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A. Douglas Kinghorn · Heinz Falk ·

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Yoshinori Asakawa · Ji-Kai Liu Editors
112
Progress in the
Chemistry of
Organic Natural
Products
Progress in the Chemistry of Organic Natural
Products
Series Editors
A. Douglas Kinghorn , College of Pharmacy, The Ohio State University,
Columbus, OH, USA
Heinz Falk , Institute of Organic Chemistry, Johannes Kepler University, Linz,
Austria
Simon Gibbons , School of Pharmacy, University of East Anglia, Norwich, UK
Jun’ichi Kobayashi, Graduate School of Pharmaceutical Sciences, Hokkaido
University, Sapporo, Japan
Yoshinori Asakawa , Faculty of Pharmaceutical Sciences, Tokushima Bunri
University, Tokushima, Japan
Ji-Kai Liu , School of Pharmaceutical Sciences, South-Central University for
Nationalities, Wuhan, China
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Alvaro Viljoen, Department of Pharmaceutical Sciences, Tshwane University of
Technology, Pretoria, South Africa
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A. Douglas Kinghorn Heinz Falk
• •
Simon Gibbons Jun’ichi Kobayashi

• •
Yoshinori Asakawa Ji-Kai Liu

•
Editors
Progress in the Chemistry

of Organic Natural Products
Volume 112
With contributions by
Francisco A. Macías Alexandra G. Durán José M. G. Molinillo
Chuan-Yun Xiao Qing Mu Simon Gibbons
Samantha S. Yee Lin Du April L. Risinger
123
Editors
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College of Pharmacy Institute of Organic Chemistry
The Ohio State University Johannes Kepler University
Columbus, OH, USA Linz, Oberösterreich, Austria
Simon Gibbons Jun’ichi Kobayashi

School of Pharmacy Graduate School of Pharmaceutical Science
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Norwich, UK Fukuoka, Japan
Yoshinori Asakawa Ji-Kai Liu

Faculty of Pharmaceutical Sciences School of Pharmaceutical Sciences
Tokushima Bunri University South Central University for Nationalities
Tokushima, Japan Wuhan, China
ISSN 2191-7043 ISSN 2192-4309 (electronic)

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Contents
Allelopathy: The Chemical Language of Plants . . . . . . . . . . . . . . . . . . . 1

Francisco A. Macías, Alexandra G. Durán, and José M. G. Molinillo
The Phytochemistry and Pharmacology of Hypericum . . . . . . . . . . . . . . 85
Chuan-Yun Xiao, Qing Mu, and Simon Gibbons
Taccalonolide Microtubule Stabilizers . . . . . . . . . . . . . . . . . . . . . . . . . . 183
Samantha S. Yee, Lin Du, and April L. Risinger
v
Allelopathy: The Chemical Language
of Plants
Francisco A. Macías, Alexandra G. Durán, and José M. G. Molinillo
Contents
1 Introduction.......................................................................................................................... 2
2 Exudation............................................................................................................................. 3
2.1 Plant–Plant Interaction................................................................................................ 3
2.2 Plant–Microbe Interaction .......................................................................................... 25
3 Leaching .............................................................................................................................. 32
4 Volatilization........................................................................................................................ 48
5 Decomposition ..................................................................................................................... 52
6 Applications ......................................................................................................................... 70
7 Future Studies...................................................................................................................... 70
References .................................................................................................................................. 71
F. A. Macías (&) A. G. Durán J. M. G. Molinillo

Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO),
Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz,
C/República Saharaui 7, 11510 Puerto Real, Cadiz, Spain
e-mail: famacias@uca.es
A. G. Durán
e-mail: alexandra.garcia@uca.es
J. M. G. Molinillo
e-mail: chema.gonzalez@uca.es
© The Editor(s) (if applicable) and The Author(s), under exclusive license to 1
Springer Nature Switzerland AG 2020
A. D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi, Y. Asakawa, J.-K. Liu (eds.),
Progress in the Chemistry of Organic Natural Products, Vol. 112,
https://doi.org/10.1007/978-3-030-52966-6_1
2 F. A. Macías et al.
1 Introduction
In Nature, the oldest method of communication between living systems is the

chemical language. Plants in particular, due to their lack of mobility, have devel-
oped the most sophisticated way of chemical communication, which is mainly
based on specialized metabolites belonging to secondary metabolism [1, 2]. The
most relevant aspects regarding the chemical language of plants will be described in
this chapter. Only those examples with a growing body of evidence of allelopathic
phenomena will be discussed and these will be categorized by plant families and
listed in alphabetical order.
The term allelopathy (Greek: ἀkkήkxm, allelon = each other, pάho1,
pathos = suffering, mutual interaction) was introduced for the first time by Hans
Molisch (1937) to refer to biochemical interactions (both inhibitory and stimula-
tory) between plants, including microorganisms [3, 4]. This definition was slightly
modified by Rice (1974) to any direct or indirect, beneficial or destructive effect by
one plant (including microorganisms) on another through the production of
chemical compounds (allelochemicals) released into the environment [5]. The most
commonly accepted definition is described by the International Allelopathy Society
(IAS) (1996), which recommended the term allelopathy to mean the science that
concerns any process involving mainly secondary metabolites, produced by plants,
algae, bacteria, and fungi, that influence the growth and development of agricultural
and biological systems (Fig. 1) [6–8].
Allelochemicals can be released into the environment by four main pathways:
(i) exudation from roots, (ii) leaching from aerial parts by rain, fog, or dew,
(iii) volatilization, and (iv) decomposition of plant remains [9, 10] (Fig. 2). These
compounds can affect the development of neighboring plants, mainly on germi-
nation and root or shoot growth.
Fig. 1 Different interactions

