 M 358.390
C1,Hll07 M 362.379 Constit. of Eupatorium sessilifolium. Oil. [o:]~4 +23.9° (c,
Constit. of C. hyrcanica and C. repens (Acroptilon 1.3 in CHC1 3).
repens). Causes nervous disorder (equine nigropallida1 Herz, W. et al, J. Org. Chern., 1975, 40, 199 (isol)
encephalomalica) in horses. Cryst. (MeOH). Mp 155- Karlsson, B. et al, Tetrahedron Lett., 1975, 2245 (struct)
1570. (O:]D + 101°. Karlsson, B. et al, Acta Crystallogr., Sect. B, 1979, 35, 244 (cryst
struct, Spicatin)
8-(3-Chloro-2-hydroxy-2-methylpropanoyl): [41787-75-1]. Bohlmann, F. et al, Phytochemistry, 1979, 18, 1401 (Eupasessifolide
Acroptilin. Chlorohyssopifolin C A)
C 1,H13Cl07 M 398.839 Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 162 (5-
Constit. of Acroptilon repens and C. spp. Cryst. Mp Desoxyeuparotin)
197-1999. [o:Jn + 100° (c, 1.3 in MeOH).
[54278-78-3]
Gonzales, A.G. eta/, J. Chern. Soc., Perkin Trans. 1, 1976, 1663
(struct)
Mompon, B. et al, Tetrahedron, 1977, 33, 2199 (Subluteolide)
Bohlmann, F. et al, Phytochemistry, 1980, 19, 692; 1982, 21, 1434
(isol, struct)
Stevens, K.L., Phytochemistry, 1982, 21, 1093 (struct)
Stevens, K.L. et al, J. Nat. Prod. (Lloydia), 1990, 53, 218 (isol,
pmr, cmr, cryst struct, Repin)

492
10,14-Epoxy-3,8-dihydroxy-4(15)... - 9,10-Epoxy-1,15-dihydroxy-8-oxo-... Sq-01913 - Sq-01918

10,14-Epoxy-3,8-dihydroxy-4(15),11(13)- Sq-01913 3,4-Epoxy-5,8-dihydroxy-2-oxo- Sq-01916

guaiadien-12,6-olide 1(10),11(13)-guaiadien-12,6-olide

HO

0
C15H 180 5 M 278.304 ,o,
C 15H 1 M 292.288
(1~,1~,511.,611.,8~,10~)-form
(3«,411.,511.,611.,8/1)-form
8-Ac: [32534-03-5]. Artefrtu~sin 8-(3-Methyl-2-butenoyl): [79421-63-9). Guevariolide
Ct,H 200 6 M 320.341 C20H 220 7 M 374.390
Constit. of Artemisia franserioides. Cryst. Constit. of Guevaria sodiroi. Gum. [oc]i;4 -228° (c, 0.15
(EtOAc/CHp~. Mp 197-198°. [oc]~ +33° (c, 0.6 in in CHCI 3).
Py). Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1144.
Lee, K.H. eta/, Phytochemistry, 1971, 10, 205.
3,4-Epoxy-8,9-dihydroxy-2-oxo- Sq-01917
2,3-Epoxy-4,10-dibydroxy-11(13)-guaien- Sq-01914 1(10), 11(13)-guaiadien-12,6-olide
12,6-olide

0
,o,
C 15H 1 M 292.288
(3«,4«,5«,6«,8P,9fl)-form
C 15H 200 5 M 280.320 8,9- Dihydroxy-2-oxo/udartin
(1«,211.,111.,411.,511.,611.,1011.)-form [93552-70-6] Anobin 8-Tig/oyl:
Constit. of Achillea nobilis. Cryst. (EtOH). Mp 175.5- C20H 220 7 M 374.390
177.50.
Constit. of Lasiolaena santosii. Gum.
Adekenov, S.M. et a/, Khim. Prir. Soedin., 1984, 20, 603. 8-(2-Acetoxymethyi-2E-butenoyl):
CnH 240 9 M 432.426
3,4-Epoxy-2,8-dihydroxy-10-guaien-12,6- Sq-01915 From L. santosii. Gum.
olide 8-(2-Acetoxymethyl-2E-butenoyl), 9-Ac:
C24H 260 10 M 474.463
Constit. of L. santosii. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.

9,10-Epoxy-1,15-dibydroxy-8-oxo- Sq-01918
3,11(13)-guaiadien-12,6-olide
0
C 15H 200 5 M 280.320
(1 P.1«,4«,5«,8P,l1/I)-form
Di-Ac: [38555-39-4). Christinine
CI,H2407 M 364.394
Constit. of Stevia serrata. Cryst. (Me2COjisopropyl
ether). Mp 164-165°. [oc]n + 19.7° (c, 3.6 in CHCI 3). 0
Salmon, M. eta/, J. Org. Chern., 1973, 38, 1759. ctsH1,o, M 292.288
(1«,5«,611.,911.,10«)-form
1-Tigloyl: [65580-16-7). Euperfolide
C20H 220 7 M 374.390
Constit. of Eupatorium perfoliatum. Oil.
Bohlmann, F. eta/, Phytochemistry, 1977, 16, 1973.

493
1,8-Epoxy-4,11(13)-guaiadien-12,6-... - 1,10-Epoxy-3-guaien-12,6-olide
1,8-Epoxy-4,11(13}-guaiadien-12,6-olide Sq-01919
C 15H 180 3 M 246.305
(1fJ,6«.,7fJH,8fl,1 0«. )-form [52940-08-6] 1 ,8-Epoxyosmitopsin
Constit. of Osmitopsis asteriscoides. Cryst. (Et20jpet.
ether). Mp 132.2°. [ex]i;' -301° (c, 0.9 in CHC1 3).
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1409.
1(10)-Epoxy-3,11(13}-guaiadien-12,6-olide Sq-01920
ctJ
(}I~
0 From A. adamsii. Oil. [ex]~4 -8° (c, 0.3 in CHC1 3).
C 15H 180 3 M 246.305
(1 /1,5«.,6«.,1 Of/)-form [84692-91-1] Argillbin
Constit. of Artemisia glabella. Cryst. (hexane). Mp 100-
1020. [ex]i? +45.6° (c, 0.3 in CHC1 3).
Adekenov, S.M. et al, Khim. Prir. Soedin., 1982, 18, 655; Chern.
Nat. Compd. (Engl. Trans/.), 623 (iso/, ir, uv, ms)
Zdero, C. et a/, Phytochemistry, 1990, 29, 189 (iso/, pmr)
3,4-Epoxy-10(14),11(13)-guaiadien-12,6- Sq-01921
olide
C15H 180 3 M 246.305
(1«.,3rx.,4«.,5«.,6«.)-form [10180-89-9] Estafiatin
Constit. of Artemisia mexicana and from Cotula
coronopifolia. Cryst. (Et20jhexane). Mp 104-106°. [ex]~
-9.9° (CHC1 3).
11ex,13-Dihydro: 3ex,4ex-Epoxy-10(14)-guaien-12,6ex-olide.
11«.,13-Dihydroestafiatin
C15H 200 3 M 248.321
Constit. of A. sieversiana. Oil. [ex]i;' +94° (c, 0.05 in
CHC1 3).
11P,l3-Dihydro: Constit. of A. adamsii. Oil.
10ex,14-Epoxide: 3,4:10,14-Diepoxy-11(13)-guaien-
12 ,6-olide. 1Orx.,14-Epoxyestafiatin
C15H 180 4 M 262.305
Constit. of Stevia alpina. Cryst. (EtOAcjCHC1 3). Mp
113-1W.
10fi,14-Epoxide: 10/1,14-Epoxyestafiatin
C15H180 4 M 262.305
Constit. of S. alpina. Cryst. (Et0AcjCHCl 3). Mp 159-
161°.
Sanchez-Viesca, F. eta/, Tetrahedron, 1963, 19, 1285 (iso/, uv, ir,
pmr)
Bohlmann, F. et a/, Chern. Ber., 1966, 99, 2828 (isol)
494
Sq-01919 - Sq-01922
Edgar, M.T. eta/, J. Org. Chern., 1979, 44, 159 (synth)
Macaira, L.A. eta/, Tetrahedron Lett., 1980, 773 (synth)
Demuznek, M. et a/, Tetrahedron Lett., 1982, 23, 2501 (synth)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1003, 1009 (isol)
de Heluani, C.S. eta/, Phytochemistry, 1989, 28, 1931 (isol, cryst
struct)
1,10-Epoxy-3-guaien-12,6-olide Sq-01922
«>
r~--
o
C15H 200 3 M 248.321
(1«.,5rx.,6rx.,10rx.,ll«.)-form [6831-14-7] Arborescin
Constit. of Artemisia arborescens. Also from Matricaria
globifera. Cryst. Mp 145°. [exln +63° (CHC1 3).
!J.4-1somer, 3-hydroperoxy: 1ex, lOex- Epoxy-3-hydroperoxy-4-
guaien-12,6ex-olide. 3-Hydroperoxy-4,5-dehydro-3,4-
dihydroarborescin
C15H 200 5 M 280.320
!J. 4- Isomer, 3-hydroxy: 1ex, 1Oex- Epoxy-3-hydroxy-4-guaien-
12,6a.-olide. 3-Hydroxy-4,5-dehydro-3,4-dihydroarborescin
C15H 200 4 M 264.321
From A. adamsii. Oil.
8ex-Hydroxy: 1a., lOa.- Epoxy-8a.-
hydroxy-3-guaien-12,6a.-olide. 8«.-Hydroxyarborescin
C15H2004 M 264.321
From A. adamsii. Oil. [a.]~4 + 58° (c, 0.2 in CHC1 3).
2a.-Hydroxy: 1a., 1Oa.-Epoxy-2a.-hydroxy-
3-guaien-12,6a.-olide. 2rx.-Hydroxyarborescin
C15H 200 4 M 264.321
From A. adamsii. Oil.
2fi-Hydroxy: 1a.,10a.-Epoxy-2fi-hydroxy-3-guaien-12,6a.-
olide. 2fl-Hydroxyarborescin
C15H 200 4 M 264.321
From A. adamsii. Oil.
!J.2 Isomer, 4a.-hydroperoxy: 1a.,10a.-Epoxy-4a.-hydroperoxy-
2-guaien-l2,6a.-olide. 4rx.-Hydroperoxy-2,3-dehydro-3,4-
dihydroarborescin
C15H 200 5 M 280.320
From A. adamsii. Oil. [a.]i;' - 105° (c, 0.5 in CHC1 3).
!J.4 Isomer, 3-oxo: 1a.,10a.-Epoxy-3-oxo-4-
guaien-12,6a.-olide. 3-0xo-4,5-dehydro-3 ,4-dihydroarborescin
C15H 180 4 M 262.305
From A. adamsii. Oil. [a.]i;' -25° (c, 0.6 in CHC1 3).
(1~,5~,6~,10~,10~)-form [25319-03-3] Sieversinin
Constit. of A. sieversiana. Cryst. (EtOH). Mp 141-142°.
[a.] 0 + 57° (CHC1 3). Shown not to be identical with
either Arborescin or 1, 10-diepiarborescin. The
stereochemistry assigned in CA appears to be incorrect.
Suchy, M. eta/, Collect. Czech. Chern. Commun., 1964, 29, 1829
(struct)
Nazarenko, M.V. eta/, Khim. Prir. Soedin., 1966, 2, 399
(Sieversinin)
Ando, M. eta/, J. Org. Chern., 1982, 47, 3909 (synth, sterochem)
Bohlmann, F. et a/, Phytochemistry, 1985, 24, 1003 (derivs)
2,3-Epoxy-4(15)-guaien-12,6-olide - 3,4-Epoxy-2-hydroxy-1(10),11(13)-... Sq-01923 - Sq-01928

2,3-Epoxy-4(15)-guaien-12,6-olide Sq-01923 2-Ketone: [129196-87-8]. 1«,10«-Epoxy-2-oxo-3,11(13)-

guaiadien-12,6rz-olide
CtsH 160 4 M 260.289
Constit. of K. lasiophthalma. Gum.
(1P,2«,6«,10p)-form [129196-88-9]
Constit. of K. lasiophthalma. Gum.
(1P,2P,6«,10p)-form
11 p,13-Dihydro: [129262-13-1]. 1p,1OP-Epoxy-2P-hydroxy-J-
guaien-12,6rz-olide
CtsH 180 3 M 246.305 CtsHw04 M 264.321
Drawing error in the paper. Constit. of K. lasiophthalma.
(2rz,3rz,6rz)-form De Gutierrez, A.N. eta/, Phytochemistry, 1990, 29, 1219 (isol,
2rz,3rz-Epoxy-11 rz,13-dihydrodehydrocostus lactone pmr)
Constit. of Artemisia sieversiana. Oil.
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 1009. 1,10-Epoxy-8-hydroxy-3,11(13)-guaiadien- Sq-01927
12,6-olide
4,5-Epoxy-11(13)-guaien-12,6-olide Sq-01924

C 15H 180 4 M 262.305

C 15H 20 0 3 M 248.321 (1P,5rz,6rz,8rz,1 Op)-form
(JP,4rz,5rz,6rz,7rz,10rz)-form [52940-07-5] 4,5-Epoxyosmitopsin Ac: [126829-70-7]. 81X-Acetoxy-1p,10P-epoxy-3, 11(13)-
Constit. of Osmitopsis asteriscoides. Cryst. (Et20/pet. guaiadien-12, 61X-olide
ether). Mp 119.3°. [1X]i;4 -203° (c, 0.8 in CHC1 3). C 17H 200 5 M 304.342
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1409. Constit. of P. eenii. Cryst. Mp 190° dec.
(1.;,5rz,6«,8.;,Jo.;)-form
10,14-Epoxy-4(15)-guaien-12,6-olide Sq-01925 11P,13-Dihydro, Ac: [6883-63-2]. Globicin
C17H 120 5 M 306.358
Constit. of Matricaria globifera. Cryst. (EtOH). Mp 148-
1500. [1X]i? +66° (c, 0.2 in CHC1 3).
Prochazka, V. eta/, Collect. Czech. Chern. Commun., 1963, 28,
1202 (Giobicin)
Zdero, C. eta/, Phytochemistry, 1990, 29, 189 (isol, pmr)

0 3,4-Epoxy-2-hydroxy-1(10),11(13)- Sq-01928
guaiadien-12,6-olide
C 1sH 20 0 3 M 248.321
(6«,10rz,11PH)-form [128722-88-3]
Constit. of Vladimiria souliei. Gum.
Jp-Hydroxy, 4P,J5-dihydro: [128722-89-4]. 10rz,l4-Epoxy-
3P-hydroxy-12 ,6rz-guaianolide
C 15H 110 4 M 266.336
Constit. of V. souliei. Gum.
Tan, R.X. et at, Phytochemistry, 1990, 29, 1209 (isol, pmr)
0
C 15H 180 4 M 262.305
1,10-Epoxy-2-hydroxy-3,11(13)-guaiadien- Sq-01926
(2rz,3rz,4rz,6rz)-form [129263-32-7]
12,6-olide Constit. of Kaunia /asiophthalma. Gum.
Ac: [129263-33-8].
C17H 200 5 M 304.342
Constit. of K. lasiophthalma. Cryst. (EtOAcjheptane).
Mp 192-193°.
(2-Methy/propenoyl): [129196-89-0].
C 19H 1z05 M 330.380
Constit. of K. /asiophthalma. Gum.
(2-Methylbutanoyl):
C 15H 180 4 M 262.305 C20 H 160 5 M 346.422
(lrz,2rz,6rz,10rz)-form [129262-12-0] Constit. of K. lasiophthalma. Cryst. Mp 123-125°.
Constit. of Kaunia lasiophthalma. Cryst. Mp 129-130°. Tig/oyl: [129196-91-4].
C 20 H 1P 5 M 344.407

495
3,4-Epoxy-8-hydroxy-1(10),11(13)-.•• - 1,10-Epoxy-8-hydroxy-2-oxo-3,7(11)-... Sq-01929 - Sq-01932

Constit. of K. lasiophthalma. Cryst. Mp 125-127°. Constit. of B. oppositifo/ia. Cryst. (EtOAcfhexane). Mp

2-Ketone: [81 053-59-0]. 31X,41X-Epoxy-2-oxo-1(1 0), 11(13)- 140-142°. [1X]n + 14.3° (CHC1 3).
guaiadien-12,61X-olide. 2-0xoludartin (1 rx.,5rx.,6rx.,8rx.,l Op)-form
C 1 ~H 16 0 4 M 260.289 11P,I3-Dihydro, Ac: [35144-09-3]. Viscidulin A
lsol. from K. ignorata. Cryst. (EtzOfpet. ether). Mp 182- C 17 H 2zO~ M 306.358
1830. [1X]~4 -34° (c, 1.4 in CHC1 3). Constit. of Artemisia cana. Cryst.(EtzOfpet. ether). Mp
(2P.3rx.,4rx.,6rx.)-form 124°. [1X]n +77° (c, 2.14 in CHC1 3).
Ac: [92592-62-6]. 2P-Acetoxy-31X,41X-epoxy-1(10),11(13)- de Vivar, A.R. eta/, Can. J. Chern., 1969, 47, 2849 (isol, struct)
guaiadien-12,61X-olide. 2fJ-Acetoxy-3rx.,4rx.-epoxy-3 ,4- Shafizadeh, F. eta/, J. Org. Chern., 1972, 37, 3168 (Viscidulin A)
dihydrokauniolide. 2P-Acetoxyludartin Herz, W. et al, Phytochemistry, 1972, 11, 371 (Bahifolin)
C 17 H 20 0~ M 304.342 Herz, W. et al, J. Org. Chern., 1980, 45, 3163 (cryst struct)
lsol. from Grosvenoria coelocaules. Cryst. (EtzO). Mp
191°. [1X]i; +92° (c, 0.17 in CHC1 3). 3,4-Epoxy-8-hydroxy-10(14),11(13)- Sq-01931
(2P.3P,4P,6rx.)-form [129262-11-9] guaidien-12,6-olide
Constit. of K. lasiophthalma. Gum.
11P,13-Dihydro: [129196-86-7]. 3p,4fJ-Epoxy-2fJ-hydroxy-
1(10)-guaien-12,6rx.-olide
C 1 ~H 20 0 4 M 264.321
Constit. of K. lasiophtha/ma. Gum.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 2375; 1984, 23,
1187.
De Gutierrez, A.N. et al, Phytochemistry, 1990, 29, 1219. 0
Ct~H 18 04 M 262.305
3,4-Epoxy-8-hydroxy-1(10),11(13)- Sq-01929 (1rx..Jrx.,4rx.,5rx.,6rx.,8rx.)-form
guaiadien-12,6-olide 8-Hydroxyesta.fiatin
8-(2-M ethylpropenoyl):

1~-0H
C 19 Hzz0~ M 330.380
Constit. of Lychnophora blanchetii. Gum.
o-- I
(1rx..3.;,4.;,5rx.,6rx.,8rx.)-form
HI - 11 p,J3-Dihydro: [35191-38-9]. 3,4-Epoxy-8-hydroxy-10(1 4)-
0 guaien-12,6-o/ide. Viscidulin C
0 c.~H 2004 M 264.321
Constit. of Artemisia viscidula. Cryst.(EtzOjpet. ether).
(3rx.,4rx.,5rx.,6rx.,8rx. )-form Mp 147°. [1X]n +49° (c, 1.955 in CHC1 3).
Ac: [33204-39-6]. Arteglasin A 11P,l3-Dihydro, Ac: [35144-10-6]. Viscidulin B
C 17 H 20 0~ M 304.342 C 17 H 22 0~ M 306.358
Constit. of Artemisia doug/asiana and Chrysanthemum Constit. of A. viscidula. Cryst. (CHC1 3/Et20). Mp 132-
indicum. Cryst. (CH 2Cl 2/Et20). Mp 207-208°. [IX]~ 1330. [1X]n + 59.8° (c, 2.3 in CHC1 3).
+ 110° (c, 0.8 in CHC1 3).
Shafizadeh, F. et al, J. Org. Chern., 1972, 37, 3168.
Lee, K.H. et al, Phytochemistry, 1971, 10, 405 (isol) Bohlmann, F. et al, Phytochemistry, 1980, 19, 2669.
Schmalle, H.W. et al, Acta Crystallogr., Sect. B, 1977, 33, 2213
(struct)
1,10-Epoxy-8-hydroxy-2-oxo-3,7(11 )- Sq-01932
10,14-Epoxy-8-hydroxy-3,11(13)- Sq-01930 guaiadien-12,6-olide
guaiadien-12,6-olide

(1 a,5a,6a,8~, 10~)-form
13

0 C 1 ~H 16 0~ M 276.288
(1P,5P,6P,8rx.,l0p)-form [86948-40-5] GuiUonein
C 1 ~H 18 04 M 262.305
Constit. of roots of Guillonea scabra. Cryst. (MeOH).
(1rx.,5rx.,6rx.,8p,10p)-form [24268-44-8] Bahia I Mp 225-230°. [1X]~ +7° (c, 0.12 in CHC13).
Constit. of Bahia pringlei. Cryst. (Me2COfdiisopropy1
Pinar, M. et a/, Phytochemistry, 1983, 22, 987 (isol, cryst struct)
ether). Mp 209-2WO. [IXJi:l +47.7° (c, 1 in CHC13).
8-(4-Hydroxy-2-hydroxymethyi-2Z-butenoyl): [24268-45-9].
Bahia II
C20 H 240 7 M 376.405
Constit. of B. pringlei. Cryst. (Et0Acfdiisopropy1 ether).
Mp 133-134°. [o:]~ +47.7° (c, 1 in CHC1 3).
8-(3-Furoyl): [35682-60-1]. Bahifolin
C20H 220 7 M 374.390

496
3,4-Epoxy-8-hydroxy-2-oxo-1(10)... - 10,14-Epoxy-2,5,8-trihydroxy-... Sq-01933 - Sq-01938

3,4-Epoxy-8-hydroxy-2-oxo-1(10),11(13)- Sq-01933 Ct7Hu08 M 356.372

guaiadien-12,lH»Iide Constit. of Artemisia montana. Cryst. Mp 192-194°.
Nagaki, M. eta/, Phytochemistry, 1989, 28, 2731 (iso/, pmr, cmr)

~~~sOH
0- I
H,
3,4-Epoxy-2,5,8-trihydroxy-10(14),11(13)-
guaiadien-12,lH»Iide
Sq-01936

0 -
0
CtsH160 5 M 276.288
(3«,4«.5«,6«/lf/)-form
8- Hydroxy-2-oxoludartin
8-Tigloyl:
C~ 12 0 6 M. 358.390 CtsH180 6 M 294.304
Constit. of Lasiolaena santosii. Gum. [1X]i;" -83.3° (c, (1«,2P,3«,4«.S«,6«/lf/)-form
0.55 in CHC1 3). 8-Angeloyl: [20071-53-8]. E11pat11ndin
8-(2-Acetoxymethyi-2E-butenoyl): C20 H 240 7 M 376.405
C12H 240 8 M 416.427 Constit. of Eupatorium rotundifolium. Tumour inhibitor.
Constit. of L. santosii. Gum. Cryst. (CHCl 3/C6H 6jpet. ether). Mp 188-189°. [11.]~
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613. -80° (c, 0.44 in EtOH).
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3876.
3,4-Epoxy-2,5,8,9-tetrahydroxy- Sq-01934
1(10),11(13)-guaiadien-12,6-olide 3,4-Epoxy-2,8,9-trihydroxy-1(10),11(13)- Sq-01937
guaiadien-12,lH»Iide
HO
I

0
CtsH180 7 M 310.303 0
(2P,3«,4«.S«,611./lll.,9p)-form CtsH 180s M 278.304
9-Angeloyl, 2-Ac: [90734-99-9]. ZoapattUWiide C (2«,3P,4P.S«,6«,8«,9p)-form
C12H 260 9 M 434.442
Constit. of Montanoa tomentosa. Cryst. (CHC1 3/Et20). 9-Angeloyl: [117823-99-1]. Bacchariolide A
Mp ll7-ll8°. C20H 240 7 M 376.405
Constit. of Baccharis salicina. Gum.
2-Ketone, 9-angeloyl: 311.,4«-Epoxypllmilin
C20H 220 8 M 390.389 (2P,3«,4«.S«,6«,8«,9f/)-form
Constit. of Berlandiera pumila, B. texana and B. lyatra. 9-Angeloyl, 2-Ac: [90735-00-5]. Zoapatanolide D
Cryst. Mp 178-183° dec. C12H 260 8 M 418.443
2-Ketone, 9-angeloyl, 8-Ac: 8-Acetyl-3«,411.-epoxypllmilin Constit. of Montanoa tomentosa. Cryst. (CHC1J1Et20).
C12H 240 9 M 432.426 Mp 205-207°.
Constit. of M. tomentosa. Gum. Quijano, L. eta/, Phytochemistry, 1984, 23, 125 (Zoapatanolide D)
Parodi, F.J. eta/, Phytochemistry, 1988, 1:1, 2987 (Bacchariolide A)
Fischer, N.H. et al, J. Heterocycl. Chern., 1982, 19, 181.
Quijano, L. et al, Phytochemistry, 1984, 23, 125.
Seaman, F.C. et al, Phytochemistry, 1984, 23, 817 (isol, cryst 10,14-Epoxy-2,5,8-trihydroxy-3,11(13)- Sq-01938
struct, derivs) guaiadien-12,6-olide
2,3-Epoxy-1,4,8,10-tetrahydroxy-12,6- Sq-01935
guaianolide

CtsHts06 M 294.304
(1«,2P.S«,6«/JP,l011.)-form
0 8-Ange/oy/: [10191-01-2]. E11parotin
C15H120 7 M 314.335 C20H 240 7 M 376.405
(1«,2«,3«,4«.5«,6«/1«,1011.,11Pll)-form Constit. of Eupatorium rotundifolium. Tumour growth
inhibitor. Cryst. (EtOAcfpet. ether). Mp 199-200° (vac.).
8-Ac: (125180-60-1). Ezoyomoginin [1X]i; -124° (c, 1.25 in EtOH).

497
10,14-Epoxy-2,8,9-trihydroxy-... - Ezomontanin Sq-01939 - Sq-01944

8-Ange/oyl, 2-Ac: [10215-89-1]. Euparotin acetate Constit. of Tanacetum cilicium. Cryst. Mp 153°.
CnH:11;08 M 418.443 (lrx.,2P)rx.,4rx.,6rx.,10rx.)-form [128386-05-0]1sotanciloide
Constit. of E. rotundifolium. Tumour inhibitor. Cryst. CtsH:zoO, M 296.319
(CHC1 3/C6H 6 jpet. ether). Mp 156-157° (vac.). [ex]~ Constit. of T. cilicium. Gum.
-191° (c, 0.54 in EtOH).
Oksiiz, S., Phytochemistry, 1990, 29, 887 (isol, pmr)
Kupchan, S.M. et al, J. Org. Chern., 1969, 34, 3876 (struct, isol)
Kupchan, S.M. eta/, J. Med. Chern., 1971, 14, 1147 (pharmacal)
McPhail, A.T. eta/, Tetrahedron, 1973, 29, 1751 (abs config) 3,4-Epoxy-2,8,10-trihydroxy-11(13)- Sq-01942
guaien-12,6-olide
10,14-Epoxy-2,8,9-trihydroxy-3,11(13)- Sq-01939
guaiadien-12,6-olide

CtsH:w06 M 296.319
0 (1rx.,2p)rx.,4rx.,5rx.,6rx..SP,JOrx.)-form
CtsH180 6 M 294.304 8-(2-Methylbutanoyl): [73021-06-4].
(1rx.,2P,5rx.,6rx..SP,9rx.,10rx.)-form C20H 280 7 M 380.437
8-Tigloyl: [76461-22-8]. Agriantholide Constit. of Eupatorium anomalum. Gum. [cx] 0 -56.9° (c,
Cwli240 7 M 376.405 0.03 in CHC1 3).
Constit. of Agrianthus pungens. Gum. 8-(3-Methy/butanoyl): [73021-07-5].
3rx.,4cx-Epoxide, 8-tigloyl: C20H 280 7 M 380.437
C20H 240 8 M 392.405 Constit. of E. anomalum. Gum.
Constit. of A. pungens. Gum. Herz, W. et al, Phytochemistry, 1979, 18, 1337.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 1873.
Eufoliatorin Sq-01943
1,2-Epoxy-3,4,10-trihydroxy-11(13)- Sq-01940 [62197-65-3]
guaien-12,6-olide

0
0 C20H 240 7 M 376.405
C 15H 200 6 M 296.319 Constit. of Eupatorium perfoliatum. Cryst.
(EtOAcjhexane). Mp 224°.
(lrx.,2rx.)rx.,4P,5rx.,6rx.,10rx.)-form [103001-39-4] Artecanin hydrate
Constit. of Artemisia xanthochroa. Cryst. Mp 142°. Herz, W. et al, J. Org. Chern., 1977, 42, 2264.
(1 rx.,2rx.)rx.,4P,5rx.,6rx.,1 0/1)-form
Ajajinin . Ezomontanin Sq-01944
Constit. of Ajania fastigiata. Cryst. (C 6H 6 /Et0Ac). Mp 8cx-Acetoxy-1P.4P-epidioxy-10cx-hydroxy-2,11 (I 3)-guaiadien-
162-164°. 12 ,6cx-olide
Yusupov, M.I. et al, Khim. Prir. Soedin., 1983, 19, 650 (Ajafinin) [111455-72-2]
Tashkodzhaev, B. eta/, Khim. Prir. Soedin., 1986, 22, 270 (cryst
struct, Ajafinin)
Huneck, S. et al, Phytochemistry, 1986, 25, 883 (Artecanin hydrate)

3,4-Epoxy-1,2,10-trihydroxy-11(13)- Sq-01941
guaien-12,6-olide

0
C17H 200 7 M 336.341
Constit. of Artemisia montana. Cryst. Mp 147-148°.
11P,J3-Dihydro: [111455-73-3]. 11,13-Dihydroezomontanin
C17Hu07 M 338.357
0 Constit. of A. montana. Cryst. Mp 163-164°.
Koreeda, M. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1988,
CtsH200, M 296.319 108, 434 (isol, pmr, cmr, ir)
(1P,2rx.)rx.,4rx.,6rx.,10rx.)-form [128286-95-3] Tanciloide Nagaki, M. eta/, Phytochemistry, 1989, 28, 2731 (isol)

498
Gnididione - 1(10),3,11(13)-Guaiatrien-12,6-... Sq-01945 - Sq-01951

Gnididione Sq-01945 8P-Angeloyloxy: BP-Angeloyloxyguaiagrazielolide

[60498-89-7] C10H100 6 M 356.374
Constit. of Grazielia intermedia. Gum. [a]i;' -66.7° (c,
0.12 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1069.

1(10),2,4-Guaiatrien-12,6-olide Sq-01949

C 15H 160 3 M 244.290

Constit. of Gnidia latifolia. Cryst. (MeOH). Mp 110-111°.
[a]~ + 372° (c, 1 in CHC1 3).
Kupchan, S.M. eta/, J. Org. Chern., 1977, 42, 348 (isol)
Jacobi, P.A. eta/, J. Am. Chern. Soc., 1984, 106, 3041; 1990, 55,
202 (synth)
Dell, C.P. eta/, J. Chern. Soc., Chern. Commun., 1987, 349 (synth)
Buttery, C.D. eta/, J. Chern. Soc., Perkin Trans. I, 1990, 1601 c,sH 180 1 M 230.306
(synth)
(6p,llrx.)-form [110210-00-9] Tannunolide B
C 15H 180 1 M 230.306
3,10(15)-Guaiadien-12,6-olide Sq-01946 From Tanacetum annuum. Yellow cryst. (Et 20). Mp
Grilllctone 101-102°. [aJn -29.8° (c, 1.52 in CHC13).
[38647-27-7] (6p,llp)-form [110209-99-9] Tannunolide A
Constit. ofT. annuum. Yellow cryst. (Et20). Mp 108-
1090. [aJn -100° (c, 1 in CHC1 3).
Barrero, A.F. eta/, Phytochemistry, 1987, 26, 1531.

1(1 0),2,4(15)-Guaiatrien-12,6-olide Sq-01950

C15H 1c,01 M 232.322

Constit. of Ferula grigorjevii and F. penninervis. Cryst. Mp
79-81°. [aln -125°.
Kir'yalov, N.P. eta/, Khim. Prir. Soedin., 1972, 8, 446; Chern. Nat.
Compd. (Engl. Trans/.), 445 (isol struct)
Nurmukhamedova, M.R. eta/, Khim. Prir. Soedin., 1982, 18, 261;
Chern. Nat. Compd. (Engl. Trans/.), 244 (isol) c,sH 180 1 M 230.306
(5rx.,6rx.,llrx.H)-form
4,11(13)-Guaiadien-12,6-olide Sq-01947 Tannunolide C
Constit. of Tanacetum annuum. Cryst. (Et20). Mp 137-
\
1380. [aJn -106.9° (c, 1.09 in CHC1 3).

~
Barrero, A. F. eta/, Phytochemistry, 1990, 29, 3575 (isol, pmr, cmr)

1(1 0),3,11(13)-Guaiatrien-12,6-olide Sq-01951

0
C 15H100 1 M 232.322
(lp,6rx.,7rx.,10rx.)-form [53527-48-3] Osmitopsin
Constit. of Osmitopsis asteriscoides. Oil.
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1409.
c,sH 180 1 M 230.306
Guaiagrazielolide Sq-01948 (5rx.,6rx.)-form [81066-45-7] Kauniolide
[79404-31-2] Constit. of Kaunia arbuscularis. Gum.
11 p,l3-Dihydro: 1(10),3-Guaiadien-12,6-olide. 11P,13-
Dihydrokauniolide
C15H 100 1 M 232.322
Constit. of K. arbuscularis. Gum. [a]i;' + 14.3° (c, 0.5 in
CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2375; 1984, 23, 1187
(is of)

0
c,sH140 4 M 258.273
Parent compd. appears to be currently unknown.

499
3,10(14),11(13)-Guaiatrien-12,6-... - 3-Hydroxyambrosin damsinate Sq-01952 - Sq-01956

3,10(14),11(13)-Guaiatrien-12,6-olide Sq-01952 2,3,7 ,8,1 0,11-Hexahydroxy-4-guaien-12,6- Sq-01955

olide

HO H,OH

Ct5Hta02 M 230.306
(1«,5rx.,6rx.)-form [68151-26-8] lsodehydrocostus lactone
Constit. of Saussurea lappa. Light-green mobile liq.
Kalsi, P.S. et a/, Phytochemistry, 1983, 22, 1993.
4(15),9,11(13)-Guaiatrien-12,6-olide Sq-01953
C15H 180 2 M 230.306
(1«,5rx.,6«)-form [37936-58-6] Erenumtlrine. Vanillosmin
Constit. of Eremanthus elaeagnus and Vanillosmopsis
erythropappa. Cryst. (hexane). Mp 73-74°. [ex]~ -110°
(c, 1 in CHCI 3).
Vichnewsk:i, W. et al, Phytochemistry, 1972, 11, 2563 (isol)
Corbella, A. et al, Phytochemistry, 1974, 13, 459 (isol)
Garcia, M. eta/, Phytochemistry, 1976, 15, 331 (struct)
da Silva, A.J.R. et a/, Org. Magn. Reson., 1981, 16, 230 (cmr)
Ando, M. et al, Chern. Lett., 1984, 493 (synth)
4(15),1 0(14),11(13)-Guaiatrien-12,6-olide Sq-01954
Ho-:tr1aw
r ~OH (1~,2~,3Cl,6~,7~0H,l0~,11Cl)-/orm
0
Ct5H 220 8 M 330.334
(1 p,2P,3rx.,6p,7pOH,Brx.,l op,Jl rx. )-form
2-0ctanoyl, 3-angeloyl, 8-butanoyl, 10-Ac: [67526-95-8].
Thapsigargin
C34H 51,012 M 650.762
Constit. of Thapsia garganica. The abs. config. is
unprecedented and is presumably associated with the
presence of the 7-0H group.
I> Skin irritant. Stimulates production of histamine.
2-Hexanoyl, 3-angeloyl, 8-butanoyl, 10-Ac: [67526-94-7].
Thapsigargicin
C32 H,11;012 M 622.708
Constit. of T. garganica. Gum.
I> Skin irritant.
(lrx.,2rx.,3P,6«,7rx.OH,BP,JOrx.,llfJ)-form
2-(3-Methyl-2-butenoyl), 3-angeloyl, 8-(2-methylbutanoyl),
10-Ac: [99270-55-0]. Thapsivillosin K
C32 H 440 12 M 620.692
Constit. ofT. villosa. Cryst. (C6H 6fhexane). Mp 119-
1210. [cx]i;' -28.6° (c, 2.5 in CHC13). The abs. config. is
likely to be the opposite of that indicated ie. same as
those of Thapsigargin and Thapsigargicin.
Christensen, S.B. et al, Tetrahedron Lett., 1980, 3829 (isol)
Christensen, S.B. et al, J. Org. Chern., 1982, 47, 649 (cryst struct)
Christensen, S.B. et al, J. Org. Chern., 1983, 48, 396 (cmr)
De Pascual Teresa, J. eta/, Phytochemistry, 1985, 24, 2071
( Thapsivillosin I()

~
Christensen, S.B. et al, Tetrahedron Lett., 1985, 26, 107 (abs
config)

3-Hydroxyambrosin damsinate Sq-01956

~~'
0
Ct5Ht80 2 M 230.306
(lrx.,5rx.,6rx.)-form [477-43-0] Dehydrocostus lactone
Constit. of Saussurea lappa, Veronica hirsuta and
Zaluzania tribolia. Cryst. Mp 60S. [cx] 0 -20° (CHCI 3). 0
11P,l3-Dihydro: [4955-03-7]. 4(15),10(14)-Guaiadien-12,6-
olide. Mokkolactone. Dehydrodihydrocostus lactone 0
C15H 20 0 2 M 232.322 C30H 380 6 M 494.627
Constit. of Saussurea lappa and the Chinese drug Sen-
Constit. of Ambrosia hispida. Cryst. (CHCI 3fhexane). Mp
mokko. Cryst. Mp 35-37°. [cx] 0 + 18.2° (CHCI 3).
150-152°.
Hik:ino, H. et a/, Chern. Pharm. Bull., 1964, 12, 632 (isol, struct)
Herz, W. et al, Phytochemistry, 1981, 20, 1601.
Mathur, S.B. et al, Tetrahedron, !965, 21, 3575 (struct)
Bankar, N.S. et al, Indian J. Chern., 1972, 10, 952 (isol)
Ando, M. eta/, Chern. Lett., 1984, 493 (synth)

500
1-Hydroxy-3,9-guaiadien-12,6-olide - 10-Hydroxy-3,11(13)-guaiadien-12,6-... Sq-01957 - Sq-01962

1-Hydroxy-3,9-guaiadien-12,6-olide Sq-01957 4-Hydroxy-1 0(14), 11(13)-guaiadien-12,6- Sq-01960

olide

0
Ct~H:zo0 3 M 248.321
Constit. of Artemisia adamsii. C 1 ~H:zo03 M 248.321
(1 rx.,5rx.,6«,11 ri)-form (1rx.,4rx.,5rx.,6rx.)-form [126621-30-5]
1rx.-Hydroxy-11/1,13-dihydrokauniolide Constit. of Arctotis auriculata.
Constit. of Artemisia adamsii. Oil.
llfl,J3-Dihydro: [68421-48-7]. 4oc-Hydroxy-10(14)-guaiaen-
~ 10 • 14 -Isomer: 1rx.-Hydroxy-3,10(11)-guaiadien-12,6rx.-olide
12,6oc-olide. Compressanolide
C 1 ~H:zo0 3 M 248.321 Isol. from Michelia compressa. Yellow oil.
Isol. from A. adamsii. Oil. [oc] 0 + 18° (c, 0.1 in CHC1 3).
Ogura, M. et al, Phytochemistry, 1978, 17, 957 (isol)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1003. Devreese, A.A. et al, Tetrahedron Lett., 1980, 4767 (synth)
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 195 (isol, pmr)
4-Hydroxy-1(1 0),2-guaiadien-12,6-olide Sq-01958
10-Hydroxy-1,3-guaiadien-12,6-olide Sq-01961

Ct~H:zo0 3

Tannunolide D
M 248.321
(4rx.,5rx.,6rx.,11rx.)-form

Constit. of Tanacetum annuum. Cryst. (Et 20). Mp 127-

C 1 ~H:w0 3
«3--
M 248.321
0

(6rx.,JOfJ,llrx.)-form [24399-20-0] Artabsin. Prochamazulenogenin

131°. [oc] 0 -62.2° (c, 1 in CHC1 3). Constit. of Artemisia absinthium and A. sieversiana.
Cryst. (EtOH). Mp 133-135°. [ex]~ -49°.
(4rx.,5rx.,6rx.,11 fl)-form
Tannunolide E Herout, V. et al, Collect. Czech. Chern. Commun., 1953, 18, 854
Constit. ofT. annuum. Cryst. (Et20). Mp 114-119°. [oc] 0 (isol)
Vokac, K. et al, Collect. Czech. Chern. Commun., 1912, 37, 1346
+ 31.13° (c, 0.99 in CHC1 3). (struct)
(4fl,5rx.,6rx.,11 fl)-form
DesacetoxyltUltricin
Constit. of Ursinia saxatilis. Cryst. (Et20). Mp 154°. 10-Hydroxy-3,11(13)-guaiadien-12,6-olide Sq-01962
[oc]i;i + 26° (c, 0.4 in Et20). [21956-65-0]
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1357 (isol, cryst
struct)
Barrero, A.F. et al, Phytochemistry, 1990, 29, 3575 (Tannunolides)

4-Hydroxy-1(1 0),11(13)-guaiadien-12,6- Sq-01959

olide

HO~'~ H,
0
C 1 ~H:zo03 M 248.321
(1 rx.,5rx.,6rx.,l Orx.)-form
Cumambranolide. 8-Deoxycumambrin B
Constit. of Artemisia nova and A. tripartita ssp. rupicola.
Prisms (Etpjpet. ether). Mp 117-118°.
0 10-0-fl-D-glucopyranoside: [100187-65-3]. Macrocliniside G
C 1 ~H:zo0 3 M 248.321 C21 H 34,08 M 410.463
(4rx.,5rx.,6rx.)-form [68370-47-8] Micheliolide Constit. of Macroclinidium trilobum. Needles (MeOH
Constit. of Michelia compressa. Cryst. (Et20). Mp 141°. aq.). Mp 128-129°. [oc]i,S +39.8° (c, 1.86 in MeOH).
Ogura, M. et al, Phytochemistry, 1978, 17, 957. (lrx.,5rx.,6rx.,l0fl)-form
10-Epicumambranolide. 10-Epi-8-deoxycumambrin B
Ct~H:zo03 M 248.321
Constit. of Stevia yaconensis. Cryst. (Etp). Mp 123-
1240.
Irwin, M.A. et al, Phytochemistry, 1969, 8, 305 (isol)

501
10-Hydroxy-4,11(13)-guaiadien-12,6-... - 1-Hydroxy-3,9,11(13)-guaiatrien-... Sq-01963 - Sq-01968
Miyase, T. et al, Chern. Pharm. Bull., 1985, 33, 4445 Constit. of Laserpitium prutenicum. Oil. (1X]i;' -60.5° (c,
(Macroclinoside G) 0.66 in Et20).
Sosa, V.E. et al, Phytochemistry, 1989, 28, 1925 (isol, cryst struct)
Bohlmann, F. et al, Chern. Ber., 1971, 104, 1611.

10-Hyd.roxy-4,11(13)-guaiadien-12,6-olide Sq-01963

cr>t>=l3
5-Hyd.roxy-1(10),2,4(15),11(13)- Sq-01966
guaiatetraen-12,6-olide

r
0
C 1sH:zo03 M 248.321
(1P,6rz.,JOJI)-form ClsH 160 3 M 244.290
10-Hydroxycichopumilide
Constit. of Cichorium pumilum. Cryst. Mp 137°. (5«,6«)-form
9-Desacetoxyanhydroathamontanolide
11P,J3-Dihydro: 10P-Hydroxy-4-guaien-12,6rz.-olide Constit. of Ursinia nana. Gum. [1X]n +4° (c, 0.1 in
C 1sH22 0 3 M 250.337 CHC1 3).
From C. pumilum. Cryst. (Et20). Mp 176°. [1X]i;' +38°
(c, 0.1 in CHC1 3). Bohlmann, F. et al, Phytochemistry, 1982, 21, 1309.
El-Masry, S. et al, Phytochemistry, 1984, 23, 183.
8-Hyd.roxy-1(10),2,4,11(13)-guaiatetraen- Sq-01967
10-Hyd.roxy-4(15),11(13)-guaiadien-12,6- Sq-01964 12,6-olide
olide

0 C 1sH 160 3 M 244.290

(6«,8«)-form [126829-63-8]
CuH:zo03 M 248.321
Ac: Pentziafulvenolide
(1 «.Srz.,6rz.,l0rz. )-form
C 17H 180 4 M 286.327
0-P-D-Glucopyranoside: Brachynereolide Constit. of Pentzia eenii. Yellow oil.
C11 H 34,08 M 410.463 (6ft,8«)-form [126829-71-8]
Constit. of Brachylaena nereifolia. Gum, cryst. as tetra-
Ac. Mp 83° (tetra-Ac). Ac: 6-EpipentziafulveiWiide
Constit. of P. eenii. Yellow oil.
llp,JJ-Dihydro, 0-P-D-glucopyranoside: 11P,J3-
Dihydrobrachynereolide Zdero, C. et al, Phytochemistry, 1990, 29, 189 (isol, pmr)
C11H 310 8 M 412.479
Constit. of B. nereifolia. Gum, cryst. (as tetra-Ac). Mp 1-Hyd.roxy-3,9,11(13)-guaiatrien-12,6- Sq-01968
185-186° (tetra-Ac). olide
(1P.S«,6rz.,l0rz.)-form (63543-05-5] Trijloculoside
Constit. of Vernonia spp. Oil.
Bohlmann, F. et al, Phytochemistry, 1977, 16, 778.
Zdero, C. et al, Phytochemistry, 1987, 26, 2597.

11-Hyd.roxy-1(10),3-guaiadien-12,6-olide Sq-01965

0
C1sH 180 3 M 246.305
(lrz.,6rz.)-form [129215-18-5]
Constit. of Kaunia lasiophthalma. Cryst. Mp 152-153°.
fl 10 0 4>-Jsomer: [129196-85-6]. 1rz.-Hydroxy-3,10(14),11(13)-
guaiatrien-12 ,6rz.-olide
0
ClsH 180 3 M 246.305
C 1sH:zo03 M 248.321 Constit. of K. lasiophthalma. Gum.
(5«,6rz.,ll /I)-form De Gutierrez, A.N. eta/, Phytochemistry, 1990, 29, 1219 (iso/, pmr,
Angeloy/: [33439-65-5]. Prutenin cmr)
C:zoH11;04 M 330.423

502
2-Hydroxy-3,10(14),11(13)-... - 3-Hydroxy-4(15),10(14),11(13)-... Sq-01969 - Sq-01970

2-Hydroxy-3,10(14),11(13)-guaiatrien- Sq-01969 Constit. of A. acerifo/ia. Amorph. powder. [IX]~ +59.7°

12,6-olide (c, 0.50 in MeOH).
0-[p-D-Glucopyranosyl(l-+3)-P-D-glucopyranoside]: [94474-
62-1]. Macrocliniside B
C 27H 380 13 M 570.589
Constit. of Macroclinidium trilobum. Amorph. powder.
[IX]~ -18.3° (c, 1.15 in H 20).
3-0-[p-D-Glucopyranosyl-(l-+4)-P-D-glycopyranosyl-(l-+3)-
P-D-glucopyranoside]: [100187-63-1]. Macrocliniside I
C 33 H 480 18 M 732.731
0 Constit. of M. trilobum. Amorph. powder. [IX]~ -13.0°
C15H1803 M 246.305 (c, 1.35 in H 20).
(2rx.,6rx.)-form 3-0-(6-0-p-Hydroxyphenylacetyl-P-D-glucopyranoside ):
Me ether: [126705-53-1]. 21X-Methoxy-3,10(14),11(13)- [100202-28-6]. Crepiside A
guaiatrien-12,6a.-olide C29H 340 10 M 542.582
CI,H2003 M 260.332 Constit. of Crepis japonica. Amorph. powder. [IX]~
Constit. of Peyrousea umbellata. Gum. + 12.3° (c, 0.65 in Py).
(2P,6rx.)-form [76937-87-6] 3-0-(4-0-p-Hydroxyphenylacetyl-P-D-glucopyranoside):
Constit. of P. umbellata. Gum. [100202-26-4]. Crepiside B
C29H 340 10 M 542.582
111X,l3-Dihydro: 2P-Hydroxy-3,10(14)-guaiadien-
Constit. of C. japonica. Amorph. powder. [IX]~ -6.7° (c,
12,61X-olide. 2P-Hydroxy-8-desoxy-ll«,13-dihydrorupicolin B
0.52 in MeOH).
C15H2003 M 248.321
lsol. from Artemisia sieversiana. Oil. 111X,l3-Dihydro: llr~-,13-Dihydroza/uzanin C
C1 5H 200 3 M 248.321
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 1009.
Constit. of A. fragrans. Gum. [1X]ii -17° (c, 0.25 in
Zdero, C. eta/, Phytochemistry, 1989, 28, 3101.
CHC13).
111X,l3-Dihydro, Ac: 3P-Acetoxy-4(15),10(14)-guaiadien-
3-Hydroxy-4(15),10(14),11(13)-guaiatrien- Sq-01970 12,61X-olide
12,6-olide CI7Hn04 M 290.358
Constit. of Vladimiria souliei.
11P,J3-Dihydro: 31X-Hydroxy-4(15), 10(14)-guaiadien-12,6-
o/ide. 11P,I3-Dihydroza/uzanin C
C15H 200 3 M 248.321
Constit. of B. tranS!!aalensis. Gum. [1X]ii + 11° (c, 0.23 in
CHC1 3)(as acetate).
11P,l3-Dihydro, P-D-Glucopyranoside:
C21 H 300 8 M 410.463
C15H1803 M 246.305 Constit. of B. nereifolia. Cryst. Mp 96°.
(lrx.,3p,5rx.,6rx.)-form [16838-87-2] Za/uzanin C 11P,l3-Dihydro, 3-(3-methylbutanoyl): Diaspanolide A
Constit. of Zaluzania spp. Shows activity against P-388 C20H 280 4 M 332.439
leukaemia. Cryst. (Me 2COfdiisopropy1 ether). Mp 103- Constit. of D. uniflora. Oil. [1X]i; + 373.8° (c, 0.011 in
1040. [1X] 0 + oo (CHC1 3). CHC1 3). .

Ac: [16838-85-0]. Zaluzanin D (Jrx.,3rx.,5rx.,6rx.)-form [67667-64-5] 3-Epizaluzanin C. Isozaluzanin

C 17H 20 0 4 M 288.343 c
Constit. of Z. spp. Cryst. (Et0Acjdiisopropy1 ether). Constit. of Vernonia anisochaetoides and Saussurea
Mp 103-104°. [1X] 0 + 0° (CHC1 3). lappa. Cryst. (also descr. as oil). Mp 143°. [1X]ii -55.6°
3-Methyl-2-butenoyl: [57576-43-9]. Vernojlexin (c, 0.24 in CHC1 3).
C 20H 1,.04 M 328.407 Romo de Vivar, A. et a/, Tetrahedron, 1967, 23, 3903 (isol, struct)
Constit. of the roots of Vernonia jlexuosa. Bitter taste. Dominguez, X.A. eta/, Planta Med., 1975, 28, 89 (isol, pharmacal)
Cryst. (EtOH). Mp 73-75°. Bohlmann, F. eta/, Phytochemistry, 1978, 17, 475; 1979, 18, 1343;
1982, 21, 647, 2120 (iso/, derivs)
Angeloyl: Ando, M. eta/, Chern. Lett., 1982, 501 (synth)
C 20H 240 4 M 328.407 Ka1si, P.S. eta/, Phytochemistry, 1983, 22, 1993 (isol)
Constit. of Zinnia multiflora. Oil. Miyase, T. eta/, Chern. Pharm. Bull., 1984, 32, 3043, 3912; 1985,
3-(3-Methylbutanoyl): Dillspanolide B 33, 4445, 4451 (isol, derivs)
Nishimura, K. eta/, Phytochemistry, 1986, 25, 2375 (derivs)
C 20H 260 4 M 330.423
Adegawa, S. eta/, Chern. Pharm. Bull., 1987, 35, 1479
Constit. of Diaspananthus uniflora. Oil. [1X]i; +235.3° (c, (Diaspanolides)
0.034 in CHC1 3). Zdero, C. eta/, Phytochemistry, 1987, 26, 2597 (deriv)
0-P-D-Glucopyranoside: [57576-33-7]. Vernoflexuoside.
Glucozaluzanin C
C 21 H 180 8 M 408.447
Constit. of the roots of V. jlexuosa, Ainsliaea acerifolia,
Macroclinidium trilobum and Brachylaena spp. Cryst.
(MeOH aq. or H 20) with bitter taste. Mp 104-105°. [IX]~
-18.4° (c, 0.93 in MeOH).
3-0-(2-0-Ca.lfeoylglucoside): [93236-48-7]. Ainsliaside A
C 30H 340 11 M 570.592

503
4-Hydroxy-2,10(14),11(13)-... - 8-Hydroxy-3,10(14),11(13)-... Sq-01971 - Sq-01975

4-Hydroxy-2,10(14),11(13)-guaiatrien- Sq-01971 C17H 200 4 M 288.343

12,6-olide Isol. from Matricaria zuurbergensis. Cryst. (Et20jpet.
ether). Mp 176°. [a]i,l +92° (c, 1.17 in CHC1 3).
(5rz,6rz,8/f)-form [84582-26-3] Bp.Hydroxy-2-
desoxodehydroleucodin. Dessarraciny/bahia III
Constit. of Stevia myriadenia and Bahia oppositifo/ia.
Gum or cryst. [a]i;l -32° (c, 0.27 in CHC1 3).
0-(4-Hydroxy-2-hydroxymethyi-2E-butenoyl):
Eupalulkonenin A
C20H 240 6 M 360.406
0 Constit. of S. myriadenia and Eupatorium chinense var.
Ct5H1803 M 246.305 hakonense. Gum. [a]~ -95° (c, 0.2 in MeOH).
(4P,6rz)-form [126705-54-2] 0-(2,5-Dihydro-5-hydroxy-3-furancarboxy/ate): [100045-37-
Constit. of Peyrousea umbellata. Gum. 2].
Zdero, C. et al, Phytochemistry, 1989, 28, 3101 (isol, pmr) C20 H:n06 M 358.390
Constit. of S. mercedensis. Oil. Mixture of 5' -epimers.
0-(2-Hydroxymethyi-2Z-butenoyl): [89900-51-6]. Bahia Ill
7-Hydroxy-4(15),10(14),11(13)-guaiatrien- Sq-01972
C20 H 240 5 M 344.407
12,6-olide Constit. of B. oppositifolia. Cryst. (MeOAcjC 6H 6).
11P,J3-Dihydro: 8-Hydroxy-1(10),3-guaiadien-12,6-olide. ap-
Hydroxy-11 p,J3-dihydrokauniolide
C15H 200 3 M 248.321
Constit. of Kyrsteniopsis dibolii. Oil.
(5~,6rz,8/f)-form
11a,l3-Dihydro, 0-(4-hydroxy-2-hydroxymethyi-2Z-
butenoyl): [62748-23-6]. Petiolaride
0 C20H 260 6 M 362.422
C15H 180 3 M 246.305 Constit. of Ageratina petiolaris. Oil. [a]i;l - 52.SO (c, 2.9
(lrz,5rz,6rz,7rz(OH))-form in CHC1 3).
7rz-Hydroxy-3-deoxyza/uzanin C Bohlmann, F. et al, Chern. Ber., 1977, 110, 301 (Petiolaride)
lsol. from Podachaenium reminens. Cryst. Mp 132-133°. Bohlmann, F. et al, Phytochemistry, 1977, 16, 136; 1982, 21, 2021
(isol)
Fronczek, F.R. et al, J. Nat. Prod. (Lloydia), 1984, 47, 1036 (isol, Ito, K. et al, Phytochemistry, 1982, 21, 715 (Eupahakonenin A)
pmr) Nelson, P. et al, Phytochemistry, 1983, 22, 2755 (Bahias)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1986, 799 (derivs)
8-Hydroxy-1(10),2,4-guaiatrien-12,6-olide Sq-01973 Jakupovic, J. et al, Planta Med., 1988, 54, 533 (isol, pmr)

8-Hydroxy-3,10(14),11(13)-guaiatrien- Sq-01975
12,6-olide

C15H 180 3 M 246.305

(6rz,8rz,ll rzH)-form
Ac: Brz-Acetoxy-6-epitfliUUlnolide A
C 17H 200 3 M 272.343 C15H 180 3 M 246.305
Constit. of Tanacetum annuum. Cryst. (Et 20). Mp 137- (lrz,5rz,6rz,8/f)-form [21677-87-2] Ligustrin
1400. Constit. of Eupatorium ligustrinum and of Eriophyllum
Barrera, A.F. et al, Phytochemistry, 1990, 29, 3575 (isol, pmr, cmr) staechadifolium. Cryst. (Me2CO/Et20). Mp 135-137°.
[aln +56°.
8-Hydroxy-1(10),3,11(13)-guaiatrien-12,6- Sq-01974 8-(4-Hydroxy-2-hydroxymethy/-2E-butenoyl): [82430-68-0].
Eupalulkonenin B
olide C20H 240 6 M 360.406
Constit. of Stevia setifera and Eupatorium chinense var.
hakonense. Oil. [a]i;l +4.9° (c, 0.7 in CHCI 3), [a]~ + 22°
(c, 0.19 in MeOH).
(5cx,6cx,8cx}:form 0-(4-Hydroxy-2-methyl-2E-butenoyl): [100045-33-8].
C20H 240 5 M 344.407
Constit. of S. mercedensis. Oil.
8-0-(2,5-Dihydro-5-hydroxy-3-furancarboxy/ate): [100045-
34-9].
C15H180 3 M 246.305 C20H:n0 6 M 358.390
(5rz,6rz,8rz)-form Constit. of S. mercedensis. Oil. Mixt. of 5'-Epimers.
Ac: Zuurbergenin (lrz,5P,6rz,8/f)-form

504
8-Hydroxy-4(15),9,11(13)-guaiatrien-... - 4-Hydroxy-9-guaien-12,6-olide Sq-01976 - Sq-01979

Epiligustrin Isol. from Saussurea involucra/a and Centaurea

C 15H 180 3 M 246.305 canariensis. Needles (Et20jpet. ether). Mp 134-135°. [1X]i?
Constit. of Leucanthemopsis pulverulenta. Cryst. (EtzO). +15° (c, 0.17 in MeOH).
Mp 132°. [1X]n + 77.4° (c, 0.9 in CHC1 3). Not interrelated 11P,13-Dihydro,-O-P-D-glucopyranoside: [98571-07-4].
with Ligustrin. C21 H:14P 8 M 410.463
[100045-35-0, 100045-38-3) Isol. from S. involucrata. Needles. Mp 219-221°.
Romo, J. et al, Tetrahedron, 1968, 24, 6087 (isol) (1 ft,5«.,6«.,8«. )-form
Bohlmann, F. et al, Phytochemistry, 1979, 18, 673; 1981, 20, 2239 8-(3-Methyl-2-butenoyl): [63543-08-8]. Vernudifloride
(isol, stereochem) C20H 2P 4 M 328.407
Ito, K. et al, Phytochemistry, 1982, 21, 715 (synth, pmr)
De Pascual Teresa, J. et al, Phytochemistry, 1984, 23, 1178
Constit. of Vernonia spp. Oil. [1X]~4 + 163° (c, 6.4 in
(Epiligustrin) CHC1 3).
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1986, 799 (derivs) Bohlmann, F. et al, Phytochemistry, 1977, 16, 778; 1980, 19, 2669;
1981, 20, 2773.
Gonzalez, A.G. et al, Tetrahedron Lett., 1982, 23, 895.
8-Hydroxy-4(15),9,11(13)-guaiatrien-12,6- Sq-01976 Li, Y. et al, Phytochemistry, 1989, 28, 3395.
olide
9-Hydroxy-4(15),10(14),11(13)-guaiatrien- Sq-01978
12,6-olide

C 15H 180 3 M 246.305

(1«.,5«.,6«.,8«. )-form 0
8«.-Hydroxyeremanthin C 15H 180 3 M 246.305
8-(3-M ethylbutanoyl): (1 «.,5«.,6«.,9«. )-form
C20H 260 4 M 330.423 9-Hydroxycyclocostuno/ide
Constit. of Centratherum punctatum. Gum. [1X]~4 +66.7°
9-Angeloyl: [73021-33-7].
(c, 0.36 in CHC1 3).
C20H 2P 4 M 328.407
(1 «.,5«.,6«.,8/f)-form Constit. of Zinnia acerosa. Oil.
lliX,l3-Dihydro: [74323-36-7]. 8P-Hydroxy-4(l5),9- 9-(3-Methyl-2-butenoyl): [73021-32-6].
guaiadien-l2,61X-olide. 8P-Hydroxydihydroeremanthin C20H 240 4 M 328.407
Constit. of lnula aschersonia. Cryst. (Et20jpet. ether). Constit. of Z. acerosa. Oil.
Mp 135-137°. [1X]i;4 -47.8° (c, l in CHC1 3).
3-0-P-D-Giucopyranoside: lxerisoside D
Papano, G.Y. et al, Phytochemistry, 1980, 19, 152. C21 H 280 8 M 408.447
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2669.
Constit. of lxeris repens. Amorph. powder. [1X]i;1 -21.0°
(c, 0.6 in MeOH).
8-Hydroxy-4(15),11(13),10(14)-guaiatrien- Sq-01977 (1 «.,5«.,6«.,9/f)-form
12,6-olide 0-P-D-Glucopyranoside: [109605-93-8]. Diaspanoside B
CuH 280 8 M 408.447
Isol. from Diaspananthus uniflora. Amorph. powder. [1X]i?
-55.0° (c, 0.3 in MeOH).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1343 (isol)
Adegawa, S. et al, Chern. Pharm. Bull., 1987, 35, 1479
(l cx,5cx,6cx,8cx )-form (Diaspanoside B)
Warashina, T. et al, Phytochemistry, 1990, 29, 3217 (lxerisoside)
0
4-Hydroxy-9-guaien-12,6-olide Sq-01979
C,sH,803 M 246.305 Artausin
(1 «.,5«.,6«.,8«. )-form
8-Hydroxydehydrocostuslactone
Cryst. (EtOAcjpet. ether). Mp 106-108°. [1X]n +61°
(CHCI 3).
8-(2-Hydroxymethy/propenoyl): [81421-79-6]. Subexpinnatin
C19H120 5 M 330.380
Constit. of Centaurea canariensis. Oil. [1Xln +62° (c, 3 in
CHC1 3).
8-(3-Methylbutanoyl):
C 15H 220 3 M 250.337
C10H 260 4 M 330.423
Constit. of Artemisia austriaca. Cryst. (EtOH). Mp 201-
Constit. of Centratherum punctatum. Gum. 2040.
11 p,J 3-Dihydro: [81421-77 -4]. 81X- Hydroxy-4(15), IO(l4)-
Adekenov, S.M. et al, Khim. Prir. Sqedin., 1987, 23, 148; Chern.
guaiadien-l2,61X-olide. 8«.-Hydroxy-11 ,13- Nat. Compd. (Engl. Trans/.), 127.
dihydrodehydrocostuslactone
C 15H 200 8 M 328.318

505
8-Hydroxy-2-oxo-3,11(13)-guaiadien-... - 8-Hydroxy-2-oxo-1(10),3,7(11)-... Sq-01980 - Sq-01984

8-Hydroxy-2-oxo-3,11(13)-guaiadien-12,6- Sq-01980 Constit. of Crepidiastrum keiskeanum. Amorph. powder.

olide [iX]:.J -34.5° (c, 0.58 in MeOH).
3,4P-Dihydro: [53023-32-8]. 15-Hydroxy-2-oxo-1(10)-guaien-
12 ,6-olide. Dihydropicridin
CtsH2004 M 264.321
Constit. of Picridium crystallinum. Cryst. Mp 175-177°.
[1X]n -26° (c, 4 in CHC1 3).
3,4P-Dihydro, 11,13-didehydro: [30436-69-2]. 15-Hydroxy-2-
oxo-1 (1 0),11 (13)-guaiadien-12 ,6-olide. Picridin
CtsH 180 4 M 262.305
(lf.,5f,,6~,a~,10f/)-form
Constit. of P. crystallinum. Oil.
Ac: [90746-97-7]. Montanone Barrera, J.B. eta/, J. Chern. Soc. C, 1966, 1298 (Jacquinelin)
Gonzalez, A.G. et a!, Phytochemistry, 1974, 13, 611 (Picridin,
C17H20 0 5 M 304.342 Dihydropicridin)
Constit. of Artemisia montana. Gum. St. Pyrek, J. eta/, Pol. J. Chern. (Rocz. Chern.), 1977, 51, 2165
Nayaki, M. et a/, Phytochemistry, 1984, 23, 462 (iso{) (is of)
Adegawa, S. eta!, Chern. Pharm. Bull., 1985, 33, 4906
(Crepidiasides)
11-Hydroxy-2-oxo-1 (1 0),3-gu'aiadien-12,6- Sq-01981
olide
5-Hydroxy-2-oxo-1(10),3,11(13)- Sq-01983
guaiatrien-12,6-olide

(5cr.,6cr.)-form

(5p,6p,llf/)-form
0
0-(3-Methyl-2-butenoyl): [112766-69-5]. Ferulide
C20H 240 5 M 344.407 CtsHt604 M 260.289
Constit. of Ferula penninervis. Cryst. Mp 135-137°. (5~,6~)-form [126705-51-9]

Abdullaev, N.D. eta/, Khim. Prir. Soedin., 1987, 23, 200 (isol) Constit. of Peyrousea umbellata. Cryst. Mp 173°. [1X]i;'
Tashkhodzhaev, B. et a/, Khim. Prir. Soedin., '1988, 24, 55; Chern. -8° (c, 2.95 in CHC1 3).
Nat. Compd. (Engl. Trans/.), 46 (crys(sttuct) 11P,13-Dihydro: [74636-03-6]. 51X-Hydroxy-2-oxo-1(10),3-
guaiadien-12,61X-olide. Parishin C
15-Hydroxy-2-oxo-1(10),3-guaiadien-12,6- Sq-01982 CtsHts04 M 262.305
olide Isol. from Artemisia tridentata ssp. tridentata and A.
leucodes. Mp 247-255° (241-243°).
(5~,6/f)-form

111X,13-Dihydro: 51X-Hydroxy-2-oxo-l(l 0),3-guaiadien-12,6P-

olide. 5-Hydroxyachillin
CtsHt804 M 262.305
-- 13 lsol. from Ursinia saxatilis. Gum. [1X]i;' -60° (c, 0.4 in
CHC1 3).
0 Kasymov, S.Z. eta/, Khim. Prir. Soedin., 1979, 15, 658; Chern.
C15H180 4 M 262.305 Nat. Compd. (Engl. Trans/.), 577 (synth, pmr)
Ohno, N. eta/, Phytochemistry, 1980, 19, 103 (Parishin C)
(5~,6~,11~)-form [7726-34-3] Jacquinelin Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1357 (isol)
Constit. of Sonchus jacquini, S. pinnatus, S. radicatus Zdero, C. eta/, Phytochemistry, 1989, 28, 3101 (isol, pmr)
and Lactuca serriola. Cryst. (EtOAcjC 6H 6). Mp 76°, Mp
165-167° (double Mp). [1X]n +27.5° (c, 2.03 in MeOH). 8-Hydroxy-2-oxo-1(10),3,7(11)-guaiatrien- Sq-01984
Incorr. given as Jacquilenin in CA.
12,6-olide
Ac: Cryst. (EtOAcjpet. ether). Mp 155-156°. [1X]n +28.SO
(c, 2.25 in MeOH).
15-0-P-D-Glucopyranoside: [101921-35-1]. Crepidiaside B
C11H 280 9 M 424.447
Constit. of Crepidiastrum keiskeanum. Needles (MeOH).
Mp 237-240°. [1X]:.J -62.SO (c, 0.32 in MeOH).
11 ,13-Didehydro: 15-Hydroxy-2-oxo-1(10),3,11(13)-
guaiatrien-12,6-olide. 8-Deoxylactucin ,
C 15H 200 4 M 264.321
Constit. of Lactuca serriola. Cryst. (CH 2Cl 2Jhexane). CtsHt604 M 260.289
Mp 143-148°. (5rx.,6rx.,Bf/)-form [83991-72-4] Desangelylsluliridin
11 ,13-Didehydro, 15-0-P-D-glucopyranoside: [101921-36-2]. Constit. of Guillonea scabra. Cryst. (MeOH). Mp 226-
Crepidiaside A 2290. [1X]ii +41° (c, 0.86 in CHC1 3).
C11H 300 9 M 426.463 Angeloyl: [77369-07-4]. Shairidin
C20 H 220 5 M 342.391

506
8-Hydroxy-2-oxo-1(10),3,11(13)-... - Involucratin Sq-01985 - Sq-01987

Constit. of G. scabra. Cryst. (Etp). Mp 145-146°. [ex)~ C10H:w06 M 360.406

+21° (c, 0.72 in CHC1 3). Constit. of A. schischkinii. Amorph.
Pinar, M. eta/, Phytochemistry, 1982, 21, 1802. [35879-92·6]
Herz, W. et al, J. Am. Chern. Soc., 1961, 83, 1139 (isol)
8-Hydroxy-2-oxo-1(10),3,11(13)- Sq-01985 White, E.H. eta/, Tetrahedron, 1963, 137 (isol)
Rybalko, K.S., Zh. Obshch. Khim., 1963, 33, 2734 (Leucomisin)
guaiatn"en-12,6-olide White, E.H. eta/, Tetrahedron Lett., 1969, 25, 2099 (struct)
Serkerov, S.V. et a/, Khim. Prir. Soedin., 1970, 6, 425; 1982, 18,
452 (Badkhyzin)
Konovalova, O.A. eta/, Khim. Prir. Soedin., 1971, 741 (isol, struct,
Grossmisin)
Bachelor, F.W. et a/, Can. J. Chern., 1972, 50, 333 (struct)
Gonzalez, A.G. eta/, An. Quim., 1976, 72, 695 (isol)
Zakharov, P.l. eta/, Khim. Prir. Soedin., 1977, 13, 344 (ms)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1595 (isol)
Yong-Long, eta/, J. Nat. Prod. (Lioydia), 1981, 44, 722 (isol)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 162 (2-
C 15H 160 4 M 260.289 Methyl-2,3-epoxybutyroy/oxydehydroleucodin)
(5rz,6rz,8rz)-form Collado, I.G. eta/, J. Chern. Soc., Perkin Trans. I, 1987, 1641
Ac: [69904-98-9]. 11,13-Dehydromatricarin (struct)
C 17H 180 5 M 302.326 Martinez, V. eta/, J. Nat. Prod. (Lioydia), 1988, 51, 211 (pmr,
Constit. of Athanasia and Pentzia spp. Cryst. (Etpjpet. cmr)
Ulubelen, A. eta/, Planta Med., 1988, 54, 473 (8P-Hydroxyachillin)
ether). Mp 146°. [ex]~ + 120.8° (c, I in CHC1 3). Campos, V. eta/, Acta Crystallogr., Sect. C, 1989, 45, 678 (cryst
11P,13-Dihydro: [10180-88-8]. 8-Hydroxy-2-oxo-1(10),3- struct)
guaiadien-12 ,6-o/ide. Austricin. Desacetylmatricarin. Turdybekov, K.M. et a/, Khim. Prir. Soedin., 1989, 788; Chern.
Austrisin Nat. Compd. (Engl. Trans/.), 1989, 25, 699 (cryst struct)
C 15H 180 4 M 262.305
lsol. from Artemisia tilesii, A. austriaca, A. leucodes, A. 9-Hydroxy-3-oxo-4(15),1 0(14),11(13)- Sq-01986
juncea and Achillea lanulosa. Cryst. + IH 20 guaiatrien-12,6-olide
(C6H 6/Me 2CO). Mp 123-125°, Mp 143-146° (double
Mp, hydrate).
llp,JJ-Dihydro, Ac: [5989-43-5]. Matricarin. Artilesin A
C 17H 100 5 M 304.342 (1 cx,5cx,6cx,9cx )-form
Constit. of Artemisia spp. Also from Matricaria
chamomilla and Achillea lanulosa. Cryst. (C6H 6 jpet.
ether). Mp 193-195°. [ex]~ +23.SO (c, 0.65 in CHC1 3).
llex,13-Dihydro: [36031-36-4). Grossmisin. 8ex- 0
Hydroxyachillin
Constit. of Achillea lanulosa and Artemisia caucasica. C 15H 160 4 M 260.289
Cryst. Mp 161-162°. [ex]i;1 + 110° (c, 1.6 in MeOH). (lrz,5rz,6rz,9rz)-form [84886-42-0]
Identity of Grossmisin and 8ex-hydroxyachillin not 9-Hydroxydehydrozaluzanin C
confirmed. Grossmisin reported as having a double Mp., Constit. of Dicoma anomala. Gum.
120-135° and 156-158°. (I rz,5rz,6rz,9f/)-form [71305-85-6]
llex,13-Dihydro, Ac: [35866-60-5]. Constit. of Vernonia scorpioides. Oil.
C 17H 100 5 M 304.342 Bohlmann, F. eta/, Phytochemistry, 1979, 18, 289; 1982, 21, 2029.
Constit. of Achillea lanulosa. Cryst. Mp 193-194°. [ex] 0
+ 116° (c, 1.6 in CHC1 3). Involucratin Sq-01987
llex,13-Dihydro, angeloyl: [6695-00-7]. Badkhyzin
C10H:w0s M 344.407
Constit. of Ferula spp. Cryst. Mp 139-140°. [ex) 0 +68°.
11 ex,13-Dihydro, 1p,Jop-epoxide: 1,10-Epoxy-8-hydroxy-2-
oxo-3-guaien-12 ,6-olide. I p,J OP-Epoxy-Brz-hydroxyachi/Jin
C15H 180 4 M 262.305
Constit. of Achillea lanata and A. frigida. Cryst.
(EtOAcjpet. ether). Mp 273° dec.
(5rz,6rz,8f/)-form
0-(2-Methyl-2,3-epoxybutanoyl): BP-(2-Methyl-2,3- C10H 27N04 M 345.438
epoxybutyroyloxy)dehydroleucodin Constit. of Saussurea involucrata. Needles. Mp > 300°.
C10H 220 6 M 358.390 Li, Y. et al, Phytochemistry, 1989, 28, 3395 (isol, pmr, cmr)
Constit. of Trichogonia santosii. Oil. [ex]~ -96° (c, 0.69
in CHC1 3).
11rx.,13-Dihydro: 8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-
o/ide. BP-HydroxyachiUin
C 15H 180 4 M 262.305
Constit. of A. schischkinii. Cryst. Mp 168°. [ex]i;1 + 154°
(c, 1.2 in MeOH).
11rx.,13-Dihydro, 31;,41;-epoxid.e, 0-(3-methyl-2-butenoyl):
Schischkinin A

507
Lactucin 8-0-hypoglabrate- 2-0xo-1(10),3,11(13)-guaiatrien-... Sq-01988 - Sq-01992

Lactucin 8-0-hypoglabrate Sq-01988 13-0xo-1(10),4(15),5,7(11),8- Sq-01991

(81249-28-7] guaiapentaen-12,6-olide
Lettucenin A

~m
[97915-46-3]

-0
I
C15H 110 3 M 240.258
Phytoalexin from Lactuca sativa var. capitata. Shows
antifungal props. Unstable yellow cryst. Mp 175-176°.
0
Takasugi, M. et a/, J. Chern. Soc., Chern. Commun., 1985, 621.
C30H310 7 M 504.579
Isol. from Hypochoeris glabra. Cryst. (EtpjC6H 6). Mp
181°. [ex]i: + 118° (c, 1.35 in CHC1 3). 2-0xo-1(10),3,11(13)-guaiatrien-12,6-olide Sq-01992
11ex,13-Dihydro: [81241-44-3]. Brx.-Hypoglabroyloxyjaquinelin [36150-07 -9]
C30H340 7 M 506.594
Isol. from H. glabra. Cryst.(Et20/C6H6). Mp 190°.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2371.

Lappaphen a Sq-01989
[110325-70-7]
0
CISH1603 M 244.290
(5«.,6«.)-form
Dehydroleucodin. Lidbeckialactone
CISH1603 M 244.290
\ Constit. of Lidbe.ckia pectinata, Pentzia elegans and A.
OHO tridentata. Cryst. (Et20jpet. ether). Mp 131°. [1X] 0 +77°.
0 111X,l3-Dihydro: [5956-04-7]. 2-0xo-1(10),3-guaiadien-Ii,61X-
C27 H 260 4S1 M 478.632 olide. Achillin
Constit. of Arctium lappa. Yellow needles (EtOAcjhexane). CISH1803 M 246.305
Mp 19l.SO. [ex]~ +96° (c, 0.67 in CHC1 3). Constit. of Achillea spp. and Artemisia spp. Cryst.
11-Epimer: [110415-32-2]. Lappaphen b (C 6H6 /pet.ether). Mp 144-145°. [1X]i; + 160° (c, 1.2 in
C 27H 260 4S1 M 478.632 EtOH).
Constit. of A. lappa. Yellow needles (EtOAcjhexane). Jlfi,13-Dihydro: [17946-87-1]. Leucodin.
Mp 146°. [ex]~ - UO (c, 0.23 in CHC1 3). Desacetoxymatricarin. Leukodin. Leucomisin
Washino, T. eta/, Agric. Bioi. Chern., 1987, 51, 1475. CISH1803 M 246.305
Constit. of Artemisia spp., Achillea spp., and Stevia
2-0xo-1(10),3,5,7(11),8-guaiapentaen- Sq-01990 pilosa. Prisms (EtOH). Mp 204-206°. [1X] 0 + 58° (c, 1.3
in CHC1 3).
12,6-olide
3,6,9- Trimethylazuleno[4,5-blfuran-2,7-dione, 9CI. 111X,l3-Dihydro, 1p,JOfi-epoxide: 1p, lOP-Epoxy-2-oxo- 3-
Malaphyllidin guaien-12,6ex-olide. 1p,1 OP-EpoxyachiUin
CISH1804 M 262.305
[70476-06-1] Constit. of Artemisia lanata and A. assoana. Cryst. Mp
236-238°. [1X] 0 + 102° (c, 0.18 in CHC13).
2~-Aicohol: 2~-Hydroxy-1(10),3,11(13)-guaiatrien-12,61X­
olide. 2-Hydroxy-8-deacetoxyzuurbergenin
CISH1803 M 246.305
Constit. of Ursinia nana. Gum.
3-Chloro: 3-Chloro-2-oxo-1(10),3,11(1 3)-guaiatrien-12,6-
o/ide. 3-Chlorodehydroleucodin
0
C15H 15Cl03 M 278.734
C 15H 110 3 M 240.258 Constit. of Kaunia lasiophthalma. Cryst. Mp 162-5-
Constit. of Ferula malacophy/la. Cryst. Mp 256° dec. 164.SO.
Bagirov, V.Yu. et a/, Khim. Prir. Soedin., 1978, 810. 3-Hydroxy: 3-Hydroxy-2-oxo-1(10),3,11(1 3)-guaiatrien-12,6-
o/ide. 3-Hydroxydehydroleucodin
CISH1604 M 260.289
Constit. of K. lasiophthalma. Gum.
1fi,JOP-Epoxide: 1fi,IOP-Epoxy-2-oxo-3,11(13)-guaiadien-
12,6ex-olide. 1p,1 OP-Epoxydihydroleucodin

508
2-0xo-3,10(14),11(13)-guaiatrien-... - 3-0xo-10(14)-guaien-12,6-olide Sq-01993 - Sq-01997

ClsHI 60 4 M 260.289 Constit. of Cichorium intybus. Cryst. (hexane). Mp 145-

lsol. from Artemisia doug/asiana. Cryst. Mp 126-127°.
(5p,6fJ)-form
/sodehydrolellcodin
Constit. of Montanoa imbricata. Oil.
White, E.H.S. eta/, Tetrahedron, 1969, 25, 2099 (synth)
Marx, J.N. et a/, Tetrahedron, 1969, 25, 2117 (isol)
Shafizadeh, F. et a/, J. Org. Chern., 19.72, 37~ 3168 (isol)
Bohlmann, F. eta/, Tetrahedron Lett., 1972, 621 (isol)
Gonzalez, A.G. eta/, An. Quim., 1976, 72C, 695 (isol) 3-0xo-1-guaien-12,6-olide
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1309 (2-Hydroxy-8-
1460.
Kariyone, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1955,
75, 39; CA, SO, 890 (struct)
Naito, S., Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1955, 75, 93,
325; CA, SO, 891, 1680 (struct, synth)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 460 (isol, struct)
Monde, K. eta/, Phytochemistry, 1990, 29, 3449 (Cichoralexin)
Sq-01995
I

o=a)
deacetoxyzuurbergenin)
Seaman, F.C. eta/, Phytochemistry, 1986, 25, 2663
(/sodehydroleucodin)
Martinez, V.M. eta/, J. Nat. Prod. (Lloydia), 1988, Sl, 221 (pmr,
cmr)
Marco, J.A. et a/, J. Nat. Prod. (Lloydia), 1989, 52, 547 (cryst
struct, pmr, cmr)
:Ht>--
De Gutierrez, A.N. eta/, Phytochemistry, 1990, 29, 1219 (3- o
Ch/orodehydro/eucodin, 3-Hydroxydehydro/eucodin)
Rodriguez, G. eta/, Phytochemistry, 1990, 29, 3028
C15H 200 3 M 248.321
(Epoxydihydroleucodin) (4rx.,5rx.,6rx.,l0rx.,llrx.)-form [60733-13-3] Hypoclulerin
Constit. of Hypochaeris setosus. Cryst. Mp 110-112°.
[1X]n -64° (CHC1 3).
2-0xo-3,10(14),11(13)-guaiatrien-12,6- Sq-01993
Gonzalez, A.G. eta/, Phytochemistry, 1976, IS, 991 (iso/, struct)
olide Gonzalez, A.G. eta/, Cryst. Struct. Commun., 1977, 373 (cryst
struct)

3-0xo-9-guaien-12,6-olide Sq-01996

0
C 15H 1,03 M 244.290
(lrx.,5rx.,6rx.)-form
2-0xodesoxyligllstrin 0
Constit. of Stevia yaconensis. Cryst. Mp 185°. [1X]~4 CISH2003 M 248.321
+ 250° (c, 0.62 in CHC13). (lrx.,4rx.,5rx.,6rx.,llrx.)-form [63599-46-2] Eregoya;.idin
10rx,J4-Dihydro: [4668-72-8]. 2-0xo-3,11(13)-guaiadien-12,6- Constit. of Eremanthus goyazensis. Cryst. Mp 186-188°.
o/ide. Arbiglovin 11 ,13-Didehydro: [63569-75-5]. 3-0xo-9,11(13)-guaiadien-
Constit. of Artemisia biglovii. Cryst. (Me2C0jhexane). 12,6-o/ide. Eregoyazin
Mp 201-203°. [1X]n + 199°. CISHI803 M 246.305
Herz, W. eta/, J. Org. Chern., 1965, 30, 4340 (Arbig/ovin) lsol. from E. goyazensis. Mp 178-181°.
Marx, J.N. eta/, Tetrahedron, 1972, 28, 3583 (Arbiglovin) (1~,4~,5rx.,6rx.)-form
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835 (2-
0xodesoxy/igustrin) 11,13-Didehydro: [85993-31-3]. Glabellin
Constit. of Artemisia glabella aerial parts.
2-0xo-3-guaien-12,6-olide Sq-01994 Vichnewski, W. eta/, J. Org. Chern., 1977, 42, 3910 (isol)
Herz, W. eta/, J. Org. Chern., 1980, 45, 2503 (cryst struct)
da Silva, A.J.R. eta/, Org. Magn. Reson., 1981, 16, 230 (cmr,
struct)
Adekenov, S.M. eta/, CA, 1983, 99, 3025s (Glabel/in)

04>
3-0xo-1 0(14)-guaien-12,6-olide Sq-01997

C15H 200 3 M 248.321

(lrx.,5rx.,6rx.,10rx.,llrx.)-form [82460-83-1] Carpesialactone
lsol. from roots of Hypochoeris o/igocepha/a and from
; ilt)--
seeds of Carpesium abrotanoides. Viscous liq. with bitter
0
taste. Bp5 200-202°. The identity of Bohlmann's sample
with an earlier sample of undetd. 10 and 11 stereochem. C15H 200 3 M 248.321
is not certain. (1 rx.,4rx.,5rx.,6rx.,ll rx. )-form [38142-65-3] Dihydroestafiatone
I> Powerful irritant. Constit. of Centaurea webbiana. Cryst. (hexane). Mp 82-
(lp,5rx.,6rx.,JOP,Jlrx.)-form 83.SO. [1X]i,O + 140° (c, 3.34 in CHC13).
Cichoralexin Gonzalez, A.G. eta/, An. Quim., 1972, 68, 333; CA, 77, 123813g.

509
3,7,8,10,11-Pentahydroxy-4-guaien-... - 2,8,10,11-Tetrahydroxy-3-guaien-... Sq-01998 - Sq-02003

3,7,8,1 0,11-Pentabydroxy-4-guaien-12,6- Sq-01998 Constit. of P. japonica. Tumour promotor (induces

olide ornithine decarboxylase activity). Cryst. Mp 225-226°.
[ocln -6.3° (c, 4.4 in CHC1 3).
I> Tumour promotor.
Asakawa, Y. et al, Planta Med., 1980, 39, 233.
Asakawa, Y. et al, Phytochemistry, 1981, 20, 257.

3,4,8,15-Tetrahydroxy-10(14),11(13)- Sq-02001
guaiadien-12,6-olide

C 15H 220 7 M 314.335

(1fJ,3rx.,6fJ,7fJ,8rx.,10rx.,11rx.)-form
3-Angeloyl, 8-(2-methylbutanoyl), 10-Ac: [50657-07-3].
Trilobolidet
C27H 380 10 M 522.591
Constit. of root of Laser trilobum. Cryst. (diisopropyl
ether). Mp 191-192°. [a]i,6 +73.3° (c, 0.18 in MeOH).
CtsH21,06 M 296.319
Holub, M. et al, Collect. Czech. Chern. Commun., 1968, 33, 2911; (1rx.,3fJ,4fJ,5rx.,6rx.,8rx.)-form
1973, 38, 1551 (isol, struct)
Holub, M. et al, Tetrahedron Lett., 1984, 25, 3755 (isol) 8-(3-Chloro-2-hydroxy-2-methylpropanoyl), 3-Ac: [66761-10-
Kutschabsky, L. et al, Z. Chern., 1984, 24, 24 (cryst struct) 2]. Linichlorin C
Christensen, S.B. et al, Tetrahedron Lett., 1985, 26, 107 (abs C21 H 27C10 9 M 458.892
config) Constit. of Centaurea linifolia. Cryst. (EtOAcjpet.
ether). Mp 160-162°. [ocln + 83° (c, 0.4 in CHC1 3).
Picrioside A Sq-01999 (1rx.,3fJ,4rx.,5rx.,6rx.,8rx. )-form
11 p,JJ-Dihydro: [88664-02-2]. 3,4,8,15- Tetrahydroxy- 10(14)-
guaien-12,6-olide. Saussureolide
C 15H 220 6 M 298.335
Constit. of Saussurea a./finis. Gum.
Gonzalez, A.G. et al, Can. J. Chern., 1978, 56, 491 (Linichlorin C)
Das, S. et al, Phytochemistry, 1983, 22, 1989 (Saussureolide)

1,5,8,9-Tetrahydroxy-3,10(14),11(13)- Sq-02002
guaiatrien-12,6-olide

C36H 420 13 M 682.720

Constit. of Picris hieracioides. Needles. Mp 222-223°.
11P,13-Dihydro: Picrioside B
C36H 440 13 M 684.736
Constit. of P. hieracioides. Needles. Mp 215-217°. [oc]~
+43.3° (c, 0.45 in CHC1 3 jMeOH).
Uchiyama, T. eta/, Phytochemistry, 1990, 29, 2947 (isol, pmr, cmr) CtsH 180, M 294.304
(1 rx.,5rx.,6rx.,8rx.,9fJ)-form
Porelladiolide Sq-02000 8-(2,3-Epoxy-2-methylbutanoyl), 9-Ac: [117274-10-9].
[79396-08-0] Skutchiolide A
C22 H 260 9 M 434.442
0 Constit. of Squamopappus skutchii. Gum.
Vargas, D. et al, Phytochemistry, 1988, 27, 1413.

2,8, 10,11-Tetrahydroxy-3-guaien-12,6- Sq-02003

olide

C 15H 160 4 M 260.289

Constit. of Parella japonica. Tumour promotor (induces
ornithine decarboxylase activity). Cryst. Mp 194-195°.
[ocln -64.SO (c, 1.8 in CHC1 3).
I> Tumour promotor.
C 15H 2z06 M 298.335
3a,4a-Epoxide:
C 15Ht60 5 M 276.288 (1 fJ,2fJ,5fJ,6fJ,8rx.,1 Ofl,l1 rx. )-form
2,8, 10, 11- Tetrahydroxy- 3-slovenolide

510
3,4,8,10-Tetrahydroxy-1-guaien-12,6-... - 3,11,13-Trihydroxy-4(15),10(14)-... Sq-02004 - Sq-02009

2-0-(2-Methy/butanoyl), 8-0-ange/oy/, 11-Ac: 1,4,1 0-Trihydroxy-2,11(13)-guaiadien- Sq-02006

C27 H 380 9 M 506.592 12,6-olide
Constit. of roots of Laser trilobum. Gum. [ex]~ -66.4°.
2-0-Ange/oy/, 8-0-(2-methy/butanoyl), 10,11-di-Ac: [41929-
11-7]. Archangelolide
C29H 41.010 M 548.629
Constit. of Laser trilobum and Laserpitium archangelica.
Cryst. (Et20). Mp 109-112°. [exJn -120.2° (MeOH).
8-(3-Methy/-2-butenoyl), 2,10,11-tri-Ac:
Cu;H340 10 M 506.549 0
Constit. of Thapsia villosa. Amorph. powder. [ex]~
C 15H 200 5 M 280.320
-108° (c, 0.29 in MeOH).
(11;,4/;,5«,6«,1 01;)-form [96627-14-4] Pyrethroidinin
8-(2-Methy/butanoyl), 2,10,11-tri-Ac:
Constit. of Pyrethrum pyrethroides. Cryst.
C20H 360 10 M 436.498 (EtOAcjhexane). Mp 170-172°. [ex]~ +850° (c, 0.8 in
Constit. of T. villosa. Amorph. [ex]~ -113° (c, 0.21 in
EtOH).
MeOH).
Abduazimov, B.Kh. eta/, Khim. Prir. Soedin., 1984, 20, 751.
8-(3-Methy/-2-butenoyl), 10,11-di-Ac:
C24H 320 9 M 464.511
Constit. of T. villosa. Amorph. powder. [exJn - 129° (c, 3,4,8-Trihydroxy-10(14),11(13)-guaiadien- Sq-02007
0.2 in MeOH). 12,6-olide
8-(2-Methy/butanoyl), 10,11-di-Ac:
C24H 340 9 M 466.527
Constit. ofT. villosa. Amorph. powder. [ex]~ -50° (c,
0.24 in MeOH).
Holub, M. eta/, Collect. Czech. Chern. Commun., 1973, 38, 731;
1978, 43, 2444 (iso/, struct)
Holub, M. eta/, Tetrahedron Lett., 1984, 25, 3755 (isol)
Smitalova, Z. eta/, Collect. Czech. Chern. Commun., 1986, 51, 0
1323 (isol)
Smitt, U.W. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 1479 (derivs) CtsH200s M 280.320
(1«,3/;,41;.5«,6«,8«)-form
3,4,8,10-Tetrahydroxy-1-guaien-12,6-olide Sq-02004 8-(2-Hydroxymethy/propenoyl): [79331-12-7]. Acrorepiolide
C 19H 240 7 M 364.394
OH Constit. of Acroptilon repens. Gum. [ex]~4 + 16° (c, I in

HO-~'
CHC1 3).
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 1152.
s-OH
HO~ I -H
H, - 3,9, 10-Trihydroxy-4, 11(13)-guaiadien- Sq-02008
12,6-olide
0
CuH22 0 6 M 298.335
(3«,4«.5«,6tX.,8tX.,JOp,lltX.)-form
8-Ac: [119403-32-6]. 8ex-Acetoxy-3ex,4ex,10P-trihydroxy-1-
HO-
guaien-12,6ex-olide
C17H2407 M 340.372
Constit. of Artemisia arborescens. Cryst. (EtOH). Mp
140-145°. 0
Grandolini, G. eta/, Phytochemistry, 1988, 27, 3670 (isol, pmr) C 15Hz00 5 M 280.320
(3«,6«,9«,10«)-form [128366-58-5]
1,3, 10-Trihydroxy-4,11(13)-guaiadien- Sq-02005 Constit. of Ajania achil/eoides. Amorph. [ex]~4 + 71 o ( c,
12,6-olide 0.38 in CHC1 3).
Zdero, C. eta/, Phytochemistry, 1990, 29, 1585 (isol, pmr)

3,11,13-Trihydroxy-4(15),10(14)- Sq-02009
guaiadien-12,6-olide

CtsH200s M 280.320
(11;,3/;,5«,101;)-form [96154-30-2] Sanclrillin
Constit. of Achillea santo/ina. Cryst. (Me2 CO). Mp 233°.
Mallabaev, A. eta/, Khim. Prir. Soedin., 1984, 20, 793.
C 15H 200 5 M 280.320
(1«,3«.5«,6«,11«)-form [94410-23-8] Sibthorpin

511
4,9,10-Trihydroxy-2,11(13)-... - 2,5,8-Trihydroxy-3,10(14),11(13)-... Sq-02010 - Sq-02013

Constit. of Cynara sibthorpiana. Oil (as di-Ac). [ex]~ 4-Hydroperoxide: 1«-Hydroxy-4«-peroxybishopsolicepolide

+14.1° (c, 0.17 in CHC1 3) (di-Ac). C17H 100 7 M 336.341
(1«,3/1,5«,6«,11«)-form [22738-70-1] Solstitialin. Solstitialin A From B. soliceps. Oil. [exln + 57° (c, 0.37 in CHCI 3).
Isol. from yellow star thistle Centaurea so/stitia/is. Cause (1«,4«,5«,6«,8/1)-form
of star thistle poisoning in horses. Cryst. Mp 206-207°. 11 p,13-Dihydro, 8-Ac: 8ex-Acetoxy-1,4-dihydroxy-1, I O(l4)-
t>Toxic. guaiadien-12,6ex-o/ide. Neoezoguaianin
13-Ac: C 17H 110 6 M 322.357
C17H110 6 M 322.357 lsol. from Artemisia montana. Cryst. Mp 180-181°.
Isol. from C. so/stitialis. (1 «,4/1,5«,6«,8/1)-form
4ft,15-Dihydro: [70894-20-1]. 3,11,13- Trihydroxy-10(14)- 8-(2-Methy/propanoyl): [93767-40-9]. Subcordatolide A
guaien-12 ,6-o/ide. CyllllTatriol C 19H 1,.06 M 348.395
C15H 110 5 M 282.336 Constit. of Calea subcordata. Gum.
Constit. of Cynara corduncu/us and C. scolymus. Cryst. 8-(2-Acetoxy-2-methy/-2E-butenoyl): [ 102907-28-8].
(EtOAc). Mp 178-179°. [ex]~ +56° (c, 0.6 in JtliiUiicolide A
CHCI 3/MeOH). C11H 160 8 M 418.443
3-Deoxy: 11,13-Dihydroxy-4(15),10(14)-guaiadien-12 ,6- Constit. of Calea jamaicensis. Gum.
o/ide. 3-Deoxysolstitia/in A [99305-1 0-9]
C 15H 100 4 M 264.321
Constit. of Centaurea imperia/is. Ober, A.G. et a/, Phytochemistry, 1984, 23, 1289; 1986, 25, 877
(Subcordatolide A, Jamaico/ide A)
Zarghami, N. eta/, Chern. Ind. (London), 1969, 1556 (Solstitialin Singh, P. et a/, Phytochemistry, 1985, 24, 2110 (isol)
acetate) Nagaki, M. eta/, Phytochemistry, 1989, 28, 2731 (Neoezoguaianin)
Thiessen, W.E. eta/, Acta Crystal/ogr., Sect. B, 1970, 26, 554
(cryst struct, Solstitialin)
Bernhard, H.O. eta/, Helv. Chim. Acta, 1979, 62, 1288 2,3,8-Trihydroxy- Sq-02012
(Cynara trio/) 4(15),1 0(14),11(13)guaiatrien-12,6-olide
Omar, A.A. eta/, Phytochemistry, 1984, 23, 2381 (Sibthorpin)
Rustaiyan, A. eta/, Planta Med., 1984, 50, 193 (Deoxyso/stitialin)

4,9,10-Trihydroxy-2,11(13)-guaiadien- Sq-02010
l2,CH»Iide

0
C15Ht80 5 M 278.304
(1«,2/l,3«,5«,6«,8«)-form
8-(2-Methy/propenoyl): [83217-88-3]. Repdiolide
C19H 110 6 M 346.379
0 Constit. of Centaurea repens. Oil. [exJii + 88.4° (c, 1.43 in
C15H100 5 M 280.320 CHCI 3).
4ex,15-Epoxide, 8-(2-methy/propenoyl): 4«,15-
(4«,6«,9«,10«)-form [128366-57-4]
Constit. of Ajania achilleoides. Amorph. [ex]~ -77° (c, Epoxyrepdiolide
0.26 in CHCI 3). C 19H110 7 M 362.379
Constit. of C. repens. Cryst. Mp 129-136°. [ex]~0 +94.9°
Zdero, C. et al, Phytochemistry, 1990, 29, 1585 (isol, pmr) (c, 0.215 in CHC1 3).
(1«,2~,3~,5«,6«,8«)-form
1,4,8-Trihydroxy-2,10(14),11(13)- Sq-02011 2,3,8- Trihydroxydehydrocostunolide
guaiatrien-12,6-olide 8-(2-M ethy/propenoyl):
C19H 110, M 346.379
Constit. of Acroptilon repens. Gum. [ex]~4 + 28° (c, 1 in
CHCI 3).
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 1152.
Stevens, K.L., Phytochemistry, 1982, 21, 1093.

2,5,8-Trihydroxy-3,10(14),11(13)- Sq-02013
0 guaiatrien-12,6-olide
C1sH180 5 M 278.304
Bishopsolicepolide is unknown.
(1«,4«,5«,6«,8«)-form
8-Ac: 1«,4«-Dihydroxybishopsolicepolide
C 17H 100 6 M 320.341
From Bishopanthus soliceps. Oil. [exln +44° (c, 0.14 in
CHCI 3).
0
1-Hydroperoxide, 8-Ac: 1«-Peroxy-4«-
hydroxybishopsolicepolide C 15H 180 5 M 278.304
C17H 100 7 M 336.341 (1«,2fJ,5«,6«,8f/)-form
Constit. of B. so/iceps. Oil.

512
3,8,9-Trihydroxy-4(15),10(14),11(13) ... - 8,10,11-Trihydroxy-3-guaien-12,6-...
8-Angeloyl: 8-Angeloyloxy-5-hydroxypreeupatundin
C20H 240 6 M 360.406
Constit. of Eupatorium rotundifolium. Oil.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 1233.
3,8,9-Trihydroxy-4(15),10(14),11(13)-
guaiatrien-12,6-olide
0 b
C 15H 180 5 M 278.304
(lrx..3P.Srx.,6rx.,Bp,9f/)-form
3-Ac: [96382-98-8]. 9P-Hydroxykandllvanolide
C 17H 200 6 M 320.341
From Centaurea kandavanensis. Cryst. Mp 193-194°.
[IX]~ + 8° (c, 0.36 in CHC1 3).
Rustaiyan, A. et al, Planta Med., 1984, SO, 363.
4,8,9-Trihydroxy-1(1 0),2,11(13)-
guaiatrien-12,6-olide
C 15H 180 5 M 278.304
(4rx..Srx.,6rx.,Brx.,9rx. )-form
8,9-Di-Ac: [72635-12-2].
C 19H 210 7 M 362.379
Constit. of Athanasia montana. Cryst. (Et20/pet. ether).
Mp 159°. [1X]~4 + 233° (c, 0.5 in CHC1 3).
8-(Methylpropanoyl), 9-Ac: [72635-05-3].
C11H 260 7 M 390.432
Constit. of A. montana. Oil.
(4P.Srx.,6rx.,Brx.,9rx. )-form
Di-Ac: [72635-06-4].
Constit. of A. montana. Cryst. (Et20jpet. ether). Mp
147°. [1X]~4 +221° (c, 1 in CHC1 3).
8-(2-Methylpropanoyl), 9-Ac: [72635-07-5].
Constit. of A. montana. Oil.
8-(2-Methylbutanoyl), 9-Ac: [72635-08-6].
C12H 280 7 M 404.459
Constit. of A. montana. Oil.
(4rx..Srx.,6rx.,Brx.,9f/)-form
9-Angeloyl: [117274-13-2]. Heliopsolide
C20H 240 6 M 360.406
Constit. of Heliopsis helianthoides. Oil.
9-Angeloyl, 8-Ac: [117274-04-1].
C12H 260 7 M 402.443
Constit. of H. helianthoides. Oil.
(4P.Srx.,6rx.,Brx.,9f/)-form
9-Angeloyl, 8-Ac: [117274-11-0].
Constit. of H. helianthoides. Oil. [IX]~ + 10° (c,0.39 in
CHC1 3).
9-(2 ,3-Epoxy-2-methylbutanoyl), 8-Ac:
Sq-02014 - Sq-02018
C22 H 260 8 M 418.443
Constit. of H. helianthoides. Oil.
[117274-14-3)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 995.
Jakupovic, J. et al, Phytochemistry, 1988, 27, 2235.
Sq-02014
2,4,10-Trihydroxy-1(5)-guaien-12,6-olide Sq-02016
H~f?
\OH
4 I (2cx,4cx,6cx,10P,llcx)-/orm
HO/
6 --
C 15H 120 5 M 282.336
(2rx.,4rx.,6rx.,10p,Jlrx.)-form [81907-05-3] Artabsinolide C
Constit. of Artemisia absinthium. Cryst. (EtOAc). Mp
135-137°. [1X]n -22° (c, 0.1 in CHC1 3).
2-Ketone: [82078-63-5]. 4,10-Dihydroxy-2-oxo-1(5)-guaien-
12,6-o/ide. Artabsinolide A
Ct 5 H 100 5 M 280.320
Constit. of A. absinthium. Cryst. (EtOH). Mp 160-162°.
Sq-02015 [1X]n + 9° (c, 0.1 in CHC1 3).
(2P,4P,6a.,IOp,II rx. )-form
Constit. of A. absinthium. Cryst. (EtOAc). Mp 143-145°.
[1X]n -51 o (c, 0.1 in CHC1 3).
2-Ketone: [76564-29-9]. Artabsinolide B. Artemoline
C 15 H 2~Ps M 280.320
Constit. of A. absinthium. Cryst. (EtOAcjhexane). Mp
180-182°, Mp 205°. [1X]n +20° (c, 0.1 in CHC1 3).
Kasymov, S.Z. eta/,. Khim. Prir. Soedin., 1979, 15, 658; Chern.
Nat. Compd. (Engl. Trans/.), 577.
Beauhaire, J. et al, J. Chern. Soc., Perkin Trans. 1, 1982, 861.
4,8, 10-Trihydroxy-11(13)-guaien-12,6- Sq-02017
olide
C 15H 120 5 M 282.336
[93930-14-4] Vestolide
(lrx.,4~.Srx.,6rx.,9P,IOrx.)-form
Constit. of Vicoa vestita. Oil.
Sachdev, K. eta/, Phytochemistry, 1984, 23, 2379.
8,10,11-Trihydroxy-3-guaien-12,6-olide Sq-02018
C 15H 120 5 M 282.336
Confusion concerning the 10-config. of some of these
compds. apparently due to a drawing error in one of the
papers showing it as 101X-.
(IP.SP,6P,Brx.,IOp(OH),Ilrx.)-form
513
2,4,8-Trihydroxy-3-oxo-1(10),11(13)-... - 5,8,14-Trihydroxy-2-oxo-1,(10) ... Sq-02019 - Sq-02022

8,10,11- Trihydroxy-3-sloveno/irk (1«,5«,6«,8P,J 0/1)-form

11-Ac: 11«-Acetoxy-8«,1OP-dihydroxy-3-sloveno/irk 8- Tigloyl: [73971-73-0].
Ct,H:z,P6 M 324.373 C20H 240 7 M 376.405
Constit. of Laserpitium siler. Noncryst. [1X]i? -55.1° (c, Constit. of Picradeniopsis woodhousei. Oil. [1X]n +48° (c,
0.13 in MeOH). 0.11 in CHC1 3).
10,11-Di-Ac: 10,11-Diacetoxy-8-hydroxy-3-slovenolirk Herz, W. eta/, J. Org. Chern., 1980, 45, 3163.
C19H 260 7 M 366.410
From L. siler. Noncryst. 5,8,9-Trihydroxy-2-oxo-1(10),3,11(13)- Sq-02021
8-(2-Methylbutanoyl), 10,11-di-Ac: guaiatrien-12,6-olide
C24H 340 8 M 450.528
Constit. of roots of Laser trilobum. Cryst. Mp 126-127°.
8-(3-Methyl-2-butenoyl), 11-Ac: [30557-67-6]. Montanolirk
C22 H 300 7 M 406.475
Isol. from Laserpitum siler and L. archangelica. Mp 132-
1330. [1X]i? -72.2° (c, 3.5 in CHC13).
8-Angeloyl, 11-Ac: [38114-47-5]. 1somontanolide
C22H 300 7 M 406.475 0
lsol. from fruits of L. siler. Mp 176°. [1X]i? -25.2°.
CtsH 160 6 M 292.288
8-Angeloyl, 10,11-di-Ac: Acetylisomontanolirk
(5«,6«,8«,9/1)-form
C24H 320 8 M 448.512
Isol. from roots and rhizomes of L. siler. Mp 134°. [1X]i? 9-Angeloyl: [1405-19-2]. Pumilin
-78.2°. C20 H 22 0 7 M 374.390
Constit. of Berlandiera pumila and B. texana. Cryst.
8,11-Diangeloyl: [68852-48-2]. Gradolide
(EtOAc). Mp 244-245° dec.
C25 H 340 7 M 446.539
Constit. of L. siler. Cryst. Mp 154°. [1X]i? -50.9°. 9-Angeloyl, 8-Ac: 8-Acetylpumi/in
C22H 240 8 M 416.427
8-(2-Methylpropanoyl), 10,11-di-Ac: [68799-88-2].
lsol. from Montanoa tomentosa. Gum.
Polhovolide
C23H 320 4 M 372.503 9-(2-Methylpropenoyl), 8-Ac: 8-Acetyl-9-rksacylpumi/in 9-
Constit. of L. siler. Cryst. (diisopropy1 ether). Mp 98- methacrylate
990. [1X]i? -83.SO (c, 0.3 in CHC1 3). C21 H 22 0 8 M 402.400
lsol. from M. tomentosa. Mp 222.5-223.5°.
Holub, M. eta/, Collect. Czech. Chern. Commun., 1970, 35, 3296;
1972, 37, 1186; 1978, 43, 2444, 2471. Fischer, N.H. eta/, J. Heterocycl. Chern., 1982, 19, 181 (isol)
Smitalova, Z. eta/, Collect. Czech. Chern. Commun., 1984, 49, 852. Seaman, F.C. eta/, Phytochemistry, 1984, 23, 817 (isol)
Holub, M. et a/, Tetrahedron Lett., 1984, 25, 3755.
5,8,14-Trihydroxy-2-oxo-1,(10),3,11(13)- Sq-02022
2,4,8-Trihydroxy-3-oxo-1(10),11(13)- Sq-02019 guaiatrien-12,6-olide
guaiadien-12,6-olide

CtsH 160 6 M 292.288

CtsH 1806 M 294.304 (5«,6«,8/1)-form
(2ft,4~,5«,6«,8«)-form 8-Tigloyl: 5-Hydroxyeupasessifo/ide B
4-Me ether: [86925-82"8]. Ajajin C20H 220 7 M 374.390
C16H 200 6 M 308.330 Constit. of Eupatorium rotundifolium. Oil.
Constit. of Ajania fastigiata. Cryst. Mp 212-213°. [IX]~ Bohlmann, F. et a/, Phytochemistry, 1980, 19, 1233.
+34.7° (c, 3.57 in MeOH).
Yusupov, M.l. eta/, Khim. Prir. Soedin., 1983, 19, 390.

3,8,10-Trihydroxy-2-oxo-3,11(13)- Sq-02020
guaiadien-12,6-olide

M 294.304

514
4,5:9,10-Diepoxy-3,6,13-trihydroxy-... - 2,4-Dihydroxy-10(14),11(13)-... Sq-02023 - Sq-02027

Bohlmann, F. eta/, Phytochemistry, 1979, 18, 131 (Puberolide)

Yu, S. et a/, Phytochemistry, 1988, 27, 2887.

12,8-Guaianolides Gao, F. eta/, Phytochemistry, 1990, 29, 551 (Hymenoratin G)

2,4-Dihydroxy-9,11(13)-guaiadien-12,8- Sq-02026
olide

4,5:9,10-Diepoxy-3,6,13-trihydroxy-12,8- Sq-02023
guaianolide
(1 ~,2a,4a,5a,8a)-form
,o

HO~,·
0
-0
C15H 200 4 M 264.321
0 'H' 0 (I p,2r¥-,4r¥-,5r¥.,8r¥. )-form
HO CH2 0H 2-Ac: [14682-46-3]. GaiUardin
C 17H 220 5 M 306.358
CI5H2007 M 312.319 Constit. of Gaillardia pulchella, lnula britannica and /.
(3/!,,4r¥-,5r¥-,6r¥.,8r¥.,9P,I op,II r¥-H)-form oculus-christi. Cryst. (C 6H 6fpet. ether). Mp 199-200° (in
3-Tigloyl: [62197-62-0]. Eufoliatin vacuo). [IX]~ -15°.
C 20H 260 8 M 394.421 (lp,2r¥-,4r¥-,5r¥.,8f/)-form [25941-24-6] Pleniradin
Constit. of Eupatorium perfoliatum. Powder Constit. of Baileya pleniradiata. Cryst. Mp 94-97°. [1X]n
(MeOH/CHCI 3). Mp 227-229°. [1X]n - 27.SO (c, 0.0121 in +35°.
MeOH).
2-Ac: [25873-32-9]. Neogaillardin
Herz, W. eta/, J. Org. Chern., 1977, 42, 2264. C 17H 220 5 M 306.358
Constit. of G. pulchella. Oil.
2,4-Dihydroxy-1(1 0), 11(13)-guaiadien- Sq-02024 (11!,,21!,,41!,,51!,,81!,)-form [65207-29-6] Halshalin
12,8-olide Constit. of Helenium autumnale. Cryst. Mp 180-181°.
[1X]n -66.2° (c, 0.5 in MeOH).

H~
\ Kupchan, S.M. eta/, J. Pharm. Sci., 1965, 54, 1703 (Gaillardin)
21f" Dullforce, T.A. eta/, J. Chern. Soc. B, 1971, 1399 (Gaillardin)
Inayama, S. et a/, Phytochemistry, 1973, 12, 1741 (Neogaillardin)
Ho- ' o Kondo, Y. eta/, Tetrahedron Lett., 1977, 2155 (Halshalin)
H 0 Herz, W. eta/, J. Org. Chern., 1979, 44, 1873 (Pleniradin)
r
C 15H 200 4 M 264.321 2,4-Dihydroxy-10(14),11(13)-guaiadien- Sq-02027
(2r¥-,4r¥-,5r¥.,8f/)-form 12,8-olide
2-Ac: [79464-34-9]. lnuchinenolide B
Ct,H 22 0 5 M 306.358
Constit. of Inula britannica. Oil. [1X]i? -57.2° (c, 1.3 in f!n_o
HO~O
CHCI 3).
Ito, K. et a/, Phytochemistry, 1981, 20, 271.

2,4-Dihydroxy-5,11(13)-guaiadien-12,8- Sq-02025 C15H200 4 M 264.321

olide (I P,2r¥-,4r¥-,5r¥-,1 Of/)-form [54964-49-7] Florilenalin
Constit. of Helenium autumnale. Oil.
2-Ac:
C 17H 220 5 M 306.358
(l a,2a,4a,8a, 1Oa )-form
From Loxothysanus sinuatus. Cryst. Mp 127°. [1X]i;' + 79°
(c, 5.28 in MeOH).
Di-Ac: Cryst. Mp 128-129°.
lliX,l3-Dihydro: [57095-90-6]. Dihydroflorilenalin
C 15H 200 4 M 264.321 C15H2204 M 266.336
(lr¥-,2r¥-,4r¥.,8r¥.,10r¥.)-form [117634-61-4] Constit. of H. autumnale. Cryst. Mp 208°.
Constit. of Gaillardia pulchella. Kozuka, M. eta/, Chern. Pharm. Bull., 1975, 23, 1895
(lr¥-,2P,4P,Br¥-,10r¥.)-form (Dihydrojlorilenalin)
McPhail, A.T. et al, J. Chern. Soc., Perkin Trans. 2, 1975, 492
2-Ac: [68776-44-3]. Puberolide (Florilenalin)
Ct,H 2205 M 306.358 Bohlmann, F. et al, Phytochemistry, 1985, 24, 1021
Constit. of Helenium puberulum. Oil. (Acetyiflorilenalin)
(lr¥-,2r¥-,4r¥-,8P,10r¥.)-form Gao, F. eta/, Phytochemistry, 1990, 29, 551 (isol, pmr, cmr)
111X,l3-Dihydro: [126771-22-0]. 2,4-Dihydroxy-5-guaien-
12,8-olide. Hymenoratin G
C15H220 4 M 266.336
Constit. of Hymenoxys odorata.

515
3,5-Dihydroxy-4(15),10(14)-... - 1,4-Epidioxy-2,5-guaiadien-12,8-... Sq-02028 - Sq-02033

3,5-Dihydroxy-4(15),1 0(14)-guaiadien- Sq-02028 1-(2-Methylbutanoyl): Biennin B

12,8-olide C20H 300 5 M 350.454
Constit. of Hymenoxys biennis. Powder.
Gao, F. et al, Phytochemistry, 1990, 29, 3875 (isol, pmr)

HO 3,4-Dihydroxy-9-guaien-12,8-olide Sq-02031
[38769-25-4]
0

C15H20 04 M 264.321
(1«,3P,5«,8«.,11PH)-form [106310-46-7]
Constit. of Arctotis arctotoides. Oil. [oe]i;' -74° (c, 0.5 in
CHC1 3).
10oe,J4-Epoxide: [106310-47-8]. C15H 2204 M 266.336
C15H200 5 M 280.320
(1 «.,3«.,4«.,5«,8P,11 p)-form
From A. arctotoides. Oil. [«.]~4 -29° (c, 0.09 in CHC1 3).
Carolenalin
10,14-Dihydro, JOP-hydroxy,l4-chloro, 3-Ac: [106310-45-6]. Constit. of Helenium autumnale. Oil.
3-Acetoxy-14-ch/oro-5,10-dihydroxy-4(15)-guaien-12,8-
3-Ac: Cryst. Mp 160-161°. [«.] 0 -91.7° (c, 1 in MeOH).
o/ide. Arctodecurrolide
Ct7HztC10, M 356.802 3-(2-Methyl-2-butenoyl): [38769-36-7]. Carolenin
Constit. of A. arctotoides. Oil. [rx]i;' + 33° (c, 0.5 in C20 H 280 5 M 348.438
CHC1 3). Constit. of H. autumnale. Oil. [rx]i,S -101.9° (c, 0.6 in
MeOH).
Jakupovic, J. et al, Planta Med., 1986, 365.
McPhail, A.T. et al, Tetrahedron Lett., 1973, 4087.

3,5-Dihydroxy-4(15),10(14),11(13)- Sq-02029
guaiatrien-12,8-olide Dugaldiolide Sq-02032
[94099-87-3]

HO-

C15H 180 4 M 262.305

Struct. revised in 1989. C15H 2205 M 282.336
(1 «.,3P,5«.,8«. )-form 2«.-Tigloyloxy: 2«.- Tigloyloxydugaldiolide
3-Desacetyl-10,14-desoxoarctolide C20 H 280 7 M 380.437
Constit. of Arctotis grandis. Gum. [rx]i;' +40° (c, 0.44 in Constit. of Dugaldia hoopesii. Oil. [«.]~4 + 25° (c, 0.3 in
CHC1 3). CHC1 3).
3-Ac: [74334-29-5]. Deoxyarctolide. Desoxoarctolide Bohlmann, F. et al, J. Nat. Prod. (Lloydia), 1984, 47, 658.
C 17H 200 5 M 304.342
From A. grandis. 1,4-Epidioxy-2,5-guaiadien-12,8-olide Sq-02033
3-Ac, JOP,14-epoxide: [64390-62-1]. 3P-Acetoxy-10p,14- 2,5-Guaiadien-12,8-o/ide 1,4-endoperoxide
epoxy-5-hydroxy-4(15), 11 (13)-guaiadien-12,8«.-o/ide.
I
Arctolide I

~
f
Ct7Hzo06 M 320.341
From A. grandis. Cryst. (MeOH/Et 20). Mp 144-145°. 0
[«.] 0 +64.1° (c, 0.42 in MeOH).
0 """' 0
Samek, Z. eta/, Collect. Czech. Chern. Commun., 1977, 42, 2217 I
(isol) I

Halim, A.F. et a/, Planta Med., 1980, 38, 183 (isol) C15H1s04 M 262.305
Halim, A.F. eta/, Phytochemistry, 1983, 22, 1510 (isol) The two isomers (1«.,4«.)-form and (lp,4p)-form could not
Budesinsky, M. eta/, Collect. Czech. Chern. Commun., 1989, 54,
be separated. Constit. of Geigeria plumosa. Gum.
166, 473, 1919 (pmr, cmr, struct)
[125289-92-1, 125409-44-1]
Sq-02030 Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr)
2,4-Dihydroxy-1(5)-guaien-12,8-olide

HOr;/;n=O
\

OH
C15H22 0 4 M 266.336
(1 «,4«,8P,J opH,11 «H)-form

516
4,5-Epoxy-10(14),11(13)-guaiadien-... - 1,3,5-Guaiatrien-12,8-olide Sq-02034 - Sq-02040

4,5-Epoxy-10(14),11(13)-guaiadien-12,8- Sq-02034 1(10),3-Guaiadien-12,8-olide Sq-02037

olide

~
~0
C15H100 2 M 232.322
CISH1703 M 245.297
(1 rx.,4rx..Srx.,8rx.)-form (4rx.,8P,Jlrx.)-form
Constit. of Stevia samaipatensis. Oil.
4rx..Srx.-Epoxyiml,iscolide
Constit. of Inula anatolica. Oil. Trivial name is Zdero, C. eta/, Phytochemistry, 1988, 27, 2835.
misleading.
Topca, G. eta/, Phytochemistry,·1990, 29, 3666 (iso/, pmr) 1(10),4-Guaiadien-12,8-olide Sq-02038

~0
3,4-Epoxy-1-hydroxy-11(13)-guaien-12,8- Sq-02035
olide

I
I
I

C 15H100 2 M 232.322
(Brx.,llrx.)-form [72145-15-4] Helisp/endiolide
Constit. of Helichrysum splendidum. Oil. [a]i;' + 78.4° (c,
C 15H 100 4 M 264.321 1.5 in CHC1 3).
Ac: Calocepluzlin Bohlmann, F. eta/, Phytochemistry, 1979, 18, 885.
C 17H120 5 M 306.358
Constit. of Calocephalus brownii. Cryst. Mp 146-147°.
[a]~ +28° (c, 0.3 in CHC1 3). 1(10),11(13)-Guaiadien-12,8-olide Sq-02039
Batterham, T.J. eta/, Aust. J. Chern., 1966, 19, 143.

4,5-Epoxy-2-hydroxy-11(13)-guaien-12,8- Sq-02036
olide
0
13

C 15H100 2 M 232.322
(4rx..Srx.,8rx.)-form [66873-37-8] ColumeUarin
Constit. of Callitris columellaris. Cryst. by sub!. Mp
43.5-44°. [aln -44.7°.
C 15H 100 4 M 264.321 11ft,l3-Dihydro: [66873-38-9]. 1(10)-Guaien-12,8-olide.
(1rx.,2rx.,4rx..Srx.,8p,JOrx.)-form DihydrocolumeUarin
C 15H120 2 M 234.338
Ac: [100664-34-4]. Mexicanin G Constit. of C. columellaris. Cryst. by sub!. Mp 77-77.SO.
C 17H120 5 M 306.358 [aln + 18.9°.
Constit. of Helenium mexicanum. Cryst. Mp 214-216°.
[a]i,S +40° (c, 1 in CHC1 3). Brecknell, D.J. eta/, Aust. J. Chern., 1979, 32, 2455.
11P,13-Dihydro, 0-(2-methylbutanoyl)(S-): [72264-71-2].
Hymenosignin 1,3,5-Guaiatrien-12,8-olide Sq-02040
C10H 300 5 M 350.454
Constit. of Hymenoxys insignis. Cryst. (C 6H 6 /hexane).
Mp 111-113°. [a]n + 10.8° (c, 0.015 in CHC1 3).
11P,l3-Dihydro, angeloyl: [126771-21-9]. Hymenoratin F
C10H 280 5 M 348.438
lsol. from Hymenoxys odorata.
lla,13-Dihydro, tigloyl: 2-0-Tigloylhymenoratin E
C10H 280 5 M 348.438 CISH1802 M 230.306
Isol. from H. biennis. Powder. (Bp,JOpH,llPH)-form [125289-69-2] Geigeriafulvenolide
lla,13-Dihydro, angeloyl: [126873-98-1]. Hymenoratin E Constit. of Geigeria ornativa. Orange-red cryst. Mp
103°. [a]i;' +200° (c, 0.72 in CHC1 3).
CzoH21105 M 348.438
Isol. from H. odorata. Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (isol, pmr, cmr)
Herz, W. eta/, J. Org. Chern., 1980, 45, 493 (Hymenosignin)
Romo de Vivar, A. eta/, Phytochemistry, 1985, 24, 2977
(Mexicanin G)
Gao, F. eta/, Phytochemistry, 1990, 29, 551, 3875 (Hymenoratins)

517
1(10),2,4-Guaiatrien-12,8-olide - 3-Hydroxy-4,11(13)-guaiadien-12,8-... Sq-02041 - Sq-02046

1(10),2,4-Guaiatrien-12,8-olide Sq-02041 (4«,8«,1 Ofl)-form

Constit. of Apalochlamys spectabilis. Gum.

~0
Zdero, C. et al, Phytochemistry, 1990, 29, 3201 (isol)

3-Hydroxy-1(5),11(13)-guaiadien-12,8- Sq-02045
olide
I
I

C 15H 180 1 M 230.306

(Bfl,ll«)·form [117825-12-4] Ste,isamolitk
Constit. of Stevia samaipatensis. Yellow cryst.
(Etpjpet. ether). Mp 96-97°. [a]~ -279° (c, 0.71 in
CHC1 3).
Zdero, C. et al, Phytochemistry, 1988, 27, 2835. C 15H 100 3 M 248.321
(3fl,Br~.)-form
3,1 0(14),11(13)-Guaiatrien-12,8-olide Sq-02042 Ac: [125164-70-7]. 3fl-Acetoxy-1(5),11(l3)-guaiadien-12,8a-
olide

~O
Ct 7H 110 4 M 290.358
Constit. of Pechue/-Loeschea /eibnitziae. Oil.
(la,5a,8a)-fmm L\ 5•6 isomer, Ac: [125164-71-8]. 3ft-Acetoxy-5,11(l3)-
guaiadien-12,8a-olide
Constit. of P. leibnitziae.
Zdero, C. et al, Phytochemistry, 1989, 28, 3097 (isol, pmr)
Ct5Hts01 M 230.306
(1«,5«,8«)-form [73020-91-4] Ziniolitk 3-Hydroxy-4,11(13)-guaiadien-12,8-olide Sq-02046
Constit. of Zinnia multiflora. Oil. [a]~ + 140.2° (c, 1.64
in CHCI 3). H
I
(lr~.,5r~.,Bfl)-form [73696-08-9] Xantholitk A
Constit. of Xanthium canadense. Inhibits larval growth HO-
of Drosophila melanogaster. Cryst. Mp 71-72°. [aJn (1cx,3cx,8~,10~)-form
+ 170.5°. 0
JlfJ,13-Dihydro: [74320-17-5]. 3,10(14)-Guaiadien-12,8-olide.
Xantholitk B C15H 100 3 M 248.321
C 15H 100 1 M 232.322
(1 r~.,3r~.,8fl,1 Ofl)-form
Constit. of X. canadense. Inhibits larval growth of D.
3r~.-Hydroxydesoxoacha/ensolide
melanogaster. Cryst. Mp 76-77°.
Constit. of Stevia polyphylla. Oil.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1343.
3-Me ether: 3a-M ethoxy-4, II (13)-guaiadien-12,8/l-olide
Tahara, T. et al, Tetrahedron Lett., 1980, 1861.
C16H 110 3 M 262.348
Constit. of S. polyphylla. Oil.
4(15),10(14),11(13)-Guaiatrien-12,8-olide Sq-02043 3-Deoxy: 4,11(13)-Guaiadien-12,8/l-olide. 3-
Desoxoachalensolide
HI ~ C 15H 100 1 M 232.322
Constit. of S. po/yphylla. Oil. [a]~ + 162° (c, 1.55 in
CHCI 3).
0 3-Deoxy, llfJ,13-dihydro: 4-Guaien-12, 8fl-olide. llfJ,13-
Dihydrotksoxoacha/ensolitk
C 15H 110 2 M 234.338
CtsHtsOz M 230.306 Constit. of S. polyphylla.
[77370-03-7] Elehirtanolitk
(lr~.,4r~.,Bfl)-form 3-Ketone: see 3-0xo-4,11(13)-guaiadien-12,8-olide, Sq-
Constit. of Elephantopus hirtiflorus and Stevia achalensis. 02064
Oil. (1 r~.,3fJ,BfJ,1 Ofl)-form
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2669 (isol) 3fl-Hydroxytksoxoacha/ensolitk
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1986, 799 (isol) Constit. of S. polyphylla. Cryst. (Etp). Mp 128-129°.
[a]~ + 116° (c, 0.5 in CHC1 3).
10-Hydroperoxy-4-hydroxy-1,11(13)- Sq-02044 Ac:
guaiadien-12,8-olide C 17H 110 4 M 290.358
Constit. of S. polyphylla. Oil. [a]~ + 139° (c, 2.2 in
CHCI3).

~-q Me ether: 3fJ-Methoxy-4,11(l3)-guaiadien-12,8fJ-olide

C 16H 1P 3 M 262.348
Constit. of S. polyphylla. Oil.
~0 11fJ,13-Dihydro: 3fJ-Hydroxy-4-guaien-12,8fJ-olide. 3/1-
Hydroxy-11 fJ,13-dihydrotksoxoacha/ensolide
C 15H 110 3 M 250.337
M 280.320

518
4-Hydroxy-1(10),11(13)-guaiadien-... - 4-Hydroxy-10(14),11(13)-guaiadien-... Sq-02047 - Sq-02050

Constit. of S. polyphylla. Cryst. (Etp). Mp 116°. Constit. of Postia bombycina. Cryst. Mp 140°. [cxJi:
Oberti, J.C. eta/, J. Org. Chern., 1983, 48, 4038 (iso[) -38° (c, 0.2 in CHCI 3).
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835 (iso[) 9P,JOP-Epoxide: [125675-13-0]. 9P,10P-Epoxy-4cx-hydroxy-
11 (13)-guaien-12,8cx-olide
4-Hydroxy-1(10),11(13)-guaiadien-12,8- Sq-02047 C 15Hzo04 M 264.321
Constit. of P. bombycina. Oil. [cxJi: -36° (c, 0.15 in
olide
CHCI 3).
6cx-Acetoxy: [125675-16-3]. 6cx-Acetoxy-4cx-hydroxy-
9, 11 ( 13)-guaiadien-12,8cx-olide
(4ct,5ct,8ct)-form C17H110 5 M 306.358
Constit. of P. bombycina. Gum. [cxJi: -49° (c, 1.3 in
CHCI 3).
6cx-Acetoxy, 9P,JOP-epoxide: [125675-14-1]. 6cx-Acetoxy-
C 1 ~H 20 0 3 M 248.321 9p, 1op-epoxy-4cx-hydroxy-11 (13)-guaien-12,8cx-olide
Ct7H120 6 M 322.357
(4rz..Srz.,8rz.)-form Constit. of P. bombycina. Cryst. Mp 227°. [cxJi: -68° (c,
Constit. of Helichrysum dasyanthum. Gum. 0.12 in CHC1 3).
(4rz..Srz.,8fl)-form [1461-34-3] Pseudoivalin
(lp,4rx..Srz.,8fl)-form
Constit. of Iva microcephala and Ca/ocephalus brownii. 2-Deoxypleniradin
Cryst. (Me 2C0jpentane). Mp 122-123°. [cxln -145° (c, 1
Constit. of Hymenoxys scaposa var. villosa.
in CHCI 3).
4-0-cx-L-Rhamnopyranoside: 2-Deoxypleniradin-4-0-rx.-L-
Ac: rhamopyranoside
C 17H120 4 M 290.358 C21 H 300 7 M 394.464
Constit. of C. brownii. Cryst. (Et20jpentane). Mp 167-
Constit. of Helenium radiatum. Cryst. Mp 163-164°. [cxJi:
1690. [cxJn -180° (c, 1 in CHCI 3). -134.8° (c, 1.02 in CHC1 3).
111;,,13-Dihydro: Dihydropseudoivalin 14-Acetoxy: 14-Acetoxy-2-deoxypleniradin
C 1 ~H 12 0 3 M 250.337
C17H 110 5 M 306.358
Constit. of /. microcephala. Oil. Constit. of Hymenoxys scaposa var. villosa.
Herz, W. eta/, J. Org. Chern., 1965, 30, 118 (isol, struct)
0-(6- Ace tyi-P-D-glucopyranoside): [1 02903-90-2].
Batterham, T.J. eta/, Aust. J. Chern., 1966, 19, 143 (ms)
Gitany, R. et a/, Acta Crystal/ogr., Sect. B, 1974, 30, 1900 (cryst C23H 310 9 M 452.500
struct) lsol. from H. lemmonii.
Jakupovic, J. eta/, Phytochemistry, 1989,28, 1119 (iso[) Hikino, H. et a/, Chern. Pharm. Bull., 1968, 16, 1601 (iso[)
Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 3127 (isol, pmr)
Petenatti, E. et a/, Phytochemistry, 1990, 29, 3669 (iso/, pmr, cmr)
4-Hydroxy-5,11(13)-guaiadien-12,8-olide Sq-02048 Gao, F. eta/, Phytochemistry, 1990, 29, 895, 1601 (iso/, pmr, cmr)

;-;>--r-'{
\

4-Hydroxy-10(14),11(13)-guaiadien-12,8- Sq-02050
0 olide
( 1ct,4ct,8ct, I Oct )-form

~ ( 1ct,4ct,5ct,8ct }form
C 1 ~H 20 0 3 M 248.321
(1 rz.,4rz.,8rz.,l Orz. )-form 0
Isol. from Apa/ochlamys spectabilis. Cryst. Mp 169°.
(1 p,4rz.,8P,J Orz. )-form
C 15Hzo0 3 M 248.321
llcx,13-Dihydro, 4-0-P-D-g/ucopyranoside: Lemmonin D
C23H 310 9 M 452.500 (1 rz.,4rz.,5rz.,8rz. )-form
lsol. from Hymenoxys lemmonii. [cxJn -20.4° (c, 1.1 in 1-Epiinuviscolide. !1-epi-Inuvisco/ide
MeOH). C 1 ~Hzo0 3 M 248.321
Constit. of Dittrichia graveolens. Oil.
Gao, F. eta/, Phytochemistry, 1990, 29, 1601.
Zdero, C. eta/, Phytochemistry, 1990, 29, 3201. 11P,13-Dihydro: 4-Hydroxy-10(14)-guaien-12,8-o/ide.
11 p,13-Dihydro-1-epi-inuviscolide
C 1 ~H 11 0 3 M 250.337
4-Hydroxy-9,11(13)-guaiadien-12,8-olide Sq-02049 Constit. of D. graveolens. Oil.
10cx,14-Dihydro: 4-Hydroxy-11(13)-guaien-12,8-olide.
1Orz.,l4-Dihydro-1-epi-inuviscolide
C 15H120 3 M 250.337
Constit. of lnula anatolica. Oil.
0 (1 p,4rz..Srz.,8rz. )-form [631 09-30-8] lnuviscolide
Constit. of/. viscosa. Oil. [cx]~4 -18.6° (c, 0.35 in
CHC1 3).
C 1 ~Hzo0 3 M 248.321 4-0-(6-Acetyi-P-D-glucopyranoside):
(1rz.,4rz.,5rz.,8fl)-form [21688-81-3] Helenium lactonet C23 H 310 9 M 452.500
Constit. of Helenium autumnale. Cryst. (EtOAc). Mp Constit. of Hymenoxys lemmonii. [cxJn -30.4° (c, 0.8 in
lll-112°. [cxln -88° (c, 2.5 in CHCI 3). MeOH).
(1P,4rz..Srz.,8rx.)-form [125675-15-2] 11 cx,13-Dihydro: 11 rz.,13-Dihydroinuviscolide

519
15-Hydroxy-3,10(14)-guaiadien-12,8-... - 3-Hydroxy-4(15),10(14),11(13)-... Sq-02051 - Sq-02053

C1sH120 3 M 250.337 3-Hydroxy-4(15),9,11(13)-guaiatrien-12,8- Sq-02052

Constit. of Gnephosis brevifolia. Gum. olide
11P,13-Dihydro: (84093-50-5]. 11P,13-Dihydroinuviscolide
CISH2203 M 250.337
Constit. of Geigeria aspera. Gum. [1X]~4 +28° (c, 0.13 in
CHCI 3). HO
(Jp,4rx.,5rx.,8f/)-form (108885-57-0]8-Epiinuviscolide. 8-epi-
lnuvisco/ide 0
C 1sH 200 3 M 248.321
Constit. of Bedfordia arborescens. Oil. CtsH 180 3 M 246.305
4-0-(6-Acetyl-P-D-glucopyranoside): Lemmonin A (1~,3~,5~,8~)-form [98093-98-2] Macrotanacin
C23H 320 9 M 452.500 Constit. of Tanacetum macrophillum. Cryst. Mp 205-
Constit. of H. lemmonii. [1Xln -24.8° (c, 0.99 in MeOH). 2070.
111X,13-Dihydro: Constit. of Helichrysum splendidum. Gum. Todorova, M. eta/, Planta Med., 1985, 174.
lliX,l3-Dihydro, 4-0-P-D-glucopyranoside: Lemmonin C
C21H 320 8 M 412.479 3-Hydroxy-4(15),10(14),11(13)-guaiatrien- Sq-02053
Constit. of H. lemmonii. [1X]n -39.3° (c, 0.6 in MeOH).
· 12,8-olide
111X,l3-Dihydro, 4-0-(6-acetyl-P-D-glucopyranoside):
Lemmonin B
C23H 340 9 M 454.516
Constit. of H. lemmonii. [1X]n -27° (c, 2 in MeOH).
(1 cx,3~,5cx,8cx )-form
lliX,l3-Dihydro, 4-0-(2,6-diacetyl-P-D-glucopyranoside):
C2SH360 10 M 496.553 0
Constit. of Geigeria ornativa. Gum. [IX]~ -23° (c, 0.8 in
HCI 3). C 15H 180 3 M 246.305
(1 p,4P,5rx.,8f/)-form [I 08885-58-I] 4,8-Diepiinuvisco/ide. 4,8- Bis-
(lrx.,3P,5rx.,8rx.)-form
epi-inuviscolide Isol. from Arctotis aspera. Cryst. (MeOH). Mp 128-
C1sH200 3 M 248.321 1310.
Constit. of B. arborescens. Oil.
Ac:
[128529-96-4, 128529-97-5, 129885-15-0] C17H 200 4 M 288.343
Bohlmann, F. et al, Chern. Ber., 1977, 110, 1330 (iso/, struct) Constit. of A. aspera.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679 (isol)
Zdero, C. eta/, Phytochemistry, 1987, 26, 1207 (isol, struct) P-D-Glucopyranoside: [94474-63-2]. Macrocliniside C
Rustaiyan, A. eta/, Phytochemistry, 1987, 26, 2603 (deriv) C21 H 280 8 M 408.447
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 3183; 1989, 28, 1119 Constit. of Macroclinidium trilobum. Amorph. powder.
(isof) [1X]i,S + 13.6° (c, 1.10 in Hp).
Ortega, A. eta/, Heterocycles, 1989, 29, 635 (synth) 0-[p-D-Glucopyranosyl-(1--+ 3)-P-D-glucopyranoside]: [94474-
Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (isol) 64-3]. Macrocliniside D
Gao, F. eta/, Phytochemistry, 1990, 29, 1601 (Lemonins)
Topcu, G. et a/, Phytochemistry, 1990, 29, 3666 (iso, pmr)
C27H 380 13 M 570.589
Constit. of M. trilobum. Cryst. (MeOH). Mp 238-241°.
[1X]i,S -4.9° (c, 0.41 in Hp).
15-Hydroxy-3, 10(14)-guaiad.ien-12,8-olide Sq-02051 0-[p-D-Glucopyranosyl-(1--+4)-P-D-glucopyranoside]: [94474-
65-4]. Macrocliniside E

~0
C27H 380 13 M 570.589
Constit. of M. trilobum. Amorph. powder. [1X]i,S +25.7°
(c, 0.53 in H 20).

HOH2~0 :
3-Ketone: 3-0xo-4(15),10(14),11(13)-guaiatrien-12,8rx.-olide
CISH1603 M 244.290
Constit. of A. aspera.
C 15H2003 M 248.321 (.lrx.,3p,5rx.,8f/)-form
(lrx.,5rx.,8P,llrx.)-form 3P-Hydroxyelehirtanolide
Constit. of Stevia samaipatensis. Oil. 3-Methylbutanoyl:
Ac: 15-Acetoxy-3,10(14)-guaiadien-12,8P-olide C20 H 260 4 M 330.423
C17H120 4 M 290.358 Constit. of Elephantopus hirtiflorus.
Constit. of S. samaipatensis. Oil. [1X]n + 125° (c, 3.6 in Bohlmann, F. et a/, Phytochemistry, 1980, 19, 2669 (3P-
CHCI 3). Hydroxyelehirtanolide)
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835. Miyase, T. eta/, Chern. Pharm. Bull., 1984, 32, 3912
(Macroclinisides)
Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 195.

520
5-Hydroxy-3,11(13)-guaiatrien-12,8-... - 6-Hydroxy-2-oxo-1(10),3-guiadien-... Sq-02054 - Sq-02061

5-Hydroxy-3,11(13)-guaiatrien-12,8-olide Sq-02054 6-Hydroxy-2-oxo-3-guaien-12,8-olide Sq-02058

H

~0
I

0
~0 I
C 15H 200 3 M 248.321
ClsHzo04 M 264.321
(1 rx.,5rx.,8p,l Ofl)-form (6rx.,8fl)-form
Constit. of Stevia polyphylla. Oil.
6-0-(3-methy/-2-butenoyl): [125289-77-2].
Zdero, C. et at, Phytochemistry, 1988, 27, 2839. C20 H 260 5 M 346.422
Constit. of Geigeria ornativa. Cryst. Mp 89°. [1X]~4 -86°
6-Hydroxy-4(15),10(14),11(13)-guaiatrien- Sq-02055 (c, 0.15 in CHCI 3).
12,8-olide Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (iso/, pmr, cmr)

Sq-02059

ClsH!s03 M 246.305
(lrx.,5rx.,6rx.,8rx.)-form [70321-49-2] Chrysostomalide
Ac: [70329-68-9]. 61X-Acetoxy-4(15), 10(14), 11 (13)-guaiatrien- ClsH200 4 M 264.321
81X-olide · (4rx.,5rx.,6rx.,ap,J op,JJ rx. )-form [84093-51-6] lsogeigerin
C 17H 200 4 M 288.343 Constit. of Geigeria aspera. Cryst. (Etpjpet. ether) (as
Constit. of Baeria spp. Cryst. (Etpjpet. ether). Mp acetate). Mp 145° (acetate). [1X]~4 +64° (c, 0.27 in
129°. [1X]i;1 +7o (c, 0.1 in CHC1 3). CHCI 3) (acetate).
2-Methy/propanoy/: [70329-69-0]. Bohlmann, F. et a/, Phytochemistry, 1982, 21, 1679.
C 19H 240 4 M 316.396
Constit. of B. spp. Cryst. (pet. ether). Mp 104°.
6-Hydroxy-3-oxo-4-guaien-12,8-olide Sq-02060
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 2032.

4-Hydroxy-9-guaien-12,8-olide Sq-02056
o~o
~0
~0 OH
C 15H 200 4 M 264.321
HO I

(JP,6rx.,8P,10P,llrx.)-form [436-45-3] Geigerin. Pyrethrosin

Constit. of Geigeria aspera. Cryst. + 1H2 0. Mp 90-
ClsH 220 3 M 250.337 1000, Mp 191-192° (double Mp). [IX]!:? -64° (c, 1.1 in
(1 p,4a.,5rx.,8rx.,ll fl)-form CHCI 3).
Constit. of Helichrysum sp/endidum. Cryst. Mp 113°. Barton, D.H.R. et a/, J. Chern. Soc., 1964, 2518.
[1X]~4 -99° (c, 0.19 in CHC1 3). Boocock, D.G.B. eta/, J. Chern. Soc., Chern. Commun., 1966, 90
Jakupovic, J. et a/, Phytochemistry, 1989, 28, 1119. (ms)

6-Hydroxy-3-oxo-4,11(13)-guaiadien-12,8- Sq-02057 6-Hydroxy-2-oxo-1(10),3-guiadien-12,8- Sq-02061

olide olide

0~-00 ~O (5o,6a,8o,Jio)-fo=

C 15H 180 4
~
M 262.305 ClsH180 4
HO I

M 262.305
(lrx.,6P,8rx.,10fl)-form [56297-74-6] Mikanokryptin (5rx.,6rx.,8rx.,llrx.)-form [30860-27-6] Ferulidin
Constit. of Mikania micrantha. Cryst. (MeOH). Mp 248- Constit. of Ferula oopoda. Mp 170-172°.
2500. [IX]~ +264° (c, 0.1 in MeOH). Ac: [117232-60-7]. 6-Acetylferu/idin
Herz, W. eta/, Phytochemistry, 1975, 14, 233. C17H 200 5 M 304.342
Reynolds, W.F. eta/, Can. J. Chern., 1985, 63, 849 (pmr, cmr) Constit. of Artemisia lanata. Cryst. (EtOAc). Mp 207-
2100.
(5rx.,6p,8rx.,llrx.)-form [117255-07-9] Carmenin

521
2-0xo-3,5-guaiadien-12,8-olide - 2-0xo-1(5)-guaien-12,8-olide Sq-02062 - Sq-02067

Constit. of A. /anata. Cryst. (CHC1 3jMeOH). Mp 273- C15H 200 3 M 248.321

2750. Constit. of Pechuel-Loeschea leibnitziae. Gum. [a]~ +4°
Serkerov, S.Y. et al, Khim. Prir. Soedin., 1970, 6, 428 (struct) (c, 0.8 in CHC1 3).
Aguilar, J.M. et al, Phytochemistry, 1988, 27, 2229 (isol, struct) (l«.,Bfl,J0/1)-form [87302-42-9] Achalensolide
Constit. of Stevia achalensis and D. thieleana. Cryst.
2-0xo-3,5-guaiadien-12,8-olide Sq-02062 (MeOH/Etp). Mp 176-177°. [aJn +226.8° (c, 0.34 in
CHC13).
[125289-76-1]
(1 fJ,BfJ,J 0/1)-form
11P,J3-Dihydro: [5655-56-1]. 3-0xo-4-guaien-12,8/J-olide
lsol. from Geigeria alata. Cryst. Mp 133°. [a]~4 -17° (c,
0.67 in CHC1 3).
Samek, Z. et al, Collect. Czech. Chern. Commun., 1977, 42, 2441
(isol)
Holub, M. et al, Collect. Czech. Chern. Commun., 1982, 47, 670
C15H 180 3 M 246.305 (struct, abs config)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1160 (isol)
8/J-form Oberti, J.C. eta[, J. Org. Chern., 1983, 48, 4038 (isol, struct)
Constit. of Geigeria ornativa. Oil. Castro, V. eta[, Justus Liebigs Ann. Chern., 1983, 974 (isol)
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr) Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr, cmr)

3-0xo-1,11(13)-guaiadien-12,8-olide Sq-02063 2-0xo-1(10),3,5-guaiatrien-12,8-olide Sq-02065

(4cx,5cx,8cx, 10~)-form

CISHI603 M 244.290
C15H 180 3 M 246.305
(8«.,11«-H)-form [29455-13-8] Ferulin
(4«.,5«.,8«.,10/1)-form [86687-95-8] Constit. of Feru/a oopoda. Cryst. Mp 176-178°.
Constit. of Decachaeta thie/eana. Oil.
Serkerov, S.V., Khim. Prir. Soedin., 1970, 6, 134, 371; 1980, 16,
(4fl.5«,8«.,10/l)-form [71609-03-5] Thieleanine 629; Chern. Nat. Compd. (Engl. Trans/.), 130, 375, 448.
Constit. of D. thieleana. Cryst. Mp 175-177°.
lla,l3-Dihydro: [86630-19-5]. 3-0xo-1-guaien-12,8-o/ide
2-0xo-1 (1 0),3,11 (13)-guaiatrien-12,8-olide Sq-02066
C 15H 200 3 M 248.321 Virginolide
Constit. of D. thieleana. Oil.
[7 430-29-7]
(4fJ.SfJ,8fJ,JOJI)-form
11P,l3-Dihydro: [125356-44-7]. Desoxy-13-epiisogeigerin

~0
(incorr.)
C15H 200 3 M 248.321
Isol. from Geigeria a/ata. Cryst. Mp 106°. [a]~ + 163°
(c, 0.17 in CHC1 3).
(4«-.SfJ,BfJ,l 0/1)-form
11P,l3-Dihydro: Desoxy-4,5-bisepiisogeigerin C15H 160 3 M 244.290
C 15H 200 3 M 248.321 Constit. of Helenium virginicum. Cryst. (Me 2COjhexane).
lsol. from D. alata. Cryst. Mp 104°. [a]n + 113° (c, 0.32 Mp 133-135°. [a]~ +4.45° (c, 1.0 in CHC1 3).
in CHC1 3). Herz, W. et al, J. Org. Chern., 1967, 32, 507.
Alvarado, S. et al, Phytochemistry, 1979, 18, 330.
Castro, V. et al, Justus Liebigs Ann. Chern., 1983, 974. 2-0xo-1(5)-guaien-12,8-olide Sq-02067
Zdero, C. et al, Phytochemistry, 1989, 28, 3105.

~0
3-0xo-4,11(13)-guaiadien-12,8-olide Sq-02064

( 1cx,8cx, 10~)-form
C15H 180 3 M 246.305
0
(4fJ,8fJ,J 0/1)-form
Constit. of Decachaeta thieleana. Oil.
(1«.,8«.,10/1)-form [65017-97-2] Xerantholide Castro, V. eta[, Justus Liebigs Ann. Chern., 1983, 974.
C15H 180 3 M 246.305
Constit. of Anthemis austriaca, Decachaeta thieleana and
Xeranthemum cylindriceum. Cryst. (MeOHjEtOAc). Mp
190-192° (183°). [a]~ +223.3° (c, 0.38 in CHC1 3).
11P,13-Dihydro: 3-0xo-4-guaien-12,8a-o/ide. llfJ,J3-
Dihydroxerantholide

522
4,9,10-Trihydroxy-1,11(13)-..• - Absintholide Sq-02068 - Sq-02071

4,9,10-Trihydroxy-1,11(13)-guaiadien- Sq-02068
12,8-olide
Akihalin
[65128-07-6]
Guaiane dimers

Absinthin Sq-02070
[1362-42-1]
OH
C 15HZ1,05 M 280.320
Constit.--of Helenium autumna/e. Cryst. Mp 209-211°. [1X] 0
+ 75.2° (c, 0.4 in MeOH).
Kondo, Y. eta/, Tetrahedron Lett., 1977, 2155.

3,4,9-Trihydroxy-1(10)-guaien-12,8-olide Sq-02069
: 0
"{
0
C30 H 400 6 M 496.642
Constit. of Artemisia absinthium and A. sieversiana. Cryst.
(MeOH). Mp 182-183° dec. [1X] 0 + 180°.
C 15H 22 0 5 M 282.336 6' -Epimer: [11 029-90-6]. lsoabsinthin
(3rz,4rx.OH,8P,9P,J1rx.H)-form [79236-42-3] Carolenalol C~4006 M 496.642
lsol. from Helenium autumnale. Cryst. Mp 65-67°. [IX]~ Constit. of A. absinthium. Cryst. (MeOH). Mp 172-174°.
-93.SO (c, 0.14 in MeOH). 11-Epimer: 11-Epiabsinthin
9-Ketone: [57566-25-3]. 3oc,41X-Dihydroxy-9-oxo-1(10)- C30H 400 6 M 496.642
guaien-12,8P-olide. Caroklllllone Constit. of A. sieversiana. Oil. [1X]i;' + 159° (c, 0.34 in
C 15H 20 0 5 M 280.320 CHC1 3).
Constit. of H. autumnale. Cryst. (CHC1 3/hexane). Mp 10',11'-Diepimer: 10',11'-Epiabsinthin
245-247°. C30H 400 6 M 496.642
9-Ketone, 3-angeloyl: 3-0-Angeloy/caroknalone From A. sieversiana. Oil. [1X]i;' + 107° (c, 0.62 in CHC1 3).
C 20Hu;06 M 362.422 10' ,11 ,11'-Triepimer: 10' ,11 ,11'-Epiabsinthin
lsol. from H. autumnale. Oil. [IX]~ -90.1° (c, 0.66 in C30H 400 6 M 496.642
MeOH). From A. sieversiana. Oil. [1X]~4 +46° (c, 0.35 in CHC1 3).
9-Ketone, 3-tigloyl: 3-0-Tigloy/caro/enalone
Beauhaire, J. eta/, Tetrahedron Lett., 1980, 3191; 1981, 2269 (isol,
C 20Hu;06 M 362.422 struct)
From H. autumnale. Oil. [IX]~ -91.9° (c, 0.68 in Bohlmann, F. eta/, Phytochemistry, 1985, 24, 1009 (isol, derivs)
MeOH).
McPhail, A.T. eta/, J. Chern. Soc., Perkin Trans. 2, 1976, 332. Absintholide ·sq-02071
Ikoigawa, M. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1981,
101, 605. [91997-90-9]
0
~

XA~-~OH
~HoH
~0
0
C30H 380 8 M 526.625
Constit. of Artemisia absinthium. Cryst. (C6H 6). Mp 227-
2280. [1X]~ + 127° (c, 1.3 in CHC1 3).
Beauhaire, J. eta/, Tetrahedron Lett., 1984, 25, 2751.

523
Anabsin - Decathieleanolide Sq-02072 - Sq-02077

Anabsin Sq-02072 Artesieversin Sq-02075

[72542-39-3] [97626-46-5]

0
X
0
C 30H 400 7 M 512.642
Constit. of Artemisia absinthium. Cryst. Mp 276° dec. [a]i;5
+ 110° (c, 1.7 in Me 2CO). C 30H 380 6 M 494.627
Constit. of Artemisia sieversiana. Oil.
18-Deoxy: [6903-12-4]. Anabsinthin
C30H 400 6 M 496.642 Bohlmann, F. et al, Phytochemistry, 1985, 24, 1009.
lsol. from A. absinthium. Cryst. (C 6H 6). Mp 267° (260°).
[a]~ + 113° (CHC1 3). Biennin C Sq-02076
Kasyrov, Sh.Z. et al, Khim. Prir. Soedin., 1979, 495; Chern. Nat.
Compd. (Engl. Trans/.), 430 (struct, bib£)

Artanomaloide Sq-02073
[112823-41-3]

C 30H 420 7 M 514.658

C 32H 31,08 M 548.632 Constit. of Hymenoxys biennis. Powder (EtOAc).
Constit. of Artemisia anomala. Gum. (a]i)4 -17° (c, 0.2 in
Gao, F. et al, Phytochemistry, 1990, 29, 3875 (isol, pmr, cmr)
CHC1 3).
Jakupovic, J. et al, Phytochemistry, 1987, 26, 2777.
Decathieleanolide Sq-02077
[86030-18-4]
Artelein Sq-02074
[103654-30-4]

C 30H 340 6 M 490.595

C30H 360 8 M 524.610 Constit. of Decachaeta thieleana. Cryst. (CHC13/Et20). Mp
Constit. of Artemisia leucodes. Cryst. Mp 465-466°. 245°. [a]i)4 +68° (c, 0.4 in CHC1 3).
Mallabaev, A. eta/, Khim. Prir. Soedin., 1986, 22, 42 (isol, cryst Castro, V. et al, Justus Liebigs Ann. Chern., 1983, 974.
struct)

524
Gochnatiolide A - Ornativolide Sq-02078 - Sq-02083

Gochnatiolide A Sq-02078 Helisplendidilactone Sq-02081

[87606-12-0]

C 30 H 400 5 M 480.643
Constit. of Helichrysum splendidum. Cryst. Mp 172°. [cx]i;
C 30H 300 7 M 502.563 -64° (c, 0.21 in CHC1 3).
Constit. of Gochnatia paniculata. Gum. Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1119.
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 191.
Mexicanin F Sq-02082
Gochnatiolide B Sq-02079 [97452-14-7]
[87606-11-9]

C 30H 300 7 M 502.563 C28H 310 6 M 464.557

Constit. of Gochnatia paniculata. Gum. Constit. of Hellmium mexicanum. Cryst. Mp 311-315°. [cx]i,5
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 191. + 102° (c, 0.4 in EtOH).
Romo de Vivar, A. eta/, Tetrahedron Lett., 1985, 26, 579 (cryst
Handelin Sq-02080 struct)
[62687-22-3]
Ornativolide Sq-02083
[125305-15-9]

-OAc

0
~~~--
',,
pH
-OAc
If I
0 -
0
C34H 410 10 M 610.700 C30H 340 7 M 506.594
Constit. of Handelia trichophylla.
Constit. of Geigeria ornativa. Cryst. Mp 220° dec. (cx]i;
Tarasov, V.A. et al, Khim. Prir. Soedin., 1976, 745. + 129° (c, 0.14 in CHCI3).
2,3-Dihydro: [125289-70-5]. Dihydroorlllltil'olide
C30H 360 7 M 508.610
Constit. of G. ornativa. Gum.
Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (isol, pmr)

525
Pungiolide A - Chlorochrymorin Sq-02084 - Sq-02090

Pungiolide A Sq-02084 Bedfordiolide Sq-02087

[108885-55-8]

_Jl
0
-~0
r
H
H
I

o
C15H 22 0 3 M 250.337
Constit. of Bedfordia arborescens. Oil.
Zdero, C. et al, Phytochemistry, 1987, 26, 1207.
C30H 360 7 M 508.610
Constit. of Xanthium pungens. Cryst. Mp 182°. Bissecotanapartholide Sq-02088
l'ft,5'ft-Epoxide: Pungiolide B [102907-31-3]
C30H 360 8 M 524.610
Constit. of X. pungens. Cryst. Mp 165°.
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 2211 (isol, pmr, cmr)
0

Seco-, cyclo-, abeo- and CI5HI805 M 278.304

0

•
norgumanes
Constit. of Artemisia xanthochroa. Oil.
Huneck, S. et al, Phytochemistry, 1986, 25, 883.

Canambrin Sq-02089
[29135-44-2]
Alpinolide Sq-02085

0~~-
[94359-67-8]

HO -
0
0
CI5H2005 M 280.320
Constit. of Ambrosia canescens. Cryst. (EtOAcjisopropyl
ether). Mp 209-210°. [1X] 0 -134° (CHC1 3).
Ct5Hn0 3 M 250.337 Romo, J. et al, Phytochemistry, 1970, 9, 1611.
Constit. of rhizomes of Alpinia japonica. Needles. Mp 41-
430, [1X]i? -19.7° (c, 0.5 in CHC13). A 9,10-secoguaiane
deriv. Chlorochrymorin Sq-02090
Itokawa, H. et al, Chern. Lett., 1984, 1687. [52525-23-2]

coa.JH
1,4-Azulenedicarboxylic acid Sq-02086

COOH
M 216.193 Ct5H1,Cl05 M 314.765
Di-Me ester: 1,4-Dicarbomethoxyazulene Constit. of Chrysanthemum morifolium. [oc] 0 -18.3° (c, 0.4
C14H 120 4 M 244.246 in CHC1 3).
Cons tit. of lxiolaena leptolepis. Violet oil. Osawa, T. et al, Tetrahedron Lett., 1973, 5135.
Lehmann, L. et al, Phytochemistry, 1988, 27, 2994.

526
Clavukerin A- 1,4-Dimethyl-7-ethylazulene Sq-02091 - Sq-02096

aavukerin A Sq-02091 Constit. of Centaurea c/ementei. Cryst. (EtOAcjpet. ether).

2,3,3a,4,5,6-Hexahydro-1,4-dimethylazu/ene, 9CI. 2,8- Mp 193-195°.
Dimethylbicyc/o[5.3.0]deca-5,7-diene 16-Epimer: C/ementein B
[87687-54-5] C11 H:u;07 M 390.432
Constit. of C. c/ementei. Cryst. (EtOAcjMeOH). Mp
189-191°.
Absolute 16-Epimer, 4,15-dihydro: C/ementein C
configuration C11 H 180 7 M 392.448
Constit. of C. c/ementei. Cryst. (EtOAcjpet. ether). Mp
211-213°.
C 11H 18 M 162.274 Massanet, G.M. eta/, Tetrahedron Lett., 1983, 24, 1641 (isol)
Constit. of soft corals Clavularia koellikeri and Cespitularia Collado, I.G. eta/, Tetrahedron, 1986, 42, 3611 (struct, corifig)
sp. Oil. [ex)~ -53° (CHC1 3).
Bowden, B.F. et al, Aust. J. Chern., 1983, 36, 211 (isol) 4,10-Dihydroxy-4,5-seco-1(5), 11(13)-
Kobayashi, M. et al, Chern. Pharm. Bull., 1983, 31, 2160; 1984, 32,
Sq-02095
1667 (isol, cryst struct) guaiadien-12,8-olide
[125289-94-3]
aavukerin C Sq-02092
1,2,3,4,5,6-Hexahydro-1,4-dimethyl-1-azulenyl
hydroperoxide, 9CI. 1,2,3,4,5,6-Hexahydroxy-1-
hydroperoxy-1 ,4-dimethy/azu/ene
[91283-76-0] 0

Q)
OOH
C 1 ~H 11 04
(4/;,BP,JOrx.)-form
M 266.336

l Oex-Hydroxy-4H -tomentosin
Constit. of Geigeria plumosa. Oil. [ex]~4 +62° (c, 2.55 in
C 11H 180 1 M 194.273 CHCl 3).
Constit. of the soft coral Clavularia koellikeri. Unstable 4-Ketone: [125289-95-4]. 10ex-Hydroxy-4-oxo-4,5-seco-
oil. [ex)~ -61 o (CHCl 3). l(5), ll(l3)-guaiadien-l2,8P-olide. lOex-Hydroxytomentosin
Kobayashi, M. et al, Chern. Pharm. Bull., 1984, 32, 1667. Ct~H 10 04 M 264.321
Constit. of G. plumosa and G. ornativa. Oil.
Clavularin A Sq-02093 10-Deoxy, 10,14-didehydro: [125289-96-5]. 4-Hydroxy-4,5-
6-M ethy/-7-(3-oxobutyl)-2-cyc/ohepten-1-one, 9CJ seco-1(5),10(14),11(1 3)-guaiatrien-12,8P-olide. l O(l4)-
Dehydro-4H-tomentosin
[86582-92-5] C 1 ~H 10 0 3 M 248.321
Constit. of G. plumosa. Oil. [ex]~4 +68° (c, 0.38 in
CHCL 3).
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr, cmr)

1,4-Dimethyl-7-ethylazulene Sq-02096
C 11H 180 1 M 194.273 Chamazulene. Camazulene. Lindazulene
Constit. of Clavularia koellikeri. Cytotoxic. Oil. [529-05-5]
7-Epimer: [86746-90-9]. Clllvularin B
C 11H 180 1 M 194.273
Constit. of C. koel/ikeri. Cytotoxic. Oil.
Endo, M. et al, J. Chern. Soc., Chern. Commun., 1983, 322 (pmr,
struct)
Urech, R. eta/, J. Chern. Soc., Chern. Commun., 1984, 989 (synth,
struct)
Urech, R. et al, Aust. J. Chern., 1986, 39, 433 (synth) Ct4Ht, M 184.280
Still, I.W.J. eta/, Tetrahedron Lett., 1987, 28, 2489 (synth) Isol. as artifact from various sesquiterpene oils, e.g. from
Achillea and Artemisia spp. Blue oil. Bp 12 161°.
Clementein Sq-02094 I> C04780000.
[86939-93-7] Picrate: Cryst. (MeOH). Mp 116°.
3,6-Dihydro: [18454-88-l]. 7-Ethyl-3,6-dihydro-1,4-
dimethy/azulene
Ct4Ht8 M 186.296
Minor constit. of Artemisia absinthium. Pale-yellow
unstable oil.
5,6-Dihydro: [18454-89-2]. 7- Ethy/-5 ,6-dihydro-1 ,4-
dimethy/azu/ene
C14H18 M 186.296
Minor constit. of A. absinthium. Orange-black unstable
M 390.432 oil.

527
1,4-Dimethyl-2,3,3a,4,5,6-... - Mandassidione Sq-02097 - Sq-02103

Takeda, K. et al, Chern. Pharm. Bull., 1953, 75, 3865 (struct) Ivambrin Sq-02101
Bertelli, D.J. et al, Tetrahedron, 1968, 24, 2079 (isol, struct)
Mukherjee, D. et al, J. Am. Chern. Soc., 1979, 101, 251 (synth) [33204-43-2]

1,4-Dimetbyl-2,3,3a,4,5,6- Sq-02097
hexahydroazulene, 9CI
[85209-83-2]

C15H 110 4 M 266.336

Constit. of Iva ambrosiaefo/ia. Cryst. (EtOAc). Mp 156-
C 11H 18 M 162.274 1570.
Constit. of a Cespitularia sp. Oil. [1X]n -50.8° (c, 0.95 in 2-Ac: [33204-41-0]. Apachin
CHC1 3). C 17H:z..05 M 308.374
Bowden, B.F. eta/, Aust. J. Chern., 1983, 36, 211. Constit. of I. ambrosiaefo/ia. Cryst. (diisopropyl ether).
Mp 80-81.5°. [a]i; -147° (CHCI 3).
4-Formyl-1-azulenecarboxyUc acid, 9CI Sq-02098 2-Deoxy, 9a-hydroxy, 4-ketone: [37163-90-9]. lvalbatin
Ct5H:zo04 M 264.321

~
Constit. of I. dealbata. Unstable oil. [a]~ -84° (CHC1 3).
2-Deoxy, 9a-acetoxy, 4-ketone: Cryst. (EtOH). Mp 127-

Ho£-V 1280. [a]i? -136° (c, 2.0 in CHC1 3).

Yoshioka, H. et al, Phytochemistry, 1971, 10, 401 (isol)
Sundararaman, P. et al, Tetrahedron Lett., 1973, 3809 (struct)
C 11H 80 3 M 200.193
Chikamatsu, H. et al, J. Org. Chern., 1973, 38, 585 (isol)
Me ester: [43110-60-7]. 4-Formyl-1-methoxycarboxy/azu/ene
C 13H 100 3 M 214.220
Constit. of He/ichrysum bracteatum. Dark-blue cryst. Lumisantonin Sq-02102
(Etpjpet. ether). Mp 126.SO. [467-41-4]
Bohlmann, F. et al, Chern. Ber., 1973, 106, 1337.

IsosecotanaparthoUde
[102926-01-2]
Sq-02099
0~--
0
C 15H 180 3 M 246.305
lsol. from Artemisia monogyna and A. kurramensis. Mp
153.5-155°. [a]i;l -150.8° (c, 2.63 in CHC13). Presumably
an artifact.
Satoda, I. et al, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1959, 79,
267.
C,5H 180 5 M 278.304 Satoda, I. et al, CA, 1960, 54, 232l3b.
Constit. of Artemisia xanthochroa. Oil.
Huneck, S. et al, Phytochemistry, 1986, 25, 883. Mandassidione Sq-021 03
3-Methyl- 2-[2-( 1-methy/ethenyl)-5-oxohexy~- 2-cyc/openten-
lvalbin Sq-02100 1-one, 9CI
[7544-65-2] [118855-38-2]

C 15H 110:z M 234.338

C 15H 110 4 M 266.336 Constit. of Cyperus articulatus. Oil. [a]i; -9.10° (c, 0.74 in
Constit. of Iva dealbata. Cryst. Mp 160-162°. [a]~ -44.7° CHC13). A cleaved guaiane.
(c, 1.835 in CHCI 3).
Nyasse, B. eta/, Phytochemistry, 1988, 27, 3319.
Herz, W. et al, J. Org. Chern., 1967, 32, 682.

528
Microhelenin E - Tanaphillin Sq-02104 - Sq-02110

Microhelenin E Sq-02104 Subexpinnatin C Sq-02108

[82611-89-0] [99305-07-4]

R 1 =0H,R 2 =H 0
C 17H 1z04 M 290.358
C14H 160 4 M 248.278
Constit. of Centaura canariensis. Cryst. Mp 186-188°.
Constit. of Helenium microcephalum. Cryst. (C6H 6). Mp
l35-l36.SO. [cx]i; +47.2° (c, 1.2 in CHC1 3). 8-(2-Hydroxymethy/-2-propenoyl): [99305-08-5].
Subexpinnatin B
Kasai, R. eta/, J. Nat. Prod. (Lloydia), 1982, 45, 317.
C11 H 160 6 M 374.433
From C. canariensis. Non-cryst.
Microhelenin F Sq-02105 Collado, I.G. et al, Phytochemistry, 1985, 24, 2107 (iso[)
[83283-01-6] Collado, l.G. et al, J. Org. Chern., 1987, 52, 3323 (synth)
As Microhe1enin E, Sq-021 04 with
R 1 = H, R 2 = OH Tanapartholide Sq-02109

C14H1604 M 248.278
Constit. of He/enium microcephalum. Gum. [cx]i; -33.3° (c,
0.3 in Py).
Kasai, R. et al, J. Nat. Prod. (Lioydia), 1982, 45, 317.

Norpechuelol Sq-02106
[83161-58-4]
CISHI804 M 262.305

~-OH Constit. of Tanacetum parthenium.

3-Methoxy: [128286-96-4]. 3-Methoxytanapartholide
C 16H 100s M 292.331
Constit. of T. cilicium. Gum.
C 12H 180 1 M 194.273 Todorova, H. et a/, Planta Med., 1985, 174 (isol, pmr)
Constit. of Pechuel-Loeschea leibnitziae. Oil. [cx]n + 14° (c, Oksiiz, S., Phytochemistry, 1990, 29, 887 (isol, cmr, pmr)
1.4 in CHC13).
8-Ketone: [83161-57-3]. Norpechuelone Tanaphillin Sq-02110
C 12H 160 1 M 192.257
1-Hydroxy-3,1 0-dioxo-1 ,10-seco-4,11 ( 13)-guaiadien-12,6-
Constit. of P. leibnitziae. Oil. [cx]i;' + 10° (c, 0.2 in
o/ide
CHC1 3).
[98093-97 -1]
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1160.

