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REVIEW www.rsc.org/npr | Natural Product Reports

Marine natural products

John W. Blunt,*a Brent R. Copp,b Murray H. G. Munro,a Peter T. Northcotec and Michele R. Prinsepd
Received 30th October 2009
First published as an Advance Article on the web 7th January 2010
DOI: 10.1039/b906091j

Covering: 2008. Previous review: Nat. Prod. Rep., 2009, 26, 170

This review covers the literature published in 2008 for marine natural products, with 829 citations
(613 for the period January to December 2008) referring to compounds isolated from marine
microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians,
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bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and
microorganisms. The emphasis is on new compounds (1065 for 2008), together with the relevant
biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses,
and syntheses that lead to the revision of structures or stereochemistries, have been included.

1 Introduction determined for all stereocentres in a compound, the identifying

2 Reviews diagram number is distinguished by addition of a † symbol.
3 Marine microorganisms and phytoplankton Configurations shown for compounds not labelled with † should be
4 Green algae assumed to be relative. A new section in this review (Mangroves and
5 Brown algae the intertidal zone) includes metabolites from both true- and semi-
6 Red algae mangrove plants and other entities such as sea-grasses, succulents
7 Sponges and microorganisms isolated from the intertidal zone. Further
8 Cnidarians discussion of the rationale for this change is given in that section.
9 Bryozoans A disturbing trend has been noted in which duplicate publication
10 Molluscs of the same new compound is occurring in different journals, often
11 Tunicates (ascidians) originating from the same research group. Sometimes this
12 Echinoderms duplication is disguised by the use of different names for the same
13 Mangroves and the intertidal zone compounds.
14 Miscellaneous
15 Conclusion
16 Acknowledgement 2 Reviews
17 References
A comprehensive review of marine natural products reported in
2006 has appeared,1 as well as the highlights of compounds
reported in 2007.2 Deep-sea natural products have been
reviewed,3 as have bioactives from Okinawan waters.4 There
1 Introduction have been two reviews of the drug potential for marine natural
This review is of the literature for 2008 and describes 1065 new products,5,6 and further reviews relating to specific types of
compounds from 371 articles, an increase of 11% from the number bioactivity, such as antitumour and cytotoxicity,7–12 anti-
of compounds reported for 2007. This is the first year that the inflammatory,13 marine antiviral products,14 antimalarial
number of new compounds being reported has exceeded 1000. As in epsipeptides from microorganisms,15 and aromatase inhibitors.16
previous reviews, the structures are shown only for new compounds, Marine toxins have been extensively reviewed in papers on
or for previously reported compounds where there has been palytoxin,17 pectenotoxins,18 cyanobacterial toxins as
a structural revision or a newly established stereochemistry. allelochemicals,19 polyether biotoxins,20 azaspiracids,21
Previously reported compounds for which first syntheses or new yessotoxins, domoic acid, neurotoxins from dinoflagellates,24
22 23

bioactivities are described are referenced, but separate structures are
generally not shown. Where the absolute configuration has been
a
Department of Chemistry, University of Canterbury, Christchurch, New
Zealand. E-mail: john.blunt@canterbury.ac.nz
b
Department of Chemistry, University of Auckland, Auckland, New
Zealand
c
School of Chemical and Physical Sciences, Victoria University of
Wellington, Wellington, New Zealand
d
Department of Chemistry, University of Waikato, Hamilton, New
Zealand
vectors for saxitoxins,25 biotoxins from Mexican algal blooms,26
toxins from cone snails,27 structural features of dinoflagellate
toxins,28 brevetoxin,29 polyether toxins from planktonic dino-
flagellates,30 and cyclic imine toxins.31 Regulatory methods used
for the determination of marine toxins have been reviewed.32
Other specific compounds or classes of compounds were
reviewed in papers on lamellarins,33–35 acetylenic compounds,36
aeruginosins,37 FMRFamide and related peptides from
mollusca,38 guanidine alkaloids,39,40 antiangiogenic alkaloids,41
manzamine alkaloids,42 neurotoxic alkaloids from

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cyanobacteria,43 bromopyrroles,44 cephalostatins and ritter-
azines,45,46 discodermolide,47 zoanthamine alkaloids,48 fur-
anocembranoids, pseudopteranes and gersolanes,49 tetramic and
John Blunt obtained his BSc
(Hons) and PhD degrees from
the University of Canterbury,
followed by postdoctoral
appointments in Biochemistry at
the University of Wisconsin–
Madison, and with Sir Ewart
Jones at Oxford University. He
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took up a lectureship at the
University of Canterbury in
1970, from where he retired as
an Emeritus Professor in 2008.
His research interests are with
John Blunt
natural products, and the appli-
cation of NMR techniques to
structural problems.
Brent Copp received his BSc
(Hons) and PhD degrees from
the University of Canterbury,
where he studied the isolation,
structure elucidation and struc-
ture–activity relationships of
biologically active marine
natural products under the
guidance of Professors Blunt
and Munro. He undertook
postdoctoral research with Jon
Clardy at Cornell and Chris
Ireland at the University of
Brent Copp Utah. 1992–93 was spent
working in industry as an isola-
tion chemist with Xenova Plc, before returning to New Zealand to
take a lectureship at the University of Auckland, where he is
currently an Associate Professor.
Murray Munro, now an Emer-
itus Professor at the University
of Canterbury, has worked on
natural products, mainly of New
Zealand origin, right through his
career. This started with diter-
penoids (PhD), followed by
alkaloids during a postdoctoral
spell with Alan Battersby at
Liverpool. Following a sabbat-
ical with Ken Rinehart at the
University of Illinois in 1973, an
interest in marine natural prod-
Murray Munro ucts developed with a particular
focus on bioactive compounds.
In recent years his research interests have widened to include
terrestrial and marine fungi and actinomycetes as well as marine
invertebrates.
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tetronic acids,50 fatty acids,51 amphidinolides,52 sphingolipids,53
3-alkylpyridinium and 3-alkylpyridines from sponges,54 tri-
terpenoids,55 macrolactins,56 steroids from starfish,57 glyco-
sphingolipids from starfish and sea feathers,58 sulfated glycosides
from echinoderms,59 triterpene glycosides from sea cucumbers,60
briarane diterpenoids,61 sesquiterpenoids,62 spongistatins,63
cyclobutane alkaloids,64 thyrsiferol and analogues,65 and myco-
sporines.66 Ecological topics were covered in a general review67
and papers on marine fungal biotechnology,68 symbiosis of
sponges and microbes,69 Antarctic ecology,70 ecobiology of bre-
vetoxin, ciguatoxin and cyclic imines,71 and the ecological
implications of modulators of the transcription factor NF-kB.72
Compounds from specific types of organisms have been reviewed
in articles on mangroves,73 marine cyanobacteria,74,75 bioactives
from marine microorganisms,76 and fungi from the South China
Sea.77 Biosynthesis topics were covered in papers on microor-
ganism–invertebrate assemblages,78 terpenoid drugs using engi-
neered microorganisms,79 polyacetylenes,80 and the biosynthesis
of disulfide bridges and their role in the control of folding in
many conotoxins.81 Reviews of methodologies of interest to
marine natural product discovery programs appeared in papers
on countercurrent separation82 and high impact technologies.83
The fourth in a companion series providing a broad review of
Peter Northcote received his
BSc and PhD degrees from the
University of British Columbia,
Canada, where he was a member
of R. J. Andersen’s marine
natural products research group.
He carried out postdoctoral
research with Professors Blunt
and Munro at the University of
Canterbury before taking
a position as a senior research
scientist at Lederle Laborato-
ries, American Cyanamid Co.
Peter Northcote He joined the faculty of the
Victoria University of
Wellington in 1994, where he is currently an Associate Professor in
organic chemistry.
Mich ele Prinsep received her
BSc (Hons) and PhD degrees
from the University of Canter-
bury, where she studied the
isolation and structural elucida-
tion of biologically active
secondary metabolites from
sponges and bryozoans under the
supervision of Professors Blunt
and Munro. She undertook
postdoctoral research on cyano-
bacteria with Richard Moore at
the University of Hawaii before
Michele Prinsep returning to New Zealand to
take up a lectureship at the
University of Waikato, where she is currently a Senior Lecturer.
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synthetic aspects of marine natural products, covering publica-
tions in 2006, has appeared,84 while more specific reviews that
appeared in 2008 relating to the synthesis of marine natural
products will be referenced in the sixth of this broad review
series. The MarinLit database85 has been updated and was used
as the literature source for the preparation of this present review.
3 Marine microorganisms and phytoplankton
Microorganisms continue to be a productive focus for much of
marine natural products research. Unhappily, however, a feature
that seems to be creeping into this area is the isolation of
unidentified microorganisms from loosely described, or uniden-
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tified, sources. This lack of proper documentation and charac-
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terisation is of concern and appears to be bypassing the attention
of journal editors. Unless molecular approaches are used there
can be difficulty in identifying a microorganism especially in
instances of non-sporulation, but the reporting of locations and
origins should not be problematic. Most journals have guidelines
for the reporting of biological sources. Researchers are therefore
urged to give as much detail as possible about the microorgan-
isms studied. A novel mycothiol homologue, N-propionyl-des-
acetyl-mycothiol 1, was isolated from thirteen of seventeen
cultured strains of actinomycetes obtained predominantly from
Guam and was the main thiol present when nutrients were
depleted and secondary metabolite production occurred.86 Four
polyketides, salinipyrone A 2 and B 3 and pacificanone A 4 and B
5, each comprised of acetate, propionate and butyrate units, were
isolated from culture of Salinispora pacifica (sediment, Palau).
Salinipyrone A 2 exhibited moderate inhibition of interleukin-5
production without cytotoxicity to HCT-116 cells.87 Culture of
Salinispora arenicola (sediment, Palau) yielded the diketopiper-
azines cyclomarazine A 6 and B 7 and a cyclic heptapeptide
cyclomarin D 8. Stable isotope feeding experiments on the
cyclomarin A88 producer, a Streptomyces sp., led to the eluci-
dation of the biosynthesis of this metabolite, while DNA
sequence analysis and gene inactivation experiments identified
the biosynthetic gene cluster in S. arenicola. Further experiments
elucidated the biosynthesis of amino acid residues in the
cyclomarin series and showed that one residue was derived
from a newly identified pathway by condensation of
isobutyraldehyde and pyruvate with subsequent methylation via
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S-adenosylmethionine.89 In a study that typifies the direction
that much natural product research is heading in, sequencing of
the genome of the marine actinomycete Salinispora tropica and
analysis of all identifiable natural product gene clusters indicated
that in the S. tropica genome, a high proportion was dedicated to
natural product biosynthesis and that the majority of the
seventeen identified biosynthetic loci were novel. Bioinformatic
analysis was used in the structural elucidation of a polyene
macrolactam, salinilactam A 9, and in turn, structural analysis
assisted in the genome assembly, demonstrating the power and
utility of combining genomic analysis with traditional isolation
techniques.90 Culture of a Marinispora sp. (sediment, Mission
Bay, San Diego) yielded lynamicins A–E 10–14, chlorinated
bisindole pyrroles with broad-spectrum activity against Gram-
positive and Gram-negative organisms, in addition to activity
against methicillin-resistant Staphylococcus aureus (MRSA)
and vancomycin-resistant Enterococcus faecium (VREF).91
Marinopyrroles A 15 and B 16 are halogenated axially chiral
bispyrroles obtained from culture of a Streptomyces sp. (sedi-
ment, La Jolla, California). Although they exist as a single
atropisomer at room temperature they can be racemised at
a higher temperature. Marinopyrroles A 15 and B 16 exhibited
potent activity against MRSA and moderate activity against
HCT-116 cancer cells.92 The napyradiomycins are chlorinated
meroterpenoid antibiotics produced by several species of acti-
nomycetes including marine sediment-derived Streptomyces.93
Cloning and sequence analysis of the biosynthetic gene cluster
that codes for the napyradiomycins indicated that vanadium-
dependent chloroperoxidases were implicated in the biosynthesis
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to normal (Vero) cells.99 Culture of a Streptomyces strain

(sediment, Laguna de Terminos, Gulf of Mexico) has yielded
two dodecanoic acid derivatives, a butenolide 31 and the respective
acid 32.100
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of these metabolites. Heterologous expression of the cluster in S.

albus produced a number of napyradiomycins, including the new Phaechromycins F–H 33–35 are polyketides isolated from
analogue 17.94 Cultivation of a Streptomyces species (saline mud, culture of a Streptomyces species (deep sea sediment, Western
Tokushima, Japan) yielded two new terpenoids, a 5-dimethyl-
Pacific Ocean) with weak to modest cytotoxicity against the
allylindole-3-carboxylic acid 18, and a quinone 19 which was HeLa cell line.101 Culture of a Streptomyces-related actinomycete
weakly active against B. subtilis.95 Essramycin 20 is a tri- (marine sediment, location not given) yielded the spiroaminals
azolopyrimidine antibiotic obtained from culture of a Strepto- marineosin A 36 and B 37, selective inhibitors of HCT-116 cells.
myces sp. (sediment, Paltium coast, Egypt) and was active
against a range of Gram-positive and Gram-negative bacteria.96
Culture of a Streptomyces sp. separated from the sponge
Halichondria panicea (Baltic Sea, Germany) yielded the strepto-
phenazines A–H 21–28, several of which showed weak to moderate
activity against B. subtilis and Staphylococcus lentus. Addition of
subinhibitory concentrations of antibiotics to the cultivation media
affected the pattern of streptophenazine production depending on
the antibiotic added.97 Cultivation of a Streptomyces strain asso-
ciated with the ascidian Aplidium lenticulum (Great Barrier Reef)
led to the isolation of cinnamoylphosphoramide 29, a weak
inhibitor of acetylcholinesterase.98 A Streptomyces sp. (sediment,
Hawaii) yielded a polyether metabolite 30 with antiprotozoal
activity against both chloroquine-susceptible and chloroquine-
resistant clones of Plasmodium falciparum, but without cytotoxicity

Marineosin A 36 was an order of magnitude more active than

marineosin B 37 and displayed selective cytotoxicity against
melanoma and leukaemia cell lines.102 Cultivation of a Bacillus
subtilis strain from the intestines of the sardine Sardinops