encompassed by allelopathy
Allelopathy: The Chemical Language of Plants 3
Fig. 2 The main pathways

for the release of
allelochemicals
2 Exudation
The most widely known allelochemicals have been identified in root exudates. The
synthesis and exudation of allelochemicals in root exudates is typically enhanced by
abiotic and biotic stress conditions encountered by the plant, which include plant
competitors, extreme temperature, drought, and UV exposure [11]. These exudates
play a key role in the rhizosphere and some of the most relevant aspects are
described below.
2.1 Plant–Plant Interaction
2.1.1 Asteraceae
Centaurea diffusa Lam.
Centaurea diffusa (Asteraceae), also known as diffuse knapweed, is native to the

eastern Mediterranean Eurasian range and it is an exotic invasive species and a
prominent threat in North American grasslands [12]. This plant has invaded more
than 1.4 million ha since its introduction as a seed contaminant prior to 1907 [13].
This species is one of the main examples in the field of allelopathy, and it has been
Fig. 3 Structure of 8-hydroxyquinoline (1), a putative allelochemical from C. diffusa roots. Image
adapted from USDA APHIS PPQ, Bugwood.org
suggested that the allelochemicals exuded or leached from this weed might explain
its invasion success [14]. It has been reported that 8-hydroxyquinoline (1) (Fig. 3)
is exuded from its roots, and this compound has shown phytotoxic activity on
neighboring species [15]. The concentration of this compound was three times
higher in C. diffusa-invaded North American soils than in its native Eurasian soils.
Furthermore, it has a strong affinity for divalent and trivalent cations such as
aluminum, magnesium, and iron. Since this species mostly invades alkaline cal-
careous soils, the relationship between this compound and nutrition uptake was
investigated. Studies carried out by Tharayil and co-workers [16] demonstrated that
8-hydroxyquinoline is used by the plant to facilitate iron uptake (a nutrient deficient
in most of its invaded soils) in its complexed form. This represents a possible
adaptive mechanism that confers a competitive advantage over native species in
alkaline soils. This compound can be released from the roots of C. diffusa following
a diurnal rhythm. The authors indicated that this temporal pattern is similar to the
exudation of phytosiderophores by the roots of graminaceous species to enhance
their uptake of metals. The phytotoxicity of 8-hydroxyquinoline was influenced by
the presence of metals and it was significantly reduced when complexed with metal
ions, including copper and iron [17].
However, in subsequent studies clear evidence was not found that this species
produces this compound at ecologically meaningful concentrations. For instance,
Norton et al. were unable to detect 8-hydroxyquinoline (1) in experimental or field
collected soils infected by C. diffusa, and Quintana et al. did not detect it in root
exudates or root extracts of in vitro growth [13, 14]. Additional studies are required
to establish the role of this putative phytotoxin, to corroborate its presence in a soil
environment and to ascertain how soil factors and microorganisms mediate its
allelopathic activity [18].
Flaveria bidentis (L.) Kuntze
Flaveria bidentis (Asteraceae) is an annual herb that is native to South America and
was discovered as an exotic plant in China. It is also known as “eco-killer” due to
its high adaptation to new environments, high rate of germination, and
well-developed root system, as well as the production of large amounts of allelo-
chemicals that inhibit the growth of surrounding plants. Despite this potential
allelopathic activity, there are very few studies on its root exudates [19]. Recently,
Xing and co-workers [20] identified by GC/MS a large variety of compounds
suggested as allelochemicals.
Psacalium decompositum (Gray) Rob. ex Brett.
Psacalium decompositum (Gray) (Asteraceae) is a shrub that is native to northern

Mexico and southern North America and it is called locally “matarique” or “ma-
turin” [21]. The infusion of both the roots and rhizomes of this plant has been used
for the treatment of rheumatism, pains, diabetes, snakebites, and renal, hepatic, and
gastrointestinal ailments [22]. Phytochemical studies have revealed that the most
abundant constituents in the hexane extract of its roots are two sesquiterpene
compounds (furanoeremophilanes), namely, cacalol (2) and cacalone (3) [23]
(Fig. 4). These particular compounds possess an unusual tetrahydronaphthofuran
structure and their isolation led to the first report of this kind of backbone in Nature
[21]. Cacalol is an unstable compound that forms a homodimer upon exposure to
UV radiation and it is also oxidized by oxygen and light [24]. Additionally, these
sesquiterpenes and related structures have been found in aqueous decoctions of the
roots and rhizomes, thus explaining the pungent odor and bitter taste of the tradi-
tional infusions used for medicinal purposes. These compounds were detected by
thin-layer chromatography using standards, after extraction of the aqueous infusion
with chloroform and then ethyl acetate. Moreover, it has been reported that cacalol
(2) inhibits ATP synthesis, proton uptake, and electron transport at the oxygen
evolution level. A concentration of 60 µM of cacalol completely inhibited the
electron transport from water to 2,6-dichlorophenolindophenol (DCIP). This sug-
gested that cacalol could act as an allelochemical agent to interfere with the growth
of photosynthetic organisms [24].
The effect of the aqueous extract (obtained from 1 g of roots soaked with 100 cm3
of distilled water for 4 h), n-hexane extract, and cacalol (2) on the germination and
radicle growth of Amaranthus hypochondriacus L. and Echinochloa crus-galli L.
was studied. Significant inhibition of the germination of A. hypochondriacus and on
the radicle growth of both species was noted, especially by the aqueous extract and 2.
In previous studies it was suggested that the hydroxy group of 2 plays an important
OH O O O
O O O O
OH
2 (cacalol) 3 (cacalone) 4 (cacalol acetate) 5 (methyl cacalol)
Fig. 4 Structures of the main constituents of Psacalium decompositum (cacalol and cacalone) and
synthetic derivatives (cacalol acetate and methyl cacalol)
role in the inhibition of oxygen evolution in photosynthesis. Therefore, two synthetic