Postiasecoguaianolide Sq-021 07
1,10-Dioxo-1 ,10-seco-4,11(13)-guaiadien-12,8-o/ide 0
[125675-17-4]

0
C1sH180s M 278.304
Constit. of Tanacetum macrophil/um.
Todorova, M. et al, Planta Med., 1985, 174.
CISHI804 M 262.305
Constit. of Postia bombycina. Oil. [cx]i;' +24° (c, 0.15 in
CHC1 3).
Rustaiyan, A. eta/, Phytochemistry, 1989, 28, 3127 (isol, pmr)

529
Ambrosic acid - 11,13-Dihydroxy-4-oxo-2-... Sq-02111 - Sq-02114

Constit. of G. fastigiata and Baileya multiradiata. Shows

in vivo antitumour activity. Cryst. (Me 2COjdiisopropy1
Pseudoguaianes ether). Mp 197-199°. [cc]~ -85.8°.
6-Tigloyl: [26305-86-2]. Linearifolin A
C20H 240 6 M 360.406
Constit. of Hymenoxys spp. Cryst. (Me2CO). Mp 187-
1880. [cc]i; -90° (c, 1.5 in CHC1 3).
Ambrosic acid Sq-02111 llrx,13-Dihydro, 6-angeloyl: [6995-10-4]. Fastigilin A
1rx,8rx-Epoxy-4-oxo-11 (1 3)-pseudoguaien-12-oic acid C20H 21,06 M 362.422
[6617-14-7] Constit. of G. fastigiata and B. multiradiata. Cryst. (H 20
or Me2C0jpet. ether). Mp 175-177°. [rx]i; -81.6°.
11cc,13-Dihydro, 6-(3-methylbutanoyl): [6995-11-5].
Fastigilin B
C20H 260 6 M 362.422
Constit. of G. fastigiata, B. multiradiata and H. acaulis.
Cryst. (Me 2C0jpet. ether). Mp 259-261°.
11 rx,13-Dihydro, 6-(2-methylpropenoyl): [25873-31-8].
C15H 200 4 M 264.321 Radiatin
Constit. of Ambrosia artemisiifolia. Cryst. Mp 211-213°. C 19H 240 6 M 348.395
[rx]n + 77° (CHC1 3). Constit. of B. multiradiata and B. pleniradiata. Cryst.
Inayama, S. et al, Chern. Pharm. Bull., 1974, 22, 1435 (isol) (MeN0 2/C 6H 6). Mp 183-185°.
Inayama, S. eta/, Tetrahedron Lett., 1974, 809 (cryst struct) 9-Ketone, 6-angeloyl: [64937-26-4]. Multisatin
C20 H 220 6 M 358.390
Conchosin A Sq-02112 Constit. of B. multiradiata. Cryst. (Me 2C0jheptane).
[28625-28-7] Mp 257-260°.
(lrx.,5p,6p,Brx.,9p,JOrx.)-form
9-Ac: [38927-55-8]. Amblyodin
Ct,H 200 6 M 320.341
Constit. of G. amblyodon. Cryst. (Me 2CO/Et20). Mp
220-222°.
(lrx.,5P,6f.,8f.,9f.,l0rx.)-form
111;,,13-Dihydro, 6-tigloyl: [26620-65-5]. Baileyolin
C20 H 260 6 M 362.422
0 Constit. of B. multiradiata. Cryst. (C 6H 6/CHC1 3). Mp
CtsH 180 5 M 278.304 180-182°. [cc]~ -74.6° (CHC1 3).
Constit. of Parthenium confertum. Cryst. (Me 2CO/CHC1 3). Waddel, T.G. eta/, Phytochemistry, 1969, 8, 2371 (Baileyolin)
Mp 150-152°. [rx]i: -29.4° (EtOH). Herz, W. eta/, J. Org. Chern., 1970, 35, 4117 (Linearifolin A)
de Vivar, A.R. et al, Tetrahedron, 1970, 26, 2775. Herz, W. eta/, Phytochemistry, 1972, 11, 2093; 1974, 13, 1187
(Gaillardipinnatin, Amblyodin, Desacetylgaillardipinnatin)
Dominguez, X.A. eta/, Planta Med., 1976, 30, 356 (Baileyolin)
6,9-Dihydroxy-4-oxo-2,11(13)- Sq-02113 Einck, J.J. eta/, J. Am. Chern. Soc., 1978, 100, 3544 (Radiatin)
pseudoguaiadien-12,8-olide Pettit, G.R. eta/, J. Org. Chern., 1978, 43, 1092 (Fastigilins,
Multisatin)
HI OH

~O (lo,5~,6a,8o,9~,10.)jo~ 11,13-Dihydroxy-4-oxo-2-pseudoguaien-
12,8-olide
Sq-02114

~0
OH 13

C 15H 180 5 M 278.304

(lrx..SP,6«,8rx.,9P,10rx.)-form
8-Ac: [53866-46-9]. Desacetylgaillardipinnatin
C 17H 200 6 M 320.341 HOH2 C OH
Constit. of Gaillardia amblyodon. Cryst. C 15H 200 5 M 280.320
(EtOAcjhexane). Mp 167-170°. [rx]~ -523.SO (c, 0.04 in
(1 rx..SP,BP,J Orx.,ll f.)-form [51292-63-8] Hymenoftorin
CHC1 3).
Constit. of Hymenoxys grandiflora. Antileukaemic agent.
Di-Ac: [53915-42-7]. Gaillardipinnatin Cryst. Mp 197-199°. [rxln -54°.
C 19H 220 7 M 362.379
Herz, W. eta/, J. Org. Chern., 1974, 39, 2013.
Constit. of G. pinnatifolia. Cryst. (Me 2C0jpet. ether).
Mp 270°.
(1 rx..SP,6rx.,Bp,9p,J Orx. )-form
6-Angeloyl: [64937-25-3]. Muhigilin
C20H 240 6 M 360.406
Constit. of Baileya multiradiata. Oily cryst.
(EtOAcjhexane).
6-(3-Methyl-2-butenoyl): [6995-12-6]. Fastigilin C
CwH240 6 M 360.406

530
4,6-Dihydroxy-1(10),11(13)-... - 2,4-Dihydroxy-11(13)-pseudoguaien-... Sq-02115 - Sq-02118

4,6-Dihydroxy-1(10),11(13)- Sq-02115 2,4-Dihydroxy-11(13)-pseudoguaien-12,8- Sq-02118

pseudoguaiadien-12,8-olide olide
H<;> HI

~-0 (l(J(,20(,40(,5~,80(,1Q(J()-form
0
~0
C 15H 200 4 M 264.321 C 15H 220 4 M 266.336
(4C.,5P,6P,8fl)-form (Jrx.,2rx.,4rx.,5p,Brx.,10rx.)-form [6754-35-4] Pulchellin A. Pulchellin
Wedelijloride Constit. of Gaillardia pulchella. Cryst. (EtOAc). Mp 166-
6-(Methylpropenoyl): 1670. [1X]~ -36.2° (c, 2.43 in CHCI 3).
C 19H 240 5 M 332.396 2,4-Di-Ac: [23754-36-1]. Pulchellin diacetate
Constit. of Wedelia grandiflora. Gum. C19H 160 6 1\1 350.411
6-(Methylpropenoyl), 4-Ac: From Loxothysanus sinuatus. Oil.
C11H 21;06 M 374.433 2-0-(3-Methylbutanoyl): Pulchellin 2-0-isollalerate
Constit. of W. grandiflora. Gum. C20H 310 5 M 352.470
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2047.
From L. sinuatus. Oil. [IX]~ -13° (c, 0.43 in CHC1 3).
2-Tigloyl: [97605-30-6]. Pulchellin 2-0-tiglate
C2oH 280 5 M 348.438
11,12-Dihydroxy-4-pseudoguaianone Sq-02116 From L. sinuatus. Oil.
(1rx.,2rx.,4rx.,5p,ap,10f/)-form

~
111X,l3-Dihydro, 4-ketone: 21X-Hydroxy-4-oxopseudoguaian-
12,8P-olide. 2rx.-Hydroxy-11 rx.,JJ-dihydroqonfertin

~OH
CH,OH CtsH22 0 4 M 266.336
Constit. of Stevia isomeca. Oil.
111X,l3-Dihydro, 4-ketone, 2-Ac: 2rx.-Acetoxy-llrx.,13-
C 15H 160 3 M 254.369 dihydroconfertin
(Jrx.,5p,10f/)-form C17H 240 5 M 308.374
12-Ac: From S. isomeca. Cryst. Mp 158°. [1X]n + 141° (c, 1.3 in
C 17H 28 0 4 M 296.406 CHC1 3).
Constit. of Jungia stuebelii. (1 rx.,2rx.,4p,sp,arx.,1 Orx. )-form
11,12-Di-Ac: Gum. [1X]~4 +70° (c, 0.71 in CHC13). 4-Epipulchellin
Constit. of G. pulchella. Oil. Mp 133-134° (as di-Ac).
Bohlmann, F. et a/, Phytochemistry, 1983, 22, 1201.
(1 rx.,2rx.,4rx.,5p,ap,1 Orx. )-form [28230-81-1] Neopulchellin
Constit. of G. pulchella. Cryst. Mp 166.5-167.5°. [1X]i;
1,4-Dihydroxy-11(13)-pseudoguaien-12-oic Sq-02117 +43° (c, 1 in CHCI 3).
acid 2-Ac: 6-Deoxychamissonolide
C 17H 240 5 M 308.374
Constit. of Arnica chamissonis. Cryst. (EtOH). Mp 204-
206.SO. [1X]i," +57.1° (c, 1.16 in CHCI 3).
4-Ketone, 6-(4-0-acetyl-P-v-glucopyranoside): [26836-43-1].
Paucin
C23 H 320 10 M 468.500
Constit. of Baileya pauciradiata and B. pleniradiata.
C 15H2404 M 268.352 Cryst. Mp 178-179°. [1X]i; +51.7°.
(1ft,4rx.,5rx.,10rx.)-form [116425-59-3] Vestic acid (1 rx.,2rx.,4P,5P,8P,J Orx. )-form
Constit. of Vicoa vestita. Needles (CHC1 3 /Me2CO). Mp 4-Epineopulche/lin
190-192°. [1X]n -18.6° (c, 1 in MeOH). Constit. of G. pulchella. Oil.
(1 rx.,4p,5rx.,1 Of/)-form (1 rx.,2C. ,4C. ,5p,ap,1 Of/)-form
4-Ac: 2-Ac: [16909-97-0]. Ste11int
C 17H 160 4 M 294.390 C17H 240 5 M 308.374
Constit. of Brasilia sickii. Gum. [IX]~ + 23° (c, 1.2 in Constit. of Stevia rhombifolia. Cryst. (Me2CO/Et20).
CHCI 3). Mp 184-186°. [1X]i," + 161° (CHC1 3).
4-Ac, Me ester: (1rx.,2C.,4C.,5P,8rx.,10f/)-form
C 18H 280 4 M 308.417 Di-Ac: [79383-83-8]. lnuchinenolide C
Isol. from B. sickii. C19H 160 6 M 350.411
4-Ketone: [22844-19-5]. 4-0xo-11(13)-pseudoguaien-12-oic Constit. of Inula britannica. Oil. [1X]i," -25.9° (c, 1.1 in
acid. Damsinic acid CHCI 3).
Constit. of Ambrosia ambrosioides. Cryst. Mp 112-113°. Herz, W. eta/, Tetrahedron, 1963, 19, 483 (iso/, uv, ir, pmr)
Doskotch, R.W. eta/, J. Org. Chern., 1970, 35, 486 (struct) Rios, T. eta/, Tetrahedron, 1967, 23, 4265 (Stevin)
Lansbury, P.T. eta/, Tetrahedron, 1978, 1909 (synth) Aota, K. eta/, J. Org. Chern., 1970, 35, 1448 (isol)
Wender, P.A. eta/, J. Am. Chern. Soc., 1979, 101, 2196 (synth) Yanagita, M. eta/, Tetrahedron Lett., 1970, 3007 (Neopulchel/in)
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1213 (isol) Cox, P.J. eta/, J. Chern. Soc., Perkin Trans. 2, 1977, 259 (Paucin)
Sachdev, K. et al, Indian J. Chern., Sect. B, 1987, 26, 503 (isol) Ito, K. et a/, Phytochemistry, 1981, 20, 271 (Inuchinenolide C)

531
3,4-Dihydroxy-11(13)-pseudoguaien-... - 4,14-Dihydroxy-11(13)-pseudoguaien-••• Sq-02119- Sq-02122

Willuhn, G. et al, Tetrahedron, 1981, 37, 773 (6- CtsHt80 4 M 262.305

Deoxychamissonolide)
Inayama, S. et al, Heterocycles, 1985, 23, 377 (synth)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1017
(Dihydroconfertins)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1021
(Hydroxydihydroconfertin, Acetoxydihydroconfertin)
Harimaya, K. et al, Heterocycles, 1988, 27, 83; 1990, 30, 993
(Epipulchellin, Epineopulchellin)
Yu, S. et al, Phytochemistry, 1988, 27, 2887 (derivs)
Zdero, C. et al, Phytochemistry, 1989, 28, 1653 (derivs)
3,4-Dihydroxy-11(13)-pseudoguaien-12,6- Sq-02119
olide
Constit. of Parthenium tomentosum. Cryst. Mp 195-198°.
de Villiers, J.P. et al, J. Chern. Soc., 1963, 4989 (Geigerinin)
Romo, J. et al, Tetrahedron, 1966, 22, 1499; 1967, 23, 527 (isol,
struct)
Oretega, A. et al, Can. J. Chern., 1968, 46, 1539 (Hymenoratin)
Geissman, T.A. et al, Phytochemistry, 1969, 8, 145 (isol)
Maldonado, E. et al, Phytochemistry, 1985, 24, 2981
(Dehydroperuvinine)
Bloszyk, E. et al, Collect. Czech. Chern. Commun., 1989, 54, 1903
(cryst struct, abs conjig, Geigerinin)
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr)
Gao, F. eta[, Phytochemistry, 1990, 29, 551, 1601 (Hymenoratin,
Geigerinin)

HO-if;
H6at>=
4,6-Dihydroxy-11(13)-pseudoguaien-12,8-
olide
I
Sq-02121

0 ~-q
C 15Hu04 M 266.336
(lrx..3rx.,4rx.,5fJ,6fJ,10/I)-form [5090-67-5] Ambrosio/
H~A~o
Constit. of Ambrosia psilostachya and A. dumosa. Cryst. C 15H 120 4 M 266.336
by subl. Mp 116-117°. (ex]~ -111.3° (c, 5.1 in CHC1 3).
(4fJ,6rx.,8rx.)-form
Mabry, T.J. et al, J. Org. Chern., 1966, 31, 681.
4-Ac: [125675-19-6]. 4P-Acetoxy-6ex-hydroxy-11(13)-
pseudoguaien-12,8ex-o/ide
3,4-Dihydroxy-11(13)-pseudoguaien-12,8- Sq-02120 C 17H 240 5 M 308.374
olide Constit. of Postia bombycina. Oil. [ex]i;' -16° (c, 0.4 in
CHC1 3).
H'
6-Ac: [125675-18-5]. 6ex-Acetoxy-4p-hydroxy-11(13)-
HO-e->--q pseudoguaien-12,8ex-o/ide
C 17H 240 5 M 308.374
H~o (1 a:,3a:,4~,5~,8a:, 1Oa:)-form Constit. of P. bombycina. Oil. [ex]i;' -28° (c, 0.2 in
CHC1 3).
C 15H 120 4 M 266.336
4-Ketone: [63568-73-0]. 6-Hydroxy-4-oxo-11(13)-
pseudoguaien-12 ,B-olide. Carpesiolin. 6ex-Hydroxy- 2,3-
(lrx..3rx.,4fJ,5fJ,8rx.,10rx.)-form [6902-72-3] Geigerinin. dihydroaromaticin
Neohymenoratin C 15H 100 4 M 264.321
lsol. from Geigeria aspera, G. africana, G. fi/ifolia and Constit. of Carpesium abrotanoides and Telekia speciosa.
Hymenoxys lemmonii. Cryst. (MeOH). Mp 202-203°. Cryst. (CHC1 3/hexane). Mp 122-123°. [ex]~ + 115.3° (c, 1
[ex]~ -10.7° (c, 2.3 in EtOH). in CHC13).
(lrx..Jrx.,4fJ,5fJ/lfJ,IOrx.)-form [19908-77-1] Hymenoratin. Odoratin 4-Ketone, Ac: [54999-07-4]. Ergo/ide
t C 17H 220 5 M 306.358
Isol. from H. odorata. Cryst. (Me2CO). Mp 165-167°. Constit. of Erigeron khorassanicus. Cryst. (EtOH). Mp
[ex]n + 71° (dioxan). 179-180°. [ex)i? + 123° (c, 4.88 in EtOH).
(lrx..3fJ,4fJ,5fJ,8fJ,JOfl)-form [6605-88-5] Cumanin Maruyama, M. et al, Phytochemistry, 1977, 16, 782 (Carpesiolin)
Constit. of Ambrosia spp. Cryst. (Me2CO/Etp). Mp Kok, P. et al, J. Org. Chern., 1979, 44, 4553 (synth, struct)
120°. (ex)n + 161° (CHC1 3). Bohlmann, F. et al, Phytochemistry, 1979, 18, 887 (Carpesiolin)
3-Ac: [21956-51-4]. Nagao, K. et al, Chern. Pharm. Bull., 1981, 29, 2733; 1983, 31, 414
C 17H 240 5 M 308.374 (synth)
Constit. of A. psilostachya. Cryst. (EtOAc). Mp 140- Ovezdurdyev, A. et al, Khim. Prir. Soedin., 1986, 22, 532
(Ergo/ide)
1430. (ex)n + 147° (c, 1 in CHC1 3). Rustaiyan, A. et al, Phytochemistry, 1989, 28, 3127 (isol, pmr)
3,4-Di-Ac: [6605-89-6].
C 19H 260 6 M 350.411
Constit. of A. psilotachya. Cryst. by subl. Mp 109°. (ex]n
4,14-Dihydroxy-11(13)-pseudoguaien-12,6- Sq-02122
+ 64° (CHC1 3). olide
3-Ketone: [13743-58-3]. 4fJ-Hydroxy-3-oxo-11(13)-

H~
pseudoguaien-12,8P-olide. Peruvinine
C 15H 100 4 M 264.321
Constit. of A. peruviana and G. ornativa. Cryst.
(Me2COjEt20). Mp 169-171°. [ex)n +34° (CHC1 3). The
sample from G. ornativa descr. as a gum and not
compared with the prev. descr. Peruvinine.
3-Ketone, 1,2-didehydro: 4P-Hydroxy-3-oxo-1,11(13)- 0
psuedoguaiadien-12,8P-olide. J-Dehydroperu11inine M 266.336

532
4,15-Dihydroxy-11(13)-pseudoguaien-... - 2,3-Epoxy-4-hydroxy-11(13)-... Sq-02123 - Sq-02127

(lrx.,4P.SP,6P,JOfl)-form Constit. of R. mol/is. Cryst. (CHC1 3/hexane). Mp 128-

4-Ac: [5492-09-1]. Hysterin 1290. [aJn + 80° (c, 0.02 in CHC1 3).
C 17 H 1,.0~ M 308.374 15-Ac:
Constit. of Parthenium bipinnatifidum and P. C17H140 5 M 308.374
hysterophorus. Cryst. (diisopropyl ether). Mp 166-168°. Constit. of R. mol/is. Cryst. (CHC1 3jhexane). Mp 150°.
[aln -80° (c, 1 in CHC1 3). [aJn + 136° (c, 0.5 in CHC13}.
Romo de Vivar, A. eta/, J. Org. Chern., 1966, 31, 673 (isol, uv, ir, 4-Ketone, 15-Ac: [76467-21-5]. 15-Acetoxy-4-oxo-ll(l3)-
pmr) pseudoguaien-12,8P-olide. Rudmo/Jitrin
Vivar, A.R. eta/, Phytochemistry, 1978, 17, 279 (isol) Constit. of R. mol/is. Cryst. (CHClJihexane). Mp 140-
Demuynck, M. et a/, J. Org. Chern., 1979, 44, 4863 (synth, struct) 1410. (aJn + 10.8° (c, 0.17 in CHC13).
Herz, W. eta/, J. Org. Chern., 1981, 46, 1356.
4,15-Dihydroxy-11(13)-pseudoguaien-12,6- Sq-02123
olide 11,13-Epoxy-2,4-dihydroxy-12,6- Sq-02125

"m
pseudoguaianolide

H<r·~
(lrx.,4P.SP,6P,JOfl)-form 0
Desacy/Jigulatin C
C 1 ~Hn0~ M 282.336
C 1 ~Hn0 4 M 266.336
Constit. of Rudbeckia grandiflora. Gum. (1 rx.,2P,4P.SP,6P,JOp,ll rx. )-form
Di-Ac: [65179-91-1]. Ligulatin C 2-Ac: [100664-33-3]. Parthoximenthine
C1,H:u;06 M 35o.4ll C17H140 6 M 324.373
Constit. of Parthenium argentatum and P. tomentosum. Constit. of Parthenium tomentosum. Cryst.
Cryst. (Me2COjhexane). Mp i34-138°. (EtOAcjhexane). Mp 183-186°.
4-Ketone, 15-Ac: [31299-06-6]. Ligulatin B. lncanin Maldonado, E. eta/, Phytochemistry, 1985, 24, 2981.
C 17 Hn0~ M 306.358
Constit. of P. spp. Cryst. (CHC1 3jdiisopropy1 ether). 3,4-Epoxy-2,6-dihydroxy-11(13)- Sq-02126
Mp 167-168°. [a]~ -52.1° (c, 0.6 in MeOH). pseudoguaien-12,8-olide
14-Acetoxy, 15-Ac: 14,15-Diacetoxy-4-hydroxy-11 (13)-

~-0
pseudoguaien-12,6-olide. 14-Acetoxytetraneurin D
(incorr.) ·
CI,Hl607 M 366.410
d'~o
Constit. of P. lozanianum. Oil. [a]i;' -112° (c, 0.4 in
CHC1 3). The published name 14-Acetoxytetraneurin D
ignores the additional !-hydroxy group of Tetraneurin
D. C 1 ~H10 0~ M 280.320
14-Acetoxy, 4-ketone, 15-Ac: [65129-90-0]. Ligulatin A (lrx.,2P,JP,4P.SP,6P,Brx.,JOrx.)-form
C 19H140 7 M 364.394 6-Ac: [5257-99-8]. Gaillardilin
Constit. of P. spp. C 17Hn06 M 322.357
Rodriguez, E. eta/, Phytochemistry, 1971, 10, 1145. Constit. of Gaillardia pinnatifida and G. arizonica. Cryst.
Rodriguez, E., Biochem. Syst. Ecol., 1977, 5, 207. (Me2CO/pet. ether). Mp 197-199°. [ali:' -2.03° (c, 1 in
lsman, M.B. eta/, Phytochemistry, 1983, 22, 2709. CHC1 3).
Maldonado, E. eta/, Phytochemistry, 1985, 24, 2981.
Jakupovic, J. eta/, Phytochemistry, 1987, 26, 761. Herz, W. et a/, Tetrahedron, 1966, 22, 693.
Vasquez, M. eta/, Phytochemistry, 1988, 27, 2195.
2,3-Epoxy-4-hydroxy-11(13)- Sq-02127
4,15-Dihydroxy-11(13)-pseudoguaien-12,8- Sq-02124 pseudoguaien-12,8-olide
olide I

q~¥'
-o
6

H I 0
H20H rt
I 5 I Ct~H:u,0 4 M 264.321
C 1 ~Hn04 M 266.336 6P-Hydroxy: [97643-93-1]. 2a,3a-Epoxy-4P,6P-dihydroxy-
(lrx.,4P.SP,BP,JOfl)-form [76467-15-7] Rudmollin 11 ( 13)-pseudoguaien-12,8a-olide. 6P-Hydroxyanuualin
Constit. of Rudheckia mol/is. Cryst. (CHC1 3jhexane). C 15 H:u,O~ M 280.320
Mp 210-211°. [aln + 110.4° (c, 0.5 in Py). Constit. of Loxothysanus sinuatus. Oil.
4-Ac: [76467-16-8]. 6P-Acetoxy: [97941-37-2]. 6P-Acetoxyamaralin
C 17 H 14 0~ M 308.374 C 17H:z:z06 M 322.357

533
10,14-Epoxy-4-oxo-11(13)-••. - 6-Hydroxy-4-oxo-2,11(13)-•.. Sq-02128 - Sq-02132

Constit. of Helenium amarum. Oil. [cx]i;4 +40° (c, 0.1 in
CHC1 3).
6cx-Hydroxy, 8-epimer: [20505-32-2]. 2cx,3cx-Epoxy-4p,6cx-
dihydroxy-11 (13)-pseudoguaiaen-12,8P-olide. Autrmt(lolide
C 15H 180 5 M 280.320
Constit. of H. autumna/e. Cryst. (EtOAcfhexane). Mp
188-190°. [ex]~ +20.6° (c, 1.8 in CHCI 3).
(1«,2«,3«,4P.SP,8tz.,l0tz.)-form [6831-10-3] Amaralin
Constit. of Helenium amarum. Has analgesic activity.
Cryst. (C6HJ. Mp 195-198°. [cx] 0 +5° (CHC13).
Lucas, R.A. et al, J. Org. Chern., 1964, 29, 1549 (isol, struct)
von Dree1e, R.B. et al, J. Am. Chern. Soc., 1975, 97, 5256
(Autumnolide)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1021, 1315 (iso/)
10,14-Epoxy-4-oxo-11(13)-pseudoguaien- Sq-02128
12,8-olide
11,13-Dihydro: 1-Hydroxy-4-oxo-2-pseudoguaien-12,6-olide.
Dihydroparthenin
C15H180 4 M 264.321
Constit. of P. hysterophorus. Cryst. Mp 145°.
1,2-Dihydro: [2571-81-5]. 1-Hydroxy-4-oxo-11(13)-
pseudoguaien-12,6-o/ide. Coronopilin. 1,2-
Dihydroparthenin
C15H180 4 M 264.321
Constit. of P. incanum, Ambrosia psilostachya, A.
artemisiifolia, I. nevadensis and I. acerosa. Cryst.
(Me2CO/diisopropyl ether). Mp 177-178°. [cx]i} -30.2°
(c, 4.2 in EtOH).
Herz, W. et al, J. Org. Chern., 1961, 26, 5011 (Coronopilin)
Herz, W. et al, J. Am. Chern. Soc., 1962, 84, 2601 (iso/, struct)
Geissman, T.A. et al, J. Org. Chern., 1964, 29, 2553 (Coronopilin)
Kok, P. eta/, Bull. Soc. Chim. Be/g., 1978, 87, 615 (synth)
Heathcock, C.H. et al, J. Am. Chern. Soc., 1982, 104, 6081 (synth)
Fronczek, F.R. eta/, Acta Crystal/ogr., Sect. C, 1989, 45, 2006
(Parthenin, cryst struct)
Ta1war, K.K. et al, Phytochemistry, 1989, 28, 1091
(Dihydroparthenin)

2-Hydroxy-3-oxo-1,11(13)- Sq-02131
pseudoguaiadien-12,8-olide

CtsHta04 M 262.305
(lrx..SP,8rx.,lfh)-form [72776-47-7] Pulicariolide
Constit. of Pulicaria crispa. Oil. [cx]i;4 + 15.4° (c, 0.33 in
CHCI 3). 0
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1231.
CtsHt80 4 M 262.305
11(13)-Epoxy-4-oxo-2-pseudoguaien-12,6- Sq-02129 (5p,Bp,JOtz.)-form [117480-00-9] Cooperin
olide Constit. of Psilostrophe cooperi. Cryst. (CHCI3/Et0Ac).

chyy
Mp 202°.
Stuppner, H. eta/, Phytochemistry, 1988, 27, 2681.

6-Hydroxy-4-oxo-2,11(13)- Sq-02132
cr~ pseudoguaiadien-12,8-olide
0 H'
C15H 180 4 M 262.305
(l«.SP,6P,JOP,Iltz.)-form [65179-88-6]
~0(1o,5,,6a,8o,I0o)-fo'm
Stramonin B
Constit. of Parthenium tomentosum. Cryst.
(Et20/CHC13). Mp 175-176°. [cx]ii -125° (c, 1.14 in C15H 180 4 M 262.305
CHC13). (lrz.SP,6rz,8rz,l0rz)-form
Grieco, P.A. et al, J. Org. Chern., 1978, 43, 4552. 8-Epihelena/in
Constit. of Loxothysanus sinuatus. Cryst. Mp 179°. [cx]i;4
1-Hydroxy-4-oxo-2,11(13)- Sq-02130 -7° (c, 0.84 in CHCI 3).
pseudoguaiadien-12,6-olide Ac: [3668-14-2]. Bigelovin
C17H 180 5 M 304.342
Constit. of He/enium bige/ovii, Gaillardia fastigiata and
G. pinnatifida. Cryst. (Et20jpet. ether). Mp 190-191°.
(cx] 0 +46.1° (EtOH).
6-Tigloy/: 8-Epihelanalin tig/ate
C:zeH:z.Ps M 344.407
From L. sinuatus. Oil.
11,13-Dihydro: see 6-Hydroxy-4-oxo-2-pseudoguaien-12,8-
C15H 180 4 M 262.305 olide, Sq-02137 '
I> 809635000. (lrz.SP,6tz.,BP,10tz.)-form [6754-13-8] Helenalin
Constit. of H. spp. Also from Gaillardia spp. Has
(l«.SP,6P,JO/I)-form [508-59-8] Part/renin sternutatory and vermifugal props. and is toxic to fish.
Bitter principle of Parthenium hysterophorus and Iva Antitumour agent. Cryst. (EtOH or C 6H 6). Mp 225-
nevadensis. Cryst. (H20). Mp 163-166°. [cx]~ +7.02° (c, 2280. [cx]~ -102.8° (CHC1 3}.
2.71 in CHC13). I> BD9630000.

534
11-Hydroxy-2-oxo-3,9-... - 2-Hydroxy-4-oxo-11(13)-pseudoguaien-... Sq-02133 - Sq-02136

Ac: [10180-86-6]. Angustibalin Constit. of Melanoselinum decipiens. Cryst. (C6H 6fpet.

C 17Hz00 5 M 304.342 ether). Mp 224-226°. [aln -74° (c, 0.1 in EtOH).
Constit. of Balduina angustifolia. Needles (CH 2Cl 2). Mp Gonzalez, A. G. et al, An. Quim., 1974, 70, 1028.
181°. [a]i; -54° (c, 0.1 in C6H 6).
(2- Methylpropenoyl): 10-Hydroxy-4-oxo-12,6-pseudoguaianolide Sq-02134
C 19H110 5 M 330.380
Constit. of Monactis macbridei. Oil. [a]i;l -42° (c, 0.18 HO
in CHC1 3).
0-(2-Hydroxymethylpropenoyl): [79421-62-8]. Kingiolide
C 1 ~zz0 6 M 346.379
Constit. of Kingianthus paradoxus. Gum. [ali;' -70.1 o (c,
6.5 in CHC1 3).
(l~,sp,6p,8~,10~)-form [5945-41-5] Mexicanin I. 6{1-
Hydroxyaromatin
Constit. of H. spp. and G. pinnatifida. Cryst.
(CHCl 3fMeOH). Mp 260-263° (257-260°). [aJn +42.SO C,sH120 4 M 266.336
(CHC1 3) ( + 32°). Also descr. as an oil by Bohlmann, et (1~,5P,6ft,JO~,ll~)-form [25362-52-1] Franserin
a/. Constit. of Franseria ambrosioides and Ambrosia
Ac: [5988-99-8]. Linifolin A ambrosioides. Cryst. (EtOAcjEtzO). Mp 225-227°.
C 17H100 5 M 304.342 Romo, J. et al, Can. J. Chern., 1968, 46, 1535 (isol, struct)
Constit. of H. linifolium. Cryst. (Me2COjpet. ether). Mp Dominguez, X.A. eta/, Rev. Latinoam. Quim., 1985, 16, 72 (isol,
195-198°. [a]~ + 33° (c, 0.4 in CHC1 3). stereochem)
(1 ~.sp,6p,ap,J o~ )-form
Ac: [6895-47-2]. Balduilin 1-Hydroxy-4-oxo-11(13)-pseudoguaien- Sq-02135
C 17Hz00 5 M 304.342 12,8-olide
Constit. of B. uniflora. Cryst. (C6H 6). Mp 231-232°. [1X]~4
+ 57° (c, 1.05 in CHC1 3).
lla,13-Epoxide: [128286-76-0]. Vi/losin A
C,sH 180 5 M 278.304 ~0
Isol. from Hymenoxys scaposa var. villosa.
Herz, W. et al, J. Am. Chern. Soc., 1963, 85, 19 (pmr)
Herz, W. et al, Tetrahedron, 1963, 19, 1359; 1965, 21, 1711; 1966,
~0
22, 1907 (Balduilin, Bigelovin) C 15H100 4 M 264.321
Dominguez, E. et al, Tetrahedron, 1963, 19, 1415 (Mexicanin I) (l~,sp,ap,J0/1)-form[6617-45-4] Peruvin
Mazhar-Ul-Haq, et al, J. Chern. Soc. B, 1969, 956 (cryst struct, Constit. of Ambrosia spp. Cryst. (Me2CO/Etz0). Mp
Helena/in) 191-193°. [aJn + 155° (CHC1 3).
Lee, K.-H. eta/, J. Pharm. Sci., 1972, 61, 626 (isol)
Pettit, G.R., J. Med. Chern., 1974, 17, 1013 (pharmacol, Helena/in) Joseph-Nathan, P. et a/, Tetrahedron, 1966, 22, 1723.
Ohfune, Y. et al, J. Am. Chern. Soc., 1978, 100, 5946 (synth, bib/,
Helena/in) 2-Hydroxy-4-oxo-11(13)-pseudoguaien- Sq-Q2136
Roberts, M.R. eta/, J. Am. Chern. Soc., 1979, 101, 7626 (synth)
Bolhrnann, F. et al, Phytochemistry, 1981, 20, 1146 (Kingiolide) 12,6-olide
Grieco, P.A. et al, J. Am. Chern. Soc., 1982, 104, 4233 (synth)

~ (la,2o<,4~,6~,10~)-fo'm
Grieco, P.A. eta/, J. Org. Chern., 1983, 48, 360 (synth)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1315 (6P-
Hydroxyaromatin)
De Vivar, A.R. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 284 (cryst
struct, Linifolin A)
Watson, W.H. eta/, Acta Crystallogr., Sect. C, 1990, 46, 1524
(cryst struct)
Gao, F. et al, Phytochemistry, 1990, 29, 895 (Villosin A) 0
C,5H100 4 M 264.321
11-Hydroxy-2-oxo-3,9-pseudoguaiadien- Sq-02133 (1~,2~,4p,6p,JO/I)-form [28238-83-7]/voxanthin
12,6-olide Constit. of Cycloachaena xanthifolia. Cryst. Mp 164-
1660. [a]~0 +47.7°.
(1~,2p,4p,6p,JO/I)-form [33649-13-7] Bipinnatin
Constit. of Parthenium spp. Cryst. (Me2CO). Mp 196-
1980. [a]i; -9.1° (c, 0.5 in MeOH).
Novikov, V.J. et al, Khim. Prir. Soedin., 1969, 4, 375 (isol)
Samek, Z. et al, Collect. Czech. Chern. Commun., 1970, 35, 3818
(struct)
Rodriguez, E. et a/, Phytochemistry, 1971, 10, 1145 (isol, struct)
Baiza, F., Phytochemistry, 1988, 27, 1421 (isol, cmr)
C 15H 180 4 M 262.305 Fronczek, F.R. eta/, Acta Crystallogr., Sect. C, 1989, 45, 2006
(1~,5~,6p,l1~)-form (cryst struct)
Angeloyl: [57082-62-9]. Decipienin C
C10HZ405 M 344.407

535
6-Hydroxy-4-oxo-2-pseudoguaien-... - 8-Hydroxy-4-oxo-11(13)-pseudoguaien-... Sq-02137- Sq-02138

6-Hydroxy-4-oxo-2-pseudoguaien-12,8- Sq-02137 Mexicanin C

olide Constit. of H. mexicanum. Cryst. Mp 251-252°. {1X]n
-80° (CHC13).
I
H' Ange/oyl: [16503-32-5]. Bre11ilin A

~ (1o,5~,6a,8~.IO.,llo)-fwm
0
C 28H 260 4 M 330.423
Constit. of H. a/ternifolium. Cryst. (Et 20jhexane). Mp
116-117°. [1X]n -264° (c, 1 in CHC1 3).
(lr~.,5p,6~:~.,8p,IO~:~.,ll/1)-form
HO HI
Angeloy/: [3668-12-0]. Thurberilin
C 15H 280 4 M 264.321 C28H 260 5 M 346.422
(1«,5P,6«,8P,JO~:~.,ll/1)-form [34257-95-9] Plenolin Constit. of H. thurberi. Cryst. (Me 2COjdiisopropyl
Constit. of Baileya pleniradiata and Helenium autumnale. ether). Mp 162°. {1X]i;' +20° (c, 0.4 in 95% EtOH).
Antitumour agent. Cryst. Mp 223-226°. (1«,5P,6P,8«,10r~.,llr~.)-form
I> BD9638000. Desacetylisotenulin
Ac: [36505-53-0]. Arnicolide A Isol. from H. bigelovii. Cryst. (EtOH). Mp 255° (225°).
C 17H 120 5 M 306.358 [IX]~ -15° (c, 0.31 in CHC1 3).
Constit. of Arnica montana. Cryst. (Etp). Mp 177-178°. Ac: [10092-04-3]. lsotenulin
[1X]~ -112.8° (c, 0.13 in MeOH). C17H120s M 306.358
3-Methyl-2-butenoyl: [90042-11-8]. 6-0-Senecioylplenolin Isol. from H. tenuifolium, H. arizonicum and H.
CwH21;05 M 346.422 bigelovii. Cryst. (H 20). Mp 160-161°. [1X]n +6° (c, 1.57
Constit. of Centipeda minima. Cryst. (MeOH). Mp 187- in EtOH). Prob. artifact.
1900. [1X]ii -47.6° (c, 0.0013 in CHC1 3). Herz, W. et a/, Tetrahedron, 1963, 19, 1359 (Mexicanin C,
3-Methylbutanoyl: [34532-66-6]. Arnicolide B lsotenulin)
C10H 280 5 M 348.438 de Vivar, A.R. et al, Tetrahedron, 1966, 22, 3279 (Thurberilin)
Constit. of A. montana. Cryst. (pet. ether). Mp 116-117°. Herz, W. eta/, J. Org. Chern., 1968, 33, 2780 (Brevi/in A)
[IX]~ -96.8° (c, 0.23 in MeOH). Poplawski, J. eta/, Collect. Czech. Chern. Commun., 1971, 36, 2189
(Arnicolides)
Angeloyl: [63569-07-3]. Microhelenin C Mazar-Ul-Haque, et al, J. Chern. Soc., Perkin Trans. 2, 1974, 223
C 28H 260 5 M 346.422 (cryst struct, Isotenulin)
Constit. of H. microcephalum. Gum. [IX)i! -85° (c, 1.3 in Lee, K.-H. eta/, Tetrahedron Lett., 1974, 1149 (Plenolin)
MeOH). McPhail, A.T. eta/, J. Chern. Soc., Perkin Trans. 2, 1975, 487
2-Methylpropanoyl: [34532-67-7]. Arnicolide C (cryst struct, Plenolin)
Lee, K.H. et al, Phytochemistry, 1977, 16, 393 (Microhelenins)
C19H26 0 5 M 334.411 Kubo, I. eta/, Agric. Bioi. Chern., 1984, 48, 3147
Constit. of A. montana. Cryst. (Me2C0jpet. ether). Mp (Desacetylisotenulin)
137-138°. [IX]~ -91.1° (c, 0.25 in MeOH). Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1984, 503 (derivs)
2-Methylpropenoyl: [34532-68-8]. Arnicolide D Wu, J.-B. et al, Chern. Pharm. Bull., 1985, 33, 4091 (6-
C 19H240 5 M 332.396 Senecioylplenolin)
Constit. of A. montana. Cryst. (pet. ether). Mp 100-102°. Bohlmann, F. eta/, Phytochemistry, 1985, 24, 1021 (derivs)
[1X]n + 7o.
2-Methylbutanoyl: [63569-08-4]. Microhelenin B 8-Hydroxy-4-oxo-11(13)-pseudoguaien- Sq-02138
C 28H 280 5 M 348.438 12,6-olide
Constit. of H. microcephalum. Cryst. (CHC1 3). Mp 111-
1130. [IX]~ -84.9° (c, 1.75 in MeOH).
Tigloyl:

cr·'Q=
C 28H 260 5 M 346.422 cf>--OH
Constit. of Monactis macbridei. Oil. [1X]ii -94° (c, 0.2 in
CHC1 3).
3-Methyl-2-butenoyl:
C 28 H 260 5 M 346.422 0
Constit.,of M. macbridei. Cryst. (Etpjpet. ether). Mp C 1sH280 4 M 264.321
183°. [1X]ii -104° (c, 0.09 in CHC1 3). (1 r~.,5p,6p,8~:~.,10r~.H)-form [17066-68-1] Deacetylconfertijlorin
0-(2-Hydroxymethylpropenoyl): Constit. of Ambrosia confertijlora. Cryst. (MeOH). Mp
C 19H 240 6 M 348.395 202-204°. [IX]~ + 17.2° (c, 2.75 in MeOH).
Constit. of M. macbridei. Oil. Ac: [17066-70-5]. Confertijlorin
0-(2,3-Epoxy-2-methy/propanoyl): C 17H 120 5 M 306.358
C 19H 240 6 M 348.395 Constit. of A. confertiflora. Cryst. (MeOH). Mp 145°.
Constit. of M. macbridei. Oil. [1X]~4 -91° (c, 0.1 in {IX]~ +25.0° (c, 5 in MeOH).
CHC1 3). Fischer, N.H. et al, Tetrahedron, 1967, 23, 2529 (iso[)
0-(4-Hydroxy-2-methylenebutanoyl): Vargas, D. et al, J. Nat. Prod. (Lloydia), 1986, 49, 133 (cryst
C 28H 260 6 M 362.422 struct)
Constit. of M. macbridei. Oil. {1X]~4 -47° (c, 0.2 in
CHC1 3).
2,3-Dihydro, 2P-hydroxy, 2-methy/butenoy/:
C 19H 260 6 M 350.411
Constit. of M. macbridei. Oil. {1X]~4 +2.SO (c, 0.08 in
CHC1 3).
(1«,5P,6«,8P,10r~.,ll«)-form

536
6-Hydroxy-1,11(13)-pseudoguaiadien-... - Mexicanin H Sq-02139 - Sq-02143

6-Hydroxy-1,11(13)-pseudoguaiadien-12,8- Sq-02139 Constit. of F. crispa. Oil. [oc]~ + 10° (c, O.i in CHC1 3).
olide 4-Ketone, 11,13-dihydro, llfl-hydroxy: 11-Hydroxy-4-
oxopseudoguaian-12,8-olide. 11 fl-Hydroxy-11 ,13-dihydro-
\
8-epiconfertin

N'>..o
\

C 15Hn04 M 266.336
(Sp,oo,sp,!Oa),fo"" Constit. of Bedfordia arborescens. Gum.
0 (1«.,4«.,5fJ,8fJ,10f/)-form [68832-40-6] Dihydroconfertin

~ Constit. of lnula spp. Cryst. Mp 147°. [oc]~ + 83.3° (c,

0.6 in CHC1 3).
C 15H 180 4 M 262.305 4-Ketone: [19908-69-1]. Confertin. Anhydrocumanin
(5fl,6«.,8fl,10rz)-form [5989-52-6] Mexicflllin A C1 5H 100 3 M 248.321
Constit. of Helenium mexicanum. Cryst. Constit. of Ambrosia spp. Cryst. (Me2CO/hexane). Mp
(Me 2C0fhexane). Mp 138-140°. [ocJn -27° (CHC1 3). 145-146°.
(5fl,6fl,8«.,10«)-form 4-Ketone, 11/1,13-Dihydro: llfl,JJ-Dihydroconfertin
Ac: Linifolin Bt C 15Hn03 M 250.337
C 17H 100 5 M 304.342 Constit. of D. graveolens. Oil. [oc]~4 + 17° (c, 0.26 in
Constit. of H. linifolium. Cryst. (C6H 6 /pet. ether). Mp CHC1 3).
149-151°. (1«.,4fl,5fl,8«.,10«)-form
11/1,13-Dihydro, Ac: [6586-77-2]. lsoheleniflmlll'in 2-Deoxy-4-epipukhellin
C 17Hn05 M 306.358 Constit. of Ondetia linearis. Cryst. Mp 135°. [oc]~ +43°
Constit. of H. amarum. Cryst. (Et 20fhexane). Mp 124- (c, 0.59 in CHC1 3).
1260. [oc]~ + 1.8° (c, 0.25 in CHC1 3). Romo, J. et al, Can. J. Chern., 1968, 46, 1535 (isol)
Marshall, J.A. et al, J. Am. Chern. Soc., 1976, 98, 4312 (synth)
Herz, W., J. Org. Chern., 1962, 27, 4043; 1968, 33, 2780 (struct)
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1165 (isol, struct)
Herz, W. et al, J. Am. Chern. Soc., 1963, 85, 19 (isol)
Wender, P.A. et al, J. Am. Chern. Soc., 1979, 101, 2196 (synth)
Herz, W. et al, Tetrahedron, 1966, 22, 1709 (struct)
Bohlmann, F. et al, Phytochemistry, 1979, 18, 887 (8-Epiconfertin)
E1 Sohly, M.A. et al, J. Nat. Prod. (Lloydia), 1981, 44, 617
Heathcock, C.H. eta/, J. Am. Chern. Soc., 1982, 104, 1907 (synth)
( /soheleniamarin)
Schultz, A.G. et al, J. Am. Chern. Soc., 1982, 104, 5800 (synth)
Ziegler, F.E. eta/, J. Am. Chern. Soc., 1982, 104, 7174 (synth)
4-Hydroxy-11(13)-pseudoguaien-12-oic Sq-02140 Zdero, C. et al, Phytochemistry, 1987, 26, 1207 (deriv)
acid Rustaiyan, A. et al, Phytochemistry, 1987, 26, 2603 (derivs)
Kennedy, M. et a/, J. Chern. Soc., Chern. Commun., 1988, 1028
(synth)

H~~H
Zdero, C. eta/, Phytochemistry, 1989, 28, 1653 (2-Deoxy-4-
epipulchellin)
Abdel-Mogib, M. et al, Phytochemistry, 1990, 29, 2581 (deriv)