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melanosticta (Toyama Bay, Japan) yielded bacilosarcins A 38
and B 39. These isocoumarins, in addition to the coisolated
amicoumacin A,103,104 were growth inhibitors of barnyard
millet.105 Fermentation of a Bacillus sp. (sediment, East China
Sea) yielded macrolactin S 40 with activity against E. coli,
S. aureus and B. subtilis.106
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Proximicins A–C 41–43 are aminofuran antibiotics isolated
from Verrucosispora maris (sediment, Sea of Japan) (41) and
from a Verrucosispora strain (sediment, Raune Fjord, Norway)
(42 and 43). Proximicin B 42 displayed moderate growth
inhibition of Gram-positive bacteria whilst proximicin C 43 was
slightly inhibitory to Brevibacillus brevis.107 All three proximicins
41–43 were inhibitory to carcinoma cell lines (gastric adenocar-
cinoma, hepatocellular carcinoma (Hep G2) and breast
carcinoma (MCF 7)), inducing upregulation of p53 and the
cyclin kinase inhibitor p21.108
Of the three diapolycopenedioic acid xylosyl esters A–C 44–46
isolated from culture of Rubritalea squalenifaciens from the
sponge Halichondria okadai (Miura peninsula, Kanagawa,
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Japan), 44 exhibited potent antioxidative activity in a superoxide
suppression model.109 Cultivation of Saccharopolyspora cebuen-
sis, derived from the sponge Haliclona sp. (Cebu, Philippines),
yielded the macrolactams cebulactam A1 47 and A2 48.110 Sac-
charothrixins A–C 49–51 are angucyclinones isolated from
cultivation of the actinomycete Saccharothrix espanaensis sepa-
rated from the mollusc Anadara broughtoni (Peter the Great Bay,
Sea of Japan, Russia) which exhibited modest antibacterial
activity.111 A series of cyclic tetrapeptides were isolated from
culture of marine bacteria: culture of a Pseudomonas sp. sepa-
rated from the seaweed Diginea sp. (Ishigaki Is., Okinawa,
Japan) gave peptides 52 and 53, whilst culture of a Pseudoalter-
omonas sp. associated with the sponge Halisarca ectofibrosa
(Burapha, Gulf of Thailand) yielded 54 and 55, in addition to 52.
Peptide 54 was prepared via peptide solid-phase synthesis.112
Zafrin 56 is a broad-spectrum antibiotic isolated from Pseudo-
monas stutzeri separated from the intestinal tract of a ribbonfish
(Desmodema sp.) (Baluchistan Coast, Pakistan), with a proposed
mode of action involving disruption of the cytoplasmic
membrane.113 The fermentation broth of a Photobacterium sp.
isolated from seawater (Onna Beach, Okinawa) yielded two
depsipeptides, unnarmicin A 57 and C 58, which selectively
inhibited two Pseudovibrio bacterial strains.114 Fermentation of
the marine gliding bacterium Rapidithrix sp., obtained from silt
(Ariake Inland Sea, Japan), led to the ariakemicins A 59 and B
60, linear hybrid polyketide-peptides, which selectively inhibited
Gram-positive bacteria and were slightly cytotoxic to A549
human lung cancer cells and baby hamster kidney cells. Aria-
kemicins A 59 and B 60 were inseparable positional isomers
characterised as a relatively unstable mixture.115 A new side-
rophore 61 was isolated from an unidentified bacterial strain
from an unidentified Indonesian sponge.116 Culture of Pseu-
doalteromonas rubra obtained from the sponge Mycale armata
(Kaneohe Bay, Oahu, Hawaii) and a nudibranch (Waikiki,
Oahu, Hawaii) yielded 2-(p-hydroxybenzyl)prodigiosin (HBPG)
62, which displayed identical activity to prodigiosin in human
topoisomerase I inhibition and against human adenocarcinoma
cells.117 Chejuenolides A 63 and B 64 are 17-membered carbo-
cyclic tetraenes isolated from Hahella chejuensis (sediment, Gejae
Is., Korea), which were weak inhibitors of protein tyrosine
phosphatase 1B.118 A red glyco-carotenoic acid ester 65 with
potent antioxidant activity (superoxide suppression) was isolated
from culture of Planococcus maritimus from sediment (Clyde
estuary, UK).119 Nine gentisyl alcohol derivatives – a trimer
(terrestrol A 66), seven dimers (terrestrols B–H 67–73) and
a monomer (74) – were isolated from fermentation of a sediment-
derived Penicillium terrestre (Jiaozhou Bay, China). These
derivatives displayed moderate cytotoxicity to several cancer cell
lines, moderate radical scavenging activity against DPPH, with
terrestrol G 72 also moderately inhibitory to protein tyrosine
kinases.120 80 -Hydroxyzearalanone 75 and 20 -hydroxyzearalanol
76 are resorcyclic acid lactone derivatives obtained from culture
of a Penicillium sp. derived from cotton clothing drifting off
Namhae Is., Gyeongnam, Korea.121 50 -Hydroxyzearalenol 77,
obtained with three other known zearalenols from the marine
Fusarium sp. O5ABR26, was moderately active against Pyricu-
laria oryzae.122 One of two eremophilane sesquiterpenes obtained
from culture of Penicillium sp. (mud, Bering Sea), was previously
known as an acetate derivative of sporagen-AO 1123 obtained
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from a terrestrial mycophilic fungus,124 but was isolated here as
a natural product for the first time.125 The new compound, 78,
displayed activity against several cancer cell lines as did a co-
isolated sesquiterpene126 previously isolated from the fungus
Alternaria citri. Alcanivorone 79, an a-pyrone produced by
Alcanivorax jadensis (Deutsche Sammlung von Mikroorganis-
men und Zellkulturen) and three other Alcanivorax strains iso-
lated from seawater (Heita Bay, Kamaishi, Japan), had modest
activity against B. subtilis, S. aureus and Salinivibrio costicola and
was only produced by all strains when sodium pyruvate was
present in the culture medium. This was concordant with the
results of incorporation experiments with sodium [2-13C] pyru-
vate, which indicated biosynthesis from four pyruvate mole-
cules.127 Ayamycin 80 is a novel chlorinated metabolite with
broad-spectrum antimicrobial activity, isolated from Nocardia
sp., separated from Laurencia spectabilis (Ras-Gharib Coast,
Red Sea, Egypt).128 Three co-isolated known compounds,
chrysophanol 8-methyl ether,129 aspholedin130 and justicidin B,131
were also antimicrobial. Asperiamides B 81 and C 82 are cere-
brosides obtained from culture of Aspergillus niger (seawater,
Quanzhou Gulf, Fujian Province, China). The co-isolated afla-
toxins averufin132 and nidurufin133 displayed moderate inhibition
of Tobacco Mosaic Virus multiplication.134 Circumdatins C135
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and G,136 along with a new circumdatin, I 83, are benzodiazepine
alkaloids obtained from culture of Exophiala sp. separated from
the sponge Halichondria panicea (Bogil Is., Jeonnam Province,
Korea). All three compounds exhibited strong UV-A protecting
activity.137 Circumdatins A and B were originally isolated from
the terrestrial fungus Aspergillus ochraceus and reported as
betaines.135 Investigation of a marine strain of A. ostianus,
separated from an unidentified marine sponge (Pohnpei,
Micronesia), resulted in the re-isolation of circumdatins A and B
and revision of the structures to pentacyclic oxepins 84 and 85. A
new compound, circumdatin J 86, was also isolated, as was the
known circumdatin D,138 which had weak MRSA activity.139
Culture of an A. flavus from the green alga Enteromorpha tubu-
losa (Putian, Pinghai, China) yielded two 5-hydroxy-2-pyrone
derivatives, 87 and 88. Pyrone 87 induced cyclic adenosine
monophosphate production in GPR12-transfected CHO and
HEK293 cells.140 Seven prenylated indole diketopiperazine
alkaloids, 89, spirotryprostatin C–E 90–92, two fumitremorgin B
derivatives, 93 and 94, and 13-oxyverruculogen 95, resulted from
the fermentation of A. fumigatus from a holothurian, Stichopus
japonicus (Lingshan Is., Qingdao, China). All compounds were
evaluated against several cancer cell lines and compounds 92–94
displayed somewhat better susceptibility than the others to
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several of the cell lines.141 Three diketopiperazines (6-methox-
yspirotryprostatin B 96, 18-oxotryprostatin A 97 and 14-
hydroxyterezine D 98), a spiro compound (14-norpseurotin A
99) and a 29-nordammarane triterpenoid 100 were isolated from
fermentation of A. sydowi separated from driftwood (beach at
Baishamen, Hainan, China). Compounds 96–98 displayed weak
activity against the A549 cell line, whilst 99 and 100 exhibited
significant activity against E. coli, B. subtilis and Micrococcus
lysoleikticus.142 Notoamides F–K 101–106 are prenylated indole
alkaloids from fermentation of an Aspergillus sp. separated from
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the mussel Mytilus edulis (Noto Peninsula, Japan Sea). Notoa-
mide I 104 displayed weak cytotoxicity to HeLa cells.143 Three
14-membered macrolides, aspergillide A–C 107–109, were iso-
lated from a culture of A. ostianus originally separated from an
unidentified marine sponge (Pohnpei, Micronesia) and were
cytotoxic to L1210 cells.144 Two dimeric naphtho-g-pyrones, 110
and 111, from culture of A. carbonarius (sediment, Weizhou Is.,
Guangxi Province, China), displayed weak activity against
Mycobacterium tuberculosis.145
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Two new hexahydroanthrones, tetrahydrobostrycin 112 and

1-deoxytetrahydrobostrycin 113, were isolated from a marine-
derived Aspergillus sp. (Manado, Indonesia). Tetrahydrobos-
trycin 112 was weakly active against S. aureus and E. coli, but
1-deoxytetrahydrobostrycin 113 was only active against S.
aureus.146 Both compounds were also isolated from an uniden-
tified terrestrial endophytic fungus.147 Fermentation of Gym-
nascella dankaliensis, separated from the sponge Halichondria
japonica (Osaka Bay, Japan), yielded gymnastatins Q 114 and R

115 and dankastatins A 116 and B 117, which were all cytotoxic
to P388 cells. Additionally, gymnastatin Q 114 inhibited growth
of BSY-1 (breast) and MKN7 (stomach) human cancer cell
lines.148 From a culture of an Acremonium sp. from estuarine
sediment (Huon River, Tasmania, Australia), the acremolides
A–D 118–121 were characterised. The configurations of the
amino acid portions of the acremolides were assigned by using
the new C3 Marfey’s method.149 Fermentation of a Rhizopus sp.
from the bryozoan Bugula sp. (Jiaozhou Bay, China) yielded six
new ergosterols 122–127, all cytotoxic against several cancer cell
lines.150 Investigation of algicolous fungi associated with marine culture of an Acremonium sp. associated with the red alga
algae has yielded two aromatic polyketides. Acremonisol A was Plocamium sp. (Helgoland, Germany). Compound 128 was iso-
previously reported as a synthetic precursor to differanisole A,151 lated from fermentation of Nodulisporium sp. separated from an
but was isolated as a natural product for the first time from unidentified alga (Corfu, Greece).152 Investigation of the culture

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broth of an unidentified fungal strain derived from marine algae

(Hatijou Is., Japan) yielded a new compound, 1-deoxyru-
bralactone 129, and talaroflavone, previously isolated from
terrestrial153 and freshwater fungi,154 but isolated here from the
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marine environment for the first time. Both compounds were

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selective inhibitors of a selection of eukaryotic DNA poly-

merases.155 Ascochytatin 130 is a spirodioxynaphthalene isolated
from fermentation of an Asochyta sp. derived from floating rope
(Nagasaki prefecture, Japan) and displayed strong inhibition of
Gram-positive bacteria and C. albicans, in addition to cytotox-
icity to A549 and Jurkat cancer cells.156 Culture of a Zygosporium
sp. isolated from coral (Palau) produced a sulfoalkylresorcinol
131 that inhibited the polymerisation of a tubulin homologue in
vitro and was also slightly active against multi-drug-resistant
bacteria.157

Culture of the yeast Pichia membranifaciens from the sponge

Petrosia sp. (Jeju Is., Korea) produced five new metabolites, the
pichiafurans A–C 132–134, and the pichiacins A 135 and B 136.
Of the known compounds also isolated were 4-hydroxyphenethyl
propionate, a known synthetic product158 but isolated here from
a natural source for the first time, tyrosol acetate159 and 4-
methoxyphenethyl acetate,160 known terrestrial natural products
but isolated for the first time from a marine source.161 Cyto-
sporins D 137 and E 138 are metabolites of Eutypella scoparia
isolated from the gastropod Onchidium sp. (Lingshui County,
Hainan province, China).162 Culture of a marine Phomopsis sp.
(source not given) resulted in the isolation of two 10-membered Six open-chain cytochalasins Z10–Z15 150–155 were isolated
macrolides, phomolide A 139 and B 140 and a benzofuran from fermentation of Spicaria elegans (sediment, Jiaozhou Bay,
derivative 141. All compounds had significant antibacterial and China); 150 and 151 were moderately cytototoxic to A549
antifungal activity.163 Scopularides A 142 and B 143 are cyclic cells.167 Efrapeptin J 156 is a pentadecapeptide isolated from
depsipeptides isolated from the culture broth of Scopulariopsis cultivation of Tolypocladium sp. (sea mud, Aomori Prefecture,
brevicaulis separated from the sponge Tethya aurantium (Limski Japan), which together with efrapeptins F168 and G,169 were
Fjord, Croatia). The cyclic depsipeptides were inhibitors of down-regulators of the molecular chaperone GRP78.170 Nigro-
several tumour cell lines and weak inhibitors of Gram-positive spoxydons A–C 157–159 and nigrosporapyrone 160 were iso-
bacteria.164 Culture of Chaetomium globosum separated from the lated from fermentation of a Nigrospora sp. separated from an
fish Mugil cephalus (Katsuura Bay, Japan) yielded the chaeto- Annella species (sea fan; Similan Is., Thailand). Nigrospoxydon
mugilins A–F 144–149, all of which were inhibitory to P388 and A 157 displayed modest activity against S. aureus and
HL-60 cells, while chaetomugilins A 144, C 146 and F 149 were MRSA.171Chlorohydroaspyrones A 161 and B 162 were isolated
selectively cytotoxic to a panel of 39 human cancer cell lines.165,166 from culture of Exophiala sp. separated from the sponge

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Halichondria panicea (Bogil Is., Jeonnam Province, Korea) and previously reported curvularin macrolides 171–176.175–177 Of the
displayed mild activity against S. aureus and MRSA.172 Culti- new compounds, 170, 171, 174 and 175 were cytotoxic to
vation of a Chaetomium sp. separated from an unidentified a number of human tumour cell lines.178 Chaetominedione 177,
marine alga (Kamari, Santorini, Greece) yielded chaetox- a tyrosine kinase inhibitor, was isolated from culture of
anthones A–C 163–165, of which chaetoxanthone B 164 dis- Chaetomium sp. separated from the alga Valonia utricularis
played selective effects against the protozoan Plasmodium (Azores).179 The tetronic acid nodulisporacid A 178 was isolated
falciparum, while chaetoxanthone C 165 also displayed selective
effects against Trypanosoma cruzi.173 Fermentation of a Curvu-
laria sp. separated from the red alga Acanthaphora spicifera
(Fingers Reef, Apra Harbour, Guam), yielded the ten-membered
lactones curvulide A 166, curvulide B1 167 and B2 168, and
compound 169.174 The macrolide apralactone A 170 was also
isolated from the fungus along with the enantiomers of the