derivatives with higher lipophilicity (cacalol acetate (4) and methyl cacalol (5))
(Fig. 4) were prepared in order to evaluate their influence on the activity. The results
showed that the methyl ether 5 was less active than the other compounds and a potent
radicle growth inhibition of E. crus-galli was observed for the acetate 4. However,
significant effects were not observed in A. hypochondriacus for the latter compound.
These results indicated that substitution of the free hydroxy group in the cacalol
structure did not enhance the activity on radicle growth inhibition for either species,
although greater selectivity was achieved. An enzymatic biotransformation of
cacalol acetate (4) to cacalol (2) inside the seeds of E. crus-galli was proposed.
Regarding A. hypochondriacus, this biotransformation would not occur and cacalol
acetate would remain in its seeds without any effect [21, 25]. The typical pappus of
the Asteraceae is shown in Plate 1.
Plate 1 Asteraceae. Pappus (flower structure) of Asteraceae. Cabrera de Mar (Barcelona). Image
from Creative Commons Attribution-Share Alike 3.0 Unported license. (https://commons.
wikimedia.org/wiki/File:Papus_(Asteraceae).jpg)
2.1.2 Brassicaceae
Brassica napus L.
Brassica napus (Brassicaceae) (Plate 2), commonly known as canola, is one of the
main crops for the production of vegetable oil for human consumption and animal
nutrition worldwide. Recently, this plant has also been used for the production of
biodiesel [26]. Asaduzzaman et al. [27] evaluated the allelopathic potential of this crop
against annual ryegrass by comparing different canola genotypes (strongly and weakly
competitive). Metabolomic analysis by LC-QTOF-MS of shoots, roots, and root
exudates was performed. A greater number of secondary metabolites were found in the
roots than in the shoot extracts, and a few of these compounds were identified in the root
exudates. Previous research findings have also led to the same conclusion in the study
of other species. It is suggested, therefore, that shoots and roots contain many
metabolites, but only some of these are released into the soil environment in a process
that depends on particular plant-soil conditions. Significant differences were observed
between growth inhibition of annual ryegrass and the tested canola genotypes,
including in chemical composition. Sinapyl alcohol (6), 4-hydroxybenzoic acid (7),
and 3,5,6,7,8-pentahydroxyflavone (8) (Fig. 5) were found in the root exudates of the
most suppressive genotypes, and it was suggested that these compounds were probably
responsible for the allelopathic activity that was observed [27]. Furthermore, Uremis
and co-workers [28] evaluated the allelopathic potential of different canola cultivars on
the seed germination and shoot and root growth of several weed species. Root exudates
showed inhibition of seed germination although root and shoot extracts had higher
Plate 2 Brassicaceae.
Brassica napus L. Image from
Tilo Hauke (http://commons.
wikimedia.org/wiki/File:
Brassica_napus_2.jpg)
O OH
O OH
HO HO O
OH
O HO OH
OH OH O
6 (sinapyl alcohol) 7 (4-hydroxybenzoic acid) 8 (3,5,6,7,8-pentahydroxyflavone)
Fig. 5 Metabolites isolated from the root exudates of Brassica napus that are probably
responsible for the allelopathic activity observed
inhibition potential. It was demonstrated that those cultivars with higher levels of
benzyl and allyl isothiocyanate had stronger allelopathic effects.
2.1.3 Boraginaceae
Echium spp.
Isohexenylnaphthazarins (alkannin and shikonin derivatives) are found in the root

periderm of several Boraginaceous plants, including Echium species (Fig. 6) [29].
Fig. 6 Isohexenylnaphthazarins released from the roots of Echium spp.

Plate 3 Boraginaceae.
Viper’s bugloss (Echium
vulgare) flower. Copyright
Evelyn Simak and licensed
for reuse under
creativecommons.org/
licenses/by-sa/2.0. (https://
www.geograph.org.uk/reuse.
php?id=5801578)
These compounds are characteristically red and are often light- and oxygen-labile,
which makes their isolation difficult and methods for their separation rather few in
number [30]. It has been suggested that in the soil the naphthoquinones released by
Echium vulgare (Plate 3) roots may act as defense compounds and they are pro-
duced potentially as a result of plant stress [31, 32].
Durán and co-workers [33] quantified the content of these allelochemicals by
LC-MS-MS from the periderm roots of two Echium spp., namely, E. plantagineum
and E. gaditanum, to assess their impact on their native and invaded ranges. E.
plantagineum, also known as Paterson’s curse or Salvation Jane, is a successful
invader in Australia that was introduced in the 1800s [34]. In contrast to the above,
E. gaditanum is perennial and its toxicity does not have a major impact on agri-
culture in its native range. Phytochemical studies of this plant are uncommon and
previously only the fatty acid composition of the seed oil has been reported [35].
The results highlighted that the abundance of certain pigments is closely related to
climatic conditions. Thus, root extracts from both species collected in late spring
were more inhibitory in the wheat coleoptile bioassay. Acetylshikonin (9) and
acetylalkannin (10) versus dimethylacrylshikonin (11) and dimethylacrylalkannin
(12) were present in the highest concentrations in extracts from both species.
R R
OH O O OH O O
OH O OH O
9 R = COCH3 (acetylshikonin) 11 R = COCH=C(CH3)2 (dimethylacrylshikonin)
10 R = COCH3 (acetylalkannin) 12 R = COCH=C(CH3)2 (dimethylacrylalkannin)
2.1.4 Euphorbiaceae
Euphorbia himalayensis (Klotzsch) Boiss.
Euphorbia himalayensis is a noxious weed to livestock and humans, in addition to