Hymenoratin D Sq-02142
[126794-74-9]
C 15H:w03 M 252.353

~~~00
4fl-form [130395-57-2]
Constit. of Xanthium pungens. Gum.
Ahmed, A.A. et al, Phytochemistry, 1990, 29, 2211 (isol, pmr, cmr)

4-Hydroxy-11(13)-pseudoguaien-12,8-olide Sq-02141

C10H 280 6 M 364.438

~
Constit. of Hymenoxys odorata.
( lcx,4oc,5P,8cx, 1OP)-/orm Gao, F. et al, Phytochemistry, 1990, 29, 551 (isol, pmr, cmr, cryst
0 struct)

C 15Hn0 3 M 250.337 Mexicanin H Sq-02143

(1«.,4«.,5fl,8«.,10f/)-form \

~0
4-Ketone: 4-0xo-11 (1 3)-pseudoguaien-12,8-olide. 8-epi-
Confertin. 2,3-Dihydroaromomaticin
C 15H 100 3 M 248.321
Constit. of Francoeuria crispa and Telekia speciosa.
Cryst. (Et20). Mp 151°. [oc]~ + 115° (c, 0.7 in CHC1 3), J~o
[oc]~ + 142° (c, 0.12 in CHC1 3).
4-Ketone, 11/1,13-Dihydro: 4-0xopseudoguaian-12,8-olide. C1sH180 5 M 278.304
11/1,13-Dihydro-8-epiconfertin Constit. of Helenium mexicanum. Cryst. Mp 150-151°. [a.Jn
-44.6°.
C 15Hn03 M 250.337
From Dittrichia graveolens. Oil. [oc]~4 +62° (c, 0.4 in Romo, J. et al, Tetrahedron Lett., 1966, 1029.
CHC1 3).
4-Ketone, JOa.-hydroxy: 10-Hydroxy-4-oxo-11(13)-
pseudoguaien-12,8-olide. 10«.-Hydroxy-8-epiconfertin
C 15H 200 4 M 264.321

537
Microhelenin A - Parthoxetin Sq-02144 - Sq-02149'

Microhelenin A Sq-02144 4-0xo-2,11(13)-pseudoguaiadien-12,8- Sq-02147

[61490-63-9] olide
H'

~-o (lcx,5P,8cx,10cx)-form

~0
CtsHta04 M 262.305 CtsH180 3 M 246.305
Constit. of Helenium microcepha/um. Cryst. Mp 140-141°. (1«,5/l,Brr.,lO«)-form [5945-42-6] Aromaticin. 6-Deoxymexicanin
{-a]~-+89° (c, 1 in MeOH). Constit. of Helenium aromaticum and H. amarum. Cryst.
Lee, K.-H. et al, J. Pharm. Sci., 1976, 65, 1410. (Me2CO). Mp 232-234°. [cxJn + 18° (CHC1 3).
(1«,5/l,BfJ,lO«)-form [6754-14-9] Aromatin. 6-Deoxyhe/ena/in
4-0xo-1,11 (13)-pseudoguaiadien-12,6- Sq-02145 From H. aromaticum. Cryst. (Etpjhexane). Mp 159-
olide 1600. [cx]n -6° (CHC1 3).
Neoambrosin (1«,5fJ,8fl,10fJ)-form
[18446-70-3] llcx,13-Dihydro: 4-0xo-2-pseudoguaien-12,8P-olide. 2,3-
Dehydro-11 «,13-dihydroconfertin
C15H 200 3 M 248.321
lsol. from Stevia isomeca. Cryst. Mp 167°.
Romo, J. et a/, Tetrahedron, 1964, 20, 79 (isol, struct)
Pinhey, J.T. eta/, Aust. J. Chern., 1965, 18, 543 (pmr)
Nakazaki, M. et al, Tetrahedron Lett., 1966, 2615 (synth)
Ziegler, F.E. et al, J. Am. Chern. Soc., 1982, 104, 7174 (synth)
Lansbury, P.T. et al, Tetrahedron, 1982, 38, 2797 (synth, bib/)
Bohlmann, F. et al, Phytochemistry, 1985, 24, 1017 (deriv)
C 15H 180 3 M 246.305
Constit. of Hymenoclea sa/sola and H. monogyra. Cryst.
(EtOAcjhexane). Mp 126-127°. [ex]~ -66° (c, 2 in 2-0xo-3-pseudoguaien-12,6-olide Sq-02148
CHCl 3).
Geissman, T.A. et al, Phytochemistry, 1967, 6, 1563 (isol)
Toribio, F.P. et al, Phytochemistry, 1969, 8, 313 (isol)
Rodriguez, E. et al, Phytochemistry, 1971, 10, 1145 (struct)

4-0xo-2,11(13)-pseudoguaiadien-12,6- Sq-02146
olide

~
C15H 200 3 M 248.321
(U,,5~,6«,11~,11~)-form [107656-76-8] Artesovin
Constit .. of Artemisia szowitsiana. Cryst. (EtOH aq.).
Mp 142-144°.
Serkerov, S.V. et al, Khim. Prir. Soedin., 1986, 22, 609.
0
Partboxetin Sq-02149
C 15H 180 3 M 246.305
[102607-35-2]
(1«,5fJ,6fl,JOfJ)-form [509-93-3] Ambrosin
Constit. of Ambrosia spp. and Hymenoclea subola. Also
from Parthenium incanum. Anticancer agent. Cryst. Mp
146°. [cx]i; -154.5°.
2,3-Dihydro: [1216-42-8]. 4-0xo-11(1 3)-pseudoguiaen-12,6-
o/ide. Damsin. 2,3-Dihydroambrosin
C 15H 200 3 M 248.321
Constit. of A. maxima, A. hispida and A. de/toidea.
Cryst. (diisopropyl ether). Mp 1UO. [cxJn -72° (c, 4.3 in
CHC13). C19H:w08 M 380.394
Constit. of Parthenium fruticosum. Cryst. (CHC13jhexane).
Suchy, M. et al, Collect. Czech. Chern. Commun., 1963, 28, 2257
(Damsin) Mp 53-55°. [cx]n +78.4° (c, 0.153 in CHCl 3).
Emerson, M.T. eta/, Tetrahedron Lett., 1966, 6151 (cryst struct) Ortega, A. eta/, Phytochemistry, 1986, 25, 699 (isol, cryst struct)
Torrance, S.J. et al, J. Pharm. Sci., 1975, 64, 887.
Grieco, P.A. eta/, J. Am. Chern. Soc., 1977, 99, 7393; 1982, 104,
4226 (synth)
Quallich, E. et al, J. Am. Chern. Soc., 1979, 101, 7627 (synth)

538
Pulchellidine - 4,10,15-Trihydroxy-12,6-... Sq-02150 - Sq-02154

Pulcbellidine Sq-02150 Dominguez, X.A. eta/, Rev. Latinoam. Quim., 1970, 1, 136
(Neoleonine)
[23367-86-4) Herz, W. eta/, Phytochemistry, 1974, 13, 1171 (stereochem)
In_ayama, S. et a/, Chem. Pharm. Bull., 1977, 25, 1928 (cryst struct)
Gill, S. eta/, Phytochemistry, 1980, 19, 2049 (isol)
Inayama, S. eta/, Heterocycles, 1982, 17, 219 (Pulchelloids)
Harimaya, K. et a/, Heterocycles, 1990, 30, 993 (Pulchel/oid D)

2,11,13-Tribydroxy-4-oxo-12,8- Sq-02152
pseudoguaianolide

C20H 33N04 M 351.485

Sesquiterpene alkaloid from Gaillardia pulchella
(Compositae). Cryst. (Me 2COjEtp). Mp 185-186°.
[a]~- 5 -22.SO (c, 1.33 in EtOH).
B,HBr: Mp 208-210°.
Di-Ac: Mp 135-136°. [a]i; -24.0° (c, l in CHCl 3).
CtsH 220 6 M 298.335
8,11-Diepimer: [28513-27-l]. Neopulchellidine
(1 rz,2rz,5p,ap,l Orz,ll /I)-form
C:zoH33N0 4 M 351.485
Alkaloid from G. pulchella (Compositae). Mp 131-134°. 2-(2R-Methylbutanoyl): [51292-61-6). Florigrandin
[a]i} -13° (c, l in CHCl 3). The ll-config. is not clearly C20H300 7 M 382.453
shown. Constit. of Hymenoxys grandiflora. Cryst.
(Me 2COjEtp). Mp 173-175°. [aJn +187°.
Yanagita, M. et al, Tetrahedron Lett., 1969, 2073; 1970, 131 (ir,
pmr, isol, stereochem) Herz, W. eta/, J. Org. Chem., 1974, 39, 2013; 1982, 47, 3011 (iso/,
Sekita, T. eta/, Tetrahedron Lett., 1970, 135 (cryst struct) cryst struct)
Yanagita, M. eta/, Tetrahedron Lett., 1970, 3007
(Neopulchellidine) 9,11,13-Tribydroxy-4-oxo-2-pseudoguaien- Sq-02153
Inayama, S. eta/, Heterocycles, 1985, 23, 377 (synth)
12,8-olide
2,4,6,9-Tetrabydroxy-11(13)- Sq-02151

~
pseudoguaien-12,8-olide

~~00
H~ C15H 200 6 M 296.319
HOH2 C OH

(lrz,5P,Brz,9P,IOrz,llf/)-form [53915-43-8]
CISH1106 M 298.335
9-Ac: Amblyodiol
(Irz,2rz,4rz,5P,6P,8rz,9P,IOrz)-form
Ct,HllO, M 338.357
6,9-Di-Ac: [7706-45-8]. Spathulin Constit. of Gaillardia amblyodon. Cryst. (EtOAcfC 6H6).
Ct,H26 0 8 M 382.410 Mp 204-206°. [a]i;' -50° (c, 0.08 in CHCl 3).
Constit. of Gaillardia spathulata. Cryst. (Me 2C0jpet.
Herz, W. et a/, Phytochemistry, 1974, 13, 1187 (isol)
ether). Mp 261-262°. [a]i;' + 17° (c, l in EtOH). Herz, W. eta/, J. Org. Chem., 1982, 47, 1594 (cryst struct)
2-Angeloyl, 6-Ac:
C22H300 8 M 422.474
Constit. of G. grandiflora. Cryst. Mp 226°. [IX]~ + 39.6° 4,10,15-Tribydroxy-12,6- Sq-02154
(c, 1.1 in CHCl 3). pseudoguaianolide
2-0-(3-Methy/butanoyl), 6-Ac:
C22H310 8 M 424.490
Constit. of G. grandiflora. Cryst. Mp 185°. [a]~ +26° (c
1 in CHCl 3). '

2-0-(2-Methy/butanoyl): [81263-00-5]. Pulchel/oid B

C 20H300 7 M 382.453
Constit. of G. pu/chella. Cryst. Mp 167-169°.
2-Ange/oy/: [81276-53-l]. Pu/che/loid A
C20H 280 7 M 380.437 CtsH240 5 M 284.352
Constit. of G. pulchella. Cryst. Mp 165-167°.
(lrz,4p,6p,JOrz,llPH)-form [117047-27-5] Rudbeckin A
2,4-Diangeloy/: [130223-09-5). PulcheUoid D Constit. of Rudbeckia grandijlora. Gum.
CzsH340 8 M 462.539
Vasquez, M. eta/, Phytochemistry, 1988, 27, 2195.
Constit. of G. pu/chella. Oil.
(I.; ,2.; ,4.;,5.; ,6.;,a.;,9.;,I00:)-form
6-Pentanoyl, 9-Ac: Neo/eonine
C22H310 8 M 424.490
Constit. of G. mexicana. Cryst. Mp 218-220°. [aJn + 36°.
Herz, W. eta/, J. Org. Chem., 1967, 32, 1042 (isol, struct)

539
1,4,14-Trihydroxy-11(13)-... - 2,4,6-Trihydroxy-11(13)-... Sq-02155 - Sq-02158

1,4,14-Trihydroxy-11(13)-pseudoguaien- Sq-02155 4-(2-Methylpropanoyl): Desacetyhetraneurin D 4-0-

12,6-olide isobutyrate
C1,H280 6 M 352.427
Constit. of P. lozanianum. Oil. [ex]~4 -69° (c, 0.3 in

~
CHCI3).
15-(2-Methy/propanoyl), 4-Ac: [109291-66-9]. 15-
Desacetyhetraneurin C isobutyrate
~~H 3007 M 394.464
Constit. of P. /ozanianum. Cryst. Mp 174°. [ex]i; -46° (c,
0.7 in CHC1 3).
0
4-Ketone, 15-Ac: [22621-72-3]. Tetraneurin A
Ct5H 120 5 M 282.336 C 17H 120 6 M 322.357
(1«,4P,5P,6P,10/f)-form Constit. of P. a/pinum var. tetraneuris. Mp 186-188°.
4-Ac: [25383-30-6]. Tetraneurin E [cx]i; +3.7° (c, 2.0 in MeOH).
C 17H 140 6 M 324.373 4-Ketone, 15-(2-methy/propanoyl): [102607-34-1]. Isochiapin
Constit. of Parthenium confertum var. /yratum and P. B
integrifolium. Cryst. (Me2CO). Mp 200-201°. [ex]~ C 19H 260 6 M 350.411
-70.3° (c, 0.55 in MeOH). Constit. of P. fruticosum. Cryst. (Me 2CO/hexane). Mp
4,14-Di-Ac: [25383-32-8]. Tetraneurin F 154-156°. [exln -47.7° (c, 0.195 in CHC1 3).
CI,H2607 M 366.410 Ruesch, H. et al, Tetrahedron, 1969, 25, 805 (isol)
Constit. of P. confertum var. /yratum. Mp 135-136°. [ex]~ Yoshioka, H. et al, Tetrahedron, 1970, 26, 2167 (struct)
-47.4° (c, 0.59 in MeOH). Ortega, A. et al, Phytochemistry, 1986, 49, 699 (lsochiapin B)
Jakupovic, J. et al, Phytochemistry, 1987, 26, 761 (cmr, isol, derivs)
4-Ketone, 14-Ac: [28587-45-3]. Tetraneurin B
C 17H 120 6 M 322.357
Constit. of P. a/pinum var. tetraneuris and P. 2,3,4-Trihydroxy-11(13)-pseudoguaien- Sq-02157
/ozanianum. Cryst. (CHCI 3fpet. ether). Mp 194-195°. 12,8-olide
[ex]~ -44.7° (c, 0.62 in MeOH).
2,3-Didehydro, 4-ketone, 14-Ac: [28625-29-8]. Conchosin B
C 17H 200 6 M 320.341 H~qH,
Constit. of P. confertum. Cryst. (Me 2CO/Et20). Mp HO-
138-144°.
Yoshioka, H. et al, J. Org. Chern., 1970, 35, 2888. H ~ 0
Yoshioka, H. eta/, Tetrahedron, 1970, 26, 2167. 13
de Vivar, A.R. eta/, Tetrahedron, 1970, 26, 2775 (Conchosin B)
CtsH110 5 M 282.336
(1«,2«,3«,4P,5P,BP,10«)-form
1,4,15-Trihydroxy-11(13)-pseudoguaien- Sq-02156
2,3-Di-Ac: [51292-55-8]. Hymenograndin
12,6-olide C 19H 260 7 M 366.410
Constit. of Hymenoxys grandiflora. Antileukaemic agent.
Cryst. (MeOH). Mp 153-154°. [exln +80.7° (c, 1.5 in
CHCI 3).
Tri-Ac: [72264-72-3].
C21H 280 8 M 408.447
Constit. of H. insignis. Gum. [1X]n +60° (c, 0.016 in
CHC13).
111X,l3-Dihydro, tri-Ac: [62121-29-3]. Hymenolane
C 15H 120 5 M 282.336 C21 H 300 8 M 410.463
(1«,4P,5P,6P,JO/f)-form Constit. of H. odorata. Cryst. Mp 215.5-216.SO.
4-Ac: [1 09291-64-7]. 15-Desacetyhetraneurin C 11P,13-Dihydro, tri-Ac: Hymenoltme B
C 17H 140 6 M 324.373 C 21 H 300 8 M 410.463
Constit. of Parthenium /ozanianum. Oil. [ex]i; -31° (c, 1 !sol. from H. odorata.
in CHC1 3). Herz, W. et al, J. Org. Chern., 1974, 39, 2013; 1980, 45, 493 (isol,
15-Ac: [28587-47-5]. Tetraneurin D cryst struct, pmr, cmr)
C 17H 140 6 M 324.373 Pettersen, R.C. et al, J. Chern. Soc., Perkin Trans. 1, 1976, 1399
Constit. of P. /ozanianum and P. fruticosum. Cryst. (Hymenolane)
Gao, F. eta/, Phytochemistry, 1990, 29, 551 (Hymenolane B)
(Me2CO). Mp 203.5-205.SO. [cx]~ -72.8° (c, 0.54 in
MeOH).
4,15-Di-Ac: [28587-46-4]. Tetraneurin C 2,4,6-Trihydroxy-11(13)-pseudoguaien- Sq-02158
C19H260 7 M 366.410 12,8-olide
Constit. of P. a/pinum var. tetraneuris and P.

~~O
/ozanianum. Cryst. (CHCI 3fpet. ether). Mp 145°. [ex]~
-109° (c, 0.05 in MeOH).
15-(2-Methy/propanoyl): Desacetyhetraneurin D 15-0- (lo,2o,4tt,5,,6a,8o,10o),{o'm
isobutyrate
C 19H 280 6 M 352.427
Constit. of P. /ozanianum. Cryst. Mp 213°. [ex]i; -42° (c,
1.5 in CHCI 3). M 282.336

540
Altamisic acid - Biennin A Sq-02159 - Sq-02160

(I rz.,2rz.,4rz,5P,6rz,8rz.,I Orz. )-form C15H 200 5 M 280.320

6rx- Hydroxypulchellin Isol. from Hymenoxys scaposa var. villosa.
Constit. of Gaillardia pulchella. Herz, W. eta/, J. Org. Chern., 1967, 32, 216; 1968, 33, 2780; 1969,
4-Angeloyl: Pulchelloid C 34, 2915 (Alternilin, Flexuosins)
C20Hm06 M 364.438 Evstatova, R.I. eta/, Khim. Prir. Soedin., 1971, 7, 270 (Arnifolin)
Constit. of G. pulchella. Cryst. Mp 98.5-100°. [rx]i; Chugunov, P.V. eta/, Khim. Prir. Soedin., 1971, 7, 276; Chern.
Nat. Compd. (Engl. Trans/.), 265 (Britannin)
-130° (c, 0.1 in MeOH).
Kondo, Y. eta/, Heterocycles, 1977, 6, 19 (Picrohelenin)
(I rz.,2rz.,4rz,5P,6rz,8P,I Orz. )-form Willuhn, G. eta/, Tetrahedron, 1981, 37, 773 (Chamissonolide)
2-Ac: [78853-98-2]. Chamissonolide Chien, M. eta/, CA, 1983, 99, 85072s (Britannin)
C 17H 140 6 M 324.373 Inayarna, S. et a/, Heterocycles, 1983, 20, 1501 (Pu/chelloid C)
Constit. of Arnica chamissonis. Cryst. (EtOH). Mp 202- Adekenov, S.M. eta/, Collect. Czech. Chern. Commun., 1990, 55,
1568 (cryst struct, Britannin)
203.5". [rx]i,O + 54.8° (c, 1.11 in CHCI 3). Gao, F. eta/, Phytochemistry, 1990, 29, 895 (Vil/osin B,
2,4-Di-Ac: 4-Acetylchamissonolide Acetylchamissonolide)
C,,H11;07 M 366.410
Isol. from Hymenoxys scaposa var. villosa.
2-(2-Methylpropanoyl):
C 19Hm06 M 352.427
Isol. from H. scaposa var. villosa.
6-(3-Methylbutenoyl): [6805-36-3]. Flexuosin B Seco-, cyclo-, abeo- and
C20Hm06 M 364.438
Con tit. of Helenium jiexuosum. Cryst. Mp 137° approx.
(variable). [rx]~6 +44.2° (c, 4.78 in CHCI 3). norpseudoguaianes
4-Ketone, 6-angeloyl: [25644-08-0]. Arnifolin
C20 H 260 6 M 362.422
Constit. of Arnica foliosa and A. montana. Cryst. Mp
128-137°. [rx]i,O +52.6° (c, 3 in CHC1 3). Altamisic acid Sq-02159
(I rz.,2rz,4P,5P,6rz,8p,J Orz. )-form
2-Ac: [61826-50-4]. Picrohelenin
C 17H 140 6 M 324.373
Constit. of Helenium autumnale. Cryst. Mp 170°.
(Irx.,2p,4rx.,5P,6rz,8rz.,IOrz.)-form
2-Ac: [25374-95-2]. Alternilin
C 17H 140 6 M 324.373
Constit. of H. alternifolium. Cryst. (CHCI 3). Mp 193-
1950. [rx]i; + 11.2° (c, 1 in CHCI 3).
C,sHzlPs M 280.320
(Irz,2P,4rx.,5p,6p,8rx.,IOrz.)-form Constit. of Ambrosia tenuifolia. Cryst. Mp 141-142°.
6-Ac: [6851-56-5]. Flexuosin A Me ester: Methyl altamisate. 1'-Noraltamisin
C 17H 140 6 M 324.373 Ct,H22 0 5 M 294.347
Constit. of H. flexuosum. Cryst. (C 6H 6, EtOH or Constit. of A. confertiflora. Cryst. (Me 2CO/diisopropyl
EtOAc). Mp 220-221.5". [rxJi!' + 12.4° (c, 5 in CHCI 3). ether). Mp 93-95°. [rx]~ +34.1° (c, 0.2 in MeOH).
2,6-Di-Ac: 2-Acety/ftexuosin A Et ester: [67604-04-0]. Altamisin
C 19H 260 7 M 366.410 C17H 140 5 M 308.374
Constit. of H. autumnale. Cryst. (Et20fpet. ether). Mp Constit. of A. cumanensis. Cryst. (hexane). Mp 101-102°.
124-126°. [rx] 0 +34.9°.
(Irz.,2rz.,4rz,5P,6P,8rz,IOrz.)-form Borges, J. eta/, Tetrahedron Lett., 1978, 1513.
6p-Hydroxypulchellin Oberti, J.C. eta/, Phytochemistry, 1986, 25, 1355.
2-Ac: [97643-92-0]. 6P-Hydroxypulchellin 2-0-acetate Delgado, G. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 83.
C 17H 140 6 M 324.373
lsol. from Loxothysanus sinuatus. Cryst. Mp 87°. [rx]~4 Biennin A Sq-02160
+ 14° (c, 0.97 in MeOH).
2-(3-Methylbutanoyl): [97605-31-7]. 6P-Hydroxypulchellin 2-
0-isol'alerate
C20H 31,06 M 366.453
lsol. from L. sinuatus. Cryst. Mp 127°.
4-Angeloyl, 6-Ac: 6P-Acetoxypulchellin 4-0-angelate 0
C22 H 300 7 M 406.475
Constit. of G. pulchella.
(I rz.,2rz,4P,5P,6rz,8rz.,I Orz. )-form C 15H 220 5 M 282.336
2,6-Di-Ac: [33627-28-0]. Britannin. Britanin Isol. from Hymenoxys biennis. Powder.
C 19H 260 7 M 366.410 8-Epimer, 4-(2-methylbutanoyl): [126794-72-7]. Hymenoratin
Constit. of lnula britannica, /. linariaefolia and /. B
caspica. Cryst. (EtOH). Mp 192-194°. [rx] 0 -26° (c, 5 in Constit. of H. odorata.
CHC1 3). Struct. revised in 1989. Gao, F. eta/, Phytochemistry, 1990, 29, 551, 3875 (isol, pmr, cmr)
(I rz.,2rz,5P,6P,8P,J Orz. )-form
4-Ketone: [128286-77-1]. Villosin B

541
Caespitenone - Hymenoxon Sq-02161 - Sq-02167

Caespitenone Sq-02161 4-Hydroxynorpsilotropin Sq-02165

[73019-81-5]

q~q
H~o
C15H 200 2 M 232.322 CI4Hia05 M 266.293
Constit. of Parella spp. Oil. [ex] 0 -34° (c, 0.2 in CHC1 3). 4a.-form [76306-83-7]
Constit. of Psilostrophe villosa. Oil.
Asak:awa, Y. et al, Phytochemistry, 1980, 19, 603.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 1492.

Confertdiolide Sq-02162
[66674-28-0]
Hymenoratin C Sq-02166
[126794-73-8]

C1sH1804 M 262.305 C15H 200 4 M 264.321

Constit. of Parthenium confertum. Cryst. Constit. of Hymenoxys odorata.
(Me2COjisopropy1 ether). Mp 156-158°. [ex]~ -95.3°
(CHC1 3). Gao, K. et al, Phytochemistry, 1990, 29, 551 (isol, pmr, cmr)

de Vivar, A.R. et al, Phytochemistry, 1978, 17, 279.

Hymenoxon Sq-02167
Greenein Sq-02163 [57377-32-9]
[25080-56-2]
HO~~'
rf>_o
0 3
0 4

OH 0
J~o C 15H 220 5 M 282.336
Constit. of Hymenoxys odorata, H. richardsonii and
C1sH2004 M 264.321 Duyaldia hoopesii. Cryst.
Constit. of Hymenoxys greenei. Cryst. (Me 2CO/Etp). Mp I> LV1599200.
175-176°. [ex] 0 + 114° (c, 0.3 in MeOH). 3-Me ether:
Herz, W. et al, J. Org. Chern., 1970, 35, 2611. C 17H 2P 5 M 308.374
Constit. of Geigeria ornativa. Oil.
Heleniamarin Sq-02164 4-Me ether:
[66607-74-7] C11H240 5 M 308.374
Constit. of G. ornativa. Oil.
4-Et ether: [20087-13-2). Hymenolide
C 17H 260 5 M 310.389
Constit. of H. odorata. Cryst. (EtOAc). Mp 136-138°.
[ex) 0 -48.6° (c, 1.4 in CHC1 3).
3-Epimer:
C 15H 220 5 M 282.336
Constit. of Psilostrophe gnaphaloides.
C17H220 5 M 306.358
Constit. of Helenium amarum. Cryst. (Etp). Mp 151-153°. 4-Epimer: Hymenovin B
[ex]~ +58 .SO (c, 0.25 in CHC1 3). C 15H 220 5 M 282.336
Constit. of H. odorata.
Ottersen, T. et al, Acta Chern. Scand., Ser. B, 1978, 32, 79.
3,4-Diepimer: Hymenovin C
C15H 220 5 M 282.336
Constit. of H. odorata.
2ex-Acetoxy:
C11H240 7 M 340.372
Constit. of Psilostrophe villosa. Oil.
2ex- Tigloyloxy:
C20H 300 7 M 382.453
Constit. of P. villosa. Oil.
2ex-Acetoxy, 4-Et ether:
542
lncaspin - Microlenin Sq-02168 - Sq-02173

C 1,H280 7 M 368.426 Constit. of A. dumosa. Cryst. Mp 185-186°. Stereochem.

Constit. of P. vi/losa. Oil. undetd. May be identical with Lagosin.
2rx.-Tigloyloxy, 4-Et ether: Seaman, F.C. et a/, Rev. Latinoam. Quim., 1979, 10, 85 (Dumosin)
CnH 340 7 M 410.506 del Castillo, J.B. eta/, An. Quim., 1981, 77, 52 (Lagosin)
Consit. of P. villosa. Oil.
Herz, W. et al, J. Org. Chern., 1970, 35, 2611 (Hymenolide) Unearifolin B Sq-02171
Ivie, G.W. eta/, J. Agric. Food Chern., 1975, 23, 841 (isol, struct) [26358-40-7]
Pettersen, R.C. eta/, J. Chern. Soc., Perkin Trans. 2, 1976, 1399
(cryst struct)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 1492 (derivs)
Herz., W. eta/, Phytochemistry, 1987, 26, 457 (derivs)
Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (derivs)
Gao, F. eta/, Phytochemistry, 1990, 29, 551 (derivs)

Incaspin Sq-02168
[95523-33-4]

C20H 240 6 M 360.406

Constit. of Hymenoxys spp. Cryst. (Me2CO). Mp 214-215°.
(cxJn -103.8° (c, 0.8 in CHC13).
Herz, W. eta/, J. Org. Chern., 1970, 35, 4117.

Mexicanin E Sq-02172
4-0xo-15-nor-2,11(13)-pseudoguaiadien-12,8-olide
C 19H 260s M 334.4ll
[5945-40-4]
Constit. of lnula caspica. Cryst. (EtOH). Mp 220-222°.
[cx]),S + 116.9° (CHCl 3). Anomalous struct.
Adekenov, S.M. eta/, Khim. Prir. Soedin., 1984, 20, 797; Chern.
Nat. Compd. (Engl. Trans/.), p 757.

lnulicin Sq-02169
[33627-41-7]
C14H1,03 M 232.279
Constit. of Helenium mexicanum. Cryst. (Et20/hexane).
Mp 100.5-101.5°. [cxJn -62° (dioxan).
I> C04853000.
Romo, J.A. eta/, Tetrahedron, 1963, 19, 2317 (isol, struct)
0 Romo, J. et al, Tetrahedron Lett., 1966, 1029 (ms)
Ul-Haque, M. et al, J. Chern. Soc. B, 1967, 355 (cryst struct)
C 17H 240s M 308.374 Lee, K.-H. eta/, Phytochemistry, 1977, 16, 393 (isof)
Constit. of lnula japonica. Cryst. Mp 125-126°. [cxln + 90°.
I>GU3l18500. Microlenin Sq-02173
Deacetyl: [33620-72-3]. Deacety6nu6cin [60622-41-5]
C 1sHn04 M 266.336
Constit. of l.japonica. Cryst. Mp 174-176°. [cxln +90°.
Kiseleva, E.Ya. eta/, Khim. Prir. Soedin., 1971, 7, 263; CA, 75,
110445c (isof)
Evstratova, R.I. eta/, Khim. Prir. Soedin., 1974, 10, 730; CA, 82,
156506y (isof)

Lagosint Sq-02170
[81968-96-9]
C29H 340 7 M 494.583
Constit. of Helenium microcephalum. Cryst. Mp 280° dec.
(ex]~ + 10° (c, 1 in Py).
Lee, K.-H. eta/, J. Chern. Soc., Chern. Commun., 1976, 341.
0

C 1sH 1,0s M 276.288

Constit. of Ambrosia cumanensis. Cryst. (MeOH). Mp 193-
1940.
Stereoisomer(?): Dumosin
CISHI60S M 276.288

543
4-0xo-3,4-secoambrosan-12,6-olid-3-... - Tenulin Sq-02174- Sq-02179

4-0xo-3,4-secoambrosan-12,6-olid-3-oic Sq-02174 Psilostachyin C Sq-02177

acid [6466-67-7]

OHC-.l1
HOOCY>u
0

0
C15H 220 5 M 282.336 C 15H100 4 M 264.321
Constit. of Ambrosia artemisiifolia. Cryst. (Me 2C0jpet. Constit. of Ambrosia psilostachya, A. peruviana and A.
ether). Mp 171.5-176°. [cx]i? -0.88° (c, 0.91 in Me 2CO). de/toidea. Cryst. Mp 223-225°. [cx]i;' -82° (c, 0.6 in
Stefanovic, M. et al, Phytochemistry, 1987, 26, 850. CHCl 3).
111•11 -lsomer, JOcx-hydroxy: [87321-96-8]. JOrx.-
Hydroxyisopsilostachyin C
Psilostachyin Sq-02175
CtsH100 5 M 280.320
[3533-47-9] Constit. of A. cumanensis. Viscous oil. [cx]i? -0.47° (c,
0.4 in CHCl 3).
Kagan, H.B. et al, J. Org. Chern., 1966, 31, 1629 (struct)
0 Mabry, T.J. et al, Tetrahedron, 1966, 22, 1139 (isol)
Greico, P.A. et al, J. Am. Chern. Soc., 1977, 99, 7393 (synth)
Borges-Del-Castillo, J. et al, Phytochemistry, 1983, 22, 787 (IOIX-
Hydroxyisopsilostachyin)

4,5-Seconeopulchell-5-ene Sq-02178
C 15H 100 5 M 280.320
Constit. of Ambrosia psilostachya. Cryst. HO I

(CH 2Cl2 jisopropyl ether). Mp 215°. [cx]i;' -125.2° (c, I H'

4.76 in CHCl 3).
Jlcx,13-Dihydro: [114246-84-3]. 11,13-Dihydropsilostachyin
C15H 220 5 M 282.336
HOH,~Q
~~0
Constit. of A. confertiflora. Cryst. Mp 225-226°. [cx]i;'
-70° (c, l in MeOH).
5-Epimer: [27696-09-9]. Cordi/in C 15H 120 4 M 266.336
C15H 100 5 M 280.320 2-Ac: [93373-41-2].
Constit. of A. cordifolia. Cryst. (Me 2COjhexane). Mp C 17H 240 5 M 308.374
2l0-2UO. [cx] 0 -100° (c, 1.05 in CHCl 3). Constit. of Gaillardia pulchel/a.
Mabry, T.J. et a[, Tetrahedron, 1966, 22, 1139 (Psilostachyin) 4-Ac: [117634-70-5].
Herz, W. et al, Phytochemistry, 1973, 12, 1415 (Cordi/in) C 17H 240 5 M 308.374
Delgado, G. et al, J. Nat. Prod. (Lloydia), 1988, 51, 83 Constit. of G. pulchel/a.
(Dihydropsilostachyin) Bohlmann, F. et al, Phytochemistry, 1984, 23, 1979 (isol)
Yu, S. et a/, Phytochemistry, 1988, 23, 2887 (iso/)
Psilostachyin B Sq-02176
[6995-02-4] Tenulin Sq-02179
[19202-92-7]

C1sH180 4 M 262.305
Constit. of Ambrosia psi/ostachya. Cryst. Mp 123°. [cx]i;' C 17H120 5 M 306.358
-5° (c, 0.7 in CHCl 3). Constit. of Helenium tenuifolium, H. e/egans, etc. Fish
2,3-Didehydro, lcx,JOcx-epoxide: [77026-67-6]. Paulitin poison; has mild sternutatory action. Cryst. (Hp). Mp
C 15H 160 5 M 276.288 196-198°. [cx]i? -21.7° (EtOH).
Constit. of A. cumanensis. Cryst. (CHCl 3/Et20). Mp I> BD9640000.
168-170°. [cx]i? +31° (c, O.l in CHC1 3).
Herz, W. et al, J. Org. Chern., 1975, 40, 2557.
2,3-Didehydro, lP,JOP-epoxide: [76930-30-8]. lsopaulitin
C15H 160 5 M 276.288
Constit. of A. cumanensis. Cryst. (EtOH). Mp 147-150°.
[cx]i? -20° (c, 0.12 in CHCl3).
Mabry, T.J. et al, Tetrahedron, 1966, 22, 1943 (isol, struct)
Raszeja, W. et al, Planta Med., 1977, 32, 319 (isol, pmr)
Del Castillo, J.B. et al, An. Quim., 1981, 77, 52 (isol)

544
Themoidin- 10,12-Aromadendranediol Sq-02180 - Sq-02186

Themoidin Sq-02180 3,10(14)-Aromadendradiene Sq-02183

Dihydropsi/otropin
[25062-26-4]

0~1;1'
0 8

If n o C 15H 22 M 202.339
13
(1«,5P,6«,7«)-form [53526-64-0] fJ-Spathu/ene
C 15Hn04 M 266.336 Constit. of the the oil of Schinus mol/e.
Constit. of Hymenoxys anthemoides. Cryst. (Me2COjEt20). Terhune, S.J. eta/, Phytochemistry, 1974, 13, 865.
Mp 219-220°. [1X]n +61.8° (c, 0.55 in MeOH).
8-Epimer: [25062-24-2]. Anthemoidin. Dihydrovermeerin 1(1 0),3- Aromadendradien-2-one Sq-02184
C 15Hn04 M 266.336
Constit. of H. anthemoides. Cryst. (Me2CO/Et20). Mp
220-221°. [1X]n -115.SO (c, 0.14 in MeOH).
11,13-Didehydro: [26305-91-9]. Psilotropin. Floribundin
C 15H 20 0 4 M 264.321
Constit. of H. spp. and Psi/ostrophe cooperi. Rosettes
(pet. ether). Mp 144-145°. [IX]~ +63.8° (c, 0.46 in
EtOH).
8-Epimer, 11,13-didehydro: [16983-23-6]. Vermeerin C 15H 200 M 216.322
CtsH 200 4 M 264.321 (1«,6P,7fl)-form [80442-75-7] Tridensenone
Constit. of Geigeria aspera and G. africana. Cryst. Constit. of Bazzania tridens. Cryst. Mp 89-90°. [1Xln
(CHCI 3/Et20). Mp 147°. [1X]n -58° (c, 1.5 in EtOH). -55 .SO (c, 0.5 in CHC13).
Anderson, L.A.P. eta/, Tetrahedron, 1967, 23, 4153 (Vermeerin) Toyota, M. et a/, Phytochemistry, 1981, 20, 2359.
Herz, W. eta/, J. Org. Chern., 1970, 35, 2611 (Themoidin,
Anthemoidin) 4,10-Aromadendranediol Sq-02185
de Silva, L.B., Phytochemistry, 1970, 9, 59 (Psilotropin)
4,10-Dihydroxyaromadendrane

Aromadendranes
C 15Hu;01 M 238.369
1(5),3-Aromadendradiene Sq-02181 (1«,4P,5P,6«,7«,10«)-form
Constit. of Brasilia sickii. Cryst. Mp 132°. [1X]~4 -17° (c,

«i
I 0.1 in CHC1 3).
(1P,4«,5P,6«,7«,10fl)-form [109360-94-3] A/Joaronuulendrane-
4«,10/J-diol
Constit. of Ambrosiaperuviana. Cryst. Mp 112-113°.
[IX]~ + 7o (c, 0.45 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1213.
C 15Hn M 202.339 Goldsby, G. eta/, Phyt(lchemistry, 1987, 26, 1059.
(6«,7«,10«)-form [111778-06-4]
Constit. of Tolu balsam (from Balsamum tolutanum). 10,12-Aromadendranediol Sq-02186
Oil.
Friedel, H.D. eta/, Helv. Chim. Acta, 1987, 70, 1753.

1(1 0),4-Aromadendradiene Sq-02182

«i
I

C 15Hu;01 M 238.369
(JP,4«,5P,6«,7«,10P,Jlfl)-form [55812-89-0] Flourensadiol
Constit. of Flourensia cernua. Cryst. (CHCI 3). Mp 125-
1260.
C 15H 22 M 202.339
Pettersen, R.C. eta/, Acta Crystallogr., Sect. B, 1975, 31, 1124.
(6«,7«)-form [112362-74-0]
Constit. of Tolu blasam (from Balsamum tolutanum).
Oil.
Friedel, H.D. et al, Helv. Chim. Acta, 1987, 70, 1753.

545
10,14-Aromadendranediol - 1(10)-Aromadendrene Sq-02187 - Sq-02191

10,14-Aromadendranediol Sq-02187 Constit. of Eucalyptus globulus and Thryptomene kochii.

14-Hydroxyviridijlorol Also from E. eudesmoides, E. Caesia, E. gongylocarpa,
Prostanthera sieberi and P. rotundifolia. Needles (EtOH
aq.). Mp 88.SO. Bp 283°. [1X]~ -35.3° (CHC1 3).
3,5-Dinitrobenzoyl: Cryst. (pet. ether). Mp 139.5°, Mp 196-
1980 (double Mp).
(1P,4rK,5P,6rK,7rK,10rK)-form
10-0-[2-(2-M ethylpropanoyl)-P-v-fucopyranoside]:
C25 H 420 6 M 438.603
Constit. of Calendula arvensis.
C15H 260 2 M 238.369 10-0-(2- Tigloyl-P-v-fucopyranoside ):
Constit. of Pulicaria paludosa. Oil. [1X]i;1 + 2.6° (CHCI 3). C26H 420 6 M 450.614
San Feliciano, A. et a/, Phytochemistry, 1989, 28, 2717 (iso/, pmr, Constit. of C. arvensis.
cmr)
(lp,4rK,5P,6rK,7rK,l0f/)-form [552-02-3] Viridijlorol. Himbaccol
Constit. of oil of Melaleuca viridiflora, Himantandra
Aromadendrane 1-isonitrile Sq-02188 baccata and Juniperus oxycedrus. Cryst. Mp 73-75°. [1X]n
[112757-34-3] +4° (CHCI 3), [IX]~ -10° (EtOH).
0-(2-0-Acetyl-3-0-angeloyi-P-v-fucopyranoside): [104472-
69-7]. Pittosporanoside A 1
C28H 440 7 M 492.651
Constit. of Pittosporum tobira. Needles. Mp 138-139°.
[1X]n + 15.7° (c, 5 in CHCI 3).
0-(2-0-Acetyl-4-0-angeloyl-P-v-fucopyranoside): [104472-
70-0]. Pittosporanoside A 2
C16H 25N M 231.380 C28H 440 7 M 492.651
Metab. of marine sponge Acanthella acuta. Cryst. Mp 65- Constit. of P. tobira. [1X]n + 17.3° (c, 3 in CHCI 3).
660. [1X]n -13.7° (c, 1.4 in CHCI 3). (1p,4P,5rK,6rK,7~¥.,1 0~¥. )-form
Isothiocyanate: [112767-01-8]. Aromadendrane 1- Ledol. Ledum camphor. Porschcamphor
isothiocyanate Constit. of Ledum palustre and of Valeriana officina/is,
C16H 25NS M 263.446 Bacchris genistelloides, Piper spp., Aristolochia indica
Metab. of A. acuta. Oil. [1X]n -32.8° (c, 0.7 in CHCI 3). and others. Cryst. (pet. ether). Mp 105°. Bp 282-283°.
Has - NCS replacing - NC. [1X]n + 8° (EtOH).
Mayo!, L. eta/, Tetrahedron, 1987, 43, 5381. Birch, A.J. eta/, Aust. J. Chern., 1955, 8, 550 (isol)
Biichi, G. eta/, Tetrahedron Lett., No.6, 1959, 14 (struct, synth)
Graham, B.A. eta/, Aust. J. Chern., 1960, 13, 372 (struct)
1-Aromadendranol Sq-02189 Biichi, G. eta/, J. Am. Chern. Soc., 1969, 91, 6473 (synth, abs
conjig)
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 1908 (occur)
Marshall, J.A. eta/, J. Org. Chern., 1974, 39, 1971 (synth)
( 1cx,4cx,5~,6cx, 7ex, IOcx )-form Pakrashi, S.C. eta/, J. Org. Chern., 1980, 45, 4765 (isol)
Tahoka, D. et a/, Chern. Lett., 1986, 1121 (Pittosporanosides)
De Tommasi, N. et al, J. Nat. Prod. (Lloydia), 1990, 53, 830
C15H 260 M 222.370 (deriv)
(1«,4«,5P,6«,7«,10«)-form [5986-49-2] Palustrol
Constit. of Baccharis genistelloides and Ledum palustre. 1(10)-Aromadendrene Sq-02191
Oil. Bp2 ll8°. [1X]~ -17.8°.
(1P,4P,5«,6P,7P,10fl)-form
Constit. of Caspitularia aff. subviridis. Oil.
Dolejs, L. eta/, Collect. Czech. Chern. Commun., 1961, 26, 811
(isol)
Braekman, J.C. eta/, Bull. Soc. Chim. Be/g., 1989, 98, 869 (isol,
cryst struct)
C15H 24 M 204.355
10-Aromadendranol Sq-02190 (4P,5rK,6rK,7rK)-form [21747-46-6] Ledene. Viridiflorene
Ledene and Viridiflorene appear to be identical although
this is not specifically referred to in the literature.
Constit. of oil of Melaleuca alternifolia. Oil. Bp3 ll0-
ll30. [IX)~ +48.4°.
(lcx,4cx,5Mcx, 7cx, 1Ocx)-form Birch, A.J. eta/, Tetrahedron Lett., 1959, 3, 15 (isol)
Swords, G. eta/, J. Agric. Food Chern., 1978, 26, 734 (isol)

C15H 260 M 222.370

(1«,4rK,5P,6rK,7rK,10rK)-form [489-41-8] Globulol

546
1-Aromadendrene - 10(14)-Aromadendrene-4,8,13-triol Sq-02192 - Sq-02198

1-Aromadendrene Sq-02192 [489-39-4] ( + )-Aromadendrene

(lfl,4fl,5r~.,6fl,7fl)-form
Constit. of Agathis australis, Artemisia vestita and E.
I
oils. Oil. Bp 260-265°. [ex] 0 +24.SO.

~
Dolejs, L. et al, Collect. Czech. Chern. Commun., 1960, 25, 1483
(isol)
Biichi, G. eta/, J. Am. Chern. Soc., 1969, 91, 6473 (synth, abs
conjig, bib/)

10(14)-Aromadendrene-4,8-diol Sq-02196
C 15H 24 M 204.355
(4«,5/1,6«,7«,10«)-form [111821-79-5]
Constit. of Tolu balsam (from Balsamum to/utanum).
Oil. [ex]i,S +42° (c, 0.2 in pentane).
Friedel, H.D. eta/, Helv. Chim. Acta, 1987, 70, 1753.

4-Aromadendrene Sq-02193
C1sH240 2 M 236.353
I
(1«,4fJ,5fJ,6«,7«,8« )-form [85526-81-4] 8r~.-Hydroxyspathulenol

~
Constit. of Parthenium argentatum and Cineraria
(lcx,6cx, 7cx, lOcx)-form fruticulorum. Cryst. Mp l56-l57.SO. [ex]i,6 +7.1° (c, l.7l
in CHCl 3). Also descr. as gum.
8-Cinnamoy/: [107812-57-7]. Guayulin C
C 24 H3e.03 M 366.499
Constit. of P. argentatum. Cryst. Mp 111-112°. [ex]i,6
C,sH 24 M 204.355
-7.8° (c, 2.95 in CHCl 3).
(1«;6«,7«,10«)-form [112421-19-9] 1-Epi-«-gurjunene
Constit. of Tolu balsam (from Balsamum to/utanum). 8-(4-Methoxybenzoyl): [107812-58-8]. Guayulin D
Oil. (ex]i,S -68° (c, 0.2 in pentane). C23 H3eP4 M 370.488
From P. argentatum. Oil.
(lfl,611.,7«,10«)-form [489-40-7] 11.-Gurjunene
Constit. of inter alia, gurjun balsam from Dipterocarpus [92618-94-5]
dyeri. Oil. Bp 10 114-116°, Bp 3 75-77°. Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2531 (8-
Hydroxysp,athulenol)
Streith, J. eta/, Bull. Soc. Chim. Fr., 1963, 1960 (isol, struct) Crevoisier, M. eta/, Acta Crystallogr., Sect. C, 1984, 40, 979 (cryst
Friedel, H.D. et al, Helv. Chim. Acta, 1987, 70, 1753 (isol, cmr) struct)
Martinez, M. eta/, J. Nat. Prod. (Lioydia), 1986, 49, 1102 (isol,
9-Aromadendrene Sq-02194 deriv)

10(14)-Aromadendrene-4,9-diol Sq-02197

C 15H24 M 204.355
(lfl,4«,5fl,6«,7«)-form [112421-20-2]
Constit. of Tolu balsam (from Ba/samum tolutanum).
Oil. [ex]i,S -78° (c, 0.6 in pentane). C 15H 240 2 M 236.353
Friedel, H.D. eta/, Helv. Chim. Acta, 1987, 70, 1753. (4fl,9fl)-form [123688-26-6]
Constit. of Sideritis varoi. Cryst. Mp 129-131°. [ex] 0 -5°
(c, 1 in CHCl 3).

rn
10(14)-Aromadendrene Sq-02195
9-Ac: [123688-32-4]. 9P-Acetoxy-10(14)-aromadendren-4P-ol
C17H 260 3 M 278.391
Constit. of S. varoi. Cryst. Mp 76-78°. [ex] 0 + 3.2° (c, 1
in CHCl 3).

~
Garcia-Granados, A. et al, Can. J. Chern., 1989, 67, 1288 (isol,
( l cx,4cx,5p,6cx, 7ex )-form pmr, cmr)

C 15H 24 M 204.355 10(14)-Aromadendrene-4,8,13-triol Sq-02198

(14682-34-9] (- )-Aromadendrene
(1r~.,4«,5fJ,6r~.,7«)-form
Constit. of Bixa ore/lana and Eucalyptus sideroxylon.
Oil. [ex] 0 - U0 (EtOH). rh~OH
(lfl,4r~.,5fl,6fl,7f/)-form
Alloaromadendrene. ex- Aromadendrene
Constit. of many essential oils. incl. Ledum palustre, Hm'CH20H
Croton spp. E. g/obulus, Metrosideros scandens,
Perovskia scrophulariaefolia, Glycyrrhiza triphyl/a. Oil. C15H 240 3 M 252.353
Bp 2 96°. [ex]~ -21.6°. n0 18 1.5010. (1«,4fl,5fl,6«,7«,811.)-form

547
1(5)-Aromadendren-7-ol - 4-Aromadendren-3-one Sq-02199 - Sq-02205

8«,13-DihydroxyspatlrukiWI Metab. of Laurencia subopposita. Oil. [a]~ +99° (c, 1 in

Isol. from Ciner.aria fruticu/orum. Solid. [ex] 0 -2.7° (c, CHC1 3).
0.15 in CHC1 3). Wratten, S.J. eta/, J. Org. Chem., 1977, 42, 3343.
13-A/dehyde: 4,8-Dihydroxy-10(14)-aromadendren-13-al. 8«-
Hydroxy-13-oxospatlrukiWI 10(14)-Aromadendren-4-ol Sq-02203
C15H 210 3 M 250.337
Isol. from C. fruticulorum. Gum. [ex] 0 -25° (c, 0.1 in

-~
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 2531.

1(5)-Aromadendren-7-ol Sq-02199
Ii~

~OH
C 15H 240 M 220.354
(1«,4/l,5/l,6«,7«)-form [6750-60-3] Spatlruknol
Constit. of the essential oil of Eucalyptus spathulata var.
grandiflora. Oil. [ex] 0 + 56°.
3,5-Dinitrobenzoyl: Cryst. Mp 148°.
C 15H 240 M 220.354 Bowyer, R.C. eta/, Chem. Ind. (London), 1963, 1245 (iso/, struct)
Juell, S. eta[, Arch. Pharm. (Weinheim, Ger.), 1976, 309, 458 (pmr)
(4/l,6Jl,7Jl,10f/)-form Surburg, H. et al, Chem. Ber., 1981, 114, 118 (synth)
Constit. of the soft coral Xenia novae-britanniae. Cryst.
(EtOAc). Mp 121-124°. [ex] 0 +66° (c, 0.1 in CHCl3).
Bowden, B.F. eta/, Aust. J. Chem., 1987, 40, 1483.
1(10)-Aromadendren-9-one Sq-02204

1(10)-Aromadendren-4-ol Sq-02200

C 15H 210 M 218.338

(4«,5Jl,6«,7«)-form [34413-94-0] Squamulosone
Constit. of Phebalium squamulosum. Cryst. (hexane). Mp
C 15H 240 M 220.354 45-46°. [ex] 0 -234° (c, 1.2 in CHC1 3).
(4/l,5«,6«,7«)-form [88395-46-4]1sospartlruknol Batey, I.L. et al, Aust. J. Chem., 1971, 24, 2173.
Constit. of Clary sage oil (Salvia sclarea). Cryst. Mp 69-
70.SO. [ex] 0 +99° (c, 0.6 in CHC1 3).
4-Aromadendren-~ne Sq-02205
Maurer, B. eta/, Helv. Chim. Acta, 1983, 66, 2223.

1-Aromadendren-10-ol Sq-02201
10-Hydroxy-1-aromadendrene
(lcx,6~, 7~, I 0~)-form

C 15H 220 M 218.338

(1«,6Jl,7Jl,10f/)-form [53584-68-2] Cyclocolorenone
Constit. of Plagiochila acanthophylla and Porella
verucosa. Oil. [ex] 0 +404° (c, 0.9 in CHC13).
C 15H 240 M 220.354 (1Jl,6«,7«,10«)-form
(4«,5«,6«,7«,10/1)-form [63181-42-0] Constit. of Pseudowintera colorata and Solidago
Metab. of Laurencia subopposita. Oil. [ex]~ -46° (c, l in canadensis. Oil. Bp 5 136-138°. [ex]~ -400° (c, 8.75 in
CHC13). EtOH).
Wratten, S.J. et al, J. Org. Chem., 1977, 42, 3343. 2,4-Dinitrophenylhydrazone: Red cryst. (EtOAc). Mp 217-
2180.
10(14)-Aromadendren-1-ol Sq-02202 (1«,6«,7«,10rx.)-form [1911-75-7]
Cryst. Mp 68-68.SO. [ex] 0 -198° (c, 6.9 in CHC1 3).

If) Biichi, G. et al, J. Am. Chem. Soc., 1966, 88, 3403 (struct)
Caine, D. et al, J. Org. Chem., 1972, 37, 3751 (synth)

rtt
Matsuo, A. et al, Experientia, 1974, 30, 321 (isol)

C 15H 240 M 220.354

(1/l,4«,5«,6«,7«)-form [63181-41-9]1/J-
Hydroxyalloaromadendrene

548
Axamide 2 - Zierone Sq-02206 - Sq-02211

Axamide 2 Sq-02206 Metab. of the sponge Epipo/asis kushimotoensis. Cryst. Mp

[56012-89-6] 92°. [cx] 0 +91.2° (c, 1.0 in CHC13).
Tada, H. eta/, Chern. Pharm. Bull., 1985, 33, 1941.

lhCHO
Epipolasinthiourea B Sq-02209
[97915-90-7]

~
As Epipolasin B, Sq-02208 with
X= -NHCSNHCH 2CH 2Ph
C16H 17NO M 249.395 C24H 36N 2S M 384.628
Constit. of Axinella cannabina. Oil. [cx) 0 + 37.5° (c, 0.9 in Metab. of sponge Epipo/asis kushimotoensis. Oil.
CHC1 3). Tada, H. eta/, Chern. Pharm. Bull., 1985, 33, 1941.
1-Epimer: [1 08739-41-9). 10rx.-Formamidoalloaromadendrane
C16H17NO M 249.395 1,4, 10-Trihydroxy-2-aromadendren-12-oic Sq-0221 0
Constit. of A. cannabina. Oil.
acid
Isocyanide: [55907-33-0). Axisonitrile 2
C16H 15N M 231.380
From A. cannabina. Oil. [cx] 0 +29° (c, 0.5 in CHC1 3). H OH
Has -NC re1acing -NHCHO.
1-Epimer, isocyanide: [108739-39-5]. 10rx.-
lsocyanoalloaromadendrane HO H
C16H 15N M 231.380
lsol. from A. cannabina. Oil. [cx] 0 -17.21 o (c, 0.7 in HOOC '
CHC1 3). C15H110 4 M 266.336
lsothiocyanate: [56012-90-9). Axisothiocyanate 2 (1 p,4rx.,5rx.,6p,7p,1 op,1Orx.,11 p)-form
C16H15NS M 263.446 Me ester:
lsol. from A. cannabina. Oil. [cx] 0 + 12.8° (c, 1.5 in C16H 240 5 M 296.363
CHC1 3). Has -NCS replacing -NHCHO. Constit. of Clavularia koe/likeri. Oil. [cx]D -72° (c, 0.52
1-Epimer, isothiocyanate: [108739-40-8]. 10rx.- in CHC1 3).
/sothiocyanatoaUoaromadendrane Braekman, J.C. eta/, Tetrahedron, 1981, 37, 179 (cryst struct)
C16H15NS M 263.446
From A. cannabina. Oil. [cx] 0 -6.95° (c, 0.9 in CHC1 3). Zierone Sq-02211
Fattorusso, E. et a/, Tetrahedron, 1975, 31, 269 (iso/) Elleryone
Ciminiello, P. eta/, Can. J. Chern., 1987, 65, 518 (isol, struct)
[6754-66-1]
12,13-Dihydroxy-1(1 0)-aromadendren-2- Sq-02207
one
Absolute

~
configuration

C15H110 M 218.338
Constit. of volatile oil of Ziera macrophylla and from
Evodia elleryana. Viscous oil. Bp 18 147-149°. [cx] 0 -179°
HOH2C CH20H (c, 1.32 in CHC1 3).
CtsH1103 M 250.337 Semicarbazone: Cryst. (EtOH). Mp 182°. [cx) 0 -142° (c,
2.86 in CHC1 3).
(4rx.,5p,6rx.,7rx.)-form
Hildebrand, R.P. et a/, Aust. J. Chern., 1959, 12, 436 (iso/)
Di- Ac: 12,13-Diacetoxy-1(10)-aromadendren-2-one Takeshita, H. eta/, Tetrahedron Lett., 1972, 1775 (struct)
CI,H2605 M 334.411
Constit. of Gnephosis brevifolia. Oil.
Jakupovic, J. eta/, Phytochemistry, 1988, '1:1, 3181.

Epipolasin B Sq-02208
[97950-06-6]

~
)-}d
X= -NCS
M 263.446 "'
549
Anastreptene - Hanegokedial Sq-02212 - Sq-02217

Cycloaromadendranes Secoaromadendranes

Anastreptene Sq-02212 4-(2,2-Dimethyl-3-(4-methyl-3- Sq-02215

[64340-33-6] furanyl)cyclopropyl)-2-butanone, 9CI
1,3-Epoxy-2-nor-1 ,10-seco-1(5),3-aromadendradien- 10-one
[122890-34-0]

C15H22 M 202.339
Constit. of Anastrepta orcadensis and other Hepaticae.
Cryst. (EtOH). Mp 91-93°. [tX] 0 + 32° (pentane).
Andersen, N.H. et a/, Phytochemistry, 1977, 16, 1731. C14H 200 2 M 220.311
Andersen, N.H. eta/, Tetrahedron, 1978, 34, 41. Constit. of Mylia taylorii. Oil. [tX] 0 -25.8° (c, 2.98 in
CHC1 3).
Myliol Sq-02213 Harrison, L.J. eta/, Phytochemistry, 1989, 28, 1261.
[34562-58-8]
Furanoplagiochilal Sq-02216
[74320-16-4]

C 15H 220 M 218.338

Constit. of Mylia taylorii. Unstable cryst. Mp 111°.
3-Ketone, 4tX,15-dihydro: [64604-08-6]. Dihydromylione A
C15H 2z0 M 218.338 Ct5Ht80 2 M 230.306
Constit. of M. taylorii. Oil. [tX] 0 -34.1°. Constit. of Plagiochila yokogurensis. Oil. [tX] 0 -80° (c, 0.83
Matsuo, A. et a/, Experientia, 1977, 33, 991. in CHCI 3).
Nozaki, H., J. Chern. Soc., Perkin Trans. 2, 1979, 514. Asakawa, Y. eta/, Phytochemistry, 1980, 19, 2147.

Trinoranastreptene Sq-02214 Hanegokedial Sq-02217

[86160-98-7] Plagiochilal A
[73407-82-6]

OX!H~
OHC
C 12H 16 M 160.258 I '

"'
I
Constit. of Calypogeia granulata. Oil.
Takeda, R. et a/, Bull. Chern. Soc. Jpn., 1983, 56, 1265.
C15H200 2 M 232.322
Constit. of Plagiochila hattoriana andP. semidecurrens.
Cryst. Mp 66-68°. [tX] 0 -10.4°.
Matsuo, A. et a/, J. Chern. Soc., Chern. Commun., 1979, 1010 (isol)
Asakawa, Y. eta/, Phytochemistry, 1980, 19, 2147 (isol)
Taylor, M.D. eta/, Tetrahedron Lett., 1983, 24, 1867 (synth)

550
Hanegoketrial - Plagiochiline C Sq-02218 - Sq-02223

Hanegoketrial Sq-02218 Ovalimethoxy I Sq-02221

[73616-89-4] [80482-85-5]

OH~C~
OHC
I '

"
I

CtsHt803 M 246.305 CtaH 260 4 M 306.401

Constit. of Plagiochila semidecurrens. Oil. [1X] 0 + 200° (c, 1 Constit. of Plagiochila semidecurrens. Oil. [1X] 0 + 55.8° (c,
in CHC1 3). 2.2 in CHC1 3).
Matsuo, A. eta/, J. Chern. Soc., Perkin Trans. I, I98I, 28I6 (isol, 3-Epimer: [74320-14-2]. Ovalimethoxy II
struct) Constit. of P. semidecurrens. Oil. [1X] 0 + 2° (c, 1.5 in
CHC1 3).
Melicophyllone A Sq-02219 Matsuo, A. eta/, J. Chern. Soc., Perkin Trans. I, I98I, 28I6 (isol,
struct)
[116963-85-0]
I
Plagiochilide Sq-02222

o~I;I' s
[67779-72-0]

?~
~ 7

I o

C 15H 180 3 M 246.305

0

Constit. of Melicope triphylla. Plates. Mp 106-107°. [1X] 0

-371 o (CHC1 3). C 15H 200 2 M 232.322
~
7-Hydroxy: [116963-86-1]. MelicophyUone B Cons tit. of Plagiochila yokogurensis. Cryst. M p 110-111°.
CtsHt80 4 M 262.305 [1X]n -6o.
Constit. of M. triphyl/a. Needles. Mp 171-172°. [1X] 0 Asakawa, Y. eta/, Tetrahedron Lett., I978, I553.
-38° (CHC1 3). Mues, R. eta/, Phytochemistry, I979, 18, I568 (cmr)
Asakawa, Y. eta/, Phytochemistry, I980, 19, 2I47 (isol)
71X,8P-Dihydroxy: Melicophyllone C
CtsHt80 5 M 278.304
Constit. of M. triphylla. Needles. Mp 254°. [1X] 0 -56.23° Plagiochiline C Sq-02223
(Me2CO). Ova/ifoliene
Wu, T.-S. et a/, J. Chern. Soc., Chern. Commun., I988, 956 (cryst [73100-51-3]
struct)
Jong, T.-T. eta/, J. Chern. Res. (S), I989, 273; J. Chern. Res. (M),
I70I (isol)

Ovalifolienal Sq-02220
[73616-90-7]

(D
AcOH2 C H "'
Ct9H:I60s M 334.411
Constit. of Plagiochila asplenioides andP. semidecurrens.
Oil. [1X] 0 + 24.SO (c, 2.1 in CHC1 3).
14-Deacetoxy: [74320-19-7]. Deacetoxyovalifoliene.
Plagiochiline H
C 17H 240 3 M 276.375
C 19H 2,.06 M 348.395 Constit. of P. semidecurrens and P. yokogurensis. Oil.
Constit. of Plagiochila semidecurrens. Plant growth [1X] 0 +22° (c, 2.4 in CHC1 3).
regulator (inhibits growth of rice seedlings). Oil. [1X] 0 91X- Acetoxy: 9(1;-Acetoxyovalifoliene
+93.7° (c, 3.7 in CHC1 3). C 21 H 280 7 M 392.448
8-0xo: [73407-81-5]. Ovalifolielllllone Constit. of P. semidecurrens. Oil. [1X] 0 +53.2° (c, 0.6 in
C 1 ~:z:z0 7 M 362.379 CHC1 3).
Constit. of P. decurrens. Cryst. Mp 203°. [1X] 0 + 149.8° Asakawa, Y. et a/, Phytochemistry, I979, 18, 1355; I980, 19, 2I4I
(c,l.6 in CHC1 3). (isol)
Matsuo, A. et a/, J. Chern. Soc., Perkin Trans. I, I98I, 28I6 (isol) Matsuo, A. eta/, J. Chern. Soc., Perkin Trans. I, I98I, 28I6 (isol,
Matsuo, A. et a/, Nippon Kagaku Kaishi (J. Chern. Soc. Jpn.), struct)
I98I, 665.

551
Plagiochiline F - 4-Cubebanol Sq-02224 - Sq-02230

Plagiocbiline F Sq-02224 Taylorione Sq-02227

[73100-53-5] 1,10-Seco-1(5),4( 15)-aromadendradien-10-one
[55304-00-2]

C 1,H160 7
~H
M 366.410
~-_/ C&OAc

Constit. of Plagiochila asp/enioides. Oil. [or:)n + 30.4° (c, 1.2 C 15H 110 M 218.338
in CHC1 3). Revised struct. Constit. of Mylia tay/orii. Oil. [or:]n -28.1°
(c, in CHC1 3).
Asakawa, Y. eta/, Phytochemistry, I919, 18, 1355.
2,4-Dinitropheny/hydrazone: Cryst. Mp 131-132°.
Matsuo, A. et al, J. Chem. Soc., Perkin Trans. I, I979, 2652 (isol,
Plagiochiline G Sq-02225 struct)
[73039-18-6] Nakayama, T. eta/, Chem. Lett., I919, I245 (synth)

H Cubebanes
AcOH2C 'cH20H
C11H:za09 M 424.447
Constit. of Plagiochila ovalifolia. Oil.
4,10-Chromolaevanedione Sq-02228
Ac: [73100-52-4). Plagiochiline D
[100338-87-2]
C13H 300 10 M 466.484
Constit. of P. asplenioides. [or:]n +21° (c, in 1.4 CHC1 3).
10-Epimer, Ac: [73137-02-7]. Plagioclriline E
0
C13H 300 10 M 466.484
Constit. of P. asplenioides. Oil. [or:]n +22° (c, in CHC1 3).
Asakawa, Y. eta/, Phytochemistry, I919, 18, 1355; I980, 19, 2I41.

Plagiochiline I Sq-02226 C 14H 110 1 M 222.327

[74320-18-6] Constit. of Chromolaena /aevigata. Oil.
AcO 0-, Misra, L.N. et al, Tetrahedron, I985, 41, 5353.

9~
~
4,11-Cubebanediol Sq-02229

HOH2C J'--.
C 17H 140 5 M 308.374
Constit. of Plagiochila yokogurensis. Oil. [or:]n + 11.5° (c,
0.52 in CHC1 3).
Ac: [67779-73-1]. Plagioclriline A C 15H 160 1 M 238.369
C 1,H160 6 M 350.411 (4or:,5or:,6P,J Oar: )-form
Constit. of P. yokogurensis and P. semidecurrens. Shows 11-Jlydroxycubebol
insect antifeedant activity. Plant growth regulator Constit. of Hemizonia congesta. Gum. [or:)i;' -33.7° (c,
(inhibits rice seedling growth). Oil. [or:)n +32.3° (c,l.6 in 0.35 in CHC1 3).
CHC1 3). Bohlmann, F. eta/, Phytochemistry, I98I, 20, 2383.
Ac,13-acetoxy: [70447-97-1]. Plagioclriline B
C11H:za08 M 408.447
Constit. of P. semidecurrens and P. hattoriana. Cryst.
4-Cubebanol Sq-02230
Mp 104-105°. [or:Jn +25.7° (c, 1.3 in CHC13). I
I

Asakawa, Y. eta/, Phytochemistry, I980, 19, 2I4I, 2I47.

Matsuo, A. eta/, J. Chem. Soc., Perkin Trans. I; I98I, 28I6. <{)
~
C 15H 160 M 222.370
(4«,5«,6P,JOor:)-form [23445-02-5]

552
3-Cubebene - Ivaxillarin Sq-02231 - Sq-02235

Cubeb camphor
Constit. of fruits of cubeb (Piper lowong). Cryst. (pet.
ether). Mp 61-62°. [IX]~ -61.6° (CHC1 3), [1X]~ -48.3°.
P-D-Galactopyranoside: [112543-27-8]. Arvoside A
Ivaxillaranes
C21 H 360 6 M 384.512
Constit. of Calendula arvensis. [1X] 0 -27.6°.
Tanaka, A. et al, J. Chern. Soc., Perkin Trans. I, I972, I72I
(synth, stereochem) Aspergeigeric acid Sq-02233
Torii, S. et al, Bull. Chern. Soc. Jpn., I976, 49, 771 (synth)
Pizza, C. et al, J. Nat. Prod. (Lioydia), I987, 50, 784 (Arvoside)

3-Cubebene Sq-02231
I
I

~
C15H21.02 M 232.322
Me ester: [84093-59-4].
C16H 220 2 M 246.349
Constit. of Geigeria aspera. Gum. [1X]~4 -43° (c, 0.3 in
CHC13).
C15H 24 M 204.355
Bohlmann, F. et al, Phytochemistry, I982, 21, I679.
(5rz.,6P,7P,10rz.)-form [17699-14-8]rz.-Cubebene
Constit. of oil of cubeb. Oil. [IX]~ -20.0° (CHC1 3).
11-Hydroxy: 3-Cubeben-11-ol. 11-Hydroxy-rz.-cubebene 3-Hydroxy-5,11(13)-ivaxallaradien-12-oic Sq-02234
C 15H 240 M 220.354 cid
Constit. of Eupatorium serotinum. Oil.
Piers, E. eta/, Can. J. Chern., I971, 49, I2 (synth)
Tanaka, A. eta/, J. Chern. Soc., Perkin Trans. I, I972, I72I
(synth)
Martin, S.S. eta/, Phytochemistry, I976, IS, I13 (biosynth)
Thiessen, W.E., Acta Crystallogr., Sect. B, I977, 33, 3838 (cryst
struct)
Connolly, J.D. et al, Phytochemistry, I982, :U, 233 (synth) C 15H 200 3 M 248.321
Bohlmann, F. et al, Phytochemistry, I982, 21, 1153 (deriv) Ac: [125289-98-7].
C 17H 220 4 M 290.358
4(15)-Cubebene Sq-02232 Constit. of Geigeria rigida.
Zdero, C. eta/, Phytochemistry, I989, 28, 3I05 (isol, pmr)
I
I

~
lvaxillarin Sq-02235
[13260-04-3]

C15H24 M 204.355
(5rz.,6p,10rz.)-form [13744-15-5] P-Cubebene
Constit. of oil of bubeb and of the liverwort Seapania
parvitexta. Oil. [1X] 0 -72.3°.
11-Hydroxy: 4(15)-Cubeben-11-ol. 11-Hydroxy-p-cubebene
C15H 240 M 220.354
Constit. of Eupatorium serotinum. Cryst. (pet. ether).
Mp 85°. [1X]~ -44° (c, 1.35 in CHC1 3).
Piers, E. et al, Can. J. Chern., I97I, 49, I2 (synth)
Tanaka, A. eta/, J. Chern. Soc., Perkin Trans. I, I972, I72I
(synth, stereochem)
Matsuo, A. et al, Bull. Chern. Soc. Jpn., I973, 46, 1010 (isol)
Thiessen, W.E., Acta Crystallogr., Sect. B, I977, 33, 3838 (abs
config)
Bohlmann, F. eta/, Phytochemistry, I982, 21, II 53 (deriv)
Ct5Hta04 M 262.305
Constit. of Iva axil/aris. Cryst. (C 6H 6 /Et0Ac). Mp 186-
1880. [cx]i;' -240.8° (c, 0.72 in MeOH).
5-Deoxy, 4,5-didehydro: [10518-13-5]. Anhydroivaxillarin
c.5H 1,03 M 244.290
Constit. of/. axillaris. Cryst. (pet. ether). Mp 133-135°.
[cx] 0 -18°.
3P-Aicohol, 3-Ac: [14026-85-8]. Axivalin
C 17H 220 5 M 306.358
Constit. of/. axillaris and Geigeria rigida. Cryst. (pet.
ether). Mp 138-140°. [1X]i," -132.4° (c, 0.4 in CHC1 3).
Herz, W. eta/, J. Org. Chern., I966, 31, 3232 (isol)
Anderson, G.D. eta/, Tetrahedron Lett., I972, 4423 (struct)
Anderson, G.D. eta/, Acta Crystallogr., Sect. B, I973, 29, 2783
(cryst struct, Axivalin)
McLeod, A.L. eta/, Phytochemistry, I982, 21, I647 (isol)
Zdero, C. eta/, Phytochemistry, I989, 28, 3105 (iso/, pmr, cmr)

553
3-0xo-4,11(13)-ivaxallaradien-12-... - Cyperotundone Sq-02236 - Sq-02239

3-0xo-4,11(13)-ivaxallaradien-12-oic acid Sq-02236

[125289-97-6]
Patchoulanes

A
I

O COOH
Cyperenol Sq-02238
C 15H 180 3 M 246.305 [16981-80-9]
Constit. of Geigeria plumosa. Oil. I

~
Zdero, C. et al, Phytochemistry, 1989, 28, 3105 (isol, pmr)

Zaluzanin A Sq-02237
[14026-80-3] HOH 2 C
CtsH240 M 220.354
Constit. of Cyperus scariosus. Cryst. Mp 94°. [a]~ - 12.1°
(c, 4.3 in CHC13).
Ac: [115334-13-9]. Cyperenyl acetate
C17H 21;01 M 262.391
Constit. of Cirsium dipsacolepis. Oil. [a]n -5.1° (c, 0.8
in CHC1 3).
15-Aldehyde: [115334-16-2]. Cyperenal
C 15H 100 4 M 264.321 C15H 22 0 M 218.338
Constit. of Zaluzania augusta. Cryst. (MeOH). Mp 265°. Constit. of C. dipsacolepis. Oil. [aln +9.6° (c, 0.4 in
[aJn -10° (EtOH). CHC13).
3-Ac: [14051-18-4]. Zaluzanin B 15-Carboxylic acid: Cyparenoic acid
C 17H 220 5 M 306.358 C15H 220 1 M 234.338
Constit. of Z. augusta. Cryst. (Me2CO/Et20). Mp 223- Constit. of Sandwithia guyanensis. Cryst.
2250. [aJn -12° (CHC1 3). (Me2C0jhexane). Mp 162-164°. [a]i,S -18.8° (c, 0.08 in
Di-Ac: Cryst. (Etpjhexane). Mp 108-109°. [aln +22° CHC1 3).
(CHC1 3). Deoxy: [2387-78-2]. Cyperene. Cyperene /. 4-Isopatchoulene
Romo, J. eta/, Tetrahedron, 1967, 23, 29. CtsH24 M 204.355
Guerrero, C. et a/, Rev. Latinoam. Quim., 1985, 16, 62 lsol. from Cyperus rotundus and other plants. Bp 5 104°.
(stereochem) [a]~ -20° (neat). n20 1.5058.
Trivedi, B. eta/, Tetrahedron Lett., 1964, 1197 (Cyperene)
Nera1i, S.B. et al, Tetrahedron Lett., 1967, 2447 (Cyperenol)
Dreyfus, H. et al, Tetrahedron Lett., 1969, 3757 (abs config)
Jacobs, H. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 835 (Cyparenoic
acid)
Takano, S. eta/, Phytochemistry, 1988, 27, 1197 (Cyperenyl
acetate, Cyperenal)

Cyperotundone Sq-02239
Cyperenone. Articulone. /sopatchoulenone
[3466-15-7]

oy&
I

C15H 220 M 218.338

Constit. of Cyperus scariosus, C. rotundus and C.
articulosus. Cryst. (pet. ether). Mp 46-47.SO. Bp0 _5 136-
1380. [aJn +40.4° (c, 3.2 in CHC1 3).
2,4-Dinitrophenylhydrazone: Red cryst. (EtOH). Mp 231-
2320.
Hikino, H. et al, Tetrahedron, 1967, 23, 2169 (struct)
Hikino, H. eta/, Chern. Pharm. Bull., 1968, 66, 43 (synth)
Neville, G.A. eta/, Tetrahedron, 1968, 24, 3891 (pmr, ms, bib/)

554
3-lsopatchoulene - P..Patchoulene Sq-02240 - Sq-02246

3-lsopatchoulene Sq-02240 Nerali, S.B. et al, Sci. Cult., 1969, 35, 110.
[2552-44-5]
I

yS)
I

Rearranged
C 1 ~H 24 M 204.355
Constit. of Cyperus scariosus. Oil. [a]~ -24.9°.
patchoulanes
Uppal, S.K. et al, Phytochemistry, 1984, 23, 2367.

oc-Patchoulene Sq-02241
Norpatchoulenol Sq-02244
(560-32-7]
[41429-52-1]

®
I

H
C 1 ~H 24 M 204.355
Isol. from essential oils, e.g. Parabenzoin trilobium, C14H:n0 M 206.327
Nardostachys jatamansi, patchouli oil. Bp0 . 14 53.5-54.5°. Odiferous constit. of patchouli oil. Cryst. by sub!. Mp 155-
Prob. artifact of dehydration of patchouli alcohol. Bp 1600.
refers to a mixt. with y-patchoulene. Niwa, H. et al, Tetrahedron Lett., 1984, 25, 2797 (synth)
~ 10 • 14 - Isomer: [508-55-4]. y-Patchoulene
C 1 ~H 24 M 204.355 1,12-Patchoulanediol Sq-02245
Isol. from essential oils, e.g. patchouli oil, P. trilobum,
I
as artifact of dehydration. Oil. HOI

HOH~
Biichi, G. et al, J. Am. Chern. Soc., 1961, 83, 927 (synth)
Tsubaki, N. et al, Bull. Chern. Soc. Jpn., 1967, 40, 597 (isol)
Ruecker, G. et al, Phytochemistry, 1976, 15, 224 (isol, ms)

Patchoulenol Sq-02242
[17806-54-1] C 1 ~H 21;0 2 M 238.369
Constit. of Pogostemon cab/in and prod. of biological
oxidation of Patchouli alchohol. Cryst. (hexane/C 6H 6).

~
Mp 132.5-133°.
Trifilieff, E., Phytochemistry, 1980, 19, 2467 (isol, struct)
Niwa, H. et al, Tetrahedron Lett., 1984, 25, 2797 (synth)
OH
C 1 ~H 24 0 M 220.354 IJ-Patchoulene Sq-02246
Constit. of Cyperus scariosus. Cryst. Mp 74°. [a]~ -54.23° 1,2 ,3,4,5,6, 7,8-0ctahydro-1 ,4,9,9-tetramethyl-4, 7-
(c, 3.8 in CHC1 3). methanoazulene, 9CI
Ketone: [5986-54-9]. Patchoulenone [514-51-2]
C 1 ~H:n0 M 218.338

¢i!:>
I

Constit. of C. rotundus. Cryst. (MeOH). Mp 52.5°. (a]n

-97.1° (c, 8 in CHCI 3).
Trivedi, B. et al, Collect. Czech. Chern. Commun., 1964, 24, 1675
(isol)
Hikino, H. et al, Chern. Pharm. Bull., 1965, 13, 629 (struct) CtsH24 M 204.355
Nerali, S.B. et al, Tetrahedron Lett., 1967, 2447 (isol) Constit. of guaiac wood oil (Bulnesia sarmienti) and
Hikino, H. et al, Chern. Pharm. Bull., 1968, 16, 43 (synth) patchouli oil (Pogostemon patchouli). Also in oil of
Valeriana wallichii. Oil. Bp0 . 6 66.8°. [a]~ -42.6° (c, 10.5
Scariodione Sq-02243 in CHC1 3). n~ 1.4978.

ow
[19419-60-4] ~ 1 • 2 -Isomer: [53823-16-8]. J-Patchoulene
I
C15H 24 M 204.355
I Semisynthetic. Oil. [a]~ -61.7° (EtOH).
Biichi, G. et al, J. Am. Chern. Soc., 1961, 83, 927 (isol, struct)
Bates, R.B. et al, J. Am. Chern. Soc., 1962, 84, 1307 (synth)
Narayanan, C.S. et al, Tetrahedron, 1964, 20, 963 (isol)
Mookherjee, B.D. et al, J. Agric. Food Chern., 1974, 22, 771 (.5-
0 Patchoulene)
C 1 ~H10 0 1 M 232.322 Akhita, A. et al, Phytochemistry, 1987, 26, 2705 (biosynth)
Constit. of Cyperus scariosus. Cryst. Mp 45°.

555
Patchouli alcohol- 6-Valerenen-11-ol Sq-02247 - Sq-02251

Patchouli alcohol Sq-02247 Anhydrovalerenol

Patchoulol. Patchouli camphor Constit. of soft coral, Xeniidae sp. Oil. [1Xln -150°
[5986-55-0l (CHC1 3). The name anhydrovalerenol is misleading.

®
Kobayashi, M. eta/, Chern. Pharm. Bull., 1982, 30, 3431.

4,7(11 )-Valerenadien-12-ol Sq-02250

I
H

~
C 15H 260 M 222.370
Constit. of patchouli oil (Pogostemon patchouli). Also in
Pogostemon p/ectranthoides and Valeriana wallichii.
(1 ~. lOcx, 7(11 )E)-form
Cryst. (pentane). Mp 55-56°. [ali? -129° (c, 4.02 in
CHC1 3).
Dobler, M. et al, Proc. Chern. Soc., London, 1963, 383 (cryst CH20H
struct)
Mirrington, R.N. et al, J. Org. Chern., 1972, 37, 2871 (synth) CtsH240 M 220.354
Naf, F. et al, Helv. Chim. Acta, 1974, 57, 1868; 1981, 64, 1387 (1P,10a.,7(11)E)-form [101628-22-21 Vakrenol. IX- Va/erenol
(synth) Found as the free alcohol and as esters in Valeriana
Yamada, K. et al, Tetrahedron, 1979, 35, 293 (synth) officina/is. Oil.
Neszmelyi, A. eta/, J. Chern. Soc., Chern. Commun., 1981, 999
(cmr) 12-Aldehyde: [4176-16-31. 4,7{11)-Valeradien-12-al.
Akhila, A. et al, Phytochemistry, 1988, 27, 2105 (biosynth) Valerenal
Cory, R.M. et al, Tetrahedron Lett., 1990, 31, 6839 (synth) C 15H 220 M 218.338
Constit. of V. officina/is. Oil.
12-Aldehyde, semicarbazone: Mp 176-177°.
(1P,10p,7(11)E)-form
10-epi-a.- Vakrenol. 10-Epivalerenol
Valeranes Constit. of Zexmenia gnaphaloides.
12-Aldehyde: 10-epi-a.- Vakrenal. 10-Epivalerenal
C 15H 220 M 218.338
Constit. of Z. gnaphaloides. Oil. [ali; + 5.2° (c, 1.1 in
CHC1 3).
2-Hydroxy-4,7(11)-valerenadien-12-oic Sq-02248 (lp,10a.,7(11)Z)-form
acid 12-Aldehyde: Constit. of Z. gnaphaloides. Oil.
Stoll, A. eta/, Helv. Chim. Acta, 1957, 40, 1205 (Valerenal)
Bates, R.B. eta/, Chern. Ind. (London), 1965, 1731 (struct, synth,
Valerenal)
Bohlmann, F. et al, Chern. Ber., 1980, 113, 2410.
Bos, R. et a/, Phytochemistry, 1986, 25, 133 ( Valerenol)

6-V alerenen-11-ol Sq-02251

COOH
C 15H 220 3 M 250.337
Cryst. (Etp). Mp 169-169.5°.
(lcx,4~,5cx,6E, 10~)-:form
(1P,2P,10a.)-form [1619-16-51 Valerenolic acid
Constit. of the roots of Valeriana officina/is. [ali? -93.8°
(c, 0.79 in EtOH).
Ac: Acetylvakrenolic acid
C 17H 240 4 M 292.374 C 15H 260 M 222.370
Constit. of V. officina/is. Oil (as Me ester). [ali? -61° (c, (1 a.,4P,5a.,6E,1 0/1)-form [84249-42- 3llsovakrenenol
1.75 in EtOH)(Me ester). Constit. of soft coral, Xeniidae sp. Semisolid. [aln +45°
Stoll, A. et a/, Justus Liebigs Ann. Chern., 1957, 603, 158 (isol) (CHC1 3).
Birnbaum, G.I. et al, J. Org. Chern., 1978, 43, 272 (cryst struct)
(la.,4p,5rx,6Z,10f/)-form [84249-43-41 Vakrenenol
Constit. of X. spp. Oil. [aln + 123° (CHC1 3).
6(8),7(11)· V alerenadiene Sq-02249 Kobayashi, M. et al, Chern. Pharm. Bull., 1982, 30, 3431 (isol,
pmr, cmr, cryst struct)

Absolute
configuration

C 15H 24 M 204.355
(1a.,4P,5a.,l0f/)-form [84249-44-51

556
2-Africananol - 10-Hydroxy-2-africanen-4-one Sq-02252 - Sq-02256

2(6)-Africanen-1-one Sq-02255

Africananes

2-Africananol Sq-02252
C 15H 120 M 218.338
Jrx.-form [90851-05-1] Africanone
Constit. of Lippia integrifolia. Oil. [1X]i:' -0.12° (c, 0.85
in CHC1 3).
(2a.,3a.,6a.)-form Dartayet, G.H. eta/, Phytochemistry, 1984, 23, 688.

C 15H 260 M 222.370 1~Hydroxy-2-africanen-4-one Sq-02256

(2rx.,3rx.,6rx.)-form [104975-19-1]/soafricanol 8-Hydroxy-4-senoxyrien-3-one
C15H260 M 222.370
Constit. of fungus Leptographium lundbergii. Oil. [1X]i;l
+ 11.4° (c, 0.59 in CHC1 3).
(2rx.,3p,6rx.)-form [53823-07-7] Africanol
Constit. of Lemnalia africana. Cryst. Mp 58-60°. [1X]n
+59.SO (c, 0.5 in CHC1 3).
Tursch, B. et a/, Tetrahedron Lett., 1974, 747 (Africanol) C 15H 120 2 M 234.338
Karlsson, R., Acta Crystal/ogr., Sect. B, 1976, 32, 2609 (cryst lOP-form
struct) Ac: Cryst. Mp 78-79°.
Abraham, W.R. eta/, Tetrahedron, 1986, 42, 4475 (lsoafricanol)
Angeloyl: [69971-31-9].
C 20H 280 3 M 316.439
3-Africananol Sq-02253 Constit. of Senecio oxyriifolius. Oil. [1X]i; +44.1 ° (c, 3.06
in CHC1 3).

HO~
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1669 (isol)
Bryson, I. et a/, Tetrahedron Lett., 1979, 3891 (synth)

C 15H 260 M·222.370

Jrx.-form [104975-20-4] Leptographiol
Constit. of fungus Leptographium lundbergii. Viscous oil.
[1X]i;l + 17.6° (c, 1.0 in CHC1 3).
JP-form [104900-63-2]/soleptographiol
C15H260 M 222.370
Constit. of L. lundbergii. Oil. [1X]i;l + 14.6° (c, 0.63 in
CHC1 3).
Abraham, W.-R. eta/, Tetrahedron, 1986, 42, 4475.

3(15)-Africanene Sq-02254
9(15)-Africanene
[74016-87-8]

C 15H 24 M 204.355
Constit. of Sinularia erecta. Oil. [1X]i; + 86° (c, 3.7 in
CHC1 3).
Kashman, Y. eta/, Experientia, 1980, 36, 891.

557
1,8-Epoxy-2,6-himachaladiene - 1,3,5-Himachalatriene Sq-02257 - Sq-02264

Constit. of Cedrus deodara, C. atlantica and C. libani. Oil.

Bp2 93-94°. [IX]~ -187.1° (neat). n~ 1.5082.
Himachalanes Bredenberg, J.B. et a/, Acta Chern. Scand., 1961, 15, 685 (isol,
struct)
Joseph, T.C. eta/, Tetrahedron, 1968, 24, 3809, 3841 (isol, struct)
Wenkert, E. eta/, Synth. Commun., 1973, 3, 45 (synth)
Oppolzer, W. eta/, Helv. Chim. Acta, 1981, 64, 2592 (synth)

1,8-Epoxy-2,6-himachaladiene Sq-02257
2,7-Himachaladiene Sq-02261
y-Himachalene

~ [53111-25-4]

C 15H 220
~
M 218.338
(lrz,Brz)-form [64825-86-1] Oxidohimachalene
Constit. of Cedrus deodara. Bp 2_5 101-103°. [1X]n +20.7°
C 15H 24 M 204.355
(c, 1.3 in CHCI 3).
Constit. of the essential oil of anise and of Pterocaulon
Shankaranarayan, R. et al, Tetrahedron, 1977, 33, 1207. virgatum. Oil. [1X]i; -9° (c, 0.24 in CHC1 3).
Plattier, M. et a/, Recherches, 1974, 19, 145 (struct)
4,7-Epoxy-1-himachalen-3-ol Sq-02258 Tabacchi, R. eta/, Helv. Chim. Acta, 1974, 57, 849 (isol)
3,10-0xido-5-himachalen-4-ol Bohlmann, F. et al, Phytochemistry, 1985, 24, 505 (isol)
[87376-74-7]
2,7(14)-Himachaladien-15-ol Sq-02262

~
rz-Torosol
[113807-90-2]

HO~
C 15H 240 2 M 236.353
(31;,4fl,7fl)-form
Constit. of Artemisiafilifolia. Cryst. (Et20jpet. ether)
(as acetate). Mp 145° (acetate), Mp 133°. [1X]~4 +64° (c, C 15H 240 M 220.354
0.27 in CHC1 3) (acetate). Constit. of Cedrus libanotica. Oil. [IX]~ -180.2° (c, 2.7 in
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 503. CHC1 3).
Avcibasi, H. et a/, Phytochemistry, 1987, 26, 2852.
2,6-Himachaladiene Sq-02259
fl-Himachalene 2,7-Himachaladien-15-ol Sq-02263
[1461-03-6] fl-Torosol
[113807-91-3]

C 15H 24 M 204.355
HOH,C~
Constit. of Cedrus deodara, C. atlantica and C. libani. Oil. C 15H 240 M 220.354
Bp4 121-122°. [IX]~ +225.8° (neat). n~ 1.5113. Constit. of Cedrus libanotica.
Challand, B.D. eta/, J. Chern. Soc., Chern. Commun., 1967, 704 Avcibasi, H. eta/, Phytochemistry, 1987, 26, 2852.
(synth)
Joseph, T.C. et al, Tetrahedron, 1968, 24, 3809, 3841 (isol, struct)
Wenkert, E. eta/, Synth. Commun., 1973, 3, 45 (synth) 1,3,5-Himachalatriene Sq-02264
Piers, E. et al, J. Chern. Soc., Chern. Commun., 1979, 166 (synth) ar-Himachalene
Oppolzer, W. et al, Helv. Chim. Acta, 1981, 64, 2592 (synth) [19419-67-1]

2,7(14)-Himachaladiene
rz-Himachalene
[3853-83-6]
Sq-02260

u,ccQ
C 15H 22 M 202.339
Constit. of Cedrus deodara. Oil. Bp 2_5 109-110°. [IX]~ + 5.9°
(c, 1 in CHC1 3).
Pandey, R.C. et al, Tetrahedron, 1968, 24, 3829 (isol, synth)
M 204.355 Mehta, G. eta/, J. Org. Chern., 1974, 39, 2618 (synth)

558
1,3,5-Himachalatrien-5-ol - 5-Hydroxy-2-himachalen-12,7-olide Sq-02265 - Sq-02270

1,3,5-Himacbalatrien-5-ol Sq-02265 2-Himacbalen-7-ol Sq-02269

Podocep/uUol

~
[66656-01-7]

Ct 5H160 M 222.370
7«.-form (1891-45-8] Himac/uUol
C 15H 120 M 218.338
Constit. of Cedrus deodara. Antispasmodic agent. Cryst.
Constit. of Lasianthaea podocepha/a. Oil. [IX]~ + 10.6° (c,
(MeCN). Mp 67-68°. [1X]n + 72.9° (c, 1.8 in CHCI 3).
0.75 in CHC1 3).
Bisarya, S.C. et al, Tetrahedron, 1968, 24, 3861 (isol)
Bohlmann, F. et al, Chern. Ber., 1978, 111, 843.
Narula, A.P.S. et al, Tetrahedron, 1977, 33, 813 (synth)
Bhan, P. et al, J. Chern. Res. (S), 1982, 344 (cryst struct)
2-Himacbalene-4,7-diol Sq-02266
5-Hydroxy-2-bimacbalen-12,7-olide Sq-02270
HO I

~
(4a,1P}form

CtsH160 2 M 238.369 H,
I

(4«.,7/1)-form [57308-23-3] lsocentdarol C 15H120 3 M 250.337

Constit. of Cedrus deodara. Cryst. Mp 165°. [1X]n +5.0°
(1P,5«,6«.,7/I)-form
(c, 1 in EtOH).
I -Hydroxyhimaclullanolide
(4f.,7f.)-form [69256-30-0]
Angeloyl: [79396-09-1].
Xeroferol
C20 H 280 4 M 332.439
Cryst. Mp 142-144°.
Constit. of Acritopappus longifo/ius. Oil. [IX]~ +20.4° (c,
4-(3-Hydroxy-4-methoxybenzoyl): [69184-32-3]. Xeroferin 1.5 in CHCI 3).
C23H 320 15 M 548.497
Bell, E.A. et al, Biochem. J., 1964, 91, 358 (occur, biosynth)
Constit. of Ferula xeromorpha. Cryst. (EtOAcfhexane). Hirst, G.E. et al, Biochem. J., 1964, 91, 361 (ir, pmr)
Mp 118-120°. Bohlmann, F. et al, Phytochemistry, 1981, 20, 275 (isol)
Kulshreshtha, O.K. et al, Phytochemistry, 1976, 15, 557
(lsocentdmol)
Bizhanova, K. et al, Khim. Prir. Soedin., 1978, 581 (Xeroferol,
Xeroferin)

2-Himacbalene-7,12-diol Sq-02267

CtsHl602
~ ~
M 238.369
H CHOH
12 2

7/J-form [97457-08-4]
Constit. of Blumea gariepina. Oil.
Bohlmann, F. et al, Phytochemistry, 1985, 24, 505.

3-Himacbalene-2,7-diol Sq-02268

C 15H160 2
~
M. 238.369
(2p,7/l)-form [57308-24-4] Centdarol
Constit. of Cedrus deodara. Cryst. Mp 140°. [1X]n -97.3°
(c, 1 in EtOH).
Kulshreshtha, O.K. et al, Phytochemistry, 1975, 14, 2237.

559
8,10-Dihydroxy-3-longipinen-5-one - 3-Longipinene Sq-02271 - Sq-02276

10-Hydroxy-3(15)-longipinen-2-one Sq-02274
[81916-01-0]
Longipinanes

8,10-Dihydroxy-3-longipinen-5-one
7,9-Dihydroxy-2-/ongipinen-1-one
Sq-02271
C 15H 220 2
XJQOH
M 234.338

~OH 12«-form
ent-12P- Hydroxy- 2(1 0)-/ongipinen- 3-one
Cryst. (hexane). Mp 91-92°. [o:]~ -50.4° (c, 1.4 in

~OH
CHC1 3).
Ac:
Ct,H240 3 M 276.375
C 15H 220 3 M 250.337 Constit. of Marsupel/a aquatica. Cryst. (hexane). Mp 95-
(8«,10/1)-form [97335-21-2] 960. [o:]~ -17.1° (c, 4.9 in CHC1 3).
Constit. of Lavandula stoechas and Stevia salicifolia. Huneck, S. et al, Phytochemistry, 1982, 21, 143.
Cryst. (CHC1 3). Mp 183-184°. [o:] 0 +48° (c, 2 in EtOH).
8- Ac: 8o:-Acetoxy-1 OP-hydroxy-3-/ongipinen-5-one. 9o:- 4-Longipinanone Sq-02275
Acetoxy-1P-hydroxy-2-longipinen-1-one 2-Longipinanone
C 17H 240 4 M 292.374
Constit. of L. stoechas. [87421-00-9]
Roman, L.U. et al, J. Org. Chern., 1985, 50, 3965 (isol, struct)
U1ube1en, A. et al, Phytochemistry, 1988, 27, 3966 (isol, deriv)

10,12-Dihydroxy-3-longipinen-5-one Sq-02272
7,13-Dihydroxy-2-/ongipinen-1-one

C 15H 240 M 220.354

Constit. of Artemisia fi/ifolia. Oil. [o:]~ + 19° (c, 1.34 in
CHC13).
[81915-99-3]
Bohlmann, F. et al, Phytochemistry, 1983, 22, 503.

C 15H 22 0 3 M 250.337 3-Longipinene Sq-02276

«-Longipinene
lOP-form [100045-39-4]
Constit. of Stevia acha/ensis. Oil. [o:]~ +64° (c, 0.65 in [5989-08-2]

rA
CHC1 3).
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1985, 1764; 1986,
799 (isol)
(+)-form
10-Hydroxy-3-longipinen-5-one Sq-02273 15~
7-Hydroxy-2-oxo-o:-/ongipinene
CISH24 M 204.355

~
(+)-form
Constit. of Pinus spp. Bp 10 102-106°. [o:]i; +36.9° (c, 2.2
in CHC1 3). ni; 1.4924.

~OH (-)-form
Constit. of Scapania undulata.
!130 5>-Jsomer: 3(1 5)- Longipinene. P-Longipill(!ne
C 15H 220 2 M 234.338
Constit. of S. undulata.
10«-form
Erdtman, H. et al, Acta Chern. Scand., 1963, 17, 2351 (isol, uv,
Constit. of Stevia polycephala. Oil. pmr)
Bohlmann, F. et al, Chern. Ber., 1977, 110, 3572. Miyashita, M. et al, J. Am. Chern. Soc., 1974, 96, 1917 (synth)

560
3(15)-Longipinen-4-ol - Longicyclene Sq-02277 - Sq-02282

3(15)-Longipinen-4-ol Sq-02277 CzsH360 6 M 432.556

Mfll'supeUol Constit. of P. texana. Oil.
[69624-76-6] [115794-33-7]
Bohlmann, F. eta/, Chern. Ber., 1975, 108, 3543.
Roman, L.U. eta/, Tetrahedron, 1981, 37, 2769 (Rastevione)
Amaro, J.M. et al, Phytochemistry, 1988, 27, 1409
(Triflorestevione)

8,9,10-Trihydroxy-3-Iongipinen-S-one Sq-02280
7,8 ,9-Trihydroxy-1-oxo-oc-/ongipinene
C 13H 240 M 220.354
Constit. of Marsupella emarginata. Oil. [cx]n + 13.4° (c,
1.34 in CHC1 3).
4-Ketone: [69624-75-5]. 3(15)-Longipinen-4-one.
Mfll'supellone
C 13Hzz0 M 218.338
Constit. of M. emarginata. Oil. [cxJn -1.9° (c, 3.5 in
CHC1 3). C13Hzz04 M 266.336
14-Acetoxy, 4-ketone: [69624-77-7]. 14-Acetoxy-3(15)-
(8rx.,9P,JO/I)-form
longipinen-4-one. 14-Acetoxymarsupellone. 9- 8-Ange/oy/, 9-(3-methylbutanoyl): [58226-70-3].
Acetoxymarsupe//one C15H 360 6 M 432.556
Ct,H240 3 M 276.375 Constit. of Polypteris texana. Oil.
Constit. of M. emarginata. Oil. [oc]n +6.9° (c, 1 in 8,9-Diange/oy/: [58130-66-8].
CHC1 3). C15H 340 6 M 430.540
Matsuo, A. et at, Chern. Lett., 1979, 73. Constit. of P. texana. Oil.
2,3-Dihydro: see 8,9,10-Trihydroxy-5-/ongipinanone, Sq-
3-Longipinen-5-one Sq-02278 02279
Bohlmann, F. et al, Chern. Ber., 1975, 108, 3543.
1-0xo-oc-/ongipinene. Jlulgfll'one B
[64180-68-3]

Longifolanes
C13Hzz0 M 218.338
Constit. of Tanacetum tanacetioides and essential oil of
Chrysanthemum vulgare. Oil or cryst. Mp 35.5-36°. [cxln
10,15-Epoxylongifolane Sq-02281
3,7-Epoxylongifolane
+63.4° (c, 1.1 in CHC1 3), [oc]~ +81.3° (c, 3.1 in CHCI 3).
[65556-52-7]
BohlmaJIJJ, F. et al, Chern. Ber., 1977, 110, 3572.
Uchio, Y., Tetrahedron, 1978, 34, 2893.

8,9,10-Trihydroxy-5-Iongipinanone Sq-02279

OH
I
C13Hu0 M 220.354
Famesane numbering system used in preference to several
(3a,8a,9a, I OJ3}:form
other numbering systems in the lit. Constit. of
H heartwood of Juniperus conferta. Cryst. Mp 38-39°. [oc]i:'
C13H 240 4 M 268.352 - 144.8° (CHCI 3).
(3rx.,8rx.,9rx.,l0f/)-form Doi, K. eta/, Tetrahedron Lett., 1971, 4003 (isol, struct)
Jadhar, P.K. et a/, Tetrahedron Lett., 1976, 4855 (synth)
9,10-Ditig/oyl: [115794-33-7]. Trijlorestevione
C15H 360 6 M 432.556
Constit. of Stevia triflora. Oil. Longicyclene Sq-02282
9,10-Diange/oy/: [80388-43-8]. Rastevione [1137-12-8]
C15H 360 6 M 432.556
lsol. from S. serrata. Cryst. (CHCI 3jhexane). Mp 130-
1310.
(3P,8rx.,9p,JO/I)-form
8-Ange/oy/, 9-(3-methy/butanoyl): [58170-12-0].
C15H 380 6 M 434.572
Constit. of Polypteris texana. Oil.
8,9-Diange/oy/: [58130-65-7]. M 204.355

561
15-Longifolanol - Longibornyl bromide Sq-02283 - Sq-02287

Constit. of Pinus longifolia oil. d~0 0.931. Bp 2 82°. [acln 3(15)-Longifolen-8-ol Sq-02285
+ 36.6° (neat). ni? 1.4888. 7( 15)-Longifolen-5-ol
Nayak, V.R. eta/, Tetrahedron Lett., 1963, 243 (iso/, uv, ir, pmr)
Welch, S.C. et a/, J. Org. Chern., 1974, 39, 2665 (synth)

15-Longifolanol Sq-02283
lsolongifolol
[1139-17-9]

C 15H 240 M 220.354

8ft-form [35049-12-8]
Constit. of Juniperus conferta. Cryst. Mp 86-87°. [ac]~
+ 13.SO (CHC1 3).
Jadhav, P.K. eta/, Tetrahedron Lett., 1976, 4855 (synth)
Jadhav, P.K. eta/, Indian J. Chern., Sect. B, 1978, 16, 952 (synth)

C 15H 260 M 222.370

Cryst. (pet. ether). Mp 112-lW. [ac]i;l -46.9°.
Aldehyde: [25491-00-3]. 15-Longifolanal. /solongifolic
aldehyde. lsolongifolal
C 15H 240 M 220.354
Oil. Bp 35 170°.
Longibornanes
Carboxylic acid: [487-74-1]. 15-Longifolanoic acid.
/solongifolic acid
C 1sH 240 2 M 236.353
Longiborneol Sq-02286
Cryst. (AcOH). Mp 136°. [ac]46 -12.7° (EtOH).
Juniperol. Kuromatsuol. M acrocarpol
Nayak, V.R. et a/, Tetrahedron, 1963, 19, 2293 (lsolongifolic acid)
Patnekar, S.G. eta/, Tetrahedron, 1967, 23, 919 (lso/ongifolol) (465-24-7]
Mehta, G. et a/, Tetrahedron, 1968, 24, 4105 (lso/ongifolic
aldehyde)

Longifolene Sq-02284
Kuromatsuene. Junipene. Juniperene
[475-20-7]
ClsH24 M 204.355
Widespread in plants, found in turpentines. Plant growth
regulator (promotes wheat coleoptile growth). Oil. Bp706
254-256°, Bp 36 150-151°. [1X]n +41.05°.
Corey, E.J. eta/, J. Am. Chern. Soc., 1964, 86, 478 (synth)
Thierry, J.-C., Tetrahedron Lett., 1969, 2663 (cryst struct)
Huneck, S. et a/, Phytochemistry, 1972, 11, 2429.
Karrer, W. eta/, Konstitution und Vorkommen der Organischen
Pjlanzensto.ffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985, Longibornyl bromide
no. 1930a (occur)
Volkmann, R.A. et a/, J. Am. Chern. Soc., 1975, 97, 4777 (synth)
Dev, S., Ace. Chern. Res., 1981, 14, 82 (rev)
I
OH
C 1sH2P M 222.370
Constit. of many Juniperus, Pinus and Cupressus spp. also
Dacrydium spp., Cedrus deodara. Plant growth regulator
(inhibits cress root growth, promotes wheat seed
germination). Cryst. (pentane). Mp 112°. [acln +25.4°
(EtOH).
Ketone: [465-26-9]. Longicamphor
Constit. of Cupressus spp. Oil. Bp 20 50°. [acln +22° (c,5.8
in EtOH).
Akiyoshi, S. et a/, Tetrahedron, 1960, 9, 237 (struct)
Huneck, S. eta/, Phytochemistry, 1972, 11, 2429.
Welch, S.C. eta/, J. Org. Chern., 1974, 39, 2665 (synth)
Kuo, D.L. eta/, Can. J. Chern., 1988, 66, 1794 (synth)
Sq-02287
Longifolene hydrobromide

~
Dev, S., Prog. Chern. Org. Nat. Prod., 1981, 40, 49 (rev)
Schulz, A.G. eta/, J. Org. Chern., 1985, 50, 915 (synth)
Kuo, D.L. eta/, Can. J. Chern., 1988, 66, 1794 (synth)

Br
C 15H 25 Br M 285.266
Formed by reaction of HBr with longifolene. Cryst. Mp
69-70°. [acJn +5° (c,5.1 in EtOH).
Naffa, P. eta/, Bull. Soc. Chim. Fr., 1954, 1410 (synth)

562
Dehydropinguisenol - (X-Pinguisene Sq-02288 - Sq-02295

Constit. of P. vernicosa and P. elegantula. Oil. [ex]~

-60.2° (c, 0.91 in CHC1 3).
Pinguisanes [67594-77-8)
Asakawa, Y. et a/, Bull. Soc. Chim. Fr., 1976, 1469 (isol)
Fukuyama, Y. eta/, Phytochemistry, 1988, 27, 3557 (isol, struct)

Pinguisanin Sq-02292
Dehydropinguisenol Sq-02288
[73020-90-3]
[78161-07-6]
15

c(p HO
I
C 15H 200 2
~
<(0~
M 232.322
Struct. revised in 1987. Constit. of Porella platyphylla.
C 15H 200 2 M 232.322 Cryst. Mp 50-51°. [exJn +18° (c, 1.7 in MeOH).
Not the dehydro deriv. of Pinguisenol, Sq-02297. Constit.
4,15-Didehydro: [76192-77-3]. Dehydropinguisanin
of Trocholejeunea sandvicensis. Oil. [exln + 5.6° (c, 2.5 in
CHCI 3). C,sH 180 2 M 230.306
Constit. of Trocholejeunea sandvicensis. Oil. [exln +4.4°
Asakawa, Y. eta/, Phytochemistry, 1980, 19, 2651. (c, 5.8 in CHC1 3).
Asakawa, Y. eta/, Phytochemistry, 1979, 18, 1349; 1980, 19, 2651
Naviculol Sq-02289 (isol)
Asakawa, Y. eta/, J. Chern. Res. (S), 1987, 82 (struct)

HOH,~ Pinguisanolide Sq-02293

[73020-89-0]
0

~
C 15H 21,0 M 222.370
Constit. of Porella navicularis. Oil. [exln +48.5° (c, 1.14 in
CHCI 3).
Toyota, M. et a/, Phytochemistry, 1989, 28, 1661.
C,sH200 3 M 248.321
Struct. revised in 1990. Strictly no longer a pinguisane.
Norpinguisanolide Sq-02290 Constit. of Porella platyphylla. Oil.
[119285-62-0] Asakawa, Y. eta/, Phytochemistry, 1979, 18, 1349 (isol)
Connolly, J.D., Proc. Phytochem. Soc. Europe, 1990, 29, 41 (struct)

~0 Pinguisenal
[76192-76-2]
Sq-02294

OH~
0
C,4H,404 M 246.262
Constit. of Porella elegantula. Plates (hexane). Mp 132-
1340. [ex]~ -125° (c, 0.47 in CHCI 3).
Fukuyama, Y. eta/, Phytochemistry, 1988, 27, 3557 (isol, pmr) C 15H 200 3 M 248.321
Struct. revised in 1987. Constit. of Trocholejeunea
Norpinguisone Sq-02291 sandvicensis. Oil. [exln+ 0° (c, 0.18 in CHC1 3).
[62121-27-1] Asakawa, Y. eta/, Phytochemistry, 1980, 19, 2651 (isol)
Asakawa, Y. eta/, J. Chern. Res. (S), 1987, 82 (strcut)
0

<=¢R
(X- Pinguisene Sq-02295
[62121-24-8]

C 14H 180 2 M 218.295

Constit. of Porella vernicosa and P. elegantula. Shows
antifungal activity. Cryst. Mp 126-127°. [exln + 2°
(CHC1 3). C,sH 24 M 204.355
12-Carboxylic acid, Me ester: [119285-56-2]. Methyl 4- Constit. of Porella spp. Oil. [1X]n -43°.
oxonorpinguisan-12-oate. Norpinguisone methyl ester Asakawa, Y. eta/, Phytochemistry, 1978, 17, 457.
(incorr.)
C,sH 180 4 M 262.305

563
P-Pinguisenediol - Spiropinguisanin Sq-02296 - Sq-02302

IJ-Pinguisenediol Sq-02296 Porellapinguisenone Sq-02300

[73020-88-9] [126585-83-9]

~OH OHCX:R

0
-OH

HO
ClsH140 1 M 236.353 C15Hn03 M 250.337
Constit. of Pore/la platyphylla. Viscous oil. [oc) 0 -42° (c, Constit. of Porella cordaeana.
0.4 in MeOH). Toyota, M. et al, Phytochemistry, 1989, 28, 3383 (isol, pmr, cmr)
Asakawa, Y. eta/, Phytochemistry, 1979, 18, 1349.
Ptycbanolide Sq-02301
Pinguisenol Sq-02297 [81674-82-0]
[62121-19-1]

C1sH160 M 222.370 C15Hn03 M 250.337

~
Constit. of Ptychanthus striatus. Cryst. (EtOAcfhexane).
Constit. of Pore/la spp. Oil.
Asakawa, Y. eta/, Phytochemistry, 1978, 17, 457.
Mp 143-144°. [cx]~4 +23.2° (c, 0.47 in CHC1 3).
Takeda, R. et al, Bull. Chem. Soc. Jpn., 1983, 56, 1125 (cryst
struct)
Pinguisone Sq-02298
[22489-40-3] Spiropinguisanin Sq-02302
[126585-84-0]

Ho0Jb
C 15H 180 1 M 232.322
Constit. of Aneura pinguis. Shows insect antifeedant 6~
activity. Cryst. Mp 63-63.5°. [a]~ +64.3° (C6H 6). 0
Deoxo: [49776-70-7]. Deoxopinguisone C15Hn05 M 282.336
C15Hn0 M 218.338 Constit. of Pore/la cordaeana. Amorph.
Constit. of Ptilidium ciliare and Pore/la vernicosa. Liq. Toyota, M. eta/, Phytochemistry, 1989, 28, 3383 (isol, pmr, cmr)
[cx) 0 -27° (CHC1 3).
Bene8ova, V. eta/, Collect. Czech. Chern. Commun., 1969, 34, 1810
(isol)
Wada, K. et al, Agric. Bioi. Chern., 1971, 35, 115.
Krutov, S.M. et al, Phytochemistry, 1973, 12, 1405 (isol, deriv)
Corbella, A. eta/, J. Chern. Soc., Perkin Trans. 1, 1974, 1875
(struct)
Asakawa, Y. eta/, Bull. Soc. Chim. Fr., 1976, 1469 (isol, deriv)
Bernasconi, S. et al, J. Chern. Soc., Perkin Trans. 1, 1981, 2395
(synth)
Uyehara, T. et al, Bull. Chern. Soc. Jpn., 1986, 59, 2521 (synth)
Baker, R. et al, J. Chern. Soc., Perkin Trans. 1, 1988, 471 (synth,
bib/)

Porellapinguisanolide Sq-02299

OHC~
~O -OH
0"
C15Hn05 M 282.336
Constit. of Pore/la cordaeana. [cx] 0 +55 .SO (c, 1.08 in
CHC13).
Toyota, M. et al, Phytochemistry, 1989, 28, 3383 (isol, pmr, cmr)

564
14,14'-Oxybis[B-angeloyloxythapsane] ... - 6(14)-Thapsen-13-ol Sq-02303 - Sq-02308

8,14-Thapsanediol Sq-02306

Thapsanes OH

~
~6 I
14,14'-Oxybis[8-angeloyloxythapsane) Sq-02303 OH

;=<
C 15H 260 3 M 254.369
Lemmich et a/ call the parent skeleton C 15H 260 thapsane
but De Pascual Teresa eta/ call it 14,15-epoxythapsane

~
(they also use an inconsistent numbering scheme).
(8«.,14«. )-form
Cryst. (Me2C0jpet. ether). Mp 158-160°. [1X]i1 -58.4°

~6
H,
(c, 0.5 in CHC1 3).
8-Ange/oy/: [92122-83-3]. 8-Angeloyloxy-14-thapsanol. 7-
Ange/oyloxy-14,15-epoxy-14-thapsanol
,OH C 20 H 320 4 M 336.470
,, Constit. of Thapsia villosa. Cryst. (Me2CO/pet. ether).
Mp 100-102°, Mp 159-161°. [1X] 0 -24.6° (c, 1.2 in
H CHC1 3).
coo 8-(3-Methy/butenoy/): 8-Senecioyloxy-14-thapsanol. 7-

~
Senecioy/oxy-14,15-epoxy-14-thapsano/
C20 H 320 4 M 336.470
!sol. from T. villosa var. minor. Cryst. (hexane). Mp
C..JI 620 7 M 654.926
142-143°. [1X] 0 -20.0° (c, 3.5 in CHC1 3).
Not named by the authors. !sol. from Thapsia villosa var.
minor. Cryst. (MeOH). Mp 182-184°. [1X] 0 -65.5° (c, 2.5 8-(4-Hydroxycinnamoyl): 8-CoulllllToyloxy-14-thapsanol. 7-
in CHC13). Coumaroy/oxy-14,15-epoxy-14-thapsano/
C24H 320 5 M 400.514
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 703.
From T. vi//osa var. minor. Mp 210-212°. [1X] 0 -40.6° (c,
1.3 in CHC1 3).
1,14-Thapsanediol Sq-02304 8-(4-Hydroxy-3-methoxycinnamoy/): 8-Feruloyloxy-14-

lh:H
thapsanol. 7-Feru/oy/oxy-14,15-epoxy-14-thapsano/
C25 H 340 6 M 430.540
From T. villosa var. minor. Mp 163-165°. [1X] 0 -30.4°
(CHC1 3).

~1 H,
Lemmich, E. eta/, Phytochemistry, 1984, 23, 809.
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 703.
OH
14-Thapsanol Sq-02307
CtsH260 3 M 254.369
13,14-Epoxy-14-thapsano/
Errors of numbering in the paper.

g;o
[128443-45-8]
(1P,J4«.)-form
1-(3-M ethyl-2-butenoy/): 1-Senecioyloxy-14-thapsanol. 3-
Senecioyloxy-14,15-epoxy-14-thapsanol (incorr.)
C 20H 32 0 4 M 336.470
!sol. from Thapsia villosa var. minor. Oil. [1X] 0 -35.7°
(CHC13). I
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 703. OH
C 15H 260 2 M 238.369
3,14-Thapsanediol Sq-02305 Constit. of Thapsia vi//osa. Cryst. Mp 110° (85.5-87°). [1X]i1
-62.0° (c, 1.0 in CHCI 3) ( -47°).

H~
de Pascual Teresa, J. et al, Phytochemistry, 1986, 25, 1171 (isol)
Smitt, U.W. et al, Phytochemistry, 1990, 29, 873 (isol, pmr, cmr)

6(14)-Thapsen-13-ol Sq-02308
H,

C 15H 260 3
(3P,J4«.)-form
M 254.369
OH
g=rCH,OH
3-Angeloyl: 3-Angeloyloxy-14-thapsanol. 7- Ange/oy/oxy-
14,15-epoxy-14-thapsano/ (incorr.) C 15H 260 M 222.370
CzoH 320 4 M 336.470 Constit. of Thapsia villosa. Gum. [1X]i1 + 56° (c, 0.05 in
!sol. from Thapsia vi//osa var. minor. Cryst. (hexane). MeOH).
Mp 100-102°. [1X] 0 -24.6° (c, 1.2 in CHC1 3).
4-Hydroxy-3-methoxycinnamoy/:
De Pascual Teresa, J. et al, Phytochemistry, 1986, 25, 703. C 25 H 340 4 M 398.541

565
Fukinanolide - Amoenin Sq-02309 - Sq-02313

Constit. of T. villosa. Gum. [cx]i;l + 23° (c, 0.05 in CzzH320 6 M 392.491

MeOH). Constit. of P. japonicus. Cryst. (pet. ether). Mp 125-
Smitt, U.W. et al, Phytochemistry, 1990, 29, 873 (isol, pmr, cmr) 1260. [cx]i)1 -105.SO (c, 1 in MeOH).
1,9-Diangeloyl: [41059-96-5]. Homofukinolide
C25H 340 6 M 430.540
Constit. of P. japonicus. Cryst. (pet. ether). Mp 184-
1860. [cx]i)1 -127° (c, 1 in CHC1 3).

Fukinanes Abe, N. et al, Tetrahedron Lett., 1968, 1993 (struct)

Katayama, C. eta/, Bull. Chern. Soc. Jpn., 1970, 43, 1976 (cryst
struct)
Naya, K. et al, Bull. Chern. Soc. Jpn., 1972, 45, 3673 (isol)

Palmosalide C Sq-02311
Fukinanolide Sq-02309
[128255-38-9]
Bakkenolide A
[19906-72-0]

H \\

C 15H:u02
~°
M 234.338
15
C,sH 200 3 M 248.321
Constit. of Coelogorgia palmosa. Cryst. Mp 147-149°.
Weimer, D.F. eta/, Tetrahedron Lett., 1990, 31, 1973 (cryst struct)
Constit. of Petasites spp. Cryst. (pentane). Mp 80.5-80.6°.
[cx]i)1 + 17° (c, 1 in MeOH).
9P-Acetoxy: [35945-70-1]. 9-Acetoxyfukinanolide
C 17H 240 4 M 292.374
Constit. of P.japonicus. Cryst. Mp 96-97°. [cx]i;l -28.5°
(c, 1 in CHC1 3). Picrotoxanes
1,9-Dihydroxy: see Fukinolidiol, Sq-02310
Sbirahata, K. et al, Tetrahedron, 1969, 25, 3179, 4671 (struct, ms)
Naya, K. eta/, Bull. Chern. Soc. Jpn., 1972, 45, 3673 (isol)
Naya, K. eta/, Chern. Lett., 1972, 241 (2-Acetoxyfukinanolide)
Hayashi, K. et al, Chern. Pharm. Bull., 1973, 21, 2806 (synth) Aduncin Sq-02312
Evans, D.A. et a/, J. Am. Chern. Soc., 1977, 99, 5453 (synth) [62655-15-6]
Greene, A.E. et al, J. Org. Chern., 1985, 50, 3943 (synth)
0
Fukinolidiol Sq-02310 ~0
[24909-95-3] o~''
o o- OH
'¥ '

~
H
C,sH,a06 M 294.304
Constit. of Dendrobium aduncum. Cryst. (MeOH). Mp 298-
3000. [cx]i: -5.8° (c, 0.4 in Me2CO).
C 15H:u04 M 266.336 Gawell, L. et al, Phytochemistry, 1976, 15, 1991.
Cryst. Mp 176.5-177.SO. [cx]i)1 -62.6° (c, 1 in MeOH).
1-Angeloyl: [18456-00-3]. &kkenolide C Amoenin Sq-02313
C10H 280 5 M 348.438 [70219-71-5]
Constit. of Petasites japonicus. Cryst. (pet. ether). Mp
167-167.SO. HOH C OH

~
1-Ange/oy/, 9-Ac: [18455-98-6]. &kkenolide B. Fukinolide.
Petasilide
C22H 300 6 M 390.475
Constit. of P. japonicus. Cryst. (pet. ether). Mp 101-
1020. [cx]i;1 -126° (c, 1 in MeOH).
~
C 15H:u06 M 298.335
1-Tigloyl, 9-Ac: [21807-96-5]. &kkenolide E Constit. of Dendrobium amoenum. Cryst. (EtOAcfhexane).
C:uH300 6 M 390.475 Mp 195-199° dec. [ex]~ + 55° (c, 1.2 in Me 2CO).
Constit. of P. japonicus. Cryst. (EtOH). Mp 168°.
Dahmen, J. eta/, Phytochemistry, 1978, 17, 1949.
1-(3-M ethylthio-2Z-propenoyl), 9-Ac: [18456-03-6].
&kkenolide D. S-Fukinolide
C21 H 28 0 6S M 408.515
Constit. of P. japonicus. Cryst. (pet. ether). Mp 200-
2010. [cx]i)1 -161° (c, 1 in CHC1 3).
1-(S-2-Methylbutanoyl), 9-Ac: [41059-95-4].
Dihydrofukinolide

566
Amotin - Dendrobine Sq-02314 - Sq-02320

Amotin Sq-02314 Okuda, T. eta/, Tetrahedron Lett., 1965, 4191 (struct)

Biollaz, M. eta/, J. Chern. Soc., Chern. Commun., 1969, 633
[70219-70-4] (biosynth)
Tanaka, K. eta/, Chern. Pharm. Bull., 1983, 31, 1972 (synth)
Gulbis, J.M. eta/, Aust. J. Chern., 1989, 42, 1881 (cryst struct)

Corianin Sq-02318
[35481-77-7]

C 15H 100 6 M 296.319

Constit. of Dendrobium amoenum. Cryst. (EtOH). Mp 255-
2560. [IX]~ -13° (c, 1.9 in Me 2CO).
Dahmen, J. eta/, Phytochemistry, 1978, 17, 1949.

Jlsteronmurin )l Sq-02315 CtsHt80 6 M 294.304

[94451-13-5] Constit. of Coriaria japonica; Cryst. Mp 215-216°.
Okuda, T. eta/, Tetrahedron Lett., 1971, 4499.

Dendrine Sq-02319
12-0xodendrobane-2-acetic acid methyl ester, 9CI
[2651-57-2]
MeOOC
C1sH180 6 M 294.304
Constit. of scale insect Asterococcus muratae. Cryst.
(EtOAcjhexane). Mp 163.5-165°. [IX]~ +42.SO (c, 1.23 in
MeOH).
!>Toxic.
Wakamatsu, K. eta/, Tetrahedron, 1986, 42, 5551 (synth)
C19H19N04 M 335.442
Capenicin Sq-02316 Minor alkaloid from Dendrobium nobile (Orchidaceae). Mp
[4678-67-5] 191-192°. [QC]~ -1J40 (c, 0.85 in CHC1 3), [1X]i;' -81° (c,
0.14 in CHC1 3).
COOMe Inubushi, Y. eta/, Tetrahedron Lett., 1965, 2723 (ir, pmr, ms,

'r\ ~>H
struct)
Granelli, I. eta/, Acta Chern. Scand., 1970, 24, 1108 (synth, abs
corifig)

~
o'(o-
0 Dendrobine Sq-02320
OH I Dendroban-12-one, 9CI

C10H 240 8 M 392.405

Constit. of Toxicodendron capense. Cryst. Mp 243-244°.
[IX]~ -71° (c, 1 in dioxan).
Corbella, A. eta/, Tetrahedron Lett., 1966, 4819.

Corilunyrtin Sq-02317
Coriamyrtione C 16H:zsN0 2 M 263.379
[2571-86-0] (-)-form [2115-91-5]
Main alkaloid from Dendrobium spp., esp. D. nobile
(Orchidaceae). Cryst. (Etp). Mp 134-136°. [1X]h4 -48.4°
(c, 1.89 in MeOH). pK. 7.80 (Hp).
N-Oxide: [40072-57-9]. Dendrobine N-oxide
C 16H:zsN0 3 M 279.378
Alkaloid from D. nobile (Orchidaceae). Needles + 1HP
(Me2CO/Et20). Mp 160-180° dec. [1X]i;l -34° (c, 0.27 in
C1sH180 5 M 278.304 MeOH).
Constit. of the leaves of Coriaria japonica also from C.
myrtifolia and C. intermedia. Cryst. Mp 230°. [1X]h4 2-Hydroxy: [29414-86-6]. 2-Hydroxydendrobine
+79°. C16H:zsN0 3 M 279.378
Alkaloid from D. findlayanum (Orchidaceae). Cryst.
I> GM2975000.
(hexane). Mp 103-105°. [IX]~ -45° (c, 0.73 in CHC1 3).
8,9-Dihydro, 8-hydroxy: [9165-75-7]. Coriatin
6-Hydroxy: [7668-75-9]. Dendramine
CtsH100 6 M 296.319 C 16H:zsN0 3 M 279.378
Isol. from fruit of C. japonica. Cryst. (EtOH). Mp 259°.
Okuda, T., Chern. Pharm. Bull., 1961, 9, 178 (Coriatin)

567
Dendrowardine - Lambicin Sq-02321 - Sq-02323

Minor alkaloid from D. nobile. Also isol. from D. Dendroxine Sq-02322

hildebrandii (Orchidaceae). Mp 186-188°. [1X]n -27° 14,10-(Methy/eneoxy)dendroban-12-one, 9CI
(CHC1 3). (7668-77-l]
6-Acetoxy: Mp 156-158°.
N-Me: N-Methyldendrobine
C 17H 28N02e M 278.414 (ion)
Quaternary alkaloid from D. nobile (Orchidaceae).
N-Me, iodide: [3847-26-5).
C17H 28IN02 M 405.318
Prisms (Me 2CO), needles (Me 2CO/Et 20). Mp 235-238°,
Mp 245-246°, Mp 253°.
C17H15N0 3 M 291.389
N-Me, picrate: Prisms (MeOH). Mp 241-243°. Minor alkaloid from Dendrobium nobile (Orchidaceae). Mp
N-(3-Methy/-2-butenyl): N-lsopentenyldendrobine ll4-ll5°. (1X]n -30.1° (EtOH). pK. 4.5 (50% EtOH).
C21 H 34N01 e M 332.505 (ion) 4-Hydroxy: (38762-85-5]. 4-Hydroxydendroxine
Quaternary alkaloid from D. nobile (Orchidaceae). C17H 15N0 4 M 307.389
N-(3-Methy/-2-butenyl), bromide: [40072-62-6]. Minor alkaloid from D. nobile (Orchidaceae). Plates + !
C11H 34 BrN01 M 412.409 H 20. Mp 208-210°.
Noncryst. [IX]~ -33° (c, 1.4 in MeOH). 6-Hydroxy: 6-Hydroxydendroxine
(±)-form [30646-45-8] C17H15N04 M 307.389
Synthetic. Needles (Et20fhexane). Mp 131-132°. Minor alkaloid from D. nobile (Orchidaceae). Amorph.
8-Epimer: [62624-23-l). 8-Epidendrobine (1X]i; +26° (c, 0.71 in MeOH).
Synthetic. Mp 105.5-108°. N-(3-Methy/-2-butenyl): N-lsopentenyldendroxine
Inubushi, Y. eta/, Chern. Ind. (London), 1964, 1689 (abs conjig) C11H 34N0 3e M 360.515 (ion)
Inubushi, Y. et al, Chern. Pharm. Bull., 1964, 12, 1175; 1966, 14, Quaternary alkaloid from D. nobile, D. friedricksianum
668 (iso/, ir, pmr, struct, N-Methy1dendrobine, 6- and D. hildebrandii(Orchidaceae).
Hydroxydendrobine) N-(3-Methyl-2-butenyl), chloride: [34146-40-2).
Inubushi, Y. et a/, Tetrahedron, 1964, 20, 2007 (ir, pmr, struct)
Okamoto, T. et al, Chern. Pharm. Bull., 1966, 14, 676 (ms, pmr, C11H 34ClN0 3 M 395.968
Dendrobine, 6- Hydroxydendrobine) Hygroscopic needles + lEtOH (Me2CO/EtpjEtOH).
Granelli, I. et a/, Acta Chern. Scand., 1970, 24, 1209 (isol, ir, pmr, Mp 108-120° dec. [1X]i; -48° (c, 0.54 in MeOH).
ms, struct, 2-Hydroxydendrobine) 6-Hydroxy, N-(3-methyl-2-butenyl): 6-Hydroxy-N-
E1ander, M. eta/, Acta Chern. Scand., 1971, 25, 717 (cd) isopentenyldelidroxine
Hedman, K. eta/, Acta Chern. Scand., 1972, 26, 3177 (derivs, isol, C11H34N04e M 376.515 (ion)
ir, pmr, conjig, synth) Quaternary alkaloid from D. nobile, D. friedricksianum
Yamada, K. et al, J. Am. Chern. Soc., 1972, 94, 8278 (synth)
Inubushi, Y. et al, Chern. Pharm. Bull., 1974, 22, 349 (synth, ir, and D. hi/debrandii(Orchidaceae).
pmr) 6-Hydroxy, N-(3-methy/-2-butenyl), chloride: [34222-69-0).
Kende, A.S. et al, J. Am. Chern. Soc., 1974, 96, 4332 (synth) C11H 34ClN04 M 411.968
Suzuki, M. eta/, Chern. Lett., 1975, 611 (synth, Dendrobine, 2- Needles + lEtOH (EtOH). Mp 144-156° dec. [1X]i; -30°
Hydroxydendrobine) (c, 0.51 in MeOH).
Borch, R.F. et al, J. Am. Chern. Soc., 1975, 97, 6282; 1977, 99,
1612 (epimer, synth, ir, pmr) Okamoto, T. et al, Chern. Pharm. Bull., 1966, 14, 672, 676 (ir, pmr,
Corbella, A. eta/, J. Chern. Soc., Chern. Commun., 1975, 288 ms, struct)
(biosynth) Hedman, K. eta/, Acta Chern. Scand., 1971, 25, 1142 (derivs, isol,
Roush, W.R., J. Am. Chern. Soc., 1978, 100, 3599; 1980, 102, 1390 ir, pmr, struct)
(synth, ir, pmr, ms) Okamoto, T. et al, Chern. Pharm. Bull., 1972, 20, 418 (4-Hydroxy,
ir, pmr, ms, struct, 4-Hydroxydendroxine)

Dendrowardine Sq-02321
Lambicin Sq-02323
[50834-48-5]
[24548-57-0]

C1,H31N04e M 338.466 (ion) C18H 140 7 M 352.383

Quaternary alkaloid from Dendrobium wardianum Constit. of Toxicodendron capense. Cryst.
(Orchidaceae). (EtOAcfheptane). Mp 180-182°. [1X]n -16.7° (c, l in
Chloride: dioxan).
C1,H31ClN04 M 373.919 Corbella, A. et al, Tetrahedron, 1969, 25, 4835.
Cryst. (Me2CO). Mp 168-172° dec. [IX]~ -28° (c, l.l in
MeOH).
B1omqvist, L. et a/, Acta Chern. Scand., 1973, 27, 1439 (iso/, ir,
pmr, cd, struct)

568
Nobiline - Pretoxin Sq-02324 - Sq-02329

Nobiline Sq-02324 Picrotoxin Sq-02327

Nobilonine [124-87-8]
[4684-24-6] C30H 340 13 M 602.591
Equimolar compd. of Picrotin, Sq-02326 and Picrotoxinin,
Sq-02328. Bitter principle from berries of the shrubs
Anamirta coccu/us, Menispermum cocculus andother spp.
Powerful nonspecific CNS stimulant; GABA antagonist.
Used in neurochemical research. Cryst. (EtOH). Mp
203-204°. [IX]~ -30° (H 20).
C 17H17N0 3 M 293.405 I> TJ9100000.
Alkaloid from Dendrobium nobile, D. hildebrandii and D. Clark, E.P., J. Am. Chern. Soc., 1935, 57, 1111 (synth)
findlayanum (Orchidaceae). Cryst. (hexane). Mp 86.5- Coscia, C.J., Cyclopentanoid Terpene Derivs., (Taylor, W.l. eta/,
880. [IX)~ +21° (c, 0.48 in CHC1 3). pK. 8.50 (Hp). Ed.), Dekker, N.Y., 1969, 147 (rev)
Corey, E.J. eta/, J. Am. Chern. Soc., 1979, 101, 5841 (synth)
B,HCI: Mp 206-208°.
Picrate: Mp 172-175°.
Picrotoxinin Sq-02328
B,Mel: Mp 275-276°.
[17617-45-7]
6-Hydroxy: [32562-94-0]. 6-Hydroxynobiline
C1,H17N04 M 309.405 0
Alkaloid from D. hildebrandii (Orchidaceae). Needles 'l--o

~
(C 6H 6). Mp 158-159.SO. [a]~ +62° (c, 0.58 in CHC1 3).
Yarnamura, S. et a/, Tetrahedron Lett., 1964, 79 (ir, pmr, ms, ord,
struct) Absolute
Onaka, T. eta/, Chern. Pharm. Bull., 1965, 13, 745 (ir, pmr, ord,
struct, abs config, synth)
Granelli, I. et a/, Acta Chern. Scand., 1970, 24, 1209 (isol)
~ configuration

CtsHt606 M 292.288
Elander, M. eta/, Acta Chern. Scand., 1971, 25, 717 (isol, pmr, ir,
Constit. of Picrotoxin, Sq-02327. An ichthyotoxin. Potent
ms, struct, abs corifig, deriv)
Suzuki, M. et a/, Chern. Lett., 1975, 611 (synth) convulsant drug. Cryst. (Hp). Mp 209.SO. [1X]n -5.85°
(c, 3.65 in CHCI 3)(0°).
I> PC5150000.
Nobilomethylene Sq-02325
Conroy, H., J. Am. Chern. Soc., 1957, 79, 5550 (struct)
[38750-01-5] Porter, L.A., Chern. Rev., 1967, 67, 441 (rev)
Jarboe, C.H. eta/, J. Med. Chern., 1968, 11, 729 (pharmacol)
Corey, E.J. et a/, J. Am. Chern. Soc., 1978, 101, 5841 (synth)
Mackay, M.F. eta/, Aust. J. Chern., 1983, 36, 2111, 2219 lcryst
struct)

Pretoxin Sq-02329
[24462-32-6]
C1sH2003 M 248.321
Constit. of Dendrobium nobile. Cryst. (hexane). Mp 159.5- ~OH
160.SO. I
I
Okamoto, T. eta/, Chern. Pharm. Bull., 1972, 20, 418.

Picrotin Sq-02326
[21416-53-5]

C1,H2408 M 380.394
Constit. of Toxicodendron capense. Cryst.
(EtOAcjheptane). Mp 128-130°. [1X]n + 3° (c, 1 in
dioxan).
CtsH 180 7 M 310.303 Di-Ac: [24462-33-7].
Constit. of Picrotoxin, Sq-02327. Cryst. (H 20). Mp 255°. Cryst. (EtOAcjheptane). Mp 190-191°. [1Xln +31° (c, 1
[IX)~ -70° (EtOH). in dioxan).
I> TJ8800000. Corbella, A. et a/, Tetrahedron, 1969, 25, 4835.
Clark, E.P., J. Am. Chern. Soc., 1935, 57, 3046 (synth)
Craven, B.M., Tetrahedron Lett., No. 19, 1960, 21 (struct)
Corey, E.J. eta/, Tetrahedron Lett., 1980, 1823 (synth)

569
Tutin - 4,6,8,9-Daucanetetrol Sq-02330 - Sq-02334

Tutin Sq-02330
Coriarin
[2571-22-4] Daucanes

Aspterric acid Sq-02331

9ft,15-Epoxy-8cx-hydroxy-4(11)-daucen-14-oic acid
[67309-95-9]
ClsHia06 M 294.304
Isol. from Coriaria spp. of New Zealand and Japan. Also
from Toxicodendron capense. Cryst. (EtOH or Hp). Mp
212-213°. [cx]~· 5 +9.25° (c, 2.5 in EtOH).
I> Poisonous. WH1316600.
8,9-Dihydro, 8-hydroxy: [19417-00-6]. lsodihydrohyenanchin.
Dihydro-8-hydroxytutin
C15H 220 4 M 266.336
ClsH 200, M 312.319 Sesquiterpene antibiotic. Metab. of Aspergillus terreus.
Constit. of T. capense and Hyaenanche globosa. Long Cryst. (hexane). Mp 158-159°. [cx]::,S -33° (EtOH).
needles (Hp). Mp 298° dec. [cx]::,S -61.3° (Hp).
Tsuda, Y. et al, J. Chern. Soc., Chern. Commun., 1978, 160 (isol)
8,9-Dihydro, 8-hydroxy, 0 2-Me: Harayama, T. et al, Tetrahedron Lett., 1983, 24, 5241 (synth)
C16H 220 7 M 326.346 Harayama, T. et al, Chern. Pharm. Bull., 1987, 35, 1434 (synth)
Constit. ofT. capense. Mp 213°. [ex]~ -59° (c, 1.0 in
dioxan).
5,8-Daucadien-14-al Sq-02332
4cx-Hydroxy: [3484-46-6]. Mellitoxin. Hyenanchin. 4- 1,4-Carotadienaldehyde
Hydroxytutin
C1sH180 7 M 310.303 [128718-21-8]
Metab. of Scolypopa australis feeding on C. capense.
Also isol. from T. capense. Cryst. Mp 225-240° dec. [cxln
+31.9°.
2- Deoxy: see Coriamyrtin, Sq-02317
Easterfie1d, T.H. et al, J. Chern. Soc., 1901, 79, 120 (isol)
Craven, B.M., Nature (London), 1963, 197, 1193 (cryst struct)
Jommi, G. et al, Chim. Ind. (Milan), 1964, 46, 549; 1965, 47, 406, C15H 220 M 218.338
865 (derivs) Constit. of Rosa rugosa. Syrup.
Hodges, R. et a/, Tetrahedron Lett., 1964, 371 (Mellitoxin)
Okuda, T. eta/, Tetrahedron Lett., 1965, 2137, (abs corifig) Hashidoko, Y. et al, Phytochemistry, 1990, 29, 867 (isol, pmr, cmr,
Ricca, G.S. et al, Gazz. Chim. /tal., 1967, 97, 1905 (pmr, ir, derivs) ms)
Corbella, A. et a/, J. Chern. Soc., Chern. Commun., 1972, 600
(biosynth) 4,8-Daucadiene Sq-02333
Wakamatsu, K. et al, Tetrahedron, 1986, 42, 5551 (synth) Daucene
Gulbis, J.M., Aust. J. Chern., 1989, 42, 1881 (cryst struct)
[16661-00-0]

C15H14 M 204.355
Constit. of Daucus carota. Oil. Bp4 96°. [cxln + 39° (c, 0.3
in CHC1 3). n~ 1.4918.
Bisepoxide: Cryst. Mp 89°. [cx]n +25° (c, 0.4 in CHC1 3).
de Broissia, H. eta/, Bull. Soc. Chim. Fr., 1972, 4314 (isol, struct)
Audenaert, F. et a/, Tetrahedron, 1987, 43, 5593 (synth)

4,6,8,9-Daucanetetrol Sq-02334

~~H
HOKir--''
)'.. OH
C15H:11.04 M 272.384
(4P,6«,8P,9rx.)-form
6-(4-Hydroxybenzoyl): [128397-56-8]. 6«-(4-
Hydroxybenz;oyloxy)-4P,8P,9rx.-daucanetriol

570
5,8,9-Daucanetriol - 8-Daucene-5,10-diol Sq-02335 - Sq-02339

C22 H 32 0 6 M 392.491 6-(4-Hydroxy-3-methoxybenzoyl): [54526-95-3]. Teferin

Constit. of Ferula sinaica. [1X]~4 + 15.8° (c, 0.5 in C23H 320 5 M 388.503
MeOH). Constit. of F. tenuisecta. Cryst. Mp 78-80°. [1X]n +86S
Ahmed, A.A., J. Nat. Prod. (Lloydia), 1990, 53, 483 (isol, pmr, (CHC1 3).
cmr) 6-(2-Hydroxybenzoyf): Jaeskeanadiol salicylllte
C22 H 300 4 M 358.477
5,8,9-Daucanetriol Sq-02335 Constit. of F. jaeschkeana. Cryst. Mp 210-213°.
6-Ange/oy/: Jaeskeanadiol angelllte
OH C20 H 320 3 M 320.471

)JJ~H
Constit. of F. jaeschkeana. Oil.
6-(4-Hydroxybenzoyl): Ferutinin
C22 H 300 4 M 358.477
Constit. of F. jaeschkeana. Mp 121-122°. [1X)i? + 66° (c,
1.36 in EtOH).
C15H 280 3 M 256.384 6-(3,4-methylenedioxybenzoyl): Jaeskeanidin
(5rx.,8rx.,9/f)-form C23 H 300 5 M 386.487
9-Ange/oy/: [63303-43-5]. Linkiol Constit. of F. jaeschkeana. Cryst. Mp 123-124°.
C20H 340 4 M 338.486 6-(3-Hydroxy-4-methoxybenzoyl): [41744-35-8]. Ferutin
Constit. of Ferula linkii. Cryst. (C 6H 6). Mp 123-125°. C23 H 320 5 M 388.503
[1X]n -17° (c, 0.3 in CHC1 3). lsol. from F. spp. Cryst. (pet. ether). Mp 130-131°. [IX]~
(5p,Bp,9rx.)-form + 101.8° (c, 1.08 in MeOH).
Pal/itriol Sriraman, M.C. eta/, Tetrahedron, 1973, 29, 985 (Jaeschkeanadiol)
Cryst. (Etp). Mp 73-73.5°. SaidhhodZhaev, A.I. et a/, Khim. Prir. Soedin., 1974, 10, 166; 1976,
9-(2 ,4,5-Trimethoxybenzoyl): Pallidin 12, 105 (derivs)
C25H 380 7 M 450.571 Kushmuradov, A.Yu. eta/, Khim. Prir. Soedin., 1974, 10, 166;
1978, 14, 725; Chern. Nat. Compd. (Engl. Trans/.), 178, 617
Constit. of Ferula pal/ida. Cryst. (EtOAcfhexane). Mp (Ferutinol, Akiferidin)
109.5-110°. [1X]i:' +27.9° (c, 0.1 in CHC1 3). Khasanov, T.Kh. et a/, Khim. Prir. Soedin., 1974, 10, 528 (Teferin)
Gonzalez, A.G. et a/, Phytochemistry, 1977, 16, 265 (isol) Razdan, T.K. eta/, Phytochemistry, 1989, 28, 3389.
Kushmuradov, A.Y. eta/, Khim. Prir. Soedin., 1990, 26, 42; Chern.
Nat. Compd. (Engl. Trans/.), 33 (isol, pmr, cryst struct)
8-I>aucene-5,7-diol Sq-02338

_(t):
8-Daucene-3,4-diol Sq-02336

Ho- r-V-\
H~
H
"-\
I
C15H 260 2 M 238.369
(6p,7rx.)-form [122769-24-8]
C 15H 260 2 M 238.369 Carotdiol
(1P,3P,4P,5rx.)-form Cryst. Mp 76-78°.
CAF603 7-Ac: [122769-22-6]. Carotdiol acetate
Metab. of Giliocladium virens. Needles. Mp 82-84°. [IX]~ C17H280 3 M 280.406
-26.2° (c, 0.5 in MeOH). Constit. of Ferula linkii. Oil.
Watanabe, N. eta/, J. Nat. Prod. (Lloydia), 1990, 53, 1176 (isol, 7-(3,4-Dimethoxybenzoyl): [122769-23-7]. Carotdiol
pmr, cmr) veratrate
C24H 340 5 M 402.530
8-Daucene-4,6-diol Sq-02337 Constit. of F. linkii. Oil.
Fraga, B.M. eta/, Phytochemistry, 1989, 28, 1649.

~
HO~
8-I>aucene-5,1~diol Sq-02339

A OH OH
I

~
C15H 260 2 M 238.369
(4P,6rx.)-form [41690-67-9] Jaeschkeanadiol. Ferutinol.
Chimganidol. Tchimganido/
Constit. of Feru/a jaeschkeana. Cryst. (pet. ether). Mp
91-92°. [1X]n +38.8° (CHC1 3). ~
6-Benzoy/: [60033-08-1]. Teferidine Ct5H2602 M 238.369
C22H 300 3 M 342.477 (5P,10rx.)-form [79803-27-3]
Constit. of F. tenuisecta and F. jaeschkeana. Oil. [1X)n Lasidiol
+37.5°. 10-Ange/oy/: Lasidiol angelllte
6-(3,4-Dihydroxybenzoyl): [70284-22-9]. Akiferidin C20H 320 3 M 320.471
C22H 300 5 M 374.476 Isol. from Lasiantheae fruticosa. Ant repellent. Oil.
Constit. of F. akitschkensis. Cryst. (EtOAcfhexane). Mp Wiemer, D.F. et a/, J. Org. Chern., 1981, 46, 5449.
52-54°. [1X]n +28.5° (c, 1.4 in CHC1 3).

571
8-Daucene-2,4,6-triol - 4,6-Dihydroxy-7-daucen-9-one Sq-02340 - Sq-02345

ro-dt,oH
8-Daucene-2,4,6-triol Sq-02340 8-Daucene-4,6,14-triol Sq-02342

H~
HOI HI HO )-!16H
) ' OH
C 15H 260 3 M 254.369
C 15H 260 3 M 254.369 (4Jl,6rx.)-form
(2Jl,4Jl,6rx.)-form [60032-03-3] Akitchenol Jaeschkeanatriol
Constit. of Ferula akitschkensisand F. jaeschkeana. 6-(4-Hydroxybenzoyl): [109517-73-9]. Feruginidin
Cryst. Mp 155-156°. [ex]~ +37.5° (c, 1.33 in CHCI 3). C22 H 300 5 M 374.476
2-A.ngeloyl: [69500-33-0]. Constit. of Ferula jaeschkeana. Needles (MeOH). Mp
C:zoH320 4 M 336.470 130°. [ex]~ +6.0° (c, 1.5 in MeOH).
Constit. of F. jaeschkeana. Gum. [exro' + 6.6° (c, 1 in Garg, S.N. eta/, J. Nat. Prod. (Lloydia), 1987, SO, 253.
CHC1 3).
6-(4-Hydroxybenzoyl): [128397 -36-4]. 8(14)-Daucene-4,6,9-triol Sq-02343
C22H 300 5 M 374.476
Constit. of F. jaeschkeana. Needles (MeOH). Mp 125- ,OH

HOq:J=
1260. [ex]~ +31° (c, 2 in CHC1 3).
2-A.ngeloyl, 6-(4-Hydroxybenzoyl): [60032-04-4].
Akitschenin. Angeloyloxyferutinianin. Angeloylferutinianin
(incorr.)
C27 H 360 6 M 456.578 ~OH
From F. akitschkensis and F. jaeschkeana. Cryst. Mp C 15H 260 3 M 254.369
210-212° (162-163°). [ex]~ -8.3° (c, 0.9 in CHC1 3). (4Jl,6rx.,9rx. )-form
2-Angeloyl, 6-(3,4-Dihydroxybenzoyl): [70284-23-0]. Isolancerotriol
Akiferidinin Constit. of Ferula rinaica. [ex]~ +63° (c, 0.31 in MeOH).
C27H 360 7 M 472.577 6-(4-Hydroxybenzoyl): [109517-72-8]. Ferugin
From F. akitschkensis. Cryst. (EtOAcjpet. ether). Mp C22 H 300 5 M 374.476
66-67°. [ex] 0 +46° (c, 1 in EtOH). Constit. of F. jaeschkeana. Needles (MeOH). Mp 140°.
Kadyrov, A.S. eta/, Khim. Prir. Soedin., 1976, 12, 102 (isol) [ex]~ + 15.0° (c, 1.5 in MeOH).
Saidkhodzhaev, A.l. eta/, Khim. Prir. Soedin., 1978, 14, 584;
Garg, S.N. eta/, J. Nat. Prod. (Lloydia), 1987, SO, 253.
Chern. Nat. Compd. (Engl. Trans/.), 502 (pmr)
Ahmed, A.A. et al, J. Nat. Prod. (Lloydia), 1990, 53, 483 (isol,
Kushmuradov, A.Yu. eta/, Khim. Prir. Soedin., 1978, 14, 725;
pmr, cmr)
Chern. Nat. Compd. (Engl. Trans/.), 617 (isol)
Garg, S.N. et al, Phytochemistry, 1990, 29, 531 (isol, pmr, cmr)
8-Daucen-5-ol Sq-02344
8-Daucene-4,6,10-triol Sq-02341
8-Carotene-4,6,10-triol
OH
I

C 15H 260 M 222.370

5fJ-form [465-28-1] Carotol
Constit. of Daucus carota. Oil. Bp 2.5 126°. [ex]~ + 29.6°.
C 15H 260 3 M 254.369 Levisalles, J. et al, Bull. Soc. Chim. Fr., 1967, 2059 (stereochem)
de Broissia, H. et al, Bull. Soc. Chim. Fr., 1972, 4314 (synth)
(4Jl,6rx.,10rx.)-form [103654-31-5]
Pallinol

Hw
Oil. [ex]~ +37.3° (c, 0.1 in CHC1 3). 4,6-Dihydroxy-7-daucen-9-one Sq-02345
6,10-Diangeloyl: [90695-04-8]. Pallinin 0
C25 H380 5 M 418.572
Constit. of Ferula pal/ida. Cryst. (EtOAcjpet. ether).
Mp 79-80°. [ex]~ -148.SO (c, 0.1 in CHC1 3).
10-Ketone: see 4,6-Dihydroxy-8-daucen-10-one, Sq-02347
Kushmuradov, A.Yu. et a/, Khim. Prir. Soedin., 1986, 22, 48. / >-.!I•
- OH
C 15H 240 3 M 252.353
(4Jl,6rx.)-form [96853-60-0] Lancerodiol
Constit. of Ferula lancerottensis.
6-(4-Hydroxybenzoyl): [96853-62-2].
C22 H 180 5 M 372.460
From F. lancerottensis. Cryst. Mp 227-228°.
6-(4-Methoxybenzoyl): [96853-59-7].
C23H300S M 386.487
From F. lancerottensis. Gum.

572
4,6-Dihydroxy-8-daucen-2-one - 8,9-Epoxy-4,6-daucanediol Sq-02346 - Sq-02350

6-(4-Hydroxy-3-methoxybenzoyl): Lancerodiol ranillllte 5,10-Dihydroxy-8-daucen-2-one Sq-02349

C 23H:11P 6 M 402.486 1,6-Dihydroxy-2-caroten-9-one
From F. orienta/is.

~
Fraga, B.M. et a/, Phytochemistry, 1985, 24, 501 (iso[)
Miski, M. eta/, J. Nat. Prod. (L/oydia), 1987, 50, 829 (iso[)

Hw-
4,6-Dihydroxy-8-daucen-2-one Sq-02346
0 ~
C 15H 240 3 M 252.353
(5«,10«)-form
10-Ac: [94595-16-1].
-\ em C 17H:11;04 M 294.390
Constit. of Sium latijugum. Cryst. (CHC1 3fhexane). Mp
C 15H 240 3 M 252.353 129-130°. [ex]~ -232.SO (c, 2.37 in CHC1 3).
(4ft,6«)-form (5P,JOrx.)-form [87860-27-3]
6-(4-Hydroxybenzoyl): [126617-09-2]. Ferutionone Siol
C 22 H 280 5 M 372.460 10-Ac: Siol acetate
Constit. of Ferula jaeschkeana. Cryst. Mp 93-94°. C 17H 21;04 M 294.390
Razdan, T.K. eta/, Phytochemistry, 1989, 28, 3389 (isol, pmr, cmr) lsol. from Sium latifolium. Cryst. Mp 130-131°. [ex]~
-252° (c, 0.28 in CHC1 3).
4,6-Dihydroxy-8-daucen-1 0-one Sq-02347 10-Angeloyl: [11053-21-7]. Vaginatin

0
C20 H 300 4 M 334.455
Constit. of Selinum vaginatum and lnula crithmoides.
Cryst. (pet. ether). Mp 77-78° (68-69°). [exln -266.7° (c,
4.32 in CHC1 3).

HO~ ,/-OH
10-(4-Methoxybenzoyl): [104758-20-5]. Fercomin
C23 H 300 5 M 386.487
Constit. of Ferula communis ssp. communis. Cryst.
(Et20/hexane). Mp 130-132°.
C15H 240 3 M 252.353
Several numbering systems are in use for daucanes. [87746-59-6)
(4P,6«)-form [79863-23-3] Casinovi, C.G. et a/, Collect. Czech. Chern. Commun., 1983, 48,
2411 (cryst struct, siol acetate)
Lap idol
Pandita, K. eta/, Indian J. Chern., Sect. B, 1984, 23, 956.
Yellow oil. [ex]~ + 123° (c, 1.2 in CHC1 3). Appendino, G. eta/, J. Chern. Soc., Perkin Trans. I, 1986, 1363
6-Angeloy/: [79863-24-4]. Lapidin (Vaginatin)
Cwli 300 4 M 334.455 Miski, M. eta/, Phytochemistry, 1986, 25, 1673 (Vaginatin,
Constit. of Ferula lapidosa. Cryst. (hexane). Mp 80-81°. Fercomin)
[ex]~ + 166° (c, 1.5 in CHC1 2).
6-(3,4,5-Trimethoxybenzoyl): [80535-89-3]. Pal6ferin 8,9-Epoxy-4,6-daucanediol Sq-02350
C24H 32 0 7 M 432.513
From F. pal/ida.
6-(3,4-Methylenedioxy-5-methoxybenzoyl): [80535-88-2]. ~
Palliferinin
HO~
C 23 H 28 0 7 M 416.470
From F. pal/ida. A em
Golovina, L.A. eta/, Khim. Prir. Soedin., 1981, 17, 318 (isol, C1sHu03 M 254.369
struct) (4P,6«)-form [94663-05-5]
Kushmuradov, A.Y. eta/, Khim. Prir. Soedin., 1981, 17, 523 (iso[) Epoxyjaeschkeanadiol
Moiseeva, G.P. eta/, Khim. Prir. Soedin., 1984, 20, 45 (cd)
6-(4-Hydroxybenzoyl): [96853-63-3]. Jaeskeanin.
Epoxyjaeschkeanadiol p-hydroxybenzoate
4,9-Dihydroxy-7-daucen-6-one Sq-02348

Hw-
C22 H 300 5 M 374.476
Constit. of Ferula orienta/is and F. jaeschkeana. Cryst.
OH
I Mp 83-85°.
6-(4-Hydroxy-3-methoxybenzoyl): [112501-40-3].
Epoxyjaeschkeanadiol vanillate
C23H 320 6 M 404.502
AO Constit. of F. orienta/is. [ex]i,l + 52.9° (c, 1.4 in CHC1 3).
C1 5H 240 3 M 252.353 Miski, M. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 829.
(4P,9«)-form [111199-26-9] Feruone
Constit. of Ferula jaeschkeana. Viscous mass. [ex]~ + 1.5°
(c, 0.15 in MeOH).
Garg, S.N. eta/, Planta Med., 1987, 53, 341.

573
8,9-Epoxy-2,4,6,10-daucanetetrol- 10-Hydroxy-2-oxo-8-daucen-12,5-... Sq-02351 - Sq-02356

8,9-Epoxy-2,4,6,1 0-daucanetetrol Sq-02351 Za1kov, L.H. et al, J. Org. Chern., 1961, 26, 981 (struct)
de Broissia, H. et al, Bull. Soc. Chim. Fr., 1972, 4314 (synth)
Dhillon, R.S. et al, Phytochemistry, 1989, 28, 639 (deriv)

H~ Ferujaesenol
[128397-34-2]
Sq-02354

HO \HI

HJ:p-
_)--OH
C 1sHu.Os M 286.367
Several numbering systems are in use for daucanes.
(2a.,4P,6a.,8a.,9a.,10a.)-form [85202-12-6]
Lapidolinol ~ OH
Cryst. Mp 260-261° dec. [IX]~ + 58° (c, 1.1 in EtOH). C 1sH140 2 M 236.353
6-Angeloyl, 2,10-di-Ac: [85179-08-4]. Lapidolin Constit. of Ferula jaeschkeana. Needles (Me 2C0jpet.
C 14H 360 8 M 452.544 ether). Mp 127-128°.
Constit. of Ferula lapidosa. Cryst. (EtOH). Mp 188- Garg, S.N. eta/, Phytochemistry, 1990, 29, 531 (isol, pmr, cmr)
1890. [1X]~ +27.7° (c, 1.3 in CHC1 3).
6-(3,4-Dimethoxybenzoyl), 2-Ac: [101021-32-3]. Lapidolidin Hercynolactone Sq-02355
C:u;H360S M 428.567 4( II), 7-Daucadien-I2 ,61X-olide
Constit. of F. lapidosa. Cryst. (Et20). Mp 163-164°. [1X]n [84881-60-7]

5Y
+26.7° (c, 1 in EtOH).
2,10-Di-Ac, 6-(3,4-dimethoxybenzoyl): (85179-07-3].
Lapidolinin
C 28 H 380 10 M 534.602
From F. lapidosa. Cryst. (EtOH). Mp 182-183°. [IX]~ Relative
+54 .SO (c, 1.1 in CHC1 3).
configuration
Kemoldidze, Z.S. eta/, Khim. Prir. Soedin., 1982, 18, 788 (isol) 0
Moiseeva, G.P. eta/, Khim. Prir. Soedin., 1984, 20, 45 (cd)
Tashkhodzhaev, B. eta/, Khim. Prir. Soedin., 1984, 20, 309 (cryst C 1sH200 1 M 232.322
struct) Constit. of liverworts Barbilophozia lycopodioides and B.
Go1ovina, L.A. et al, Khim. Prir. Soedin., 1985, 21, 673 hatcheri. Cryst. (hexane). Mp 97-98°. [1X]n -84.2° (c,
(IApidolidin) 0.875 in CHC1 3).
Huneck, S. et a/, Tetrahedron Lett., 1982, 23, 3959 (cryst struct)
7,8-Epoxy-4,6,9-daucanetriol Sq-02352
OH 10-Hydroxy-2-oxo-8-daucen-12,5-olide Sq-02356

H~
OH
I

A OH
C 1sH160 4 M 270.368
(4p,6a.,71;,81;,9/l)-form [116513-88-3] 2ft-Hydroxy-3,4-
epoxyjaeschkeanadiol
Constit. of Ferula jaeschkeana. Viscous mass. [1X]n +47° C 1sH 200 4 M 264.321
(c, 1.5 in CHC1 3). (4a.H,5P,10a.,ll/l)-form
Ga~, S.N. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 771. 10-(4-Methoxybenzoyl): [104672-14-2]. Fercolide
C23H 160 6 M 398.455
5,8-Epoxy-9-daucanol Sq-02353 Constit. of Ferula communis subsp. communis. Amorph.
(4PH,5a.,10a.,lla.)-form
10-Tigloyl: [119778-60-8]. Feruginin. Ferugenin
C20H 160s M 346.422
Constit. of F. jaeschkeana. Needles (Me 2CO). Mp 90°.
Absolute [1X]~ -466° (c, 0.6 in CHCI 3).
configuration Miski, M. et al, Phytochemistry, 1986, 25, 1673 (Fercolide)
Garg, S.N. et al, Phytochemistry, 1987, 26, 445 (Feruginin)
C 1sH160 2 M 238.369
(5P,8P,9fl)-form [887-08-1] Daucol
Constit. of carrot (Daucus carota) seed oil. Cryst. (pet.
ether at -30°). Mp 113-115°. Bp 2 124-132°. [IX]~ -16.9°
(c, 2.8 in EtOH).
Deoxy: (56484-24-3]. 5,8-Epoxydaucane. Carota-I,4P-oxide
C 1sH160 M 222.370
Constit. of D. carota. Oil.
Sykora, V. eta/, Collect. Czech. Chern. Commun., 1961, 26, 788
(struct)

574
Rugosa! A- 6-Isodaucene 14-isonitrile Sq-02357 - Sq-02362

Rugosal A Sq-02357
[121387-05-l]
Isodaucanes
CHO
(salviolanes)
CtsHn04 M 266.336
Constit. of damaged leaves of Rosa rugosa. Shows
antimicrobial activity. Needles (EtOAcjhexane). Mp 6,10-Epoxy-7(14)-isodaucane Sq-02360
145-147°. 1,5-Epoxy-4( 14)-salvialene
Hashidoko, Y. eta/, Agric. Bioi. Chern., 1989, 53, 2505 (iso/, abs [88395-47-5]
config) I
Hashidoko, Y. eta/, Phytochemistry, 1989, 28, 425.

4,6,8, 10-Tetrahydroxy-9-daucanone
OH
\
Sq-02358

Ct 5H 240
~
M 220.354
Constit. of Clary sage oil (Salvia sclarea). Cryst. Mp 61-
620. [1X]i,? +40.SO (c, l in CHC1 3).
Maurer, B. et a/, Helv. Chim. Acta, 1983, 66, 2223.

CtsHuPs M 286.367 10-Hydroxy-6-isodaucen-14-al Sq-02361

(4P,6«,8«,1 011. )-form [l 00428-90-8]
10-Angeloyl: [25491-14-9]. Laserol

<D
C20 H 3z06 M 368.469 OH
Constit. of Laserpitum latifolium. Cryst. Mp 148°. [1X]i,?
+ 108.0°.
6,10-Diangeloyl: [7067-12-l]. Laserpitine
C25 H 380 7 M 450.571
Constit. of L. latifolium. Cryst. Mp 117°. [1X]i,? + 119° .---/.. H CHO
(EtOH). " 14

6-(2- M ethylpropanoy/),1 0-angeloyl: CtsH2402 M 236.353

C24H 380 7 M 438.560 Constit. of Chromolaena laevigata. Oil.
Constit. of L. latifolium. Amorph. powder. [1X]i; + 85° 10-Ketone: [100324-71-8]. 10-0xo-6-isodaucen-14-al.
(c, 0.064 in EtOH). Alpluznamol II
9C:,-Alcohol, 6,10-diangeloyl: [16836-38-7]. Laserpitinol CtsH220 2 M 234.338
C2sH2407 M 436.460 Constit. of C. laevigata and Aphanamixis grandifolia.
Constit. of L. latifolium. Cryst. Mp 139°. [1X]i,?+ 0°. Oil. [1X]:,S +6.9° (c, 0.94 in CHC1 3). Identity of 10-0xo-6-
isodaucen-14-al and Aphanamol II not definitely establ.;
Feldmann, A., Justus Liebigs Ann. Chern., 1865, 135, 236 (isol)
same struct. and rel. stereochem. given. Props. refer to
Holub, M. eta/, Monatsh. Chern., 1967, 98, 1138 (isol)
Holub, M. et a/, Collect. Czech. Chern. Commun., 1970, 35, 3597
Aphanamol II; no opt. rotn. reported for 10-0xo-6-
(struct, abs config) isodaucen-14-al. Abs. config. not detd. for Aphanamol
Moldt, P. et a/, J. Nat. Prod. (Lloydia), 1987, 50, 974 (isol, cmr) II; for 10-oxo-6-isodaucen-14-al the abs. config. shown
above was proposed, on biogenetic grounds only.
5,10,14-Trihydroxy-8-daucen-2-one Sq-02359 10-Ketone, 14-alcohol: [91410-61-6]. 14-Hydroxy-6-
isodaucen-10-one. Aphanamoll
OH CtsH 240 2 M 236.353

¢0-CH,OH
I OH
Constit. of A. grandifolia. Oil. [1X]:,S + 13.8° (c, 0.29 in
CHC1 3).
(91410-62-7]
Nishizawa, M. eta/, J. Org. Chern., 1984, 49, 3661.
--\ Misra, L.N. et a/, Tetrahedron, 1985, 41, 5353.

CtsH2404 M 268.352 6-Isodaucene 14-isonitrile Sq-02362

(5P,l0«)-form
[112767-02-9]
10-Angeloyl: [128397-55-7]. 14-Hydroxyvaginatin

5P-NC
C 20 H~,0 5 M 350.454
Constit. of Ferula sinaica.
Ahmed, A.A., J. Nat. Prod. (Lloydia), 1990, 53, 483 (iso/, pmr,
cmr)

M 231.380

575
7(14)-lsodaucen-10-one- Perforenone Sq-02363 - Sq-02366

Metab. of marine sponge Acanthella acuta. Oil. [1X]n

+44.0° (c, 1.0 in CHC1 3).
Isothiocyanate: [112757-35-4]. 6-/sodaucene 14-
isothiocyanate
Perforanes
C 16H 15NS M 263.446
Metab. of A. acuta. Oil. [1X]n + 36.2° (c, 0.2 in CHC10.
Has - NCS replacing - NC.
Mayo!, L. eta/, Tetrahedron, 1987, 43, 5381. Perforenol Sq-02365
[70073-12-0]
7(14)-Isodaucen-10-one Sq-02363
4(1 4)-Salvialen-1-one
[73809-82-2]
HO,~_Cl Absolute

Br~r configuration

~
C 15H 13Br2Cl0 M 414.607
Constit. of Laurencia perforata. Cryst. Mp 105-107°. [1X]n
-107°.
-\H Gonzalez, A.G. et al, Tetrahedron Lett., 1978, 3931 (isol, pmr, cmr,
cryst struct)
C15H140 M 220.354
Constit. of Clary sage oil (Salvia sclarea). Cryst. Mp 31- Perforenone Sq-02366
320. [1X]~ +59.7° (c, 1.6 in CHC1 3).
[66113-28-8]
Maurer, B. et a/, Helv. Chim. Acta, 1983, 66, 2223.

Mintsulfide Sq-02364
[72445-42-2]
I

~
C 15H 220 M 218.338
Constit. of Laurencia perforata. Oil. [1X]n -120°.
-\H 31X-Hydroxy: [57566-99-1]. Perforenone A
CtsH2202 M 234.338
C 15H 14S M 236.421 Constit. of L. perforata. Mp 120-121°. [1X]n -116°.
Constit. of Mentha piperita oil. Cryst. (MeOH). Mp 64°. 31X-Chloro: [57567-00-7]. Perforenone B
[IX]~ -64.2° (c, 10 in hexane). C 15H 21 Cl0 M 252.783
Yoshida, T. et al, J. Chern. Soc., Chern. Commun., 1919, 512 (cryst Constit. of L. perforata. Cryst. Mp 190°. [1X]n -117°.
struct) 21X-Alcohol: [66113-20-0]. Guadalupol
Takahashi, K. et al, Agric. Bioi. Chern., 1981, 45, 129 (isol, synth) C 15H 140 M 220.354
Constit. of L. snyderae. Oil.
2ft-Alcohol: [66113-19-7]. Epiguadalupol
C 15H140 M 220.354
Constit. of L. snyderae. Oil.
Gonzalez, A.G. et al, Tetrahedron Lett., 1915, 2499; 1977, 3375;
1978, 481 (isol, struct, synth)
Howard, B.M. et al, Phytochemistry, 1979, 18, 1229 (Guadalupol,
Epiguadalupol)
Majetich, G. et al, Heterocycles, 1987, 25, 271 (synth)

576
Pacifigorgiol - Asteriscanolide Sq-02367 - Sq-02370

Pacifigorgianes Asteriscanes

q;
Pacifigorgiol Sq-02367 15-Asteriscanoic acid Sq-02369
Octahydro-1 ,5-dimethyl-4-(2-methyl-1-propenyl)-3aH-inden-
3a-ol, 9CI 0

(+)-form
ClsH240 3 M 252.353
Constit. of Asteriscus graveolens. Oil (as Me ester).
El Dahmy, S. eta/, Tetrahedron, 1985, 41, 309.
C 15Hu;0 M 222.370
(+)-form (84014-68-6]
Constit. of gorgonian coral Pacifigorgia cf adamsii. Asteriscanolide Sq-02370
lchthyotoxin. Oil. [ot:ln +41° (c, 1.02 in CHC1 3). [97649-15-5]
(-)-form [90988-77-5]
Constit. of Valeriano officina/is. Oil. [1X]n, -45.3° (c,
0. 724 in CHC1 3).
lzac, R.R. et a/, Tetrahedron Lett., 1982, 23, 3743 (iso/, cryst
struct)
Martin, M. eta/, Pure App/. Chern., 1982, 54, 1915 (synth)
Bos, R. eta/, Phytochemistry, 1986, 25, 1234 (isol)

Tamariscol Sq-02368 ClsHnOJ M 250.337

[90 138-52-6] Constit. of Asteriscus aquaticus. Cryst. (Et20). Mp 178°.
[1X]n + 12.1° (CHC1 3).
6,7,9,10-Tetradehydro: (96386-59-3]. 6,7,9,10-
Tetradehydroastericanolide. I, 7,8,1 0-
Tetradehydroastericano/ide
C1sH1s03 M 246.305
Constit. of A. graveolens. Cryst. Mp 172°. [1X]n + 30° (c,
0.16 in CHC1 3).
Feliciano, A.S. eta/, Tetrahedron Lett., 1985, 26, 2369 (cryst
C 15H 21;0 M 222.370 struct)
Constit. of the liverwort Frul/ania tamarisci. Oil. [1X]n El Dahmy, S. et a/, Tetrahedron, 1985, 41, 309 (iso/, deriv)
-19.7° (c, 1.1 in CHC1 3).
Connolly, J.D. eta/, Tetrahedron Lett., 1984, 25, 1401 (isol)
Tori, M. eta/, J. Chern. Soc., Perkin Trans. 1, 1990, 2849 (synth,
abs config)

577
Broderol - Ptaquiloside Sq-02371 - Sq-02376

3,9-Dihydroxy-7-illuden-1-one Sq-02373

£iQ<
Illudanes
HO \H 0
Broderol Sq-02371 C15Hn03 M 250.337
[79801-74-4] (2P,3P,9fl)-form
9-(2-0-Acetyi-P-D-glucopyranoside ): [125905-0 1-3].
Hypoloside A
C23 H 340 9 M 454.516
Constit. of Hypo/epis punctata and Dennstaedtia hirsta.
Powder (Me 2COfhexane). Mp 90-94°. [a:Ji? + 14.1 o
(MeOH).
9-[2-0-Acety/-4-(p-hydroxy-Z-cinnamoyl)-P-v-
C15Hn01 M 234.338
g/ucopyranoside]: [125676-80-4]. Hypoloside B
Constit. of Cyathus bulleri. Plates (CC14). Mp 113-115°.
[a]i; -99° (c, 0.09 in MeOH). C31 H 400 11 M 600.661
Constit. of H. punctata and D. hirsta. Powder
Ayer, A.M. eta/, Can. J. Chern., I98I, 59, 2I50. (Me 2CO/hexane). Mp 115-117°. [a:Ji? -5.12° (MeOH).
9-[2-0-Acety/-4-(p-hydroxy-E-cinnamoyl)-P-v-
1,7-Dihydroxy-2,9-illudadien-8-one Sq-02372 glucopyranoside]: [125761-28-6]. Hypoloside C
[1146-04-9] C31H400u M 600.661
Constit. of H. punctata and D. hirsta. Powder
0 (Me2COfhexane). Mp 138-140°. [a:Ji? -79° (MeOH).

m
~8~ Saito, K. eta/, Phytochemistry, 1990, 29, I475 (isol, pmr, cmr)

.-91

em Hypacrone
[41059-92-1]
Sq-02374

C15H 200 3 M 248.321

Sesquiterpene antibiotic.
I> WH0204350.
(la.,7fl)-form
llludin M
Metab. of Clitocybe illudens. Cryst. (EtOH aq.). Mp CtsHm01 M 232.322
130-131°. [a:Jn -126°. Constit. of Hypo/epis punctata. Oil. Bp0 .02 90°. A
1-Deoxy: [112953-12-5]. 7-Hydroxy-2,9-il/udadien-8-one. 6- secoilludane.
Deoxyilludin M. 6-Deoxyi//udin Hayashi, Y. et a/, Tetrahedron, I977, 33, 2509, 2513 (iso/, struct,
C15H 20 0 1 M 232.322 synth)
Prod. by Pleurotus japonicus. Anti tumour agent. Pale- Sakan, F. eta/, Bull. Chern. Soc. Jpn., 1981, 54, 2235 (synth)
yellow solid. [a:]~ - UO (c, I in MeOH).
81; -Alcohol: [34338-99-3]. 2,9-Il/udadiene-1 ,7,8-trio/. Leaianafulvene Sq-02375
DihydroiUudin M
C1sHn03 M 250.337
Metab. of C. illudens. Oil.
12-Hydroxy: see 1,7,12-Trihydroxy-2,9-i//udadien-8-one,
Sq-02377
McMorris, T.C. et a/, J. Am. Chern. Soc., I965, ff7, I594 (isol,
struct)
Matsumoto, T. eta/, Tetrahedron Lett., I970, 117I (synth)
CtsHta04 M 262.305
Singh, P. eta/, Phytochemistry, I97I, 10, 2229 (Dihydroilludin M) Constit. of Mycena leaiana. Cryst. Mp 142°. [a:Ji? + 306°
Hanson, J.R. eta/, J. Chern. Soc., Perkin Trans. I, I976, 876 (c, 0.045 in MeOH).
(biosynth) Harttig, U. eta/, Phytochemistry, 1990, 29, 3942 (iso/, pmr, cmr)
Bradshaw, A.P.W. eta/, J. Chern. Soc., Perkin Trans. I, I982,
2445 (biosynth)
Hara, M. eta/, J. Antibiot., 1987, 40, 1643 (Deoxyilludin M) Ptaquiloside Sq-02376
McMorris, T.C. et a/, Tetrahedron, 1989, 45, 5433 (cryst struct) Aquilide A
[87625-62-5]
OGle

~
M 398.452
OH

578
1,7,12-Trihydroxy-2,9-illudadien-8-... - 5,6-Dihydroxy-7-protoilluden-14-al Sq-02377 - Sq-02380

Constit. of Pteridium aqui/inum var. /atiusculum, Pteris

cretica and Histiopteris incisa. Amorph. powder. Mp 85-
890. [ex]i;1 - 188° (c, 1.00 in MeOH).
I> Potent carcinogen.
Protoilludanes
Tetra-Ac: [87701-33-5].
Cryst. (MeOH). Mp 173-174° dec.
Ojika, M. et al, Tetrahedron, 1987, 43, 5261.
Saito, K. et a/, Phytochemistry, 1990, 29, 1475 (isol, bib!) Coprinolone Sq-02379
[120912-88-1]
1,7,12-Trihydroxy-2,9-illudadien-8-one Sq-02377
[1149-99-1]

C 1 ~H 22 0 3 M 250.337
Sesquiterpene antibiotic. Constit. of Coprinus
Ct~H 20 0 4 M 264.321 psychromorbidus. Cryst. (pet. ether). Mp 105-107°. [ex]i,l
-95° (c, 1.03 in CHC1 3).
(lrx.,7fl)-form
lOudin S. Lampterol. Lunamycin. NSC 400979 6,7-Didehydro: .J6-Coprinolone
Metab. of Clitocybe i/ludens and Lampteromyces Ct~H 20 03 M 248.321
japonicus. Antineoplastic. Cryst. (EtOAc). Mp 137-138°. Constit. of C. psychromorbidus. Cryst. (CH 2Cl 2/Et0Ac).
[ex]~ -165° (EtOH). Mp 186-187°. [ex]~ -105° (c, 0.98 in CHC1 3).
I> WH0204300. Starratt, A.N. eta/, J. Chern. Soc., Chern. Commun., 1988, 590
1-Deoxy: 7,12-Dihydroxy-2,9-i//udadien-8-one. 1- (isol, struct, biosynth)
Starratt, A.N. eta/, Can. J. Chern., 1989, 67, 417 (isol, pmr, cmr)
Deoxyilludin S. 6- Deoxyi/ludin S
Ct~H 20 0 3 M 248.321
Prod. by Pleurotus japonicus. Anti tumour agent. Pale- 5,6-Dihydroxy-7-protoilluden-14-al Sq-02380

o:Y.fx
yellow solid. [ex]i,l -13° (c, 1 in MeOH).
8t;-Aicoho/: [25532-76-7]. 2,9-ll/udadiene-1,7,8,12-tetro/.
DihydroiUudin S
Constit. of L. japonicus. Amorph.
Nakanishi, K. et al, Nature (London), 1963, 197, 292 (uv, ir, pmr) HO~,
Tada, M. et al, Chern. Pharm. Bull., 1964, 12, 853 (ord, ms)
Ichihara, A. et al, Tetrahedron Lett., 1969, 3963 (Dihydroilludin S) C 1 ~H 22 0 3 M 250.337
Harada, N. et al, J. Chern. Soc., Chern. Commun., 1970, 310 (abs (5p,6rx.)-form
config)
Matsumoto, T. eta/, Tetrahedron Lett., 1971, 2049 (synth) 5-(2,4-Dihydroxy-6-methy/benzoyl): [82869-08-7].
Bradshaw, A.P.W. eta/, J. Chern. Soc., Perkin Trans. I, 1982, Melleolide. Armi/larin
2445 (biosynth) C 23 H 280 6 M 400.471
Hara, M. eta/, J. Antibiot., 1987, 40, 1643 (1-Deoxyilludin S) lsol. from Armillaria mel/ea. Antifungal agent.
McMorris, T.C. et al, Tetrahedron, 1989, 45, 5433 (cryst struct) Cryst.(MeOH aq.). Mp 198-200° (122°). [ex]n + 183.3° (c,
0.93 in CHC1 3), [ex]i? +228° (c, 0.49 in CHC1 3).
1,3,7-Trihydroxy-2(9)-illuden-8-one Sq-02378 5-(2-Hydroxy-4-methoxy-6-methy/benzoyl): [96627-13-3]. 4-
3-HydroxydihydroiOudin M. 4-Hydroxydihydroi//udin M 0-Methylmelleolide
C 24 H 300 6 M 414.497

H~
From A. mel/ea. Prisms (EtOAcjheaxane). Mp 189-191°.
[ex]~ + 71 o (c, 0.31 in CHCI 3).
5-(3-Ch/oro-6-hydroxy-4-methoxy-2-methy/benzoyl): [96684-

~; 80-9]. Armillaridin
C 24 H 29Cl06 M 448.942
From A. mel/ea. Needles (Etpjpet. ether). Mp 132-
C 1 ~H 22 04 M 266.336 1340. [ex]~ + 151° (c, 0.23 in CHC1 3).
(lrx.,3rx.,7fl)-form [82779-27-9] 0 6-Me, 5-(3-Ch/oro-6-hydroxy-4-methoxy-2-methy/benzoyl):
Isol. from C/itocybe illudens. Cryst. (EtOAcjpet. ether). 6-0-Methylarmillluidin. 4-0-M ethylarmi/laridin
Mp 196-198°. [exJn + 15.4° (c, 0.2 in MeOH). C~H 31 Cl0 6 M 462.969
Bradshaw, A.P.W. eta/, Phytochemistry, 1982, 21, 942 (cryst Metab. of A. mel/ea. Cryst. (EtOAcjhexane). Mp 132-
struct) 1360. [ex]~ + 74° (c, 0.2 in MeOH).
14-Carboxy/ic acid, 5-(2,4-dihydroxy-6-methy/benzoyl):
Armillluic acid
C23H 280 7 M 416.470
lsol. from A. mel/ea. Active against gram-positive
bacteria and yeast. Brown powder.
lex-Hydroxy, 5-(2,4-dihydroxy-6-methy/benzoyl): lrx.-
Hydroxyarmillluin. JOex-Hydroxyarmillarin
C24H 300 7 M 430.497

579
10-Hydroxymelleolide - 7-Protoilludene-1,5,6,9,14-pentol Sq-02381 - Sq-02385

Metab. of A. mel/ea. Cryst. (EtOAc/hexane). Mp 108- 6-ProtoiUudene Sq-02384

1120. [a]i,l +210° (c, 0.1 in CHC1 3). [64242-89-3]
Midland, S.L. et al, Tetrahedron Lett., 1982, 2515 (isol, cryst

&P<
struct) H
Junshan, Y. et al, Planta Med., 1984, SO, 288 (isol)
Yang, J. eta/, Planta Med., 1984, SO, 288 (Mel/eo/ide)
Donnelly, D.M.X. et al, J. Nat. Prod. (Lloydia), 1985, 48, 10;
1986, 49, Ill (4-0-Methylmelleolide)
Donnelly, D.M.X. eta/, Phytochemistry, 1990, 29, 129.
Obuchi, T. eta/, Planta Med., 1990, 56, 198 (Armillaric acid) C 15H 14 M 204.355
lsol. from Fomitopsis insularis and Ompha/otus olearis. [aJn
10-HydroxymeUeolide Sq-02381 -52° (c, 0.5 in MeOH).
[97372-45-7]
[130396-93-9]
Nozoe, S. et al, Tetrahedron Lett., 1977, 1381 (isol)
Furukawa, J. eta/, Chern. Pharm. Bull., 1985, 33, 440 (synth)
OH~Yix Oppolzer, W. et a/, Tetrahedron Lett., 1986, 27, 5471 (synth)

co:~H- 7-ProtoiUudene-1,5,6,9, 14-pentol Sq-02385

H3COOH

OH
C23H 280 7 M 416.470
Metab. of Armillaria mel/ea. C,sH140 5 M 284.352
Donnelly, D.M.X. et al, Phytochemistry, 1990, 29, 2569 (isol, pmr, (1 rz,5f/)-form
cmr)
5-(2,4-Dihydroxy-6-methylbenzoyl): [1 03847-14-9].
Melledonol
14-Nor-5-protoiUudene-7,8-diol Sq-02382 C23H 300 8 M 434.485
Prod. by Armillaria mel/ea. Antibacterial. Mp 216-218°.
[a]i,l +44.6° (c, 1 in MeOH).
HOM=><HOH 5-(2-Hydroxy-4-methoxy-6-methylbenzoyl): [1 01901-56-8].
Melleolide C
C14H 310 8 M 448.512
f 'H
\ Prod. by A. mel/ea. Antibacterial agent. Cryst. Mp 78-
800. [aln + 27.9° (c, 0.5 in CHC1 3). 9-Config. undefined
C 14H 210 1 M 222.327 but prob. as shown.
(7rz,8f/)-form [110219-85-7] Sulcatine
5-(3-Ch/oro-6-hydroxy-4-methoxy-2-methy/benzoyl):
Metab. of Laurilia su/cata. Cryst. (Etpjhexane). Mp [101922-80-9]. Mel/eo/ide D
155-160°. [a]~ -61.3° (c, 2.4 in CHC1 3). C14H 31 Cl08 M 482.957
Arnone, A. eta/, Phytochemistry, 1987, 26, 1739. From A. mel/ea. Cryst. (CH 2Cl 2 jhexane). Mp 96-98°.
5-(2-Hydroxy-4-methoxy-6-methy/benzoyl): [1 0190 1-55-7].
5,6,8,14-ProtoiUudanetetrol Sq-02383 Melleolide B
C14H310 7 M 432.513
HO H From A. mel/ea. Glass. Mp 42-45°. [a] 0 + 19.6° (c, 0.6
HOH2~' 8
in MeOH).
14-A/dehyde, 5-(2-hydroxy-4-methoxy-6-methy/benzoyl): 5'-
HO- 0-Methylmelledonal
s C14H 300 8 M 446.496
HO : H Metab. of A. mel/ea. Cryst. Mp 170-171°. [a]i,S +64.7°
C 15Hu;04 M 270.368 (c, 0.34 in MeOH).
(5p,6rx.,7rz,Bf/)-form 14-Aldehyde, 5-(2,4-dihydroxy-6-methylbenzoyl): [103847-
5-(2,4-Dihydroxy-5-methylbenzoyl): Armillane 15-0]. Mel/edonal
C23H 310 7 M 420.502 C23 H 280 8 M 432.469
Metab. of Armillaria mel/ea. Cryst. (EtOAcjhexane). Prod. by A. mel/ea. Shows antibacterial props. Mp 136-
Mp 241-244°. [a]~ -59° (c, 0.2 in MeOH). 1370. [a]i,l + 195.3° (c, 0.1 in MeOH).
Donnelly, D.M.X. eta/, Phytochemistry, 1990, 29, 179 (isol, pmr, 14-Aldehyde, 13-hydroxy, 5-(2-hydroxy-4-methoxy-6-
cmr) methylbenzoyl): 13-Hydroxy-5'-0-methylmelledonal. 15-
Hydroxy-5' -0-methylmelledonal
C14H 300 9 M 462.496
Metab. of A. mel/ea. Cryst. Mp 174-176°. [a]i,S +77.3°
(c, 0.22 in MeOH).
14-A/dehyde, 5-(3-ch/oro-6-hydroxy-4-methoxy-2-
methylbenzoyl): [117458-35-2]. Melledonal C
C14H 19Cl08 M 480.941
Metab. of A. mel/ea. Cryst. (EtOAcjhexane). Mp 200-
2050. [1X] 0 + l21° (c, 0.1 in MeOH).

580
7-Protoilludene-5,6,9,14-tetrol - 7-Protoilluden-6-ol Sq-02386 - Sq-02390

14-A/dehyde, 5-(3-ch/oro-2,4-dihydroxy-6-methy/benzoyl): 6-Protoilludene-5,8,14-triol Sq-02388

[117458-36-3]. Melledonal B
C13Hr7Cl08 M 466.914 HO H
From A. mel/ea. Cryst (EtOAcjhexane). Mp 228-232°.
(1X]n + 101° (c, 0.1 in MeOH). HOH2C r t v
Absolute
Donnelly, D.M.X. et al, Tetrahedron Lett., 1985, 26, 5343 (isol,
struct, derivs)
Arnone, A. et al, Phytochemistry, 1986, 25, 471 (Mel/eo/ides)
HO~' configuration

Donnelly, D.M.X. et al, Phytochemistry, 1987, 26, 3075 (deriv) C15H140 3 M 252.353
Arnone, A. et al, J. Chern. Soc., Perkin Trans. 1, 1988, 301, 503 (5ft,8fJ)-form [82120-02-3]
(isol, pmr, cmr, cryst struct, Melledonals) Armi/lol
Oil.
7-Protoilludene-5,6,9,14-tetrol Sq-02386 5-(2,4-Dihydroxy-6-methy/benzoyl): [82105-51-9]. Armillyl
orsellinate
OH C13H 300 6 M 402.486
HOH2 ;&P<ff? Metab. of Armillaria mel/ea. Active against gram-
HO- positive bacteria. Cryst. Mp 91-93°. [a:Ji:' -126.9° (c, 1.1
in MeOH).
s 'H
HO ' 5-(2-Hydroxy-4-methoxy-6-methy/benzoyl): Armillyl
C15H 140 4 M 268.352 e11erninate
C14H 320 6 M 416.513
5P-form Prod. by A. mel/ea. Antibacterial agent. Cryst.
5-(2,4-Dihydroxy-6-methy/benzoyl): [130396-92-8]. 13- (EtOAcjhexane). Mp 86-87°. [IX]~ -66° (c, 0.79 in
Hydroxydihydromelleolide MeOH).
C13H300 7 M 418.486
5-(3-Ch/oro-6-hydroxy-4-methoxy-2-methy/benzoyl):
Metab. of Armillaria mel/ea. Cryst. Mp 112-114°. [IXW
[102092-23-9]. Arnamiol
+29° (c, 0.1 in MeOH).
C14H 31 Cl06 M 450.958
Donnelly, D.M.X. eta/, Phytochemistry, 1990, 29, 2569 (iso/, pmr, From A. mel/ea. Cryst. (EtOAcjhexane). Mp 132-134°.
cmr) [1X]n -91° (c, 0.79 in MeOH).
Donnelly, D.M.X. et al, J. Chern. Soc., Chern. Commun., 1982,
6-Protoilludene-4,8, 14-triol Sq-02387 135; 1984, 222 (isol, struct, abs config)
Donnelly, D.M.X. et al, J. Nat. Prod. (Lloydia), 1986, 49, Ill

~
?HH (derivs)

HOH2CI 8
7-Protoilludene-4,6,14-triol Sq-02389
NeoiUudol
4 \ H (4a,8a)-form
[57566-22-0]
\
OH
C 15H140 3 M 252.353
(4rx.,8rx.)-form [16981-75-2] Illudol
Metab. of Clitocybe illudens. Cryst. (EtOAc). Mp 130-
1320. (1X]n -116° (c, 0.42 in EtOH).
(4rx.,8fJ)-form
C 15H 140 3 M 252.353
3-Epiilludol. 3-epi-II/udo/
Metab. of Clitocybe i/ludens. Cryst. (EtOAc). Mp 152-153°.
Metab. of C. candicans. Glass. Mp 42-44°. [1Xln -106°
(c, 1 in EtOH). Nair, M.S.R. et al, Tetrahedron Lett., 1975, 1267.
14-Ac:
C 17H:11P 3 M 278.391 7-Protoilluden-6-ol Sq-02390
Metab. of C. candicans. Oil. [1X]n -78.4° (c, 0.2 in

HOw~H
CHC1 3).
McMorris, T.C. et al, J. Am. Chern. Soc., 1967, 89, 4562 (isol,
struct)
Cradwick, P.D. et al, J. Chern. Soc., Chern. Commun., 1971, 431 ,H
(cryst struct) \

Matsumoto, T. eta/, Tetrahedron Lett., 1971, 3521 (synth) CtsH140 M 220.354

Semmelhack, M.F. et al, J. Am. Chern. Soc., 1980, 102, 7567; Metab. of Fomitopsis insu/aris. Oil.
1982, 104, 747 (synth)
Semme1hack, M.F. et al, Strategies Tactics Org. Synth., 1984, 201 Nozoe, S. et al, Tetrahedron Lett., 1977, 1381.
(rev)
Arnone, A. et al, J. Chern. Soc., Perkin Trans. 1, 1989, 1995 (isol,
deriv)

581
6-Hydroxy-2-sterpuren-12-oic acid - 2-Sterpuren-6-ol Sq-02391 - Sq-02397

Metab. of M. tremellosus. Cryst. Mp 160-164°. [aJn

+43° (c, 0.8 in Et20).
Sterpuric acid group Sterner, 0. et al, Tetrahedron, 1990, 46, 2389 (isol, cryst struct, abs
config)

2-Sterpurene-8,15-diol Sq-02394
7,12-Dihydroxysterpurene
6-Hydroxy-2-sterpuren-12-oic acid Sq-02391 [112163-46-9]
Sterpuric acid

q¢b<
[79367-59-2] HO

~~H CHpH
CtsH 240 1 M 236.353
C15H 220 3 M 250.337 Metabolite of fungus Stereum purpureum.
Constit. of Stereum purpureum. Phytotoxin; causative
agent of silver leaf disease. Cryst. (EtOAc). Mp 203- Abell, C. et al, Tetrahedron Lett., 1987, 28, 4887; 1988, 29, 1985
(isol, abs config)
- 207°. [a]~ + 72° (c, O.o3 in MeOH).
14-Hydroxy: [79367-60-5]. 6,14-Dihydroxy-2-sterpuren-12-
oic acid. 14-Hydroxysterpuric acid 2-Sterpurene-10,15-diol Sq-02395
C15H 220 4 M 266.336 9,12-Dihydroxysterpurene
Constit. of S. purpureum. Phytotoxin. Isol. as Me ester. [121878-52-2]
14-Hydroxy, 6,14-ethylene acetal: [79367-61-6].
C 17H 240 4 M 292.374
Constit. of S. purpureum. lsol. as Me ester.
Ayer, W.A. et al, Tetrahedron, Suppl., No. I, 1981, 379 (cryst
struct)
Ayer, W.A. et al, Can. J. Chern., 1984, 62, 531 (biosynth)
Paquette, L.A. eta/, Tetrahedron Lett., 1987, 28, 5017 (synth)
Abell, C. et a/, Tetrahedron Lett., 1988, 29, 1985 (abs config) C15H 240 1 M 236.353
Metab. of Stereum purpureum.
2-Sterpurene Sq-02392 Abell, C. eta/, Tetrahedron Lett., 1988, 29, 4337 (struct, biosynth)
1-Sterpurene
[79579-56-9] 2-Sterpurene-6,12,15-hiol Sq-02396
1-Sterpurene-3,12, 14-triol
[79579-55-8]
I H
~CH,OH
C 15H 24 M 204.355
Metab. of Stereum purpureum. Oil. [aln +65.3° (c, 0.87 in
HO CHpH
CHCl 3).
Ayer, W.A. eta/, Can. J. Chern., 1981, 59, 2536; 1984, 62, 531 C 15H 240 3 M 252.353
(isol, biosynth) Metab. of Stereum purpureum. Cryst. (Et 20). Mp 146-148°.
Gibbs, R.A. eta/, J. Am. Chern. Soc., 1988, 110, 4062 (synth) [a]~ +64° (c, 0.1 in MeOH).
Zhao, S.K. et al, J. Org. Chern., 1990, 55, 5820 (synth)
Ayer, W.A. eta/, Can. J. Chern., 1981, 59, 2536; 1984, 62, 531
(isol, biosynth)
2-Sterpurene-6,10.diol Sq-02393
TrenuuBol
2-Sterpuren-6-ol Sq-02397
[129058-89-5] 3-Sterpurenol

gyt><
I H OH I H

C 15H 240 1
~
M 236.353 C15H 240 M 220.354
Metab. of fungus Merulius tremellosus. Cryst. Mp 134- Ac: [126201-36-3]. 3-Acetoxysterpurene
1350. [cxJn -71° (c, 1.1 in Etp). C17H 11;01 M 262.391
4a-Hydroxy: [129058-90-8). 2-Sterpurene-4,6,10-triol. Metab. of Alcyonum acaule. Oil. [cxJn + 128.6° (c, 2.2 in
Tremetriol CHC1 3).
C 15H 240 3 M 252.353 Cimino, G. et al, Tetrahedron, 1989, 45, 6479.

582
Calomelanolactone - Onitin Sq-02398 - Sq-02404

IDudacetalic acid Sq-02401

1,3 ,4,6,7,8-Hexahydro-1 ,3,9-trimethoxy-7,7-
illudalanes dimethylcyc/openta[g]-2-benzopyran-5-carboxy/ic acid, 9CI
[37812-52-5]
OMe

Calomelanolactone Sq-02398 ?~
[66471-97-4] Me0~"-
0

tx(cc
C18H1406 M 336.384
Metab. of Clitocybe illudens. Cryst. (EtOAc). Mp 145-147°.
Nair, M.S.R. et al, Tetrahedron Lett., 1972, 2753 (isol)
Woodward, R.B. et al, J. Am. Chem. Soc., 1977, 99, 8007 (synth,
struct)

C1sH 180 3 M 246.305

Occurs in Pityrogramma calomelanus. Cryst. (EtOAcjpet. IDudalic acid Sq-02402
ether). Mp 160-162°. 1,3,4,7,8,9-Hexahydro-3,6-dihydroxy-8,8-dimethyl-1-
oxocyclopenta[h]-2-benzopyran-5-carboxaldehyde, 9CI
Bardonille, V. et al, Phytochemistry, 1978, 17, 275 (cryst struct)

y
[18508-77-5]
Candicamol Sq-02399 OH
[125296-43-7]
H
HOH2C ) i x
HO 0 0

HOH2~- CtsHt60 5 M 276.288

Metab. of Clitocybe illudens. Cryst. (EtOH). Mp >200°
dec. [a:Jn + 0° (EtOH).
C1sHn03 M 250.337 3-Ac: Cryst. (MeOH). Mp 168-169.5°.
Metab. of C/itocybe candicans. Pale yellow solid. Mp 56-
580. [a:)n + 30° (c, 1 in MeOH). Nair, M.S.R. et al, J. Org. Chem., 1969, 34, 240 (struct)
Woodward, R.B. et al, J. Am. Chem. Soc., 1977, 99, 8007 (synth)
Arnone, A. et al, J. Chem. Soc., Perkin Trans. 1, 1989, 1995 (isol,
pmr, cmr)
IDudoic acid Sq-02403
1,3,4,6,7,8-Hexahydro-3,9-dihydroxy-7,7-
Fomajorin D Sq-02400 dimethylcyc/openta[g]-2-benzopyran-5-carboxylicacid, 9CI
7,8-Dihydro-9-hydroxy-5,7,7-trimethylcyc/openta[g]-2-
benzopyran-1 (6H)one, 9C/ [18508-79-7]

$
[85533-03-5] OH

0
O OH
~
~ HO
1)0:>< COOH
13
C1sH180s M 278.304
Metab. of Clitocybe i/ludens. Mp 135°.
Di-Ac: Mp 153-154°.
C1sH160 3 M 244.290
Metab. of Fornes annosus. Also secreted by Heterobasidium Nair, M.S.R. et al, J. Org. Chem., 1969, 34, 240 (struct)
annosum in the presence of antagonistic fungi. Cryst.
Mp 126-127° (121.5°). Onitin Sq-02404
13-Carboxy/ic acid: [85533-02-4]. Fotnlljorin S 2,3-Dihydro-4-hydroxy-6-(2-hydroxyethyl)-2,2 ,5, 7-
CtsH 140 5 M 274.273 tetramethy/-JH-inden-1-one, 9CI
Metab. of F. annosus. Cryst. Mp 243-245°. [a:]~ -12.6° [53823-02-2]
{c, 0.16 in Me2CO).
Donelly, D.M.X. et al, Tetrahedron Lett., 1982, 23, 5451 (isol,
struct)
Sonnenbichler, J. et al, Phytochemistry, 1983, 22, 1489 (cryst
struct)
Donnelly, D.M.X. et al, J. Chem. Soc., Perkin Trans. I, 1987,
1869 (biosynth)
C15H 100 3 M 248.321
Isol. from Onychium auratum, 0. si/icu/osum, Equisetum
arvense, Cibotium barometz and Dicksonia gigantea.
Smooth muscle relaxant. Cryst. (MeOH). Mp 212-214°.
8-0-P-v-G/ucopyranoside: [78415-48-2]. Onitinoside
C11 H300 8 M 410.463
lsol. from 0. siliculosum. Cryst. (EtOAc). Mp 172-174°.

583
Pterosin J\ - Pterosin II Sq-02405 - Sq-02407

12-Hydroxy: [53823-03-3]. Onitisin Constit. of fronds of P. aquilinum subsp. wightianum.

CtsH 200 4 M 264.321 Amorph. powder. [ali:' -22° (c, 0.43 in MeOH).
Isol. from 0. auratum, Pteridium aquilinum and 5t,-Hydroxy: [98474-70-5]. Spelosin
Dennstaedtia scabra. Cryst. Mp 178-179°. [a]i; -31.16° C15H 2004 M 264.321
(c, 1 in MeOH). Constit. of fronds of Microlepia speluncae. Syrup. [a)~
Hayashi, Y. et al, Chern. Lett., 1974, 945 (synth) +83.3° (c, 0.7 in MeOH).
Banerji, A. et al, Tetrahedron Lett., 1974, 1369 (isol) 5-Hydroxy, 10-0-a-L-arabinopyranoside:
Murakami, T. et al, Chern. Pharm. Bull., 1975, 23, 1630 (isol) C20 H180 8 M 396.436
Wadhawan, V.K. et al, Acta Crystallogr., Sect. B, 1977, 33, 428
(struct) Constit. of M. speluncae, M. trapeziformis and M.
McMorris, T.C. et al, J. Nat. Prod. (Lloydia), 1977, 40, 221 (isol) substrigosa. Amorph. powder. [a)i,l + 56.9° (c, 1 in
Syrchina, A.I. et al, Khim. Prir. Soedin., 1978, 508 (isol, struct) MeOH).