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from culture of Nodulisporium sp. separated from an unidentified
soft coral (Surin Is., Phang-nga Province, Thailand) as an E,Z
equilibrium mixture. Both 178 and the known fungal metabolite
vermelhotin180 displayed moderate antiplasmodial activity, with
vermelhotin also being cytotoxic to a number of cancer cell
lines.181 Fermentation of Mycelia sterilia derived from a sponge
(source not given) gave a series of polyketides 179–181.182
Culture of Monodictys putredinis from an unidentified green alga
(Tenerife, Spain) yielded the dimeric xanthone derivatives mon-
odictyochrome A 182 and B 183 as inhibitors of cytochrome
P450 1A and the estrogen biosynthetic enzyme CYP19 (aroma-
tase), and moderate inducers of quinone reductase activity.183
Four polyketides, trichodermatide A–D 184–187, were isolated
from fermentation of the fungus Trichoderma reesei (marine
mud, Lianyungang, China) and exhibited weak cytotoxicity to
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the A375-S2 melanoma cell line.184 Culture broth of a marine-
derived fungus strain CRIF2 (order Pleosporales) obtained from
an unidentified sponge (Surin Is., Thailand) yielded two new
metabolites, (Z)-6-benzylidene-3-hydroxymethyl-1,4-dimethyl-
3-methylsulfanylpiperazine-2,5-dione 188 and (3S,30 R)-3-
(30 -hydroxybutyl)-7-methoxyphthalide 189, in addition to the
known (S)-3-butyl-7-methoxyphthalide,185 isolated for the first
time as a natural product. Both 188 and 189 exhibited weak
cytotoxic activity against a range of human tumour cell lines.186
From a culture of a Petriella sp. obtained from an aquarium
culture of the sponge Suberites domuncula (originally from the
northern Adriatic Sea near Rovinj, Croatia) were isolated
190–192, derivatives of the known terrestrial fungal metabolite
infectopyrone.187 Dihydroinfectopyrone 190 was antiproliferative
towards L5178Y mouse lymphoma cells.188 Collections of
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Lyngbya majuscula and L. sordida (New Is. and Pigeon Is., Papua
New Guinea) yielded apratoxin D 193 with potent cytotoxicity to
the H-460 human lung cancer cell line,189 whilst from a collection
of L. bouillonii (Finger’s Reef, Apra Harbour, Guam), apratoxin
E 194 was isolated and was strongly cytotoxic to several cancer
cell lines.190 Besarhanamides A 195 and B 196 are fatty acid amide
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metabolites of L. majuscula (Pulau Hantu, Singapore). Besarha-
namide A 195 was moderately toxic in the brine shrimp
bioassay.191 L. confervoides (Grassy Key, Florida) was the source
of the macrocyclic depsipeptide grassypeptolide 197, which
contains an unusually high number of D-amino acid units and has
moderate broad-spectrum antiproliferative activity against four
human cancer cell lines.192 Pompanopeptins A 198 and B 199 are
hexapeptides isolated from L. confervoides (Pompano Beach and
Fort Lauderdale, Florida). Pompanopeptin A 198 was a selective
inhibitor of trypsin in vitro.193 L. polychroa (Hollywood Beach,
Fort Lauderdale, Florida) was the source of the linear
lipopeptides dragonamide C 200 and D 201, which were weakly
cytotoxic against several cancer cell lines.194 Carriebowmide 202,
a cyclic depsipeptide from L. polychroa (Carrie Bow Cay, Belize),
contains the rare amino acids 3-amino-2-methylhexanoic acid
and methionine sulfoxide.195 A Lyngbya sp. (Kemp Channel,
Florida Keys) was the source of the cyclic depsipeptides kempo-
peptin A 203 and B 204. Kempopeptin A 203 was an inhibitor of
elastase and chymotrypsin, and kempopeptin B 204 inhibited
trypsin.196 Coibamide A 205, a depsipeptide from Leptolyngbya
sp. (Coiba National Park, Panama), was a potent cytotoxin to
cancer cells with an unprecedented selectivity profile in the NCI 60
cell line panel.197 The unusual metabolite largazole 206, the first
thioester reported from cyanobacteria, was isolated from a Sym-
ploca sp. (Key Largo, Florida). Largazole 206 displayed highly
selective cytotoxicity towards transformed mammalian cell
lines.198,199 In the first of seven published syntheses of largazole
reported in 2008, largazole was synthesised by an eight-step,
covergent route.200 Symplocamide A 207, a depsipeptide isolated
from the cyanobacterium Symploca sp. (Sunday Is., Papua New
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Guinea), was both a potent chymotrypsin inhibitor and an
inhibitor of H-460 lung cancer and neuro-2a neuroblastoma
cells.201 Symploca laete-viridis (Ala Moana Beach, Oahu, Hawaii)
was the source of a dolastatin 14 analogue, malevamide E 208, an
ion channel inhibitor of Ca2+-release-activated Ca2+ channels.202
From Oscillatoria nigro-viridis (Curacao, Netherlands Antilles,
Panama), the lipopeptides viridamide A 209 and B 210 were
isolated. Viridamide A 209 displayed strong antitrypanosomal
and antileishmanial activity.203 Tumonic acids D–I 211–216 are
acylproline derivatives isolated from Blennothrix cantharidosmum
(Duke of York Is., Papua New Guinea) with modest antimalarial
activity and quorum-sensing inhibitory properties.204 Culture of
the benthic dinoflagellate Amphidinium sp. (Iriomote Is., Japan)
led to the isolation of the 15-membered macrolide, iriomoteolide-
3a 217, which contains an allyl epoxide and was potently cytotoxic
towards human B lymphocyte DG-75 cells and Epstein–Barr
virus (EBV) infected Raji cells.205 Brevisamide 218 is an unprec-
edented monocyclic ether alkaloid obtained from culture of
Karenia brevis (Wilson’s 58 clone) and was proposed as a possible
model for ladder-frame initiation of biosynthesis of related
polyether metabolites.206 Culture of a Durinskia sp., a symbiotic
dinoflagellate of the Okinawan nudibranch Chelidonura
fulvipunctata, resulted in isolation of durinskiol B 219, a close
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analogue of durinskiol A207,208 previously isolated from the same
species.209 Belizeanic acid 220 was isolated from culture of
Prorocentrum belizeanum (IEO de Vigo collection clonal culture)
as a potent protein phosphatase 1 inhibitor.210 Culture of Karlo-
dinium veneficum (inland bays of Delaware, USA) yielded the
amphipathic karlotoxin 1 221, a powerful haemolytic icthyo-
toxin.211 In another study, three other karlotoxin congeners were
identified, and a novel LC/MS method for quantitation devel-
oped.212 Culture of Heterocapsa circularisquama (Hiroshima
Prefecture Fisheries and Marine Technology Center, Japan)
yielded three new glycolipids 222–224 along with a lipid previ-
ously reported from the dinoflagellate Heterosigma akashiwo,213
which had cytolytic activity towards oyster heart and gill cells.214
Culture of the diatom Phaeodactylum tricornutum (Provasoli-
Guillard National Centre for Culture of Marine Phytoplankton)
yielded the galactolipid 225, in addition to a monogalactosyl
diacylglycerol previously isolated from the dinoflagellate
Heterosigma akashiwo.213 Both lipids induced apoptosis in
immortalised mammalian epithelial cells.215 The absolute
configuration of pericosine D, a metabolite of the fungus
Periconia byssoides separated from the sea hare Aplysia
kurodai,216 was determined as 226 by synthesis.217 Total synthesis
of the cell adhesion inhibitor peribysin E, a metabolite of sea
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hare-derived Periconia byssoides,218 was accomplished from car-
vone and necessitated a stereochemical revision of the structure to
227.219,220 Total synthesis of the acyclic peptide tasiamide,
originally isolated from the cyanobacterium Symploca sp.,221 led
to reassignment of the absolute configuration as 228.222 Exam-
ination of the NMR spectroscopic data of products of
a combinatorial synthesis of a substructure of the dinoflagellate
metabolite amphidinol 3 (AM3)223 led to revision of the C-2
configuration to R.224 Using isotropic small bicelles, the solution
conformation of AM3 was probed and it was established that
AM3 takes turn structures at the tetrahydropyran rings leaving
most of the hydrophobic region at the bicelle surface with the
polyolefin penetrating the interior.225 The absolute configura-
tion of amphidinolide Q, a metabolite of the cultured dinofla-
gellate Amphidinium sp.,226 was elucidated as 229.227
Stereocontrolled synthesis of the A/B-ring fragment of the
Gambierdiscus toxicus metabolite gambieric acid B228 led to
reassignment of the absolute configuration of the polycyclic
ether region (230).229 The absolute configuration of goniodomin
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A, an actin-targeting polyether macrolide originally isolated
from the dinoflagellate Alexandrium hiranoi (formerly Gonio-
doma pseudogoniaulax)230 was established as 231 by NMR
spectroscopic analysis, synthesis of model compounds, degra-
dation experiments and comparison with reference
compounds.231 Following the successful synthesis of three
members of the ciguatoxin family,232 synthetic analogues based
on modifications of the central 9-membered F ring were
prepared for SAR studies. This established that perturbations in
this region led to a very significant loss of affinity and toxicity in
these analogues.233 The haemolytic toxin H2-a, found in the
red-tide dinoflagellate Heterocapsa circularisquama, was identi-
fied as a porphyrin derivative, but was only partially charac-
terised.234 Streptopyrrolidine, a known synthetic compound,235
was isolated as a natural product for the first time from
fermentation of a Streptomyces sp. (deep sea sediment, Ayu
Trough, Pacific Ocean). Streptopyrrolidine displayed significant
antiangiogenesis activity without accompanying cytotoxicity
towards HUVEC cells.236 Semi-vioxanthin, a known terrestrial
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fungal metabolite237,238 with antibiotic activity, has now been
isolated from a marine source for the first time (marine-derived
fungus) and shown to regulate TNF-a production through
NF-kB and MAPK signaling pathways and thus most likely to
possess immunoregulatory factors.239 A number of very-long-
chain polyunsaturated fatty acids were identified from
culture of a strain of Amphidinium carterae (originally isolated
from a ditch in Essex, UK) and the first syntheses of two
even-numbered240 and two odd-numbered representatives
were completed.241 Of the odd-numbered acids, (all-Z)-
11,14,17,20,23-nonacosapentaenoic acid was previously repor-
ted as a component of mammalian spermatozoa242 but is now
isolated from a marine source for the first time. This report
represents the first isolation of (all-Z)-11,14,17,20,23,26-non-
acosahexaenoic acid.241 4-Hydroxy-10-methyl-11-oxododec-2-
en-1,4-olide was previously isolated as a metabolite of
marine-derived Streptomyces243,244 and the stereochemistry at
C-4 determined as S. The remaining stereogenic centre, C-10,
was not assigned. Total synthesis of (4S,10R)-4-hydroxy-10-
methyl-11-oxododec-2-en-1,4-olide suggested a (10R) configu-
ration following comparison with data from the natural
compound.245 Total synthesis of the Streptomyces metabolite
salinamide A,246,247 a bicyclic depsipeptide with potent anti-
inflammatory activity, was achieved in a 28-step linear
sequence.248 Aburatubolactam A, a macrolactam produced by
Streptomyces sp. originally separated from a Japanese marine
mollusc,249 was synthesised by a 23-step route based on
coupling of two domains.250 Total syntheses of the Pseudomonas
metabolites pseudopyronines A251 and B251,252 were achieved
from methyl b-oxocarboxylic ester starting materials. Both
compounds are potent and relatively selective inhibitors of
parasitic protozoa, particularly Leishmania donovani, and also
inhibit recombinant fatty acid biosynthetic enzymes from
Plasmodium falciparum and Mycobacterium tuberculosis.253
Zygosporamide, a cytotoxic cyclic depsipeptide from the
marine-derived fungus Zygosporium masonii,254 was syn-
thesised.255 Two syntheses of trichodermamide B, a cytotoxic
dipeptide isolated from the marine fungus Trichoderma
virens,256 were completed. The first of these utilised a tandem
nitrosation–oxaza-Cope rearrangement,257 whilst the second
was an enantioselective synthesis from quinic acid.258 Total
syntheses of three antifungal resorcylate lactones, 15G256b259,260
15G256i261 and 15G256p261 from the marine fungus Hypoxylon
oceanicum, were completed via a biomimetic selective late-stage
aromatisation reaction.262 Total synthesis of a molecule with the
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stereochemistry proposed for the fungal metabolite LL15G256g
from Hypoxylon oceanicum,260 also isolated as arthrichitin from
Arthrinium phaesospermum,263 indicated that the proposed
stereochemistry for the natural product was incorrect and
should be re-examined.264 Total synthesis of the originally
assigned structure for vannusal B, a C30 compound isolated
from the tropical ciliate Euplotes vannus,265 and comparison of
spectrosocopic data indicated that the proposed structure was
not correct.266 A prodigiosin analogue, previously isolated from
a marine Pseudomonas species,267 was isolated from a marine
bacterium as an inhibitor of NADPH oxidase in macrophage
cells.268 The product of a gene cluster identified in the marine
actinomycete Salinispora tropica catalysed the initial biosyn-
thetic reaction in the formation of the cyclohexenone moiety
from L-tyrosine in the sporolides A and B.269,270 Biosynthesis of
scorpinone,271 a 2-azaanthraquinone originally isolated from
the fungus Amorosia littoralis272 (Bahaman marine sediment),
was investigated through feeding experiments with labelled
acetate and found to be derived from a heptaketide linear
precursor.273
4 Green algae
About thirty papers have been published annually over the past
few years on various aspects of the chemistry of the Chlorophyta,
and these have included the characterisation of about ten new
metabolites per annum. A Fijian population of Tydemania
expeditionsis (Herald Pass) has yielded two cytotoxic, unsatu-
rated fatty acids 232 and 233 along with the known
3(z)-hydroxyoctadeca-4(E),6(Z)-dienoic acid.274 All three
compounds showed modest cytotoxicity against a panel of twelve
human tumour cell lines.275 Improved detection of fatty acids and
lipids in microalgae without sample preparation was reported
using a direct thermal desorption–GCGC–MS approach.276
Using cytotoxicity-guided fractionation the first lanostane-type
triterpenoid disulfate 234 and three known cycloartane disul-
fates277 235–237 were characterised from Tydemania expedi-
tionsis (Guam). X-Ray analysis established the absolute
configurations and led to a reassignment of the C-5 configuration
for 235–237. Weak to modest cytotoxicity (31–6 mM) was
observed for all four compounds and three hydrolysis products
238–240 against a panel of human tumour cell lines; the hydro-
lysis products were more cytotoxic. In addition, 237 had signif-
icant antifungal properties.278
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Chaetomorpha basiretorsa Setchell (Naozhou Island, China) was
the source of five previously identified sterols and 241 claimed as
a new stigmasterol based on NMR and X-ray crystal structure
analysis. However, there was a mismatch between the claimed
3a-OH orientation and that shown in the crystal structure
perspective diagram, which suggests that the orientation should
be 3b-OH, in which case stigmast-4,28-dien-3b,6b-diol 242
would be a new compound.279
A bioassay-guided strategy led to the identification of linolenic
and linoleic acids as potent PPAR a/g agonists from Chlorella
sorokiniana. PPAR a/g, belonging to the nuclear receptor
super-family, are therapeutic targets for hyperglyceridemia and
insulin resistance.280 In further studies on green microalgae the
first isolation and structural determination of a cyclic b-(1/2)
glucan from Chlorella pyrenoidosa was reported,281 and
a predominantly 4-sulfated, 3-linked galactan was characterised
from Codium isthmocladum.282 Two species of the edible Mon-
stoma sp. (M. latissimum and M. nitidum) were the source of
rhamnose-rich sulfated polysaccharides with heparin-active
properties.283,284
5 Brown algae
Some fifty papers are published annually on various aspects of
the chemistry of the brown algae including the isolation of up to
fifty new metabolites, predominantly terpenoids. However, by
far the majority of the publications are concerned with the
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chemistry and biological properties of the brown algal poly-
saccharides (fucoidans), and these properties have been
reviewed.285 A polyunsaturated monoglyceride 243 was isolated
from Sargassum sagammianum (Jeju Is., Korea) using a COX-2-
guided fractionation. This compound 243 served as a template
for the synthesis of a series of fifteen monoglycerides to probe the
influence that the number, position and chain length had on
COX-2 inhibition.286
The previously identified 7-methoxy-9-methylhexadeca-4,8-
dienoic acid287 was established as an inhibitor of phospholipase
A2.288 Apo-90 - and 130 -fucoxanthinone289,290 and loliolide291 were
reported for the first time from Cladostephus spongiosus f. verti-
cillatus (Tipaza, Algeria).292 In a chemotaxonomic study, the
more polar metabolites from Bifurcaria bifurcata (Oualidia,
Morocco) were re-examined and two new linear diterpenoids,
244 and 245, characterised. The isolation of 245 marked the first
isolation of a 10-hydroxygeranylgeraniol derivative from B.
bifurcata.293
From the Australian alga Cystophora moniliformis (Port Philip
Bay, Victoria, Australia) two epimeric, cyclic farnesylacetone
derivatives 246 and 247, a linear terpenoid 248 and six previ-
ously described terpenoids were characterised.294 Dolastane
derivatives 249–253 were obtained from Dilophus spiralis
(Elafonissos Is., Greece). The absolute configuration was
established for 249 and on biosynthetic considerations trans-
ferred to 250–253.295
In a survey of Sargassum siliquastrum (Jeju Is., Korea)
eleven new meroditerpenoids, 254–264, and nine known
compounds belonging to the nahocol or isonahocol classes
were reported.
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All but 264, a unique dihydroquinone, showed moderate to

significant radical-scavenging activities (DPPH assay). This lack
of activity for 264 was ascribed to the absence of a free phenolic
group.296 Five new sargaquinoic acid derivatives, 265–269, and
four previously identified compounds were isolated from
S. sagamianum (Manazuru, Japan). Derivative 269 showed
modest activity against a range of Hela cells.297 Chromane-type Four meroditerpenoids, 272–275, and three derivatives, 276–278,
meroditerpenoids, 270 and 271, came from an alternative were identified from Cystoseira baccata (Sidi Bouzid,
Japanese Sargassum species, S. micracanthum (Toyama Bay).298 Morocco).299 A feature of this collection was the trans-orientation