affecting the performance of crops in the Tibetan Plateau. Liu and co-workers [36]
isolated three compounds from the root extracts, including 4-O-[b-D-xylopyranosyl]-
3,3′-di-O-methylellagic acid (13), 3,3′-di-O-methylellagic acid (14), and esulone A
(15) (Fig. 7). Furthermore, these compounds were also identified in the rhizosphere
soil. Root exudates showed inhibitory growth activity on wheat seedlings at lower
concentrations while an increase in plant growth was produced when the concentration
O O
O HO
Xyl O O
O O
O O
O O
OH OH
O O
13 (4-O-[ß-D-xylopyranosyl]-3,3'-di-O-methylellagic acid) 14 (3,3'-di-O-methylellagic acid)
O
AcO
HO
AcO O
BzO
BzO OH
15 (esulone A)
Fig. 7 Possible allelochemicals from root exudates of E. himalayensis

Plate 4 Euphorbiaceae. Euphorbia milii Des Moul. flowers. This file is licensed under the
Creative Commons Attribution-Share Alike 3.0 Unported license. (https://commons.wikimedia.
org/wiki/File:Euphorbia_Milii_flowers.jpg)
was higher. This finding suggests that the combination of these allelochemicals could
provide a selective plant growth regulator. It was also proposed that these allelochemicals
enable this species to become a successful competitor. To illustrate a typical
Euphorbiaceae species, the flowers of Euphorbia milii are shown in Plate 4.
2.1.5 Fabaceae
Mucuna pruriens (L.) DC.
Mucuna pruriens (Fabaceae), also named velvet bean, is a popular Indian medicinal
plant widely distributed throughout India and in other parts of the tropics, including
Central and South America [37]. This plant has also been cultivated for inter-
cropping with maize, sorghum, and millet in tropical regions to provide soil and
crop benefits and for the management of various pests. In this way, the quantity of
synthetic agrochemicals needed for the crops is reduced. The main allelochemical,
which is exuded from the roots of this species, is the non-protein amino acid
3,4-dihydroxyphenyl-L-alanine [38] 16 (L-DOPA) (Fig. 8) and this reaches 1 ppm
in water culture solution and 50 ppm in the vicinity of the roots. These concen-
trations are sufficient to affect the growth of surrounding plants by inhibition of seed
and root growth. For instance, the growth of maize roots and the activities of
phenylalanine ammonia-lyase (PAL), tyrosine ammonia-lyase (TAL), and peroxi-
dase (POD) were reduced, while the contents of phenylalanine, tyrosine, and lignin
were increased after exposure to L-DOPA (16) (39). These findings suggest that the
inhibition of these activities could lead to a major incorporation of phenylalanine
HO COOH HO NH2
–CO2
NH2
HO HO
DOPA decarboxylase
16 (L-DOPA) 17 (dopamine)
Fig. 8 Detoxification of L-DOPA to form dopamine through the action of L-DOPA decarboxylase
and tyrosine levels into the cell wall and this would be followed by lignin depo-
sition. Therefore, cell expansion is restricted and the root growth reduced.
Moreover, this allelochemical has also been found in large amounts in leaves and
seeds from this species [40]. These phytotoxic effects are generally less damaging in
Gramineae and Leguminosae species. It has been reported that some plants are able to
detoxify L-DOPA (16) to form dopamine (17) or 3-O-methyldopa through the action
of L-DOPA-decarboxylase and catechol-O-methyltransferase, respectively [41].
Dopamine (17) (Fig. 8) is an allelochemical that is widespread in animals and has
also been detected in many plant families. For example, Wichers et al. [42] used
HPLC coupled with mass spectrometry to identify 17 in 2–3-week-old leaves of
Mucuna pruriens. The dopamine content of the leaves even exceeded the content of L-
DOPA (16), the most abundant allelochemical in Mucuna. However, 17 could not be
detected in the roots, stems, or seeds at any stage of development. Matsumoto [43]
reported that Mucuna metabolizes 16 to 17 in leaves as a protective mechanism
against the toxicity of 16. Dopamine (17) has also been detected in numerous other
plant families; for example, 17 is one of the major bioactive components of Portulaca
oleracea L. [44], potato (Solanum tuberosum), the pulp of yellow banana (Musa
acuminata), and fuerte avocado (Persea americana) [45, 46].
However, the role of dopamine (17) in plants has not been widely studied. In
some studies, 17 has been proposed as a precursor for alkaloids and others revealed
its allelopathic activity as it is involved in processes such as flowering, nitrogen
fixation, and photophosphorylation of chloroplasts. For example, 17 has been
shown to inhibit soybean root elongation [47].
Trifolium pratense L.
Trifolium pratense (Fabaceae) (Plate 5), also known as red clover, is a forage plant
that is widely distributed worldwide and has a wide range of biological activities
[48, 49]. Although its phytotoxicity on other plants has been reported, the identity
of the responsible active metabolites has not been further explored. It was found in
recent studies that isoflavonoids, namely, (6aR,11aR)-maackiain (18) and
(6aR,11aR)-trifolirhizin (19), are the major components in root extracts of this
species (Fig. 9). Furthermore, some of the compounds from the soil were identified
as allelochemicals, showing remarkable phytotoxic activity on one of the most
widely distributed weed species, Poa annua [50].
Plate 5 Fabaceae. Trifolium pratense. Photograph courtesy Ivar Leidus (https://reativecommons.