Murakami, T. et al, Phytochemistry, 1980, 19, 1743 (isol) 14-Hydroxy: [62043-47-4). Pterosin X
Wu, T.-S. et al, Phytochemistry, 1981, 20, 527 (deriv) C15H 200 4 M 264.321
Salake, T. et a/, Chern. Pharm. Bull., 1984, 32, 4620 (isol) lsol. from P.fauriei. Syrup. [a]i,l + 31.1° (c, 0.29 in
Yang, M.S., Planta Med., 1986, 25 .(pharmacal) MeOH).
Raju, B. et al, Indian J. Chern., Sect. B, 1987, 26, 914 (synth)
14-Hydroxy, 4-0-P-D-glucopyranoside: [62043-49-6).
Pteroside X
Pterosin A Sq-02405 C11 H300 9 M 426.463
2,3-Dihydro-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7- lsol. from P. fauriei. Syrup. [aln -10.3° (c, 0.58 in
trimethyi-JH-inden-1-one, 9CI. 6-(2-Hydroxyethyl)-2- MeOH).
hydroxymethy/-2,5, 7- trimethy/-1-indanone
15-Hydroxy: [62043-46-3). Pterosin W
[35910-16-8) C1 5H 2004 M 264.321
lsol. from P. fauriei. Syrup. [a]i,l + 51.2° (c, 0.215 in
HJC 0 MeOH).
HOH2CH2C0 ,CH20H Absolute 15-Hydroxy, 4-0-P-D-g/ucopyranoside: [62043-48-5].
H3 C~CH3 configuration Pteroside W
C11 H 300 9 M 426.463
C 15H2003 M 248.321 lsol. from P. fauriei.
I> NK8932000. 4-Deoxy, 4-ch/oro: [84299-81-0]. 3R-Hydroxypterosin H
(S)-form C15H 19Cl01 M 266.767
Constit. of Pteridium aquilinum. Cryst. (C 6H 6). Mp 125- From P. aquilinum subsp. wightianum. Syrup.
1270. [aln -21.8° (CHC1 3). (S)-form [61138-81-6]
14-P-D-G/ucoside: [35910-15-7]. Pteroside A Cryst. (MeOHJCC1 4). Mp 190-192°. [alii +6.3° (c, 0.255
C11 H300 8 M 410.463 in MeOH).
Constit. of P. aquilinum. 4-0-P-D-Glucopyranoside: (JS)-Pteroside D
Fukuoka, M. et al, Chern. Pharm. Bull., 1971, 19, 1491; 1972, 20, C11 H300 8 M 410.463
426; 1974, 22, 723; 1979, 27, 731 (isol, struct, abs conjig) Constit. of Hypolepis punctata. Oil.
Hikino, H. et a/, Chern. Pharm. Bull., 1972, 20, 210 (Pteroside A)
Banerji, A. eta/, Tetrahedron Lett., 1974, 1369 (deriv) Fukuoka, M. eta/, Chern. Pharm. Bull., 1971, 19, 1491; 1972, 20,
426; 1974, 22, 723; 1979, 27, 731 (isol, struct, abs conjig)
Murakami, T. et al, Chern. Pharm. Bull., 1975, 23, 1630 (deriv)
Chen, C.-M. et al, Chern. Pharm. Bull., 1976, 24, 2241 (isol) Hikino, H. et al, Chern. Pharm. Bull., 1971, 19, 2425 (Pteroside D)
Hayashi, Y. eta/, Chern. Lett., 1974, 945 (synth)
Marakami, T. eta/, Chern. Pharm. Bull., 1976, 24, 1961 (Pterosin
Pterosin D Sq-02406 X, Pteroside X, Pterosin W, Pteroside 1¥)
2,3-Dihydro-3-hydroxy-6-(2-hydroxyethyl)-2,2 ,5, 7- Murakami, T. et al, Chern. Pharm. Bull., 1976, 24, 2241 (3S-
tetramethy/-JH-inden-1-one, 9Cl. 3-Hydroxy-6-(2- Pteroside D)
Chen, C.-M. et al, Chern. Pharm. Bull., 1976, 24, 2241 (isol)
hydroxyethyl)-2,2 ,5 ,7-tetramethy/-1-indanone Tanaka, N. et al, Chern. Pharm. Bull., 1982, 30, 3640 (isol)
OH Kuraishi, T. eta/, Chern. Pharm. Bull., 1985, 33, 2305 (isol, deriv)

Pterosin II Sq-02407
6-(2-Ch/oroethyl)-2,3-dihydro-2,2,5,7-tetramethyi-JH-inden-
(R)-form
1-one, 9Cl. 6-(2-Ch/oroethyl)-2,2,5,7-tetramethyl-1-indanone.
Hypolepin A
C15H 200 3 M 248.321 [39004-41-6)
(R)-form [34169-70-5]

OH,~
Constit. of Pteridium aquilinum. Oil. [alii -4.3° (c,
0.115 in MeOH).
4-0-P-D-Glucopyranoside: [35943-38-5]. Pteroside D
C11H 300 8 M 410.463
Constit. of P. aquilinum. C1sH 19ClO M 250.767
Constit. of the leaves of Hypolepis punctata. Mp 87.5-88°.
10-0-a-L-Arabinopyranoside: [98474-71-6).
Cwli180 7 M 38o.437 Hayashi, Y. et al, Chern. Lett., 1972, 375 (isol, struct, synth)
Constit. of fronds of Microlepia speluncae. Needles Yoshihira, K. et al, Chern. Pharm. Bull., 1972, 20, 426 (isol, struct)
McMorris, T.C. et a/, J. Nat. Prod. (Lioydia), 1977, 40, 221 (synth)
(CHC1 3/MeOH). Mp 164-166°. [a)n +43.9° (c, 1 in
MeOH).
10-0-P-D-Glucopyranoside: [84299-80-9].
C11H 300 8 M 410.463

584
Pterosin J - Pterosin M Sq-02408 - Sq-02411

Pterosin J Sq-02408 4-0-P-o-G/ucopyranoside:

6-(2-Ch/oroethyl)-2,3-dihydro-3-hydroxy-2,5,7-trimethyi-1H- C21H300, M 426.463
inden-1-one. 6-(2-Ch/oroethyl)-3-hydroxy-2,5,7-trimethy/-1- Constit. of Hypolepis punctata. Syrup.
indanone 10-0-IX-L-Arabinopyranoside:
[41411-02-3] C20H 280 8 M 396.436
Constit. of fronds of Microlepia speluncae and M.
trapeziformis. Needles (CHC1 3/MeOH). Mp 209-211°.
[IX]~ -21.7° (c, 0.46 in MeOH).
15-Hydroxy: [95377-46-1]. Jamesonin
C 1 ~H 20 0~ M 280.320
Constit. of Jamesonia scammanae. Amorph. [1X]i;' +9.6°
(c, 0.35 in MeOH).
C 14H 17Cl02 M 252.740
(lOR,llS)-form [69753-99-7]
Constit. of Pteris ryukyuensis and of the leaves of
Needles (C6H 6). Mp 85-87°. [1X]i: + 78° (c, 0.28 in
Pteridium aquilinum. Cryst. (C6H 6fhexane). Mp 136-
MeOH).
1370. [1X]n +83.SO (c, 0.17 in CHC1 3).
4-0-P-D-Giucopyranoside: Constit. of H. punctata. Oil.
Fukuoka, M. eta/, Chern. Pharm. Bull., 1972, 20, 2282 (isol,
struct) Fukuoka, M. eta/, Chern. Pharm. Bull., 1972, 20, 2282; 1974, 22,
Kuroyanagi, M. et a/, Chern. Pharm. Bull., 1974, 22, 723 (abs 723; 1979, 27, 731 (isol, struct, abs config)
config) Chen, C.-M. eta/, Chern. Pharm. Bull., 1976, 24, 2241 (deriv)
Tanaka, N. eta/, Chern. Pharm. Bull., 1978, 26, 1339 (isol) Satake, T. eta/, Chern. Pharm. Bull., 1984, 32, 4620 (Jamesonin)
Yoshihira, K. eta/, Chern. Pharm. Bull., 1978, 26, 2346 (isol) Kuraishi, T. eta/, Chern. Pharm. Bull., 1985, 33, 2305.
Fukuoka, et a/, Chern. Pharm. Bull., 1978, 26, 2365 (struct)
Kuroyanagi, M. eta/, Chern. Pharm. Bull., 1979, 27, 731
(stereochem)
Pterosin M Sq-02411
2,3-Dihydro-4-hydroxy-6-(2-hydroxyethyl)-2,5,7-trimethyi-
1H-inden-1-one, 9CI. 4-Hydroxy-6-(2-hydroxyethyl)-2,5,7-
Pterosin K Sq-02409 trimethy/-1-indanone
6-(2-Chloroethyl)-2,3-dihydro-2-(hydroxymethyl)-2,5,7-
trimethyl-1H-inden-1-one, 9CI. 6-(2-Ch/oroethyl)-2-
hydroxymethy/-2,5,7-trimethy/-1-indanone

Ct4Ht80 3 M 234.294
(R)-form [52744-25-9]
Aglycone from Onychium japonicum. Cryst. (H20 or
C 1 ~H 19 Cl0 2 M 266.767 EtOAc).
(S)-form [41411-03-4] Di-Ac: Cryst. (EtOH). Mp 77-79°.
Constit. of the leaves of Pteridium aquilinum. Cryst.
(hexane). Mp 85-87°. [1X]n -20° (CHC1 3), [1X]n -37.SO (c, 0-P-D-Glucopyranoside: [52715-92-1]. Pteroside M
0.14 in MeOH). C20H 280 8 M 396.436
From 0. japonicum. Cryst. (EtOH). Mp 192°. [IX]~
Dech/oro, 4-methoxy: [56670-45-2]. Pterosin V + 129° (c, 1.2 in Me2CO aq.).
Ct,H 22 0 3 M 262.348
Isol. from Dennstaedtia scabra. Oil. [1X]i;1 -4° (c, 0.69 in 4-Carboxy/ic acid: [52528-78-6]. Pterosin E. 2,3-Dihydro-
MeOH). 2,4,6-trimethyl-3-oxo-1H-indene-5-acetic acid, 9CI. 2,4,6-
Trimethy/-3-oxo-5-indanacetic acid, SCI. BH4
Fukuoka, M. eta/, Chern. Pharm. Bull., 1972, 20, 2282 (iso/, Constit. of Pteridium aquilinum leaves. Cryst. (CC14).
struct, synth; 11978, 26, 2365.
Kuroyanagi, M. eta/, Chern. Pharm. Bull., 1974, 22, 723; 1978, 26,
Mp 160-162°.
2365 (abs config) 4-Deoxy, 4-chloro: [34175-98-9]. Pterosin F. 6-(2-
Murakami, T. eta/, Chern. Pharm. Bull., 1975, 23, 1630 (Pterosin Ch/oroethyl)-2 ,3-dihydro-2,5, 7-trimethyi-1H -inden-1-one,
V) 9CI
Yoshihira, K. eta/, Chern. Pharm. Bull., 1978, 26, 2346 (isol) Ct4H7C10 M 226.661
Kuroyanagi, M. eta/, Chern. Pharm. Bull., 1979, 27, 592, 731. Constit. of bracken P. aquilinum. Cryst. (hexane). Mp
66-67°. [1X]n -9.2° (C6H6).
Pterosin L Sq-02410 12-Hydroxy: [35964-50-2]. Pterosin G
2,3-Dihydro-3-hydroxy-6-(2-hydroxyethyl)-2- Ct4Hta03 M 234.294
(hydroxymethyl)-2,5,7-trimethyi-1H-inden-1-one, 9CI. 3- Isol. from P. aquilinum. Mp 152-153°. Has (S) config.
Hydroxy-6-(2-hydroxyethyl)-2-hydroxymethy/-2,5,7- Yoshihira, K. eta/, Chern. Pharm. Bull., 1971, 19, 1491; 1972, 20,
trimethyl-1-indanone 426; 1974, 22, 723; 1978, 26, 2346 (iso/, uv, ir, pmr)
Fukuoka, M. et a/, Chern. Pharm. Bull., 1972, 20, 426; 1974, 22,
723; 1978, 26, 2365; 1979, 27, 731 (iso/, uv, ms, ir, pmr, struct,
abs config)
Kuroyanagi, M. eta/, Chern. Pharm. Bull., 1974, 22, 723; 1979, 27,
592, 731 (abs config)
Nambudiry, M.E.N. et a/, J. Chern. Soc., Perkin Trans. I, 1974,
317 (synth, pmr)
Hasegawa, M. eta/, Phytochemistry, 1974, 13, 509 (isol)
C 1 ~H 20 04 M 264.321 McMorris, T.C. eta/, J. Nat. Prod. (Uoydia), 1977, 40, 221 (isol,
(JOR,llR)-form [41411-04-5] synth)
Constit. of Pteridium aquilinum. Needles (C6H 6). Mp Raju, B. eta/, Indian J. Chern., Sect. B, 1987, 26, 914 (synth)
134-135°. [IX]~ +22.2° (c, 0.36 in MeOH).

585
Pterosin N - Lactarorufin C Sq-02412 - Sq-02416

Pterosin N Sq-02412 15-Hydroxy, 4-0-P-v-g/ucopyranoside: [62043- 52-1].

2,3-Dihydro-2-hydroxy-6-(2-hydroxyethyl)-2,5,7-trimethyi- Pteroside U
1H-inden-1-one, 9Cl. 2-Hydroxy-6-(2-hydroxyethyl)-2,5,7- C20H 280 10 M 428.435
trimethy/-1-indanone lsol. from P.fauriei. Cryst. Mp 149-151°. [1X]i,2 +2.3° (c,
[54797-11-4] 0.865 in MeOH).
14-Deoxy, 15-hydroxy: [56227-00-0]. Pterosin S
C,4H,a04 M 250.294

HOH,~OH lsol. from P. kiuschiuensis. Mp 118-119°. [1X]i; +71° (c,

0.53 in MeOH).
14-Deoxy, 15-hydroxy, 4-0-P-v-g/ucopyranoside: [62043-50-
C,4H,s03 M 234.294 9]. Pteroside S
lsol. from Pteridium aquilinum. Cryst. (Me 2CO). Mp 165- C20 H 280 9 M 412.436
1670. [1X]n -18.8° (MeOH). lsol. from P. inaequalis.
Kuroyanagi, M. et al, Chern. Pharrn. Bull., 1974, 22, 2762 (isol) 14-Deoxy, 5C:.-hydroxy: [54797-09-0]. Fterosin Q
C,4H,a04 M 250.294
lsol. from P. oshimensis, other P. spp. and Histiopteris
Pterosin P Sq-02413 incisa. Syrup. [1X]i; +90° (c, 1 in MeOH).
2,3-Dihydro-6-(2-hydroxyethyl)-5-(hydroxymethyl)-2,7-
14-Deoxy, 5C:.-hydroxy, 10-0-P-v-arabinoside: Pterosin Q
dimethyi-1H-inden-1-one, 9Cl. 6-(2-Hydroxyethyl)-5-
arabinoside
hydroxymethy/-2,7-dimethy/-1-indanone
c,9H 21;08 M 382.410
lsol. from P. oshimensis. Syrup. [1X]i; + 25° (c, 1 in
MeOH).
14-Deoxy, 5C:.-hydroxy, 10-0-P-v-g/ucopyranoside: [54797-
08-9]. Pteroside Q
C20 H 280 9 M 412.436
C,4H,a03 M 234.294 lsol. from P. oshimensis and H. incisa. Syrup. [1X]i; +24°
(S)-form [56374-22-2] (c, 1 in MeOH).
lsol. from Pteridium aquilinum. Cytotoxin. Cryst. Murakami, T. et a/, Chern. Pharm. Bull., 1974, 22, 2758; 1975, 23,
(CHC1 3/C 6H 6). Mp 115-117°. [1X]n +4.6° (MeOH). 936, 1890; 1976, 24, 1961.
4-0-P-v-G/ucopyranoside: [54854-88-5]. Pteroside P Tanaka, N. et al, Chern. Pharm. Bull., 1978, 26, 1339; 1982, 30,
C20 H 28 0 8 M 396.436 3640.
Constit. of P. aquilinum. Cryst. (MeOH/CHC1 3). Mp
191-193°. [1X]n -14.9° (MeOH).
Kuroyanagi, M. eta/, Chern. Pharrn. Bull., 1974, 22, 2762; 1979,
27, 592 (isol)

Isolactaranes
Saito, M. et al, Experientia, 1975, 31, 829.

Pterosin T Sq-02414
2,3-Dihydro-3-hydroxy-6-(2-hydroxyethyl)-5-
(hydroxymethyl)-2,7-dimethyi-1H-inden-1-one,9CI. 3-
Hydroxy-6-(2-hydroxyethyl)-5-hydroxymethy/-2,7-dimethy/-
Dihydrosterepolide Sq-02415
1-indanone
[79380-67 -9]
[56227-01-1]
0

o>--~
I
'\...-

HOHi: O
C,sH,804 M 262.305
C,4H,s04 M 250.294 Sesquiterpene antibiotic. lsol. from Stereum purpureum.
lsol. from Pteris kiuschiuensis. Syrup. [1X]t' +91° (c, 1 in
Fungal toxin. Mp 210-212°.
MeOH).
Ayer, W.A. eta/, Tetrahedron Lett., 1981, 2071 (isol, struct)
4-0-P-v-G/ucopyranoside: [62043-51-0]. Pteroside T
C 20H 280 9 M 412.436
lsol. from P. inaequalis. Cryst. Mp 118-121°. [1X]i,2 +33° Lactarorufin C Sq-02416
(c, 1.2 in MeOH). lsolactarorufin
12-Hydroxy: [84299-78-5]. 12-Hydroxypterosin T. 11- [62024-77-5]
Hydroxypterosin T
C,4H 180 5 M 266.293
Constit. of fronds of Pteris bella. Amorph. powder. [1X]n
+ 54° (c, 0.3 in MeOH).
15-Hydroxy: [56227-02-2]. Pterosin U
C,4H 180 5 M 266.293
lsol. from P. kiuschiuensis. Mp 129-130°. [1X]i;' +73.1° (c,
0.47 in MeOH).
M 266.336

586
Merulactone - Blennin B Sq-02417 - Sq-02423

Constit. of Lactarius rufus. Cryst. Mp 191°. [ex]~ +8.4°. Sterepolide Sq-02421

Daniewski, W.M. eta/, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1970, [79380-66-8]
18, 585.
Kontiz, A. eta/, Tetrahedron Lett., 1977, 38, 3401 (cryst struct) 0

Merulactone Sq-02417 o
~ I

olf><
HO '. I 0
0--./
Ct5H 160 4 M 260.289
Sesquiterpenoid antibiotic. lsol. from Stereum purpureum.
Fungal toxin. Mp 228-232°.
(±)-form
Mp 192-193°.
C 15H:ze03 M 248.321
Metab. of fungus Meru/ius tremellosus. Oil. [ex] 0 -38° (c, Ayer, W.A. et a/, Tetrahedron Lett., 1981, 2071 (isol, struct)
Trost, B.M. eta/, J. Am. Chern. Soc., 1985, 107, 4586 (synth)
1.5 in Etp).
Sterner, 0. eta/, Tetrahedron, 1990, 46, 2389 (isol, struct)

Merulanic acid Sq-02418

[129058-91-9]
HO
Lactaranes

OH~ COOH
Blennin A
Lactarorujin N
[62860-40-6)
Sq-02422

ott},
Ct5H:ze04 M 264.321
Metab. of fungus Merulius tremellosus.
Me ester: [129058-97-5].
Cryst. Mp 121-124°. [ex) 0 -59° (c, 2.5 in CHC1 3).
Sterner, 0. eta/, Tetrahedron, 1990, 46, 2389 (iso/, struct)

Merulialol Sq-02419

Hp
Ct5Hn03 M 250.337
H Constit. of Lactarius blennius and L. necator. Oil. [ex]~
+49.9° (CHC1 3), [ex]~ -15.1 o (c, 1 in CHC1 3).
12-Hydroxy: 12-Hydroxyblennin A. 15-Hydroxyblennin A
C15H120 4 M 266.336
Constit. of L. torminosus. Cryst. Mp 144°. Tentative
0
stereochem. C-11 config. not detd.
C15H 120 3 M 250.337 Vidari, G. eta/, Phytochemistry, 1976, 15, 1953 (isol)
Mixt. of epimers. Metab. of fungus Merulius tremellosus. Widen, K.G. eta/, Phytochemistry, 1979, 18, 1226 (12-
Cryst. Mp 62-67°. [ex) 0 +30° (c, 3.0 in CHC1 3). Hydroxyb/ennin A)
[129058-93-1, 129101-68-4] de Bernardi, M. eta/, Phytochemistry, 1980, 19, 99 (isol)
Daniewski, W.M. eta/, Pol. J. Chern. (Rocz. Chern.), 1981, 55,
Sterner, 0. eta/, Tetrahedron, 1990, 46, 2389 (isol, struct)
1247 (isol)

Merulidial Sq-02420 Blennin B Sq-02423

[68053-32-7] [62824-37-7]
OH

OH~ CHO
C15H:ze03 M 248.321
lsol. from Meru/ius tremellosus. Antibiotic active against Ct5Hzt,04 M 264.321
various bacteria, fungi and yeasts. Pale-yellow oil or Constit. of Lactarius blennius. Oil. [ex]~ + 70.78° (Me2CO).
cryst. Mp 34°. A.max 270 nm (e 3 660) (MeOH). Vidari, G. et al, Phytochemistry, 1976, 15, 1953.
I> OX4000000.
Quack, W. et a/, J. Antibiot., 1978, 31, ]37 (iso/, uv)
Giannetti, B.M. et a/, Tetrahedron, 1986, 42, 3579 (struct)
Sterner, 0. et a/, Tetrahedron, 1990, 46, 2389 (cryst struct)

587
Blennin C- 2,9-Epoxylactarotropone Sq-02424 - Sq-02430

Blennin C Sq-02424 lsol. from L. vellereus, L. pergamenus and L. helvus.

[62824-38-8] Cryst. (Etp). Mp 65-66°. [a]~ +6.0° (c, 0.6 in MeOH).
Prob. artifact.

oA_p<
CHPH Nozoe, S. eta/, Tetrahedron Lett., 1971, 3125 (isol, struct)
Magnusson, G. eta/, Acta Chern. Scand., Ser. B, 1974, 28, 841
(Me ether)
Battaglia, R. eta/, J. Nat. Prod. (Lioydia), 1980, 43, 319
0 \ (Furoscrobiculin C)
\ Sterner, 0. eta/, Acta Chern. Scand., Ser. B, 1988, 42, 43 (isol)
C15H 210 3 M 250.337
Constit. of Lactarius scrobicu/atus and L. blennius. Pale- 4,8-Dihydroxylactariusfuran Sq-02428
yellow oil. [a]~ -73° (CHCI 3). [114728-44-8]
Vidari, G. eta/, Phytochemistry, 1976, 15, 1953 (iso/, struct)

0~
De Bernardi, M. eta/, Tetrahedron, 1986, 42, 4277 (abs co'!fig)

Blennin D Sq-02425

HO~'-
[72601-39-9]

C15H2103 M 250.337
Constit. of Lactarius spp. Oil. [a]i;l +4° (c, 0.7 in CHC1 3).
Di-Ac: Cryst. Mp 70-75°. [a]~4 +56° (c, 0.6 in CHCI 3).
Sterner, 0. eta/, Acta Chern. Scand., Ser. B, 1988, 42, 43.

CtsH210 4 M 266.336 5,14-Epoxy-3(15),5,7(14)-lactaratrien-8-ol Sq-02429

Constit. of Lactarius blennius. Oil. [a]~ +51° (Me 2CO).
4,4a,5,6,7,7a,8,9-0ctahydro-6,6-dimethyl-8-
de Bernardi, N. eta/, Phytochemistry, 1980, 19, 99. methy/eneazu/eno[5,6-c]furan-4-ol, 9CI
[89002-38-0]
3,8:5,14-Diepoxy-5,7(14)-lactaradiene Sq-02426
3,8:5,14-Bisepoxy-5,7(14)-/actaradiene

CtsH 21,01 M 232.322

CtsH21,01 M 232.322 Constit. of Lactarius vellereus. Oil. [a]~ + 2.8° (c, 0.88 in
(3rx.,8rx.)-form [74778-23-7] Furanether B CHCI 3). Also formed by dec. of fatty acid esters of
Constit. of Lactarius scrobicu/atus. Oil. [a]~ +48.6° velutinal.
(CHCI 3). A 2•3-Jsomer: 5,14-Epoxy-2,5,7(14)-lactaratrien-8-ol
(Jp,B/1)-form [72601-35-5] Furanether A CtsH21,01 M 232.322
Constit. of Russula sardonia. Yellow oil. [a]~ +26° lsol. from L. vellereus, L. pergamenus and L. helvus.
(CHCI 3). Cryst. (hexane). Mp 34-44°. [a]~ + 123° (c, 0.6 in
Battaglia, R. et a/, J. Nat. Prod. (Lloydia), 1980, 4J, 319 MeOH).
(Furanether B) Magnusson, G. eta/, Acta Chern. Scand., Ser. B, 1974, 28, 841
Andina, D. eta/, Phytochemistry, 1980, 19, 93 (Furanether A) (deriv)
K.ihlberg, J. eta/, Tetrahedron Lett., 1983, 24, 4631.
3,8-Dihydroxylactariusfuran Sq-02427
[59684-34-3] 2,9-Epoxylactarotropone Sq-02430
[124208-78-2]
OH

~
~ I OH
C15H 210 3 M 250.337 C15H 160 4 M 260.289
Constit. of Lactarius spp. Oil. Constit. of Lactarius scrobicu/atus. Oil.
8-Et ether: [74686-33-2]. Furoscrobiculin C. 8-Ethoxy-3- Bosetti, A. et a/, Phytochemistry, 1989, 28, 1427.
hydroxy/actariusfuran
C17H 160 3 M 278.391
Constit. of L. scrobiculatus. Oil. [a]~ + 12.8° (CHC1 3).
3-Me ether:
C 16H140 3 M 264.364

588
Furantriol - Lactarolide A Sq-02431 - Sq-02438

Furantriol Sq-02431 Furoscrobiculin D Sq-02435

[126794-78-3] [7260 1-34-4]

0~}:'
~ HO H CHpH
C 15H 220 4 M 266.336 C 15H 220 3 M 250.337
Constit. of Lactarius mitissimus. Cryst. Mp 57-58°. [cxJ14 Constit. of Lactarius scrobiculatus. Cryst. Mp 142-143°.
+ 16.0° (c, 0.7 in EtOH). [cx]n + 10.8° (CHC1 3).
Daniewski, W.M. et al, Phytochemistry, 1990, 29, 527 (isol, pmr, Battaglia, R. eta/, J. Nat. Prod. (Lloydia), 1980, 43, 319.
cmr)

3-Hydroxy-8-oxo-2(9),6-lactaradien-5,14- Sq-02436
Furosardonin A Sq-02432 olide
[74638-12-3]

oqp
[124208-79-3]
OH 0

~ OH
C 15H 200 2 M 232.322 C 15H 180 4 M 262.305
Constit. of Russula sardonia. Cryst. Mp 71-73°. [cx]i? Constit. of Lactarius scrobiculatus.
-14.7° (CHC1 3).
Bosetti, A. et al, Phytochemistry, 1989, 28, 1427.
Andina, D. et al, Phytochemistry, 1980, 19, 93 (isol, struct)
De Bernardi, M. et al, Tetrahedron, 1986, 42, 4277 (abs config)
Lactaral Sq-02437
Furoscrobiculin A Sq-02433 [54462-53-2]

o:(_p<
[74742-43-1] CHO

o-h
~~,
C 15H 200 2 M 232.322
\
\

Constit. of Lactarius vellereus and L. pergamenus. Oil. [cx]i:

C 15H 180 3 M 246.305 -7.6° (c, 1.1 in CHC1 3).
Constit. of Lactarius scrobiculatus. Oil. [cx]i? -23° (CHC1 3). Froberg, J. et al, Acta Chern. Scand., Ser. B, 1974, 28, 265 (synth)
Battaglia, R. eta/, J. Nat. Prod. (Lloydia), 1980, 43, 319. Magnusson, G. et al, Tetrahedron, 1974, 30, 1431 (isol)
Janis, S.P. et al, Tetrahedron Lett., 1982, 23, 5509 (synth)
De Bernardi, M. et al, Tetrahedron, 1986, 42, 4277 (abs conjig)
Furoscrobiculin B Sq-02434
[72601-37-7] Lactarolide A Sq-02438

00-Yv [71305-94-7]

\(V'
I OH
C 15H 200 2 M 232.322
Constit. of Lactarius scrobicu/atus. Oil. [cxln + 115°
(CHC1 3).
Battaglia, R. eta/, J. Nat. Prod. (Lloydia), 1980, 43, 319. C 15H 220 5 M 282.336
Constit. of Lactarius spp. Solid (CH 2Cl2/pentane). Mp
153-155°. [cx]i? +59.8° (Me 2CO).
3-Et ether: [71305-63-0].
C 17H 260 5 M 310.389
Constit. of L. spp. Solid (Et 20jpentane). Mp 171-173°.
[cx]i? + 18.SO (Me2CO).
14-Ketone, se-a/coho/: [71305-97-0]. Lactarolide B
C 15H 220 5 M 282.336
Constit. of L. spp. Solid (Me2CO/Et20). Mp 212-216°.
[cx]i? -3.SO (Me2CO).

589
Lactarorufin D - Pyrovellerolactone Sq-02439 - Sq-02443

14-Ketone, 5(',-a/coho/, 3-Et ether: [71305-64-1]. 8-Norlactaranelactone Sq-02441

C 17H 260 5 M 310.389 1,6, 7,8- Tetrahydro-5, 7, 7-trimethyl-3H -indeno[4,5-clfuran-3-
Constit. of L. spp. Solid (Me 2COjpentane). Mp 180- one, 9CI
1830. [~X]~ +2.1° (Me2CO). [124193-03-9]
14-Deoxy: [35008-20-9]. Lactarorujin A
CtsH 210 4 M 266.336
Consit. of L. rufus. Cryst. Mp 156-158°. [1X]~ +7°.
4-Deoxy, 12-hydroxy: [52483-05-3]. Lactarorujin B
C 15H 210 5 M 282.336
Constit. of L. rufus. Cryst. Mp 213°. [~X]~ +24°.
3,14-Dideoxy: 3-Deoxylactarorufin A
Ct5Hlz0 3 M 250.337 Ct4Ht60 2 M 216.279
Isol. from L. necator. Mp 116-122°. [1X]~ +70° (c, 1 in Constit. of Lactarius scrobiculatus. Cryst. Mp 93-96°.
CHC1 3). Bosetti, A. et at, Phytochemistry, 1989, 28, 1427.
Bogucka-Ledochowska, M. eta/, Tetrahedron Lett., 1976, 2267.
Krajewski, J.W. eta/, Cryst. Struct. Commun., 1977, 6, 779. Piperdial Sq-02442
Daniewski, W.M. eta/, Pol. J. Chern. (Rocz. Chern.), 1977, 51,

OHt:w
1395; 1987, 61, 123. [1 00288-36-6]
de Bernardi, M. eta/, Phytochemistry, 1979, 18, 293.
Bogucka-Ledochowska, M. eta/, Z. Kristallogr., Kristallogeom., OHC OH
Kristallphys., Kristallchem., 1979, 149, 57 (cryst struct,
Lactarorufin B)
Andina, D. eta/, Phytochemistry, 1980, 19, 93 (isol)
Christensen, J.R., Diss. Abstr. Int., B, 1983, 44, 800 (synth)

Lactarorufin D Sq-02439 C 15H 210 3 M 250.337

[94346-70-0] Constit. of Lactarius necator, L. torminosus, L. piperatus
and Russula queletii (prod. following injury). Pungent
HO

:d:);x
I
oil. [~X)i;l + 77° (c, 0.8 in Et20).
14-A/cohol: [100288-35-5]. Piperalol
C 15H 240 3 M 252.353
Constit. of L. necator, L. piperatus, L. torminosus and R.
queletii (prod. following injury). Pungent oil. [1X]i,3 + 57°
m) H (c, 4.3 in Et 20).
C 15H 210 4 M 266.336 5,14-Bisalcohol: [118918-26-6]. 8-Epipipertriol
Constit. of Lactarius necator. Needles (CHC1 3). Mp 160- Ct5H260 3 M 254.369
1620. [~X]~ +93° (c, 1.0 in CHC1 3). Constit. of L. necator. Cryst. Mp 108-114°. [~X]~ -36.6°
4-Epimer: [94286-87-0]. Lactarorujin E (c, 1 in CHC1 3). The name 8-epipertriol is a misnomer
C15H21 0 4 M 266.336 since it appears to have the same 8-config. as the other
Constit. of L. necator. Needles (CHC1 3). Mp 125-130°. natural products.
[~X]~ + 58° (c, 1.0 in CHC1 3). Sterner, 0. et al, Tetrahedron Lett., 1985, 26, 3163 (isol, struct)
Daniewski, W.M. eta/, Tetrahedron, 1984, 40, 2757 (cryst struct) Daniewski, W.M. et al, Phytochemistry, 1988, 27, 3315 (isol, deriv)
Daniewski, W.M. eta/, Pol. J. Chern. (Rocz. Chern.), 1987, 61, 123
(isol) PyroveUerolactone Sq-02443
[68582-98-9]
Lactaroscrobiculide B Sq-02440
[7260 1-38-8]

C 15H 200 2 M 232.322

Isol. from Lactarius pergamenus and L. helvus, also obt. by
pyrolysis of Vellerolactone, Sq-02446. Cryst.
(C6H 6/hexane). Mp 41-44°. [1X]i1 -73° ..
C 15H 200 3 M 248.321 (±)-form
Constit. of Lactarius scrobiculatus. Cryst. Mp 155-156°. Mp 72-74°.
[1X]~ +22.3° (MeOH).
Magnusson, G. et al, Acta Chern. Scand., Ser. B, 1973, 27, 1573,
Battaglia, R. et a/, J. Nat. Prod. (Lioydia), 1980, 43, 319. 2396 (isol, uv, pmr, cmr)
Jakupovic, J. et al, Phytochemistry, 1989, 28, 2741 (isol, pmr, cmr, Froborg, J. et al, J. Am. Chern. Soc., 1978, 100, 6728 (synth,
deriv) struct)

590
Sardonialactone A - Marasmic acid Sq-02444 - Sq-02449

Sardonialactone A Sq-02444

Marasmanes
[74638-11-2]

5,8-Dihydroxy-14-nor-7-marasmanone Sq-02447
5,8-Dihydroxy-13-nor-7-marasmanone
CtsHn04 M 266.336 [113540-62-8]
Constit. of Russula sardonia. Solid.
4-Ac: Cryst. Mp 200-201°.
Andina, D. et al, Phytochemistry, 1980, 19, 93.

Velleral Sq-02445
[50656-61-6]
C14H220 3 M 238.326
OHC H Constit. of Lactarius vellereus. Oil. [a]~ -83.3° (c, 0.3 in

OHC~
CHCI 3).
8-Ketone, 7P-alcohol: [113540-60-6]. 5,7-Dihydroxy-14-nor-
8-nuuasnumone. 5,7-Dihydroxy-13-nor-8-marasmanone
C 14H 220 3 M 238.326
C 15H 200 2 M 232.322 Constit. of L. vellereus. Cryst. Mp 88-91°. [a]~ -125.9°
Constit. of Lactarius vellereus and L. pergamenus. Cryst. (c, 1.6 in CHCI 3).
(hexane). Mp 86.5-87.SO. [a]~ -25° (c, 2.1 in CHCI 3). Daniewski, W.M. et al, Phytochemistry, 1988, 27, 187.
Magnusson, G. et a/, Tetrahedron, 1973, 29, 1621 (iso/, struct)
Froberg, J. eta/, J. Am. Chern. Soc., 1978, 100, 6728 (synth, lsovelleral Sq-02448
conjig)
[37841-91-1]

Vellerolactone Sq-02446 H
[68852-08-4] OHCM><

qY+J< C 15H 200 2

OHC'

M 232.322
•H
I

0~ Isol. from several Lactarius spp. Shows antibiot. props.

Mp 105-106°. [a]~ +293° (c, 2.0 in CHCI 3).
C 15H 200 2 M 232.322 I> Mutagenic.
Isol. from Lactarius vellereus, L. pergamenus and L. helvus. Magnusson, G. et a/, Tetrahedron Lett., 1972, 1105 (isol, struct,
Bright-yellow oil. [a]i; +364°. pmr)
(±)-form Kihlberg, J. et al, Tetrahedron Lett., 1983, 4631 (abs cotifig)
Mp 78-80°. Bergman, R. et al, J. Chern. Soc., Chern. Commun., 1990, 865
(synth)
Magnusson, G. et al, Acta Chern. Scand., Ser. B, 1973, 27, 1573, Thompson, S.K. eta/, J. Org. Chern., 1990, 55, 3004 (synth)
2396 (isol, uv, pmr, cmr)
Froborg, J. et al, J. Am. Chern. Soc., 1978, 100, 6728 (synth,
struct) Marasmic acid Sq-02449
[2212-99-9]
H

9
OH~C
HO- H
0
0
C 15H 180 4 M 262.305
Metab. of Marasmius conigenus and a basidiomycete
Flagelloscypha piletii. Cryst. Mp 173-174°. [aln + 182°
(c, 1.4 in CHCI 3).
I> OP8050000.
9-Hydroxy: [109883-99-0]. 9Jl-Hydroxynuuasmic acid. 5a-
Hydroxymarasmic acid
ctsH180 5 M 278.304
From a basidiomycete. Light yellow oil. [a]~ + 12.0° (c,
0.2 in Me 2CO).

591
Furodysin - Furodysinin hydroperoxide Sq-02450 - Sq-02452

Helrnlinger, D. eta/, Tetrahedron Lett., 1970, 349 (synth)

Cradwick, P.D. eta/, J. Chern. Soc., Chern. Commun., 1971, 431
(cryst struct)
Breckman, R.K. et al, J. Am. Chern. Soc., 1980, 102, 7146 (synth)
Greenlee, W.J. eta/, Tetrahedron, 1980, 36, 3367 (synth)
Furodysinin group
Boekman, R.K. eta/, J. Am. Chern. Soc., 1982, 104, 3216 (synth)
Heim, J. eta/, J. Antibiot., 1988, 41, 1752 (isol)
Anke, H. eta/, Z. Naturforsch., C, 1989, 44, I (deriv)
Furodysinin Sq-02451
[70546-63-3]

"CQJ
H

Furodysin group
C15H 200 M 216.322
Constit. of Dysidea spp. Cryst. (hexane). Mp 55°. [1X] 0
Furodysin Sq-02450 +64° (c, 0.5 in CHCI 3).
[70546-62-2] 81X-Hydroxy: [72236-79-4].
C1sH200z M 232.322
14 H lsol. from D. herbacea. Oil. [IX]~ -10° (c, 0.3 in CC14).

~
8P-Hydroxy: [81702-30-9].
C15H 200 2 M 232.322
Constit. of D. herbacea. Oil. [IX]~ -54.6° (c, 0.8 in
C15H 200 M 216.322 CC14).
Constit. of Dysidea spp. Cryst. (hexane). Mp 75°. [1X] 0 8P-Acetoxy: [81619-61-6].
+36° (c, 0.5 in CHCI 3). Ct,H120 3 M 274.359
8P-Acetoxy: Constit. of D. herbacea. Oil. [1X]i; -41° (c, 1 in CHC13).
Ct,H120 3 M 274.359 14-Hydroxy: [81619-62-7].
Constit. of D. herbacea. Oil. [1X]i; -32° (c, 0.2 in CC14). C15H 200 2 M 232.322
14-(Acetylmercapto): [70546-64-4]. Thiofurodysin acetate From D. herbacea. Oil. [IX]~ + 2° (c, 0.25 in CC14).
C17H120 2S M 290.426 14-Mercapto: [70913-80-3]. Thiofurodysinin
Constit. of a D. sp. Oil. C15H 200S M 248.388
[70913-81-4] From D. avara. Oil.
Kaslauskas, R. eta/, Tetrahedron Lett., 1978, 4951 (Furodysin,
14-(Acetylthio): Thiofurodysinin acetate
Thiofurodysin acetate) C17H 220 2S M 290.426
Dunlop, R.W. et a/, Aust. J. Chern., 1982, 35, 95 lsol. from a D. sp. Oil. [1X] 0 +49.3° (c, 12 in CHC13).
(Acetoxyfurodysin) !J.1•14-Isomer: [81619-64-9]. Isofurodysinin
CtsH 200 M 216.322
lsol. from D. herbacea. Oil. [IX]~ + 36.SO (c, 0.2 in
CHC14).
Kaslauskas, R. et al, Tetrahedron Lett., 1978, 4951 (isol, struct)
Dunlop, R.W. eta/, Aust. J. Chern., 1982, 35, 95 (derivs)
Capon, R.J. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 1136 (isol,
deriv)

Furodysinin hydroperoxide Sq-02452

[1 03202-15-9]

~OOH
C16H 240 4 M 280.363
Metab. of the nudibranch Chromodoris funerea. Cryst.
(Et20jhexane). Mp 142-143°. [1X] 0 -63.4° (c, 0.5 in
CHCI 3).
Faulkner, D.J. et a/, J. Org. Chern., 1986, 51, 3528 (isol, ir, pmr,
cmr, cryst struct)

592
Furodysinin lactone - Botrydienal Sq-02453 - Sq-02457

Furodysinin lactone Sq-02453

[89837-72-9]
t4 H 0H
Botrydial group
~0
Botryaloic acid Sq-02455
C 15H 200 3 M 248.321 [7 5207-65-7]
Constit. of Hypse/odoris zebra. Oil.
14-(Acety/thio): [122771-73-7]. 14-Acetyhhioxyfurodysinin OHC
loctone. 15-Acety/thioxyfurodysinin lactone
C 17H120 4S M 322.424
~COOH
Metab. of sponge Dysidea sp. Potent LTB4 receptor
partial agonist. Cryst. Mp 144-145°. [1X]n -178°
(CHC1 3). ~
Grode, S.H. eta/, J. Nat. Prod. (Lloydia), I984, 47, 76. C 15H 240 5 M 284.352
Carte, B. eta/, Tetrahedron Lett., I989, 30, 2725 (deriv) Metab. of Botrytis cinerea. Cryst. (Et 20)(as Me ester). Mp
115-117° (Me ester). [1X]n +67° (c, 0.43 in CHC13)(Me
OblongoUde Sq-02454 ester).
[97344-05-3] 4-Ac:
C 17H 260 6 M 326.389
Metab. of B. cinerea. Cryst. (Etp) (as Me ester). Mp
106-108° (Me ester). [1X]n +81° (c, 0.46 in CHC1 3)(Me
ester).
Bradshaw, A.P.W. eta/, J. Chern. Soc., Perkin Trans. I, I980, 741.

Botrydial Sq-02456
C 14H 200 2 M 220.311 [54986-75-3]
Prod. by Phomopsis ob/onga. Insect deterrent. Needles. Mp

~=r
105-106°. [1X]i? -190°.
Dihydro: [97344-00-8].
Rhombs. Mp 93-94°.
Begley, M.J. eta/, J. Chern. Soc., Perkin Trans. I, I985, 86I (isol,
struct) AcO H
Ciaydon, N. eta/, Phytochemistry, I985, 24, 937 (props)
Shing, T.K.M., J. Chern. Soc., Chern. Commun., I986, 49 (synth, C 17H 260 5 M 310.389
abs config) Metab. of Botrytis cinerea. Shows antibiotic activity.
Cryst. (pet. ether). Mp 108-110°. [1X]i? +34° (c, 1.4 in
CHC1 3).
Fehlhaber, H.-W. eta/, Chern. Ber., I974, 107, I720 (isol)
Hanson, J.R. eta/, J. Chern. Soc., Chern. Commun., I976, 72
(synth)
Bradshaw, A.P.W. eta/, J. Chern. Soc., Chern. Commun., I98I,
II69 (biosynth)

Botrydienal Sq-02457
2,3,5,6· Tetrahydro-1 ,3,3,6-tetramethyi-1H-indene-1 ,7-
dicarboxa/dehyde, 9CI
[97165-23-6]

C 15H 200 2 M 232.322

~
Metab. of Botryotinia squamosa. Phytotoxin. Needles. Mp
69-70°. [IX]~ + 190° (c, 0.18 in hexane).
2,3-Didehydro: [97165-24-7]. 2,3-Dihydro-1,3,3,6-
tetramethyi-JH-indene-1, 7-dicarboxa/dehyde, 9CI.
Dehydrobotrydienal
C,sH 180 2 M 230.306
Metab. of B. squamosa. Oil. [IX]~ -22° (c, 0.14 in
hexane).
Kimata, T. eta/, Tetrahedron Lett., I985, 26, 2097.

593
Botryoloic acid- 2-Hydroxy-11-spirovetiven-14-al Sq-02458 - Sq-02463

Botryoloic acid Sq-02458

[75207-64-6)

HOOC I
Spirovetivanes
~C~OH
(vetispiranes)
AcO H
C 17H 180 6 M 328.405
Metab. of Botrytis cinerea. Cryst. (MeOH aq.)(as Me Cyclodehydroisolubimin Sq-02461
ester). Mp 123-125° (Me ester). [exln + 34° (c, 0.24 in 4,10-Epoxy-11-spirovetiven-2-one
CHCI 3)(Me ester). [72055-93-7]
Bradshaw, A.P.W. et al, J. Chem. Soc., Perkin Trans. I, 1980, 741.

Dihydrobotrydial Sq-02459
[54433-86-2)

~
CtsH120 2 M 234.338
Constit. of potatoes infected with Phytophthora infestans.
Oil. [ex)~ -6.SO (c, 0.46 in CHCI 3).
Coxon, D.T. et al, J. Chem. Soc., Chem. Commun., 1979, 348.
AcO H
C17H 280 5 M 312.405 2,3-Dihydroxy-11-spirovetiven-14-al Sq-02462
Metab. of Botrytis cinerea. Cryst. (pet. ether). Mp 158- Oxylubimin. 4-Hydroxylubimin
1600. [ex)~ + 56° (c, 0.94 in pet. ether). [55784-90-2)
De-Ac: [97165-22-5]. Deacetyldihydrobotrydial
C 15Hu04 M 270.368
Metab. of B. squamosa. Prisms. Mp 163-165°. [ex)i:
+22.4° (c, 1.2 in MeOH).
10-Me ether: 0-Methyldihydrobotrydial
C 18H 34,05 M 326.432
Metab. of B. squamosa. Cryst. Mp 93°. [ex)i,O + 85° (c, 1
in MeOH). CtsH 240 3 M 252.353
10-Me ether, de-Ac, 15-oxo: Deacetyl-0- Stress metab. of Datura stramonium and of potatoes
methyldihydrobotrydialone infected with Phytophthora infestans. Cryst. Mp 96-98°
C16H 300 5 M 302.410 (85-86°). [ex)~ + 55° (c, 0.5 in EtOH).
Metab. of B. squamosa. Cryst. Mp 236-237°. [ex)i,O + 106° Birnbaum, G.I. et al, J. Chem. Soc., Chem. Commun., 1976, 330
(c, 0.49 in MeOH). (biosynth)
Fehlhaber, H.-W. et al, Chem. Ber., 1974, 107, 1720 (isol, struct) Matsunaga, A. et al, Bull. Chem. Soc. Jpn., 1977, 50, 1217 (struct)
Bradshaw, A.P.W. eta/, J. Chem. Soc., Perkin Trans. I, 1981, Birnbaum, G.l., Can. J. Chem., 1977, 55, 1619 (cryst struct)
1469; 1982, 2187 (biosynth) Stoessl, A. et at, Can. J. Chem., 1978, 56, 645 (biosynth)
Kimata, T. et a/, Tetrahedron Lett., 1985, 26, 2097 Murai, A. et al, Bull. Chem. Soc. Jpn., 1984, 57, 2286, 2291 (synth)
(Deacetyldihydrobotrydial) Iwata, C. et al, Tetrahedron Lett., 1985, 26, 3231 (synth)
Nakajima, H. et al, Agric. Bioi. Chem., 1986, 50, 2123 (isol, cryst.
struct) 2-Hydroxy-11-spirovetiven-14-al Sq-02463
Kimura, Y. et al, Agric. Bioi. Chem., 1988, 52, 1845 (isol, pmr, Lubimin
cmr)
[35951-50-9)
Norbotryal acetate Sq-02460
[64066-09-7)
HO,~CHO 10
3 ,

~
I
I

OAc CtsH 240 2 M 236.353

Stress product from Solanum tuberosum. Phytoalexin of
Ct6Hz..03 M 264.364 infected potato tubers. [ex]~ +39° (c, I in EtOH).
Metab. of Botrytis cinerea. Oil. Bp0 _5 84°. [ex)i,O + 102° (c,
10-Epimer: [64024-09-5). Epilubimin
0.2 in CHCI 3).
CtsH2402 M 236.353
Cuevas, 0. et al, Phytochemistry, 1977, 16, 1061. Isol. from infected potatoes.
10-Epimer, 3P-Hydroxy: [69350-60-3). 2,3-Dihydroxy-11-
spirovetiven-14-a/. Epioxylubimin
C 15H 240 3 M 252.353

594
14-Hydroxy-11-spirovetiven-2-one - 1,7(11),10(14)-Spirovetivatriene Sq-02464 - Sq-02468

!sol. from infected potatoes. Cryst. (diisopropy1 ether). 1(10),7(11)-Spirovetivadien-2-one Sq-02466

Mp 123-124°. [cx] 0 -12.1° (CHC1 3). fJ- Vetivone. P- Vetiverone
Hardwiger, L., Plant Physiol., 1971, 47, 346 (isol) [18444-79-6]
Birnbaum, G.l. et al, J. Chern. Soc., Chern. Commun., 1976, 330
(biosynth)
Birnbaum, G.l. et al, Can. J. Chern., 1977, 55, 1619 (cryst struct)
Katsui, N. et al, Bull. Chern. Soc. Jpn., 1977, 50, 1217 (struct)
Katsui, N. et al, Bull. Chern. Soc. Jpn., 1982, 55, 2424 (derivs) Absolute
Stoess1, A. et al, Can. J. Chern., 1983, 61, 1766 (biosynth)
Murai, A. et al, Bull. Chern. Soc. Jpn., 1984, 57, 2286, 2291 (synth) configuration
Coolbear, T. et al, Phytochemistry, 1985, 24, 1963 (biosynth)
C 15H 110 M 218.338
Constit. of vetiver oil. Solid. Mp 44-44.5°. Bp 2 141-142°.
14-Hydroxy-11-spirovetiven-2-one Sq-02464
[cx] 0 -38.9° (EtOH).
/solubimin
Semicarbazone: Cryst. (Py). Mp 228-229°. [cx] 0 -38.9°
[60077-68-1]
(AcOH).
Marshall, J.A. et al, J. Am. Chern. Soc., 1967, 89, 2750 (struct)
Biichi, G. eta/, J. Org. Chern., 1976, 41, 3208 (synth)
Dauben, W.G. et al, J. Am. Chern. Soc., 1977, 99, 7307 (synth)
Ibuka, T. eta/, Can. J. Chern., 1979, 57, 1579 (synth)
Murai, A. eta/, Tetrahedron Lett., 1981, 1033 (synth)
Posner, G.H. eta/, J. Org. Chern., 1988, 53, 6031 (synth, bib[)

CtsH240 1 M 236.353 1(10),11-Spirovetivadien-2-one Sq-02467

Possible precursor of 2-Hydroxy-11-spirovetiven-14-a1, Sq- Solavetivone
02463 in infected potatoes. Oil. [cx] 0 +34.4° (CHC1 3). [54878-25-0]
10-Epimer: Epiisolubimin

0~~
CtsH 24 0z M 236.353
lsol. from infected potatoes. Oil.
(92541-83-8)
Kalan, E.B. et al, Phytochemistry, 1976, 15, 775 (isol, struct)
Stoessl, A. et al, Can. J. Chern., 1978, 56, 645 (biosynth)
Katsui, N. et al, Bull. Chern. Soc. Jpn., 1982, 55, 2424 (isol, struct) : >--13
C 15H 210 M 218.338
1(10), 11-Spirovetivadiene Sq-02465 Stress metab. from tubers of Solanum tuberosum. Oil. [cx] 0
PreiiUUlspirodiene - 119° (EtOH).
[82189-85-3] 14-Hydroxy: [103573-06-4]. 14-Hydroxy-1(10),11-
spirovetivadien-2-one. Oxysolavetivone. 15-
Hydroxyso/avetivone
C 15H 21 0 1 M 234.338
Intermediate metabolite in the pathway to the
phytoa1exins of potato. Oil. [cx]if -91.6° (c, 1.00 in
EtOH).
13-Hydroxy: 13-Hydroxy-1(10),1 1-spirovetivadien-2-one.
CtsH24 M 204.355 Aglycone A3
Constit. of Premna latifolia and P. integrifolia. C 15H 110 1 M 234.338
14-Aldehyde: [82178-33-4]. 1(10),11-Spirovetivadien-14-a/. Constit. of flue-cured Virginia tobacco.
Premnaspiral Coxon, D.T. eta/, Tetrahedron Lett., 1974, 2921 (isol, struct)
C 15H 110 M 218.338 Anderson, R.C. eta/, J. Chern. Soc., Chern. Commun., 1977, 27
Constit. of P. latifolia. Oil. (isol, abs config)
14-Aidehyde, 2,4-dinitrophenylhydrazone: Cryst. Mp 160°. Yamada, K. et al, J. Chern. Soc., Chern. Commun., 1977, 554
(synth)
5-Epimer: [90760-94-4]. Agarospirene. Spirovetivene Murai, A. eta/, J. Chern. Soc., Chern. Commun., 1982, 32
CtsH 24 M 204.355 (biosynth)
From the liverwort Scapania robusta. Murai, A. eta/, Bull. Chern. Soc. Jpn., 1984, 57, 2276, 2282 (synth)
Bheemasankara, C. eta/, Indian J. Chern., Sect. B, 1982, 21, 267 Murai, A. eta/, Chern. Lett., 1986, 771 (derivs)
(isol) Iwata, C. et al, Chern. Pharm. Bull., 1987, 35, 544 (synth)
Wu, C.L. et al, CA, 1984, 101, 51670; 1985, 102, 3225
(Agarospirene) 1,7(11),10(14)-Spirovetivatriene Sq-02468
Rao, C.B. eta/, Indian J. Chern., Sect. B, 1985, 24, 403 (isol)
fJ- Vetispirene. P-Isovetivenene
[28908-27-2]

M 202.339

595
1(10),6,11-Spirovetivatriene - 11,12,13-Trisnor-1(10)-... Sq-02469 - Sq-02474

Constit. of vetiver oil. Oil. [aln -90°. 3,11,12-Trihydroxy-1(10)-spirovetiven-2- Sq-02472

Andersen, N.H. et al, Tetrahedron Lett., 1970, 1759 (isol, struct) one
Dauben, W.G. et al, J. Am. Chern. Soc., 1977, 99, 7307 (synth)
[84321-96-0l
lbuka, T. eta/, Can. J. Chern., 1979, 57, 1579 (synth)

1(10),6,11-Spirovetivatriene Sq-02469
«- J?etispirene
[28908-28-31
C15H 2P 4 M 268.352
Constit. of potato tubers infected with Phoma exigua.
Amorph. [ali; +88.7° (c, 0.15 in MeOH).
Malmberg, A.G., Phytochemistry, 1982, 21, 1818.

2,3,14-Trihydroxyvetispiranolide Sq-02473
C 15H 22 M 202.339
Constit. of vetiver oil. Oil. [aln + 220°.
Andersen, N.H. et a/, Tetrahedron Lett., 1970, 1759 (iso/, struct)
Dauben, W.G. eta/, J. Am. Chern. Soc., 1977, 99, 7307 (synth)
lbuka, T. eta/, Tetrahedron Lett., 1979, 159 (synth)
Yan, T.-H. eta/, Tetrahedron Lett., 1982, 23, 3227 (synth)
Balme, G., Tetrahedron Lett., 1985, 26, 2309 (synth)

C 15H 200 5 M 280.320

1(10),3,11-Spirovetivatrien-2-one Sq-02470
(2P,3« )-form
Anhydro-P-rotunol
14-Angeloyl: 14-Angeloyloxy-2P,3«-dihydroxylletispiranolide
[34206-82-11 C20 H 260 6 M 362.422
lsol. from Peyrousea umbellata. Gum.
Zdero, C. eta/, Phytochemistry, 1989, 28, 3101 (isol, pmr, cmr)

11,12,13-Trisnor-1(10)-spirovetivene-2,7- Sq-02474
dione
6,10-Dimethy/spiro[4.5]dec-6-ene-2,8-dione
C 15H 200 M 216.322

OYQ
Stress metab. from tubers of Solanum tuberosum. Cryst. [84413-75-21
Mp 44-44.SO. [aln + 57° (EtOH).
Coxon, D.T. eta/, Tetrahedron Lett., 1974, 2921 (iso/, struct)
Dauben, W.G. et al, J. Am. Chern. Soc., 1975, 97, 1622 (synth)
Marx, J.N. eta/, J. Org. Chern., 1987, 52, 336 (synth)

1(10)-Spirovetiven-11-ol Sq-02471 0
Hinesol C12H 160 2 M 192.257
[23811-08-71 Constit. of potato tubers infected with Phoma exigua.
Amorph. [ali; - UO (c, 0.14 in MeOH).
Malmberg, A.G., Phytochemistry, 1982, 21, 1818.

C15H:u,O M 222.370
Constit. of Atracty/odes lancea. Cryst. (MeOH). Mp 59-
600. [ali? -40.2°.
P-v-Fucopyranoside: [61368-06-7].
C21 H 360 5 M 368.512
Constit. of Carthamus oxyacantha. Cryst. (Et20). Mp
145-148°. [al~4 -35.SO (c, 3.5 in CHC1 3).
7,10-Diepimer: [1460-73-71. Agarospirol
Constit. of Agar wood oil. Bp0. 1 90-91°. [alii -5.7° (c,
28.7 in CHC1 3).
Varma, K.R. eta/, Tetrahedron, 1965, 21, 115 (isol)
Marshall, J.A. eta/, J. Org. Chern., 1970, 35, 4068 (struct, synth)
Rustraiyan, A. et a/, Chern. Ber., 1976, 109, 3953 (isol)
Biichi, G. eta/, J. Org. Chern., 1976, 41, 3208 (synth)
Dauben, W.G. eta/, J. Am. Chern. Soc., 1977, 99, 7307 (synth)
lbuka, T. eta/, Can. J. Chern., 1979, 57, 1579 (synth)
Ibuta, T. et a/, Tetrahedron Lett., 1979, 159 (synth)
Lafontaine, J. et al, Can. J. Chern., 1980, 58, 2400 (synth)
Iwata, C. eta/, Chern. Pharm. Bull., 1982, 30, 2738 (synth)
Murai, A. eta/, Bull. Chern. Soc. Jpn., 1984, 57, 2276 (synth)

596
3,5-Acoradiene - 4(15),5-Acoradiene Sq-02475 - Sq-02481

3,11-Acoradiene Sq-02478
Jl-Acortuliene
Acoranes [28477-64-1]

3,5-Acoradiene Sq-02475
1,8-Dimethy/-4-(1-methylethyl)spiro[4.5]deca-6,8-diene, 9CI.
1-/sopropyl-4,8-dimethylspiro[4.5]deca-4,8-diene. C15H24 M 204.355
Acortulilu!lle. 6,8-Acoradiene Constit. of Juniperus rigida. Oil. [1X]n +23°.
[899 55-08-8] Tomita, B. et a/, Tetrahedron Lett., 1970, 1371 (isol)
Marx, J.N. eta/, J. Org. Chern., 1975, 40, 1602 (synth)
Oppolzer, W. et al, Helv. Chim. Acta, 1977, 60, 2388 (synth)

4,7(11)-Acoradiene Sq-02479
.,..Acortuliene. IX-Aiaskene
(28400-12-6]
C 15H 24 M 204.355
Constit. of Calea prunifolia and Angelica sinensis. Oil. [IX]~
+ 76° (c, 0.13 in CHCI 3).
[67304-11-4]
Pesaro, M. et al, J. Chern. Soc., Chern. Commun., 1978, 203 (synth)
Baldwin, S.W. et al, Tetrahedron Lett., 1982, 23, 1235 (synth)
Chen, Y. et a/, CA, 1984, 100, 188755 (isol) C15H24 M 204.355
Castro, V. et al, J. Nat. Prod. (Uoydia), 1984, 47, 802 (isol) Constit. of Chamaecyparis nootkatensis. Oil.
Andersen, N.H. eta/, -Phytochemistry, 1970, 9, 1325 (isol)
3,7(11)-Acoradiene Sq-02476 Andersen, N.H. et al, Tetrahedron Lett., 1972, 899 (struct)
Marx, J.N. et al, J. Org. Chern., 1975, 40, 1602 (synth)

(+)-form
Absolute 4,11-Acoradiene Sq-02480
configuration rx.-Acortuliene
[24048-44-0]

_fQ
C15H24 M 204.355
(+)-form [28400-13-7] ~Acortuliene
Constit. of Juniperus rigida. Oil. [1X]n + 15.SO.
(-)-form [28908-21-6] Jl-Aiaskene
Constit. of Chamaecyparis nootkatensis. Oil.
Andersen, N.H. eta/, Phytochemistry, 1970, 9, 1325 (isol) C15H24 M 204.355
Tomita, B. eta/, Tetrahedron Lett., 1970, 1371 (isol) Constit. of Juniperus rigida. Oil. [1X]n -20°.
Andersen, N.H. et al, Tetrahedron Lett., 1972, 899 (struct) Tomita, B. et al, Tetrahedron Lett., 1970, 143 (isol)
Marx, J.N. et al, J. Org. Chern., 1975, 40, 1602 (synth) Oppolzer, W. et al, Helv. Chim. Acta, 1983, 66, 522 (synth)
So1as, D. et a/, J. Org. Chern., 1983, 48, 670 (synth)
3,10(14)-Acoradiene Sq-02477 Yamamoto, Y. eta/, J. Org. Chern., 1990, 55, 3971 (synth)
8-Methy/-1-methylene-4-( J-methylethyl)spiro[4.5]dec-7-ene,
9CI. J-Isopropyl-8-methyl-4-methylenespiro[4.5]dec-7-ene. 4(15),5-Acoradiene Sq-02481
4( 14),8-Acoradiene 6,8(15)-Acoradiene
[94131-46-1] (94131-45-0]

ClsH 24 M 204.355 CI5H24 M 204.355

Constit. of Calea prunifolia. Oil. [IX]~ +47° (c, 0.8 in Isol. from Ca/ea prunifolia. Oil.
CHCI 3). Castro, V. eta/, J. Nat. Prod. (Uoydia), 1984, 47, 802.
Castro, V. et a/, J. Nat. Prod. (Uoydia), 1984, 47, 802.

597
4(15),5-Acoradien-3-ol - 4-Acoren-3-one Sq-02482 - Sq-02488

4(15),5-Acoradien-3-ol Sq-02482 3-Acoren-11-ol Sq-02486

8(1 5),9-Acoradien-7-o/. Slri:;ukfUICoradienol fl-Acorenol
[90332-94-8] [28400-11-5]

~ OH
Ht
5h
C 15H:11;0 M 222.370
CtsH240 M 220.354 Constit. of Juniperus rigida. Oil. [ex]n + 0°.
Constit. of Chloranthus japonicus. Cryst. (hexane). Mp
128.5-130°. [ex]~ -203° (c, 0.66 in CHC1 3). Tomita, B. et al, Tetrahedron Lett., 1970, 1371 (iso[)
Guest, I.G. et al, J. Chem. Soc., Chem. Commun., 1973, 526
Kawabata, J. eta/, Agric. Bioi. Chem., 1984, 48, 713. (synth)
Oppolzer, W. et al, Helv. Chim. Acta, 1977, 60, 2388 (synth)
2,9-Acoranedione Sq-02483 Iwata, C. et al, Chem. Pharm. Bull., 1985, 33, 1961 (synth)
Acorone
[10121-28-5] 4-Acoren-11-ol Sq-02487

l=b
11.-Acorenol
[28296-85-7]

C 15H 240 2 M 236.353

0

Constit. of Acorus calamus. Cryst. (heptane). Mp 100°. C 15Hu;0 M 222.370

5b
H6'
[ex]:i + 139.5° (EtOH). Constit. of Juniperus rigida. Oil. [ex]n -36.1°.
McEachan, C.E. eta/, J. Chem. Soc. C, 1966, 579 (cryst struct) Tomita, B. et al, Tetrahedron Lett., 1970, 1371 (iso[)
Andersen, N.H. et al, Tetrahedron Lett., 1972, 899 (abs co'!fig) Guest, I.G. et al, J. Chem. Soc., Chem. Commun., 1973, 526
Marx, J.N. et al, J. Org. Chem., 1975, 40, 1602 (synth) (synth)
McCrae, D.A. et al, J. Org. Chem., 1977, 42, 1607 (synth) Lansburg, P.T. et al, J. Am. Chem. Soc., 1974, 96, 896 (synth)
Ackroyd, J. eta/, Helv. Chim. Acta, 1985, 68, 338 (synth)
Rao, G.S.R.S. et al, Indian J. Chem., Sect. B, 1986, 25, 783 (synth)
4-Acoren-3-one Sq-02488
A.corenone
3,9,11-Acoratriene Sq-02484 [5956-05-8]
Acoratriene
I
[38227-38-2]
~
~
A~
~\~
;--....
C15H 240 M 220.354
C 15H 22 M 202.339 Constit. of Acorus calamus and also Libanotis
Synthetic acorane sesquiterpene. Oil. transcaucasica and Daucus carota. Oil. Bp0 . 1 61°. [ex]~
Marshall, J.A. eta/, Fortschr. Chem. Org. Naturst., 1974, 31, 283 -22.3°. n~ 1.5039.
(rev) 1-Epimer: [21653-33-8]. 3-Acoren-4-one. A.corenone B
Kato, T. et al, J. Chem. Soc., Chem. Commun., 1984, 1077 (synth) CtsH240 M 220.354
Constit. of Bothrioch/oa intermedia. Oil.
4-Acorene-2,8-dione Sq-02485 McClure, R.J. et al, J. Chern. Soc., Chem. Commun., 1968, 1135
A.coronene (cryst struct)
[33983-45-8] Trost, B.M. et al, J. Am. Chem. Soc., 1975, 97, 5873 (synth)
Oppolzer, W. eta/, Helv. Chim. Acta, 1977, 60, 2388 (synth)
Rascher, W. eta/, Tetrahedron, 1977, 33, 575 (synth)
Lange, G.L. eta/, Tetrahedron Lett., 1977, 4479 (synth)
Naegeli, P., Tetrahedron Lett., 1978, 2127 (synth)
White, J.D. eta/, J. Am. Chem. Soc., 1981, 103, 1813 (synth)
Baldwin, S.W. eta/, Tetrahedron Lett., 1982, 23, 1235 (synth)
Iwata, C. eta/, J. Chem. Soc., Chem. Commun., 1984, 781 (synth)
Nagumo, S. et al, J. Chem. Soc., Chem. Commun., 1990, 1778
C 15H 220 2 M 234.338 (synth)
Constit. of Acorus calamus. Cryst. (hexane). Mp 69°. [ex]n
+66.8° (c, 1 in dioxan).
Minato, H. eta/, Chem. Pharm. Bull., 1971, 19, 638.

598
Acoric acid- 15-Bromo-1,3(15),7-chamigratrien-9-... Sq-02489 - Sq-02493

Acoric acid Sq-02489

Chamigranes
[5956-06-9]
COOH

C 15H 240 4
~~
M 268.352
Constit. of Acorus calamus. Cryst. (Etpjpet. ether). Mp
10-Bromo-2,7-chamigradiene
10-Bromo-IX-chamigrene
[57473-87-7]
Sq-02491

166-168°. [IX]~ +27° (c, 1 in CHC1 3).

Birch, A.J. et al, J. Chern. Soc., 1964, 2923 (isol)
Birch, A.J. et al, J. Chern. Soc., Perkin Trans. I, 1972, 1186 (synth)
Rao, G.S.R.S. et a/, Indian J. Chern., Sect. B, 1981, 20, 1089
(synth)

15-Nor-2-acoren-4-one Sq-02490 CtsH 23Br M 283.251

1-Methyl-4-(J-methylethyl)spiro[4.5]dec-6-en-8-one, 9C/. 1- Metab. of Laurencia pacifica and L. glandulifera. Oil. [1X]n
Isopropyl-4-methylspiro[4.5]dec-6-en-8-one. 8-Desmethyl-6- -71.1° (c, 0.18 in CHC1 3), [1X]n -81° (c, 0.92 in CHC1 3).
acoren-8-one. 15-~or-6-acoren-8-one Howard, B.M. eta/, Tetrahedron Lett., 1976, 2519.
[82570-36-3]

_(00
10-Bromo-1,3,7(14)-chamigratrien-9-ol Sq-02492
2-Bromo-1 ,1 ,9-trimethylspiro[5.5]undeca-7,9-dien-3-ol, 9Cl.
Obtusadiene
[113262-62-7]
Br
C 14H 120 M 206.327 I

Constit. of Calea prunifolia. Oil. [1X]~4 +3° (c, 1 in CHC13).

Castro, V. et al, J. Nat. Prod. (Lloydia), 1984, 47, 802. H0,~
0 .
·~

I .J 15

CtsH21 Br0 M 297.234

Constit. of the red alga Laurencia obtusa. Oil. [IX]~ -52.0°
(c, 2.8 in CHC1 3).
!:>.3· 15 -/somer: [113235-90-8]. 10-Bromo-1,3(15),7(14)-
chamigradrien-9-ol. /soobtusadiene
CtsH 21 BrO M 297.234
Constit. of L. obtusa. Oil. [IX]~ -11.7° (c, 0.7 in CHCI 3).
1,2-Dihydro,10-epimer: 10-Bromo-2,7(11)-chamigradien-9-ol
CtsH 23 BrO M 299.250
Metab. of L. nipponica. Oil. [1X]n -58.9° (c, 0.4 in
CHCI 3).
Gerwick, W.H. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 1131.
Wright, A.D. et al, J. Nat. Prod. (Lloydia), 1990, 53, 845.

15-Bromo-1,3(15),7-chamigratrien-9-one Sq-02493
[71565-19-0]

0~
Br
C 15H 19Br0 M 295.218
Constit. of Laurencia majuscula.
Suzuki, M. eta/, Tetrahedron Lett., 1979, 879.

599
10-Bromo-3-chamigrene-1,9-diol - 10-Bromo-2-chloro-7-chamigren-3-ol Sq-02494 - Sq-02499

10-Bromo-3-chamigrene-1,9-diol Sq-02494 2-Bromo-3-chloro-7(14),8-chamigradien-5- Sq-02497

2-Bromo-3,11-dihydroxy-P-chamigrene ol
Nidifidienol
Br
I [55890-19-2]
HO,~

CtsH13Br0 2 M 315.249
HO

l-Ac: [126005-79-6]. 1-Acetoxy-10-bromo-3-chamigren-9-ol.

11-Acetoxy-2-bromo-3-hydroxy-P-chamigrene
C17H 25 Br03 M 357.287
C 15HzzBrC10
~
M 333.695
Br

Constit. of Laurencia nidifica. Oil.

Constit. of Laurencia obtusa. Oil. [1X]i; + 49° (c, 0.13 in Waraszkiewicz, S.M. et al, Tetrahedron Lett., 1975, 281.
CHC1 3).
Di-Ac: [126005-80-9]. 1,9-Diacetoxy-10-bromo-3- 10-Bromo-4-chloro-3,7(14)-chamigradien- Sq-02498
chamigrene. 3,11-Diacetoxy-2-bromo-P-chamigrene
C19H 27 Br04 M 399.324 9-ol
Metab. of L. obtusa. Oil. [1X]i; +93° (c, 0.36 in CHC1 3). Elatol
Martin, J.D. et a/, Phytochemistry, !989, 28, 3365 (isol, pmr, cmr)
[55303-97-4]
Br
I
10-Bromo-7-chamigren-2-one Sq-02495
4-Bromo-IX-chamigren-8-one HO,w
~ Cl
I I
C15HzzBrCIO M 333.695
Constit. of Laurencia elata. Oil. [1X]n + 83.SO (c, 0.365 in
MeOH).
Ac: Cryst. (hexane). Mp 157-158°.
Debromo: [61661-37-8]. 4-Chloro-3,7(14)-chamigradien-9-ol
C15H 13Br0 M 299.250 C15H 13Cl0 M 254.799
Constit. of Laurencia glandulifera. Cryst.(MeOH). Mp 78- Constit. of L. obtusa. Oil. [1X]n +98°.
790. [1X]n -88° (c, 2.46 in CHC1 3).
Sims, J.J. eta/, Tetrahedron Lett., 1974, 3487 (cryst struct, abs
1:!,_10 4>-Jsomer: [53767-98-9]. 10-Bromo-7(U)-chamigren-2- config)
one. 4-Bromo-P-chamigren-8-one Gonzalez, A.G. et al, Tetrahedron Lett., 1976, 3051 (isol)
CMIHlJBrO M 299.250
Constit. of the essential oil of L. glandulifera. Mp 116- 10-Bromo-2-chloro-7-chamigren-3-ol Sq-02499
1170. [1X]n -57°. Glanduliferol
Suzuki, M. eta/, Tetrahedron Lett., 1974, 821 (isol)
[54278-86-3]
Suzuki, M. et al, Tetrahedron, 1979, 35, 823 (abs config)

~OH
2-Bromo-3-chloro-7(14),9-chamigradiene Sq-02496
Nidifidiene
[54928-02-8]

~ Cl

l~l
C15H 24 BrC10 M 335.711
Constit. of Laurencia glandulifera. Gum. [1X]n -21.7° (c,
Br 1.7 in CHC1 3).
Suzuki, M. et al, Tetrahedron Lett., 1974, 1807 (isol)
C15H 22 BrCI M 317.695 Suzuki, M. et al, Tetrahedron, 1979, 35, 823 (abs config)
Constit. of Laurencia nidifica. Cryst.
Waraszkiewicz, S.M. eta/, Tetrahedron Lett., 1974, 2003.

600
10-Bromo-2-chloro-7(14)-chamigren-3-... - 10-Bromo-7,8-epoxy-2,9-... Sq-02500 - Sq-02507

10-Bromo-2-chloro-7(14)-chamigren-3-ol Sq-02500 2-Bromo-3-chloro-5-hydroxy-7(14),9- Sq-02504

Hurgadol chamigradien-8-one

C 1 ~H 24 BrCIO
~OH
M 335.711
Cl
C 1 ~H 20 BrCI0 2
0~
M 347.678
Br

Ac: 5-Acetoxy-3-chloro-7(14),9-chamigradien-8-one. 11-

Metab. of Laurencia obtusa. Cryst. Mp 121°. [1X]n -1.7° (c, Acetoxy-8-bromo-9-chloro-5,5,9-trimethyl-1-
0.71 in CHCI 3). methylidenespiro(5.5]undec-3-en-2-one
Ayyad, S.-E.N. eta/, Phytochemistry, 1990, 29, 3193 (iso/, cryst C17H 22 BrCI03 M 389.716
struct) From A. dactylomela. Cryst. Mp 105-106°. (1X]i,<' -27.8°
(c, 0.54 in CHCI 3).
2-Bromo-3-chloro-7-chamigren-9-one Sq-02501 Sakai, R. eta/, Helv. Chim. Acta, 1986, 69, 91.
Laurencenone D
[116384-28-2] 10-Bromo-5,1 0:2,7-diepoxy-3(15)- Sq-02505
chamigrene

0~
C 1 ~H 21 BrC10 M 333.695
Metab. of Laurencia obtusa. Solid.
Br ¢& b---
cl~H21Br02 M 313.234
Kennedy, D.J. eta/, Phytochemistry, 1988, 27, 1761. Constit. of Laurencia nipponica. Cryst. Mp 78-79°. [1X]i;'
-54.8°.
3-Bromo-2-chloro-7-chamigren-9-one Sq-02502 Kikuchi, H. eta/, Bull. Chern. Soc. Jpn., 1985, 58, 2437.
Laurencenone A
[73465-61-9] 10-Bromo-5,10-epoxy-3,8-chamigradiene- Sq-02506
2,7-diol

0~.,
4-Bromo-4,7-epoxy-1,5,5,9-tetramethylspiro[5.5]undeca-2,8-
diene-1 ,10-diol

C 1 ~H 21 BrCIO M 333.695
6
hr
H~
Metab. of Laurencia obtusa. Oil.
Kennedy, D.J. et a/, Phytochemistry, 1988, 27, 1761.

em
I

2-Bromo-3-chloro-5,10-epoxy-7(14)- Sq-02503
chamigrene C 1 ~H 21 Br0 3 M 329.233
Nidifocene Constit. of Laurencia nipponica. Cryst. (Me2COjisopropyl
[60545-17-7] ether). Mp 73-75°. (1X]n - 11.7°.
Kurata, K. eta/, Chern. Lett., 1981, 773.

~
10-Bromo-7,8-epoxy-2,9-chamigradiene- Sq-02507
5,15-diol
(8651 0- 25-0)

Br
C 1 ~H 22 BrCIO M 333.695
Constit. of Laurencia nidi.fica. Cryst. (hexane). Mp 79-81°.
Waraszkiewicz, S.M. eta/, Tetrahedron Lett., 1977, 2311 (isol,
cryst struct)

601
10-Bromo-2,3-epoxy-7-chamigrene - 4-Chloro-3,7-epoxy-9-chamigranone Sq-02508 - Sq-02514

C 15H:zoBr20 2 M 392.130 Constit. of Chamaecyparis taiwanensis. Oil. Bp 13 110-113°.

Isol. from L. majuscula. Cryst. (CH 2C12 jhexane). Mp [ex]~ -52.7° (CHC1 3).
124-125°. [ex]~ +51.7° (c, 1.1 in EtOH). Ito, S. eta/, J. Chem. Soc., Chem. Commun., 1967, 186 (struct)
Kurata, K. et a/, Chem. Lett., 1983, 561 (cryst struct) Tanaka, A. eta/, J. Chem. Soc., Chem. Commun., 1967, 188
Caccamese, S. eta/, Tetrahedron, 1987, 43, 5893 (cryst struct, (synth)
deriv) Ireland, R.E. eta/, J. Org. Chem., 1984, 49, 1001 (synth)
Martin, J.D. et al, Pure Appl. Chem., 1986, 58, 395 (synth)
10-Bromo-2,3-epoxy-7-chamigrene Sq-02508
4-Bromo-8,9-epoxy-ex-chamigrene 2,7-Chamigradiene Sq-02512
[53767-99-0] «-Chamigrene
[19912-83-5]

C15H 24 M 204.355
Constit. of Schisandra chinensis. Oil. [exJn -30° (c 0.36 in
C15H23BrO M 299.250 CHC1 3).
Constit. of Laurencia glandulifera. Cryst. (MeOH). Mp 53-
540. [exJn -92° (c, 0.98 in CHC13). Ohta, Y. eta/, Tetrahedron Lett., 1968, 2483 (struct)
Kato, T. et a/, Tetrahedron, 1970, 26, 4287 (synth)
Suzuki, M. et a/, Tetrahedron Lett., 1974, 821 (isol) Fniter, G., Helv. Chim. Acta, 1977, 60, 515 (synth)
Suzuki, M. et a/, Tetrahedron, 1979, 35, 823 (cryst struct, abs Suzuki, M. eta/, Tetrahedron, 1979, 35, 823 (abs conjig)
conjig)

4-Chloro-3,7-chamigradien-9-one Sq-02513
9-(Bromomethylene)-1,2,5- Sq-02509 Laurencenone B
trimethylspiro(S.S]undeca-1,7-dien-3-one [I 08925-15-11
[101686-86-6)

Ct5Ht9Br0
ift'"'
M 295.218 Ct5H21 C10 M 252.783
(E)-form Metab. of Laurencia obtusa. Oil.
Constit. of Aplysia dactylomela. Oil. Dechloro: [61661-47-0]. 3,7-Chamigradien-9-one. 1,5,5,9-
(Z)-form Tetramethylspiro[5.5]undeca-l ,8-dien-3-one, 9CI.
From A. dactylomela. Cryst. Mp 97-99.5°. [ex]~ +33.SO Laurencenone C. ent-9-0xo-ex-chamigrene
(c, 0.074 in CHC1 3). C15H220 M 218.338
Sakai, R. et a/, Helv. Chim. Acta, 1986, 69, 91. Metab. of L. obtusa and Marchantia polymorpha. Oil.
[exJn -43° (c, 1 in CHC1 3).
[61661-46-9, 116907-14-3]
2,7(14)-Chamigradien-15-al Sq-02510
Cluunigrenal Gonzalez, A.G. eta/, Tetrahedron Lett., 1976, 3051.
Kennedy, D.J. et al, Phytochemistry, 1988, 27, 1761.
[19912-84-6] Asakawa, Y. eta/, Phytochemistry, 1990, 29, 1577.

c;oCHO
4-Chloro-3,7-epoxy-9-chamigranone Sq-02514
[108906-79-2]

C15H220 M 218.338
Constit. of Schisandra chinensis. [ex]n -80.5° (c, 0.6 in
o~,a
CHC1 3).
Ohta, Y. eta/, Tetrahedron Lett., 1968, 2483.
~', ,
'd
2,7(14)-Chamigradiene Sq-02511 Ct5H23C10 2 M 270.798
~Ciuunigrene Constit. of Laurencia obtusa. Oil.
[18431-82-8] Brennan, M.R. eta/, Phytochemistry, 1987, 26, 1053.

M 204.355

602
2-Chloro-3-hydroxy-7-chamigren-9-... - 2,10-Dibromo-3-chloro-5,7-... Sq-02515 - Sq-02520

2-Chloro-3-hydroxy-7-chamigren-9-one Sq-02515 2,10-Dibromo-7-chamigren-3-ol Sq-02518

[108925-14-0] 2,10-Dibromo-3-hydroxy-a-chamigrene
[89203-65-6]

C 15H 23Cl01

CHC1 3).
M 270.798
Constit. of Laurencia obtusa. Oil. [a]i; -46° (c, 0.22 in

C 15H 14Br10
~OH
M 380.162
Br
Brennan, M.R. eta/, Phytochemistry, 1987, 26, 1053.
Constit. of Laurencia nipponica. Oil. [a]~ -27° (c, 2.13 in
9,15-Dibromo-1,3(15)-chamigradien-7-ol Sq-02516 CHCI 3).
3-Bromo-9-bromomethy/ene-1,5,5-trimethylspiro[5.5]undec-7- Suzuki, M. eta/, Bull. Chem. Soc. Jpn., 1983, 56, 3824.
en-J-ol
2,10-Dibromo-3-chloro-7(14),9- Sq-02519

Br~ ' / """' (E)-form

chamigradien-8-ol

HO ' "'--
Br
C 15H 11Br10 M 378.146
(E)-form [86161-35-5]
Constit. of the digestive gland of the sea hare Aplysia
dacty/omela. Cryst. Mp 84-86°. [aln -64° (c, 0.29 in C 15H 11 Br1CIO M 412.591
CHCI 3). Constit. of Laurencia nipponica. Oil. [ali? -24.2° (c, 1.88
(Z)-form [86105-62-6] inCHC1 3).
From A. dactylomela. Oil. 8-Ketone: [98752-13-7]. 2,10-Dibromo-3-chloro-7(11),9-
cha~gradJen-8-one
Gonzalez, A.G. eta/, Tetrahedron Lett., 1983, 24, 847 (isol, cryst
struct, abs config) C 15H 19Br1CIO M 410.575
From L. nipponica. Pale-yellow oil. [a]i,l + 1.95° (c, 1.59
in CHCI 3).
10,15-Dibromo-1,3(15),7(14)- Sq-02517
8-Ketone,JO-debromo: [102043-63-0]. 2-Bromo-3-ch/oro-
chamigratnen-9-ol 7(11),9-c~gradJen-8-one
[70449-76-2] C 15H 10BrCIO M 331.679
Constit. of Ap/ysia dactylomela. Cryst. Mp 98-100°. [aln
Br
I + 19.6° (c, 0.64 in CHCI3).
H0,~
10
6
(3(J5)Z,6R,9R,JOS)-form
Suzuki, M. et a/, Bull. Chem. Soc. Jpn., 1985, 58, 2435.
Sakai, R. eta/, Helv. Chim. Acta, 1986, 69, 91.

I 3 ,._ 2,10-Dibromo-3-chloro-5,7-chamigranediol Sq-02520

[54462-54-3]
Br
C 15H 10Br10 M 376.130 Br
(3(15)Z,6R,9R,10S)-form [73651-01-1]
lsol. from Laurencia majuscu/a. Oil. [aln -4°.
(3{15)Z,6S,9S10R)-form [71565-17-8]
Isol. from L. majuscula. Oil. [aln + 2. 7° (c, 0.002 in
CHCI 3).
(3( 15)E,6S,9S,1 OR)-form
Br
Constit. of L. majuscu/a. Oil. [aln -40.0° (c, 0.01 in
CHCI 3). C 15H 15Br1Cl01 M 432.622
Suzuki, M. et al, Tetrahedron Lett., 1979, 879 (cryst struct, abs 5-Ac: 5-Acetoxy-2 ,I0-dibromo-3-ch/oro-7-chamigranol.
config) Acetoxyintricatol
Suzuki, M. et at, CA, 1980, 92, 215566z. C 17H 17Br1Cl03 M 474.659
Coli, J.C. eta/, Aust. J. Chem., 1989, 42, 1591 (isol, pmr, cmr) Constit. of Laurencia intricata. Cryst.(CC14 jhexane).
McMillan, J.A. eta/, Tetrahedron Lett., 1974, 2039.

603
2,10-Dibromo-3-chloro-7-chamigrene - 3,10-Dibromo-4-chloro-7(14)-... Sq-02521 - Sq-02526

2,10-Dibromo-3-chloro-7-chamigrene Sq-02521 2,10-Dibromo-3-chloro-7(14)-chamigren-9- Sq-02524

[57685-65-l] ol
[124649-22-5]

C 15H 13Br1Cl M 398.607 C15H13Br1C10 M 414.607

Constit. of Laurencia g/andulifera. Oil. [exln -14° (c, 1.45 Metab. of Laurencia majuscula. Oil. [exln -3.6° (c, 0.04 in
in CHC1 3). CHC1 3).
!J.10 4>-Jsomer: [54928-01-7]. 2,10-Dibromo-3-ch/oro-7(14)- Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1591 (iso/, pmr, cmr)
chamigrene. Nidificene
C15H 13Br1C1 M 398.607 3,10-Dibromo-2-chloro-7(14)-chamigren-9- Sq-02525
Constit. of L. nipponica and L. nidifica. Cryst. (hexane).
Mp 76-77°. [ex]); +30.6° (c, 1.4 in CHC1 3). ol
Obtusol
!J.10 4>-Jsomer, 8ex-Hydroxy: [89299-70-7]. 2,10-Dibromo-3-
chloro-7(14)-chamigren-8-ol. 2,10-Dibromo-3-ch/oro-8- [73494-22-1]
hydroxy-P-chamigrene

HO~:r
C 15H13 Br1Cl0 M 414.607
From L. nipponica. Oil. [ex]:;' + 3.33° (c, 1.2 in CHC1 3).
[88586-20-3)
Waraszkiewicz, S.M. et a/, Tetrahedron Lett., 1974, 2003
(Nidi.ficine) I ,
Suzuki, M. et a/, Tetrahedron, 1979, 35, 823 (abs config) Br
Suzuki, M. eta/, Bull. Chern. Soc. Jpn., 1983, 56, 3824. Cl
C15H 13Br1C10 M 414.607
3,10-Dibromo-2-chloro-7(14)-chamigrene Sq-02522 Constit. of Laurencia obtusa. Cryst. Mp 145-146°. [exln
Obtusane + 100.
[73436-46-1] 10-Debromo: [73465-57-3]. 3-Bromo-2-chloro-7(14)-
chamigren-9-ol
C15H 14BrC10 M 335.711

~
Constit. of L. obtusa. Mp 81-82° (as acetate). [ex]n + 11°
(acetate).
7S,14-Epoxide: 3,1 0-Dibromo-2-ch/oro-7,14-epoxy-9-

IY;r Cl
chamigrano/. Obtusol epoxide
C15H 13BrC101

(c, 1.69 in CHC1 3).

M 350.702
Isol. from L. obtusa. Needles. Mp 103-105°. [ex]i; +5.9°
C 15H 13Br1C1 M 398.607 Gonzalez, A.G. eta/, Tetrahedron Lett., 1976, 3051; 1979, 2717
Constit. of Laurencia obtusa. Cryst. Mp 174-175°. [exln (cryst struct, isol)
+38°. Martin, J.D. eta/, Phytochemistry, 1989, 28, 3365 (epoxide)
Gonzalez, A.G. eta/, Tetrahedron Lett., 1979, 2719.
3,10-Dibromo-4-chloro-7(14)-chamigren-9- Sq-02526
2,10-Dibromo-3-chloro-7 -chamigren-9-ol Sq-02523 ol
lsoobtusol
[73494-23-2]

C 15H 13Br1Cl0 M 414.607

Metab. of Laurencia nipponica. Cryst. (diisopropy1 ether). C15H13Br1Cl0 M 414.607
Mp 119-120°. [ex]~ +25.3° (c, 1.39 in CHC1 3). Constit. of Laurencia obtusa. Cryst. Mp 118-120°. [exln
Suzuki, M. eta/, Bull. Chern. Soc. Jpn., 1988, 61, 3371. +33°.
10-Debromo: [73465-58-4]. 3-Bromo-4-chloro-7(14)-
chamigren-9-ol
C15H 14BrC10 M 335.711

604
2,10-Dibromo-3-chloro-5,10;7,8-... - 2,10-Dibromo-5,10-epoxy-2,8-... Sq-02527 - Sq-02532

Constit. of L. obtusa. Cryst. (as acetate). Mp 102-104° 2,10-Dibromo-3-chloro-5,1 0-epoxy-8- Sq-02530

(acetate). [01:]n + 73° (acetate). chamigren-7-ol
Gonzalez, A.G. et al, Tetrahedron Lett., 1976, 3051; 1979, 2717 Pacifenol
(isol, cryst struct) [33880-90-9]

hi
2,10-Dibromo-3-chloro-5,1 0;7,8-diepoxy-9- Sq-02527
chamigranol
Johnstonol

~
[35671-09-1]

HO~----? Br
C 15H 21 Br2Cl0 2 M 428.590
0' Constit. of the red alga Laurencia pacifica. Cryst. (pet.
'c1 ether). Mp 149-150.5°.
Br Sims, J.J. et al, J. Am. Chern. Soc., 1971, 93, 3774.
C 15H 21 Br2Cl03 M 444.590
Constit. of the red alga Laurencia johnstonii and the sea 2,10-Dibromo-3-chloro-7,8-epoxy-9- Sq-02531
hare Aplysia californica. Cryst. (EtOAc). Mp 178°. chamigren-5-ol
Sims, J.J. et al, Tetrahedron Lett., 1972, 195 (isol, struct) Prepacifenol
Ireland, C. et al, J. Org. Chern., 1976, 41, 2461 (synth)
[41060-07-5]
4,10-Dibromo-3-chloro-7,8- Sq-02528 Br
epoxychamigrane
4,10-Dibromo-3-ch/oro-7,8-epoxy-01:-chamigrene
[8484 7-86-9]

~
Br
C 15H 21 Br2Cl02 M 428.590
Constit. of Laurencia filiformis and L. pacifica. Mp 109-
1260 (solidifies and remelts at 147°).
9P,10P-Epoxide: [55304-01-3]. 2,10-Dibromo-7-ch/oro-
Br 7,8;9,10-diepoxy-5-chamigrano/. Prepacifenol epoxide
C 15H 21 Br2Cl0 3 M 444.590
C 15H 23 Br2C10 M 414.607 Constit. of Aplysia californica. Cryst. Mp 98-99°.
lsol. from Laurencia okamurai. Cryst. Mp 123.5-124°. [01:]i;l
+ 13° (c, 0.4 in CHC13). 5-Deoxy: [58967-05-8]. 2,10-Dibromo-3-chloro-7,8-epoxy-9-
chamigrene. Deoxyprepacifenol
Howard, B.M. eta/, Tetrahedron Lett., 1975, 1687 (synth)
Ojika, M. et al, Phytochemistry, 1982, 21, 2410 (isol)
C 15H 21 Br2Cl0 M 412.591
Bano, S. et al, Planta Med., 1987, 53, 508 (isol, cmr) Constit. of Aplysia ca/ifornica and L. majuscula. Cryst.
(pentane). Mp 125°.
Sims, J.J. eta/, J. Am. Chern. Soc., 1973, 95, 972 (isol)
2,10-Dibromo-3-chloro-7,8-epoxy-9- Sq-02529 Fenical, W. et al, J. Phycol., 1975, 11, 104 (isol)
chamigranol Ireland, C. et al, J. Org. Chern., 1976, 41, 2461 (isol)
4,10-Dibromo-3-chloro-7,8-epoxy-9-hydroxy-01:-chamigrane Ireland, C. eta/, J. Org. Chern., 1976, 41, 2461
(Deoxyprepacifenol)

HO,~Br
Fronczek, F.R. et al, Acta Crystallogr., Sect. C, 1989, 45, 1102
(Deoxyprepacifenol, cryst struct, abs config)

2,10-Dibromo-5,10-epoxy-2,8- Sq-02532
01 chamigradien-7-ol
I \
Cl [8651 0-24-9]
Br

~
C 15H 23 Br2Cl02 M 430.606
Constit. of Laurencia glomerata. Gum. [01:]i; + 32.7° (c,
0.91 in CHC1 3).
Elsworth, J.F. et al, J. Nat. Prod. (Lloydia), 1989, 52, 893 (isol, Absolute
pmr, cmr) configuration
OH Br
C15H 20Br20 2 M 392.130
Constit. of red alga Laurencia nipponica. Oil. [01:]n -28.3°
(c, 4.0 in CHCI 3).
Kurata, K. eta/, Chern. Lett., 1983, 561.

605
Laurencial - Laureacetal E Sq-02533 - Sq-02539

Laurencial Sq-02533
[86330-91-8]
Secochamigranes
0~
Laureacetal B Sq-02536
C•sH21 Cl0 2 M 268.782 [69369-25-l]
Constit. of red alga Laurencia nipponica. Cryst.
(hexanejdiisopropyl ether). Mp 124-126°. [ocln + 11.2°
(c, 0.25 in CHC1 3). 0--/"y)~
Kurata, K. eta/, Chern. Lett., 1983, 299 (isol, cryst struct)
Ho~6
Majusculone Sq-02534 'ti
1,5,5-Trimethylspiro[5.5jundeca-1,7-diene-3,9-dione, 9Cl. 15- CisH 21 Br03 M 329.233
N or-1, 7-chamigradiene-3 ,9-dione Constit. of Laurencia nipponica. Cryst. (isopropyl
[112642-49-6] ether/hexane). Mp 105-106°. [ocln +8.4° (c, l in CHC1 3).
Suzuki, T. et a/, Chern. Lett., 1979, 301.

Laureacetal C Sq-02537
[84744-66-l]

(b-~
C 14H 180 2 M 218.295
Constit. of the red alga Laurencia majuscula. Cryst.
(diisopropyl ether). Mp 91.1-92.0°. [oc]~ + 145° (c, 0.965
in CHC1 3). Absolute
Suzuki, M. eta/, Bull. Chern. Soc. Jpn., 1987, 60, 3795. configuration
0 'H

Pinnatazone Sq-02535 C1sH2003 M 248.321

Constit. of red alga Laurencia nipponica. Cryst.
2-Bromo-3-ch/oro-5,10:7,8-diepoxychamigrane
(diisopropyl ether). Mp 118-119°. [ocln +9.8° (c, 1.53 in
[119765-94-5] CHC1 3).
Kurata, K. eta/, Chern. Lett., 1983, 29.

Laureacetal D Sq-02538
[85933-22-8]
Cl

x~-J..
I

Br
C 15H 22 BrCl02 M 349.694 Absolute
Constit. of Laurencia pinnatifida. Cryst. (MeOH). Mp 190- configuration
1920. [ocJn +4.34° (c, 0.23 in CHC1 3). 0 I
H
3,4-Diepimer: [119400-88-3]. Almadioxide X=Br
Constit. of L. intricata. Cryst. (CH 2Cl2 /hexane). Mp
C15H 20 Br20 2 M 392.130
206°. [ocJn +4° (c, 0.7 in CHC1 3).
Constit. of red alga Laurencia nipponica. Cryst.
Atta-ur-Rahman, eta/, Phytochemistry, 1988, 27, 3879 (isol, cryst (hexanejdiisopropyl ether). Mp 126-127°. [ocln + 166° (c,
struct) 0.25 in CHC1 3).
Aknin, M. et a/, Tetrahedron Lett., 1989, 30, 559 (cryst struct)
Kurata, K. eta/, Chern. Lett., 1983, 557 (cryst struct)

Laureacetal E Sq-02539
[85933-21-7]
As Laureacetal D, Sq-02538 with
X= Cl
ClsH 20 BrC102 M 347.678
Constit. of red alga Laurencia nipponica. Cryst.
(hexanejdiisopropyl ether). Mp 119-120°. [ocln +99.5°
(c, 0.42 in CHCI 3).
Kurata, K. eta/, Chern. Lett., 1983, 557 (cryst struct)

606
Acanthisonitrile 3 - Kylinone Sq-02540 - Sq-02546

5,7,11-Cineratrien-9-one Sq-02543
[85526-88-1]
Miscellaneous
spirosesquiterpenes
ClsH200 M 216.322
Acanthisonitrile 3 Sq-02540 Constit. of Cineraria fruticulorum. Oil. [cx]~4 + 375° (c, 0.5
[112766-99-1] in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2531 (iso/)
Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1985, 560 (synth)

Gleenol Sq-02544
Glehnol
[72203-99-7]

H>-
C 16H 25N M 231.380
Metab. of marine sponge Acanthel/a acuta. Oil. [cxJn
-3l.SO (c, 1.2 in CHC13).
/sothiocyanate: [112767-00-7]. Acanthisothiocyanate 3
C 16H 25NS M 263.446 OH
Metab. of A. acuta. Oil. [cxJn -12.9° (c, 0.3 in CHC1 3). C 15H 260 M 222.370
Has -NCS replacing -NC. Constit. of Picea glehnii. Oil. [cx]i,O - 10° (c, 5 in CHC1 3).
Mayo!, L. et al, Tetrahedron, 1987, 43, 5381. Kurvyakov, P.l. et al, Khim. Prir. Soedin., 1979, 164.

Axamide 3 Sq-02541 7-Isopropyl-2,1 O-dimethylspiro(4.5)dec-l- Sq-02545

[59633-82-8] en-6-ol
I
2,10-Dimethyl-7-(J-methylethyl)spiro[4.5]dec-l-en-6-ol, 9CI
[119432-99-4]

C 16H 27NO
~
M 249.395
Constit. of Axinella cannabina. Oil. [cxJn -6.86° (c, 1 in
CHC1 3). I

lsothiocyanate: [59633-81-7]. Axisothiocyanate 3 ~

C 15H 25NS M 251.435 C 15H 260 M 222.370
From A. cannabina. Oil. [cxJn + 165.2° (c, 1 in CHC1 3). Constit. of a Eurypon sp. Oil. [cx)n + 1.3° (c, 0.6 in CHC1 3).
Has -NCS replacing -NHCHO. Related to Axisisonitrile 3.
Isocyanide: [59633-83-9]. Axisonitrile 3 Barrow, C.J. et al, Aust. J. Chern., 1988, 41, 1755.
C 16H 25N M 231.380
Isol. from A. cannabina. Cryst. (pet. ether). Mp 101- Kylinone Sq-02546
1030. [cxJn +68.44° (c, 1 in CHC1 3).
[72036-07 -8]
Blasio, B.Di. eta/, Tetrahedron, 1976, 32, 473.

Biscineradienone Sq-02542

C 15H 21 Br2Cl0 M 412.591

Constit. of Laurencia pacifica. Oil. [cx]i;5 +31° (c, 1.9 in
MeOH).
Selover, S.J. eta/, J. Org. Chern., 1980, 45, 69.

C30H400 2 M 432.645
Constit. of Cineraria fruticulorum. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2531.

607
Laurenone A - Vitrenal Sq-02547 - Sq-02554

Laurenone A Sq-02547 Spirojatamol Sq-02551

[93552-60-4] [128487-46-7]

CQy I

C 15H 240 2 M 236.353 C 15H 260 M 222.370

Constit. of red alga Laurencia nipponica. Oil. [1X]n + 152° Constit. of roots of Nardostachys jatamansi. Viscous oil.
(CHCl 3). [1X]n + 18.0° (c, 4.20 in CHCl3).
2-Epimer: [93603-63-5]. Laurenone B Bagchi, A. et al, Tetrahedron, 1990, 46, 1523 (isol, struct)
C 15H 240 2 M 236.353
Constit. of L. nipponica. Oil. [1X]n + 58.2° (CHCl 3).
Spirolaurenone Sq-02552
Fukuzawa, A. et al, Chern. Lett., 1986, 1349 (cryst struct)
[30925-25-8]

Mirabolide Sq-02548 Br

¢tz~H,
I

r\'~0>=o
~~
CtsH 2z0 2 M 234.338
Parent compd. unknown. C 15H 23Br0 M 299.250
Constit. of the essential oil of Laurencia glandulifera. Oil.
]-Hydroxy: [90039-69-3]. 1-Hydroxymirabolide
[1X]n -70.6° (c, 1.26 in CHCl 3).
C 15H 22 0 3 M 250.337
Constit. of Wunderlichia mirabilis. Oil. [1X]~4 + 26° (c, Semicarbazone: Cryst. Mp 165-170°.
0.18 in CHCl 3). Suzuki, M. et a/, Tetrahedron Lett., 1970, 4995 (isol, struct)
Suzuki, M. eta/, Tetrahedron, 1980, 36, 1551 (abs config)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1984, 228.
Murai, A. et al, Tetrahedron Lett., 1982, 23, 2887 (synth)

9,11(13)-Ratibidadien-12,8-olide Sq-02549 Spironippol Sq-02553

[80981-64-2]
~Yi~>=
~0 ~OH Relative
y~
15
configuration
C 15H 100 2 M 232.322
(4S,5S,7R,8R)-form [94137-83-4] C15H 24 0 2 M 236.353
Constit. of Ratibida columnifera. Gum. Constit. of Laurencia nipponica. Cryst. Mp 135-136°. [aln
!!. 10 •15 -Jsomer: [94137-79-8]. 10(15),11(13)-Ratibidadien-12,8- +59.1°.
olide Fukuzawa, A. et al, Tetrahedron Lett., 1981, 22, 4087 (cryst struct)
C 15H 200 2 M 232.322
Constit. of R. columnifera. Gum.
Herz, W. et al, J. Org. Chern., 1985, 50, 610.
Vitrenal Sq-02554
[77283-84-2]
Spiroeuryolide Sq-02550 \

OHC()() Absolute
configuration
A
' I

C15H 220 M 218.338

CtsH 180 2 M 230.306 Constit. of Lepidozia vitrea. Plant growth inhibitor. Oil.
Constit. of Euryops arabicus. [1X]n + 107° (c, 1.55 in CHC1 3).
Hafez, S. et al, Phytochemistry, 1989, 28, 843. Hirota, H. et al, Chern. Lett., 1982, 1143 (synth)
Matsuo, A. et al, J. Chern. Soc., Perkin Trans. 1, 1984, 215 (abs
corifig)
Kodama, M. eta/, Bull. Chern. Soc. Jpn., 1986, 59, 1897 (synth)

608
3-Cedranol - 3(15)-Cedren-9-ol Sq-02555 - Sq-02560

Constit. of Cupressus funebris. Oil.

Cedranes
[11028-42-5, 22567-43-7]
Hill, H.C. et al, J. Chern. Soc. C, 1968, 93 (ms)
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pjlanzensto.ffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
no. 1921 (occur)
Kirtany, J.K. et al, Indian J. Chern., 1973, 11, 508 (a-Funebrene)
Lansbury, P.T. eta/, J. Am. Chern. Soc., 1974, 96, 896 (synth, bib/)

Cf+OH
3-Cedranol Sq-02555 Paknikar, S.K. et a/, Tetrahedron Lett., 1975, 2973 (a-Funebrene)
Breitholle, E.G. et al, Can. J. Chern., 1976, 54, 1991 (synth, bib/)
Wender, P.A. et al, J. Am. Chern. Soc., 1981, 103, 688 (synth)
So1as, D. eta/, J. Org. Chern., 1983, 48, 670 (synth)
Horton, M. et al, Tetrahedron Lett., 1983, 24, 2125 (synth)
Joseph-Nathan, P. eta/, J. Nat. Prod. (Lloydia), 1984, 47, 924
H (cmr)
CISH260 M 222.370
Jfl-form [77-53-2] Cedro/. P-Cedrol. Cedar camphor. Cypress 3-Cedren-9-ol Sq-02558
camphor
Widespread in the Cupressaceae, eg. Juniperus,
Cupressus, Tetraclinis spp. Needles (MeOH aq.). Mp
86-87°. [1X]n + lO.SO (c, 5 in CHC1 3).
Ac: [77-54-3].
Used in perfumery.
C 15H 240 M 220.354
Hill, H.C. et al, J. Chern. Soc. C, 1968, 93 (ms)
Amirthalingam, V. et al, Acta Crystallogr. (Suppl.), 1969, 5129 9fl-form [19902-30-8] a-Biotol
(cryst struct, abs config) Constit. of the essential oil of the wood of Biota
Opdyke, D.L.J., Food Cosmet. Toxicol., Suppl., 1975, 745 (rev) orienta/is. Cryst. Mp 78°. [IX]~ -27.3° (CC14).
Breitholle, E.G. et al, J. Org. Chern., 1978, 43, 1964 (synth, bib/) Tomita, B. et al, Tetrahedron Lett., 1968, 843 (isol, struct)
Yates, P. eta/, Tetrahedron, 1981, 37, 4401 (synth) Trifilieff, E. et al, Tetrahedron Lett., 1975, 4307 (synth)
Joseph-Nathan, P. et a/, J. Nat. Prod. (Lloydia), 1984, 47, 924 Brun, P., Tetrahedron Lett., 1977, 2269 (synth)
(cmr) Grewal, R.S. et al, J. Chern. Soc., Chern. Commun., 1987, 1290
Khan, V.A. eta/, Khim. Prir. Soedin., 1985, 21, 41 (cryst struct) (synth)
Yates, P. eta/, Can. J. Chern., 1988, 66, 2805 (synth)
3(15)-Cedrene Sq-02556
[546-28-1] 3(15)-Cedren-8-ol Sq-02559

ClsHu
efT H
M 204.355
(7«H,JOPII)-form
(7ct.H,10PII)-form

C 15H 240
H~
M 220.354
8fl-form [24048-41-7] P-Isobiotol
H

fl-Cedrene. 8(15)-Cedrene Constit. of the wood of Biota orienta/is. Cryst. Mp

Widespread in plants, e.g. in Juniperus, Cunninghamia, 76.SO. [1X]i,O -7.8°.
Sciadopitys, Thujopsis spp. Oil. Bp5 120°. [1X]i,O +9.7°. nn Tomita, B. et al, Mokuzai Gakkaishi, 1969, 15, 47; CA, 71, 50250t.
1.5040.

m
(7pH,JOall)-form [40768-80-7] 7,10-Diepi-fl-cedrene. 2,5-diepi- 3(15)-Cedren-9-ol Sq-02560
P-Cedrene
lsol. from S. verticillata. Oil. [1X]i;' + 15.4° (c, 0.72 in
CHC1 3).
Acharya, S.P. et al, J. Org. Chern., 1970, 35, 196 (synth, bib/)
Norin, T. eta/, Tetrahedron Lett., 1973, 17.
HO H

4+'
3-Cedrene Sq-02557 C 15H 240 M 220.354
9fl-form [19902-26-2] P-Bioto/
Cons tit. of the essential oil of Biota orienta/is. Cryst.
Mp 84°. [1X]~4 +43.8° (CC14).
(2o,6a)-fo'm Tomita, B. et a/, Tetrahedron Lett., 1968, 843 (isol, struct)
Grewal, R.S. eta/, J. Chern. Soc., Chern. Commun., 1987, 1290
H (synth)
CisHu M 204.355 Yates, P. eta/, Can. J. Chern., 1988, 66, 2805 (synth)
(2«,6«)-form [469-61-4] a-Cedrene; 8-Cedrene
Occurs in cedarwood and many other oils. Oil. Bp760
262-263°, Bp 12 124-126°. n~ 1.5001.
t> PB7725000.
(2ft,6p)-form [50894-66-1] a-Funebrene

609
2,4-Dihydroxy-3-cedrene-1,5-dione - 4-Hydroxy-3-cedrene-1,5-dione Sq-02561 - Sq-02567

2,4-Dihydroxy-3-cedrene-1,5-dione Sq-02561 3-Hydroxy-12-cedranoic acid Sq-02564

I

(2a,6a,IO~H}/"'m
~OH
*H 4--1--COOH
H
H
C15H 240 3 M 252.353
C 15H 200 4 M 264.321
3P-form [18319-38-5] Cedrolic acid
(2«,6«,10Pil)-form [38044-10-9] 1-Perezol Constit. of Juniperus utahensis. Cryst. Mp 181-187°. [1X]n
Constit. of the root of Perezia hebeclada. Cryst. -47° (c, 3.2 in CHC1 3).
(Me 2C0jhexane). Mp 182-184°.
Runeberg, J., Acta Chern. Scand., 1961, 19, 945 (isol)
2-Angeloyl: [38044-08-5]. «-Perezol Baggaley, K.H. et a/, Tetrahedron, 1968, 24, 3399 (struct)
C20 H 260 5 M 346.422
Constit. of P. hebeclada. Cryst. (Me2CO/hexane). Mp
3-Hydroxy-14-cedranoic acid Sq-02565

7ftH
154-158°. Obt. only in a mixt. with P-Perezol.
(2p,6p,10«1/)-form
2-Angeloyl: [38044-09-6]. P-Perezol
C20H 260 5 M 346.422
Constit. of P. hebeclada. Obt. only as mixt. with IX-
Perezol (see above).
H
Joseph-Nathan, P. eta/, Phytochemistry, 1972, 11, 1803 (isol)
Joseph-Nathan, P. eta/, Tetrahedron, 1980, 36, 731 (stereochem) C15H 240 3 M 252.353
Joseph-Nathan, P. eta/, J. Nat. Prod. (Lloydia), 1986, 49, 79 (cmr) 3P-form [60237-70-9] Isocedrolic acid
Constit. of Juniperus squamata. Cryst. Mp 259-261°. [1X]n
1,2-Dihydroxy-3-cedren-4-one Sq-02562 -24.8° (c, 0.5 in MeOH).
Kuo, Y.H. et a/, Experientia, 1976, 32, 827.

3-Hydroxy-9-cedranone Sq-02566

~OH
C 15H 220 3 M 250.337
(JR,2p,6p,JO«I/)-form [97777-72-5] Coreosenarione
Constit. of Coreopsis spp. Cryst. (EtzOjpet. ether). Mp C15H 240 2
oJ-t+
M 236.353
179°. 3P-form [58613-27-7] 4-Ketocedrol
Bohlmann, F. et a/, Phytochemistry, 1985, 24, 1295. Constit. of Juniperus squamata. Cryst. Mp 129-130°. [1X]n
-21.5° (c, 1.4 in MeOH).
3,12-Epoxycedrane Sq-02563 Trifilieff, E. eta/, Tetrahedron Lett., 1975, 4307 (synth)
Kuo, Y.H. et a/, Experientia, 1976, 32, 686 (isol, struct)
,__C);Q Trifilieff, E. eta/, J. Chern. Res. (S), 1978, 64 (synth)

<J__1J I
4-Hydroxy-3-cedrene-1,5-dione
IX- Pipitzol
Sq-02567

C15H 240 M 220.354 [2211-20-3]

3P-form [18319-31-8] 8,14-Cedranoxifk

~ (2a,6o<)-fo~
Constit. of Juniperus foetidissima. Oil. Bp0.1 100°. [1X]n
-96° (c, 1.9 in CHC1 3).
12-0xo: [18319-32-9]. 12,3-Cedranolifk. 14,8-Cedranolide
C15H 220 2 M 234.338
From J.foetidissima. Oil. Bp0. 1 120°. [1X]i,l -66.4° (c, 1.5
in CHC1 3). H
Baggaley, K.H. eta/, Acta Chern. Scand., 1968, 22, 1709.
C15H 200 3 M 248.321
(2«,6«)-form
Constit. of Perezia cuernavacana and obt. by pyrolysis
of Perezone. Cryst. (Me2CO/hexane). Mp 146-147°. [1X]i?
+ 192° (CHC13).
(2p,6JI)-form [2211-21-4] P-Pipitzol
Isol. from P. cuernavacana or by pyrolysis of Perezone.
Cryst. (EtOAcfhexane). Mp 131-132°. [1X]i? -172°
(CHC1 3).
Walls, F. et al, Tetrahedron, 1966, 22, 2387 (isol, struct)
Taira, Z. eta/, Cryst. Struct. Commun., 1977, 6, 23 (cryst struct)
Joseph-Nathan, P. eta/, Tetrahedron, 1980, 36, 731 (stereochem)
610
5-Hydroxy-3-cedren-15-oic acid- 5,12,14-Trihydroxy-3-cedren-15-... Sq-02568 - Sq-02570

Sanchez, I.H. et al, Tetrahedron, 1985, 41, 2355 (synth) 5,12,14-Trihydroxy-3-cedren-15-oic acid Sq-02570
Joseph-Nathan, P. et al, J. Nat. Prod. (Lloydia), 1986, 49, 79 (cmr)
Joseph-Nathan, P. et al, J. Org. Chern., 1987, 52, 759 (synth) 14 OH
Pak, H. et al, J. Org. Chern., 1990, 55, 3009 (synth)
HOHffi-C-OOH
5-Hydroxy-3-cedren-15-oic acid Sq-02568 (5~, 7a.H)-form

H CH2 0H

m~H C15H 220 5 M 282.336

(5P,7rzH)-form [24205-56-9] Laksholic acid
Constit. of lac. Cryst. (CHC1 3jEtOH). Mp 181-183°. [rx.Jn
+49.4° (CHC1 3).
H
14-Carboxylic acid: [4448-95-7]. 5,12-Dihydroxy-3-cedrene-
CISH2203 M 250.337 14,15-dioic acid. Shellolic acid
5P-form CISH2006 M 296.319
Renecraviotonic acid. 2fi-Hydroxy-rx.-cedren-15-oic acid Constit. of Kusmi shellac. Cryst. (Hp). Mp 206°. [rx.]llt,
Constit. of lsocoma coronopifolia. Oil. +26.3°.
Dominguez, X.A. et al, Phytochemistry, 1986, 25, 2893. (5P,7PH)-form [24205-61-6] Epilaksholic acid. epi-Laksholic
acid
5-Hydroxy-14-oxo-3-cedren-15-oic acid Sq-02569 Constit. of lac. Cryst. (CHC1 3 jEtOH). Mp 201-203°. [rx.ln
+63.7° (CHC1 3).
14-A/dehyde: [24205-55-8]. 5,12-Dihydroxy-14-oxo-3-cedren-
5~~~
OC$TH COOH
15-oic acid. Jalaric acid. Jalaric acid A
C15H 2o0s M 280.320
Isol. from lac resin from Laccifer lacca. Cryst. (MeCN).
(5~, 7a.)-form
Mp 178-180°. [rx.Ji:' +36.8° (c, 0.7 in EtOH).
14-A/dehyde, 5-0-(16-hydroxy-9Z-hexadecenoyl): [54045-02-
CISH2004 M 264.321 2]. Jalaric ester I
(5p,7rz.)-form [24393-98-4] Laccijalaric acid C31 H 480 7 M 532.716
Constit. of lac resin from Laccifer /acca. Cryst. Constit. of the soft resin of Palas seedlac. Gum. [rx.Jn
(EtOAc). Mp 164-165°. [rx.]~ +26.3° (c, 1.5 in EtOH). + 68.6° (CHC1 3).
14-A/dehyde, 5-0-(9R,10R,16-trihydroxyhexadecanoyl):
4-(16-Hydroxy-9Z-hexadecenoyl): [53837-80-2]. Laccijalaric
[53837-82-4]. Jalaric ester II
ester I
C31 H 480 6 M 516.717 C31 H500 9 M 566.731
Constit. of Palas seedlac. Gum. [rx.ln +68.6° (CHC1 3). Constit. of P. seedlac. Foam. [rx.ln + 69.9° (CHC1 3).
Wadia, M.S. et al, Tetrahedron, 1969, 25, 3841 (Laksholic acid,
4-(9R,JOS,16- Trihydroxyhexadecanoyl): [53837-81-3].
Epilaksholic acid, Jalaric acid)
Laccijalaric ester II Yates, P. et al, Tetrahedron, 1970, 26, 3135, 3159 (Shellolic acid)
CJIH5008 M 550.731 Singh, A.N. et al, Tetrahedron, 1974, 30, 867 (Jalaric esters)
From Palas seedlac. Foam. [rx.Jn +65.6°. Subramanian, G.B.V. et al, J. Chern. Soc., Perkin Trans. I, 1976,
14-Carboxylic acid: [24393-97-3]. 5-Hydroxy-3-cedrene- 2045 (Jalaric acid)
14,15-dioic acid. Epilaccishellolic acid. epi-Laccishellolic
acid
Constit. of lac resin from L. /acca. Cryst. (MeOH). Mp
235-236°. [rx.Jn +43° (EtOH).
14-A/coho/: [24393-99-5]. 5,14-Dihydroxy-3-cedren-15-oic
acid. Epilaccilaksholic acid
CISH2204 M 266.336
Constit. of lac resin.
(5p,7p)-form
14-Carboxylic acid: [24393-95-1]. Laccishellolic acid
C15H 200 5 M 280.320
From L. lacca lac resin. Cryst. (MeOH). Mp 196-198°.
14-A/coho/: [33051-49-9]. Laccilaksholic acid
CISH2204 M 266.336
Constit. of lac resin.
Singh, A.N. et al, Tetrahedron, 1969, 25, 3855; 1974, 30, 867.
Khurana, R.G. et al, Tetrahedron, 1970, 26, 4167 (isol)

611
4,12;14,15-Diepoxy-5(15)-isocedren-... - 14,15-Epoxy-4-isocedrene-3,14,15-•.. Sq-02571 - Sq-02576

14,15-Epoxy-4-isocedrene-3,8,9,14,15- Sq-02574
pentol
Isocedranes
OH

4,12; 14,15-Diepoxy-5(15)-isocedren-14-ol Sq-02571

H0'2f]J H I
C15H210 6
(3fl,8fl,9fl)-form

C19H44,010
M 298.335

3-Angeloyl, 8-(2-methylbutanoy/),14,15-di-Ac: [69993-67-5].

M 548.629
Constit. of Perezia multiflora. Oil.
C15H 100 3 M 248.321 3-Angeloyl, 8-(3-methylbutanoy/),14,15-di-Ac: [69993-68-6].
(4fl,l4rz)-form C19H400 10 M 548.629
11-Deoxotrixikingolide. 12-Deoxytrixikingo/ide Constit. of P. multiflora. Oil.
2-Methylbutanoyl: [69993-49-3]. Bohlmann, F. eta/, Chern. Ber., 1979, 112, 427.
C:zoll180 4 M 332.439
Constit. of Trixis inula. Oil.
14,15-Epoxy-4-isocedrene-3,8,14,15-tetrol Sq-02575
Bohlmann, F. eta/, Chern. Ber., 1979, 112, 435.
OH
14,15-Epoxy-14-bydroxy-3,5(15)- Sq-02572 OH
isocedradien-12-oic acid
Trixol

H
C15H 210 5 M 282.336
8fl-form
3-Angeloyl,l4,15-di-Ac: [69993-64-2]. 3-Angeloyl-8-
hydroxyproustianol
C15H 180 4 M 262.305 C24H 320 8 M 448.512
14rz-form [96853-71-3] Constit. of Proustia pyrifolia. Oil.
Constit. of Trixis paradoxa. Oil. 3,8-Diangeloyl,14,15-di-Ac: 3-Angeloyl-8-
Gonzalez, A.G. et al, An. Quirn., 1984, 80, 319. angeloyloxyproustianol
C19H 380 9 M 530.614
14,15-Epoxy-14-bydroxy-5(15)-isocedren- Sq-02573 Constit. of Perezia multiflora. Oil.
12,4-olide Bohlmann, F. eta/, Chern. Ber., 1979, 112, 427.

HiftT-31
14,15-Epoxy-4-isocedrene-3,14,15-triol Sq-02576
OH
9 12 OH
: 0 HO-
H I

C15H 180 4 M 262.305

(4fl,l4rz)-form [70024-56-5]
H
Trixikingolide, 9CI
Parent compd. not known. C15H210 4 M 266.336
2-Methylbutanoyl: [69993-42-6]. (3fl,l4rz,15fl)-form
C10H260 5 M 346.422 14,15-Di-Ac: Proustianol
Constit. of Trixis wrightii. Oil. C19H 260 6 M 350.411
3-Methylbutanoyl: [70022-64-9]. Parent compd. not known.
C10H260 5 M 346.422 3-Angeloyl, 14,15-di-Ac: [69993-62-0]. 3-Angeloylproustianol
Constit. of T. wrightii. Oil. C24 H320 7 M 432.513
Bohlmann, F. eta/, Chern. Ber., 1979, 112, 435. Constit. of Proustia pyrifolia. Oil. [1X]i;' -5.3° (c, 1 in
CHC1 3).
Bohlmann, F. et al, Chern. Ber., 1979, 112, 427.

612
14,15-Epoxy-5(15)-isocedrene-... - 4-Isocedren-15,14-olide Sq-02577 - Sq-02581

14,15-Epoxy-5(15)-isocedrene-9,12,14-triol Sq-02577 4-Isocedrene-14,15-diol Sq-02579

/so-~-cedrene-14, 15-diol

HOH~C
HOH2C c::?
/~,

12

'oH
H H
C 1sH200s M 280.320 C 1sH140 2 M 236.353
(4P,9rx.,12rx.,I4rx.,)-form Di-Ac: [87798-02-5].
9-(3-Methylbutanoyl), 14-(2-methylbutanoyl): [69993-48-2]. C19H 280 4 M 320.428
C2SH360 7 M 448.555 Constit. of Jungia stuebelii. Gum. [~]~4 + 52° (c, 0.38 in
lsol. from Trixis inula. CHCI 3).
9-(3-Methyl-2-butenoyl), 14-(2-methylbutanoyl): [69993-47- Dialdehyde: (69993-61-9]. 4-/socedrene-14,15-dial. /so-~­
1]. cedrene-14, 15-dial
C2SH340 7 M 446.539 C 1sH 200 2 M 232.322
From T. wrightii. Constit. of J. malvaefolia. Oil.
12-Ketone, 14-(2-methylbutanoyl), 9-Ac: [69993-46-0]. Bohlmann, F. eta/, Chern. Ber., 1979, 112, 427.
C 22H 280 6 M 388.460 Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1201.
lsol. from T. inula. Oil.
12-Ketone, 9-(2-methylbutanoyl), 14-(3-methylbutanoyl): 4-Isocedren-14,15-olide Sq-02580
[69993-45-9]. /so-~-cedren-14,15-olide
C2SH 340 7 M 446.539 [87797-99-7]
From T. inula~ Oil.
12-Ketone, 9-(3-methyl-2-butenoyl), 14-(2-methylbutanoyl):
(69993-43-7].
C2SH320 7 M 444.524
lsol. from T. wrightii. Oil.
~
04+
12-Ketone, 9-(3-methylbutanoyl), 14-(2-methylbutanoyl):
[69993-44-8]. H
C2SH 340 7 M 446.539 C 15H 200 2 M 232.322
Isol. from T. inula. Oil. Constit. of Jungia stuebelii. Gum. [~]i;' +60° (c, 0.45 in
(4P,9rx.,I2P,14rx.)-form CHCI3).
9-(3-Methylbutanoyl), 14-(2-methylbutanoyl): [70050-81-6]. 14-Alcohol: [87798-00-3]. 14,15-Epoxy-4-isocedren-14-ol
lsol. from T. inula. C 15H 220 2 M 234.338
9-(3-Methyl-2-butenoyl), 14-(2-methylbutanoyl): (70050-80- From J. stuebelii. Gum. [~]~4 + 33° (c, 0.1 in CHCI 3).
5]. Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1201.
From T. wrightii.
12-Deoxy, 9-(3-methyl-2-butenoyl), 14-(2-methylbutanoyl): 4-Isocedren-15,14-olide Sq-02581
[69993-50-6]. /so-~-cedren-15 ,14-olide
C2SH340 6 M 430.540
From T. wrightii. 0

~
Bohlmann, F. et a/, Chern. Ber., 1979, 112, 435.

4-Isocedren-15-al Sq-02578
1so-~-cedren-15-a/
[73213-55-5] H
C1sH200 2 M 232.322

0~ Constit. of Jungia stuebelii. Gum. [~]i;' + 86° (c, 0.62 in

CHC1 3).
9~- Hydroxy: [87797-96-4]. 9rx.-Hydroxy-4-isocedren-15 ,14-
olide
H C 1sH 200 3 M 248.321
C 1sH220 M 218.338 Constit. of J. stuebelii. Gum (as diacetate). [~]i;' +95°
Constit. of Jungia malvaefolia. Oil. Bp0 . 1 120°. (~]~4 + 71.4° (c, 0.25 in CHCI 3) (diacetate).
(c, 5 in CHCI 3). up-Hydroxy: [87797-98-6]. 14P-Hydroxy-4-isocedren-15,14-
Bohlmann, F. eta/, Chern. Ber., 1979, 112, 427. olide
C 1sH200 3 M 248.321
From J. stuebelii. Gum. [~]~4 + 70° (c, 0.1 in CHCI 3).
Bohlmann, F. et a/, Phytochemistry, 1983, 22, 1201.

613
4-lsocedren-15,14-olid-12-oic acid - 6(13)-Zizaen-3-ol Sq-02582 - Sq-02588

4-Isocedren-15,14-olid-12-oic acid Sq-02582 Constit. of vetiver oil. Oil. Bp 10 120-122°. [1X]n +40.4° (c,
14-Hydroxyiso-rx-cedrene-12,15-dioic acid 14,15-lactone 5.2 in CHC1 3).
Deljac, A. et al, Can. J. Chern., 1972, 50, 726 (synth)

at~H
Coates, R.M. eta/, J. Am. Chern. Soc., 1972, 94, 5386 (synth)
Hanayama, N. eta/, Tetrahedron, 1973, 29, 945 (isol, struct)
Piers, E. et al, Can. J. Chern., 1982, 60, 2965 (synth)
Barker, A.J. et al, J. Chern. Soc., Perkin Trans. I, 1983, 1901
(synth)

Hstt ~~0~
I 6(13)-Zizaen-12-oic acid Sq-02586
C 13H 180 4 M 262.305
Constit. of Jungia stuebelii. Gum (as Me ester). [rx]~ + 10°
(c, 0.15 in CHC1 3)(Me ester).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1201.

7-Oxo-14-nor-4-isocedren-15-al Sq-02583
C 13H 110 1 M 234.338
[16203-25-1] Zizanoic acid. Khusenic acid
0~
2r~.H-form

~
Constit. of the essential oil of vetiver ( Vetiveria
zizanioides). Cryst. (MeOH). Mp 80-81°. [IX]~ + 21.8° (c,
2.95 in CHCI 3).
2/lH-form [22387-77-5] Epizizanoic acid
H
Ct5H110 1 M 234.338
c.4H.80 1 . M 218.295 Minor constit. of vetiver oil. Cryst. (MeOH aq.). Mp
Constit. of Jungia stuebelii. Gum. [1X]14 + 52° (c, 0.38 in 109-llO.SO. [1X]i,l -2.2° (c, 2.75 in CHC1 3).
CHC1 3). MacSweeney, D.F. et al, Tetrahedron, 1971, 27, 1481 (synth)
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1201. Hanayama, N. eta/, Tetrahedron, 1973, 29, 945 (isol, struct)
Liu, H.-J. eta/, Can. J. Chern., 1982, 60, 1081 (synth)

2(12)-Zizaen-13-ol Sq-02587
lsotricyclovetivenol. lsokhusimol

Zizaanes [26128-00-7]

12-Nor-6(13)-zizaen-2-one Sq-02584
Khusimone
[30557-76-7] C 15H 140 M 220.354
Constit. of vetiver oil. Oil. Bp0.3 158-163°. [IX]~ +29.3°.

<ft
Umarini, D.C. et a/, CA, 1970, 72, 43897b.

6(13)-Zizaen-3-ol Sq-02588
0 l..--...J

C 14H 100 M 204.311

Constit. of vetiver oil. Cryst. (pet. ether). Mp 78°.
Umrani, D.C. et a/, Flavour Ind., 1970, 1, 623 (isol)
Biichi, G. eta/, J. Org. Chern., 1977, 42, 3323 (synth)
Liu, H.-J. eta/, Can. J. Chern., 1979, 57, 708; 1982, 60, 1081 C15H 140 M 220.354
(synth) Struct. revised in 1984.
Oppolzer, W. et al, J. Am. Chern. Soc., 1982, 104, 6478 (synth) 3r~.-form [281 02-79-6] Zizanol
Oppolzer, W. eta/, Tetrahedron Lett., 1983, 24, 4975 (synth) Constit. of vetiver oil. Cryst. Mp 58.5-60°. [IX]): + 10.4°
Sakurai, K. eta/, Agric. Bioi. Chern., 1989, 53, 1449 (synth) (CHCI 3).
3fl-form
6(13)-Zizaene Sq-02585 3-Epizizanol
Tricyclovetivene. Khusimene. Khusene. Zizaene Cryst. Mp 73-75°.
[18444-94-5] Homma, A. et a/, Tetrahedron Lett., 1970, 231 (isol)
Kang, S.H. et a/, J. Org. Chern., 1984, 49, 3830 (struct, cmr)

Absolute
configuration
M 204.355

614
6(13)-Zizaen-12-ol - Neoanisatin Sq-02589 - Sq-02594

6(13)-Zizaen-12-ol Sq-02589 Constit. of the bark of Illicium dunnianum. Needles

(CHC1 3). Mp 245-246°. [~X]i;' +61° (c, 0.1 in dioxan).

~
6-Deoxy: [116085-01-9]. 6-Deoxydunnianin
C:z:zH280 6 M 388.460
Constit. of the bark of I. dunnianum. Needles

12~
W/-fonn (CHC1 3 jhexane). Mp 222-223°.
Kouno, I. et al, J. Chern. Soc., Perkin Trans. I, 1988, 1537 (isol,
pmr, cmr)
C 15H 2,.0 M 220.354
2rx.H-form [16223-63-5] Tricyclovetivenol. Khusimol. Khusenol Jinkoholll Sq-02592
Constit. of vetiver oil (Vetiveria zizanioides). Oil. Bp 14 [86703-03-9]

<;Q,CH,OH
171-174°. [!X]D +34.6°.
p-Bromobenzoyl: Cryst. (EtOH). Mp 77-79°.
12-A/dehyde: [82509-29-3]. 6(13)-Zizaen-12-a/. Zizanal
C 15H 22 0 M 218.338
Constit. of V. zizanioides. Insect repellent. Oil. [~X]i?
+69.SO (c, 0.233 in CHC1 3).
C 15H 260 M 222.370
2PH-form
Constit. of Agarwood. Cryst. (CHC1 3). Mp 79-81°. [~Xln
12-A/dehyde: [82463-21-6]. Epizizanal +32.4° (c, 0.26 in CHC1 3).
C 15Hn0 M 218.338
Nakanishi, T. et al, J. Chern. Soc., Perkin Trans. I, 1983, 601.
From V. zizanioides. Insect repellent. Oil. [~X]i? -5.9° (c,
0.287 in CHC1 3).
Coates, R.M. et al, J. Chern. Soc., Chern. Commun., 1969, 999 Majucin Sq-02593
(cryst struct) [114687-97-7]
Hanayama, N. et al, Tetrahedron, 1973, 29, 945 (isol, struct)
Jain, S.C. et al, Tetrahedron Lett., 1982, 23, 4639 (aldehyde)

Prezizaanes
C 15H 100 8 M 328.318
Constit. of Illicium majus. Needles (MeOH). Mp 251-252°.
[~X]i;' -74° (c, 0.15 in dioxan).
Anisatin Sq-02590 3-Deoxy: [114687-98-8]. Neomajucin
[5230-87-5] C 15H 200 7 M 312.319
Constit. of I. majus. Octahedra (EtOAc). Mp 220-222°.
[1X]~4 -75° (c, 0.25 in dioxan).
Yang, C.-S. et al, Tetrahedron Lett., 1988, 29, 1165 (cryst struct)

Neoanisatin Sq-02594
[15589-82-9]

C 15H 100 8 M 328.318

An 8,9-secoprezizaane. Isol. from seeds of Illicium
anisatum. Cryst. (HzO). Mp 227-228°. [~X]i,S -27° (c, 2 in
dioxan).
I> Convulsant poison.
@~"
HO O
Lane, J.F. et al, J. Am. Chern. Soc., 1952, 74, 3211 (isol)
Yamada, K. et al, Tetrahedron Lett., 1965, 4797 (struct) C 15H 100 7 M 312.319
Wong, M.G. et al, Aust. J. Chern., 1988, 41, 1071 (cryst struct,
Constit. of the seeds of Illicium anisatum. Cryst. (H20).
pmr)
Mp 237-238°. [~X]i,S -25° (c, 1 in dioxan).
Yamada, K. et al, Tetrahedron, 1968, 24, 199.
Dunnianin Sq-02591
[116085-00-8]

~OH
PhCOO~,kOH
M 404.459

615
2-0xo-6-deoxyneoanisatin - Clovene Sq-02595 - Sq-02600

2-0xo-6-deoxyneoanisatin Sq-02595 Pseudoanisatint Sq-02598

[128129-58-8] [31090-37-6]

HO O

C 15H 180 7
~
M 310.303
0

Toxic constit. of Illicium majus. Cryst. (CHCI 3/Et0Ac).

ClsHn06 M 298.335
Constit. of Illicium anisatum. Cryst. (EtOAc). Mp 207-
2080. The name '1'-Anisatin was also given to a C21
Mp 211-213°. [1X] 0 +67.4°.
constit. of I. anisatum(struct. unknown).
Yang, C.-S. eta/, Chern. Pharm. Bull., 1990, 38, 291 (isol, struct)
7-Deoxy: 7-Deoxypseudoanisatin. 6-Deoxypseudoanisatin
ClsH 220 5 M 282.336
7-Prezizaanol Sq-02596 Constit. of the bark of Illicium dunnianum. Prisms
7-Hydroxyprezizane. Prezizanol (EtOAc). Mp 234-235°. [1X]~ + J60 (c, 2 in EtOH).
Okigawa, M. eta/, Tetrahedron Lett., I97I, 75 (isol)
Kouno, I. eta/, J. Chern. Soc., Perkin Trans. I, I984, 25II (cryst
struct)
(la,2~H,5a,7~0H,8a)-form Kouno, I. eta/, J. Chern. Soc., Perkin Trans. I, I988, I537 (deriv)

C 15H 260 M 222.370

(1«,2PH,5«,7POH,8«.)-form
Constit. of Eremophila georgei. Oil or cryst. Mp 34°.
Bp0_1 100°. [1X] 0 -48.3° (c, 0.1 in CHC1 3). Clovanes
(lP,2«.H,5P,7POH,8fJ)-form [66512-57-0] Allokhusiol. Jinkohol
Constit. of Vetiveria zizanioides and Aquilaria agallocha.
Liq. or cryst. Mp 34°. [1X] 0 -6.1° (c, 0.76 in CHC13),
[1X] 0 +45° (c,1.2 in CHC1 3). Discrepancy in opt. rotns. Clovanediol Sq-02599
not explained. Identity of Allokhusiol and Jinkohol
apparently not fully establ. [2649-64-1]
Ghisalberti, E.L. eta/, J. Chern. Soc., Perkin Trans. I, 1975, 1300
(cryst struct)
Carrol, P.J. et a/, Phytochemistry, 1976, 15, 777 (iso/, struct)
Ganguly, R.N. eta/, Indian J. Chern., Sect. B, 1978, 16, 20 (isol,
stuct)
Nakaniski, T. eta/, Phytochemistry, I98I, 20, I597 (isol, struct)
Sakurai, K. eta/, Tetrahedron, I990, 46, 76I (synth)
C 15H 260 2 M 238.369
Coilstit. of Dipterocarpus pilosus, Salvia canariensis and
Prezizaene Sq-02597 Viguiera oaxacana. Cryst. (MeCN). Mp 152-153°. [1X] 0
+50.

~
~ (+)-form
Gupta, S. eta/, Tetrahedron, I97I, 27, 635 (isol, struct)
Gonzalez, A.G. et a/, An. Quim., I975, 70I (isol)
Delgado, G. eta/, J. Nat. Prod. (Lloydia), I984, 47, I042 (cmr)

Clovene Sq-02600
C1sH24 M 204.355
[469-92-1)
(+)-form [31145-21-8)
Constit. of vetiver oil. Oil. [1X] 0 + 55° (c, 0.02 in MeOH).
(-)-form [60410-32-4]
Constit. of Eremophila georgei. Oil. [1X] 0 -47° (CHC1 3).
Anderson, N.H. eta/, Chern. Ind. (London), I97I, 62 (isol, pmr,
abs con.fig)
Carrol, P.J. eta/, Phytochemistry, I976, 15, 777 (isol) C 15H 24 M 204.355
Vette!, P.R. et a/, J. Org. Chern., I980, 45, 5430 (synth)
Sakurai, K. eta/, Tetrahedron, I990, 46, 76I (synth) Dehydn. prod. from IX-Caryophyllene alcohol. Liq. Bp 12 _5
115°. [1X]i,S -23.4° (c, 3.13 in CHC1 3).
Aebi, A. et a/, J. Chern. Soc., I954, 4659 (struct)
Becker, D. eta/, J. Chern. Soc., I965, 1338 (synth)
Doyle, P. et a/, J. Chern. Soc., I965, 1344 (synth)
Ackroyd, J. et a/, Helv. Chim. Acta, I984, 67, 1963 (synth, bib/)

616
Pseudoclovene A - 9(12)-Capnellene-2,5,8,10-tetrol Sq-02601 - Sq-02607

Pseudoclovene A Sq-02601 Gadwood, R.C., J. Chern. Soc., Chern. Commun., 1985, 123 (synth)
pseudo-Clovene A Hayasaka, K. et a/, Tetrahedron Lett., 1985, 26, 873 (synth)
[20212-91-3]

Absolute
configuration Capnellanes
CtsH:w M 204.355
Oil.
Ferguson, G. et a/, J. Chern. Soc., Chern. Commun., 1967, 1123 9(12)-Capnellene Sq-02605
(synth) 8(1 3)-Capnel/ene
Hawley, D.M. et aJ, J. Chern. Soc. B, 1969, 599 (abs corifig)
[68349-51-9]

Precapnellanes
C15H 24 M 204.355
Constit. of Capnella imbricata. Oil. [ex]~ - 145° (c, 0.4 in
CHC1 3).
3,10-Precapnellad.iene Sq-02602
Ayanoglu, E. eta/, Tetrahedron Lett., 1978, 1671 (isol)
Precaplll!lladiene Stevens, K.E. eta/, Tetrahedron Lett., 1981, 22, 4393 (synth)
(72715-05-0] Fujita, T. eta/, Tetrahedron Lett., 1982, 23, 4091 (synth)
Oppolzer, W. eta/, Tetrahedron Lett., 1982, 23, 4669 (synth)
Little, D.R. eta/, J. Am. Chern. Soc., 1983, 105, 928 (synth)
Mehta, G. eta/, J. Chern. Soc., Chern. Commun., 1983, 824 (synth)
Paquette, L.A. eta/, Can. J. Chern., 1984, 62, 2415 (synth)
lyoda, M. eta/, J. Chern. Soc., Chern. Commun., 1987, 1607
(synth)
Wang, Y. eta/, J. Org. Chern., 1990, 55, 4504 (synth)
Meyers, A.I. eta/, J. Org. Chern., 1990, 55, 791, 3966 (synth)
C 15H 24 M 204.355 Stille, J.R. eta/, J. Org. Chern., 1990, 55, 843 (synth)
Constit. of Capnella imbricata. Oil.
Ayanoglu, E. eta/, Tetrahedron, 1979, 35, 1035 (iso/, struct) 9(12)-Capnellene-8,10-d.iol Sq-02606
Mehta, G. et a/, J. Org. Chern., 1987, 52, 2875 (synth)
Petasis, N.A. eta/, Tetrahedron Lett., 1990, 31, 6799 (synth)

4(13)-Precapnellene-3,6-d.iol Sq-02603 ~OH

C15H 240 2 M 236.353
(BfJ,JOrx.)-form (61228-59-9]
Constit. of Capnella imbricata. Cryst. (hexane). Mp 113-
IW. [cx]i;l +41° (c, 0.15 in CHC1 3).
C 15H 160 2 M 238.369
Sheikh, Y.M. eta/, Tetrahedron, 1976, 32, 1171 (isol, struct)
(3rx.,6fJ,9fJH)-form [67382-31-4] Poitediol Pattenden, G. et a/, J. Chern. Soc., Perkin Trans. 1, 1988, 1077
Constit. of Laurencia poitei. Mp ca. 40°. [cx] 0 -62.6° (c, (synth)
4.3 in CHC1 3).
Fenical, W. et a/, J. Org. Chern., 1978, 43, 3628 (isol, struct) 9(12)-Capnellene-2,5,8,1 0-tetrol Sq-02607
Gadwood, R.C. eta/, J. Am. Chern. Soc., 1984, 106, 3869 (synth)

3-Precapnellen-6-ol Sq-02604

~
C 15H 160 M 222.370
~ C15H 240 4 M 268.352
(2/l,Srx.,BfJ,J Orx. )-form [71596-73-1]
Constit. of Capnella imbricata. Cryst. (EtOH). Mp 219°.
6fl-form [58542-75-9] Dactylol [cx]i; + 17° (c, 0.9 in MeOH).
Constit. of Aplysia dactylomela. Cryst. (hexane). Mp 8-Ac: [97480-34-7]. 8fl-Acetoxy-9(12)-capnellene-2fJ,5rx.,JOrx.-
50.3-51.5°. (cx] 0 +22.SO (c, 1.76 in CHC1 3). triol
Schmitz, F.J. eta/, Tetrahedron, 1978, 34, 2719 (isol) Ct1H160 5 M 310.389

617
9(12)-Capnellene-3,8,10,14-tetrol - 4,15:6,7-Diepoxy-1,8-dihydroxy-5-... Sq-02608 - Sq-02612

Constit. of C. imbricata. Karlsson, R., Acta Crystallogr., Sect. B, 1977, 33, 1143 (cryst
2,5-Di-Ac: [97480-29-0]. 2P,5rz-Diacetoxy-9(12)-capnellene- struct)
Kaisin, M. eta/, Tetrahedron, 1985, 41, 1067 (deriv)
8P,l Orz-diol
Ct,H280 6 M 352.427
Constit. of C. imbricata. Cryst. (Et20jhexane). Mp 65- 9(12)-Capnellene-5,8, 10-triol Sq-02611
660.
Kaisin, M. et a/, Bull. Soc. Chim. Be/g., 1979, 88, 253 (isol, struct)
Kaisin, M. et a/, Tetrahedron, 1985, 41, 1067 (isol, deriv)

9(12)-Capnellene-3,8,10,14-tetrol Sq-02608

HOH,~OH C 15H 240 3 M 252.353

(5rz,8P,10rz)-form [61228-60-2]
Constit. of Capnella imbricata. Cryst. (EtzO). Mp 132-
1330. [o:]i} + 34.02° (c, 1.3 in CHC1 3).
HO 5-Ac: [97480-27-8]. 5rz-Acetoxy-9(12)-capnellene-8p,JOrz-diol
C 15H 240 4 M 268.352 C 17H 260 4 M 294.390
(Jp,Sp,JOrz)-form [65563-83-9] Constit. of C. imbricata. Cryst. (hexane). Mp 94-96°.
Constit. of Capnella imbricata. Cryst. Mp 192-195°. 8-Ac: [97480-30-3]. 8P-Acetoxy-9(12)-capnellene-5rz,10rz-diol
8-Ac: [97480-32-5]. 8P-Acetoxy-9(12)-capnellene-3p,JOrz,l4- C 17H 260 4 M 294.390
triol Constit. of C. imbricata.
C 17HuPs M 310.389 Sheikh, Y.M. eta/, Tetrahedron, 1976, 32, 1171 (iso/)
Constit. of C. imbricata. Kaisin, M. eta/, Tetrahedron, 1985, 41, 1067 (deriv)
3,14-Di-Ac: 3p,J4-Diacetoxy-9(12)-capnellene-8P,10rz-diol
C 1,H280 6 M 352.427
Constit. of C. imbricata.
Sheikh, Y.M. eta/, Tetrahedron, 1977, 33, 2115 (isol)
Kaisin, M. eta/, Tetrahedron, 1985, 41, 1067 (isol)
Mase, T. eta/, Tetrahedron Lett., 1986, 27, 5245 (synth) Hirsutanes
9(12)-Capnellene-2,8,10-triol Sq-02609

4,15:6,7-Diepoxy-1,8-dihydroxy-5- Sq-02612
hirsutanone
OH

C 15H 240 3 M 252.353 0~

~
Absolute
[61228-61-3]
(2~,8P,10rz)-form
configuration
Constit. of Capnella imbricata. Oil.
2-Ac: [97480-31-4]. 2-Acetoxy-9(12)-capnelleRe-Sp,JOrz-diol C15H 200 5 M 280.320
C17Hu;04 M 294.390
I> WH0203000.
Constit. of C. imbricata.
(lrz,4P,6P,7P,8p)-form [33404-85-2] Coriolin
Sheikh, Y.M. eta/, Tetrahedron, 1976, 32, 1171 (iso/)
Kaisin, M. eta/, Tetrahedron, 1985, 41, 1067 (deriv) Metab. of Corio/us consors. Antibiotic active against
gram-positive bacteria, Trichomonas and Yoshida
sarcoma cells. Cryst. Mp 175°. [o:ln -20.7° (c, 0.03 in
9(12)-Capnellene-3,8,10-triol Sq-02610 CHC1 3).
I> WH0203000.

~OH 1-0ctanoyl: [33400-89-4]. Coriolin B

C23H 340 6 M 406.518
Metab. of C. consors. Shows antitumour props. Cryst.
Mp 215-216°.
1-(2-Hydroxyoctanoyl): [33400-90-7]. Coriolin C
HO
C23H 340 7 M 422.517
C 15H 240 3 M 252.353 Metab. of C. consors.
(3p,sp,lOrz)-form [54928-07-3] (±)-form [74183-96-3]
Constit. of Capnella imbricata. Cryst. (Et 20). Mp 114- Mp 151-154°.
1170. [o:Jn +2° (c, 0.31 in CHCI 3). [74183-95-2]
3-Ac: [97480-26-7]. 3P-Acetoxy-9(12)-capnellene-8p,JOrz-diol Takahashi, S. eta/, Tetrahedron Lett., 1969, 4663; 1970, 1637;
C 17H 260 4 M 294.390 1971, 1955 (iso/, struct)
Constit. of C. imbricata. Nakamura, H. et al, J. Antibiot., 1974, 27, 301 (abs config)
Sheikh, Y.M. eta/, Tetrahedron, 1976, 32, 1171 (iso/, struct) Danishefsky, S. et al, Tetrahedron Lett., 1980, 3439 (synth)
Shibasaki, M. eta/, Tetrahedron Lett., 1980, 3587 (synth)
Trost, B.M. et a/, J. Am. Chern. Soc., 1981, 103, 7380 (synth)

618
6,7-Epoxy-5-hydroxy-4(15)-hirsuten-... - 9-Hydroxy-6-hirsuten-5-one Sq-02613 - Sq-02617

Hifwx
Tatsuta, K. eta/, Tetrahedron, 1981, 37, 4365 (synth) 5,7,9-Hirsutanetriol Sq-02615
lseki, K. et a/, Tetrahedron, 1981, 37, 4411 (synth)
Mehta, G. eta/, J. Chern. Soc., Chern. Commun., 1982, 540 (synth) HO $)H
Koreeda, M. eta/, J. Am. Chern. Soc., 1983, 105, 7203 (synth)
Wender, P.A. eta/, Tetrahedron Lett., 1983, 24, 5325 (synth)
Demuth, M. eta/, Helv. Chim. Acta, 1984, 67, 2023 (synth)
Ito, T. eta/, Tetrahedron, 1984, 40, 241 (synth)
Schuda, P.F. et a/, Tetrahedron, 1984, 40, 2365 (synth)
Demuth, M. eta/, J. Am. Chern. Soc., 1986, 108, 4149 (bibl) C 15H 21,03 M 254.369
Van Hijfte, L. et a/, J. Org. Chern., 1987, 52, 4647 (synth)
(5rT.,7ft,9rT.)-form
Arthrosporol
6,7-Epoxy-5-hydroxy-4(15)-hirsuten-12-oic Sq-02613 Metab. of an unidentified fungus (UMAH 4262). Cryst.
acid (Et20). Mp 163-164°. [ocJn -29° (c, 2 in CHCI 3).
5-Ketone: 7,9-Dihydroxy-5-hirsutanone. Arthrosporone
0 ti CtsH 240 3 M 252.353

~CXXJH
H
~ Amouzou, E. et a/, J. Nat. Prod. (Lloydia), 1989, 52, 1042 (iso/,
C 15H 200 4 M 264.321
(5p,6p,7/l)-form [3650-17-7] Hirsutic acid C
Metab. of Stereum hirsutum. Cryst. (EtOH). Mp 182°.
[ocm + 1w (c, 1 in CHCI 3).
5-Ketone: [51741-93-6]. 6ft,7ft-Epoxy-5-oxo-4(15)-hirsuten-
12-oic acid. Complicatic acid_ Dehydrohirsutic acid C.
Hirsutic acid N
C 15Ht80 4 M 262.305
Metab. of S. complicatum. Shows antibiotic activity. Oil.
[ocJn -79° (c, 1.1 in CHCI 3).
Comer, F.W. et a/, J. Chern. Soc. B, 1966, II (cryst struct)
Comer, F.W. eta/, Tetrahedron, 1967, 23, 4761 (struct)
Sarkar, T.K., J. Chern. Soc., Perkin Trans. I, 1973, 2454 (synth)
Mellows, G. eta/, Phytochemistry, 1973, 12, 2717 (isol, struct,
deriv)
Feline, T.C. et a/, J. Chern. Soc., Chern. Commun., 1974, 63
(biosynth)
Hashimoto, H. eta/, Tetrahedron Lett., 1974, 3745 (synth)
Trost, B.M. et a/, J. Am. Chern. Soc., 1979, 101, 1284 (synth)
Shibasaki, M. eta/, Tetrahedron Lett., 1982, 23, 5311 (synth)
Greene, A.E. eta/, J. Org. Chern., 1985, 50, 3957 (synth)
Schuda, P.F. eta/, J. Org. Chern., 1986, 51, 2742 (synth, bib/)
6,7-Epoxy-1-hydroxy-4(15)-hirsuten-5-one Sq-02614
0 H
Metab. of fungus UAMH 4262. Cryst. (Etpjhexane).
Mp 139-141°. [1X]n -140.8° (c, 0.9 in CHCI 3).
pmr)
4(15)-Hirsutene Sq-02616
Decahydro-2,3,3b-trimethyl-4-methylene-JH-
cyclopenta[a]pentalene, 9Cl. Hirsutene
[59372-72-4]
C 15H 24 M 204.355
Metab. of Corio/us co~ors. Oil.
Nozoe, S. et a/, Tetrahedron Lett., 1976, 195 (struct, synth)
Misumi, S. eta/, Chern. Lett., 1982, 855 (synth)
Dawson, B.A. eta/, Can. J. Chern., 1984, 62, 2521 (synth, bib/)
Funk, R.L. eta/, J. Org. Chern., 1984, 49, 5021 (synth)
Hewson, A.T. eta/, J. Chern. Soc., Perkin Trans. I, 1985, 2625
(synth)
Magnus, P. eta/, J. Org. Chern., 1985, 50, 1621 (synth)
Curran, D.P. eta/, Tetrahedron, 1985, 41, 3943 (synth)
Ley, S.V. eta/, Tetrahedron, 1985, 41, 4765 (synth)
Iyoda, M. eta/, J. Chern. Soc., Chern. Commun., 1986, 1049
(synth)
Disanayaka, B.W. eta/, J. Org. Chern., 1987, 52, 2905 (synth)
Hua, D.H. eta/, J. Org. Chern., 1988, 53, 507 (synth)

~
Sternbach, D.O. eta/, J. Org. Chern., 1990, 55, 2725 (synth)
Cossy, J. et a/, Tetrahedron, 1990, 46, 1859 (synth)
Sarkar, T.K. eta/, Tetrahedron Lett., 1990, 31, 3465 (synth)

9-Hydroxy-6-hirsuten-5-one Sq-02617
C 15H 200 3 M 248.321
Sesquiterpene antibiotic.
(lrT.,6ft,7/1)-form [80677-96-9] Hypnophilin
Prod. by Pleurotel/us hypnophilus. Active against gram-
positive and -negative bacteria, fungi, yeasts and
tumours. Oil. [oc]~ -82.9° (c, 0.9 in CHC1 3). Similar to
Coriolin and Pleurotellic acid.
C 15H 210z M 234.338
Kupka, J. eta/, Arch. Microbiol., 1981, 130, 223 (isol, props)
Steglich, W., Pure Appl. Chern., 1981, 53, 1233 (rev)
91T.-form
Giannetti, B.M. et a/, Tetrahedron, 1986, 42, 3587. Anhydroarthrosporone
Van Hijfte, L. eta/, J. Org. Chern., 1987, 52, 4647 (synth) Metab. of an unidentified fungus (UAMH 4262). Cryst.
Fevig, T.L. eta/, J. Am. Chern. Soc., 1988, 110, 5064 (synth) (Etpjhexane). Mp 118-119°. [ocln +62° (c, 2 in CHCI 3).
Weinges, K. et a/, Angew. Chern., Int. Ed. Engl., 1990, 29, 682 Amouzou, E. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 1042 (iso/,
(synth) pmr)

619
Ceratopicanol - Pentalenolactone Sq-02618 - Sq-02622

Rearranged hirsutanes Pentalenanes

Ceratopicanol Sq-02618 Pentalenene Sq-02620

[115873-01-3] 1,2,3,3a,5a,6,7,8-0ctahydro-J ,4,7,7-
tetramethy/cyc/openta[c]penta/ene, 9CI
H [73306-73-7]

HO~~ H
~'
I

C1sH260 M 222.370
Metab. of fungus Ceratocystis piceae. Gum. [cx]i? +6.4° (c,
0.50 in CHC1 3).
Hanssen, H.-P. et al, Tetrahedron, 1988, 44, 2175 (struct)
C1sH 24 M 204.355
~
Metab. of Streptomyces griseochromogenes. Oil.
Seto, H. et al, J. Antibiot., 1980, 33, 92 (isol)
Pleurotellol Sq-02619 Paquette, L.A. et al, J. Am. Chern. Soc., 1983, 105, 7358 (synth)
[80677-95-8] Cane, D.E. et al, Bioorg. Chern., 1984, 12, 312 (biosynth)
Piers, E. et al, J. Chern. Soc., Chern. Commun., 1984, 959 (synth)
Mehta, G. et al, J. Am. Chern. Soc., 1986, 108, 8015 (synth)
Pattenden, G. et a/, Tetrahedron, 1987, 43, 5637 (synth)
Hudlicky, T. et al, Tetrahedron, 1987, 43, 5685 (synth)
Ihara, M. et al, J. Chern. Soc., Perkin Trans. 1, 1988, 2963 (synth)
Piers, E. et a/, Can. J. Chern., 1989, 67, 160 (synth)
Shizuri, Y. et al, Tetrahedron Lett., 1990, 31, 7167 (synth)
CtsHt80 3 M 246.305
Sesquiterpene antibiotic. From Pleurotel/us hypnophilus. Pentalenic acid Sq-02621
Active against gram-positive and -negative bacteria, [69394-19-0]
fungi, yeasts and tumours. Oil. [cx]i? -86.SO (c, 0.015 in
CHC1 3). H<;> H
Carboxylic acid: [80677-94-7]. Pleurotellic acid
CtsHt 60 4 M 260.289
Prod. by P. hypnophilus. Active against gram-positive
and -negative bacteria, fungi and tumours. Needles. Mp
148°. [cx]i? -70.8° (c, O.o7 in CHC1 3).
>QJ~"
Kupka, J. et al, Arch. Microbial., 1981, 130, 223 (isol, props)
C1sH 220 3 M 250.337
Giannetti, B.M. et al, Tetrahedron, 1986, 42, 3587. Metab. of Streptomyces spp.
Seto, H. et al, Tetrahedron Lett., 1978, 4411 (isol)
Crimmins, M.T. et al, J. Org. Chern., 1984, 49, 2076 (synth)
Hud1icky, T. eta/, Tetrahedron, 1987, 43, 5685 (synth)
Ihara, M. et al, J. Chern. Soc., Perkin Trans. 1, 1988, 2963 (synth)

Pentalenolactone Sq-02622
Arenemycin E. P A 132. Antibiotic P A 132
[31501-48-1]

C 1sH 160s M 276.288

Sesquiterpene antibiotic. lsol. from Streptomyces sp. 8403
MC 1• Tumour inhibitor. Cryst. Mp 61-62°. [cx]i! -172°
(c, 1 in MeOH).
t> WH1317900.
Takeuchi, S. et al, Tetrahedron Lett., 1969, 2737; 1977, 2943 (isol,
struct, ir, uv, ms, pmr, cmr)
Martin, D.G. et al, Tetrahedron Lett., 1970, 4901 (cryst struct)
Keller-Schierlein, W. eta/, Arch. Microbial., 1972, 84, 301 (isol, uv,
ir, pmr)

620
Pentalenolactone E- 5,11-Dihydroxy-1-silphinen-3-one Sq-02623 - Sq-02627

Danishefsky, S. et al, J. Am. Chern. Soc., 1978, 100, 6536 (synth) Sesquiterpene antibiotic. lsol. from Streptomyces
Cane, D.E. et al, J. Am. Chern. Soc., 1981, 103, 1838 (biosynth) chromofuscus, S. arenae and S. omiyaensis. Mp 203-205°.
Plavac, F., Diss. Abstr. Int., B, 1982, 42, 4798 (synth) [rx]~ -160.1° (c, 3 in CHC1 3).
Keller-Schierlein, W. eta[, Arch. Microbiol., 1972, 84, 301 (isol, uv,
Pentalenolactone E Sq-02623 ir, pmr, props)
[72715-03-8] Seto, H. et al, J. Antibiot., 1984, 37, 1076 (isol, ir, pmr, cmr)

H Pentalenolactone P Sq-02626
Xi)cooH [93361-68-3]

C1sHt80 4 M 262.305
1,)H
J-o -mCOOH
ti~H
Sesquiterpene antibiotic. Constit. of Streptomyces spp.
Cane, D.E. eta[, Tetrahedron Lett., 1979, 2973 (isol) 0 0
Paquette, L.A. eta[, J. Am. Chern. Soc., 1981, 103, 6526 (synth) C15H 160 5 M 276.288
Ohtsuka, T. et al, Tetrahedron Lett., 1983, 24, 3851 (synth) Sesquiterpene antibiotic. Isol. from Streptomyces
Thomas, P.J. et al, J. Am. Chern. Soc., 1984, 106, 5295 (synth) omiyaensis and S. chromofuscus.
Marino, J.P. et al, J. Org. Chern., 1987, 52, 4139 (synth)
Taber, D.F. et al, Tetrahedron, 1987, 43, 5677 (synth) Keller-Schierlein, W. et al, Arch. Microbiol., 1972, 84, 301 (isol)
Hua, D.H. eta[, Tetrahedron Lett., 1987, 28, 5465 (synth) Seto, H. et al, J. Antibiot., 1984, 37, 1076 (isol, struct)
Mori, K. et al, Tetrahedron, 1988, 44, 2835 (synth)

Pentalenolactone F Sq-02624
[85416-36-0]
HI Silphinanes
if)~" 5,11-Dihydroxy-1-silphinen-3-one Sq-02627

~em
C 15H 180 5 M 278.304
Sesquiterpene antibiotic. lsol. from Streptomyces sp.
Intermed. in biosynth. of other Pentaleno1actones. Oil.
Struct. shown has recently been corrected from 9-
epimer.
1rx-Hydroxy: [70206-77-8]. Pentalenolactone H o
CtsHt80 6 M 294.304 C 15H 220 3 M 250.337
Metab. of S. spp. Oil.
5-Angeloyl: 5rx.-Angeloyloxy-II fJ-hydroxysilphinen-3-one
9-Epimer, 1-oxo: [67055-57-6]. Pentalenolllctone G
C28H 280 4 M 332.439
CtsH 160 6 M 292.288
lsol. from Cineraria geifo/ia var. glabra.
lsol. from S. sp. Mp 125.SO (as Me ester).
5-Ange/oy/, 11-Ac: llfJ-Acetoxy-5rx.-angeloyloxysilphinen-3-
Seto, H. et al, Tetrahedron Lett., 1978, 923, 4411 (isol, cmr, struct,
deriv) one
Danishefsky, S. et al, J. Am. Chern. Soc., 1979, 101, 7020 (synth) C22 HJ(,05 M 374.476
Parsons, W.H. et al, J. Am. Chern. Soc., 1980, 102, 889 (synth) Isol. from C. geifolia. [rxln -69° (c, 0.7 in CHC13).
Cane, D.E. et al, J. Am. Chern. Soc., 1981, 103, 1838 (biosynth) 5- Tigloy/, 11-Ac: II fl-Acetoxy-5rx.-tigwyloxysilphinell-3-one
Tillman, A.M. et al, J. Antibiot., 1983, 36, 170 (deriv) CnH300 5 M 374.476
Ohtsuka, T. et al, Tetrahedron Lett., 1983, 3851 (synth) lsol. from C. geifo/ia.
Cane, D.E. et al, J. Am. Chern. Soc., 1984, 106, 5295 (synth)
Seto, H. eta[, J. Antibiot., 1984, 37, 816 (pmr, cmr, cryst struct) 5-(2-Methy/propanoyl), 11-Ac: llfJ-Acetoxy-5rx.-
Pirrung, M.C. et al, J. Org. Chern., 1988, 53, 227 (synth) isobutyryloxysilphinen-3-one
C21 H 300 5 M 362.465
From C. geifolia.
Pentalenolactone 0 Sq-02625
Arenemycin D 5-Propanoy/, 11-Ac: IIfJ-Acetoxy-5rx.-propionyloxysilphinell-
3-one
[93361-64-9]
C20H 280 5 M 348.438
From C. geifolia.

--(h:;uou
Jakupovic, J. et al, Phytochemistry, 1985, 24, 3048.

HO
~p
M 294.304

621
1-Silphinene - 2-Silphiperfolanol Sq-02628 - Sq-02633

1-Silpbinene Sq-02628
Silphinene
[74284-57-4] Silphiperfolanes
'-/)
cb< I
I
5-Hydroxy-6-silpbiperfolen-13-oic acid Sq-02631

'$-~H
C15H24 M 204.355
Constit. of Silphium perfoliatum. Oil. [cx]t' -21.3° (c, 3.7 in
CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 259 (isol)
Leone-Bay, A. eta/, J. Org. Chern., 1982, 47, 4113 (synth) OH
Paquette, L.A. eta/, J. Am. Chern. Soc., 1983, 105, 7352 (synth)
Tsunoda, T. et a/, Tetrahedron Lett., 1983, 24, 83 (synth) C 15H 220 3 M 250.337
Sternbach, D.D. eta/, J. Am. Chern. Soc., 1985, 107, 2149 (synth) 5/l-form [106941-43-9] Cantabrenolic acid
Wender, P.A. eta/, Tetrahedron Lett., 1985, 26, 2625 (synth) Constit. of Artemisia cantabrica':
Crimmins, M.T. eta/, Tetrahedron Lett., 1987, 28, 5063 (synth)
Me ester: [106941-36-0].
Viscous oil. [cxJt' -47.9° (c, 1.2 in CHC1 3).
1-Silpbinene-3,5-d.iol Sq-02629 5-Ketone: [106941-40-6]. 5-0xo-6-si/phiperfolen-13-oic acid.
3,5-Si/phinenedio/ Cantabrenonic acid

(29
C15H200 3 M 248.321
From A. cantabrica.
5-Ketone, Me ester: [106941-35-9].
Cryst. (hexane). Mp 70°. [cx]t' -36.9° (c, 1 in CHC1 3).
5-Ketone, 6cx,7cx-epoxide: [106941-42-8]. 6,7-Epoxy-5-oxo-6-
Hd ' (m silphiperfo/en-13-oic acid. Epoxycantabronic acid
C 15Hu02 M 236.353 C15H2004 M 264.321
Revised stereochem., but still not certain. From A. cantabrica.
5-(3-Methy/butanoyl): [81957-79-1]. 5-Ketone, 6cx,7cx-epoxide, Me ester: [106941-34-8].
C 10H 320 3 M 320.471 Cryst. (hexane). Mp 63°. [cxJt' -5.2° (c, 0.8 in CHCI 3).
Constit. of Cal/ilepis salicifolia. Oil. [cx]t' + 14.SO (c, 3 in San Feliciano, A. eta/, J. Nat. Prod. (Lioydia), 1986, 49, 845 (isol,
CHC1 3). struct)
3-Ketone, 5-Ac: Srr.-Acetoxysilphinen-3-one Piers, E. et a/, J. Chern. Soc., Chern. Commun., 1990, 1324 (synth)
C 17H 240 3 M 276.375
Isol. from Cineraria geifolia var. glabra. 11-0xo-5-silpbiperfolen-13-oic acid Sq-02632
3-Ketone, 5-propanoy/: Srr.-Propionyloxysilphinene-3-one Subergorgic acid
CtaH2603 M 290.402 [97718-45-1]
lsol. from C. geifolia.
3-Ketone, 5-ange/oy/: Srr.-Angeloyloxysilphinen-3-one
<;Jl280 3 M 316.439
Isol. from C. geifolia.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 139; 1985, 24, 3048.

3-Silpbinenone Sq-02630 C 15H 100 3 M 248.321

3-0xosi/phinene Constit. of coral Subergorgia suberosa. Shows cardiotoxic
props. Cryst. Mp 179-180°, Mp 200-202°.
[84607-62-5]
Wu, Z. et a/, CA, 1982, 98, 68827 (isol)
Groweiss, A. eta/, Tetrahedron Lett., 1985, 26, 2379 (cryst struct)
Iwata, C. eta/, J. Org. Chern., 1988, 53, 1623 (synth)

C 15H 220 M 218.338 2-Silpbiperfolanol Sq-02633

Constit. of Dugaldia hoopesii. Oil. Bp0_1 85°. [cx] 0 +7.1° (c, [124649-23-6]
0.4 in CHC1 3).
Bohlmann, F. eta/, J. Nat. Prod. (Uoydia), 1984, 47, 658 (isol)
Ihara, M. eta/, J. Chern. Soc., Perkin Trans. 1, 1987, 1331 (synth)
Ue, M. eta/, Chern. Lett., 1990, 149 (synth)

M 222.370

622
5,7(14)-Silphiperfoladien-13-... - 5-Silphiperfolen-3-ol Sq-02634 - Sq-02639

Metab. of Laurencia majuscula. Oil. [aln -57° (c, 0.01 in Constit. of S. perfoliatum. Oil. [ali: -100.3° (c, 1.9 in
CHC1 3). CHC13).
[124596-90-3) Bohlmann, F. et al, Phytochemistry, 1980, 19, 259.
Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1591 (isol, pmr, cmr)
6-Silpbiperfolene Sq-02638
5,7(14)-Silpbiperfoladien-13-oic acid Sq-G2634 [74284-56-3)

d:>-
Cantabradienic acid
[106941-41-71

1
I

C15H24 M 204.355
Constit. of Siliphium perfoliatum. Oil. [oc]~4 -92.8° (c, 0.8
Ct5Hllp2 M 232.322 in CHC1 3).
Constit. of Artemisia cantabrica. Bohlmann, F. eta/, Phytochemistry, 1980, 19, 259.
Me ester: [106941-33-7]. Curran, D.P. et al, Tetrahedron, 1987, 43, 5653 (synth)
Pale-yellow oil. [ali: -22.3° (c, 0.5 in CHCI 3). Meyers, A.I. eta/, Tetrahedron, 1987, 43, 5663 (synth)
San Feliciano, A. et al, J. Nat. Prod. (Lioydia), 1986, 49, 845.
5-Silpbiperfolen-3-ol Sq-02639
6-Silpbiperfolanol Sq-02635

C15H1,o M 212.291 Ct5H 240 M 220.354

Metab. of Laurencia majuscula. Oil. [aln -19.4° (c, 0.3 in 3P-form
CHCI 3). Constit. of Artemisia laciniata. Oil.
Wright, A.D. et a/, J. Nat. Prod. (Lioydia), 1990, 53, 845 (isol, Brendel, J. eta/, Tetrahedron Lett., 1989, 30, 2371 (synth)
pmr, cmr)

5-Silpbiperfolanone Sq-02636
5-0xo-5,6-dihydrosi/phiperfolene
[75088-71-0l

Y\/
(t?-- 1 0
C 15H 240 M 220.354
Constit. of Liabum fiorihundum. Oil. [al~4 - 173° (c, 1.4 in
CHC13).
6,7-Didehydro: [77887-60-6]. 6-Si/p/ri/perfolen-5-one
C 15H 220 M 218.338
lsol. from Espeletiopsis guacharaca. Oil. [ali: -40° (c,
1.3 in CHCI3).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 579.

5-Silpbiperfolene Sq-G2637

C 15H 24
ffl-
M 204.355
1
I
7a.H-form

7rx.H-form [74284-82-51
Constit. of Siliphium perfoliatum. Oil. [ali: -31.5° (c,
0.65 in CHCI 3).
7PH-form [74311-20-91

623
2,5,8-Presilphiperfolanetriol - 2-Isocomene Sq-02840 - Sq-02644

Presilphiperfolanes Isocomanes

2,5,8-Presilphiperfolanetriol Sq-02640 2,11-Cyclo-13-isocomanol Sq-02642

3,5-Cycloisocomen-13-ol
~ [88153-55-3]

H~ I OH £~0H
C 15H~03 M 254.369
C15Hz,.0 M 220.354
(2P,5P.Sfl)-form Constit. of Schistostephium spp. Oil.
2-0-Angeloyl, 5-Ac: 5P-Acetoxy-2p-angeloyloxy-8P- 13-Aldehyde: [88153-54-2]. 2,11-Cyclo-13-isocoiiUUUll. 3,5-
hydroxypresilphiperfolane Cycloisocomen-13-al
CnH340 5 M 378.508 C15Hn0 M 218.338
Constit. of Senecio anteuphorbium. Cryst. (2-propanol). From S. spp. Oil.
Mp 75-75.5°. [ex]n + 11.0° (c, 0.63 in CHCl 3).
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1623.
5-Ketone, 2-angeloyl: 2P-Angeloyloxy-8p-hydroxy-5-
presilphiperfolone
c~ 3804 M 334.455 2-Isocomanone Sq-02643
Constit. of Ursinia nana. Gum. Isocomen-5-one
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1331. [103771-84-2]

8-Presilphiperfolanol
9CI. 8-Hydroxypresilphiperfolene
[80931-08-4]
Sq-02641
Decahydro-1,1,2a,5-tetramethyl-7b-cyclopent[cd]inden-7b-ol,
q} I 0
~ C15Hl40 M 220.354

d)<
Constit. of Helichrysum nudifolium. Oil.
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 1133.

I
I 2-Isocomene Sq-02644
«-lsocomene. Berkheyaradulene. lsocomene
C15Hu;0 M 222.370
[65372-78-3]
BP-form

<55-
Constit. of Eriophyllum staechadifolium and Flourensia
heterolepis. Oil. [ex]~ -18.4° (c, 3.6 in CHC13).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2239.

I
I

C15Hl4 M 204.355
Constit. of lsocoma wrightii and Berkheya radula. Oil.
Bp0 _35 65-70° (bath). [ex]~ -85° (c, 3.5 in CHCl 3).
Bohlmann, F. et al, Chem. Ber., 1977, 110, 3777 (isol)
Zalkow, L.H. eta/, J. Chem. Soc., Chem. Commun., 1977, 456
(isol)
Pirrung, M.C. et al, J. Am. Chem. Soc., 1979, 101, 7130; 1981,
103, 82 (synth)
Paquette, L.A. et al, J. Am. Chem. Soc., 1981, 103, 1835 (synth)
Dauben, W.G. et al, J. Org. Chem., 1981, 46, 1103 (synth)
Oppolzer, W. eta/, Tetrahedron, 1981, 37, 4359 (synth)
Wender, P.A. eta/, Tetrahedron, 1981, 37, 4445 (synth)
Wenkert, E. et al, J. Am. Chem. Soc., 1983, 105, 20JO (synth)
Ranu, B.C. et a/, Tetrahedron Lett., 1984, 25, 2447 (synth)
Tobe, Y. et al, J. Chem. Soc., Chem. Commun., 1985, 898 (synth)
Manzardo, G.G.G. et al, Helv. Chim. Acta, 1986, 69, 659 (synth)
Snider, B.B. et al, J. Org. Chem., 1988, 53, 4508 (synth)

624
3(13)-lsocomene - 10-Panasinsanene Sq-02645 - Sq-02651

3(13)-Isocomene Sq-02645 Constit. of C. salicifolia. Oil.

P-lsocomene 14-Aldehyde: [91940-88-7]. 2-Isocomen-14-al. 12-Isocomenal
[74311-15-2] C 1 ~H 11 0 M 218.338
Constit. of C. salicifolia. Oil.

£} I
I
14-Carboxylic acid, Me ester: Methyl 2-isocomen-14-oate
Ct,H240 1 M 248.364
Constit. of C. salicifolia. Oil.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 139.

Ct~H 24 M 204.355 2-Isocomen-5-one Sq-02649

Constit. of Berkheya spp. Oil.
Arnicenone
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1831 (isol)
Oppolzer, W. et al, Tetrahedron, 1981, 37, 4359 (synth) [76333-73-8]

-l"fo
Tobe, Y. et a/, J. Chern. Soc., Chern. Commun., 1985, 898 (synth)

W-
2-Isocomen-9-ol Sq-02646

Hffi-
1-Hydroxyisocomene
I
I

C 1 ~Hn0 M 218.338
Constit. of Arnica parryi. Cryst. by subl. Mp 80-85°. [oc]~
+614° (c, 0.1 in C6H6).
C1~H240 M 220.354 2,4-Dinitrophenylhydrazone: Cryst. Mp 192°.
9P-form [81427-02-3] Schmitz, R. eta/, Phytochemistry, 1980, 19, 1477.
Constit. of Pulicaria dysenterica. Not obt. pure.
Ac: 9P-Acetoxy-2-isocomene. 1P-Acetoxyisocomene
Ct7Hu;01 M 262.391
Constit. of P. dysenterica. Oil. Bp0. 1 110°. [oc]~ + 76.5°
(c, 1.5 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1981, 20, 2529. Panasinsanes
2-Isocomen-13-ol Sq-02647
13-Hydroxyisocomene
3(15)-Panasinsanene Sq-02650

<t}c~OH
P-Panasinsene
[56684-97-0]

~-
I
I

Ct~H 24 0 M 220.354
Constit. of Schistostephium spp. Oil. [oc]~ -96° (c, 0.13 in
CHC1 3).
13-Aldehyde: 2-Isocomen-13-al. rx.-lsocomen-13-al
C 1 ~Hn0 M 218.338 C 1 ~Hl4 M 204.355
From S. spp. Oil. [oc]~ -108° (c, 0.13 in CHC1 3). Constit. of the oil of Panax ginseng. Oil. [oc]~ -3°
(MeOH).
13-Carboxylic acid: 2-Isocomen-13-oic acid. rx.-lsocomen-13-
oic acid Yoshihara, K. et al, Bull. Chern. Soc. Jpn., 1975, 48, 2078.
McMurry, J.E. eta/, Tetrahedron Lett., 1980, 2477 (synth)
C 1 ~Hn0 1 M 234.338
From S. spp. Oil. [oc]~4 -49° (c, 0.67 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1983, 22, 1623. 10-Panasinsanene Sq-02651
rx.-Panasinsene
2-Isocomen-14-ol [56633-28-4]
Sq-02648
12-Hydroxyisocomene

~-
[81915-89-1]

(!poH Ct~H 24 M 204.355

I
I Constit. of the oil of Panax ginseng. Oil.
Ct~H 24 0 M 220.354 Yoshihara, K. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 2078 (isol,
Constit. of Callilepis salicifolia. Oil. [oc]~ -78° (c, 0.6 in struct)
CHC1 3). McMurry, J.E. et al, Tetrahedron Lett., 1980, 2477 (synth)
3-Methylbutanoyl:
CzoH310 1 M 304.472

625
3-Panasinsanol - Quadrone Sq-02652 - Sq-02657

3-Panasinsanol Sq-02652 Constit. of Liabum eggersii. Oil. Bp 0 . 1 130°.

l:i-->
2,4-Dinitrobenzoyl: Cryst. (MeOH). Mp 89°.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 579.

Hd(J--
3a0H-fo'm
9-0xo-2-modhephen-14-al Sq-02655
Pulicaral
[119767-05-4]
C 15H 260 M 222.370 12 0

¢OS
JrxOH-form [109785-99-1] Panasinsanol B
C 15H 260 M 222.370
Constit. of Panax ginseng. Oil. [a]i;' -44.3° (c, 0.70 in
CHC1 3).
JPOH-form [80374-27-2] Panasinsanol A
Constit. of P. ginseng. Oil. (a]i;' -51.9° (c, 0.54 in C15H200 2 M 232.322
CHC1 3). Constit. of Pulicaria paludosa. Cryst. (CH 2Cl 2). Mp 70°.
Iwabuchi, H. et al, Chern. Pharm. Bull., 1987, 35, 1975. (a]i;l -58.9° (c, 0.3 in CHCI 3).
12-Carboxylic acid: (119767-06-5]. 9-0xo-2-modhephen-14-
carboxylic acid. Pulicaric acid
C15H 200 3 M 248.321
Constit. of P. paludosa. Oil. [1X]~4 -57.6° (c, 0.7 in

Modhephanes
CHCI 3).
San Feliciano, A. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1153
(isol, pmr, cmr)

2-Modhephene Sq-02653
Modhephene
[68269-87-4] Quadranes

lsoquadrone Sq-02656
[81130-69-0]
C15H24 M 204.355
Constit. of Isocoma wrightii. Oil. Bp 0 . 25 65-70°.

~0
Za1kow, L.H. et al, J. Chern. Soc., Chern. Commun., 1978, 420
(isol)
Za1kow, L.H. et al, J. Nat. Prod. (Lloydia), 1979, 42, 96 (isol)
Karpf, M. et al, Helv. Chim. Acta, 1981, 64, 1123 (synth)
Oppolzer, W. eta/, Helv. Chim. Acta, 1981, 64, 1575, 2489 (synth)
Schostarez, H. et al, Tetrahedron, 1981, 37, 4431 (synth)
Wender, P.A. et al, J. Am. Chern. Soc., 1982, 104, 5805 (synth) ro 0
\ I 6

Smith, A.B. eta/, J. Org. Chern., 1982, 47, 1785 (synth)

Wrobel, J. et al, J. Org. Chern., 1983, 48, 139 (synth) C15H2003 M 248.321
Tobe, Y. eta/, J. Chern. Soc., Chern. Commun., 1984, 1259 (synth) Metab. of Aspergillus terreus. Cryst. (EtOAcjhexane). Mp
Mehta, G. et al, J. Chern. Soc., Chern. Commun., 1985, 768 (synth) 166-167°. [a]i,O -2° (c, 0.9 in CHC1 3).
Mundy, B.P. et al, J. Org. Chern., 1985, 50, 5727 (synth)
Kraus, G.A. et al, J. Org. Chern., 1990, 55, 5423 (synth) 6-Hydroxy: [93078-74-1]. 6-Hydroxyisoquadrone
C15H 2004 M 264.321
From A. terreus. Cryst. (EtOAcjhexane). Mp 159-160°.
Z-Modhephen-12-ol Sq-02654 [a]i,O + 22° (c, I in CHCI 3).
13-Hydroxymodhephene
Nakagawa, M. et a/, Agric. Bioi. Chern., 1984, 48, 2279.
[7 5088-7 5-4]

)-M Quadrone Sq-02657

Octahydro-10,10-dimethyl-6,8b-ethano-8bH-indeno[1,7-

),V-J
I
cd]pyran-1 ,4-dione,9C/
(66550-08-1]
CHzOH
C 15H 240 M 220.354
Oil.
Ac: [75088-74-3]. 0
C 17H 260 2 M 262.391

M 248.321

626
Terrecyclol - Norecasantalol Sq-02658 - Sq-02660

Sesquiterpene antibiotic. Metab. of Aspergillus terreus.

Shows antitumour props. Cryst. (MeOH). Mp 185-186°.
[am -50° (c, 0.1 in EtOH).
8P-Hydroxy: [91682-93-8]. 8-Hydroxyquadrone
Campherenanes
C 15Hllp4 M 264.321
From A. terreus. Shows antitumour props. Cryst.
(EtOAcjhexane). Mp 136-137°. [a]~4 -51° (c, 0.3 in
EtOH). Campherenol Sq-02659
(±)-form [7 4807 -65-1] [18530-03-5]
Mp 140-142°.

~
Ranieri, R.L., Tetrahedron Lett., 1978, 499 (isol, cryst struct)
Burke, S.D. eta/, Tetrahedron Lett., 1983, 24, 2949 (synth)
Cane, D.E. eta/, Tetrahedron Lett., 1984, 25, 1119 (biosynth)
Kon, K. et a/, Tetrahedron Lett., 1984, 25, 3739 (abs config)
Nakagawa, M. eta/, Agric. Bioi. Chern., 1984, 48, 2279 (8- AA~·
Hydroxyquadrone)
Smith, A.B. et a/, J. Org. Chern., 1984, 49, 4094 (synth, abs config, C 15H160 M 222.370
bib£) Constit. of Cinnamomum camphora. Oil. [aln -62.1° (c, 3.9
Iwata, C. eta/, Chern. Pharm. Bull., 1985, 33, 436 (synth) in CHCI 3).
Piers, E. eta/, Tetrahedron Lett., 1985, 26, 2735 (synth) 2-Ketone: [18530-02-4]. Campherenone
Wender, P.A. et a/, J. Org. Chern., 1985, 50, 4418 (synth)
Cane, D.E. eta/, Bioorg. Chern., 1986, 14, 417 (biosynth) ClsH140 M 220.354
Imanishi, T. eta/, J. Chern. Soc., Chern. Commun., 1987, 1802 Constit. of C. camphora. Oil. [aln -33° (c, 10 in
(synth) CHCI 3).
Magnus, P. eta/, J. Org. Chern., 1987, 52, 1483 (synth) 7- Epimer: [18530-04-6]. Epicampherenol. epi-Campherenol
Liu, H.-J. eta/, Can. J. Chern., 1988, 66, 528 (synth) C1 5H 160 M 222.370
Neary, A.P. eta/, J. Chern. Soc., Chern. Commun., 1989, 1090 Oil. [a]D +15.3°.
(synth)
[34051-02-0)
Hikino, H. eta/, Tetrahedron Lett., 1967, 5069 (synth)
Terrecyclol Sq-02658 Eck, C.R. eta/, J. Chern. Soc., Perkin Trans. I, 1974, 1938 (synth,
[90044-37-4] bib£)

~0 I
<fH20H
cx-Santalanes
C 15H120 1 M 234.338
Sesquiterpene antibiotic. Metab. of Aspergillus terreus. Oil.
Norecasantalol Sq-02660
7-Carboxy/ic acid: [83058-94-0]. Terrecyclic acid A 10,11,12,13- Tetranor-a-santa/an-9-o/. Nortricycloekasantalol
ClsH100 3 M 248.321
[59460-65-0]
Metab. of A. terreus. Shows a wide spectrum of
antimicrobial and antitumour props. Cryst.
(hexanejEt 20). Mp 177-179°. [a]~ +33.9° (c, 0.177 in
CHCI 3).
HOH,~
Danishefsky, S. et al, J. Am. Chern. Soc., 1981, 103, 4136 (synth)
Nakagawa, M. et a/, J. Antibiot., 1982, 35, 778, 783 (isol)
Hirota, A. eta/, J. Antibiot., 1982, 35, 783; 1984, 37, 475; 1986,
39, 149 (cmr, struct, abs config) CuH 180 M 166.263
Nakagawa, M. eta/, Agric. Bioi. Chern., 1984, 48, 117. Constit. of Santa/urn album oil. Oil. Bp 10 114-117°.
Hirota, A. eta/, Agric. Bioi. Chern., 1984, 48, 835 (biosynth) Aldehyde: [59300-38-8]. Norecasantalal. 10,11,12,13-
Beale, J.M. eta/, J. Antibiot., 1984, 37, 1376 (biosynth, bib£) Tetranor-a-santa/an-9-a/. Nortricycloekasantalal
Cane, D.E. eta/, Tetrahedron Lett., 1984, 25, 1119 (biosynth) CuH 160 M 164.247
Kon, K. et a/, Tetrahedron Lett., 1984, 25, 3739 (synth, abs config) Constit. of S. album oil. Oil. Bp 222-224°.
Wender, P.A. eta/, J. Org. Chern., 1985, 50, 4418 (synth)
Hirota, A. eta/, Tetrahedron Lett., 1985, 26, 3845 (biosynth) Carboxylic acid: [59300-52-6]. Norecasantalic acid.
Cane, D.E. eta/, Bioorg. Chern., 1986, 14, 417 (biosynth) 10,11,12,13- Tetranor-a-santalan-9-oic acid.
Hirota, A. eta/, J. Antibiot., 1986, 39, 149 (abs config) Nortricycloekasantalic acid
C 11 H 160 1 M 180.246
Constit. of S. album oil. Cryst. (EtOH). Mp 93°. [aln
-33.3° (EtOH).
Demole, E. eta/, Helv. Chim. Acta, 1976, 59, 737.

627
9-0xo-(X-santalan-12-oic acid - (X-Santal-10-en-9-one Sq-02661 - Sq-02667

9-0xo-rx-santalan-12-oic acid Sq-02661 rx-Santal-10-en-12-oic acid Sq-02665

Ketosantalic acid
HOOC
H~
C 15H 110 2 M 234.338
(JOE)-form [74642-79-8] rx.-Santalen-12-oic acid
C 15H 220 3 M 250.337 Constit. of Ayapana amygdalina. Oil.
Constit. of Indian sandalwood oil. Oil. Bp0 . 3 180°. [tx]~ Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1997.
-30° (c, 1.4 in CHC1 3).
Me ester, semicarbazone: Cryst. (EtOH). Mp 183~185°. rx-Santal-1 0-en-12-ol Sq-02666
Ranibai, P. eta/, Indian J. Chern., Sect. B, 1986, 25, 1006. tx-Santalol

rx-Santalan-1 0-one Sq-02662 HOH2 C~

Dihydro-rx.-santalen-10-one. Dihydro-tx-santa/en-12-one
~ (7R,IOE)-form

C 15H 240 M 220.354

Perfumery ingredient.
(7R,JOE)-form [14490-17-6]
Oil. Bp0. 5 113-119°. [tx]~ +18.09° (CHC1 3).
Aldehyde: [59331-83-8]. tx-Santal-10-en-12-al. rx.-Santalal
C 15Hz,P M 220.354
Constit. of Severinia buxifolia. Oil. [tx]i;' +3.7° (c, 1.28 in C 15H 220 M 218.338
Constit. of Santa/urn album. Oil.
CHC1 3).
(7R,10Z)-form [115-71-9]
Wu, T.-S. eta/, Phytochemistry, 1984, 23, 595.
Constit. of sandalwood oil. Oil. Bp 14 166-167°. [tx]i;'
+ 17.SO (c, 3.3 in CHC1 3).
rx-Santal-1 0-ene Sq-02663 t> SB3400000.
rx.-Santalene Aldehyde: [13827-97-9].
[512-61-8] Oil. Bp 10 153°. [tx]~ +35.3° (CHC1 3).
Aldehyde, semicarbazone: Mp 220°.
(7S,JOZ)-form [19903-72-1]
Oil. [tx] 0 -18.6° (c, 3.48 in CHC1 3).
Aldehyde: [19903-70-9].
Constit. of the root of Piqueria trinerva. Oil. Bp0 . 3 105°.
[tx]~ -35.2° (c, 6.25 in CHC1 3).
C 15H 24 M 204.355 Aldehyde, semicarbazone: Mp 223°.
Constit. of sandalwood oil. Oil. Bp753 252°. [tx] 0 -15°.
Lewis, R.G. eta/, Tetrahedron Lett., 1967, 401 (synth)
Epoxide: 10,11-Epoxy-rx.-santa/ane. I 2,I 3-Epoxy-tx-santalene Bohlmann, F. eta/, Tetrahedron Lett., 1968, 1533 (iso/, synth)
C 15H 240 M 220.354 Corey, E.J. et al, J. Am. Chern. Soc., 1970, 92, 6314 (synth)
lsol. from Severinia buxifolia. Oil. [tx]i;' +2.4° (c, 5.5 in Julia, M. eta/, Bull. Soc. Chim. Fr., 1973, 3065 (synth)
CHC1 3). Sato, K. eta/, Bull. Chern. Soc. Jpn., 1976, 49, 3351 (synth)
Demole, E. eta/, Helv. Chim. Acta, 1976, 59, 737 (iso/, aldehyde)
Julia, M. et a/, Bull. Soc. Chim. Fr., 1973, 3065 (synth)
Hodgson, G.L. eta/, J. Chern. Soc., Perkin Trans. I, 1973, 2113
(synth, abs config) rx-Santal-1 0-en-9-one Sq-02667
Monti, S.A. et al, J. Org. Chern., 1978, 43, 2282 (synth) rx.-Santalen-9-one. tx-Santalen-11-one
Wu, T.-S. et a/, Phytochemistry, 1984, 23, 595 (epoxide)

rx-Santal-10-ene-12,15-dioic acid Sq-02664

H~ C 15H 110 M 218.338

Constit. of Severinia buxifo/ia. Oil. [tx]i;' -47.8° (c, 5 in
COOH CHC1 3).
Wu, T.-S. eta/, Phytochemistry, 1984, 23, 595.
C 15H 200 4 M 264.321
(10E)-form [74513-99-8] rx.-Santalene-12,15-dioic acid
Constit. of Ayapana amygdalina. Oil.
Di-Me ester: Oil. [tx]i: -7.2° (c, 0.33 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1997.

628
Santalone - P-Santal-10-ene-3,8-diol Sq-02668 - Sq-02672

Santalone Sq-02668 ~Santala-3(15),1 0-dien-12-ol Sq-02671

10,11,12,13- Tetranor-a.-santalan-8-one
[59300-51-5]
0 (10Z}:form

C 11H 160 M 164.247

4;:; CISH240
(JOZ)-form [77-42-9] fJ-Santalol
Constit. of sandalwood oil (Santalum album). Perfumery
ingredient. Oil. Bp 17 177-178°. [a.]46 -87.1°.
Constit. of the oil of Santalum album. Oil. (JOE)-form
Demole, E. et al, Helv. Chim. Acta, 1976, 59, 737. Aldehyde: [59331-82-7]. P-Santal-3(15), 10-dien-12-al. P-
Santalal
C 15H 120 M 218.338
lsol. from S. album oil.
Demole, E. et al, Helv. Chim. Acta, 1976, 59, 737 (aldehyde)

P-Santalanes
Baumann, M. eta/, Justus Liebigs Ann. Chem., 1979, 743 (synth)
Brunke, E.-J. et al, Justus Liebigs Ann. Chem., 1982, 1105 (abs
co'!fig)
Monti, H. et al, Tetrahedron Lett., 1982, 23, 5539 (synth)
Solas, D. et al, J. Org. Chem., 1983, 48, 1988 (synth, bib!)

Norbicycloekasantalal Sq-02669 ~Santal-1 0-ene-3,8-diol Sq-02672

10,11,12,13- Tetranor-P-santal-3(15)-en-9-al
[37720-84-6]

C 11 H 160
OH~
M 164.247
CISH2602 M 238.369
(3P,8R)-form [55804-04-1] C/ausantalene
Constit. of Clausena indica. Cryst. Mp 114°. [a.]n +27.7°
Constit. of Santalum album. (c, 1.9 in CHC1 3).
Gibson, T. et al, Tetrahedron Lett., 1972, 2207.
Joshi, B.S. et al, Experientia, 1975, 31, 138.

~Santala-3(15),10-diene Sq-02670
fJ-Santalene
[511-59-1]

CISH24 M 204.355
Constit. of sandalwood oil. Oil with cedar-like odour. Bp9
125-127°. [a.]D -35°.
l:Iodgson, G.L. et al, J. Chem. Soc., Perkin Trans. 1, 1973, 2113
(synth, abs co'!fig)
ECk, C.R. eta/, J. Chem. Soc., Perkin Trans. 1, 1974, 1938 (synth)
Christenson, P.A. et al, J. Org. Chem., 1979, 44, 2012 (synth)
Bertrand, M. et al, Tetrahedron Lett., 1979, 15 (synth)
Oppolzer, W. eta/, Helv. Chim. Acta, 1985, 68, 2100 (synth)
Takano, S. eta/, J. Chem. Soc., Chem. Commun., 1987, 1720
(synth)
Arai, Y. eta/, Bull. Chem. Soc. Jpn., 1988, 61, 467 (synth)

629
Cyclosativene - 7(12)-Sativene Sq-02673 - Sq-02676

Prehelminthosporol Sq-02675
[1619-13-2]
Sativanes

Cyclosativene Sq-02673
[22469-52-9)

C15H 24 M 204.355
Constit. of Abies magnifica. [ocJn +94.1° (c, 0.5 in CHC1 3).
Kido, F. eta/, Tetrahedron Lett., 1969, 3169 (abs config)
Piers, E. eta/, Can. J. Chem., 1975, 53, 2849 (synth)
Baldwin, S.W. eta/, J. Org. Chem., 1980, 45, 1455 (synth)
Heissler, D. eta/, Tetrahedron Lett., 1980, 4707 (synth)
Helminthosporal Sq-02674
1, 7- Dimethyl-4-( J-methylethyl)bicyc/o[3 .2.1]oct-6-ene-6,8-
dicarboxaldehyde, 9CJ. 4-/sopropy/-1,7-
dimethylbicyc/o[3.2.1]oct-6-ene-6,8-dicarboxaldehyde
[723-61-5]
C1sH240z M 236.353
Metab. of Cochliobolus sativus and C. setariae. Shows
antiviral activity in vitro. Phytotoxin and plant growth
regulator. Gum. Mixt. of epimers.
Ac: [81509-30-0].
Mp 65-67°. [a]i,7 -1.6° (c, 0.92 in CHC1 3).
Ketone (lactone): Preltelmintlwsporolactone
ClsH210 1 M 234.338
From a Bipolaris sp. Phytotoxin. Needles (MeOH aq.).
Mp 78.5-79°. [a]i,7 -119.8° (c, 0.96 in CHC13).
9-Hydroxy: [26770-82-1). 9-Hydroxypreltelmintltosporol
C•sH 240 1 M 236.353
Metab. of C. sativus. Shows antiviral props. in vitro.
Gum.
9-Acetoxy: Cryst. (Etpjpet. ether). Mp 135-137°. [a]i?
+9.3° (c, l.l in CHC1 3).
Aldridge, D.C. eta/, J. Chem. Soc. C, 1970, 686.
Nukina, M. eta/, J. Am. Chem. Soc., 1975, 97, 2542 (props)
Nukina, M. eta/, Agric. Bioi. Chem., 1976, 40, 2121 (props)
Cutler, H.G. eta/, J. Agric. Food Chem., 1982, 30, 658 (props)
Pena-Rodriguez, L.M. et a/, J. Nat. Prod. (Lioydia), 1989, 52, 899
(Prehelminthosporo/actone)

7(12)-Sativene Sq-02676
Sativene. Ylangocamphene

C15Hn01 M 234.338
Prod. by Helminthosporium sativum and Cochliobolus
sativus. Phytotoxin. Cryst. Mp 56-59°. [a]n -49° (c, 1.2
in CHC1 3).
14-A/coho/: [1619-29-0). Helmintltosporol
ClsH240 1 M 236.353
Metab. of H. sativum. Cryst. (hexane). Mp 98°. [a]n
-28.7° (c, 1.9 in CHC1 3).
de Mayo, P. eta/, Can. J. Chem., 1965, 43, 1357 (isol)
Corey, E.J. eta/, J. Am. Chem. Soc., 1965, 87, 5728 (synth)
Sommereyns, G. et a/, Arch. Int. Physio/. Biochem., 1977, 85, 431
(iso/, props)
Piers, E. et a/, Can. J. Chem., 1977, 55, 1039 (synth, bib/)
Yanagiya, M. eta/, Tetrahedron Lett., 1979, 20, 1761 (synth)
Shizuri, Y. et a/, J. Chem. Soc., Chem. Commun., 1986, 63 (synth)
Gray, B.D. et al, J. Chem. Soc., Chem. Commun., 1987, 1136