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of the bridgehead methyls of the hydrindane system. All
previous cyclic meroditerpenoids from Cystoseira spp. have
had a cis-orientation.300 From Halidrys siliquosa (Brittany,
France) a chromene 279, four new meroditerpenoids 280–283
and four known metabolites were identified. An interesting
feature was the potential for tautomeric acyloin isomerisation.301
The phloroglucinol derivative, 6,60 -bieckol,302 re-isolated from
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Ecklonia cava (Jeju Is., Korea), was a non-cytotoxic, effective
inhibitor of the cytopathic effects of HIV-1 on CEM-SS cells.303
Dolabelladientriol, derived from 10,18-diacetoxy-8-hydroxy-2,6-
dolabelladiene,304 blocked the synthesis and integration of the
HIV-1 provirus, inhibiting viral replication.305 Consecutive
Claisen rearrangements were used in the synthesis of the anti-
proliferative prenylated quinones306 from Perithalia capillaries
(New Zealand).307
6 Red algae
New red algal metabolites continue to be dominated by terpenes
and halogenated polyphenols, but with only half the number
reported in 2008 compared with 2007. An extract with anti-
inflammatory properties from Gracilaria verrucosa (Jeju Is.,
S. Korea) yielded four 11-deoxyprostaglandins 284–287, the
ceramide 288 and a keto fatty acid 289 along with a range of
other known fatty acids. The anti-inflammatory activity was
however associated with some of those known fatty acids, and
led to the synthesis of twenty-five analogues for investigation of
activities.308 The glycolipid, lithanoside 290, isolated from the
coralline alga Hydrolithon reinboldii (Denny’s Reef, Fiji)
along with five other known compounds, was modestly
cytotoxic against a panel of twelve human cell lines and weakly
antimalarial.274
Two laurane-derived brominated sesquiterpenes 291 and 292,
along with the known laur-11-en-1,10a-diol,309 but reported here
for the first time as a natural product, were obtained from
Laurencia tristicha (Shanwei, Guangdong Province, China).310
An unidentified Laurencia sp. (Pulau Tioman, Malaysia) yielded
the brominated sesquiterpenes tiomanene 293, acetylmajapolene
A 294 and acetylmajapolene B 295 (the latter as a diastereoiso-
meric mixture).311 An enantioselective synthesis from (S)-cam-
pholenaldehyde of the sesquiterpene (+)-laurokamurene B,
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lute configuration of laurokamurenes.313 Three brominated
diterpenes 296–298 were isolated from Sphaerococcus corono-
pifolius (Palaiokastritsa Bay, Corfu Is.) and the structure of
the previously reported 299314 was revised.315 In a second
paper,316 the same group reported an additional four bromi-
nated diterpenes 300–303 from the same collection of
S. coronopifolius, and a structural revision of the previously
reported diterpene 304.317
An extract from Laurencia saitoi (Yantai, China) provided the
parguerane diterpene derivative 305 together with nine other
known parguarane, thyrsiferol and laurane compounds.318 A
new squalene-derived triterpene polyether, omaezakianol 306,
was isolated from Laurencia omaezakiana Masuda (Enoshima,
Japan) along with 15,16-anhydrothyrsiferol 307.319 The squale-
noid-derived triterpenoid laurenmariannol 308 together with the
known thyrsiferol320 and aplysiol A321 (claimed here as a new
compound called (21S)-21-hydroxythyrsiferol) were isolated
from Laurencia mariannensis (Hainan and Weizhou Is., China).
Both laurenmariannol and aplysiol A showed modest cytotoxic
activity against P388 tumour cells.322
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Two a-pyrone macrolides, neurymenolide A 309 and B 310, were
isolated from Neurymenia fraxinifolia (Taveuni, Fiji). Neury-
menolide A existed as interconverting atropisomers arising from
restricted rotation about the a-pyrone ring system, and displayed
moderate activity against MRSA and VREF.323 The rare
cytotoxic, cyclic pentapeptide galaxamide 311, obtained from
Galaxaura filamentosa (Xisha Is., South China Sea), was also
synthesised.324
Three new bromophenols 312–314 were obtained from Poly-
siphonia urceolata (Qingdao coast, China) and displayed modest
potency in the DPPH radical-scavenging assay.325 The highly
oxygenated bromophenol urceolatin 315, obtained from Poly-
siphonia urceolata (Qingdao coast, China), contained an
unprecedented naturally occurring benzylphenanthro[4,5-
bcd]furan unit, and showed significant DPPH radical-scavenging
activity.326 Brominated phenols continue to be investigated for
their significant antimicrobial properties, with six isolated from
an extract of Odonthalia corymbifera (Korea). These compounds,
together with synthetic analogues, provided information on
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constants are indicative of a trans relationship in furanosides.337

7-Methyl-9-oxo-dec-7-enoic acid 322 was isolated from an Ircinia
sp. (Red Sea).338 The moderately cytotoxic inconspicamide 323
was isolated from Stelletta inconspicua (Oshima-shinsone,
Kagoshima Pref., Japan) dredged from 150 m depth.339 A series
of brominated acetylenic fatty acids 324–329, isolated as methyl
esters, came from an unidentified sponge (Madang, Papua New
Guinea).340

structure–activity relationships in the series for antimicrobial

activity.327 Potassium 4-(hydroxymethyl)benzenesulfonate and
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1-methoxyphenethyl alcohol, described previously as synthetic

products, were isolated from Bostrychia tenella (Ubatuba,
Brazil).328 The intra-cellular storage, transport and exocytosis of
halogenated compounds in Laurencia obtusa was studied.329 Two
inhibitors of Taq DNA polymerase were isolated from Sym-
phyocladia latiuscula, and shown to be the known 2,3,6-tri-
bromo-4,5-dihydroxybenzyl alcohol and the methyl ether.330 The
known metabolite 1,1,3,3-tetrabromo-2-heptanone was identi-
fied as the antibacterial and putative antifouling agent from
Bonnemaisonia hamifera.331

7 Sponges
The number of new sponge metabolites reported for 2008 (278) is
similar to that for 2007. The localisation of secondary metabo-
lites in sponge tissue was demonstrated using MALDI-TOF
imaging. This technique creates an image of the spatial position
of molecular and fragment ions associated with a variety of
secondary metabolites in a sample of biological tissue.332 Two
double-headed sphingolipid-like compounds, rhizochalin B 316
and rhizochalinin B 317, were obtained as peracetates from an
Oceanapia sp. (Scott Reef, NW Australia).333 Leucettamol A (+)-Duryne 330 (Cribrochalina dura)341 and the enantiomer were
(Leucetta aff. microrhaphis),334 a polyunsaturated sphingolipid- synthesised, establishing the E nature of the central double bond
like compound, prevented the formation of active proteasomes and the overall absolute configuration.342 Both enantiomers of
by inhibiting the association of Ubc13 and Uev1A.335 Strep- the potent cytotoxin dideoxypetrosynol (Petrosia sp.),343 isolated
sichordaia lendenfeldi (Indonesia) was the source of the cytotoxic as a racemic mixture, were synthesised separately.344 An enan-
strepsiamides A–C 318–320.336 Vesparioside B 321, a mixture of tiospecific synthesis of bitungolide F (Theonella swinhoei)345
long-chain homologues, was isolated from Spheciospongia ves- established the absolute configuration.346 Plakortis angulospicu-
paria (Grand Bahama Is., Bahamas). A computational study was latus (Baı́a de Todos os Santos, Bahia, Brazil) yielded the cyclic
used to show that small-magnitude 1H–1H vicinal coupling peroxide plakortenone 331.347

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atives 332–336,348 while a naphthahydroquinone derivative,

xestosaprol C 337, was isolated from Xestospongia sapra (Ker-
ama Islands, Okinawa).349

were obtained from Theonella swinhoei (Okinawa) as acetonides

and the structures confirmed by comparison with samples
prepared from onnamide A.

An empirical rule to establish the relative stereochemistry of 1,5-

diols from 1H NMR chemical shifts was proposed.355 Sponges
continue to be a rich source of novel and biologically active
peptides. The brine-shrimp-toxic taumycins A 347 and B 348

Exiguaquinol 338, isolated from Neopetrosia (Xestospongia)

exigua (Queensland, Australia) inhibited the Helicobacter pylori
enzyme glutamate racemase, an enzyme which interconverts L-
and D-glucose and so is of importance in constructing bacterial
cell walls.350 Cacospongia mycofijiensis (Beqa Lagoon, Fiji)
yielded the unusual and modestly cytotoxic g-thiopyrone CTP-
431 339.351 Poipuol (Hyrtios sp.)352 was synthesised.353 The mildly
cytotoxic amides ciliatamide A–C 340–342 were obtained from
Aaptos ciliata (Oshima-Shinsone, Kagoshima Pref., Japan), and
compounds 341 and 342 were found to be antileishmanial.354 The
onnamide derivatives 21,22-dihydroxyonnamide A1–A4 343–346

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were isolated from Fascaplysinopsis sp. (Madagascar); 347 was
cytotoxic to human UT-7 leukaemic cells.356 A re-investigation of
cyclocinamide A (Psammocinia sp.)357 confirmed the speculative
(11S,14S) assignments in contrast to the (14R) configuration of
cyclocinamide B (Corticium sp.)358 and also confirmed the lack of
activity in solid tumours.359 Jaspamides H 349 and J–L 350–352,
isolated from Jaspis splendans (Tonga, Vanuatu), were potently
cytotoxic and caused microfilament disruption.360
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An enantioselective synthesis of cyclotheonamide C (Theonella
swinhoei) was achieved.361,362 A synthesis of the proposed struc-
ture of scleritodermin A (Scleritoderma nodosum)363 revealed
spectroscopic differences leading to the proposal and synthesis of
a revised (2E,14S) structure, 353, spectroscopically identical to
the natural product.364 Callyspongia aerizusa (Ambon, Indo-
nesia) yielded the cytotoxic proline-rich peptide callyaerin G
354.365 The cytotoxic peptide stylopeptide 2 355 was isolated
from Stylotella sp. (Papua New Guinea).366 Phakellistatin 12
(Phakellia costata)367 was synthesised enantioselectively on solid-
phase support.368 The cyclic depsipeptide homophymine A 356,
isolated from Homophymia sp. (New Caledonia) inhibited HIV-1
infection in the nanomolar range with cytotoxicity at micromolar
levels.369 Potent agonists of human sensory neuron-specific G
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protein coupled receptor (SNSR), the polydiscamides B–D 357–
359, were obtained from Ircinia sp. (Porpoise Cay, Great Barrier
Reef, Australia). These peptides are the first examples of non-
endogenous agonists of this receptor involved in the modulation
of pain.370 The cytotoxic koshikamide B 360 was isolated inde-
pendently by two groups from Theonella sp. (Shimokoshiki Is.,
Kagoshima Pref., Japan and Palau, Micronesia).371 An enan-
tiospecific synthesis of papuamide B 361 (Theonella sp.)372
resulted in a revision of the relative configuration of the 2,3-
diaminobutanoic acid residue of the side chain from (2S,3R) to
(2S,3S) and established the configuration of the 2,3-dihydroxy-
2,6,8-trimethyldec-4,6-dienenoic acid residue as (2S,3R,8R).373
Macrocyclic polyketidesare an important feature of sponge
secondary metabolite chemistry. Several new latrunculin-type
metabolites, latrunculol A–C 362–364, 18-epi-latrunculol 365
and latrunculones A 366 and B 367, were isolated from Caco-
spongia mycofijiensis (Beqa Lagoon, Fiji), a known source of this
type of macrolide. All compounds were cytotoxic, but 365 did
not affect microfilament formation, the mode of action associ-
ated with other latrunculins.374 Latrunculin A (Negombata
(Latrunculia) magnifica)375 was found to inhibit prostate tumour
cell invasion and hypoxia inducible factor-1 (HIF-1) activation
of breast tumour cells.376 The cytotoxic phorbasides C–E 368–
370 were isolated from a Phorbas sp. (Muiron Is., Western
Australia). The structure and absolute configuration of the
unusual methyl-2-O-methyl-a-L-evalose moiety was determined
by synthesis from L-rhamnose.377 The absolute configuration of
exiguolide 371 (Geodia exigua)378 was established by the total
synthesis of the enantiomer.379 Superstolide A, originally isolated
from Neosiphonia superstes,380 was synthesised enantiospecifi-
cally.381,382 Spongistatin-1 (Spongia sp.)383 induces apoptosis in
leukaemia cells including those that overexpress the protein
XIAP, an inhibitor of apoptosis.384 A yeast non-lethal gene
deletion library was used to establish the cellular target of the
potent cytotoxin neopeltolide (Daedalopelta sp.)385 as the cyto-
chrome bc1 complex of mitochondria.386 An enantiospecific
synthesis of clavosolide D (Myriastra clavosa)387 was achieved.388
Brine shrimp bioassay-guided isolation led to the macrolides
scalarin A 372 and B 373 and tulearin A 374 from
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a Fascaplysinopsis species (Salary Bay, Tulear, Madagascar).
Compounds 372 and 374 were also cytotoxic to leukaemia
cells.389 A separate collection of the same sponge yielded the
cytotoxic scalarin C 375, and the authors suggested that the
previously described scalarins A and B were degradation prod-
ucts of C.390,391 A cytotoxic chondropsin-type macrolide 376,
isolated from Siliquariaspongia mirabilis (Chuuk Lagoon,
Micronesia), was named mirabilin,392 although the unrelated
mirabilins A–E are aromatic alkaloids previously isolated from
the sponge Arenochalina mirabilis.393 A cytotoxic and antibac-
terial bromophenol 377 was isolated from a Dysidea sp.
(Micronesia).394 Ceratinophenol A 378 was isolated from
Pseudoceratina arabica (Sharm El-Sheikh, Red Sea, Egypt).395
Suberea mollis (Hurghada, Red Sea) was found to contain the
moderately antimicrobial subereaphenol A 379.396 The same
sponge later yielded subereaphenols B 380 and C 381 for which
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antioxidant activity was reported.397 Alkaloids continue to be
a prominent feature of sponge secondary metabolism. A Dysidea
species (Palau Sinok, Karimunjawa, Indonesia) yielded the
highly chlorinated sintokamides A–E 382–386. Compound 382
inhibited the androgen receptor of prostrate cancer cells.398 It
was established that dysiherbaine, originally isolated from
a sponge identified as Dysidea herbacea399 but now considered to
be Lendenfeldia chondrodes, was localised in the cells of the
symbiotic cyanobacteria Synechocystis species. Both dysi-
herbaine-containing and dysiherbaine-absent sponges contained
the same Synechocystis cyanobacterium, but only in some
sponges did this bacterium produce the metabolite.400 What was
claimed to be the ‘‘previously unreported maleimide 5-oxime’’
was isolated from Cliona patera (Gulf of Thailand, Thailand).401
However, the same authors had reported this compound from
a different sponge in 2007.402 (Z)-Dysidazirine (Dysidea
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fragilis)403 was synthesised.404 The related and moderately cyto-
toxic halogenated 2H-azirines 387–389 were isolated from Dys-
idea fragilis (Pohnpei, Micronesia).405 Stellettamide C 390
(Stelletta sp.)406 was synthesised enantiospecifically and the
absolute configuration proposed as antipodal (1R,4R,8aS) to
that of stellettamides A and B on the basis of an opposite (–) [a]D.
The natural (+)-stellettamide A was also synthesised.407 The bis-
pyrrolizidine alkaloids bistellettazine A–C 391–393 and related
bistellettazole 394 were isolated from Stelletta sp. (Great
Australian Bight, Southern Australia).408
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Alkylpyridinium and related piperidine alkaloids are a feature of
sponge metabolism, a biosynthetic hypothesis having previously
been put forward involving condensations of aminoaldehydes.409
Support for this hypothesis was obtained from synthetic model
studies where the skeletons of halicyclamines and manzamines
were formed from the same proposed precursor.410 Xestamines C
(Xestospongia wiedenmayeri)411 E and H (Calyx podatypa)412
were synthesised.413 The weakly cytotoxic simplexidine 395 was
obtained from Plakortis simplex (Bahamas).414 The cytotoxic and
antibacterial alkaloid 396 was isolated from Haliclona viscosa
(Svalbard, Spitzbergen, Norway) as a minor metabolite. The
proposed structure was confirmed by synthesis.415
Halicyclamine A (Haliclona sp.), originally reported as inhibitory
to inosine 50 -dehydrogenase (IMPDH),416 was also inhibitory to
several Mycobacterium species including M. tuberculosis and
showed similar activity to IMPDH-overexpressing strains, indi-
cating that the antibacterial activity was independent of the
IMPDH inhibition.417 A Pachychalina species (Martinique,
Caribbean Sea) yielded the moderately cytotoxic pachychalines
A–C 397–399.418
Nakinadines B–F 400–404 were obtained from Amphimedon sp.
(Nakijin, Japan); nakinadines C 401 and D 402 were cytotoxic.419
A series of cytotoxic indole alkaloids, trachycladindole A–G
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405–411, were obtained from Trachycladus laevispirulifer
(GreatAustralian Bight, South Australia).420
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Acanthostrongylophora ingens (Ujung, Pandang, Indonesia)
yielded acanthomine A 412, cytotoxic to both mammalian cancer
cells and brine shrimp larvae.421 The bis-indole dictazolines A 413
and B 414, isolated from Smenospongia cerebriformis (Solarte
Isle, Pacific Coast of Panama),422 are closely related to the soft
coral metabolites tubastrindoles A and B (Tubastraea sp.).423
Aaptamine (Aaptos aaptos)424 and 5,6-dibromo-N,N-dimethyl-
tryptamine (Smenospongia sp.)425 had significant antidepressant
activity in mice.426 A remarkable find was the presence of an
enantiomeric series of discorhabdins in different populations of
Latrunculia species in New Zealand.427 Renierol (Haliclona sp.)428
was an inhibitor of xanthine oxidase, an enzyme involved in
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gout, and lowered uric acid levels in K oxonate-induced hyper-
uricaemic mice.429 A new Petrosia species (Phuket Is., Thailand)
yielded 2-bromoamphimedine 415 as well as the known petros-
amine (Petrosia sp.),430 which was found to be a potent
acetylcholinesterase inhibitor.431 Purpurone (Iotrochota sp.),
previously thought to be an artifact of the hydrolytic extraction
procedure employed,432 was re-isolated from an Iotrochota sp.
(Hainan Island China) under mild conditions, reaffirming its
status as a genuine marine metabolite.433 Agelas mauritiana
(Guadalcanal, Solomon Islands) yielded debromodispacamides
B 416 and D 417. These structures were confirmed in the same
study by synthesis.434
Calcaridine A 418 (Leucetta sp.)435 was synthesised and the
relative stereochemistry established from X-ray analysis of the
epimer.436 Dibromoagelaspongin (Agelas sp.)437 was synthesised
using successive Pummerer-like oxidative cyclisations.438 The
moderately cytotoxic cylindradines A 419 and B 420 were iso-
lated as scalemic mixtures from Axinella cylindratus (Seto Inland
Sea, Ehime Pref., Japan).439 Axinellamine B (Axinella sp.)440 was
synthesised.441 A re-isolation and X-ray analysis led to a reas-
signment442 of the structure of spiroleucettadine (Leucetta sp.)443
as 421, which differs from both the original proposal and that
suggested during an attempted synthesis.444
The antimicrobial nagelamides K 422 and L 423 were isolated
from an Agelas sp. (Seragaki, Okinawa).445 From the same
sample of sponge, the antifungal nagelamides M 424 and N 425
were also isolated.446 An unorthodox affinity-column-based
protocol was used to obtain sceptrin (originally isolated from
Agelas sceptrum)447 from Agelas conifera. Sceptrin demonstrated
an ability to bind to MreB, the bacterial equivalent of actin.448
The unnatural (+) enantiomer of monobromophakellin
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from Aplysina fulva (Bahia, Brazil) in a study of bromotyrosine

metabolites of this species from several sites in the western
Atlantic Ocean.458 Subereamollines A 436 and B 437 were
isolated from the same sponge (Suberea mollis, Hurghada, Red
Sea, Egypt) from which subereaphenols B 380 and C 381 were
obtained.397
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Hydroxymoloka’iamine 438 and moloka’iakitamide 439,

obtained from the same sponge that yielded ceratinophenol A
378, had significant parasympatholic effects on isolated rabbit
heart and jejunum.395