org/licenses/by-sa/4.0)
HO O O O
Glc
O O O O
O O
18 ((6aR,11aR)-maackiain) 19 ((6aR,11aR)-trifolirhizin)
Fig. 9 Allelochemicals identified in Trifolium pratense
2.1.6 Juglandaceae
Juglans nigra L.
Juglans nigra (Juglandaceae) (Plate 6), also named black walnut, is one of the most
notable and oldest examples in allelopathy since juglone (20) (5-hydroxy-1,4-
naphthoquinone) was the first allelopathic agent to be described. Juglone (20) is
mainly obtained from the leaves, roots, and husks of species belonging to this family
and it has shown growth inhibitory effects for the whole plant on herbaceous and
woody species, such as tomato, alfalfa, soy, and cucumber [51–54]. Pliny the Elder
(23–79 AD) was the first to observe that “the shadow of walnut trees is poison to all
plants within its compass” [55]. In living plant tissues, a colorless non-toxic reduced
Plate 6 Juglandaceae.
Juglans nigra, Walnut tree.
Photograph Georg Slickers,
licensed under the Creative
Commons Attribution-Share
Alike 2.5 license. (https://es.
m.wikipedia.org/wiki/
Archivo:Walnut-tree_
20041012_2599.JPG)
OH OH OH OH OH O
H2O [–H2]
O Glc OH O
22 (glucoside) 21 (hydrojuglone or 1,4,5-trihydroxy- 20 (juglone)
naphthalene)
Fig. 10 The presence of hydrojuglone in living tissues of walnut tree and subsequent formation of
the allelopathic compound, juglone
form of this compound, hydrojuglone (21), is abundant—especially in the leaves,

fruit hulls, and roots of walnut. When this compound is exposed to air or to an
oxidizing compound, hydrojuglone is oxidized to its toxic form, juglone (20)
(Fig. 10). Therefore, plants in the vicinity of the walnut tree are affected by absorbing
20 through their roots [53]. With respect to biosynthesis, juglone is presumed to be
produced by hydrolysis of its glucoside 22.
2.1.7 Poaceae
Avena fatua L.
Avena fatua (Poaceae) (Plate 7), or wild oat, is one of the worst annual grass weeds
in the world (especially on wheat and other cereals). It has been reported that
phenolic acids (such as p-coumaric (93), vanillic (46), and ferulic (44) acids) and
Plate 7 Poaceae. Avena

fatua L. This file is licensed
under Creative Commons
Attribution—Partage dans les
Mêmes Conditions 4.0
International. (https://fr.
wikipedia.org/wiki/Fichier:
Avena_fatua-Folle_avoine-
20150527.jpg)
scopoletin are the major compounds released from its roots [56]. Additionally, it
has been demonstrated that the concentration of these phenolic acids depends on the
plant growth stage. The highest concentration of these allelochemicals in the rhi-
zospheric soil was recorded at the stem extension and heading stages [57].
Oryza sativa L.
Rice, Oryza sativa (Poaceae or Gramineae), is one of the main food crops world-
wide [58]. Previous studies have shown that the allelopathic activity of this species
is varied and dependent on the origin. Large amounts of allelochemicals are
released from rice plants under biotic and abiotic conditions for defense and pro-
tection [59]. Among these compounds, phenolic acids (vanillic (46) or benzoic (47)
acids), diterpenoids, and momilactones have been described [60–63]. A study
performed by Khanh et al. relied on the allelopathic responses of two rice varieties
(Koshihikari and Jasmine) under abiotic stresses: temperature and complete sub-
mergence (one of the most harmful abiotic stresses). The results revealed that the
total phenolic content was higher in extracts and root exudates from rice seedlings
under the abiotic stresses evaluated, especially for the Koshihikari variety. Five
phenolic acids were found to be involved in the allelopathic response, with syringic
and benzoic acids being the most prominent. Moreover, root exudates of
Koshihikari rice seedlings reduced the number of total weeds by up to 60% at 32°C
[64]. Likewise, the secretion of the allelochemical momilactone B was increased by
the presence of barnyardgrass seedlings or barnyardgrass root exudates [65].
Li and co-workers [66] investigated whether the phenomenon of rice allelopathy