(synth)
(-)-form
ClsH24 M 204.355
(+)-form [3650-28-0]
Oil. [a]n + 191° (CHC1 3).
(-)-form [6813-05-4]
Constit. of Helminthosporium sativum. Oil. [a]n -186°
(CHC1 3).
4-Epimer: [16641-59-1]. Copacampltene
C15H 24 M 204.355
Semisynthetic, obt. from Copabomeol. Oil. [a]n +28°
(c, 1.2 in CHCI 3).
de Mayo, P. eta/, J. Am. Chem. Soc., 1965, 87, 3275 (isol, struct)
Kolbe, M. et al, Acta Chem. Scand., 1967, 21, 585 (Copacamphene)
Hodgson, G.L. eta/, J. Chem. Soc., Perkin Trans. 1, 1973, 2113
(abs con.fig, synth)
Eck, C.R. eta/, J. Chem. Soc., Perkin Trans. I, 1974, 1938 (synth)
Piers, E. et a/, Can. J. Chem., 1975, 53, 2849 (synth)
Bakuzis, P. eta/, J. Org. Chem., 1976, 41, 3261 (synth)
Oppolzer, W. eta/, Helv. Chim. Acta, 1984, 67, 1154 (synth)
Snowden, R.L., Tetrahedron, 1986, 42, 3277 (synth)
Sigrist, R. eta/, Helv. Chim. Acta, 1988, 71, 788 (synth)

630
Sativenediol - 12-Cyclocopacamphanol Sq-02677 - Sq-02680

Sativenediol Sq-02677 Cyclocopacamphane Sq-02679

Cyclocopacamphene
[24112-86-5]

(-)-cis-form

C15H240 2 M 236.353 C15H24 M 204.355

(-)-cis-form [55556-01-9]
Constit. of vetiver oil. Oil. [oc]~· 5 + 35.0° (CHC1 3).
Metab. of Cochliobolus setariae and Helminthosporium Kido, F. eta/, Tetrahedron Lett., 1969, 3169 (iso/)
sativum. Plant growth promotor. Oil. [oc]i; -119° (c, Hagiwara, H., Bull. Chern. Soc. Jpn., 1975, 48, 3723 (synth)
Piers, E. eta/, Can. J. Chern., 1975, 53, 2849 (synth)
0.94 in CHC1 3).
(-)-trans-form [55537-09-2]
From C. setariae and H. sativum. Plant growth 12-Cyclocopacamphanol Sq-02680
promotor. Needles. Mp 176°. [oc]i,7 -3.4° (c, 1.4 in Cyclocopacamphenol
CHC1 3). [30810-34-5]
(±)-cis-form [60426-94-0]
Cryst. (MeCN). Mp 56-57°.
Di-Ac: [72675-81-1].
Mp 87.5-88°.
[59952-94-2, 59952-95-3)
Nukina, H. eta/, J. Am. Chern. Soc., 1975, 97, 2542 (iso/, struct)
McMurry, J.E. et a/, J. Org. Chern., 1976, 41, 3953 (synth, pmr) C 15H 240 M 220.354
Piers, E. et a/, Can. J. Chern., 1977, 55, 1039 (synth) · Constit. of Vetiveria zizanioides (vetiver oil). Oil. Isol. as
Yanagiya, M. eta/, Tetrahedron Lett., 1979, 1761 (synth) an inseparable mixt. with Epicyclocopacamphenol.
Sigrist, R. et a/, Helv. Chim. Acta, 1988, 71, 788 (synth)
12-Carboxy/ic acid: [24120-98-7]. 12-Cyclocopacamphanoic
acid. Cyclocopacamphenic acid
ClsH 220 2 M 234.338
Constit. of vetiver oil. Mp 151.5-152.SO. [oc]~ -14.7°
(CHC1 3).
Copacamphanes I 1-Epimer: Epicyclocopacamphenol
ClsH 240 M 220.354
Isol. from vetiver oil. Obt. only as a mixt. with
Cyclocopacamphenol.
11-Epimer, 12-carboxylic acid: [24112-85-4].
2-Copacamphanol Sq-02678 Epicyclocopacamphenic acid
Isol. from vetiver oil. Cryst. Mp 168-168.5°. [oc]i,0· 5
+ 78.3° (c, 3.6 in CHC1 3).
Kido, F. eta/, Tetrahedron Lett., 1969, 3169.
Homma, A. eta/, Tetrahedron Lett., 1970, 231 (iso/)

ClsHuO M 222.370
2rx.-form [21966-93-8] Copaborneol
Constit. of Pinus silvestris. Cryst. (pet. ether). Mp 47.5-
480. [oc]~ + 27.4° (c, 1 in CHC1 3).
Ketone: [21966-94-9]. 2-Copacamphanone. Copacamphor
C1sH240 M 220.354
Constit. Espeletiopsis guacharaca. Oil. [oc]i; + 111° (c, 0.8
in CHC1 3).
Westfelt, L., Acta Chern. Scand., 1966, 20, 2829 (iso/)
Ko1be-Haugwitz, M. et a/, Acta Chern. Scand., 1970, 24, 1623
(struct)
Piers, E. et a/, Can. J. Chern., 1975, 53, 2838 (synth)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2399 (Copacamphor)

631
Cyclosinularan-12-ol- 3-Copaene Sq-02681 - Sq-02686

Sinularanes Copaanes

Cyclosinularan-12-ol Sq-02681 2,4(15)-Copaadiene Sq-02684

~H
C 15H 240 M 220.354 C15H 22 M 202.339
Ac: 12-AcetoxycyclosiiUt/iuiiiU!
(1«,6«,7«11)-form [27597-38-2] Copadiellt!
C 17Hv;02 M 262.391 Constit. of the essential oil of Cyperus rotundus. Oil. Bp 1
Constit. of Clavu/aria in.flata. Oil. [1X]n +20.SO (e, 0.4 in
130-140° (bath). [1X]n +17.3° (CHCI 3).
CHC13).
Kapadia, V.H. et al, Tetrahedron Lett., 1967, 4661.
Brackman, J.C. et al, Tetrahedron, 1981, 37, 179 (cryst struct)

3-Copaen-15-al Sq-02685
7(15)-Sinularene Sq-02682
Siularellt!

OH~
(64845-75-6]

C15H 200 2 M 232.322

C 15H 24 M 204.355
Constit. of Sinularia mayi. Oil. [IX]~ -142° (c, 0.55 in
CC14).
Beechan, C.M. et al, Tetrahedron Lett., 1977, 2395 (isol)
Collins, P.A. et al, Aust. J. Chem., 1979, 32, 1819 (synth)
Oppolzer, W. et al, Tetrahedron Lett., 1982, 23, 4673 (synth)
Piers, E. et al, Can. J. Chem., 1985, 58, 996 (synth)
Antczak, K. et al, Can. J. Chem., 1987, 65, 114 (synth)
(1fJH,6fJH,7~11)-(1)-form [24306-83-0] BracllylaenaloM A
Constit. of Brachylaena hutchinsii. Oil.
(1fJH,6fJH,7~11)-(2)-form [24268-43-7] BracllylaenaloM B
Constit. of B. hutchinsii. Oil.
Brooks, C.J.W. et al, J. Chem. Soc., Chem. Commun., 1969, 630.
3-Copaene Sq-02686
1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02·'1]dec-3-ene,

,m,
9CI. 8-1sopropyl-1,3-dimethyltricyclo[4.4.0.02·'1]dec-3-ene
7(15)-Sinularen-12-ol Sq-02683 [3856-25-5]

C 15H 240 M' 220.354

~
C 15H 240 M 220.354
(11XH,6a.H,1a.H)-form

Ac: 12-AcetoxysiiUtliuellt! (1«H,6fi.H,7fl.ll)-form [14912-44-8] Ylllllgellt!. IX- Ylangene

C17H 260 2 M 262.391 . lsol. from various essential oils, esp. Schizandra
Constit. of Clavularia in.flata. Oil. [1X]n -92.2° (c, 0.346 chinensis. Oil. [IX]~ +50 .SO.
in CHCl3).
(1fJH,6fJH,7r~.ll)-form
Brackman, J.C. et al, Tetrahedron, 1981, 37, 179.
r~.-Copaellt!
Constit. of the oils of African Copaiva balsam and
Sindora wallichii. Also from various other higher plant
oils and from the brown alga Dictyopteris divaricata.
Oil. Bp 246-251°. [1X]n -13.3° (CHCI3). ,W 1.4722.
11-Hydroxy: [41370-56-3]. 3-Copaen-11-ol. r~.-Copaen-11-ol
C 15H 240 M 220.354
Constit. of the essential oil of Parabenzoin praecox.
Cryst. Mp 99.5-100.5°. [1X]n +9.2° (CHC1 3).
15-Hydroxy: [41610-70-2]. 3-Copaen-15-o/. 15-Copaenol
C 15H 240 M 220.354
Constit. of Pilgerodendron uniferum. Oil. [1X]i,S -28.6° (c,
0.2 in CHCI 3).

632
3-Copaen-8-ol- 3-lshwaranone Sq-02687 - Sq-02691

[115728-41-1]
Mot!, 0. et al, Collect. Czech. Chern. Commun., 1962, 27, 987 (isol,
Ylangene)
Irie, T. et al, Bull. Chern. Soc. Jpn., 1964, 37, 1053 (isol, ac- Ishwaranes
Copaene)
Kapadia, V.H. et al, Tetrahedron, 1965, 21, 607 (pmr)
de Mayo, P. et al, Tetrahedron, 1965, 21, 619 (ir)
Ohta, Y. et al, Tetrahedron Lett., 1969, 1601 (struct, abs conjig,
Ylangene) Ishwarane Sq-02689
Karrer, W. et al, Konstitution und Vorkommen der Organischen
Pflanzenstoffe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,
[26620-70-2]

00
no. 1907 (occur)
Ohara, K. et al, Bull. Chern. Soc. Jpn., 1973, 46, 641 (ac-Copaen-II-
ol)
Corey, E.J. et al, J. Am. Chern. Soc., 1973, 95, 2303 (synth)
I
Oyarzun, M.L. et al, Phytochemistry, 1988, 27, 1121 (!5-Copaenol)
C 13H 24 M 204.355
3-Copaen-8-ol Sq-02687 Constit. of the roots of Aristolochia indica. Oil. Bp 1 80-82°.
«-Copaen-8-o/ [1X)n -40.33° (c, 3.7 in CHC1 3).
Govindachari, T.R. et al, Tetrahedron, 1970, 26, 615 (isol)
Kelly, R.B. et al, Can. J. Chern., 1972, 50, 5455 (synth)
Cory, R.M. et al, J. Chern. Soc., Chern. Commun., 1977, 587
(synth)
Piers, E. et al, J. Chern. Soc., Chern. Commun., 1977, 880 (synth)
Cory, R.M. et al, Org. Magn. Reson., 1978, 11, 252 (cmr)
Hagiwara, H. et al, J. Chern. Soc., Perkin Trans. I, 1980, 963
(cmr)
C 13H 2•.0 M 220.354
8«-form [58569-25-8] 1-Ishwaranol Sq-02690
lsol. from root of Angelica archangelica. [28957-57-5]
8-Ketone: 3-Copaen-8-one. «-Copaen-8-one
C 13H 22 0 M 218.338 OH
I

Constit. of Neomirandea guevarii. Oil. [1X]i;' + 14° (c, 0.53

in CHC13).
Taskinen, J., Acta Chern. Scand., Ser. B, 1975, 29, 999.
Tamayo-Castillo, G. et al, Phytochemistry, 1989, 28, 938.
~ I

Ct 3H 240 M 220.354
3-Copaen-2-one Sq-02688 1«-form
lshwarol

lO
Constit. of Aristo/ochia indica. Oil. Bp 1 110°. [IX]~
+ 13.65°.
Ketone: [22471-56-3]. 1-lshwaranone. lshwarone
C 13H 220 M 218.338
Ht Constit. of A. indica. Cryst. (pentane). Mp 57°. [IX]~
~ +22.9° (c, 1.35 in CHC1 3).
C 13H 220 M 218.338 Fuhrer, H. et al, Tetrahedron, 1970, 26, 2371 (isol, struct)
(l«H,6«H,7PH)-form [1209-91-2] Mustakone Govindachari, T.R. et al, Indian J. Chern., 1971, 9, 1310 (isol)
Cory, R.M. et al, Org. Magn. Reson., 1978, 11, 252 (cmr)
Constit. of Cyperus rotundus and C. articulatus. Oil. Bp 1 Piers, E. et al, Can. J. Chern., 1980, 58, 2613 (synth)
128-129°. [IX]~ -42.5° (c, 1.85 in CHC1 3).
2,4-Dinitrophenylhydrazone: Cryst. (EtOH). Mp 141-142°.
3-Ishwaranone Sq-02691
Kapadia, V.H. et al, Tetrahedron, !965, 21, 607 (isol) 3-0xoishwarane
Nyasse, B., Phytochemistry, 1988, 27, 3319 (isol, pmr)
[41756-76-7]

o(B I
I
I

C 13H 220 M 218.338

Constit. of Aristolochia debilis. Cryst. (pentane). Mp 45-
460.
Semicarbazone: Cryst. (EtOH). Mp 215-215.SO.
Nishida, R. et al, Agric. Bioi. Chern., 1973, 37, 341 (isol)
Cory, R.M. et al, Org. Magn. Reson., 1978, 11, 252 (cmr)

633
Isoishwarone- 11(13)-Rotunden-12-ol Sq-02692- Sq-02696

lsoishwarone Sq-02692
:~~~;~~~~~~:-ishwaren-1-one Rotundanes
0

~Absolute
lyP configuration
ll-Rotundene Sq-02694
I Rotundene
C15H 220 M 218.338 [65128-08-7]
Constit. of Aristo/ochia indica. Oil. Bp0.7 100°. [IX]~
-74.61°.
Govindachari, T.R. eta/, J. Chern. Soc., Chern. Commun., 1969,
823 (abs corifig)
Ganguly, A.K. eta/, Tetrahedron Lett., 1969, 133 (isol)
Kelly, R.B. et al, J. Chern. Soc., Chern. Commun., 1970, 1102 C15H 24 M 204.355
(synth)
Constit. of the oil of Cyperus scariosus. Oil. [1X] 0 -15.63°
(CHC1 3).
7 ,11-Seco-11-ishwaranol Sq-02693 Nerali, S.B. eta/, Indian J. Chern., 1970, 8, 854 (isol)
7,12-Seco-12-ishwarano/ Paknikar, S.K. et a/, Tetrahedron Lett., 1977, 2121 (struct)
[74912-09-7] Paknikar, S.K. eta/, Indian J. Chern., Sect. B, 1979, 18, 178
(struct)
HO\

cEf
11-Rotundene-13,15-diol Sq-02695
' 13,15-Dihydroxyrotundene
7 I
I H'
I
I
I
~CH,OH
C15H 260 M 222.370
Constit. of Aristo/ochia indica. Cryst. (MeCN). Mp 150°. 151 :H:
(IX]~ -20.4°. HOH2 C
Pakrashi, S.C. et al, J. Org. Chern., 1980, 45, 4765. C 15H 240 2 M 236.353
15-Ac, 13-Me ether:
C18H 280 3 M 292.417
Constit. of Trixis vautheri. Oil.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1649.

11(13)-Rotunden-12-ol Sq-02696
Rotundenol
[65128-09-8]

y1JoH
C15H 240 M 220.354
Constit. of the oil of Cyperus scariosus. [1X]n + 55.35°
(CHC1 3).
Nera1i, S.B. et al, Indian J. Chern., 1970, 8, 854 (isol)
Paknikar, S.K. et al, Tetrahedron Lett., 1977, 2121 (struct)

634
Mayurone - 3-Thujopsen-5-one Sq-02697 - Sq-02702

Branca, S.J. eta/, J. Org. Chem., 1977, 42, 3165 (synth)

Johnson, C.R. eta/, J. Am. Chem. Soc., 1982, 104, 4290 (synth)

Thujopsanes Nabeta, K. eta/, Agric. Bioi. Chem., 1986, 50, 2915 (biosynth)

3-Thujopsen-15-oic acid Sq-02701

Hinokiic acid. Widdringtonic acid /. Widdrenic acid
[546-53-21

WrooH
Mayurone Sq-02697 I
15-Nor-1-thujopsen-3-one
[4677-90-11

C15H 120 1 M 234.338

C14H 200 M 204.311
Constit. of Thuja spp. and Thujopsis dolabrata. Cryst. (pet.
ether). Mp 70-71°. [ali? +253.4° (CHC1 3).
Chetty, C.L. et a/, Tetrahedron Lett., 1965, 3773 (isol)
Ito, S. et al, Tetrahedron Lett., 1965, 3777 (isol)
Ito, M. et al, Bull. Chem. Soc. Jpn., 1972, 45, 1914 (synth)
McMurry, J.E. et al, J. Org. Chem., 1974, 39, 2217 (synth)
3-Thujopsen-5-one
Branca, S.J. eta/, J. Org. Chem., 1977, 42, 3165 (synth)
Matsuo, A. et al, Phytochemistry, 1985, 24, 777 (synth)
Constit. of Widdringtonia spp., Chamaecyparis thyoides
and Juniperus spp. Cryst. Mp 169-170° (166°). [ali?
-90.4°.
Erdtman, H. et al, Acta Chem. Scand., 1959, 13, 1124 (isol)
Forsen, S. et a/, Acta Chem. Scand., 1961, 15, 1676 (pmr)
Ta1vitie, A. eta/, Finn. Chem. Lett., 1976, 149 (struct)
Sq-02702
0

3(15),4-Thujopsadiene
Thujopsadiene
[24048-40-61
Sq-02698

C15H 120 M 218.338

~
ent-form [97170-17-7] Thujopsenone
Constit. of the liverwort Marchantia polymorpha. Oil.
[aln -80° (c, l.l in CHC1 3).
Matsuo, A. eta/, Phytochemistry, 1985, 24, 777.
C 15H 12 M 202.339
Constit. of Biota orienta/is. Liq. Bp 10 ll5°.
Nakatsuka, T. et al, Mokuzai Gakkaishi, 1969, 15, 46 (isol)
Branca, S.J. et a/, J. Org. Chem., 1977, 42, 3165 (synth)

7-Thujopsanol Sq-02699

C 15H 21;0 M 222.370

Error in authors' structure diag. (shown with C=O
group).
(ent-7/l)-form
Constit. of Marchantia polymorpha. Oil.
Asakawa, Y. et al, Phytochemistry, 1990, 29, 1577 (isol, pmr, cmr)

3-Thujopsene Sq-02700
Thujopsene. Widdrene
[470-40-61

Absolute
configuration

C 15H 14 M 204.355
Constit. of Thujopsis dolabrata, Widdringtonia spp. and
other woods with the characteristic fragrance of pencil
wood. Liq. Bp 12 121-122°. [aln -79.7°.
Norin, T., Acta Chem. Scand., 1961, 15, 1676; 1963, 17, 738 (iso/,
struct)
Dauben, W.G. eta/, J. Am. Chem. Soc., 1963, 85, 3673 (synth)

635
3-Bourbonene - 3(15)-Gymnomitrene-1,10-diol Sq-02703 - Sq-02709

Norbourbonone Sq-02706
15-Nor-4-bourbonone
Bourbonanes [13844-03-6]

ilii
H

3-Bourbonene Sq-02703
IX-Bourbonene
[5208-58-2]
C14H 220 M 206.327
H Constit. of Geranium bourbon. Cryst. Mp 23-25°. [IX]~
-213° (c, 0.39 in CHC1 3).

~
Giannotti, C. eta/, Bull. Soc. Chim. Fr., 1968, 2452 (isol, struct)
Tomioka, K. eta/, Tetrahedron Lett., 1982, 23, 3401 (synth)

CtsH 24 M 204.355
Minor constit. of the essential oil of Geranium bourbon.
Oil. [IX]~ +24.7°.
Kfepinsky, J. eta/, Tetrahedron Lett., 1966, 359 (isol) Gymnomitranes
Kfepinsky, J. eta/, Tetrahedron, Suppl., No. 8, 1966, 53 (struct)
Brown, M. et a/, J. Org. Chern., 1968, 33, 162 (synth)
White, J.D. eta/, J. Am. Chern. Soc., 1968, 90, 6171 (synth)

3(15)-Gymnomitrene Sq-02707
4(15)-Bourbonene Sq-02704 P-Btubatene. P-Pompene. Gymnomitrene
P-Bourbonene
[39863-73-5]
[5208-59-3]
H

CtsH24 M 204.355
~
Constit. of the essential oil of Geranium bourbon. Oil. [IX]~
-92.12°.
Kfepinsky, J. et a/, Tetrahedron Lett., 1966, 359 (isol)
Kfepinsky, J. eta/, Tetrahedron, Suppl., No. 8, 1966, 53 (struct)
White, J.D. eta/, J. Am. Chern. Soc., 1968, 90, 6171 (synth)
Tomioka, K. eta/, Tetrahedron Lett., 1982;'23, 3401 (synth)
C15H 24 M 204.355
Constit. of Bazzania pompeana, Barbilophozia spp. and
Gymnomitrion obtusum. Oil. [1X]n -26° (c, 5 in CHC13).
Andersen, N.H. eta/, Phytochemistry, 1973, 12, 2709 (isol)
Connolly, J.D. et al, J. Chern. Soc., Perkin Trans. I, 1974, 2487
(isol)
Matsuo, A. eta/, Tetrahedron Lett., 1975, 241 (isol)
Nozaki, H. et a/, Bull. Chern. Soc. Jpn., 1978, 51, 47 (cryst struct)
Welch, S.C. eta/, J. Org. Chern., 1980, 45, 4080 (synth)

4,7-Epoxy-1,5-dihydro-8-hydroxy-11(13)- Sq-02705 3-Gymnomitrene Sq-02708

bourbonen-12,6-olide IX-Btubatene. IX-Pompene
[53060-59-6]

C15H24 M 204.355
Constit. of Bazzania pompeana and Barbilophozia spp. Oil.
CtsH180 4 M 262.305 [1X]n +48.3°.
(1P,41X,SP,6P,71X,81X)-form Andersen, N.H. eta/, Phytochemistry, 1973, 12, 2709 (isol)
8-Tigloyl: Matsuo, A. et a/, Tetrahedron Lett., 1975, 241 (struct)
CzoH 240 5 M 344.407
Constit. of Vernonia arkansana. Gum. [IX]~ + 16.8° (c, 3(15)-Gymnomitrene-1,10-diol Sq-02709
0.5 in CHC1 3).
8-(2-Methylpropenoy{):
C1gH 22 0 5 M 330.380
ts~OH
3 10
Constit. of V. arkansana. Gum. H OH
Bohlmann, F. eta/, Phytochemistry, 1981, :ZO, 473.

C 15H 240 1 M :.. 6.353

(JS,J0/1)-form

636
3-Gymnomitrene-1,10,15-triol - 8-Acetyloctahydro-3a,7,7-trimethyl-.•. Sq-02710- Sq-02714

Minor constit. of Gymnomitrion obtusum. Oil. Bp0 _01 3(15)-Gymnomitren-1-ol Sq-02712

110°. (o:) 0 + 14° (c, 2.84 in CHC1 3).

~
Di-Ac: [55650-01-6]. 1,10-Diacetoxy-3(15)-gymnomitrene
C1,H2110 4 M 320.428
Minor constit. of G. obtusum. Oil. Bp0 _01 110°. (tx] 0 + 14°
(c, 2.84 in CHC13).
3P,l5-Epoxide, di-Ac: [55626-39-6). 1,10-Diacetoxy-3,15- ~
epoxygymnomitrane C15H 140 M 220.354
C 1,H280 5 M 336.427 (1S)-form [41410-53-1) Gymnomitrol
Constit. of G. obtusum. Cryst. (pet. ether). Mp 155-156°. Constit. of Gymnomitrion obtusum. Cryst. Mp 114-ll6°.
(o:] 0 -60° (c, 0.58 in CHcl;). (o:) 0 + 7° (c, 2.3 in CHCl3).
10-Deoxy, 3P,l5-epoxide, l-Ac: 1-Acetoxy-3,15- 4o:-Hydroxy, l-Ac: 4rr.-Hydroxygymnomitryl «elate
epoxygymnomitrane C17H 260 3 M 278.391
C17H 260 3 M"278.391 Constit. of Plagiochila trabeculata. Oil.
Constit. of G. obtusum. Cryst. by subl. Mp 149-150°. 4o:-Hydroxy, 1-cinnamoyl: 4rr.-Hydroxygymnomitryl
[o:] 0 -27° (c, 2.25 in CHCI 3).
cilllltlnUlte
Connolly, J.D. et al, J. Chern. Soc., Perkin Trans. 1, 1974, 2487. C14H:14,03 M 366.499
Constit. of P. trabeculata. Oil.
3-Gymnomitrene-1,10,15-triol Sq-02710 4-0xo, l-Ac: 4-0xogymnomitryl «etate
C17H 140 3 M 276.375
HO~~H Constit. of P. trabeculata. Oil.
Connolly, J.D. et al, J. Chern. Soc., Perkin Trans. 1, 1974, 2487
(isof)
Coates, R.M. et al, J. Am. Chern. Soc., 1982, 104, 2198 (synth,
bib{)
C 15Hz..03 M 252.353 Toyota, M. eta/, Phytochemistry, 1988, rT, 2161 (derivs)
(JS,J0/1)-form
1,10-Di-Ac: 1,10-Diacetoxy-3-gymnomitren-15-ol
C1,H280 5 M 336.427
Constit. of Gymnomitrion obtusum. Oil. Bp0_05 160°. [o:] 0
+ 35o (c, 0.8 in CHC1 3).
10-Deoxy, l-Ac: 1-Acetoxy-3-gymnomitren-15-ol
Miscellaneous bicyclic
C17H 260 3 M 278.391
Constit. of G. obtusum. Oil. Bp0 .005 100°. [o:] 0 +52° (c,
4.8 in CHC1 3).
sesquiterpenoids
Connolly, J.D. et al, J. Chern. Soc., Perkin Trans. 1, 1974, 2487.

3(15)-Gymnomitren-12-ol Sq-02711
Sq-02713
[129602-37-5]

~ tL~H
I I
I I

C15H140 M 220.354 C15H 160 5 M 276.288

Constit. of Marsupella emarginata var. patens. Cryst. Mp
88-90°. (o:) 0 -28.1° (c, 1.4 in CHC1 3).
15-Aldehyde: [129602-38-6]. 3(12)-Gymnomitren-15-111
C15Hn0 M 218.338
Constit. of M. emarginata var. patens. Oil. [o:) 0 -10.0°
(c, 0.5 in CH03).
15-Carboxylic acid: [129602-39-7]. 3(12)-Gymnomitren-15-
Pigment from root of Cassia semicordata. Cryst. Mp 191-
1920.
Delle Monache, G. eta/, Tetrahedron Lett., 1989, 30, 6203.
8-Acetyloctahydro-3a,7,7-trimetbyl-2(1H)- Sq-02714
azulenone, 9CI
4,5-Seco-3,5-longibornanedione

01?-
oic fiCid
C15Hn02 M 234.338 [87376-72-5)
Constit. of M. emarginata var. patens. Cryst. Mp 131-
1320. (o:) 0 -0.7° (c, 1.4 in CHCl 3).
Matsuo, A. eta/, Phytochemistry, 1990, 29, 1921 (isol, pmr, cryst
struct)

C15H140 2 M 236.353
Constit. of Artemisiafilifolia. Gum. [o:]~ +22° (c,2.67 in
CHC13). Not a longibomane.
Bohlmann, F. et al, Phytochemistry, 1983, 22, 503.

637
Agassizin- 2-Bromo-4-(4-bromo-3,3-... Sq-02715 - Sq-02722

Agassizin Sq-02715 ot-Bergamotene Sq-02720

[79827-32-0] Bergamotene
[13474-59-4]

Q)J
0

CISH180 M 214.307 CISH24 M 204.355

Constit. of the nudibranch Hypselodoris spp. Oil. [a:Jn Constit. of oils of carrot (Daucus carota), bergamot (Citrus
-94° (c, 1.2 in MeOH). bergamia), also C. aurantifolia, C. medica and
cottonseed oil (Gossypium hirsutum). Oil. d20 0.855. [a]~
Hochlowski, J.E. eta/, J. Org. Chem., 1982, 47, 88. -44.1 o (CHC1 3). n~ 1.4904.
Kovats, E., Helv. Chim. Acta, 1963, 46, 2705 (pmr, ms, struct)
Allohimachalol Sq-02716 Larsen, S.D. eta/, J. Am. Chem. Soc., 1977, 99, 8015.
[19435-77-9] Kulkarni, Y.S. et a/, J. Org. Chem., 1985, 50, 2809 (synth)
Snider, 8.8. eta/, J. Org. Chem., 1988, 53, 4508 (synth)
OH

Q;)
I
JJ-Bergamotene Sq-02721
6-Methyl-2-methylene-6-(4-methyl-3-
pentenyl)bicyclo[3.l.l]heptane, 9CI
[6895-56-3]
C 15H 21;0 M 222.370
Constit. of Cedrus deodara. Cryst. (MeCN). Mp 85-86°.
[a:Jn + 37.4° (c, 3.3 in CHC1 3).
Bisarya, S.C. eta/, Tetrahedron, 1968, 24, 3801, 3869 (iso/, struct) trans-form
CISH24 M 204.355
Alpiniol Sq-02717 trans-form [15438-94-5]
[89808-61-7] Constit. of Indian valerian root oil (from Valeriana
wallichi) and isol. from Aspergillus fumigatus. Oil. Bp 1
120-130°. [1X]n +35.8° (c, 4.0 in CHCI 3).
cis-form [15438-93-4]
Oil. Bp0 _5 105-125°. [a:Jii +40.2° (c, 1.74 in CHCI 3).
[35334-59-9)
Gibson, T.W. eta/, J. Am. Chem. Soc., 1969, 91, 4771 (synth)
Corey, E.J. eta/, J. Am. Chem. Soc., 1971, 93, 7016 (synth)
CISH2402 M 236.353 Hogg, J.W. eta/, Cosmet. Perfum., 1974, 89, 64, 66, 69 (ir, pmr)
Constit. of rhizome of Alpinia japonica. Cryst. Mp ll5- Nozoe, S. eta/, Tetrahedron Lett., 1976, 4625 (isol)
ll80. [1X]n -12.7° (c, 0.35 in CHC1 3). Cane, D.E. eta/, Tetrahedron Lett., 1976, 4737 (biosynth)
ltokawa, H. eta/, Chem. Lett., 1984, 451 (cryst struct) Corey, E.J. eta/, Tetrahedron Lett., 1985, 26, 3535 (synth)
Kulkarni, Y.S. eta/, J. Org. Chem., 1987, 52, 1568.

4-Ambiguen-1-ol Sq-02718
2-Bromo-4-(4-bromo-3,3-
dimethylcyclohexyl)-1-methyl-7-
oxabicyclo(2.2.1)heptane, 9CI Sq-02722
[88556-03-0]

C 15H:u;0 M 222.370
Constit. of Helichrysum bilobum ssp. bilobum. Oil. [1X]~4
-45° (c, 0.89 in CHC1 3).
Jakupovic, J. eta/, Phytochemistry, 1989, 28, 543.
C 15H 24Brz0 M 380.162
Constit. of Laurencia obtusa. Cryst. (hexane). Mp 100-
Bazzanenol Sq-02719 1020. [1X]n -8.7° (c, 2.86 in CHCI 3).
[28290-28-0] Gonzalez, A.G. eta/, Tetrahedron Lett., 1983, 24, 4143 (cryst
struct)

OH

CISH240 M 220.354
Constit. of Bazzania pompeana. Oil. [1Xln + 19.1°.
Hayashi, S. eta/, Experientia, 1970, 26, 347.

638
Bullerone - 4,10-Dihydroxy-2,8-neolemnadien-5-... Sq-02723 - Sq-02730

BuUerone Sq-02723 Constit. of Cyperus rotundus. Cryst. + Hp. Mp 41-42°.

[107724-17-4] Bp0.1 120° (bath). [1X]n +31.4° (CHC1 3).
Hikino, H. eta/, Chern. Pharm. Bull., 1966, 14, 1439, 1441; 1967,
15, 1349 (isol, ir, pmr, ord, struct, synth)
Kapadia, V.H. et a/, Tetrahedron Lett., 1967, 4661.

5,7a-Dihydro-1,4,4,7 a-tetramethy l-4H- Sq-02728

indene, 9CI
2,2,6,7-Tetramethylbicyclo[4.3.0]nona-1(9),4,7-triene
C 1 ~H 18 0 3 M 246.305
Constit. of Cyathus bulleri. Yellow oil. [99901-21-0]
Ayer, W.A. eta/, Can. J. Chern., 1987, 65, 15.

CascariUadiene Sq-02724
[59742-39-1]

C 13H 18 M 174.285
Constit. of Quince fruit flavour (Cydonia oblonga). Oil.
Ishihara, M. eta/, J. Org. Chern., 1986, 51, 491.

1,5-Dihydroxyeriocephaloide Sq-02729
C 1 ~H 24 M 204.355 [112848-38-1]
Constit. of oil of Croton eleuteria. Oil.
C1aude-Lafontaine, A. eta/, Bull. Soc. Chim. Fr., 1976, 88.

Chanootin Sq-02725
[5948-27-6]

HO~ C 1 ~H 20 0 4 M 264.321
(1P,5fl)-form
HOV Constit. of Eriocephalus kingesii. Oil.
0 Zdero, C. et a/, Phytochemistry, 1987, 26, 2763.
C 1 ~H 18 0 3M 246.305
Constit. of Chamaecyparis nootkatensis. Cryst. (MeOH). 4,10-Dihydroxy-2,8-neolemnadien-5-one Sq-02730
Mp 172-173°.
Norin, T., Ark. Kemi, 1964, 22, 129 (isof)
Kalsson, B. eta/, Acta Crystallogr., Sect. B, 1973, 29, 1209 (cryst HO,~O
10
struct) 4
- OH
Cyperanic acid Sq-02726
C 1 ~H 22 0 3 M 250.337
[117869-89-3]
(4P,10rx.)-form

H~OH
4-Ac: 4-Acetoxy-10-hydroxy-2,8-neo/emnadien-5-one
C 17H 240 4 M 292.374
Constit. of Lemnalia africana. Cryst. Mp 111-112°. [1X]n
+440° (c, 1.16 in CHC1 3).
Di-Ac: 4,10-Diacetoxy-2,8-neo/emnadien-5-one
C 1 ~H 22 0 4 M 266.336 C 19 HuP~ M 334.411
Constit. of Dittrichia viscosa. Oil. [1X]n + 26.3° (c, 0.004 in Constit. of L. africana. Oil. [1X]n +222° (c, l.l in
CHC1 3). CHCI 3).
Me ester: Cryst. (Etp). Mp 62-64°. Izae, R.R. eta/, Tetrahedron, 1981, 37, 2569.
Ceccherelli, P. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 1006 (isol,
pmr, cmr)

Cyperolone Sq-02727
[13741-46-3]

H~
M 236.353

639
3,4-Dihydroxypallenone - Herbadysidolide Sq-02731 - Sq-02738

3,4-Dihydroxypallenone Sq-02731 Ferreyrantholide Sq-02735

[115334-57-1]

O~H 0
0
C 15H:11,03 M 254.369
Constit. of Pallensis spinosa. Gum. c1sH1,o4 M 260.289
Constit. of Ferreyranthus fruticosus. Oil.
Ahmed, A.A. eta/, Phytochemistry, 1990, 29, 3355 (isol, pmr, cmr)
Jakupovic, J. eta/, Phytochemistry, 1988, 27, 1113.

Dipterolone Sq-02732
Fomannosin Sq-02736
[53755-54-7]
[18885-59-1]

of$ I

rrrb
I

C 15Hu;02 M 238.369
Constit. of Dipterocarpus macrocarpus. Cryst. Mp 92-93°.
(IX]~ + 170.4° (c, 0.939 in CHC1 3).
HOH':C O
Krishnamurty, H.G. et al, Indian J. Chem., 1974, 12, 520.
CtsH180 4 M 262.305
Metab. of the wood-rotting fungus Fornes annosus. Toxic
Disyhamifolide Sq-02733 to pine seedlings. Unstable noncryst. semisolid.
[79404-34-5] 4,5-Dihydro: [24017-74-1].
Cryst. Mp 71-72°.
Kepler, J.A. et al, J. Am. Chem. Soc., 1967, 89, 1260 (struct)
McPhail, A.T. et al, J. Chem. Soc. B, 1968, 1104 (cryst struct)
Miyano, K. eta/, Tetrahedron Lett., 1974, 1545 (synth)
Kosugi, H. eta/, Chem. Lett., 1977, 1491 (synth)
Cane, D.E. et al, J. Am. Chem. Soc., 1978, 100, 3208; 1979, 101,
1908 (config, bib/)
Cane, D.E. eta/, Tetrahedron Lett., 1980, 437 (biosynth)
Semmelhack, M.F. eta/, J. Am. Chem. Soc., 1981, 103, 2427;
CJI220 7 M 374.390 1982, 104, 747 (synth)
Constit. of Disynaphia halimifo/ia. Cryst. (Et20). Mp 270°.
[IX]~ +27° (c, 0.2 in CHC13). Herbacint Sq-02737
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1077. 4,5 ,5a,6,7,9a-Hexahydro-5a,6,9a-trimethy/naphtho[ 1,2-
bifuran
Faurinone Sq-02734 [106793-86-6)

w
(21682-87-1]

C 15H 260
<tY
M 222.370
0~
.
C 15 H~,O M 216.322
I
I

The name Herbacin is also used for a flavonoid. Isol. from

Constit. of essential oil of Valeriana officina/is. Oil.
marine sponge Dysidea herbacea. Needles (C6HJ. Mp
Hikino, H. eta/, Chem. Pharm. Bull., 1968, 16, 1779 (isol) 40-41°. [1X] 0 +9.2° (c, 0.2 in CHC1 3).
Bos, R. et al, Phytochemistry, 1983, 22, 1505 (struct)
Sarma, N.S. et al, Indian J. Chem., Sect. B, 1986; 25, 1001 (isol,
struct)
Rambabu, M. et al, Indian J. Chern., Sect. B, 1987, 26, 1156.

Herbadysidolide Sq-02738
(68299-90-l]

~"
~-J\J
H
M 234.338

640
4,5,6,9,10,10a-Hexahydro-10a-•.. - Koidzumiol Sq-02739- Sq-02746

Constit. of Dysidea herbacea. Cryst. Mp 55-56°. [a:Jn -47° 7-lsopropyl-5-methylbicyclo(2.2.2)oct-5-en- Sq-02743

(c, 0.42 in CHCI 3). 2-one
Charles, C. et al, Bull. Soc. Chim. Be/g., 1978, ffT, 481. [73069-42-8]

4,5,6,9,1 0,1 Oa-Hexahydro-1 Oa-methoxy-

6,7,8-trimethyl-6,10-methano-2H-
cyclonona(b)furan-2-one, 9CI Sq-02739
[79827-33-1]

Cl6H:u03
Db
M 262.348
MeO 0 0
CuH 180

CHCI3).
M 178.274
Constit. of Angelica archangelica. Oil. [a:]~ +345° (c, 0.9 in

Escher, S. eta/, Helv. Chim. Acta, 1979, 62, 2061.

Constit. of Hypselodoris spp. Oil. [1X]n + 38° (c, 0.47 in
MeOH).
Hochlowski, J.E. et al, J. Org. Chern., 1982, 47, 88. Jasionone Sq-02744

Isoacanthodoral
1,3,4,7,8,8a-Hexahydro-1 ,1 ,6-trimethyl-4a(2H)-
naphthaleneacetaldehyde, 9CI
[90839-03-5]
Sq-02740

cct 0

cp
r"'CHO ClsH140 M 220.354
Parent compd. apparently unknown.
11-Hydroxy: [119765-85-4]. 11-Hydroxyjasionone
C15H 140 1 M 236.353
Constit. of Jasonia montana. Oil.
Ahmed, A.A. eta/, Phytochemistry, 1988, 27, 3875.
C 15H 1•.0 M 220.354
Constit. of Acanthodoris nanaimoensis.
4-Bromopheny/urethane: Oil. [1X]n -39° (hexane). Jhanilactone Sq-02745
Ayer, S.W. et al, J. Org. Chern., 1984, 49, 2653. [67191-89-3]

Isohimachalone
[64550-94-3]
Sq-02741
~OH
0/ H
C 13Hzo03 M 224.299
Constit. of Eupatoriumjhanii. Cryst. Mp 71-72°. [a:Jn -5°
(CHCI 3).
Ac: Cryst. Mp 148-149°.
Gonzalez, A.G. eta/, Experientia, 1978, 34, 554 (cryst struct)
C 15H 1•.0 M 220.354
Constit. of the essential oil of Cedrus deodara. Oil. Bp1. 5
145-147° (bath). [a:Jn + 101.4° (c, 0.36 in CHC1 3). Koidzumiol Sq-02746
Shankaranarayan, R. eta/, Tetrahedron, 1977, 33, 885. [74323-41-4]

Isoparvifolinone Sq-02742
[83161-81-3]

C1 5H 160 M 222.370
Constit. of Artemisia koidzumii. Oil.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 149.
c15H180 1 M 230.306
(R)-form
Constit. of Perezia alamani var. oolepis. Cryst.
(CHCI 3/hexane). Mp 157-158°. [1X]n +854° (c, 1 in
CHCI 3). The (R)-config (not (S) as given in CA) follows
from that for Parvifoline, Sq-02763 from which it was
synthesised.
Joseph-Nathan, P. et a/, Phytochemistry, 1982, 21, 1129.

641
Manicoline A - Pallescensin A Sq-02747- Sq-02754

Manicoline A Sq-02747 Nakafuran 8 Sq-02751

[79820-32-9] [76844-25-2]

0
H~N=-
I ,H Absolute
""-
configuration
OH
CtsHltN0 2 M 247.336
Alkaloid from the root bark of Dulacia guianensis C 15H 100 M 216.322
(Olacaceae). Pale-yellow cryst. (EtOAc). Mp 197-199°. Constit. of Dysidea fragilis. Shows antifeedant props. Oil.
[a]i; +69° (c, 0.9 in CHC1 3 + 10% MeOH). [a]i,S +24.2° (c, 2.65 in CHC1 3).
Polonsky, J. eta/, J. Chern. Soc., Chern. Commun., 1981, 731 (isol, 5a-Hydroxy: 5-Hydroxynakafuran 8
uv, pmr, ms, cryst st~uct) C15H200 2 M 232.322
Constit. of D. etheria. Oil. [a] 0 -65.3° (c, 2.07 in
Marmelerin Sq-02748 CHC1 3).
[93304-72-4] 5a-Acetoxy: 5-Acetoxynakafuran 8
C17H 220 3 M 274.359
Constit. of D. etheria. Oil. [a] 0 -31.1° (c, 3.06 in
CHC1 3).
5-0xo: 5-Ketonakafuran 8
c.5H 180 2 M 230.306
Constit. of D. etheria. Oil. [a] 0 +35.1° (c, 1.51 in
C15Ht80 M 214.307 CHC1 3).
Constit. of Croton sonderianus. Oil. [a]i; -63° (c, 1 in
CHC1 3). Schulte, G. eta/, Helv. Chim. Acta, 1980, 63, 2159.
Cardellina, J.H. et a/, J. Org. Chern., 1988, 53, 882 (iso/, pmr, cmr)
Picrate: Cryst. Mp 95-98°. Uyehara, T. eta/, J. Chern. Soc., Chern. Commun., 1989, 1841
McChesney, J.D. et a/, J. Org. Chern., 1984, 49, 5154. (synth)
Reddy, N.K. eta/, Indian J. Chern., Sect. B, 1989, 28, 372 (synth)
Nakafuran 9 Sq-02752
Mexicanin D Sq-02749 [76844-26-3]
Neohelenalin. Flexuosin
[5945-70-0]

C 15H 200 M 216.322

Constit. of Dysidea fragilis. Shows antifeedant props. Oil.
[a]i,S -106° (c, 0.33 in CHC1 3).
C 15Ht80 4 M 262.305
Constit. of Helenium mexicanum, H. ooclinium and Schulte, G. eta/, Helv. Chim. Acta, 1980, 63, 2159.
Balduina angustifolia. Cryst. Mp 252-253°. [a] 0 + 107°
(CHC1 3). Nanaimoal Sq-02753
Herz, W. et a/, J. Am. Chern. Soc., 1960, 82, 2276; 1963, 85, 19 1,2,3 ,4,5 ,6, 7,8-0ctahydro-2,5 ,5-trimethy/-2-
(isol, struct) naphthaleneaceta/dehyde, 9Cl
[89320-84-3]
Microcionin 1 Sq-02750
[59805-75-3]

C15H 240 M 220.354

Constit. of nudibranch Acanthodoris nanaimoensis.
Ayer, S.W. eta/, Tetrahedron Lett., 1984, 25, 141 (iso/, synth)
C 15H 220 M 218.338
Constit. of Microciona toxystila. Oil. [a] 0 + 7°. Pallescensin A Sq-02754
Cimino, G. eta/, Tetrahedron Lett., 1975, 3723. [56881-68-6]

C 15H 220 M 218.338

Constit. of Disidea pa/lescens. Oil. [a] 0 +9.7°.
642
Pallescensin B - Palutropone Sq-02755 - Sq-02762

Cimino, G. eta/, Tetrahedron Lett., 1975, 1425 (isol, struct) Pallescensin F Sq-02759
Matsumoto, T. eta/, Chern. Lett., 1978, 105 (stereochem, synth)
Nasipuri, D. eta/, J. Chern. Soc., Perkin Trans. 1, 1979, 2776 [56881-48-2]
(synth) 0

QJl
Gariboldi, P. eta/, J. Org. Chern., 1982, 47, 1961 (synth)
Smith, A.B. eta/, J. Org. Chern., 1984, 49, 3685 (synth)
Shishido, K. eta/, Heterocycles, 1990, 31, 597 (synth)

Pallescensin B Sq-02755
C 15H 180 M 214.307
[56881-69-7]
Cons tit. of Disidea pa/lescens. Oil.
Cimino, G. et a/, Tetrahedron Lett., 1975, 1421 (isol)
Matsumoto, T. eta/, Bull. Chern. Soc. Jpn., 1983, 56, 491 (synth)

Pallescensin G Sq-02760
[56881-49-3]

qJJ
0

C 15H 20 0 M 216.322
Constit. of Disidea pallescens. Oil. [aln +62.6°.
Cimino, G. eta/, Tetrahedron Lett., 1975, 1425.
Ct5H 180 M 214.307
Pallescensin C Sq-02756 Constit. of Disidea pallescens. Oil. [aJn - 289°.
[56881-70-0] Cimino, G. et a/, Tetrahedron Lett., 1975, 1421 (isol)
Matsumoto, T. eta/, Bull. Chern. Soc. Jpn., 1983, 56, 491 (synth)

Pallescensolide Sq-02761
[93474-11-4]

g9
0

C,sH 180 M 214.307

Constit. of Disidea pallescens. Oil. [aln +424°.
Cimino, G. eta/, Tetrahedron Lett., 1975, 1425.

Pallescensin D Sq-02757 C16H 240 3 M 264.364

[56881-71-1] Constit. of Dysidea amblia. Cryst. Mp 53-56°. [aln -57.4°
(c, 0.9 in CHC1 3).
Guella, G. eta/, Helv. Chim. Acta, 1985, 68, 39.

Palutropone Sq-02762
1,2-Dihydro-4-methyl-6H-/Jenzocyclohepten-6-one, 9CI
[81916-09-8]

~0
C,sH 180 M 214.307
Constit. of Disidea pallescens. Oil. [aln -45.3°.
Cimino, G. eta/, Tetrahedron Lett., 1975, 1425.
l)J
C 12H 120 M 172.226
Constit. of Grindelia pa/udosa. Oil.
Pallescensin E Sq-02758
5,10-Dihydro-6, 7-dimethyl-4H -benzo[5 ,6]cyclohepta[1,2- 1,2-Dihydro: Dihydropalutropone
blfuran, 9CI C 12H 140 M 174.242
Constit. of G. pa/udosa. Oil. [a]~4 + 18° (c, 0.1 in
[56881-47-1]
CHC1 3).

H,CccY
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 167.

H3 C
C 15H 160 M 212.291
Constit. of Disidea pallescens. Oil.
Cimino, G. et a/, Tetrahedron Lett., 1975, 1421.
Baker, R. eta/, J. Chern. Soc., Perkin Trans. 1, 1981, 3087 (struct,
synth)

643
Parvifoline - Tanavulgarol Sq-02763 - Sq-02770

Parvifoline Sq-02763 Spiniferin 1 Sq-02767

[62706-41-6] [59806-73-4]

C 15H 160 M 212.291

Constit. of Pieraplysilla spinifera. Unstable oil. [1X]n -4.2°.
C 15H 100 M 216.322
Cimino, G. et al, Tetrahedron Lett., 1975, 3727 (isol)
(R)-form Cimino, G. et al, Experientia, 1978, 34, 1425 (struct)
Constit. of Coreopsis parvifo/ia and Perezia carpholepis. Marshall, J.A. et al, J. Am. Chern. Soc., 1983, 105, 5679 (synth)
Needles (Me 2COjhexane). Mp 85-86°. [1X]n -173° (c,
1. 73 in CHC1 3). Spiniferin 2 Sq-02768
Ac: Cryst. (Me 2COfhexane). Mp 59-61°. [1X]n -98°
[59806-74-5]
(CHC1 3).
Bohlmann, F. et al, Chern. Ber., 1977, 110, 468 (isol, struct)
Joseph-Nathan, P. et al, Phytochemistry, 1982, 21, 669 (struct)
Joseph-Nathan, P. et al, J. Nat. Prod. (Lloydia), 1988, 51, 675 (abs
config)

C 15H 160 M 212.291

Perforene Sq-02764 Constit. of Pleraplysilla spinifera. Unstable oil.
[59557-94-7] Cimino, G. et al, Tetrahedron Lett., 1975, 3727 (isol)

H,C(t)a
Cimino, G. et al, Experientia, 1978, 34, 1425 (struct)

Sbigol Sq-02769
CH3 Br [11017-56-4]

C15H 10BrCl M 315.680

Constit. of Laurencia perforata. Oil. [1X]n -3°.
Gonzalez, A.G. et al, Tetrahedron Lett., 1976, 205.

Pinthuamide Sq-02765
[122279-83-8]
0
C19H 220 6 M 346.379
Constit. of the root of Gossypium hirsutum. Potent seed
germination stimulant for Striga lutea. Cryst.
(C6H 6 /hexane). Mp 200-202° dec.
Cook, C.E. et al, J. Am. Chern. Soc., 1972, 94, 6198 (isol)
Coggon, P. et al, J. Chern. Soc., Perkin Trans. 2, 1973, 455 (cryst
C15H 19N04 M 277.319 struct)
Metab. of fungus Ampul/iferina sp. Needles (EtOAc). Mp Heather, J.B. et al, J. Am. Chern. Soc., 1976, 98, 3661 (synth)
190-193°. [IX]~ + 73.4° (c, 1.0 in EtOH). MacAlpine, G.A. et al, J. Chern. Soc., Perkin Trans. I, 1976, 410
Kimura, Y. et al, Tetrahedron Lett., 1989, 30, 1267 (cryst struct) (synth)
Johnson, A.W. et al, J. Chern. Soc., Perkin Trans. I, 1981, 1734
(bib/)
rt-Pseudowiddrene Sq-02766 Brooks, D.W. et al, J. Org. Chern., 1985, SO, 628, 3779 (synth,
[32540-28-6] cryst struct)
Dailey, O.D., J. Org. Chern., 1987, 52, 1984 (synth)
Berlage, U. et al, Tetrahedron Lett., 1987, 28, 3091, 3095 (synth)

Tanavulgarol Sq-02770
[112663-82-8]
C15H 24 M 204.355

~OH
Constit. of Thujopsis dolabrata. Oil. [1X]~6 +67.7° (CHC1 3).
Ito, S. et al, Tetrahedron Lett., 1974, 1041.

C1sH2402 M 236.353
Constit. of Tanacetum vulgare. Oil. [IX]~ + 80° (c, 0.3 in
CHC1 3).
Chandra, A. et al, Phytochemistry, 1987, 26, 3077.

644
Tehranolide - Widdrol Sq-02771 - Sq-02776

Tehranolide Sq-02771 Constit. of Dysidea fragilis. Oil. [IX]~ +92.6° (c, 0.27 in

<t;Yo
CHC1 3).
HO H / Schulte, G. et al, J. Org. Chem., 1980, 45, 552.

Vernoeggersic acid Sq-02775

[97510-41-3]

C 15H 110 6 M 298.335

Constit. of Artemisia diffusa. Cryst. Mp 99°.
Rustaiyan, A. et al, Phytochemistry, 1989, 28, 2723 (isol, pmr, cmr)

2,4,5,7a-Tetrahydro-1,4,4,7 a-tetramethyl- Sq-02772

1H-inden-2-ol, 9CI CuH310 4 M 384.514
2,2,6,7-Tetramethylbicyc/o[4.3.0]nona-1(9),4-dien-8-ol Constit. of Verbesina eggersii. Gum. [IX]~ -39° (c, 0.2 in
[9990 1-23-2] CHC13).
Banerjee, S. et al, Phytochemistry, 1985, 24, 1106.

~OH Widdrol Sq-02776

~ (6892-80-4]

C 13H 200 M 192.300

Constit. of Quince fruit flavour (Cydonia oblonga). Oil.
(IX]~ -40° (c, 0.67 in MeOH).
8-Ketone: [99901-22-1]. 1,4,5,7a-Tetrahydro-1,4,4,7a-
tetramethyl-2H-inden-2-one, 9CJ. 2,2,6,7-
Tetramethylbicyc/o[4.3.0]nona-1(9),4-dien-8-one
C 13H 180 M 190.285
From C. oblonga. Oil. [IX]~ + 11° (c, 0.2 in MeOH).
71X-Hydroxy: [99901-24-3]. 2,4,5,7a- Tetrahydro-1,4,4, 7a-
tetramethyl-1H-indene-1,2-diol, 9CI. 2,2,6,7-
Tetramethylbicyc/o[4.3.0]nona-1(9),4-diene-7,8-diol
C 13H 200 1 M 208.300
From C. oblonga. Oil. [IX]~ -6° (c, 0.35 in MeOH).
Ishihara, M. et al, J. Org. Chern., 1986, 51, 491.
1,5,5,8-Tetramethylbicyclo(4.2.1)non-7- Sq-02773
ene-9-acetaldehyde, 9CI
3,4-Seco-4-longibornen-3-al
[87479-93-4]
Absolute
configuration
C 15H 160 M 222.370
Constit. of Thujopsis dolabrata and Widdringtonia spp..
Also Cupressus arizonica, Chamaecyparis thyoides and
Juniperus spp. Cryst. (pet. ether). Mp 98°. [1X]n + 105°
(c, 2.3 in CHC13).
5rx,61X-Epoxide: Widdrol epoxide
C 15H 160 1 M 238.369
lsol. from wood of W. juniperoides. Mp 154°. [1Xln -9°.
Erdtman, H., Acta Chern. Scand., 1958, 12, 267 (isol)
Enzell, C., Acta Chern. Scand., 1962, 16, 1553 (epoxide)
Ito, S. eta/, Tetrahedron Lett., 1964, 3375 (struct)
Burlingame, A.L., J. Am. Chern. Soc., 1967, 89, 3232 (ms)
Sekizaki, H. eta/, Bull. Chern. Soc. Jpn., 1978, 51, 3603 (synth)
Danishefsky, S. eta/, J. Am. Chem. Soc., 1980, 102, 6891 (synth)
Uyehara, T. et al, Tetrahedron, 1987, 43, 5605 (synth)

'-A~
~'CHO

C 15H 140 M 220.354

Constit. of Artemisiajilifolia. Oil. [IX]~ +89° (c, 4.21 in
CHC1 3). Not a longibomane.
[64854-51-9]
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 503 (isol)
Satyanarayana, N. eta/, Synth. Commun., 1985, 15, 331 (synth)

Upial Sq-02774
[72378-77-9]

~CHO
,0
M 248.321

645
Acanthodoral - rx-Caryophyllene alcohol Sq-02777 - Sq-02784

[87064-18-4)
Shitole, M.R. eta/, Tetrahedron Lett., 1983, 24, 2411, 4739 (iso/,
Miscellaneous tricyclic cryst struct)
Kuo, D.L. eta/, Can. J. Chern., 1988, 66, 1794 (synth)

sesquiterpenes Antibiotic AA 57
1-Chloromethyl-1 ,2,4,4a,6a, 7-hexahydro-1-hydroxy-7,8-
Sq-02781
dimethyl-2-oxopentaleno[l ,6a-c]pyran-5-carboxylic acid, 9CI.
AA 57
[68026-87 -9]
Acanthodoral Sq-02777
[90857-63-9]
H COOH
CHO
I
C!Hz H

~-- HO~O
0
C 15H 17Cl05 M 312.749
C 15H 240 M 220.354 lsol. from Streptomyces spp. Has antibiotic props, active
Constit. of Acanthodoris nanaimoensis. against gram-positive and -negative bacteria. Cryst. Mp
4-Bromophenylurethane: Cryst. (hexane). Mp 109-110°. 123°. [IX]~ -143° (c, 1 in CHCI3).
Ayer, S.W. et a/, J. Org. Chern., 1984, 49, 2653. Me ester: Mp 130°.
Aizawa, S. eta/, J. Antibiot., 1978, 31, 729 (isol, struct)
Albene Sq-02778
3a,4,5,6,7,7a-Hexahydro-3a,7a-dimethyl-4,7-methano-1H- Aquatolide Sq-02782
indene, 9Cl. 2,6-Dimethyltricyclo[5.2.1.0 2 •6]dec-3-ene [125132-06-1]

iib
[38451-64-8]

\ H ,'
C 12H 18 M 162.274 0~
0
Constit. of Petasites and Adenostyles spp. Cryst. Mp 110-
1150. [1X]i? -9.2° (c, 0.54 in CHC1 3). CtsHta03 M 246.305
Constit. of Asteriscus aquaticus. Cryst. Mp 142-143°. [1X] 0
Kreiser, W. eta/, Tetrahedron, 1978, 34, 131 (isol)
Baldwin, J.E. eta/, J. Org. Chern., 1981, 46, 2442; 1983, 48, 625; +66.3° (c, 0.45 in CHCI 3).
1986, 51, 1133 (abs config, synth, struct) San Feliciano, A. eta/, Tetrahedron Lett., 1989, 30, 2851.

Allocedrol Sq-02779 4-Bromo-2,5,6-trimethyl-11-

[50657-30-2] methylenetricyclo(6.2.1.0 1•6]undecan-3-
one Sq-02783
I

0~
Br~
C 15H 26 0 M 222.370
Constit. of Juniperus rigida. Cryst. (hexane). Mp 81.SO. [1X] 0 C1sH2tBrO M 297.234
+68°. Metab. of Laurencia tenera. Unstable cryst. [1X] 0 -190.2°
Tomita, B. eta/, Phytochemistry, 1973, 12, 1409. (c, 0.004 in CHCI 3).
Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1695 (isol, pmr, cmr)
Alloisolongifolene Sq-02780
[87064-18-4] rx-Caryophyllene alcohol Sq-02784
Apollanol
[4586-22-5]

C 15H 24 M 204.355
Acid-catalysed rearrangement prod. of Longifolene, Sq-
02284. Oil. [1X] 0 -40.6° (CHCI 3). M 222.370

646
P-Caryophyllene alcohol - Guimarediol Sq-02785 - Sq-02792

Constit. of Cedrus atlantica also obt. from acid treatment oc-Duprezianene Sq-02789
of Humulene. Cryst. Mp 118.5-119.SO. Opt. inactive [7980 1-29-9]
(meso-).
Corey, E.J. et al, J. Am. Chern. Soc., 1965, trT, 5733 (synth)
Gemmell, K.W. et a/, J. Chern. Soc. B, 1970, 947 (cryst struct)
Adams, D.R. et al, J. Chern. Soc., Perkin Trans. 1, 1975, 1502
(isol)

1}-Caryophyllene alcohol Sq-02785 C 1 ~H 24 M 204.355

Constit. of Cupressus dupreziana. Oil.
[472-97-9]
Piovetti, L. et al, Phytochemistry, 1977, 16, 103 (isol)
Kirtany, J.K. et al, Indian J. Chern., Sect. B, 1981, 20, 506 (struct)

Germazone Sq-02790
[62332-96-1]

f0ro
H
C 1 ~H 16 0 M 222.370
Constit. of Palmarosa and other oils. Oil.
Naves, Y., Parfums, Cosmet. Savons Fr., 1970, 13, 354 (isol)

~
Barrow, C.J. et al, Aust. J. Chern., 1988, 41, 1755 (pmr, cmr)
I
Cerapicol Sq-02786 C 1 ~Hu0 M 218.338
1,4,4,8- Tetramethyltricyclo[6.2.1.0 2•6]undecan-JJ-o/ Constit. of Germanium macrorrhizum. Mp 36-38°.
[62065-27-4] Semicarbazone: Cryst. Mp 126-128°.
Tsankova, E. et a/, Tetrahedron, 1978, 34, 603.

Glutinopallal Sq-02791
[113540-85-5]

C 1 ~H 160 M 222.370
Metab. of fungus Ceratocystis piceae. Oil. [IX]~ +24.7° (c,
1.00 in CHC1 3).
Hanssen, H.-P. et al, Tetrahedron, 1988, 44, 2175 (struct)

Culmorin Sq-02787 C 16 H 20 0~ M 292.331

[18374-83-9] 0 5-0ctadecanoy/: StearylglutinopallaJ
C 34 H~0 6 M 558.797
Metab. of Lactarius g/utinopallens.

H~
0 5-Hexadecanoy/: Palmitylglutinopallal
C3zH 500 6 M 530.743
Absolute Metab. of L. glutinopallens.
configuration Favre-Bonvin, J. et al, Phytochemistry, 1988, 27, 286.
OH
C 1 ~H 16 0 1 M 238.369 Guimarediol Sq-02792
Metab. of Fusarium spp. Cryst. Mp 175°. [IX]~ -14.SO. [94835-99-1]
Barton, D.H.R. eta/, J. Chern. Soc., Chern. Commun., 1967, 30
(struct)
Roberts, B.W. eta/, J. Am. Chern. Soc., 1969, 91, 3400 (synth)
Hanson, J.R. et al, J. Chern. Soc., Perkin Trans. 1, 1976, 2471
HO~
(biosynth) ·
Reddy, R.T. et al, Indian J. Chern., Sect. B, 1986, 25, 457 (synth) Br~
C 15H 23Br01 M 315.249
Dipterol Sq-02788 Constit. of red alga Laurencia sp.
[53755-55-8] 4-Ac: Cryst. Mp 94-95°. [1X]i; + 30° (c, 1.2 in CHCI 2).
Gonzalez, A.G. et al, Chern. Lett., 1984, 1865 (cryst struct)

~H
C 1 ~H 160 M 222.370
Constit. of Dipterocarpus macrocarpus. Cryst. Mp 120-
121°. [1X]~4 + 53.8° (c, 0. 743 in CHC1 3).
Krishnamurty, H.G. et al, Indian J. Chern., 1974, 12, 520.

647
3-Hydroxylongibornane-3,5-... - lsorhodolaureol Sq-02793 - Sq-02800

3-Hydroxylongibomane-3,>endoperoxide Sq-02793 9-lsocyanopupukeanane Sq-02797

[87376-73-6] [57462-28-9]

C15H 1•.03
:~~
M 252.353
\~
Constit. of Artemisiafi/ifolia. Cryst. (pet. ether). Mp 142°.
[ex]~ -68° (c, 1.48 in CHC13).
\
~ I
Absolute
configuration

C16H:zsN M 231.380
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 503.
Constit. of the secretion of Phyllidia varicosa. Oil.
9-Epimer: 9--Epi-9--isocyfiiWpupuketiiUUU!
lsoclovene Sq-02795 C16H:zsN M 231.380
[5975-39-3] Constit. of P. bourguini. Shows ichthyotoxic and
antifungal props. Oil. [exln +31° (c, 0.048 in CHC1 3).
[70329-80-5]
Burreson, B.J. et al, J. Am. Chern. Soc., 1975, 97, 4763 (isol)
Corey, E.J. et al, J. Am. Chern. Soc., 1979, 101, 1608 (synth)
Yasarnoto, H. eta/, J. Am. Chern. Soc., 1979, 101, 1609 (synth)
Piers, E. eta/, Justus Liebigs Ann. Chern., 1982, 973 (synth)
Fusetani, N. eta/, Tetrahedron Lett., 1990, 5623 (epimer)
C15H 24 M 204.355
Rearr. prod. ofcaryophyllene. Viscous liq. Bp 12 130-131°.
Isokhusenic acid Sq-02798
[ex]~ -56.6°.
(16202-79-2]
Goswami, P. et a/, Indian J. Chern., Sect. B, 1976, 14, 299 (struct)
Kellner, D. et a/, Tetrahedron Lett., 1983, 24, 3397 (synth)

~
Baraldi, P.G. et al, Tetrahedron Lett., 1983, 24, 5669 (synth)

2-lsocyanopupukeanane Sq-02796
[73069-50-8] HOOC
C 15H 220 1 M 234.338
Constit. of Vetiveria zizanioides.
Komae, H. eta/, J. Org. Chern., 1968, 33, 1771.

Absolute Isolongifolene Sq-02799

configuration
[113 5-66-6]

C16H:zsN M 231.380
Secreted by the nudibranch Phyllidia varicosa. Cryst.
(Me<>H aq.). Mp 81-82°.
[72715-04-9, 72748-63-1]
Hagadone, M.R. eta/, Helv. Chim. Acta, 1979, 62, 2484 (cryst
struct, abs cmifig)
Corey, E.J. eta/, Tetrahedron Lett., 1979, 2745 (synth)
Frater, G. eta/, Helv. Chim. Acta, 1984, 67, 1702 (synth)
C 15H 24 M 204.355
Acid-catalysed rearr. prod. of Longifolene. Liq. Bp0 _4 82-
830. (exJn -78.1° (c, 5.5 in EtOH).
Ranganathan, R. eta/, Tetrahedron, 1970, 26, 621 (struct)
Sobti, R.R. et al, Tetrahedron, 1970, 26, 649 (synth)
Piers, E. et al, Can. J. Chern., 1979, 57, 2314 (synth)

lsorhodolaureol Sq-02800
[124596-91-4]

C 15H 22BrC10 M 333.695

Metab. of Laurencia majuscu/a. Cryst. Mp 120.5-122°. [exJn
+61° (c, 0.07 in CHC1 3).
Coli, J.C. et al, Aust. J. Chern., 1989, 42, 1591 (isol, pmr, cmr)

648
Italicene - P-Neoclovene Sq-02801 - Sq-02809

ltalicene Sq-02801 Longihomocamphenylone Sq-02805

[94535-52-1]

C 15H 24 M 204.355 C 15H 240 M 220.354

Constit. of Helichrysum oil. Oil. [IX]~ -53.8° (c, 3.0 in Oxidn. prod. of Longifolene. Cryst. Mp 55-57°.
CHC1 3).
Munavalli, S. et al, Bull. Soc. Chirn. Fr., 1964, 729 (struct)
7-Epimer: [94482-89-0]. lsoitalicene Mehra, M.M. et al, Tetrahedron, 1965, 21, 637 (synth)
C 15H 24 M 204.355
Constit. of H. oil. [IX]~ + 35.4° (c, 1.4 in CHC1 3).
11-Methyl-7- Sq-02806
Leimner, J. et al, Chern. Lett., 1984, 1769 (isol, struct, synth)
oxatetracyclo(6.3.1.0 1• 6.0"• 11 )dodecane
Hexahydro-5a-methyl-3H-1,6:3,8a-dimethano-JH-
Khusiol Sq-02802 cyclopent[c]-oxepin, 8Cl
[66512-59-2] [28344-11-8]

~OH C12H 180 M 178.274

C 15H 21;0 M 222.370 lsol. from sandalwood oil Santa/urn album. Mp 178-180°.
Constit. of oil of Vetiveria zizanioides. Cryst. by subl. Mp Kretschmar, H.C. et al, Tetrahedron Lett., 1970, 37 (isol, prnr,
81°. [1X]n -66° (c, 1.4 in CHC1 3). struct, synth)
p-Nitrobenzoyl: Cryst. Mp 138-139°. Demole, E. et al, Helv. Chirn. Acta, 1976, 59, 737 (isol)
Ganguly, R.N. et al, Indian J. Chern., Sect. B, 1978, 16, 23.
Myltaylenol Sq-02807
Lemnalol Sq-02803 [97915-44-1]

WF
[22570-34-1]

HOCH2
Absolute
C 15H 240 M 220.354
configuration
Constit. of Mylia taylorii. Cryst. Mp 69-70.SO. [a:Jn -59°.
C 15H 240 M 220.354 Takaoka, D. et al, J. Chern. Soc., Chern. Cornrnun., 1985, 482.
Constit. of Lemnalia tenuis. Cryst. Mp 46-47°. [1X]i? -9.3°
(c, O.oi in CHC1 3). Neoclovene Sq-02808
Kikuchi, H. et al, Tetrahedron Lett., 1982, 23, 1063 (cryst struct) [4545-68-0]
Kulkarni, Y.S. et al, J. Org. Chern., 1987, 52, 1568 (synth)

Longifolic acid
[487-73-0]
Sq-02804
a Abrolut<
\ ) \ - configuration

C 15H 24 M 204.355
Acid-catalyzed rearr. prod. of Caryophyllene. Bp0 . 03 52°.
[a:]i; -72° (c, 1. 78 in CHC1 3).
McKillop, T.F.W. et al, J. Chern. Soc. C, 1971, 3375 (synth)

C 15H 240 2 M 236.353 P-Neoclovene Sq-02809

Obt. by oxidn. of Longifolene. Cryst. (EtOH aq.). Mp [56684-96-9]
143-144°. [IX]~ -32.6° (c, 5.8 in EtOH).
Nayak, U.R. et al, Tetrahedron, 1963, 19, 2293 (synth)
Dev, S., Fortschr. Chern. Org. Naturst., 1981, 40, 49 (rev)

M 204.355

649
Pardalianchol- Punctaporonin E Sq-02810 - Sq-02816

Constit. of Panax ginseng. [1X]i; -30° (MeOH). Constit. of Gaillardia pulchella. Cryst. (MeOH/CHC1 3).
Yoshihara, K. eta/, Bull. Chern. Soc. Jpn., 1975, 48, 2078 (isol, Mp 225-227°. [1X]~ -66° (c, 1 in EtOH).
struct) Inayama, S. et a/, Chern. Pharm. Bull., 1975, 23, 2998.

Pardalianchol Sq-02810 Punctaporonin A Sq-02814

[71939-79-2] Punctatin A. M 95464. Antibiotic M 95464
[91161-74-9]

HO~zc
f H OH
6

C 15Hi..O M 220.354 HO
Constit. of Doronicum pardalianches. Oil. [1X]i;' -71.9° (c, C 15H 240 3 M 252.353
0.95 in CHC1 3). Sesquiterpene antibiotic. Metab. of Poronia punctata.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 668. Cryst. (EtOAc). Mp 187-192°. [1X]i:' -26° (c, 1 in
MeOH). Not to be confused with homoisofiavone
Perforatone Sq-02811 Puncta tins.
[57566-98-0] 6-Epimer: [102734-12-3]. Punctaporonin D. Punctatin D. M
167906. Antibiotic M 167906
CtsH 240 3 M 252.353
From P. punctata. Plates (EtOH). Mp 199-201°. [1X]i:'
+ 125° (c, 1 in MeOH).
Paquette, L.A. eta/, J. Am. Chern. Soc., 1986, 108, 3841 (synth,
abs con.fig)
Poyser, J.P. eta/, J. Antibiot., 1986, 39, 167 (iso/, struct)
C 15H 22 Br20 M 378.146 Sugimura, T. eta/, J. Am. Chern. Soc., 1987, 109, 3017 (synth)
Constit. of Laurencia perforata. Cryst. Mp 106-108°. [1Xln Anderson, J.R. eta/, J. Chern. Soc., Perkin Trans. I, 1988, 823
+ 186° (c, 1.58 in CHC13). (isol, struct)
1,9-Diepimer:
C 15H 22 Brp M 378.146 Punctaporonin C Sq-02815
Constit. of L. tenera. Cryst. Mp 112-113°. [1X]n -25° (c, Punctatin C
0.002 in CHC1 3). [93672-19-6]
Gonzalez, A.G. et a/, Tetrahedron Lett., 1975, 2499 (isol)
Coli, J.C. eta/, Aust. J. Chern., 1989, 42, 1695 (isol, pmr, cmr, HC? H 1;1
HOOCCH2 CH2 COO~
cryst struct)

Pseudoclovene B Sq-02812 0 \
pseudo-Clovene B H H
[37592-80-6]
HO \
H C 19H 280 7 M 368.426

~
Metab. of Poroniapunctata. Cryst. (EtOAc). Mp 158-161°.
Absolute [1X]i:' -14° (c, 1 in MeOH). Not to be confused with
configuration homoisofiavone Punctatins.
Anderson, J.R. eta/, J. Chern. Soc., Perkin Trans. I, 1988, 823
CtsH24 M 204.355 (iso/, struct)
Rearr.'prod. ofCaryophyllene. Liq. Bp 10 111-112°. [1X]i:'
+ 3} (c, 1.66 in CHC13).
0
Punctaporonin E Sq-02816
Crane, R.I. eta/, J. Chern. Soc., Chern. Commun., 1972, 385 Punctatin E. M 171950. Antibiotic M 171950
(struct)
Chatterjee, S. et a/, J. Chern. Soc., Perkin Trans. I, 1979, 2914 [106673-28-3]
(synth)
Maity, S.K. eta/, Indian J. Chern., Sect. B, 1990, 29, 501 (synth)

Pulchellon Sq-02813
[58210-32-5]

J}o
I
I Ct 5H2403 M 252.353
Sesquiterpene antibiotic. !sol. from Poronia punctata.
Cryst. (EtOAc). Mp 176°. [1X]i:' -39° (c, 1 in MeOH).
Subl. at 157-165°.
4-Epimer: [106758-24-1]. Punctaporonin F. Punctatin F. M
189122. Antibiotic M 189122
I
CtsH240 3 M 252.353
HO
M 210.272

650
Rhodolauradiol - 2,6,6,8-Tetramethyltricyclo[6.2.1.0··· Sq-02817 - Sq-02823

From P. punctata. Cryst. (EtOAc). Mp 205-208°. [1X]i;l Constit. of Senecio crassissimus. Cryst. (2-propano1). Mp
+80° (c, 1 in MeOH). Subl. at 150°. 93-96°. [1X]~4 -10.9° (c, 0.23 in CHC1 3).
Poyser, J.P. eta/, J. Antibiot., 1986, 39, 167 (isol, struct) 6-Deoxy, 5-oxo:
C15H:w0 2 M 236.353
Rhodolauradiol Sq-02817 Constit. of Eurypon sp. Oil. [1X]n -3.3° (c, 0.9 in
CHC1 3).
(83108-35-4]
6-Deoxy, 5-oxo, 3-Me ether:
C16H 260 2 M 250.380
HO~ Constit. of a E. sp. Oil. [1X]n -5.6° (c, 0.9 in CHC1 3).
Dideoxy, 3,4-didehydro, 51X-hydroxy:
Br~Cl C 15H:w0 M 220.354
Constit. of a E. sp. Oil. [1X]n -12.8° (c, 0.9 in CHC1 3).
C 15H:wBrC10 2 M 351.710 Bohlmann, F. eta/, Phytochemistry, 1981, 20, 469 (isol)
Constit. of a Laurencia sp. Oil. Barrow, C.J. eta/, Aust. J. Chern., 1988, 41, 1755 (derivs)
10-Deoxy, 1,10-didehydro: [83108-36-5]. Rhodolaureol
C 15H 22 BrC10 M 333.695 Senoxydene Sq-02821
Constit. of a L. sp. Cryst. (hexane). Mp 57-58°. [1X]n
+ 139° (c, 1.2 in CHC1 3).
Gonzalez, A.G. eta/, J. Chern. Soc., Chern. Commun., 1985, 260.

Sambucinic acid Sq-02818

[115491-57-1]
C15H:w M 204.355
The proposed struct. (illus.) has been shown to be
incorrect by synthesis. Constit. of Senecio oxyodontus.
Oil.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1747 (isol)
Paquette, L.A. eta/, J. Am. Chern. Soc., 1983, 105, 6975.

C 15H 220 3 M 250.337

Metab. of Fusarium sambucinum. Cryst. Mp 200-207°.
Seychellene Sq-02822
[20085-93-2]
Riisslein, L. et a/, Helv. Chim. Acta, 1988, 71, 588 (isol, pmr, cmr,
cryst struct)

Santonic acid Sq-02819

[510-35-0] Absolute
configuration

C 15H:w M 204.355
Constit. of oil of Patchouli. Oil. Bp0.1 70°. [1X]n -72° (c,
0.4 in CHC1 3).
Wolff, G. eta/, Tetrahedron, !969, 25, 4903 (iso/, struct)
Frater, G., Helv. Chim. Acta, 1974, 57, 172 (synth)
Wolff, G., Recherches, 1974, 19, 85 (rev)
Yamada, K. eta/, Tetrahedron, 1979, 35, 293 (synth)
Jung, M.E. eta/, J. Am. Chern. Soc., 1981, 103, 6677 (synth)
C,sHzo04 M 264.321 Hagiwara, H. et a/, J. Chern. Soc., Chern. Commun., 1985, 1047
Cryst. (EtOH). Mp 170-172°. Bp 15 285°. [1X]i,6 -74° (synth)
(CHC1 3). Welch, S.C. et a/, J. Org. Chern., 1985, SO, 2668, 2676 (synth, bibl)
Me ester: [39953-23-6]. Akhila, A. eta/, Phytochemistry, 1988, 27, 2105 (biosynth)
Cryst. (MeOH). Mp 66-67.SO. [1X]i,6 -52.3° (CHC1 3). Hagiwara, H. eta/, J. Chern. Soc., Perkin Trans. !, 1990, 2109
(synth)
Hortmann, A.G. eta/, J. Org. Chern., 1972, 37, 4446.

2,6,6,8-
Senecrassidiol Sq-02820
Tetramethyltricyclo(6.2.1.0 1•5)undecan-7-
[79433-54-8] ol Sq-02823
Octahydro-3,6,8,8-tetramethyl-JH-3a,6-methanoazulen-7-ol,
9CI

q}~HI
/

C 15H 260 M 222.370

M 238.369 7fJ-form [60389-81-3]

651
Tricyclohumuladiol - Xanthipungolide Sq-02824 - Sq-02830

Constit. of Eremophila georgei. Cryst. Mp 39-42°. [1X]n 4,11,11-Trimethyltricyclo(6.3.1.0 2•5)dodec- Sq-02827

-32° (c, 1.1 in CHCI 3). 7-en-6-one
4-Bromobenzoy/: [60389-85-7].
Cryst. Mp 122°. [1X]n -11 o (c, 0.45 in CHC13).
Ketone: [60389-80-2]. 2,6,6,8-
Tetramethytricyc/o[6.2.1.01·5]undecan-7-one
C 15H 240 M 220.354
From E. georgei.
Ghisalberti, E.L. et ai,J. Chem. Soc., Perkin Trans. 1, 1976, 1300
(cryst struct) C15H 110 M 218.338
Carrol, P.J. et al, Phytochemistry, 1976, 15, 777 (isol, struct) Constit. of a Eurypon sp. Oil.
Kernan, M.R. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1353 (isol,

'0
Tricyclohumuladiol Sq-02824 pmr, cmr)
[21446-02-6]
Vulgarone A Sq-02828
OH
[62065-10-5]

-(2)5
OH
H
H

C 15H 260 1 M 238.369 0

Constit. of hop oil. Cryst. (EtP/MeOH). Mp 207°. [1X]i:+ C15H110 M 218.338
0° (c, 2.7 in MeOH). Constit. of Chrysanthemum vulgare. Oil. [IX]~ + 113.7° {c,
Naya, Y. et al, Bull. Chem. Soc. Jpn., 1969, 42, 2405 (isol, struct) 0.95 in CHCI 3).
Namikawa, M. et al, Chem. Lett., 1978, 391 (synth) Uchio, Y., Tetrahedron, 1978, 34, 2893.

4,11,11- Waitziacuminone Sq-02829

Trimethyltricyclo[6.3.1.02•5)dodecane- [125467-36-9]
6,8-diol Sq-02825

-OH

C15H 240 M 220.354

CisH260 1 M 238.369 Constit. of Waitzia acuminata. Oil.
Constit. of a Eurypon sp. Oil. [1X]n - 10° (c, 0.002 in Jakupovic, J. et al, Phytochemistry, 1989, 28, 1943.
CHCI 3).
Kernan, M.R. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1353 (isol, Xanthipungolide Sq-02830
pmr, cmr)
0
4,11,11-Trimethyltricyclo(6.3.1.02•5)dodec- Sq-02826
6-en-8-ol

C15H 180 3 M 246.305

Constit. of Xanthium pungens. Cryst. Mp 87°.
C15H 240 M 220.354 Ahmed, A.A. et al, Phytochemistry, 1990, 29, 2211 (isol, pmr, cmr)
Constit. of a Eurypon sp. Cryst. (hexane). Mp 115°. [1X]n
-6.1° (c, 0.03 in CHCI 3).
Kernan, M.R. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1353 (isol,
pmr, cmr)

652
Cycloseychellene - Solanascone Sq-02831 - Sq-02835

Naematolln C Sq-02834

Tetracyclic
[130009-40-4]
OH

sesquiterpenes ~-OH
~OAc
Cycloseychellene Sq-G2831 C 17H:11;06 M 326.389
Metab. of Naemato/oma fasciculare. Needles. Mp 142°.
[52617-34-2] [IX]~ -19° (c, 0.31 in dioxan).
6-Epimer: [129929-74-4]. Naemato6n G
Metab. of N.fasciculare. Needles. Mp 176-177°. [IXFn
-64.5° (c, 0.16 in dioxan).
Doi, K. et a/, J. Chqn. Soc., Chem. Commun., 1990, 725 (isol,
cryst struct)
ClsH14 M 204.355
Constit. of Pogostemon cab/in. Oil. Solanascone Sq-02835
Terhune, S.J. et a/, Tetrahedron Lett., 1973, 4705 (isol) [68690-84-6]
Welsh, S.C. eta/, J. Org. Chem., 1981, 46, 4819; 1985, 50, 2676
(struct, synth) -
Niwa, H. eta/; Tetrahedron_Lett., 1983, 24, 937 (synth)
Akhila, A. eta/, Phytochemistry, 1988, rT, 2105 (biosynth) 0~~/ /
2 9
ll-Hydroxy-4-jungistoeben-3-one Sq-G2832 I 0
I

~OH
C 15H 220 M 218.338
Constit. of Nicotiana tabacum and produced by
photocyclisation of solavetivone. Oil. [IX]~ + 20.3° (c,
1.97 in CDC1 3).
Oxime: Cryst. Mp 121-123°.
C 15H 100 2 M 232.322 2,3-Didehydro: [88125-ll-5]. 2)-Dehydrosoltuuucone
ClsH100 M 216.322
Ac: 12-Acetoxy-4-jugistuebe•J-one Constit. of flue-cured tobacco leaves. Oil.
C 17H 220 3 M 274.359
Constit. of Jungia stuebelii. Gum. [IX]~ + 10° (c, 0.15 in 3P-Hydroxy, 3-0-P-sophoroside: [88848-60-6]. 1/J-
CHC13). Hydroxysoltuuucone JJ-sophoroside
CnH420u M 558.622
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 1201.
Constit. of tobacco. [1X]n -l.SO (c, 0.54 in EtOH).
9-Hydroxy, 9-0-P-D-glucopyranoside: 9-
v-Longifollc acid Sq-o2833 GIIIcopyrtiiUJsy/oxysoltuuucone
Pseudolongifo/ic acid C21H320 7 M 396.480
[19888-35-8] Constit. of flue-cured tobacco leaves.
10-Hydroxy, 10-0-P-D-glucopyranoside: 10-

~
GIIIcopyrtiiUJsy/oxysoltuuucone
C21H320 7 M 396.480
Constit. of flue-cured tobacco leaves.
Fujimori, T. et a/, J. Chem. Soc., Chem. Commun., 1978, 563 (isol,
struct)
Nishikawaji, S. eta/, Phytochemistry, 1983, 22, 1819 (isol)
HOOC Kodama, H. eta/, Agric. Bioi. Chem., 1984, 48, 3131; 1985, 49,
C 15H 220 2 M 234.338 2537 (pmr, deriv)
Oxidn. prod. of Longifolene. Cryst. (EtOH aq.). Mp 171- Tazaki, H. eta/, Agric. Bioi. Chem., 1989, 53, 3037 (derivs)
1720. [1X]i: + 18.3° (c, 4.5 in EtOH).
Nayak, U.R. eta/, Tetrahedron, 1963, 19, 2293 (synth)
Mehta, G. eta/, Tetrahedron, 1968, 24, 4105 (struct)
Dev, S., Fortschr. Chem. Org. Naturst., 1981, 40, 49 (rev)

653
Diterpenoids

655
Acanthoaustra lide - 1,4-Dihydroxy-2,7(19),10,14-... Di-00001 - Di-00007

Chlorodesmin Dl-00004
1,16,17,20-Tetraacetoxy-1 ,3(20),6,10,15-phytapentaen-13-
Phytanes one
[72877-82-8)
OAc

Acanthoaustralide Dl-00001
1,6-Dihydroxy-2,10,14-phytatrien-18,7-olide
[79404-42-5]
CZIIH3809
Constit. of Chlorodesmis fastigiata. Oil.
10,11-Dihydro: 1,16,17,20-Tetraacetoxy-1,3(20),6,15-
17 ~
phytatetraen-13-one. 10)1-Dihydrochlorodesmin
OH C~OH CZIIH4009 M 520.6I9
Constit. of C. fastigiata. Oil.
Czoli310 4 M 336.470
Constit. of Acdnthospermum australe. Gum. Wells, R.J. et al, Experientia, 1979, 35, 1544.
l-Ac:
CnH340 5 M 378.508 Dictyodendrillolide Dl-00005
Contit. of A. australe. Gum. [ex)~ + 7° (c, 0.2 in CHC1 3). 1-Acetoxy-2,6,10,14-phytatetraen-20,1-olide
17-Hydroxy: 17-Hydroxyocflllthotlllstra/ide [117585-47-4]
C10H 310 5 M 352.470
Constit. of Melampodium longipilum.
17-Acetoxy: 17-Acetoxyactlllthotlllstra/ide
CnH340 6 M 394.507
Constit. of M. /ongipilum. Gum. CzzH310 4 M 360.492
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1081. Constit. of a Dictyodendrilla sp. Oil. [ex]~ +21.9° (c, 0.43
Quijano, L. et al, Phytochemistry, 1984, 23, 829 (deriv) in CHC1 3).
Cambie, R.C. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1014.
Ambliofuran Dl-00002
3-(4,8,12- Trimethyl-3,7,11-tridecatrienyl}furan, 9CI. 1,20- 1,16-Dihydroxy-2,6,10,14-phytatetraen-18- Dl-00006
Epoxy-1 ,3(20),6,10,14-phytapentaene oic acid
[76215-29-7]

C10H 300 M 286.456 C10H 310 4 M 336.470

Constit. of Dysidea amblia. Oil. (2Z,6E,10Z)4E)-f orm [8093I-02-8) Wyethic acid
6,7,10,11,14,15-Hexahydro: [54869-li-3). 3-(4,8,12- Constit. of Wyethia helenioides.
Trimethyltridecyl}furan, 9CI. I ,20- Epoxy- I ,3(20)- Bohlmann, F. et al, Phytochemistry, 1981, 20, 2245.
phytadiene. Phytofurflll
C10H 360 M 292.504
Constit. of Burley tobacco. Oil. 1,4-Dihydroxy-2,7(19),10,14-phytatetraen- Dl-00007
18,19-Dihydroxy: [84765-52-6]. 1,20-Epoxy-1,3(20),6,10,14-
13-one
phytapentaene-18,19-dio/. Conypodot6ol 13,16-Dihydroxy-2,6,14-trimethyl-10-methylene-2,6,14-
Czoll300 3 M 3I8.455 hexadecatrien-4-one
Constit. of Conyza podocephala. Gum.
Dare, D.L. et al, J. Chem. Soc., Perkin Trans. 1, 1973, 1130.
Fujimori, T. et al, Agric. Bioi. Chem., 1974, 38, 2273.
Demo1e~E. et al, Helv. Chim. Acta, 1978, 61, 2318.
Walker, R.P. et al, J. Org. Chem., 1981, 46, 1098 (Ambliofuran) CzoH310 3 M 320.47I
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1693 (Conypododiol)
(2E,4R,10E)-form
Constit. of Cystoseira crinita. Oil. [exln +96.5° (c, I in
Centipedic acid Dl-00003 EtOH).
1,20-Epoxy-] ,3(20),6,10,14-phytapentaen-18-oic acid
4-Ketone: 1-Hydroxy-2,7(19),10,14-phytatetraene-4,13-
[72943-98-7] dione. 16-Hydroxy-2,6,14-trimethyl-10-methylene-2,6,14-
hexadecatriene-4,13-dione
C10H 300 3 M 318.455
Constit. of C. crinita. Oil.
M 316.439 Amico, V. et al, Phytochemistry, 1981, 20, 1085.
C10HZ1103
Constit. of Centipeda orbicularis. Oil.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1067 (isol, struct)
Kramp, W. eta[, Justus Liebigs Ann. Chem., 1986, 226 (synth)

657
1,7-Dihydroxy-2,5,10,14-... - 11,15-Epoxy-3(20)-phytene-1,2-diol Di-00008 - Di-00016

1,7-Dihydroxy-2,5,10,14-phytatetraen-13- Dl-00008 C21 H 300 4 M 346.466

one Constit. of D. asperatum. Gum.
10,16-Dihydroxy-2,6,1 0,14-tetramethyl-2 ,6, 11,14- Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1335.
hexadecatetraen-4-one, 9CI
7,8-Epoxy-1-hydroxy-2,5,10,14- Dl-00013
phytatetraen-13-one
0
7,8-Epoxy-1-hydroxy-3,7,11 ,15-tetramethyl-2,5,10,14-
C 20 H 320 3 M 320.471 hexadecatetraen-13-one
(2E,5E,7f.,lOE)-form [79404-60-7]
Constit. of Cystoseira crinita. Oil. [1X] 0 -16.1° (c, I in
EtOH).
Amico, V. eta/, Phytochemistry, 1981, 20, 1085. 0
C20H 300 3 M 318.455
1,19-Dihydroxy-2,6-14-phytatrien-18-oic Dl-00009 (2E,5E,7(.,8f.,lOE)-form
Constit. of Bifurcaria bifurcata. Oil.
acid
Combaut, G. eta/, Phytochemistry, 1983, 22, 1787.

1,20-Epoxy-1,3(20),1 0,14-phytatetraene- Dl-00014

18,19-dioic acid
C 20 H 340 4 M 338.486
10
(2E,6Z,ll f.)-form 17 I~
19-Ac: [129350-24-9]. Divaricatic acidt
C22H 360 5 M 380.523
COOH
18
COOH I 0'
Constit. of Pteronia divaricata. Oil. M 348.438
C20H280s
Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr) (JOZ)-form
18-Me ester: [111150-39-1]. Microglossic acid
3,15-Dihydroxy-1,6,13-phytatrien-12-one Dl-0001 0 C21H300 5 M 362.465
2,14-Dihydroxy-2,6,10,14-tetramethyl-3,10,15-hexadecatrien- Constit. of Microglossa zeylanica. Oil.
5-one 10,11-Dihydro, 18-Me ester: [111150-38-0]. 10,11-
Dihydromicroglossic acid
C21H320 5 M 364.481
From M. zeylanica. Oil.
Gunatilaka, A.A.L. eta/, Phytochemistry, 1987, 26, 2408.
C 20H 340 3 M 322.487
(3(.,6E,J3E)-form 10,11-Epoxy-1 ,3(20),6, 14-phytatetraen-13- Dl-00015
Constit. of Helichrysum oreophilum. Oil. one
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 1133.

Dimerobrasiolide Dl-00011
4-(11 ,12-Dihydroxy-4,8,12-trimethyl-3,7-tridecadienyl)-
2(5H)-furanone, 9CI. 14,15-Dihydroxy-2,6,10-phytatrien- C20H 300 2 M 302.456
1,20-olide (6£)-form [126737-44-8] Haplomitrenone
[83790-31-2] Constit. of Haplomitrium mnioides. Pale yellow oil. [1X] 0
+ 7.8° (c, 1 in CHC13).
Asakawa, Y. et a/, Phytochemistry, 1990, 29, 585 (isol, pmr, cmr,
ms)
0
11,15-Epoxy-3(20)-phytene-1,2-diol Dl-00016
C 20H 320 4 M 336.470
Constit. of Dimerostemma brasilianum. Gum. [1X] 0 + oo (c, OH
0.9 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1343. CHPH

Dimeroperatic acid Dl-00012

2,6,10,14-Phytatetraen-1 ,20-o/id-17-oic acid
C 20H 380 3 M 326.518
[79694-64-7] Constit. of Anisopappus pinnatifidus.
0 Zdero, C. eta/, Phytochemistry, 1989, 28, 1155.

C 20H 280 4 M 332.439

Constit. of Dimerostemma asperatum. Gum.
Me ester:

658
Furcellataepoxylactone - 16-Hydroxy-2,6,10,14-phytatetraene-... Di-00017 - Di-00023

FurceUataepoxylactone Di-00017 7-Hydroxy-1,3,5,10,14-phytapentaen-13- Di-00021

1,20-Diacetoxy-6, 7-epoxy-1 ,3(20),10,14-phytatetraen-19,4- one
olide 10-Hydroxy-2,6,10,14-tetramethy/-2,6,11 ,13,15-
hexadecapentaen-4-one, 9CI
OAc
0
-:P'
OH
C10H 300 1 M 302.456
(3E,5E,JOE)-form [68582-63-8]
C14H 310 7 M 432.513 Constit. of Didiscus sp. Oil. [1X]i? + 0°.
Constit. of Pseudoch/orodesmis furcel/ata. Oil. [IX]~ + 1.6°
(c, 0.7 in CHC1 3). Et ether: [68582-64-9]. 7-Ethoxy-1,3,5,10,14-phytapentaen-
13-one
Paul, V.J. et al, Phytochemistry, 1988, 27, 1011. C11H 340 1 M 330.509
Constit. of D. sp. Oil.
Furodivaricatic acid Dl-00018 13-Deoxo, Et ether: [68582-65-0]. 7-Ethoxy-1,3,5,10,14-
[129349-99-1] phytapentaene. 7-Ethoxy-3,7,11 ,15-tetramethy/-
1,3,5,10,14-hexadecapentaene
C11H 340 M 314.510
Constit. of D. sp. Oil.
(3Z,5E,JOE)-form [68602-58-4]
C11H 310 5 M 376.492 Constit. of D. sp. Oil.
Constit. of Pteronia divaricata. Oil. Et ether: [68629-49-2].
Zdero, C. et al, Phytochemistry, 1990, 29, 1231 (isol, pmr) Constit. of D. sp. Oil.
13-Deoxy, Et ether: [68582-66-1].
Gerailyllinalol-19,9-olide Dl-00019 Constit. of D. sp. Oil.
[130395-46-9] Ravi, B.N. et al, J. Org. Chern., 1979, 44, 968.

1-Hydroxy-2,6,10,14-phytatetraene-18,19- Dl-00022
dioic acid

C 10H 300 3 M 318.455

Constit. of Baccharis pteronioides. Gum.
Jakupovic, J. et al, Phytochemistry, 1990, 29, 2217 (isol, pmr)
C10H 300 5 M 350.454
1-Hydroxy-12-oxo-2,6, 14-phytatrien-19-al Dl-00020 (2Z,6E,JOE)-form
2-(6-Hydroxy-4-methyl-4-hexeny/idene)-6,10-dimethy/-7-oxo- Ac: [116139-49-2]. Oleaxillaric acid
9-undecena/, 9CI. 10-Formy/-16-hydroxy-2,6,14-trimethy/- C11H 310 6 M 392.491
2,10,14-hexadecatrien-5-one Cons tit. of Olearia axillar is.
Warning, U. et al, J. Nat. Prod. (Lloydia), 1988, 51, 513.

0 16-Hydroxy-2,6,10,14-phytatetraene-1,19- Dl-00023
dioic acid
2-(9-Hydroxy-4,8-dimethy/-3,7-nonadienyl)-6-methyl-2,6-
octadienedioic acid
C10H 310 3 M 320.471 16
(2Z,6E)-form [110601-42-8] (6E)-JO,ll-Dihydro-12,19- HOH2C
dioxogeranylnerol
Constit. of Milleria quinqueflora. Oil.
!:>P-Isomer, 15-hydroxy: [110601-43-9]. 1,15-Dihydroxy-12-
oxo-2,6,13-phytatrie,...19-al. 10-Hydroxy-2-(6-hydroxy-4- (2Z,6E,10Z,l4E).jorm
methy/-4-hexylidene)-6,10-dimethyl-7-oxo-8-undecena/, C10H 300 5 M 350.454
9CI. 15-Hydroxy-12,19-dioxo-13,14-dehydro-10,11,14,15- (2Z,6E,JOZ,14E)-form [79579-43-4]
tetrahydrogerany/nero/. 10-Formyl-2, 16-dihydroxy-2,6, 14-
Constit. of Eremophila exilifo/ia. Oil.
trimethy/-3, 10, 14-hexadecatrien-5-one
C10H 32 0 4 M 336.470 16-Aldehyde: 16-0xo-2,6,10,14-phytatetraene-1 ,19-dioic acid
Constit. of M. quinqueflora. Oil. C10H 180 5 M 348.438
Constit. of E. exi/ifolia. Oil.
Jakupovic, J. et al, Phytochemistry, 1987, 26, 2011.
(2Z,6E,JOZ,UZ)-form [79579-45-6]
Constit. of E. exilifolia. Oil.
Ghisa1berti, E.L. et al, Aust. J. Chern., 1981, 34, 1491.

659
1-Hydroxy-2,6,10,14-phytatetraen-19-... - Isoacanthoaustralide Di-00024 - Di-00030

1-Hydroxy-2,6,10,14-phytatetraen-19-oic Dl-00024 ]-Aldehyde: (111950-82-4]. 13-0xo-2,6,10,14-phytatetraen-1-

acid al. 13-0xo-3,7,11 ,15-tetramethyl-2,6,10,14-
hexadecatetraen-1-al. Elegflllonal
lsol. from C. balearica.
(1Z,6E,10E)-form
]-Aldehyde: [111997-20-7]. lsoelegflllonal
From C. balearica. Oil.
Francisco, C. eta/, Phytochemistry, 1978, 17, 1003.
CzoH310 3 M 320.471 Biard, J.F. eta/, Tetrahedron Lett., 1980, 1849.
(1E,6E,10E)-form Amico, V. eta/, Phytochemistry, 1987, 26, 2637 (Eleganonal,
Gertu~ylgeraniol-19-oicacid Isoe/eganonal)
Constit. of Conyza pyrifolia.
Me ether: 3-Hydroxy-1,6,10,14-phytatetraen-12-one Dl-00028
C 21 H 33 0 3 M 333.490 14-Hydroxy-2,6,10,14-tetramethyl-2,6,10,15-
Constit. of C. pyrifolia. hexadecatetraen-5-one
Zdero, C. eta/, Phytochemistry, 1990, 29, 3167 (isol)
0

17-Hydroxy-2,6,10,14-phytatetraen-1,20- DI-G0025 ~

olid-18-oic acid OH
C10H 310 1 M 304.472
0 (6E,1 OE)-form
11-0xogertu~yllinalool
Constit. of Helichrysum krebsianum. Oil. [cx]~4 + 5.1 o (c,
0.34 in CHC1 3).
10,11-Dihydro: 3-Hydroxy-1,6,14-phytatrien-12-one. 14-
(6E,1 OE,UZ)-form Hydroxy-2,6,10,14-tetramethyl-2,10,15-hexadecatrien-5-
(JOE)-17-Hydroxygutiesolbriolide one. 11-0xo-10,11-dihydrogerflllyUinalol
Constit. of Gutierrezia solbrigii. Gutieso1brio1ide is CzoH340 1 M 306.487
unknown. Isol. from H. oreophilum. Oil.
(6E,10Z,14Z)-form Bohlmann, F. eta/, Phytochemistry, 1980, 19, 873; 1986, 25, 1133.
17-hydroxygutiesolbriolide
Constit. of G. solbrigii.
Ac: 17-Acetoxygutiesolbriolide
Ichthyouleolide Dl-00029
1-Hydroxy-2 ,6,1 0,14-phytatetraen-18,8-o/ide
CnH:ll,06 M 390.475
Constit. of G. solbrigii. [85538-65-4]
Jakupovic, J. eta/, Tetrahedron, 1985, 41, 4537.

17-Hydroxy-2,6,10,14-phytatetraen-20,1- Dl-00026
olid-18-oic acid 19

,::? CzoH300 3 M 318.455

Constit. of Ichthyothere ulei. Gum. [cx]i;' -33.6° (c, 0.67 in
CHzOH CHCI 3).
19-Acetoxy: [85527-33-9]. 19-Acetoxyichthyouleo/ide
CzoH280 5 M 348.438
CnH3z05 M 376.492
(6E,l OZ)-form Constit. of /. ulei. Gum.
17-Hydroxyisogutiesolbriolide
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2317.
Constit. of Gutierrezia solbrigii. lsogutieso1briolide is
unknown.
Ac: 17-Acetoxyisogutiesolbriolide Isoacanthoaustralide Dl-00030
CnH300 6 M 390.475 1,7-Dihydroxy-2,10,14-phytatrien-18,6-o/ide
Constit. of G. solbrigii. [79404-43-6]
Jakupovic, J. eta/, Tetrahedron, 1985, 41, 4537.

1-Hydroxy-2,6,10,14-phytatetraen-13-one Dl-00027
16-Hydroxy-2,6,10,14- Tetramethyl-2,6, 10,14-
hexadecatetraen-4-one

0
Cwfl 310 1 M 304.472 CzoH 310 4 M 336.470
(1E,6E,10E)-form [67880-32-4] Elegflllolone l-Ac:
Constit. of Cystoseira elegans. Oil. C11H 340 5 M 378.508
2,3-Epoxide: 2,3-Epoxy-1-hydroxy-6,10,14-phytatrien-13-one
c10H 310 3 M 320.471
Constit. of Bifurcaria bifurcata.

660
Ligantrol- 2,6-Phytadiene-1,16,17',18-tetrol Di-00031 - Di-00038

Constit. of Acanthospermum austra/e. Gum. [IX]~ +9.SO 18-Carboxy/ic acid: 2,6,10,14-Phytlltetraene-1 ,16,18-trioic
(c, 0.2 in CHC1 3). acid
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1081. C10H 280 6 M 364.438
Constit. of E. g/utinosa. Oil.
Ligantrol Dl-00031 (2Z,6Z,10E,14E)-form
11 ,14-Epoxy-2,6-phytadiene-1 ,10,15,18-tetro/ 18-Carboxy/ic acid:
C:zoH280 6 M 364.438
[53198-13-3)
Constit. of E. g/utinosa. Oil.
18-Carboxy/ic acid, 2,3S-dihydro: 6,10,14-Phytlltriene-
1 ,16,18-trioic acid
Ho1--- CJI300 6 M 366.453
Constit. of E. g/utinosa.
Ghisa1berti, E.L. et al, Aust. J. Chern., 1981, 34, 1491.
c;.,Il360 5 M 356.501
Constit. of Liatris e/egans. Gum. [IX]~ +5.1°.
18-Ac: [53198-14-4]. 1,3(20)-Phytadiene Dl-00035
CnH310 6 M 398.539 7,11,15- Trimethy/-3-methy/ene-1-hexadecene, 9CI.
Constit. of L. e/egans. [1X] 0 +25°. Neophytadiene. y- Phytadiene
Herz, W., J. Org. Chern., 1975, 40, 192. [504-96-1]

Mikanifuran Dl-00032
3-Methy/-2-(3,7,11-trimethyl-2,6,10-dodecatrienyf}furan, 9CI.
1,4-Epoxy-1,3,6,10,14-phytapentaene C:zoH31 M 278.520
[80442-35-9] Constit. of tobacco. Oil. Bp0_5 124-126°. [IX]~ -4° (neat).
Rowland, R.L., J. Am. Chern. Soc., 1957, 79, 5007.
Bhati, A., Perfum. Essent. Oil Rec., 1962, 53, 685.

v0 ' 1,3-Phytadiene Dl-00036

3,7,11 ,15-Tetramethy/-1 ,3-hexadecadiene
C:zoH300 M 286.456
Constit. of Mikania sessi/ifo/ia. Oil.
Bohlmann, F.~ et al, Phytochemistry, 1981, 20, 1899 (struct)
Kramp, W. et al, Justus Liebigs Ann. Chern., 1986, 226 (synth) C:zoH31 M 278.520
(E)-form [67669-03-8]
Naviculide Dl-00033 Constit. of zooplankton. Oil.
3-Hydroxy-1,6,10,14-phytatetraen-18,13-o/ide (Z)-form [67710-88-7]
Constit. of zooplankton. Oil.
Blumer, M. et al, Science (Washington, D.C.), 1965, 147, 1148
(isol, struct)
Hites, R.A., J. Org. Chern., 1974, 39, 2634 (synth)

C:zoH:11,03 M 318.455 2,4-Phytadiene Dl-00037

Constit. of Pore//a navicu/aris. Oil. 3,7,11 ,15-Tetramethy/-2,4-hexadecadiene
Toyota, M. et al, Phytochemistry, 1989, 28, 1661.

18-0xo-2,6,10,14-phytatetraene-1,16-dioic Dl-00034
acid C10H 31 M 278.520
6-Formy/-2,10,14-trimethyl-2,6,10,14-hexadecatetraenedioic (2E,4E,7R,11R)-form [58864-82-7]
acid Constit. of zooplankton. Oil.
HOOC Blumer, M. et al, Science (Washington, D.C.), 1965, 147, 1148
(isol, struct)
Scott, J.W. et al, Helv. Chim. Acta, 1916, 59, 290 (synth)

2,6-Phytadiene-1,16,17,18-tetrol Dl-00038
2,6-Bis(hydroxymethyl)-10,14-dimethy/-10,14-hexadecadiene-
1,16-dio/. 16,17,18,20-Tetrahydroxy-10,11,14,15-
(2Z,6Z,lOE, 14E)-form tetrahydronery/geraniol
C:zell:z1,05 M 348.438
(2Z,6Z,JOE,J4E)-form [79579-49-0]
Constit. of Eremophila g/utinosa. Cryst. (diisopropyl
ether). Mp 101-102°.
2,3S-Dihydro: 18-0xo-6,10,14-phytatriene-1,16-dioic acid C:zoH310 4
C:ze11300 5 M 350.454 Constit. of Pteronia incana. Gum.
Constit. of E. g/utinosa. Oil. [1X] 0 -3° (c, 0.8 in CHC1 3). Zdero, C. et al, Phytochemistry, 1990, 19, 1231 (isol, pmr)

661
Phytane - 1,6,10,14-Phytatetraene-3,13-diol Di-00039 - Di-00047

Phytane Dl-00039 (2E,6E,JOE,l3E)-form [116988-16-0]

2 ,6,10,14- Tetramethylhexadecane Constit. of Bifurcaria bifurcata. Oil.
[638-36-8] Semmak, L. eta/, Phytochemistry, 1988, 27, 2347.

1,6,10,13-Phytatetraene-2,14-diol Di-00044
2,6,1 0,14- Tetramethyl-3 ,6,10,15-hexadecatetraene-2, 14-diol
C20H 42 M 282.552
~
(6R,10R,UR)-form [18651-07-5]
Found in human liver, meteorites, oil shale and other OH """"'
OH
sediments. Oil. Bp 15 179.SO. C20 H 340 2 M 306.487
Kates, M. eta/, Biochemistry, 1967, 6, 3329. (6E,JOE,13E)-form [84093-71-0]
Constit. of Geigeria burkei. Gum.
1-Phytanoic acid Di-00040 Bohlmann, F. et at, Phytochemistry, 1982, 21, 1679.
3,7,11,15-Tetramethylhexadecanoic acid. Phytanic acid
1,6, 10,14-Phytatetraene-3,5-diol Dl-00045
COOH 3,7,11,15-Tetramethyl-1,6,10,14-hexadecatetraene-3,5-diol,
9CI

(3R,1R,11R)-form
C2oH400 2 M 312.535
C2oH 340 2 M 306.487
(3R,7R,1IR)-form [18654-64-3]
Isol. from the liver of patients with Refsum's disease (31;,51;,6E,JOE)-form [84093-63-0] 5-Hydroxygerany/Jinalol
and constit. of oil shale and butter. Oil. Bp 7 . 5 221°. [ocHllo Constit. of Geigeria burkei. Gum.
-3.8° (c, 4 in MeOH/CHC1 3). 9-Acetoxy: 9-Acetoxy-5-hydroxygeranyllinalol
(3S,7R,1IR)-form [14721-66-5] C22H3604 M 364.524
Constit. of oil shale. Oil. Constit. of G. burkei. Gum.
Kates, M. eta/, Biochemistry, 1967, 6, 3329 (struct) 9-Acetoxy, 5-Ac: [84093-65-2]. 5,9-Diacetoxygeranyllinfllol
Cox, R.E. et at, J. Chern. Soc., Chern. Commun., 1970, 1639 (isol, C24H 380 5 M 406.561
struct) Constit. of G. burkei. Gum.
Lough, A.K., Prog. Chern. Fats Other Lipids, Part I, 1973, 14 (rev) 13-Acetoxy: [84093-66-3]. 13-Acetoxy-5-
hydroxygeranyllinalol
1,3(20),6,10,14-Phytapentaene Dl-00041 C22H3604 M 364.524
7,11,15- Trimethyl-3-methylene-1 ,6,10,14-hexadecatetraene Constit. of G. burkei. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679.

1,6,10,14-Phytatetraene-3,9-diol Di-00046
"""" """" """" ,?'
C20H 32 M 272.473 3,7,11 ,15- Tetramethyl-1 ,6,10,14-hexadecatetraene-3,9-diol
(6E,JOE)-form [70901-63-2] P-Springene OH
Constit. of the dorsal gland of Antidorcas marsupia/is.
Oil.
Burger, B.V. eta/, Z. Naturforsch., C, 1981, 36, 340 (isol) C2oH3402 M 306.487
Vig, O.P. et at, Indian J. Chern., Sect. B, 1982, 21, 183 (synth) (E,E)-form
Vig, O.P. et at, Indian J. Chern., Sect. B, 1985, 24, 247 (synth)
9-Hydroxygerany/Jinalool
Constit. of Nicotiana sylvestris and of Geigeria burkei.
1,6,10,13,15-Phytapentaen-3-ol Dl-00042 Oil. [oc]n -6.7° (c, 0.8 in CHC1 3).
3,7,11 ,15-Tetramethyl-1 ,6,10,13,15-hexadecapentaen-3-ol Wallin, I. eta/, Acta Chern. Scand., Ser. B, 1980, 34, 391.
Bohlmann, F. et at, Phytochemistry, 1982, 21, 1679.

1,6,10,14-Phytatetraene-3,13-diol Di-00047
C20H 320 M 288.472 3,7,1 1,15- Tetramethy/-1 ,6,10,14-hexadecatetraene-3,13-diol,
(31;,6E,JOE,l3E)-form 9CI
Constit. of Geigeria burkei. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679. ~

OH
2,6, 10,13,15-Phytapentaen-1-ol Di-00043 C20 H 340 2 M 306.487
3,7,11 ,15-Tetramethyl-2,6,10,13,15-hexadecapentaen-1-ol, (31;,6E,JOE,131;)-form [84093-61-8]13-Hydroxygerany/Jinalol
9CI Constit. of Geigeria burkei. Gum. [oc]~4 + 82.2° (c, 0.5 in
CHC1 3) .
.# CHPH 13-Ac: [84093-62-9]. 13-Acetoxygeranyl/inalol
C22H 360 3 M 348.525
M 288.472 Constit. of G. burkei. Gum.
13-0[/J-L-Fucopyranosy/(1-->6)-P-D-glucopyranoside]:
C32 H 5P 11 M 614.772

662
1,6,10,14-Phytatetraene-3,17-diol - 2,6,10,14-Phytatetraene-1,19-diol Di-00048 - Di-00053

Constit. of fronds of Arachniodes maximowiczii. Syrup. Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613, 1623.
[cx]i; -35° (c, 2.0 in MeOH). Valls, R. eta/, Phytochemistry, 1986, 25, 751.
Semmak, L. et at, Phytochemistry, 1988, 27, 2347.
3,13-Di-0-P-D-glucopyranoside:
C32H540 12 M 630.771
Constit. of fronds of A. maximowiczii. Syrup. [cx]i; -38° 2,6,10,14-Phytatetraene-1,16-diol Di-00051
(c, 3.2 in MeOH). 2,6,10,14- Tetramethyl-2,6,10,14-hexadecatetraene-1 ,16-diol
13-Ketone: [84093-73-2]. 3-Hydroxy-1 ,6,10,14-phytatetraen-
13-one. 14-Hydroxy-2,6,10,14-tetramethy/-2,6,10,15- 16
HOHzC "'<:::: ~ "'<:::: CHzOH
hexadecatetraen-4-one, 9C1. 13-0xogeranyllinalol
C20H 32 0 2 M 304.472 C20 H 340 2 M 306.487
Constit. of G. burkei. Gum. (2E,6E,10E,14E)-form [79577-80-3]16-
13-Ketone, 14,15-Epoxide: [85194-00-9]. 14,15-Epoxy-3- Hydroxygeranylgeraniol
hydroxy-1 ,6,1 0,14-phytatetraen-13-one Constit. of Mikania goyazensis. Gum.
C20H 32 0 3 M 320.471 16-Carboxy/ic acid,1-Ac: [80368-54-3]. 1-Acetoxy-2,6,10,14-
Constit. of G. burkei. Gum. [cx]i;' -13.6° (c, 0.28 in phytatetraen-16-oic acid. Koanoadmantic acid
CHC1 3). C22 H 340 4 M 362.508
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1679 (isol, struct) Constit. of Koanophyllon admantium. Gum(as Me ester).
Tanaka, N. eta/, Chern. Pharm. Bull., 1986, 34, 1015 (isol, derivs)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1903; 1982, 21,
1349.
1,6,10,14-Phytatetraene-3,17-diol Dl-00048 Kramp, W. et at, Justus Liebigs Ann. Chern., 1986, 226 (synth)
2,6,10,14- Tetramethyl-2,6,10,15-hexadecatetraene-1 ,14-diol
2,6,10,14-Phytatetraene-1,18-diol Dl-00052
6,10-Dimethyl-2-(4-methyl-3-pentenyl)-2,6,10-dodecatriene-
"'<:::: 1,12-diol, 9Cl. 11-Hydroxymethyl-3,7,15-trimethy/-2,6,10,14-
C20H 340 2 M 306.487 hexadecatetraen-1-o/
(3S,6E,JOE,14Z)-form
20-Hydroxygeranyllinalool
Constit. of Nicotiana sylvestris. Oil. [cx] 0 +9° (c, 1 in
CHC1 3).
Wallin, I. et a/, Acta Chern. Scand., Ser. B, 1980, 34, 391.
HOH2C '
C20H 340 2 M 306.487
2,6,1 0,14-Phytatetraene-1 ,9-diol Di-00049 (2E,6E,10E)-form [64702-55-2]
3,7,11 ,15- Tetramethyl-2,6,10,14-hexadecatetraene-1 ,9-dio/ Oil.
18-Aldehyde: 1-Hydroxy-2,6,10,14-phytatetraen-18-al. 11-
Formyl-3,7,15-trimethyl-2,6,10,14-hexadecatetraen-1-o/
"""= ""::: ~ CH2 0H C20 H 3z03 M 320.471
Constit. of Croton kerrii. Oil.
C20 H 340 2 M 306.487
(2E,6E,10Z)-form [64849-48-5]
(2E,6E,9R,10E)-form [60346-04-5] Crinitol
Constit. of C. kerrii. Oil.
Constit. of Cystoseira crinita. Oil. [cx] 0 -3°.
[64702-56-3]
Fattorusso, E. et a/, Tetrahedron Lett., 1976, 937.
Kubo, I. et a/, Chern. Lett., 1985, 249 (abs config) Sato, A. et a/, Phytochemistry, 1980, 19, 2207.

2,6, 10,14-Phytatetraene-1, 12-diol Di-00050 2,6,10,14-Phytatetraene-1,19-diol Di-00053

3,7,11 ,15- Tetramethy/-2,6,10,14-hexadecatetraene-1 ,12-dio/ 2-(4,8-Dimethy/-3, 7-nonadienyl)-6-methy/-2 ,6-octadiene-1 ,8-
dio/, 9CI. 18-Hydroxygeranylgeranio/. Plaunotol, INN.
OH
I
Kelnal. Plaugenol. CS 684

18 19

C20H 340 2 M 306.487

C20H 340 2 M 306.487
(2E,6E,10E,12S)-form
Isol. from leaves of Croton sublyratus (Plau-noi) and C.
12-Hydroxygeranylgeraniol
columnaris. Antiulcer agent used as native drug. Oil.
Constit. of Bifurcaria bifurcata. Oil. [cx] 0 - 12.47° (c, Major constit. of Kelnac.
0.93 in CHCI 3).
Bis(3,5-dinitrobenzoyl): Cryst. (MeOH/Et20). Mp 83-84°.
1-Carboxylic acid: [117007-28-0]. 12-Hydroxy-2,6,10,14-
phytatetraen-1-oic acid Ogiso, A. eta/, Chern. Pharm. Bull., 1978, 26, 3117 (iso/,
pharmacal, synth, ir, pmr, ms)
C20 H 320 3 M 320.471
Kobayashi, S. eta/, Oyo Yakuri, 1982, 24, 599 (pharmacal)
lsol. from B. bifurcata. Oil. [cx] 0 +4.19° (c, 8.1 in Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
CH2Cl2). Pharmaceutical Press, London, 1982/1989, 2366.
(2E,6Z,10Z,12f,)-form Ogiso, A. et a/, CA, 1986, 104, 213053 (rev, pharmacal)
Sato, K. et a/, Chern. Lett., 1988, 1433 (synth, ir, pmr)
18-Hydroxy: 2,6,10,14-Phytatetraene-1,12,18-trio/. 12,18-
Dihydroxygeranylgeraniol
C20H 340 3 M 322.487
lsol. from Zinnia tenuifolia. Gum. [cx]i;' +35.9° (c, 0.3 in
CHC1 3).

663
2,6,10,14-Phytatetraene-1,20-diol - 2,6,10,14-Phytatetraene-1,17,18-... Di-00054 - Di-00062

2,6,10,14-~ytatetrae~1,2~ol Dl-00054 2,6,10,14-~ytatetraene-1,18,19,20-tetrol Dl-00058

3, 7,11- Tris(hydroxymethyl)-15-methy/-2,6,10,14-
CH2 0H hexadecatetraen-1-o/
~ -::?
CH2 0H
Czolf340 1 M 306.487
(2E,6E,JOE)-form
20-Hydroxygerflllylnerol CzoH340 4 M 338.486
Constit. of Kingianthus paradoxus. Gum. (2E,6Z,10Z)-form
Di-Ac: Constit. of Viguiera gilliesii. Oil.
C14H 380 4 M 390.562 Guerreiro, E., Phytochemistry, 1986, 25, 748.
Metab. of Chlorodesmis fastigiata. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1146 (isol) 1,6,10.14-Pbytatetraene-3,5,13-triol Dl-00059
Wright, A.D. eta/, J. Nat. Prod. (Lloydia), 1990, 52, 845 (deriv) 3,7,11 ,15-Tetramethy/-1 ,6,10,14-hexadecatetraene-3,5,13-
triol
2,6,10,14- ~ytatetrae~ 1,8,12,19-tetrol Dl-00055
OH OH CH2 0H

C18H 340 3 M 322.487

(6E,10E)-form [125289-87-4] 5,13-Dihydroxygeranyllinalol
Czoll340 4 M 338.486 Constit. of Geigeria ornativa. Oil.
(2Z,6Z,8f.,JOE,J2f.)-form Zdero, C. eta/, Phytochemistry, 1989, 28, 3105 (isol, pmr)
· 8,12,19- Trihydroxygerflllylnerol
Constit. of Balsamorhiza sagittata. Oil.
2,6,1 0,14-Phytatetraene-1t5,13-triol Dl-00060
6,7-Epoxide: 6,7-Epoxy-2,10,14-phytatriene-1,8,12,19-tetro/
Czoll340 5 M 354.486 .#
From B. sagittata. Oil.
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 2029.
C18H 340 3 M 322.487
2,6,10,14-~ytatetraene-1,12,19,20-tetrol Dl-00056 (2E,5f.,6E,JOE,13f.)-form
5,13-Dihydroxygerflllylgeraniol
HO Constit. of Ophryosporus fioribundus. Gum.
Zdero, C. eta/, Phytochemistry, 1990, 29, 3247 (iso/, pmr)

2,6,10,14-Phytatetraene-1,12,19-triol Dl-00061
Czoll 340 4 M 338.486
OH
(2E,6Z,10E,l2f.)-form
19-Ac: 19-Acetoxy-12,20-dihydroxygerflllylnerol
C11H 360 5 M 380.523
Constit. of Lasiolaena morii. Gum. C18H 340 3 M 322.487
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 161. (2E,6Z,10E,l2f.)-form
12,19-Dihydroxygeranylgeraniol
2,6,1 0,14-Pbytatetraene-1,16,18,20-tetrol Dl-00057 Constit. of Lasiolaena santosii. Gum.
6,14-Bis(hydroxymethyl)-2,10-dimethy/-2,6,10,14- 10,11-Dihydro, 12-oxo: 1,19-Dihydroxy-2,6,14-phytatrien-
hexadecatetraene-1 ,16-diol. 16,18,20-Trihydroxygeranylnerol 12-one. 10,11-Dihydro-19-hydroxy-12-oxogerflllylgeraniol
[125180-53-2] C18H 340 3 M 322.487
Constit. of L. santosii. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.

2,6,10,14-Pbytatetraene-1,17,18-triol Dl-00062
CHPH 6-(Hydroxymethyl)-2,10,14-trimethy/-2,6,10,14-
hexadecatetraene-1 ,16-dio/, 9C1
Czoll340 4 M 338.486
Constit. of Viguiera sy/vatica. ~
Tamaya-Castil1o, G. eta/, Phytochemistry, 1989, 28, 2737 (isol, 17 CH 0H 18 CH 0H
2 2
pmr)
C18H 340 3 M 322.487
(2E,6E,JOZ,14Z)-form [102904-51-8]17,18-
Dihydroxygeranylgeraniol
18-Ac: 18-Acetoxy-17-hydroxygerflllylgeraniol

664
2,8,10,14-Phytatetraene-1,17,20-... - 2,6,10,14-Phytatetraen-1-ol Di-00063 - Di-00066

C22H 360 4 M 364.524 1,6, 10,14-Phytatetraen<~ol Dl-00065

Constit. of Chiliotrichium rosmarinifolium. Oil. 3,7,11 ,15-Tetramethyl-1 ,6,10,14-hexadecatetraen-3-ol
Jakupovic, J. et al, Tetrahedron, 1986, 42, 1305. [1113-21-9]

2,6,10,14-Phytatetraene-1,17,20-triol

(3R,6E, 1OE)-form
C20H 340 M 290.488
CH2 0H CH2 0H
(3R,6E,JOE)-form
C20H 340 3 M 322.487 Geranyllinalool
(2E,6E,10E,14Z)-form Constit. of Picea abies. Oil. BPo.oos ll5°. [1X]n -10.1°.
17,20-Dihydroxygeranylnerol (3S,6E,10E)-form
Constit. of Bejaranoa semistriata. Gum. Constit. of Jasmin oil. BPo.oos ll5°. [1X]n + 14.SO.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1639. [2211- 30- 5]
Demole, E. et al, Bull. Soc. Chim. Fr., 1958, 1128 (synth, ir)
2,6,10,14-Phytatetraene-1,18,19-triol Dl-00064 Kimland, B. eta/, Acta Chern. Scand., 1967, 21, 825 (pmr)
6-(Hydroxymethyl)-10-methy/-2-(4-methyl-3-pentenyl)- Vig, O.P. et al, Indian J. Chern., 1969, 7, 574.
2 ,6,10-dodecatriene-1 ,12-diol, 9C/
2,6,1 0,14-Phytatetraen-1-ol Dl-00066
CHzOH 3, 7,11,15- Tetramethyl- 2,6,10,14-hexadecatetraen-1-ol

CHzOH (2E,6Z, 1OE)-form

18
C20H 340 M 290.488
C20H 340 3 M 322.487 (2E,6E,10E)-form [24034-73-9] Geranylgeraniol
(2E,6Z,10E)-form [117232-54-9]18,19-Dihydroxynerylgeraniol Widespread in plants, e.g. found in linseed oil. Oil.
Constit. of Vittadinia gracilis. Oil. Bp0 . 35 145°. n~ 1.4932.
18-Aldehyde: [117255-04-6]. 1,19-Dihydroxy-2,6,10,14- 0-(2 ,3-Dihydroxypropyl)(R-): [64604-13-3]. 1-0-
phytatetraen-18-al. 12-Hydroxy-6-(hydroxymethyl)-10- Geranylgeranylglycerol
methyl-2-(4-methyl-3-pentenyl)-2,6,10-dodecatrienal, 9CI. C23H 400 3 M 364.567
18-0xo-19-hydroxynerylgeraniol Constit. of Dilophus fascia/a. Viscous liq. [1X]n -2.1° (c,
C20H 320 3 M 320.471 1.5 in CHC1 3).
Constit. of V. gracilis. Oil. Aldehyde: [13920-12-2]. 2,6,10,14-Phytatetraen-1-al.
(2Z,6Z,10Z)-form 3,7,11 ,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-al.
18,19-Dihydroxygeranylnerol Geranylgeranial
19-Ac: 19-Acetoxy-18-hydroxygeranylnerol C20H 3z0 M 288.472
C22H 360 4 M 364.524 Oil. BPo.s 150°.
Constit. of Ageratina ligustrina. Aldehyde, semicarbazone: Mp ll8°.
(2E,6E,10Z)-form Aldehyde,141;,,151;,-Epoxide: [108613-62-3]. 13-(3,3-
19-Aldehyde: 1,18-Dihydroxy-2,6,10,14-phytatetraen-19-al. Dimethyloxiranyl)-3,7,11-trimethyl-2,6,10-tridecatrienal,
18-Hydroxy-19-oxogeranylgeranial 9Cl. 14,15-Epoxy-2,6,10-phytatrien-1-ai
C20Hn03 M 320.471 C20 H 320 2 M 304.472
!sol. from Conyza pyrifolia. Gum. !sol. from Cystophora moniliformis. Oil. [1X]n - 17° (c,
19-Carboxylic acid: 1,18-Dihydroxy-2,6,10,14-phytatetraen- 0.98 in CHC1 3).
19-oic acid. 18-Hydroxygeranylgeraniol-19-oic acid (2Z,6E,10E)-form
C20H 320 4 M 336.470 Aldehyde,141;,,151;,-epoxide: [115075-54-2].
Constit. of Microglossa pyrrhopappa. !sol. from C. moniliformis. Oil. [1X]n -22° (c, 0.4 in
19-Carboxylic acid, l-Ac: CHC1 3).
C22H 340 5 M 378.508 Nagasampagi, B.A. eta/, Tetrahedron Lett., 1967, 189 (pmr)
Constit. of M. pyrrhopappa. Buggy, M.J. eta/, Phytochemistry, 1974, 13, 125 (biosynth)
(2E,6E,10E)-form Khan, N. eta/, J. Chern. Soc., Perkin Trans. I, 1975, 1457
(aldehyde)
18,19-Dicarboxylic acid: 1-Hydroxy-2,6,10,14- Amico, V. et al, Experientia, 1977, 33, 989 (deriv)
phytatetraene-18, 19-dioic acid. Geranylgeraniol-18,19- Altman, L.J. et al, J. Am. Chern. Soc., 1978, 100, 6174 (aldehyde)
dioic acid Coates, R.M. et a/, J. Org. Chern., 1978, 43, 4915 (cmr)
C20H 34P 5 M 350.454 Ahlqvist, L. eta/, Prog. Chern. Fats Other Lipids, 1978, 16, 231
Constit. of M. pyrrhopappa. (rev)
Van Altena, I.A. eta/, Aust. J. Chern., 1988, 41, 49 (aldehyde
6,7-Dihydro, 18,19-dicarboxylic acid: 1-Hydroxy-2,10,14-
epoxides)
phytatriene-18,19-dioic acid. 6,7-Dihydrogeranylgeraniol-
18,19-dioic acid
C20H 32 0 5 M 352.470
Constit. of M. pyrrhopappa.
Zdero, C. et al, Phytochemistry, 1988, 27, 2251; 1990, 29, 3167,
3233.
Tamayo-Castillo, G. et al, Phytochemistry, 1988, 27, 2893.

665
2,6,10-Phytatriene-1,14,15,20-... - 1,16,18,20-Tetrahydroxy-2,7(19) ... Di-00067 - Di-00073

2,6,10-Phytatriene-1,14,15,20-tetrol Di-00067 2-Phyten-1-ol Dl-00071

3-Hydroxymethy/-7,11 ,15-trimethy/-2,6,1 0-hexadecatriene- 3,7,11 ,15-Tetramethy/-2-hexadecen-1-o/. Phytol
1,14,15-trio/

HO
(2E, 7R, 11 R)-form
OH C20H 400 M 296.535
C20H 360 4 M 340.502 (2E,7R,JJR)-form [150-86-7]
(2E,6E,JOE,14~,15~)-form [119877-40-6] Constit. of nettles and other plants. Oil. Bp0 .02 132°. [cxm
Constit. of Tithonia pedunculata. Oil. [cxJn + 0°. +0.2°.
I> TJ3490000.
Perez, A.-L. et al, Phytochemistry, 1988, 27, 3897.
]-Aldehyde: [13754-69-3]. 2-Phyten-1-a/. 3,7,11,15-
Tetramethyl-2-hexadecena/. Phytal
1,6,10-Phytatriene-3,14,15-triol Dl-00068 C20H 380 M 294.520
2,6,1 0,14- Tetramethy/-6,1 0 ,15-hexadecatriene-2,3 ,14-trio/, Constit. of Tetragonia tetragonoides. Oil.
9CI
(2Z,7R,JJR)-form [5492-30-8]
OH Constit. of Gracilaria andersoniana. Oil.
Burrell, J.W.K. et al, J. Chern. Soc. C, 1966, 2144 (synth, abs
config)
Shilleter, D.N. eta/, Phytochemistry, 1970, 9, 153 (biosynth)
C20H 360 3 M 324.503 Goodman, R.A. et al, J. Am. Chern. Soc., 1973, 95, 7553 (cmr)
Sims, J.J. et a/, Phytochemistry, 1976, 15, 1076 (isol)
(3~,6E,10E,14~)-form [84093-67-4] 14,15-Dihydro-14,15- Aok:i, T. et al, Phytochemistry, 1982, 21, 1361 (isol)
dihydroxygeranyllina/ol Schmid, M. et al, Helv. Chim. Acta, 1982, 65, 684 (synth)
Constit. of Geigeria burkei. Gum. Gramatica, P. eta/, Tetrahedron, 1987, 43, 4481 (synth)
5-Hydroxy: [84093-68-5]. 1 ,6,10-Phytatriene-3 ,5,14,15-
tetra/. 2,6,10,14- Tetramethy/-6,10,15-hexadecatriene- 1,4,9,20-Tetraacetoxy-1,3(20),6,10,14- Dl-00072
2,3,12,14-tetrol phytapentaen-19-al
C20H 360 4 M 340.502 4-Acetyloxy-2-[3,6-bis(acetyloxy)-4-(acetyloxymethylene)-5-
Constit. of G. burkei. Gum. hexenylidene]-6,10-dimethy/-5,9-undecadienal, 9CI
9-Acetoxy: [84093-69-6]. [93888-68-7]
C22H 380 5 M 382.539
Constit. of G. burkei. Gum.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1739.

1-Phytene-3,4-diol Dl-00069
3,7,11 ,15- Tetramethy/-1-hexadecene-3,4-dio/
OAc
OH
C28H 380 9 M 518.603
Metabolite of many Halimeda species of green algae.
Yellow oil. [cx]i;l -1.5° (c, 1.2 in CHC1 3).
C20H 400 2 M 312.535 Paul, V.J. et al, Tetrahedron, 1984, 40, 3053.
Constit. of Lemna minor. Oil. [cxJn + 1.5° (c, 1 in CHC1 3).
(3~,4~)-form 1,16,18,20-Tetrahydroxy-2,7(19),10,14- Dl-00073
4-Hydroxyisophytol phytatetraen-6-one
Cons tit. of Lemna minor. Oil. [cxJn + 1.5" (c, 1 in 1,16-Dihydroxy-3,11-bis(hydroxymethyl)-15-methyl-7-
CHC1 3). methy/ene-2,10,14-hexadecatrien-6-one, 9CI
Previtera, L. et al, Phytochemistry, 1984, 23, 194.
0
3(20)-Phytene-1,2-diol Di-00070
7,11,15- Trimethy/-3-methy/ene-1 ,2-hexadecanedio/, 9CI
[100605-94-5]
C20H 320 5 M 352.470
(2E,10Z,l4E)-form [125180-54-3] 16,18,20-Trihydroxy-6-oxo-
7,19-tkhydro-6,7-dihydogeranylnerol
Constit. of Viguiera sy/vatica.
C20H 400 2 M 312.535 Tamaya-Castillo, G. eta/, Phytochemistry, 1989, 28, 2737 (isol,
Constit. of Senecio gal/icus. Oil. [cxJn -1.2° (c, 0.5 in pmr)
CHC1 3).
Di-Ac:
C24H 440 4 M 396.609
Constit. of S. gal/icus. Oil.
Urones, J.G. et al, Phytochemistry, 1987, 26, 1113.

666
Thymifodioic acid - U doteafuran Di-00074- Di-00081

Thymifodioic acid Dl-00074 17,18,19-Trihydroxy-2,14-phytadien-20,1- Dl-00078

1,20-Epoxy-1,3(20),6,10,14-phytapentaene-18,19-dioic acid olide
13-Hydroxy-4,8-bis(hydroxymethyl)-12-methyl-11-tridecenyi-
2(5H)-furanone, 9CI
_..-:; Ia'
_..-:; COOH

17 COOH C20 H 340 5 M 354.486

C20H 260 5 M 346.422 (71!,,111!,,14Z)-form
Constit. of Baccharis thymifolia. Oil. 17,18,19-Trihydroxy-6,7,10,11-tetrahydrogeranylgeraniol
17-Acetoxy: 17-Acetoxythymifodioic acid 20,1-lactone
C 11H:zs0 7 M 404.459 18-Ac: [102904-52-9].
From B. thymifolia. C11H 360 6 M 396.523
Saad, J.R. eta/, Phytochemistry, 1987, 26, 3033. Constit. of Nardophyllum lanatum. Oil.
18,19-Di-Ac: [102904-53-0].
Tomexanthin Di-00075 C14H 380 7 M 438.560
1-Acetoxy-7,20-epoxy-6,15-dihydroxy-2 ,13-phytadien-12-one Constit. of N. lanatum. Oil.
[90746-99-9] Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305.

16,17,18-Trihydroxy-2,6,10,14- Dl-00079
OAc phytatetraen-1,20-olide
16,17,18- Trihydroxynery/geran-1 ,20-olide
HO

CuH 360 6 M 396.523

Constit. of Montanoa tomentosa. Oil. 0
17 CHpH CHPH
Seaman, F.C. eta/, Phytochemistry, 1984, 23, 464.
CzoH 34P 5 M 350.454
Trifarin Di-00076 Constit. of Pteronia eenii. Oil.
[69625-34-9] 16-Deoxy: 17,18-Dihydroxy-2,6,10,14-phytatetraen-1,20-
o/ide. 17,18-Dihydroxynerylgeran-1,20-o/ide
'-"::::: OAc C10H 300 4 M 334.455
Constit. of P. eenii. Oil.
AcO 17-Deoxy: 16,18-Dihydroxy-2,6,10,14-phytatetraen-1 ,20-
olide. 16,18-Dihydroxynerylgeran-1,20-o/ide
C14H 380 4 M 390.562 C20H 300 4 M 334.455
Constit. of Caulerpa .flexi/is. Oil. Constit. of P. eenii. Oil.
6,7,10,11- Tetrahydro: Bisdihydrotrifarin Zdero, C. et a/, Phytochemistry, 1990, 29, 1231 (isol, pmr)
Cl4H410 4 M 394.593
Constit. of Pseudoch/orodesmis furcellata. Oil. [a:]~
+ 1.6° (c, 0.68 in CHCI 3). 1,5,15-Trihydroxy-2,6, 10, 13-phytatetraen- Dl-00080
Blackman, A.J. et a/, Tetrahedron Lett., 1978, 3063 (isol) 12-one
Paul, V.J. eta/, Phytochemistry, 1988, 27, 1011 (deriv)

1,10,17-Trihydroxymelfusanolide Dl-00077
6,11-Epoxy-1 ,10,17-trihydroxy-2,14-phytadien-18,7-o/ide HO

CwH3z04 M 336.470
(2E,51!,,6E,JOE,13E)-form
13, 14-Dehydro-14, 15-dihydro-5, 15-dihydroxy-12-
oxogerany/geranio/
Constit. of Ophryosporus .floribundus.
C20H 310 6 M 368.469
Zdero, C. eta/, Phytochemistry, 1990, 29, 3247 (isol, pmr)
Melfuranolide is currently unknown. Constit. of
Me/ampodium diffusum. Gum.
17-Ac: 17-Acetoxy-1,10-dihydroxymelfusano/ide Udoteafuran Dl-00081
C 11H 340 7 M 410.506 1,20-Epoxy-1 ,3(20),6,10,14-phytapentaen-19-a/
Constit. of M. diffusum. Gum. [77256-96-3]
[92356-84-8]
Quijano, L. eta/, Phytochemistry, 1984, 23, 833.

667
Udoteal - 2,6,10-Trimethyl-7-(3-methylbutyl)... Di-00082 - Di-00087

C20H 280 2 M 300.440

Constit. of Udotea flabellum. Oil.
Nakatsu, T. et al, J. Org. Chern., 1981, 46, 2435.
Irregular linear
Udoteal
1,20-Diacetoxy-1 ,3(20),6,10,14-phytapentaen-19-a/
Dl-00082
diterpenes
[82309-29-3]
OAc

2,10-Dimethyl-7-(3-methylbutyl)-6- Dl-00085
methylenedodecane, 9CI
~ 6- M ethy/-3-(3-methylbutyl)- 2-(4-methy/pentyl)-1-octene
OAc [99317-08-5]
C24H 340 5 M 402.530
lsol. from Udoteafiabellum. Feeding deterrent. Oil.
6,7-Dihydro: 1,20-Diacetoxy-1,3(20),10,14-phytatetraen-19-
a/. 6,7-Dihydroudoteal
C24H 360 5 M 404.545
Metabolite of Penicillus dumetosus. Possesses
antibacterial and antifungal props. Oil. [1X]i,S +0.7° (c,
1.3 in CHC1 3). C20H 40 M 280.536
Paul, V.J. et al, Phytochemistry, 1982, 21, 468 (isol, struct) Constit. of hypersaline sediments. Bp0 _3 150° (bath).
Paul, V.J. et al, Tetrahedron, 1984, 40, 2913 (deriv) Dunlop, R.W. et al, Org. Geochem., 1985, 8, 313 (isol, struct)
Ghisalberti, E.L. et al, J. Chern. Res. (S), 1986, 338 (synth)
Vittadinal Dl-00083
10,19-Epoxy-2,6,14-phytatrien-18-a/ Peucelinendiol Dl-00086
[117232-53-8] 7-Hydroxymethyl-2,6,10,14-tetramethyl-2,9,13-
pentadecatrien-6-ol
CHPH [72776-48-8]

C20H 320 3 M 320.471

I sol. from Vittadinia gracilis. Oil.
C20 H 360 2 M 308.503
11-Epimer: (117232-50-5]. Epivittadinal Constit. of Peucedanum oreoselinum. Oil. (1X]i;4 + 5.5° (c, 1.2
C20H 320 3 M 320.471 in CHC14).
Cons tit. of V. gracilis. Oil.
Lemrnich, E., Phytochemistry, 1979, 18, 1195 (isol)
Zdero, C. et al, Phytochemistry, 1988, 27, 2251. Moran, J.R. et al, Bull. Chern. Soc. Jpn., 1988, 61, 4435 (synth,
struct)
Zoapatanol Dl-00084
7,20-Epoxy-] ,6-dihydroxy-2,14-phytadien-12-one 2,6,10-Trimethyl-7-(3- Dl-00087
[71117-51-6] methylbutyl)dodecane, 9CI
[89255-51-6]

0
C20H 34 0 4 M 338.486
Constit. of Montanoa tomentosa. Utero-evacuant
substance. Oil. C20H 42 M 282.552
t> RA9710000. Mixt. of diastereomers. Constit. of Rozel Point crude oil
Levine, S.D. et al, J. Am. Chern. Soc., 1979, 101, 3404 (struct) and recent sediments. Sedimentary biological marker.
Chen, R. et al, J. Am. Chern. Soc., 1980, 102, 6609 (synth) Oil.
Nicolaou, K.C. et al, J. Am. Chern. Soc., 1980, 102, 6611 (synth) [83037-85-8, 83060-10-0, 83060-11-1, 83060-12-2)
Cotter, M.L., Org. Magn. Reson., 1981, 17, 14 (cmr)
Kanojia, R.M. et al, J. Org. Chern., 1982, 47, 1310 (isol, struct) Yon, D.A. et al, Tetrahedron Lett., 1982, 23, 2143.
Cookson, R.C. et al, J. Chern. Soc., Perkin Trans. 1, 1985, 1589
(synth)

668
Albocycline - 2,5-Epoxy-6,10,14-trimethyl-9,13-... Di-00066 - Di-00092

Prod. by S. bruneogriseus. Weakly active against gram-

positive bacteria. Needles + ! H 20 (diisopropyl
Linear homo- and etherfcyclohexane). Mp 86-87.5°. [ex]~ +6.9° (c, 0.35 in
MeOH).

norditerpenoids
Miyairi, N. et al, J. Antibiot., Ser. A, 1966, 19, 56 (deriv)
Nagahama, M. et al, Chem. Pharm. Bull., 1971, 19, 649, 655, 660
(isol)
Suzuki, M., CA, 1972, 78, 15094t (ms)
Thomas, R.C. et al, J. Antibiot., 1982, 35, 1658 (cryst struct, bib[)
Furusaki, A. et al, Bull. Chem. Soc. Jpn., 1983, 56, 3042 (cryst
struct)
Albocycline,9CI Dl-00088 Harada, K. et al, J. Antibiot., 1984, 37, 1187 (isol, synth, struct,
lngramycin. T A 2407. Antibiotic T A 2407 nmr)
Tanner, D. et al, Tetrahedron, 1987, 43, 4395 (synth, bib[)
[25129-91-3]

Clibadic acid Dl-00089

[116310-63-5]

~H 3806 M 434.572
C 18H 280 4 M 308.417 Constit. of Clibadium pittierii. Gum.
Macrolide-type antibiotic. From Streptomyces spp. Shows
Tamayo-Castillo, G. et al, Phytochemistry, 1988, 17, 1868.
limited in vitro activity mainly against staphylococci.
Plates. [ex]~ -90° ,(c, 1 in MeOH). Indefinite Mp.
Albocyclines Ml to M8 were isol. as minor components. 14,15-Dihydroxy-1,2-dinor-6,10-pbytadien- Dl-00090
I> AY8940000. 3-one. .
Ac: Mp 84°. 13,14-Dihydroxy-6,10,14-trimethyl-5,9-pentadecadien-2-one
p-Bromobenzoyl: Cryst. Mp 90-92.5°. OH
I
0-De-Me: [11033-23-1]. Cilleromycin B
C 17H 160 4 M 294.390
From S. cinerochromogenes. Weakly active against
gram-positive bacteria. Plates (Me2CO/C6HJ. Mp 149- C 11H 320 3 M 296.449
1500. [ex) 0 - 110° (MeOH). (6E,10E,14R)-form [81373-96-8]
I> GD6252000. Isol. from Cystophora moniliformis. Viscous oil. [ex]~
8,9-Epoxide: [93752-55-7]. Albocycline Ml -9.7° (c, 1 in CH20 2).
C1aH280 5 M 324.416 Ravi, B.N. et al, Aust. J. Chem., 1982, 35, 171.
Prod. by S. bruneogriseus, also synthetic. Weakly active
against gram-positive bacteria. Oil. [ex]~ -10.0° (c, 0.35
in MeOH). A.....,. 220 nm (EtOH). 12,15-Epoxy-1,2-dinor-6,10-phytadien-3- Dl-00091
12-Hydroxy: [93752-56-8]. Albocycline M2
one
C 18H 280 5 M 324.416 6,10,14-Trimethyl-11,14-epoxy-5,9-pentadecadien-2-one
Prod. by S. bruneogriseus. Weakly active against gram-
positive bacteria. Oil. [exfJ -112.0° (c, 0.5 in MeOH).
11-Hydroxy: [93752-58-0]. Albocycline M5
C18H 280 5 M 324.416
Prod. by S. bruneogriseus. Weakly active against gram- C•aH300 2 M 278.434
positive bacteria. Oil. [ex)~ -90° (c, 0.2 in MeOH). (6E,JOE)-form
10-J/ydroxy: Albocycline M7 Constit. of Cytophora moniliformis. Oil. [ex]~ +28.1° (c,
ClaH280 5 M 324.416 1.1 in CH0 3).
Prod. by S. bruneogriseus. Weakly active against gram- Ravi, B.N. et al, Aust. J. Chem., 1982, 35, 171.
positive bacteria. Oil. [ex]~ -13.5° (c, 0.1 in MeOH).
18-Hydroxy: [93752-57-9]. Albocycline M4 2,5-Epoxy-6,10,14-trimethyl-9,13- Dl-00092
C 18H 280 5 M 324.416 pentadecadiene-2,6-diol
Prod. by S. bruneogriseus. Weakly active against gram- ex-(4,8-Dimethyl-3,7-nonadienyl)tetrahydro-5-hydroxy-ex,5-
positive bacteria. Oil. [exFn -55.1° (c, 0.15 in MeOH). dimetliyl-2-furanmethanol
11-Hydroxy, 2,3-dihydro: [93775-29-2]. Albocycline M3
C 18H 31,05 M 326.432
Prod. by S. bruneogriseus. Weakly active against gram-
positive bacteria. Needles (C6~fcyclohexane). Mp 123-
124.50. [ex]~ -25.6° (c, 0.5 in MeOH).
10-Hydroxy, 2,3-dihydro: [93752-59-1]. Albocycline M6 C 11H 320 2 M 280.450
C1aH300 5 M 326.432 2-Me ether: [115028-54-1]. 2-(5-Methoxy-5-
methyltetrahydro-2-furanyl)-6,10-dimethyl-5,9-undecadien-
2-ol

669
ft,6-Epoxy-6,10,14-trimethyl-9,13-... - 2,6,10,14-Tetramethylpentadecane Di-00093 - Di-00101

c.,H340 3 M 310.476 Pretomentol Di-00097

Constit. of Cystophora moniliformis. Oil. [1X]n + 11 o (c, [99877-58-4]
1.3 in CHC1 3).
van Altena, I.A., Aust. J. Chern., 1988, 41, 49.

5,6-Epoxy-6,10, 14-trimethyl-9, 13- Dl-00093

pentadeca~en-~ne
4-[3-(4,8-Dimethy/-3,7-nonadienyl)-3-methy/oxiranyl]-2- C21 H3604 M 352.513
butanone, 9CI Constit. of Montanoa tomentosa. Gum.
[115028-53-0] Quijano, L. eta/, Phytochemistry, 1985, 24, 2741.

Pretomexanthol Dl-00098
[99877-56-2]
C 18H 300 2 M 278.434
Constit. of Cystophora moniliformis. Unstable oil.
van Altena, I.A., Aust. J. Chern., 1988, 41, 49.

Helogynic acid Dl-00094 C21 H360s M 368.512

[114437-14-8] Constit. of Montanoa tomentosa. Gum.
Quijano, L. et al, Phytochemistry, 1985, 24, 2741.

Prezoapatanol Dl-00099
[99877-57-3]

C23H 360 6 M 408.534

Constit. of He/ogyne apaloidea. Oil.
Zdero, C. et al, Phytochemistry, 1988, 27, 616.

~ 1 H 360 4 M 352.513
14-Hydroxy-1,2-~nor-6,10,15-phytatrien- Dl-00095 Constit. of Montanoa tomentosa. Gum.
3-one Quijano, L. et al, Phytochemistry, 1985, 24, 2741.
13-Hydroxy-6,10,14-trimethy/-5,9,14-pentadecatrien-2-one
OH 2,6,10,14-Tetramethylheptadecane Dl-00100
I
0 [18344-37-1]

C 18H 300 2 M 278.434

(6E,10E,14R)-form [81373-97-9]
lsol. from Cystophora moni/iformis. Oil. [IX]~ -8.3° (c, I C2tH44 M 296.579
in CHCI 3). Isol. from Soudan shale and Nonesuch seep oil (109 years
old).
Ravi, B.N. et al, Aust. J. Chern., 1982, 35, 171.
Johns, R.B. et al, Geochim. Cosmochim. Acta, 1966, 30, 4437 (isol)
McCarthy, E.D. et al, Tetrahedron Lett., 1967, 4437 (synth)
14-Methylene-2,10-phyta~ene-1,12,19,20- Dl-00096 Shlyakhov, A.F. et al, J. Chromatogr., 1975, 104, 337 {g/c)
tetrol
2,6,10,14-Tetramethylpentadecane Dl-00101
Pristane. Norphytane
[1921-70-6]

C 21 H 380 4 M 354.529
(1E,10E)-form C1,H40 M 268.525
11,19,10-Trihydroxy-14-methylenegeranylnerol t> RZ1880000.
Constit. of Lasio/aena morii. Gum. (6RS,1 OSR)-form
19-Ac: meso-form
C23H4C,Os M 396.566 Obt. from shark liver oil, herring oil, Bute inlet wax,
Constit. of L. morii. Gum. wool wax, zooplankton and crude oil. Oil. Mp -100°.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 161. Bp 296°, Bp 10 158°. Chiral forms may also occur
naturally; in most cases the opt. rotn. of isol. samples
has not been measured.
Hallgren, B. et al, Acta Chern. Scand., 1963, 17, 543.
Kates, M. et al, Biochemistry, 1967, 6, 3329 (abs config, bib[)
Jain, T.C. et al, Can. J. Chern., 1969, 47, 4359 (isol)
Goodman, R.A. et al, J. Am. Chern. Soc., 1973, 95, 7553 (cmr)
Carman, C.J. et al, Macromolecules, 1973, 6, 719 (cmr)

670
2,6,10,14-Tetramethylpentadecanoic ... - 4,8,12-Trimethyl-1,3,7,11-... Di-00102 - Di-00110

2,6,10,14-Tetramethylpentadecanoic acid Di-00102 C19H 360 M 280.493

Pristanic acid Constit. of Tetragonia tetragonoides. Oil.
[1189-37-3] Aoki, T. et al, Phytochemistry, 1982, 21, 1361.

6,1 0,14-Trimethyl-5,9-pentadecadiene- Di-001 07

COOH 2,12-dione, 9CI
Ct,H 380 2 M 298.508
Component of butterfat, Californian petroleum and sheep 0
perinephric fat. Oil. A mixture of 6R- and 6S-forms :::,....
occurs in nature.
CtaH300 2 M 278.434
Cason, J. et al, Tetrahedron, 1965, 21, 471 (isol, struct)
E1djam, L. et al, Acta Chern. Scand., 1966, 20, 2313 (synth) (E,E)-form [84321-90-4]
Nakajima, K. eta/, Agric. Bioi. Chern., 1974, 38, 1859 (biosynth) Constit. of Sargassum micracanthum. Liq.
Cox, R.E. eta/, Biochim. Biophys. Acta, 1974, 360, 166 (biosynth, Shizuri, Y. eta/, Phytochemistry, 1982, 21, 1808.
stereochem)

6,1 0,14-Trimethyl-5, 10-pentadecadiene- Dl-00108

2,6, 10,14-Tetramethyl-1-pentadecene Dl-00103 2,12-dione, 9CI
Zamene. Norphytene
[71802-03-4]
[2140-82-1]

C1,H 38 M 266.509 CtaH3002 M 278.434

Produced from liver oils of elasmobranch fishes and occurs Constit. of Sargassum micracanthum. Liq.
in shale oil. Oil. Bp2 128°. Shizuri, Y. et al, Phytochemistry, 1982, 21, 1808.
Kikumasa, S. et al, J. Org. Chern., 1967, 32, 177 (synth)
Larcheveque, M. et a/, Tetrahedron Lett., 1975, 3851 (synth) 6,10,14-Trimethyl-5,9,13-pentadecatrien-2- Di-001 09
one, 9CI
Tomentanol Dl-00104 [762-29-8]
[I 07390-07 -8]
#'13
14
0
C 18H 300 M 262.434
(5E,9E)-form [1117-52-8] Farnesylacetone
Present in various plants, e.g. tobacco, tomato. ni?
C21H3604 M 352.513 1.4816. Other stereoisomers also prepd.
Constit. of Montanoa tomentosa. Gum. Semicarbazone: Mp 81-82°.
Oshima, Y. et al, Phytochemistry, 1986, 25, 2567. 13R,l4-Epoxide: [66067-35-4]. 12-(3,3-Dimethy/oxiranyl)-
5,9-dodecadien-2-one, 9CI. Farnesylacetone epoxide
Tomentol Di-00105 CtaH 300 2 M 278.434
Constit. of Cystophora moniliformis. Oil. [cx]n -3.2° (c, I
[89116-69-8] in CHCI 3).
Isler, 0. et al, Helv. Chim. Acta, 1958, 41, 786 (synth)
Laats, K. et al, CA, 1969, 70, 106666g; 1975, 83, 97600v (synth)
Kazlauskas, R. et al, Experientia, 1978, 34, 156 (epoxide)
Ferezou, J.-P. et a/, Helv. Chim. Acta, 1978, 61, 669 (biosynth)
Enzell, C.R. eta/, Mass Spectrom. Rev., 1986, S, 39 (ms)

CltH3604 M 352.513 4,8,12-Trimethyl-1,3,7 ,11-tridecatetraene Dl-00110

Constit. of Montanoa tomentosa. Gum.
!l.D-Isomer: [71117-50-5]. Montano/
C 21 H 360 4 M 352.513
C16 H 26
"""'
M 218.381
"""' """' """'
Constit. of M. tomentosa. Oil.
Levine, S.D. eta/, J. Am. Chern. Soc., 1979, 101, 3404 (Montano/)
(3E,7E)-form [62235-06-7]
Cotter, M.L., Org. Magn. Reson., 1981, 17, 14 (cmr) Constit. of essential oil of E/ettaria cardamomum.
Kanojia, R.M. eta/, J. Org. Chern., 1982, 47, 1310 (Montano/) Constit. of flower fragrances e.g. Rosa spp., Magnolia
Quijano, L. eta/, Phytochemistry, 1985, 24, 2337 (Tomentol) lilifiora. Oil.
[107554-13-2, 107554-14-3, 107554-15-4]
6,10,14-Trimethyl-2- Di-00106 Maurer, B. eta/, Tetrahedron Lett., 1986, 27, 2111.
methylenepentadecanal Boland, W. et a/, Helv. Chim. Acta, 1989, 72, 247 (biosynth, bib/)
[83725-57-9]

CHO

671
2,6,10-Trimethylundecanoic acid- 2-[(3,4,4a,5,6,8a-Hexahydro-4,7-... Di-00111 - DI-Q0116

2,6,10-Trimethylundecanoic acid Dl-00111 2-((2,3,3a,4,5,7a-Hexahydro-3,6-dimethyl-

2-benzofuranyl)ethylidene)-6-methyl-5-
~COOH heptenoic acid, 9CI Dl-00115
H ,'

4>-L::<
C14H2102 M 228.374
(2R,6R)-form [31653-13-1]
Constit. of Californian petroleum.
Cason, J. et a/, Tetrahedron, 1965, 21, 471 (isol)
Cox, R.E. eta/, J. Chem. Soc., Chem. Commun., 1970, 1639
(struct)
C 20 H 300 3 M 318.455
Compd. not named in the reference. Constit. of
Eremophila foliosissima.
Me ester: [112239-41-5].
Bp0_25 175° (bath). [1X] 0 -49.SO (c, 0.6 in CHC1 3).
Prenylbisabolanes Forster, P.G. eta/, Tetrahedron, 1987, 43, 2999.

2-((3,4,4a,5,6,8a-Hexahydro-4,7-dimethyl-
2H-1-benzopyran-2-yl)methylene)-6-
4-Acetoxy-6-(4-hydroxy-4-methyl-2- methyl-5-heptenoic acid, 9CI Dl-00116
cyclohexenyl)-2-(4-methyl-3-pentenyl)-2-
heptenoic acid Dl-00112

Absolute
configuration

C20H 300 3 M 318.455

Compd. not named in the lit. Constit. of Eremophila
foliosissima.
C 22H 340 5 M 378.508
Compd. not named in the reference. Constit. of Me ester: [112239-43-7].
Oil. Bp0 _3 220° (bath). [cx] 0 -94.1° (c, 0.5 in CHC13).
Eremophi/a foliosissima.
Me ester: [112239-52-8]. Forster, P.G. et a/, Tetrahedron, 1987, 43, 2999.
Unstable oil.
Forster, P.G. eta/, Tetrahedron, 1987, 43, 2999.

9-Geranyl-rx-terpineol Dl-00113
OH

C 20H 340 M 290.488

Constit. of Helichrysum nudifolium. Oil.
Jakupovic, J. et a/, Phytochemistry, 1986, 25, 1133.

16-HellicaUenal Dl-00114
[72145-14-3]

CHO
16

C 20H 300 M 286.456

Constit. of Helichrysum heterolasium. Oil. [cx]~4 + 16° (c, 1
in CHCI 3).
14,15-Dihydro, 16-carboxy/ic acid: [72253-64-6]. 14,15-
Dilrydro-16-helicallenoic acid
C 20H 320 2 M 304.472
Constit. of H. heterolasium. Oil.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 889.

672
Agelasidine B - Ambliolide Di-00117- Di-00122

Ageline A Dl-00120
Agelasine F
10,15-Cyclophytanes [88929-28-6]

Agelasidine B Dl-00117
[96617-50-4]

C16H 40N 5E9 M 422.635 (ion)

Cl3H41 NP 2S M 423.662
!sol. from the Okinawan sea sponge Age/as nakamurai.
Shows antispasmodic and antibacterial activity.
B,HCI: Syrup. [1X]i,5 -2.5° (c, 0.43 in MeOH). Ambliol A
Nakamura, H. et al, J. Org. Chern., 1985, 50, 2494 (isol, uv,t ir,
pmr, cmr, struct)
Constit. of sponge Age/as sp:-Active against gram-positive
bacteria. ATPase inhibitor, weak ichthyotoxin.
Chloride: [88855-15-6].
C16H40CIN5 M 458.088
Plates (MeCN) or powder. Mp 178-180° (175-176°). [1X]i,5
- 5.SO (c, 2.5 in MeOH), [1X]n -8.4° (c, 3 in CHC1 3).
Capon, R.J. et a/, J. Am. Chern. Soc., 1984, 106, 1819.
Wu, H. et al, Tetrahedron Lett., 1984, 25, 3719 (isol, struct, nmr)
Dl-00121
[76215-30-0]

a~
Agelasidine C Dl-00118
[96617-52-6]
\
OH
\18

C20 H 320 2 M 304.472

Constit. of Dysidea amblia. Oil. [IX]~ -3.9° (c, 2.5 in
CHC1 3).
C:13H 41 N 30 2S M 423.662 15-Bromo, 8-oxo, Ac: 1-Bromo-8-ketoambliol A acetate
Isol. from the Okinawan sea sponge Age/as nakamurai. C22H 31 Br0 4 M 439.388
Shows antispasmodic and antibacterial activity. Metab. of a Dendrilla sp. Oil. [IX]~ + 18.2° (c, 1.2 in
B,HCI: Syrup. [1X]i,5 + 8.5° (c, 2.0 in MeOH). CHC1 3).
Nakamura, H. et a/, J. Org. Chern., 1985, 50, 2494 (isol, uv, ir, 5-Deoxy, 5,18-didehydro: [76249-87-1]. Dehydroambliol A
pmr, cmr, struct) C20 H 300 M 286.456
Isol. from D. amblia. Oil. [IX]~ - 1.3° (c, 1.8 in CHC1 3).
Agelasine E Dl-00119 The name Dehydroambliol A is somewhat misleading.
[92599-00-3] Walker, R.P. et al, J. Org. Chern., 1981, 46, 1098 (isol)
Sullivan, B. et al, J. Org. Chern., 1984, 49, 3204 (deriv)

Ambliolide Dl-00122
[76215-28-6]

C16H 40N 5E9 M 422.635 (ion)

Isol. from the Okinawan sea sponge Age/as nakamurai.
ATP-ase inhibitor.
a~OMe \
OH
Chloride: [92599-01-4]. \

C16H 40CIN 5 M 458.088 Cz1H 340 4 M 350.497

Powder. Mp 180-182°. [1X]i,5 -17.1° (c, 1.88 in MeOH). Constit. of Dysidea amblia. Oil. [IX]~ -4° (c, 2.2 in
Wu, H. et al, Tetrahedron Lett., 1984, 25, 3719 (uv, pmr, cmr, ms, CHC1 3).
struct) Walker, R.P. eta/, J. Org. Chern., 1981, 46, 1098.

673
Anhydrovitamin A1 - Hebemacrophyllide Di-00123 - Di-00130

Anhydrovitamin AI Dl-00123 Ac: Pale-yellow cryst. (pet. ether). Mp 65-66°.

[1224-78:8] 15-Aldehyde: [739-13-9]. 5,6-Monoepoxyvitamin A aldehyde.
5,6-Epoxy-5,6-dihydroretinal, 9CI
C:zoHzs02 M 300.440
Yellow cryst. (pet. ether). Mp 101-102°.
Jungalwala, F.B., Biochem. J., 1965, 95, 17 (struct)
John, K.V. et al, J. Chromatogr., 1965, 18, 53 (tic)

5,8-Epoxyvitamin A Dl-00128
C:zollzs M 268.441
Constit. of Silonia silondia and Pungassius punga eggs.
Orange cryst. Mp 76-77°.
Ghosh, M.C. et al, Indian J. Biochem. Biophys., 1972, 9, 209 (isol) 0
Pekkarinen, L. et al, Acta Chern. Scand., Ser. A, 1976, 30, 285
(isol) C:zoH300 2 M 302.456
Oil.
Axerophthene Dl-00124 15-Aldehyde: 5,8-Epoxyvitamin A aldehyde
Axerophtene C:zollzs03 M 316.439
[6895-29-0] Cryst. (Et20jpet. ether). Mp 104-105°.
Jungalwala, F.B. et al, Biochem. J., 1965, 95, 17 (struct)
John, K.V. et al, J. Chromatogr., 1965, 18, 53 (tic)

Hebeclinolide Dl-00129
15,16-Epoxy-2-oxo-9,10-seco-1(10),8,13(16),14-labdatetraen-
C:zoH30 M 270.457 17,12-olide
Shows slight Vitamin A activity. Thick yellow oil. (63147-18-2]
Englert, G. et al, Helv. Chim. Acta, 1975, 58, 2367 (cmr)
Gourey, J.G. et al, J. Chern. Soc., Chern. Commun., 1976, 779
(synth)

6a.H-form
Caulerpol Dl-00125
(62123-23-3]
0
C:zoH240 4 M 328.407
Can be considered as a cycloph_ytane deriv~~;tive_ or as -~
'secofabdane. lso[ from Hebeclinium macrophyllum. Oil.
C:zoH340 M 290.488 [oc]~ -6° (c, 1.5 in CHC1 3). Mixt. of 6-epimers.
Constit. of Caulerpa brownii. Bp0 _1 120°. [ocJn -84.8° 6rx.H-form
(MeOH). 2tx-Hydroxy: 3-Hydroxyhebec/inolide
Blackman, A.J. et al, Tetrahedron Lett., 1976, 2729. C:zoH240 5 M 344.407
Constit. of H. macrophyllum. Cryst. (as acetate). Mp
Dinortrixagone Dl-00126 112° (acetate). 3-Numbering refers to secolabdane struct.
8-(6-Methylene-2,2-dimethylcyclohexyl)-6-methyl-3,5- Occurs as a mixt. of 6-epimers; Mp refers to acetate of
octadien-2-one 61XH-form.
Bohlmann, F. et al, Chern. Ber., 1977, 110, 1321 (isol)
Warning, U. et al, Phytochemistry, 1987, 26, 2331 (deriv)

Hebemacrophyllide Dl-00130
2-0xo-9,10-seco-1(10),8,13-labdatrien-15,16-o/ide
C 1aHzs0 M 260.419
Constit. of Bellardia trixago. Oil. [ocJn + 13.7° (c, 0.77 in 19 0
CHC13). 0
de Pascual, T.J. et al, Tetrahedron, 1982, 38, 1837.

5,6-Epoxyvitamin A 0
Dl-00127
5,6-Epoxy-5,6-dihydroretinol, 9Cl. 5,6-Monoepoxyvitamin A C:zoHzs03 M 316.439
Can be considered as a cyclophytane or as a
[739-11-7)
secolabdane (2 different num6ering systems,
cyclophytane system shown). Parent compd. is
unknown.
7tx-Acetoxy: [111508-89-5]. 7rx.-AcetoxyhebemtlCrophyl/ide.
6P-Acetoxyhebemacrophyllide
C22 H 300 5 M 374.476
C:zoH300 2 M 302.456 Constit. of Hebeclinium macrophyllum. Oil.
Unstable oil.

674
3-Hydroxyretinal - Retinal Di-00131 - Di-00137

19-Hydroxy: 19-HydroxyltebeiiiiiCropllyllitk. 17- Isotrixagoyl oxide Dl-00134

Hydroxyhebemacrophy/lide (83631-61-2]
<;.H210 4 M 332.439
Constit. of H. macrophyllum. Oil. !sol. as a mixt. of 6-
epimers.
6-Epimer, 7a.-acetoxy: (111508-90-8]. 6-Epi-7«-
tiCetoxyltebeiiiiiCropllyl/ide. 5-epi-6P-
Acetoxyhebemacrophyllide
CzzH300 5 M 374.476 <;.H310 M 288.472
From H. macrophyllum. Oil. Constit. of Bellardia trixago. Oil.
19-Aidehyde: 19-0xoltebeiiiiiCropllyllide. 17-
De Pascual Teresa, J. eta/, Tetrahedron, 1982, 38, 1837.
0xohebemacrophyllide
Czoll:u;04 M 330.423
From H. macrophyllum. Oil. Isol. as a mixt. of 6- Jbanic acid Dl-00135
epimers. [70902-35-1]
[111508-87-3, 111508-88-4, 111534-68-0, 111534-69-1]

a~
Warning, U. et al, Phytochemistry, 1987, 26, 2331.

3-Hydroxyretinal Dl-00131
(60046-53-9]
<;.H:za03 M 316.439
Constit. of Eupatorium jhanii. Oil (as Me ester). [a.]n -93°
(c, 1 in CHC13) (Me ester).
Gonzalez, A. G. et al, An. Quim., 1979, 75, 128.
HO'
Czoll:zaOz M 300.440 Laurencianol Dl-00136
Oil.
[84323-26-2]
Barua, R.K. eta/, Biochem. J., 1966, 101, 250.
I

4-Hydroxyretinoic acid Dl-00132 NOH CH2Cl

~ """<::::: COOH
o.-y--:t:fou Absolute
configuration

<;.H35Br1Cl03 M 518.755
OH Constit. of marine alga Laurencia obtusa. Antibacterial
agent. Cryst. (C 6H 6fhexane). Mp 114-116°.
Czoll280 3 M 316.439
Caccamese, S. eta/, Tetrahedron Lett., 1982, 23, 3415 (isol, cryst
Metab. of retinoic acid. Cryst. (EtOAc). Mp 178-181°. struct)
Me ester: Cryst. (EtOAc). Mp 110-112°.
4-Ketone: [38030-57-8]. 4-0xoretinoic acid Retinal Dl-00137
Czoll160 3 M 314.424
Vitamin A 1 aldehyde. Retinene 1• Retinaldehyde
Cryst. (EtOAc/THFjhexane). Mp 186-189° (159-161°).
[116-31-4]
4-Ketone, Me ester: Cryst. (hexane). Mp 93-95°.
Rosenberger, M. et a/, J. Org. Chem., 1982, 47, 1698.
CHO
lsotrixagol Dl-00133
[83631-62-3]
Czoll280 M 284.441
Forms part of the Rhodopsin complex. Cryst. Mp 64-65°.
~ VH6407000.
Semicarbazone: Yellow cryst. (CHC1 3/Et20). Mp 199-201°.
3,4-Didehydro: (472-87-7]. Vitamin A 2 aldellyde. Retinene2
<;.H340 M 290.488 <;.H160 M 282.425
Constit. of Bellardia trixago. Oil. [a.]n + 11.7° (c, 0.92 in Constit. of liver oil. Orange-red cryst. Mp 77-78°.
CHQ3). Ball, S. et al, Biochem. J., 1948, 42, 516 (synth)
De Pascual Teresa, J. et al, Tetrahedron, 1982, 38, 1837. Arens, J.F. et a/, Reel. Trav. Chim. Pays-Bas (J. R. Neth. Chem.
Soc.), 1949, 68, 604 (synth)
Sebrell, W.H. et al, The Vitamins, Academic Press, Vol. I, 1967
(rev)
Patel, D.J. et al, Nature (London), 1969, 221, 825 (pmr)
Hamanaka, T. et al, Acta Crystallogr., Sect. B, 1972, 28, 214 (cryst
struct)
Gilardi, R.G. et al, Acta Crystallogr., Sect. B, 1972, 28, 2605 (cryst
struct)
Yasaka, W.J. et al, J. Nutr. Sci. Vitaminol., 1973, 19, 369 (isol)

675
Retinoic acid - Trixagodiol A
Honig, B. eta/, Annu. Rev. Biophys. Bioeng., 1974, 3, 151 (rev)
Englert, G., Helv. Chim. Acta, 1975, 58, 2367 (cmr)
Shriver, J. eta/, J. Am. Chern. Soc., 1976, 98, 2407 (cmr)
Simmons, C.J. eta/, Acta Crystal/ogr., Sect. B, 1981, 37, 2197
(cryst struct)
Asato, A.E. eta/, J. Am. Chern. Soc., t983, 105, 2923 (synth)
Retinoic acid, 9CI Dl-00138
3,7-Dimethyl-9-(2,6,6-trimethylcyclohexenyl)-2,4,6,8-
nonatetraenoic acid. 15-Apo-P-caroten-15-oic acid. Tretinoin,
INN, BAN, USAN. Vitamin A acid. Numerous
proprietary names
~ COOH
(13£)-form
Crolf280 1 M 300.440
(13£)-form [302-79-4]
Shows vitamin A activity. Keratolytic agent. Cryst.
(MeOH). Mp 181.5°.
I> Exp. teratogen. VH6475000.
(13Z)-form [4759-48-2] lsotretinoin, BAN, USAN, INN.
Accutane. Roaccutane. Roacutan. Ro 4-3780
Keratolytic antineoplastic agent, used to treat cystic
acne. Cryst. (EtOH). Mp 189-190° (174-175°).
I> VH6440000.
Dowling, J. eta/, Vitam. Horm. (N.Y.), 1960, 18, 515 (rev)
Starn, c;::.H., Acta Crystallogr., Sect. B, 1972, 28, 2936 (cryst struct)
Borua, A.B. eta/, Tetrahedron Lett., 1972, 1823 (synth)
Julia, M. et a/, Bull. Soc. Chim. Fr., 1973, 746 (synth)
Cainelli, G. eta/, Gazz. Chim. Ita/., 1973, 103, 117 (isom)
Englert, G., Helv. Chim. Acta, !975, 58, 2367 (cmr)
Bard, D.R. eta/, Br. J. Cancer, 1977, 35, 110 (pharmacol, tox)
McCormick, A.M. eta/, Anal. Biochem., 1978, 86, 25 (hplc)
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 1616, 1656.
Perry, M.D. eta/, Clin. Pharm., 1983, 2, 12 (rev)
De Paolis, A.N., J. Chromatogr., 1983, 258, 314 (tic)
Bernard, M. et al, J. Org. Chern., 1983, 48, 3164 (synth)
Ward, A. et a/, Drugs, 1984, 28, 6 (rev, Isotretinoin)
Bestmann, H.J. eta/, Justus Liebigs Ann. Chern., 1984, 1740
(synth)
Chytil, F., Pharmacol. Rev., 1984, 36, 93 (rev, pharmacol, props)
Madani, K.A., Nutr. Res., 1986, 6, 107 (rev)
Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th Ed.,
Akademie-Verlag, Berlin, 1987, 5902.
Perly, B. eta/, Z. Naturforsch., B, 1988, 43, 1072 (pmr)
Sax, N.l., Dangerous Properties of Industrial Materials, 6th Ed.,
Van Nostrand-Reinhold, 1984, 2364.
Retinol, 9CI, INN Dl-00139
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-
nonatetraen-1-ol. 15-Apo-P-caroten-15-ol. Vitamin A 1•
Afaxin. Axerol. Gadol. Prepalin. Testavol. Vitamin A.
Numerous proprietary names
[68-26-8]
C 36H 600 1 M 524.869
Constit. of many fish-liver oils, milk, egg-yolk, etc. Yellow
cryst. Mp 63-64°. Bp0.000001 137-138°.
I> VH6750000.
Ac: [127-47-9]. Retinol acetate. Vitamin A acetate. Other
proprietary names
C11H 310 1 M 328.494
676
Di-00138 - Di-00140
Cryst. (MeOH). Mp 57-58°.
I> VH6825000.
Propanoyl: [7069-42-3]. Retinol propanoate. Axerofluid.
Axerophthol propionate. Vitamin A propionate
C13H 340 1 M 342.520
ni11.6042. Fluid to -10°.
Hexadecanoyl: [79-81-2]. Retinol palmitate. Vitamin A
palmitate. Arovit. Other synonyms
C36 H 600 1 M 524.869
Found in fish liver oils. Mp 28-29°.
I> VH6860000.
3,4-Didehydro: [79-80-1]. 3,4-Didehydroretinol. !Vitamin A 2•
Dehydroretinol. 3-Dehydroretinol
C10H 280 M 284.441
Constit. of fresh-water fish oils. Golden-yellow oil. Mixt.
of stereoisomers. Has 40% biological activity of Vit. A 1.
15-A/dehyde: see Retinal, Di-00137
15-Carboxylic acid: see Retinoic acid, Di-00138
Isler, 0. eta/, Adv. Org. Chern., 1963, 4, 115 (synth, rev)
Fr. Pat., I 452 791, (1966); CA, 66, 105072r (synth, pfopanoate)
Isler, 0. eta/, Chim. Ind. (Milan), 1967, 49, 1317 (rev)
Sebrell, W.H. eta/, The Vitamins, Academic Press, Vol. I, 1967
(rev)
Westermann, F.H., Int. J. Vitamin Nutr. Res., 1972, 42, 104
(metab, palmitate)
Oberhiinsli, W.E. et a/, Acta Crystallogr., Sect. B, 1974, 30, 161
(cryst struct)
Mukaiyama, T. eta/, Chern. Lett., 1975, 1201 (synth)
Englert, G., Helv. Chim. Acta, 1975, 58, 2367 (cmr)
Baumann, C., Method. Chim., 1978, 11, 200 (rev, Vit. A 2)
Cardillo, G. eta/, J. Chem. Soc., Perkin Trans. 1, 1979, 1729
(synth)
Mehta, R.R. eta/, J. Chern. Soc., Perkin Trans. 1, 1982, 12, 2921
(synth, acetate)
Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
Pharmaceutical Press, London, 1982/1989, 7821, 7822, 7823.
Pitt, G.A., Proc. Nutr. Soc., 1983, 42, 43 (struct, activity, rev)
Pure Appl. Chern., 1983, 55, 722 (nomencl)
Williams, J.B. eta/, J. Lipid Res., 1984, 25, 638 (metab, acetate)
Goodman, D.S. et a/, Retinoids, 1984, 2, 1, 177 (metab, biosynth,
rev)
Liu, R.S.H. eta/, Tetrahedron, 1984, 40, 1931 (rev)
Harbison, G.S. eta/, J. Am. Chern. Soc., 1985, 107, 4809 (cmr,
acetate)
Ajima, A. et a/, Biotechno/. Lett., 1986, 8, 547 (synth,
hexadecanoate)
Otera, J. eta/, J. Org. Chern,, 1986, 51, 3834 (synth)
Sundaresan, P., J. Sci. Ind. Res., 1987, 46, 105 (rev, metab)
Vaezi, H.F. et a/, Org. Prep. Proced. Int., 1987, 19, 187 (synth, Vit.
A,)
Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th Ed.,
Akadernie-Verlag, Berlin, 1987, 5941, 6719, 8103.
Hosoda, A. et al, Tetrahedron Lett., 1987, 28, 65 (synth)
Trixagodiol A Dl-00140
[83631-59-8]
a~C~OH
Crolf340 1 M 306.487
Constit. of Bel/ardia trixago. Oil. [ocln + 10.1° (c, 2.14 in
CHC1 3).
De Pascual Teresa, J. eta/, Tetrahedron, 1982, 38, 1837.
Trixagodiol C- 3-Bromo-13-labdene-8,15-diol Di-00141 - Di-00146

Trixagodiol C Dl-00141 Trixagotriol Dl-00144

[83631-57-6] [83631-56-5]

~-~CH2 0H )(.._,~CH2 0H
u HO lA. HO
CzoH340 1 M 306.487 CzoH360 3 M 324.503
Constit. of Bellardia trixago. Oil. Constit. of Bel/ardia trixago. Oil.
1!..9•19-Isomer: [83631-58-7]. Trixagodiol B De Pascual Teresa, J. eta/, Tetrahedron, 1982, 38, 1837.
CzoH340 1 M 306.487
Isol. from B. trixago. Oil. [1X]n + 7.4° (c, 1.92 in CHC1 3).
De Pascual Teresa, J. et a/, Tetrahedron, 1982, 38, 1837.

Trixagoene
[69903-59-9]
Dl-00142
Labdanes

3-Bromo-9,13-labdanediol Dl-00145
CzoH 31 M 272.473 OH
Constit. of Bellardia trixago. Oil.
de Pascual, T.J. eta/, Tetrahedron, 1982, 38, 1837.
I

Trixagol Dl-00143 B
[69903-57-7] (3~,13S)-form
CzoH37 Br01 M 389.415
a~CH,OH (3P,13S)-form
ent-13-Epiconcinndiol
Isol. from Chondria tenuissima. Cryst. (CHC1 3fhexane).
Mp 101.5-102°. [1X]~ -17.34° (c, 0.445 in CHC1 3).
CzoH340 M 290.488 (ent-3P,I3R)-form [50326-69-7] Concinndiol
Constit. of Bel/ardia trixago. Oil. [1X]n + 8° (c, 0. 76 in
Constit. of Laurencia concinna. Cryst. (hexane). Mp
CHC1 3).
212°.
Ac: Trixagoyl acetate
Sims, J.J. eta/, J. Chern. Soc., Chern. Commun., 1973, 470 (isol,
C11H 360 1 M 332.525 struct)
Constit. of B. trixago. Oil. [1X]n + 3.8° (c, l.l2 in Yamaguchi, Y. eta/, Tetrahedron Lett., 1985, 26, 343 (synth)
CHC1 3). Oztuncr, A. et a/, Phytochemistry, 1989, 28, 3403 (iso/, pmr, cmr,
9,10-Epoxide: 9,10-Epoxytrixagol. 6,7-Epoxytrixago/ cryst struct)
CzoH340 1 M 306.487
Constit. of B. trixago. Oil. 3-Bromo-13-labdene-8,15-diol Dl-00146
Malonyl, Me ester:
C14H 380 4 M 390.562
Constit. of B. trixago. Oil. [1X]n +6.6° (c, 1.4 in CHC1 3).
Malonyl, Et ester:
C25 H400 4 M 404.589
Constit. of B. trixago. Oil. Br'
Malonyl, 2-methy/propy/ ester:
C17H 440 4 M 432.642 CzoH 35 Br01 M 387.399
Constit. of B. trixago. Oil. [1X]n + 1° (c, 0.98 in CHC1 3). (ent-3P.BP,13E)-form [17941-22-9] Aplysin 20
Malonyl, trixagoyl ester: Ditrixagoylmalollllte Constit. of Aplysia kurodai. Cryst. (MeOH). Mp 146-
C43H 680 4 M 649.008 1470. [IX]!:; -78.1 o (c, 1 in MeOH).
Constit. of B. trixago. Oil. Yamamura, S. eta/, Bull. Chern. Soc. Jpn., 1971, 44, 2560 (isol)
De Pascual Teresa, J. eta/, Tetrahedron, 1982, 38, 1837 (isol) Murai, A. eta/, Tetrahedron Lett., 1984, 25, 4955 (synth)
Armstrong, R.J. eta/, Can. J. Chern., 1983, 61, 2530 (synth) Yamaguchi, Y. eta/, Tetrahedron Lett., 1985, 26, 343 (synth)
Nishizawa, M. eta/, J. Org. Chern., 1986, 51, 806 (synth)

677
3-Bromo-14-labdene-8,13-diol - 15,16-Diacetoxy-7,13(16),14-... Di-00147- Di-00153

3-Bromo-14-labdene-8, 13-diol Dl-00147 C23 H 340 5 M 390.519

Constit. of Salvia villosium. Gum.
Zdero, C. et a/, Phytochemistry, 1988, 27, 227.

Corymbivillosol Dl-00151
[113493-23-5]

coow
r r C H 2 0H
C20H 35 Br02 M 387.399
(3ft,81X.,l3S)-form [78012-27-8] lsoconcinndiol
Constit. of Laurencia snyderae. Cryst. (CHC1 3). Mp 173-
1740. ~CH 2 00C)

H)j:J
Howard, B.M. et a/, Phytochemistry, 1980, 19, 2774 (iso[)
Rodriguez, M.L. eta/, Acta Crystallogr., Sect. C, 1989, 45, 306
(cryst struct, abs config)

C43H 680 6 M 681.007

3-Bromo-13(16)-labdene-8,14,15-triol Dl-00148 Constit. of Corymbium villosum. Gum. [aJii -17° (c, 0.18
OH in CHC1 3).
3-Ac:
C45H 700 7 M 723.044
rrCH20H
From C. villosum. Gum. [a]~4 -18° (c, 0.16 in CHC1 3).

-~-OH Zdero, C. eta/, Phytochemistry, 1988, 27, 227.

Br~ Cycloschkuriadiol Di-00152

ent-8a,J3S:J5,16R-Diepoxy-14,16-labdanediol
C20H 35 Br03 M 403.399 [77129-31-8]
(ent-3p,ap,Uf.)-form [115346-29-7] Venustanol
Constit. of Laurencia venusta. Cryst. Mp 97-99°. [IX.]ii
- 10.8° (c, 0.562 in MeOH).
Suzuki, M. et a/, Phytochemistry, 1988, 27, 1209.

Conyzanol A Dl-00149
OH
C20H 340 4 M 338.486
Constit. of Schkuhria multiflora. Oil.
OMe 16-Ac:
CzzH360 5 M 380.523
Constit. of S. multiflora. Oil. [a]~4 -6.8° (c, 2.4 in
CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 881.
C22 H 360 7 M 412.522
Constit. of Conyza stricta.
15,16-Diacetoxy-7,13(16),14-labdatriene Di-00153
16-Epimer: Conyzanol B
C22 H 360 7 M 412.522 AcO ,::r
Costit. of C. stricta. ,::r OAc
[130281-72-0, 130325-01-8)
Ahmed, M. eta/, Phytochemistry, 1990, 29, 2715 (isol, pmr, ms)

7, 13-Corymbidienolide Di-00150

~
(coo rYy17 C24H 360 4 M 388.546
(ent-13E,14E)-form
Metab. of Caulerpa trifaria. Rods (CH 2Cl2 jpet. ether).
Mp 62.5-63°. [aJn -8° (c, 6.6 in CHC1 3).
coo"xP
Capon, R.J. eta/, Phytochemistry, 1983, 22, 1465.
C23H 340 4 M 374.519
Constit. of Corymbium villosum. Cryst. Mp Ill 0. [alii
-161° (c, 0.54 in CHC1 3).
tl 8•11-Isomer, 7P-hydroxy: 7p-Hydroxy-8(17),13-
corymbidienolide

678
8,17:15,16-Diepoxy-6,9-dihydroxy-... - 2,3-Dihydroxy-7,13-labdadien-15-... Di-00154 - Di-00159

8,17:15,16-Diepoxy-6,9-dihydroxy- Dl-00154 2,3-Dihydroxy-12,17-dioxo-7,13- Dl-00157

13(16),14-labdadien-19-oic acid labdadien-15-oic acid
o moH

HO~

C 20H 11;05 M 346.422 C20 H 280 6 M 364.438

(6rz,BP,9rz)-form
(2rz,3rx.,13Z)-form
19-+6 Lactone: ·[55784-80-0]. 8,17:15,16-Diepoxy-9-
2,3-Diange/oy/: 2rz-Angeloyloxybrickellidiffusic acid
hydroxy-13(16),14-labdadien-19,6-o/ide. Leonotinin
C 30H 400 8 M 528.641
Minor constit. of Leonotis nepetaefolia. Cryst.
Obt. from Brickellia diffusa.
(CHC1 3 /Etp). Mp 184-186°. [cxJn +60° (c, 2 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 691.
Purushothaman, K.K. eta/, J. Chern. Soc., Perkin Trans. I, 1974,
2661.
3,15-Dihydroxy-8(17),13-labdadien-19-al Dl-00158

q;To
8,17:15,16-Diepoxy-6,9-dihydroxy- Dl-00155
13(16),14-labdadien-19,20-olide # CHPH

(3a, 13E}form

C20H 320 3 M 320.471

(3rz,l3E)-form [117254-99-6] Jrx.-Hydroxyisoagatholal
Constit. of Juniperus thurifera. Cryst. (CH 2Cl2fhexane).
C 20H 160 6 M 362.422
Mp 129°. [ex]~ -0.7° (CHC1 3).
(6p,ap~9rz)-form
(Jp,JJE)-form [117255-05-7] 3P-Hydroxyisoagatholal
6-Ac: [29461-24-3]. Nepetaefuran Cryst. (CH 2Cl2 /hexane). Mp 134°. [a]~ +22.3° (CHC1 3).
C 12H 280 7 M 404.459
3-Ac: [117232-44-7].
Constit. of Leonotis nepetaefolia. Cryst. (EtOH aq.). Mp
C12H 340 4 M 362.508
241-242°. [a]i,S +32.3° (c, 1.3 in MeOH).
Constit. of J. thurifera. Oil. [aW - 14.5° (CHC1 3).
White, J.D. et al, J. Org. Chern., 1973, 38, 720.
San Feliciano, A. eta/, Phytochemistry, 1988, 27, 2241.

7,8:9,13-Diepoxy-1,6,15-labdanetriol Di-00156
2,3-Dihydroxy-7 ,13-labdadien-15-oic acid Dl-00159
I

6
~15
HO ( CH 20H rJcooH
/
Hoyty
0

H
HO~
C 20H 340 5 M 354.486 C 20H 320 4 M 336.470
(ent-lrz,6rz,7rz,Brz,9rz,l3R)-form (ent-2rz,3rx.,13E)-form
'15-(3-Methy/-2-butenoyl): [87462-32-6]. Erigerol Di-Ac:
C15H 400 6 M 436.587 C24H 360 6 M 420.545
Constit. of Erigeron philadelphicus. Cryst. (EtOH). Mp Constit. of Re/hania fruticosa.
159-161°. Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol)
Waddell, T.G. et al, J. Org. Chern., 1983, 48, 4450 (isol, cryst
struct)
Kienzle, F. et al, Helv. Chim. Acta, 1990, 73, 1108 (synth)

679
2,3-Dihydroxy-8(17),13-labdadien-15-... - 15,16-Dihydroxy-8(17),13-labdadien-... Di-00160 - Di-00166

2,3-Dihydroxy-8(17),13-labdadien-15-oic Dl-00160 12, 15-Dihydroxy-8(17), 13-labdadien-19- Dl-00163

acid oic acid
COOH OH
I

CHPH
(2p,3p, 13£)-form

COOH
C 20 H 32 0 4 M 336.470
Cwfl32 0 4 M 336.470 (12S)-form [126221-41-8]
(2ft,3ft,13E)-form Constit. of Guizotia scabra. Cryst. (EtOAc/MeOH). Mp
Me ester: 179-180°. [cx)i? -29° (c, 0.4 in MeOH).
C 21 H 340 4 M 350.497 Fujimoto, Y. eta/, Phytochemistry, 1990, 29, 319 (iso/, pmr, cmr,
Constit. of Nolana rostrata. Oil. [cx]i,S -52.8° (c, 1.08 in cryst struct)
CHC1 3).
(2P,3ft,J3Z)-form 13,16-Dihydroxy-8(17),14-labdadien-18- Dl-00164
Constit. of N. rostrata. Amorph. powder oic acid
(EtOAcjheptane). [cx]i,S -16.7° (c, 0.61 in CHC1 3).
Di-Ac: 2P,3fJ-Diacetoxy-8(17),13Z-labdadienoic acid HO

HSf!t~H
C 24H 360 6 M 420.545
Cryst. (EtOAcfheptane). Mp 122-125°. [cx]i,S -55.SO (c, 1
in CHC1 3).
Garbarino, J.A. eta/, Phytochemistry, 1986, 25, 2833.

2,17-Dihydroxy-7,13-labdadien-15-oic acid Dl-00161

C 20 H 320 4 M 336.470
# COOH (ent-131!.)-form
Constit. of fruits of Xylopia aromatica.
Moraes, M.P.L. eta/, Phytochemistry, 1988, 27, 3205.

14,15-Dihydroxy-8(17),13(16)-labdadien- Dl-00165
Cwfl32 0 4 M 336.470 19-oic acid
(ent-2rx.,J3E)-form [52914-34-8] OH
Constit. of Dodonaea microzyga. Cryst. (MeOH). Mp I

228-230°. [cx]n + 13° (c, 1 in Py).

Jefferies, P.R. eta/, Aust. J. Chern., 1974, 27, 1097.

3,18-Dihydroxy-8(17),13-labdadien-15-oic Dl-00162
acid

(Y~OOH C20H 320 4 M 336.470

(14S)-form

HO'~
Constit. of Juniperus communis. Oil (as Me ester). [cxJn
+43° (c, 1.6 in CHC1 3) (Me ester).
de Pascual Teresa, J. eta/, Phytochemistry, 1980, 19, 1153.
, CH2 0H
15,16-Dihydroxy-8(17),13-labdadien-19- Dl-00166
Cwfl320 4 M 336.470 oic acid
(ent-3ft,J3E)-form [40737-95-9]
Constit. of Gutierrezia solbrigii.
3-Ange/oy/: [99624-40-5).
C25H 380 5 M 418.572
Constit. of G. so/brigii.
3-Ketone: see 18-Hydroxy-3-oxo-8(17),13-/abdadien-15-oic
acid, Di-00316
Jakupovic, J. eta/, Tetrahedron, 1985, 41, 4537.

C 20H 320 4 M 336.470

(IJE)-form [40737-45-9]

680
2,18-Dihydroxy-8(17),13-labdadien-... - 2,13-Dihydroxy-8,14-labdadien-7-one Di-00167 - Di-00172

Sciadopic acid C31 H 460 10 M 578.698

Me ester: [6813-12-3). Methyl sciadopate Constit. of G. solbrigii. Gum.
C21 H 340 4 M 350.497 Jakupovic, J. et al, Tetrahedron, 1985, 41, 4537.
Constit. of Sciadopitys verticillata. Cryst. (Me 2CO aq.).
Mp 108.SO. [cx] 0 -0.7° (CHC1 3). 3,19-Dihydroxy-8(17),13-labdadien-16,15- Dl-00170
Sumimoto, M., Tetrahedron, 1963, 19, 643 (isol) olide
Mills, J.S. et al, Tetrahedron, 1974, 30, 4021 (struct)
0

~OCo
2,18-Dihydroxy-8(17),13-labdadien-15,16- Di-00167

HO'w
olide

w~o C20 H 300 4

HOH2 C 1
M 334.455
H

(ent-3p)-form [4176-97 -OJ 14-Deoxyandrographolide

~OH Constit. of Andrographis paniculata. Cryst. (Etpjpet.
ether). Mp 175°. The name 14-deoxyandrographolide is
C20H 300 4 M 334.455
incorrect as andrographolide has a 12, 13-double bond.
(ent-2«.)-form
19-0-P-D-Glucopyranoside: [82209-72-1). Andropanoside
Constit. of Gutierrezia solbrigii. Gum.
C26H 400 9 M 496.597
Jakupovic, J. et al, Tetrahedron, 1985, 41, 4537. Constit. of A. paniculata. Needles (MeOH/Me 2CO). Mp
199-200°. [cx)i;' -35.1° (c, 0.57 in Py).
2,19-Dihydroxy-8(17),13-labdadien-16,15- Dl-00168 Ba1main, A. et al, J. Chern. Soc., Perkin Trans. 1, 1973, 1247.
olide Fujita, T. et al, Chern. Pharm. Bull., 1984, 32, 2117
(Andropanoside)

12,15-Dihydroxy-7,13-labdadien-16,15- Dl-00171
olide
OH

OH

C20H 300 4 M 334.455

(ent-2«.)-form [81727-18-6) Phlogantholide A
C20H 300 4 M 334.455
Constit. of Phlogacanthus thyrsiflorus. Cryst.
(CHC1 3 jpet. ether). Mp 144-146°. [ex]~ -39.1° (CHC1 3). (ent-121;,151;)-form
Constit. of Acritopappus hagei. Gum. [cx]i;' -10.7° (c, 5.7
19-0-P-D-Glucopyranoside: Phloganthoside
in CHC1 3) (as di-Ac).
C26H 400 9 M 496.597
Constit. of P. thyrsiflorus. Amorph. Mp 193-194° (as Bohlmann, F. et al, Phytochemistry, 1980, 19, 2695.
penta-Ac). [cx)~6 -22.9° (CHC1 3) (penta-Ac).
Barna, A.K. et al, Phytochemistry, 1985, 24, 2037; 1987, 26, 491. 2,13-Dihydroxy-8,14-labdadien-7-one Dl-00172
OH

:
3,18-Dihydroxy-8(17),13-labdadien-15,16- Dl-00169
olide

CX>=o
HO"
HOH2
W C20H 320 3
(2rx.,13R)-form
M 320.471

Constit. of Waitzia acuminata.