(Phakellia flabellata)449 was synthesised.450 Stereoselective

synthesis of a series of 2-aminopyrimidine ring-containing
compounds, including isoptilocaulin (Ptilocaulis sp.),451 7-epi-
neoptilocaulin (8a,8b-dehydroptilocaulin) 426 (Batzella sp.)452
and mirabilin B 427 (Arenochalina mirabilis),393 established the
absolute configurations. The syntheses of netamines E 428 and G Dispyrin (Agelas dispar)459 and purpurealidin (Psammaplysilla
429 (Biemna laboutei)453 in the same study resulted in structural purpurea)460 were synthesised from tyramine.461 In a separate
revisions and the suggestion of a similar revision for netamines A synthetic study, dispyrin was found to be a potent ligand and
and C to 430 and 431.454 antagonist of a1D and a2A adrenergic and H2 and H3 histamine
receptors.462 Aplysamine 6 440, obtained from a Pseudoceratina

Ageladine A (Agelas nakamurai)455 was found to be a useful

intracellular pH-indicating dye.456 A Pseudoceratina species
(Hainan Is., China) contained 432 along with the bromotyrosine
derived alkaloids 433 and 434.457 Aplysinafulvin 435 was isolated

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sp. (Queensland Australia), was an isoprenylcysteine carboxyl

methyltransferase inhibitor.463 Clavatadines A 441 and B 442,
inhibitors of blood coagulation factor XIa, were isolated from
Suberea clavata (Swain Reefs, Great Barrier Reef, Australia).464
Pseudoceratina purpurea (Bise, Okinawa) yielded the weakly
cytotoxic 20-N-methylpurpuramine-E 443.465 The adenosine A1
receptor antagonist and moderately cytotoxic ianthesine E 444
was isolated from a Pseudoceratina sp. (Swain Reefs, Great
Barrier Reef, Australia).466 An Aplysinella species (Micronesia)
contained the cytotoxic aplysinillin 445.467
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of human tumour cell lines.469 A two-sponge association of

a Jaspis and a Poecillastra species (Korea) yielded the cytotoxic
cyclobispsammaplin A 449 and psammaplin M 450.470

The weakly cytotoxic purealidins T 446 and U 447 were obtained

from a Pseudoceratina sp. (Hainan Is., China).468 Bastadin 24 448
and seven previously reported bastadins were isolated from
Ianthella quadrangulata (Heron Is., Great Barrier Reef, Aus-
tralia). Bastadin 24 was selectively cytotoxic towards a selection
Psammaplin A (Psammaplysilla sp.)471 was a fish antifeedant and
present in Aplysinella rhax as the ‘‘ecological pro-drug’’ psam-
maplin A sulfate (Aplysinella rhax)472 from which psammaplin
A was rapidly produced when the sponge was wounded.473
A revised dimeric structure was proposed for zamamistatin
(Pseudoceratina pupurea),474 originally described as a spiro-
dimer,475 based on the observation of a monomeric nitrile
decomposition product.476 The compound was spectroscopically
identical to aeroplysinin-1 (Verongia aerophoba).477 Four purine
alkaloids, nigricine 1–4 451–454, were isolated from Petrosia
nigricans (Palau Baranglompo, Indonesia).478

A pteridine alkaloid, asteropterin 455, with cathepsin B inhibi-

tion activity, was isolated from Asteropus simplex (Shikine Is.,

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Japan),479 while the meroterpenoid 19-hydroxypolyfibrospongol

456 was isolated from Dysidea arenaria (Hainan Is., China).480

An unidentified deepwater sponge obtained from the Norfolk

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Rise, New Caledonia, contained alisiaquinones A–C 457–459

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and alisiaquinol 460, which were inhibitors of protein farnesyl

transferase and active against several strains of Plasmodium
falciparum. Dysidea septosa (Lingshui Bay, Hainan Is., China) contained
lingshuiolides A 471 and B 472, lingshuiperoxide 473, iso-
dysetherin 474 and spirolingshuiolide 475.491

Alisiaquinone C was also active against P. vinkei infection

in mice.481 Dactylospongia elegans (Inner Gneerings Reef,
Mooloolaba, Australia) yielded isohyatellaquinone 461,
7,8-dehydrocyclospongiaquinone 462 and 9-epi-7,8-
dehydrocyclospongiaquinone 463 as well as the previously
described dictyoceratidaquinone (Spongia sp.).482 The relative
stereochemistry of dictyoceratidaquinone was determined. In the
same study, an undescribed species of Dactylospongia from the
same location was found to contain the enantiomer of 461 as well
as neomamanuthaquinone 464.483

The sequiterpenoids axinisothiocyanate M 476 and N 477,

axinythiocyanate A 478, axinysones A–E 479–483 and axinyni-
trile A 484 were isolated from Axinyssa isabela (Gulf of
California, Mexico). Compounds 477 and 483 were mildly

Strongylophorines 2, 3 and 8 (Strongylophora durissima)484,485

were HIF-1 inhibitors.486 An unidentified sponge of the family
Spongiidae (Unten Port, Okinawa) yielded the modestly cyto-
toxic nakijiquinones G–I 465–467, which were HER2 kinase
inhibitors.487 The proteasome inhibitor acanthosulfate 468 was
isolated from Acanthodendrilla sp. (Boracay Is., Philippines).488
The sesquiterpenoids isomicrocionin-1 469 and isomicrocionin-3
470 and an enantiomer of the known microcionin-1 (Microciona
toxystila)489 were obtained from a Fasciospongia species.490

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cytotoxic. Axinynitrile A 484 was enantioselectively synthesised axinisothiocyanates A–L 497–508, were obtained from an
from (+)-aristolone to establish the absolute configuration.492 An Axinyssa species (Gulf of California, Mexico); 498 and 506 were
Axinyssa species (Sanya, Hainan, China) yielded isofarnesyl cytotoxic.499
formamide 485, 7-formamido-7,8-dihydro-a-bisabolane 486 and
4,5-epi-10-isothiocyanatoisodauc-6-ene 487.493 The cytotoxic
formamide 488 along with 489 were obtained from an Axinyssa
sp. (Hainan Is., China).494
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Axiplyns A–E 490–494, isolated from Axinyssa aplysinoides

(Misali Is., Tanzania), were toxic to brine shrimp.495

The unusual sulfur- and nitrogen-containing phorbasins D–F

509–511 were obtained from a Phorbas sp. (Great Australian
Bight, South Australia). Phorbasin E 510 was cytotoxic.500
Meanwhile, in a study of Phorbas gukulensis (Gagu-Do,
S. Korea), three related compounds were isolated and named
phorbasins G–I 512–514.501 The authors of the first study then
published the structures of a five further cytotoxic phorbasins
from the same Australian Phorbas sp., andunaware of the
Korean study, named them as phorbasins G–K 515–519.502

Halichonadin F 495 was isolated from Halichondria sp. (Unten

Port, Okinawa). The relative configuration at C-10 was
confirmed by synthesis of the 10-epi-isomer from aromaden-
drene. Halichonadin C (Halichondria sp.)496 was also isolated as
a trimeric CuI complex.497 In a separate study on the same
sponge, the cytotoxic heterodimeric sesquiterpenoid hal-
ichonadin E 496 was characterised.498 A series of isothiocyanates,

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In the same study, a bisabolene-type diterpenoid which appears

to be identical to the just-described phorbasin H 513 was
also isolated.505 Cyanthiwigin F (Myrmekioderma styx)506 was
synthesised from a symmetrical 1,4-diketocyclohexane by double
catalytic enantioselective alkylation and the absolute configura-
tion confirmed.507 Cyanthiwigins W and Z506 were also
synthesised enantioselectively.508 Diacarnus megaspinorhabdosa
(Pulau Baranglompo Is., Indonesia) yielded diacarperoxides
A–G 537–543 and the norsesterterpenoid diacardiol A 544;
diacarperoxide D 540 was cytotoxic.509 A series of furano- and

While the Korean phorbasins G–I were published slightly earlier

than the Australian versions, they differ considerably in oxygenation
of the six membered ring, and perhaps in the interest of clarity, should
be renamed. Spongian diterpenes 520–523, ligands of thyrotropin-
releasing hormone receptor 2, were isolated from a Spongia sp.
(Wreck Reef, Coral Sea, Australia).503 Agelas cf. mauritiana
(Guadalcanal, Solomon Islands) yielded agelasines J–L 524–526,
which were antimalarial in tests against Plasmodium falciparum.504

Gagunins H–O 527–536, isolated from a Phorbas sp. (Gagu-do,

S. Korea), were moderately cytotoxic and weakly inhibitory
towards isocitrate lyase.

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butenolide sesterterpenoids 545–564 were isolated from a Sarco-
tragus sp. (Soheuksan Is., S. Korea). Compounds 558 and 559
were antibacterial, 549 and 550 cytotoxic, while 552 (which was
drawn incorrectly) was inhibitory towards isocitrate lyase. The
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absolute configurations of 565,510 previously reported as
a synthetic analogue, and 548 (Sarcotragus sp.)511 were also
assigned.512 The furanosesterterpenoid esters 566–568 were iso-
lated from Coscinoderma mathewsi (Mooloolaba, Queensland,
Australia).513 Rhopaloic acid (Rhopaloeides sp.)514 was syn-
thesised using a [3 + 3] cyclisation to form the pyran ring.515 The
cytotoxic aplysinoplides A–C 569–571 were isolated from Aply-
sinopsis digitata (Oshima-shinsone, Kagoshima Pref., Japan).516
Manoalide (Luffariella variabilis),517 manoalide-25-acetate
(Thorectandra excavatus)518 and secomanoalide (L. variabilis),519
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inhibited quorum sensing in bacteria.520 24-Ethylmanoalide 572
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was obtained from Luffariella cf. variabilis (Mayotte Is., Indian
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Ocean). Since no ethanol was used in the isolation, 572 was
presumed to be a natural product.521 From Hyattella cribriformis
(Kanyakumari Coast, India), 24b-methoxyscalarolide 573522 was
isolated, while the cytotoxic scalarane-type sesterterpenoids 574
and 575 were characterised from Hyrtios erectus (Kavieng,
Papua New Guinea).523 A series of cytotoxic scalarane
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sesterterpenoids 576–585 were obtained from a Smenospongia
species (Soheuksan Is., S. Korea); sesterterpenes 577, 579–581
and 585 were antibacterial.524 A Lendenfeldia species (Saipan,
Mariana Islands, Micronesia) contained the scalarane terpenoid
586 along with furospongolide (Dysidea herbacea)525 which was
an HIF-1 inhibitor.526 Hyrtiosal (Hyrtios erectus)527 was an
HIV-1 integrase inhibitor with a novel binding site.528 A
moderately cytotoxic nor-sterol 587 was isolated from Axinella
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carteri (Derawan Is., Indonesia),529 while the nor-steroids 588–
590, isolated as ethyl esters from Acanthella cavernosa (Hainan
Is., China), were inhibitors of the settling of Balanus albicostatus
larvae.530 Ircinia aruensis (Naozhou Is., China) yielded the
epoxysterols 591–596, of which 591–593 were shown to be
moderately cytotoxic.531 In the same study that described the
isolation of polyacetylenes, the isolation of polyacetylenic sterol
esters 597–599 was also described.340 Topsentiasterol sulfate F
600, along with the halogenated chlorotopsentiasterol sulfate D
601 and iodotopsentiasterol D 602, were obtained from a Top-
sentia sp. (Vang Fong Bay, Vietnam). Chlorotopsentiasterol
sulfate D 601 was an inhibitor of molluscan endo-1,3-b-D-glu-
canase.532 The protein kinase Cz inhibitory sterol sulfates sphe-
ciosterols A–C 603–605 were isolated from Spheciospongia sp.
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(Cagayan de Oro, Philippines).533 Mycalosides J 606 and K 607
were isolated from Mycale laxissima (San-Felipe Is., Cuba).534
Three independent groups535–537 have reported syntheses of the
steroidal alkaloid cortistatin A (Corticium simplex).538 The iso-
malabaricane triterpenoids rhabdastrellins A–F 608–613 were
isolated from Rhabdastrella aff. distincta (Hainan Is., China).
Rhabdastrellin A 608 was moderately cytotoxic.539
8 Cnidarians
There was a slight rise in the number of new metabolites reported
from cnidarians compared with previous years. Principal compo-
nent analysis of fatty acids provides some discrimination of octo-
corals at the family level.540 The absolute configuration of a new
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unsaturated fatty acid 614, isolated from Sinularia sp. (Ishigaki Is.,
Okinawa), was determined using the Ohrui–Akasaka method.541

The structure of an anti-inflammatory butenolide, previously

reported from Euplexaura flava (Ishigaki Is., Okinawa),542 was
confirmed by synthesis.543 Stereoselective synthesis was a power-
ful tool in the stereochemical corrections of the oxylipin sol-
andelactones (Solanderia secunda)544 with full accounts of the
revisions for solandelactones E545,546 and F546 published. Similar
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synthetic methodologies were used to determine (and revise) the

configurations of the other solandelactones A 615, B 616,546 C
617, D 618, G 619 and H 620.547 Claviridic acids A–E 621–625 reported from an Indonesian collection of the soft coral
are mildly cytotoxic prostanoids isolated from Clavularia viridis Lobophytum sp.554
(Kenting, Taiwan).548

The structure and absolute configuration of (–)-isishippuric acid

A purple pigment, produced in sclerites of Gorgonia ventalina in
A (Isis hippuris)555 was confirmed by stereoselective synthesis.556
response to biotic insults, was a polyene carotenoid.549 Five new
The rearranged sesquiterpene trocheliophorin 640, possibly
purine and pyrimidine alkaloids 626–630 were reported from
a catabolite of the well-known cnidarian natural product (and
a collection of Subergorgia suberosa (South China Sea).
co-metabolite) sarcophytin, was isolated from an Indian Ocean
Compounds 628 and 629 were claimed as new compounds, but
(Mandapam Coast) collection of Sarcophyton trocheliopho-
with different names, in two separate publications by the same
rum.557 Caryophyllane sesquiterpenoids sinunorcaryophyllenol
authors.550,551 A Gulf of Aqaba (Israel) collection of S. hicksoni
641 (Sanya, Hainan Province, South China Sea)558 and rum-
yielded the unusual cyclic peptides hicksoanes A–C 631–633.552
phellatin D 642 (unknown location)559 were isolated from the soft
The absolute configuration of 631 was determined by a combi-
corals Sinularia sp. and Rumphella antipathies, respectively. In
nation of degradative and NMR data analysis. All three
the case of the latter metabolite, mild inhibition of human
compounds exhibited feeding deterrence towards goldfish. Five
neutrophil elastase release was observed.
new examples of aplysinopsin dimers tubastrindoles D–H 634–
638 were reported from extracts of the stony coral Tubastraea
aurea (Odomari, Kagoshima, Japan).553 A new congener of the
zoanthamine alkaloids, lobozoanthamine 639, was recently

Two sesquiterpenes, 643 and 644, and a related carboxylic acid

645 were reported from a Taiwanese collection of Sinularia
sp.560 Polydactins A 646 and B 647 (Sinularia polydactyla,