could be related to root fineness (roots 0.2 mm diameter). The results showed
that allelopathic rice cultivars had higher length, a greater number of root tips of fine
roots, and a direct correlation between the phenolic acids content in root exudates,
and allelopathic activity was noted. These findings were not evident in roots with a
diameter greater than 0.2 mm. It is believed that fine-root traits could accumulate
more allelochemicals and release them into the environment. Moreover, the release
of greater quantities of allelochemicals could be related to phytohormone regula-
tion. It has been proposed that the phytohormones jasmonic acid and salicylic acid
play a crucial role in the signaling pathway in rice-barnyard recognition [67, 68].
Phragmites australis (Cav.) Trin. ex Steud.
Phragmites australis (Poaceae) is one of the most invasive species in the world
[69]. Several studies have shown that aqueous extracts of different parts of this plant
(leaves, stems, rhizomes, and roots), as well as root exudates, have strong phyto-
toxic effects on the germination and growth of other plant species [70]. This activity
has been related to the presence of phenolic compounds. Moreover, gallic acid was
identified as the major compound in leaf extracts, which showed the highest
activity, followed by the inflorescence, rhizomes, roots, and finally stems. Aqueous
extracts caused oxidative stress through the production of reactive oxygen species,
which resulted in cell death and inhibition of plant growth. A decrease in water
uptake and a delay in total carbohydrate degradation were also noted, thus pro-
viding evidence of a negative effect on the overall germination process [71].
Secale cereale L. (rye)
Secale cereale became a crop about 2000 years ago. It is used as a grain, forage,
green manure crop, or for hay, as well as a cover crop or mulch for allelopathic
weed control. The major allelochemicals reported and identified for the first time in
this species are benzoxazinoids [72]. Macías and co-workers described for the first
time the allelochemical pathway of benzoxazinoids released by rye (donor plant) on
Avena fatua L. (target plant) [73]. This kind of compound has been found in S.
cereale as well as in other Gramineae crops. Glucosylated benzoxazinoids are
found inside the plants and they are released into the environment without the sugar
moiety [74]. These compounds can be classified into three categories: benzoxa-
zolinones (23, 24), lactams (25), and hydroxamic acids (26, 27) [75] (Fig. 11).
These metabolites have attracted great interest due to the wide spectrum of bio-
logical bioactivities and remarkable allelopathic effects reported [76]. Additionally,
these compounds are transformed by soil microbiota into benzoxazolin-2-one
(BOA) and 2-aminophenol derivatives, which are subsequently oxidized to
2-amino-3H-phenoxazin-3-one (28) (APO) and other related products (Fig. 12).
These findings showed that, besides the allelochemicals released into the envi-
ronment, the degradation products after biotic and abiotic stresses are also decisive.
benzoxazolinones lactams
O O O OH
O
O O
N N N O
H H H
23 24 25
(benzoxazolin-2-one) (7-methoxy-benzoxazolin-2-one) (2-hydroxy-1,4-benzoxazin-3-one)
(BOA) (MBOA) (HBOA)
hydroxamic acids
O OH O O OH
N O N O
OH OH
26 27
(2,4-dihydroxy-1,4-benzoxazin-3-one) (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)
(DIBOA) (DIMBOA)
Fig. 11 Benzoxazinoids found in rye and other cereal plants
Fig. 12 Allelochemical pathway of benzoxazinoids released by S. cereale on A. fatua. Reprinted

with permission from J. Agric. Food Chem. (2014), 62:9450. Copyright (2014) American
Chemical Society
Fig. 13 Main allelochemical O

exuded from the roots of OH
sorghum
O
O
29 (sorgoleone)
Sorghum bicolor (L.) Moench
Sorgoleone (29) (Fig. 13) is one of the main allelochemicals exuded from the roots of
sorghum (Sorghum bicolor (L.) Moench) [77]. It has shown phytotoxic activity
against a wide variety of plant species, but is most active on small-seeded plants. This
allelochemical is released continually from the roots during its growing season,
thereby some persistence in soil has been estimated and its half-life is around ten days.
This property is due to its hydrophobic character, which leads to a strong sorption in
the soil with organic matter and other hydrophobic components [78]. The molecular
target sites affected by this allelochemical include photosynthetic and mitochondrial
electron transport. It has been demonstrated that sorgoleone does not have an effect on
the photosynthesis of older plants but it can cause inhibition of photosynthesis in
young seedlings [79]. Moreover, through the use of different microscopic techniques,
it has been demonstrated that this allelochemical, its resorcinol analog, and other
related hydroquinones are exuded from the tips of root hairs [31, 80].
It is worth noting that the phytotoxic activity of sorgoleone (29) can be com-
pared with those of commercial herbicides, including atrazine and metribuzin [81].
Recently, Uddin and co-workers [82] evaluated the crop selectivity of this com-
pound using its formulated wettable powder (WP) form. The results revealed that
sorgoleone as a 4.6WP (4.6% 29) product inhibited most of the weed species tested
and most crop species showed tolerance to it. This opens up the possibility of
developing more effective environmentally friendly herbicides.
Triticum aestivum L. (wheat)
Wheat constitutes one of the major crops and it is a staple food for more than 35%
of the world population [83]. A study performed by Kong and co-workers
demonstrated that (–)-loliolide (see later on: 50) and jasmonic acid are found in the
root exudates of a diverse range of plant species and these compounds could act as
signaling chemicals to trigger an allelochemical response in wheat [84, 85]. The
allelochemicals discussed above (benzoxazinoids) are also present in wheat and
they affect the growth of plant competitors [86, 87]. A higher concentration of
2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA, 27) was observed
when wheat was co-cultivated with other weed species. Additionally, this con-
centration was higher in roots than in shoots and the responses were
density-dependent. It is worth noting that below-ground plant–plant interactions
potentially affect the performance of plants and alter interspecific and intraspecific
interactions [88].
2.1.8 Solanaceae
Solanum lycopersicum L.
Solanum lycopersicum (Plate 8), commonly known as tomato, is an important