C20H 300 4 M 334.455 2-Ketone: 13R-Hydroxy-8,14-lllbdadiene-2,7-dione
C20H 300 3 M 318.455
(ent-3p)-form Constit. of W. acuminata.
3-Angeloyl: [99624-43-8).
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1943.
C25H 360 5 M 416.556
lsol. from Gutierrezia solbrigii. Gum.
3-Angeloyl, 18-0-P-D-glucopyranoside: [99624-44-9).

681
ent-3P,15-Dihydroxy-7,13-labdadien-... - 2,19-Dihydroxy-7-labden-15-oic acid Di-00173 - Di-00179

ent-3P,15-Dihydroxy-7,13-labdadien-2-one Di-00173 lsol. from Relhania fruticosa.

Dawson, R.M. eta/, Aust. J. Chern., 1966, 19, 2133.

H:rp
fTcHpH Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173.

3,19-Dihydroxy-8(17),11,13-labdatrien- Dl-00177
16,15-olide
0
C20 H 32 0 3 M 320.471
Constit. of Baccharis boliviensis. Gum.
15-Aldehyde: ent-3p-Hydroxy-2-oxo-7,13-/abdadien-15-al
C20H3003 M 318.455
Constit. of B. boliviensis. Oil. Both E- and Z-isomers
occur.
15-Aldehyde, 3-deoxy: ent-2-0xo-7,13-labdadien-15-al
C20 H 300 2 M 302.456 HO~
Cons tit. of B. boliviensis. Oil. I
HOH2C
Zdero, C. et al, Phytochemistry, 1989, 28, 531.
C20 H 280 4 M 332.439
13,18-Dihydroxy-8,14-labdadien-7-one Dl-00174 (ent-3P,l1E)-form [42895-58-9]
Constit. of Andrographis paniculata. Cryst. (EtzO). Mp
203-204°.
Balmain, A. et al, J. Chern. Soc., Perkin Trans. I, 1973, 1247.

8,15-Dihydroxy-13-labden-19-al Di-00178

HOH 2 ~ CHPH
C20H 320 3 M 320.471
(ent-13R)-form
Constit. of Austrobrickellia patens. Oil.
Jakupovic, J. et al, Phytochemistry, 1986, 25, 1927. CHO
C20 H 340 3 M 322.487
3,8-Dihydroxy-15-labdanoic acid Di-00175
(8«,13£)-form [117232-45-8]
Constit. of Juniperus thurifera. Cryst. (CH 2C12 /hexane).
COOH
Mp 134°. [oc]~ + 17.8° (CHCI 3).
San Feliciano, A. et al, Phytochemistry, 1988, 27, 2241.

HO' 2,19-Dihydroxy-7-labden-15-oic acid Di-00179

C20H 360 4 M 340.502 [fcooH

(ent-3P,8«,13S)-form [37409-51-1] Lithofellic acid
Constit. of a Mexican bezoar. Cryst. (EtOH). Mp 204- HOY'YY
2070. [oc]~ +13.1° (c, 1 in CHCI 3).
Albert, D. et al, Bull. Soc. Chim. Be/g., 1973, 82, 785.
~
CH 0H 2
6,8-Dihydroxy-15-labdanoic acid Di-00176
[14787-32-7] C20H 340 4 M 338.486
(ent-2«,13~)-form
14
19-Ac: ent-19-Acetoxy-2«-hydroxy-7-/abden-15-oic acid
COOH
C 22 H 36 0~ M 380.523
Constit. of Relhania corymbosa.
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol)
(ent-6a.,8a.)-form

C20H 360 4 M 340.502

(ent-6«,8«,13£)-form
Constit. of Dodonaea lobulata. Cryst. by subl. Mp 54.6°.
[oc] 0 - W (c, 1 in EtOH).
(ent-6P,8« )-form
13E,l4-Didehydro: ent-6P,8«-Dihydroxy-13E-/abden-15-oic
acid
C20H 340 3 M 322.487

682
3,19-Dihydroxy-7-labden-15-oic acid - 7,18-Dihydroxy-8(17)-labden-15-... Di-00180 - Di-00186

3,19-Dihydroxy-7-labden-15-oic acid Di-00180 6,15-Dihydroxy-8-labden-17-oic acid Di-00183

rrCOOH

HO
~
ri-Y
CH 0H 2 C 20 H 340 4 M 338.486
C2oH340 4 M 338.486 (6P,l3f.)-form
(ent-3«.,13f,)-form Constit. of Halimium verticillatum.
3-Ac: ent-3«.-Acetoxy-19-hydroxy-7-labden-15-oic acid Urones, J.G. et a/, Phytochemistry, 1989, 28, 557.
C 22 H 360 5 M 380.523
Constit. of Relhania corymbosa. 7,8-Dihydroxy-13-labden-15-oic acid Dl-00184
19-Ac: ent-19-Acetoxy-3«.-hydroxy-7-labden-15-oic acid [14787-33-8]
C22H 360s M 380.523 15
Constit. of R. corymbosa. ,:r COOH
13E,l4-Didehydro, 3-Ac: ent-3«.-Acetoxy-19-hydroxy-7,13E-
Iabdadien-15-oic acid
C 22H 340 5 M 378.508
Constit. of R. fruticosa.
13E,l4-Didehydro, 19-Ac: ent-19-Acetoxy-3«.-hy(lroxy-
7,13E-Iabdadien-15-oic acid C 20H 360 4 M 340.502
C 22H 340 5 M 378.508 (ent-7P,8«.,13E)-form
Constit. of R. fruticosa. Constit. of Dodonaea lobulata. Cryst. (Me 2CO/pet.
13E,l4-Didehydro, 19-aldehyde, 3-Ac: ent-3«.-Acetoxy-19- ether). Mp 69-70° dec. [cx]i,<' + 9° (c, 1.4 in CHC1 3).
oxo-7,13E-labdadien-15-oic acid Dawson, R.M. eta/, Aust. J. Chem., 1966, 19, 2133.
C 22H 320 5 M 376.492
Constit. of R. fruticosa.
7,15-Dihydroxy-8-labden-17-oic acid Dl-00185
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol)
CHzOH
6,8-Dihydroxy-13-labden-15-oic acid Dl-00181
~ COOH
(7 ex, 13~)-:form

C 20 H 340 4 M 338.486
(7«.,13C,)-form
C 20H 340 4 M 338.486 7-Me ether: 15-Hydroxy-7«.-methoxy-8-labden-17-oic acid
(ent-6«.,8«.,13£)-form C21H 360 4 M 352.513
Constit. of Cistus laurifolius. Oil. Constit. of Halimium verticil/atum. Oil (as Me ester).
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 1185.
[cx]i;1 + 21.36° (c, 1.1 in CHC1 3) (Me ester).
(7p,J3f,)-form
6,15-Dihydroxy-7-labden-17-oic acid Di-00182 Di-Ac: 7P,J5-Diacetoxy-8-labden-17-oic acid
C 24H 380 6 M 422.561
15
Constit. of H. verticil/atum. Oil (as Me ester). [cx)i;1
CHzOH
+24.0° (c, 1.32 in CHCI 3) (Me ester).
Urones, J.G. eta/, Phytochemistry, 1989, 28, 557.

7,18-Dihydroxy-8(17)-labden-15-oic acid Dl-00186

COOH
C 20H 340 4 M 338.486
(6«.,13S)-form
Havardic acid C
Constit. of Grindelia havardii. Oil (as Me ester). [cx]i;
-2.4° (c, 3.1 in CHCI 3)(Me ester).
6-Ketone, 15-carboxylic acid: 6-0xo-17-labdene-15,17-dioic 18 /
acid. Havardic acid D HOCH2
C 20H 300 5 M 350.454 (7cx, 13R)-form
lsol. from G. havardii. C 20H 340 4 M 338.486
Jolad, S.D. eta/, Phytochemistry, 1987, 26, 483. (7«.,13R)-form [103994-23-6) Cordobic acid
Constit. of Grindelia discoidea. Oil (as Me ester). [cx]i;
- 12.7° (CHC1 3) (Me ester).
683
15,16-Dihydroxy-8(17)-labden-18-••• - 3,19-Dihydroxy-11-oxo-8(17),13-... Di-00187 - Di-00192

18-Ac: 15,19-Dihydroxy-13-labden-7-one Dl-00190

C:zzH360 5 M 380.523

QXCH,OH
From G. discoidea. Oil (as Me ester). [1X]i;5 -13.9°
(CHC1 3) (Me ester).
(7fl,J3R)-form
7-Epicordobic acid
From G. discoidea. Oil (as Me ester). [1X]n + 14.9°
(CHC13) (Me ester). I9CH20H
Timmermann, B.N. et al, Phytochemistry, 1986, 25, 1389. C20H 340 3 M 322.487
(8fJH,13E)-form [66471-78-1] ViUenolone
15,16-Dihydroxy-8(17)-labden-18-oic acid Dl-00187 Constit. of Sideritis chamaedryfolia. Cryst. M p 88-91°.
[1X]~ -4.1° (c, 1.1 in CHC1 3).
19-Ac: [66471-73-6].
C:zzH360 4 M 364.524
Constit. of S. chamaedryfo/ia. Oil. [IX]~ + 5.2° (c, 0.93 in
CHC1 3).
Rodriguez, B., Phytochemistry, 1978, 17, 281.

C 20H 340 4 M 338.486 6,16-Dihydroxy-17-oxo-7,13-labdadien-15- Dl-00191

(ent-13S)-form oic acid
15, 16-Dihydroxy-8(17)-eperuen-18-oic acid
Constit. of Ricinocarpus muricatus. Cryst. (Me2CO). Mp COOH

~
152-153°. [1X]n -38° (c, 3 in EtOH).
Henrick, C.A. et al, Tetrahedron, 1965, 21, 1175.

q:;tHO
I : CH20H
3,7-Dihydroxy-13-labden-15,12-olide Dl-00188 (ent-6CJ., 13E)-form

0
OH
C20H 300 5 M 350.454
(ent-6«.,13E)-form
Constit. of Acritopappus confertus.
HO' (ent-6fl,l3E)-form
Isol. from A. confertus.
CzoH 320 4 M 336.470
Bohlmann, F. et al, Phytochemistry, 1983, 22, 2243.
(3«.,7«.,8fJH,12S)-form
7-Ac: [69204-72-4]. 71X-Acetoxy-31X-hydroxy-13-labden-
3,19-Dihydroxy-11-oxo-8(17),13- Dl-00192
15,12S-olide. EviUosin
C:zzH 340 5 M 378.508 labdadien-15, 16-olide
Constit. of Eupatorium villosum. Cryst. (EtOAcfhexane).
Mp 160-161°. [1X]i;5 + 135.5° (c, 1 in CHC1 3).
Manchand, P.S. et al, J. Org. Chern., 1979, 44, 1322.

6,9-Dihydroxy-13-labden-15,16-olide Dl-00189 HO'

'H
\CH2 0H
C 20 H 280 5 M 348.438
(ent-3/1)-form [42895-57-8]14-Deoxy-11-oxoandrographolide
Constit. of Andrographis panicu/ata. Cryst.
(CHC1 3/Etz0). Mp 98-100°. [1X]n -13° (CHC1 3). The
name 14-deoxy-11-oxoandrographolide is incorrect as
~ 32 0 4 M 336.470 andrographolide has a 12,13-double bond.
(6fl,8«.H,9«. )-form Balmain, A. et al, J. Chern. Soc., Perkin Trans. I, 1973, 1247.
6-Ac: [61263-49-8]. 6P-Acetoxy-91X-hydroxy-13-labden-15, 16-
o/ide. Vitexilactone
C:zzH 340 5 M 378.508
Constit. of the leaves of Vitex cannabifolia. Cryst.
(MeOH). Mp 150-151°. [1X]i;5 -12.6° (c, 1.23 in CHC1 3).
Taguchi, H., Chern. Pharm. Bull., 1976, 24, 1668.

684
3,8-Dihydroxy-17-oxo-13-labden-15-... - 15,16-Epoxy-3,12-dihydroxy-8(17)... Di-00193 - Di-00199

3,8-Dihydroxy-17-oxo-13-labden-15-oic 01-00193 8,12-Epoxy-5,11-dihydroxy-12,14- 01-00196

acid labdadien-1-one
COOH

HO'

C10H 320 5 M 352.470

C10H300 4 M 334.455
(ent-JP,BP,JJZ)-form [74513-95-4]
(5«.,8«.,11S,12Z)-form [37298-92-3] Scapanin A
Constit. of Ayapana amygdalina. Oil (as Me ester). [o:]i;'
Constit. of liverwort Scapania undulata. Needles (Et 20).
+ 18° (c, 0.3 in CHC1 3) (Me ester).
Mp 194-196°. [o:]~4 +25.1° (c, 0.92 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1997.
Huneck, S. et al, J. Chern. Res. (S), 1986, 162.

Dimethyl sciadinonate 01-00194

15,16-Epoxy-3,9-dihydroxy-13(16),14- 01-00197
[6813-10-1] labdadien-7-one

C20H 300 4 M 334.455

3-Ac: [71698-14-1]. 3-Acetoxy-15,16-epoxy-9-hydroxy-
Me 13(1 6),14-labdadien-7-one. Calyone
C22H 280 6 M 388.460 C22H 32 0 5 M 376.492
Growth inhibitor of silkworm larvae from leaves of Constit. of Roylea calycina. Cryst. (MeOHjpet. ether).
Sciadopitys verticillata. Cryst. Mp 122°. [o:Jn -45° Mp 142°. [o:]~ -45.7° (c, 21 in CHC1 3).
(CHC1 3). Prakesh, 0. et al, J. Chern. Soc., Perkin Trans. I, 1979, 1305.
Chang, C.-F. et al, Agric. Bioi. Chern., 1975, 39, 1167.
15,16-Epoxy-8,9-dihydroxy-13(16),14- 01-00198
12,17-Epoxy-2,3-dihydroxy-7,13- 01-00195 labdadien-7-one
labdadien-15,12-olide

C10H 300 4 M 334.455

(8P,9«.)-form
HO' 8-Ac: [76475-16-6]. Galeopsin
(2tt,3tt, 12R)-form C22 H 320 5 M 376.492
Cwlf 280 5 M 348.438 Constit. of Galeopsis angustifo/ia. Cryst.
(EtOAcjhexane). Mp 154-156°. [o:]~ +25.7° (c, 0.42 in
(1«.,3«.,12R)-form CHC1 3).
Diangeloyl: Rodriguez, B. et al, Phytochemistry, 1980, 19, 1805 (isol)
C30H 400 7 M 512.642 Garcia-Alvarez, M.C. et al, An. Quim., 1981, 316 (synth)
Constit. of Brickellia diffusa. Gum. [o:]i;' -43° (c, 0.3 in
CHC1 3).
15,16-Epoxy-3,12-dihydroxy- 01-00199
(1«.,3«.,12S)-form
8(17),13(16),14-labdatrien-2-one
3-Angeloyl: 1-Hydroxy-17,0-dihydrobrickellidi.ffusic acid
spiroketal lactone OH
C25H 340 6 M 430.540
Constit. of B. diffusa. Gum. [o:Jn + 59° (c, 0.4 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 691.

C10H 280 4 M 332.439

(ent-3ft,11~)-form

685
8,12-Epoxy-5,11-dihydroxy-13-labden-... - 15,16-Epoxy-9-hydroxy-13(16),14-... Di-00200 - Di-00206

Constit. of Planaltoa lychnophoroides. Gum. 15,16-Epoxy-6,9-dihydroxy-3-oxo- Di-00203

12-Ketone: ent-15,16-Epoxy-3p-hydroxy-8(11),13(16), 14- 13(16),14-labdadien-19-oic acid
/abdatriene- 2, 12-dione. Jrx.-Hydroxyaustrofolin
C 10H 260 4 M 330.423
Constit. of P. lychnophoroides. Gum. [a:]~4 -24° (c, 0.19 0
in CHC13).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 465.

8,12-Epoxy-5,11-dihydroxy-13-labden-1- Di-00200
one C10H 280 6 M 364.438
(6P,BPH,9rx. )-form
19-+6 Lactone: [19898-90-9]. 15,16-Epoxy-9-hydroxy-3-oxo-
13(1 6),14-labdadien-19 ,6P-olide. Peregrinone. Peregrinin
C10H 260 5 M 346.422
lsol. from Marrubium peregrinum and M. incanum.
Cryst. Mp 172-173°. [a:] 0 +48° (c, 1 in MeOH).
Canonica, L. eta/, Tetrahedron Lett., 1968, 3149.

C 10H 320 4 M 336.470 8,12-Epoxy-6,16-dioxo-13-labden-15-oic Di-00204

(5rx.,8rx.,11S,12R,13E)-form [88036-90-2] Scapanin B acid
Constit. of liverwort Scapania undulata. Plates (Etp).
Mp 208-2UO. [a:Ji: +47.7° (c, 2.5 in CHC1 3). OHC COOH
Huneck, S. et al, J. Chern. Res. (S), 1986, 162.

8,13-Epoxy-6, 7-dihydroxy-14-labden-11- Di-00201

one

~H/~
Yl!.-o OH
(6~,7cx,8cx,13R)-form
C 10H 280 5 M 348.438
(ent-81;,121;,13Z)-form
Constit. of Acritopappus confertus.
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243.
C 10H 32 0 4 M 336.470
(6P,7rx.,8rx.,13R)-form 8,13-Epoxy-2-hydroxy-1 ,14-labdadien-3- Di-00205
7-Ac: [72243-75-5]. 7a:-Acetoxy-8a:,13R-epoxy-6p-hydroxy- one
14-labden-11-one. Coleonol E
C 22H 340 5 M 378.508
Constit. of Coleus forskohlii. Oil.
(6P,7P,Brx.,JJR)-form [64657 -19-8]
Constit. of C. forskohlii. Cryst. Mp 121-122°.
6-Ac: [64657-18-7].
C 22H 340 5 M 378.508
Constit. of C. forskohlii. Cryst. Mp 162-165°. [a:]i,5 C10H 300 3 M 318.455
-89.4° (c, 2.45 in CHC1 3). (8rx.,13R)-form [129134-91-4]
Bhat, S.V. eta/, Tetrahedron Lett., 1977, 1669. Constit. of Lagarostrobus colensoi (Dacrydium colensoi).
Painuly, P. et al, Indian J. Chern., Sect. B, 1979, 18, 214. Cryst. (Et2bjhexane). Mp 102-103°. [a:Ji? +46° (c, 1.3 in
CHC1 3).
8,13-Epoxy-6,9-dihydroxy-14-labden-11- Di-00202 Cambie, R.C. eta/, Aust. J. Chern., 1990, 43, 791 (isol, pmr, cmr)
one
15,16-Epoxy-9-hydroxy-13(16),14- Di-00206
labdadien-7-one

CzoH 320 4 M 336.470

(6p,8rx.,9rx.,13R)-form [70868-07-4] Coleosol
Constit. of Coleus forskohlii. Cryst. (C 6H 6 /hexane). Mp C10H 300 3 M 318.455
192°. [a:] 0 -134° (c, 1 in CHC1 3). (8PH,9rx.)-form [18676-07-8] Hispanolone
Jauhari, P.K. et al, Indian J. Chern., Sect. B, 1978, 16, 1055 (isol)
Singh, S. et al, Indian J. Chern., Sect. B, 1984, 23, 952 (cd)

686
8,13-Epoxy-6-hydroxy-15-labdanal - 15,16-Epoxy-17-hydroxy-7,13(16),14-... Di-00207 - Di-00212

Constit. of Ballota hispanica. Cryst. (EtOAcjpet. ether). 15,16-Epoxy-6-hydroxy-7,13(16),14- Dl-00210

Mp 142-144°. [IX]~ -17.6° (c, 0.33 in CHC13). labdatrien-17-oic acid
Savona, G. et al, Heterocycles, 1978, 9, 257.

8,13-Epoxy-6-bydroxy-15-labdanal Dl-00207

C10H 280 4 M 332.439

6rx.-form [73489-03-9]
6-Ac, Me ester: Cryst. (pet. ether). Mp 85°. [IX]~ + 59.9° (c,
1.3 in CHCl3).
C 20H 340 3 M 322.487
6-(2-M ethylpropanoyl):
(ent-6rx.,8rx.,13R)-form C24H 340 5 M 402.530
Di-Me acetal: Oil. [1X]n -25.4° (c, 1 in CHC13). Constit. of Gutierrezia mandonii. Oil.
Di-Me acetal, 6-Ac: ent-6«-Acetoxy-8rx.,13R-epoxy-15,15- 6-(2-Methylbutanoy/):
dimethoxylllbdane C 25H 360 5 M 416.556
Constit. of Cistus laurifolius. Cryst. (hexane). Mp 67- Constit. of G. mandonii. Oil.
690. [1X]n -47.1° (c, 1 in CHC1 3). 6-(3-M ethylbutanoyl):
Teresa, J. de P. et al, An. Quim., Ser. C, 1981, 77, 184. ~H 360 5 M 416.556
Constit. of G. mandonii. Oil.
8,13-Epoxy-3-bydroxy-15-labdanoic acid Dl-00208 Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1533.

COOH 15,16-Epoxy-7-bydroxy-8(17),13(16),14- Dl-00211

labdatrien-19-oic acid

HO'

C:zoH340 4 M 338.486
(3rx.,8p,13S)-form
3«-Hydroxygomeric acid
Constit. of Sideritis nutans. Oil. C:zoHm04 M 332.439
Fernandez, C. et a/, Phytochemistry, 1986, 25, 2825. 7rx.-form
7-Hydroxylambertianic acid
Constit. of Gutierrezia dracunculoides. Gum. [IX]~ +4.1°
15,16-Epoxy-3-bydroxy-8(17),13(16),14- Dl-00209 (c, 0.41 in CHCl3) (Me ester).
labdatrien-18-oic acid Bohlmann, F. eta/, Phytochemistry, 1981, 20, 105.

15,16-Epoxy-17-hydroxy-7,13(16),14- Dl-00212
labdatrien-19-oic acid
17-Hydroxyisolambertianic acid

C 20H 21;05 M 346.422

(ent-3/1)-form
3-Ac: [79726-68-4]. ent-3fl-Acetoxy-15,16-epoxy- I COOH
8(17),13(16),14-labdatrien-18-oic acid C 20H 280 4 M 332.439
CzzH280 6 M 388.460 Constit. of Gutierrezia dracunculoides. Gum.
Constit. of Dodonaea petiolaris. Cryst. (MeOH). Mp Ac:
233-235°. [1X]n +60° (c, 0.7 in Py). CnH:11,05 M 374.476
Jefferies, P.R. eta/, Aust. J. Chern., 1981, 34, 1001 (cryst struct) Constit. of G. dracunculoides. Gum. [IX]~ + 11.5° (c, 1 in
CHC13).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 105.

687
15,16-Epoxy-20-hydroxy-8(17),13(16) ... - 9,13-Epoxy-17-hydroxy-7-labden-15-... Di-00213 - Di-00218

15,16-Epoxy-20-hydroxy-8(17),13(16),14- Dl-00213 9,13-Epoxy-3-hydroxy-7-labden-15-oic Dl-00216

labdatrien-19-oic acid acid
COOH
0

HOH2
C20 H 28 0 4 M 332.439 C20 H 310 4 M 336.470
20-+19 Lactone: [57459-42-4]. 15,16-Epoxy-8(17),13(16),14- (3ft,9rx.,13~)-form
/abdatrien-20,19-o/ide. Potamogetonin 3ft-Hydroxygrindelic acid
C20H160 3 M 314.424 Constit. of Grindelia spp. Oil (as Me ester). [1X]~4 -23°
Constit. of Potamogeton ferrugineus. Liq. [a]~ -23° (c, (c, 0.13 in CHC1 3) (Me ester).
0.48 in MeOH).
Bohlmann, F. et al, Phytochemistry, 1982, 21, 167.
Smith, C.R. et al, J. Org. Chern., 1976, 41, 593 (isol)
Hasegawa, S. et al, Chern. Lett., 1983, I (struct)
Bastard, J. et al, J. Nat. Prod. (Lloydia), 1984, 47, 592 (struct, cmr) 9,13-Epoxy-6-hydroxy-7-labden-15-oic Dl-00217
acid
15,16-Epoxy-3-hydroxy-8,13(16),14- Dl-00214
labdatrien-7-one
COOH

(6tX,9tX,13.S )-form

HO

C20H 28 0 3 M 316.439 C20 H310 4 M 336.470

3~-form
(6«.,9«.,13S)-form [80931-19-7] 6«.-Hydroxygrindelic acid
Constit. of Grindelia spp. Cryst. (EtOAcjhexane). Mp
Ac: [71641-12-8). 3-Acetoxy-15,16-epoxy-8,13(16),14-
106-108°. [1X] 0 + 19.3° (c, 0.6 in CHC1 3).
labdatrien-7-one. Calyenone
CuH 300 4 M 358.477 Me ester: Oil. [a]i;' -28.2° (c, 0.57 in CHCI 3).
Constit. of Roylea calycina. Cryst. (MeOHjpet. ether). 6-Formyl:
Mp 102°. [a]i; -24.2° (c, 2 in CHC13). CZIH 310 5 M 364.481
Prakash, 0. et al, J. Chern. Soc., Perkin Trans. I, 1979, 1305. Constit. of G. spp. Oil (as Me ester). [a]~4 -27.SO (c, 0.4
in CHC1 3) (Me ester).
6-Ketone: 9,13-Epoxy-6-oxo-7-labden-15-oic acid. 6-
15,16-Epoxy-9-hydroxy-7,13(16),14- Dl-00215
0xogrindelic acid
labdatrien-6-one C20H 300 4 M 334.455
Constit. of G. robusta and G. squarrosa. Cryst. (EtOAc).

~0
Mp 208-210°. [a] 0 -93° (c, 0.11 in dioxan).
(6ft,9rx.,13S)-form [80952-79-0]
Constit. of G. humilis. Cryst. (EtOAcjhexane). Mp 147-
1500. [a] 0 -42.9° (c, 0.6 in CHCI 3).
0 Rose, A.F. et al, Phytochemistry, 1981, 20, 2249 (isol)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 167 (isol)
C20H 280 3 M 316.439
9«.-form [23534-56-7] Solidagenone. Solidago,diterpene A 9,13-Epoxy-17-hydroxy-7-labden-15-oic Di-00218
Constit. of Solidago canadensis and S. gigantea. Cryst.
(EtOH). Mp 131-132°. [1X] 0 -15.2° (c, 1 in CHC1 3).
acid
Prob. artifact.
Anthonsen, T. et a/, Tetrahedron, 1969, 25, 2233. COOH

(9tX, 13S)-form
C20H 310 4 M 336.470
(9rx.,l3S)-form [59219-62-4] 17-Hydroxygrindelic acid.
Oxygrindelic acid
Constit. of Grindelia squarrosa and Haplopappus
tenuisectus. Cryst. (as Me ester). Mp 115-116° (Me
ester). [1X] 0 -106° (c, 2.7 in CHC1 3) (Me ester).

688
9,13-Epoxy-18-hydroxy-7-labden-15-... - 8,13-Epoxy-6-hydroxy-14-labden-11-... Di-00219- Di-00222

Ac: 17-Acetoxygrindelic acid 18-Carboxylic acid: 9,13-Epoxy-7-labdene-15,18-dioic acid

C22H 340 5 M 378.508 C20H 300 5 M 350.454
From G. spp. Constit. of G. spp. Oil (as Me ester). [oc]ii -15.3° (c,
Propanoyl: 0.52 in CHC1 3) (Me ester).
C 23H 360 5 M 392.534 Rose, A.F., Phytochemistry, 1980, 19, 2689.
From G. spp. Oil (as Me ester). (oc]i; -2l.SO (c, 0.2 in Bohlmann, F. et al, Phytochemistry, 1982, 21, 167.
CHCI 3).
2-Methylpropanoyl: 9,13-Epoxy-19-hydroxy-7-labden-15-oic Dl-00220
C14H 380 5 M 406.561 acid
From G. spp.
I
2-Methy/butanoy/:

cif~H
C 25H 400 5 M 420.588
From G. spp.
3-Methylbutanoyl:
C 25H 400 5 M 420.588
From G. spp. Oil (as Me ester). (oc]ii -18.4° (c, 1.35 in
CHCI 3) (Me ester).
(ent-9rx.,13S)-form
C20H 320 4
/
M 336.470
CH,O~
17-Carboxylic acid: [114420-29-0]. ent-9oc,13-Epoxy-1-
labdene-15,11-dioic acid. 17-Carboxygrindelic acid (9rx.,13S)-form
C 20H:14P 5 M 350.454 19-Hydroxygrindelic acid
Constit. of G. camporum. Oil (as Me ester). [oc]~ -70.3° Constit. of Grindelia spp. Oil (as Me ester). [oc]~4
(c, 2.5 in CHCI 3). 13-Config. not certain from the paper. -103.SO (c, 0.5 in CHCI 3) (Me ester).
Braun, T. et al, Acta Chern. Scand., 1962, 16, 1675 (isol, struct) Bohlmann, F. et al, Phytochemistry, 1982, 21, 167.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1749; 1982, 21, 167.
Hoffmann, J.J. et a[, Phytochemistry, 1988, 27, 493 (17-
Carboxygrindelic acid) 8,13-Epoxy-3-hydroxy-14-labden-2-one Dl-00221

9,13-Epoxy-18-hydroxy-7-labden-15-oic Dl-00219
acid

C20H 320 3 M 320.471

(3ft,8rx.,13R)-form
Constit. of Lagarostrobus colensoi (Dacrydium co/ensoi).
Needles (EtOH). Mp 72-74°. [oc]i? +44° (c, 4.4 in
CHCI 3).
C 20H 320 4 M 336.470 Cambie, R.C. eta[, Aust. J. Chern., 1990, 43, 791 (isol, pmr, cmr)
(9rx.,13S)-form
18-Hydroxygrindelic acid 8,13-Epoxy-6-hydroxy-14-labden-11-one Dl-00222
Constit. of Chrysothamnus nauseosus. Oil. [ocln -82.6°
(c, 1.9 in CHCI 3).
18-Ac:
C 22H 340 5 M 378.508
Constit. of Grindelia spp.
~-'
18-(Methy/propanoyl):
C 24 H 380 5 M 406.561
Constit. of G. spp. OH
18-(2-M ethylbutanoyl): C20H 320 3 M 320.471
C25 H 400 5 M 420.588 (6P.Srx.,13R)-form [121817-29-6]
Constit. of G. spp. Oil (as Me ester). [oc]ii -15° (c, 0.4 Isol. from Coleus forskoh/ii. Cryst.
in CHCI 3) (Me ester). (EtOAcjcyclohexane). Mp 120-121°. [oc]i? -133° (c, 0.1
18-(3-Methylbutanoyl): in CHCI 3).
C 25H 44P 5 M 420.588 Gabetta, B. et al, Phytochemistry, 1989, 28, 859.
Constit. of G. spp.
18-Succinoy/:
C14H 360 7 M 436.544
Constit. of C. nauseosus. Oil. [1X]n -55° (c, 0. 7 in
CHCI 3).
18-Aldehyde: 9,13-Epoxy-18-oxo-7-labden-15-oic acid. 18-
0xogrindelic acid
C 20H 300 4 M 334.455
Constit. of G. spp. Oil (as Me ester). [oc]ii -30.9° (c,
0.34 in CHCI 3) (Me ester).

689
8,13-Epoxy-9-hydroxy-14-labden-11-... - 8,12-Epoxy-16-hydroxy-14-oxo-12-... Di-00223 - Di-00228

8,13-Epoxy-9-hydroxy-14-labden-11-one Dl-00223 19-+6 Lactone: [62340-62-9]. 15,16-Epoxy-7-oxo-

8,13(16),14-labdatrien-19,6P-olide. Ballonigrin
C20H 240 4 M 328.407
Constit. of Ballota nigra. Cryst. Mp 212°. [cx]~ +2° (c,
0.25 in CHC1 3).
3-0xo, 19-+6 lactone: [62340-63-0]. 15,16-Epoxy-3,7-dioxo-
8,13(16),14-labdatrien-19,6-olide. Ballonigrinone
C20 H 220 5 M 342.391
From B. rupestris. Mp 217°. [cx]~ -11° (c, 0.46 in
C20H 320 3 M 320.471
CHCI 3).
(8«.,9«.,13R)-form [72963-78-1] Coleol
18-Hydroxy, 19-+6 lactone: [69075-71-4]. 15,16-Epoxy-18-
Constit. of Coleus forskohlii. Viscous oil. [cxln + 7° (c,
hydroxy-7-oxo-8,13(16),14-labdatrien-19,6-olide. 18-
1. 7 in CHC1 3).
Hydroxyballonigrin
Katti, S.B. et al, Indian J. Chern., Sect. B, 1979, 17, 321.

owj
From B. acetobulosa. Cryst. Mp 171°. [cxln -2.4° (c, 0.2
in CHCI 3).
8,13-Epoxy-19-hydroxy-14-labden-2-one Dl-00224 Savona, G. et al, J. Chern. Soc., Perkin Trans. I, 1977, 322; 1978,
1271.

15,16-Epoxy-20-hydroxy-12-oxo- 01-00227
8(17),13(16),14-labdatrien-19-oic acid

HOH 2C \
C20H 320 3 M 320.471
(8«.,13R)-form
19-Hydroxy-2-oxomanoyl oxide
Constit. of Dacrydium colensoi. Cryst. (pet. ether). Mp
113-114°.
Grant, P.K. et al, Tetrahedron, 1965, 21, 3599. H
C20H 260 5 M 346.422
9,13-Epoxy-18-hydroxy-14-labden-7-one Dl-00225 19-+20 Lactone: [6704-58-1]. 15,16-Epoxy-12-oxo-
8(17),13(16),14-labdatrien-19,20-olide. Sciadinone
C20 H 240 4 M 328.407
Constit. of the leaves of Sciadopitys verticillata. Cryst.
Mp 207°. [cxJn -59.9° (CHCI 3).
Kaneko, C. eta/, Chern. Pharm. Bull., 1963, 11, 271.

8,12-Epoxy-16-hydroxy-14-oxo-12-labden- Di-00228
15-al
C20 H 320 3 M 320.471 0
OHC
(ent-9«.,13R)-form
Constit. of Austrobrickellia patens. Oil.
18-Aldehyde: ent-9ot,13R-Epoxy-7-oxo-14-labden-18-al
C20H 300 3 M 318.455
From A. patens. Oil.
18-Carboxylic acid: ent-9«.,13R-Epoxy-7-oxo-16-labden-18-
oic acid
C20H 300 4 M 334.455
From A. patens. C20H 300 4 M 334.455
Jakupovic, J. et al, Phytochemistry, 1986, 25, 1927. (8«.,12E)-form
Ac: [74513-43-2]. 16-Acetoxy-8,12-epoxy-14-oxo-12-labden-
Dl-00226 15-al
15,16-Epoxy-6-hydroxy-7-oxo-
C22H 320 5 M 376.492
8,13(16),14-labdatrien-19-oic acid Constit. of Silphium perfoliatum. Oil.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1987.
0

M 346.422

690
9,13-Epoxy-18-hydroxy-6-oxo-7-... - 8,13-Epoxy-2,3-labdanediol Di-00229 - Di-00234

#OH
9,13-Epoxy-18-hydroxy-6-oxo-7-Iabden- Dl-00229 14,15-Epoxy-8(17),12-Iabdadien-16-oic Di-00232
15-oic acid acid

COOH

I
HOH2 C C20H 300 3 M 318.455
C20H34.0s M 350.454 (12E,l4~)-form
(9rz,13S)-form Me ester: Methyll4~,15-epoxy-8(17),12E-labdadien-16-oate
Ac: 18-Acetoxy-6-oxogrindelic acid Cz1H3203 M 332.482
CnH320 6 M 392.491 Constit. of Aframomum daniellii. Oil. [1X]i,' + 10° (c, 0.6
Isol. from Grindelia spp. in CHCI3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 167. Kimbu, S.F. et al, J. Nat. Prod. (Lloydia), 1987, 50, 230.

9,13-Epoxy-7,14-labdadiene-2,3,20-triol Dl-00230 8,13-Epoxy-15-labdanal Dl-00233

_./CHO

8 (8~, 13R}:form

I
H

C20HJz04 M 336.470 C20H 340 2 M 306.487

(2rz,3rz,9rz,l3R)-form (8P,J3R)-form [97549-56-9]
2-Angeloyl, 3,20-di-Ac: 31X,20-Diacetoxy-21X-angeloyloxy-
Isol. from Baccharis scoparia. Oil. [1X]i;' -15° (c, 0.74 in
91X,l3R-epoxy-7, 14-labdadiene
CHCI 3).
C:19H42 0 7 M 502.647 (ent-8P,13R)-form [58917-28-5] Gomeraldehyde
Constit. of Waitzia acuminata. Constit. of Sideritis gomerae.
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1943. 15-Carboxylic acid: [58917-30-9]. ent-8P,l3R-Epoxy-15-
labdanoic acid. Gomeric acid
C20H 340 3 M 322.487
15,16-Epoxy-13(16),14-Iabdadiene-6,9,19- Dl-00231 Constit. of S. gomerae. Cryst. (pet. ether). Mp 113-115°.
trioI [1X]n -34° (c, 0.1 in CHCI 3).
15-Alcohol: ent-8P, 13 R- Epoxy-15-labdanol. Gomerol
C20H 360 2 M 308.503
0 Constit. of S. nutans. Oil.
(ent-8P,13S)-form
13-Epigomeraldehyde
From S. gomerae.
HOH 2 C OH 15-Carboxylic acid: ent-8P,I3S-Epoxy-15-labdanoic acid.
CmH3z04 M 336.470 13-Epigomeric acid
(6P,9rz)-form [560-58-7] Marrubenol C20H 340 3 M 322.487
Constit. of Marrubium vulgare, Cryst. (EtOH aq.). Mp From S. gomerae. Cryst. (MeOH). Mp 127-129°. [1X]n
138°. [IX]~ + 19.9° (c, 1 in MeOH). -20° (c, 0.6 in CHCI 3).
19-Carboxylic acid, 19-+6 lactone: [465-92-9]. 15,16-Epoxy- 15-Alcohol: ent-8p, 13S-Epoxy-15-labdanol. 13-Epigomerol
91X-hydroxy-13(16), 14-labdadien-19,6P-olide. Marrubiin. C20H360 2 M 308.503
Marrubium bitter From S. nutans. Oil.
C20H:zs04 M 332.439 Gonzales, A.G. et a/, Phytochemistry, 1975, 14, 2655 (isol)
Isol. from M. vulgare and Leonotis leonurus. Cryst. Bohlmann, F. eta/, Phytochemistry, 1985, 24, 511 (isol)
(EtOH). Mp 160°. [1X]n + 33.3° (c, 1 in CHCI3). Fernandez, C. eta/, Phytochemistry, 1986, 25, 2825 (isol)
Reed, R.I. et al, J. Chern. Soc., 1963, 5933 (ms)
Abbondanza, A. eta/, Tetrahedron Lett., 1965, 4337 (biosynth) 8,13-Epoxy-14-labdene-2,3-diol Dl-00234
Wheeler, D.M.S. eta/, Tetrahedron, 1967, 23, 3909 (synth)
Fulke, J.W.B. eta/, J. Chern. Soc. C, 1968, 807 (isol)
Stephens, L.J. eta/, Tetrahedron, 1970, 26, 1561 (struct)
Mangoni, L. eta/, Tetrahedron, 1972, 28, 611 (synth)
Almqvist, S. et a/, Acta Chern. Scand., Ser. B, 1975, 29, 695 (cmr)

C20H 340 3 M 322.487

(2P,3P,8rz,13R)-form [24583-55-9] 2,3-Dihydroxymanoyl oxide

691
8,13-Epoxy-14,15-labdanediol - 15,16-Epoxy-7,12,13(16),14-... Di-00235 - Di-00241

Constit. of Dacrydium kirkii. Cryst. (EtOH aq.). Mp Constit. of Sideritis mugronensis. Amorph. solid by sub!.
145-150°. Mp 285° dec. [<X]~ -2.3° (c, 1.5 in CHC1 3).
Cambie, R.C. et a/, Aust. J. Chern., 1969, 22, 1691. Rodriguez, B. et a/, Tetrahedron, 1973, 29, 2837 (isol)
Valverde, S. eta/, Phytochemistry, 1977, 16, 1841 (struct)
8,13-Epoxy-14,15-labdanediol Dl-00235
8,13-Epoxy-14,15,18-labdanetriol Di-00239
HO H
H OH
\

'

C20H 360 3 M 324.503 HOH 2 C

(ent-8rx.,13S,14S)-form [57129-38-1] Barbato/ C20H 360 4 M 340.502
Constit. of Sideritis arborescens. Cryst. (hexane). Mp (ent-8rx.,13R,14S)-form [17904-37-9] ap,13R-Epoxy-14R,15,18-
100-105°. [<X]~ -13.6° (c, 0.25 in EtOH). eperuanetrio/
v. Castenn-Lichterfelde, C. eta/, Experientia, 1975, 31, 757. Constit. of Goodenia ramelii. Cryst. (C 6H 6). Mp 164-
1650. [<Xln -21° (c, 1.9 in EtOH).
8,13-Epoxy-14,15,16,19-labdanetetrol Di-00236 Coates, P. eta/, Tetrahedron, 1968, 24, 795.

'o~g:
8,13-Epoxy-14,15,19-labdanetriol Dl-00240

CHPH
CH20H

H
HOH2C
I
C20H 360 5 M 356.501 HOH2C
(ent-8rx.,14f,)-form C20 H 360 4 M 340.502
19-Ac: [126794-66-9]. ent-19-Acetoxy-8<X,13-epoxy- (ent-8rx.,13S,14S)-form
I4.;,15, 16-labdanetriol. ent-19-Acetoxy-14,15,16- ent-14,15,19-Trihydroxymanoy/ oxide
trihydroxymanoyl oxide Constit. of Florestina tripteris. Gum.
C22H 380 6 M 398.539
Dominguez, X.A. eta/, Phytochemistry, 1988, 27, 613.
Constit. of Palafoxia arida. Gum.
Zdero, C. eta/, Phytochemistry, 1990, 29, 573 (isol, cmr, pmr)
15,16-Epoxy-7,12,13(16),14-labdatetraen- Dl-00241
9,13-Epoxy-3,15,16,18-labdanetetrol Dl-00237 6-one

'
CH 2 0H
' CH 2 0H
0

C20 H 260 2 M 298.424

(12Z)-form [56324-54-0] Hedychenone
c2oH36o5
Constit. of Hedychium spicatum. Cryst. (hexane). Mp
(3p,apH,9rx.,13S)-form [23554-81-6] Lagochilin
135-136°. [<X]n + 142° (CHC1 3).
Constit. of Lagochilus inebrians. Cryst. Mp 157-158°.
7-Hydroxy: [60149-05-5]. 15,16-Epoxy-7-hydroxy-
Abramov, M.M. eta/, Dokl. Akad. Nauk SSSR, 1958, 3, 41 (isol)
7,12,13(16),14-labdatetraen-6-one. 7-Hydroxyhedychenone
Gafner, G. et a/, J. Chern. Soc., Chern. Commun., 1974, 249
(struct) From H. spicatum. Cryst. (hexane). Mp 108-109°. [<X]n
+ 125°.
Sharma, S.C. eta/, Phytochemistry, 1975, 14, 1059; 1976, 15, 827.
8,13-Epoxy-7,14,15-labdanetriol Dl-00238

C2oH3604 M 340.502
(7p,8rx.,13R,14R)-form [52591-03-4] Borjatriol

692
12,15-Epoxy-8(17),12,14-labdatriene - 15,16-Epoxy-8(17),13(16),14-.•• Di-00242 - Di-00248

12,15-Epoxy-8(17),12,14-labdatriene Di-00242 15,16-Epoxy-8(17), 13(16),14-labdatriene- Dl-00246

3,18-diol

,(D
HO'~O
' CH2 0H
C20H 300 M 286.456 C20H 300 3 M 318.455
ent-form [67779-53-7] Pumiloxide
(ent-3/1)-form
Constit. of Pinus pumila. Cryst. Mp 88-89°.
3-Angeloyl:
7P-Hydroxy: ent-12, 15-Epoxy-8(17), 12, 14-labdatrien- 7a.-of.
C25H 360 4 M 400.557
7p.Hydroxypumiloxide
Constit. of Gutierrezia solbrigii. Gum.
C20H 300 2 M 302.456
Constit. of Stevia myriadenia. Gum. [a.J14 -40° (c, 0.3 in Jakupovic, J. eta/, Tetrahedron, 1985, 41, 4537.
CHC1 3).
Raldagin, V.A. et a/, Khim. Prir. Soedin., 1978, 14, 345 (isol) 15,16-Epoxy-8(17),13(16),14-labdatriene'- Dl-00247
Mohanraj, S. eta/, J. Org. Chern., 1981, 46, 1363 (synth) 6,19-diol
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2021 (isol)
Cambie, R.C. eta/, Aust. J. Chern., 1990, 43, 1151 (synth)

15,16-Epoxy-7,13(16),14-labdatriene Dl-00243
~0
HOH2 C H OH
C20 H 300 3 M 318.455
(ent-6rr.)-form [16981-22-9] Psiadol
Constit. of Psiadia altissima. Cryst. (Et 20jpet. ether).
C20H300 M 286.456 Mp 138-140°. [a.]i; -58° (c, 1 in dioxan).
ent-form [117249-10-2] Canonica, L. eta/, Gazz. Chim. Ita/., 1969, 99, 260.
Constit. of Acrisione denticulata. Oil.
Aal, M.A. eta/, Phytochemistry, 1988, 27, 2599. 15,16-Epoxy-8(17),13(16),14-labdatriene- Dl-00248
7,18-diol
15,16-Epoxy-7,13(16),14-labdatriene-2,3- Dl-00244
diol

HOH2
C20 H 300 3 M 318.455
C20H 300 3 M 318.455 (ent-7rr.)-form
(ent-2rr.,3f/)-form 18-Hydroxyaustrochaparol
Constit. of Baccharis salicifolia. Oil. [a.J14 -ll o (c, 0. 74 7-Ac: [74635-79-3].
in CHC1 3). C22H3204 M 360.492
Zdero, C. eta/, Phytochemistry, 1986, 25, 2841. Constit. of Austroeupatorium chaparense. Oil.
Di-Ac: [74635-78-2].
15,16-Epoxy-8(17),13(16), 14-labdatriene- Dl-00245 C24 H 340 5 M 402.530
3,6-diol Constit. of A. chaparense. Oil. [a.J14 -11.1° (c, 0.18 in

W
CHCI 3).

.CX) 18-Aldehyde, 7-Ac: [74635-77-1]. 18-0xoaustrochaparo/

acetate
C22 H 300 4 M 358.477
Constit. of A. chaparense. Oil. [a.]i;' +0.9° (c, 4 in
HO' CHCI 3).
OH Bohlmann, F. eta/, Phytochemistry, 1980, 19, 111.
C20H 300 3 M 318.455
(ent-3P,6rr.)-form [23727-29-9]/sopsiathJ/
Constit. of Psiadia altissima. Cryst. (diisopropyl
ether/heptane). Mp 64-65°. [a.Ji? -41° (CHCI 3).
Canonica, L. eta/, Gazz. Chim. Ita/., 1969, 99, 276.

693
15,16-Epoxy-8(17),13(16),14-... - 15,16-Epoxy-8,13(16),14-labdatrien-... Di-00249 - Di-00254

15,16-Epoxy-8(17),13(16),14-labdatriene- Dl-00249 15,16-Epoxy-8(17), 13(16),14-labdatrien- Dl-00252

2,12-dione 19-oic acid

(+)-form

HOOC\
19

C20H 180 3 M 316.439

C20H:11,03 M" 314.424 (+)-form [4966-13-6] Lambertianic acid
Constit. of Pinus lambertiana. Cryst. (hexane). Mp
ent-form [62868-70-6] Austrofolin
126.5-127.SO. [ex]~ + 55° (c, 3 in 95% EtOH).
Constit. of Austroeupatorium inulaefolium. Cryst.
(Et20jpet. ether). Mp 79-80°. [ex]~4 + 12° (c, 1.27 in 12-0xo: 15,16-Epoxy-12-oxo-8(17),13(16),14-labdatrien-19-
CHC1 3). oic acid. 12-0xolambertianic acid
C20H 260 4 M 330.423
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 1034.
Constit. of Brickellia glomerata. Gum.
(-)-form [1235-77-4]
15,16-Epoxy-7,13(16),14-labdatrien-18-oic Dl-00250 ent-form. DanieUic acid. lllurinic acid
acid Constit. of Daniellia oliveri. Cryst. (MeOH). Mp 129-
130.50. [exln -58° (c, 1 in MeOH).
19-Alcohol: [23727-36-8]. ent-15,16-Epoxy-8(17),13(16),14-
labdatrien-19-ol. Daniello/
C20 H 300 2 M 302.456
Constit. of Xanthocephalum linearifolium. Oil. [ex]i; -14°
(c, 1 in CHC1 3).
Haeuser, J. eta/, Tetrahedron, 1961, 12, 205 (isol, struct)
Enzell, C. et a/, Ark. Kemi, 1965, 23, 367 (ms)
M 316.439 Narayanan, C.R. et a/, Tetrahedron Lett., 1965, 3639 (pmr)
Dauben, W.O. eta/, Tetrahedron, 1966, 22, 679 (isol)
ent-form Mills, J.S., Phytochemistry, 1973, 12, 2479 (isol)
Constit. of leaves of Stevia Iucida. Oil. [ex]n -7.03° (c, Bell, R.A. et a/, Can. J. Chern., 1976, 54, 141 (synth)
0.2132 in CHC1 3). Bohlmann, F. eta/, Phytochemistry, 1979, 18, 204(} (Daniello[)
Salmon, M. et a/, Phytochemistry, 1983, 22, 1512. Calderon, J.S. eta/, Phytochemistry, 1987, 26, 2639 (deriv)

15,16-Epoxy-8(17),13(16),14-labdatrien- Di-00251 15,16-Epoxy-7,13(16),14-labdatrien-17-ol Di-00253

18-oic acid

M 302.456
C20H 180 3 ent-form
17-Hydroxyisopolyahhin
ent-form [10267-14-8] Polyalthic acid
Constit. of Polyalthia fragrans and Sequoia sempervirens. Constit. of Acritopappus morii. Oil.
Also from Ricinocarpus stylosus. Sea snail repellent. Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695.
Cryst. (pet. etherjC 6H 6). Mp 102°. [ex]~ -46° (c, 5 in
EtOH). 15,16-Epoxy-8,13(16),14-labdatrien-3-ol Dl-00254
Gopinath, K.W. eta/, Helv. Chim. Acta, 1961, 44, 1040 (isol)
Henrick, C.A. eta/, Aust. J. Chern., 1964, 17, 915 (isol)
Enzell, C. eta/, Ark. Kemi, 1965, 23, 367 (ms)
Narayanan, C.R. eta/, Tetrahedron Lett., 1965, 3639 (pmr)
Pelletier, S.W. et a/, J. Chern. Soc., Chern. Commun., 1967, 96
(synth)
Ohta, K. eta/, Agric. Bioi. Chern., 1978, 42, 1957 (isol)

C20H 300 2 M 302.456

3P-form [86450-74-0] Baiyanol
Needles. Mp 85.5-86°. [ex]i;l +64.0° (c, 1.47 in CHC1 3).
3-0-[p-v-Glucopyranosyl-( 1 ~ 2)-P-v-xylopyranoside]:
[86450-75-1]. Baiyunoside
C3 tH480 11 M 596.714
Constit. of Phlomis betonicoides (Bai-Yun-Shen)
previously thought to be Salvia digitaloides. Powder.
[ex]i,6 + 13.8° (c, 2.50 in MeOH).

694
15,16-Epoxy-8(17),13(16),14-... - 8,12-Epoxy-13-labdene-15,16-diol Di-00255 - Di-00258

3-0-[rx.-L- Rhamnopyranosyl-( 1-+ 2)-P-D-glucopyranoside]: Serebryakov, E.P. eta/, Tetrahedron, 1970, 26, 5215 (synth)
[100414-77-5]. Phlomisoside I Hanson, J.R. eta/, Phytochemistry, 1972, 11, 703 (biosynth)
C32H 54P 11 M 610.740 Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073 (iso[)
A1mqvist, S., Acta Chern. Scand., Ser. B, 1975, 29, 695 (cmr)
Constit. of P. betonicoides. Powder. [rx.]j,6 -77° (c, 2.3 in
Tabacchi, R. eta/, Helv. Chim. Acta, 1975, 58, 1184 (iso[)
MeOH).
3-0-Sophoroside: [100414-78-6]. Phlomisoside II
C32 H 500 12 M 626.740 8,12-Epoxy-12-labdene-15,16-dial Di-00257
Constit. of P. betonicoides. Powder. [rx.]~ + 15.4° (c, 2.3 OHC
in MeOH).
CHO
Tanaka, T. eta/, Chern. Pharm. Bull., 1983, 31, 780; 1985, 33,
4275.
Nishizawa, M. eta/, J. Org. Chern., 1987, 52, 4878.
Mori, K. et a/, Tetrahedron, 1987, 43, 3409 (synth)
Yamada, H. eta/, Tetrahedron Lett., 1987, 28, 4315 (synth)

15,16-Epoxy-8(17),13(16),14-labdatrien-7- Di-00255
ol C20H 300 3 M 318.455
(8rr.,12Z)-form
Constit. of Silphium perfoliatum. Oil. [rx.]~ + 37.7° (c, 0.3
in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1987.

8,12-Epoxy-13-labdene-15,16-diol Di-00258
C20H 300 2 M 302.456
(ent-7rr.)-form [74636-02-5] Austrocluzparol. 7-
Hydroxypolya/thin
Constit. of Acritopappus morii. Oil. [rx.]~ + 8.SO (c, 6.1 in
CHC13).
Ac: [74635-76-0].
C22 H 320 3 M 344.493
Isol. from Austroeupatorium chaparense. Oil. [rx.]~ + 10°
(c, 0.2 in CHCI 3).
C20H 340 3 M 322.487
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 111, 2695.
(8rr.,12R,13E)-form [74513-49-8]16-Hydroxycarterochaetol
Constit. of Silphium perfo/iatum. Cryst. (Etpjpet.
8,13-Epoxy-14-labdene Dl-00256 ether). Mp 175°. [rx.]~ -48.4° (c, 2.3 in CHCI 3).
16-Ac: [74513-37-4].
C22 H 360 4 M 364.524
Constit. of S. perfoliatum. Oil. [rx.]~ -16.3° (c, 1.2 in
CHC13).
(8cx, 13R)-form 15,16-Di-Ac: [74513-36-3].
C24H 380 5 M 406.561
Constit. of S. perfoliatum. Oil. [rx.]~4 -19.8° (c, 3.7 in
C20H 340 M 290.488 CHC1 3).
(8rr.,13R)-form [596-84-9] Manoyl oxide 16-Aldehyde: [74513-50-1]. 8rr.,12R-Epoxy-15-hydroxy-13E-
Constit. of Dacrydium colensoi, Cupressus sempervirens Iabden-16-al
and Juniperus oxycedrus. Cryst. (MeOH aq.). Mp 29°. C20H 320 3 M 320.471
Bp0 _3 135-137°. [rx.]); + 19.6° (EtOH). Constit. of S. perfoliatum. Oil.
(8P,13R)-form 15,16-Dia/dehyde: 8rr.,12R-Epoxy-13E-Iabdene-15,16-dial
8-Epimanoyl oxide. 8-epi-Manoyl oxide C20H 300 3 M 318.455
Constit. of Chamaecyparis nootkatensis. Cryst. Mp 44- Constit. of S. perfoliatum. Oil.
450. [rx.Jil -9.5° (c, 2.1 in CHCI 3).
13S,J4S-Epoxide: [74513-42-1]. 8rr.,12R:13S,US-Diepoxy-
(8p,J3S)-form [28235-38-3] 8,13-Diepimanoyl oxide. 8,13- 15,16-labdanediol
diepi-Manoyl oxide C20 H340 4 M 338.486
Constit. of C. nootkatensis. Cryst. Mp 79-84°. [rx.Jil Constit. of S. perfoliatum. Oil.
+23.4° (c, 0.6 in CHCI 3).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1987.
(8rr.,JJS)-form [1227-93-6] 13-Epimanoyl oxide. 13-epi-Manoy/
oxide
Constit. of Jack pine bark. Cryst. (MeOH). Mp 94-96°.
[rx.]~ + 37.SO (c, 10 in CHCI 3).
(ent-8rr.,13S)-form [27642-41-7] Oleary/ oxide
Metab. of Gibberella fujikuroi and constit. of 0/earia
paniculata and Solidago missouriensis. Cryst. (MeOH).
Mp 98-99.SO. [rx.]~4 -37° (c, 0.25 in EtOH).
Bower, G.L. eta/, Phytochemistry, 1967, 6, 151 (iso[)
Cheng, Y.S. eta/, Phytochemistry, 1970, 9, 2517 (iso[)

695
8,13-Epoxy-9(11)-labdene-14,15-diol - 8,13-Epoxy-14-labdene-3,6,7-triol Di-00259 - Di-00265

8,13-Epoxy-9(11)-labdene-14,15-diol Dl-00259 3-Ac: [88143-06-0]. 3-Acetylvarodiol

C22H 360 4 M 364.524
OH From S. varoi. Syrup. [1X]n -24° (c, 1 in CHC1 3).
I
12-Ac: [88143-07-1]. 12-Acetylvarodiol
CHzOH C22H 360 4 M 364.524
From S. varoi. Syrup. [1Xln -57.3° (c, 1 in CHC13).
Di-Ac: [88143-08-2]. Diacetylvarodiol
C24H 380 5 M 406.561
From S. varoi. Cryst. Mp 156-158°. [1X]n -17.3° (c, 1 in
CHC1 3).
C20H 340 3 M 322.487
Algarra, J. eta/, Phytochemistry, 1983, 22, 1779.
(8r~.,13R,14R)-form [127942-98-7] Blepharizol B
Constit. of Blepharizonia plumosa.
8,13-Epoxy-14-labdene-16,18-diol Dl-00263
Jolad, S.D. et a/, Phytochemistry, 1990, 29, 905 (iso/, pmr, cmr, ms)

69v
fH20H
8,13-Epoxy-14-labdene-1,18-diol Di-00260

(ent-8cx, 13R)-form

C20H3403
CH20H
(ent-8rx.,13R)-form [96890-05-0] Jabugodiol
CmH340 3 M 322.487 Constit. of Sideritis arborescens. Gum. [1X]i:' -25.3° (c, 1
(1P,8«,13R)-form [62871-02-7] Jhanidiol in CHC1 3).
Constit. of Eupatorium jhanii. Cryst. Mp 189°. [1X]n (ent-8rx.,13S)-form [96947-63-6] Epijabugodiol
+90° (c, 0.8 in CflC1 3). From S. arborescens. Cryst. Mp 194-196°. [1X]i:' -44.05°
18-Ac: (c, 1 in EtOH).
C22H 360 4 M 364.524 Garcia-Grandos, A. eta/, Phytochemistry, 1985, 24, 517.
Constit. of E. jhanii. Liq.
Di-Ac: 8,20-Epoxy-14-labdene-2,3,7 ,13-tetrol Dl-00264
C24H 380 5 M 406.561
Constit. of E. jhanii. Liq.
Gonzalez, A.G. eta/, Phytochemistry, 1977, 16, 107.
HO,~
~
8,13-Epoxy-14-labdene-3,7-diol Dl-00261
/"~
HO/~'OH
C20H 340 5 M 354.486
(2rx.,3rx.,7rx.,8p,l3R)-form
2-Angeloyl: 2rx.-Angeloyloxy-8p,20-epoxy-14-lllbdene-
3rx.,7rx.,13R-triol
C20H 340 3 M 322.487 C25H 400 6 M 436.587
Constit. of Waitzia acuminata.
(3p,7r~.,8r~.,13R)-form
2-Ange/oy/, 3-Ac: 3rx.-Acetoxy-2rx.-angeloyloxy-8p,20-epoxy-
7-Ac: [116359-96-7]. Hamachilobene E 14-lllbdene-7rx.,l3R-diol
C22 H 360 4 M 364.524 C17H 420 7 M 478.625
lsol. from Frullania hamachiloba. Cryst. Mp 90-92°. Constit. of W. acuminata.
[1X]n + 0° (c, 0.76 in CHC1 3).
Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943.
Toyota, M. eta/, Phytochemistry, 1988, 27, 1789.

8,13-Epoxy-14-labdene-3,6,7-triol Dl-00265
8,13-Epoxy-14-labdene-3,12-diol Dl-00262
/~

(3Mcx, 7cx,8cx, 13R)-form

C20H 340 4 M 338.486

(3p,6rx.,7rx.,8rx.,13R)-Jorm
C20H 340 3 M 322.487
3,6-Di-Ac: Hamachilobene A
(ent-3P,12«)-Jorm [88142-96-5] Jlarodiol
C24H 380 6 M 422.561
Isol. from Sideritis varoi. Cryst. Mp 136-138°. [1X]n
+42.3° (c, 1 in EtOH).

696
8,13-Epoxy-14-labdene-6,16,18-triol - 8,12-Epoxy-13-labden-1-ol Di-00266 - Di-00268

Constit. of Frullania hamachiloba. Cryst. Mp 136-138°. Bruun, T. eta/, Acta Chern. Scand., 1962, 16, 1675 (pmr, ms,
[ocln + 38.6° (c, 0.36 in CHC1 3). struct)
Mangoni, L. eta/, Gazz. Chim. !tal., 1962, 92, 983, 995
7-Ketone, 3,6-di-.Ac: [116359-99-0]. Hamachilobene B (Epoxydihydrogrindelic acid)
C24H 360 6 M 420.545 O'Connell, A.M., Acta Crystallogr., Sect. B, 1973, 29, 2232 (cryst
Constit. of F. hamachiloba. Cryst. Mp 154-156°. [oc]n struct)
+37.8° (c, 0.26 in CHC1 3). Adinolfi, M. et a/, Gazz. Chim. !tal., 1976, 106, 625 (synth)
(3p,6r~.,7p,8r~.,l3R)-form Hoffmann, J.J. eta/, J. Org. Chern., 1982, 47, 1725 (isol, deriv)
Kimura, A. et a/, Chern. Lett., 1983, 15 (synth)
3,6-Di-Ac: [116359-98-9]. Hamachilobene C Sierra, M.G. et a/, J. Org. Chern., 1984, 49, 4984 (synth)
C24H 380 6 M 422.561 Timmermann, B.N. eta/, Phytochemistry, 1985, 24, 1031 (derivs)
Constit. of F. hamachiloba. Cryst. Mp 94-95°. [oc]n Adinolfi, M. et a/, Phytochemistry, 1988, 27, 1878 (cd, abs config)
+ 19.1° (c, 1.46 in CHC1 3).
3,7-Di-Ac: [116359-97-8]. Hamachilobene D 8,12-Epoxy-13-labden-1-ol Dl-00268
C24H 380 6 M 422.561
Constit. of F. hamachiloba. Cryst. Mp 144-146°. [ocln
+46.4° (c, 0.58 in CHC1 3).
Toyota, M. eta/, Phytochemistry, 1988, 27, 1789.

8,13-Epoxy-14-labdene-6,16,18-triol Di-00266

C20 H 340 2 M 306.487

(lp,ar~.,12S,13E)-form [104189-10-8]
Constit. of liverwort Scapania undulata. Cryst.
(Et20jpet. ether). Mp 132-133°. [<Xln -48.6° (c, 0.85 in
CHCI 3).
6ft-Hydroxy: [104189-02-8]. 8r~.,12S-Epoxy-13E-Iabdene­
CzoH3404 lp,6p-diol
C20H 340 3 M 322.487
[96947-64-7] Epijabugotriol
(ent-6r~.,8r~.,13R)-form
Constit. of S. undulata. Cryst. (CHCI 3 jpet. ether). Mp
!sol. from Sideritis arborescens. Cryst. Mp 227-228°. [oc]i?
- 51.34o (c, 0.5 in EtOH). 174-176°. [oc]n -57.6° (c, 0.99 in CHCI 3).
Jloc-Hydroxy: [104189-12-0]. 8r~.,12R-Epoxy-13E-Iabdene-
Garcia-Granados, A. eta/, Phytochemistry, 1985, 24, 517.
1p,llr~.-diol
C20 H 340 3 M 322.487
9,13-Epoxy-7-labden-15-oic acid Dl-00267 Constit. of S. undulata. Cryst. (Etpjpet. ether). Mp
186-187°. [ocJn -19.7° (c, 1.95 in CHCI 3).
COOH
lloc-Hydroxy, 1-ketone: [104189-11-9]. 8r~.,l2R-Epoxy-llr~.­
_) hydroxy-13E-Iabden-1-one
C20 H 3p 3 M 320.471
17
Constit. of S. undulata. Needles (Etpjpet. ether). Mp
95-96°. [oc]n +9.8° (c, 1.37 in CHCI 3).
6ft-Hydroxy, 1-deoxy: [104189-01-7]. 8r~.,12S-Epoxy-13E­
Iabden-6P-ol
C20 H 340 2 M 306.487
C20 H32 0 3 M 320.471 Constit. of S. undulata. Cryst. (CHCI 3 jpet. ether). Mp
(9a.,13R)-form [98103-38-9] 13-Isogrindelic acid 170-172°. [oc]n -51.1° (c, 2.16 in CHCI 3).
Constit. of Grindelia spp. 6ft,11oc-Dihydroxy: 8r~.,l2R-Epoxy-13E-Iabdene-lp,6p,llr~.­
Me ester: Cryst. Mp 41-42°. [oc]i; -17.98° (c, 2.05 in triol
CHCI 3). C20 H 340 4 M 338.486
Constit. of S. undulata. Cryst. (MeOH). Mp 178-180°.
(9r~.,13S)-form [1438-57-9] Grindelic acid
[ocJn -29.8° (c, 0.02 in MeOH).
Constit. of G. robusta and G. squarrosa. Cryst. (AcOH).
Mp 100-101°. [oc]n -102.2° (c, 0.7 in CHCI 3). 6ft,Jloc-Dihydroxy, 1-ketone: [104189-09-5]. 8r~.,12R-Epoxy-
6p,llr~.-dihydroxy-13E-Iabden-1-one
17-Grindeloxy ester: [98046-81-2]. 17-Grindeloxygrindelic C20H 320 4 M 336.470
acid
Constit. of S. undulata. Cryst. (MeOH). Mp 260-261°.
C40 H 6P 6 M 638.926 [<X]n + 29.3° (c, 0.28 in MeOH). ·
From G. spp.
Huneck, S. eta/, J. Chern. Res. (S), 1986, 162.
17-Grindeloxy ester, Me ester: Resin. Mp 44-46°. [oc]i;
-123.15° (c, 1.5 in CHCI 3).
7oc,8oc-Epoxide: 7oc,8oc:9,13-Diepoxy-15-labdanoic acid. 7,8-
Epoxydihydrogrindelic acid. 7,8-Epoxygrindelic acid
C20 H 32 0 4 M 336.470
!sol. from resin of G. robusta. Platelets (C6H 6 jpet.
ether). Mp 102.5-104°.
7oc,8oc-Epoxide, Me ester: Cryst. (pet. ether). Mp 59-60°.
[oc]n -82.1° (c, 1.36 in CHCI 3).

697
8,12-Epoxy-13-labden-15-ol - 8,13-Epoxy-14-labden-12-ol Di-00269 - Di-00273

8,12-Epoxy-13-labden-15-ol Di-00269 14,15-Dihydro: 8a,13R-Epoxy-3a-/abdanol. 14,15-Dihydro-

C 20H 340 2 M 306.487
(8«,12S,13E)-form [72074-11-4] Carterochaeto/
Constit. of Carterothamnus anomalochaeta and Greek
tobacco. Oil. [a]i;' -14.2° (c, 1.5 in CHC1 3).
15-Carboxylic acid: [72023-08-6]. 8a, 12S- Epoxy-13Z-labden-
15-oic acid. Carterochaetic acid
C 20 H 320 3 M 320.471
Constit. of C. anomalochaeta. Cryst. (pet. ether) (as Me
ester). Mp 143° (Me ester). [a]~4 -44.SO (c, 0.62 in
CHC1 3) (Me ester).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 621.
Wahlberg, I. eta/, Acta Chern. Scand., Ser. B, 1983, 37, 209; 1988,
42, 708 (isol, pmr, cmr, synth)
3«-hydroxymanoyl oxide
Constit. of Juniperus pseudosabina. Cryst. Mp 86-87°.
(ent-3«,8«,13R)-form [74311-13-0] ent-3«-Hydroxy-13-
epimanoy/ oxide
Constit. of Subtribus espeletiinae. Cryst. (EtzO/pet.
ether). Mp 135-136°. [a]i;' -33.3° (c, 1.2 in CHC1 3).
(ent-3ft,8«,13S)-form [42895-91-0] Ribeno/
Isol. from Sideritis canariensis. Cryst. Mp 84-86°. [aln
-31° (c, 0.21 in CHC1 3).
3-Ketone: [29461-31-2]. ent-8«,13S-Epoxy-14-labden-3-one
C 20 H 3z0 2 M 304.472
Isol. from roots of Solidago missouriensis. Cryst.
(MeOH). Mp 94-95°. [a]~ -53° (c, 2.47 in CHC1 3).
Laidlaw, R.A. eta/, J. Chern. Soc., 1963, 644 (3-0xomanoyl oxide)
Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073.
Gonzalez, A.G. eta/, Phytochemistry, 1973, 12, 1113 (Ribenol)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 267.
Pandita, K. eta/, Indian J. Chern., Sect. B, 1987, 26, 453 (14,15-
Dihydro-3<~.-hydroxymanoyl oxide)
8,13-Epoxy-14-labden-6-ol Dl-00272

8,13-Epoxy-14-labden-2-ol 101-00270

(2cx,8cx, 13R)-form
C 20H 340 2 M 306.487
(6«,8«,13S)-form [65894-40-8]
C 20 H 340 2 M 306.487 Constit. of Pinus spp.
(2«,8«,13R)-form [29065-31-4] 2-Hydroxymanoy/ oxide Conner, A.H. eta/, Phytochemistry, 1977, 16, 1777.
Constit. of Dacrydium colensoi. Cryst. (pet. ether). Mp
54.5-56.SO.
8,13-Epoxy-14-labden-12-ol Dl-00273
2-Ketone: 8,13-Epoxy-14-labden-2-one. 2-0xomanoy/ oxide
C2oH3202 M 304.472 OH
I
Isol. from D. colensoi. Cryst. (MeOH). Mp 77-78°.
ent-(2«,8«,13S)-form
ent-2«-Hydroxy-13-epimanoy/ oxide (8cx, 12cx, 13R):form
Constit. of Sideritis perfoliata. Cryst. (hexane). Mp
134.5-135°. [a]J:? -40.4° (c, 0.47 in CHC1 3).
Grant, P.K. eta/, Chern. Ind. (London), 1960, 1300 (2-0xomanoyl
oxide)
Grant, P.K. eta/, J. Chern. Soc., 1965, 3846 (struct)
C20H 340 2 M 306.487
Almquist, S.O. eta/, Acta Chern. Scand., Ser. B, 1975, 29, 695 (8«,12«,13R)-form
(cmr) 12-Ketone: [37551-74-9]. 8«,13R-Epoxy-14-/abden-12-one
Sezik, E. eta/, Phytochemistry, 1985, 24, 2739 (isol) C 20H 320 2 M 304.472
Constit. of sun-cured Greek tobacco. Cryst. (pentane).
8,13-Epoxy-14-labden-3-ol Di-00271 Mp 93-93.SO. [a]~ +90° (c, 0.39 in CHC1 3).
(8«,12«,13S)-form
12«-Hydroxy-13-epimanoy/ oxide
Isol. from Turkish tobacco (Nicotiana tabacum). Mp
141-142°. [a]i,S +44° (CHC1 3).
12-Ketone: [37551-73-8]. 8a,13S-Epoxy-14-labden-12-one.
(3cx,8cx,13R)1"orm Co/eonone
C20H 320 2 M 304.472
Isol. from Coleus forskohlii and sun-cured Greek
C 20H 340 2 M 306.487
tobacco. Cryst. (pentane). Mp 86-88° (82-82.SO). [a]~
(3«,8«,13R)-form -142° (c, 0.26 in CHC1 3).
3-Ketone: 8a, 13R-Epoxy-14-labden-3-one. 3-0xomanoyl (ent-8«,12«,13R)-form [88198-30-5]
oxide ent-8a,13R-Epoxy-14-labden-12a-ol. Varo/
C20H 320 2 M 304.472 Constit. of Sideritis varoi. Cryst. Mp 138-140°. [aln
Isol. from Xylia dolabriformis. Cryst. (MeOH aq.). Mp -37.SO (c, 1 in CHC1 3).
99-99.5°. [aln + 54° (c, 5 in CHC1 3).
Giles, J .A. et a/, Tetrahedron, 1962, 18, 169 (isol)
Aasen, A.J. eta/, Acta Chern. Scand., 1972, 26, 832 (isol, struct)

698
8,13-Epoxy-14-labden-16-ol - 15,16-Epoxy-20-oxo-8(17),13(16),14-... Di-00274- Di-00279

Wahlberg, I. et al, Acta Chern. Scand., Ser. B, 1977, 31, 453 19-Hydroxymanoyl oxide
(synth) Constit. of Polemonium viscosum. Cryst. Mp 47-48°. [1X]n
Kalti, S.B. eta/, Indian J. Chern., Sect. B, 1979, 17, 321 (iso/) + 13.1° (c, 0.013 in CHCI 3).
Algarra, J. et al, Phytochemistry, 1983, 22, 1779 (isol)
Ac: 19-Acetoxymanoyl oxide
C11H 360 3 M 348.525
8,13-Epoxy-14-labden-16-ol Dl-00274 Constit. of P. viscosum. Oil. [1X]n + 31.SO (c, 0.003 in
16-Hydroxymanoyl oxide CHCI 3).
19-Carboxylic acid: [56687-75-3]. 8rr.,13R-Epoxy-14-labden-

gg~;'H 19-oic acid

lsol. from Pinus sylvestris. Cryst. (as Me ester). Mp 83-
850 (Me ester). [1X]n -43.2° (c, 1.2 in EtOH) (Me ester).
(8rr.,J3S)-form
19-Hydroxy-13-epimanoyl oxide
Constit. of Baccharis to/a. Cryst. (hexane). Mp 109°.
C20H 340 1 M 306.487 San Martin, A. et a/, Phytochemistry, 1980, 19, 1985.
Bardyshev, 1.1. eta/, Khim. Prir. Soedin., 1982, 18, 480.
(ent-8rr.,J3S)-form Stierle, D.B. et al, Phytochemistry, 1988, 27, 517.
ent-16-Hydroxy-13-epimanoyl oxide
Isol. from Sideritis java/ambrensis.
14~,15-Epoxide, 16-Ac: ent-16-Acetoxy-81X,13R:14,15-
8,12-Epoxy-13-labden-15,12-olide Dl-00277
diepoxylabdane. Schkuhrianol acetate 0
C11H 360 4 M 364.524
Constit. of Schkuhria multiflora. Oil.
[63543-07-7]
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 881. (8cx,12R)-:form
Alcarez, M.V. eta/, Phytochemistry, 1989, 28, 1267.

8,13-Epoxy-14-labden-18-ol Dl-00275

~'~ C20H 300 3 M 318.455

(8rr.,l2R)-form [1235-78-5] P-Levantenolide
Constit. of Turkish tobacco. Cryst. (hexane). Mp 208-
~ (8cx,l3R)-:form 2090. [1X)iii -59.6° (CHCI 3).
(8rr.,l2S)-form [30987-48-5] rr.-Levantenolide
CH2 0H
Constit. of Turkish tobacco. Cryst. (hexane). Mp 210°.
C20H 340 1 M 306.487 [IX]~ +60.4° (CHCI 3).
(8rr.,J3R)-form [62929-59-3] Jhanol Enzell, C. et al, Ark. Kemi, 1965, 23, 367 (ms)
Constit. of Eupatoriumjhanii. Cryst. Mp 139-141°. [1X]n Gonzalez, A.G. et al, Tetrahedron Lett., 1976, 1897; 1976, 2725
+ 27° (c, 0.65 in CHC1 3). (struct, synth)
Ac:
C11H 360 3 M 348.525 8,13-Epoxy-14-labden-11-one Dl-00278
Constit. of E. jhanii. Liq.
(ent-8rr.,13S)-form
8fl,13R-Epoxy-14-eperuen-18-ol
lsol. from Beyeria spp. Cryst. (pet. ether). Mp 185-
185.50. [1X]n -47° (c, 4.9 in CHC1 3).
Carboxylic acid: ent-8rr.,l3S-Epoxy-14-labden-18-oic acid.
8fl,13R-Epoxy-14-eperuen-18-oic acid
C20H 310 3 M 320.471 C20H 320 2 M 304.472
Constit. of B. spp. Cryst. (C 6H 6). Mp 236-236.SO. [1X)n
(8rr.,l3R)-form [61242-47-5]
-44° (c, 2.5 in CHCI 3).
Constit. of Coleus forskohlii. Cryst. (2-propanol). Mp
Jefferies, P.R. et a/, Aust. J. Chern., 1965, 18, 1441. 96-97°. [IX]~ -103.2° (c, 0.2 in CHCI).
Gonzalez, A.G. et al, Phytochemistry, 1977, 16, 107.
Gabetta, B. eta/, Phytochemistry, 1989, 28, 859.

8,13-Epoxy-14-labden-19-ol Dl-00276
15,16-Epoxy-20-oxo-8(17),13(16),14- Di-00279
_j labdatrien-19-oic acid

0
(Sex, 13R)-:form

CHPH
ClOH340z M 306.487
(8rx.,13R)-form M 330.423

699
15,16-Epoxy-6,8,9,17,20-... - 15,16-Epoxy-6,7,9-trihydroxy-13(16)•.. Di-00280 - Di-00283

Me ester: [85448-00-6]. Constit. of C. forskohlii. Cryst. Mp 208-210°. [1X] 0

C 21 H 28 0 4 M 344.450 +2.92° (c, I in CHCl 3).
Constit. of seeds of Scadiopitys verticillata. Oil. [IX]~ 7-Ac: [66575-29-9]. Coleonol. Forskolin. Colforsin, USAN
+ 36.2° (c, 0.58 in CHCl 3). C 22 H 340 7 M 410.506
Hasegawa, S. eta/, Chern. Lett., 1983, 1. Constit. of C. forskohlii. Antihypertensive agent used to
treat glaucoma. Cryst. Mp 230-232°. [1X]i,S -26.2° (c,
15,16-Epoxy-6,8,9, 17,20-pentahydroxy- Di-00280 1.68 in CHCl 3).
13(16),14-labdadien-19-oic acid (11X,6p,71X,91X,13S)-form
6-Ac: [67921-06-6]. Coleonol C
From C. forskohlii. Cryst. (Me2CO /hexane). Mp 205-
0 2060. [1X] 0 -6.7° (c, l in CHCl 3).
[64657-11-0, 112420-42-5, 114298-68-9]
Tandon, J.S. eta/, Indian J. Chern., Sect. B, 1977, 15, 880; 1978,
16, 341.
Bhat, S.V. eta/, Tetrahedron Lett., 1977, 1669 (isol)
Lindner, E. eta/, Arzneim.-Forsch., 1978, 28, 284; 1983, 33, 1436
(pharmacal)
C 20H:14P 8 M 398.452 Martindale, The Extra Pharmacopoeia, 28th/29th Ed.,
(6P,BP,91X)-form Pharmaceutical Press, London, 1982/1989, 16542.
19~20 Lactone, 6-Ac: [29722-58-5]. Nepetaefuranol
De Souza, N.J. eta/, Med. Res. Rev., 1983, 3, 201 (rev, pharmacal)
Viswanathan, N. eta/, Indian J. Chern., Sect. B, 1985, 24, 583
C 22 H 31,08 M 422.474
(Coleonol)
Constit. of Leonotis nepetaefolia. Cryst. (CH2Cl2). Mp Saksena, A.K. eta/, J. Chern. Soc., Chern. Commun., 1985, 1748
253-255°. [1X]i,S + 17.2°. (synth, bib[)
White, J.D. eta/, J. Org. Chern., 1973, 38, 720. Saksena, A.K. eta/, Tetrahedron Lett., 1985, 26, 551 (struct,
co/eono/ B, bib[)
Ramakurnar, S. et a/, Z. Kristal/ogr., Kristal/ogeom., Kristallphys.,
15,16-Epoxy-3,6,9,19-tetrahydroxy- Dl-00281 Kristallchem., 1985, 173, 81 (cryst struct)
13(16),14-labdadien-7-one Lichey, J. eta/, Drugs of the Future, 1986, 11, 59 (pharmacal)
Prakash, 0. eta/, J. Chern. Soc., Perkin Trans. 2, 1986, 1779 (pmr,
cmr, config, Colforsin)
Ziegler, F. eta/, J. Am. Chern. Soc., 1987, 109, 8115 (synth,
Colforsin)
Hrib, N.J. eta/, Tetrahedron Lett., 1987, 28, 19 (synth, Colforsin)
Hashimoto, S. eta/, J. Am. Chern. Soc., 1988, 110, 3670 (synth)
Nicolaou, K.C. eta/, J. Chern. Soc., Chern. Commun., 1989, 512
(synth, Co/forsin)
Kanematsu, K. eta/, J. Chern. Soc., Chern. Commun., 1989, 1028
C20H3006 (synth, Co/forsin)
(Jp,6p,8~,91X)-form Akhila, A. eta/, Phytochemistry, 1990, 29, 821 (bib/, biosynth)
3,19-Di-Ac: [86575-87-3]. Leosibirin
C 24H 340 8 M 450.528 15,16-Epoxy-6,7,9-trihydroxy-13(16),14- Di-00283
Constit. of Leonurus sibiricus. Oil. [IX]~ -0.7° (c, 0.3 in labdadien-19-oic acid
CHCl 3).
6-Ketone, 7f,-alcohol, 3,19-di-Ac: [86575-86-2]. 15,16-
Epoxy-3,7,9,19-tetrahydroxy-13(16),14-labdadien-6-one.
lsoleosibirin
C 24H 340 8 M 450.528
Constit. of L. sibiricus. Oil. [IX]~ + 7.1° (c, 0.63 in
CHCI 3).
Savona, G. eta/, Phytochemistry, 1982, 21, 2699.
C 20 H 300 6 M 366.453
8,13-Epoxy-1,6,7,9-tetrahydroxy-14- Di-00282 (6p,71X,BPH,91X)-form
labden-11-one 19~6 Lactone, 7-Ac: [63028-21-7]. 71X-Acetoxy-l5,l6-
[66428-84-0] epoxy- 7,9-dihydroxy-13(16), 14-labdadien-19 ,6P-olide. 7-
Acetoxymarrubin
C 22 H 300 6 M 390.475
Constit. of Ballota nigra. Cryst. Mp 170°.
7-Ketone, 19~6 lactone: [61289-05-2]. 15,16-Epoxy-9-
hydroxy-7-oxo-13(16),1 4-labdadien-19,6P-olide.
Ballotinone
C 20H 260 5 M 346.422
Constit. of B. nigra. Cryst. (EtOAcjpet. ether). Mp
C 20H 320 6 M 368.469 194°. [1X]~ + 57° (c, 0.3 in CHCl 3).
{11X,6P,7P,81X,91X,l3R)-form [64657-20-l] Savona, G. eta/, J. Chern. Soc., Perkin Trans. 1, 1976, 1607; 1977,
Constit. of Coleus forskohlii. Cryst. Mp 177-180°. 322.
6-Ac: [64657-21-2]. Coleonol B
C 22 H 340 7 M 410.506

700
15,16-Epoxy-6,8,9-trihydroxy-13(16) ... - Espinosanolide Di-00284 - Di-00289

15,16-Epoxy-6,8,9-trihydroxy-13(16), 14- Dl-00284 15,16-Epoxy-7,8,9-trihydroxy-13(16),14- Dl-00287

labdadien-19-oic acid labdadien-6-one

\
0

C10H 300 5 M 350.454

C 10H 300 6 M 366.453 (6P,8f.,9rx.)-form
(6p,Bp,9rx. )-form 7-Ac: [95261-28-2). Galeuterone
C22H320, M 392.491
19-+6 Lactone: [26549-00-8]. Leonotin. BP- Constit. of Ga/eopsis reuteri. Cryst. (EtOAcjhexane).
Hydroxymarrubiin
Mp 187-189°. [1X]!:,9 +88.1° (c, 0.36 in CHC1 3).
C10H 180 5 M 348.438
Constit. of Leonotis nepetaefolia and L. dysophyl/a. Savona, G. et al, Phytochemistry, 1984, 23, 2958.
Cryst. Mp 175°. [1X] 0 +62.7° (c, 0.9 in EtOH).
Kaplan, E.R. et al, J. Chern. Soc. C, 1970, 1656. 8,13-Epoxy-6,7 ,9-trihydroxy-14-labden-11- Dl-00288
one
15,16-Epoxy-6,9,20-trihydroxy-13(16),14- Dl-00285
labdadien-19-oic acid 0 0 __//

H (6~,7cx,8cx,9cx,13R)-form
H
OH
C10H 320 5 M 352.470
(6p,7rx.,8rx.,9rx.,13R)-form
C10H 300 6 M 366.453 6-Ac: [72165-14-l]. Coleonol F
C21H 340 6 M 394.507
(6p,BpH,9rx. )-form
Constit. of Coleus forskohlii.
19-+20 Lactone: [51116-54-2]. 15,16-Epoxy-6P,91X-
7-Ac: [72963-77-0]. Coleonol D
dihydroxy-l3(l6), 14-/abdadien-19 ,20-o/ide
C21 H 340 6 M 394.507
C 10H 180 5 M 348.438
Constit. of C.forskohlii. Cryst. (Me2COfhexane). Mp
Cryst. (EtOH aq.). Mp 187-188°. [1X) 0 + 13° (c, 1.2 in 154°.
CHC1 3).
6,7-Di-Ac: Cryst. Mp 135°.
19-+20 Lactone, 6-Ac: [51419-49-9]. Dubiin
C21H 300 6 M 390.475 (6P,7P,8rx.,9rx.,l3R)-form
Constit. of leaves of Leonotis dubia. Cryst. (EtOAc). Mp Constit. of C. forskohlii. Cryst. (2-propanol). Mp 148-
187-188°. [1X] 0 -17° (c, l.l in CHC1 3). 1490. [1X]i? -25.9° (c, 0.1 in CHC13).
Eagle, G.A. et al, J. Chern. Soc., Perkin Trans. 1, 1973, 1701. 7-Ac:
C21H 340 6 M 394.507
Constit. of C.forskohlii. Cryst. (hexane). Mp 135-136°.
15,16-Epoxy-6,9,19-trihydroxy-13(16),14- Dl-00286 [1X)i? -23.1 o (c, 0.1 in CHC1 3).
labdadien-7-one Katti, S.B. et a/, Indian J. Chern., Sect. B, 1979, 17, 321.
Pa%u1y, P. et al, Indian J. Chern., Sect. B, 1979, 18, 214 (Coleonol

Gabetta, B. et al, Phytochemistry, 1989, 28, 859 (isol)

Espinosanolide Dl-00289
61X-Hydroxy-7,13-labdadien-16,15-olid-17-carboxylic acid

C10H 300 5 M 350.454

(6p,8pH,9rx.)-form [63543-36-2] Ballotenol
Constit. of Ballota nigra. Cryst. (EtOAc). Mp 140-145°
dec.
Savona, G. eta/, J. Chern. Soc., Perkin Trans. 1, 1976, 1607; 1977,
497 (isol, struct)

C10H 180 5 M 348.438

2-Methy/butanoy/: [126771-06-0].
C25 H 360 6 M 432.556
Constit. of Gutierrezia espinosae.
Angeloy/: [126794-68-1).

701
Ghiselinin - 7-Hydroxy-8(17),13-labdadien-16,15-... Di-00290 - Di-00296

C25H 340 6 M 430.540 Constit. of Aristolochia cymbifera. Oil (as Me ester). [rx]i,S
Constit. of G. espinosae. -11 o (c, 0.35 in CHCI 3)(Me ester).
Zdero, C. eta/, Phytochemistry, 1990, 29, 567 (iso/, pmr) Lopes, L.M.X. eta/, Phytochemistry, 1986, 27, 2265.

Ghiselinin Di-00290 8-Hydroxy-13(16),14-labdadien-19-oic Di-00293

9rx,11S; 15 ,16-Diepoxy-7,13(16),14-labdatriene acid
[79827-31-9]

I~
OH

H
HOOC
C 20 H 3P 3 M 320.471
(ent-8rx. )-form
Constit. of Sideritis varoi. Gum. [rx.]~ -25.03° (c, I in
C2oH2102 M 300.440 EtOH).
Constit. of the nudibranch Hypselodoris spp. Oil. [rx.Jn Garcia-Granados, A. eta/, Phytochemistry, 1985, 24, 1789.
+ 7.5° (c, 0.27 in MeOH).
Hoch1owski, J.E. eta/, J. Org. Chern., 1982, 47, 88. 13-Hydroxy-7,14-labdadien-19-oic acid Di-00294

Gutespinolide Di-00291

C20H3203 M 320.471
(13S)-form (39702-13-1]
Constit. of Agathis robusta. Noncryst. [rx.Jn +21° (c, 0.2
in EtOH) (as Me ester).
Carman, R.M. eta/, Aust. J. Chern., 1973, 26, 209.
C 20H 260 4 M 330.423
2-Methylpropanoyl: [126771-04-8].
C 24H 320 5 M 400.514 15-Hydroxy-7 ,13-Iabdadien-17-oic acid Di-00295
Constit. of Gutierre;;ia espinosae. Oil.
7" CH2 0H
2-Methylbutanoyl:
C 25 H 340 5 M 414.541
Constit. of G. espinosae. Oil. [rx]~4 +85° (c, 2.66 in
CHC1 3).
Angeloyl: (126771-05-9].
C25H 320 5 M 412.525
Constit. of G. espinosae. Oil. C 20 H 320 3 M 320.471
12-Epimer, 2-methylbutanoyl: (13£)-form
C 25 H 340 5 M 414.541 Constit. of Halimium viscosum. Oil. [rx.]~ -46.6° (c, 0.82
Constit of G. espinosae. Oil. in CHCI 3).
[126770-80-7, 126873-97-0] Ac: 15-Acetoxy-7,13E-Iabdadien-17-oic aCid
C22H340 4 M 362.508
Zdero, C. eta/, Phytochemistry, 1990, 29, 567 (iso/, pmr)
From H. viscosum. Oil. [rx.]~ -53.4° (c, 1.48 in CHCI 3).
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 711.
6-Hydroxy-8(17),13-labdadien-15-oic acid Dl-00292
7-Hydroxy-8(17),13-labdadien-16,15-olide Dl-00296

C20H 320 3 M 320.471

(ent-6P,13 E)-form C20H 300 3 M 318.455
(ent-7rx.)-form
Constit. of Acritopappus morii.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695.

702
12-Hydroxy-7,13-labdadien-15,16-... - 8-Hydroxy-15-labdanoic acid Di-00297 - Di-00302

12-Hydroxy-7,13-Iabdadien-15,16-olide Dl-00297 19-Hydroxy-8(17),13-Iabdadien-16,15- Dl-00300

WAoo
olide
OH

C10H 300 3 M 318.455

(ent-12~)-form [88862-26-4]
Constit. of Acritopappus confertus. Gum. 'H
CH20H
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243. 19

C10H 300 3 M 318.455

16-Hydroxy-8(17),13-Iabdadien-15,16- Di-00298 ent-form [82209-74-3] Andrograpanin
olide Constit. of Andrographis paniculata. Needles
(Me 2COjhexane). Mp 104-106°. [oc]i;1 -35.0° (c, 1.02 in
OH CHC1 3).
P-D-Glucopyranoside: [27215-14-1]. Neoandrographolide
C26H4008 M 480.597
Isol. from A. paniculata. Cryst. Mp 167-168°. [ocln -48°
(Py).
Chan, W.R. et al, Tetrahedron, 1971, 27, 5081
(Neoandrographolide)
Fujita, T. eta/, Chern. Pharm. Bull., 1984, 32, 2117
CwH 300 3 M 318.455 (Andrograpanin)
16~-form
Ac: [113235-86-2]. Lagerstronolide 16-Hydroxy-8(17),13-labdadien-15,16-olid- Dl-00301
C22H3204 M 360.492
Constit. of Lagerstroemia lancasteri. Cryst.
19-oic acid
(CHCI 3/MeOH). Mp 162°. [ocln -7.1° (c, 0.2 in CHC1 3). 0
Chaudhuri, P.K., Phytochemistry, 1987, 26, 3361.

19-Hydroxy-8(17),13-labdadien-15,16- Di-00299
olide
Medigenin COOH
[11052-63-4]
C10H 280 5 M 348.438
16~-form
0 Constit. of Calocedrus formosana. Cryst. Mp 175-176°.
Fang, J.-M. et al, Phytochemistry, 1989, 28, 1173.

8-Hydroxy-15-Iabdanoic acid Dl-00302

CH20H
C2oH3003 M 318.455
Constit. of Melodinus monogynus. Cryst.
(Me2COjpentane). Mp 165-167°. [oc]~ -45° (c, 1 in
~COOH
yu·'OH
MeOH). (Sex, 13S)-form
P-Ce/lobioside: [11052-68-9]. Medinin
C32H~,0 13 M 642.739 C10H 360 3 M 324.503
Constit. of M. monogynus. Cryst. (CHC1 3/Me 2CO aq.).
Mp 120-122°. [ocJn -26° (c, 1 in MeOH). (8rx.,13S)-form [10267-24-0] Labdllnolic acid
Constit. of Cistus labdaniferus. Gum. [aln -7° (c, 1 in
ent-form CHC1 3).
19-Carboxy/ic acid: ent-8(17),13-Labdadien-15,16-olid-19- Me ester: Cryst. Mp 73-74°. [a]n -8° (c, 2 in CHC1 3).
oic acid
C10H 280 4 M 332.439 (ent-8rx.,13S)-form
Isol. from Conyza schimperi. Gum. ent-Labdllnolic acid
Constit. of Dodonaea lobulata. Cryst. (as Me ester). Mp
Sethi, A. et a/, Phytochemistry, 1988, 27, 2255.
72-74° (Me ester). [aln + 10° (CHC1 3) (Me ester).
Zdero, C. et al, Phytochemistry, 1990, 29, 3167.
ent-(8rx.,13R)-form
ent-Brx.-Hydroxy-13R-Iabdan-15-oic acid. ent-13-epi-
Labdano/ic acid
Constit. of Trachylobium verrucosum. Cryst. (as Me
ester). Mp 74c 75° (Me ester). [aln -3° (c, 11 in CHC1 3)
(Me ester).

703
2-Hydroxy-8(17),12,14-labdatrien-18-... - 6-Hydroxy-7-labdene-15,19-... Di-00303 - Di-00308

ent-(8P,I3S)-form 6-Hydroxy-8(17),12,14-labdatrien-19-oic Dl-00305

ent-8P-Hydroxy-13S-labdlln-15-oic acid acid

w
From T. verrucosum. Cryst. (pet. ether) (as Me ester).
Mp 83° (Me ester). [exln -5° (c, 1.9 in CHCI3) (Me
ester).
Henrick, C.A. et al, Tetrahedron Lett., 1964, 3475 (isol)
Hugel, G. et al, Tetrahedron, Suppl., No. 8, 1966, 203 (isol)
Bjamer, K. eta/, Acta Crystal/ogr., Sect. B, 1968, 24, 855 (bib/,
cryst struct)
Imamura, P.M. eta/, Phytochemistry, 1977, 16, 1842 (cmr) HOOC \ OH
(6a.,12Z)-form
2-Hydroxy-8(17),12,14-labdatrien-18-oic Dl-00303 6-Ac: 6-Acetoxy-8(17),12,14-labdatrien-19-oic acid
acid CnH 310 4 M 360.492

HO,qgc
Constit. of Phyllocladus trichomanoides. Noncryst. solid.
[85527-56-6]
Mp 112-115°.
6-Ac, Me ester: [65003-65-8].
Cryst. Mp 57-61°.
Cambie, R.C. et a/, Aust. J. Chern., 1981, 34, 1073.

7-Hydroxy-8(17),12,14-labdatrien-18-oic Dl-00306
HOOC \H
acid
CzoH31P 3 M 318.455
(ent-2P,I2Z)-form
2rz-Hydroxy-12Z-ozic acid
Constit. of Ichthyothere terminalis.
Me ester: [85527-27-1].
Gum. [ex]~ -20° (c, 0.1 in CHC1 3).
2-Ketone: [85668-48-0]. ent-2-oxo-8(17),12Z,l4-labdatrien-
18-oic acid. 2-0xo-12Z-ozic acid C20 H 31P 3 M 318.455
C20H 280 3 M 316.439 (7rz,l2E)-form
Constit. of/. terminalis. 7-Ac: 7rz-Acetoxycommunic acid
2-Ketone, Me ester: [85527-28-2]. C12H 310 4 M 360.492
Gum. [ex]~ - W (c, 0.2 in CHC1 3). Constit. of Chromolaena col/ina. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 2317. Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1141.

6-Hydroxy-8(17),12,14-labdatrien-18-oic Di-00304 16-Hydroxy-6,8(17),13-labdatrien-15-oic Di-00307

acid acid
COOH

w
~
WCH,OH ~
COOH
C20H 300 3 M 318.455 C20H 300 3 M 318.455
(ent-6rz,12E)-form (ent-13E)-form
Zanzibaric acid Constit. of Acritopappus confertus.
Ac: ent-6ex- Acetoxy-8( 17), 12E, 14-labdatrien-18-oic acid. Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243.
Zanzibaric acid
C12H 310 4 M 360.492
Isol. from resin of Trachylobium verrucosum. Cryst. 6-Hydroxy-7-labdene-15,19-dioic acid Dl-00308
(Et 20jpet.ether) (as Me ester). Mp 143-144° (Me ester).

w
[ex]n -37° (c, 1 in CHC1 3) (Me ester). ~COOH
Hugel, G. eta/, Bull. Soc. Chim. Fr., 1965, 2903.

HOOC OH
C20 H 310 5 M 352.470
(ent-6P,131;)-form
19-+6 Lactone: Hartwrightia acid
C20H 300 4 M 334.455

704
7-Hydroxy-8(17)-labden-15-oic acid - 16-Hydroxy-6-oxo-7,13-labdadien-15-..• Di-00309 ...:. Di-00314

Constit. of Hartwrightia .floridana. Gum (as Me ester). 15-Hydroxy-7-oxo-8,13-labdadiene- Dl-00312

[IX]~ +0.9° (c, 0.53 in CHC1 3) (Me ester). 16,15:19,6-diolide
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 843.

7-Hydroxy-8(17)-labden-15-oic acid Dl-00309

0

~~H
YJ'OH

C20H 340 3 M 322.487

(7rx.,13S)-form [80995-92-2] Cistenolic acid. Sa/vic acid
Constit. of Cistus symphytifolius andEupatorium salvia.
Cryst. (MeOHjMe2CO). Mp 139-14i 0 • [1X)n -2l.SO (c, C:zoH240 6 M 360.406
0.232 in CHC13). 15f.-:form [65408-90-4] Rupestralic acid
Ac: Constit. of Ballota rupestris. Cryst. (EtOAc). Mp 186°.
CnH360 4 M 364.524 In equilib. with open-chain form.
Constit. of E. salvia. Savona, G. eta/, Heterocycles, 1977, 7, 161.
Ac, Me ester:
C23H 380 4 M 378.551 12-Hydroxy-16-oxo-7,13-labdadien-15-oic Dl-00313
Constit. of E. salvia. Oil. acid
Calabuig, M.T. eta/, Phytochemistry, 1981, 20, 2255.
OH

N'cooH
Gonzalez, A.G. eta/, Phytochemistry, 1990, 29, 321.

12-Hydroxy-8(17)-labden-19-oic acid
HO
15
Dl-0031 0
c;traffi
C:zoH31,04 M 334.455
(ent-81JH,J2,,13Z)-form
Constit. of Acritopappus confertus.
Bohlmann, F. et a/, Phytochemistry, 1983, 22, 2243.
C20H 340 3 M 322.487
(12R* ,13R*)-form [19892-25-2] 16-Hydroxy-6-oxo-7,13-labdadien-15-oic Dl-00314
threo-form acid
Constit. of Juniperus phoenicea. [1X]n +25.6° (c, 0.8 in
EtOH) (as Me ester). COOH
(12R* ,13S*)-form [19892-03-6]
erythro-:form ~
Constit. of J. phoenicea. [1X]n +41.9° (c, 0.9 in EtOH)
(as Me ester). w~OH (ent-13E)-form
Tabacik, C. et a/, Phytochemistry, 1971, 10, 2147.

0
17-Hydroxy-13-labden-15,16-olide Dl-00311
[97457-13-1] C:zoH300 4 M 334.455
(ent-13E)-form
Constit. of Acritopappus confertus. Cryst. (as Me ester).
Mp 130° (Me ester). [IX]~ +29° (c, 0.51 in CHC13) (Me
ester).
16-Ac:
CnH320 5 M 376.492
From A. confertus.
C:zoH31,03 M 318.455 16-Me ether: ent-16-Methoxy-6-oxo-7,13-labdadien-15-oic
Constit. of Baccharis eggersii. Oil. [IX]~ + 12° (c, 0.18 in acid
CHC1 3). <;1H3l04 M 348.481
17-A/dehyde: [97457-11-9]. 17-0xo-13-labden-15,16-olide From A. confertus.
C:zoH2110 3 M 316.439 (ent-13Z)-form
From B. eggersii. Oil. 16-Ac: Con~tit. of A. confertus.
Bohlmann, F. et a/, Phytochemistry, 1985, 24, 511. 16-A/dehyde: ent-6,16-Dioxo-7,13Z-Iabdadien-15-oic acid

705
16-Hydroxy-17-oxo-6,13-labdadien-15-... - 6-Hydroxy-7-oxo-8-labden-15-... Di-00315 - Di-00320

C20H 20 0 4 M 332.439 (ent-16p)-form [79383-81-6] Acritolongifolide B

From A. confertus. lsol. from A. longifolius.
Bohlmann, F. et a/, Phytochemistry, 1983, 22, 2243. Bohlmann, F. eta/, Phytochemistry, 1981, 20, 275 (iso[)

16-Hydroxy-17-oxo-6,13-labdadien-15-oic Di-00315 13-Hydroxy-7-oxo-8-labdene-15,16:19,6- Dl-00318

acid diolide
COOH

I
N
I CH20H
0

CHO
17
~
H
C20H 300 4 M 334.455
C20H 160 6 M 362.422
(ent-8PH,13E)-form
(6p,13~)-form [71135-32-5] 13-Hydroxyballonigrinolide
16-Ac: Constit. of Ballota lanata. Cryst. (Me2CO). Mp 227°.
C22H 310 5 M 376.492
[cx]n + 15° (c, 0.25 in MeOH).
Constit. of Acritopappus confertus. Gum (as Me ester).
[ex]~ -78° (c, 0.57 in CHC1 3) (Me ester). Savona, G. eta/, Phytochemistry, 1978, 17, 2132.
17-Carboxy/ic acid, 16-Ac: ent-16-Acetoxy-6,13E-
labdadiene-15,17-dioic acid 3-Hydroxy-17-oxo-13-labden-15-oic acid Dl-00319
C 22H3z06 M 392.491
From A. confertus. COOH
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243.

18-Hydroxy-3-oxo-8(17),13-labdadien-15- Di-00316
oic acid HO'
(ent-3~,8ctH, 13Z)-form
COOH
C20 H 3z04 M 336.470
(ent-3P,8«H,13Z)-form [74513-93-2]
(13E)-form Constit. of Ayapana amygdalina.
3-Ketone: [74513-91-0]. ent-3,17-Dioxo-13Z-labden-15-oic
acid ·
C20H 300 4 M 334.455
C20H3004 M 334.455 Constit. of A. amygdalina. Oil (as Me ester). [cx]~4
(13E)-form -16.6° (c, 1 in CHC1 3) (Me ester).
Me ester: (ent-3P,8PH,13Z)-form [74513-94-3]
C11 H 310 4 M 348.481 Constit. of A. amygdalina. Oil. [cxln + 16.8° (c, 1 in
Constit. of Nolana rostrata. Gum. CHC1 3).
Me ester, 18-Ac: Oil. [cx]i;' + 35.4° (c, 0.9 in CHC1 3). 3-Ketone: [74513-92-1].
Constit. of A. amygdalina. Oil (as Me ester). [cx]~4
(13Z)-form
+20.8° (c, 0.5 in CHC1 3).
Constit. of N. rostrata. Cryst. (EtOAcjheptane). Mp 84-
860. [cx]i;' +28.5° (c, 2 in CHC1 3). Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1997.
18-Ac: 18-Acetoxy-3-oxo-8(17),13Z-labdadjen-15-oic acid
C11H 310 5 M 376.492 6-Hydroxy-"7-oxo-8-labden-15-oic acid Di-00320
Constit. of N. rostrata. Amorph. powder
(EtOAcjhexane). [cx]i;' +37.5° (c, 1.1 in CHC1 3). COOH
Garbarino, J.A. et a/, Phytochemistry, 1986, 25, 2833.

16-Hydroxy-17-oxo-7,13-labdadien-15, 16- Dl-00317

olide
C 20 H 3z04 M 336.470
~0 (6P,13~)-form
: i Ho...Ld 6-Ac:
~CHO (mt-100)-fo"" C11H 340 5 M 378.508
Constit. of Cistus labdaniferus. Oil (as Me ester). [cx]n
-25° (c, 1.16 in CHC1 3) (Me ester).
de Pascual Teresa, J. et a/, Phytochemistry, 1982, 21, 899.
C 20H 200 4 M 332.439
(ent-16«)-form [79383-82-7] Acritolongifolide A
lsol. from Acritopappus longifolius.

706
8(17),12-Labdadiene-15,16-dial - 7,13-Labdadiene-2,15-diol Di-00321 - Di-00325

8(17),12-Labdadiene-15,16-dial Di-00321 8(17),13-Labdadiene-15,19-dioic acid Dl-00324

15
CHO COOH

CHO
15

COOH
19
C20H 300 2 M 302.456
(12£)-form [104263-85-6] C20 H 300 4 M 334.455
Constit. of Curcuma heyneana and Alpinia galanga. Oil. HE-form [640-28-8] Agathic acid. Agathenedicarboxylic acid.
[oc]i,O + W (c, 0.23 in MeOH). Kauric acid. Copaldicarboxylic acid
15-Alcohol: 15-Hydroxy-8{17),12E-Iabdadien-16-al C20 H 300 4 M 334.455
C2oH3P2 M 304.472 Constit. of Agathis australis and A. microstachya. Cryst.
Constit. of rhizomes of A. formosana. Oil. [oc]i,O + 20° (c, (MeOH). Mp 203-204°. [ocJn +56.1° (EtOH).
0.1 in CHC1 3). 15-Me ester:
8fi,17-Epoxide: [71641-23-1]. 8P,J7-Epoxy-12E-Iabdene- C2tH3p4 M 348.481
15,16-dial Major constit. of A. microstachya. Cryst. Mp 64-65°.
C20H 300 3 M 318.455 [ocJn +63° (EtOH).
Constit. of Aframomum daniellii. Cryst. (C 6H 6jpet. 19-Me ester:
ether). Mp 90-92°. [ocln +28.1° (c, 1.41 in CHCI 3). C21 H 3P 4 M 348.481
(ent-12£)-form Constit. of A. australis. [ocln +65° (EtOH).
Constit. of A. speciosa. Oil. [oc]i,S -15° (c, 0.04 in Bory, S. eta/, Bull. Soc. Chim. Fr., 1963, 2310 (struct)
EtOH). Enzell, C. et al, Ark. Kemi, 1965, 23, 367 (ms)
Carman, R.M. eta/, Aust. J. Chern., 1966, 19, 2403 (isol)
[84413-88-7]
Bastard, J. et al, J. Nat. Prod. (Lloydia), 1984, 47, 592 (cmr)
Kimbu, S.F. et al, J. Chern. Soc., Perkin Trans. I, 1979, 1303 Zdero, C. et al, Phytochemistry, 1990, 29, 326 (iso/, pmr, cmr)
(epoxide)
Itokawa, H. eta/, Chern. Pharm. Bull., 1980, 28, 3452 (isol)
Kim, T.H. eta/, J. Chern. Soc., Chern. Commun., 1983, 730 (synth) 7,13-Labdadiene-2,15-diol Dl-00325
Itokawa, H. et a/, Phytochemistry, 1988, 27, 435 (isol)
Firman, K. et a/, Phytochemistry, 1988, 27, 3887 (isol)
Morita, H. eta/, Planta Med., 1988, 54, 117 (isol, pmr, cmr, struct)
1

7,13-Labdadiene-15,18-dioic acid Dl-00322

( " ( C H OH
HOW 2 I
COOH H
C20H 340 2 M 306.487
(ent-2tx.,13E)-form
Constit. of Ophryosporus heptanthus and 0. jioribundus.
Gum.
15-Ac: ent-15-Acetoxy-7,13-labdadien-2tx.-ol
COOH C22H 360 3 M 348.525
C20H 300 4 M 334.455 Constit. of 0. heptanthus. Gum.
(13Z)-form [85994-68-9] Batudioic acid 15-Carboxylic acid: [52914-35-9]. ent-2tx.-Hydroxy-7,13E-
Constit. of Baccharis tucumanensis. Oil (as Di-Me ester). Iabdadien-15-oic acid
[oc]it -12.7° (c, 1.29 in CHCI 3) (Di-Me ester). C2uH3203 M 320.471
Tonn, C.E. et al, Phytochemistry, 1982, 21, 2599. Constit. of Dodonaea microzyga. Cryst. (MeOH). Mp
134-135°. [ocJn -37° (c, 1.1 in Py).
7,13(16)-Labdadiene-15,19-dioic acid Dl-00323 15-Carboxylic acid, 2-angeloyl: [63147-19-3]. Dendroidinic
acid
COOH C25H 380 4 M 402.573
Isol. from Ageratina dendroides. Oil.
(ent-2p,13E)-form
Constit. of Baccharis sternbergiana. Oil. [oc]~ -5° (c, 0.8
in CHCI 3).
15-Ac: ent-15-Acetoxy-7,13-labdadien-2P-ol
C22 H 360 3 M 348.525
C20 H 300 4 M 334.455 Constit. of B. sternbergiana. Oil. [oc]~4 -9.SO (c, 2.13 in
Constit. of Gutierrezia Iucida. Oil. [oc)~4 + 11.2° (c, 8 in CHCI 3).
CHCI 3) (as di-Me ester). 2-Ketone: ent-15-Hydroxy-7, 13-labdadien-2-one
Bohlmann, F. et al, Phytochemistry, 1979, 18, 1533. C20H 320 2 M 304.472
Constit. of B. sternbergiana.
Jefferies, P.R. et al, Aust. J. Chern., 1974, 27, 1097.
Bohlmann, F. eta/, Chern. Ber., 1977, 110, 1321 (Dendroidinic
acid)
Zdero, C. et al, Phytochemistry, 1989, 28, 531; 1990, 29, 3247.
Ferracini, V.L. eta/, Phytochemistry, 1989, 28, 1463.
707
7 ,13-Labdadiene-3,15-diol - 7 ,13-Labdadiene-15,19-diol Di-00326 - Di-00329

7,13-Labdadiene-3,15-diol Oi-00326 7,13-Labdadiene-6,15-diol 01-00327

HO' (3tX, 13E)-form

C20H 340 2 M 306.487 C20H 340 2 M 306.487

(3rt,13E)-form (6p,J3E)-form
15-Carboxy/ic acid: [73695-98-4]. 3rt-Hydroxy-7,13E- Constit. of Solidago canadensis. Gum. [a:]~4 -14° (c, 0.3
labdadien-15-oic acid in CHC1 3).
C20H 32 0 3 M 320.471 6-Ketone: 15-Hydroxy-7,13E-labdadien-6-one
Isol. from Chrysothamnus nauseosus. Oil. C20 H 3z0 2 M 304.472
(3p,J3E)-form Constit. of S. canadensis. Gum.
15-Carboxy/ic acid: [73696-00-1]. 3P-Hydroxy-7,13E- 6-Ketone, 13S,J4-dihydro: 6-0xo-7-labden-15-oic acid. 6-
labdadien-15-oic acid 0xocativic acid
C20H 32 0 3 M 320.471 C20 H 320 3 M 320.471
From C. nauseosus. Oil. Constit. of Cistus labdaniferus. Prisms (MeOH aq.). Mp
114-115°. (a:] 0 + 13° (CHC1 3).
15-Carboxy/ic acid, 3-Ac: [87667-65-0]. Sempevirenic acid
Isol. from Solidago sempervirens. Cryst. (MeOH). Mp Halsall, T.G. eta/, J. Chern. Soc., 1960, 1324 (6-0xocativic acid)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2655 (isol)
185°. [1X] 0 +70°.

c;+r
15-Carboxylic acid, 3-ketone: [73695-96-2]. 3-0xo-7,13E-
labdadien-15-oic acid 7,13-Labdadiene-15,16-diol Oi-00328
C20H 300 3 M 318.455
!sol. from C. nauseosus. Oil. ~~H2 0H
(3p,13Z)-form
CH,OH
15-Carboxy/ic acid: [73697-44-6]. 3p-Hydroxy-7,13Z-
Iabdadien-15-oic acid
C20 H 32 0 3 M 320.471
From C. nauseosus. Oil.
(ent-3rt,l3E)-form C20 H 340 2 M 306.487
Constit. of Corymbium villosum. Gum. [a:Ji;' -9° (c, 2.81 (ent-13Z)-form
in CHC1 3). Gum. [a:]~4 + 1.8° (c, 0.34 in CHC1 3).
3-Ac: Di-Ac:
C2zH3603 M 348.525 C24H 380 4 M 390.562
From C. villosum. Gum. Constit. of Baccharis intermixta. Gum.
15-Ac: 15-Carboxy/ic acid: ent-16-Hydroxy-7,13Z-labdadien-15-oic
C 22H 360 3 M 348.525 acid
From C. villosum. Gum. C20 H 320 3 M 320.471
15-(3-Methylbutanoyl): Constit. of Acritopappus confertus. Gum (as Me ester).
C25 H42 0 3 M 390.605 [a:]~4 -2.3° (c, 1.22 in CHC1 3) (Me ester).
From C. villosum. Gum. Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695; 1981, 20, 281.
15-(3-Methylpentanoyl):
C26H 440 3 M 404.632
From C. villosum. Gum.
7,13-Labdadiene-15,19-diol 01-00329
3-Malonyl:
C23 H 360 5 M 392.534
From C. villosum. Gum (as Me ester).
3-Malonyl, 15-(3-methylbutanoyl):
C28 H440 6 M 476.652
From C. villosum. Gum (as Me ester).
CHPH
3-Malonyl, 15-(3-methylpentanoyl):
C29H 460 6 M 490.679 C20H 340 2 M 306.487
From C. villosum. Gum (as Me ester). (E)-form [66471-77-0] Villenol
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1889. Constit. of Sideritis chamaedryfolia. Cryst.
Purushothaman, K.K. eta/, Phytochemistry, 1983, 22, 1042 (Me 2C0jhexane or C6H 6 /hexane). Mp 106-108°. [a:Jii
(Semipervirenic acid) +4.3° (c, 0.41 in CHC1 3).
Zdero, C. eta/, Phytochemistry, 1988, 27, 227. 19-Ac: (66471-74-7].
CnH360 3 M 348.525
Constit. of S. chamaedryfolia. Oil. Bp0 .07 190°. [a:]i,"
-7.4° (c, 1.13 in CHCI 3).
Rodriguez, B., Phytochemistry, 1978, 17, 281.

708
7,14-Labdadiene-2,13-diol - 8,14-Labdadiene-13,19-diol Di-00330 - Di-00335

W
7,14-Labdadiene-2,13-diol Dl-00330 8,13-Labdadiene-15,19-diol Dl-00333

HOWOH ~

\
CH 20H
15

HOH 2 C
19
C20H 340 2 M 306.487
(ent-2«,131;)-form C20H 340 2 M 306.487
Constit. of lxiolaena /epto/epis. Oil. (13E)-form [22550-16-9]
Lehmann, L. eta/, Phytochemistry, 1988, 27, 2994. Constit. of Araucaria cunninghami. Cryst. Mp 141-143°.
[aJn +54° (CHC1 3).
7,14-Labdadiene-3,13-diol Dl-00331 15-Ac: [52936-73-9].
C22 H 360 3 M 348.525
Constit. of A. cunninghami. Oil.
Di-Ac: [27994-08-7].
C24H 380 4 M 390.562
Constit. of A. cunninghami. Oil.
19-A/dehyde: [53021-98-0]. 15-Hydroxy-8,13E-Iabdadien-19-
a/
C20H 320 2 M 304.472
C 20H 340 2 M 306.487 Constit. of A. cooki. Oil. [aJn +68° (c, 1.4 in CHC1 3).
(3«,13R)-form 15-Carboxy/ic acid: 19-Hydroxy-8,13E-Iabdadien-15-oic
Constit. of Waitzia acuminata. acid
Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943. C20H 320 3 M 320.471
Constit. of A. cooki. Oil (as Me ester). [aJn + 56°
8,13-Labdadiene-7,15-diol Dl-00332 (CHC1 3) (Me ester).
19-Carboxy/ic acid: [53077-96-6]. 15-Hydroxy-8,13E-
Iabdadien-19-oic acid
C20H 320 3 M 320.471
Constit. of A. cunninghami. Cryst. (C6H 6 /hexane). Mp
124-125°. [aJn + 128° (c, 1 in CHC1 3}.
(7a., 13E)-form
Caputo, R. et a/, Phytochemistry, 1974, 13, 471, 475.

C~ 340 2 M 306.487 8,13(16)-Labdadiene-14,15-diol Dl-00334

(7«,13E)-form
OH
7-Ketone, 15-Ac: 15-Acetoxy-8,13E-Iabdadien-1-one
C22H 340 3 M 346.509
Constit. of Parentucellia /atifolia. Oil. [a]~ -45° (c, 1 in CHPH
CHC1 3}.
15-Carboxy/ic acid, 7-ketone: [115374-33-9]. 7-0xo-8,13E-
/abdadien-15-oic acid. Rhinocerotinoic acid
C20H 31,03 M 318.455
Isol. from Eltyropappus rhinocerotis. Cryst. Mp 186-
1890. [a]i?· 5 +42° (c, 1 in CHC1 3). C20H 340 2 M 306.487
(ent-7«,13£)-form (ent-141;)-form
ent-8,13-Labdadiene-7«,15-diol Constit. of Gypothamnium pinifolium. Oil. [a]i;4 -61° (c,
Constit. of Gypothamnium pinifolium. 0.82 in CHC1 3).
7-Ketone: ent-15-Hydroxy-8,13-labdadien-7-one Zdero, C. et al, Phytochemistry, 1988, 27, 2953.
C20H 320 2 M 304.472
Constit. of G. pinifolium. 8,14-Labdadiene-13,19-diol Dl-00335
(ent-7P,J3E)-form

~'
~ :OH
Constit. of G. pinifolium.

W
Zdero, C. et al, Phytochemistry, 1988, 27, 2953.
Dekker, T.G. et al, S. Afr. J. Chern., 1988, 41, 33.
Urones, J.G. eta/, Phytochemistry, 1990, 29, 2223 (isol, pmr, cmr)
(13R)-form
HOH 2 C
C20 H 340 2 M 306.487
(13R)-form [52936-80-8]
Constit. of Araucaria cooki and A. angustifolia. Cryst.
(C6H 6/hexane). Mp 89-91°. [aln +76° (c, 1.2 in CHC1 3).
19-A/dehyde: 13R-Hydroxy-8,14-labdadien-19-a/
C20H 320 2 M 304.472
Constit. of A. cooki. Oil. [aln +95° (c, 1.1 in CHC1 3).
709
8(17),13-Labdadiene-2,15-diol - 8(17),13-Labdadiene-7,15-diol Di-00336 - Di-00338

(13S)-form [39702-12-0] 8(17),13-Labdadiene-3,15-diol Dl-00337

Constit. of Agathis robusta. Noncryst. [cxJn + 121° (c, 0.8
in EtOH).
Carman, R.M. et al, Aust. J. Chern., 1973, 26, 209.
Caputo, R. et al, Phytochemistry, 1974, 13, 471.

8(17),13-Labdadiene-2, 15-diol Dl-00336

CH2 0H HO~
(3a., 13Z)-form

C20H 340 2 M 306.487

(3rx.,13Z)-form
(2a., 13Z}:form Constit. of Juniperus pseudosabina. Cryst. (C6H 6). Mp
65°.
15-Ac:
C 20H 340 2 M 306.487 C22H 360 3 M 348.525
(2rx.,13Z)-form Constit. of J. pseudosabina. Cryst. (C 6H 6). Mp 86°.
Constit. of Brickellia eupatoriedes. Gum. (3p,I3E)-form
2-Ketone: 15-Hydroxy-8(17),13-lllbdadien-2-one 15-Carboxy/ic acid: [63399-38-2]. 3P-Hydroxy-8(17),13E-
C20H 320 2 M 304.472 labdadien-15-oic acid
Constit. of Ophyrosporus chi/ca. Oil. C20H320 3 M 320.471
2-Ketone, 15-carboxy/ic acid: 2-0xo-8(17),13-lllbdadien-15- Cryst. (EtzO). Mp 157.5-158.SO. [cxJi? +40.7° (c, 0.2 in
oic acid CHC1 3).
Constit. of Nolania rostrata. Gum. [a]i; + 55.4° (c, 0.81 15-Carboxy/ic acid, 3-Ac: [63399-37-1]. 3P-Acetoxy-
in CHC1 3). 8(17),13E-IIlbdadien-15-oic acid
(2P,I3E)-form C22 H 340 4 M 362.508
Constit. of Metasequoia glyptostroboides. Cryst.
15-Carboxy/ic acid, 2-Ac: 2P-Acetoxy-8(17),13E-IIlbdadien-
(EtzO/pet. ether). Mp 161-162°.
15-oic acid
C22H 340 4 M 362.508 (ent-3p,I3E)-form
Constit. of N. filifolia. Amorph. powder (as Me ester). 15-Carboxy/ic acid: ent-3P-Hydroxy-8(17),13-lllbdadien-15-
[cx]i; -20.1 o (c, 1.5 in CHC1 3) (Me ester). oic acid
(2P,I3Z)-form C20H 320 3 M 320.471
Constit. of the Copaiba tree.
15-Carboxy/ic acid, 2-Ac: 2P-Acetoxy-8(17),13Z-IIlbdadien-
15-oic acid (ent-3P,I3Z)-form
C22 H 340 4 M 362.508 15-Carboxy/ic acid: [74559-97-0]. ent-3P-Hydroxy-
Constit. of N. filifolia. Cryst. (EtOAcjpet. ether) (as Me 8(17), 13Z-Iabdadien-15-oic acid
ester). Mp 101-103° (Me ester). [cx]i; -13.SO (c, 1.11 in C20 H 3z03 M 320.471
CHC1 3) (Me ester). Constit. of Ayapana amygdalina. Oil (as Me ester). [cx]i;'
(ent-2P,I3E)-form -2.8° (c, 0.5 in CHC1 3)(Me ester).
15-Aldehyde: ent-2P-Hydroxy-8(17),13E-IIlbdadien-15-al 15-Carboxy/ic acid, 3-ketone, 8cx,17-epoxide: [74513-98-7].
C20H 320 2 M 304.472 ent-8p,17-Epoxy-3-oxo-13Z-IIlbden-15-oic acid
Constit. of Baccharis sternbergiana. Oil. [cx)i;' -20° (c, C20 H 300 5 M 350.454
0.5 in CHC1 3). Isol. from A. amygdalina. Oil (as Me ether). [cxJn + 0°
(Me ester).
15-A/dehyde, 2-ketone: ent-2-0xo-8(17),13E-IIlbdadien-15-al
C20H 300 2 M 302.456 (ent-3rx.,13E)-form
From B. sternbergiana. Oil. [cx]i;' -20° (c, 0.4 in CHC1 3). Cyclic malonyl ester: see 7,13-Corymbidienolide, Di-00150
(ent-2P,13Z)-form Dimeric malonyl ester: see Corymbivillosol, Di-00 151
Braun, S. et al, Tetrahedron, 1977, 33, 145.
15-Aldehyde: ent-2P-Hydroxy-8(17),13Z-IIlbdadien-15-al Bohlmann, F. et al, Phytochemistry, 1979, 18, 1997.
C20H 320 2 M 304.472 Armstrong, R.J. et al, Can. J. Chern., 1986, 64, 584 (synth, bib/)
From B. sternbergiana. Oil. Pandita, K. et al, Indian J. Chern., Sect. B, 1987, 26, 453 (isol)
15-Aldehyde, 2-ketone: ent-2-0xo-8(17),13Z-IIlbdadien-15-al Dhar, K.L. eta/, Indian J. Chern., Sect. B, 1990, 29, 911 (isol, pmr,
C20H 300 2 M 302.456 cmr)
From B. sternbergiana. Oil.
(ent-2rx.,I3E)-form 8(17),13-Labdadiene-7,15-diol Dl-00338
Constit. of Ophyrosporus jloribundus. Gum. 15
Bohlmann, F. et al, Phytochemistry, 1982, 21, 181; 1984, 23, 1513. CHpH
Garbarino, J.A. et al, Phytochemistry, 1986, 25, 2833; 1988, 27,
1795.
Zdero, C. et al, Phytochemistry, 1990, 29, 3247 (isol, pmr) (7a., 13E)-form

C20H340 1 M 306.487
(7rx.,13E)-form
Di-Ac:
C24H 380 4 M 390.562

710
8(17),13-Labdadiene-9,15-diol - 8(17),13-Labdadiene-15,19-diol Di-00339 - Di-00341

Constit. of Parentucellia latifo/ia. Oil. [IX]~ -31° (c, 1.1 15-Carboxy/ic acid, 3-Ac: ent-18-Acetoxy-8(17),13E-
in CHC1 3). labdadien-15-oic acid
(ent-7P,13E)-form C22H3404 M 362.508
15-Carboxy/ic acid: ent-7ft-Hydroxy-8(17),13-labdadien-15- Isol. from Trachylobium verrucosum. Oil (as Me ester).
oic acid [1Xln -48° (c, 0.9 in CHC1 3) (Me ester).
C20H 320 3 M 320.471 18-Carboxylic acid: [77096-82-3]. ent-15-Hydroxy-
lsol. from Cistus /ibanotis. Oil (as Me ester). [1X]n -13.4° 8(17), 13E-labdadien-18-oic acid. Viscidic acid A
(c, 1.56 in CHC1 3) (Me ester). lsol. from Chrysothamnus viscidiflorus. Oil.
15-Carboxy/ic acid, 7-ketone: ent-7-0xo-8(17),13E- 18-Carboxylic acid, 15-Ac: [77096-81-2]. ent-15-Acetoxy-
labdadien-15-oic acid 8(17),13E-labdadien-18-oic acid. Viscidic acid B
C20H 300 3 M 318.455 Isol. from C. viscidiflorus. Oil. [1X]~4 -31° (c, 0.24 in
Isol. from C. libanotis. Oil (as Me ester). [1Xln -3.4° (c, CHC1 3).
0.96 in CHC1 3) (Me ester). 15,18-Dicarboxylic acid: [41988-89-0]. ent-8(17), 13-
(ent-7rz,13E)-form Labdadiene-15,18-dioic acid. Guamaic acid
7-Ac: [74635-75-9]. C20 H 300 4 M 334.455
C22H3603 M 348.525 Constit. of Hynenaea oblongifolia. Liq. (as di-Me ester).
Constit. of Austroeupatorium chaparense. Oil. [1X]n -41 o (c, 0.9 in CHC1 3) (di-Me ester).
Bohlmann, F. et al, Phytochemistry, 1980, 19, Ill. Hugel, H. et al, Tetrahedron, Suppl. 8, 1966, 203.
de Pascual Teresa, J. et al, An. Quim., 1982, 78, 324. Delle Monache, F. et al, Ann. Chim. (Rome), 1970, 60, 233
Drones, J.G. et al, Phytochemistry, 1990, 29, 2223 (isol, pmr, cmr) (Copaiferolic acid)
Norin, T. et al, Acta Chem. Scand., 1971, 25, 607 (Dehydropinifolic
acid)
8(17),13-Labdadiene-9,15-diol Dl-00339 Sayama, Y. et al, Agric. Bioi. Chern., 1971, 35, 1068 (Kayadiol)
Norin, T. et al, Acta Chern. Scand., Ser. B, 1980, 34, 301 (synth)
Le-Van, N. et al, Phytochemistry, 1980, 19, 1971 (Viscidic acids)
CHPH Cunningham, A. et al, Phytochemistry, 1983, 12, 633 (Guamaic
acid)
Zdero, C. et al, Phytochemistry, 1990, 29, 329 (ent-Copaiferolic
acid)

8(17), 13-Labdadiene-15, 19-diol Dl-00341

C20H 340 2 M 306.487
(ent-9rz,13E)-form
Constit. of Gypothamnium pinifolium.
Zdero, C. et al, Phytochemistry, 1988, 27, 2953.
(13£)-form
8(17),13-Labdadiene-15,18-diol Dl-00340

~CH2 0H
~
C20H3402
(13£)-form [1857-24-5] Agathadiol. Contortadiol
15 Constit. of Pinus spp. Cryst. (diisopropyl etherjMeOH).
Mp 107-108°. [1X]n +31° (c, 2 in CHC1 3).
'CH2 0H 15-A/dehyde: [10266-89-4]. 19-Hydroxy-8(17),13E-
18
labdadien-15-al
C20H 340 2 M 306.487 C20 H 320 2 M 304.472
(13E)-form Isol. from Juniperus thurifera. Cryst. Mp 112°. [rx]~
Kayadiol. 4-Epiagathadiol. 4-epi-Agathadiol + 26.8° (CHC1 3).
Constit. of leaves of Torreya nucifera. Cryst. 19-Aldehyde: [17990-11-3]. 15-Hydroxy-8(17),13E-
(Me2CO/hexane). Mp 114.5-115.5°. [1X]n +45.8° (c, 1.4 labdtJdien-19-al. /soagatholal
in CHC1 3). C20H 320 2 M 304.472
15-Carboxy/ic acid: [28644-96-4]. 18-Hydroxy-8(17),13- Consist. of Thujopsis dolabrata and P. contorta. Oil. [1X]n
labdadien-15-oic acid. Copaiferolic acid +22.5° (c, 1 in CHC1 3).
C20H 320 3 M 320.471 19-Aldehyde, 15-0-P-D-xylopyranoside:
Isol. from Copaifera multijuga. C25H 400 6 M 436.587
15,18-Dicarboxylic acid: [33123-07 -8]. 8(1 7),13- LabdtJdiene- lsol. from T. do/abrata. Amorph. solid (EtOAc). Mp
15,18-dioic acid. Dehydropinifolic acid 132-140° dec. [1X]i;' -35° (c, 1 in CHC1 3).
C~ 3004 M 334.455 15-Carboxylic acid: [25671-16-3]. 19-Hydroxy-8(17),13E-
Constit. of Pinus sylvestris. Cryst. (Me2CO/diisopropyl /abdadien-15-oic acid. Agatholic acid
ether). Mp 190-192°. [1Xln +39° (c, 1.6 in EtOH). C20H 320 3 M 320.471
(ent-13E)-form Constit. of Manila copal. Cryst. (MeOH/EtOAc). Mp
15-Carboxylic acid: [126371-45-7]. ent-Copaiferolic acid 184-186°. [1X]n +42° (c, 2 in EtOH).
C20H 320 3 M 320.471 19-Carboxylic acid: [1909-91-7]. 15-Hydroxy-8(17),13E-
lsol. from Hap/opappus deserticola. labdadien-15-oic acid
15-Carboxylic acid, Me ester: [75330-78-8]. C20H 320 3 M 320.471
C21H340 3 M 334.498 Constit. of Araucaria cunninghami. Oil (as Me ester).
Isol. from H. deserticola. Oil. [1X]n +51 ° (c, 0.9 in CHC13) (Me ester).

711
8(17),14-Labdadiene-3,13-diol - 8(17),14-Labdadiene-13,18-diol Di-00342 - Di-00346

15-Carboxy/ic acid, 19-a/dehyde: [19605-75-5]. 19-0xo- 8(17),14-Labdadiene-6,13-diol Dl-00343

8(1 7),13E-Iabdadien-I5-oic acid. Agathalic acid
C20H:34P 3 M 318.455
Constit. of Agathis spp. Gum. [1X]n + 24.SO (EtOH).
15,19-Dioic acid: see 8(17),13-Labdadiene-15,19-dioic acid,
Di-00324
(13Z)-form
15-A/dehyde: [117404-55-4]. 19-Hydroxy-8(17),13Z-
labdadien-15-al
C20 H 340 2 M 306.487
C 20H 320 2 M 304.472
Isol. from J. thurifera. Cryst. Mp ll5°. [1X]i;' + 14.1° (6rx.,13R)-form [1438-66-0] Larixol
(CHC1 3). Constit. of Larix sibirica. Cryst. (C6 H 6). Mp 103-104°.
[1X]n + 57o (CHCI 3).
Enzell, C., Acta Chern. Scand., 1961, 15, 1303 (Agatholic acid)
Enzell, C. et al, Ark. Kemi, 1965, 23, 367 (ms, Agatholic acid) 6-Ac:
Rowe, J.W. et al, Tetrahedron Lett., 1965, 2633 (Agathadiol, C22H 360 3 M 348.525
Isoagatholal) Constit. of L. europaea. Cryst. Mp 82°. [1X]n +67°
Carman, R.M. et al, Aust. J. Chern., 1968, 21, 1923 (Agathalic (CHCI 3).
acid)
Bruns, K., Tetrahedron Lett., 1970, 3263.
Caputo, R. et al, Phytochemistry, 1974, 13, 475 (19-Carboxylic
acid)
Hasegawa, S. et al, Phytochemistry, 1980, 19, 2479. 8(17),14-Labdadiene-7,13-diol Dl-00344
San Feliciano, A. et al, Phytochemistry, 1988, 27, 2241 (IS-
aldehyde)

8(17),14-Labdadiene-3, 13-diol Dl-00342

C20 H 340 2 M 306.487

(7rx.,13R)-form [24583-54-8] 7rx.-Hydroxymanool
(3cx, 13R)-form
Constit. of Dacrydium kirkii. Cryst. by sub!. Mp 131-
1320. .
C20 H 340 2 M 306.487 Cambie, R.C. et al, Aust. J. Chern., 1969, 22, 1691.
(3rx.,13R)-form
3rx.-Hydroxymanool
Constit. of Juniperus pseudosabina. Cryst. 8(17),14-Labdadiene-9,13-diol Dl-00345
(hexanejC6H 6). Mp 75-76°. [IX]~ + 14.6° (c, 0.8 in
CHC1 3).
3-Ketone: 13R-Hydrozy-8(17),14-labdadien-3-one OH """'
C20H 320 2 M 304.472
From J. pseudosabina. Cryst. (MeOH). Mp 72-73°. [IX]~
+25.7° (c, 1.628 in CHCI 3).
(ent-3rx.,13S)-form
ent-Jrx.-Hydroxy-13-epimanool C20H 340 2 M 306.487
lsol. from Croton sublyratus. Cryst. (Me2CO). Mp 86- (9rx.,131;)-form [60394-20-9] Jungermanool
870. [1X)i; -30.4° (c, I in CHCI 3). Constit. of Jungermannia torticalyx. Cryst. Mp 124-125°.
3-Ac: [1X]D -49.3°.
C 22H 360 3 M 348.525 Matsuo, A. et al, Experientia, 1976, 32, 966.
Constit. of J. pseudosabina. Semi-solid. [IX]~ + 37.9°
(CHCI 3). 8(17),14-Labdadiene-13,18-diol Dl-00346
Di-Ac:
C24H 380 4 M 390.562 OH
Constit. of J. pseudosabina. Semi-solid.
Kitazawa, E. eta/, Phytochemistry, 1981, 20, 287 (isol)
Pandita, K. et a/, Indian J. Chern., Sect. B, 1987, 26, 453 (isol) (13R)-form
Dhar, K.L. eta/, Indian J. Chern., Sect. B, 1990, 29, 911 (isol, pmr,
cmr)

CzoH3402
(13R)-form [4549-12-6] Torreferol. 18-Hydroxymanoo/
Constit. of Torreya nucifera. Cryst. (Me 2CO/hexane).
Mp 125-126°. [1X]~ +51.8° (c, 0.8 in CHCI3).
(13S)-form [33947-55-6] 13-Epitorreferol. 13-epi-Torrefero/
Constit. of T. nucifera and of the bark of Pinus
contorta. Cryst. Mp 148-149° (145-146°). [IX]~ +58.SO (c,
0.3 in CHCI 3).
(ent-13S)-form

712
8(17),14-Labdadiene-13,19-diol - 12,14-Labdadiene-8,11-diol Di-00347 - Di-00352

Constit. of Trachylobium verrucosum. Cryst. (Et 20). Mp 12,14-Labdadiene-3,8-diol Dl-00349

149-150°. [cx] 0 -59° (c, 0.7 in CHC1 3).
Hugel, G. et al, Tetrahedron, Suppl., No. 8, 1966, 203 (isol)
Sayama, Y. et al, Agric. Bioi. Chern., 1971, 35, 1068 (isol)
Manning, T.D.R. et al, Aust. J. Chern., 1973, 26, 2735 (isol)

8(17),14-Labdadiene-13,19-diol Di-00347
C20 H 340 2 M 306.487
(ent-3rz,8rz,l2E)-form
ent-3rz-Hydroxyabienol
Constit. of Grazielia dimorpholepsis. Gum. [cx]~4 -27° (c,
0.3 in CHCI 3).
H (13R)-form Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1069.
19CH20H
C 20H 340 1 M 306.487 12,14-Labdadiene-6,8-diol Di-00350
(13R)-form [1908-44-7] Torulosol ~
Constit. of Cupressus torulosa and other woods
including Tetraclinis articulataand Dacrydium biforme.
Cryst. (diisopropyl ether). Mp 110-111°. [cx] 0 +31° (c, 2
in CHCI 3).
19-Aldehyde: [1857-21-2]. 13R-Hydroxy-8(17),14-lal#adien-
19-al. Torulosal
C10H 310 1 M 304.472 C20 H 340 2 M 306.487
Constit. of heartwood of C. torulosa, Araucaria cooki, (6P,8rz,12E)-form
T. articulata and D. biforme. Unstable oil. [cx] 0 + 29° 6P-Hydroxy-12E-abienol
(CHC1 3). ni]l.52l. Constit. of Koanophyllon conglobatum. Oil.
19-Carboxylic acid: [1909-90-6]. lJR-Hydroxy-8(17),14- Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1190.
labdadien-19-oic acid. Cupressic acid. Torulosic acid
C20H 320 3 M 320.471
Minor constit. of resin of Cupressus spp. and Tetraclinis 12,14-Labdadiene-7,8-diol Dl-00351
articulata. Cryst. (as Me ester). Mp 70-71 o (Me ester).
(cx] 0 + 52.3° (c, 1.3 in CHCI 3) (Me ester). Pro b. artifact.
(13S)-form
19-Carboxylic acid: [39702-14-2]. 13-Epicupressic acid. 13S-
Hydroxy-8( 17), 14-labdadien-19-oic acid (7~,8cx, 12E)-:form
C20 H 320 3 M 320.471
Constit. of Agathis robusta. Oil (as Me ester). [cxln +64°
(c, 1.1 in EtOH) (Me ester). C20 H 340 2 M 306.487
(7P,8rz,l2E)-form [70387-36-9] Nidorellol
(3650-30·4]
Constit. of Nidorella spp. Oil. [cxln -21° (c, 0.4 in
Enzell, C., Acta Chern. Scand., 1961, IS, 1303 (struct) CHCI 3).
Barreto, H.S. et al, Acta Chern. Scand., 1961, IS, 1313 (isol)
Gough, L.J., Chern. Ind. (London), 1964, 2059 (isol, acid) (7p,8rz,12Z)-form
Carman, R.M. et al, Aust. J. Chern., 1973, 26, 209. Constit. of Greek tobacco. Oil. [cx]n +6.7° (c, 0.3 in
Caputo, R. et al, Tetrahedron, 1973, 29, 2047 (synth) CHCI 3).
Caputo, R. et a/, Phytochemistry, 1974, 13, 471 (isol) (ent-7rz,8P,12E)-form [73496-12-5]
Constit. of Porella perrottetiana. Cryst. Mp 111-112°.
11,14-Labdadiene-8,13-diol Dl-00348 [cx] 0 -11° (c, 1.1 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1769.
Asakawa, Y. eta/, Phytochemistry, 1979, 18, 1681.
Wahlberg, I. et al, Acta Chern. Scand., Ser. B, 1982, 36, 573.
Quijano, L. et al, Phytochemistry, 1982, 21, 1369.

(8cx,llE,13R)-form 12,14-Labdadiene-8, 11-diol Dl-00352

HO

C20H 340 2 M 306.487

(8rz,11E,13R)-form [66966-02-7]
Constit. of Nicotiana tabacum. Oil.
(8rz,11E,13S)-form [66890-73-1] C20 H 340 2 M 306.487
From N. tabacum. Oil. (8rz,llf,,12E)-form
Wahlberg, I. et a/, Acta Chern. Scand., Ser. B, 1979, 33, 541.

713
12,14-Labdadiene-8,18-diol - 8(17),14-Labdadiene-2,3,7,13,20-... Di-00353 - Di-00359

Constit. of liverwort Scapania undulata. Cryst. CzoH 310 1 M 304.472

(CHCI 3/pet. ether). Mp 114-116°. [exln +24.4° (c, 1.50 in Isol. from S. varoi. Syrup. [exln -17° (c, I in CHCI 3).
CHCI 3). Rodriquez, B. eta/, An. Quim., 1979, 75, 110.
Huneck, S. et al, J. Chern. Res. (S), 1986, 162. A1garra, J. eta/, Phytochemistry, 1983, 22, 1779 (aldehyde)

12,14-Labdadiene-8,18-diol Dl-00353 8,14-Labdadiene-2,3,7,13,20-pentol Dl-00357

rf'toH ~

HOH~
CzoH340 1 M 306.487 CzoH 340 5 M 354.486
(ent-8rx.)-form (2rx..Jrx.,7rx.,13R)-form
18-Hydroxyabienol 2-Angeloyl, 3,20-di-Ac: 3rx.,20-Diacetoxy-2rx.-angeloyloxy-
Constit. of Austrobrickellia patens. Oil. 8,14-labdadiene-7rx.,13R-diol
Jackupovic, J. eta/, Phytochemistry, 1986, 25, 1927. C19H 440 8 M 520.662
Constit. of Waitzia acuminata.
12,14-Labdadiene-9,18-diol Dl-00354 Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943.

8(17),13-Labdadiene-2,3,15,16,18-pentol Dl-00358
15
~CH2 0H
I r~CH20H
HO;;f :
\
CHPH
HO'
CzoH340 1 M 306.487 I H
(8rx.H,9rx.,12E)-form [72776-60-4] I CH20H
Constit. of Bishovia boliviensis. Oil. [ex]i;' + 11.9° (c, 4.7
C10H 340 5 M 354.486
in CHCI3).
(ent-2rx..JP,13Z)-form
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1234.
3-Angeloyl: [99624-41-6].
C15H 400 6 M 436.587
13(16),14-Labdadiene-6,8-diol Dl-00355 Constit. of Gutierrezia solbrigii.
[96896-75-2] Jakupovic, J. et a/, Tetrahedron, 1985, 41, 4537.

8(17),14-Labdadiene-2,3,7,13,20-pentol Dl-00359
~

CzoH 340 1 M 306.487

(ent-6rx.,8rx.)-form
18-Deoxyandalusol
C10H 340 5 M 354.486
Constit. of Sideritis arborescens. Gum. [ex]~ - 32.7° (c, I
in CHCI3). (2rx..Jrx.,7rx.,13R)-form
Garcia-Granados, A. eta/, Phytochemistry, 1985, 24, 517. 2-Angeloyl, 20-Ac: 20-Acetoxy-2«-angeloyloxy-8(17),14-
labdadiene-3rx.,7rx.,13R-triol
C17H 410 7 M 478.625
13(16),14-Labdadiene-8,18-diol Di-00356 Constit. of Waitzia acuminata.
2-Angeloyl, 20-(2-methy/butanoyl): 2rx.-Angeloyloxy-20-(2-
.~ methylbutanoyloxy)-8(17),14-labdadiene-3rx.,7rx.,13R-triol
C30H 480 7 M 520.705
~OH Constit. of W. acuminata.
2-Ange/oyl, 3,20-di-Ac: 3rx.,20-Diacetoxy-2rx.-angeloyloxy-
HOH~ 8(17),14-labdadiene-7rx.,l3R-diol
C19H 440 8 M 520.662
CzoH340 1 M 306.487 Constit. of W. acuminata.
(ent-8rx.)-form [70868-53-0] 6-Deoxyandalusol Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943.
Constit. of Sideritis arborescens. Amorph. solid. Mp 63-
670. [ex]~ -17.SO (c, 0.76 in CHCI3).
18-Aldehyde: ent-Brx.-Hydroxy-13(16),14-labdadien-18-al

714
11,13(16)-Labdadiene-6,7,8,14,15-... - 7,13-Labdadiene-2,3,15-triol Di-00360 - Di-00366

11,13(16)-Labdadiene-6,7,8,14,15-pentol Dl-00360 8,13-Labdadiene-2,6,7,15-tetrol Dl-00363

OH

C10H 340 4 M 338.486

OH (2rz.,6P,7rz.,13E)-form
2,7-Di-Ac, 0 6-(3-methy/butanoyl): 2rz.,7rz.-Diacetoxy-6P-
C10H 340 5 M 354.486 isollaleroyloxy-8,13E-Iabdlldien-15-ol
C29H 460 7 M 506.678
(6rz.,7p,8rz.,11E,l4f.)(l)-form [114437-32-0] Sterebin G
Constit. of marine pulmonate Trimusculus reticulatus.
Constit. of Stevia rebaudiana. Powder. [ocln -5.9° (c, 0.5
in MeOH). Oil. [oc]n +41.2° (c, 0.35 in CHC1 3).
Manker, D.C. eta/, Tetrahedron, 1987, 43, 3677.
(6rz.,7P,Brz.,11E,141;)(2)-form [114927-19-4] Sterebin H
Cmlf340 5 M 354.486
From S. rebaudiana. Powder. [oc]n -6.7° (c, 0.5 in 8(17), 14-Labdadiene-2,7, 13,20-tetrol Dl-00364
MeOH). 14-Epimer of Sterebin G.
Oshima, Y. et al, Phytochemistry, 1988, 27, 624.

7,13-Labdadiene-2,15,16,17-tetrol Dl-00361

CHPH
CHPH
CHPH C10H 340 4 M 338.486
(2rz.,7rz.,13R)-form
2-Ange/oyl, 20-Ac: 20-Acetoxy-2rz.-angeloyloxy-8(17),14-
lllbdadiene-7rz.,l3R-diol
C10H 340 4 M 338.486 C17H 420 6 M 462.625
(2p,13Z)-form [130395-45-8] Constit. of Waitzia acuminata.
Constit. of Baccharis potosina. Gum. Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943.
Jakupovic, J. et al, Phytochemistry, 1990, 29, 2217 (isol, pmr)
11,13-Labdadiene-6,7,8,15-tetrol Dl-00365
7,14-Labdadiene-2,3,13,20-tetrol Dl-00362
CH20H
7"

Cmlf340 4 M 338.486
(2rz..3rz.,13R)-form
2-Ange/oy/, 20-Ac: 20-Acetoxy-2rz.-angeloyloxy-7,14- C10H340 4 M 338.486
lllbdlldiene-3rz.,l3R-diol
(6«,7P,Brz.,11E,l3E)-form [114343-74-7] Sterebin E
C17H 420 6 M 462.625
Constit. of Stevia rebaudiana. Powder. [ocln + 29.9° (c,
Constit. of Waitzia acuminata. 0.17 in MeOH).
2-Ange/oy/, 20-(2-methy/butanoyl): 2rz.-Angeloyloxy-20-(2-
(fi«,7P,8rz.,llE,13Z)-form [114489-87-1] Sterebin F
metlrylbutanoyloxy)-7,14-lllbdatliene-Jrz.,JJS-diol
Constit. of S. rebaudiana. Powder. [ocln +40.3° (c, 0.16
C 30 Ho~~~0 6 M 504.706 in MeOH).
Constit. of W. acuminata.
Oshima, Y. et al, Phytochemistry, 1988, 27,'624.
Jakupovic, J. et al, Phytochemistry, 1989, 28, 1943.

7,13-Labdadiene-2,3,15-triol Dl-00366

HO~~CH,OH
HO~ (ent-2a.,3a.,13E)-form

C10H 340 3 M 322.487

(ent-2rz.,3rz.,13E)-form

715
7,13-Labdadiene-3,11,15-triol - 8(17),13-Labdadiene-3,7,15-triol Di-00367 - Di-00372

Constit. of Baccharis salicifolia. 7,14-Labdadiene-2,3,13-triol Dl-00369

15-Ac: ent-15-Acetoxy-7,13-labdlldiene-2rx.,3rx.-diol
C12H 360 4 M 364.524
Constit. of Ophryosporus heptanthus. Gum. ~
(ent-2rx.,3fJ,J3E)-form
HO~OH
lsol. from B. paniculata. Oil. [a]i; -6.64° (c, 5.98 in
CHC1 3). HO~
15-A/dehyde: ent-2rx.,3fJ-Dihydroxy-7,13-labdlldien-15-al
C:zoH320 3 M 320.471 C:zoH340 3 M 322.487
lsol. from B. paniculata. Oil. [a]ii + 2.SO (c, 11.56 in (ent-2rx.,3rx.,l31;)-form
CHC1 3). Constit. of Ixiolaena leptolepis. OiL
(ent-2fJ,3fJ,J3E)-form Lehmann, L. eta/, Phytochemistry, 1988, 27, 2994.

HOW
lsol. from B. sternbergiana.
Zdero, C. eta/, Phytochemistry, 1986, 25, 2841; 1989, 28, 531. 7,14-Labdadiene-2,13,20-triol Dl-00370
Ferracini, V.L. eta/, Phytochemistry, 1989, 28, 1463 (deriv)
Faini, C.L.F. eta/, Phytochemistry, 1990, 29, 324.

7,13-Labdadiene-3,11,15-triol Dl-00367
HO

C:zoH 340 3 M 322.487

(ent-2rx.,131;)-form
HO' Constit. of Ixiolaena leptolepis. Oil.
Lehmann, L. eta/, Phytochemistry, 1988, 27, 2994.
C:zoH 340 3 M 322.487
(ent-3fJ,lll;,l3E)-form 8,13-Labdadiene-6,7,15-triol Di-00371
3,15-Di-Ac:
C24H 38 0 5 M 406.561 CHPH
Constit. of Lasiolaena santosii. Gum. [a]~ + 15° (c, 0.3
in CHC13).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1613.

7,13-Labdadiene-15,16,17-triol Dl-00368

<?' C:zoH 340 3 M 322.487

(6fJ,7rx.,13E)-form
0 6-(3-M ethylbutanoyl): 6P-Isova/eroy/oxy-8, 13E-labdadiene-
7a,15-diol
C25H 420 4 M 406.604
Constit. of marine pulmonate Trimusculus reticulatus
C:zoH340 3 M 322.487 and its defensive mucus. Oil. [1X]n +38.7° (c, 0.83 in
(ent-13Z)-form CHC1 3).
Constit. of Achyrocline a/ata. Gum (as tri-Ac). [a]~ -2° Manker, D.C. et a/, Tetrahedron, 1987, 43, 3677.
(c, 0.4 in CHC1 3) (tri-Ac).
15-Carboxy/ic acid: ent-16,17-Dihydroxy-7,13Z-Iabdlldien- 8(17),13-Labdadiene-3,7,15-triol Dl-00372
15-oic acid
C:zoH320 4 M 336.470
Isol. from Acritopappus confertus. Gum (as Me ester).
(""TcHpH
[a]~ +4.9° (c, 2.2 in CHC1 3) (Me ester).
15-Carboxy/ic acid, 17-aldehyde: ent-16-Hydroxy-17-oxo- riAy (ent-3a.,7a.,13E)-form
7,13Z-Iabdlldien-15-oic acid
C:zoH34,04 M 334.455
HO~OH
Isol. from A. confertus. C:zoH340 3 M 322.487
15-Carboxy/ic acid, 16-Ac: ent-16-Acetoxy-17-hydroxy- (ent-3rx.,7rx.,l3E)-form
7,13Z-Iabdlldien-15-oic acid
3,15-Malonyl diester: see 7,13-Corymbidieno/ide, Di-00150
C:zoH 340 5 M 354.486
(ent-3fJ,7fJ,13Z)-form
Constit. of A. confertus.
15-Carboxy/ic acid: [74513-88-5]. ent-3fJ,7fJ-Dihydroxy-
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2475, 2695.
8(17),13-labdlldien-15-oic acid
C:zoH3p 4 M 336.470
Isol. from Ayapana amygdalina. Oil (as Me ester). [a]~
-20.6° (c, 0.5 in CHC1 3) (Me ester).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1997.

716
8(17),13-Labdadiene-3,15,16-triol - 12,14-Labdadiene-6,8,18-triol Di-00373- Di-00378

01-00373 Constit. of Aristeguietia buddleaefolia. Oil. [a]i;' -3.7°

(c, 2.3 in CHCl 3).
18-(4-Hydroxy-E-cinnamoyl), l-Ac:
c31H410, M 510.669
Constit. of A. buddleaefolia. Oil.
18(4-Hydroxy-Z-cinnamoyl), l-Ac:
C3tH4z06 M 510.669
Constit. of A. buddleaefolia. Oil.
Bohlmann, F. et al, Phytochemistry, 1980, 19, 977.

12,14-Labdadiene-6,7,8-triol Oi-00377

8(17},13-Labdadiene-6,15,18-triol 01-00374 (6ct, 7~,8ct,l2E)-form

CzoH 340 3 M 322.487

(6r~.,7p,Br~.,l2E)-form[70387-38-1] 6r~.-Hydroxynidorellol
Constit. of Nidorella spp. Oil.
6-Ange/oy/: 6r~.-Angeloyloxynidorellol
C25 H 400 4 M 404.589
C20H3403 Constit. of Stevia monardaefolia. Cryst. Mp 114-ll5°.
6r~.-form
[a] 0 -34.8° (CHCl 3).
(6r~.,7p,ap,J2Z)-form [62868-75-1] Austroinulin
6-Benzoyl: Scoparinol
C27H 380 4 M 426.595 lsol. from Austroeupatorium inulaefolium and S.
rebaudiana. Needles (MeOH). Mp 74-77°. [a]i; +33.6°
Constit. of Scoparia dulcis. Gum. [a]i;' +2.0° (c, 1 in
CHC1 3). (c, 0.48 in CHCl 3), [a]~ +24.0° (c, 0.50 in CHCl 3).
6-Ac: [75207-46-4]. 6a-Acetoxy-12, 14-labdadiene-7P,8P-diol
Ahmed, M. et al, Phytochemistry, 1990, 29, 3035 (isol, pmr)
C11H 360 4 M 364.524
lsol. from S. rebaudiana. Cryst. (EtOAc). Mp 173-174°.
8(17),13-Labdadiene-7,15,19-triol 01-00375 [a]i; + 36.8° (c, 0.46 in CHCl 3).
7-Ac: 7P-Acetoxy-12,14-labdadiene-6a,8P-diol
C22H 360 4 M 364.524
CH2 0H From S. rebaudiana. Needles (hexane). Mp 148-149°.
15 [a]~ + 14.9° (c, 0.67 in CHCl 3).
H (6p,7p,8r~.,l2E)-form [92694-04-7] 6P,7P-Dihydroxy-12E-abienol
1
CH2 0H Constit. of Koanophyllon conglobatum. Oil. [a]~4 + 10° (c,
19 0.25 in CHCl 3).
C20H 340 3 M 322.487 7-Ac: 7P-Acetoxy-12,14-labdadiene-6p,8a-dio/
(7r~.,l3E)-form [66471-79-2] Villenatriol C11H 360 4 M 364.524
Constit. of Sideritis chamaedryfolia. Amorph. [a]bB From K. conglobatum. Oil.
-41.2° (c, 0.62 in CHCl 3). Softens at 62-65°. Bohlmann, F. et al, Chern. Ber., 1977, 110, 1034 (isol)
19-Ac: [66471-75-8]. Bohlmann, F. et al, Phytochemistry, 1978, 17, 1769; 1984, 23, 1190
(isol)
C22 H 360 4 M 364.524 Sholichin, M. eta/, Phytochemistry, 1980, 19, 326 (isol)
Constit. of S. chamaedryfolia. Syrup. [a]i,O -30° (c, 1.41 Quijano, L. et al, Phytochemistry, 1982, 21, 1369 (isol)
in CHCl 3). Darise, M. et al, Agric. Bioi. Chern., 1983, 47, 133 (isol, struct, ahs
Rodriguez, B., Phytochemistry, 1978, 17, 281. config)

12,14-Labdadiene-1,8,18-triol 01-00376 12,14-Labdadiene-6,8, 18-triol 01-00378

HOH2
C20H 340 3 M 322.487 CzoH340 3 M 322.487
(lp,Br~.,l2E)-form
(6p,Br~.,l2E)-form
lP-Hydroxyaristin 6P,l8-Dihydroxy-12E-abienol
Oil. Constit. of Koanophyllon conglobatum. Oil.
18-/cosanoy/, l-Ac: Bohlmann, F. et al, Phytochemistry, 1984, 23, 1190.
C41 H 740 5 M 659.044

717
13(16),14-Labdadiene-3,6,8-triol - 7,14-Labdadien-13-ol Di-00379 - Di-00384

13(16),14-Labdadiene-3,6,8-triol Dl-00379 7,13-Labdadien-15-oic acid Dl-00382

gVOOOH Absolute
configuration

C20H3p 2 M 304.472
C20 H 340 3 M 322.487
(ent-IJE)-form [14022-43-6]
(ent-3P,6rt,8rt)-form [77887-59-3]/soandalusol 7, 13-Eperuadien-15-oic acid
Cryst. (EtOH). Mp 102-105°. [ex]i? -33.9° (c, 1.5 in Constit. of wood of Oxystigma oxyphyllum and
MeOH). Hymenaea courbaril.
6-Ac: 6-Acetylisoandalusol Me ester: Oil. [ex]~ -26.4° (c, 1.2 in CHC1 3).
C22 H 360 4 M 364.524
Constit. of Sideritis foetens. Cryst. (Me2COjhexane). p-Phenylphenacyl ester: Cryst. Mp 109-111°. [exln -29.8°
Mp 117-117.5°. [ex]i? -47.8° (c, 0.7 in CHCl 3). (c, 0.155 in CHCI 3).
Garcia-Alvarez, M.C. et al, Phytochemistry, 1980, 19, 2405. Bevan, C.W.L. eta/, J. Chern. Soc. C, 1968, 1067 (isol)
Imamura, P.M. et al, Phytochemistry, 1977, 16, 1842 (cmr)

13(16),14-Labdadiene-6,8,18-triol Dl-00380
7,13-Labdadien-15-ol Dl-00383

C20H 340 3 M 322.487

#
HOH2 C ' OH

(ent-6rt,8rt)-form [62279-93-0] Andalusol

C20 H340 M 290.488
Constit. of Sideritis arborescens. Cryst. (E)-form
(Me 2COjhexane). Mp 167-170°. [ex]i? -38.2° (c, 0.7 in Constit. of Nicotiana setchellii. Oil. [ex]~ + 12.1° (c, 0.69
EtOH). in CHC1 3).
6-Ac: Ac:
C21H360 4 M 364.524 C22H 360 2 M 332.525
Constit. of S. foetens. Cryst. (Me2COjhexane). Mp lsol. from Cistus incanus ssp. creticus. [exln + 6° (c, 0.1 in
111.5-112°. [ex]i? -64.4°.(c, 0.6 in CHC1 3). CHCI 3).
18-Ac: Suzuki, H. et al, Phytochemistry, 1983, 22, 1294.
Demetzos, C. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1365 (isol,
C21 H360 4 M 364.524 pmr)
Constit. of S.foetens. Syrup. [ex]i? -27.4° (c, 1.5 in
CHC1 3).
Lopez, M.A. eta/, J. Org. Chem., 1977, 42, 2517 (isol)
7,14-Labdadien-13-ol Dl-00384
Garcia-Alvarez, M.C. et a/, Phytochemistry, 1980, 19, 2405 (isol)

6,8(17)-Labdadien-15-oic acid Di-00381

(13R)-form

C20H 340 M 290.488

(13S)-form
(IJR)-form
Constit. of Aster spathulifolius. Oil. [ex]D -2.4° (MeOH).
C20H320 2 M 304.472 0-(6-Deoxy-ex-L-idopyranoside ):
(IJS)-form [80931-03-9] Cistadienic acid C26H 440 6 M 452.630
Constit. of Cistus symphytifolius. Oil. [exln -6° (c, 0.182 Constit. of A. spathulifolius. Amorph. [exln -61°
in CHC1 3). (MeOH).
Me ester: Oil. [ex]~ + 5.8° (c, 1.21 in CHCI 3). 0-(4-Acetyl-6-deoxy-ex-L-idopyranoside ):
(ent-JJS)-form C28H 460 6 M 478.668
Constit. of Hartwrightiafloridana. Gum (as Me ester). Constit. of A. spathulifolius. [exln -46.8° (MeOH).
[exln + 1.1° (c, 0.36 in CHC1 3) (Me ester). (13S)-form
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 843 (isol) Oil. Bp0 _01 130°. [exln +20° (c, 0.7 in hexane).
Calabuig, M.T. et al, Phytochemistry, 1981, 20, 2255 (isol) Carman, R.M. et al, Aust. J. Chern., 1973, 26, 215 (synth)
De Pascual, T.J. et al, Phytochemistry, 1982, 21, 899 (isol) Uchio, Y. et al, Tetrahedron Lett., 1980, 3775 (isol)

718
8,13-Labdadien-15-ol- 11,13-Labdadien-8-ol Di-00385 - Di-00390

8,13-Labdadien-15-ol Dl-00385 Constit. of Oxystigma oxyphyllum and Pinus montico/a.

Oil. Bp0 _4 171° (as Me ester). [ex)i; +46° (c, 0.5 in
MeOH) (Me ester).
13,;,14,;-Epoxide: 13,14-Epoxy-8(17)-labden-15-ol
C 20H 340 2 M 306.487
Constit. of Hemizonia lutescens. Gum. [ex]i;' + 7° (c, 0.4
(13£)-form in CHC1 3).
(ent-13E)-form
C 20H 340 M 290.488 15-Carboxy/ic acid: [20257-75-4]. ent-8(17), 13E-Labdadien-
(13E)-form 15-oic acid. Copa/ic acid
Constit. of Nicotiana setchellii. Oil. [ex]i;' + 76.5° (c, 0.665 C 20 H 3z02 M 304.472
in CHC1 3). Constit. of Trachylobium verrucosum and Hymenaea
(ent-13E)-form [61217-44-5] courbaril. Oil. Bp0 _005 160°. [ex] 0 -6.9° (c, 1.15 in
Constit. of Araucaria bidwillii. Oil. [ex) 0 -20°. CHC1 3).
Ac: [61217-43-4]. [14022-42-5]
C 22H 360 2 M 332.525 Nakano, T. eta/, J. Org. Chern., 1961, 26, 167 (Copalic acid)
Constit. of A. bidwillii. Oil. [ex] 0 -18°. Sandermann, W. et at, Tetrahedron Lett., 1967, 2685 (isol)
Bevan, C.W.L. eta/, J. Chern. Soc. C, 1968, 1067 (struct)
Caputo, R. et al, Phytochemistry, 1976, 15, 1401 (isol) Cambie, R.C. et a/, Aust. J. Chern., 1969, 22, 1691 (isol)
Suzuki, H. et al, Phytochemistry, 1983, 22, 1294 (isol) Overton, K.H. eta/, J. Chern. Soc. C, 1971, 312 (synth)
Zinke!, D.F. eta/, Phytochemistry, 1971, 10, 1161 (isol)
8,14-Labdadien-13-ol Dl-00386 Manh, D.D.K. eta/, Tetrahedron, 1975, 31, 1903 (synth)
Imamura, P.M. eta/, Phytochemistry, 1977, 16, 1842 (cmr)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2383 (epoxide)

(13R)-form
8(17), 14-Labdadien-13-ol Dl-00389

C 20H 340 M 290.488

(13R)-form [10314-43-9] 1somanool
Oil. Bp0 _01 130°. [ex] 0 +64° (c, 1.1 in hexane).
(13S)-form [10314-42-8) 13-epi-Isomanool. 13-Epiisomanoo/
Oil. Bp0 _01 130°. [ex] 0 +88° (c, 0.8 in hexane).
Carman, R.M. eta/, Aust. J. Chern., 1973, 26, 215.
8(17),12-Labdadien-3-ol
C 20H 340 M 290.488
(3rz.,12E)-form
Constit. of Juniperus pseudosabina. Oil.
Pandita, K. et at, Indian J. Chern., Sect. B, 1987, 26, 453.
8(17), 13-Labdadien-15-ol
(13R)-form
C20H 340 M 290.488
(13R)-form [596-85-0] Manool
Constit. of Dacrydium biforme, D. kirkii, D. bidwil/i,
Cupressus sempervirens, C. toru/osa, andTetrac/inis
Dl-00387 articulata. Cryst. Mp 53°. Bp0 _2 144-145°. [ex]~ +30.4°.
(13S)-form [1438-62-6] 13-Epimanoo/. 13-epi-Manoo/
Constit. of Pinus contorta and Larix decidua. Cryst.
(hexane). Mp 36.5-38.SO. [ex)~ +51 o (c, 1.3 in CHC1 3).
(ent-13S)-form [29461-42-5] ent-13-Epimanool
Constit. of Trachylobium verrucosum. Oil. [ex] 0 -46° (c,
1 in CHC1 3).
Rowe, J.W. et a/, J. Org. Chern., 1964, 29, 1554 (isol)
Enzell, C. et at, Ark. Kemi, 1965, 23, 367 (ms)
Hugel, G. eta/, Tetrahedron, Suppl., No. 8, 1966, 203 (isol)
Bruns, K., Tetrahedron Lett., 1970, 3263 (abs conjig)
Overton, K.H. et at, J. Chern. Soc. C, 1971, 312 (synth)
Almqvist, S. eta/, Acta Chern. Scand., Ser. B, 1975, 29, 695 (cmr)
Bastard, J. eta/, J. Nat. Prod. (Lloydia), 1984, 47, 592 (cmr)
Dl-00388
11,13-Labdadien-8-ol Dl-00390

(13£)-form

C20H 340 M 290.488

(13£)-form [10395-43-4]
Constit. of Dacrydium kirkii. Oil. Bp 1 172-173°. [ex] 0
+33.2°.
C 20H 340 M 290.488
15-Carboxy/ic acid: [24470-48-2). 8(17),13E-Labdadien-15-
(8cx,11E,13E)-form [25578-83-0] Neoabienol
oic acid. Anticopalic acid
Constit. of Abies sibirica. [1X]i? + 12.6° (c, 3.8 in CHC1 3).
C 20H 320 2 M 304.472
Chirkova, M.A. eta/, Khim. Prir. Soedin., 1969, 5, 247.

719
12,14-Labdadien-8-ol - 8(17),13-Labdadien-16,15-olid-19-••• Di-00391 - Di-0039~i'

12,14-Labdadien-8-ol 01-00391 Constit. of Ageratum fastigiatum. Gum. [1X]i;4 + 10° (c,

0.27 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 983.

(Sex, 12£)-form 7 ,13-Labdadien-15,16-olid-19-oic acid

[734S9-06-2)

Cmll340 M 290.4SS 0
(8rz,12E)-form [17990-15-7] Abienol
Constit. of Pinus strobus. Cryst. (MeCN). Mp 51-52.5°.
[aJn +25° (c, 1.2 in CHC1 3).
(8rz,l2Z)-form [17990-16-S] / COOH
Constit. of Abies spp. and Nicotiana spp. Cryst. Mp 40°. C10H 280 4 M 332.439
(aJn +22° (c, 0.9 in CHC1 3). Constit. of Gutierrezia Iucida. Oil (as Me ester). [1X)~4 + 20°
Carman, R.M., Aust. J. Chem., 1966, 19, 1535 (struct) (c, 9.5 in CHC1 3) (Me ester).
Mills, J.S. eta/, J. Chem. Soc. C, 1967, 2514 (synth) Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1533.
Zinke!, D.P. eta/, Phytochemistry, 1972, 11, 3387 (isol)
Colledge, A. eta/, Ann. Tab., Sect. 2, 1974, 177 (biosynth)
8(17),13-Labdadien-15,16-olid-18-oic acid 01-00396
13(16),14-Labdadien-8-ol 01-00392

Sex-form
C10H 280 4 M 332.439
C10H 340 M 290.4SS ent-form
Brz-form [I 0207-79-1] /soabienol Constit. of Ricinocarpus muricatus. Cryst. (C 6H 6jpet.
Constit. of the needles of Pinus sy/vestris and ether). Mp 190-191°. [1X]n -61° (c, 4.5 in EtOH).
Jungermannia infusca. Cryst. Mp 6S-6S.SO. [a]~ -6.4° Henrick, C.A. eta/, Tetrahedron, 1965, 21, 3219.
(CHC1 3).
(ellt-Brz)-form 8(17),13-Labdadien-16,15-olid-19-oic acid 01-00397
Constit. of Sideritis hirsuta. Cryst. Mp 50-51°. [a]~ Demethylpinusolide. Pinusolidic acid
-0.49° (c, I in CHC1 3).
0
Ekman, R. eta/, Acta Chem. Scand., Ser. B, 1977, 31, 921
(Isoabienol)
Cabrera, E. eta/, Phytochemistry, 1983, 22, 2779 (isol)
Toyota, M. eta/, Phytochemistry, 1989, 28, 3415 (iso/, pmr, cmr)

7,13-Labdadien-15,16-olide 01-00393

C10H 280 4 M 332.439

0
lsol. from Bricke//ia g/omerata. Gum.
Me ester: (316S5-SO-O]. Pinusolide
C21 H 300 4 M 346.466
Constit. of the oleorosin of Pinus sibirica and P.
koraiensis. Fine needles (pet. ether). Mp S3-S4°. [a]i;'
C10H 300 2 M 302.456 + 24° (MeOH).
ent-form 15c!;-Hydroxy: 15-Hydroxy-8(17),13-/abdadien-16,15-o/id-19-
Constit. of Acritopappus /ongifo/ius. Gum. oic acid. 15-Hydroxypinusolidic acid
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 275. C 10 H 28 0~ M 34S.43S
lsol. from Platyc/adus orienta/is. Cryst. Mp 74-75°. [cx]i;'
7,13-Labdadien-16,15-olide 01-00394 +30.SO (c, I in CHC1 3).
Raldugin, V.A. eta/, Khim. Prir. Soedin., 1970, 6, 541; Chern. Nat.
Compd. (Engl. Trans/.), 559 (isol, struct, synth)
Calderon, J.S. eta/, Phytochemistry, 1987, 26, 2639 (isol)
Kuo, Y.-H. et a/, Heterocycles, 1990, 31, 1705 (15-
Hydroxypinuso/idic acid)

M 302.456

720
8,15-Labdanediol - 7,12,14-Labdatriene-6,17-diol Di-00398 - Di-00403

8,15-Labdanediol Dl-00398 8(17),12,14-Labdatriene Dl-00401

Biformene
-H [5957-33-5]
15
-OHCHpH
(8cx, 13R)-form

C10H380 1 M 310.519
(8r~.,13R)-form[10267-22-8]
Constit. of the leaf gum of Aeonium lindleyi and Cistus (E)-form
labdaniferus. Amorph. Mp 83-84°. [1X]i? -10° (c, 1.7 in
CHC1 3). C10H31 M 272.473
ent-(8«,13R)-form [1891-84-5] (E)-form
ent-13R-Labdane-81X,l5-diol. 8,15-Eperuanediol Constit. of Dacrydium biforme, D. kirkii and Palafoxia
Constit. of Ricinocarpus muricatus. Cryst. (pet. ether at rosea. Viscous oil. [1X]n +47.3° (c, 1.54 in CHC1 3).
-15°). Mp 75-76°. [1X]n +4° (c, 9 in CHC1 3).
(Z)-form
15-Carboxylic acid: see 8-Hydroxy-15-labdanoic acid, Di- Constit. of D. biforme and D. kirkii. Viscous oil. Mp
00302 18°. [1X]n +46.5° (c, 1 in CHCI 3).
[13902-99-3)
(ent-12Z)-form
Henrick, C.A. eta/, Tetrahedron, 1965, 21, 1175 (isol)
Carman, R.M. et al, Aust. J. Chern., 1973, 26, 879 (struct)
lsol. from Helianthus decapetalus. Oil. [1X]i;4 -16° (c, 0.25
Gonzalez, A.G. et a/, Tetrahedron Lett., 1976, 1897 (cmr) in CHC1 3).
Hirota, H. et al, Bull. Chern. Soc. Jpn., 1988, 61, 4023 (synth) Carman, R.M. et al, Aust. J. Chern., 1967, 20, 157.
Bohlmann, F. et al, Phytochemistry, 1979, 18, 115; 1980, 19, 863.
7,8, 15-Labdanetriol Dl-00399
8(17),13(16),14-Labdatriene Dl-00402
Sclarene
[511-02-4]

C~ 38 0 3 M 326.518
(7P,8«,13R)-form [52329-57-4] Gymnospermin
Constit. of Gymnosperma glutinosa. Cryst. (C6H6 or
EtOAc). Mp 148-148.SO. [1X]i! -8.3° (c, 0.6 in CHCI 3). C10H 31 M 272.473
Miyakado, M. et al, Phytochemistry, 1974, 13, 189. Constit. of Agathis australis and Dacrydium biforme.
Unstable oil.
8,15,18-Labdanetriol Dl-00400 Carman, R.M. eta/, Aust. J. Chern., 1967, 20, 157.

CHPH 7,12,14-Labdatriene-6,17-diol Dl-00403

(8cx, 13R}form

C10H3803
(8«,13R)-form
Constit. of Cistus labdaniferus. Cryst. (MeOH). Mp 188- C10H 310 1 M 304.472
1890. (ent-6P,l2E)-form
(ent-8«,13R)-form [36052-39-8] 8,15,18-Eperuanetriol Cryst. Mp 70°. [1X]i;4 - W (c, 0.13 in CHCI3).
Constit. of Ricinocarpus muricatus. Cryst. (C 6H6). Mp 6-Ac: ent-6P-Acetoxy-7,12E,14-IIlbdatrien-17-ol
121-122°. [1X]n -13° (c, 8.2 in EtOH). CzzH340 3 M 346.509
Constit. of Rutidosis murchisonii. Oil.
Tabacik-Wlotzka, C. eta/, Bull. Soc. Chim. Fr., 1963, 2299.
Henrick, C.A. et al, Tetrahedron, !965, 21, 1175. 6,17-Di-Ac: ent-6p,17-Diacetoxy-7,12E,14-IIlbdatriene
C14H 360 4 M 388.546
From R. murchisonii. Oil.
17-Carboxylic acid: ent-6P- Hydroxy- 7, 12E, 14-labdatrien-11-
oic acid
Oil.
17-Carboxylic acid, 6-Ac: ent-6P-Acetoxy-7,12E,U-
IIlbdatrien-17-oic acid

721
8(17),12,14-Labdatriene-3,19-diol - 8(17),12,14-Labdatrien-18-ol Di-00404 - Di-00410

C22H 320 4 M 360.492 Constit. of Callitris columellaris and Juniperus oxycedrus.

Constit. of R. murchisonii. Oil. Cryst. (MeOH). Mp 129-130° (115-117°). [ocJn +53.6°
Zdero, C. eta/, Phytochemistry, 1987, 26, 1759. (CHC1 3).
19-A/dehyde: [56709-03-6]. 8(17),13(16),14-Labdatrien-19-a/.
8(17},12,14-Labdatriene-3,19-diol Dl-00404 Myrceocommunal
C20H 300 M 286.456
lsol. from J. oxycedrus.
~ Atkinson, P.W. et a/, Tetrahedron, 1970, 26, 1935 (isol, ms)

W
I~
Carman, R.M. eta/, Aust. J. Chern., 1971, 24, 353 (isol, pmr)
Teresa, J.P. eta/, An. Quim., 1972, 68, 1061; 1978, 74, 966 (isol)
HO'
HOH2 C H 8(17),12,14-Labdatrien-3-ol Dl-00408
C20H 320 2 M 304.472 3-Hydroxybiformene
(ent-3P,12E)-form
Constit. of Mikania alvimii. Gum. [oc]~4 -14° (c, 0.3 in
CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 173. (3cr., 12£)-form

8(17},12,14-Labdatriene-18,19-diol Dl-00405

w
C20H 320 M 288.472
~ (3r~.,12E)-form [71052-16-9]
Constit. of Palafoxia rosea and of Juniperus
pseudosabina. Oil. [oc]i;' +4° (c, 29.6 in CHC1 3).
(3p,l2E)-form [71052-17-0]
Constit. of P. rosea. Oil. [oc]~4 + 13.SO (c, 12.3 in CHC1 3).
HOH2C CHpH Ac: [71052-18-1]. Jr~.-Acetoxybiformene
C20H 320 2 M 304.472 C22H 340 2 M 330.509
Constit. of P. rosea. Cryst. (pet. ether). Mp 118°. [oc]~4
(ent-12E)-form
+51° (c, 3 in CHC1 3).
Constit. of Mikania alvimii. Gum. [ocln -7° (c, 0.2 in
CHC1 3). 3-Ketone: [71052-19-2]. 8(17),12£,14-Labdatrien-3-one. 3-
0xo-12E-biformene
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 173.
C2oH 300 M 286.456

H::r
Constit. of P. rosea and of J. pseudosabina. Oil. [oc]i;'
7,11,14-Labdatriene-6,13,17-triol Dl-00406 +5° (c, 4.5 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 115.
Pondita, K. et al, Indian J. Chern., Sect. B, 1987, 26, 453.

8(17),12,14-Labdatrien-7-ol Dl-00409
~CHPH

~OH
C20H 320 3 M 320.471
(ent-6P,JJE,13~)-form
6,17-Di-Ac: ent-6p,J7-Diacetoxy-7,11E,14-Iabdatrien-13~-ol
C 24 H 36 0~ M 404.545
Constit. of Rutidosis murchisonii. Oil. C20H 320 M 288.472
Zdero, C. eta/, Phytochemistry, 1987, 26, 1759. (7p,J2E)-form [82451-46-5] Raimonol
Constit. of Nicotiana raimondii. Cryst. Mp 101-103°.
[oc]~ +24.8° (c, 0.55 in EtOH).
8(17),13(16),14-Labdatrien-19-oic acid Dl-00407
Noma, M. eta/, Phytochemistry, 1982, 21, 395.
Myrceocommunic acid. L1.P(I 6>-Communic acid
[31323-66-7]
8(17),12,14-Labdatrien-18-ol Dl-00410

M 302.456
C20 H 320 M 288.472
~
~
(ent-12Z)-form [19654-88-7] Ozol

722
8(17),12,14-Labdatrien-19-ol- 7-Labdene-15,19-dioic acid Di-00411 - Di-00415

Constit. of Danie/lia ogea. Oil. [1X]n -27° (c, 1.6 in 8(17),13(16),14-Labdatrien-7-ol Dl-00412
CHC1 3).
18-Aldehyde: ent-8(17), 12Z, 14- Labdatrien-18-al. 18-
0xobiformene
C20H 300 M 286.456
Constit. of Helianthus decapetalus. Oil.
18-Carboxylic acid: [5573-13-7]. ent-8(17), 12Z,l4-
Labdatrien-18-oic acid. Ozic acid
C20H 300 2 M 302.456
Constit. of D. ogea. Cryst. (MeOH). Mp 141-143°. [1X]i;1
-47° (CHC1 3).
Bevan, C.W.L. eta/, J. Chern. Soc. C, 1968, 1063. C20 H 320 M 288.472
Bohlmann, F. et al, Phytochemistry, 1980, 19, 863.
7P-form [87458-63-7] Isoraimonol
Constit. of Nicotiana raimondii. Cryst. Mp 70-72°. [a]i;
8(17), 12,14-Labdatrien-19-ol Dl-00411 + 18.1 o (c, 0.24 in EtOH).
Noma, M. eta/, Phytochemistry, 1982, 21, 395.

6,8(17),13-Labdatrien-15,16-olide Dl-00413

(12£)-form 0

C20H 32 0 M 300.440
(12E)-form [10178-31-1] Elliotinol ent-form
Constit. of the oleoresin of slash pine (Pinus e/liottii) Constit. of Acritopappus longifolius. Gum. [a]i: +go (c,
and of Agathis australis. Cryst. by subl. Mp 14-15°. [1X]i; 0.2 in CHC1 3).
+ W (c, 2 in EtOH).
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 275.
p-Nitrobenzoyl: Cryst. (EtOH). Mp 128-130°. [1X]i; + 74° (c,
2 in EtOH).
Carboxylic acid: [2761-77-5]. 8(17),12E,l4-Labdatrien-19-
7-Labdene-15, 18-d.ioic acid Dl-00414
oic acid. Communic acid
COOH
C20H 30 0 2 M 302.456
Constit. of Juniperus, Cupressus, Pinus spp. etc., also
Hermas villosa and Agathis australis. Plates
(Me 2C0jpet. ether) or oil. [a]i; +40° (c, 1 in EtOH).
Carboxylic acid, Me ester: Cryst. (MeOHjEtzO). Mp 105-
1060. [a]n +45° (c, 2 in CHC1 3).
(12Z)-form [1156-07-6] Communol C20H 320 4 M 336.470
Constit. of A. australis. Oil. (JJS)-form
Carboxylic acid: [1231-35-2]. 8(17),12Z,l4-Labdatrien-19- Constit. of Ericameria linearifolia. Oil (as di-Me ester).
oic acid. Elliotinoic acid [ali: + 16.44° (c, 4.34 in CHC1 3) (di-Me ester).
C20H 300 2 M 302.456 13f.-form
Constit. of A. australis and H. villosa. Unstable oil.
18-Alcohol: 18-Hydroxy-7-labden-15-oic acid
Carboxylic acid, Me ester: Cryst. by subl. Mp 41-42°. [1X]n C20H 340 3 M 322.487
+45° (c, 2.3 in CHC1 3). Constit of Grindelia discoidea.
Narasimhachari, N. et a/, Can. J. Chern., 1961, 39, 2572 (isol)
Dentali, S.J. eta/, Phytochemistry, 1987, 26, 3025.
Arya, V.P. et a/, Tetrahedron, 1961, 16, 255 (iso/, struct)
Carman, R.M. eta/, Aust. J. Chern., 1964, 17, 395; 1966, 19, 2403
(iso/, pmr) 7-Labdene-15,19-d.ioic acid Dl-00415
Norin, T., Acta Chern. Scand., 1965, 19, 1020 (pmr, conjig)
Joye, N.M. eta/, J. Org. Chern., 1965, 30, 429.
Thomas, B.R., Acta Chern. Scand., 1966, 20, 1074 (isol) COOH
Bohlmann, F. eta/, Chern. Ber., 1974, 107, 1416 (isol)

COOH
C20H 320 4 M 336.470
(13f.)-form
Constit. of Gutierrezia Iucida. Oil.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1533.

723
8(17)-Labdene-15,18-dioic acid - 7-Labdene-15,17-diol Di-00416- Di-00420

8(17)-Labdene-15,18-dioic acid Dl-00416 2-Ac, 15-0-(4-acetoxycinnamoy/):

C33H460 6 M 538.723
Constit. of A. pseudoarborea. Oil. [cx]i; -0.9° (c, 0.9 in
CHCI 3).
2-Ac, 15-0-(4-acetoxy-3-methoxycinnamoy/):
WOOOH(BS),{o'm C34H 480 7 M 568.749
Constit. of A. pseudoarborea. Oil. [cx]~4 -I .SO (c, 0.5 in
COOH CHC1 3).
C 20H 310 4 M 336.470 2-Ac, 15-0-(3,4-diacetoxycinnamoy/):
(138)-form [1412-99-3] Pillifolic acid C3!1H480 8 M 596.759
Constit. of Pinus silvestris. Cryst. (Me2COjisopropyl Constit. of A. pseudoarborea. Oil. [cx]i; - 1.4° (c, 2.0 in
ether). Mp 194-195°. [cx)0 +26° (c, 1.5 in EtOH). CHC1 3).
(ent-138)-form (2P,13~)-form
ent-Pillifolic acid Constit. of Stevia samaipatensis. Oil.
Constit. of Hymenaea ob/ongifolia and Trachylobium 15-Carboxylic acid: ent-2cx-Hydroxy-7-labden-15-oic acid.
verrucosum. Cryst. (Me2CO/CH 2Cl2). Mp 191-192°. [cx] 0 Dihydrodendroidinic acid
-25° (c, 1.4 in EtOH). C 20H 340 3 M 322.487
(ent-13R)-form Constit. of Pleurocoronis p/uriseta.
8(17)-Eper•ene-15,18-dioic acid Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2433
Constit. of Ricinocarpus muricatus. Needles or prisms. (Dihydrodendroidinic acid)
Mp 151-152°, Mp 158-159° (dimorph.). [cx] 0 -36° (c, 5.4 Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2127 (isol)
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835 (isol)
in EtOH).
Jakupovic, J. eta/, Phytochemistry, 1989, 28, 2741 (isol, pmr, cd)
Enzell, C. et a/, Acta Chern. Scand.; 1962, 16, flJ7.
Enzell, C. et a/, Ark. Kemi, 1965, 23, 367 (ms)
Henrick, C.A. et a/, Tetrahedron, 1965, 21, 3219. 7-Labdene-3,15-diol Di-00419
Hugel, G. eta/, Tetrahedron, Suppl., No. 8, 1966, 203. 15
Cunningham, A. eta/, Phytochemistry, 1973, 12, 633. CHPH

13-Labdene-15,17-dioic acid Dl-00417

(31X, 13R)-form
HO'

(ent-8CJ.H,I3E)-form C20H360z M 308.503

(3rz,13R)-form
3-Ketone: 15-Hydroxy-7-labden-3-one
C 20H 340 1 M 306.487
c~3lo4 M 336.470 Constit. of Stevia samaipatensis. Oil.
(ent-BrzH,lJE)-form [74513-90-9]
15-Carboxy/ic acid, 3-ketone: [59806-19-8]. 3-0xo-7-/abden-
Constit. of Ayapana amygdalina. Oil (as Me ester). [cx]~4
15-oic acid. 3-0xocativinic acid
+ 37° (c, 0.1 in CHC1 3) (Me ester).
C 20H 310 3 M 320.471
(ent-8rzH,13Z)-form [74513-89-6] lsol. from Brickellia voreaicaefolia. Cryst. (Et 20/pet.
Constit. of A. amygda/ina. Oil (as Me ester). [cx]i; ether). Mp 75-76°. [ex]~ -35.4° (c, 1.3 in CHCI 3).
-20.2° (c, 0.1 in CHCI 3) (Me ester).
(3rz,l3~)-form
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1997. 15-Carboxylic acid: [73696-03-4]. 3rz-Hydroxy-7-labden-15-
oic acid
7-Labdene-2,15-diol Dl-00418 C 20H 340 3 M 322.487
Constit. of Chrysothamnus nauseosus. Oil.
(3P,13~)-form
15-Carboxy/ic acid: 3/J-Hydroxy-7-labden-15-oic acid
(21X, 13R)-form lsol. from C. nauseosus . Oil.
Bohlmann, F. eta/, Chern. Ber., 1976, 109, 1436.
Bohlmann, F. et a/, Phytochemistry, 1979, 18, 1889.
Zdero, C. eta/, Phytochemistry, 1988, 27, 2835.
c~ 36 0 1 M 308.503
(2rz,13R)-form
7-Labdene-15,17-diol Dl-00420
15-Carboxy/ic acid: [125180-45-2]. lrz-Hydroxy-7-labden-15-
oic acid
Isol. from Brickellia laciniata, also as various esters.
(2rz,13~)-form
Cryst. (Etpjpet. ether). Mp 70°. [cx]i; -1.SO (c, 0.61 in
CHC1 3).
2,15-Di-Ac: 2rz,15-Diacetoxy-7-lllbdene 13S-form
C 24H 400 4 M 392.578
Constit. of Aristeguietia pseudoarborea. Oil. [cx]i; - 1.6° M 308.503
(c, 1.5 in CHC1 3).

724
8(17)-Labdene-2,15-diol - 8(17)-Labdene-15,18-diol Di-00421 - Di-00424

17-Carboxy/ic acid: 15-Hydroxy-7-/abden-17-oic acid. 15-A/dehyde: JP-Hydroxy-8(17)-labden-15-al

Havardic acid B C20 H340 1 M 306.487
C20H340 3 M 322.487 Isol. from A. imbricata. Oil.
Constit. of Crindelia havardii. Oil (as Me ester). [cx]i;l 15-Carboxy/ic acid: JP-Hydroxy-8(17)-labden-15-oic acid
-65° (c, 4.2 in CHC1 3) (Me ester). C20H340 3 M 322.487
15,17-Dioic acid: 7-Labdene-15,17-dioic acid. Havardic acid lsol. from A. imbricata. Bp0 . 5 200° (as Me ester). [cxln
A + 52° (c, 0.5 in CHC1 3) (Me ester).
C20H320 4 M 336.470 Chandra, G. et al, J. Chern. Soc., 1964, 3648 (isol, uu, ir, ms)
Constit. of G. havardii. Oil (as di-Me ester). [cx]i;l -56°
(c, 4.3 in CHC1 3) (di-Me ester).
8(17)-Labdene-14, 15-diol Dl-00423
(131;.)-form
Di-Ac: 15,17-Diacetoxy-7-lllbdene OH
C14H 400 4 M 392.578
Constit. of Halimium verticillatum. Oil. [cx]i;1 -9.7° (c,
0.83 in CHC1 3).
17-Carboxy/ic acid:
C:zoH340 3 M 322.487
Isol. from H. viscosum and H. verticillatum. Oil. [cx]i;1
-24.1° (c, 1.31 in CHC1 3).
C20 H360 1 M 308.503
17-Carboxy/ic acid, 15-Ac: 15-Acetoxy-7-lllbden-17-oic acid
(13~,141;.)-form
C22H360 4 M 364.524
From H. viscosum and H. verticil/atum. Oil. [cx]i;1 - 36.6° Constit. of Hemizonia congesta. Gum. [cx]i;' +82° (c,
(c, 1 in CHC1 3). 0.71 in CHC1 3).
14-Ac:
17-Carboxy/ic acid, 15-Ac, Me ester:
C22H 380 3 M 350.540
C13H 31.04 M 378.551
From H. viscosum. Oil. [cx]i;1 -84.SO (c, 1.18 in CHC1 3). Constit. of H. lutescens. Gum.
15-Ac:
17-Carboxy/ic acid, 15-0-Z-cinnamoy/: 15Z-Cinnamoyloxy-
17-lllbden-17-oic acid C22H 380 3 M 350.540
Constit. of H. lutescens. Gum.
c~40o4 M 452.633
Cons~it. of H. verticillatum. Oil (as Me ester). [cx]i;1 Bohlmann, F. et al, Phytochemistry, 1981, 20, 2383.
-25.SO (c, 2.1 in CHC1 3) (Me ester).
15,17-Dioic acid: Constit. of H. verticillatum. Oil (as di-Me 8(17)-Labdene-15,18-diol Dl-00424
ester). [cx]i;1 -21.8° (c, 0.77 in CHC1 3) (di-Me ester).
Jolad, S.D. et al, Phytochemistry, 1987, 26, 483.
Urones, J.G. et al, Phytochemistry, 1987, 26, 3037; 1989, 28, 557.
:
!(-H
I CHPH
15
8(17)-Labdene-2,15-diol Dl-00421
H
1 CHPH
18

C20H 360 1 M 308.503

(ent-IJS)-form
Constit. of Trachylobium verrucosum. Oil. [cxln -36° (c,
0.9 in CHC1 3).
C20H360 1 M 308.503 Bis-4-nitrobenzoy/: Cryst. (Etp). Mp 122.4°.
(ent-2rz,131;.)-form 15-Carboxy/ic acid: [28644-60-2]. ent-18-Hydroxy-8(17)-
Constit. of Baccharis sternbergiana. Oil. lllbden-15-oic acid
2-Ketone: ent-15-Hydroxy-8(17)-lllbden-2-one C20H 340 3 M 322.487
C20H340 1 M 306.487 . Constit. of T. verrucosum. Oil (as Me ester). [cxln -37°
From B. sternbergiana. Oil. [cx]i;' -24° (c, 0.3 in CHC1 3). (c, 2.3 in CHC1 3) (Me ester).
Bohlmann, F. et al, Phytochemistry, 1984, 23, 1109. 18-Carboxy/ic acid: ent-15-Hydroxy-8(17)-labden-18-oic
acid. 15-Hydroxy-8(17)-eperuen-18-oic acid
C20H 340 3 M 322.487
8(17)-Labdene-3,15-diol Dl-00422 Constit. of Ricinocarpus muricatus. Cryst. (C 6H 6jpet.
ether or MeOH aq.). Mp 136-137°. [cxln -51° (c, 1.1 in
CHPH EtOH).
15,18-Dioic acid: see 8(17)-Labdene-15,18-dioic acid, Di-
00416
Henrick, C.A. et al, Tetrahedron, !965, 21, 3219.
Hugel, G. et al, Tetrahedron, Suppl., No. 8, 1966, 203.

C20H360 1 M 308.503
(Jp,JJ~)-form
Isol. from Araucaria imbricata. Platelets (pet. ether). Mp
lW. [cxJn +29° (c, 0.6 in CHC1 3).

725
8(17)-Labdene-15,19-diol- 13-Labdene-8,15-diol Di-00425 - Di-00426

8(17)-Labdene-15,19-diol Dl-00425 13-Labdene-8,15-diol Di-00426

(13R)-:form
(Set, 13E)-form

C20 H 360 2 M 308.503

C20H 360 2 M 308.503 (8«,13E)-form [10267-31-9]
(13R)-form [6605-69-2]/mbricatadiol Constit. of tobacco and of Cistus symphytifolius. Cryst.
Constit. of Araucaria imbricata. Cryst. Mp 114-116°. (pet. ether). Mp 131-134° (129°). [1X]n -0.5° (CHCI 3).
[1X]~ +24.4° (CHC1 3).
15-Ac: 15-Acetoxy-13E-labden-81X-ol
19-Aldehyde: 15-Hydroxy-8(17)-labden-19-al. lmbricatolal. C22 H 380 3 M 350.540
15-Hydroxyimbricatolal (incorr.) Constit. of Parentucellia latifolia. Oil. [IX]~ -22° (c, 1.1
C20H 340 2 M 306.487 in CHCI 3).
lsol. from A. imbricata. 15-Aldehyde: [89576-50-1]. 8«-Hydroxy-13E-IIlbden-15-al
19-Aldehyde, 15-formyl: 15-Formylimbricato/al. 15- Constit. of Juniperus thurifera. Cryst. Mp 105°. [IX]~
Formyloxyimbricatolal (incorr.) + 12.1° (CHCI 3).
C21 H 340 3 M 334.498 15-Carboxylic acid: 8«-Hydroxy-13-/abden-15-oic acid
From A. imbricata. Oil. [1X]i; + 17.6° (c, 1.2 in CHC1 3). C20 H 340 2 M 306.487
19-Aldehyde, 15-Ac: Acetylimbricatollll Constit. of Haplopappus deserticola. Oil (as Me ester).
C22H 360 3 M 348.525 [1X]n + 14° (c, 0.13 in CHCI 3).
Constit. of A. imbricata. [IX]~ +20°. (8«,13Z)-form
19-Carboxylic acid: [6832-60-6]. 15-Hydroxy-8(17)-labden- 15-Aldehyde: [89576-51-2].
19-oic acid. lmbricatolic acid Constit. of J. thurifera. Cryst. (CH 2Cl 2/hexane). Mp
C20H 340 3 M 322.487 109°. [IX]~ +5.2° (CHCI 3).
lsol. from A. imbricata. [IX]~ +49° (CHCI 3) (as Me
ester). (8P,13E)-form
19-Carboxylic acid, 15-Ac: Acetylimbricatolic acid 15-Ac: 15-Acetoxy-13E-labden-8P-ol
C22H 360 4 M 364.524 C22H 380 3 M 350.540
Constit. of A. imbricata. Oil (as Me ester). Bp0 . 1 173° Constit. of P. latifolia. Oil. [IX]~ +42° (c, 1.1 in CHCI 3).
(Me ester). [IX]~ +47.4° (CHC1 3) (Me ester). (5P,8«,13E)-form [11056-03-4] Vulgarolt
(JJS)-form Constit. of Marrubium vulgare. Cryst. (C 6H 6 /pet. ether).
Mp 152-153°. [IX]~+ 0°.
Dialdehyde: [7090 1-87-0]. 8(1 7)- Labdene-15, 19-dial.