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Hainan Is., South China Sea) exhibited modest cytotoxicity
in vitro.561
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Five new capnellane-skeleton sesquiterpenes 648–652, isolated
from a Green Is. (Taiwan) collection of Capnella imbricata, failed
to exhibit anti-inflammatory activity (iNOS and COX-2), while
known structurally-related members of the family were active.562
Acetoxycapnellenes 653–656 and an epoxyprecapnellene 657
were reported from the soft coral Dendronephthya rubeola (Bali,
Indonesia).563
A library of semisynthetic esters of capnellene-8b,10b-diol was
prepared and evaluated against a panel of human tumour cell
lines; only modest variations in potency were identified.564 Nar-
dosinane sesquiterpenes 658–660 were isolated from an Indone-
sian collection of Nephthea sp.,565 while the structurally-related
nardosinanols A–I 661–669 and lemnafricanol 670, possessing
a novel skeleton, were reported from Kenyan specimens of
Lemnalia sp., Paralemnalia clavata, Lemnalia africana and Rhy-
tisma fulvum fulvum.566 Moderate toxicity to brine shrimp larvae
was observed for 663, 667 and 670.
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The highly oxygenated guaiane lactones 1-epimenverin B
671, menverin F 672, 1-deoxymenverin F 673 and menverin
G 674 were isolated from a Menella sp. (Hainan Province,
China).567 The absolute configuration at C-8 of 672–674 was
assigned as (S) by interpretation of electronic circular
dichroism (ECD) data; all other configurations remained as
relative only.
A detailed evaluation of the in vitro and in vivo anti-inflam-
matory activites of lemnalol (Lemnalia cervicorni)568 was pub-
lished.569 By studying the presence of terpene metabolites and
biosynthetic capability between populations of healthy and
naturally bleached Plexaurella fusifera, it was concluded that
the zooxanthellae played no role in sesquiterpene production by
the soft coral.570 Enantioselective synthesis of the soft coral
diterpene clavirolide C (Clavularia viridis)571 confirmed the
structure and defined the absolute configuration.572 The rear-
ranged dolabellane diterpene 675 was obtained as the acetate
from Clavularia inflata.573 Sinulodurins A 676 and B 677
(Sinularia dura, Palau) exhibited antiproliferative activity and
also decreased disaggregation and cell migration in an in vitro
model of metastasis.574
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Stereoselective synthesis yielded diastereomers of the mildly
antimycobacterial soft coral diterpene erogorgiaene
(Pseudopterogorgia elisabethae),575 with one isomer having greater
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biological potency.576 A new anti-inflammatory pseudopterosin,
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iso-pseudopterosin E 678, was isolated from P. elisabethae.577
A C-glycoside analogue of pseudopterosin A methyl ester
exhibited similar potency to the natural O-glycoside natural
products in a range of inflammatory, phagocytosis and adeno-
sine receptor assays, indicating that the pseudopterosins are not
glycosidase-activated pro-drugs.578 Size-reduced seco-pseu-
dopterosins also maintained similar biological properties to the
natural products.579 Ten new verticillane-type diterpenes were
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reported from collections of Cespitularia erecta (679, Batangas,
Philippines)580 and C. hypotentaculata (cespihypotins M–V, 680–
689, Green Is., Taiwan).581,582 Of 684–689, only cespihypotin
T 687 was cytotoxic (moderate). A considerable number of
cembranoid-related marine natural products were published in
2008. Furancembrane gibberosene A 690 and regular cembranes
gibberosenes B–G 691–696 were isolated from Sinularia gibber-
osa (Kenting, Taiwan).583 The mildly COX-2-inhibiting die-
poxysarcophytonene 697 and sarconphytonol 698 were reported
from extracts of the soft coral Sarcophyton latum (Monkey Is.,
Hainan Province, China).584 Of five 10-oxocembranoids grandi-
lobatins A–E 699–703 isolated from Sinularia grandilobata
(Pingtung County, Taiwan), only 702 exhibited any (modest)
cytotoxicity. Grandilobatins B 700 and D 702 had differing
effects on the expression of iNOS and COX-2 in macrophage
cells.585 A Reunion Is. (Indian Ocean) collection of Sarcophyton
flexuosum yielded cembranes flexusine A 704 and B 705 and
epimukulol 706,586 while epoxy-eneones leptodienone A 707 and
B 708 were isolated as mildly cytotoxic constituents of
Leptogorgia laxa (Gulf of California, Mexico).587 Three new
cembranes 709–711 were isolated from Sarcophyton mililatensis
(Baycanh Is., Vietnam), and 709 exhibited a stimulatory effect on
osteoblastic cells in vitro.588 A fourth cembrane was claimed as
new by the authors, but had in fact been previously reported
from an Okinawan collection of Sarcophyton sp.589 In a disturb-
ing development, two publications originating from the same
laboratory have described a number of soft coral cembrane
diterpene metabolites with inconsistent relative configuration
assignments and with different trivial names being assigned to
identical chemical structures. In the first paper, sinulaflexiolides
A–K 712–722 were reported from a Sanya Bay (China) collection
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of Sinularia flexibilis and the structures assigned by standard
spectroscopic methods.590 In the second paper, specimens of
Dendronephthya sp. (same collection location) yielded cembranes
dendronpholide A–R 723–740, again with structures assigned by
standard NMR spectroscopic methods.591 The structure reported
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for dendronpholide G 729 is a duplicate of the structure assigned
to sinulaflexiolide E 716, while similar duplication exists between
dendronpholide H 730 and sinulaflexiolide F 717, requiring these
pairs of trivial names to be separately regarded as synonyms. The
spectroscopic data reported for dendronpholide A 723 were
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essentially identical to those reported for sinuflexiolide K 722;
however, the structures were presented as epimeric at C-13. A
similar situation exists for the pair of metabolites den-
dronpholide B 724 and sinuflexiolide J 721 – identical NMR
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spectroscopic data, but C-13 epimeric configurations again
depicted. The lead author of the publications agrees that errors
exist (personal communication), and a correction is expected.
Regular cembranes 741 and 742, in addition to a-methylene-g-
lactone cembranoids 743 and 744, were reported from South
China Sea (Lingshui Bay, Hainan) collections of the soft coral
Lobophytum sp.592 The absolute configuration of crassumolide A
745, one of six metabolites including crassumolides B–F 746–750
isolated from L. crassum (Kenting, Taiwan), was determined.593
Many of the cembranoids, in addition to a number of known
metabolites isolated from the extract, exhibited cytotoxicity and
inhibited expression of pro-inflammatory marker proteins. A
study of the stereochemical aspects of claimed new natural
products 751–754 and a number of known lactonic cembranoids,
including sinulariolide B isolated from a South China Sea
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collection of L. crassum, has been published.594 The structure,
relative and absolute configuration (1R,2R,3R,12S,13R) of sin-
ularolide B, recently reported as a ‘new’ compound from a
Hainan collection of Sinularia gibberosa,595 was defined by X-ray
analysis, comparison of a solid-state CD spectrum with that
calculated using the time-dependent density functional theory
approach,594 and by Mosher’s analysis.596 The structural novelty
of sinularolide B, 751, 753 and 754594,596 is debatable, as they
appear to be stereochemically related to the lobolide cembranes
previously reported from Lobophytum crassum (Red Sea).597,598
Novel or not, the absolute configurations of these and related
cembranes have been defined.596 Trans-fused a-methylene-g-
lactone-containing durumolides A–E 755–759 were isolated and
characterised from an extract of Lobophytum durum (Dongsha
Is., South China Sea).596 Durumolide C 757 is identical in all
respects to presinularolide B 752.594 Lobophytolides A–F 760–
765 were isolated from a Hainan (South China Sea) collection of
Lobophytum sp.599 Lobophytolide A 760 was the enantiomer of
a semi-synthetically prepared gorgonian cembrolide,600 adding
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further support to the empirical rule that cembrane diterpenes
sourced from organisms of the order Alcyonacea bear a C-1a
configuration, whilst cembranes isolated from the order Gorgo-
nacea belong to the b series. Lobophytolide D is an epimer (at
C-3 or C-13, depending upon which numbering scheme is used)
of sinularolide E.595 The lobophytolide study599 also summarised
observations regarding 1H and 13C chemical shifts associated
with the configuration of the alcohol substitution at C-13 (C-3)
and the cis/trans-lactone ring junction. 17-Hydroxysarcophyt-
oxide 766 and sarcophine analogue 767 were obtained from
extracts of Sarcophyton sp. (Gulf of Suez, Egypt).601 Diketo-g-
lactone-containing cembranoids sarcostolide A–G 768–774
(Sarcophyton stolidotum, Kenting, Taiwan) were reported as
exhibiting mild levels of cytotoxicity.602 Pingtung (Taiwan)
collections of Sinularia querciformis yielded 3-lactones queri-
formolide A–D 775–778, while 776 and granosolides A 779 and B
780 were isolated from specimens of S. granosa.603 The structure
of 776, which appeared to be identical to that reported for
notandolide (Sinularia notanda),604 was confirmed by an X-ray
analysis, and the absolute configurations of 775 and 776
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determined. iNOS and COX-2 protein expression was inhibited
by 777 and two previously reported 3-lactones. Danielid 781 was
the only new metabolite of a number of cembranes and sesqui-
terpenes isolated from Sinularia asterolobata (Bali, Indonesia).605
Bipinnatins K–Q 782–788, a series of furanocembranoid-related
metabolites, were isolated from Pseudopterogorgia kallos (West
Indies): the structures and relative configurations of 783 and 785
were secured by X-ray analysis.606 Modest cytotoxicity and
nACh receptor activity was observed for some of the diterpenes.
Lipidyl pseudopteranes A–F 789–794 were isolated from the soft
coral P. acerosa (Sweetings Cay, Bahamas).607 Biomimetic
synthesis of 789 was achieved by reaction of pseudopterolide, of
known absolute configuration,608 with palmitic acid. This,
combined with ECD measurements, established the absolute
configuration of 789. The relative configuration at C-11 of 792
could not be defined. Both 789 and 792 were modest inhibitors of
the function of protein tyrosine phosphatase 1B. Due to
conformational mobility of the 14-membered macrocycle, many
of the relative stereochemical assignments of the bis-cembranoids
ximaolide F 795 and G 796 (Sarcophyton tortuosum, Ximao Is.,
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Hainan, South China Sea) were based upon biosynthetic argu-
ments.609 The cladiellin/eunicellane diterpene sinensin 797 was
isolated from a South China Sea collection of the gorgonian
Muricella sinensis.610 Asymmetric total synthesis and X-ray
analysis611 defined the absolute configuration of (+)-vigulariol
(Vigularia juncea).612 Gorgonians of the genera Briareum,
Junceella and Ellisella are renowned for their abilities to elabo-
rate the briarane diterpenes. In addition to new members of the
briaexcavatin family of briaranes (I–L, 798–801) the known
congeners excavatolides C and E613 were isolated from cultured
specimens of Briareum excavatum,614 and the absolute
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configuration of excavatolide E determined. In the same publi-
cation was reported the isolation of a chlorinated briarane, fra-
gilide C 802, from Junceella fragilis. In two subsequent
publications, the same research group reported briaexcavatins
M–T 803–810 from the same source (cultured Briareum excava-
tum).615,616 The latter study also reported robustolides J 811 and
K 812 from Ellisella robusta (Southern Taiwan). Frajunolides
E–K 813–819 (Junceella fragilis, Tai-Tong County, Taiwan)
include five chlorinated examples.617 Eight briaranes, 820–827,
were isolated from extracts of J. juncea (Southern Taiwan) and
presented in two separate reports.618,619 Unfortunately, the
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already confusing landscape of briarane metabolite trivial names
has been further clouded by the authors ascribing the trivial
names of ‘junceols A–H’ to 820–827: junceol has been used
previously (by some of the same authors) to name an unrelated
sesquiterpene.620 One of the studies also reported the structure of
fragilide D (J. fragilis),618 which was identical to that presented
for frajunolide G 815.617 An Okinawan collection of Pachycla-
vularia sp. was the source of brianodins A–D 828–831.621 The
absolute configurations of brianodins C 830 and D 831 were
determined. Brianodin A 828 exhibited modest cytotoxicity. A
publication reporting two briarane diterpenes (Ellisella
robusta)622 claimed the novelty of robustolide H 832, but the
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reversal of two 13C NMR assignments would establish identity
with gemmacolide C.623 The study also presented the X-ray
analysis of 833, which the authors named robustolide I. This
structure, which contained a diene in the s-cis conformation, was
isomeric with a previously reported s-trans conformation diter-
pene.624 The absence of NMR data in the more recent paper
made it uncertain whether the metabolites were one and the
same. A North Sulawesi (Indonesia) collection of Xenia sp.
afforded the xenicane diterpenes xenimanadins A–D 834–837.625
The absolute configuration of xenimanadin A 834 was deter-
mined. Pregnanes 838–841 (Eunicella cavolini, Lichadonissia
Isles, Greece) exhibited mild growth inhibitory effects towards
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breast MCF-7 cells in vitro.626 The absolute configuration of 840
was determined and related to 838, 839 and 841 by chemical
interconversions. Five 3-ketosteroids, griffinisterones A–E 842–
846, were isolated from Dendronephthya griffini (dredging, Tai-
wan Strait) and the (24S) configuration of 842 secured by X-ray
analysis, while preparation of the diastereomeric phenylglycine
methyl ester derivatives established the (20R) configuration of
846.627 A second publication presented the structures of griffi-
nisterones F–I 847–850 and griffinipregnone 851 from the same
collection.628 The polyoxygenated steroids 852–860 isolated from
collections of Sinularia sp. and S. facile (Taiwan) exhibited
combinations of weak cytotoxicity and moderate anti-inflam-
matory activity.629,630 Parathiosteroids A–C 861–863 were
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isolated as mildly cytotoxic constituents of a Madagascan
collection of the soft coral Paragorgia sp.631 The structures and
absolute configurations were confirmed by synthesis and a small
library of analogues prepared to evaluate structure–activity
relationships. A new sterol, 864, isolated from Nephthea sp.
(Xisha Is., South China Sea), exhibited mild cytotoxicity.632 23-
Keto-cladiellin-A 865, isolated from the invasive soft coral
Chromonephthea braziliensis (Saco dos Cardeiros, Brazil), was
a feeding deterrent in field assays.633 The 4-methylated steroids
nebrosteroids A–H 866–873 (Nephthea chabroli, Tsau-Lou-Cho
Is., Taiwan),634 1-keto-steroids stoloniferones R–T 874–876 and
the 24-methylenecholesterol analogue 877 (Clavularia viridis,
Green Is., Taiwan)635 exhibited variable effects on gene
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expression of pro-inflammatory marker proteins. The unusual
3,5-epoxysterol 878 was claimed as a metabolite of Plexaura
flexuosa (Mochima Bay, Venezuela).636 Steroids, previously
reported from Leptogorgia sarmentosa,637 have been synthesised
and were mildly cytotoxic.638,639 Purified metabolites from the
gorgonians Subergorgia suberosa and Scripearia gracillis exhibi-
ted a range of antibacterial properties and inhibited the
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settlement of barnacle and bryozoan larva.640 Bioassay-directed
investigation of extracts of the nematocysts of the fire coral
Millepora dichotoma var. tenera (Aka Is., Okinawa, Japan)
yielded an 18 kDa protein (MCTx-1) that was potently cyto-
toxic.641 Seven colour morphs of the anthozoan Corynactis cal-
ifornica yielded six closely related Green Fluorescent Protein-like
proteins that had varying emission spectra.642
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9 Bryozoans
Research on metabolites from bryozoans continues to be very
limited. Pterocella vesiculosa (Alderman Islands, New Zealand)
yielded four alkaloids, pterocellins C–F 879–882, of which the
latter two, pterocellins E 881 and F 882, are dimers. Pterocellins
C–F 879–882 exhibited variable levels of activity against
B. subtilis, with 879 and 880 exhibiting strong activity. Pterocellin
D 880 also displayed modest activity against P388 cells and
Trichophyton mentagrophytes.643
10 Molluscs
While 2007 saw a peak in the number of new metabolites
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reported from molluscs, the number reported in 2008 dropped
off by 20%. New examples of a C37 carotenoid, isolated as
a mixture of esters 883, were reported from the clam Paphia
amabillis (Mimase, Japan).644 The structure proposed for a serine
protease inhibitor isolated from the green mussel Perna viridis
884 was not consistent with the reported NMR spectroscopic
data.645 New paralytic shellfish poisoning (PSP) saxitoxin
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analogues 885–887 were isolated from mussels (Mytilus edulis
and M. trossulus) collected during an intense bloom of Alexan-
drium tamarense off the coast of Nova Scotia, Canada.646 Lack of
sample prevented toxicological studies. New esters of okadaic
acid 888–895 were identified in both seawater and the hepato-
pancreas of Mytilus edulis (Flødevigen, Norway).647 Details of
the MS–MS methodology used for identification of the toxins
was reported separately.648 The ability of marine organisms to
excrete domoic acid was studied.649 The use of surface plasmon
resonance-based methodology for detection of polyether toxins
of the yessotoxin family has been described.650 As part of
a mechanism of action study of spirolides A and B, it was found
that the presence of a methyl group on the imine-containing ring
makes the toxins resistant to hydrolytic conditions in shellfish.651
The three-dimensional structure of mytilin, a 34-residue peptide
(Mytilus galloprovincialis), was determined by NMR spectro-
scopic methods, and structurally-related synthetic peptides
evaluated for antibacterial and antiviral properties.652 A cysteine-
free peptide conorfamide-Sr2 896, purified from the venom
extract of Conus spurius (Caribbean Sea, Yucatan Peninsula),
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exhibited paralytic activity towards limpets, but hyperactivity in
mice.653 At the other extreme of cysteine incorporation was
conotoxin vi15a 897, a 27-residue peptide containing eight
cysteines (C. virgo, Hainan, China), which qualifies as a member
of the V-superfamily of conotoxins.654 Investigation of a cDNA
library prepared from C. parius venom duct (unstated location)
led to the discovery of c-conotoxin PrIIIE 898, which inhibited
nicotinic acetylcholine receptors (nAChR) and induced flaccid
paralysis of fish.655 a4/7-Conotoxin Lp1.1 899 (C. leopardus,
South China Sea) induced seizures and paralysis in fish and
reversibly inhibited nAChRs.656 Investigation of the natural
products chemistry of a South African collection of the intertidal
pulmonate limpet Trimusculus costatus yielded three new
metabolites 900–902657 as well as the known labdane 903.658 A
(3S) configuration was assigned to 901, while X-ray analysis of
a camphanate derivative of 903 determined the absolute labdane
configuration. Modest cytotoxicity was observed for 900 and 901
towards an oesophageal cancer cell line in vitro. Two labdanes
904 and 905 were reported from a Chilean collection of T.
peruvianus.659 Two non-contiguous carbon skeleton poly-
propionates micromelone A 906 and B 907 were isolated from
the opistobranch mollusc Micromelo undata (Tenerife).660 Ster-
eoselective synthesis established a corrected structure for
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kulokekahilide-2 908,661 a cyclic depsipeptide isolated from the
carnivorous mollusc Philinopsis speciosa,662 diastereoisomeric to
that originally reported. Further investigation of the predator–
prey relationship between the sea hare Syphonota geographica
and the sea-grass Halophila stipulacea yielded acetate 909
exclusively from the sea-grass, while potential bio-trans-
formation products 910 and 911 were found only in extracts of
the mollusc.663 The structure of the moderately cytotoxic tri-
azabicyclooctane metabolite aplaminal 912, isolated from the sea
hare Aplysia kurodai, was confirmed by X-ray analysis;664 the
absolute configuration was established by enantioselective
synthesis.665 Stable-isotope biosynthetic studies of lignarenones 1
and 2, u-phenyl-conjugated trienones isolated from Scaphander
lignarius,666 suggested a PKS-like process primed with benzoic
acid, derived from phenylalanine.667 A biomimetic racemic
synthesis of the proposed revised structure668 of the Tridachia
crispata-derived metabolite tridachiahydropyrone669 913 was
reported.670 A Panamanian collection of the sacoglossan mollusc
Elysia diomedea yielded the endoperoxide 914 and the pyrones
915 and 916.671 The observation of rearrangement of 914 with
triethylamine to yield the known vicinal diexpoxide elysiapyrone
A672 prompted speculation of the biosynthetic intermediacy of
914, likely to be in turn derived from a putative polypropionate
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alkenyl chain-containing precursor reacting with singlet oxygen. a number of simple bactericidal compounds.683 Mildly cytotoxic
Four new members of the kahalalide family of cyclic depsipep- oxygenated diterpenes 921 and 922 were isolated from the
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tides V–Y 917–920 were reported from an Hawaiian collection of nudibranch Chromodoris sp. (Mooloolaba, Australia).684
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E. rufescens.673 Structure–activity relationship studies of kaha-