edible crop in Southern Europe, the Americas, the Middle East, and India.
Numerous metabolites have been described with a wide range of biological
activities, although phytotoxicity studies on tomato are scarce. Recently, Rial and
co-workers [89] isolated a-tomatine (30) from the roots of tomato and this com-
pound was also identified in root exudates by LC-MS/MS (Fig. 14). The
Plate 8 Solanaceae. Solanum lycopersicum L. This file is licensed under the Creative Commons
Attribution 3.0 United States license. (https://commons.wikimedia.org/wiki/File:Starr-090814-
4325-Solanum_lycopersicum-fruit-Industrial_area_Mokulele_Hwy-Maui_(24854266132).jpg)
N
H
OH O
O
HO
O O OH
O O O
O
OH O
HO OH
HO HO OH
HO
HO HO
30 (α-tomatine)
Fig. 14 Allelochemical released from the roots of S. lycopersicum

phytotoxicity of 30 was tested on L. sativa, E. crus-galli, and L. perenne and the

most affected parameter was root length. Moreover, 30 showed stimulation of the
germination of the tomato parasite (P. ramosa), thus acting as a chemical signal.
These results highlight the multipurpose behavior of this allelochemical.
2.1.9 Cupressaceae
Cunninghamia lanceolata (Lamb.) Hook.
Chinese fir (Cunninghamia lanceolata) (Plate 9) is a subtropical coniferous tree

species that has a considerable litterfall and fine roots. This species is grown
widely in the subtropical areas in China and covers around a quarter of the plan-
tation area, thus making it an important economic commodity for industrial wood
production. However, there is a regeneration failure and productivity decline in
successive plantations [90, 91]. It has been reported that the roots of Chinese fir
release into the soil environment the allelochemical cyclic dipeptide 31,
(6-hydroxy-1,3-dimethyl-8-nonadecyl-[1,4]-diazocane-2,5-diketone) (Fig. 15), which
causes self-growth inhibition and thereby regeneration failure and productivity
decline. This cyclic dipeptide has also been found in leaf litter and soils, in which its
concentration was higher in replanted Chinese fir plantations [91]. In order to
mitigate this problem, several experimental studies have demonstrated that there is a
positive interaction when this species is grown with broadleaf species, specifically
Plate 9 Cupressaceae. Cunninghamia lanceolata branch. This file is licensed under the Creative
Commons Attribution-Share Alike 3.0 Unported license. (https://commons.wikimedia.org/wiki/
File:Cunninghamia_lanceolata_branch.jpg)
HN N
O 16
HO
31 (6-hydroxy-1,3-dimethyl-8-nonadecyl-[1,4]-diazocane-2,5-diketone)
Fig. 15 Allelochemical described from the root exudates of Chinese fir
with Mitrephora macclurei Weeras. & R. M. K. Saunders and Eucalyptus decipiens

Endl. Significant differences were observed and these included an increase in the
total and available amount of phosphorus, reducing release and increasing degra-
dation of the allelochemical cyclic dipeptide, improvement of the soil microbial
community by increasing arbuscular mycorrhizal fungi community development,
and production and distribution of Chinese fir roots. This novel mechanism has led
to a reduction in problems related to self-growth inhibition or autotoxicity [88].
Nevertheless, when Chinese fir and C. camphora (Cinnamomum camphora (L.)
J. Presl) were grown together, an unfavorable response was produced, and this
resulted in growth inhibition of Chinese fir and changes in the composition of the
soil microbial community. These results highlighted the key role of root–root
interactions and the various complex processes that take place. Further research is
required to specify which compounds are responsible for these interspecific inter-
actions between Chinese fir and broadleaf tree species [92].
Other significant examples of autotoxicity are produced by phenolic acids
exuded from the roots of Camellia sinensis. These cases are described below.
2.1.10 Theaceae
Camellia sinensis L.
Camellia sinensis (Theaceae) (Plate 10), tea tree, is cultivated extensively in many
countries in Asia and Africa and it produces one of the most popular beverages.
However, tea yield and quality decrease rapidly after the initial establishment of
these trees. It has been reported that autotoxicity is the main factor in regeneration
failure and productivity decline [93–95]. A study performed by Cao and co-workers
[96] identified seven phenolic acids in root exudates and soil extracts, including
ferulic (44), cinnamic (45), vanillic (46), p-coumaric (93), caffeic, chlorogenic, and
gallic acids. Furthermore, it was also noted that the content of total phenolic acids in
soil extracts increased with the age of tea trees and therefore these compounds
could be responsible for the autotoxicity, which results in a decline in productivity
in successive plantations.
Plate 10 Theaceae. Camellia sinensis L. This file is licensed under the Creative Commons
Attribution-Share Alike 3.0 Unported license. (https://commons.wikimedia.org/wiki/File:
Camellia_sinensis_Bois_Cheri.jpg?uselang=fr)
2.1.11 Root Parasitic Plants: Chemical Signaling Hunters
Broomrapes are obligate plant-parasitic plants from the genera Orobanche and
Phelipanche (family Orobanchaceae). They cause significant damage and yield loss
in a variety of main crops, including sunflower, fava bean, tomato, and carrot,
among others [97]. The damage depends on the specific broomrape-host association
but, in general, parasitized crops suffer from reduction of total biomass and negative
effects on the crop photosynthetic machinery and hormonal balance [98]. Seeds
from parasitic plants can remain dormant in the soil for many years as they wait for
a chemical signal exuded from the root of the host to start their germination and
development of the haustorium [99]. All such features make the control of these
plants difficult and not fully effective, with only a few herbicides able to control
broomrapes selectively [100]. One of the main ways to control parasitic weeds is
the inhibition or stimulation of parasitic seed germination and haustorium growth.
The latter strategy (stimulation of parasitic seed germination) is also known as
“suicidal germination” and more recently as the “honey-pot strategy” [101, 102].
Strigolactones (apocarotenoids that regulate shoot branching) (Fig. 16) are
among the most potent germination-inducing factors for broomrapes [103]. These
allelochemicals are released from the host plant, into the soil environment, to
promote arbuscular mycorrhizal fungi symbiosis and facilitate nutrition uptake by
the plant. Nevertheless, this chemical signal is used by the plant for its own
adaptation and it benefits the parasitic plants as a perception of their hosts and thus
as a trigger to germinate [104]. The strigolactones isolated from host and non-host
plants, and also identified in the root exudates [105], include didehydro-orobanchol
(identified from roots of Poaceae and Solanaceae species), orobanchol (32) (the first
germination and haustorium inducing molecules
subclass of flavonoids
O O O hydroquinones
O O OH
OH
OH
HO O
O O O O
OH O O
O O O OH OH
OH 36 (dihydrosorgoleone)
32 (orobanchol) 33 (orobanchyl acetate) 35 (peonidin)
O sesquiterpene lactones
O
NC cyanatophenol
O
O O
Allelopathy: The Chemical Language of Plants
O O O
O
O OH
O 42 (ryecianatine A)
strigolactones 34 (5-deoxystrigol)
37 (dehydrocostus lactone) 38 (costunolide)
benzo[1,3]dioxolecarbonitrile
coumarins
O O O O
O
HO O O GlcO O O O O O NC O
39 (scopoletin) 40 (scopolin) 41 (ayapin) 43 (ryecarbonitrile A)
inhibitors of the germination of parasitic plants or haustorium growth
Fig. 16 Allelochemicals reported to inhibit or stimulate the germination of parasitic plants or haustorium growth
23
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At the bar as prysoner holding vp his hand. 1559, 63.
[84] Whiche in other’s cause, coulde. 1559, 63.