Junicedral (ent-8«,13E)-form [22338-63-2] Aplumamixol
C20 H 32 0 2 M 304.472 Constit. of Beyeria spp. and Aphanamixis polystacha.
lsol. from Juniperus communis. Oil. [1X]n + 16.1° (c, 0.99 Cryst. (pet. ether). Mp 131-132°. [1X]n +0.6° (c, 1.4 in
in CHC13). CHC1 3).
Dicarboxylic acid: [41787-69-3]. 8(17)-Labdene-15,19-dioic (ent-Bp,13E)-form
acid. Mercusic acid. Junicedric acid 15-Carboxylic acid: ent-BP-Hydroxy-13-labden-15-oic acid
C20H 320 4 M 336.470 C20 H 340 3 M 322.487
Isol. from Pinus merkusii, J. oxycedrus and Brickellia Isol. from Trachylobium verrucosum. Oil (as Me ester).
glomerata. Cryst. (EtOH/EtOAc) or gum. Mp 121-128°. [1X]n -37° (c, 0.8 in CHC1 3) (Me ester).
[1X]n + 33.8° (c, 1 in EtOH). (ent-8l;,13E)-form
(ent-13S)-form 15-Aldehyde: Isol. from Acritopappus longifolius. Oil. [1X]~4
Dicarboxylic acid: [29455-26-3]. ent-8(17)-Labdene-15, 19- -29.1° (c, 1.4 in CHCI 3).
dioic acid. Oliveric acid (ent-8l;,13Z)-form
C20H 320 4 M 336.470 15-Aldehyde: Constit. of A. longifolius. Oil.
Isol. from Daniellia oliveri. Cryst. (MeOH). Mp 142°.
Asselineau, C. et a/, Bull. Soc. Chim. Fr., 1961, 1429 (synth)
[1X]n -2° (c, 1 in EtOH). Hugel, G. et a/, Tetrahedron, Suppl. 8, 1966, 203 (iso/, acid)
Bruns, K., Tetrahedron, 1968, 24, 3417. Chandrasekharan, S. eta/, J. Indian Chern. Soc., 1968, 45, 208
Haeuser, J. eta/, Tetrahedron, 1970, 16, 3461. (Aphanamixol)
De Pascual Teresa, J. eta/, An. Quim., 1974, 70, 1015; 1977, 73, Carman, R.M., Aust. J. Chern., 1973, 26, 879 (struct)
568 (Junicedral) Popa, D.P. et a/, Khim. Prir. Soedin., 1975, 11, 772; Chern. Nat.
Garbarino, J.A. eta/, J. Nat. Prod. (Lloydia), 1987, 50, 935. Compd. (Engl. Trans/.), 752 (Vulgarol)
Calderon, J.J. eta/, Phytochemistry, 1987, 26, 2639. Gonzalez, A.G. eta/, Phytochemistry, 1975, 14, 2655 (iso/)
Wahlberg, I. et a/, Acta Chern. Scand., Ser. B, 1979, 33, 541-(iso/)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 275 (aldehyde)
Calabuig, M.T. eta/, Phytochemistry, 1981, 20, 2255 (isol)
Nishizawa, M. eta/, J. Org. Chern., 1986, 51, 806 (synth)
San Filiciano, A. eta/, Phytochemistry, 1988, 27, 2241 (aldehyde)
Zdero, C. eta/, Phytochemistry, 1990, 29, 326 (8-Hydroxy-13-
/abden-15-oic acid)
Urones, J.G. et a/, Phytochemistry, 1990, 29, 2223 (iso/, pmr, cmr)

726
13-Labdene-9,15-diol - 7-Labdene-2,3,15-triol Di-00427 - Di-00431

13-Labdene-9,15-diol Di-00427 Blephllrizol A

Constit. of Blepharizonia plumosa.
Jolad, S.D. et al, Phytochemistry, 1990, 29, 905 (isol, pmr, cmr, ms)

13-Labdene-2,3,8,15-tetrol Di-00430

r r C H 20H

C20H 360 2 M 308.503 HOwl'//

(8PH,9ft,13E)-form [17140-23-7] Peregrinol OH
Constit. of Marrubium peregrinum. Cryst. Mp 130- HO H
130.50. [1X]i;' + 10.1° (CHCl3).
Salei, L.A. et a/, Khim. Prir. Soedin., 1967, 301 (isol) C20 H 360 4 M 340.502
Popa, P.D. et al, Rastit. Resur., 1973, 9, 384; CA, 80, 12454 (isol) (ent-2rx.,3rx.,8rx.,13E)-form
Constit. of Ophryosporus floribundus.
14-Labdene-8,13-diol Di-00428 Zdero, C. et al, Phytochemistry, 1990, 29, 3247 (isol, pmr)

7-Labdene-2,3,15-triol Di-00431

(Sex, 13R):form

C20H 360 2 M 308.503 (2cx,3cx, 13R):form

(8rx.,13R)-form
13-Episclareol. 13-epi-Sclareol
Constit. of Polemonium viscosum. Needles (MeOH aq.).
Mp 125-127°. [1X]n +6.6° (c, 0.016 in CHC1 3). (2rx.,3rx.,13R)-form
(8rx.,13S)-form [515-03-7] Sclareol
Constit. of Salvia sclarea. Also from S. schimperi.
Intermed. used in perfumery industry for manuf. of
synthetic ambergris odourants. A potent inhibitor of
growth of rust fungi. Cryst. (pet. ether). Mp 105.5-
106.00. [1XH)! -6.25° (EtOH).
6-Deoxy-IX-L-idopyranoside: [77451-20-8]. (ent-2rx.,3rx.,13C,)-form
C26H 460 6 M 454.646
Constit. of Aster spathulifolius. Cryst. [1X]n -33.2°
(MeOH).
(ent-8ft,l3S)-form [74638-09-8]
Constit. of Gnaphalium undulatum. Oil (as di-Ac). [1X]~4
-5.5° (c, 2 in CHC1 3) (di-Ac).
Bigley, D.B. et al, J. Chern. Soc., 1960, 4613 (isol)
Almqvist, S. et al, Acta Chern. Scand., Ser. B, 1975, 29, 695 (isol,
struct)
Bohlmann, F. et al, Phytochemistry, 1980, 19, 71 (isol)
Uchio, Y. et al, Tetrahedron Lett., 1980, 21, 3775 (isol)
Bemardinelli, G. eta/, Acta Crystallogr., Sect. C, 1988, 44, 715
(cryst struct)
Stierle, D.B. et al, Phytochemistry, 1988, 27, 517 (13-Episclareol) (ent-2rx.,3p,J3C,)-form
Banthorpe, D.V. et al, Phytochemistry, 1990, 29, 2145 (biosynth,
bib[)
8(17)-Labdene-7,13,14,15-tetrol Di-00429
OH
I
C20 H 360 3 M 324.503
15-Carboxylic acid: [88202-36-2]. 21X,31X-Dihydroxy-8-
labden-15-oic acid. 2rx.,3rt-Dihydroxycativic acid
C20H 340 4 M 338.486
Isol. from Baccharis petiolata and Brickellia
veronicaefolia. Cryst. (MeOH). Mp 150-152°. [1X]n
+ 11.81 o (MeOH), [1X]i;' -1.45° (CHC1 3).
Isol. from Baccharis salicifolia. Oil.
15-Carboxylic acid: ent-21X,31X-Dihydroxy-7-labden-15-oic
acid. ent-21X,31X-Dihydroxycativic acid
C20H 340 4 M 338.486
Isol. from B. salicifolia.
15-Carboxylic acid, 3-angeloyl:
C25 H 400 5 M 420.588
Constit. of Brickellia paniculata. Oil. [1X]n + 11.1° (c,
0.915 in CHC1 3).
15-Carboxylic acid, 3-angeloyl, Me ester:
C2,H420s M 434.615
From Brickellia eupatoriedes. Gum.
15-Carboxylic acid, 2-(3-methyl-2-butenoyl), 3-Ac, Me ester:
C28 H 440 6 M 476.652
Constit. of Aristeguieta pseudoarborea. Oil.
Bohlmann, F. et al, Phytochemistry, 1982, 21, 181 (isol)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2127 (isol)
Gomez, F. et a/, Phytochemistry, 1983, 22, 1292 (isol)
Calderon, J.S. et al, Phytochemistry, 1983, 22, 1783 (isol, pmr)
Zdero, C. et al, Phytochemistry, 1986, 25, 2841; 1990, 29, 2611
(isol, struct, abs co'lfig)
Gianello, J.C. et al, Phytochemistry, 1990, 29, 656 (isol, pmr, cmr)

C20H 360 4 M 340.502

(7rx.,13R,14R)-form

727
7-Labdene-13,14,15-triol - 13-Labdene-2,8,15-triol Di-00432 - Di-00437

7-Labdene-13,14,15-triol Dl-00432 8(17)-Labdene-3,7, 15-triol Dl-00435

13,14,15-Trihydroxy-7-labdene [97165-49-6]
OH
I

(3p, 7cx, 13S}:form

C20H 360 3 M 324.503

C20H 360 3 M 324.503 (3P,7rz,13S)-form
(13R,l4R)-form 15-Carboxylic acid: [126017-09-2). 3p,7rz-Dihydroxy-8(17)-
Constit. of Madia sativa. Gum. [cx]~4 +4.1° (c, 1.0 in labden-15-oic acid
CHC1 3). C 20 H 340 4 M 338.486
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1103. lsol. from Eupatorium salvia. Oil.
(3P,7rz,131;)-form
8-Labdene-3,7,15-triol Dl-00433 Constit. of Halimium viscosum. Oil. [cxJi? -16.9° (c, 1.1
in CHC13).
de Pascual Teresa, J. eta/, Phytochemistry, 1985, 24, 791.
Gonzalez, A.G. et a/, Phytochemistry, 1990, 29, 321.
(3p,7cx,13S}:form
8(17)-Labdene-13,14,15-triol Dl-00436
OH
C 20H 360 3 M 324.503
(3p,7rz,13S)-form
7-Me ether: [114359-99-8]. 7rz-Methoxy-8-labdene-3p,l5-diol
C 21 H 38 0 3 M 338.529
Constit. of Halimium viscosum.
7-Me ether, 3,15-Di-Ac: Oil. [cx)i? + 24.3° (c, 0.8 in CHC1 3).
7-Ketone: [114360-00-8]. 3P,15-Dihydroxy-8-labden-7-one
C 20H 340 3 M 322.487 C 20H 360 3 M 324.503
Constit. of H. viscosum. (131;,141;)-form
7-Ketone, 3,15-Di-Ac: Oil. [cxJi? +26.2° (c, 0.72 in CHC1 3). Constit. of Hemizonia spp. Gum.
(3p,7p,13S)-form 15-Ac:
C22H 380 4 M 366.540
3-Me ether: 3P-Methoxy-8-labdene-7p,l5-diol Constit. of H. lutescens. Gum. [a)~4 + 10° (c, 0.8 in
C 21 H 380 3 M 338.529 CHC1 3).
Constit. of H. viscosum. Oil.
15-Ac, 14-propanoyl:
[114420-21-2) C25H4205 M 422.604
Urones, J.G. et a/, Phytochemistry, 1988, 27, 501; 1990, 29, 2927 Constit. of H. lutescens. Gum.
(isol, pmr, cmr, synth)
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 2383.

8-Labdene-13,14,15-triol Dl-00434 Dl-00437

13-Labdene-2,8,15-triol
13,14,15-Trihydroxy-8-labdene
OH
I

HOWOH ~CH2 0H

C 20H 360 3 M 324.503

(ent-2rz,8rz,13E)-form
C 20H 360 3 M 324.503 Constit. of Gutierrezia solbrigii. Gum.
(13R,l4R)-form Jakupovic, J. et a/, Tetrahedron, 1985, 41, 4537.
Constit. of Madia sativa. Gum.
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 1103.

728
13-Labdene-3,8,15-triol - 14-Labden-8-ol Di-00438 - Di-00443

13-Labdene-3,8,15-triol Dl-00438 7-Labden-15-oic acid Dl-00441

[100664-56-0]
IS
CHpH

(13S)-form
(3p,8cx, 13£)-form

c~360 3 M 324.503 C10H 340 2 M 306.487

(3P,8«,13E)-form (JJS)-form [468-82-6] Cati11ic acid
Constit. of an Acacia sp. Cryst. Mp 160-161°. [ex]n Constit. of Prioria copaifera. Cryst. (MeOH or AcOH).
-3.3° (c, 0.5 in CHC1 3). Mp 80-82°. Bp 1 194-195°. [ex]n -6.6° (EtOH).
15-Carboxy/ic acid: [100664-58-2]. 3ft,8«-Dihydroxy-13E- (ent-JJR)-form [15770-53-3]
illbden-15-oic acid 7-Eperuen-15-oic acid
Constit. of A. sp, Cryst. (EtOAc). Mp 123-124.SO. [ex]n lsol. from wood of Oxystigma oxyphyllum. Oil (as Me
+ 10.4° (c, 1.9 in MeOH). ester). [exln -8° (Me ester).
(ent-3«,8«,13£)-form Zeiss, H.H. eta/, J. Am. Chern. Soc., 1957, 79, 1201 (isol)
Constit. of Ophryosporus floribundus. Enzell, C. eta/, Ark. Kemi, 1965, 23, 367 (ms)
Bevan, C.W.L. et al, J. Chern. Soc. C, 1968, 1067 (isol)
3-Ac:
C12H 380 4 M 366.540
Constit. of 0. floribundus. Cryst. Mp 151°. [ex]i: -44° (c, 8(17)-Labden-15-oic acid Dl-00442

w
0.52 in CHC1 3).
3-Ketone: 8,15-Dihydroxy-13-/abden-3-one
C10H 340 3 M 322.487
~H
Constit. of 0. floribundus. Cryst. Mp 134°. COOH
Forster, P.G. eta[, Phytochemistry, 1985, 24, 2991.
Zdero, C. eta[, Phytochemistry, 1990, 29, 3247. (ent-13R)-form

C10H 340 2 M 306.487

13-Labdene-8,12, 15-triol Dl-00439 (ent-JJR)-form [20784-69-4] Eperuic acid
Constit. of oleoresin of Eperua falcata and other spp.
Liq. Bp0.7 190°.
Me ester: Liq. Bp 1 164°. [ex]~ -28.2° (c, 3.98 in CHC1 3).
9-0ctadeceny/ ester:
C38H 680 2 M 556.954
Constit. of E. falcata. Oil. Bp0 .0002 235-240°. [ex]~ -7.1°
(c, 2.4 in CHC1 3).
(ent-JJS)-form [561-91-1]
c~360 3 M 324.503 Constit. of Trachylobium verrucosum. Mp 136° (as
(8«,12S,13E)-form [101758-45-6]
cyclohexylamine salt). [exln - 14° (cyclohexylamine salt).
Constit. of leaves of Greek tobacco. Cryst. Mp 108- King, F.E. et al, J. Chern. Soc., 1955, 658 (isol)
llO.SO. [ex]n +4.7° (c, 0.43 in CHC1 3). Henrick, C.A. et al, Tetrahedron, 1965, 21, 1175 (struct)
Hugel, G. et al, Tetrahedron, Suppl. 8, 1966, 203 (isol, struct)
Nishida, T. et al, J. Chern. Soc., Chern. Commun., 1985, 1489 (cmr)
Wahlberg, I. et al, Acta Chern. Scand., Ser. B, 1988, 42, 708 (isol,
pmr, cmr) 14-Labden-8-ol Dl-00443
[117101-04-9]
13-Labdene-8,15,16-triol Dl-00440

C10H 360 M 292.504

C10H 360 3 M 324.503 (ent-Bf/)-form
(8«,13Z)-form [130395-42-5] Constit. of Aristo/ochia cymbifera. Oil. [ex]i,S -5° (c, 0.60
Constit. of Baccharis salicifolia. Gum. in CHC1 3).
8-0-P-Xy/opyranoside: [130395-43-6]. Lopes, L.M.X. et a/, Phytochemistry, 1988, 27, 2265.
C25H 440 7 M 456.618
Constit. of B. salicifolia. Gum.
8-0-P-Fucopyranoside:
C26H 460 7 M 470.645
Constit. of B. salicifolia. Gum.
Jukupovic, J. et al, Phytochemistry, 1990, i9, 2217 (isol, pmr)

729
Lasiocoryin - Nivenolide Di-00444 - Di-00449

Lasiocoryin 01-00444 Nepetaefolin 01-00447

9rx,13<!:15,16R-Diepoxy-3P,16R,18-/abdanetrio/ 6P-Acetoxy-8P,J7:9rx,13:15,16-triepoxy-14-labden-19,20-o/ide
(53823-01-1] (29606-32-4]

C20H340s M 354.486 CuHl1107 M 404.459

Constit. of Lasiocorys capensis. Cryst. Mp 175°. [rxln +6°. Constit. of Leonotis nepetaefo/ia. Cryst. (MeOH/Me 2CO).
Gafner, G. eta/, J. Chem. Soc., Chem. Commun., 1974, 249 Mp 260° dec. [rx]i; -14.6° (c, 0.9 in CHCI 3).
(struct) 14,15-Dihydro, 15R-methoxy: [43207-64-3].
Rivett, D.E.A., J. S. Afr. Chem. /nst., 1975, 28, 305 (isol) Methoxynepetaefolin
C23H 320 8 M 436.501
Leonitin 01-00445 Isol. from L. nepetaefo/ia. Cryst. Mp 275-278°. [rx]i:'
20-Acetoxy-9rx,13R-epoxy-15,16:19,6P-labdanedio/ide -35.8° (c, 1.2 in CHC1 3).
[68961-02-4] Manchand, P.S., Tetrahedron Lett., 1973, 1903
(Methoxynepetaefolin)
v. Dreele, R.B. eta/, J. Am. Chem. Soc., 1975, 97, 6236.
Blount, J.F. eta/, J. Chem. Soc., Perkin Trans. I, 1980, 264 (cryst
struct)
0
Nepetaefolinol Oi-00448
9rx,13<!-Epoxy-6p-hydroxy-16,15:19,20-/abdanediolide
[55784-79-7]

0
CuH300 7 M 406.475
Constit. of Leonotis /eonitis. Cryst. (EtOH). Mp 242-243°.
[rxJn -1° (c, 1.2 in CHCl 3).
Eagle, G.A. eta/, J. Chem. Soc., Perkin Trans. I, 1978, 994.

Leosibiricin 01-00446
9rx,13<!:15,16-Diepoxy-8-hydroxy-7-oxo-14-/abden-19,6P-
olide C20Hl806 M 364.438
[86575-85-1] Constit. of Leonotis nepetaefo/ia. Cryst. (EtpjCHCl 3). Mp
297°. [rxln +25° (c, 1.6 in CHC1 3).
Purushothaman, K.K. eta/, J. Chem. Soc., Perkin Trans. 1, 1974,
2661.

Nivenolide Dl-00449
ent-8(17),13-Labdadien-16,15-o/id-18-oic acid
[67890-42-0]
0
0
C12Hl807 M 404.459
Constit. of Leonurus sibiricus. Unstable oil. [rx]~ + 33° (c,
0.09 in CHC1 3).
Savona, G. eta/, Phytochemistry, 1982, 21, 2699.

C20Hl804 M 332.439
Constit. of Croton niveus. Cryst. (Me2CO/diisopropyl
ether). Mp 170-171°. [rxJn -38_50 (CHC1 3).
Rojas, E.T. eta/, Phytochemistry, 1978, 17, 574.

730
6-0xo-7,13-labdadien-15,16-olide - Premarrubenol Di-00450 - Di-00456

6-0xo-7,13-labdadien-15,16-olide Di-00450 Constit. of Acritopappus rnorii. Oil. [oc]i;l -44.3° (c, 1.64
in CHC1 3) (Me ester).
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695.

Precalyone Di-00454
3-Acetoxy-9,13: 15,16-diepoxy-14-labden-7-one
[71641-11-7]

C:zoH:II.OJ M 316.439
ent-form [88862-04-8]
Constit. of Acritopappus confertus. Cryst. Mp 171°. [oc]i;l
+30° (c, 0.03 in CHCI 3).
16e-Hydroxy: ent-16-Hydroxy-6-oxo-7,13-labdadien-15,16-
olide AcO
C:zoH 280 4 M 332.439
From A. confertus. Cryst. Mp 154°. [oc]i;l +60° (c, 0.03 C 11HJz05 M 376.492
in CHCI 3). Constit. of Roylea calycina. Cryst. (pet. ether). Mp 172-
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243. 1730. [oc]i; -17.1° (c, 2 in CHCI 3).
Prakash, 0. et a/, J. Chern. Soc., Perkin Trans. 1, 1979, 1305.
6-0xo-7,11,13-labdatrien-16,15-olide Di-00451
Pregaleuterone Dl-00455
7P-Acetoxy-9oc,13e:15,16-diepoxy-8e-hydroxy-14-labden-6-
0 one
[95261-29-3]

C:zoH 260 3 M 314.424

(JJE)-form
Constit. of Hedychiurn spicatum. Needles C11H 310 6 M 392.491
(Me 2CO/hexane). Mp 156°. [oc] 0 +95° (c, 1.2 in CHC1 3). Constit. of Galeopsis reuteri. Syrup. [oc]l:i +36° (c, 0.33 in
Sharma, S.C. et a/, Indian J. Chern., Sect. B, 1983, 22, 93. CHC1 3).
Savona, G. et a/, Phytochemistry, 1984, 23, 2958.
6-0xo-7,12,14-labdatrien-17,11-olide Di-00452
Premarrubenol Dl-00456
9oc,13.;:15,16-Diepoxy-14-labdene-6P,J9-diol
[72055-92-6]

C:zoH 260 3 M 314.424 HOH2

(ent-11S,l2E)-form [110201-83-7]
Constit. of Rutidosis rnurchisonii. Oil.
Zdero, C. eta/, Phytochemistry, 1987, 26, 1759.
16-0xo-8(17)-labden-15-oic acid
C:zoH 310 4 M 336.470
Constit. of Marrubiurn supinurn. Cryst. (Me2CO/hexane).
Mp 162-164°. [oc]~ -45° (c, 0.33 in CHCI 3).
Savona, G. eta/, Phytochemistry, 1979, 18, 859.
Dl-00453

C:zoH320 3 M 320.471
(ent-13~)-form

731
Premarrubiin - 3,14,19-Trihydroxy-8(17),12-... Di-00457- Di-00462

Premarrubiin Di-00457 Sciadin Dl-00460

9,13:15,16-Diepoxy-14-labden-19,6P-olide 12S,20:15,16-Diepoxy-8(17),13(16),14-labdatrien-19,20-olide

--a
[6813-08-7]

(13R)-form

0 0
C10H:11P 4 M 332.439 C20H 240 4 M 328.407
Constit. of the heartwood of Sciadopitys verticillata. Cryst.
(13R)-form [72059-02-0]
(EtOH). Mp 160°. [1X]n + 10.3° (CHC1 3).
Constit. of Marrubium vulgare. Oil. [1X]n +29° (c, 1 in
CHC1 3). Sumimoto, M., Tetrahedron, 1963, 19, 643 (isol)
Bastard, J. et a/, J. Nat. Prod. (Lloydia), 1984, 47, 592 (crnr)
(JJS)-form [24703-43-3]
Constit. of M. vulgare. Oil. [1X]n -41° (c, 0.6 in EtOH).
Laonigro, G. eta/, Gazz. Chirn. Ita/., 1979, 109, 145.
2,3,18-Trihydroxy-8(17),13-labdadien- Dl-00461
15,16-olide
Preperegrinine Dl-00458
91X,13R:15,16-Diepoxy-3-oxo-14-labden-19,6P-olide
[90578-31-7] HOWl CQ=o
HO~

HOH2 \H
CzoH34Ps M 350.454
(ent-2rr.,3JI)-form [99624-45-0]
3-Angeloyl:
CzsH 360 6 M 432.556
Isol. from Gutierrezia solbrigii. Gum.
C20H 21;0s M 346.422 Jakupovic, J. et a/, Tetrahedron, 1985, 41, 4537.
Constit. of Marrubium friwaldskyanum. Syrup. [IX]£~ -41.7°
(c, 0.28 in CHC1 3). 3,14,19-Trihydroxy-8(17),12-labdadien- Dl-00462
Savona, G. et a/, Phytochemistry, 1984, 23, 191. 16,15-olide

Prerotundifuran Dl-00459
91X,13R: 15,16-Diepoxy-14-labden-6P-ol Ho-
[50656-73-0]

HO'

CzoH34Ps M 350.454
(ent-3p,14R)-form [5508-58-7] Andrographolide
Constit. of Andrographis paniculata. Cryst. (MeOH). Mp
C22 H 340 4 M 362.508 230-231°. [IX]~ -126° (AcOH).
Constit. of Vitex rotundifolia. Mp 204-205°.
Talukdar, P.B. eta/, 1ndian J. Chern., 1968, 6, 252 (isol)
Asaka, Y. eta/, Chern. Lett., 1973, 937. Patra, A. eta/, Org. Magn. Reson., 1981, 16, 74; 17, 301 (crnr)
Hirotsu, K. eta/, Chern. Lett., 1973, 1035 (cryst struct) Fujita, T. eta/, Chern. Pharrn. Bull., 1984, 32, 2117 (cryst struct)

732
2,3,19-Trihydroxy-7-labden-15-... - Clutiolide Di-00463 - Di-00468

2,3,19-Trihydroxy-7-Iabden-15-oic acid Dl-00463

rrCOOH Secolabdanes
HOY+Y

HO~ Blepharizone Dl-00466

CHPH 9,12-Epoxy-9 ,13S,14-trihydroxy-8,9-seco-8-labdanone
[127970-60-9]
C20H 340 5 M 354.486
(ent-2rx.,3rx.,l3f,)-form
19-Ac: ent-19-Acetoxy-2rx.,3rx.-dihydroxy-7-labden-15-oic acid
C22 H 360 6 M 396.523
Constit. of Relhania corymbosa.
19-Aldehyde, 2-Ac: ent-2rx.-Acetoxy-3rx.-hydroxy-19-oxo-7-
labden-15-oic acid
CnH340 6 M 394.507
Constit. of R. corymbosa. C20H 360 5 M 356.501
Constit. of Blepharizonia plumosa.
13E,l4-Didehydro, 19-aldehyde, di-Ac: 2,3-Diacetoxy-19-
oxo-7,13E-Iabdadien-15-oic acid Jo1ad, S.D. et al, Phytochemistry, 1990, 29, 905 (isol, pmr, cmr, ms)
C24H 340 7 M 434.528
Constit. of R. fruticosa. Camporic acid Dl-00467
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol) ent-7R,9S;9,13~-Diepoxy-8-oxo-8,9-seco-15-labdanoic acid

17,18,19-Trihydroxy-13-Iabden-16,15-olide Di-00464 COOH

C20H320 5 M 352.470
Constit. of Grindelia camporum. Oil (as Me ester). [a]~
-5.7° (c, 3.4 in CHC1 3) (Me ester).
HOH2 C CH2 0H Hoffmann, J.J. et al, Phytochemistry, 1988, 27, 493.
C20H 320 5 M 352.470
(ent-BPH)-form [55803-62-8] Wightionolide Clutiolide Dl-00468
Constit. of Andrographis wightiana. Cryst. (EtOAc). Mp
176°. [aln -17.5° (c, 2.085 in AcOH). 0
Govindachari, T.R. eta/, Tetrahedron, 1965, 21, 3237 (isol)
Joshi, B.S. et al, J. Chem. Soc., Perkin Trans. 1, 1974, 2517 (struct)

8,15,19-Trihydroxy-13-Iabden-7-one Dl-00465

C20Hn0 5 M 342.391
Constit. of Clutia abyssinica. Cryst. (MeOH). Mp 165-
1660. [aln -68.9° (c, 0.189 in CHC1 3). A seco1abdane.
2,3-Dihydro: Dihydroclutiolide
C20H 240 5 M 344.407
C20H 340 4 M 338.486 Constit. of C. abyssinica. Cryst. (MeOH). Mp ll9-l20°.
(8p,J3E)-form [66471-76-9] Villenatriolone [aJn -90° (c, 0.186 in CHC13).
Constit. of Sideritis chamaedryfolia. Cryst. 2,3-Dihydro, 6-deoxo, 19-oxo: lsodihydroclutiolide
(Me2COjhexane). Mp 159-160°. [ali: -78.6° (c, 0.66 in C20H 240 5 M 344.407
EtOH). Constit. of C. abyssinica. Cryst. (MeOH). Mp 156-157°.
Rodriguez, B., Phytochemistry, 1978, 17, 281. [aJn -44.4° (c, 0.18 in CHC1 3).
Waigh, R.D. et al, Phytochemistry, 1990, 29, 2935 (isol, pmr, cmr)

733
11,10-Epoxy-9,10-seco-8,10(20),13-... - 18-Hydroxy-7,8-seco-6,12,14-... Di-00469- Di-00476

11,16-Epoxy-9,10-seco-8,10(20),13- Dl-00469 Galeopsitrione Dl-00473

labdatrien-15-ol 15,16-Epoxy-8,9-seco-13( 16),14-/abdadiene-7,8,9-trione
(87440-59-3]

C20H 340 2 M 306.487

Labdane numbering shown. Constit. of Ophryosporus
.floribundus. Gum.
C20H 280 4 M 332.439
Zdero, C. eta/, Phytochemistry, 1990, 29, 3247 (isol, pmr)
Constit. of Galeopsis angustifolia. Syrup. [IX]~ -7.SO (c,
0.61 in CHC1 3).
8,13-Epoxy-2,3-seco-14-labdene-2,3-dioic Dl-00470 Perez-Sirvent, L. et a/, Phytochemistry, 1983, 22, 527.
acid
Helipterol Dl-00474

C20H 320 5 M 352.470 C20H 340 M 290.488

(8rz,l3R)-form Constit. of Helipterum venustum. Oil. [IX]~ + 13° (c, 0.31 in
1,3-Dicarboxy-1,3-secomanoyl oxide CHC13).
Constit. of Dacrydium colensoi. Cryst. (pet. ether). Mp Zdero, C. et al, Phytochemistry, 1989, 28, 517.
191-192°.
Grant, P.K. eta/, J. Chern. Soc., 1965, 3846. 13-Hydroxy-7,8-seco-6, 14-labdadien-8-one Di-00475

Galeolone
7,9;15,16-Diepoxy-9-hydroxy-8,9-seco-6,13(16),14-
Di-00471
'
/abdatrien-8-one
[87440-58-2]

C20H 340 2 M 306.487

(ent-131;)-form [118855-41-7] Secomanool
Constit. of Fleischmannia microstemon. Oil. [1X]~4 -15°
(c, 1.2 in CHC13).
Tamayo-Castillo, G. et al, Phytochemistry, 1988, 27, 3322.
C20H 280 4 M 332.439
Constit. of Ga/eopsis angustifolia. Syrup. [1X)i,O + 31.4° (c, 18-Hydroxy-7,8-seco-6,12,14-labdatrien-8- Dl-00476
0.59 in CHC1 3). one
Perez-Sirvent, L. et al, Phytochemistry, 1983, 22, 527.

Galeopsinolone Dl-00472
15,16-Epoxy-6~hydroxy-8,9-seco-7,11-cyclo-7(1 1),13(16),14-
/abdatrien-9-one 0
8
[87440-57-1]
CH20H
0

Q);o
C20H 3p 2 M 304.472
(11E)-form [92631-77-1] 11E,U-Secokoanolabdadiene
Constit. of Koanophyllon conglobatum. Oil. [IX]~ -9° (c,
0.5 in CHC1 3).
OH Bohlmann, F. eta/, Phytochemistry, 1984, 23, 1190.
C:zoH28 0 3 M 316.439
Constit. of Ga/eopsis angustifolia. Cryst. (EtOAcfhexane).
Mp 153-154°. [1X]~ -117.9° (c, 0.273 in CHC1 3).
Perez-Sirvent, L. et al, Phytochemistry, 1983, 22, 527.

734
15-Hydroxy-8,9-seco-13-labdene-8,9-... - Strictanonoic acid Di-00477 - Di-00483

15-Hydroxy-8,9-seco-13-labdene-8,9-dione 01-00477 9,10-Seco-8,10(20),13-labdatriene- 01-00481

[118448-88-7] 11,15,16-triol

C20 H 340 3 M 322.487

C20H 340 3 M 322.487 Labdane numbering shown. Constit. of Ophryosporus
(ent-13E)-form .floribundus. Gum.
Constit. of Gypothamnium pinifolium. 11-Deoxy: 9,10-Seco-8,10(20),13-/abdatriene-15,16-diol
Zdero, C. et al, Phytochemistry, 1988, 27, 2953. C20 H 340 2 M 306.487
Constit. of 0 . .floribundus. Gum.
8-0xo-7 ,8-seco-12,14-labdadien-7-oic acid 01-00478 16-Deoxy: 9,10-Seco-8,10(20),13-/abdatriene-11,15-diol
C20H 340 2 M 306.487
Constit. of 0 . .floribundus. Gum.
16-Deoxy, 101X,20-epoxide: 10,20-Epoxy-9,10-seco-8,13-
/abdadiene-11 ,15-diol
C20H 340 3 M 322.487
Isol. from 0 . .floribundus. Gum.
11-Deoxy, 101X,20-epoxide: 10,20-Epoxy-9,10-seco-8,13-
C20H 32 0 3 M 320.471 /abdadiene-15 ,16-diol
C20H 340 3 M 322.487
(ent-11E)-form [83991-76-8] Secoathrixic acid
Isol. from 0 . .floribundus. Gum.
Constit. of Athrixia elata. Gum.
Zdero, C. et al, Phytochemistry, 1990, 29, 3247 (isol, pmr)
Bohlmann, F. et al, Phytochemistry, 1982, 21, 1806.

Seconidorella lactone 01-00482

Rotalin B 01-00479 1,10:15,16-Diepoxy-6-hydroxy-5-oxo-5,10-seco-14-/abden-
[119979-80-5] 20,12-olide
[83161-73-3]

C20H 33 Br02 M 385.383

Metab. of sponge Mycale rota/is. Amorph. solid. [1X]n
+ 13.9° (c, 0.43 in CHC1 3).
Corriero, G. et al, Tetrahedron, 1989, 45, 277.

9,10-Seco-8,10(20),13-labdatriene-3,11,15- 01-00480
trioI C20 H 260 6 M 362.422
Constit. of Nidorella hottentotica. Gum.
6-Ange/oy/:
C25H 320 7 M 444.524
Constit. of N. hottentotica. Gum. [1X]i;l -7.7° (c, 0.64 in
CHC1 3).
C20H 340 3 M 322.487 Bohlmann, F. et al, Phytochemistry, 1982, 21, 1109.
Labdane numbering shown. Constit. of Ophryosporus
.floribundus. Strictanonoic acid 01-00483
3-Ketone: 11,15-Dihydroxy-8,10(20),13-/abdatrien-3-one 6R,9S;9,13S-Diepoxy-8-oxo-8,9-seco-15-/abdanoic acid.
CwH320 3 M 320.471 Chrysothame
Constit. of 0 . .floribundus. Gum. [80865-69-6]
Zdero, C. et al, Phytochemistry, !990, 29, 3247 (isol, pmr)

M 352.470

735
Acrostalidic acid- 7,8-Dihydroxy-14,15-dinor-11-labden-... Di-00484 - Di-00489

Strictanonoic acid and Chrysothame originally descr. as Bacchalatifolin Dl-00486

13-epimers. Constit. of Chrysothamnus panicu/atus and
Grindelia stricta. Cryst. (C6H 6 jpet. ether). Mp 108-109°. ( " " f C H20H
[a]~ -16.6° (c, 1.76 in CHC1 3).

27~'¢
Hoffmann, J.J. eta/, J. Org. Chem., 1982, 47, 1725 (isol)
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 167 (isol)
Sierra, M.G. eta/, J. Chem. Soc., Chem. Commun., 1985, 1045
(synth)
Gonzalez-Sierra, M. eta/, /. Chem. Soc., Perkin Trans. I, 1989,
1393 (abs config, synth)

HO
C38 H640 6 M 616.920
Constit. of Baccharis latifolia.

Norlabdanes Zdero, C. eta/, Phytochemistry, 1989, 28, 531.

8,13:13,17-Diepoxy-14,15-dinorlabdane Dl-00487

Acrostalidic acid Dl-00484 ~0

13,14,15,16-Tetranor-6-/abden-12,17-olid-19-oic acid
[55374-11-3] ~~ (Sex, 13S}:form

0
CtsH31,01 M 278.434
(8«,13S)-form
Constit. of Pinus montico/a. Cryst. Mp 115-116°.
(8P,13R)-form
Constit. of P. monticola. Cryst. Mp 121-122°.
Conner, A.H. eta/, Phytochemistry, 1980, 19, 1121.
C16H 220 4 M 278.347
Metabolite of Acrostalagmus spp. Cryst. (EtOAc). Mp 210- 6,17-Dihydroxy-14,15-dinor-7,11- Dl-00488
2110. labdadien-13-one
Sato, M. eta/, J. Chem. Soc., Perkin Trans. 1, 1976, 2407.

C18H180 3 M 292.417
(ent-6P,Jl E)-form
Di-Ac: ent-6p,J7-Diacetoxy-14,15-dinor-7,11E-Iabdadien-13-
one
CzzH 310 5 M 376.492
Constit. of Rutidosis murchisonii. Oil. [a]i;l -138° (c, 0.1
in CHC1 3).
Zdero, C. eta/, Phytochemistry, 1987, 26, 1759.

7,8-Dihydroxy-14,15-dinor-11-labden-13- Dl-00489
one
0

C18H 31p 3 M 294.433

(7P,8«,11 E)-form
Sterebin D

736
8,16-Dihydroxy-17-nor-6,13-... - 14,15-Dinor-13-oxo-7-labden-17-... Di-00490 - Di-00495

Constit. of Stevia rebaudiana. Powder. [1X]n +22.8° (c, 15,16-Dinor-8(17),11-labdadien-13-one Dl-00492

0.05 in MeOH). 15,16-Bisnor-8(17),11-/abdadien-13-one
61X-Hydroxy: [107647-14-3]. 61X,7P,81X-Trihydroxy-14,15-
dinor-11-labden-13-one. Sterebin A 0
C18H 300 4 M 310.433
Isol. from leaves of S. rebaudiana. Needles (Me 2CO).
Mp 157-158°. [1X]n +39.6° (c, 0.63 in Me2CO).
61X-Acetoxy: Sterebin B
C 20H 3P 5 M 352.470
Constit. of S. rebaudiana. Powder. [1Xln + 15.9° (c, 0.11
in MeOH).
C 18H 280 M 260.419
61X-Hydroxy, 7-Ac: Sterebin C
C2oH 320 5 M 352.470 (llE)-form
Constit. of S. rebaudiana. Powder. [1X]n + 34.8° (c, 0.07 Constit. of Alpinia speciosa. Cryst. Mp 145.5-146.0°.
in MeOH). [1X]~ +4.SO (c, 0.3 in CHC1 3).
Oshima, Y. et a/, Tetrahedron, 1986, 42, 6443. Itokawa, H. et a/, Chern. Pharm. Bull., 1980, 28, 3452.

8,16-Dihydroxy-17-nor-6,13-labdadien-15- Dl-00490 14,15-Dinor-8-labdene-7,13-dione Dl-00493

oic acid 14,15-Bisnor-8-/abdene-7,13-dione
[72446-33-4]
15
COOH

~CH2 0H
r¥
~OH
CtsH2802 M 276.418
C19H300 4 M 322.444 Constit. of Greek tobacco. Oil. [1Xln + 28° (c, 0.08 in
(ent-8P,13E)-form CHCI 3).
Constit. of Acritopappus confertus. Vlad, P.F. eta/, Zh. Obshch. Khim., 1980, 50, 195 (synth)
16-Ac, 8-formy/: Wahlberg, I. eta/, Acta Chern. Scand., Ser. B, 1988, 42, 708 (isol,
C22H320, M 392.491 cmr)
From A. confertus. Gum (as Me ester). [1X]i;l -68° (c,
0.64 in CHC1 3) (Me ester). 14,15-Dinor-7-labden-13-one Dl-00494
8-Ketone, 16-Ac: ent-16-Acetoxy-8-oxo-17-nor-6,13£- 14,15-Bisnor-17-/abden-13-one
/abdadien-15-oic acid [7361 0-60-3]
C2tHJOOs M 362.465
From A. confertus. 0
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243.

3,8-Dihydroxy-13,14,15,16-tetranor-12- Dl-00491
labdanoic acid

CtsH 300 M 262.434

Constit. of Parentucellia latifolia. Oil.
Drones, J.G. et a/, Phytochemistry, 1990, 29, 2223 (iso/, pmr, cmr,
synth)

14,15-Dinor-13-oxo-7-labden-17-oic acid Di-00495

Ct,H 280 4 M 284.395
(3«,8«)-form
8-Ac, Me ester: Methyl8«-acetoxy-3«-hydroxy-13,14,15,16-
tetranorlabdan-12-oate
C19H320s M 340.459
Constit. of Salvia aethiopis. Gum. [1X]n -0.79° (c, 1.05 in
CHC1 3).
Gonzalez, M.S. et a/, Tetrahedron, 1989, 45, 3575. CtsH280 3 M 292.417
Constit. of Ha/imium viscosum. Oil (as Me ester). [1X]i;1
-52.0° (c, 0.70 in CHC1 3) (Me ester).
De Pascual Teresa, J. eta/, Phytochemistry, 1986, 25, 711.

737
8,13-Epoxy-14,15-dinor-12-labden-3-... - 8,13-Epoxy-3-nor-2,3-seco-14-labden-... Di-00496 - Di-00502

8,13-Epoxy-14,15-dinor-12-labden-3-ol Dl-00496 1,2-Epoxy-3-hydroxy-13, 14,15,16-

tetranor-7,9(11)-labdadiene-12,17:19,6-
diolide Dl-00499

CtaH300 2 M 278.434
(3P,8~)-form
Constit. of Cystophora moniliformis. Viscous oil. [1X]i:'
+6.2° (c, 1.3 in CH 2C12).
Ravi, B.N. eta!, Aust. J. Chern., 1982, 35, 171.
Ct6Ht606 M 304.299
11,12-Epoxy-8-hydroxy-14,15-bisnor-13- Dl-00497 (lp,2p,3p,6p)-form [76235-83-1] Wenti/actone A
Metab. of Aspergillus wentii. Phytotoxin. Cryst.
labdanone (MeOH/EtOAc). Mp 258°.
0 Domer, J.W. eta!, Phytochemistry, 1980, 19, 1157.

12,15-Epoxy-8(17),12,14-labdatrien-16-ol Dl-00500
[130451-53-5]

CtsH3003 M 294.433
(8rz,JJS,12R)-form [120056-06-6]
Constit. of Greek tobacco. Cryst. Mp 93-95°. [1X] 0 + 11°
(c, 0.18 in CHC1 3).
[119934-96-2] C20H 300 2 M 302.456
Wahlberg, I. et a/, Acta Chern. Scand., Ser. B, 1988, 42, 708 (isol, Oil.
pmr, cmr, cryst struct) Ac: [130451-51-3].
C22 H 320 3 M 344.493
9,13-Epoxy-4-hydroxy-18-nor-7-labden- Dl-00498 Constit. of Turraeanthus africanus. Oil. [1X]i:' + 21 o
15-oic acid (CHC1 3).
Cambie, R.C. eta/, Aust. J. Chern., 1990, 43, 1151 (synth, pmr,
COOH cmr)

#CH,OH
8,13-Epoxy-15-nor-14-labdanol Di-00501

C19H3004 M 322.444
(4rz,9rz,l3~)-form
4-Hydroxy-18-norgrinde/ic acid
Constit. of Grindelia spp. Oil (as Me ester). [1X]i;' - 32.SO C19H 340 2 M 294.476
(c, 0.2 in CHC1 3) (Me ester). (ent-8rz,13R)-form [107439-19-0] Sidnutol
4-Formyl: Constit. of Sideritis nutans. Cryst. Mp 99-102°. [1X] 0 -7°
C20H 300 5 M 350.454 (c, 0.1 in CHCI 3).
Constit. of G. spp. Oil (as Me ester). [1X]i;' -35° (c, 0.1 Fernandez, C. eta!, Phytochemistry, 1986, 25, 2825.
in CHC13) (Me ester).
[81916-28-1] 8,13-Epoxy-3-nor-2,3-seco-14-labden-2,4- Dl-00502
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 167. olide

C19H 300 3 M 306.444

(8rz,l3R)-form
2-0xo-3-oxamanoy/ oxide

738
8,12-Epoxy-13,14,15,16-... - Haplomitrenolide A Di-00503 - Di-00507

Constit. of Dacrydium colensoi. Cryst. (pet. ether). Mp Grindelistrictic acid Dl-00505

173-174°. 9R,13S-Epoxy-8,17-dinor-8,9-seco-7,9-labdanolid-15-oic acid
Grant, P.K. et al, J. Chem. Soc., 1965, 3846. [81916-08-7]
COOH
8,12-Epoxy-13,14,15,16-tetranorlabdane Dl-00503
Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-bifuran, 9C/.
1,1 ,4a,6-Tetramethyl-5-ethyl-6,5-oxidodecahydronaphthalene

8a.-form
C 18H:za0 5 M 324.416
Constit of Grindelia stricta. Oil (as Me ester). [rx.ln -26.1°
C 16H:za0 M 236.397 (c, 0.8 in CHC1 3) (Me ester).
Terpenoid numbering shown. Bohlmann, F. eta/, Phytochemistry, 1982, 21, 167 (isol)
8«.-form [6790-58-5] Ambrox. Bicyclofarnesyl epoxide. Olivieri, A.C. et al, J. Org. Chem., 1986, 51, 2824 (synth)
A.mbroxide. n-Epoxide Gonzalez-Sierra, N. eta/, J. Chem. Soc., Perkin Trans. I, 1989,
Volatile constit. of Ambergris tincture. Obt. comly. by 1393 (struct)
degradn. of natural Sclareol. Important amber
perfumery ingredient. Cryst. (pet. ether). Mp 75-76°. Haplodesertoic acid Dl-00506
8fl-form [68365-88-8]/soambrox. lsoepoxide ent-14,15-Dinor-13-oxo-8(17)-labden-18-oic acid. ent-14,15-

0
Mp 60°. Bisnor-13-oxo-8(17)-labden-18-oic acid
Stoll, M. et al, Helv. Chim. Acta, 1950, 33, 1251; 1951, 34, 1664
(Y

Hstt
(synth, config)
Hinder, M. et al, Helv. Chim. Acta, 1953, 36, 1995 (synth, ir)
Lucius, G. et al, Arch. Pharm. (Weinheim, Ger.), 1958, 291, 57;
CA, 52, 14635e (config)
Torii, S. et al, J. Org. Chem., 1978, 43, 4600 (synth)
Oh}off, G. et al, Helv. Chim. Acta, 1985, 68, 2022.
Gonzalez-Sierra, M. et al, Heterocycles, 1987, 26, 2801 (synth)
Decorzaut, R. et al, Tetrahedron, 1987, 43, 1871 (synth)
Koyama, H. et al, Tetrahedron Lett., 1987, 28, 2863 (synth) C18H:za0 3 M 292.417
Biichi, G. et al, Helv. Chim. Acta, 1989, 72, 996 (synth, ir, pmr) Me ester: [126254-98-6]. Methyl haplodesertoate
C 19 H~P 3 M 306.444
15,16-Epoxy-2,3,19-tribydroxy-18-nor- Dl-00504 Constit. of Haplopappus deserticola. Oil.
8(17),13(16),14-labdatrien-12-one Zdero, C. et al, Phytochemistry, 1990, 29, 326 (isol, pmr)

0 Haplomitrenolide A Dl-00507

HO,~
[126737-46-0]

HO'~
oH
HOH2 C
C 19H 11,05 M 334.411
(ent-2/J.Jfl)-form [93236-22-7]
Constit. of A.ustroeupatorium inulaefolium. Cryst. Mp
179° dec.
7-0xo, 8a.,l4-dihydro: [93236-23-8]. ent-15,16-Epoxy-
2fl,3fl,l9-trihydroxy-18-nor-11(16),14-labdadiene-7,12- C10H 240 4 M 328.407
dione Constit. of Haplomitrium mnioides. Needles. Mp 178-180°.
C1,H260, M 350.411 [a.Jn + 76.7° (c, 0.5 in CHC1 3).
From A. inulaefolium. Cryst. Mp 207°. 9a.-Hydroxy: [126737-45-9]. Haplomitrenolide B
Oberti, J.C. eta/, Phytochemistry, 1984, 23, 2003. C10H 240 5 M 344.407
Constit. of H. mnioides. Cryst. Mp 194-196°. [rx.ln
-37.SO (c, 0.2 in Py).
20-Carboxylic acid, Me ester: [126737-47-1].
Haplomitrenolide C
C21H 240, M 372.417
Constit. of H. mnioides. Needles. Mp 195-196°. [rx.ln
+ 12l.2° (c, 0.25 in Py).
Asakawa, Y. et al, Phytochemistry, 1990, 29, 585 (isol, pmr, cmr,
ir, cd)

739
2-Hydroxy-14,15-dinor-7-labden-13-... - 3-Hydroxy-17-nor-8-oxo-13-labden-15-... Di-00508- Di-00514

2-Hydroxy-14,15-dinor-7-labden-13-one 01-00508 8-Hydroxy-15-nor-12-labden-14-al Dl-00512

~:HO
C 18H:34,02 M 278.434 C19H 320 2 M 292.461
2a.-form (8a.,12E)-form [83841-47-8]
Constit. of Waitzia acuminata. Constit. of Greek tobacco. Oil. [1X]D + 13° (c, 0.3 in
Jakupovic, J. eta/, Phytochemistry, 1989, 28, 1943. CHC13).
Wahlberg, I. eta/, Acta Chern. Scand., Ser. B, 1982, 36, 573.
7-Hydroxy-14,15-d.inor-8(17)-labden-13- Dl-00509
one 15-Hydroxy-17-nor-8-labden-7-one Dl-00513
7-Hydroxy-14,15-bisnor-8(17)-/abden-13-one

CI,H320 2 M 292.461
C1aH31,02 M 278.434 (JJS)-form [108657-51-8] Havardiol
7a.-form [59489-11-1] Constit. of Grindelia havardii. Oil. [IX]~ + 22.4° (c, 0.3 in
Constit. of Eupatorium salvia. Oil. CHCI 3).
Francis, M.J., Tetrahedron, 1976, 32, 95 (synth, ir, pmr) 15-Carboxylic acid: [108657-50-7]. 17-Nor-7-oxo-8-labden-
Gonzalez, A. G. eta/, Phytochemistry, 1990, 29, 321 (isol, pmr, 15-oic acid. Havardic acid F
cmr) C 19H 300 3 M 306.444
From G. havardii. Cryst. (as Me ester). Mp 82-83° (Me
8-Hydroxy-14,15-d.inor-11-labden-13-one Dl-00510 ester). [IX]~ +31.3° (c, 0.5 in CHCI 3) (Me ester).
Jolad, S.D. eta/, Phytochemistry, 1987, 26, 483.
0
3-Hydroxy-17-nor-8-oxo-13-labden-15-oic Dl-00514
acid
COOH

C1aH3002 M 278.434
(Ba..JJE)-form [42569-64-2]
Constit. of tobacco. Cryst. (Et20fhexane). Mp 126-127°. HO'
[1X]l: + 13.2° (c, 0.7 in CHC13).
C 19H 300 4 M 322.444
Hlubucek, J.R. eta/, Acta Chern. Scand., Ser. B, 1974, 28, 141
(isol) (ent-3P.J3Z)-form [74513-96-5]
Pelletier, S.W. eta/, J. Org. Chern., 1975, 40, 1607 (synth) · 31X-Hydroxyayapanonic acid
Wahlberg, I. eta/, Acta Chern. Scand., Ser. B, 1978, 32, 203 Constit. of Ayapana amygdalina. Oil (as Me ester). [1X]i:
(synth) -74.2° (c, 1 in CHCI 3) (Me ester).
3-Ketone: [74513-97-6]. ent-17-Nor-3,8-dioxo-13Z-Iabden-
19-Hydroxy-15,16-d.inor-8(17)-labden-13- Dl-00511 15-oic acid
one C 19H 280 4 M 320.428
[65894-39-5] Constit. of A. amygdalina.
Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1997.

C1aH3002
HO~~
M 278.434
Constit. of Pinus spp. Bp0.2 159-163°. [IX]~ +63° (c, 2.5 in
CHC1 3).
19-Carboxy/ic acid: see Haplodesertoic acid, Di-00506
Conner, A.H. et al, Phytochemistry, 1977, 16, 1777.

740
3-Hydroxy-13,14,15,16-tetranor-... - 15-Nor-14-oxo-8(17),12-labdadien-18-... Di-00515 - Di-00521

3-Hydro~y-13,14,15,16-tetranor-7,9(11)- Dl-00515 ent-form [78795-77-4] Acritoconfertic acid

labdadiene-12,17;19,6-diolide Constit. of Acritopappus confertus. Gum.
Bohlmann, F. et a/, Phytochemistry, 1980, 19, 2695.

Isoacrostalidic acid Dl-00518

13,14,15,16-Tetranor-6-/abden-12,8-olid-19-oic acid
[55306-06-4]

C 16H 180s M 290.315

(3/1,6/1)-form [76236-26-5] Wentilactone B
lsol. from Aspergillus wentii. Phytotoxin. Cryst.
(MeOH/EtOAc). Mp 260°.
Q9
HOOC \H
Ct 6H 220 4 M 278.347
Domer, J.W. et a/, Phytochemistry, 1980, 19, 1157. Constit. of Acrostalagmus spp. Cryst. (EtOAc). Mp 204-
2060.
17-Hydro~y-13,14,15,16-tetranor-8,9(11)- Dl-00516 Sato, M. et al, J. Chern. Soc., Perkin Trans. I, 1976, 2407.
labdadiene-12,17;19,6-diolide
0 18-Nor-8(17),13-labdadiene-4,15-diol Dl-00519

,?"' CH2 0H

'OH

C19H 320 2 M 292.461

C 16H 180s M 290.315 (4rx,13E)-form [51513-06-5]
(6fl,l7S)-form [23660-06-2] Antibiotic LL-Z 1271"1. LL-X Constit. of Pinus contorta. Gum.
1271y Manning, T.D.R. et al, Aust. J. Chern., 1973, 26, 2735.
Mould metab. from an Acrostalagmus sp. Shows
antifungal activity. Mp 238-240°. A.rnax 257 nm (e 15 400)
(MeOH).
19-Nor-8(17),13-labdadien-15-oic acid Dl-00520
Ac: Mp 205-209°.
Me ether: [23660-12-0]. Antibiotic LL-Z 1271rx.. LL-Z
1271rx.. PR 1387. Antibiotic PR 1387
C 17H 100s M 304.342
Mould metab. from an A. sp. and Oidiodendron
truncatum. Shows antifungal activity. Plant growth
regulator. Mp 214-216°. [rx.Jn -203° (c, 0.29 in MeOH).
C19H:11,02 M 290.445
7rx.,8rx.-epoxide, Me ether: [90578-11-3]. Antibiotic PR 1388.
(13E)-form [74513-32-9]19-Noranticopa/ic acid
PR 1388
Constit. of Agathis /anceolata. Cryst. 1\fp 64-68°. [rx.Jn
C17H 100 6 M 320.341 +45° (c, 1 in CHCI 3).
From 0. truncatum. Cryst. Mp 232-233°. [or:Jn + 84.0° (c,
0.3 in MeOH). Khac, D.D. et al, Phytochemistry, 1979, 18, 1839.
Ellestad, G.A. et al, J. Am. Chern. Soc., 1970, 92, 5483 (isol,
struct) 15-Nor-14-oxo-8(17),12-labdadien-18-oic Dl-00521
Adinolfi, M. eta/, Tetrahedron Lett., 1972, 695; Gazz. Chim. /tal., acid
1973, 103, 1271 (synth)
Kakisawa, H. eta/, J. Chern. Soc., Chern. Commun., 1973, 802
(biosynth, cmr) I ('r'CHO

SP
Welch, S.C. et al, J. Am. Chern. Soc., 1977, 99, 549 (synth)
Anderson, N.R. et al, Tetrahedron Lett., 1984, 25, 469 (deriv)

17-Hydro~y-13,14,15,16-tetranor-7- Dl-00517
labden-12-oic acid
C19H 180 3 M 304.428
COOH

qbCH,OH
(ent-12E)-form [81920-05-0]
Constit. of Mikania a/vimii. Gum. [rx.]i;' -13° (c, 0.16 in
CHCI 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 173.

M 266.380

741
13,14,15,16-Tetranor-12,8-... - 14,15,16-Trinor-13,8-labdanolide Di-00522 - Di-00526

13, 14, 15,16-Tetranor-12,8-labdanolide Dl-00522 13,14,15,16-Tetranor-8(17)-labdene-12,19- Dl-00525

dioic acid
Acrosta/ic acid
[55306-07-5]
COOH

C 16Hu;02 M 250.380
Brx.-form [564-20-5] NQrambreinolide
Degradn. prod. of ambrein, etc. Found in tobacco.
Cryst. (pet. ether or MeOH aq.). Mp 122-125°. [ocln
+42° (c, 0.25 in CHCI 3).
C,6H240 4
HOOW
M 280.363
Constit. of Acrostalagmus spp. Cryst. (EtOAc). Mp 219-
2200.
Joe-Hydroxy: [123844-63-3]. 3oc-Hydroxy-13,14,15,16-
tetranor-12,8-labdanolide. 3rx.-Hydroxynorambreinolide 7{J-Hydroxy: [32179-19-4]. 7{J-Hydroxy-13,14,15,16-
C16H 260 3 M 266.380 tetranor-8( 17)-labdene-12, 19-dioic acid. Antibiotic LL-Z
Constit. of Salvia aethiopis. Cryst. (Etpjhexane). Mp 1271p. LL-Z 1271/J
190-191°. [ocln +22.2° (c, 1.08 in CHCI 3). C,6H240 5 M 296.363
From A. spp. Mp 200° dec. [ocln +22.5° (MeOH).
(ent-Brx.)-form [95406-08-9] ent-Norambreinolide
Constit. of Sideritis nutans. Cryst. (EtOAcjpet. ether). Ellestad, G.A. eta/, Tetrahedron Lett., 1971, 497 (deriv)
Sato, M. et a/, J. Chern. Soc., Perkin Trans. 1, 1976, 2407 (isol)
Mp 120-122°.

g?o
Carman, R.M., Aust. J. Chern., 1966, 19, 1535 (synth, bib[)
Fernandez, C. eta/, Phytochemistry, 1985, 24, 188 (isol) 14,15,16-Trinor-13,8-labdanolide Di-00526
Gonzalez, M.S. et al, Tetrahedron, 1989, 45, 3575 (3rx.-
Hydroxynorambreinolide)

13,14,15,16-Tetranor-7-labden-12-al Di-00523
1,4,4a,5,6, 7,8,8a-Octahydro-2,5 ,5,8a-tetramethyl-1-
naphthaleneacetaldehyde, 9CI

C 17H 280 2 M 264.407

Brx.-form [468-84-8] Ambreinolide
Constit. of Cistus labdaniferus. A key degradation
product of di- and tri-terpenes. Used in manuf. of
perfumes. Cryst. (hexane). Mp 142-144°. [oc]i? +33.3° (c,
2.565 in CHC1 3).
C 16H 260 M 234.381 [7663-46-9)
ent-form [88862-14-0] Schenk, H.R. et al, Helv. Chim. Acta, 1952, 35, 817 (synth)
Constit. of Acritopappus confertus. Gum. Corey, E.J. et al, i. Am. Chern. Soc., 1963, 85, 3979 (synth)
Demole, E. et al, Helv. Chim. Acta, 1967, SO, 1314 (synth)
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243. Sobti, R.R. et al, Tetrahedron Lett., 1968, 2215 (synth)
De Pascual Teresa, J. eta/, An. Quim., 1979, 75, 335 (isol)
13,14,15,16-Tetranor-8(17)-labden-12-al Dl-00524 Daniewski, W.M. et al, J. Org. Chern., 1985, SO, 3963 (synth)
y-Bicyclohomofarnesal
[3243-36-5]

~0
C16H 260 M 234.381
Used in perfumery. Oil with strong amber odour. Bp0. 17
78°. [oc]~ +24° (c, 1.9 in CHC1 3).
2-0xo: [125458-76-6]. 2-0xo-13,14,15,16-tetranor-8(17)-
labden-12-al. 2-0xo-y-bicyclohomofarnesal
C 16H 240 2 M 248.364
Oil. BPo.oi 125o.
Sundaraman, P. eta/, J. Org. Chern., 1977, 42, 806 (synth)
Cambie, R.C. et al, Aust. J. Chern., 1989, 42, 497, 1115 (synth,
pmr, bib[)

742
Agelasine C - 15,16-Epoxy-3,5-dihydroxy-13(16),14-... Di-00527 - Di-00532

(ent-UR)-form [67988-03-8]
Isol. from H. umbel/atum. Cryst. (benzoic acid). Mp
Halimanes 148°. [ocJn + 70.SO (c, 2.04 in EtOH).
[67987-98-8)
de Pascual Teresa, J., An. Quim., 1978, 74, 488 (iso[)
Urones, J.G. et a/, Phytochemistry, 1990, 29, 1247 (isol, pmr, cmr)

Agelasine C Dl-00527 2,15-Dihydroxy-1(10)-halimen-18-oic acid Dl-00530

C20H3404
(ent-2a.,l31;)-form
2P-Hydroxyhydrohalimic acid
C26H 40N 5 Eil M 422.635 (ion) lsol. from Halimium viscosum. Cryst. (C6H 6 /hexane).
Isol. from the Okinawan sea sponge Age/as nakamurai. Mp 79-80°.
Shows antimicrobial activity. ATP-ase inhibitor. 18-+2 Lactone, 15-Ac: ent-15-Acetoxy-1(10)-halimen-18,2a.-
Chloride: [92664-79-4]. olide. ent-15-Acetoxy-9, 10-friedo-1(1 0)-/abden-18,2-o/ide
C26 H40 ClN5 M 458.088 C22 H 340 4 M 362.508
Mp 176-179°. [oc]i;l -55.1° (c, 2.04 in MeOH). Constit. of Halimium viscosum. Oil. [a]~ + 33.3° (c, 1.95
Nakamura, H. eta/, Tetrahedron Lett., 1984, 25, 2989 (uv, pmr, in CHC1 3).
cmr, struct) De Pascual Teresa, J. et a/, An. Quim., 1979, 75, 140.
De Pascual Teresa, J. et al, Phytochemistry, 1985, 24, 791.
5,10:15,16-Diepoxy-3-hydroxy-13(16),14- Dl-00528
halimadien-20,12-olide 3,19-Dihydroxy-5-halimen-15-oic acid Dl-00531

COOH

HO~ C20H 240 4 M 328.407

(ent-3a.,131;)-form
C20H 260 5 M 346.422 Isot from Relhania corymbosa.
(ent-3P,5a.,l Oa.,J2PII)-form [1 02904-50-7] Ja.-Hydroxy-Sp,J OP- Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 3173.
epoxychiliolide
lsol. from Chiliotrichium rosmarinifolium. Cryst. (EtzO). 15,16-Epoxy-3,5-dihydroxy-13(16),14- Dl-00532
Mp 19l.SO. [oc]i;' +90° (c, 0.17 in CHC1 3). halimadien-20,12-olide
Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305.

14,15-Dihydroxy-1(10),13(16)-halimadien- Dl-00529
18-oic acid
OH
I

C20 H 280 5 M 348.438

(ent-3P,5P,J2PII)-form
3a.,5a.-Dihydroxychiliolide
C2oH3204 M 336.470 C20H 280 5 M 348.438
(ent-148)-form [67988-04-9] Constit. of Chiliotrichium rosmarinifolium. Cryst. Mp
Constit. of Halimium viscosum and H. umbellatum. 207°. [oc]~4 +22° (c, 0.48 in CHC1 3). Chiliolide is
unknown.
Me ester: [67987-94-4].
Constit. of H. viscosum. Oil. [ocln +62.8° (c, 1.93 in 5-Deoxy, 5,6-didehydro: 15,16-Epo.xy-3-hydroxy-
CHC1 3). 5,13(16),14-ha/imatrien-20,12-o/ide. Ja.-Hydroxy-5,6-
dehydrochiliolide

743
15,16-Epoxy-13(16),14-halimadiene-••• - 15,16-Epoxy-6-hydroxy-5(10),13(16) ... Di-00533 - Di-00538

C:zeli260 4 M 330.423 15,16-Epoxy-5(10),13(16),14-halimatrien- Dl-00536

Constit. of C. rosmarinifolium and Nardophyl/um 20,12-olid-19-oic acid
lanatum. Amorph. solid. [a]~ + 58° (c, 0.9 in CHCI 3).
Jakupovic, J. et a/, Tetrahedron, 1986, 42, 1305 (isol)
Harde, C. et a/, Tetrahedron, 1988, 44, 81 (synth)

15,16-Epoxy-13(16), 14-halimadiene- Dl-00533

17,12:20,7-diolid-19-oic acid

C10H 240 5 M 344.407

(ent-12PH)-form
Me ester: [78791-49-8]. Penduliflaworosin
C21 H 260 5 M 358.433
Constit. of Croton pendu/ifiorus. Cryst. (MeOH). Mp
100-101°. [a]~ + 112° (c, 0.007 in CHC1 3).
C:zelf120 7 M 374.390
Adesogan, E.K., J. Chern. Soc., Perkin Trans. 1, 1981, 1151.
(5rx.,7p,BpH,12rx.H)-form
Me ester: [70447-99-3]. Diasin Dl-00537
15,16-Epoxy-5-hydroxy-2,12-dioxo-
C21H 240 7 M 388.416
Constit. of Croton diasii. Cryst. (MeOH). Mp 158-160°. 1(10),13(16),14-halimatrien-18-oic acid
[ali? + W (CH 2 Cl~.
De Alvarenga, M.A. eta/, Phytochemistry, 1978, 17, 1773.

15,16-Epoxy-13(16),14-halimadien-5-ol Dl-00534

~ 0
~

C10H 240 6 M 360.406

Me ester: [28487-86-7]. Clrettaplumin I
C21H 260 6 M 374.433
Constit. of Adenochlaena siamensis. Cryst., Mp 158-159°.
(5~,8aH)-:form [aln -72.7° (c, 2 in Me2CO).
C10H 320 2 M 304.472 Sato, A. et a/, Tetrahedron Lett., 1971, 839.
(5p,Brx.H)-form [76215-27-5] Ambliol B
Constit. of Dysidea amblia. Oil. [ali:' -3.4° (c, 1.5 in 15,16-Epoxy-6-hydroxy-5(10),13(16),14- Dl-00538
CHC1 3). halimatrien-20,12-olide-18,19-dioic acid
(5P,BPH)-form [93601-06-0] Ambliol C
From D. amblia. Cryst. (hexane). Mp 45-46°. [1X]n
-37.8° (c, 2 in CHC1 3).
Walker, R.P. eta/, J. Org. Chern., 1981, 46, 1098; 1984, 49, 5160
(isol, struct)
Piers, E. eta/, J. Chern. Soc., Chern. Commun., 1989, 1222 (synth)

15,16-Epoxy-5,13(16),14-halimatrien-18- Dl-00535
oic acid
Koanophyllic acid A
[80368-53-2]
C20H 120 8 M 390.389

@~
(ent-6P,J2PH)-form
Ac, di-Me ester: [62025-46-1]. MaUotucin B
C24H:zs09 M 460.480
Constit. of Mallotus repandus. Cryst. Mp 131.5-132.SO.
COOH Kawashima, T. eta/, Heterocycles, 1976, 5, 227.

C:zeH:zs03 M 316.439
Constit. of Koanophyl/on conglobatum. Gum.
Bohlmann, F. eta/, Phytochemistry, 1981, 20, 1903.

744
13,14-Epoxy-15-hydroxy-1(10)-... - 13-Hydroxy-1(10),14-halimadien-19-... Di-00539 - Di-00545

13,14-Epoxy-15-hydroxy-1(10)-halimen- Dl-00539 3-Ketone, 15-carboxy/ic acid: [89900-53-8]. 3-0xo-5(10)-

18-oic acid ha/imen-15-oic acid. Sa/mantic acid
C 28H 3z03 M 320.471
From C. laurifolius.
3-Ketone, 15-carboxy/ic acid, Me ester: [89900-50-5].
C21 H 340 3 M 334.498
From C. laurifolius. Oil. [a]i,2 -3.2° (c, 1.25 in CHCI 3).
de Pascual Teresa, J. et al, Phytochemistry, 1983, 22, 2783.

14-Halimene-5,13-diol Dl-00543
C:zoH310 4 M 336.470 OH
ent-form [128988-50-1]
Constit. of Halimium viscosum.
Urones, J.G. et al, Phytochemistry, 1990, 29, 1247 (isol, pmr, cmr,
ir)

1(10),13-Halimadiene-2,15-diol Dl-00540
C 28 H 360 1 M 308.503
(ent-SP,J3~)-form
Pleuroziol
Constit. of Pleurozia gigantea. Oil. [aln +3° (c, 1 in
CHCI 3).
Asakawa, Y. et at, Phytochemistry, 1990, 29, 2597 (isot, pmr, cmr)
C 28H 340 1 M 306.487
(ent-2rx.,l3E)-form
5-Halimen-18-oic acid Dl-00544
Constit. of Baccharis po/ifolia. Oil.
2-Ketone: ent-15-Hydroxy-1(10),13-halimadien-2-one
C 28H 310 1 M 304.472
Constit. of B. polifolia. Oil.
Zdero, C. et a/, Phytochemistry, 1986, 25, 2841.

5,13-Halimadien-16,15-olid-18-oic acid Dl-00541

Koanophyllic acid C C 28H 340 1 M 306.487
[80368-51-0] (13;;,)-form [80368-52-1] Koanophyllic acid B
Constit. of Koanophyllon conglobatum. Gum.

(tr~
Bohlmann, F. et at, Phytochemistry, 1981, 20, 1902.

13-Hydroxy-1(10),14-halimadien-19-oic Dl-00545
acid
COOH
C:zoH280 4 M 332.439
Constit. of Koanophyllon conglobatum. Gum.
16-Deoxo, 15-oxo: [80377-42-0]. 5,13-Ha/imadien-15,16-
o/id-18-oic acid. Koanophyllic acid D
C 28H 280 4 M 332.439
Constit. of K. conglobatum. Gum. Cl8H3z03 M 320.471
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1903. (ent-13~)-form [107110-07-6] Friedolabdaturbinoic acid
Constit. of Eupatorium turbinatum. Oil (as Me ester).
5(10)-Halimene-3,15-diol Dl-00542 [a]i;' -47° (c, 7.44 in CHC1 3) (Me ester).
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 2677.

HO'

C:zoH360 1 M 308.503
(ent-3P,BPH,J3~)-form [89900-52-7] Salmantidiol
Constit. of Cistus /aurifolius. Cryst. Mp 74-75°. [a]i,2
-8.4° (c, 0.76 in CHC13).

745
3-Hydroxy-5-halimen-15-oic acid- 15-0xo-1(10),13-halimadien-18-... Di-00546 - Di-00551

3-Hydroxy-5-halimen-15-oic acid Di-00546 6P-Hydroxy: 6P-Hydroxyisochiliolide lactone

C20H 240 6 M 360.406
COOH Constit. of Conyza pyrifolia. Gum.
6P-Angeloyloxy: 6P-Angeloyloxyisochiliolide lactone
C25H 300 7 M 442.508
Constit. of Microglossa pyrrhopappa. Gum.
6P-(2-Methylbutanoyloxy): 6P-(2-
Methylbutanoyloxy )isocholiolide lactone
C25 H 310 7 M 444.524
C20H 340 3 M 322.487 Constit. of M. pyrrhopappa. Gum.
(ent-3rx,l31;)-form 7P-Angeloyloxy: 7P-Angeloyloxyisochiliolide lactone
Constit. of Relhania corymbosa. C25H 300 7 M 442.508
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol) Constit. of M. pyrrhopappa. Gum.
8p-Hydroxy: 8p-Hydroxyisochiliolide lactone
15-Hydroxy-1(10)-halimen-18-oic acid Dl-00547 C20H 240 6 M 360.406
Constit. of M. pyrrhopappa. Cryst. Mp 264°. [oc]~ +68°
(c, 0.19 in CHC1 3).
7P,8P-Epoxy: 7p,sp-Epoxyisochiliolide lactone
C20 H1z0 6 M 358.390
Constit. of M. pyrrhopappa. Cryst. Mp 295-300°. [oc]~
+64° (c, 0.16 in CHC1 3).
8,17-Didehydro: 8,17-Didehydroisochiliolide lactone
C20 H110 5 M 342.391
C 20H 340 3 M 322.487 Constit. of M. pyrrhopappa. Cryst. Mp 225-230°.
(ent-131;)-form [70868-66-5] Hydrohalimic acid 8,17-Didehydro, 7P-hydroxy: 8,17-Didehydro-7P-
Constit. of Halimium viscosum. Oil (as Me ester). [ocJn hydroxyisochiliolide lactone
+31.8° (c, 1.16 in CHC1 3) (Me ester). C20H 110 6 M 358.390
De Pascual Teresa, J. et al, An. Quim., 1979, 75, 140. Constit. of C. pyrifolia. Gum.
8,17-Didehydro, 7P-acetoxy: 7P-Acetoxy-8,17-
12-Hydroxy-13,14,15,16-tetranor-1(10)- 01-00548 didehydroisochiliolide lactone
C20 H110 6 M 358.390
halimen-18-oic acid lsol. from M. pyrrhopappa.
Jakupovic, J. et al, Tetrahedron, 1986, 42, 1305.
g:;~OH Zdero, C. et al, Phytochemistry, 1990, 29, 3167, 3235 (derivs)

2-0xo-1(10),13-halimadien-15-oic acid Dl-00550

;::r COOH
' COOH 0
C 16H 21;03 M 266.380
ent-form
Constit. of Halimium viseosum.
Me ester: Oil. [ocJn + 79.6° (c, 1.5 in CHC1 3). C20H 300 3 M 318.455
.Ac: [109163-64-6]. (8PH,13E)-form [72023-10-0] Relhanic acid
C 18H 28 0 4 M 30~.417 Constit. of Relhania acerosa. Oil. [!X]~ +53° (c, 2.6 in
Constit. of H. viscosum. CHC13) (as Me ester).
Urones, J.G. et al, Phytochemistry, 1987, 26, 1077; 1990, 29, 3597 Bohlmann, F. !tal, Phytochemistry, 1979, 18, 631.
(isol, pmr, cmr)
15-0xo-1(10),13-halimadien-18-oic acid Dl-00551
lsochiliolide lactone Dl-00549
[102904-59-6] CHO

(ent-13E)-form

C20H 300 3 M 318.455

(ent-13E)-form [109181-77-3]
Constit. of Halimium viscosum.
Me ester: [109163-59-9].
Oil. [oc]i,2 + 64.12° (c, 1.05 in CHC1 3).
Czoll240 5 M 344.407 15-Carboxylic acid: [109163-62-4]. 1(10),13E-Halimadiene-
Constit. of Chiliotrichium rosmarinifolium. Amorph. solid. 15 ,18-dioic acid
[oc]~ +40° (c, 0.26 in CHC1 3). C20H 300 4 M 334.455

746
Secochiliolide aldehyde - 8,16;16,17-Bisepoxyacritoconfertoic ... Di-00552 - Di-00556

Constit. of H. viscosum. Oil (as di-Me ester). [IX]~ C 24H 380 7 M 438.560
+ 73.35° (c, 1.2 in CHC1 3)(di-Me ester). Constit. of H. viscosum.
(ent-13Z)-form [109163-65-7] Urones, J.G. eta/, Phytochemistry, 1990, 29, 1247 (isol, pmr, cmr)
Constit. of H. viscosum.
Me ester: [109163-58-8]. 14,15,16-Trinor-1(10)-halimene-13,18- Dl-00554
Oil. [IX]~ +61.54° (c, 1.31 in CHC1 3). dioic acid
15-Carboxylic acid: [109163-61-3]. 1(10),13Z-Halimadiene-

qS~H
15 ,18-dioic acid
C 20H 300 4 M 334.455
Constit. of H. viscosum. Oil (as di-Me ester). [IX]~
+68.43° (c, 0.8 in CHC1 3) (di-Me ester).
Urones, J.G. et a/, Phytochemistry, 1987, 26, 1077.

COOH
Secochiliolide aldehyde Di-00552
ent-15 ,16-Epoxy-3-oxo-3 ,4-seco-4,13(16),14-halimatrien- Ct7H2604 M 294.390
20,121X-olide ent-form
Constit. of Halimium viscosum. Oil (as di-Me ester). [1X]n
+ 53.6° (c, 1.1 in CHC1 3) (di-Me ester).
Urones, J.G. eta/, Phytochemistry, 1990, 29, 3597 (isol, pmr, cmr)

Rearranged labdanes
19

CwH 260 4 M 330.423

Constit. of Chiliotrichium rosmarinifolium. Oil. [1X]i;' + 13°
(c, 0.12 in CHC1 3). Abeoanticopalic acid Di-00555
3-Carboxylic acid: [102904-56-3]. ent-15,16-Epoxy-3,4-seco- [109291-59-0]
4, 13(16), 14-halimatrien-20, 121X-olid-3-oic acid.
Secochiliolide acid
C 20H 260 5 M 346.422
Constit. of C. rosmarinifolium and Nardophyllum
lanatum. Oil. [1X]i;' + 14° (c, 0.35 in CHC1 3).
19-Hydroxy, 3-carboxylic acid: ent-15,16-Epoxy-19-
hydroxy-4, 13( 16), 14-halimatrien-20, 121X-olid-3-oic acid.
l~Hydroxysecochiliolide acid C20H 300 2 M 302.456
C 20H 260 6 M 362.422 Constit. of Pinus strobus.
Constit. of N. lanatum (as Me ester). Me ester: [109291-61-4].
Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305. Oil. [1X]~ +41.SO (c, 1.3 in CHC1 3).
Zinke!, D.F. eta/, Phytochemistry, 1987, 26, 769.
13,14,15-Trihydroxy-1(10)-halimen-18-oic 01-00553
acid 8,16; 16,17-Bisepoxyacritoconfertoic acid Dl-00556

(ent-J3S,14R)-form

C 20H 340 5 M 354.486

(ent-13S,UR)-form C 20H 260 5 M 346.422
14,15-Di-Ac: [128988-51-2]. Constit. of Acritopappus confertus.
C 24H 380 7 M 438.560 Bohlmann, F. et a/, Phytochemistry, 1983, 22, 2243.
Constit. of Halimium viscosum.
(ent-13R,14S)-form
14-Ac: [128988-52-3].
C 22H 360 6 M 396.523
Constit. of H. viscosum.
14,15-Di-Ac: [129097-54-7].

747
Chettaphanin II - Gypopinifolone Di-00557 - Di-00564

Chettaphanin II Dl-00557 13(16), 14-Gnaphaladien-8-ol Dl-00561

[33140-19-1]

C20H 320 M 288.472

8rx.-form [103784-21-0]
Constit. of Helichrysum nudifolium. Oil.
C21 H 240 4 M 340.418
Jakupovic, J. eta/, Phytochemistry, 1986, 25, 1133.
Constit. of Adenochlaena siamensis. Cryst. Mp 127-128°.
[cx] 0 -592° (c, 2 in Me2CO).
Sato, A. eta/, Tetrahedron Lett., 1971, 839. 14-Gnaphalene-8,13-diol Dl-00562

16,17-Dihydroxy-7-acritoconfertenoic acid Dl-00558

C20H 340 2 M 306.487

(ent-8P,13S)-form [74638-10-1]
Constit. of Gnaphalium undulatum. Cryst. (C6H 6). Mp
142-145°. [cx]~4 +33.6° (c, 0.25 in CHCI 3).
Bohlmann, F. et a/, Phytochemistry, 1980, 19, 71.

C20H 280 5 M 348.438

Gutierrezial Dl-00563
16-Ac:
C22 H 300 6 M 390.475 [93372-66-8]
Constit. of Acritopappus confertus. Gum (as Me ester).
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 2243.

Fregenedadiol Dl-00559

C20H 260 4 M 330.423

Constit. of Gutierrezia sarothrae. Cryst. (pet. ether)(as Me
ester). Mp 128° (Me ester). [ex]~ +427° (c, 0.06 in
CHCI3)(Me ester).
Bohlmann, F. eta/, Phytochemistry, 1984, 23, 2007.
C20H 32 0 2 M 304.472
Constit. of Halimium viscosum. Oil. [cx]~4 -11.25° (c, 0.48
in CHC13). Gypopinifolone Dl-00564
Urones, J.G. eta/, Phytochemistry, 1990, 29, 3042 (isol, pmr, cmr) [118462-76-3]

8(17),13-Gnaphaladien-15-oic acid Dl-00560

dfCOOH C20H 340 3 M 322.487

Constit. of Gypothamnium pinifolium. Oil.
C20H 300 2 M 302.456 Zdero, C. eta/, Phytochemistry, 1988, 27, 2953.
(13E)-form [109291-60-3] Cycloanticopalic acid
Constit. of Pinus strobus.
Me ester: [109291-62-5].
[cxJi? + 87.SO (c, 1.4 in CHCI 3).
Zinke!, D.F. eta/, Phytochemistry, 1987, 26, 769.

748
Neoconcinndiol hydroperoxide- 8,13-Epoxy-3-nor-14-colensen-2-one Di-00565 - Di-00570

Neoconcinndiol hydroperoxide Dl-00565

Colensanes
[64504-60-5]
OH

8,13-Epoxy-2-hydroxy-14-colensen-3-oic Dl-00568
acid

OOH
CJI340 4 M 338.486
Constit. of Laurencia snyderae. Cryst. Mp 158-159°. [a:]~
-35° (c, 0.8 in MeOH).
Howard, B.M. et al, J. Am. Chern. Soc., 1977, 99, 6440.
C 10H 320 4 M 336.470
Richardianidin 1 Dl-00566 (2fl,8rx.,l3R)-form [24035-63-0] 2fl-Hydroxy-2rx.-colensenoic acid
[117232-63-0] Constit. of Dacrydium co/ensoi. Cryst. (as Me ester). Mp
66-68° (Me ester).

_:rh
2~--o
Grant, P.K. et al, Aust. J. Chern., 1969, 22, 1265.

15,16-Epoxy-2-hydroxy-1-hydroxymethyl-
14-colensen-3,1'-olide
Dl-00569

: H OAc
CzzH240 7 M 400.427
Novel 6, 7-seco-6,11-cyclolabdane skeleton. Constit. of
Cluytia richardiana. Cryst. (MeOH). Mp 220-222°. [a:)n
+8° (c, 0.4 in CHC1 3).
Isomer: [117210-47-6]. Ricluudillnidin 2 C 11H 310 4 M 348.481
C 22H 240 7 M 400.427 (lrx.,2fl,8rx.,l3R)-form [28644-78-2] 2fl-Hydroxy-Irx.-
Constit. of C. richardiana. Mp 266-268°. [a:]n -0.02° (c, hydroxymethykolensene-2rx.-carboxylic acid lactone
0.14 in CHC1 3). Lactonised onto C(l) instead of C(2). Costit. of Dacrydium co/ensoi. Cryst. (hexane). Mp 208-
Mossa, J.S. et al, Tetrahedron Lett., 1988, 29, 3627 (cryst struct) 2090.
Grant, P.K. et al, Tetrahedron, 1970, 26, 1631.
Rotalin A Dl-00567
[119979-81-6] 8,13-Epoxy-3-nor-14-colensen-2-one Dl-00570

~-~
~ (8a,13R)-form

C 19H:14,01 M 290.445
C 10H 310 M 288.472 (8rx.,13R)-form [1757-94-4] Colensenone
Metab. of sponge Mycale rota/is. Oil. [a:)n -1.8° (c, 2.8 in Constit. of the heartwood of Dacrydium colensoi. Cryst.
CHC1 3). (MeOH aq.). Mp 99-100°.
Corriero, G. et al, Tetrahedron, 1989, 45, 277. (ent-Brx.,l3S)-form [38049-39-7] Tiganone
Constit. of Sideritis canariensis. Solid. Mp 96-99°. [a:Jn
-37° (c, 1.1 in CHCI 3).
Grant, P.K. et al, J. Chern. Soc., 1962, 3740 (Colensenone)
Enzell, C. et al, Ark. Kemi, 1965, 23, 367 (ms)
Gonzalez, A.G. et al, An. Quim., 1971, 67, 1245 (Tiganone)

749
Agelasine A - Cardiophyllidin Di-00571 - Di-00575

Bacchomagellins Di-00573

Clerodanes

Agelasine A Di-00571 CH2 0R

[56271-74-0]
Bacchomagellin A R = OCCH 2COOH
Bacchomagellin B R = OCCH2CH 2COOH

tO
N NH2
Inseparable mixture of compounds.
Bacchomagellin A
I C46H 700 11 M 799.052
Me
Constit. of Baccharis magellanica.
Bacchomagellin B
C26H40N 5Ell M 422.635 (ion) C48 H 740 11 M 827.106
Constit. of the Okinawan sponge Age/as nakamurai. From B. magellanica.
ATPase inhibitor. Zdero, C. eta/, Phytochemistry, 1986, 25, 2841.
Chloride:
C26H 40C1N5 M 458.088 Bartemidiolide Di-00574
Cryst. Mp 173-174°. [cx]i;5 -31.3° (c, 0.59 in MeOH). 3cx,4cx: 15,16-Diepoxy-13(16),14-clerodadiene-19,2P,:20,12-
8,9,10- Triepimer: [92664-76-1]. Agelasine B diolide
C26H 40N 5Ell M 422.635 (ion) [114360-14-4]
Constit. of A. nakamurai. ATPase inhibitor.
8,9,10- Triepimer, chloride: 0
C26H 40C1N5 M 458.088
Cryst. Mp 167-170°. [cx]i;5 -21.5° (c, 1.00 in MeOH).
~ A
Nakamura, H. eta/, Tetrahedron Lett., 1984, 25, 2989 (uv, pmr,
cmr, struct)

Ageline B Di-00572
[88874-28-6]
0 0
C20H 220 6 M 358.390
Constit. of Baccharis artemisioides. Cryst. (MeOH). Mp
224-225°. [cx]i;5 +84.4° (c, 0.7 in CHC1 3).
Tonn, C.E. eta/, Phytochemistry, 1988, 27, 489 (isol, cryst struct)

Cardiophyllidin Dl-00575

C31 H 43N 60 1Ell M 531.720 (ion)

Constit. of sponge Age/as sp. Active against gram-positive
bacteria. Weak ichthyotoxin. Absolute
[88855-18-9, 88855-19-0] configuration
Capon, R.J. eta/, J. Am. Chern. Soc., 1984, 106, 1819.
C20H 200 6 M 356.374
Constit. of Salvia cardiophylla. Cryst. Mp 239-241°.
Gonzalez, A.G. eta/, Tetrahedron Lett., 1988, 29, 363 (cryst struct)

750
18-Chloro-12,20:15,16-diepoxy-... - 3,12-Clerodadiene-15,16-dial Di-00576 - Di-00580

18-Cbloro-12,20:15,16-diepoxy-4,7,19,20- 6-Ketone, 19-Ac: [82225-40-9]. ent-19-Acetoxy-18-chloro-

tetrahydroxy-7 ,13(16),14-clerodatrien-6- 15, 16-epoxy-4p-hydroxy-3,6-dioxo-13(16), 14-clerodadien-
20,12-olide. Tafricanin A
one Dl-00576
C 22 H 25Cl08 M 452.887
Constit. ofT. africanum. Cryst. (EtOH). Mp 189-191°
dec. [1X]i? + 32.9° (c, 0.9 in CHC1 3).
Hanson, J.R. et a/, J. Chern. Soc., Perkin Trans. 1, 1982, 1005
(iso[)
De La Torre, M.C. eta/, Phytochemistry, 1990, 29, 988 (isol, pmr)
-OH
Clerocidin Dl-00579
PR 1350. Antibiotic PR 1350
I
[87501-14-2]
CIH2C \ 0 i
HOcHpH
C:zoHzsCl07 M 412.866
(ent-4P,12PH,20rx. )-form
19,20-di-Ac: Teuvincentin A
C 24H 29Cl09 M 496.940
Constit. of Teucrium polium. Cryst. (EtOAcjhexane).
Mp 200-201° dec. [1X]i? -92.7° (c, 0.192 in CHC1 3).
Carreiras, M.C. et a/, Phytochemistry, 1988, 28, 1453 (isol, cryst Probable
struct) absolute
configuration
3-Chloro-18,19-epoxy-4,19-dihydroxy-13- Dl-00577
cleroden-15, 16-olide C40H 560 10 M 696.876
Dimer which can equilibrate with the corresponding

~
monomer in suitable solvs. Diterpene antibiotic. Isol.
from the fungus Oidiodendron truncatum. Active against
gram-positive and -negative bacteria and P388
Cl-~T
HO r.oH
c
I
leukaemia cells. Powder. [1X]i? + 85° (c, 1 in EtOH).
Derivs. all exist in monomeric form.
l.....Q I> LD 50 250 mgjkg (i.p. mice).
C:zoH 29Cl05 M 384.899 MeOH compd.: [87500-88-7]. PR 1381. Antibiotic PR 1381
(3rx.,4P,5rx.,19p)-form Shows similar activity to Clerocidin. Cryst. (MeOH).
Mp 139-141°. [1X]i:' + 102.8° (c, 1 in EtOH).
19-Me ether: [35020-26-9]. Gutierolide
CuH31 Cl05 M 398.926 Ger. Pat., 3 147 726, (1982); CA, <n, 90422 (isol, props)
Andersen, N.R., J. Antibiot., 1983, 36, 753 (iso[)
Constit. of Gutierrezia dracunculoides. Cryst. (EtOH).
Andersen, N.R. et al, Tetrahedron Lett., 1984, 25, 465, 469 (cmr,
Mp 207-209°. [1X]i,l -103° (MeOH). Abs. config. may be ms, pmr, corifig)
doubtful in the light of recent reversal of several abs.
configs. in the Clerodane group.
3,12-Clerodadiene-15,16-dial Dl-00580
Cruse, W.B.T. et al, J. Chern. Soc., Chern. Commun., 1971, 1278.

18-Chloro-15,16-epoxy-4,6,19-trihydroxy- Dl-00578
3-oxo-13(16), 14-clerodadien-20,12-olide

C:zoH:lC,01 M 302.456
(ent-5rx.,13E)-form [55890-21-6] Unaridial
Constit. of Linaria japonica. Oil. [1X]n + 13° (CHC1 3).
Bis-2,4-dinitrophenylhydrazone: Yellow cryst. (EtOAc). Mp
207-209°. [IXUl -24° (c, 0.75 in Py).
0 I
Kitagawa, I. eta/, Chern. Pharm. Bull., 1976, 24, 294.
Cl&C \ \ OH
HO CH20H

C:zoHzsCl07 M 412.866
(ent-4P,6P,12PH)-form
7,19-Di-Ac: [82225-39-6]. Tafricanin B
C 24H 29Cl09 M 496.940
Constit. of Teucrium africanum. Cryst. (EtOH). Mp 255-
2560. [1X]i? + 14.6° (c, 0.9 in CHC1 3).

751
3,13-Clerodadiene-15,17-diol - 4(18),12-Clerodadiene-15,16-diol Di-00581 - Di-00584

3,13-Clerodadiene-15,17-diol Dl-00581 3,13-Clerodadiene-15,18-diol Di-00582

C 20 H340 2 M 306.487 HOH2C

(ent-13£)-form C20H3402 M 306.487
3,13-Kola.,adiene-15,17-diol (ent-13£)-form
Constit. of Symphyopappus reticulatus. Gum. Di-Ac: ent-15,18-Diacetoxy-3,13-c/erodadiene. 15,18-
15-A/dehyde: ent-17-Hydroxy-3,13E-clerodadien-15-al. !17- Diacetoxy- 3, 13-ko/avadiene
Hydroxy-3,13E-kolavadien-15-al C24H380 4 M 390.562
C20H 320 2 M 304.472 Constit. of Baccharis incarum. Oil. [cx]i,S -31.4° (c, 0.83
Constit. of S. reticu/atus. Gum. [cx]i;' +20.1° (c, 0.72 in in CHC1 3).
CHC1 3). Dicarboxylic acid: [26380-58-5]. ent-3,13-C/erodadiene-
17-Carboxy/ic acid: ent-15-Hydroxy-3,13E-c/erodadien-11- 15,18-dioic acid. Kola11ic acid
oic acid. Bacchasalicylic acid C2oH 300 4 M 334.455
CwH320 3 M 320.471 Constit. of Hardwickia pinnata. Cryst. Mp 228-230°. [cxJn
Constit. of Baccharis salicifolia. Oil. -115.3° (EtOH).
17-Carboxy/ic acid, 15-0-P-v-xy/opyranoside: Dicarboxylic acid, 15-Me ester: Monomethyl kolavate
C25 H 400 7 M 452.587 C21H 320 4 M 348.481
Constit. of B. salicifolia. Isol. from wood of Gossweilerodendron ba/samiferum.
15-A/dehyde, 17-carboxy/ic acid: [126239-80-3]. ent-15-0xo- Gum. [cx]i? -1 W (CHC1 3).
3, 13E-c/erodadien-11-oic acid. 15-0xo-3, 13E-kolavadien- 13,14-Dihydro: see 3-C/erodene-15,18-dio/, Di-00599
11-oic acid. 13E-Symphyoreticulic acid (ent-5rz,l3E)-form
C20H:14,03 M 318.455 Dicarboxylic acid: [51014-28-9]. Haplopappic acid
Constit. of S. reticulatus and Jungermannia infusca. C20H 300 4 M 334.455
Gum or oil. [cxln -50° (c, 6.15 in CHC1 3). Isol. from Hap/opappus foliosus and H. angustifolius.
131;,14-Dihydro: ent-3-Cierodene-15,17-diol. 3-Ko/avene- Cryst. (EtOH). Mp 242-244°. [cxJn + 117.6° (c, 0.5 in
15,17-dio/ CHC13).
C20H360 2 M 308.503 Ekong, D.E.U. et al, J. Chern. Soc. C, 1969, 2153 (isol)
Isol. from S. reticulatus. Gum. [cx]i;' + 18.5° (c, 1 in Silva, M. eta/, Phytochemistry, 1973, 12, 1755 (Haplopappic acid)
CHC1 3). McCrindle, R. et al, J. Chern. Soc., Chern. Commun., 1974, 453
131;,14-Dihydro, 15-a/dehyde: ent-17-Hydroxy-3-cleroden- (Haplopappic acid)
15-al. 17-Hydroxy-3-ko/aven-15-a/ Misra, R. eta[, Tetrahedron, 1979, 35, 979, 2301 (Kolavic acid)
C21 H360 2 M 320.514 Givovich, A. et a[, Phytochemistry, 1986, 25, 2829 (isol)
lsol. from S. reticulatus. Gum.
131; ,14-Dihydro, 17-a/dehyde: ent-15-Hydroxy-3-cleroden-17- 3,14-Clerodadiene-13,18-diol Dl-00583
al. 15-Hydroxy-3-ko/aven-17-a/
C21 H 360 2 M 320.514
Constit. of S. reticulatus. Gum.
15,17-Dia/dehyde: [126239-82-5]. ent-3,13E-Cierodadiene-
15,17-dial
C20H 300 2 M 302.456
lsol. from J. infusca. Oil. [cxJn -72.8° (c, 0. 74 in CHC1 3). JsCHPH
(ent-13Z)-form C20H340 2 M 306.487
15-A/dehyde: ent-17-Hydroxy-3,13Z-clerodadien-15-al. 17-
(ent-5rz,l31;)-form [56497-92-8] Sagittariol
Hydroxy-3,13Z-kolavadien-15-al Constit. of Sagittaria sagittifolia. Cryst. (C 6H 6 jhexane).
C20H 320 2 M 304.472
Mp 109°. [cxJn +41° (CHC1 3).
Constit. of S. reticu/atus. Gum.
Sharma, S.C. et al, Phytochemistry, 1975, 14, 1055; 1984, 23, 1194
15,17-Dia/dehyde: [126239-81-4]. ent-3,13Z-Clerodadiene- (struct)
15,17-dial
C20 H 300 2 M 302.456
lsol. from J. infusca. Oil. [cxJn -62.7° (c, 1.32 in CHC1 3). 4(18), 12-Clerodadiene-15,16-diol Dl-00584
15-A/dehyde, 17-carboxy/ic acid: [126239-79-0]. ent-15-0xo-
3, 13Z-c/erodadien-17-oic acid. 15-0xo-3, 13Z-kolavadien-
17-oic acid. 13Z-Symphyoreticulic acid
C20 H 300 3 M 318.455
Constit. of S. reticulatus and J. infusca. Cryst. Mp 103-
1050. [cx]n -48° (c, 5.92 in CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1981, 20, 1657.
Zdero, C. et a[, Phytochemistry, 1986, 25, 2841. C20 H340 2 M 306.487
Toyota, M. eta[, Phytochemistry, 1989, 28, 3415. (ent-13Z)-form [96888-24-3]/solinaridiol
Cryst. (CHC1 3). Mp 87-88°. [cxJn + 19.8° (c, 1.2 in
CHC1 3).
752
4(18),13-Clerodadiene-3,15-diol - 4(18),13-Clerodadiene-12,15,16-... Di-00585 - Di-00589

Di-Ac: [96888-18-5]. 3,13-Clerodadiene-15,16,17-triol Dl-00588

C24H 380 4 M 390.562
Constit. of Linaria saxatilis. Oil. [1X] 0 -50.6° (c, 1.8 in .,p CH20H
CHCI 3). CH20H
Dialdehyde: [85120-60-1]. ent-4(18),12-Clerodadiene-15,16- -CH20H
dial. lsolinllridial 17

Constit. of L. saxatilis. Oil. [1X] 0 + 10.7° (c, 1.4 in

CHCI 3).
Teresa, J. de P. et al, An. Quim., 1982, 78, 425 (isol) C10H 340 3 M 322.487
San Feliciano, A. et al, Tetrahedron, 1985, 41, 671 (isol) (ent-8«H,13Z)-form
Piers, E. et al, J. Chern. Soc., Chern. Commun., 1988, 1245 (synth) Constit. of Baccharis boliviensis.
17-0-P- Xylopyranoside:
4(18),13-Clerodadiene-3,15-diol Dl-00585 ~H4207 M 454.603
Constit. of B. boliviensis.
17-Carboxylic acid: ent-15, 16-Dihydroxy- 3, 13-c/erodadien-
17-oic acid. 16-Hydroxybacchasalicylic acid
CzoH310 4 M 336.470
Constit. of B. boliviensis.
HO' 17-Carboxylic acid, 15-Ac: 16-Hydroxybacchasalicylic acid
15-0-acetate
C10H 340 2 M 306.487 C 12H 340 5 M 378.508
(ent-Jfl,JJE)-form [24513-43-7] Agbanindiol A Constit. of B. salicifolia. Oil. [1X]t' -45° (c, 2 in
Constit. of Gossweilerodendron balsamiferum. Cryst. (pet. CHC1 3)(as Me ester).
ether). Mp 85-87°. [IX]~ -9.2°. Zdero, C. et al, Phytochemistry, 1989, 28, 531.
Ekong, D.E.U. et al, J. Chern. Soc. C, 1969, 2153.
4(18),13-Clerodadiene-12,15,16-triol Dl-00589
3,13-Clerodadiene-15,16;18,19-diolide Dl-00586
OH
0 1 ~H20H

116
_, CH2 0H

CzoH3403 M 322.487
(ent-12S,13E)-form [96888-13-0] lsolinllritriol
Cryst. (EtOAc). Mp 160-161°. [1X] 0 +44.2° (c, 1 in
CHC13).
12,15-Di-Ac: [96888-25-4].
M 330.423 C:z.cH380 5 M 406.561
ent-form Constit. of Linaria saxatilis. Oil. [1X] 0 + 10.8° (c, 2.4 in
Constit. of Baccharis pedicellata and B. marginalis. CHCI3).
Cryst. (Et20). Mp 130-132°. [1X]i; -146.4° (c, 1.1 in 12,16-Di-Ac: [96888-23-2].
CHCI 3). C24H 380 5 M 406.561
Faini, F. et al, Phytochemistry, 1987, 26, 3281. Constit. of L. saxatilis. Oil. [1X] 0 + 32.3° (c, 1 in CHC13).
15,16-Di-Ac: [96888-22-1].
3,13-Clerodadiene-15,16,18,19-tetrol Dl-00587 C:z.cH380 5 M 406.561
Constit. of L. saxatilis. Oil. [1X] 0 +21.8° (c, 1.2 in
CHpH CHC13).
Tri-Ac: [96947-58-9].
~H40 06 M 448.598
Constit. of L. saxatilis. Oil. [1X] 0 + 17.3° (c, 1.1 in
'
HOH2C CHpH
I
CHC13).
San Feliciano, A. et al, Tetrahedron, 1985, 41, 671.

C10H 340 4 M 338.486

(ent-JJZ)-form [117590-96-2] lewenol A
Constit. of Portulaca cv. jewel. Oil. [IX]~ -87.6° (c, 0.37
in EtOH).
Ohsaki, A. et al, Phytochemistry, 1988, 27, 2171.

753
2,4(18)-Cierodadien-15-oic acid - 3,13-Cierodadien-15,12-olid-18-... Di-00590 - Di-00594

2,4(18)-Cierodadien-15-oic acid
Dl-00590 King, T J. eta/, J. Chern. Soc., Chern. Commun., 1967, 575; 1969,
683 (Plathyterpol)
Misra, R. eta/, Tetrahedron Lett., 1968, 2685 (synth)
Anthonsen, T. eta/, Acta Chern. Scand., 1969, 23, 1068
(Kolavelool)
Juneja, R.K. et a/, Indian J. Chern., Sect. B, 1986, 25, 748 (18-
Deoxysagittarol)

4(18),13-Clerodadien-15-ol Dl-00593
c~32 0 2 M 304.472
(ent-13f.)-form [68268-63-3] lsodehydropopu/ifolic acid
Constit. of Cistus popu/ifolius.
De Pascual Teresa, J. eta/, An. Quim., 1978, 74, 476.
(13£)-form
3,13-Cierodadien-15-ol Dl-00591
C20H 340
(13£)-form [68799-37-1] Bedfordiaditerpellfllcohol
Constit. of Bedfordia salicina. Oil.
(13£)-form (ent-13£)-form
15-Carboxy/ic acid: [52936-75-1]. ent-4(18),13E-
Ckrodadien-15-oic acid
C20H 320 2 M 304.472
c~ 34 o M 290.488 Isol. from Araucaria bidwilli. Oil (as Me ester). [ocln +9°
(13£)-form [68852-38-0] lsobedfordilu/iterpeNllcohol (c, 2 in CHC1 3) (Me ester).
Constit. of Bedfordia sa/icina. Oil. (ent-13Z)-form
(ent-13£)-form [19941-83-4] Kolavenol 15-Carboxy/ic acid: [120552-37-6]. ent-4(18),13Z-
Constit. of Hardwickia pinnata and roots of Solidago Cierodadien-15-oic acid
elongata. Oil. Bp0 .025 140-150° (bath). [ocln -45.7° C20H 320 2 M 304.472
(CHC1 3). lsol. from Ageratina ixiocladon.
3,5-Dinitrobenzoyl: Cryst. (EtOH). Mp 105-106°. 15-Carboxy/ic acid, 4oc,J8-epoxide: [120552-39-8]. ent-4P,18-
15-Carboxy/ic acid: [25436-90:2]. ent-3, 13-Clerodadien-15- Epoxy-13-ckroden-15-oic acid
oic acid. Kolavenic acid C20H 320 3 M 320.471
C~ 32 0 2 M 304.472 Constit. of A. ixiocladon.
Constit. of H. pinnata and S. altissima. 15-Carboxy/ic acid, 4P,I8-epoxide: [120662-27-3]. ent-4«,18-
15-Carboxy/ic acid, Me ester: [23527-24-4]. Epoxy-13-ckroden-15-oic acid
C 21 H 340 2 M 318.498 C20H 320 3 M 320.471
Isol. from roots of S. elongata. Liq. Bp0 .4 179-180°. [ocln Constit. of A. ixiocladon.
-65.6° (CHC1 3). Caputo, R. eta/, Phytochemistry, 1974, 13, 467.
Misra, R. eta/, Tetrahedron Lett., 1964, 3751; 1968, 2681 (isol, Bohlmann, F. et al, Phytochemistry, 1978, 17, 1173.
struct, abs conjig) Tanayo-Castillo, G. eta/, Phytochemistry, 1989, 28, 139.
Anthonsen, T. et al, Acta Chern. Scand., 1969, 23, 1068 (isol)
Ferguson, G. eta/, J. Chern. Soc., Chern. Commun., 1975, 299
(stereochem) 3,13-Clerodadien-15,12-olid-18-oic acid Dl-00594
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1173 (isol)
Hubert, T.D. eta/, Phytochemistry, 1985, 24, 1197 (isol, cmr)
Iio, H. eta/, J. Chern. Soc., Chern. Commun., 1987, 358 (synth) 0
Lopes, L.M.X. et al, Phytochemistry, 1987, 26, 2781 (cmr)

3,14-0erodadien-13-ol Di-00592

HOOC
(ent- 5cx,8 ~H, 13~)-form C20H 280 4 M 332.439
(ent-5«,12f.)-form [113963-47-6] Ephemeric acid
Constit. of Ephemerantha comata. Cryst.
C20H 340 M 290.488 (CHC1 3/hexane). Mp 183-185°. [ocln -75.0° (c, 0.56 in
CHC1 3).
(ent-5«,8PH,13f.)-form [16910-19-3] Plathyterpol
Constit. of the heartwood of Plathymenia reticulata. Oil. P-v-Glucopyranosy/ ester: [113963-46-5]. Ephemeroside
Bp0.2 142-144°. [oc]n -28° (c, 0.2 in CHC1 3). The C26H 280 9 M 484.502
stereochem. shown may be incorrect. Constit. of E. comata. Viscous liq. [ocln -43.2° (c, 1 in
MeOH).
(ent-5«,8«H,13f.)-form
Niwa, M. et al, Phytochemistry, 1987, 26, 3293.
18-Deoxysagittarol
Constit. of Sagittaria sagittifolia. Viscous liq.
(ent-5P,8«H,l3f.)-form [19941-81-2] Kolavelool
Isol. from o1eroresin of Hardwickia pinnata and roots of
Solidago elongata. Oil. [oc]i; -40.4° (CHC1 3).

754
3,13-Clerodadien-15,16-olid-19-... - 3-Clerodene-15,18-diol Di-00595 - Di-00599

3,13-Clerodadien-15,16-olid-19-oic acid Dl-00595 3,13(16),14-Clerodatrien-17-al Dl-00597

( 5a.,8a.H)-form

C:zoH 280 4 M 332.439 C:zoH 300 M 286.456

Oil. ent-form [126286-67 -7]
(5rx.,8rx.H)-form Constit. of Jungermannia infusca. Oil. [1X]n -63.7° (c,
19-0-IX-L-Arabinopyranosyl ester: 1.93 in CHC1 3).
C25H 360 8 M 464.555 17-Carboxylic acid: [125002-94-0]. ent-3,13(16),14-
Constit. of Gutierrezia texana. Oil. [IX]~ -19° (c, 0.77 in Cierodatrien-17-oic acid
MeOH). C10H 300 2 M 302.456
(5P,8PH)-form Isol. from J. infusca. Cryst. [ocln -43.6° (c, 1.26 in
19-Alcohol: [70387-33-6]. 19-Hydroxy-3,13-clerodadien- CHC13).
15,16-olide. lsonidorellalactone Toyota, M. et al, Phytochemistry, 1989, 28, 2507, 3415 (isol, pmr,
C:zoH31,03 M 318.455 cmr)
Constit. of Nidorella spp. Oil. [(l']i;4 -31.0° (c, 1.9 in
CHC1 3). 2,4(18),13-Clerodatriene-15,16-diol Dl-00598
(ent-5p,8rx.H)-form
Strigillanoic acid A
lsol. from Hoffmannia strigillosa. Oil.
16¢-Hydroxy: ent-16-Hydroxy-3,13-clerodadien-15,16-olid-
19-oic acid. Strigillanoic acid C
C:zoH 28 0~ M 348.438
From H. strigillosa.
Bohlmann, F. et al, Phytochemistry, 1978, 17, 1769. C10H 320 2 M 304.472
Gao, F. et al, Phytochemistry, 1987, 26, 209.
Jaensch, M. et al, Phytochemistry, 1990, 29, 3587. (ent-13Z)-form
Constit. of Baccharis boliviensis.
3,13-Clerodadien-16, 15-olid-18-oic acid Di-00596 Zdero, C. et al, Phytochemistry, 1989, 28, 531.

3-Clerodene-15,18-diol Dl-00599

Sa-form

{ent-8a.H, 13R)-form

CH2 0H
COOH
C10H 360 2 M 308.503
C10H 280 4 M 332.439 (ent-8rx.H,13R)-form
5rx.-form [67517-02-6] Floridiolide A 15,18-Dicarboxylic acid: [70492-74-9]. ent-3-Clerodene-
Constit. of Evodiafloribunda. Cryst. (EtOAcjhexane). 15,18-dioic acid. Haplocililltic acid
Mp 160-162°. [oc]i; -68.8° (MeOH). C:zoH32 0 4 M 336.470
17-Hydroxy: [67517-03-7]. 17-Hydroxy-3,13-clerodadien- lsol. from Haplopappus ciliatus. Cryst. (EtOH). Mp 198-
16,15-olid-18-oic acid. Floridiolide B 2010. [oc]i; -86° (c, 2.5 in EtOH).
CzoH 28 0~ M 348.438 (ent-5rx.,8~H,13~)-form [28644-71-5] Cistodiol
From E. floribunda. Oil. [oc]i; -23.17° (MeOH). Constit. of Cistus monspeliensis. Cryst. Mp 86-88°. [ocln
(ent-5/1)-form [114020-67-6] Patagonie acid. 15,16-Dihydro-16- +47.9° (CHC1 3).
oxohardwickiic acid 15,18-Dicarboxylic acid: [28644-72-6]. Cistodioic acid
Isol. from Baccharis patagonica and Grangea C:zoH3p 4 M 336.470
maderaspatana. Cryst. Mp 100-103°. [ocln -65.9° (c, 2.65 Constit. of C. monspeliensis. Cryst. Mp 255-256°. [1X]n
in CHC1 3). +63.6° (EtOH).
15-Methoxy: 15,16-Dihydro-15-methoxy-16-oxohardwickiic (ent-5P,8rx.H,13~)-form
acid
15-Carboxylic acid: ent-18-Hydroxy-3-cleroden-15-oic acid
C 21 H 31,0~ M 362.465
Constit. of G. maderaspatana. C10H 240 3 M 312.408
lsol. from Relhania corymbosa and R. genistifolia.
Billet, D. et al, J. Chern. Res. (M), 1978, 1475.
Rivera, A.P. et al, J. Nat. Prod. (Lloydia), 1988, 51, 155. 15-Carboxylic acid, Ac:
Singh, P. et al, Phytochemistry, 1988, 27, 1537. C22 H 360 4 M 364.524
Constit. of R. genistifolia.
15-Carboxylic acid, 13£,14-didehydro, Ac: ent-19-Acetoxy-
3,13-clerodadien-15-oic acid
755
3-Clerodene-15,16:19,6-diolide- 3-Cleroden-15,16-olide Di-00600 - Di-00605

C12H 340 4 M 362.508 Constit. of G. paniculata. Gum. [<X]i;' -33° (c, 0.62 in
Constit. of R. genistifolia. CHCI 3).
Berti, G. eta/, Tetrahedron Lett., 1970, 1401. Bohlmann, F. eta/, Phytochemistry, 1983, 22, 191.
Bittner, M.L. eta/, Phytochemistry, 1978, 17, 1797 (Haplociliatic
acid)
Tsichritzis, F. et a/, Phytochemistry, 1990, 29, 3173. 3-Cieroden-15-oic acid Dl-00603

3-Cierodene-15,16:19,6-diolide Dl-00600
H
0

C 20H 340 2 M 306.487

(ent-13q,)-form [68330-95-0] Populifolic acid
Constit. of Cistus popu/ifolius. Oil (as Me ester). [<X]n
-27.3° (c, 1.3 in CHC1 3) (Me ester).
C 20H 280 4 M 332.439 1,2-Didehydro: [68268-62-2]. ent-1 ,3-C/erodadien-15-oic
acid. Dehydropopulifolic acid
(ent-5«,6P,J3q,)-Jorm [71051-91-7] C20H 320 2 M 304.472
Constit. of Symphiopappus itatiayensis. Cryst. Mp 150°. Constit. of C. populifolius. Oil (as Me ester). [1X]n -73.6°
[1X]n +9.62° (c, 1 in CHCI 3). (c, 2.26 in CHC1 3) (Me ester).
Vichnewski, W. eta/, Phytochemistry, 1979, 18, 129. (ent-5«,11q,)-Jorm
3fi,4fi-Epoxide: [118173-05-0]. ent-3«,4«-Epoxy-15-
13-Cierodene-2,3,4, 15,16-pentol Dl-00601 clerodanoic acid
C 20 H 340 3 M 322.487
CHPH !sol. from Ageratina salti/lensis.
De Pascual Teresa, J. eta/, An. Quim., 1978, 74, 476.
CHpH Lopes, L.M.X. et a/, Phytochemistry, 1987, 26, 2781 (cmr)
Fang, N. eta/, Phytochemistry, 1988, 27, 3187 (epoxide)
HO"
HO
4(18)-Cieroden-15-oic acid Dl-00604
C 20H 360s M 356.501
(ent-2P,JP,4«,11Z)-form
Constit. of Baccharis boliviensis. COOH
Zdero, C. eta/, Phytochemistry, 1989, 28, 531.

3-Cierodene-6,15, 17,18-tetrol Dl-00602

C 20 H 320 2 M 304.472
(ent-13q,)-form [120552-38-7]
Constit. of Ageratina ixiocladon.
4<X,18-Epoxide: [120552-40-1]. ent-4P,18-Epoxy-15-
clerodanoic acid
C 20 H 340 3 M 322.487
HOH2 ~ Constit. of A. ixiocladon.
4fi,J8-Epoxide: [120662-28-4]. ent-4«,18-Epoxy-15-
C 20H 360 4 M 340.502
clerodanoic acid
(ent-6P,J3q,)-jorm C20H 340 3 M 322.487
3-Kolavene-6,15,17,18-tetrol Constit. of A. ixiocladon.
17-Ac: Tanayo-Castillo, G. eta/, Phytochemistry, 1989, 28, 139.
C 22H 380s M 382.539
Constit. of Gochnatia paniculata. Gum. [1X]n -28° (c, 0.3
in CHCI 3). 3-Cieroden-15, 16-olide Di-00605
17-Phenylacetyl.· 17-Phenylacetoxy-3-kolavene-6«,15,18-triol
C 28H 420s M 458.637
Constit. of G. paniculata. Gum. [1X]n -19° (c, 0.13 in
CHCI 3).
18-Aldehyde, 17-Ac: 17-Acetoxy-6«,15-dihydroxy-3-kolaven-
18-a/
C12H 360s M 380.523
C20H 320 2 M 304.472
Constit. of G. paniculata. Gum. [1X]n -38° (c, 0.2 in
CHCI 3). (ent-13q,)-form
15 ,16-Kolavenolide
18-A/dehyde, 17-pheny/acetyl: 17-Phenylacetoxy-6«,15-
dihydroxy-3-kolaven-18-al
C28H400S M 456.621

756
Clerodinin C - 4,18:15,16-Diepoxy-13(16),14-... Di-00606 - Di-00611

Constit. of Bahianthus viscidus. Gum. [ex]~ -29° (c, 0.3 (ent-3p,4p,JOrx.,l2S)-form

in CHCI 3). Constit. of Microglossa pyrrhopappa. Gum.
Bohlmann, F. et al, Phytochemistry, 1981, 20, 331. Zdero, C. et al, Phytochemistry, 1990, 29, 3233 (isol)

Clerodinin C Dl-00606 4,20:15,16-Diepoxy-13(16),14- Dl-00609

[124753-87-3] clerodadiene-3,12-diol
OEt

HO...

C20H300 4 M 334.455
(ent-3P,4P,l Orx.,l2S)-form
Constit. of Microglossa pyrrhopappa. Cryst. Mp 177°.
C26H 400 8 M 480.597
[cx]4 -85° (c, 0.11 in CHCI 3).
Constit. of Clerodendron brachyanthum. Cryst. Mp 147-
1490. [cx]i; + 30° (c, I in CHCI 3). Zdero, C. et al, Phytochemistry, 1990, 29, 3233 (isol)
15-Epimer: [124815-92-5]. Clerodinin D
C26H 400 8 M 480.597 4,18:15,16-Diepoxy-13(16),14- Dl-00610
Constit. of C. brachyanthum. Cryst. Mp 163-165°. [cx]i,l clerodadiene-3,6,12,19-tetrol
-31.5° (c, I in CHCI 3).
Lin, Y.-L. et al, Heterocycles, 1989, 29, 1489 (isol, pmr, cmr)

Clerodiol Di-00607
[124693-69-2]
OEt

CwH3006 M 366.453
(ent-3rx.,4p,6p,J2f,)-form
6-Ac: [103827-25-4]. Teupyrin B
C22 H 3P 7 M 408.491
Constit. of Teucrium pyrenaicum. Cryst.
(EtOAcjhexane). Mp 213-215°. [cx]i,6 +7.1° (c, 0.126 in
MeOH).
Fernandez, P. eta/, Phytochemistry, 1986, 25, 1405.
CuH420 9 M 498.612
Constit. of Clerodendron brachyanthum. Cryst. Mp 153- 4,18:15,16-Diepoxy-13(16),14- Dl-00611
1550. [cx]i,l + 140° (c, I in CHCI 3). clerodadiene-6,12,19,20-tetrol
Lin, Y.-L. et al, Heterocycles, 1989, 29, 1489 (isol, pmr, cmr)

3,4:15,16-Diepoxy-13(16),14-clerodadiene- Dl-00608
12,20-diol

I
I
I
I

CH20H
19

C 20 H 300 6 M 366.453
(ent-6P,12f,)-form
6,19-Di-Ac: [113305-28-5]. Teucretol
M 334.455
C24H 340 8 M 450.528

757
4,18:15,16-Diepoxy-13(16),14-••• - 3,4:15,16-Diepoxy-6,10-dihydroxy-... Di-00612 - Di-00617

Constit. of Teucrium creticum. Syrup. [ex]i;' -8.8° (c, 3,4:15,16-Diepoxy-13(16), 14-clerodadien- Dl-00615
0.341 in CHC1 3). 20,12-olide
Savona, G. eta/, Phytochemistry, 1987, 26, 3285.

4,18:15,16-Diepoxy-13(16),14- Di-00612
clerodadiene-6,12,19-triol

C:zoH260 4 M 330.423
(ent-3«,4«,5«,12PH)-form [102904-58-5] Chiliomarin
Constit. of Chiliotrichium rosmarinifolium. Oil. [ex]~
-13° (c, 0.72 in CHC1 3).
Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305.

C:zoH300 5 M 350.454
(ent-4P,6P,12R)-form [92356-81-5] Teumassilin
3,4:15,16-Diepoxy-13(16), 14-clerodadien- Di-00616
Constit. of Teucrium massiliense. Syrup. [ex]~ -3.6° (c, 20,12-olid-18-oic acid
0.561 in CHC1 3). 0
6,19-Di-Ac: 6,19-Diacetylteumassilin
C24H 340 7 M 434.528
Constit. ofT. massiliense. Cryst. (EtOAcfhexane). Mp
Q

~~
155-156°. [ex]~ -19.3° (c, 0.192 in CHC1 3).
Savona, G. eta/, Phytochemistry, 1984, 23, 849.

3,4:15,16-Diepoxy-13(16), 14-clerodadien- Di-00613

20-oic acid
°COOH
C:zoH 240 6 M 360.406
(ent-3P,4P,12«H)-form
Me ester: [58141-91-6]. Draconin
C21H 260 6 M 374.433
Constit. of Croton draco. Cryst. Mp 184-186°.
Rodriguez-Hahn, L. eta/, Rev. Latinoam. Quim., 1975, 6, 123; CA,
84, 56485p.

3,4:15,16-Diepoxy-6,1 0-dihydroxy- Di-00617

C:zoH 280 4 M 332.439 13(16),14-clerodadien-20,12-olide
(ent-3p,4p)-form [50489-67-3] Epoxyjunceic acid
Constit. of Solidago juncea. Oil. Bp0 _01 160° (Me ester).
[exln -49° (c, 2.1 in CHC1 3) (Me ester).
Henderson, M.S. eta/, Can. J. Chern., 1973, 51, 1322.
Q I

3,4;15,16-Diepoxy-13(16),14-clerodadien-
2-ol
Di-00614
~0
C20H 260 6
~
M 362.422
(ent-3P,4P,6«,10«,12«H)-form
Constit. of Microglossa pyrrhopappa. Gum.
C:zoH300 3 M 318.455 6-Angeloyl:
(ent-2P,3P,4p)-form C25 H 320 7 M 444.524
Constit. of Baccharis boliviensis. Gum. [ex]~4 + 8° (c, 5.65 Constit. of M. pyrrhopappa. Gum.
in CHC1 3). 6-(2- M ethylbutanoyl):
Me ether: ent-3p,4p;J5,16-Diepoxy-2P-methoxy-13(16),14- C25 H 340 7 M 446.539
clerodadiene Constit. of M. pyrrhopappa. Gum.
C21 H 320 3 M 332.482 Zdero, C. eta/, Phytochemistry, 1990, 29, 3233 (iso[)
Constit. of B. boliviensis. Gum.
Zdero, C. eta/, Phytochemistry, 1989, 28, 531.

758
4,18:15,16-Diepoxy-6,19-dihydroxy-... - 4,18:15,16-Diepoxy-1,19-dihydroxy-... Di-00618 - Di-00621

4,18:15,16-Diepoxy-6,19-dihydroxy- Dl-00618 6,8:15,16-Diepoxy-12,18-dihydroxy- Dl-00619

13(16),14-clerodadien-20,12-olide 13(16),14-clerodadien-20,19-olide
0 0
~ 1: ltJ

(ent-4~,6a, 12~H):form

H<l
C10H 260 6 M 362.422 C20H 260 6 M 362.422
(ent-4P,6«,12PH)-forFf1 (ent-12R,18p)-form [96386-38-8] Teuchamaedrin C
19-Ac: [81422-44-8]. Teucjaponin A Constit. of Teucrium chamaedrys. Cryst. (MeOHjEtp).
CuH:zs07 M 404.459 Mp 205-208°. [IX]~ -37.SO (c, 0.149 in Me2CO).
Constit. of Teucrium japonicum. Insect antifeedant. Malakov, P.Y. eta/, Phytochemistry, 1985, 24, 301.
Cryst. (Me 2CO/C 6HJ. [ex]~ +38.8° (c, 3.84 in CHC1 3).
6-Ketone: [70544-90-0]. ent-4P,18:15,16-Diepoxy-19- 15,16:18,19-Diepoxy-6,18-dihydroxy- Dl-00620
hydroxy-6-oxo-13(16), 14-c/erodadien-20, 12-olide.
Gnaphalin
13(16),14-clerodadien-20,12-olide
CzoH1406 M 360.406 0
Isol. from T. gnaphaloides. Cryst. Mp 171-174°. [ex]~
+46.6° (c, 0.51 in CHC1 3).
6-Ketone, 19-Ac: [64756-04-3]. Teucrin HJ. 19-
Acety/gnaphalin
C12H 260 7 M 402.443
Isol. from T. gnapha/oides and T. hyrcanicum. Cryst. Mp
227-229°. [ex]~ +8]0 (c, 0.315 in CHC1 3).
(ent-4P,6P,12«H)-form
6-Ac: 12-Epiteupolin II
CzzH:zs07 M 404.459
Constit. ofT. /amiifolium. Cryst. (Me2COjpet. ether). C10H 260 6 M 362.422
Mp 173-175°. [ex]~ + W (c, 0.33 in Me 2CO). (ent-4«H,6r~.,12PH,18«)-form [125137-21-5] Teukotschyn
(ent-4P,6P,12PH)-form Constit. of Teucrium kotschyanum. Amorph. solid. Mp
6-Ac: [72948-21-1]. Teupolin II 95-105°. [1X]~ -5.7° (c, 0.317 in CHC1 3).
CzzH:zs07 M 404.459 6-Ketone: [87376-65-6]. ent-15, 16:18,19-Diepoxy-18-
Isol. from T. polium. Cryst. (EtpjMe 2CO). Mp 187- hydroxy-6-oxo-13( 16), 14-c/erodadien-20, 12-olide.
1890. [ex]~ +52° (c, 0.2 in CH 2Cl2). Teuscorot/jn
19-Ac: [72948-20-0]. Teupolin I. Teucjaponin B lsol. from T. scorodonia. Cryst. (Me 2C0jhexane). Mp
CzzH:zs07 M 404.459 152-153°. [IX]~ +2.9° (c, 0.24 in CHC1 3).
Constit. of Teucrium polium and T. japonicum. Cryst. Marco, J.L. eta/, Phytochemistry, 1983, 22, 727 (Teuscorodin)
(Et20/CHC13). Mp 211-213°, Mp 255-258°. [1X]~ +60° Simoes, F. eta/, Phytochemistry, 1989, 28, 2763 (Teukotschyn)
(c, 0.2 in CH 2ClJ.
Di-Ac: [67987-83-1]. Montanin C 4,18:15,16-Diepoxy-1,19-dihydroxy- Dl-00621
C14H 300 8 M 446.496 13(16),14-clerodadien-6-one
Constit. ofT. montanum. Cryst. Mp 181-183°. [IX]~
+ 8.4° (c, 0.262 in CHC1 3).
Gacs-Baitz, E. eta/, Phytochemistry, 1978, 17, 1967; 1987, 26,
2110 (iso/, struct, bib[)
Savona, G. eta/, Phytochemistry, 1978, 17, 1967 (isol)
Ma1akov, P.Y. eta/, Z. Naturforsch., B, 1978, 33, 789; 1979, 34,
1570 (isol)
Gacs-Baitz, E. eta/, Heterocycles, 1982, 19, 539 (cmr)
Fayos, J. et al, J. Org. Chern., 1984, 49, 1789 (struct)
Boneva, I.M. et al, Phytochemistry, 1988, 27, 295 (deriv)

C20 H:zs05 M 348.438

(ent-1P,4p)-form
19-Ac: [67233-27-6]. Fruticolone
CuH300 6 M 390.475
Constit. of Teucrium fruticans. Cryst. (EtOAcjpet.
ether). Mp 150°. [1X]n + 28.3° (c, 0.3 in CHC1 3).

759
15,18:18,19-Diepoxy-2,18-dihydroxy-... - 3,6:15,16-Diepoxy-4-hydroxy-6-... Di-00622 - Di-00626

1-Ketone, 6P-alcoho/, 19-Ac: [67244-39-7]. 19-Acetoxy- 1,12:15,16-Diepoxy-20-hydroxy-13(16),14- Dl-00624

4,18:15,16-diepoxy-6p-hydroxy-13(16),14-c/erodadien-l- clerodadien-18,6-olide
one. /sofrutico/one
C22 H:11,06 M 390.475
Constit. ofT. fruticans. Oil. [a]n -87.8° (c, 0.25 in
CHC1 3).
Savona, G. eta/, J. Chern. Soc., Perkin Trans. I, 1978, 356.

1S,16:18,19-Diepoxy-2,18-dihydroxy-6- Dl-00622
oxo-13(16),14-clerodadien-20,12-olide
0
~
C10H 160 5 M 346.422
(ent-1 rx.,4rx.H,5rx.,6P,12rx.H)-form
20-Ac: (37299-07-3]. Gymnocolin
C22 Hzs06 M 388.460
Constit. of liverwort Gymnocolea inflata. Plant growth
regulator (inhibits cress root growth, promotes wheat
seed germination). Cryst. (MeOH). Mp 196-197°.
Huneck, S. et a/, Phytochemistry, 1972, 11, 2429.
Czoll1,,07 M 376.405 Huneck, S. et a/, Tetrahedron Lett., 1983, 24, 115 (cryst struct)
(ent-2rx.,4rx.H,18rx.,J2PH)-form [103994-20-3] Teusalvin B
Constit. of Teucrium salviastrum. Cryst. 3,4:15,16-Diepoxy-2-hydroxy-13(16),14- Dl-00625
(EtOAcjhexane). Mp 199-202°. (a]~ -10° (c, 0.052 in clerodadien-20,12-olide
CHC1 3).

Q
2-Ketone: [103994-21-4]. 15,16:18,19-Diepoxy-18-hydroxy-
2,6-dioxo-13(16),14-c/erodadien-20,12-olide. Teusalvin A
Czoll22 0 7 M 374.390
From T. salviastrum. Cryst. (EtOAc). Mp 224-227°. [a]~
+ 146° (c, 0.051 in CHC1 3).
De La Torre, M.C. eta/, Phytochemistry, 1986, 25, 1397.

4,6:15,16-Diepoxy-2-hydroxy-13(16),14- Dl-00623
clerodadiene-18,19:20,12-diolide
C10H 160 5 M 346.422
(ent-2p,Jp,4p,JOrx.,12rx.H)-form
Constit. of Microg/ossa pyrrhopappa. Gum. (a]~4 -4° (c,
0.67 in CHC1 3).
1,10-Didehydro: 3,4:15,16-Diepoxy-2-hydroxy-
1(10),13(16),14-clerodatrien-20,12-olide
C10H 240 5 M 344.407
Absolute Constit. of M. pyrrhopappa. Gum. [a]~ - 19° (c, 0.23 in
configuration CHCl3).
Zdero, C. eta/, Phytochemistry, 1990, 29, 3233 (isol)
C10H110 7 M 374.390
(ent-2rx.,4rx.,6rx.,12PH)-form [82679-43-4] Chamaedroxide 3,6:15,16-Diepoxy-4-hydroxy-6-methoxy- Dl-00626
Constit. of Teucrium chamaedtys. Cryst. (Me2CO/Et20). 13(16),14-clerodadien-20,12-olide
Mp 255-257°. [a]i,O +37.1° (c, 0.42 in Py). 3,6:15,16-Bisepoxy-4-hydroxy-6-methoxy-13(16),14-
2-Deoxy: 4,6:15,16-Diepoxy-13(16),14-c/erodadiene- c/erodadien-20,12-o/ide
18,19:20,12-dio/ide. 2-Deoxychamaedroxide
CzoH220 6 M 358.390
Constit. ofT. divaricatum. Amorph. powder. Mp 85-89°.
Eguren, L. eta/, J. Org. Chern., 1982, 47, 4157 (isol, struct)
Q
Bruno, M. et a/, Phytochemistry, 1987, 26, 2859 (deriv)

760
3,4:15,16-Diepoxy-10-hydroxy-6-oxo-... - 4,18:15,16-Diepoxy-2,6,19-... Di-00627 - Di-00631

C21 H 280 6 M 376.449 12,17:15,16-Diepoxy-7-oxo-

(3«,4P,6«)-form [129349-89-9] 3,8(17), 13(16),14-clerodatetraen-18,19-
Constit. of Pteroxia eenii. olide Dl-00630
Zdero, C. et al, Phytochemistry, 1990, 29, 1231 (isol, pmr)

3,4:15,16-Diepoxy-10-hydroxy-6-oxo-
13(16),14-clerodadien-20,12-olide
Dl-00627 0 I

Q
(ent-12CJ.H)-form

C20H 200 5 M 340.375

(ent-12«H)-form
12-Epiconycephaloide
Constit. of Baccharis scoparia. Oil. [cx]i;l -86° (c, 0.14 in
C20H 240 6 M 360.406 CHC1 3).
Incorrectly called a 1abdane in ref. 8P,17-Dihydro: 12,20:15,16-Diepoxy-7-oxo-3,13(16),14-
(4«,5«,1 op,J2Pffl-form c/erodatrien-18,19-olide
Constit. of Conyza pyrifolia. Cryst. Mp 204°. [cx]~4
C20H 220 5 M 342.391
-111° (c, 0.18 in CHC1 3). From B. scoparia. Cryst. Mp 182°. [cx]i;l -158° (c, 0.3 in
CHC1 3).
Zdero, C. et al, Phytochemistry, 1990, 29, 3167 (isol, pmr)
(ent-12PH)-form (84765-49-1] Conycephaloide
Constit. of Conyza podocephala. Cryst. (Etp). Mp 208°.
3,4:15,16-Diepoxy-7-oxo-13(16),14- Dl-00628 [cx]i;l -136° (c, l.l in CHC1 3).
clerodadien-20, 12-olide Bohlmann, F. et al, Phytochemistry, 1982, 21, 1693; 1985, 24, 511.
3,4; 15,16-Bisepoxy-7-oxo-13(16),14-c/erodadien-20,12-olide
C~ 24 0 5 M 344.407 4,18:15,16-Diepoxy-2,6,19-trihydroxy- Di-00631
Descr. in the ref. as both 6-oxo and 7-oxo. 7-oxo appears
to be correct; it has a different Mp.from the 6-isomer. 13(16),14-clerodadien-20,12-olide
(3«,4«)-form [129097-49-0] 0

'#
Constit. of Nardophyllum lanatum. Cryst. Mp 198°.
8P-Hydroxy: [129384-20-9]. 3cx,4cx; 15,16-Diepoxy-8p-
hydroxy- 7-oxo-13(16), 14-c/erodadien- 20, 12-olide
C20H 240 5 M 344.407
Constit. of P. eenii. Cryst. Mp 210°. Descr. as 6-oxo in
CA (see note above). HO
Zdero, C. eta/, Phytochemistry, 1990, 29, 1227 (isol, pmr, cmr)

3,4:15,16-Diepoxy-6-oxo-13(16),14- Dl-00629
clerodadien-20,12-olide
3,4;15,16-Bisepoxy-6-oxo-13(16),14-c/erodadien-20,12-olide C20 H 260 7 M 378.421
(ent-2«,4P,6«,12PH)-form

Q I
19-Ac: [90851-19-7]. Teumarin
C22 H 280 8 M 420.458
Constit. of Teucrium marum. Amorph. solid. Mp 98-

~?
H>70. (cx]i? +34.1° (c, 0.135 in CHC1 3).

w
Savona, G. et al, Phytochemistry, 1984, 23, 611.

C20H 240 5 M 344.407

(3«,4«)-form [129384-19-6]
Constit. of Pteronia eenii. Cryst. Mp 170°.
Zdero, C. et al, Phytochemistry, 1990, 29, 1231 (pmr, cmr)

761
4,18:15,16-Diepoxy-3,6,19-... - 4,18:15,16-Diepoxy-1,8,19-... Di-00632 - Di-00634

4,18:15,16-Diepoxy-3,6,19-trihydroxy- Dl-00632 6,19-Di-Ac: [78037-29-3]. Teucapitatin

13(16),14-clerodadien-20,12-olide C24H 300 9 M 462.496
Constit. of Teucrium capitatum. Cryst. (EtOAcjhexane).
0

0
Mp 208-210°.
6-Ketone, 7,19-di-Ac: [77912-51-7]. Capitatint
C 24 H 28 0 9 M 460.480
\
Constit. ofT. capitatum. Cryst. (EtOH/EtOAc). Mp
(ent-3a,4~,6~, 12aH)-form 165-166°.
(ent-4P,6P,7«,12PII)-form
6-Ketone, 7-Ac: [89984-04-3]. Teupolin IV
C 22H160 8 M 418.443
I

I : I
Isol. from T. polium. Cryst. (Me 2CO/Et 20). Mp 196-
0 : OH 1980. [ex]~ +90.9° (c, 0.154 in Me 2CO).
HOH2 C 6-Ketone, 7,19-di-Ac: 19-Acetylteupolin IV
C 20H 160 7 M 378.421 C 24 H 280 9 M 460.480
lsol. from T. polium ssp. pilosum. Cryst.
(ent-3«,4P,6P,12«11)-form
(EtOAcjhexane). Mp 230-234°. [ex]i;' + 132.3° (c, 0.161
6,19-Di-Ac: [107690-88-0]. Montanin G in Py).
C 24H:~,0 9 M 462.496
Constit. of Teucrium montanum var. scorpilii. Cryst. 7-Ketone, 19-Ac: [28393-22-8]. Picropoline
(Me 2COjpet. ether). Mp 239-241°. (ex]i,<l + 11.2° (c, 0.24 C 22H 160 8 M 418.443
Isol. from T. polium. Cryst. (CHCI 3/Et20). Mp 199-
in Me 2CO).
201°. [ex]i,<l +44.5° (c, 0.2 in CHCI 3).
Tri-Ac: [85564-02-9]. Teupyreinin
7-Ketone, 6,19-di-Ac: 6-Acetylpicropoline
C16H 320 10 M 504.533
Isol. from T. pyrenaicum. Cryst. (MeOH). Mp 112-114°. C 24H 280 9 M 460.480
Isol. from T. polium. Cryst. (CHC1 3 /Et 20). Mp 221-
[ex]~ -9.4° (c, 1 in CHC1 3).
2240. (ex]i,<l + 17.SO (c, 0.5 in CHCI 3).
(ent-3«,4P,6P,12PII)-form
6,7-Diketone, 19-Ac: [73114-26-8]. Picropolinone
3,19-Di-Ac: [113493-26-8]. Teumicropodin C22H 240 8 M 416.427
C 24H 300 9 M 462.496 lsol. from T. polium. Cryst. (hexanejMe 2CO). Mp 218-
Isol. from T. micropodioides. Cryst. (EtOAcjhexane). 2190. [exln +44.4° (c, 0.67 in CHCI 3).
Mp 238-241°. [ex]i;1 +42.2° (c, 0.303 in CHC1 3).
Brieskom, C.H. et a/, Chern. Ber., 1967, 100, 1998 (Picropo/ine)
6-Ketone: [107602-88-0]. 4,18:15,16-Diepoxy-3,19- Marquez, C. eta/, J. Chern. Soc., Perkin Trans. I, 1979, 2526
dihydroxy-6-oxo-3( 16),14-clerodadien-20, 12-o/ide. (Picropolinone)
Teulepicin Marquez, C. eta/, Tetrahedron Lett., 1980, 5039 (cryst struct, abs
C 20H 240 7 M 376.405 config, Capitatin, Teucapitatatin)
Isol. from T. lepicephalum. Cryst. (EtOAc). Mp 174- Malakov, P.Y. eta/, Phytochemistry, 1983, 22, 2791 (Teupo/in IV)
1760. (ex]i,<l +59 .SO (c, 0.441 in MeOH). De La Torre, M.C. eta/, Phytochemistry, 1986, 25, 2239 (19-
Acety/teupo/in IV)
6-Ketone, 19-Ac: 19-Acetylieulepicin
C22H 160 8 M 418.443
From T. lepicephalum and T. buxifolium. Cryst. 4,18:15,16-Diepoxy-1,8, 19-trihydroxy- Di-00634
(EtOAcjhexane). Mp 204-206°. [ex]i,<l + 73.4° (c, 0.496 in 13(16),14-clerodadien-6-one
CHC1 3).
Garcia-Alvarez, M.C. eta/, Phytochemistry, 1982, 21, 2559
(Teupyreinin)
Pascual, C. eta/, Phytochemistry, 1986, 25, 715 (Teupyreinin)
Savona, G. et a/, Phytochemistry, 1986, 25, 2569 (Teulepicin)
Malakov, P.Y. eta/, Z. Naturforsch., B, 1987, 42, 1000 (Montanin
G)
De La Torre, M.C. eta/, Phytochemistry, 1988, 27, 213
(Teumicropodin) OH

:o
I
I
4,18:15,16-Diepoxy-6,7,19-trihydroxy- Dl-00633
13(16},14-clerodadien-20,12-olide CH20H

0 C 20H 280 6 M 364.438

(ent-1P,8«,14/I)-form
19-Ac: (66450-97-3]. ent-19-Acetoxy-4p, 18; 15,16-diepoxy-
1p,8ex-dihydroxy-13(16), 14-clerodadien-6-one. BP-
Hydroxyfruticolone
(ent-4~,6a,7~,12~11)-form C 22 H 300 7 M 406.475
Isol. from Teucrium fruticans. Oil.
Savona, G. eta/, Phytochemistry, 1978, 17, 320.
'OH

C 20H 240 7 M 376.405

(ent-4P,6«,7P,12PII)-form

762
2,7-Dihydroxy-3,13-clerodadiene-... - 6,18-Dihydroxy-3,13-clerodadien-15-... Di-00635 - Di-00639

2,7-Dihydroxy-3,13-clerodadiene- Dl-00635 6,7-Dihydroxy-3,13-clerodadien-15-oic Dl-00638

16,15:18,19-diolide acid
0 COOH

C:zoH160 6 M 362.422 C:zoH 320 4 M 336.470

(ent-1rz,7/f)-form (ent-6p,7rz,13Z)-form
Constit. of Salvia melissodora. Cryst. (Me 2CO(hexane). 6rz,7P-Dihydroxykolavenic acid
Mp 190-192°. [ex]~ -177.6° (c, 0.2 in MeOH). 6-(2-Methylpropanoyl), 7-Ac: [100324-72-9].
2-Ac: C16H 400 6 M 448.598
C 22H 280 7 M 404.459 Constit. of Chromolaena laevigata. Oil.
Constit. of S. melissodora. Cryst. (CH 2Cl2/diisopropy1 6-Angeloyl, 7-Ac: [100324-73-0].
ether). Mp 197-199°. [ex]~ -207° (c, 0.167 in CHC1 3). C 27 H 400 6 M 460.609
7-Ac: Constit. of C. laevigata. Oil.
C 22H 280 7 M 404.459 6,7-Di-Ac: [100324-74-1].
Constit. of S. me/issodora. Cryst. (Me2CO(hexane). MI? C 24H 360 6 M 420.545
236-239°. [ex]~ -123.9° (c, 0.184 in CHC1 3). Constit. of C. laevigata. Oil.
7-Ketone, 2-Ac: ent-1rz-Acetoxy-7-oxo-3,13-clerodadiene- 13,14-Dihydro, 6-(2-methylpropanoyl), 7-angeloyl: [100324-
16,15:18,19-diolide 76-3].
Constit. of S. melissodora. Cryst. (CH 2C12 /hexane). Mp C29H 460 6 M 490.679
238-240°. [ex]~0 -239.8° (c, 0.171 in CHC1 3). Constit. of C. laevigata. Oil.
Esquivel, B. eta/, Phytochemistry, !989, 28, 561. (ent-6p,13 E)-form
7-Ketone: [128254-83-1]. ent-6P-Hydroxy-7-oxo-3,13-
2,12-Dihydroxy-3,13-clerodadiene- Di-00636 clerodadien-15-oic acid
15,16:18,19-diolide C:zoH 300 4 M 334.455
Constit. of Platchaete aucheri. Oil.
OH 7-Ketone, Me ester: Cryst. Mp 69°. [ex]~ -76° (c, 1.06 in
CHC1 3).
0 Misra, L.N. eta/, Tetrahedron, 1985, 41, 5353.
Rustaiyan, A. eta/, Phytochemistry, !990, 29, 985.

6,18-Dihydroxy-3,13-clerodadien-15-oic Dl-00639
acid
C:zoH260 6 M 362.422 9"" COOH
(ent-1rz,l1~)-form[103974-71-6] Semiatrin
Constit. of Salvia semiatratha. Cryst. (EtOAcfhexane).
Mp 203-204°. [ex]~ -133° (c. 0.2 in CHC1 3).
Esquivel, B. et a/, Phytochemistry, 1986, 25, 1484.
HOH2 C
7,12-Dihydroxy-3,13-clerodadiene- Dl-00637
C:zoH3204 M 336.470
15,6:18,19-diolide
(6rz,13E)-form
OH Me ester:
cz1ll3404 M 350.497
Constit. of Pityrodia lepidota. Cryst. (EtzO/hexane) (as
di-Ac). Mp 134-135° (di-Ac). [exln -54° (c, 3.6 in
CHC13) (di-Ac).
15-Aicohol,18-carboxy/ic acid: [104700-94-9]. ent-6P,15-
Dihydroxy-3, 13£-c/erodadien-18-oic acid. Salvicin
C:zoH320 4 M 336.470
Isol. from Pulicaria salviifolia. Creamy cryst. Mp 157-
C:zoH160 6 M 362.422 1580. [ex]~ -75.4° (c, 0.26 in MeOH).
(ent-7p,I1~)-form
Nurmukhamedova, M.R. et a/, Khim. Prir. Soedin., 1976, 22, 299;
7-Ac: [98644-42-9]. Kerlinolide Chern. Nat. Compd. (Engl. Trans/.), 277 (Salvicin)
CzzH280, M 404.459 Ghisalberti, E. et al, Aust. J. Chern., 1981, 34, 1009 (cryst struct)
Constit. of Salvia keerlii. Cryst. (Me 2CO(hexane). Mp Tashkhodzaev, B. et al, Khim. Prir. Soedin,, 1988, 63; Chern. Nat.
100-102°. [ex]~ -106.6° (c, 0.15 in MeOH). Compd. (Engl. Trans/.), 53 (cryst struct)
Esquivel, B. eta/, Phytochemistry, 1985, 24, 1769.

763
15,16-Dihydtoxy-3,13-clerodadien-18-... - 7,13-Dihydroxy-3,14-clerodadien-2-... Di-00640- Di-00645

15,16-Dihydroxy-3,13-clerodadien-18-oic Dl-00640 16,18-Dihydroxy-3,13-clerodadien-15,16- Dl-00643

acid olide
0

CHpH OH

HOOC:
C~ 32 o,. M 336.470
(5«,13Z)-form [62065-09-2] Floridiolic acid I
Constit. of Evodia .floribunda. Cryst. (Et0Ac/CHC13). I
18 CH2 0H
Mp 130°. [IX]~ -66° (EtOH).
Bally, R. et al, Tetrahedron Lett., 1976, 2777. C20H 300 4 M 334.455
ent-form
16,18-Dihydroxy-3,13-clerodadien-15-oic Dl-00641 16-Me ether, 18-Ac: ent-18-Acetoxy-16-methoxy-3,13-
acid clerodadien-15,16-olide. 18-Acetoxy-16-methoxy-3,13-
IS
kolavadien-15,16-olide
~ COOH C13H340 5 M 390.519
Constit. of Baccharis incarum. Oil. [1X]i; -152.2° (c, 0.84
in CHCI 3).
Givovich, A. eta/, Phytochemistry, 1986, 25, 2829.

CH2 0H 18,19-Dihydroxy-3,13-clerodadien-15,16- Dl-00644

18

CzoH320 4 M 336.470 olide

(ent-13Z)-form
16)8-Dihydroxykolavenic acid
Constit. of Acritopappus hagei. Gum. [IX]~ -48.4° (c, 2.6
in CHC1 3) (as Me ester).
16-Ac: ~ 5a.-form
19 I
CllH340 5 M 378.508 18 CH2 0H
Constit. of A. hagei. Gum. CH2 0H
18-Aldehyde: 16-Hydroxy-18-oxokolavenic acid C20H 300 4 M 334.455
C20H:14,04 M 334.455 5«-form
Constit. of A. hagei. Gum. Constit. of Gutierrezia texana. Cryst. (EtOAc). Mp 149-
18-Aldehyde, 16-Ac: 16-Acetoxy-18-oxokolavenic acid 1500. [1X]i; -29.7° (c, 0.75 in MeOH).
CllH320S M 376.492 18-Carboxylic acid, 18--.19 lactone: 3,13-Cierodadien-
Constit. of A. hagei. Gum.
15,16:18,19-diolide
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2695. C20H 21,04 M 330.423
Constit. of G. texana. Cryst. (EtOAc). Mp 195-196°.
6,18-Dihydroxy-3,13-clerodadien-15,16- Dl-00642 [1X]i? +41.4° (c, 1.3 in CHC1 3).
olide (ent-5/1)-form [122279-89-4] Paniculadiol
Constit. of Baccharis paniculata. Oil. [1X]i; -1.72° (c,
0.29 in CHC1 3).
Di-Ac: [122297-37-4].
C24H 340 6 M 418.529
Constit. of B. paniculata. Oil.
Gao, F. eta/, Phytochemistry, 1987, 26, 209.
HOH2 C Rivera, A.P. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 433
(Paniculadiol)
C20H 300 4 M 334.455
(5«,6«)-form 7,13-Dihydroxy-3,14-clerodadien-2-one Di-00645
Constit. of Gutierrezia texana. Oil. [IX]~ -64° (c, 1.2 in
CHCI 3). OH
Gao, F. eta/, Phytochemistry, 1987, 26, 209.
0

C20H 320 3 M 320.471

(ent-7p,8f,H,13f,)-form [38748-31-1] Stachysolone
Constit. of Stachys annua. Cryst. [1Xln -25° (c, 0.119 in
MeOH).

764
12,15-Dihydroxy-3,13-clerodadien-2-... - 6,7-Dihydroxy-2-oxo-3,13-... Di-00646 - Di-00651

Mono-Ac (isomer A): 6-Angeloyl: [129350-08-9].

C 21H 340 4 M 362.508 C15H 410 5 M 422.604
Constit. of S. annua. Mp 134-136°. [a]i,O -47.6° (c, 7.4 Constit. of Pteronia paniculata.
in CHC13). Zdero, C. et al, Phytochemistry, 1990, 29, 1231 (isol, pmr)
Mono-Ac (isomer B):
C12H 340 4 M 362.508 3,4-Dihydroxy-13-cleroden-15,16-olide Dl-00649
Constit. of S. annua. Mp 154-155.SO. [a)i; -77° (c, 7.2
in CHC1 3). 0
Di-Ac:
C 24H 360 5 M 404.545
Constit. of S. annua. Cryst. (Et20jpet. ether). Mp 91-
920. [a)~ -71.2° (c, 7.7 in CHC1 3).
(5«,7/1,13~)-form [12683-99-7) AnniUlllone
Constit. of Stachys annua.
Popa, D.P. et al, Khim. Prir. Soedin., 1969, 5, 7; 1972, 8, 295, 735; CzoH 310 4 M 336.470
1974, 10, 324; Chern. Nat. Compd. (Engl. Trans/.), 292, 717 (ent-3/1,4«,5«)-form [118173-00-5]
(struct) Cons tit. of Ageratina saltillensis.
3-Me ether: [118173-01-6]. ent-4«-Hydroxy-3/l-methoxy-13-
12,15-Dihydroxy-3,13-clerodadien-2-one Dl-0064& cleroden-15,16-olide
C 21 H 340 4 M 350.497
OH Constit. of A. saltillensis.
3-Ketone: [118173-02-7]. ent-4«-Hydroxy-3-oxo-13-cleroden-
15,16-olide
C10H 31,04 M 334.455
Constit. of A. saltillensis.
16~-Hydroxy: [118172-99-9). ent-3fl,4«,16~-Trihydroxy-13-
cleroden-15,16-olide
CwH310 3 M 320.471 CzoH 320 5 M 352.470
(ent-5«,13£)-form Constit. of A. saltillensis.
15-Angeloyl, 12-Ac: [64340-48-3]. Unarienone Fang, N. et al, Phytochemistry, 1988, 27, 3187.
C27H 400 5 M 444.610
Constit. of Linaria japonica. Oil. [aJn + 30° (CHC1 3). 2,7-Dihydroxy-3-oxo-1,4(19)-clerodadien- Dl-00650
Kitagawa, I. et al, Chern. Pharm. Bull., 1978, 26, 79. 15-oic acid

3,4-Dihydroxy-15-clerodanoic acid 01-00647 COOH

14
COOH

C10H 300 5 M 350.454

(ent-7«,13~)-form

C10H 360 4 M 340.502 7-Ac:

(ent-3«,4«,13~)-form C12H 320 6 M 392.491
Constit. of Relhania corymbosa and R. genistifolia. Constit. of Relhania genistifolia.
13,14-Didehydro (E-): ent-3«,4«-Dihydroxy-13-cleroden-15- 7-Ac, Me ester:
oic acid C13H 340 6 M 406.518
C10H 340 4 M 338.486 Constit. of R. genistifolia.
Constit. of R. genistifolia. 7-Ac, 13,14-didehydro (E-): ent-7«-Acetoxy-2-hydroxy-3-
Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol) oxo-1,4(19),13-clerodatrien-15-oic acid
C12H 300 6 M 390.475
Constit. of R. genistifolia.
4,6-Dihydroxy-15-clerodanoic acid Dl-00648 Tsichritzis, F. et al, Phytochemistry, 1990, 29, 3173 (isol)

COOH
6,7-Dihydroxy-2-oxo-3,13-clerodadien-15- Dl-00651
oic acid

COOH

C10H 360 4 M 340.502

(4«,6« )-form
4a,6a-Dihydroxy-3,4, 13, 14-tetrahydrokolavenic acid
M 350.454

765
3,7-Dihydroxy-2-oxo-3-cleroden-15-... - 8,12-Epoxy-3,13-clerodadiene-... Di-00652 - Di-00657

(ent-6«,7fl,l3E)-form lsol. from Parentucellia latifolia. Oil. [ocln + 16° (c, 1 in

6oc, 7P- Dihydroxy- 7-oxo-13E-ko/avenic acid CHC1 3).
Me ester: [100324-75-2]. Ki.ijoa, A. eta/, Phytochemistry, 1990, 29, 653 (isol, pmr, cmr)
C21H320 5 M 364.481 Urones, J.G. et a/, Phytochemistry, 1990, 29, 2223 (deriv)
lsol. from Chromolaena /aevigata. Oil.
Misra, L.N. eta/, Tetrahedron, 1985, 41, 5353. Eeniolide Di-00655
[129349-98-0]
3,7-Dihydroxy-2-oxo-3-cleroden-15-oic Dl-00652
acid

COOH
Q I

OH

0
HO~

HO \
C 20H 320 5 M 352.470
(ent-7«,131;)-form C20H 260 6 M 362.422
Constit. of Pteronia eenii. Gum. [oc]i; - 1o (c, 0.3 in
7-Ac: CHC1 3).
C22H 340 6 M 394.507
Constit. of Relhania genistifolia. Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr)
7-Ac, Me ester:
C23H 360 6 M 408.534 15,16-Epoxy-4(18),12-clerodadiene-15,16- Di-00656
Constit. of R. genistifolia. diol
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol)
OH
14,15-Dinor-2,4(18)-clerodadien-13-one Dl-00653
14,15-Bisnor-2,4(18)-c/erodadien-13-one

C20 H 320 3 M 320.471

(ent-12Z,l51;,161;)-form
Di-Ac: [96888-17-4].
C24H 360 5 M 404.545
Constit. of Linaria saxatilis. Oil. [oc]n -55.2° (c, 0.9 in
CtsH280 M 260.419 CHCI 3). Mixture of 15, Hi-stereoisomers.
ent-form [130395-27-6] San Feliciano, A. eta/, Tetrahedron, 1985, 41, 671.
Constit. of Parentucellia /atifolia. Oil.
Urones, J.G. et al, Phytochemistry, 1990, 29, 2223 (isol, pmr, cmr, 8,12-Epoxy-3,13-clerodadiene-15,16:18,19- Dl-00657
synth) diolide

14,15-Dinor-3,11-clerodadien-13-one
14,15-Bisnor-3,11-c/erodadien-13-one
Dl-00654 (Yo
rf~
0

C18H 280 M 260.419

C 20 H 240 5
xr
M 344.407
(ent-8«,13S)-form [98644-43-0] Kerlin
Constit. of Salvia keerlii. Cryst. (Me2COjhexane). Mp
ent-form [126582-61-4] 220-222°. [ocJi? -59° (c, 0.2 in MeOH).
14,15-Bisnor-3,11-ko/avadien-13-one. 14,15-Dinor-3,11-
Esquivel, B. et al, Phytochemistry, 1985, 24, 1769.
ko/avadien-13-one
Constit. of Polyalthia viridis. Gum.
11,12-Dihydro: [130466-21-6]. ent-14,15-Dinor-3-cleroden-3-
one. ent-14, 15-Bisnor-3-c/eroden-3-one
CtsH31,0 M 262.434

766
15,16-Epoxy-13(16),14-clerodadiene-... - 15,16-Epoxy-1,3,13(16),14-... Di-00658 - Di-00664

15,16-Epoxy-13(16),14-clerodadiene-2,3,4- Dl-00658 15,16-Epoxy-1,3,13(16),14- Di-00662

trioI clerodatetraene-17,12:18,19-diolide

0
Q
HO~

HO \
0
C20H 320 4 M 336.470
(ent-2P,3P,4~X)-form
Constit. of Baccharis boliviensis. Cryst. Mp 155°. [a]i:
+ 15° (c, 0.43 in CHC1 3).
Zdero, C. eta/, Phytochemistry, 1989, 28, 531. C20H 200 5 M 340.375
(ent-8pH,12~XH)-form [106009-54-5] Linearifolin
15,16-Epoxy-13(16),14-clerodadien-2-one Di-00659 Constit. of Salvia lineata. Cryst. (MeOH). Mp 229-230°.
[ali? -68.7° (c, 0.19 in MeOH).

'
Esquivel, B. eta/, Phytochemistry, 1986, 25, 2381.

0
15,16-Epoxy-3,8(17),13(16),14- Dl-00663
clerodatetraene-18,19:20, 12-diolide

C20H 300 2 M 302.456

Struct. revised in 1989.
(ent-4~XH)-form [59742-40-4] Cascarillone
Constit. of oil of Croton eleuteria. Oil.
Claude-Lafontaine, A. eta/, Bull. Soc. Chim. Fr., 1976, 88 (isol)
Iio, H. eta/, J. Chern. Soc., Perkin Trans. 1, 1989, 1360 (struct,
synth)

3,4-Epoxy- 2,15-clerodanediol Dl-00660

C20 H 200 5 M 340.375
(ent-12/1)-form [69749-03-7] Plaunolide. Swassin
Constit. of Croton nublyratus and C. joufra. Cryst. Mp
169-172°. [a]i,3 -75.2° (c, 1 in Me 2CO), [a]~ +49.4° (c,
(ent-2~,3M~,13C,)-form 0.48 in CHC1 3). Large discrepancy in opt. rotn. between
the two isolates casts some doubt on their identity.
[84799-19-9)
C20H 360 3 M 324.503
Roengsumran, S. et a/, J. Nat. Prod. (Lloydia), 1982, 25, 772 (isol)
(ent-2P,3P,4P.J3~)-form Takahashi, S. et a/, Phytochemistry, 1983, 22, 302 (isol)
3,4- Epoxy- 2, 15-kolavanediol
Constit. of Symphyopappus compressus. Gum.
15,16-Epoxy-1,3,13(16),14-clerodatetraen- Dl-00664
(ent-31¥.,4~¥.,13~)-form
18-oic acid
2-Ketone, 15-carboxy/ic acid: ent-31¥.,41¥.-Epoxy-2-oxo-15-
clerodanoic acid. 3,4-Epoxy-2-oxo-15-kolavanoic acid
C20H 32 0 4 M 336.470
Isol. from Hartwrightia fioridana. Gum (as Me ester).
[ali: + 72.8° (c, 2.2 in CHC1 3) (Me ester).
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 843, 1657.

COOH
3,4-Epoxy-13,15-clerodanediol Dl-00661
C20 Hu;03 M 314.424
(ent-101¥.)-form [70377-99-0] Nidoresedic acid. Nidoresedaic
acid
Constit. of Grangea maderaspatana. Cryst. (EtOAc). Mp
82-84°. [aln -139° (c, 0.49 in CHCI 3).
Me ester: Methyl nidoresedllte
C21 H 280 3 M 328.450
Constit. of Nidorella auriculata. Oil.
15,16-Dihydro, 15-methoxy, 16-oxo: 15,16-Dihydro-15-
C20H 360 3 M 324.503
methoxy-16-oxonidoresedic acid
[118173-06-1]
(ent-31¥.,41¥.,5~¥.,131;)-form C21 H 280 5 M 360.449
Constit. of Ageratina saltillensis. Constit. of G. maderaspatana. Gum (as Me ester). [aln
Fang, N. eta/, Phytochemistry, 1988, 27, 3187. - 120.8° (c, 0.23 in CHC1 3) (Me ester).

767
15,16-Epoxy-3,11,13(16),14-... - 15,16-Epoxy-3,13(16),14-... Di-00665 - Di-00669

(ent-10/1)-form
10-Epinidoresedic acid
Constit. of G. maderaspatana. Gum (as Me ester). [exln
-66.1° (c, 1 in CHC1 3) (Me ester).
Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1769 (isol)
Pandey, U.C. eta/, Phytochemistry, 1984, 23, 391 (isol)
Singh, P. et a/, Phytochemistry, 1988, 27, 1537 (isol)
15,16-Epoxy-3,11,13(16),14-
clerodatetraen-18-oic acid
Kazawa, K. eta/, Agric. Bioi. Chern., 1972, 36, 1245 (synth)
Anthonsen, T. eta/, Can. J. Chern., 1973, 51, 1332 (synth)
McCrindle, R. eta/, J. Chern. Soc., Perkin Trans. I, 1976, 1590.
Tokoroyama, T. eta/, J. Chern. Soc., Chern. Commun., 1983, 1516
(synth)
15,16-Epoxy-3,13(16),14-clerodatriene- Dl-00668
7,18-diol
Dl-00665

HOH2C
HOOC C 20H 300 3 M 318.455
C:zoll:u.03 M 314.424 (ent-7/1)-form [66563-31-3] .Bacchotricuneatin D
(ent-llE)-form [38017-39-9] 11,12-Dehydro/rardwickiic acid Constit. of Baccharis tricuneata. Cryst. (EtOAcjhexane).
Constit. of Croton oblongifolius. Cryst. Mp 114-115°. Mp 109-1UO. [ex]i,S -7.41° (c, 0.58 in CHC1 3).
[ex]n -186° (c, 1 in CHC1 3). Wagner, H. et a/, J. Org. Chern., 1978, 43, 3339.
Aiyar, V.N. eta/, Phytochemistry, 1972, 11, 1473.
15,16-Epoxy-3,13(16),14-clerodatriene- Dl-00669
15,16-Epoxy-3,13(16),14-clerodatrien-17- Dl-00666 18,19-diol
al
17-0xo-3,13(16),14-clerodatrien-15,16-oxide

I
I

HOH 2C ~H 2 0H
18

C 20H 180 1 M 300.440 C20H 300 3 M 318.455

ent-form [97457-12-0] ent-form [84173-40-0] Kingidiol
Constit. of Baccharis hutchisonii. Oil. Constit. of Baccharis kingii and Conyza scabrida. Cryst.
17-Carboxylic acid: ent-15,16-Epoxy-3,13(16),14- (Et20/hexane). Mp 93°. [ex]~4 -94° (c, 0.2 in CHC1 3).
clerodatrien-17 -oic acid. Bacchabolivic acid 19-Malonyl: 19-Malonylkingidiol
C 20H 180 3 M 316.439 C23H310 6 M 404.502
Isol. from B. boliviensis. Cryst. Mp 147°. From B. rhetinodes.
17-Carboxy/ic acid, xylopyranosyl ester: 18-Malonyl, 19-Ac:
C:15H360 7 M 448.555 C:15H340 7 M 446.539
Constit. of B. boliviensis. Constit. of B. rhetinodes. Oil.
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 511 (isol) 19-Carboxylic acid, 18-angeloyl: [19902-44-4]. Solidagoic
Zdero, C. et a/, Phytochemistry, 1989, 28, 531 (Bacchabolivic acid) acid B
C:15H340 5 M 414.541
15,16-Epoxy-3,13(16),14-clerodatriene Dl-00667 Isol. from Solidago serotina. Cryst. (Etpjpet.ether). Mp
134-135°. [ex]~ -28° (c, 0.7 in CHC1 3).
18-Carboxylic acid: [18411-75-1]. ent-15,16-Epoxy-19-
hydroxy-3, 13(16), 14-clerodatrien-18-oic acid. Hautriwaic
(ent-Sa.)-form acid
C 20 H 180 4 M 332.439
Isol. from Dodonea viscosa and D. attenuata. Cryst. Mp
183-184°. [ex]n -105°.
C 20H 300 M 286.456 18-Carboxylic acid, 19-Ac: Hautriwaic acid acetate
(ent-5rx.)-form [50489-20-8] CuH300 5 M 374.476
Constit. of roots of Solidago arguta. Oil. [exln + 33° (c, Isol. from Baccharis macraei and C. scabrida. Gum. [ex]i,S
1.32 in CHC1 3). -85° (c, 0.9 in CHC1 3).
(ent-5/1)-form [38611-50-6] 18-Carboxlic acid, 19-aldehyde: ent-15,16-Epoxy-19-oxo-
Annonene 3, 13( 16), 14-clerodatrien-18-oic acid. 19-0xohautriwaic
Prod. by redn. of several diterpenes. Oil. [ex]~ -58° (c, acid
1.3 in CHC1 3). C 20H 160 4 M 330.423

768
15,16-Epoxy-4(18),13(16),14-... - 15,16-Epoxy-3,13(16}~14- ..• Di-00670- Di-00673

Isol. from C. scabrida. Oil (as Me ester). [ex]~ -67° (c, C25H 380 4 M 402.573
0.15 in CHC13) (as Me ester). The name 19- Constit. of H. imbricata. Cryst. (Et20jpet. ether). Mp
0xohautriwaic acid is misleading. 103°. [exJn -35° (c, 1 in CHC1 3).
18-Carboxy/ic acid, 19-Me ether: 19-0-Methylluultriwaic Bohlmann, F. et a/, Chern. Ber., 1973, 106, 2479.
acid
C21 H 300 4 M 346.466 15,16-Epoxy-2,13(16),14-clerodatriene- Dl-00672
From C. scabrida. Oil (as Me ester).
17,12:18,19-diolide
18-Carboxy/ic acid, 19-ange/oy/: 19-0-AngeloylluJutriwaic
acid
C25H 340 5 M 414.541
From C. scabrida. Oil (as Me ester) (not pure).
18-Carboxy/ic acid, 19-(3-methy/butanoyl): 19-0-
IsovalerylluJutriwaic acid
C 25H 360 5 M 416.556
From C. scabrida: Oil (as Me ester). 0
Bohlmann, F. eta/, Chern. Ber., 1972, 105, 2123 (Hautriwaic acid)
Anthonsen, T. et al, Can. J. Chern., 1973, 51, 1332 (Solidagoic acid '
B)
Bohlmann, F. et al, Justus Liebigs Ann. Chern., 1983, 2008 (derivs) o;..__J
Bohlmann, F. et a/, Phytochemistry, 1984, 23, 1511 (Kingidiol)
Zdero, C. et al, Phytochemistry, 1986, 25, 2841. C20Hn0 5 M 342.391
Gambaro, V. eta/, Phytochemistry, 1987, 26, 475 (isol, deriv) (ent-8fJH,12rx.H)-form [67927-55-3] Salviarin
Constit. of Salvia splendens. Cryst. (EtOAcjpet. ether).
15,16-Epoxy-4(18),13(16),14- Dl-00670 Mp 218°. [exJn -85° (CHC1 3).
clerodatriene-2,3-diol 1,10-Didehydro: ent-15, 16-Epoxy-1(10),2, 13(16), 14-
c/erodatetraene-17,12:18,19-diolide. 1(10)-
Dehydrosallliarin
C20H 200 5 "M 340.375
Constit. of S. lineata. Cryst. (MeOH). Mp 198-199°.
[ex]~ -199.SO (c, 0.22 in CHC1 3).
1ex,JOex-Epoxide: ent-1, 10:15, 16-Diepoxy-2, 13(16), 14-
c/erodatriene-17, 12: 18, 19-dio/ide. 1 rz,1 Orz-Epoxysalviarin
C20H 200 6 M 356.374
CwfiJ003 M 318.455 From S. lineata. Cryst. (MeOH/diisopropyl ether). Mp
(ent-2fl,3f/)-form [24513-44-8] Agbanindiol B 255-256°. [ex]~ -90.3° (c, 0.155 in MeOH).
lsol. from Gosswei/erodendron balsamiferum. Amorph. Savona, G. et al, J. Chern. Soc., Perkin Trans. 1, 1978, 643 (isol)
[exJn + 26.4°. Esquivel, B. et al, Phytochemistry, 1986, 25, 2381 (isol, struct)
4fl,J8-Dihydro, 3-ketone: ent-15,16-Epoxy-2rz-hydroxy-
13(16),14-clerodadien-3-one 15,16-Epoxy-3,13(16),14-clerodatriene- Dl-00673
C20H:14,03 M 318.455 17,12:18,19-diolide
Isol. from Baccharis boliviensis. Gum.

0
Ekong, D.E.U. eta/, J. Chern. Soc. C, 1969, 2153.
Zdero, C. et al, Phytochemistry, 1989, 28, 531.
I
15,16-Epoxy-7,13(16),14-clerodatriene- Dl-00671 I

3,18-diol

HO' C20Hn0 5 M 342.391

HOH2 C
I
(ent-12rx.H)-form [65596-25-0] Bacchotricuneatin A
18 Constit. of Baccharis tricuneata. Cryst. (CH 2Cl2/EtOH).
C20H 300 3 M 318.455 Mp 239-241°. [ex]i; -121.4° (c, 0.94 in CHC13).
(ent-3fl,4rx.H)-form lex-Hydroxy: ent-15,16-Epoxy-1fl-hydroxy-3,13(16),14-
3-Hydroxyimbricatol c/erodatriene-17, 12: 18, 19-dio/ide. 1rz-
Hydroxybacchotricuneatin A
18-Ange/oy/: [51460-74-3].
C25H360 4 M 400.557 Cwflu06 M 358.390
Constit. of Hinterubera imbricata. Cryst. (Et20jpet. Constit. of Liatris spicata. Oil.
ether). Mp 80°. Jex-Acetoxy: 1rz-Acetoxybacchotricuneatin A. lex-
Acetylbacchotricuneatin A (incorr.)
18-(2-M ethylbutanoyl): [51460-73-2].
C25H380 4 M 402.573 CnH 2,,07 M 400.427
Constit. of H. imbricata. Cryst. (Et20jpet. ether). Mp Constit. of B. incarum. Cryst. (Et20). Mp 203-205°. [ex]i;
149°. [ex]~4 -38° (c, 0.8 in CHC13). -121.3° (c, 0.4 in CHC13).
18-(3-Methy/butanoyl): [51460-72-1].

769
15,16-Epoxy-3,13(16),14-... - 15,16-Epoxy-3,13(16),14-... Di-00674- Di-00677

7a.-Hydroxy: ent-15,16-Epoxy-7p-hydroxy-3, 13(16),14- 18,19-Epoxy-3,13(16),14-clerodatriene- Dl-00676

c/erodatriene-17,12: 18,19-dio/ide. 7rx.- 2,6,18,19-tetrol
Hydroxybacchotricuneatin A
Cw!l220 6 M 358.390
Constit. of B. incarum. Cryst. (Me 2CO). Mp 242-243°.
[a.]i: -154.6° (c, 0.24 in CHCI3).
(ent-12PH)-form
2P-Hydroxy: ent-15,16-Epoxy-2a.-hydroxy-3,13(16),14- ~.
c/erodatriene-17, 12: 18, 19-dio/ide. 2P-Hydroxy-12- 1~ , (2a,5a,6a,8~H,18a,19R}:form
epibacchotricuneatin HO-ts 0 'OH
OH
C 20H 22 0 6 M 358.390
Constit. of Vittadinia gracilis. Oil. C 20 H~,0 5 M 350.454
Wagner, H. et al, Tetrahedron Lett., 1977, 3039 (isol) (2rx.,5rx.,6rx.,8pH,18rx.,l9R)-form
Baruah, R.N. et al, Phytochemistry, 1985, 24, 2641 (isol) 6-(2Z,4E-Decadienoyl), 18,19-di-Ac: [116528-02-0].
Givovich, A. et al, Phytochemistry, 1986, 25, 2829 (deriv) Pitumbin
Zdero, C. et al, Phytochemistry, 1988, 27, 2251 (deriv) C 34H 480 8 M 584.748
Constit. of seeds of Casearia pitumba. Oil. [a.]n -71.6°
15,16-Epoxy-3,13(16),14-clerodatriene- Dl-00674 (c, 1 in CHC1 3).
18,19:20,12-diolide (2rx.,5rx.,6rx.,8PH,I8rx.,l9S)-form
2,6-Dihydroxyisozuelanin
2-(2-Methylpropanoyl), 18,19-di-Ac:
C28H 380 8 M 502.603
Constit. of C. corymbosa.
2-(2-Methylbutanoyl), 18,19-di-Ac:
C 29H 400 8 M 516.630
Constit. of C. corymbosa.
6-Me ether, 2-(2-methylpropanoyl), 18,19-di-Ac:
C29H 400 8 M 516.630
Constit. of C. corymbosa.
C 20Hn0s M 342.391 6-Me ether, 2-(2-methylbutanoyl), 18,19-di-Ac:
~H 41 08 M 530.657
(ent-12rx.H)-form [65596-26-1] Bacchotricuneatin B Constit. of C. corymbosa.
Constit. of Baccharis tricuneata. Cryst.
(CH 2Cl2fhexane). Mp 192-193°. [a.]i: -102.4° (c, 0.55 in 6-Deoxy, 18,19-di-Ac: 2-Hydroxy-3,4-dihydroisozue/anin
CHCI 3). C 24H 360 6 M 420.545
Constit. of C. corymbosa. Oil. [1X]n -68° (c, 0.16 in
7a.-Acetoxy: [116139-48-1 ]. 7rx.-Acetoxybacchotricuneatin B CHCI 3).
CnH240 7 M 400.427
Constit. of 0/earia pimeleoides. Gum. 6-Deoxy, 2,18,19-tri-Ac:
C16H 380 7 M 462.582
Wagner, H. et al, Tetrahedron Lett., 1977, 3039 (isol, struct) Constit. of C. corymbosa. Oil. [1X]n -67° (c, 0.12 in
Warning, U. et al, J. Nat. Prod. (Lloydia), 1988, Sl, 513 (deriv)
CHCI 3).
6-Deoxy, 2-(2-methylbutanoyl), 18,19-di-Ac:
15,16-Epoxy-3,13(16),14-clerodatriene- Dl-00675 C 29H 410 7 M 502.647
2~7-dione Constit. of C. corymbosa. Oil. [1X]n -61° (c, 0.09 in
CHCI3).
Guittet, E. et al, Tetrahedron, 1988, 44, 2893 (Pitumbin)
Khan, M.R. et al, Phytochemistry, 1990, 29, 3591 (isol, pmr, cmr)

15,16-Epoxy-3,13(16),14-clerodatrien-18- Dl-00677
oic acid

Cw!l:u;03 M 314.424
ent-form [80594-75-8] Eremone
Constit. of Eremocarpus setigerus. Cryst. (diisopropyl (+)-form
ether). Mp 106-107°. [1X]i: -93.1° (Py).
Jolad, S.D. et al, J. Org. Chem., 1982, 47, 1356.
HOOC
C 20 H 280 3 M 316.439
(+)-form [24470-47-1]
Constit. of Copaifera officina/is. Mp 104-106°. [1X]i?
+ 125°.
(-)-form [1782-65-6]
ent-form. Hardwickiic acid

770
15,16-Epoxy-3,13(16),14-... - 15,16-Epoxy-3(16),4,14-clerodatrien-... Di-00678 - Di-00683

Constit. of, inter alia, Hardwickia pinnata. Cryst. Mp Constit. of Baccharis tricuneata. Oil (as Me ester). [IX]~
106-107°. [1X]n -114.7° (CHC13). -37.6° (c, 6.1 in CHC13) (Me ester).
Cocker, W. et al, Tetrahedron Lett., 1965, 1983 (isol) Bohlmann, F. et al, Phytochemistry, 1979, 18, 1993.
Payne, T.G. et al, Tetrahedron, 1973, 29, 2575 (struct)
Ferguson, G. et al, J. Chern. Soc., Chern. Commun., 1975, 299
(stereochem) 15,16-Epoxy-4(18),13(16),14-clerodatrien- 01-00681
Misra, R. et al, Tetrahedron, 1979, 35, 2301 (abs config) 3-ol

15,16-Epoxy-3,13(16),14-clerodatrien-19- Dl-00678
oic acid

HO'
(51l,8~H)-form
C20H 300 1 M 302.456
(ent-3/1)-form [24513-42-6] Agbaninol
Constit. of Gossweilerodendron balsamiferum. Cryst. (pet.
C20H 280 3 M 316.439 ether). Mp 70-71°. [1X]i? -4.9°.
(5rx.,BPH)-form [19902-42-2] Solidagoic acid A Ekong, D.E.U. et al, J. Chern. Soc. C, 1969, 2153.
Constit. of the roots of Solidago serotina. Cryst.
(EtOAcjpet. ether). Mp 169-171°. [1X]i? -58° (c, 0.9 in 15,16-Ej,oxy-3,13(16),14-clerodatrien- Dl-00682
EtOH).
18,6-olide
(ent-5ft,Brx.H)-form [34327-14-5] Maingayic acid. Maingayinic
acid. Strigi/lanoic acid B
Isol. from Callicarpa maingayi and Hoffmannia
strigillosa. [1X]i? -252° (c, 3 in CHC1 3).
Kawazu, K. et al, Agric. Bioi. Chern., 1972, 36, 1245 (Maingayic
acid) . (ent-51l,6~)-form
Anthonsen, T. et al, Can. J. Chern., 1973, 51, 1332 (Solidagoic acid
A)
Jaensch, M. et al, Phytochemistry, 1990, 29, 3587.
C20H 160 3 M 314.424
15,16-Epoxy-3,13(16),14-clerodatrien-20- 01-00679 (ent-5rx.,6fl)-form [54155-35-0]
oic acid Constit. of roots of Solidago arguta. Cryst. (EtzOjpet.
ether). Mp 142-143°. [1X]n + 34° (c, 1.07 in CHC1 3).
(ent-5ft,6/1)-form
Constit. of Pulicaria gnaphaloides. Cryst. M p 161 °. [IX]~
-62.3° (c, 2.4 in CHC13).
McCrindle, R. et al, J. Chern. Soc., Perkin Trans. I, 1976, 1590.
Rustaiyan, A. et al, Phytochemistry, 1981, 20, 2772.

15,16-Epoxy-3(16),4,14-clerodatrien- 01-00683
20,12-olide-18,19-dioic acid

C 20H:11P 3 M 316.439
ent-form [50816-25-6] Junceic acid
Constit. of Solidago juncea. Oil. [1X]n -59° (c, 0.84 in
Q I

~-0
CHC13).
Henderson, M.S. et al, Can. J. Chern., 1973, 51, 1322.

15,16-Epoxy-3,13(16),14-clerodatrien-18- 01-00680
ol
H~ COOH
C20H 110 7 M 374.390
(ent-12rx.H)-form
Di-Me ester: [61661-32-3]. Crotocorylifuran
C11H 160 7 M 402.443
Constit. of Croton haumanianus. Cryst. (MeOH) or
CH2 0H
prisms (Me2COjpet. ether). Mp 200-202°. [1X]i? -164°
C20H3e,01 M 302.456 (c, l.O in CHC13).
ent-form [24513-47-1] Bacchalineol Burke, B.A. et al, Tetrahedron, 1976, 32, 1881 (synth)
Oil. Tchissambou, L. et al, Tetrahedron, 1990, 46, 5199 (isol, struct)
19-Malonyl:
C13H 310 5 M 388.503

771
15,16-Epoxy-3,13(16),14-... - 13,16-Epoxy-3-cleroden-12,14,15,18-... Di-00684 - Di-00688

15,16-Epoxy-3,13(16),14-clerodatrien- Dl-00684 Constit. of Goyazianthus tetrastichus. Gum (as di-Ac).

17,12-olid-18-oic acid [acJn +8° (c, 0.14 in CHC1 3) (di-Ac).
16-Hydroxy: ent-3,4-Epoxy-13-clerodene-2,15,16-trio/. 3,4-
Epoxy-13-kolallene-2,15,16-triol
C10H 340 4 M 338.486
Cons tit. of G. tetrastichus.
( 51l, 121lH)-form 16-Hydroxy, tri-Ac: Gum. [acln + 13° (c, 0.26 in CHC1 3).
Bohlmann, F. eta/, Phytochemistry, 1982, 21, 939.

3,4-Epoxy-13-cleroden-15,16-olide Dl-00687
0
HOOC
C10H 140 5 M 344.407
(5a.,12a.H)-form [59805-72-0] Floribundic acid
Constit. of Evodiajloribunda. Cryst. (EtOAc). Mp 250°.
[ac]i,O -130° (CHC1 3).
(ent-5P,12a.H)-form C10H 300 3 M 318.455
Barbasoic acid (ent-3a.,4a.,5a. )-form [118243-67 -7]
Me ester: [60132-72-1]. Constit. of Solidago shortii, Ageratina cronquisti and A.
C21 H 21;05 M 358.433 sa/til/ensis. Cryst. M p 91°.
lsol. from Croton ca/ifornicus. Cryst. (Et20). Mp 152- 161;,-Hydroxy: [118172-98-8]. ent-3a.,4a.-Epoxy-16C.-hydroxy-
1530. [<Xln -70°. 13-cleroden-15,16-olide
Billet, D. et a/, Tetrahedron Lett., 1975, 3825 (Floribundic acid) C10H 300 4 M 334.455
Wilson, S.R. eta/, J. Am. Chern. Soc., 1976, 98, 3669 (Barbasoic Constit. of A. sa/tillensis.
acid)
Anthonsen, T. eta/, Acta Chern. Scand., 1975, 25, 1924 (isol)
Fang, N. et a/, Phytochemistry, 1988, 27, 3187 (isol, cryst struct)
15,16-Epoxy-3,13(16),14-clerodatrien- Dl-00685
20,12-olid-18-oic acid 13,16-Epoxy-3-cleroden-12,14,15,18-tetrol Di-00688
0 OH
Q

~? C10H 340 5
18 CH2 0H

M 354.486
HOOC
(8pH,12R,13R,14R)-form [90578-12-4] Antibiotic PR 1383.
C10H 140 5 M 344.407 PR 1383
(ent-JOp,l2a.H)-form Constit. of fungus Oidiodendron truncatum. Oil.
Me ester: [79405-82-6]. Sonderianin (8pH,12R,13R,14S)-form [90639-07-9] Antibiotic PR 1389. PR
C11H 21;05 M 358.433 1389. Hexahydroclerocidin
Constit. of Croton sonderianus. Cryst. Mp 134-137°. [ac]i;" Prod. by 0. truncatum. Cryst. Mp 140-142°. [<Xln +40.6°
-55.2° (c, 5 in CHC1 3). (c, 0.23 in MeOH).
20P-Aicohol, Me ester: [125988-74-1]. Sonderianial 18-A/dehyde: [90578-10-2]. 13,16-Epoxy-12,14,15-
CZIH2805 M 360.449 trihydroxy-3-cleroden-18-a/. Tetrahydroclerocidin. PR
lsol. from C. sonderianus. Plates (hexane). Mp 130-133°. 1421. Antibiotic PR 1421
[ac]ii -85.8° (c, 7.3 in CHC1 3). Revised stereochem. C20H 320 5 M 352.470 .
Craveiro, A.A. eta/, Phytochemistry, 1981, 20, 852 (Sonderianin) Prod. by fungus 0. truncatum. Cryst. Mp 157-159°. [acln
McChesney, -J.D. eta/, Phytochemistry, 1989, 28, 3411 +69.8° (c, 0.53 in MeOH).
(Sonderianial) Andersen, N.R. eta/, J. Antibiot., 1983, 36, 753 (isol)
Andersen, N.R. eta/, Tetrahedron Lett., 1984, 25, 465, 469 (isol,
3,4-Epoxy-13-clerodene-2,15-diol Dl-00686 cryst struct)

;::r CH2 0H
16
HO,

CzoH340 3 M 322.487
(ent-2P,3a.,4a.,13E)-form
3,4-Epoxy-13-kolallene-2,15-diol

772
15,16-Epoxy-2,3-dihydroxy-13(16),14-... - 15,16-Epoxy-2,19-dihydroxy-3,8(17)... Di-00689 - Di-00693

15,16-Epoxy-2,3-dihydroxy-13(16), 14- Dl-00689 15,16-Epoxy-4,19-dihydroxy-13(16),14- Dl-00691

clerodadiene-18,19:20,12-diolide clerodadiene-19,6:20,12-diolide
0
Q
110, }1, ('L_'?
HO'~
oJ-..d
CzoH 240 7 M 376.405
(ent-2P,3P,12rx.H)-form CzoH240 7 M 376.405
3,4-Dihydro-2,3-dihydroxybacchotricuneatin
(ent-4P,6rx.,12PH)-form [73528-59-3] Teuspinin
2-Angeloyl, 3-(3-methyl-2-butenoyl): Constit. of leaves of Teucrium spinosum. Cryst. Mp 221-
C 30H 360 9 M 540.609 2250.
Constit. of Baccharis cassinaefolia.
19-Ac: [73528-60-6]. 19-Acetyheuspinin
2-(3-Methyl-2-butenoyl), 3-angeloyl: CnH260 8 M 418.443
C 30H 360 9 M 540.609 Constit. of T. spinosum. Cryst. Mp 178-179°.
Constit. of B. cassinaefolia.
Savona, G. et al, Heterocycles, 1980, 14, 193 (struct)
2-Angeloyl, 3-(2-methylbutanoyl): Eguren, L. eta/, Acta Crystallogr., Sect. B, 1981, 37, 2103 (cryst
C 30H 380 9 M 542.625 struct)
Constit. of B. cassinaefolia. Oil.
Bohlmann, F. et a/, Phytochemistry, 1981, 20, 281. 3,4-Epoxy-6,8-dihydroxy-11,13- Dl-00692
clerodadien-15,16-olide
15,16-Epoxy-3,4-dihydroxy-13(16),14- Dl-00690
clerodadiene-17,12:18,6-diolide 0

CzoH:z1P 5 M 348.438
(ent-3P,4P,6P,Brx.,ll E)-form
CzoH240 7 M 376.405
6-Benzoyl: [114436-06-5]. Scutellone F
(3p,4rx.,5rx.,BPH,12rx.H)-form [100202-27-5] Borapetol A
Constit. of stems of Tinospora tuberculata. Needles CnH3:z06 M 452.546
Constit. of Scutellaria rivularis. Needles (Me 2CO). Mp
(MeOH). Mp 137-138°. [cxJn +28.1° (c, 1.46 in Py).
213-215°. [ex]~ + 54.9° (c, 1 in CHC1 3).
3-0-P-n-Glucopyranoside: [100202-29-7]. Borapetoside A
Lin, Y.-L. et a/, Heterocycles, 1988, 27, 779.
C 26H 340 12 M 538.547
Bitter constit. of T. tuberculata. Needles (MeOH aq.).
Mp 172-173°. [cxJn +2.60° (c, 1.0 in MeOH). 15,16-Epoxy-2,19-dihydroxy-
Fukuda, N. eta/, Chern. Pharm. Bull., 1985, 33, 4438 (cryst struct) 3,8(17),13(16), 14-clerodatetraene-
18,6:20,12-diolide Dl-00693

HO

lo
I

0 CH20H
CzoH:zo07 M 372.374
(ent-2rx.,6rx.,l2PH)-form [69749-01-5] Plaunol C

773
14,16-Epoxy-4,10-dihydroxy-2,13(16) ... - 15,16-Epoxy-4,6-dihydroxy-2,13(16)... Di-00694 - Di-00697

Constit. of Croton sublyratus. Cryst. Mp 197-199°. [ex]~4 3,4P-Dihydro: [12798-53-7]. ent-15, 16-Epoxy-2,6-dihydroxy-
-13° (c, 1.3 in Me 2CO). 13(16),14-c/erodadiene-18,19:20,12-diolide. Dihydroteugin.
Kiwawa, E. et al, Chern. Pharm. Bull., 1980, 28, 227. Teucrin B
C 20 H 160 7 M 376.405
Constit. ofT. chamaedrys. Cryst. (Me 2CO/Et 20). Mp
14,16-Epoxy-4,10-dihydroxy-2,13(16),14- Dl-00694 250-252°. [ex]~ -9.8° (c, 0.37 in Py).
clerodatriene-17,21 :18,1-diolide 6-Ketone: ent-15,16-Epoxy-2-hydroxy-6-oxo-3,13(16),14-
c/erodatriene-18, 19:20, 12-dio/ide. 2P-
Hydroxyteuscordinone
C 20H 200 7 M 372.374
Constit. of T. scordium. Oil.
(ent-2rx.,6P,J2PH)-form
2p,6rx.-Dihydroxyteuscordin
Constit. ofT. scordium. Oil. [exln -40° (c, 0.15 in
MeOH).
Bruno, M. et al, Phytochemistry, 1981, 20, 2259 (struct)
Savona, G. et al, Phytochemistry, 1982, 21, 721 (struct)
Papanov, G.Y. eta/, Z. Naturforsch., B, 1982, 37, 519 (isol)
Rodriguez, M.-C. et al, Phytochemistry, 1984, 23, 2960 (struct)
C:zoll120 7 M 374.390 Jakupovic, J. eta/, Planta Med., 1985, 341 (isol)
(1 p,4rx.,5rx.,8PH,10rx.,l2rx.H)-form
10rx.-Hydroxycolumbin 15,16-Epoxy-4,6-dihydroxy-2,13(16),14- Dl-00697
!sol. from Tinospora ma/abarica. Amorph. [exJ0 +68.SO
(MeOH). clerodatriene-17,12:18, 1-diolide

Q
Atta-ur-Rahman, et al, Phytochemistry, 1988, 27, 1882.

15,16-Epoxy-1,11-dihydroxy-2,13(16),14- Dl-00695 I
clerodatriene-17,12:18,19-diolide
(l ~,4ct,5ct,6ct, 12~H)-form
0

C 20H 120 7 M 374.390

(lp,4rx.,5rx,6rx.,12PH)-form [96552-88-4] 2-Dehydrof¥cangelisinol
\
Constit. of Arcangelisia jiava. Prisms (MeOH). Mp 208-
o~c/ 2120 dec. [ex]~ +98.8° (c, 0.5 in Py).
2P,3P-Epoxide: [96552-87-3]. 2,3:15,16-Diepoxy-4,6-
C 20H 120 7 M 374.390 dihydroxy-2,13(16),14-clerodatriene-17,12:18,1-diolide. 6-
(ent-1 rx.,BpH,12rx.H)-form Hydrox,yarcangelisin
Di-Ac: [71135-81-4]. Splendidin C20H 120 8 M 390.389
C 16H 160 9 M 458.464 Constit. of A. fiava. Prisms (MeOH). Mp 274° dec. [ex]i,<'
Constit. of Salvia splendens. Cryst. (MeOH aq.). Mp + 55.27° (c, 0.54 in Py).
236°. [exJn -188° (c, 0.2 in CHC13). (1p,4rx.,5rx.,6p,12rx.H)-form
Savona, G. et a/, J. Chern. Soc., Perkin Trans. 1, 1979, 533. 2P,3P-Epoxide:
C 20 H 120 8 M 390.389
Constit. of Tinospora cordifolia. Cryst. (EtOH). Mp 258-
15,16-Epoxy-2,6-dihydroxy-3,13(16),14- Dl-00696
2600. [ex]~ + 10.0° (c, 0.5 in Me 2CO).
clerodatriene-18,19:20,12-diolide
Kunii, T. et al, Chern. Pharm. Bull., 1985, 33, 479 (isol, struct)
Hanuman, J.B. et al, J. Nat. Prod. (Lloydia), 1988, 51, 197 (deriv)

C:zoll120 7 M 374.390
(ent-2rx.,6rx.,12pll)-form [80931-33-5] Teugin. 2P,6P-
Dihydroxyteuscordin
Constit. of Teucrium fragile, T. chamaedrys and T.
scordium. Cryst. Mp 228-230°. [ex]~ -123° (c, 0.167 in
Me2CO).

774
15,16-Epoxy-4,6-dihydroxy-2,13(16)... - 15,16-Epoxy-17,19-dihydroxy-3,13(16)... Di-00698- Di-00702

15,16-Epoxy-4,6-dihydroxy-2,13(16),14- Dl-00698 15,16-Epoxy-2,19-dihydroxy-3,13(16),14- Dl-00700

clerodatriene-18,19:20,12-diolide clerodatrien-18-oic acid

HO

:::,...
I
HOOC CH20H

C 10Hn07 M 374.390 C20H 280 5 M 348.438

(ent-6«.)-form [54927-88-7] Teucrin F (ent-2«. )-form
Constit. of Teucrium chamaedrys. Mp 225-230°. [IX)~ 2P-Hydroxyhautriwaic acid
+6.0° (Py). lsol. from Baccharis sarothroides. Cryst. (C6H6). Mp
188-189°.
21X,31X-Epoxide: [54927-89-8). ent-2P,3P-Diepoxy-4,61X-
dihydroxy- 3(16), 14-c/erodadiene-18, 19:20, 12-diolide. Arriaga-Giner, F.J. et a/, Phytochemistry, 1986, 25, 719.
Teucrin G
C20 Hn08 M 390.389 15,16-Epoxy-6,7-dihydroxy-3,13(16),14- Di-00701
lsol. from T. chamaedrys. Mp 245-249°. clerodatrien-18-oic acid
Reinbol'd, A.M. eta/, Khim. Prir. Soedin., 1974, 589; CA, 82,
73223c (isol)
Rodriguez, M.-C. et al, Phytochemistry, 1984, 23, 1456 (struct)

15,16-Epoxy-4,8-dihydroxy-2,13(16),14- Dl-00699
clerodatriene-17,12;18, 1-diolide
HOOC
C20H 280 5 M 348.438
(ent-6P,7«)-form
18-+6 Lactone: [97534-14-0). ent-15,16-Epoxy-?IX-hydroxy-
3, 13(16), 14-clerodatrien-18,6P-olide. Salvinin
C20Hu;04 M 330.423
lsol. from Pulicaria salviifolia. Unstable cryst.
(EtOAcjhexane). Mp 127°. [IX]~ -128° (c, 0.22 in
MeOH).
Nurmukhamedova, M.R. et al, Khim. Prir. Soedin., 1985, 21, 201;
Chern. Nat. Compd. (Engl. Trans/.), 188.
C20Hn0 7 M 374.390
(1 p,4«.5«,8P,12«.H)-form 15,16-Epoxy-17,19-dihydroxy-3,13(16),14- Dl-00702
BP-Hydroxycolumbin clerodatrien-18-oic acid
Isol. from Chasmanthera dependens. Cryst. Mp 195-197°.
[IX)~ -24.6° (c, 0.6 in Py).
(1P,4«.5«,8~,12«.H)-form
2P,3P-Epoxide: [115334-17-3]. 2P,3P: 15,16-Diepoxy-4,8-
dihydroxy-13( 16), 14-c/erodadiene-11, 12: 18, 1P-diolide.
Tinospora clerodane """'I
HOOC CH2 0H
Isol. from Tinospora cordifolia. Cryst. (MeOH). Mp 231-
2330 dec. [IX)~ + 28.2° (c, 0.62 in DMSO).
C20H 280 5 M 348.438
Oguakwa, J.U. et al, Planta Med., 1986, 198 (8-Hydroxycolumbin)
ent-form
Bhatt, R.K. eta/, Phytochemistry, 1988, 27, 1212 (Tinospura
clerodane) 17-Ac: [18411-52-4]. ent-17-Acetoxy-15,16-epoxy-19-
hydroxy-3,13(16),14-clerodatrien-18-oic acid
CnH300 6 M 390.475
Constit. of Dodonaea attenuata. Cryst. (EtOAc). Mp
160-162°.
Payne, T.G. et a/, Tetrahedron, 1973, 29, 2575.

775
15,16-Epoxy-2,6-dihydroxy-3,13(16)... - 4,18-Epoxy-6,19-dihydroxy-1-oxo-... Di-00703 - Di-00707

15,16-Epoxy-2,6-dihydroxy-3,13(16),14- Dl-00703 13,16-Epoxy-7,12-dihydroxy-6,14-dioxo-3- Di-00705

clerodatrien-17,12-olid-18-oic acid cleroden-15-al

HOOC
C20 H180 6 M 364.438
C20H 240 7 M 376.405
(7p,apH,12R,13R)-form [100440-25-3] Terpentecin
(21X.,51X.,61X.,l21X.H)-form
Isol. from Kitasatosporia sp. Active against gram-
Me ester: [104901-06-6]. Borapetol B positive and -negative bacteria and tumours. Inhibitor
C21 H 260 7 M 390.432 of DNA synth. Powder. Mp 115-119° dec. [oc]~ -28.5°
Constit. of stems of Tinospora tuberculata. Granules (c, 0.46 in CHCI 3).
(Me 2CO aq.). Mp 117-118°. [ocln -14.1° (c, 1.165 in
Tamamura, T. et al, J. Antibiot., 1985, 38, 1664, 1819; 1988, 41,
MeOH). 648 (isol, uv, ir, pmr, struct)
6-0-P-D-Glucopyranoside, Me ester: [104901-05-5]. Isshiki, K. et al, J. Antibiot., 1986, 39, 1634 (biosynth)
Borapetoside B
C27H 360 12 M 552.574 15,16-Epoxy-3,4-dihydroxy-12-oxo- Di-00706
Constit. of stems ofT. tuberculata. Needles. Mp 153-
1540. [ocln -15.7°. 13(16),14-clerodadien-17-oic acid
Fukuda, N. et al, Chern. Pharm. Bull., 1986, 34, 2868.

4,18-Epoxy-6,19-dihydroxy-13-cleroden- Di-00704
16,15-olide
0

HO/
HO \
I
I
C20H 180 6 M 364.438
I
I
I
(ent-3P,41X.)-form
CH 2 0H Me ester: [125107-28-0]. Chiromodine
C21 H 300 6 M 378.464
C20H 34,05 M 350.454
Constit. of Croton megalocarpus. Needles (MeOH). Mp