lalide F674 identified a number of more potently antiproliferative
analogues,675 while a reverse chemical proteomics study using
biotinylated kahalalide F identified human ribosomal protein
S25 as a potential binding partner.676 Phase I clinical and phar-
macokinetic results for kahalalide F have been reported.677 The
relationship between Elysia chlorotica (and E. crispata)678 and the
algal diets is far deeper than one of simply predator–prey. This
came from the discovery that the algal oxygenic photosynthetic
gene psbO has been incorporated into the sea slug’s nuclear DNA Dialdehyde 921, located primarily in the nudibranch’s mantle
by horizontal gene transfer.679 Several synthetic analogues of the and hence suggestive of playing an ecological role, was reactive
cytotoxic depsipeptide aurilide (Dolabella auricularia)680 showed towards methanol, yielding a mixture of hemiacetals. Hemi-
potent biological activity and could be useful as molecular acetal 923 was also isolated from the organism, but shown to be
probes to determine cellular binding partners.681 Bombesin– an artefact arising from the use of methanol in the purification
dolastatin conjugates bound to cells expressing bombesin protocol. This result led to the suggestion that hemiacetal 924
receptors, but failed to exhibit cytotoxicity.682 It was established isolated from the nudibranch Cadlina luteomarginata685 using
that the ink released by Aplysia californica contained an a methanol–dichloromethane extraction protocol was also
L-amino acid oxidase enzyme that metabolised L-lysine to artefactual.

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Tambjamine D (Tambja eliora)686 acted as a pro-oxidant,
yielding DNA strand breaks and induced apoptosis in hamster
lung fibroblast cells.687 Stable-isotope precursor feeding studies
using Doriopsilla sp. (Set ubal, Portugal) established that a dri-
mane ester mixture and 15-acetoxy-ent-pallescensin688 were
derived de novo via the classical mevalonate pathway.689 The
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study also led to the characterisation of the diastereomeric
acetates of pelseneeriol-1 and -2 925 and 926. A full account of
the synthesis of the corrected structure690 of (–)-ulapualide A
(Hexabranchus sanguineus) has appeared.691
11 Tunicates (ascidians)
After a steep decline in new metabolites reported in 2006, the
numbers reported in 2007 and 2008 have returned to the average
of 35 per year. The iodinated nucleoside 927, isolated from
Diplosoma sp. (Hateruma Is., Okinawa), inhibited the division of
fertilised sea urchin eggs.692,693 The structure of amaminol B,
a bicyclic amino alcohol reported from an unidentified tunicate
(Amami Is., Japan)694 was confirmed by synthesis,695 while the
structural confirmation and assignment of absolute configura-
tion to lepadins F 928 and G 929696,697 was achieved by stereo-
selective synthesis of the enantiomers.698
The known guanidine alkaloid tubastrine, a series of saturated
930 and dimeric analogues 931–935 and a spermidine derivative
936, isolated from a New Zealand collection of Aplidium orthium,
were reported as inhibitors of human neutrophil respiratory
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burst.699 The first (racemic) synthesis of an unnamed indole
alkaloid isolated from Dendrodoa grossularia700 was reported.701
In addition to a number of known metabolites, the likely arte-
factual indoyl-glyoxalate 937 was reported from the ethanolic
extract of Syncarpa oviformis (Kuril Is., Russia).702
Aplicyanins A–F 938–943, analogues of the meridianins703
(protein kinase-inhibiting Aplidium metabolites) were isolated
from A. cyaneum (Weddell Sea, Antarctica).704 Whilst 938, 940
and 942 were either inactive or only mildly cytotoxic, 939, 941
and 943 were submicromolar growth inhibitors, with 943 also
exhibiting potent antimitotic activity. A South Korean collection
of Eudistoma sp. afforded a combinatorial collection of bromi-
nated 1-benzoyl-b-carbolines, eudistomins Y1–Y7 944–950.705
None of the compounds were cytotoxic (100 mM), but mild
antibacterial activity was observed for 949.
Non-symmetrical b-carboline dimers 951–953 were isolated from
Didemnum sp. (Sykes Reef, Great Barrier Reef, Australia), and
the structures of 951 and 952 confirmed by synthesis.706 The new
benzopentathiapene isolissoclinotoxin B 954 and pyridoacridine
alkaloids diplamine B 955 and lissoclinidine B 956 were reported
from Lissoclinum cf. badium (Papua New Guinea).707 Lissocli-
nidine B was found to inhibit ubiquitylation and degradation of
tumour suppressor p53, thereby inducing cell apoptosis in a p53-
dependent manner. Two new indolocarbazole staurosporine
alkaloids, 957 and 958, were reported from Cystodytes solitus
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(Tanzania) and, as expected for this compound class, exhibited
nanomolar potency growth inhibition of three human tumour
cell lines in vitro.708 An Indonesian collection of Diazona sp.
afforded three new members of the diazonamide family of
macrocyclic peptides, diazonamides C–E 959–961.709 All three
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compounds were two to three orders of magnitude less cytotoxic
towards a panel of human tumour cell lines than the parent
compound diazonamide A. Mollamides B 962 and C 963,
reported from Didemnum molle (Indonesia),710 and hexamolla-
mide 964, isolated from an Okinawan collection of the same
organism,711 all exhibited mild cytotoxicity. The presence of
cyclic peptides belonging to the patellamide class in ascidians has
previously been ascribed to the biosynthetic prowess of symbiotic
cyanobacteria belonging to Prochloron spp.712,713 Further genetic
studies have now extended this biosynthetic capability to include
prenylated analogues such as the patellins and trunkamide.714
The three-dimensional structures of westiellamide715/cycloxazo-
line716 cyclic hexapeptide analogues have been studied by X-ray
analysis and DFT calculations717 and the ability to coordinate
CuII investigated.718 The FeII chelating properties of the b-car-
boline alkaloids eudistomin G and H were studied by LC–ICP-
MS/ES-MS in extracts of Eudistoma gilboviride.719 Two unstable
isomeric pyrones, previously reported from the sponge Ulosa
sp.,720 were re-isolated from the ascidian Diplosoma virens, and
found to exhibit cytotoxicity via caspase activation.721 The
microbial community of the palmerolide-producing ascidian
Synoicum adareanum was investigated as a prelude to bacterial
culturing and metagenomic studies.722 Biological investigation of
a series of synthetic palmerolide A analogues identified essential
and superfluous structural features.723 The tunichromes, dehy-
drodopa-containing alkaloids previously reported from the
haemocytes of Ascidia nigra,724 undergo oxidative polymerisa-
tion and were antimicrobial towards Gram-negative bacteria.725
3-Desmethylubiquinone Q2, previously isolated from Aplidium
glabrum,726 inhibited the growth of solid Ehrlich carcinoma in
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mice and induced apoptosis in a number of tumour cell lines.727
An analogue of the ascidian-derived aminothiazole alkaloid
dendrodoine728 acted as a free radical scavenger and antioxi-
dant.729 The in vivo effects of a synthetic analogue of polycarpine
(Polycarpa clavata)730 on Ehrlich carcinoma were assessed by
MRI.731 Structural hybrids of ascidian (meridianin) and sponge
(variolin)-derived kinase inhibitors also exhibited potent inhib-
itory activity towards cyclin-dependent kinases.732 An ongoing
study of molecules combining structural features of caffeine and
the ascidian metabolite eudistomin D as adenosine receptor
binders was reported,733 while analogues of the ascidian
metabolite bengacarboline734 acted as potent cytotoxins and
accumulated cells in the S phase of DNA synthesis.735 The
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structure–activity requirements of a sulfated steroid responsible
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for sperm activation and attraction in the ascidian Ciona intes-
tinalis736 were reported.737 The cyclic depsipeptide aplidine
demonstrated in vitro and in vivo xenograft activity against
multiple myeloma.738 The clinical role played by ecteinascidin-
743 (Trabectedin, Yondelis) in the treatment of soft tissue
sarcoma was summarised,739 while the main toxicity of the drug,
myelosuppression, has been the subject of pharmacokinetic
and pharmacodynamic meta-analysis.740 Mining the genome
of Ciona intestinalis led to the identification of a new class of
antimicrobial peptide that acted by permeabilising
cytoplasmic membranes, but with very low cytolytic activity
towards mammalian erythrocytes.741 A vasopressin/oxytocin
neuropeptide and receptor was characterised in an ascidian
(C. intestinalis) for the first time.742
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12 Echinoderms
The number of new metabolites reported annually from echi-
noderms, having remained relatively constant over the 2002–
2007 period, dipped slightly in 2008. In addition to four known
gangliosides, a new monomethylated example, DSG-A 965, was
isolated from the ovaries of the urchin Diadema setosum
(Kagoshima, Japan).743 As with most gangliosides, neuritogenic
activity was observed towards rat pheochromocytoma cells in the
presence of nerve growth factor. Naphthopyrones 966 and 967
were isolated from the crinoid Comanthus parvicirrus (Caqalai
Is., Fiji) and found to inhibit TNF-a-induced NF-kB activation
by inhibiting IKKb kinase.744,745 Sterols 968 and 969 were iso-
lated from extracts of the starfish Asterias amurensis (Guangxi,
North Sea of China), with 969 and the semi-synthetic desulfated
analogue found to promote proliferation of osteoblast cells in
vitro.746 Stereoselective semisyntheses of certonardosterols D2
and D3 (Certonardoa semiregularis)747 from diosgenin were
reported.748,749 Determination of total triterpene glycoside
content in Stichopus japonicus, using a hydrolysis–precolumn
derivatisation method to quantify the levels of the unique che-
momarker D-quinovose, was reported.750 In addition to a number
of known steroids, fuscaside A 970 and B 971 and desulfated
minutoside A were reported from Lethasterias fusca (Possiet
Bay, Sea of Japan).751 Collection of the starfish Distolasterias
nipon from the same location yielded distolasterosides D6 972
and D7 973. Known analogues distolastereosides D1, D2 and D3
were found to induce murine neuroblast cell differentiation.752
Three steroidal triglycosides, kurilensosides A–C 974–976, the
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diglycoside kurilensoside D 977 and polyhydroxy steroids 978
and 979 were isolated as constituents of Hippasteria kurilensis
(Matua Is., Sea of Okhotsk) able to inhibit sea-urchin egg fer-
tilisation.753 A (24S) configuration for 974 was determined and
transferred by biosynthetic implications to 975. The structurally-
related diglycoside leviusculoside G (Henricia leviuscula)754
induced p53-dependent apoptosis in a number of cell lines.755 A
South China Sea collection of Holothuria axiloga yielded the
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known sodium sulfated metabolite holothurin B and the corre-
sponding free sulfate.756 Unfortunately, the authors chose to give
the free sulfate a trivial name (axilogoside A). Two new steroidal
tetraosides, 17-hydroxyfuscocineroside B 980 and 25-hydrox-
yfuscocineroside B 981, and the known metabolite fuscocinero-
side B,757 were isolated from the sea cucumber Bohadschia
marmorata (Hainan Is., South China Sea).758 The tetraoside 980
and the parent exhibited modest antifungal properties. Using
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combinations of ion-pair reverse-phase and cyclodextrin chiral
chromatography, three known and five new glycosides liou-
villosides A1–3 982–984, B1 985 and B2 986 were isolated from an
Antarctic collection of Staurocucmis liouvillei.759 The structurally
related tetraosides okhotoside B1–3 987–989 were reported from
Cucumaria okhotensis (Sea of Okhotsk, Kamchatka).760 The
same report also detailed extensive cell cycle and transcriptional
effects of the known co-metabolite frondoside A.761 A separate
account of the immunomodulatory activities of frondoside A
was also reported.762 The O-methyl glucuronic acid-containing
pentaosides synaptoside A 990 and A1 991 were isolated from
a Vietnamese collection of Synapta maculata.763 Only 990
exhibited cytotoxicity (mild). Holothuria grisea (Guangzhou,
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South China Sea) yielded two additional pentaosides, 17-dehy-
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droxyholothurinoside A 992 and griseaside A 993, both of which
exhibited modest cytotoxicity towards a panel of tumour cell
lines.764 In two separate accounts the structures of argusides B–E
994–997 were reported as cytotoxic constituents of the sea
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cucumber Bohadschia argus (Hainan, South China Sea).765,766
Leucospilotaside C 998, with the same aglycone as 992 and 997,
was obtained from Holothuria leucospilota.767 Holothurins A768
and B769 exhibited in vivo activity towards the causative agent of
leishmaniasis,770 while a common issue associated with saponins,
their haemolytic activity, was ameliorated somewhat in the case
of nobiliside A771 by use of a liposomal preparation.772
Membrane permeabilisation was attributed as the dominant
mode of action of the spermicidal properties773 observed for
bivittoside A.774
13 Mangroves and the intertidal zone
Recent years have seen a rapid rise in publications dealing with
mangroves. These have been associated with endophytes from
various parts of the mangrove, from the rhizosphere, or from
plant parts themselves. Like the intertidal zone, the mangrove
habitats in more tropical regions represent the terrestrial fringe
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of the marine habitat. In recent reviews the literature associated
with mangroves was restricted to new metabolites from ‘‘true’’
mangroves, but the degree of interest in, and publication of
metabolites from, ‘‘semi-mangrove’’ plants73 has led to a recon-
sideration for the presentation of the data this year. As noted
already in the Marine microorganisms section, the documenta-
tion of both the source and location of the mangrove metabolites
could be significantly improved to the benefit of all of the marine
natural products community. The stem bark of the Chinese
mangrove associate Catunaregam spinosa (Hainan Province,
China) yielded the dihydroisocoumarin 999 and iridoid 1000.775
Iridoid glycosides, marinoid A–E 1001–1005 were isolated from
the leaves of Avicennia marina (Xiamen, Fu Jiang Province,
China).776 Marinoids A–C were characterised as containing
a rare (8R) configuration. The diterpene 1006 (roots of Ceriops
tagal, Hainan Province, China) exhibited modest antifouling
activity towards Balanus albicostatus cyprids without toxicity.777
In a separate account, the same collection of C. tagal also
afforded the dimeric pimaranes tagalsins L–N 1007–1009.778 The
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stem bark of the mangrove plant Bruguiera gymnorrhiza (Hepu
County, China) yielded the lipophilic neolignan brugnanin
1010779 while the whole stems of Rhizophora stylosa yielded the
free radical scavenging (DPPH assay) flavan-3-ol glycosides
glabraoside A 1011 and B 1012.780 Three abietane diterpenes
1013–1015 and lignan 1016 were reported from the twigs of
Avicennia marina (Xiamen, China): 1013 and the hemiacetal
mixture of 1014 and 1015 exhibited mild cytotoxicity and Gram-
positive antibacterial activities.781 The seeds of Xylocarpus
granatum (Hainan Is., South China) yielded a diverse array of
new limonoids, xylogranatins F–R 1017–1029.782 Selected
examples of the limonoids exhibited antifeedant activity towards
the rice ear-cutting caterpillar Mythimna seperata. Five months
after this work appeared on-line, another group submitted
a manuscript describing the elucidation of a new alkaloid, which
they named granatoine A 1030 (fresh fruit of Xylocarpus gran-
atum, Hainan Is., South China), which was presented as
a stereoisomer of xylogranatin F 1017.783 The compounds differ
in reported [a]D (48 vs. +254 respectively). The study also
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disclosed the structure of xylocarpin L 1031. The nigram-skele-