(ent-4P,6fJ)-form 205-206°. [oc]i? -15° (c, 0.39 in MeOH).
Deacetylajugarin II
Addae-Mensah, I. et al, Phytochemistry, 1989, 28, 2759 (isol, pmr.
Constit. of Teucrium massiliense. Cryst. cmr)
(EtOAcjhexane). Mp 112-115°. [oc]i? -4° (c, 1 in
CHC1 3).
4,18-Epoxy-6, 19-dihydroxy-1-oxo-2,13- Di-00707
19-Ac: [62640-06-6]. Ajugarin II
C22H320 6 M 392.491 clerodadien-15,16-olide
Isol. from leaves of Ajuga remota. Insect antifeedant.
Cryst. Mp 188-189°.
6,19-Di-Ac: [62640-05-5]. Ajugarin I
C24H 340 7 M 434.528
Constit. of A. remota. Cryst. Mp 155-157°.
Kubo, I. et al, J. Chern. Soc., Chern. Commun., 1976, 949 (iso[)
Ley, S.V. et al, J. Chern. Soc., Chern. Commun., 1983, 503 (synth)
Savona, G. et al, Phytochemistry, 1984, 23, 849 (iso[)
Jones, P.S. et al, Tetrahedron, 1986, 42, 6519 (synth)

C20H 260 6 M 362.422

(ent-4P,6fJ)-form
Di-Ac: [79495-91-3]. Ajugareptansone B
C24H 300 8 M 446.496
Constit. of Ajuga reptans. Cryst. Mp 255-263° dec.
Camps, F. et al, Chern. Lett., 1981, 1093 (cryst struct)

776
15,16-Epoxy-3,4-dihydroxy-7-oxo-... - 18,19-Epoxy-19-hydroxy-3,13-... Di-00708 - Di-00713

15,16-Epoxy-3,4-dihydroxy-7-oxo- Di-00708 2,3-Didehydro: ent-15,16-Epoxy-6p-hydroxy-2,13(16),14-

13(16),14-clerodadien-'20,12-olide clerodatriene-18, 19:20, 12-diolide. 2,3-Dehydroteucrin E
C20H 2z0 6 M 358.390

Q
Constit. of T. scordium. Cryst. Mp 249°.
Reinbol'd, A.M. et a/, Khim. Prir. Soedin., 1974, 589 (isol)
Gacz-Baitz, E. eta/, Phytochemistry, 1978, 17, 1767.
I
Papanov, G.Y. et a/, Z. Naturforsch., B, 1980, 35, 764.

~vS:1:
Jakupovic, J. et a/, Planta Med., 1985, 341 (isol)

15,16-Epoxy-4-hydroxy-13(16),14- Di-00711

~
HO
clerodadiene-3,12-dione

C20H 260 6 M 362.422

Descr. in the ref. as both 6-oxo- and 7-oxo- but 7-oxo
appears to be correct.
(3P,4rz)-form [128988-37-4]
Constit. of Nardophyllum lanatum. Cryst. Mp 221°.
[129097-51-4]
Zdero, C. eta/, Phytochemistry, 1990, 29, 1227 (isol, pmr) 0

11,15-Epoxy-15-hydroxy-4(18),12- Di-00709 C20 H 280 4 M 332.439

clerodadien-16-al (ent-4rz)-form [118607-72-0]
Constit. of Croton argyrophylloides. Cryst.
(MeOHjhexane). Mp 122-124°. [1X]i;' +41° (c, 1.07 in
CHC1 3).
Monte, F.J.Q. et a/, Phytochemistry, 1988, 27, 3209.

2,18-Epoxy-19-hydroxy-3,13-clerodadien- Di-00712
16,15-olide

C20H 30 0 3 M 318.455
(ent-11 q,,15q,)-form [96888-27 -6] 0
Constit. of Linaria saxatilis.
Ac: Oil. [1X]n -14,70 (c, 0.25. in CHC1 3).
15-Ketone: [96888-20-9]. ent-16-0xo-4(18),12-clerodadien-
15,11-olide
C20H 280 3 M 316.439 C20 H 280 4 M 332.439
Constit. of L. saxatilis. Oil. [1X]n -5.3° (c, 1.7 in (ent-2p)-form [110668-26-3] Brevijloralactone
CH 2Cl 2). Constit. of Salvia breviflora. Cryst. Mp 126°. [1X]i,l'
San Feliciano, A. eta/, Tetrahedron, 1985, 41, 671. +0.232° (c, 2.3 in MeOH).
Ac: Brevifloralactone acetate
15,16-Epoxy-6-hydroxy-13(16),14- Di-00710 C22 H 300 5 M 374.476
Constit. of S. breviflora. Cryst. Mp ll2°.
clerodadiene-18,19:20,12-diolide
Cuevas, G. et a/, Phytochemistry, 1987, 26, 2019.

18,19-Epoxy-19-hydroxy-3,13-clerodadien- Di-00713
15,16-olide

(ent-6cx,I2~H}:form

C20 H 240 6 M 360.406

CwH2804
[75443-74-2] Teucrin H2. Teuchamaedryn
(ent-6r~-,12PH)-form
(19R)-form
B Amphiacrolide C
Constit. of Teucrium hyrcanicum and T. chamaedrys. Constit. of Gutierrezia texana and Amphiachryris
Cryst. Mp 206-208°. [1X]i,l' -5°. dracunculoides. Cryst. (EtOAc). Mp 151-153°. [1X]i?
(ent-6P,12PH)-form [54927-87-6) Teucrin E -59.2° (c, 1.2 in MeOH).
Constit. ofT. chamaedrys. Cryst. (Me 2CO/Etz0). Mp
235-238°. [1X]i,l' -25° (Me2CO).

777
15,16-Epoxy-10-hydroxy-2,7,13(16) ... - 15,16-Epoxy-4-hydroxy-2,13(16),14-... Di-00714- Di-00716

3P,4P-Epoxide: 3P,4P: 18, 19-Diepoxy-19-hydroxy-13- 15,16-Epoxy-19-hydroxy-1,3,13(16),14- Dl-00715

cleroden-15,16-olide. Amphiacrolide D clerodatetraen-18-oic acid
C20H 28 0 5 M 348.438
From G. texana and A. dracuncu/oides. Cryst.
(EtOAcjhexanejC6H 6). Mp 118-120°. [oc] 0 -15.1° (c,
0.86 in CHC1 3).
3P,4P-Epoxide, 18P-hydroxy: 3P,4P:18,19-Diepoxy-18P,19rx.-
dihydroxy-13-cleroden-15 ,16-olide
C20H 28 0 6 M 364.438
From G. texana. Oil. [oc]~ + 19.9° (c, 0.8 in CHC1 3).
3P,4P-Epoxide, 18-oxo: 3P,4P-Epoxy-19rx.-hydroxy-13- ~
clerodene-15,16:18,19-diolide I

C20H 260 6 M 362.422 HOOC CHpH

From G. texana. Oil.
C20 H 260 4 M 330.423
19-0xo: 3,13-C/erodadiene-15,16:19,18-diolide.
Amphiacrolide A ent-form
Constit. of A. dracunculoides. Cryst. (CHC1 3jhexane). Ac: 19-0-Acetyl-1,2-dehydrohautriwaic acid
Mp 84-85°. [oc] 0 + 35.9° (c, 1 in CHC1 3). C22 H 280 5 M 372.460
Gao, F. et a!, Phytochemistry, 1987, 26, 209 (isol)
!sol. from Copaifera scabrida (as Me ester) and
Harraz, F.M. eta!, J. Nat. Prod. (Lloydia), 1990, 53, 1312 (isol, Baccharis flabellata. Oil. [oc] 0 -122.3° (c, 0.62 in
pmr, cmr) CHC1 3).
Saad, J .R. et a!, Phytochemistry, 1988, 27, 1884.
15,16-Epoxy-10-hydroxy-2,7,13(16),14- Di-00714
clerodatetraene-17,12:18,19-diolide 15,16-Epoxy-4-hydroxy-2,13(16),14- Di-00716
clerodatriene-17,12:18, 1-diolide

0
@o
I

(1 ~,4cx,5cx,8cxH, !2aH)-form
0
I )
0:::::1-..0
C2oH2o06 M 356.374 0
(ent-10rx.,12rx.H)-form [85564-00-7] Salviacoccin C20H 220 6 M 358.390
Constit. of Salvia coccinea. Cryst. (MeOH). Mp 242-
2440. [oc]~ -139.8° (c, 0.49 in Py). (lp,4rx.,5rx.,Brx.H,12rx.H)-form [471-54-5]/socolumbin
!sol. from Dioscoreaphyllum cumminsii, also obt. by
2P,3P-Epoxide: 2,3:15,16-Diepoxy-10-hydroxy-7,13(16),14- isom. of Columbin. Cryst. (MeOH). Mp 190°.
clerodatriene-17,12: 18,19-diolide. Epoxysalviacoccin
C20H 20 0 7 M 372.374 Ac: Cryst. (Me2COjEtOH). Mp 225-226°. [oc] 0 +28° (c,
Constit. of S. plebeia. Cryst. (MeOH). Mp 197-199°. 1.03 in Py).
[oc]i-,8 -40.2° (c, 0.241 in Py). 2P,3P-Epoxide: [1 00938-01-0]. 2,3:15,16-Diepoxy-4-hydroxy-
7,8P-Dihydro: 15,16-Epoxy-10-hydroxy-13(16),14- 13(16),14-c/erodadiene-17,12: 18,1-dio/ide. lsojateorin. 8-
c/erodadiene-17,12: 18 ,19-dio/ide. 7,8P-Dihydrosalviacoccin Epijateorin
C20H 22 0 6 M 358.390 C2oH220 7 M 374.390
Constit. of S. greggii. Cryst. (Me2CO/Et20). Mp 268- Cryst. (MeOH). Mp 165-167°. [oc] 0 +30° (c, 3.99 in Py).
2700. [oc]~ -123.8° (c, 0.112 in Py). 2P,3P-Epoxide, 0-P-D-glucopyranoside: lsojateorinyl
Savona, G. et a!, Phytochemistry, 1982, 21, 2563.
glucoside
Garcia-Alvarez, M.C. et a!, Phytochemistry, 1986, 25, 272 (deriv) C26 H 320 12 M 536.532
Bruno, M. et a!, Phytochemistry, 1986, 25, 475 (deriv) Constit. of J. columba. Cryst. Mp 204-207°. [oc] 0 + 15.4°
(c, 0.11 in Py).
(1P,4rx.,5rx.,BPH,l2rx.H)-form [546-97-4] Columbin. Tinosporin
Constit. of Columbo root, Jatrorrhiza palmata and from
Tinospora cordifolia. Cryst. (MeOH). Mp 195-196°. [oc] 0
+52.7° (c, 1 in Py).
0-P-D-Giucopyranoside: Columbinyl glucoside
C26H 3Pu M 520.532
Constit. of J. columba. Cryst. Mp 172-176°. [oc] 0 +18.4°
(c, 1.4 in MeOH).
2fi,3fi-Epoxide: [23369-74-6]. Jateorin. Tinosporide
C20H 220 7 M 374.390
Constit. of J. pa/mata and T. cordifo/ia. Cryst. (MeOH).
Mp 239-241°. [oc]~ -17° (c, 0.5 in EtOH). Readily isom.
to 8-epimer.

778
15,16-Epoxy-4-hydroxy-2,13(16),14-... - 15,16-Epoxy-2-hydroxy-3,13(16),14-... Di-00717- Di-00720

2P,3P-Epoxide, 0-P-D-glucopyranoside: Jateorinyl glucoside Constit. of Teucrium scordium. Cryst. Mp 229-231°. [rx]~
C16H 320 12 M 536.532 -74.7° (c, 0.16 in Me 2CO).
Constit. of J. calumba. Cryst. Mp 217-221°. [rx]n +5.6° 6-Ketone: [76902-35-7]. 15,16-Epoxy-6-oxo-3,13{16),14-
(c, 0.14 in MeOH). clerodatriene-18,19:20,12-diolide. Teuscordinone. 6-
(lp,4rx.,5rx.,8rx.H,11PH)-form Ketoteuscordin
2P,3P-Epoxide: [17226-41-4]. Palmarin C20H 200 6 M 356.374
Constit. of J. palmata. Cryst. (Me 2CO/Et0Ac). Mp 253- Constit. ofT. scordium. Cryst. Mp 235°. [rx]~ -84.1° (c,
2580. [tX]D + 17° (C, 1.45 in Py). 1.2 in dioxan).
(1 p,4rx.,5rx.,8PH,11PH)-form Papanov, G.Y. et al, Phytochemistry, 1981, 20, 170 (Teuscordinone)
Gacz-Baitz, E. et al, Heterocycles, 1982, 19, 539 (cmr)
2P,3P-Epoxide: [20379-19-5]. Chasmanthin
Papanov, G.Y. eta/, Z. Naturforsch., B, 1982, 37, 519 (isol)
C20H 220 7 M 374.390
Constit. of J. palmata. Cryst. Mp 225-228°. [aln+ 0°
(Py). Mp refers to impure specimen. 15,16-Epoxy-19-bydroxy-3,13(16),14- Dl-00719
Barton, D.H.R. et al, J. Chern. Soc., 1962, 4809 (isol) clerodatriene-19,6:20,12-diolide
Ba1asubramanian, S.K. et al, J. Chern. Soc., 1962, 4816 (struct)
0

Q
Reed, R.I. et al, J. Chern. Soc., 1963, 5955 (ms)
Dreyer, D.L., Tetrahedron, 1965, 21, 75 (pmr)
Cheung, K.K. et al, J. Chern. Soc. B, 1966, 583 (cryst struct,
I
lsocolumbin)
Overton, K.H. et al, J. Chern. Soc. C, 1966, 1482 (struct)
Ferguson, G. et al, J. Chern. Soc. B, 1969, 162 (cryst struct) (ent-12a.H)-form
Ramstad, E. et al, Phytochemistry, 1975, 14, 2719 (isol,
lsocolumbin)
ltokawa, H. et al, Planta Med., 1987, 271 (Glucosides)
Swaminathan, K. et al, Acta Crystallogr., Sect. C, 1989, 4S, 134
(cryst struct, Tinosporide)
Swaminathan, K. et al, Acta Crystallogr., Sect. C, 1989, 4S, 300 CH2 0H
(cryst struct, Columbin)
"Bhatt, R.K. et a/, Indian J. Chern., Sect. B, 1990, 29, 521 (iso/, C20H 220 6 M 358.390
cryst struct, Tinosporide) (ent-11rx.H)-form
11-Epiteuscordonin. 12-Epiteuscorodonin
15,16-Epoxy-4-bydroxy-2,13(16),14- Dl-00717 Constit. of Teucrium bicolor. Cryst. (EtOAcfpet. ether).
clerodatriene-17,12:18,6-d.iolide Mp 199-203°.
(ent-11PH)-form [87376-66-7] Teuscorodonin. Teuscordonin

0
Constit. of T. scorodonia. Cryst. (EtOAcfhexane). Mp
189-191°. [rx]i; +110.8° (c, 0.204 in CHC1 3).
8,17-Didehydro: [69749-00-4]. ent-15,16-Epoxy-19-hydroxy-
3,8(17), 13(16), 14-clerodatriene-19 ,6P:20, 12-diolide.
Plaunol B
C20 H 200 6 M 356.374
0 Isol. from Croton sublyratus. Cryst. Mp 184°. [rx]~4
+41.4° (c, 0.35 in Me2CO).
Kitazawa, E. et al, Chern. Pharm. Bull., 1980, 28, 227 (Plaunol B)
Marco, J.L. et al, Phytochemistry, 1983, 22, 727 (Teuscorodonin)
Labbe, C. et al, J. Nat. Prod. (Lloydia), 1989, S2, 871
C20H 210 6 M 358.390 (Epiteuscorodonin)
(ent-41;,5rx.,6p,l1rx.H)-form
Tinospora furanolactone 15,16-Epoxy-2-bydroxy-3,13(16),14- Di-00720
Constit. of Tinospora cordifolia. Cryst. (EtOH). Mp clerodatrien-18-oic acid
178°. [rx]i? -18.1 o (c, 0.55 in CHC1 3).
Hanuman, J.B. et al, Phytochemistry, 1986, 2S, 1677.

15,16-Epoxy-6-bydroxy-3,13(16),14- Di-00718
clerodatriene-18,19:20,12-diolide (ent-2a.)-form
0
#

HOOC
C20 H 280 4 M 332.439
(ent-111.)-form
1P-Hydroxyhardwickiic acid
Isol. from Copaifera coulteri.
(ent-1p)-form
C20H 220 6 M 358.390 Ac: 1rx.-Acetoxyhardwickiic acid
(ent-6rx.,J1PH)-form [81799-92-0] 6-Hydroxyteuscordin C22 H 300 5 M 374.476

779
15,16-Epoxy-6-hydroxy-3,13(16),14-... - 15,16-Epoxy-2-hydroxy-3,13(16),14-... Di-00721 - Di-00726

lsol. from Grangea maderaspatana. Gum (as Me ester). 15,16-Epoxy-1-hydroxy-3,13(16),14- Dl-00724

[aln -1.1° (c, 2.07 in CHC1 3) (Me ester). clerodatrien-18,19-olide
Jolad, S.D. eta/, Phytochemistry, 1988, 27, 1211 (isol)

15,16-Epoxy-6-hydroxy-3,13(16),14- Di-00721
clerodatrien-18-oic acid

(ent-5a.,6a.)-form
C20 H 260 4 M 330.423
(ent-lf/)-form [51848-02-31 Bacchofertin
Constit. of Baccharis conferta.
Guerro, C. eta/, Rev. Latinoam. Quim., 1973, 4, 178.
C20H 280 4 M 332.439
(ent-5r~.,6r~.)-form [95260-26-7] Dodonic acid
Constit. of Dodonaea viscosa. Cryst. Mp 105-107°. [aln 15,16-Epoxy-12-hydroxy-3,13(16),14- Dl-00725
-20° (c, 1 in EtOH). clerodatrien-18,19-olide
(ent-5P,6f/)-form OH
18-+6 Lactone: 15,16-Epoxy-3,13(16),14-clerodatrien-18,6- I

o/ide. Salvint
C20Hu.03 M 314.424
Constit. of Pu/icaria salviifolia. Cryst. (EtOAcjhexane). (ent-12R)-form
Mp 128°. [ali? -llo.4° (c, 0.42 in MeOH).
Sachdev, K. eta/, Planta Med., 1984, 50, 448.
Nurmukhamedova, M.R. eta/, Khim. Prir. Soedin., 1985, 21, 201;
Chern. Nat. Compd. (Engl. Trans/.), 188.
C20H 240 5 M 344.407
15,16-Epoxy-6-hydroxy-3,13(16),14- Di-00722 (ent-12R)-form [113464-51-01
clerodatrien-19-oic acid 12-0-P-n-G/ucopyranoside: Rhynchospermoside A
C26H 340 10 M 506.549
Constit. of Rhynchospermum verticillatum. Amorph.
powder. [alii -162° (c, 1.93 in MeOH).
(ent-128)-form
12-0-P-n-G/ucopyranoside: [113532-65-31.
Rhynchospermoside B
C26H 340 10 M 506.549
Constit. of R. verticillatum. Amorph. powder. [alii
C20H 280 4 M 332.439 -165° (c, 0.98 in MeOH).
[112606-14-11 Kerlinic acid
(ent-5r~.,6f/)-form Seto, M. eta/, Phytochemistry, 1987, 26, 3289.
Constit. of Salvia keer/ii. Cryst. (Me2COjpet. ether). Mp
183-185°. [ali,S -236.8° (c, 0.19 in CHCI 3). 15,16-Epoxy-2-hydroxy-3,13(16),14- Di-00726
Rodriguez-Hahn, L. eta/, Can. J. Chern., 1987, 65, 2687. clerodatrien-17,12-olid-18-oic acid
15,16-Epoxy-12-hydroxy-3,13(16),14- Di-00723
clerodatrien-18-oic acid

HOOC
C20H 240 6 M 360.406
(2r~.,5r~.,12r~.H)-form
HOOC
Me ester: [96552-83-91. Tinophyllol
CzoH 28 0 4 M 332.439 C2,H 260 6 M 374.433
121;-form Constit. of Arcangelisia jlava. Prisms (MeOH). Mp 229-
12-Hydroxyhardwickiic acid 2310. [ali? -19.3° (c, 0.5 in Py).
Constit. of Croton ronderianus. Oil (as Me ester). [a]i;l 0-P-n-G/ucoside, Me ester: [102907-33-51. Tinophylloloside
-80.9° (c, 7.3 in CHC1 3) (Me ester). C27H360 11 M 536.575
McChesney, J.D. eta/, Phytochemistry, 1989, 28, 3411 (iso/, pmr, Constit. of Fibraurea tinctoria. Powder (Hp). Mp 155-
cmr) 1580. [ali} -19.2° (c, 0.25 in MeOH).
2-Ketone, Me ester: [2571-62-21. Tinophyllone

780
15,16-Epoxy-4-hydroxy-2,13(16),14-... - 15,16-Epoxy-4-hydroxy-7-oxo-2,13(16)... Di-00727 - Di-00731

C11H240 6 M 372.417 15,16-Epoxy-19-hydroxy-2-oxo-13(16), 14- Dl-00729

Isol. from root and bark of Tinomiscium philippinense. clerodadiene-19,6:20,12-diolide
Cryst. Mp 175°. [tx]i,9 -98° (CHCI 3).
Gambolvej, S.K. et al, J. Phillipine Pharm. Assoc., 1958, 45, 303
(isol)
Aguilar-Santos, G., Chern. Ind. (London), 1965, 1074 (uv, ir, pmr,
ms)
Brehm, L. et al, J. Chern. Soc. C, 1971, 2529 (cryst struct)
Kunii, T. et al, Chern. Pharm. Bull., 1985, 33, 479 (isol, struct)
ltokawa, H. et al, Phytochemistry, 1986, 25, 905 (Tinophylloloside)

15,16-Epoxy-4-hydroxy-2,13(16),14-
clerodatrien-17, 12-olid-18-oic acid
Cwli240 5 M 344.407
(ent-4P,8PH,12PH)-form
Me ester: [110382-43-9]. Cordatint
C11 H 160 6 M 374.433
Constit. of Aparisthmium cordatum. Cryst. (Me 2CO).
Mp 170"172°. [tx]i? +140° (c, 0.1 in MeOH).
Dadoun, H. et al, Phytochemistry, 1987, 26, 2108 (cryst struct)
Di-00727
0
C10H110 7 M 374.390
(ent-12PH)-form [96386-42-4] 2-Keto-19-hydroxyteuscordin
Constit. of Teucrium scordium. Cryst. (Me 2CO/Etz0).
Mp 196-199°. [tx]~ +138.8° (c, 0.17 in Me2CO). The
name given to this compd. does not agree with the
struct. of Teuscordin, its hypothetical parent; see 15,16-
Epoxy-6-hydroxy-3, 13(16), 14-clerodatriene-18, 19:20,12-
diolide, Di-00718.
Papanov, G.Y. et al, Phytochemistry, 1985, 24, 297 (isol)
15,16-Epoxy-2-hydroxy-1-oxo-13(16),14- Dl-00730
clerodadien-17, 12-olid-18-oic acid

4,18-Epoxy-6-hydroxy-13-cleroden-15,16- Di-00728 HO,

olide 0

I
HOOC
C10H 240 7 M 376.405
(ent-2P,4rzH,12PH)-form
Me ester: [92545-30-7]. Divinorin B
C11 H160 7 M 390.432
Constit. of Salvia divinorum. Cryst. Mp 213-216°. [tx]i;l
-3.39° (c, 0.44 in EtOH).
2-Ac, Me ester: [83729-01-5]. Salvinorin. Divinorin A
C13H 180 8 M 432.469
C10H 300 4 M 334.455 Constit. of S. divinorum. Psychotropic agent. Cryst. Mp
242-244°. [ex]~ -45.3° (c, 8.53 in CHC1 3).
(ent-4P,6fl)-form
Ortega, A. et al, J. Chern. Soc., Perkin Trans. I, 1982, 2505.
Ac: [82231-14-9]. Ajugarin V Valdes, L.J. et al, J. Org. Chern., 1984, 49, 4716.
C11H310s M 376.492
Constit. of leaves of Ajuga remota. Cryst. Mp 217-218°.
[tx) 0 -13.5° (c, 0.18 in CHC1 3). 15,16-Epoxy-4-hydroxy-7-oxo- Dl-00731
Kubo, I. et al, Chern. Lett., 1983, 223. 2,13(16),14-clerodatrien-18,19-olide

C10H 240 5 M 344.407

(ent-4«)-form
4-Hydroxyisobacchasmacranone

781
15,16-Epoxy-3-oxo-13(16),14-... - 15,16-Epoxy-3,4,7,12-tetrahydroxy-... Di-00732 - Di-00736

Constit. of Baccharis rnacraei. Cryst. (EtOAcjpet. 15,16-Epoxy-7-oxo-3,13(16),14- Di-00734

ether). Mp 178-179°. [a]i;5 -68.SO (c, 0.8 in CHC1 3). clerodatrien-18,19-olide
Isobacchasmacranone not known.
Gambaro, V. eta/, Phytochemistry, 1987, 26, 475.

15,16-Epoxy-3-oxo-13(16), 14-clerodadien- Di-00732

20,12-olide-18,19-dioic acid

0
octJo
I C20 H 240 4 M 328.407
ent-form [105418-88-0] Bacchasmacranone
Constit. of Baccharis rnacraei. Cryst. (EtOAcjhexane).
Mp 126-127°. [a]i;5 -176.4° (c, 0.62 in CHC13).
2P-Hydroxy: [105418-89-1]. ent-15,16-Epoxy-2a-hydroxy-7-
oxo-3, 13(16),14-clerodatrien-18, 19-olide. 2P-
I COOH Hydroxybacchasmacranone
HOOC C20 H 240 5 M 344.407
C20H 220 8 M 390.389 From B. rnacraei. Cryst. (EtOAcjhexane). Mp 198-199°.
[a]i;5 -220° (c, 0.60 in CHCI 3 jhexane).
(ent-4rxH,12rxll)-form
Gambaro, V. eta/, Phytochemistry, 1986, 25, 2175.
Di-Me ester: [61661-30-1]. Corylifuran
C22H 260 8 M 418.443
Constit. of Croton corylifolius. Cryst. (C 6H 6 /Et0Ac). 15,16-Epoxy-12-oxo-3,13(16), 14- Di-00735
Mp 181-184°. [aln +44° (c, 0.9 in CHC1 3). clerodatrien-18,6-olide
Burke, B.A. eta/, Tetrahedron, 1976, 32, 1881 (cryst struct)

15,16-Epoxy-1-oxo-2,13(16),14- Di-00733
clerodatriene-17,12:18,19-diolide

0 0
C20 H 240 4 M 328.407
' (ent-5rx,6p)-form
o;.._J Linguifolide
Constit. of Dernotarisia linguifolia. Cryst. Mp 130-133°.
C20H 200 6 M 356.374 [aJn -24° (c, 0.25 in CHCI 3).
(ent-8PH,12PII)-form [113464-53-2] Rhynchosperin A 3,4P-Dihydro: 15,16-Epoxy-12-oxo-13(16),14-c/erodadien-
Constit. of Rhynchosperrnurn verticillaturn. Needles 18,6-olide. Dihydrolinguifolide
(MeOH). Mp 236-237°. [a]i;5 -195° (c, 0.37 in CHC1 3). C20 H 260 4 M 330.423
6P-Hydroxy: [113464-52-1]. ent-15,16-Epoxy-6a-hydroxy-l- Constit. of D. linguifolia. Cryst. Mp 158-160°. [aln +22°
oxo- 2, 13(16), 14-clerodatriene-17, 12: 18, 19-diolide. (c, 0.18 in CHC1 3).
Rhynchosperin B Nagashima, F. eta/, Phytochemistry, 1990, 29, 3229 (isol)
C20H 20 0 7 M 372.374
Constit. of R. verticillaturn. Needles (MeOH). Mp 277- 15,16-Epoxy-3,4,7,12-tetrahydroxy- Di-00736
2790. [a]i;5 -202° (c, 0.35 in CHC1 3).
13(16),14-clerodadien-20-al
6P-Tigloyloxy: [113464-50-9]. Rhynchosperin C
C25H 260 8 M 454.476
Constit. of R. verticillaturn. Amorph. powder. [a]i;5
-153° (c, 1.76 in CHCI 3).
Seto, M. eta/, Phytochemistry, 1987, 26, 3289.

C 10H 300 6 M 366.453

(ent-3ft,4rx,7ft,l2S)-form
7-Ac: [10118-56-6]. Cascarillin

782
15,16-Epoxy-3,4,7,10-tetrahydroxy-... - 15,16-Epoxy-6,7,18,19-tetrahydroxy-... Di-00737 - Di-00741

C22 H 3z07 M 408.491 (ent-3P,4tT.,6P,8tT.,lltT.,l3S)-form

Constit. of Croton eleuteria. Cryst. (EtOH). Mp 203.5°. 6-Benzoyl, 11-Ac: [114489-73-5]. Scutellone A.
McEachan, C.E. eta/, J. Chern. Soc. B, 1966, 633. Scuterivulactone C1
Cz9H 380 9 M 530.614
15,16-Epoxy-3,4,7,10-tetrahydroxy- Di-00737 lsol. from S. rivularis. Prisms (Me 2CO); cryst. (EtOAc).
Mp 290-292° (268-272°). [1X]n -7.0° (AcOH), [1X]n
13(16), 14-clerodadien-20, 12-olide + 1.26° (c, 1.0 in MeOH).

Q
[112709-53-2]
Kikuchi, T. et a/, Chern. Lett., 1987, 987.
Lin, Y.-L. et a/, J. Chern. Res. (S), 1987, 320 (cryst struct)
I
Lin, Y.-L. et a/, Heterocycles, 1988, 27, 779.

L? 15,16-Epoxy-2,6,18,19-tetrahydroxy-
3,13(16),14-clerodatrien-20,12-olide
Di-00740

HO OH
I
HO
C20H 280 7 M 380.437
Incorrectly called a labdane in the ref.
(3p,4tT.,7p,Jop,J2pH)-form
Constit. of Conyza aegyptica. Gum. HO
Zdero, C. eta/, Phytochemistry, 1990, 29, 3167 (isol, pmr, cmr)
::::::,..,
I

15,16-Epoxy-4,6,18,19-tetrahydroxy- Di-00738 HOCH2 : OH

CH20H
13(16),14-clerodadien-20,12-olide
C20H 260 7 M 378.421
(ent-2tT.,6tT.,12PH)-form [103994-18-9] Teusalvin D
Constit. of Teucrium salviastrum. Amorph. (as tetra-Ac).
Mp 68-77° (tetra-Ac). [IX]~ -76. 7o (c, 0.378 in CHC1 3)
(tetra-Ac).
De La Torre, M.C. eta/, Phytochemistry, 1986, 25, 1397.

15,16-Epoxy-6,7,18,19-tetrahydroxy- Di-00741
3,13(16),14-clerodatrien-20,12-olide

C20 H 28 0 7 M 380.437
(ent-4tT.,6tT.,12PH)-form [89984-03-2] Montanin E
Constit. of Teucrium montanum. Cryst. Mp 219-223°.
[a]~ +23.SO (c, 0.136 in Me 2CO).
Papanov, G.Y. eta/, Phytochemistry, 1983, 22, 2787.

8,13-Epoxy-3,4,6,11-tetrahydroxy-15,16- Di-00739 : -oH

clerodanolide HOH2C i OH
0 CH20H
_)=o C20 H260 7 M 378.421
(ent-6tT.,7P,12PH)-form
19-Ac: Lonin
(ent-30(,40(,6~,80(, 110(, 13S)-form
C22 H 280 8 M 420.458
Constit. of Teucrium capitatum. Cryst. (MeOH/EtOAc).
I
HO OH Mp 166-167°.
C20H 32 0 7 M 384.469 Marquez, C. eta/, Tetrahedron Lett., 1981, 2823.

(ent-3tT.,4tT.,6p,8tT.,]]tT.,l3S)-form
6-Benzoyl, 11-Ac: [114489-74-6]. Scutellone C
C29 H 380 9 M 530.614
Constit. of Scutellaria rivularis. Needles (Me 2CO). Mp
228-230°. [a]~ -20.0° (c, I in CHCIJ.
(ent-3P,4tT.,6p,8tT.,]]tT.,l3R)-form
6-Benzoyl, 11-Ac: [112609-10-6]. Scuterivulactone C2
C29H 380 9 M 530.614
Constit. of S. rivularis. Amorph. (as acetate). [1X]n -31°
(CHCI 3) (acetate).

783
4,18-Epoxy-1,6,12,19-tetrahydroxy-... - 15,16-Epoxy-6,18,19-trihydroxy-... Di-00742 - Di-00745

4,18-Epoxy-1,6,12,19-tetrahydroxy-13- Dl-00742 C15H 310 7 M 444.524

cleroden-15,16-olide Constit. of P. incana. Oil.
8P,17-Epoxy: [129349-87-7]. 8P,17; 15,16-Diepoxy-
0 3cx,4p, l OP-trihydroxy-13(16), 14-clerodadien- 20, 12-olide
C:zoH160 7 M 378.421
Constit. of P. incana.
8P,J7-Epoxy, 3-Ac: [129349-88-8].
C11H 280 8 M 420.458
Constit. of P. incana. Gum.
8P,I7-Epoxy, 3-angeloyl: [129384-18-5].
C15H 310 8 M 460.523
Constit. of P. incana. Gum.
'' Zdero, C. et al, Phytochemistry, 1990, 29, 1231 (isol, pmr)
''
rn2oH
15,16-Epoxy-2,3,4-trihydroxy- Dl-00744
C:zoH300 7 M 382.453 1(10),13(16),14-clerodatrien-20,12-olide
(ent-1 rx.,4P,6P,J2R)-form

Q
6,19-Di-Ac, 1-tigloyl: [78798-40-0]. Ajugamarin
C 29H 400 10 M 548.629
Constit. of leaves of Ajuga nipponensis. Needles (CC14).

HO,g8-~? 1
Mp 93-95°. [cx]i; -20° (c, 0.4 in CC14).
6,19-Di-Ac, 1-(2-methylbutanoyl): [85447-28-5].
Dihydroajugamarin
C~ 41 0 10 M 550.645
Constit. of A. nipponensis. Amorph. solid.
Shimomura, H. et al, Chern. Pharm. Bull., 1983, 31, 2192 (cryst HO/
\
str.uct) HO '
C:zoH160 6 M 362.422
15,16-Epoxy-3,4,10-trihydroxy-13(16),14- Di-00743 (2rx.,3rx.,4p)-form
clerodadien-20, 12-olide 3-Angeloyl: [129349-90-2].
C15H 320 7 M 444.524

Q Constit. of Pteronia eenii. Oil.

Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr)

Hifw?.,
I

15,16-Epoxy-6,18,19-trihydroxy- Di-00745
3,13(16),14-clerodatrien-20,12-olide
0
j
HO \
C 20H 280 6 M 364.438
(3rx.,4p,JOp)-form [129349-80-0]
Constit. of Pteronia incana and P. eenii. Gum.
8P-Hydroxy: [129349-81-1]. 15,16-Epoxy-3rx.,4p,ap,JOfJ-
tetrahydroxy-13(16),14-clerodadien-20,12-olide
C10H 280 7 M 380.437
Constit. of P. eenii. Cryst. Mp 152°.
8P-Hydroxy, 3-Ac: [129349-82-2]. (ent-6rx.,12PH)-form [103994-19-0] Teusalvin C. 19-
C11H 300 8 M 422.474 Deacetylteuscorodol
Constit. of P. incana and P. eenii. Cryst. Mp 227°. C10H 160 6 M 362.422
8P-Hydroxy, 3-ketone: [129349-83-3]. 15,16-Epoxy- From Teucrium botrys and T. salviastrum. Cryst.
4P,BP,lOfJ-trihydroxy-13(16),14-clerodadien-20,12-olide (EtOAcfhexane). Mp 200-202°. [cx]i;' -46.2° (c, 0.197 in
C10H 160 7 M 378.421 Py).
Constit. of P. eenii. Gum. 19-Ac: [85563-66-2]. Teuscorodol
8,17-Didehydro: [129349-84-4]. 15,16-Epoxy-3cx,4P,10P- C11H 280 7 M 404.459
trihydroxy-8(17), 13(16), 14-clerodatrien- 20, 12-olide Constit. ofT. scorodonia. Amorph. powder. Mp 65-70°.
C 10H 160 6 M 362.422 [cx]i,O -55.8° (c, 0.8 in CHC1 3).
Constit. of P. eenii. Gum. 18-Aldehyde, 19-Ac: [85563-67-3]. Teuscorodal
8,17-Didehydro, 3-ketone: [129349-85-5]. 15,16-Epoxy- C11H 160 7 M 402.443
4P, 1op-dihydroxy-3-oxo-8(17), 13(16), 14-c!erodatrien- Constit. ofT. scorodonia. Cryst. (hexane). Mp 60-63°.
20, 12-olide [cx]i,O -51.4° (c, 0.36 in CHC1 3).
C10H 240 6 M 360.406 Marco, J.L. et a/, Phytochemistry, 1982, 21, 2567 (isol)
Constit. of P. eenii. Gum. [cx]~4 +48° (c, 0.3 in CHC1 3). De La Torre, M.C. et a/, Phytochemistry, 1986, 25, 1397, 2385
8,17-Didehydro, 3-angeloyl: [129349-86-6]. (is of)

784
4,18-Epoxy-3,6,19-trihydroxy-1-oxo-... - 2-Hydroxy-3,13-clerodadiene-... Di-00746- Di-00750

4,18-Epoxy-3,6,19-trihydroxy-1-oxo-13- Di-00746 From F. chloroleuca. Mp 303-304°. [IX]~ + 23.6° (c, 1.13

cleroden-15,16-olide in Py).
Hori, T. et al, Tetrahedron, 1967, 23, 2649 (Fibraurin)
Ito, K. et al, J. Chern. Soc., Chern. Commun., 1969, 653.
Kunii, T. et al, Chern. Pharm. Bull., 1985, 33, 479 (deriv)
Itokawa, H. et al, Phytochemistry, 1986, 25, 905 (Fibleucinoside,
Fibraurinoside)

3-Hydroperoxy-4(18),13-clerodadien-15- Di-00748
oic acid

,.- COOH

C 20H 280 7 M 380.437

HOO
(ent-3rr.,4p,6fl)-form
3-(2-Methylbutanoyl), 6,19-di-Ac: [79495-92-4].
M 336.470
Ajugareptansone A
C29H 400 10 M 548.629 Me ester:
Constit. of Ajuga reptans. Cryst. (EtOAcjEtzO). Mp C21 H 340 4 M 350.497
177-180°. [1X]n -6° (c, 1.98 in CHCI 3). Constit. of Solidago altissima. Oil.
Camps, F. et al, Chern. Lett., 1981, 1093 (cryst struct) (ent-3rr.,13E)-form [104189-07-3] Scapanin G
Miravitlles, C. et al, Acta Crystallogr., Sect. B, 1982, 38, 188 (cryst Constit. of liverwort Scapania undulata. Cryst.
struct, abs config) (EtzOjpet. ether). Mp 125-127°.
Singh, R.K. et al, Indian J. Chern., Sect. B, 1986, 25, 239.
Fibleucin Huneck, S. et al, J. Chern. Res. (S), 1986, 162.
Di-00747
15,16-Epoxy-41X-hydroxy-2,7,13(16),14-clerodatetraene-
17,12: 18,1P-diolide 2-Hydroxy-3,13-clerodadien-15, 16:18,6- Di-00749
[24278-14-6] diolide

0 ''

0
C20H 260 5 M 346.422
(1P,5rr.,6rr.)-form
0 Constit. of Gutierrezia texana. Oil.
C20H 200 6 M 356.374 (ent-1rr.,5rr.,6f/)-form
Constit. of Fibraurea chloroleuca. Cryst. Mp 169-172°. [1X]n 13f,,l4-Dihydro: [71051-92-8]. ent-Jrr.-Hydroxy-cis-3-
-28° (Py). clerodene-15,16:19,6P-olide
4-0-P-n-Glucopyranoside: [1 02926-02-3]. Fibleucinoside C20H 280 5 M 348.438
C26H 300 11 M 518.516 Constit. of Symphiopappus itatiayensis. Cryst. Mp 229-
Constit. of F. tinctoria. Cryst. (H 20). Mp 187.5-lll9.0°. 2300.
6f,-Hydroxy: 15,16-Epoxy-41X,6-dihydroxy-2,7,13(16),14- Vichnewski, W. et al, Phytochemistry, 1979, 18, 129 (deriv)
clerodatetraene-17, 12: 18,1ft-diolide. 6-Hydroxyfibleucin Gao, F. et al, Phytochemistry, 1987, 26, 209 (iso[)
C20H 20 0 7 M 372.374
Constit. of Arcangelisia flava. Plates (MeOH). Mp 195- 2-Hydroxy-3,13-clerodadiene-15,16:18,19- Di-00750
2040 dec. [IX]~ +59.1° (c, 0.49 in Py). diolide
2ft,3ft-Epoxide: [25254-84-6]. 2ft,3P: 15, 16-Diepoxy-41X-
hydroxy-7,13(16),14-clerodatriene-17, 12;18, 1ft-diolide.
Fibraurin
C20H 20 0 7 M 372.374
Isol. from F. chloroleuca. Cryst. (MeOH). Mp 288-289°.
[1X]n -28° (c, 1 in Py).
2ft,3ft-Epoxide, 4-0-P-n-g/ucopyranoside: [102907-32-4].
Fibraurinoside
Constit. of F. tinctoria. Cryst. (CHCI 3jMeOH). Mp 212-
214.50. [IX]~ -8.7° (c, 0.28 in MeOH).
2ft,3ft-Epoxide, 6f,-hydroxy: 2ft,3P: 15,16- Diepoxy-41X,6-
dihydroxy- 7, 13(16), 14-clerodatriene-!7, 12: 18, I P-diolide. 6-
Hydroxyfibraurin
M 346.422
C 20H 200 8 M 388.373

785
2-Hydroxy-3,13-clerodadiene-... - 2-Hydroxy-3,13-clerodadien-15-... Di-00751 - Di-00755

(ent-2«)-form [75478-98-7] Articulin 12-Hydroxy-3,13-clerodadiene- Di-00753

Constit. of Baccharis articulata. 15,16:18,19-diolide
Ac: Articulin acetate
C21H 28 0 6 M 388.460 OH
Constit. of B. articulata.
Stapel, G. et al, Planta Med., 1980, 39, 366 (isol, struct)

(ent-5r:J., 10~, 128)-form

2-Hydroxy-3,13-clerodadiene-16,15:18,19- Di-00751
diolide

C20H 260 5 M 346.422

(ent-5«,10P,12S)-form [67392-49-8) Marrubiastrol
Constit. of Leonurus marrubiastrum. Cryst. (Me 2C0jpet.
ether). Mp 179-180°. [tx}i? -70° (c, 0.35 in CHC1 3).
(ent-5p,10rr.,12~)-form [15401-87-3] 0/earin
Constit. of Olearia heterocarpa. Cryst. Mp 213°. [tx} 0
-1?0° (c, 1 in CHC1 3).
Pinhey, J.T. eta/, Aust. J. Chern., 1971, 24, 2621 (0/earin)
C20 H 21,05 M 346.422 Tschesche, R. et a/, Chern. Ber., 1978, 111, 2130 (Marrubiastrol)
(ent-2«)-form
Ac: ent-2«-Acetoxy-3,13-clerodadiene-16,15:18,19-diolide 17-Hydroxy-3,13-clerodadiene- Di-00754
C22H280 6 M 388.460
Constit. of Salvia melissodora. Cryst. (CH 2Cl2/Me0H).
15,16:18,19-diolide
Mp 202-204°. [tx}i? -209.5° (c, 0.16 in CHC1 3). 0
Esquivel, B. et a/, Phytochemistry, 1989, 28, 561.

7-Hydroxy-3,13-clerodadiene-16,15:18,19- Dl-00752
diolide
0

(ent-7cr)-form

C20H 260 5 M 346.422

(ent-5rr.,10fJ)-form [51419-53-5) Marrubialactone
Constit. of Leonurus marrubiastrum. Cryst. (MeOH).
C20H 260 5 M 346.422 Mp 212-213°.
(ent-7«)-form 17-Aldehyde: [67362-64-5]. ent-17-0xo-3, 13-clerodadiene-
Constit. of Salvia melissodora. Cryst. (EtOAcjMeOH). 15, 16:18, 19-diolide. Aldehydromarrubialactone
Mp 196-197°. [txJi? -93.3° (c, 0.15 in MeOH). C20H 240 5 M 344.407
7-Ketone: entc7-0xo-3,13-clerodadiene-16,15:18,19-olide Constit. of L. marrubiastrum. Cryst. (pet. ether). Mp
C20H 240 5 M 344.407 176-178°. [tx}i? -31.4° (c, 0.5 in CHC1 3).
Constit. of S. melissodora. Cryst. (EtOAc). Mp 89-93°. Tscheche, R. et a/, Chern. Ber., 1973, 106, 2929; 1978, 111, 2130.
[tx)i? -168.4° (c, 0.152 in CHC1 3).
(ent-7fJ)-form 2-Hydroxy-3,13-clerodadien-15-oic acid Di-00755
Constit. of S. melissodora. Cryst. (Me 2COfdiisopropyl
ether). Mp 178-179°. [tx)i? -154.SO (c, 0.165 in CHC1 3). [118173-04-9)
Ac: ent-7P-Acetoxy-3,13-clerodadiene-16,15:18,19-diolide # COOH
C21H 280 6 M 388.460
Constit. of S. melissodora. Cryst. (CH 2Cl2 jdiisopropyl
ether). Mp 178-179°. [tx}i? -110.7° (c, 0.17 in CHC1 3). (ent-2r:J.,5r:J., 13Z)-form
Esquivel, B. et al, Phytochemistry, 1988, 27, 2903; 1989, 28, 561. HO

C20 H 320 3 M 320.471

(ent-2rr.,5rr.,13Z)-form
Constit. of Ageratina salti/lensis.
2-Ketone: [118243-69-9]. ent-2-0xo-3,13-clerodadien-15-oic
acid
C20 H 300 3 M 318.455
Constit. of A. saltillensis.

786
7-Hydroxy-3,13-clerodadien-15-... - 6-Hydroxy-3,13-clerodadien-15,16-... Di-00756 - Di-00760

(ent-2rx,5P,13E)-form ent-2rx-Hydroxy-3,13-kolavadien-15,16-olide
2-Ketone: [83725-59-1]. ent-2-0xo-3,13-clerodadien-15-oic Constit. of Symphyopappus compressus. Gum. [1X]i;'
acid. 2-0xoko/avenic acid +4.1° (c, 1 in CHC1 3).
C2oH 300 3 M 318.455 31X,41X-Epoxide: ent-3P,4P-Epoxy-2p-hydroxy-3,13-
Constit. of Xylopia aethiopica. Cubes (EtOAcjpet. clerodadien-15,16-olide. 31X,41X-Epoxy-2-hydroxy-3,13-
ether). Mp 187-189°. [IX]~ -56.SO (c, 0.52 in CHC1 3). kolavadien-15, 16-olide
(ent-5P,I3Z)-form lsol. from S. compressus. Gum.
2-Ketone: Bohlmann, F. et al, Phytochemistry, 1981, 20, 1657.
C20H 300 3 M 318.455 Fang, N. et al, Phytochemistry, 1988, 27, 3187.
Constit. of A. ixiocladon.
Hasan, C.M. et al, Phytochemistry, 1982, 21, 1365 (2-0xakolavenic 2-Hydroxy-3,13-clerodadien-16,15-olide Di-00759
acid)
Fang, N. et al, Phytochemistry, 1988, 27, 3187 (isol)
Tanaya-Castillo, G. et al, Phytochemistry, 1989, 28, 137 (isol)

(ent-2cr)-form
7-Hydroxy-3,13-clerodadien-15-oic acid Di-00756

C20H 300 3 M 318.455

(ent-2rx)-form
COOH 2,15-Dihydroxykolavenic acid lactone
Constit. of Acritopappus hagei. Gum (as acetate). [1X]i;'
-5.6° (c, 0.4 in CHC1 3) (acetate).
C20H 320 3 M 320.471 2-Ketone: 2-0xo-3,13-clerodadien-16,15-olide
(ent-7P,I3E)-form C20H 280 3 M 316.439
Ac: [19941-91-4]. Solidagonic acid Constit. of A. hagei. Gum.
C22 H 340 4 M 362.508 Bohlmann, F. et al, Phytochemistry, 1980, 19, 2695.
Constit. of Solidago altissima. Cryst. (pet. ether). Mp
143-144°. [1X]i; -97.6° (EtOH). 6-Hydroxy-3,13-clerodadien-15,16-olide Dl-00760

W HC':Cro
Kusumoto, S. et al, Bull. Chern. Soc. Jpn., 1969, 42, 812.

20-Hydroxy-3,13-clerodadien-15-oic acid Dl-00757

,::7 COOH
6
I
I

OH
C20 H 300 3 M 318.455
Relative (5rx,6P,8PH)-form [24399-41-5] Elongatolide A. Solidagolactone
configuration IV
Constit. of Solidago altissima and S. elongata. Piscicide.
Cryst. (EtOAcjhexane). Mp 137-138°. [IX]~ +3.58° (c,
C20H 320 3 M 320.471 0.92 in EtOH). Also descr. as oil.
(13Z)-form [83991-78-0] Stephalic acid Ac: [24399-42-6]. Elongatolide B
Constit. of Stevia polycephala. Cryst. (EtOAcjhexane). Constit. of roots of S. elongata. Oil.
Mp 183.5-185.0°. [1X]~ +217° (c, 1 in CHC1 3).
Angeloyl: [24399-43-7]. Elongatolide C
Angeles, E. eta/, Phytochemistry, 1982, 21, 1804 (isol, cryst struct)
Piers, E. et al, J. Chern. Soc., Chern. Commun., 1989, 1665 (synth)
C2sH3604 M 400.557
Constit. of roots of S. elongata. Oil.
3P,4P-Epoxide, 6-Ac: [24399-44-8]. Elongatolide D
2-Hydroxy-3,13-clerodadien-15,16-olide Di-00758 C22H320s M 376.492
[118173-03-8] Constit.-4--roots_ p{ §. elongata. Oil.
0 3P,4P-Epoxide, 6-angeloyl: [24399-45-9]. Elongatolide E.
Solidagolactone VII
C25H360 5 M 416.556
Constit. of S. altissima. Piscicide. Cryst.
(EtOAcjhexane). Mp 119-120°. [IX]~ -28.4° (c, 1.29 in
(ent-2cr,5cr)-form EtOH).
3P,4P-Epoxide, 6-tigloyl: [92419-69-7]. Solidagolactone VIII
C2oH3003 M 318.455 C25 H 360 5 M 416.556
(ent-2rx,5rx)-form Constit. of S. altissima. Piscicide. Oil. [IX]~ -27.4° (c,
Constit. of Ageratina saltillensis. 0.341 in EtOH).
3P,4P-Epoxide: [118243-68-8]. ent-3rx,4rx-Epoxy-2rx-hydroxy- 6-Ketone: [41943-77-5]. ent-6-0xo-3,13-clerodadien-15,16-
13-cleroden-15,16-olide olide. Solidagolactone V
C20H 300 4 M 334.455 C20H 280 3 M 316.439
Constit. of A. saltillensis.
(ent-2P,5p)-form

787
16-Hydroxy-3,13-clerodadien-15,16-... - 15-Hydroxy-3,13-clerodadien-16,15-... Di-00761 - Di-00765

Constit. of S. altissima. Piscicide. Cryst. (hexane). Mp
106.5-107°. [oc]i;' + 125.2° (c, 1.15 in EtOH).
Anthonsen, T. eta/, Acta Chern. Scand., 1969, 23, 1068 (isol)
Manabe, S. et a/, Tetrahedron, 1986, 42, 3461 (isol)
Ferguson, G. eta/, J. Chern. Soc., Chern. Commun., 1975, 299
(Marrubiaside)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695 (isol)
Givovich, A. et a/, Phytochemistry, 1986, 25, 2829 (isol)
Achari, B. eta/, Phytochemistry, 1990, 29, 3671 (Clerodermic acid)

16-Hydroxy-3,13-clerodadien-15,16-olide Di-00761 19-Hydroxy-3,13-clerodadien-16,15-olide Di-00763

0

-oH

C20H3003
(BPH)-form [70387-32-5] NidoreUalactone
Constit. of Nidorella agria. Oil. [oc]i;' -23.3° (c, 2.2 in
CHC1 3).
C20H 300 3 M 318.455 (ent-81%H)-form
(ent-16R)-form StrigiUanol
Constit. of Polyalthia longifolia. Gum. [oc]i,6 -70.58° (c, lsol. from Hoffmannia strigil/osa. Oil.
O.oi in MeOH). Bohlmann, F. eta/, Phytochemistry, 1978, 17, 1769
Ac: Cryst. (EtOAcjpet. ether). Mp 175°. [oc]~6 -24.24° (c, (Nidorellalactone)
Jaensch, M. eta/, Phytochemistry, 1990, 29, 3587 (Strigillanol)
0.066 in MeOH).
(ent-161;,)-form
13.;,14-Dihydro: 16-Hydroxy-3-cleroden-15,16-olide
6-Hydroxy-3,13-clerodadien-15,16-olid-19- Dl-00764
C20 H 320 3 M 320.471 oic acid
Constit. of Acritopappus teixeirae. Gum.
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695 (isol)
Phadnis, A.P. et a/, Phytochemistry, 1988, 27, 2899 (isol)

18-Hydroxy-3, 13-clerodadien-16,15-olide Di-00762 I

I
I I
0 : OH
COOH
0
C20 H 280 5 M 348.438
(ent-6/l)-form [54153-70-7] Melisodoric acid. Melissodoric acid
Constit. of Salvia melissodora.
Rodriguez-Hahn, L. eta/, Rev. Latinoam. Quim., 1973, 4, 93 (isol)
Rodriguez-Hahn, L. eta/, Can. J. Chern., 1987, 65, 2687 (struct)

15-Hydroxy-3, 13-clerodadien-16,15-olid- Di-00765

~H2 0H
19-oic acid
C20H 300 3 M 318.455
(ent-51% )-form OH
Constit. of Acritopappus hagei. Gum.
Ac: ent-18-Acetoxy-3,13-clerodadien-16, 15-olide. 18-
Acetoxy-3 ,13-kolavadien-16,15-olide
C22 H 320 4 M 360.492
Constit. of Baccharis incarum. Oil. [oc]i;' -22.8° (c, 0.55
in CHC1 3). C20 H 28 0 5 M 348.438
18-Carboxylic acid: [52482-96-9]. Marrubiagenin (ent-151;,)-form
C20 H 280 4 M 332.439 Constit. of Hoffmannia strigillosa.
Cryst. (MeOH aq.). Mp 184-185°. Jaensch, M. eta/, Phytochemistry, 1990, 29, 3587 (isol, pmr)
18-Carboxylic acid, P-n-glucopyranosyl ester: [51419-52-4].
Marrubiaside
C26 H 380 9 M 494.581
Isol. from Leonurus marrubiastrum. Cryst. (MeOH aq.).
Mp 149-150°.
(ent-5/l)-form
18-Carboxylic acid: Clerodermic acid
C20H 280 4 M 332.439
Constit. of Clerodendron inerme. Cryst. (CHC1 3/pet.
ether). Mp 161-162°. [oc]i7 -70° (c, 0.517 in CHC1 3).
Tschesche, R. eta/, Chern. Ber., 1973, 106, 2929 (Marrubiaside)

788
18-Hydroxy-3,13(16),14-clerodatrien-•.. - 17-Hydroxy-12,17-epoxystrictic acid Di-00766 - Di-00770

18-Hydroxy-3,13(16),14-clerodatrien-2- Dl-00766 4-Hydroxy-13-cleroden-15-oic acid Dl-00768

one COOH

ow~a'-I
(ent-4jl,8cxH,l3Z):form

1!9
CH20H
C~31.0z M 302.456 CzoH340 3 M 322.487
Ac: [124902-03-0]. 18-Acetoxy-3,13(16),14-clerodatrien-2- (ent-4fl,B~~oH,13Z)-form [120662-29-5]
one Constit. of Ageratina ixioc/adon.
CnH310 3 M 344.493 (ent-4f.,J3E)-form [72184-14-6] Kola11enolic acid
Constit. of Monodora brevipes. Oil. [cx] 0 -33° (c, 0.02 in Me ester: [72184-10-2].
CHC1 3). C11H 360 3 M 336.514
19-Hydroxy, di-Ac: 18,19-Diacetoxy-3,13(16),14- Constit. of Hardwickia pinnata. Cryst. (MeCN). Mp 95-
clerodatrien-2-one 960. [cx] 0 -45° (c, 0.87 in CHC1 3).
C14H 340 5 M 402.530 Misra, R. et al, Tetrahedron, 1979, 35, 979, 2301 (isol, struct, abs
Isol. from Casearia corymbosa. Oil. [cx] 0 +45° (c, 0.1 in conjig)
CHC1 3). Tanayo-Castillo, G. et al, Phytochemistry, 1989, 28, 139 (isol)
Etse, J.T. et al, Phytochemistry, 1989, 28, 2489 (isol, pmr, cmr)
Khan, M.R. et al, Phytochemistry, 1990, 29, 3591 (isol, pmr) 6-Hydroxy-13-cleroden-15,16-olid-18-oic Dl-00769
acid
2-Hydroxy-3-cleroden-15-oic acid Dl-00767

(ent-2cx,5jl,l Ocx,l3~}:form
HooC I
OH
CzoH300 5 M 350.454
Czoll340 3 M 322.487 (ent-4«H,6fl)-form
(ent-2«,5fl,l OII.,J3f.)-form Me ester, Ac: [82225-47-6]. Ajugarill IV
Epihydroxypopulifolic acid C13H 340 6 M 406.518
Constit. of Cistus populifolius. Oil (as Me ester). [cx] 0 Constit. of Ajuga remota. Shows insecticidal and
-66.6° (c, 0.77 in CHC1 3) (Me ester). antifeedant activity. Cryst. Mp ll9-120.5°. [cx] 0 -57.SO
Me ether: [68268-61-1]. fl-Methoxypopulifolic acid (c, 0.06 in CHC1 3).
CuH360 3 M 336.514 Kubo, I. et al, J. Chern. Soc., Chern. Commun., 1982, 618 (isol)
Constit. of C. popu/ifolius. Oil (as Me ester). [cx] 0 -39.4° Kende, A.S. et al, Tetrahedron Lett., 1982, 23, 1751 (synth)
(c, 1.02 in CHC1 3) (Me ester).
(ent-2fl,5«,1011.,13f.)-form 17-Hydroxy-12,17-epoxystrictic acid Dl-00770
2-Ketone: 2-0xo-3-cleroden-15-oic acid
Czoll310 3 M 320.471
Constit. of Aristo/ochia brasiliensis. Oil.
(ent-2fl,5fl,10«,13f.)-form
Hydroxypopulifolic acid
Constit. of C. popu/ifolius. Oil (as Me ester). [cx] 0 -20.8°
(c, 0.76 in CHC13) (Me ester).
Me ether: [68330-96-1]. «-Methoxypopulifolic acid 'OH
c;,H360 3 M 336.514
Constit. of C. populifo/ius. Oil (as Me ester). [cx] 0 +7.7°
(c, 1.1 in CHC1 3) (Me ester). COOH
2-Ketone: [67996-35-4]. Oxopopulifolic acid
CzoH140 5 M 344.407
CzoH310 3 M 320.471
Constit. of C. popu/ifolius. Oil (as Me ester). [cx] 0 -16.1° (12fl,l7«):form
(c, 2.3 in CHC1 3) (Me ester). Constit. of Conyza welwitschii.
(ent-2fl,5fl,l0fl,J3f.)-form Me ether:
C11 H 160 5 M 358.433
2-Ketone: Constit. of C. palhinhae. Oil (as Me ester). [ex]~
Constit. of C. welwitschii. Mp 144° (as acetate). [cx]t'
-3° (c, 0.56 in CHC1 3) (Me ester).
-151° (c, 0.44 in CHC1 3) (acetate).
De Pascual Teresa, J. et al, An. Quim., 1978, 74, 476 (isol)
(12fl,J7fl)-form
De Pascual Teresa, J. et al, Phytochemistry, 1983, 22, 2805 (isol)
Lopes, L.M.X. et al, Phytochemistry, 1987, 26, 2781 (cmr, isol) Constit. of C. welwitschii.
Me ether:
C11 H 160 5 M 358.433

789
2-Hydroxy-3-oxo-1,4(19)-clerodadien-... - Isopicropolin Di-00771 - Di-00776

Constit. of C. welwitschii. Mp 142° (as acetate). [1X]~4 16-Hydroxy-2-oxo-3,13-clerodadien-15, 16- Di-00774

-307° (c, 0.45 in CHC1 3) (acetate). olide
17-Ketone: Strictic acid 12p,17-olide
C20H 210 5 M 342.391 0
Constit. of C. welwitschii. Gum (as Me ester). [1X]i;'
-254° (c, 4.55 in CHC1 3) (Me ester). OH
Zdero, C. eta/, Phytochemistry, 1990, 29, 2247 (iso/, pmr)

2-Hydroxy-3-oxo-1,4(19)-clerodadien-15- Dl-00771
oic acid

COOH

C:wH 280 4 M 332.439

ent-form [126616-70-4]
2-0xo-3, 13-kolavadien-15, 16-olide
Constit. of Polyalthia viridis. Gum.
Ki.ijoa, A. eta/, Phytochemistry, 1990, 29, 653 (isol, pmr, cmr)
C:wH300 4 M 334.455
(ent-13~)-form
Constit. of Relhania squarosa. 7-Hydroxy-3-oxo-4(19)-cleroden-15-oic Di-00775
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol) acid

COOH
6-Hydroxy-7-oxo-3,13-clerodadien-15,16- Dl-00772
olide

C:wH320 4 M 336.470
(ent-7rz,13~)-form
Ac:
C21H 340 5 M 378.508
C:zoH28 0 4 M 332.439 Constit. of Relhania genistifolia.
(ent-6/1)-form [128232-69-9] Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol)
Constit. of Platychaete aucheri. Cryst. Mp 167°. [1X]i;'
+65° (c, 0.23 in CHC1 3).
6-Deoxy: [128232-68-8]. ent-7-0xo-3,13-clerodadien-15,16-
Isopicropolin Di-00776
ent-61X-Acetoxy-4P,J8:7,19:15,16-triepoxy-71X-hydroxy-
o/ide
C:zoH 280 3 M 316.439 13(16),14-clerodadien-20,12-olide
Isol. from P. aucheri. Cryst. Mp 128°. [1X]i;' +89° (c, 0.3 [27968-82-7]
in CHC1 3).
Rustaiyan, A. et a/, Phytochemistry, 1990, 29, 985 (isol, pmr)

7-Hydroxy-2-oxo-3,13-clerodadien-15,16- Di-00773
olide

6-Ac:
C:zoH280 4 M 332.439 C22 H 260 8 M 418.443
(ent-7/1)-form Constit. of Teucrium polium.
Ac: Lasianthin Brieskorn, C.H. eta/, Chern. Ber., 1967, 100, 1995 (synth)
Piozzi, F., Heterocycles, 1981, 15, 1489 (iso/, struct)
C22 H 30 0 5 M 374.476
Constit. of Salvia /asiantha. Cryst. (Me2COjhexane).
Mp 174-176°. [1X]i,D -93.46° (c, 0.49 in CHC1 3).
Sanchez, A.-A. et a/, Phytochemistry, 1987, Ui, 479 (isol, cryst
struct)

790
Isoteuflin- 7-0xo-3-cleroden-15-oic acid Di-00777 - Di-00784

Isoteuftin Dl-00777 20-0xo-3,13-clerodadien-16,15-olide Dl-00781

[54168-74-0]
0

C20 H 280 3 M 316.439

ent-form [77355-57-8] Rugosolide
Constit. of Solidago nemoralis. Gum. [a]i;' -74° (c, 0.9
in CHC1 3).
0
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2655.
C19H 200 5 M 328.364
Constit. of Teucrium canadense. Amorph. solid. Mp 70-
800. [a]~ + 121.7° (c, 1.37 in CHC1 3).
7-Oxo-3-clerodene-15, 16:18, 19-diolide Dl-00782
Bruno, M. eta/, Phytochemistry, 1989, 28, 3539 (isol, pmr, cmr) H
0
7-0xo-3,13-clerodadien-15-oic acid Dl-00778

COOH

C20 H 260 5 M 346.422

(ent-13/;J-form [63640-88-0]
Cons tit. of Baccharis genistelloides. Oil.
C20H 34p 3 M 318.455 Bohlmann, F. eta/, Phytochemistry, 1979, 18, 1011 (isol)
(ent-13£)-form [128232-67-7]
Constit. of Platychaete aucheri. 3-0xo-4(19)-cleroden-15-oic acid Di-00783
Rustaiyan, A. et a/, Phytochemistry, 1990, 29, 985 (isol, pmr)
COOH
12-0xo-3,13(16)-clerodadien-15-oic acid Dl-00779

COOH

C20H 320 3 M 320.471

(ent-13~)-form
Constit. of Relhania squarosa.
Tschritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol)
C20H 300 3 M 318.455
ent-form [129272-61-3] 7-0xo-3-cleroden-15-oic acid Di-00784
Constit. of Premna schimperi. Antibacterial. 7-0xo-13,14-dihydrokolavenic acid
Waterman, P.G., J. Nat. Prod. (Lloydia), 1990, 53, 13 (isol, pmr)
COOH
16-0xo-3,13-clerodadien-15-oic acid Di-00780
COOH

C20 H 3z03 M 320.471

Constit. of Pteronia paniculata. Gum.
6a-Hydroxy: [129350-05-6]. 6a-Hydroxy-7-oxo-3-cleroden-
15-oic acid. 6a-Hydroxy-7-oxo-13, 14-dihydrokolavenic
acid
C20H 300 3 M 318.455 C20H 320 4 M 336.470
(ent-13£)-form Constit. of P. paniculata. Cryst. Mp 159°.
Constit. of Polyalthia longifolia. Gum. [a]~ -70.58° (c, 6a-Angeloyloxy: [129350-06-7].
0.01 in MeOH). C25H 380 5 M 418.572
Phadnis, A.P. et a/, Phytochemistry, 1988, 27, 2899. Constit. of P. paniculata. Gum.
6a-(2-Methylpropanoyloxy): [129350-07-8].

791
16-0xo-3-cleroden-15-oic acid- Secoeeniolide Di-00785 - Di-00790

C24 H 38 0 5 M 406.561 Pteroneeniol Di-00788

Constit. of P. paniculata. Gum. [129349-91-3]
Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr)

16-0xo-3-cleroden-15-oic acid Di-00785

CHO
'OOC
CHO /)=I
C20H 320 3 M 320.471
C25H 340 6 M 430.540
(ent-13~)-form Constit. of Pteronia eenii. Gum. [rx.]~4 -22° (c, 0.81 in
16-0xo-3-kolaven-15-oic acid CHC1 3).
Constit. of Acritopappus teixeirae. Gum.
Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr)
Bohlmann, F. eta/, Phytochemistry, 1980, 19, 2695.

Salvifaricin Di-00789
Plaunol A Dl-00786 ent-JOPH-7fi,20: 12,20:15,16- Triepoxy-1 ,3,13( 16),14-
ent-12R,20: 15,16: 19,20S- Triepoxy-19S-hydroxy- clerodatetraen-18,19-olide
3,8( 17),13(16),14-clerodatetraen-18,6rx-olide
[87321-87 -7]
[697 49-09-3]
0
Q
'

0 C20 H 200 5 M 340.375

C20 H 20 0 6 M 356.374
Constit. of Croton sublyratus. Cryst. Mp 214-217°. [rx.]~
-61.7° (c, 1 in Me 2CO).
Kitazawa, E. et a/, Chern. Pharm. Bull., 1980, 28, 227.
Plaunol D
ent-15, 16:19,20-Diepoxy- 2rx,12R,20S-trihydroxy-
3 ,8( 17), 13( 16), 14-clerodatetraen-18 ,6rx-olide
[66302-50-9]
Constit. of Salvia farinacea. Cryst. (MeOH). Mp 213-215°.
[rx.]~ -155.2° (CHC1 3).
1fi,2fi-Epoxide: [87321-88-8]. ent-1rx.,2rx.:7 fi,20: 12,20:15,16-
Tetraepoxy- 3, 13(14)-clerodatrien-18, 19-olide. Salvifarin
C20H 200 6 M 356.374
Constit. of S. farinacea. Cryst. (MeOH). Mp 220-222°.
Dl-00787 [rx.]~ -4.3° (c, 0.93 in CHC1 3).
Savona, G. eta/, Phytochemistry, 1983, 22, 784 (isol)
Rodriguez, B. et a/, Phytochemistry, 1984, 23, 1193 (struct)
Savona, G. eta/, Phytochemistry, 1984, 43, 466 (cryst struct, deriv)

Secoeeniolide Di-00790
[129349-97-9]

0
C20H 220 7 M 374.390
Constit. of Croton sublyratus. Cryst. Mp 170-172°. [rx.]~
C20 H 260 6 M 362.422
-144° (c, 1 in Me 2CO).
Constit. of Pteronia eenii.
12-Ac: [69749-02-6]. Plaunol E
Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol. pmr)
C22 H 2..08 M 416.427
Constit. of C. sublyratus. Cryst. Mp 180-181°. [rx.]~
-142° (c, 1 in Me 2CO).
Kitazawa, E. eta/, Chern. Pharm. Bull., 1980, 28, 227.

792
4,8:12,20:15,16:19,20-Tetraepoxy-... - 15,16,17,19-Tetrahydroxy-3,13-.•• Di-00791 - Di-00795

4,8:12,20:15,16:19,20-Tetraepoxy- Oi-00791 2,19:4,18:11,16:15,16-Tetraepoxy-14- 01-00793

13(16),14-clerodadien-6-ol clerodene-1,6,19-triol

I
I
I
I

:o/
I

I 1

0
I 1

"\
I

C20Hu;05 M 346.422
(ent-4ft,6f/)-form
OH
Ac: [126818-02-8]. Teubutilin A
C22H 280 6 M 388.460 C20 H 280 7 M 380.437
Isol. from Teucrium abutiloides. Mp 187-190°. [at:]~ (ent-lr,.,2p,4p,6p,JJR,13R,l6R,l9S)-form
+6.9° (c, 0.45 in CHCI 3). 1-Tigloyl, 19-Ac: [129145-61-5]. Jodrellin T
6-Ketone: [63893-14-1]. ent-4fi,8: 12,20: 19,20-Tetraepoxy- C29H 380 10 M 546.613
13(16),14-clerodadien-6-one. Teucrin P 1 Constit. of Scute/laria galericulata.
C20H:z..05 M 344.407 14,15-Dihydro, 1-tigloyl, 19-Ac: [129145-60-4]. 14,15-
Constit. ofT. polium. Cryst. (Etz0/Me 2CO). Mp 164- DihydrojodreUin T
1660. [ot:Jn + 21.4° (c, 4.06 in CHC1 3). C29H400 10 M 548.629
Popa, D.P. eta/, Khim. Prir. Soedin., 1977, 49 (Teucrin P 1) Constit. of S. galericulata. [cx]i,D -24.4° (c, 0.15 in
Malakov, P. eta/, Z. Naturforsch., B, 1979, 34, 1570 (isol, Teucrin CHC1 3).
PI) 1-Deoxy: see 2,19:4,18: II ,16:15,16- Tetraepoxy-14-
Morita, M. eta/, J. Chern. Soc., Chern. Commun., 1986, 1087 clerodene-6, 19-diol, Di-00792
(cryst struct, Teucrin P 1)
Cole, M.D. eta/, Phytochemistry, 1990, 29, 1793 (iso/, pmr)
De La Torre, M.C. eta/, Phytochemistry, 1990, 29, 579 (Teubutilin
A)
7,15,16,19-Tetrahydroxy-3,13-clerodadien- Oi-00794
2,19:4,18:11,16:15,16-Tetraepoxy-14- 01-00792 18-oic acid
clerodene-6, 19-diol

CHzOH

C20 H 3z06 M 368.469

' '
'' (ent-7p,13Z)-form
' '
/ 0...- : I 18-+19 Lactone: ent-7fi,15,16-Trihydroxy-3,!3Z-
O : OH clerodadien-18,19-olide. Portulide C

~ OH
C2oH300s M 350.454
Constit. of Portulaca cv jewel. Cryst. Mp 191-192°.
[cxm.s -113° (c, 1.24 in MeOH).
C20 H 28 0 6 M 364.438 Ohsaki, A. et a/, Phytochemistry, 1986, 25, 2414.
(ent-2P,4P,6P,l1R,13R,l6R,l9S)-form
6,19-Di-Ac: Jodrellin A 15,16,17,19-Tetrahydroxy-3,13- 01-00795
C24 H 320 8 M 448.512 clerodadien-19-oic acid
Constit. of Scute/laria woronowii. Insect antifeedant. Oil.
19-(2-Methylpropanoy[), 6-Ac: Jodrellin B
C26H360 8 M 476.566
Constit. of S. woronowii. Insect antifeedant. Oil. [cx]i,D
-ll.4° (c, O.o7 in CHC1 3).
Anderson, J.C. eta/, Tetrahedron Lett., 1989, 30, 4737.

HOOC
C20H320 6 M 368.469
(ent-13Z)-form

793
3,4,8,8·Tetrahydroxy-11,13-... - Teumicropin Di-00796 - Di-00800

18-+19 Lactone: [93767-31-8]. ent-15,16,11-Trihydroxy- Teucroxide Dl-00798

3,13Z-clerodadien-18,19-olide. Portulide A. Portulide ent-4fl,J9:15,16-Diepoxy-2cx,6cx,18-trihydroxy-13(16),14-
C:zoll3C,Os M 350.454 clerodadien-20,1 2-o/ide
Constit. of Portulaca grandiflora. Amorph. [cx]~;'- 5 [87587-49-3]
-151.1 o (c, 0.068 in EtOH).
17-Aldehyde, 18-+ 19 Lactone: ent-15,16- Dihydroxy-11 -oxo-
3,13-c/erodadien-18,19-o/ide. Portulide D
C10Hu.Os M 346.422
Constit. of P. cv Jewel. Oil. (cx]i)1· 5 -147.9° (c, 0.83 in
MeOH).
Ohsa:Jci, A. et a/, Chern. Lett., 1984, 1521 (Portulide A)
Ohsaki, A. eta/, Phytochemistry, 1986, 25, 2414 (Portulide D)

3,4,6,8-Tetrahydroxy-11, 13-clerodad.ien- Dl-00796

15,16-olide
C10H 260 7
0
Constit. of Teucrium chamaedrys. Cryst. (EtOAc). Mp 183-
1840. (cx]i)1 -29.2° (c, 0.545 in Py).
2-Deoxy: [68670-83-7]. ent-4/1,19: 15,16-Diepoxy-6cx,l8-
dihydroxy-13(16),14-clerodadien-20,12-olide. Montanin D
C10H 260 6 M 362.422
Isol. from T. montanum. Cryst. (Et20/Me 2CO). Mp 159-
1610. [cx]i; -5.7° (c, 0.224 in CHC1 3).
Malakov, P.Y. eta/, Z. Naturforsch., B, 1978, 33, 1142 (Montanin
D)
Gacs-Baitz, E. et al, Heterocycles, 1982, 19, 539 (cmr)
Garcia-Alvarez, M.C. eta/, J. Org. Chern., 1983, 48, 5123
C10H 300 6 M 366.453 (Teucroxide)
(ent-3/1,4«.,6fl,8«.,11E)-form
0 6-Benzoyl: [112609-09-3]. Scuterivulactone D Teulepicephin Di-00799
C:17H340 7 M 470.561 ent-6cx,18: 15,16-D{epoxy-3cx,4fJ,6fJ,12-tetrahydroxy-
Constit of crude Chinese drug "Ban Zhi Lian" 13(16),14-clerodadien-20,19-olide
(Scutellaria rivularis). Needles (Me 2CO). Mp 260-262°. (107602-87-9]
[cx]i,6 +57.SO (MeOH).
Kizu, H. eta/, Chern. Pharm. Bull., 1987, 35, 1656.

4,6,18,19-Tetrahydroxy-13-cleroden-15,16- Dl-00797
olide

\
I
: I
C10H 260 8 M 394.421
HOH2C 1OH 1 Constit. of Teucrium lepicephalum. Amorph. powder.
HOCHzOH 3,12-Di-Ac: Cryst. (EtOAc). Mp 217-220°. [ex]:_: -63.7° (c,
C:zoll 320 6 M 368.469 0.157 in Py).
(ent-4fJOH, 6/l)-form Savona, G. eta/, Phytochemistry, 1986, 25, 2569.
6,19-Di-Ac: [62640-07-7]. Ajugarin 111
C24H 360 8 M 452.544 Teumicropin Di-00800
Isol. from Ajuga remota. Insect antifeedant. Cryst. Mp ent-4/1,18: 12,20:15,16:19,20- Tetraepoxy-13(16),14-
243-245°. clerodadiene-3cx,6cx-diol
Kubo, I. et a/, J. Chern. Soc., Chern. Commun., 1976, 949. [113476-87-2]

M 362.422

794
Teupestalin A - Teupyrin A Di-00801 - Di-00805

Constit. of Teucrium micropodioides. Cryst. Teupolin ill Di-00803

(EtOAcfhexane). Mp 195-198°. [IX]~ -22.9° (c, 0.088 in ent-12,20: 15,16:19,20- Triepoxy-4p,J8-dihydroxy-13(16),14-
Py). clerodadien-6-one
3-Ac: 3-Acetylteumicropin [85966-25-2]
C:zzH:zs07 M 404.459
From T. micropodioides. Cryst. (EtOAcfhexane). Mp
256-259°. [1X]i? +4.1° (c, 0.195 in CHC1 3).
6-Ketone: Deacetylteupyrenone
C20H 240 6 M 360.406
lsol. from T. micropodioides. Cryst. (EtOAc/hexane).
Mp 235-240°. [IX]~ + 1.6° (c, 0.183 in CHC1 3). H
6-Ketone, 3-Ac: [85564-03-0]. Teupyrenone
C:zzH260 7 M 402.443
lsol. from T. pyrenaicum. Cryst. (EtOAcfhexane). Mp
213-215°. [1X]~ -46_50 (c, 0.8 in CHC1 3).
Garcia-Alvarez, M.C. eta/, Phytochemistry, 1982, 21, 2559 C20 H 260 6 M 362.422
( Teupyrenone) Constit. of Teucrium po/ium. Cryst. (EtP/Me2CO). Mp
De La Torre, M.C. eta/, Phytochemistry, 1988, 27, 213 178-180°. [1X]i,B -57.1° (c, 0.154 in Me2CO).
(Deacetylteupyrenone, Teumicropin, Acetylteumicropin)
Malakov, P.Y. et a/, Phytochemistry, 1982, 21, 2597.

Teupestalin A Dl-00801
Teupolin V Di-00804
ent-61X,18: 12,20:15,16:19,20- Tetraepoxy-13(16),14-
clerodadiene-4P,6-diol
[89984-00-9]

C20H 240 8 M 392.405

Constit. of Teucrium pestalozzae. Cryst. (MeOH). Mp 207-
2090. [IX]~ -22.4° (c, 0.134 in CHC13fMeOH).
De La Torre, M.C. eta/, Phytochemistry, 1990, 29, 2223 (iso/, pmr, C 20 H 260 6 M 362.422
cmr, cryst struct) Constit. of Teucrium polium. Cryst. (MeOH/Etp). Mp
194-197°. [1X]i,B -24.4° (c, 0.164 in Me2CO).
Teupestalin B Dl-00802 Malakov, P.Y. eta/, Phytochemistry, 1983, 22, 2791.

Teupyrin A Di-00805
ent-31X,12S-Diacetoxy-4,18: 15,16: 19,20-triepoxy-20R-
hydroxy-13( 16), 14-clerodadien-6-one
[103839-72-1]

HO~

C21H 240 9 M 432.426

Constit. of Teucrium pestalozzae. Amorph. solid. Mp 90-
1000. [1X]i;' -69° (c, 0.042 in CHC1 3).
De La Torre, M.C. eta/, Phytochemistry, 1990, 29, 2223 (isol, pmr,
cmr) C24 H 300 9 M 462.496
Constit. of Teucrium pyrenaicum. Amorph. powder. Mp
78-90°. [1X]i? -204_50 (c, 0.202 in CHC1 3).
Fernandez, P. eta/, Phytochemistry, 1986, 25, 1405.

795
Teusalvin E- 4,18:12,20:15,16-Triepoxy-13(16),14-... Di-00806 - Di-00810

Teusalvin E 01-00806 Teuvincentin B Di-00808

ent-15,16-Epoxy-2rx.,6oc,12R,l8-tetrahydroxy-3,13(16),14- ent-20rx.-Acetoxy-4P,J8:7,19: 12,20: 15,16-tetraepoxy-
clerodatrien-20,19-olide 13( 16), 14-clerodadiene-6p, 7rx.-diol
[103994-17-8]

HOH2 C
C 20H 260 7 M 378.421 C22H230 8 M 420.458
Constit. of Teucrium salviastrum. Amorph. Mp 104-110°. Constit. of Teucrium polium. Cryst. (EtOAcjhexane). Mp
[rx.]~ -41° (c, 0.195 in MeOH). 194-197°. [rx.]~ -27.1° (c, 0.17 in CHC1 3).
2-Deoxy: [115404-86-9]. Teuhunifin B Carreiras, M.C. et a/, Phytochemistry, 1988, 28, 1453 (isol, cryst
C 20H 260 6 M 362.422 struct)
lsol. from T. lamiifolium and T. polium. Cryst.
(Me2COjpet. ether). Mp 207-209°. [rx.]~ -49.3° (c, 0.23 4,18:11,16:15,16-Triepoxy-7,14- Di-00809
in Me 2CO).
clerodadiene-2,3,6, 19-tetrol
2-Deoxy, 12-epimer(?): Teubotrin
C20H 260 6 M 362.422
lsol. from T. botrys. Amorph. Mp 110-114°. [rx.]ii
-39.4° (c, 0.241 in CHC1 3). 12-Config. not detd.
De La Torre, M.C. eta/, Phytochemistry, 1986, 25, 1397 (Teusalvin
E)
De La Torre, M.C. et a/, Phytochemistry, 1986, 25, 2385
(Teubotrin)
Malakov, P.Y. et a/, Phytochemistry, 1988, 27, 1141 (Teulamifin B)

Teusalvin F Di-00807
ent-2P,J9:15,16-Diepoxy-6rx.,18-dihydroxy-3,13(16),14-
clerodatrien-20,12-olide C20H 280 7 M 380.437
[103994-16-7] (ent-1P,31X,4P,6P,ll R,16R)-form
3-(2-Acetoxy-2-methylbutanoyl), 6,19-di-Ac: [35481-70-0].
Clerodendrin A
C31H42012 M 606.666
Bitter principle from Clerodendron tricotomum. Insect
antifeedant. Prisms (Et 20). Mp 164-165°. [rx.] 0 +7.4° (c,
3.25 in CHC1 3).
Kato, N. eta/, J. Chern. Soc., Perkin Trans. I, 1973, 712.
'o Kato, N. eta/, J. Chern. Soc., Perkin Trans. 2, 1973, 69 (cryst
~\ struct)
\l
HOCH2 OH
4,18:12,20:15,16-Triepoxy-13(16),14- Di-00810
C20H 240 6 M 360.406 clerodadiene-3,6,19,20-tetrol
Constit. of Teucrium salviastrum. Cryst. (MeOH). Mp 216-
2190. [rx.]i,l +89.9° (c, 0.149 in CHC1 3).
De La Torre, M.C. eta/, Phytochemistry, 1986, 25, 1397 (cryst
struct)

C20 H 280 7 M 380.437

(ent-11X,4p,6p,l2PH,20fl)-form
Tetra-Ac: [85564-01-8]. Teupyreinidin
C28H 360 11 M 548.586

796
4,18:12,20:15,16-Triepoxy-13(16),14-... - 4,18:11,16:15,16-Triepoxy-3,6,15,19-... Di-00811 - Di-00814

Constit. of Teucriurn pyrenaicurn. Amorph. powder. Mp 4,18:11,16:15,16-Triepoxy-2,3,6,15,19- Di-00812

102-108°. [1X]~ +26.7° (c, 0.415 in CHC1 3). clerodanepentol
(ent-4P,6r~.,12PH,20fl)-form
3-Ketone, 19-Ac: [92356-83-7]. ent-19-Acetoxy- OH
4, 18:12,20:15,16- triepoxy-6fi,20fi-dihydroxy-3(16), 14-
clerodadien-3-one. Teujlavin
C22H:uPs M 420.458
lsol. from T. jlavurn. Cryst. (EtOAcjhexane). Mp 197-
2000. [IX]!; +5.2° (c, 0.3 in Py).
3,20-Diketone, 19-Ac: 20-0xoteuflavin
C22H260 8 M 418.443
Constit. of T. pestalozzae. Amorph. solid. [1X]i,3 + 51.2°
(c, 0.187 in CHC1 3). Strictly speaking a 20-1actone.
3,6,20-Triketone, 19-Ac: 41X,18:15,16-Diepoxy-19-acetoxy-
3,6-dioxo-13(16), 14-clerodadien-20, 12-olide. 4,8-
Epoxytafricanin A C20 H 320 8 M 400.468
C22H240 8 M 416.427
(ent-2P,3r~.,4p,6p,JJR,l3R,l5~,16S)-form
lsol. from T. pestalozzae. Cryst. (EtOAcjhexane). Mp
206-208°. [1X]i,3 + 109.6° (c, 0.135 in CHC1 3). 3-(3-Acetoxy-2-rnethylbutanoyl), 6,19-di-Ac: [I 09792-19-0].
Chamaepitin
Garcia-Alvarez, M.C. et a/, Phytochemistry, 1982, 21, 2559 (iso/)
Savona, G. eta/, Phytochemistry, 1984, 23, 843 (Teu.fiavin) C31 H.u,013 M 626.697
Pascual, C. eta/, Phytochemistry, 1986, 25, 715 (struct, Teu.fiavin) Constit. of Ajuga charnaepitys. Amorph.
De La Torre, M. eta/, Phytochemistry, 1990, 29, 988 (derivs) Camps, F. et a/, Phytochemistry, 1987, 26, 1475.

4,18:12,20:15,16-Triepoxy-13(16), 14- Dl-00811 4,18:11,16:15,16-Triepoxy-1,3,6,19- Di-00813

clerodadiene-6,19,20-triol clerodanetetrol

OH

:
''
''
CI:I20H
C20 H 3p 7 M 384.469
CloH 280 6 M 364.438
(ent-lr~.,3r~.,4p,6p,JJR,l3R,l6R)-form
(ent-4P,6P,12PH,20S)-form
1-(2S-Methylbutanoyl), 6,19-di-Ac: [72160-84-0].
Tri-Ac: [126818-03-9]. Teubutilin B
Ajugareptansin
C26H 340 9 M 490.549
C29H440 10 M 552.661
Constit. of Teucriurn abutiloides. Cryst. (EtOAcjhexane).
Constit. of Ajuga reptans. Amorph. [1X]i? -28° (c, 8.30
Mp 186-187°. [1X]i? -34.4° (c, 0.614 in CHCI3).
in CC14 ).
(ent-4P,l2PH,20~)-form
Camps, F. eta/, Tetrahedron Lett., 1979, 1709 (cryst struct, abs
6-Ketone, 19,20-di-Ac: [70544-92-2). Gnaphalidin conjig)
C24 H 31,08 M 446.496
Isol. from T. gnaphaloides. Cryst. Mp 132°. [1X)i? - 36.SO
(c, 0.14 in CHCI 3). 4,18:11,16:15,16-Triepoxy-3,6,15,19- Di-00814
Savona, G. et al, Tetrahedron Lett., 1979, 379 (Gnaphalidin)
clerodanetetrol
De La Torre, M.C. et a/, Phytochemistry, 1990, 29, 579 (Teubutilin OH
B)

C20 H 3p 8 M 400.468
(ent-3p,4p,6p,JJR,13R,15~,16S)-form

797
4,18:11,16:15,16-Triepoxy-3,6,19-... - 4,18:11,16:15,16-Triepoxy-14-... Di-00815 - Di-00818

3,6,19- Tri-Ac: [53777-57-4]. Caryoptin hemiacetal C24H 340 7 M 434.528

C26H 380 10 M 510.580
Isol. from Caryopteris divaricata. Antifeeding agent.
Cryst. (EtOAcjpet. ether). Mp 188-189°.
Hosozawa, S. eta/, Agric. Bioi. Chern., 1974, 38, 823.
4,18:11,16:15,16-Triepoxy-3,6, 19-
clerodanetriol
Constit. of leaves of Clerodendron infortunatum.
Possesses anthelmintic properties. Cryst. Mp 161-162°.
[1X]i? -37.6° (EtOH).
Barton, D.H.R. eta/, J. Chern. Soc., 1961, 5061 (struct)
Sim, G. et a/, J. Chern. Soc., 1962, 4133 (struct)
Rogers, D. eta/, J. Chern. Soc., Chern. Commun., 1979, 97 (abs
Di-00815 conjig)
Morita, M. eta/, Tetrahedron Lett., 1983, 24, 5631 (ord, cd)

4,18:11,16:15,16-Triepoxy-14-clerodene- Di-00818
H 2,3,6,19-tetrol

I
I
I
I
/ (ent-2a,3a,4~,6~,llR,I3R,16R)-:form
HOH2 C
C2oH320 6 M 368.469 I
I
I I
(ent-3«.,4P,6P,llR,l3R,l6R)-form : OH
3-(2-Methylbutanoyl), 6,19-di-Ac: [79495-90-2]. /vain II CH20H
C28H 42 0 9 M 522.634 C20 H 300 7 M 382.453
Isol. from A. iva. Cryst. Mp 158-161°. [1X]n -26.8° (c,
(ent-2«.,3«.,4P,6P,llR,l3R,l6R)-form
6.2 in CHC1 3).
14,15-Dihydro, 3-(2-methylpropanoyl), 6,19-di-Ac: [79568-
Camps, F. et a/, Chern. Lett., 1982, 1053.
28-8]. /vain I
C28 H 420 10 M 538.634
12,17:15,16:17,20-Triepoxy-3,13(16),14- Di-00816 Isol. from Ajuga iva. Amorph. [1X]n -8.0° (c, 8.0 in
clerodatrien-18,19-olide CHC1 3).

Co
14,15-Dihydro, 3-(2-methylbutanoyl), 6,19-di-Ac: [79495-88-
8]. /vain IV
C29 H440 10 M 552.661
I
Isol. from A. iva. Amorph. [1Xln + 4.1° (c, 4.2 in CHC1 3).

~
14,15-Dihydro, 15-ethoxy, 3-(2-methylpropanoyl), 6,19-di-
Ac: [79495-89-9]. /vain Ill
C30 H 460 11 M 582.687
Isol. from/. iva. Amorph. [1X]n +31.7° (c, 4.6 in CHC1 3).
(ent-2P,3«,4P,6P,II R,13R,l6R)-form
0 0) 3-(2-Methylpropanoyl), 6,19-di-Ac: Ajugachin A
C20H 220 5 M 342.391 C28 H..o010 M 536.618
Constit. of A. chamaepitys. Cryst. (Et20jpet. ether). Mp
(ent-12«.H)-form [66563-30-2] Bacchotricuneatin C
Constit. of Baccharis tricuneata. Cryst. (CH 2Cl 2jEtOH). 178-181°. [1X]~ -50.7° (c, 0.946 in CHC1 3).
Mp 188-190°. 3-(2-Methylbutanoyl), 6,19-di-Ac: [87441-78-9]. Ajugapitin
C29 H 4P 10 M 550.645
Wagner, H. eta/, J. Org. Chern., 1978, 43, 3339.
Constit. of A. chamaepitys. Cryst. (Etpjhexane). Mp
196-198°. [1X]i,O -70.3° (c, 0.26 in CHC1 3).
4,18:11,16:15,16-Triepoxy-14-clerodene- Dl-00817 3-(3-Acetoxy-2-methylbutanoyl), 6,19-di-Ac: Ajugachin B
6,19-diol CJtH440u M 608.681
Constit. of A. chamaepitys. Cryst. (Etpjpet. ether). Mp
207-209°. [1X]~ -66° (c, 0.288 in CHC1 3).
14,15-Dihydro, 3-(2-methylbutanoyl), 6,19-di-Ac:
Dihydroajugapitin
C2,H440 10 M 552.661
Constit. of A. chamaepitys. Cryst. (EtOAcjEtp). Mp
212-2J40. [1X]i,O -40° (c, 0.25 in CHC1 3).
3-Tigloyl, 6,19-di-Ac: [129145-62-6]. Galericulin
C29H 400 10 M 548.629
Isol. from Scutellaria galericulata.
Camps, F. eta/, Chern. Lett., 1982, 1053 (Ivains)
Hernandez, A. eta/, Phytochemistry, 1982, 21, 2909 (Ajugapitin)
C20H 300 5 M 350.454 Cole, M.D. eta/, Phytochemistry, 1990, 29, 1793 (Galericulin)
Accepted abs. config. was reversed in 1979. Boneva, I.M. eta/, Phytochemistry, 1990, 29, 2931 (Ajugachins)
(ent-4p,6p,JJR,l3R,l6R)-form
Di-Ac: [464-71-1]. Clerodin

798
4,18:11,16:15,16-Triepoxy-14-.•. - 4,18:12,20:15,16-Triepoxy-6,19,20-... Di-00819- Di-00822

4,18:11,16:15,16-Triepoxy-14-clerodene- 01-00819 4,18:7,20:15,16-Triepoxy-12,19,20- Dl-00821

3,6,19-triol trihydroxy-13(16),14-clerodadien-6-one
0
lj

/ (ent-3a,4~,6~, 11R, 13R, 16R)-form

I
I
I I
: OH
CHzOH
C20H3e,06 M 366.453 C20 H 260 7 M 378.421
(ent-3rx.,4P,6P,JJR,l3R,l6R)-form (ent-4P,7P,12R,20rx. )-form
Tri-Ac: [53060-58-5]. 3-Epicaryoptin. 3-epi-Caryoptin 12,19-Di-Ac: [77984-53-3]. Auropolin
C26H 360 9 M 492.565 C24H 300 9 M 462.496
Constit. of Clerodendron ca/amitosum. Cryst. Mp 171- Constit. of Teucrium polium. Cryst. (EtOAc/EtOH). Mp
1720. [a:Jn -70° (c, l in CHC1 3). 170-172°. [a:]~0 +26.0° (c, 0.33 in CHC1 3).
(ent-3P,4P,6P,JIR,13R,l6R)-form Tri-Ac: Cryst. (EtOAc/hexane). Mp 186°. [a:]l; +63.6° (c,
6,19-Di-Ac: [53683-47-9]. Caryoptinol 0.23 in CHC1 3).
C24H 340 8 M 450.528 Eguren, L. et al, J. Org. Chern., 1981, 46, 3364 (isol)
Constit. of Caryopteris divaricata. Cryst. Mp 219-220°. Camps, F. et al, Phytochemistry, 1987, 26, 1475 (cryst struct)
[1X]n -83° (c, 0.33 in CHC1 3).
Tri-Ac: [50645-63-1]. Caryoptin 4,18:12,20:15,16-Triepoxy-6,19,20- Dl-00822
C 26H 360 9 M 492.565 trihydroxy-13(16),14-clerodadien-7 -one
Isol. from Caryopteris divaricata. Antifeeding agent.
Cryst. Mp 176-177°. [1X]n -91° (c, 1.1 in CHC1 3). 0
Hosozawa, S. et al, Phytochemistry, 1974, 13, 1019 (Caryoptinol) j
Harada, N. et al, J. Am. Chern. Soc., 1978, 100, 8022 (isol)
Morita, M. et al, Tetrahedron Lett., 1983, 24, 5631 (ord, cd)

3,4:8,12:15,16-Triepoxy-1 0-hydroxy- Dl-00820

13(16),14-clerodadien-20,1-olide
[129349-92-4] I 0
I I

0 : OH
CH2 0H
~ !J
C20H 260 7 M 378.421
(ent-4p,6p,8rx.H,12PH,20rx. )-form
19,20-Di-Ac: [92631-95-3]. Isoeriocephalin
C24H 300 9 M 462.496
Constit. of Teucrium lanigerum. Cryst. (Me 2CO /EtzO).
0' Mp 232-234°. [a:Ji? -33.1° (c, 0.738 in CHC1 3).
(ent-4P,6P,BPH,l2PH,20rx. )-form
C20H 240 6 M 360.406
Tri-Ac: Teuvincentin C
(Jp,Jrx.,4rx.,8p,JOp)-form
C26H 320 10 M 504.533
Constit. of Pteronia incana. Gum. [a:]~4 + 52° (c, 0.2 in Constit. ofT. polium. Cryst. (EtOAc). Mp 220-225°.
CHC1 3). [a:]~2 -8.1° (c, 0.246 in CHC1 3).
Zdero, C. et at, Phytochemistry, 1990, 29, 1231 (isol, pmr)
Femandez-Gadea, F. et al, Phytochemistry, 1984, 23, 1113
(Isoeriocephalin)
Carreiras, M.C. et al, Phytochemistry, 1989, 28, 1453 (Teuvincentin
C)

799
4,18:12,20:15,16-Triepoxy-7,19,20-... - 6,15,17-Trihydroxy-3-cleroden-18-... Di-00823 - Di-00828

4,18:12,20:15,16-Triepoxy-7,19,20- Di-00823 CzzH310 6 M 392.491

trihydroxy-13(16),14-clerodadien-6-one Constit. of Conzya blinii. Needles (Me2CO). Mp 111-
1120. [IX]J;! -81.2° (c, 0.5 in MeOH).
0 Yang, C.-R. eta/, Phytochemistry, 1989, 28, 3131 (isol, pmr, cmr)
lj
7,18,19-Trihydroxy-3,13-clerodadien- Di-00826
16,15-olide
0

I 'OH
:o
I

CH20H
C20H 260 7 M 378.421 CH20H OH
(ent-4p,7p,J2PH,8«)-form CHzOH
19-Ac: 20-Deacetyleriocep/udin
C22H 280 8 M 420.458 C20H 300 5 M 350.454
Constit. of Teucrium lanigerum. Amorph. Mp 104-111°. (ent-7«)-form
[IX]~ + 118.9° (c, 0.582 in CHC1 3). Constit. of Salvia melissodora. Cryst.
19,20-Di-Ac: [71774-90-8]. Eriocepludin (CH 2Cl2/diisopropyl ether). Mp 149-150°. [IX]~ -53.75°
C24H 300 9 M 462.496 (c, 0.16 in CHC1 3).
Constit. ofT. eriocephalum. Cryst. (EtOAcjpet. ether). Esquivel, B. eta/, Phytochemistry, 1989, 28, 561.
Mp 197-200°. [IX]~ + 76.1° (c, 0.26 in CHC1 3).
Fayos, J. eta/, J. Org. Chern., 1979, 44, 4992. 2,3,4-Trihydroxy-13-cleroden-15-oic acid Di-00827
Femandez-Gadea, F. eta/, Phytochemistry, 1984, 23, 1113 (iso/)
Hueso-Rodriguez, J.A. eta/, Phytochemistry, 1986, 25, 175 (iso/) r" COOH

15,16,19-Trihydroxy-3,13-clerodadien-18- Di-00824
oic acid

HO~

HO \
C20H 340 5 M 354.486
(ent-2P,3P,4«,13Z)-form [97165-43~0] Tucumanoic acid
Constit. of Baccharis tucumanensis. Cryst. (as Me ester).
Mp 190-191° (Me ester). [IX]~ -5.6° (c, 0.48 in MeOH)
Cwli310 5 M 352.470 (Me ester).
(ent-13Z)-form 13(',,14-Dihydro: ent-2P,3P,41X- Trihydroxy-15-clerodanoic
18-+19 Lactone: 15,16-Dihydroxy-3,13-clerodadien-18,19- acid. Dihydrotucumanoic acid
o/ide. Portulilk B C10H 360 5 M 356.501
C20H 300 4 M 334.455 From B. pedicellata and B. marginalis. Cryst. (Me2CO).
Constit. of Portulaca cv jewel. Oil. [1X]i,2· 5 -110.9° (c, Mp 190-191°. [1X]ii -16.0° (c, 0.1 in MeOH).
1.89 in MeOH). Rossomando, P.C. eta/, Phytochemistry, 1985, 24, 787 (isol, struct)
Ohsaki, A. eta/, Phytochemistry, 1986, 25, 2414. Fiani, F. eta/, Phytochemistry, 1987, 26, 3281 (deriv)

2,18,19-Trihydroxy-3,13-clerodadien- Dl-00825 6,15,17-Trihydroxy-3-cleroden-18-oic acid Di-00828

15,16-olide
0

I I
HOOC OH
C20H 340 5 M 354.486
(ent-6ft,l3~)-form
18 -+6 Lactone: ent -15, 17-Dihydroxy-3-cleroden-!8,6P-olide.
~
19 I Gochnatol
CH20H 18-+6 Lactone, 17-Ac:
HOH2C C22 H 340 5 M 378.508
C20H 300 5 M 350.454 Constit. of Gochnatia paniculata. Gum. [1X]~4 -45° (c,
0.13 in CHCI 3).
(ent-2«)-form
15-Carboxylic acid, 18-+6 lactone: ent-11-Hydroxy-3-
19-Ac: [125675-09-4]. Blinin
cleroden-18,6-olid-15-oic acid. Gochnatoic acid

800
2,15,16-Trihydroxy-13-cleroden-3-... - 19-Acetoxyseconidoresedaic acid Di-00829 - Di-00833

15-Carboxy/ic acid, 18-+6 lactone, 17-phenylacetyl: Constit. of Z. guidonia. Amorph. [1X] 0 + 79° (c, 0.48 in
C 28H 360 6 M 468.589 CHC1 3).
Constit. of G. paniculata. Gum ( as Me ester). [1X] 0 -10° 2P-Hydroxy, 6P-cinnamoyloxy: [128572-38-3]. 6P-
(c, 0.18 in CHC1 3) (Me ester). Cinnamoyloxy-2p-hydroxyzuelanin
Bohlmann, F. eta/, Phytochemistry, 1983, 22, 191. C33H400 8 M 564.674
Constit. of Z. guidonia. Oil. [1X] 0 + 59° (c, 0.11 in
2,15,16-Trihydroxy-13-cleroden-3-one Dl-00829 CHC1 3).
A 13 (1 6l-Jsomer, 2P-acetoxy, 6P-cinnamoyloxy: [128486-33-9].
CH20H 2P-Acetoxy-6p-cinnamoyloxyisozuelanin
C35 H 420 9 M 606.711
Constit. of Z. guidonia. Oil. [1X] 0 + 50° (c, 0.04 in
(ent-2~,13Z)-form CHC1 3).
Khan, M.R. eta/, Phytochemistry, 1990, 29, 1609 (isol. pmr, cmr)
0

C20H 340 4 M 338.486

(ent-2P,13Z)-form
Constit. of Baccharis bo/iviensis. Oil (as tri-Ac). [IX]~
+ 32° (c, 0.31 in CHC1 3)(tri-Ac). Nor-, seco- and
Zdero, C. eta/, Phytochemistry, 1989, 28, 531.

Vittragraciliolide Dl-00830
abeoclerodanes
ent-121X,201X: 15,16-Diepoxy-3,13( 16),14-c/erodatriene-
17,20:18,19-dio/ide
[114703-26-3]
(4-+ 2)-Abeo-16-hydroxy-3-oxo-2,13- Di-00832
clerodadien-15,16-olide
0

OH

C20 H 200 6 M 356.374

Constit. of Vittadinia gracilis. Cryst. Mp 221°. C20 H 280 4 M 332.439
Zdero, C. et a/, Phytochemistry, 1988, 27, 2251. (ent-16(,)-form
(4-+ 2)- Abeo-3-oxo- 2, 13-kolavadien-15, 16-o/ide
Constit. of Polyalthia viridis. Gum.
Zuelanin Di-00831
[126582-62-5, 126720-74-9]
[128486-52-2]
Kijjoa, A. eta/, Phytochemistry, 1990, 29, 653 (isol, pmr, cmr)

l3 16
19-Acetoxyseconidoresedaic acid Di-00833
ent-19-Acetoxy-15,16-epoxy-5,10-seco-1 ,3,5(19)Z,J3(16),14-
c/erodapentaen-18-oic acid
[88378-98-7]

C24H 340 5 M 402.530 COOH

Parent compd. not known.
C22H 280 5 M 372.460
6P-Hydroxy, 21X-cinnamoyloxy: [128486-32-8]. 2«-
Constit. of Conyza scabrida.
Cinnamoyloxy-6p.hydroxyzuelanin
C33H400a M 564.674 Bohlmann, F. eta/, Justus Liebigs Ann. Chern., 1983, 2008.
Constit. of Zuelania guidonia. Amorph. [1X] 0 +83.0° (c,
0.12 in CHC1 3).
2rx-Hydroxy, 6P-cinnamoyloxy: [128486-31-7]. 6P-
Cinnamoyloxy-2r~.-hydroxyzue/anin
C33H 400 8 M 564.674

801
Aparisthman- 14,15-Dinor-13-oxo-3-cleroden-18-... Di-00834 - Di-00839

Aparisthman 01-00834 8,12:15,16-Diepoxy-2-hydroxy-19-nor-

[103827-26-5] 13(16),14-clerodadien-17,6-olid-18-oic
acid 01-00837

0
Ho,_ ./"'--..¥L)o

C21 H 280 5
MeOOC
M 360.449
Ct9Hzz0 7
~~0
H
HOOC
M 362.379
1 '(r
Constit. of Aparisthmium cordatum. Cryst.
(EtOAcjhexane). Mp 140-142°. [IX]~ -80.8° (c, 1 in (21X,4PH,5P,6tT.,8P,l2Pll)-form [20086-07-1] Diosbulbin C
CHC1 3). Constit. of Dioscorea bulbifera. Cryst. (Me2CO). Mp
Muller, A.H. et al, Phytochemistry, 1986, 25, 1415. 247-250° dec. [IX]~ +64.7° (c, 0.35 in Py).
Me ester: [20086-05-9]. Diosbulbin A
C20 H 240 7 M 376.405
Baccharascoparone 01-00835
Constit. of D. bulbifera. Cryst. Mp 265° dec.
15,16-Epoxy-12~-hydroxy-17-nor-7-oxo-3,13(16),14-
clerodatrien-18, 19-olide Kawasaki, T. et al, Chern. Pharm. Bull., 1968, 16, 2430 (isol)
Kamiya, K. et al, Tetrahedron Lett., 1972, 1869 (cryst struct)
OH Komori, T. et al, Chern. Pharm. Bull., 1977, 25, 1701 (abs config)

6,7-Dihydroxy-13,14,15,16-tetranor-3- 01-00838
cleroden-12-oic acid

C 19H 22 0 5 M 330.380
Constit. of Baccharis scoparia. Oil. [1X]~4 -50° (c, 0.3 in
CHC1 3).
Bohlmann, F. et al, Phytochemistry, 1985, 24, 511. Ct6Hu;04 M 282.379
(ent-6p,71X)-form [100324-77-4] 6,7-Dihydroxynorkolavenic acid
Crotocaudin . 01-00836 Constit. of Chromolaena laevigata. Oil.
ent-15,16-Epoxy-19-nor-4,11 ,13(16),14-clerodatetraene- Misra, L.N. et al, Tetrahedron, 1985, 41, 5353.
18,61X:20,12-diolide
[66275-07-?J 14,15-Dinor-13-oxo-3-cleroden-18-oic acid Oi-00839

dY
0

HOOC I

C 18H 280 3 M 292.417

ent-form [72184-13-5] Kolavonic acid
C19H 300 3 M 306.444
Constit. of Hardwickia pinnata. Oil (as Me ester). Bp0 _002
C 19H 180 5 M 326.348 125-135° (Me ester). [1X]i; -114.6° (c, 0.71 in CHC1 3)
Minor consiit. of Croton caudatus. Cryst. (CHC1 3jpet. (Me ester).
ether). Mp 199-200° dec. [1X]i,S -65° (c, 0.084 in CHC1 3). Misra, R. et al, Tetrahedron, 1979, 35, 979, 2301 (isol, struct, abs
6,10-Diepimer: [66322-19-8]. lsocrotocaudin config)
C 19H 180 5 M 326.348
Isol. from C. caudatus stem bark. Cryst. (CHC1 3 jpet.
ether). Mp 212°. [IX]~ + 152° (c, 0.11 in CHC1 3).
Chatterjee, A. et al, Tetrahedron, 1977, 33, 2407 (Crotocaudin)
Chatterjee, A. et al, Phytochemistry, 1978, 17, 1777
(lsocrotocaudin)

802
Diosbulbin B- 15,16-Epoxy-2-hydroxy-19-nor-6-oxo-... Di-00840 - Di-00845

Diosbulbin B Dl-00840 15,16-Epoxy-2-hydroxy-19-nor-13(16),14- Dl-00843

8P,I2rx: 15,16-Diepoxy-19-nor-13(16),14-clerodadiene- clerodadiene-17 ,12:18,6-diolide
17,6P: 18,2rx-diolide
[20086-06-0]

0
o-~;o
);~; ~=tion
Ct 9H 200 6 M 344.363 Ct,H 220 6 M 346.379
Constit. of Dioscorea bulbifera. Cryst. (Me 2CO). Mp 285° (21Y.,4pH,5P,61Y.,l2«H)-form [67567-15-1] Diosbulbin G
dec. [rx]~0 +92° (c, 0.75 in Py). Constit. of Dioscorea bulbifera. Cryst. (MeOH). Mp
Kawasaki, T. eta/, Chern. Pharm. Bull., 1968, 16, 2430 (isol)
215-217°. [rxln -36° (c, 0.26 in MeOH).
Komori, T. eta/, Justus Liebigs Ann. Chern., 1973, 978 (struct) Ida, Y. eta/, Justus Liebigs Ann. Chern., 1978, 818, 834 (isol, cryst
Komori, T. et a/, Chern. Pharm. Bull., 1977, 25, 1701 (abs corifig) struct)

Diosbulbinoside F Di-00841 15,16-Epoxy-6-hydroxy-19-nor-

[66756-58-9] 4,13(16),14-clerodatrien-17,12-olid-18-
oic acid Dl-00844

I
MeOOC
C 21;H340u M 538.547 .
Constit. of Dioscorea bulbifera. Cryst. (MeOH). Mp 193- Ct9H 220 6 M 346.379
1950 dec. [rx] 50 -25° (c, 0.3 in MeOH). (61Y.,l2«H)-form
Ida, Y. et a/, Chern. Pharm. Bull., 1978, 26, 435. 0-P-D-Glucopyranoside, Me ester:
C26H 340 11 M 522.548
15,16-Epoxy-6,18-dihydroxy-19-nor- Di-00842 Constit. of Tinospora cordifolia. Cryst. Mp 199-201°.
4,13(16),14-clerodatrien-20,12-olide [rx]i,O +23.8° (c, 3.14 in MeOH).
Bhatt, R.K. eta/, Phytochemistry, 1989, 28, 2419.

15,16-Epoxy-2-hydroxy-19-nor-6-oxo-
13(16),14-clerodadien-17,12-olid-18-oic
acid Dl-00845

C19H 140 5
(ent-6P,12PH)-form [68370-48-9] Montanin B 0
Constit. of Teucrium montanum. Cryst. Mp 164-165°.
[rxJn + 79° (MeOH).
,Ho
6-0-(2-Acetyl-P-D-glucopyranoside), 18-Ac: [92356-82-6]. HOOC
Teujlavoside Ct,H220 7 M 362.379
C 19H 380u M 578.612 (21Y.,4PH,5 p,l21Y.H)-form [66835-37 -8]
From T.flavum. Cryst. (Hp). Mp 100-102°. [rxh +25°
(c, 3 in Py). Me ester: Diosbulbin F
C20H 140 7 M 376.405
Ma1akov, P.Y. eta/, Tetrahedron Lett., 1978, 2025 (isol)
Constit. of Dioscorea bulbifera. Cryst. (MeOH). Mp
Gacz-Baitz, E. eta/, Heterocycles, 1982, 19, 539 (cmr)
Savona, G. eta/, Phytochemistry, 1984, 23, 843 (Teujlavoside) 211-212°. [rxln +31° (c, 0.19 in MeOH).
Butyl ester: [67567-13-9]. Diosbulbin H
C23 H 300 7 M 418.486

803
15,16-Epoxy-4-hydroxy-18-nor-1-oxo-... - 15,16-Epoxy-19-nor-3,13(16),14-... Di-00846 - Di-00848

lsol. from D. bulbi/era. Cryst. (MeOH). Mp 176-178°. 15,16-Epoxy-19-nor-3,13(16),14- Dl-00848

[aln + 59° (c, 0.24 in MeOH). clerodatriene-18,6:20,12-diolide
Ida, Y. et a/, Justus Liebigs Ann. Chern., 1978, 818.

15,16-Epoxy-4-hydroxy-18-nor-1-oxo- Dl-00846
2,13(16), 14-clerodatrien-17,12-olide
0
(ent-6a.,8a.H, lOa.H, 12~H)-form

0 0
CI,Hw0 5 M 328.364
I (ent-6«.,8«.H,JO«.H,12PH)-form [72541-00-5] Teujlin
OH Isol. from Teucrium .flavum. Needles (EtOAcjpet. ether).
~ 19 H 22 0~ M 330.380 Mp 153°. [aJn + 12° (c, 0.2 in CHC1 3).
(4«.,5«.,8PH,12«.H)-form 2P-Hydroxy: ent-15,16-Epoxy-2a-hydroxy-19-nor-
4-0-P-n-G/ucopyranoside: [120 163-16-8]. Tinosporaside 3, 13(16), 14-c/erodatriene-18,6:20, 12-dio/ide. 2P-
C 25 H 320 10 M 492.522 Hydroxyteucvidin
Cons tit. of Tinospora cordifo/ia. [aln + 65° (c, 1 in C19H 200 6 M 344.363
MeOH). Constit. of T. webbianum. Cryst. (EtOAcjhexane). Mp
201-203°. [ali? -10.3° (c, 0.136 in CHC1 3).
Khan, M.A. et a/, Phytochemistry, 1989, 28, 273.
(ent-6«.,8«-H,l OpH,l2PH)-form [53625-15-3] Teucvidin
Found in T. viscidum. Cryst. (MeOH). Mp 214°. [a]~
15,16-Epoxy-19-nor-4,6,13(16),14- Di-00847 -70° (c, 0.23 in CHC1 3).
clerodatetraene-18,6:20,12-diolide (ent-6«.,8PH,JO«.H,12PH)-form [75443-75-3] Teuchamaedryn A
IsoL from aerial parts of T. chamaedrys. Prisms
(Et 20jdiisopropyl ether). Mp 159-160°. [ali? +25°.
(ent-6P,8«.H,l Orx.H,12rx.H)-form
12-Epiteucvin
Constit. ofT. .flavum. Cryst. (EtOAcjhexane). Mp 197-
1990. [aln + 222.6° (c, 0.694 in CHC1 3).
(ent-6P,8rx.H,l Orx.H,12PH)-form [51918-98-0] Teucvin
lsol. from T. viscidum. Mp 207-208°. [a]n +88.4°
(CHC1 3).
(ent-6«.,8«-H,l OpH,l2rx.H)-form
12-Epiteucvidin
Constit. ofT. kotschyanum. Cryst. (EtOAcjhexane). Mp
C 19 H 18 0~ M 326.348 190-194°. [a]~ -155.7° (c, 0.158 in CHC1 2).
(ent-12PH)-form [41759-79-9] Teuscorolide (ent-6«.,8«-H,l Orx.H,12rx.H)-form
Constit. of Teucrium scorodonia. Cryst. 12-Epiteu.flin
(Me 2COjhexane). Mp 198-200°. [ali? + 13.SO (c, 0.31 in Constit. of T. kotschyanum. Amorph.
CHC1 3). Fujita, E. eta/, J. Chern. Soc., Chern. Commun., 1973, 793 (cryst
2a-Hydroxy: [87376-70-3]. 15,16-Epxoy-2-hydroxy-19-nor- struct, Teucvin)
4,6,13(16),14-clerodatetraene-18,6:20,12-diolide. 2«.- Uchida, I. et a/, Tetrahedron, 1975, 31, 841 (iso/, struct)
Hydroxyteuscorolide Savona, G. eta/, J. Chern. Soc., Perkin Trans. 1, 1979, 1915 (isol,
C19H 180 6 M 342.348 struct)
From T. scorodonia. Cryst. (EtOAcjhexane). Mp 243- Papanov, G.Y. eta/, Z. Naturforsch., B, 1980, 35, 754
(Teuchamaedryn A)
2460. [aJn + 20.8° (c, 0.26 in CHC1 3/Py). Node, M. eta/, Phytochemistry, 1981, 20, 757 (isol)
Marco, J.L. eta/, Phytochemistry, 1982, 21, 2567; 1983, 22, 727. Fayos, J. eta/, J. Org. Chern., 1984, 49, 1789 (12-Epiteucvin)
Savona, G. et a/, Phytochemistry, 1986, 25, 2857 (deriv)

804
15,16-Epoxy-19-nor-2-oxo-13(16),14-... - 19-Hydroxypteronia dilactone Di-00849 - Di-00854

15,16-Epoxy-19-nor-2-oxo-13(16),14- Dl-00849 6-Ketone: [66756-57-8]. 15,16-Epoxy-19-nor-6-oxo-

clerodadien-20,12-olide 13(16),14-clerodadiene-17,12:18,2-dio/ide. Diosbulbin D
C19H:zo07 M 360.363
0 Constit. of D. bulbi/era. Cryst. (MeOH). Mp 229-230°.
Q I
[a] 0 -49° (c, 0.11 in MeOH).
(2a.,4pH,5p,6a.,8pH,l2a.l/)-form
Ac: 8-Epidiosbulbin E acetate

0d3-~-o
C21 H 240 7 M 388.416
Isol. from D. bulbi/era. Cryst. Mp 223-225°. [ali? +46°
(c, 0.145 in MeOH).
3 5 Ida, Y. et al, Justus Liebigs Ann. Chern., 1978, 818 (isol, struct)
4
Murray, R.D.H. et al, Phytochemistry, 1984, 23, 623 (isol)
IH
CI.,H2404 M 316.396 Flabellata secoclerodane Dl-00852
(ent-4a.H,5a.,l2PH)-form [17633-81-7] Crotonin ent-19-Acetoxy-15,16-epoxy-5,10-seco-1(10),2,4,13(16),14-
Constit. of Croton /ucidus. Cryst. (EtOAcjhexane). Mp c/erodapentaen-18-oic acid
148-149°. [a] 0 -1.4° (CHC1 3).
[116369-02-9]
(ent-4a.H,5P,J2PII)-form
t-Crotonin
Constit. of C. cajucara. Needles. Mp 131-132°. [a] 0
+ 2.3° (c, 3.29 in CHC1 3).
3,4-Didehydro: 15,16-Epxoy-19-nor-2-oxo-3,13(16),14-
c/erodatrien-20,12-o/ide. t-Dehydrocrotonin
CI.,H2204 M 314.380
Constit. of C. cajucara. Needles. Mp 138.5-140.5°. [a] 0 COOH
+ 11.9° (c, 0.3 in CHC1 3). C21 H:z1P 5 M 372.460
Chan, W.R. et al, J. Chern. Soc. C, 1968, 2781 (isol) Constit. of Baccharis jiabellata. Oil. [a] 0 -33.8° (c, 4.5 in
Blount, J.F. et al, J. Chern. Res. (S), 1984, 114 (cryst struct) CHC1 3).
ltokawa, H. et al, Phytochemistry, 1989, 28, 1667 (isol) Saad, J.R. et al, Phytochemistry, 1988, 27, 1884.

15,16-Epoxy-5,10-seco- 6-Hydroxyisochilolide Dl-00853

1,3,5(19),13(16),14-clerodapentaene-
17,18-dioic acid Dl-00850

0
COOH
C20H:zs06 M 364.438
M 358.390 Constit. of Microg/ossa pyrrhopappa. Gum. lsochilolide is
ent-form currently unknown (1990).
Constit. of Conyza welwitschii. Zdero, C. eta/, Phytochemistry, 1990, 29, 3233 (isol)
Zdero, C. et al, Phytochemistry, 1990, 29, 2247.
19-Hydroxypteronia dilactone Dl-00854
15,16-Epxoy-6-hydroxy-19-nor-13(16),14- Dl-00851 [129384-21-0]
clerodadiene-17,12: 18,2-diolide

Q I

CI.,Hll06 M 346.379
(2a.,4pH,5p,6a.,8a.H,l2a.l/)-form [67567-14-0] Diosbulbin E C20 H 220 7 M 374.390
Constit. of Dioscorea bulbifera. Cryst. (MeOH). Mp Cons tit. of Pteronia eenii. Cryst. Mp 176-179°.
235-237°. [a] 0 + 16° (c, 0.16 in MeOH). 19-Ketone: [129349-96-8]. Pteroniatriliu:tone

805
7-Hydroxy-13,14,15,16-tetranor-3-... - 19-Nor-3,5-clerodadien-15-ol Di-00855 - Di-00860

C20H 100 7 M 372.374 Languiduline Di-00858

Constit. of P. eenii. Cryst. Mp 222°. [cc]~ -3° (c, 0.34 in [114391-81-0]
CHC1 3).
[129445-35-8]
Zdero, C. eta/, Phytochemistry, 1990, 29, 1231 (isol, pmr)

7-Hydroxy-13,14,15,16-tetranor-3- Dl-00855
cleroden-18,19-olide
[100343-67-7]

cgr:~
<;1Hn06 M 382.412
Constit. of Salvia /anguidula. Cryst. Mp 243-245°. [cc]~
-193.4° (c, 0.2 in CHC1 3).
Cordenas, J. eta/, Heterocycles, 1988, :Z7, 1809 (isol, cryst struct,
cmr)
0
C 16Hn05 M 294.347 Montanin A Dl-00859
(ent-7/1)-form ent-:6,18:15,16-Diepoxy-19-nor-4(18),5,13(16),14-
Constit. of Baccharis genistelloides. Needles. Mp 253- clerodatrien-20, 12oc-olide
2580. [cc]~ -122.4° (c, 1.2 in MeOH). [68370-49-0]
Kuroyanagi, M. et a/, Chern. Pharm. Bull., 1985, 33, 5075.

Incanpteroniolide Dl-00856
Incanpteronia/actone
[129349-95-7]

Q I

HOH,~~~
C19H 100 4 M 312.365
Constit. of Teucrium montanum. Cryst. Mp 126-127°. [cc]n
+ 11.5° (CHC13). .
Malakov, P.Y. eta/, Tetrahedron Lett., 1978, 2025.
Gacz-Baitz, E. et a/, Heterocycles, 1982, 19, 539 (cmr)
C20H:u;04 M 330.423
Constit. of Pteronia incana. Gum. [cc]~ -51° (c, 0.26 in 19-Nor-3,5-clerodadien-15-ol Di-00860
CHC1 3).
6-Hydroxy: 6-Hydroxyincanpteronialactone
C20H 260 5 M 346.422
Isol. from Microglossa pyrrhopappa. Gum.
Zdero, C. eta/, Phytochemistry, 1990, :Z9, 1231, 3233 (isol, pmr)

Jewenol B Dl-00857
C 19H 310 M 276.461
[117590-97-3]
(ent-13q,)-jorm
Constit. of Relhania corymbosa.
15-Carboxylic acid: 19-Nor-3,5-clerodtulien-15-oic acid
C1,H300 1 M 290.445
Constit. of R. corymbosa.
Tsichritzis, F. eta/, Phytochemistry, 1990, 29, 3173 (isol)

HOCH2
C10H 340 4 M 338.486
Constit. of Portulaca cv. jewel. Cryst. (MeOH aq.). Mp
123.5-124.SO. [ccJtt -59.2° (c, 0.52 in EtOH).
Ohsaki, A. eta/, Phytochemistry, 1988, '1:1, 2171.

806
17'-Nor-8-oxo-3,13(16)-clerodadiene-... - Pyrrhopappolide Di-00861 - Di-00866

17-Nor-8-oxo-3,13(16)-clerodadiene- Dl-00861 Constit. of Conyza scabrida. Oil (as Me ester). [1X]n

15,16:18,19-diolide -30° (c, 0.27 in CHC1 3) (Me ester).
5rx.-Methoxy, lOP-hydro: [88379-00-4]. 5rx.-Methoxy-5,10-
dihydroprintzianic add
C2tH3004 M 346.466
Constit. of C. scabrida.
5rx.-Hydroxy, lOP-hydro, lactone: (88379-01-5]. 5rx.-Hydroxy-
5,10-dihydroprintr.ianic acid lllctone
C10H 140 3 M 314.424
Constit. of C. scabrida.
Ct,Hn05 M 330.380 1,2-Didehydro, 5rx.-hydroxy, lOP-hydro: (88379-03-7]. 5rx.-
ent-form [66279-26-3] Demethylmarrubiaketone Hydroxy-1 ,2-dehydro-5,10-dihydroprintr.ianic ru:id
Constit. of Leonurus marrubiastrum. Cryst. (Me2C0jpet. c;..H140 4 M 330.423
ether). Mp 262-263°. [IX]~ -129.SO (c, 0.15 in CHC1 3). Constit. of C. scabrida.
Kirfel, A., Acta Crystal/ogr., Sect. B, 1978, 34, 949 (cryst struct) Bohlmann, F. et al, Phytochemistry, 1978, 17, 487 (isol)
Tschesche, R. et a/, Chem. Ber., 1978, 111, 2130 (isol) Bohlmann, F. et al, Justus Liebigs Ann. Chem., 1983, 2008 (deriv)

19-Nor-3-oxo-4-cleroden-15-oic acid Dl-00862 Pteronialactone Dl-00865

COOH
Q I

C 19H 300 3
(ent-13~)-form
M 306.444

Constit. of Re/hania corymbosa.

Tsichritzis, F. et al, Phytochemistry, 1990, 19, 3173 (isol)
<~~)=I OAc

CnH3408 M 486.561
Norstrictic acid Dl-00863 31!,-Hydroxy: 3-Hydroxypteronialilctone
C 27H 340 9 M 502.560
ent-14,15,16-Trinor-5,10-seco-1,3(19)-clerodatriene-13,18-
Constit. of Pteronia divaricata. Gum.
dioic acid
[115783-40-9] 3-0xo: [129349-94-6]. 3-0xopteronialru:tone
CnH320, M 500.544
Constit. of Pteronia divaricata. Gum. [rx.]~ +66° (c, 0.25

yS~"
in CHC1 3).
[129349-93-5, 129443-40-9]
Zdero, C. et al, Phytochemistry, 1990, '1.9, 1231 (isol, pmr)

COOH Pyrrhopappolide Dl-00866

C 17H 140 4 M 292.374
3rx.,4rx.:J5,16-Diepoxy-JO-oxo-9,10-seco-13(16),14-
clerodadien-20,12-olide
Constit. of Grangea maderaspatana. Gum (as Me ester).
[1X]n -135° (c, 0.24 in CHC13) (Me ester).
Singh, P. et al, Phytochemistry, 1988, 27, 1537.

Printzianic acid Dl-00864

[67594-75-6]

C10H 140 5 M 346.422

C:zoli:11;03 M 314.424 lsol. from Microg/ossa pyrrhopappa. Gum.
Minor constit. of Printzia laxa. Oil (as Me ester). (IX]~ 6/l-Hydroxy: 3,4:15,16-Diepoxy-6-hydroxy-10-oxo-9,10-
-50° (c, 0.2 in CHC1 3) (Me ester). seco-13(16),14-c/erodadien-20,12-o/ide. 6P-
A-5•6-Jsomer: [88424-33-3]. Isoprintzianic ru:id Hydroxypyrrhopappolide
C:zoH140 3 M 314.424 c;..H140 6 M 362.422
Constit. of P. /axa. Oil (as Me ester). Constit. of M. pyrrhopappa. Gum. Also exists as various
51X-Hydroxy, lOP-hydro: [88378-99-8]. 5rx.-Hydroxy-5,10- esters in M. pyrrhopappa.
dihydroprintr.imric ru:id 6P-Angeloyloxy, JOrx.-alcoho/: 6fl-Ange/oy/oxy-10rx.-hydroxy-
C:zoH:za04 M 332.439 10-desoxopyrrhopappolide
~H 3407 M 446.539

807
Salvigenolide - Strictic acid Di-00867 - Di-00872

Constit. of Conyza pyrifolia. Gum. Secochiliotrin Dl-00870

10rx-Alcohol, 10-angeloyl: 10rz-Angewywxy-10- ent-15,16-Epoxy-3,4-seco-4,13(16),14-halimatrien-3-oic acid
desoxopyrrhopappolide [102904-60-9]
C 25H 340 6 M 430.540
Constit. of C. pyrifolia. Gum.
Zdero, C. eta/, Phytochemistry, 1990, 29, 3167, 3233 (isol, pmr,
cmr)

Salvigenolide Dl-00867
[102818-82-6] HOOC",

0
I
I C20H 300 3 M 318.455
0 Constit. of Chiliotrichium rosmarinifolium. Oil (as Me
ester). [rx]~4 -28° (c, 4.1 in CHC1 3) (Me ester).
--40 Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305.

Solidagonal acid Dl-00871

[97868-05-8]
CnH210 7 M 398.412
Constit. of Salvia fulgens. Cryst. (MeOH). Mp 218-220°. ?" COOH
[rx]i,O -191.6° (c, 0.21 in MeOH).
Esquivel, B. eta/, Tetrahedron, 1985, 41, 3213 (cryst struct)

Saudin Di-00868
[94978-16-2] C 20 H 300 3 M 318.455
0 Constit. of Solidago altissima.
Bohlmann, F. eta/, Phytochemistry, 1985, 24, 1114.

Strictic acid Dl-00872

ent-15,16-Epoxy-5,10-seco-1,3,5(19),13(16),14-
clerodapentaen-18-oic acid. Conyzic acid. Seconidoresedic
acid
[56317-16-9]
C 20Hn07 M 374.390 12
Constit. of Cluytia richardiana. Hypoglycaemic agent.
Cryst. (Et0AcfCC14). Mp 202-203°. [rxJn -12? (c, 0.094
in CHC1 3).
Mossa, J.S. et al, J. Org. Chern., 1985, 50, 916.

Secochiliolide lactone Dl-00869 COOH

ent-15,16-Epoxy-3,4-seco-4(18),13(16),14-halimatriene-
C20 H 260 3 M 314.424
3,5P:20,12P-diolide
Constit. of Conyza stricta. Cryst. (MeOH). Mp 160°. [rxln
[102904-57-4] -190° (c, 1.1 in CHC1 3).
15,16-Dihydro, 15-methoxy, 16-oxo: ent-15-Methoxy-5,10-
seco-1 ,3,5,(19), 13-clerodatetraen-16, 15-olid-18-oic acid.
15,16-Dihydro-15-methoxy-16-oxostrictic acid
C21 Hza05 M 360.449
Constit. of Grangea maderaspatana. Gum (as Me ester).
[rxln -135° (c, 0.24 in CHC1 3) (Me ester).
12R-Hydroxy: 12-Hydroxystrictic acid
C 20H 260 4 M 330.423
0 Constit. of C. welwitschii.
,::;:? Pandey, U.C. eta/, Phytochemistry, 1984, 23, 391 (isol, struct)
Singh, P. et a/, Phytochemistry, 1988, 27, 1537 (deriv)
C 20H 240 5 M 344.407 Zdero, C. eta/, Phytochemistry, 1990, 29, 2247 (derivs)
Constit. of Nardophyllum lanatum. Oil. [rx]~ +23° (c, 0.73
in CHC1 3).
Jakupovic, J. eta/, Tetrahedron, 1986, 42, 1305.

808
13,14,15,16-Tetranor-3-clerodene-... - 14,15,16-Trinor-3-clerodene-13,18-... Di-00873- Di-00877

13,14,15,16-Tetranor-3-clerodene-12,18- Dl-00873 Constit. of Teucrium hyrcanicum and T. flavum. Cryst.

qj:OH
diol (EtOAcjpet. ether). Mp 178°. [1X)i,'l -100° (CHC1 3).
6,10-Diepimer: [94482-78-7). lsoteujlidill
C19H100 6 M 344.363
Froin T. chamaedrys. Cryst. (EtOAcjhexane). Mp 215-
2170. [1X)i; + 156° (c, 0.152 in CHC1 3).
Savona, G. eta/, J. Chern. Soc., Perkin Trans. 1, 1978, 1080 (isol,
cryst struct)
Gacs-Baitz, E. eta/, Phytochemistry, 1978, 17, 1967 (isol)
HOH2 C Rodriguez, M.C. eta/, Phytochemistry, 1984, 23, 1465 (Isoteuflidin)

C16H:zs01 M 252.396
ent-form [78795-78-5) Acritopappusol Teucrin H4 Dl-00876
Constit. of Acritopappus hagei. Gum. ent-15,16-Epoxy-2P-hydroxy-19-nor-4,13(16),14-
c/erodatrien-18,61X:20,12-diolide
12-Carboxy/ic acid: [78795-79-6). 18-Hydroxy-13,14,15,16-
tetranor-3-c/eroden-12-oic acid. Acritopappus acid [64756-05-4)
C 16H 160 3 M 266.380
Constit. of A. hagei. Gum (as Me ester, Ac). [1X)i;'
-24.3° (c, 1.7 in CHC1 3) (Me ester, Ac).
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2695.

Teucrin A Dl-00874
ent-15,16-Epoxy-7P-hydroxy-19-nor-4,13(16),14-
c/erodatriene-18,6P:20,12-diolide
[12798-51-5)

0
Ct9H 100 6 M 344.363
Constit. of Teucrium hyrcanicum.
!! 5•10-1somer: [121387-34-6]. lsoteucrin H4
C1 9H100 6 M 344.363
lsol. from T. kotschyanum. Cryst. (EtOAcjhexane) (as
acetate). Mp 191-194° (acetate). [1X)i;1 + 128.6° (c, 0.168
in CHC1 3) (acetate).
Gacs-Baitz, E. eta/, Phytochemistry, 1978, 17, 1967 (Teucrin H4)
Simoes, F. eta/, Heterocycles, 1989, 28, 111 (Isoteucrin H4)
0
C 1,H100 6 M 344.363
Constit. of Teucrium chamaedrys.
14,15,16-Trinor-3-clerodene-13,18-dioic Dl-00877
acid
6-Epimer: 6-Epiteucrill A
C1,H100 6 M 344.363
Constit. ofT. chamaedrys. Cryst. (Me2CO/hexane) (as
acetate). Mp 195-198° (acetate). [1X)i,'l +96.2° (c, 0.185 in
CHC1 3) (acetate).
QS~H
Popa, D.P. et al, Khim. Prir. Soedin., 1972, 8, 67; 1974, 10, 321;
Chern. Nat. Compd. (Engl. Trans/.), 60, 328 (isol)
Gacz-Baitz, E. eta/, Heterocycles, 1982, 19, 539 (cmr) COOH
Femandez-Gadea, F. eta/, Phytochemistry, 1983, 22, 723 (isol, Ct,Hu04 M 294.390
struct)
ent-form
Norluudwickiic acid
Teucrin H1 Dl-00875 Constit. of Grangea maderaspatana.
ent-15,16-Epoxy-31X-hydroxy-19-nor-4,13(16),14-
Di-Me ester: [74284-66-5).
c/erodatriene-181X,61X:20,12-diolide. Teuflidin. 3P-
Gum. [1X) 0 -36° (c, 0.1 in CHCI3).
Hydroxyteucvidin
Singh, P. et a/, Phytochemistry, 1988, 27, 1537.
[64660-17-9)

M 344.363

809
7,13-Abietadiene- 8,13-Abietadien-19-oic acid Di-00878 - Di-00884

Narayanan, C.R. et al, Tetrahedron Lett., 1965, 3639 (pmr)

Karrer, W. et a/, Konstitution und Vorkommen tier Organischen

Abietanes Pflanzenstojfe, 2nd Ed., Birkhiiuser Verlag, Basel, 1972-1985,

no. 1952 (occur)
Bohlmann, F. et al, Phytochemistry, 1980, 19, 2655 (ent-form)

7,13-Abietadien-1~ic acid Di-00881

4-epi-Abietic acid. 4-Epiabietic acid
7,13-Abietadiene Dl-00878
[24563-90-4]

Cmf131 M 272.473
ent-form [42895-82-9] C10H 300 1 M 302.456
Constit. of roots of Solidago missouriensis and Constit. of Juniperus phoenicea. Cryst. (as Me ester). Mp
Helichrysum chionosphaerum. Oil. (cx]i: + 127° (c, 2 in 38-40° (Me ester). [cxln -61° (CHC1 3) (Me ester).
CHCI 3). Tabacik, C. et al, Bull. Soc. Chim. Fr., 1969, 3264.
Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073 (isol)
Bohlmann, F. et al, Phytochemistry, 1980, 19, 869 (isol)
8,12-Abietadien-18-oic acid Dl-00882
[17603-06-4]
8,13-Abietadiene Dl-00879
Palustradiene
[41577-36-0]

C10H 300 1 M 302.456

Cryst. (EtOH aq.). Mp 160.5-162°. [cxln + 55°.
C10H 31 M 272.473 Burgstahler, A.W. et al, J. Am. Chern. Soc., 1964, 86, 96.
Constit. of oil of berries of Juniperus sabina. Oil. (cxln
-45.SO (c, 0.68 in CHC1 3). 8,13-Abietadien-18-oic acid Dl-00883
De Pascual Teresa, J. eta/, An. Quim., 1978, 74, 1093. Pa/ustric acid
[1945-53-5]
7,13-Abietadien-18-oic acid Dl-00880
Abietic acid
[514-10-3]

C20H 300 2 M 302.456

Constit. of Pinus palustris, P. pallasiana, P. pityusa and P.
caribaea. Cryst. (MeOH). Mp 162-167°. [cxln + 71.6°
(EtOH).
Cmf1:14,01 M 302.456 Wenkert, E. et al, J. Am. Chern. Soc., 1964, 86, 2038.
Constit. of Pinus spp .. Also from Abies sibirica, Larix spp.,
Agathis spp. and Picea jezoensis. Plates (EtOH). Mp
171-173°. [ex]~ -102° (EtOH). The Abietic acid of 8,13-Abietadien-19-oic acid Di-00884
commerce is often a resinous mixt. of acids obt. by acid 4-epi-Palustric acid. 4-Epipalustric acid
isomerisation of pine rosin. [24563-91-5]
I> TP8580000.
ent-form
ent-7, 13- Abietadien-18-oic acid
Constit. of Solidago nemoralis. Gum. [cx]i;' -25° (c, 0.2
in CHC13). Struct. not certain.
Barton, D.H.R., Q. Rev., Chern. Soc., 1949, 3, I (rev)
Org. Synth., Coli. Vol., 4, 1963, I (purifn)
Wenkert, E. et al, J. Am. Chern. Soc., 1964, 86, 2038 (synth, bib{)

810
8(14),12-Abietadien-18-oic acid- 7,13-Abietadien-18-ol Di-00885 - Di-00890

Czell34,01 M 302.456 Constit. of Solidago missouriensis. Oil. [a]~ + 111° (c,

Constit. of Juniperus phoenicea. Cryst. (as Me ester). Mp 6.1 in CHC13).
56-58° (Me ester). Bp0. 15 158-160° (Me ester). Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073.
Tabacik, C. et a/, Bull. Soc. Chim. Fr., 1969, 3264.
7,13-Abietadien-5-ol Dl-00888
8(14),12-Abietadien-18-oic acid Dl-00885
Laeropimllric acid. Sapietic acid. Levopimaric acid. P-
Pimaric acid
[79-54-9]

c;.,H310 M 288.472
(ellt-5«)-form [77355-72-7]
Constit. of Solidago nemoralis. Gum. [a]~ +24° (c, 0.1
in CHC1 3).
C,.H300 1 M 302.456
Bohlmann, F. et a/, Phytochemistry, 1980, 19, 2655.
Constit. of Pinus spp. Also from Picea jezoensis and
Agathis robusta. Cryst. (EtOH). Mp 152°. [a]~ -282°
(EtOH). 7,13-Abietadien-12-ol Dl-00889
Burgstah1er, A.W. eta/, J. Am. Chern. Soc., 1961, 83, 4660 (struct)
Ayer, W.A. et al, Can. J. Chern., 1963, 41, 1113 (pmr, struct)
Cannan, R.M. eta/, Aust. J. Chern., 1964, 17, 390 (isol)
Org. Synth., 1965, 45, 64 (synth)
Karle, 1., Acta Crysta/logr., Sect. B, 1972, 28, 2000 (cryst struct)

8(14),13(15)-Abietadien-18-oic acid
Neotlbietic acid
[471-77-2] c;.,H310 M 288.472
12/J-form [128502-92-1]
Constit. of Helichrysum formosissinum. Oil. [a]~ + 50°
(c, 0.1 in CHC13).
Jakupovic, J. eta/, Phytochemistry, 1990, 29, 1589 (isol, pmr)

7,13-Abietadien-18-ol Dl-00890
Abietillol
[666-84-2]
C,.Il300 1 M 302.456
Isol. from resins of Pinus spp., Abies spp. and Agathis
microstachys. Cryst. (EtOH aq.). Mp 173-173.5° (167-
1690) (sealed tube under N:J. [a]~ + 161.6° (c, 2.5 in
95% EtOH). Air-sensitive. Dextrosapinic acid was a
mixt. of Abietic and Neoabietic acids.
Cyc/ohexylamine salt: Needles (EtOH aq.). Mp 211-214°
dec. (a]~ + 110.2° (c,0.295 in 95% EtOH aq.).
Harris, G.C. et a/, J. Am. Chern. Soc., 1948, 70, 334, 339.
Schuller, W. et al, J. Am. Chern. Soc., 1961, 83, 2563 (isol, props, CzellnO
struct) Isol. from Pinus sy/vestris, Abies sibirica and Araucaria
Carman, R.M. et a/, Aust. J. Chern., 1966, 19, 2403 (isol) exce/sia. Cryst. or oil. Mp 85.5-87°. [a]n -132.5° (c, 2 in
EtOH), [a]n -73° (CHC13).
7,13-Abietadien-2-ol Dl-00887 18-A/dehyde: [6704-50-3]. 7,13-Abietadien-18-al. Abietbud
C,.H300 M 286.456
Constit. of Araucaria cooki, A. angustifolia, P. sylvestris,
P. sibirica and Abies sibirica. Cryst. or oil. Mp 45-48°.
HO.... [a]n -116° (CHC13).
18-Carboxylic acid: see 1,13-Abietadien-18-oic acid, Di-
00880
Erdtman, H. eta/, Acta Chern. Scand., 1963, 17, 18-"26.
Chirkova, M.A. et a/, Khim. Prir. Soedin., 1966, 2, 99.
Czell320 M 288.472 Caputo, R. et a/, Gazz. Chim. Ita/., 1974, 104, 491.
Caputo, R. et a/, Phytochemistry, 1974, 13, 471.
(ellt-2/1)-form [42895-89-6]
Oil.
Ac: [42895-85-2]. ent-2P-Acetoxy-1,13-abietadiene
C11H 340 1 M 330.509

811
7,13-Abietadien-3-one - 8,11,13-Abietatriene-2,12-diol Di-00891 - Di-00897

7,13-Abietadien-3-one Dl-00891 6,8,11,13-Abietatetraene-11,12,14-triol Dl-00894

Cryptanol
[110209-97-7]

(-)-form

C20H 300 M 286.4S6

(-)-form [29461-2S-4]
Constit. of Juniperus phoenicea. Oil. [1X]n -138.6° C20H 280 3 M 316.439
(CHC1 3). Constit. of Salvia cryptantha. Cryst. Mp 138-142°.
(+)-form Ulubelen, A. eta/, Phytochemistry, 1987, 26, 1534.
ent-form
Constit. of Solidago missouriensis. Oil. [1X]i; + 100° (c, 8,11,13-Abietatriene Di-00895
13.3 in CHCI 3). Dehydroabietane
3P-Alcohol: [4289S-87-4]. ent-7,13-Abietadien-Jrz-ol [19407-28-4]
C20H 320 M 288.472
lsol. from S. missouriensis. Oil. [1X]i; + 108° (c, 2.3 in
CHCI 3).
Anthonsen, T. et al, Acta Chern. Scand., 1973, 27, 1073 (isol)
De Pascual Teresa, J. eta/, An. Quim., 1978, 74, 465 (isol)

Abietane Dl-00892

__ ( C20H30 M 270.4S7
Constit. of Pinus pallasiana and Podocarpus ferrugineus.
Cryst. by sub!. Mp 41-44°. Bp0.05 l3S 0 • [1X]n + S0 (c, 2.82
(-)-form in CHCI 3).
Absolute Brieskom, C.H. et al, J. Org. Chern., 1964, 29, 2293.
configuration Burgstahler, A.W. eta/, J. Org. Chern., 1969, 34, 1502 (synth)
Vlad, P.F. et al, Khim. Prir. Soedin., 1971, 7, 20 (isol)
C20H 36 M 276.S04
(-)-form [19407-12-6] 8,11,13-Abietatriene-1,18-diol Di-00896
Cryst. Mp 37-38°. [1X]i; -so (c, 0.3 in hexane). [24338-63-4]
(+)-form [1837S-16-1]
ent-form
Cryst. Mp 38°. [1X]i; +so (c, 0.4 in hexane).
Burgstahler, A.W. eta/, J. Org. Chern., 1969, 34, 1562 (synth)
Fujita, E. ~~a/, Tetrahedron, 1969, 25, 1335 (synth)

6,8,11,13-Abietatetraene-11,12-diol Dl-00893 CH2 0H

C2oH300 2 M 302.4S6
1rz-form
Teideadiol
Constit. of Nepeta teydea. Cryst. (Me 2C0jpet. ether).
Mp 128°. [1X]n +98° (c, 3.3 in EtOH).
Breton, F.J.L. eta/, An. Quim., 1970, 66, 293; CA, 73, 88048n
(isol, struct)
Mizuno, H. eta/, Chern. Pharm. Bull., 1976, 24, 1527 (synth)
C20H 28 0 2 M 300.440
12-Me ether: [34327-31-6]. 12-Methoxy-6,8,11,13-
abietatetraen-11-ol 8,11,13-Abietatriene-2,12-diol D!-00897
C21 H 300 2 M 314.467
Isol. from wood of Juniperus rigida.
Yanagawa, T. eta/, CA, 1971, 75, 148545a.

C20 H300 2 M 302.4S6

2rz-form [3346S-18-8] Sa/viol. 21X-Hydroxyferruginol

812
8,11,13-Abietatriene-3,12-diol - 8,11,13-Abietatriene-15,18-diol Di-00898 - Di-00902

Isol. from roots of Salvia miltiorrhh. Cryst. (C 6H 6). 8,11,13-Abietatriene-7, 15-diol 01-00899
Mp 108°.
Di-Me ether:
C 21H 340 2 M 330.509
Constit. of S. pachystachys. Pale yellow solid (MeOH).
Mp 92°.
2-Ketone: [54825-04-6]. 12-Hydroxy-8,11 ,13-abietatrien-2-
one. 2-0xoferruginol. 2-Ketoferrugino/
lsol. from Podocarpus ferrugineus. Cryst. (heptane). Mp
232-234°. [ocln +50° (c, 0.1 in MeOH). C 20 H 300 2 M 302.456
6,7-Didehydro: 6,8,11 ,13-Abietatetraene-2oc,l2-diol. 6,7- 7P-form [105037-91-0]
Dehydrosalviol. 6, 7- Didehydrosalviol Constit. of Salvia sapinae. Cryst. (EtpjCHC1 3). Mp
C 20Hllp2 M 300.440 136°. [oc]~ +80.8° (c, 0.22 in CHC1 3).
Isol. from S. texana. Yellow oil. Pereda-Miranda, R. et a/, Phytochemistry, 1986, 25, 1931.
Hayashi, T. et al, J. Chern. Soc., Chern. Commun., 1971, 541
(Sa/viol)
Wenkert, E. et al, Phytochemistry, 1974, 13, 2545 (2-0xoferruginol) 8,11,13-Abietatriene-7,18-diol 01-00900
Matsumoto, T. et al, Bull. Chern. Soc. Jpn., 1981, 54, 581 (synth)
Gonzalez, A.G. et al, J. Chern. Res. (S), 1989, 132 (Dehydrosalviol)
Ulubelen, A. et al, J. Nat. Prod. (Lloydia), 1990, 53, 1597 (deriv)

8,11,13-Abietatriene-3,12-diol 01-00898

C20H 300 2
7rx-form
Constit. of pollen grains of Cedrus deodflra. Needles
(Me2CO). Mp 89°. [oc]i,O -3.3° (c, 0.46 in EtOH).
C 20H 300 2 M 302.456 Ohmoto, T. et a/, Chern. Pharm. Bull., 1987, 35, 229.
3P-form [564-73-8] Hinokiol. Taiwanin D
Constit. of various woods including Cupressus spp., 8,11,13-Abietatriene-12,18-diol 01-00901
Tetrac/inis spp. and Taiwania cryptomeroides. Cryst. 18-Hydroxyferruginol
(EtOH). Mp 234-235°. [oc]i,O + 74.4° (CHC1 3).
3-Ketone: [472-37-7]. 12-Hydroxy-8,11 ,13-abietatrien-3-one.
Hinokione
C 20H 180 2 M 300.440
Constit. ofT. articulata and. C. spp. Cryst. Mp 191-
1920. [ocln + 111.9°.
3-Ketone, 1oc,2oc-epoxy: 1oc,2oc-Epoxy-12-hydroxy-8, 11,13-
abietatrien-3-one. 1,2-Epoxyhinokione 'CH20H
C 20H 26 0 3 M 314.424
Constit. of Chamaecyparis obtusa. Needles C20H 300 2 M 302.456
(Etpjhexane). Mp 157-159°. [oc]i;' +224° (c, 0.66 in Constit. of Torreya nucifera. Cryst. (Me 2CO). Mp 180-
CHC1 3). 181°. [oc]~ + 70.3° (c, 0.37 in EtOH).
3-Ketone, 6,7~didehydro: [119767-14-5). 12-Hydroxy- 18-A/dehyde: 12-Hydroxy-8,11 ,13-abietatrien-18-a/. 18-
6,8,11,13-abietatetraen-3-one. Hypargenin D 0xoferruginol
C20H 260 2 M 298.424 C20 H 280 2 M 300.440
lsol. from Salvia hypargeia. Shows antibacterial props. Constit. of Torreya nucifera. Cryst. (hexane). Mp 139-
Orange amorph. solid. 1410. [ocJn +69.6° (c, 1.05 in CHC1 3).
Chow, Y.-L. et al, Acta Chern. Scand., 1962, 16, t296 (isol) Fukushima, I. et al, Agric. Bioi. Chern., 1968, 32, 1103 (isol, struct)
Erdtman, H. et al, Acta Chern. Scand., 1962, 16, 1301 (struct) Harrison, L.J. et al, Phytochemistry, 1987, 16, 1211 (deriv)
Lin, Y.-T. et al, J. Chin. Chern. Soc. (Taipei), 1963, 10, 163 (isol)
Matsumoto, T. et al, Bull. Chern. Soc. Jpn., 1981, 54, 581 (synth) 8,11,13-Abietatriene-15,18-diol 01-00902
Ozaki, N. et al, Phytochemistry, 1983, 22, 1771 (isol)
Ulubelen, A. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1178 [65894-41-9]
(Hypargenin D)

C20H 300 2
Constit. of Pinus spp.
Conner, A.H. et al, Phytochemistry, 1977, 16, 1777.
813
8,11,13-Abietatriene-3,7-dione - 8,11,13-Abietatrien-18-oic acid Di-00903 - Di-00906

8,11,13-Abietatriene-3,7-dione Dl-00903 Kondo, T. eta/, Yakugaku Zasshi (J. Pharm. Soc. Jpn.), 1962, 82,
M•gocin 1252 (isol)
Wenkert, E. et a/, J. Org. Chem., 1970, 35, 2422 (isol)
[128286-73-7] Yanagawa, T. et al, CA, 1971, 68, 148545a.
Matsumoto, T. eta/, Bull. Chem. Soc. Jpn., 1979, 52, 1459 (synth)
Snitman, D.L. et a/, Tetrahedron Lett., 1979, 2477 (synth)
Hueso-Rodriguez, J .A. et a/, Phytochemistry, 1983, 22, 2005 (isol)
Valverde, S. eta/, Phytochemistry, 1985, 24, 111.

8,11,13-Abietatrien-18-oic acid Dl-00906

Dehydroabietic acid
[1740-19-8]
C 10H 11;01 M 298.424
Constit. of Azadirachta indica. Needles (pet. ether). Mp
133-134°.
Ara, I. eta/, Phytochemistry, 1990, 29, 911 (cmr, pmr)

8,11,13-Abietatriene-2,11,12-triol Dl-00904

C 10H 180 1 M 300.440

HO, Constit. of Pinus and Cedrus spp. Also from Abies
sachalinensis and Cistus labdaniferus. Cryst. (EtOH aq.).
Mp 172-173°. [oc]~ +62° (EtOH).
t> TP8710000.
Me ester: [1235-74-1].
M 318.455 C11H 300 1 M 314.467
2rz-form Constit. of Cistus labdaniferus and P. spp. Cryst.
Euphraticol (EtOH). Mp 62-63°. Bp0 _2 152-154°. [oc]~ +60° (EtOH).
Constit. of Salvia euphratica. [oc]i_!' +48.7° (c, 0.1 in 12-Chloro: [65310-45-4]. 12-Chloro-8,11 ,13-abietatrien-18-
MeOH). oic acid. 12-Chlorodehydroabietic acid
Ulubelen, A., J. Nat. Prod. (Lioydia), 1989, 52, 1313 (isol, pmr, C 10H 17Cl01 M 334.885
cmr) Found in kraft papermill effluent. Fish toxin. Cryst.
(hexane). Mp 178-180°.
8,11,13-Abietatriene-7,11,12-triol Dl-00905 14-Chloro: [65281-76-7]. 14-Chloro-8,11 ,13-abietatrien-18-
oic acid. 14-Chlorodehydroabietic acid
C10H 17Cl01 M 334.885
Found in kraft papermill effiuent. Fish toxicant. Cryst.
(pentane). Mp 159-160°.
?a.-form 12,14-Dichloro: [65281-77-8]. 12,14-Dichloro-8,11,13-
abietatrien-18-oic acid. 12,14-Dichlorodehydroabietic acid
C 10H 16Cl10 1 M 369.330
Found in kraft papermill effiuent. Fish toxin. Cryst.
CzoH31,03 M 318.455 (hexane). Mp 219-220°.
7rz-form [95457-05-9] 15-Hydroxy: [54113-95-0]. 15-Hydroxy-8,11,13-abietatrien-
12-Me ether: 12-Methoxy-8,11,13-abietatriene-7rz,ll-diol 18-oic acid. 15-Hydroxydehydroabietic aci
C 11H 310 3 M 332.482 C10H 180 3 M 316.439
Constit. of Salvia bicolor. Oil. [oc] 0 + 20° (c, 0.3 in Constit. of Agathis spp.
CHC13). 15-Hydroxy, Me ester: [29461-23-2].
7-Ketone: 11,12-Dihydroxy-8,11 ,13-abietatrien-7-one. C 11 H 300 3 M 330.466
Demethylcryptojaponol Constit. of Picea abies. Cryst. Mp 82-83° (75-77°). [oc] 0
CzoH180 3 M 316.439 +45.6° (c, 0.4 in CHC1 3).
Constit. of S. phlomoides. Pale yellow plates Tabacik-Wlotzka, C., Bull. Soc. Chim. Fr., 1964, 618 (isol)
(EtOAcfhexane). Mp 184-187°. [oc]i_!' +31.2° (c, 0.635 in Ireland, R.E. eta/, J. Org. Chem., 1966, 31, 2543 (synth)
CHC1 3). Narayanan, C.R. et al, Tetrahedron Lett., 1968, 1565 (pmr)
Carman, R.M. eta/, Aust. J. Chem., 1970, 23, 1457 (15-
7-Ketone, 12-Me ether: [16755-52-5]. 11-Hydroxy-12- Hydroxydehydroabietic acid)
methoxy-8,11 ,13-abietatrien-7-one. Cryptojll}Jonol Norin, T. et al, Acta Chem. Scand., 1972, 26, 2289 (15-
C 11 H 300 3 M 330.466 Hydroxydehydroabietic acid)
Constit. of Cryptomeria japonica and Podocarpus Welch, S.C. et a/, Synth. Commun., 1976, 6, 27 (synth)
ferrugineus. Cryst. (MeOH). Mp 205-207°. [oc]~ +25.3° Meyer, W.L. eta/, J. Org. Chem., 1977, 42, 2769 (synth)
(CHC1 3). Kutney, J.P. et al, Helv. Chim. Acta, 1982, 65, 1343, 1351
(Chlorodehydroabietic acids)
7/J-form
12-Me ether: [34327-30-5]. 12-Methoxy-8,11,13-
abietatriene-7J1,11-diol
C 11H 310 3 M 332.482
Isol. from wood of Juniperus rigida.

814
8,11,13-Abietatrien-3-ol - 8,11,13-Abietatrien-19-ol Di-00907 - Di-00911

8,11,13-Abietatrien-3-ol Di-00907 16-Hydroxy: 8,ll,13-Abietatriene-12,16-diol. 16-

Hydroxyferruginol
C:zoH 300 2 M 302.456
Constit. of Thujopsis dolabrata. Cryst. (Etpjpentane).
[cx]i; + 36.6° (c, 0.87 in CHC1 3).
1,3-Dioxo, Me ether: [18326-18-6]. 1,3-Dioxoferruginyl
methyl ether
C 21 H 2110 3 M 328.450
From Cupressus sempervirens. Cryst. (MeOH). Mp 176-
C:zoll 300 M 286.456 1770. [cxJn +220° (c, 0.97 in CHC1 3).
3fJ-form [78078-41-8] 6,7-Didehydro: 6,8,11,13-Abietatetraen-12-ol. .116-
Constit. of Nepeta tuberosa. Cryst. (hexane). Mp 109- Dehydroferriginol
1no (nat.), Mp 136.5-138° (synthetic). [cx]D + 50.4° C:zoH280 M 284.441
(CHC1 3). lsol. from woods of Juniperus communis and P.
Ac: Mp 112-1W. [cxJn +58.9° (CHC1 3). dacrydioides. Light-yellow solid. [ex]~ -60° (EtOH).
3-Ketone: 8,11,13-Abietatrien-3-one King, F.E. eta/, J. Chern. Soc., 1957, 573 (synth)
C:zoH2110 M 284.441 Briggs, L.H. eta/, Tetrahedron, 1959, 7, 270 (Dehydroferruginol)
Constit. of Saliva wiedemannii. Kondo, Y. eta/, Chern. Pharm. Bull., 1963, 11, 678 (pmr)
Mangoni, L. eta/, Tetrahedron Lett., 1967, 2643 (1,3-
Matsumoto, T. eta/, Bull. Chern. Soc. Jpn., 1981, 54, 581 (synth, Dioxoferruginyl methyl ether)
pmr) Torii, S. et a/, Bull. Chern. Soc. Jpn., 1977, 40, 2503 (synth)
Drones, J.G. eta/, Phytochemistry, 1988, 27, 523 (isol) Nishida, T. eta/, Org. Magn. Reson., 1977, 9, 203 (cmr)
Topca, G. eta/, Phytochemistry, 1990, 29, 2346 (isol, pmr, cmr) Snitman, D.L. eta/, J. Org. Chern., 1978, 43, 4758 (synth)
Matsumoto, T. eta/, Bull. Chern. Soc. Jpn., 1979, 52, 212 (synth)
8,11,13-Abietatrien-7-ol Di-00908 Yatagai, M. eta/, Phytochemistry, 1980, 19, 1149 (15-
Hydroxyferruginol)
Hasegawa, S. eta/, Phytochemistry, 1982, 21, 643 (isol)
Matsumoto, T. et a/, Bull. Chern. Soc. Jpn., 1985, 58, 340 (synth)
Tomita, Y. eta/, J. Chern. Soc., Chern. Commun., 1989, 108
(biosynth)

8,11,13-Abietatrien-15-ol Di-00910
[7 5696-40-1]
C:zoH 300 M 286.456
7rz-form [26920-02-5]
Constit. of Pinus monticola and Juniperus oxycedrus. Oil.
[cx]i;1 -8° (c, 1.6 in CHC1 3).
7-Ketone: [26920-03-6]. 8,11,13-Abietatrien-7-one
C:zoH280 M 284.441
Constit. of P. monticola and Cedrus atlantica. Cryst. by
sub!. Mp 87-90°. [cx]i;4 + W. C:zoH300 M 286.456
Conner, A.H. eta/, Phytochemistry, 1980, 19, 1121. Constit. of Pinus monticola. Semisolid. [cx]i,S +49° (c, 0.2 in
CHC1 3).
8,11,13-Abietatrien-12-ol Di-00909 Conner, A.H. eta/, Phytochemistry, 1980, 19, 1121.
Ferruginoft
[514-62-5] 8,11,13-Abietatrien-19-ol Dl-00911
Dehydroabietinol
[24035-43-6]

C:zoH300 M 286.456
Constit. of resin of the Miro tree, Podocarpus ferrugineus.
Also from P. totara, Dacrydium spp., Cupressus spp.,
Cryptomeria japonica and roots of lnularoyleana. Oil. C:zoH 300 M 286.456
Bp0_3 175°. [cx]!:,6 +40.6° (EtOH). Constit. of Calceolaria ascendens. Oil. [cx]i,S +43.4° (c, 2 in
Ac: Cryst. (pet. ether). Mp 81-82°. [cx]!:,6 +60.3° (EtOH). CHCI 3).
15-Hydroxy: [76235-93-3]. 8,ll,13-Abietatriene-12,15-diol. Ac: [24462-15-5]. Dehydroabietinol acetate
t 15-Hydroxyferruginol C22H 320 2 M 328.494
C:zoll300 2 M 302.456 Constit. of Pinus silvestris. Mp 60-61°. [cx]i,S +54.3° (c,
Constit. of Chamaecyparis pisifera. Cryst. 1.1 in CHCI 3).
(C 6H 6/hexane). Mp 62-64.SO. [cx]i,S -8.2° (c, 0.7 in 19-( Carboxyacetyl):
MeOH). C 23H 320 4 M 372.503

815
8-Abietene-7,13-diol- 8-Abietene-14,18-diol Di-00912 - Di-00916

Constit. of C. ascendens. Oil (as Me ester). [IX]~ + 32.5° 8(14)-Abietene-3,13-diol Di-00914

(c, 0.6 in CHC1 3) (Me ester).
19-Carboxylic acid: [5155-70-4]. 8,11 ,13-Abietatrien-19-oic
acid. Callitrisic acid
C10H 280 1 M 300.440
Constit. of Ca/litris columel/aris. Cryst. (hexane). Mp
144.2°. [1X]n + 132° (c, 0.5 in EtOH).
12-Hydroxy: 8,11,13-Abietatriene-12,19-dio/. 19- HO'
Hydroxyferruginol
C10H:11,01 M 302.456 C10H 340 1 M 306.487
Constit. of Podocarpus ferrugineus. Plates (ent-3P,13f/)-form [50657-04-0] Missourienol B
(CHC1 3fhexane). Mp 185.4-186.4°. Constit. of Solidago missouriensis. Cryst. (Et20). Mp
12-Hydroxy, 19-Ac: 155-156°. [1X]~ -47° (c, 1.65 in CHC1 3).
C11H 310 3 M 344.493 3-Ketone: [50657-03-9]. ent-13P-Hydroxy-8(14)-abieten-3-
From P. ferrugineus. Gum. one. Missourienol A
12-Hydroxy, 19-carboxy/ic acid: [55051-96-2]. 12-Hydroxy- C10H 310 1 M 304.472
8,11,13-abietatrien-19-oic acid. Lambertic acid Constit. of S. missouriensis. Cryst. (Et20/CC14). Mp 80-
C10H 280 3 M 316.439 840. [IX]~ -3° (c, 2.25 in CHC1 3).
Constit. of P. /ambertius. Cryst. Mp 252-254°. [1X]i;1 Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073.
+ 121.SO (c, 0.03 in EtOH).
Carman, R.M. et at, Aust. J. Chern., 1967, 20, 2789 (synth) 8(14)-Abietene-7,13-diol Di-00915
Schmidt, E.N. et at, Khim. Prir. Soedin., 1969, 5, 187 (deriv)
Campello, J. de P. et al, Phytochemistry, 1975, 14, 243 (Lambertic OH
acid)
Welsh, S.C. eta/, J. Org. Chern., 1977, 42, 2879 (synth)
Cambie, R.C. eta/, Phytochemistry, 1984, 23, 333 (19-
Hydroxyferrugino/)
Chamy, M.C. eta/, Phytochemistry, 1987,. 26, 1763 (isol)

8-Abietene-7,13-diol Dl-00912 C10H 340 1 M 306.487

(7«,13(.)-form [50816-28-9] Junceanol Y
Constit. of Solidago juncea. Cryst. (Etpjpet. ether). Mp
136-140°. [1X]n -34° (c, 2 in CHC1 3).
Henderson, M.S. eta/, Can. J. Chern., 1973, 51, 1322.

8-Abietene-14,18-diol Dl-00916

C10H 340 1 M 306.487

(7P,13f/)-form [10441-95-9]1bozol
Constit. of lboza riparia. Cryst. (Me2CO). Mp 146-150°.
Zelnik, R. eta/, Phytochemistry, 1978, 17, 1795.

8(14)-Abietene-2,13-diol Di-00913
CH20H
18

C10H 340 1 M 306.487

14«-form [51593-41-0] Suaveolol
Constit. of Hyptis suaveolens. Cryst. (CH 2Cl2fhexane).
Mp 186-187°. [IX]~ +81.3° (c, 1.02 in CHC1 3).
18-Carboxy/ic acid: [51593-38-5]. 14-Hydroxy-8-abieten-18-
oic acid. Suaveolic acid
C10H 340 1 M 306.487 C10H 310 3 M 320.471
(ent-2«,13f/)-form Constit. of H. suaveolens. Cryst. (MeOH aq.). Mp 198-
2-Ac: [50299-50-8]. ent-21X-Acetoxy-8(14)-abieten-13P-ol. 201° dec. [IX]~ + 68.2° (c, 1.8 in CHC1 3).
Missourienol C Manchand, P.S. et a/, J. Org. Chern., 1974, 39, 2306.
C11H 360 3 M 348.525
Constit. of Solidago missouriensis. Oil. [IX]~ + 7° (c, 1.7
in CHC13).
Anthonsen, T. eta/, Acta Chern. Scand., 1973, 27, 1073.

816
8(14)-Abietene-6,7,13-triol - Carnosol Di-00917 - Di-00922

8(14)-Abietene-6,7,13-triol Dl-00917 Callicarpone Di-00920

12,13-Epoxy-15-hydroxy-8-abietene-7,11-dione
[5938-11-4]

C 20H 340 3 M 322.487

(6«,7«,13~)-form
C20H 280 4 M 332.439
6-(3-Methyl-2-butenoyl): [50816-27-8]. Junceano/ X Constit. of Callicarpa candicans. Potent fish poison. Pale
C 25H 400 4 M 404.589 yellow cryst. Mp 111-112°. [IX]~ -188° (c, 1.0 in
Cons tit. of Solidago juncea. Oil. [1X]n - 11° (c, 1.3 in CHCIJ.
CHCI 3). Kawazu, K. eta/, Agric. Bioi. Chern., 1967, 31, 498.
7-(3-Methyl-2-butenoyl): [50816-26-7]. Junceanol W
C 25 H 400 4 M 404.589
Constit. of S. juncea. Oil. Canariquinone Di-00921
71X- Ethoxy-12-hydroxy-8,12-abietadiene-20,6ft-olide
Henderson, M.S. eta/, Can. J. Chern., 1973, 51, 1322.
[121927-69-3]
8-Abieten-18-oic acid Di-00918

C22 H 280 6 M 388.460

COC>H Constit. of Salvia canariensis. Amorph. yellow solid.
C20H 320 2 M 304.472 Gonzalez, A. G. eta/, Can. J. Chern., 1989, 67, 208 (iso/, prnr, crnr)
13P-form [19407-36-4] Dihydropa/ustric acid
Cryst. (AcOH). Mp 179-181°. [1Xji: +115° (CHCI 3). Carnosol Di-00922
Me ester: 11 ,12-Dihydroxy-8,11 ,13-abietatrien-20,7ft-olide. P,icrosalvin
C21H340 2 M 318.498 [5957-80-2]
Constit. of Cistus labdaniferus. Oil. Bp0 .02 153-155°. [1X]i;'
+39°.
Tabacik-Wlotzka, C. eta/, Bull. Soc. Chirn. Fr., 1963, 2299 (isol)
Herz, W. eta/, J. Org. Chern., 1965, 30, 1881 (synth)

8,11,13-Abietriene-7,11,12-triol Di-00919

C 20 H 260 4 M 330.423
Bitter principle in Salvia carnosa, S. officina/is, S. triloba
and Rosmarinus officina/is. Cryst. (EtOH). Mp 221-226°.
[1X]n -66° (EtOH).
Di-Me ether: [25460-12-2].
Cryst. (CHCI 3). Mp 155-156°. [1X]n -73.SO (c, 0.95 in
C 20H 300 3 M 318.455 CHCI 3).
7P-form Deoxo: 7,20-Epoxy-8,11 ,13-abietatriene-11 ,12-diol. 20-
7,12-JJi-Me ether: [34327-32-7]. 7p,l2-Dimethoxy-8,11,13- Deoxocarnoso/
abietatrien-11-ol C20 H 280 3 M 316.439
C22 H 340 3 M 346.509 Constit. of Coleus barbatus. Yellow solid
lsol. from wood of Juniperus rigida. (CH 2Cl 2/hexane). Mp l73.5-l75.SO. [1X]n -78.8° (c, I in
7-Et, 12-Me ether: [34327-33-8]. 7P-Ethoxy-12-methoxy- CHCI 3).
8,11,13-abietatrien-11-ol Deoxo, 0 12 -Me: Deoxycarnoso/12-methy/ ether
C23H 360 3 M 360.536 C21 H 300 3 M 330.466
Isol. from J. rigida. Constit. of S. canariensis. Cryst. Mp 188-190°.
Yanagawa, T. eta/, CA, 1971, 75, 148545a. 61X-Hydroxy: [93780-80-4]. 61X,11,12-Trihydroxy-8,ll,l3-
abeitatrien-20, 7P-o !ide. lsorosmanol
C20H 260 5 M 346.422
Constit. of Rosmarinus officina/is. Cryst. Mp 227°.
12-Deoxy, 14-hydroxy: [92519-82-9]. 11,14-Dihydroxy-
8,11 ,13-abietatrien-20,7-olide. lsocarnosol

817
Carnosolone - 7,12-Dihydroxy-8,12-abietadiene-... Di-00923 - Di-00927

C20H 21;04 M 330.423 6-Deoxy: [126979-82-6]. 7P-Hydroxy-8,13-abietadiene-11,12-

Constit. of S. lanigera. Cryst. (MeOH). Mp 216°. [ex]~ dione
-80° (c, 0.2 in CHC1 3). C20H 280 3 M 316.439
Brieskorn, C.H. et a/, J. Org. Chern., 1964, 29, 2293 (struct, Isol. from S. miltiorrhiza. Yellow cryst.
biosynth) (EtOAcjhexane). Mp 83-84°.
Narayanan, C.R. eta/, Tetrahedron Lett., 1965, 3647 (stereochem) Hueso-Rodriguez, J.A. et al, Phytochemistry, 1983, 22, 2005.
Meyer, W.L. et al, J. Org. Chern., 1976, 41, 1005 (synth) Chang, H.M. et al, J. Org. Chern., 1990, 55, 3537 (deriv)
Nakatani, N. et al, Agric. Bioi. Chern., 1984, 48, 2081
(Isorosmanol)
A1-Hazimi, H.M.G. et al, Phytochemistry, 1984, 23, 919 7,12-Dihydroxy-8, 12-abietadiene-11,14- 01-00926
(lsocarnosol) dione
Ke1ecom, A. eta/, Phytochemistry, 1984, 23, 1677 (Deoxocarnosol) 7-Hydroxyroyleanone
Fraga, B.M. et al, Phytochemistry, 1986, 25, 269 (deriv)
16

Carnosolone Di-00923
6P,20-Epoxy-6,11 ,12-trihydroxy-8,11 ,13-abietatrien-7-one
[72994-80-0]

C20 H 280 4 M 332.439

7rx-form [21887-01-4] Horminone
Constit. of Plectranthus spp. Golden cryst. (MeOH aq.).
Mp 178°. [exJn -132° (c, 1.24 in CHC13).
7-Ac: 7rx-Acetoxyroyleanone. 7-Acetylhorminone
C20H 21;05 M 346.422 C22H300 5 M 374.476
Constit. of Coleus carnosus. Cryst. (Etpjhexane). Mp Isol. from whole plants of Horminum pyrenaicum, roots
151.8-153.6°. of Salvia spp. and leaf glands of Coleus carnosus.
Yoshizaki, F. eta/, Helv. Chim. Acta, 1979, 62, 2754. 7-Formyl: 7-0-Formylhorminone
C21H280 5 M 360.449
Conacytone Di-00924 Constit. of Plectranthus sanguineus. Yellow-orange cryst.
19,20-Epoxy-7ex,12 ,20-trihydroxy-8,12-abietadiene-11, 14-
(hexane). Mp 152.5-154°.
dione. Turbinatrone 7-Me ether: 7-0-Methylhorminone. 7ex-Methoxyroyleanone
[60385-82-2] C21H 300 4 M 346.466
Constit. of Lepechinia bullata. Yellow cryst. (CHC1 3).
Mp 126-128°.
16-Acetoxy, 12-Ac: 16-Acetoxy-12-0-acetylhorminone
C24H 320 7 M 432.513
Constit. of R. lophanthoides. Yellow needles. Mp 158°.
7P-form [21764-41-0] Taxoquinone
Isol. from Taxodium distichum. Mp 214°. [ex]~ +240° (c,
\
\
1.4 in CHC1 3).
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3912 (isol)
C20H 21;06 M 362.422 Hensch, M. et al, Helv. Chim. Acta, 1975, 58, 1921 (isol)
Constit. of Salvia ballotaeflora and Eupatorium turbinatum. Bhat, S.V. et al, Tetrahedron, 1975, 31, 1001 (isol, deriv)
Yellow cryst. (C6H 6). Mp 210-212° dec. [ex]~ -36.SO Matsumoto, T. et al, Bull. Chern. Soc. Jpn., 1979, 52, 1459 (synth)
(CHC1 3). Turbinatone descr. as an oil. Hueso-Rodriguez, J .A. et al, Phytochemistry, 1983, 22, 2005 (isol,
Dominguez, X.A. et al, Planta Med., 1976, 30, 236 (isol, struct) derivs)
Taira, Z. et al, Acta Crystallogr., Sect. B, 1976, 32, 2149 (cryst Mat1oubi-Moghadam, F. eta/, Helv. Chim. Acta, 1987, 70, 975
struct) (isol, deriv)
Jakupovic, J. et al, Phytochemistry, 1986, 25, 2677 (isol) Jonathan, L.T. et al, J. Nat. Prod. (Lloydia), 1989, 52, 571 (isol,
deriv, pmr, cmr)
6,7-Dihydroxy-8,13-abietadiene-11,12- Dl-00925
dione 7,12-Dihydroxy-8,12-abietadiene-11,14,20- Di-00927
trione

C20H 280 4 M 332.439 C20H 260 5 M 346.422

(6rx,7fl)-form [88663-97-2] Salviphlomone 7rx-form
Constit. of Salvia ph/omoides. Deep-red needles l>esacetylnemorone
(EtOAcjhexane). Mp 163-165°. [ex]~ -330.4° (c, 0.232 Isol. from Salvia nemorosa. Mp 195-197°.
in MeOH). 7-Ac: [32764-46-8]. Nemorone

818
8,20-Dihydroxy-9(11),13-abietadien-... - 11,15-Dihydroxy-5,7,9(11),13-... Di-00928 - Di-00933

CnH280 6 M 388.460 6,12-Dibydroxy-5,8,11,13-abietatetraen-7- Dl-00931

Constit. of S. nemorosa and S. lanata. Cryst. (EtOH). one
Mp 192-194° dec.
[34327-29-2]
Romanova, A.S. et al, Khim. Prir. Soedin., 1971, 7, 199 (isol)
Mukherjee, K.S. et al, Phytochemistry, 1981, 20, 1441 (isol, uv, ir)

8,20-Dibydroxy-9(11),13-abietadien-12- Dl-00928
one

CzoH260 3 M 314.424
lsol. from wood of Juniperus rigida.
Yanagawa, T. et al, CA, 1971, 75, 148545a.

CzoH300 3 M 318.455
11,12-Dibydroxy-5,8,11,13-abietatetraen- Dl-00932
Constit. of Austrocedrus chilensis. Cryst. (MeOH). Mp 7-one
149-153°. [1X]~ + J90 (c, 2.6 in CHC1 3). SalPinolone
Cairnes, D.A. et al, J. Nat. Prod. (Lloydia), 1983, 46, 135. [120278-22-0]

3,11-Dibydroxy-5,7,9(11),13- Dl-00929
abietatetraene-2, 12-dione

CzoH 260 3 M 314.424

Constit. of Salvia prionitis. Cryst. Mp 253-254°. [1X]n
+35.8° (c, 0.12 in MeOH).
Lin, L.-Z. et al, Phytochemistry, 1989, 28, 177.
CzoH:z,.04 M 328.407
3fJ-form [121688-14-0]/soblulrangin 11,15-Dibydroxy-5,7,9(11),13- Di-00933
Constit. of Pygmaeopremna herbacea. Brown solid. Mp abietatetraen-12-one
74-76°. [IX]~ -465° (c, 0.115 in CHCl3). Fuerstione. Fuerstiaquinone
Sankaram, A.V.B. et al, Tetrahedron Lett., 1989, 30, 867. [6467-01-2]

2,11-Dibydroxy-5,7,9(11),13- Dl-00930
abietatetraen-12-one
0

C:zJI 260 3 M 314.424

CzoH 260 3 M 314.424
2rz.-form
Constit. of Salvia texana. Reddish-yellow oil.
2-(4-Hydroxybenzoyl): [66656-57-3]. ParPijlorone D
C27H 300 5 M 434.531
Pigment from Plectranthus parviflorus. Deep-red cryst.
(hexanejdiisopropyl ether). Mp 159-161°.
2-(3,4-Dihydroxybenzoyl): [66656-58-4]. ParPijlorone F
C27H 300 6 M 450.530
Pigment from P. parviflorus. Deep-red glass.
Riiedi, P. et al, Helv. Chim. Acta, 1978, 61, 709 (Parviftorones)
Gonzalez, A.G. et al, J. Nat. Prod. (Lloydia), 1989, 52, 1231 (isol)
Constit. of Fuerstia africana and Plectranthus nilgherricus.
Scarlet prismatic needles (pet. ether). Mp 104-107°
approx. (unsharp).
Jfi-Acetoxy: [65714-87-6]. Jfi-Acetoxy-11,15-dihydroxy-
5, 7,9(11 ), 13-abietatetraen-12-one. 3fJ-Acetoxyfuerstione
CnH280 5 M 372.460
Pigment from the leaf glands of P. nilgherricus. Red
cryst. (CH 2Cl 2/diisopropyl ether). Mp 133-135°.
15-Deoxy: 11-Hydroxy-5,7,9(1 1),13-abietatetraen-12-one.
15-Deoxyfuerstione
CzoH 260 2 M 298.424
Constit. of Salvia moorcroftiana. Syrup. [1Xm -327.7° (c,
0.238 in CHCl 3).
Karanatsios, D. et al, Helv. Chim. Acta, 1966, 49, 1151 (struct)
Miyase, T. et al, Helv. Chim. Acta, 1977, 60, 2789 (isol, abs config)
Simoes, F. et al, Phytochemistry, 1986, 25, 755 (15-
Deoxyfuerstione)

819
11,19-Dihydroxy-5,7,9(11),13-... - 11,12-Dihydroxy-8,11,13-abietatrien-... Di-00934 - Di-00939

11,19-Dihydroxy-5,7,9(11),13- Dl-00934 12,16-Dihydroxy-8,11,13-abietatriene-3,7- Dl-00937

abietatetraen-12-one elione
Margocinin
0
[128286-74-8)

CHPH

IDH2 C '
0
C20H 21;03 M 314.424
19-(3-Methy/-2-butenoyl): [66656-54-0). Par11ijlorone A
C20H 21;04 M 330.423
C25H 320 4 M 396.525
Constit. of Azadirachta indica. Plates (CHC1 3). Mp 143-
Pigment from Plectranthus parviflorus. Orange-red oil. 1440.
BPo.ooi 120o.
Ara, I. eta/, Phytochemistry, 1990, 29, 911 (isol, pmr)
19-(4-Hydroxybenzoyl): [66656-56-2). Par11ijlorone C
C27H:ll,05 M 434.531
Pigment from P. parviflorus. Orange-red cryst. 7,15-Dihydroxy-8,11,13-abietatrien-18-oic Di-00938
(hexanejdiisopropyl ether). Mp 147-149°. acid
19-(3,4-Dihydroxybenzoyl): [66700-66-1]. Par11ijlorone E
C27H 300 6 M 450.530
Pigment from P. parviflorus. Deep-red glass.
19-(4-Hydroxy-3-methoxybenzoyl): [66656-55-1].
Parvijlorone B
C28H 320 6 M 464.557
Pigment from P. parviflorus. Deep-red glass. \
Riiedi, P. et a/, Helv. Chim. Acta, 1978, 61, 709. COOH
C20H 280 4 M 332.439
5,12-Dihydroxy-6,8,12-abietatriene-11,14- Dl-00935 7/J-form
dione Constit. of pollen of Cedrus deodara. Needles
(CHC1 3/C 6H 6). Mp 166-168°. [a)~ +24.1° (c, 0.28 in
EtOH).
Ohmoto, T. et al, Chem. Pharm. Bull., 1987, 35, 229.

11,12-Dihydroxy-8,11,13-abietatrien-20- Di-00939
oic acid
Carnosic acid. Deoxypicrosalvinic acid. Salvint
[3650-09-7]
CwH 21;04 M 330.423
5«-form [119767-16-7] Hypargenin F
Constit. of Salvia hypargeia. Antibacterial agent. Dark
red amorph. solid.
U1ube1en, A. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 1178 (isol,
pmr, cmr)

6,12-Dihydroxy-8,11,13-abietatriene-1,7- Dl-00936
dione C20H 280 4 M 332.439
lsol. from Salvia officina/is, S. canariensis, S. apiana and
Rosmarinus officina/is. Cryst. (hexane). Mp 185-190° dec.
[aJii + 191° (c, 1.07 in MeOH).
Di-Ac: Needles (hexane). Mp 212-217° (196-215° dec.).
[a]~ + 139° (c, l.l5 in CHC1 3).
Linde, H. et al, Helv. Chim. Acta, 1964, 47, 1234 (isol, uv, ir, pmr)
Wenkert, E. eta/, J. Org. Chem., 1965, 30, 2931 (isol, ir, pmr,
config)
Narayanan, C.R. et al, Tetrahedron Lett., 1965, 3647 (struct)
C20H 11;04 M 330.423 Meyer, W.L. et al, Tetrahedron Lett., 1966, 4261 (synth)
Dentali, S.J. et a/, Phytochemistry, 1990, 29, 993 (isol)
6/J-form [ll9767-12-3] Hypargenin A
Constit. of Salvia hypargeia. Antibacterial agent. Dark
yellow amorph. solid.
U1ube1en, A. eta/, J. Nat. Prod. (Lloydia), 1988, 51, 1178 (isol,
pmr,)

820
2,11-Dihydroxy-7,9(11),13-... - 6,14-Dihydroxy-8,11,13-abietatrien-... Di-00940 - Di-00946

2,11-Dihydroxy-7 ,9(11 ),13-abietatrien-12- Dl-00940 Cheng, Y.-S., Proc. Nat/. Sci. Counc., Repub. China, Part 1, 1975,
8, 124 (synth, pmr, ir)
one Ara, I. et al, J. Nat. Prod. (Lloydia), 1988, 51, 1054 (Nimosone)
Ara, I. et al, Phytochemistry, 1990, 29, 911 (isol, pmr)

5,12-Dihydroxy-8,11,13-abietatrien-7-one Dl-00944
HO,

C:wH280 3 M 316.439
2rx.-form [116425-75-3] 6-Deoxo-2rx.-hydroxytaxodione
Constit. of Salvia texana. Brownish-yellow oil.
Gonzalez, A.G. eta/, Phytochemistry, 1988, 27, 1777. C20H 280 3 M 316.439
5rx.-form
2,12-Dihydroxy-8,11,13-abietatrien-7-one Dl-00941 Nimolinin
Constit. of Azadirachta indica. Plates (hexane). Mp 113-
1140.
Ara, I. eta/, J. Nat. Prod. (Lloydia), 1989, 52, 1209 (isol, pmr,
cmr)
HO,

6,11-Dihydroxy-7,9,11(13)-abietatrien-12- Dl-00945
one
C 20H 280 3 M 316.439
2rx.-form
2rx.-Hydroxysugiol
Constit: of Salvia cardiophylla. Cryst. (EtOAcjpet.
ether). Mp 269-271°.
Gonzalez, A.G. et al, Phytochemistry, 1988, 27, 1540.

3,12-Dihydroxy-8,11, 13-abietatrien-1-one Dl-00942 C20H 280 3 M 316.439

6rx.-form
Taxodone
Isol. from Taxodium distichum. Tumour inhibitor.
Yellow plates (Et20jpet. ether). Mp 164-165°. [cx]i,S
+ 50° (c, 2.5 in CHC1 3).
6-Ketone: [19026-31-4]. 1)-Hydroxy-7,9j11),J3-abiotntriene-
6,12-dione. Taxodione
C20H 11;03 M 314.424
C20H 280 3 M 316.439 Isol. from T. distichum. Tumour inhibitor. Goldt;IYplates
3P-form (MeOH). Mp 115-IW. [cx)i,S +56° (c, 1 in CHC1 3).
1-0xohinokiol
Kupchan, S.M. eta/, J. Org. Chern., 1969, 34, 3912 (isol, struct)
Constit. of Calocedrus formosana. Cryst. Mp 228-229°. MatS\llllOto, T. et al, Bull. Chern. Soc. Jpn., 1977, 50, 1575 (synth)
[cx]i,S + 130° (c, 0.68 in Me2CO). Johnson, W.S. et al, Tetrahedron, 1982, 38, 1397 (synth)
Fang, J.-M. eta/, Phytochemistry, 1987, 26, 853. Burnell, R.H. eta/, Can. J. Chern., 1987, 65, 775 (synth)

3,12-Dihydroxy-8,11 ,13-abietatrien-7-one Dl-0~ (j ,14-Dihydroxy-8,11 ,13-abietatrien-1-one Dl-00946

C:wll280 3 M 316.439
C20H 280 3 M 316.439
3P-form [61494-71-1] Margocilin
6P-form [119767-15-6] Hypargenin E
Constit. of Azadirachta indica. Needles (CHC1 3). Mp
Cc.1stit. of Salvia hypargeia. Amorph.
249-250° (126-127°).
Ulubelen, A. et a/, J. Nat. Prod. (Lloydia), 1988, 51, 1178 (isol,
3-Ketone: [61494-73-3]. 12-Hydroxy-8,11,13-abietatriene-
pmr)
3,7-dione. Nimosone
C20H 21;03 M 314.424
lsol. from A. indica. Needles (CHC1 3). Mp 72-73°.

821
12,15-Dihydroxy-8,11,13-abietatrien-... - 15-Hydroxy-7,13-abietadien-18-... Di-00947 - Di-00952

12,15-Dihydroxy-8, 11,13-abietatrien-7-one Dl-00947 12-Hydroxy-8,12-abietadiene-11,14-dione Di-00950

Hypargenin B Royleanone
[119767-13-4] [6812-87 -9]

C20H 280 3 M 316.439 C20H 280 3 M 316.439

Constit. of Salvia hypargeia. Antibacterial agent. Orange Constit. of Inula royleana. Also from Plectranthus spp. and
amorph. solid. Podocarpus ferrugineus. Orange-yellow cryst. (AcOH).
Ulubelen, A. et at, J. Nat. Prod. (Lloydia), 1988, 51, 1178 (isol, Mp 181.5-183°. [aJn + 134° (c, 1.03 in CHC1 3).
pmr) 6,7-Didehydro: [6855-99-8]. 12-Hydroxy-6,8,12-abietatriene-
11 ,14-dione. 6,7-Dehydroroyleanone
9,13-Epidioxy-8(14)-abieten-18-oic acid Di-00948 C20 H 260 3 M 314.424
8(14)-Abieten-18-oic acid 9,13-endoperoxide Constit. of I. royleana and Plectranthus spp. Cryst.
(MeOH). Mp 167°. [aJn -620° (c, 0.2 in CHC1 3).
7a-Acetoxy, 20-hydroxy: 7rx.-Acetoxy-12,20-dihydroxy-8,12-
abietadiene-11 ,14-dione
C22H34P 6 M 390.475
Constit. of Salvia lanata. Brown plates (CHC1 3fhexane).
Mp 160-162°.
2P-Hydroxy: 2P,12-Dihydroxy-8, 12-abietadiene-ll, 14-dione.
(9cx, 13cx)-:form 2P-Hydroxyroyleanone
C20H 280 4 M 332.439
C20H 300 4 M 334.455 Constit. of S. cryptantha. Oil.
(9rx.,13rx.)-form Hersch, M. et al, Helv. Chim. Acta, 1975, 58, 1921 (isol)
Cons tit. of Elodea canadensis. Matsumoto, T. et at, Bull. Chern. Soc. Jpn., 1977, 50, 266 (synth)
3P-Hydroxy: 9,13-Epidioxy-Jp-hydroxy-8(14)-abieten-18-oic Mukherjee, K.S. et at, Phytochemistry, 1983, 22, 1296 (deriv)
acid. Jp-Hydroxy-8(14)-abieten-18-oic acid 9a,13- Ulubelen, A. et at, Phytochemistry, 1987, 26, 1534 (2P-
endoperoxide Hydroxyroyleanone)
King, J. et a/, Tetrahedron Lett., 1990, 31, 5221 (synth)
C20H34P5 M 350.454
Constit. of a Salvia sp. Cryst. (EtOAcfhexane) (as Me
ester). Mp 158-161° (Me ester). 12-Hydroxy-8,12-abietadiene-7,11,14- Di-00951
3P-Acetoxy: 3P-Acetoxy-9rx.,13rx.-epidioxy-8(14)-abieten-18- trione
oic acid. JP-Acetoxy-8(14)-abieten-18-oic acid 9a,13a- 7-0xoroyleanone. 7-Ketoroyleanone
endoperoxide [57685-32-2]
C 22H~2 0 6 M 392.491
Constit. of a S. sp. Cryst. (EtOAcfhexane) (as Me
-ester). Mp 153-155° (Me ester). [ali? -54.6° (c, 0.03 in
CHC1 3) (Me ester).
(9p,l3p)-form
Constit. of E. canadensis.
Escudero, J. et al, Phytochemistry, 1983, 22, 585.
Monaco, P. eta{, Tetrahedron Lett., 1987, 28, 4609.
C20 H 260 4 M 330.423
17-Hydroxy-8(14),13(15)-abietadien-16-al Dl-00949 Constit. of roots of Inula royleana. Red-brown cryst.
(MeOH). Mp 203-205°.
CHO Bhat, S.V. eta/, Tetrahedron, !975, 31, 1001 (isol, struct)
Matsumato, T. et al, Chern. Lett., 1976, 1311 (synth)

15-:-Hydroxy-7,13-abietadien-18-oic acid Di-00952

15-Hydroxyabietic acid

OH

C20H 300 2 M 302.456

ent-form [130395-21-0]
Constit. of Euphorbia fidjiana. Oil.
La!, A.R. et at, Phytochemistry, 1990, 29, 2239 (isol, pmr, cmr)
/
HOOC
C20 H 300 3 M 318.455
Constit. of various Agathis spp.

822
13-Hydroxy-18-abietanoic acid- 12-Hydroxy-8,11,13-abietatrien-7-... Di-00953 - Di-00958

Me ester: [29461-22-1]. 11-Hydroxy-7,9(11),13-abietatriene- Dl-00956

Gum. [ocln -70°. 2,6,12-trione
Carman, R.M. et a/, Aust. J. Chern., 1970, 23, 1457. 2-0xotaxodione

13-Hydroxy-18-abietanoic acid Dl-00953

C20H 240 4 M 328.407

Constit. of Salvia texana. Yellow oil.
C20H 340 3 M 322.487
Gonzalez, A. G. et a/, Heterocycles, 1989, 52, 1231 (isol, pmr)
13/l-form [122247-21-6]
Constit. of Pinus radiata.
3-Hydroxy-8,11,13-abietatrien-18-oic acid Dl-00957
Wilkins, A.L. et al, Aust. J. Chern., 1989, 42, 983 (isol, pmr, cmr)
3-Hydroxydehydroabietic acid

7-Hydroxy-8,11,13-abietatrien-19-al Dl-00954

3ft-form
C20H 280 2 M 300.440
7«-form [68268-75-7]
Constit. of Juniperus phoenicea. Oil.
De Pascual Teresa, J. et a/, An. Quim., 1978, 74, 465.
12-Hydroxy-8,11,13-abietatriene-6,7-dione Dl-00955
5rx-form
12-Hydroxy-8,11, 13-abietatrien-7-one
C20H 11,03 M 314.424
5«-form [119817-27-5] Prexanthoperol. Hypargenin C
C20H 21,03 M 314.424
Minor constit. of Juniperus communis and also from
Salvia hypargeia. Yellow cryst. or orange amorph. solid.
Mp 207-210°. Identity of Prexanthoperol and
Hypargenin C not definitely establ.
5/l-form [564-23-8] Xanthoperol
Constit. of Juniperus communis and other woods, e.g.
Podocarpus dacrydioides, Cryptomeria japonica. Yellow
cryst. (C6H 6). Mp 255-270° dec. [oc]~ + 132.SO (c, 1.2 in
EtOH).
Ac: Yellow cryst. (EtOH aq.). Mp 157.5-158.SO.
Me ether: Yellow cryst. (MeOH aq.). Mp 190-192°.
Brendenberg, J.B. et al, Acta Chern. Scand., 1956, 10, 1511 (isol)
Nasipuri, D. eta/, J. Chern. Soc., 1962, 4248 (synth)
Kondo, Y. eta/, Chern. Pharm. Bull., 1963, 11, 678 (struct)
Ulubelen, A. et al, J. Nat. Prod. (Lioydia), 1988, 51, 1178 (isol,
pmr, cmr) · Cambie, R.C. et al, Aust. J. Chern., 1971, 24, 217 (isol)
CooH
C20 H 280 3 M 316.439
Constit. of Salvia spp.
3-Ac, Me ester: Cryst. (EtOAcjhexane). Mp 160-161°. [ali?
+53.7° (c, 0.1 in CHC1 3).
15,16-Didehydro: [77091-10-2]. 3fJ-Hydroxy-8,11,13,15-
abietatetraen-18-oic acid
C20H 260 3 M 314.424
Constit. of S. tomentosa. Cryst. (EtOH). Mp 182-184°.
[oc]~ +86.6° (EtOH).
Ulubelen, A. et al, J. Nat. Prod. (Lloydia), 1981, 44, 119.
Escudero, J. et al, Phytochemistry, 1983, 22, 585.
Dl-00958
Sugiol. Isomicropinic acid. 7-0xoferruginol
[511-05-7]
OH
C20 H 280 2 M 300.440
Constit. of Cryptomeria japonica, Dacrydium cupressinum,
Juniperus communis and Salvia miltiorrhiza. Cryst.
(AcOH). Mp 295-297°. [a]~ +22.6° (c, 1.2 in dioxan).
5,6-Didehydro: [21764-42-1]. 12-Hydroxy-5,8,11,13-
abietatetraen-7-one. 5,6-Dehydrosugiol
C20 H 260 2 M 298.424
Constit. of Taxodium distichum. Cryst. (Me2COjpet.
ether). Mp 284-286°. [a]i;l + 13° (c, 1 in EtOH).
Kupchan, S.M. et a/, J. Org. Chern., 1969, 34, 3912 (isol)
Meyer, W.L. et al, J. Org. Chern., 1915, 40, 3686 (synth, bib[)
Matsumoto, T. et al, Bull. Chern. Soc. Jpn., 1977, 50, 1575 (bib[)
Chang, H.M. eta/, J. Org. Chern., 1990, ·55, 3537 (isol, pmr, cmr)

823
8-Hydroxy-12-oxo-13-abieten-18-... - 2,6,7,11-Tetrahydroxy-5,7,9(11),13-... Di-00959 - Di-00964

8-Hydroxy-12-oxo-13-abieten-18-oic acid Dl-00959 From R. officina/is. Pale-brown powder. [1X]i; -99.2° (c,
0.5 in EtOH).
0 11 ,12-Quinone: 71X-Hydroxy-II, 12-dioxo-8, 13-abietadien-
20,6P-olide. Rosmaquinone
C 20H 240 5 M 344.407
Constit. of Salvia canariensis. Red-yellow amorph. solid.
7-Et ether: 7-Ethoxyros11Ullfol
CnH300 5 M 374.476
Constit. of S. canariensis. Gum.
Gonzalez, A.G. et al, Experientia, 1973, 29, 1471 (Galdosol)
CzoH34,04 M 334.455 Nakatani, N. eta/, Agric. Bioi. Chern., 1981, 45, 2385 (Rosmanol)
8«.-form [130252-62-9] Nakatani, N. eta/, Agric. Bioi. Chern., 1984, 48, 2081
Constit. of Pinus sy/vestris. (Epirosmanol)
Fraga, B.N. eta/, Phytochemistry, 1985, 24, 1853 (cryst struct)
Buratti, L. eta/, Phyt()chemistry, 1990, 29, 2708 (isol, pmr, ms) Arisawa, M. et al, J. Nat. Prod. (Lloydia), 1987, 50, 1164
(Methoxyrosmanol)
9-Hydroxy-7-oxo-15-abieten-18-oic acid Dl-00960 Gonzalez, A. G. eta/, Can. J. Chern., 1989, 67, 208 (isol, pmr, cmr)

~-~
6,7,12,16-Tetrabydroxy-8,12-abietadiene- Dl-00963
11,14-dione
16
CHPH

~0
CzoH300 4 M 334.455
'h.-form (129385-69-9] Wiedenuuuric acid
Constit. of Salvia wiedemannii.
Topcu, G. et a/, Phytochemistry, 1990, 29, 2346 (isol, pmr, cmr)
CmH200 6 M 364.438
(6p,7rx.)-form
Hyptol Dl-00961
12,16-Epoxy-11 ,14-dihydroxy-8,11 ,13-abietatrien-7-one 7-Ac: [120462-43-3]. Lop/umthoidin C
C22H 300 7 M 406.475
[65563-54-4]
Constit. of Rabdosia /ophanthoides. Cryst. Mp 167-
169.SO.
16-Ac