toned triterpenes 1032–1034 were isolated from the mangrove
Hibiscus tiliaceus.784 Two diarylheptanoids 1035 and 1036,
a meroterpenoid 1037 and (unusually) a briarane diterpene 1038
were isolated from the sea-grass Cymodocea nodosa (Porto
Germeno, Greece).785 Mild antibacterial activity was exhibited
by 1035–1037. Jupiter Sound (Florida) collections of the sea-
grass Halophila johnsonii yielded an extensive range of flavone
and flavone glycosides including 1039–1045,786 while biological
evaluation of the known chemistry of the sea-grass Enhalus
acoroides (South China Sea) indicated that many of the meta-
bolites exhibit potential ecological roles including feeding deter-
rence, antibacterial and larval settlement inhibiting properties.787
Fermentation of the actinomycete Streptomyces sp. isolated
from rhizosphere soil of the mangrove Heritiera littoralis yielded
p-tolyl 3-aminopropanoate 1046 and 6-amino-3-(4-hydroxy-
benzyl)-1,4-diazonane-2,5-dione 1047, which were inhibitors of
the human hepatoma SMMC-7721 cell line.788

Fermentation of an Aspergillus sp, an endophyte from the inner

bark of the mangrove Kandelia candel (Mai Po, Hong Kong),
bark of the mangrove Acanthus ilicifolius (Dongzhai Gang,
yielded 6-demethylvermistatin 1058 and a penicillide derivative,
China), yielded two indolic enamides, terpeptin A 1048 and B
known as a synthetic compound791 but here reported as a natural
1049, which were modestly cytotoxic against A549 cells.789
product for the first time.792 A new friedelan derivative, 1059, was
isolated from culture of an unidentified endophytic mangrove
fungus (source not given, but presumably China).793 Fermenta-
tion of a Xylaria sp. obtained from seeds of a mangrove (Mai Po,
Hong Kong) yielded a ketal 1060 which was initially named
xyloketal H.794 However, this name had already been applied to

Eight aromatic polyketides, aspergiolide B 1050, three naphthyl

ribofuranosides 1051–1053, isoasperflavin 1054, variecolor-
quinone A 1055 and two isomeric bianthrones 1056 and 1057
were isolated from fermentation of A. glaucus separated from
mangrove root sediment (Fujian province, China). Of these,
aspergiolide B 1050 displayed potent cytotoxicity to HL-60 and
A549 cells whilst 1056 and 1057 were moderately cytotoxic to
these cell lines.790 Culture of a Guignardia sp. obtained from the

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another compound, isolated from the same source by the same
authors.795 A Xylaria sp. from the same source yielded xyloketal J
1061, xyloester A 1062 and xyloallenolide B 1063.796
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Phomopsin A 1064 was isolated from fermentation of the
endophyte Phomopsis sp. obtained from mangrove bark
(Zhanjiang, South China Sea) and displayed moderate inhibi-
tion of KB and KBv cells.797 Culture of a Phomopsis sp.,
identified only as a mangrove endophyte (Zhanjiang, South
China Sea coast) yielded two diaryl ethers, phomopside A 1065
and B 1066.798
Four triterpenes, 1067–1070, were isolated from fermentation of
a Phomopsis sp. obtained from the mangrove Hibiscus tiliaceus
(Dongzaigang, Hainan Province, China).799
Culture of a Penicillium sp., an endophyte of the mangrove
Cerbera manghas (probable source China) yielded 1071 and 1072
along with 3,4,5-trimethyl-1,2-benzenediol, a known synthetic
compound,800 but recorded here for the first time from a natural
source. Both 1071 and 1072 were inhibitory to MRSA.801 Culture
of a Penicillium sp., an endophyte of the mangrove Aegiceras
corniculatum (Fujian, China), yielded four polyketides,
leptosphaerone 1073, penicillenone 1074, arugosin I 1075 and
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9-demethyl FR-901235 1076, of which 1073 was cytotoxic to
A549 cells and 1074 was cytotoxic to P388 cells.802
Six tetramic acid derivatives, penicillenols A1 1077, A2 1078, B1
1079, B2 1080, C1 1081 and C2 1082, were isolated from a culture
of an endophytic Penicillium sp. obtained from the inner bark of
the mangrove Aegiceras corniculatum (Gaoqiao, China). Pen-
icillenols A1 1077 and B1 1079 were cytotoxic to the HL-60 cell
line.803 Fermentation of an endophytic fungus separated from the
Shenzhen semi-mangrove Acanthus ilicifolius yielded averantin
1083 in addition to a number of known metabolites, of which the
terrestrial fungal metabolites 10 -O-methylaverantin804 and 6,8-di-
O-methyl averufanin805 and the terrestrial natural product
derivative, 6,8-di-O-methyl averufin806 were isolated from
a marine source for the first time.807 The xanthone paecilox-
anthone 1084 was isolated from fermentation of a Paecilomyces
sp. separated from the bark of an estuarine mangrove (Taiwan
Strait) and was cytotoxic to hepG2 cells, Curvularia lunata,
E. coli and Candida albicans, in addition to displaying acetyl-
cholinesterase activity.808
Two new xanthones 1085 and 1086 were obtained from culture of
an endophytic Penicillium sp. separated from bark of the
mangrove Acanthus ilicifolius (Shenzhen, Guangdong, China).
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Xanthane 1086 was modestly active against Fusarium oxy-
sporum.809 Cultivation of an unidentified fungus separated from
an estuarine mangrove of the South China Sea coast yielded an
alternariol derivative 1087, weakly active against KB and
KBv200 cell lines.810
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Culture of the endophyte Eurotium rubrum obtained from the
mangrove Hibiscus tiliaceus (Hainan Is., China) yielded two
diketopiperazine derivatives, dehydrovariecolorin L 1088 and
dehydroechinulin 1089, together with a number of known
metabolites of which the previously reported terrestrial fungal
metabolites neoechinulin E811 and cryptoechinuline D812 dis-
played strong radical-scavenging activity.813 A new biphenyl
derivative, 1090, was isolated from culture broth of an uniden-
tified fungus isolated from rhizosphere soil of mangrove roots on
the South China Sea.814
Fermentation of a Gloesporium sp., an endophyte of the true-
mangrove Bruguiera gymnorhiza (South China Sea), yielded the
This journal is ª The Royal Society of Chemistry 2010
View Online
known synthetic compound 3-benzylpiperazine-2,5-dione815 for
the first time as a natural product, and the first isolations of 3-(2-
methylpropyl)-2,5-piperazinedione816 and 3-phenylpropanoic
acid817 from the marine environment.818 Culture of an endophytic
Fusarium sp. obtained from the leaf of the mangrove Casta-
niopsic fissa (Zhanjiang, South China Coast), yielded a copper
coordination complex, previously known as a synthetic oxygen
inhibitor,819 but now isolated for the first time as a natural
product. The complex displayed mutagenicity against several
bacterial strains and strong inhibition of three human cancer cell
lines.820 Anhydrofusarubin, a metabolite of the entomogenous
fungus Fusarium solani,821 was isolated from a marine source for
the first time from culture of an unnamed endophytic mangrove
fungus (South China Sea coast).822 A 24-membered macrolide,
macrolactin T 1091, and a polyene d-lactone, macrolactin U
1092, were isolated from culture of Bacillus marinus separated
from the intertidal succulent plant Suaeda salsa (Bohai Sea,
Eastern China).823 Miuraenamides C–F 1093–1096 are cyclic
hybrid polyketide-peptide antibiotics isolated from culture of the
slightly halophilic myxobacterium Paraliomyxa miuraensis
(near-shore soil, Japan). Miuraenamides A and B824 were also
Nat. Prod. Rep., 2010, 27, 165–237 | 223
 View Online

isolated and the absolute configuration of miuraenamide A
determined as 1097. Miuraenamide A was a selective inhibitor of
the phytopathogenic microorganism Phytophthora capsici.825
14 Miscellaneous
Blubber from a variety of Australian marine mammals contained
a diverse array of naturally occurring polybrominated dime-
thoxybiphenyls, including 1098–1100.826 Bioassay-directed frac-
tionation of the fireworm Eurythoe complanata yielded
complanine 1101 as the active principle.827 Phthalates 1102–1104
were reported as very mild cathepsin B-inhibiting components of
extracts of the seahorse Hippocampus kuda.828 Interestingly,
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publications per decade (1959–68, 91; 1969–78, 867; 1979–88,
3292; 1989–98, 6746; 1999–2008, 9753), while Fig. 2 plots the
actual numbers of publications, also on a decade basis, and
contrasts them against the total number of publications (ALL).
What stands out from these figures is that for four decades the
lead journal for publication of marine natural products research
was Tetrahedron Letters. The Journal of Natural Products over-
took Tetrahedron Letters during the 1999–2008 decade [1169
(11.9%) versus 767 (7.9%)]. Other journals consistently near the
top of the list have been J. Am. Chem. Soc., Tetrahedron,
Phytochemistry, Experientia, J. Org. Chem., J. Chem. Soc.,
Chem. Commun., Aust. J. Chem., Synlett, Chem. Pharm. Bull.,
and, despite its relatively recent origin, Org. Lett. Some of the

similar cathepsin B activities had been found for known phtha- newer journals, such as Eur. J. Org. Chem. and Bioorg. Med.
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lates derived from the marine Pseudomonas sp. PBO1.829
15 Conclusion
In the 50 years since marine natural products emerged as
a discipline, over 21 000 papers have been published in this
general area. Where have these papers been published? What
have been the trends in the preferences for particular journals
over the years? Over 1200 journals have been used for publica-
tion, but about 950 journals had fewer than six papers over this
period. Table 1 shows the numbers for those journals that pub-
lished more than 200 papers over the last 50 years. A few journals
that have only been available within the past decade have also
been included where the numbers of papers for each has been
significant. Altogether, these listed journals have provided about
50% total coverage of the literature for each decade.
Fig. 1 is a direct comparison between decades, shown on
a percentage basis, due to the large differences in numbers of the
Chem. Lett., are starting to feature in the last decade. In terms of
total publications, the two top journals are very close when
summed across the 50 years. Between them, Tetrahedron Lett.
and J. Nat. Prod. have published 4600 marine natural product
papers, 22% of the output in the field. These journals are fol-
lowed by J. Org. Chem. and Tetrahedron, (1250 papers each),
and then J. Am. Chem. Soc. (832). Org. Lett. is already in fifth
place, despite having been published only since 1999.
It is also of interest to compare the selection of journals
reporting new compounds, the correction of structures and the
assignment of stereochemistry (NEW; 8200 papers), those
papers reporting syntheses (SYN; 6300 papers) and those that
were dealing with ecological aspects (ECOL; 2100 papers)
against the whole collection of marine natural product papers
(ALL; 21 000 papers) (see Table 1). For the publication of
NEW compounds, J. Nat. Prod. is a clear leader over Tetra-
hedron Lett. and J. Org. Chem., followed by Tetrahedron,
J. Am. Chem. Soc., Phytochemistry, Chem. Pharm. Bull., and

Table 1 Preferences in the selection of journal for publishing. Shown are the total numbers of papers published in each category over the period 1959–
2008. (ALL – total number; NEW – new compounds, stereochemistry; SYN – syntheses; ECOL – ecological studies. The table has been sorted using the
ALL column.)

Journal ALL NEW SYN ECOL

Tetrahedron Lett. 2453 1117 1334 123

J. Nat. Prod. 2127 1817 118 150
J. Org. Chem. 1275 619 657 104
Tetrahedron 1248 717 518 99
J. Am. Chem. Soc. 832 305 491 39
Org. Lett. 632 145 508 13
Phytochemistry 396 269 12 50
Chem. Pharm. Bull. 314 198 82 15
Angew. Chem., Int. Ed. 243 33 196 9
J. Chem. Soc., Perkin Trans. 1 & 307 96 210 18
Org. Biomol. Chem.
Chem. Commun. 226 91 125 14
Aust. J. Chem. 220 195 28 33
Toxicon 219 14 6 38
Heterocycles 216 64 131 6
Synlett 213 33 202 3
Chem. Lett. 208 135 69 10
Experientia/Cell. Mol. Life Sci. 185 118 13 46
J. Antibiot. 172 126 11 1
Tennen Yuki Kagobutsu Toronkai Koen Yosh 170 44 70 7
Bioorg. Med. Chem. Lett. 156 51 74 1
Eur. J. Org. Chem. 124 64 57 2
Bioorg. Med. Chem. 94 37 32 5
Synthesis 82 3 76 0
Chem.–Eur. J. 61 8 49 0

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 View Online
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Fig. 1 Journal publications by decade, shown on a percentage basis.

Fig. 2 Journal publications by decade, compared against total publications 1959–2008 (ALL).

This journal is ª The Royal Society of Chemistry 2010 Nat. Prod. Rep., 2010, 27, 165–237 | 225

Aust. J. Chem. A somewhat different order is seen for the
publication of papers dealing with syntheses. Synthetic effort is
led by Tetrahedron Lett. followed by J. Org. Chem., Org. Lett.,
Tetrahedron and J. Am. Chem. Soc., but not surprisingly there
are more synthesis-oriented journals appearing on the list such as
Synlett, Angew. Chem., Int. Ed., J. Chem. Soc., Perkin Trans. 1,
Heterocycles, Chem. Commun., Chem. Pharm. Bull. and
Synthesis. The last category examined was that of papers
reporting ecological results. J. Nat. Prod. again headed the list
followed by Tetrahedron Lett., J. Org. Chem., and Tetrahedron.
Because of the smaller proportion of papers dealing with this
topic, many otherwise important journals have not met the
threshold for inclusion in Table 1. These include some of the
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more ecology-specific journals such as Mar. Biol., J. Chem. Ecol.,
Published on 07 January 2010 on http://pubs.rsc.org | doi:10.1039/B906091J
Comp. Biochem. Physiol., Mar. Ecol., Toxicon, and many others.
In summary, the dominance of J. Nat. Prod., Tetrahedron Lett.,
J. Org. Chem. and Tetrahedron as the publishing media of choice
is noted. Also apparent is the decreasing role of Tetrahedron
Lett., the growing profile of Org. Lett., and the emergence of the
newer journals such as Bioorg. Med. Chem., Bioorg. Med. Chem.
Lett., Eur. J. Org. Chem. and Chem.–Eur. J.
16 Acknowledgement
The authors thank Drs Wan-Ping Hu and Sarah Hickford for
assistance with the collection of data for this review.
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