[85] Lyke. 1559, 63.
[86] As mummers mute do stand N.
[87] Vnable to vtter a true plea of denyall. 1559, 63.
[88] When that. 1559.
[89] For halfe a ryall. 1559, 63.
[90] We could by very arte haue made the black. 1559, 63.
[91] And matters of most wrong, to haue appered most right.
1559, 63.
[92] Most wise, may chance be too too weake. N.
[93] But may be brought to stand. 1578.
[94] Stanzas 5 and 6 added 1571.
[95] Behold me one vnfortunate amongst this flocke. N.
[96] Cal’d sometime. N.
[97] By discent a gentleman. 1559, 63.
[98] ‘And’ omitted. N.
[99] State. N.
[100] To whom frowarde fortune gaue a foule checkmate.
1559, 63.
[101] In all our common. N.
[102] What so wee. 1559, 63.
[103] We did conclude. N.
[104] Both life, death, lands, and goods. N.
[105] So great gaine we did get. 1559, 63.
[106] And sises. 1578. N.
[107] Still chiefe. N.
[108] We let hang the true man. 1559, 63.
[109] Doth neuer keepe. 1559, 63.
[110] Whiche though it haue enough yet dothe it not suffyse.
1559, 63. And more at no time doth suffise. 1578.
[111] And drinke they neuer so much, yet styl for more they
cry. 1559, 63.
[112] So couetous catchers toyle. 1559, 63.
[113] Gredy and euer needy, prollyng. 1559, 63.
[114] Fayth we did professe. 1578.
[115] Makyng a solempne oth in no poynt to dygresse. 1578.
[116] Wretches. 1559, 63.
[117]
Of the judge eternall, more high to be promoted,

To mammon more then God, all wholly were deuoted.
1578.
[118] We interpreted. 1559, 63.

[119] Like a. 1559, 63.
[120] Many one. 1559, 63.
[121] To serue kings in al pointes men must sumwhile breke
rules. 1559, 63.
[122] Ful nie. 1559, 63.
[123] To crepe into whose fauour we. 1559, 63.
[124] Auayle. 1578.
[125] Wurde. 1559, 63. Sense. 1578.
[126] Sence, 1559, 63.
[127] Of land. N.
[128] Wyll. 1578.
[129]
The king thus transcendyng the limittes of his lawe,

Not raygning but raging by youthfull insolence,
Wise and wurthy persons did fro the courte wythdraw,
There was no grace ne place for auncient prudence:
Presumpcion and pryde with excesse of expence,
Possessed the palays and pillage the countrye;
Thus all went to wracke vnlike of remedye. 1559, 63.
[130] Baronye. 1559, 63.

[131] Seing no reason. 1578.
[132] Maugre all. 1559.
[133] Maugre his princely mynde they. 1578. His kingly might.
N.
[134] All men vnchecked. 1578.
[135] Which. 1578.
[136] Regally. 1571, 78.
[137] That Richard. 1578.
[138] Order. 1578.
[139]
In whyche parliament muche thynges was proponed

Concerning the regaly and ryghtes of the crowne,
By reason kyng Richarde, whiche was to be moned,
Full lytell regardynge his honour and renowne,
By synister aduyse, had tourned all vpsodowne:
For suerty of whose estate,[143] them thought it did
behooue
His corrupt counsaylours, from hym to remooue. 1559,
1563.
[140] In the beginning of the parliament was called Robert

Veer, duke of Irelande, Alexander Neuell, archebishop of
Yorke, Mighell de la Poole, erle of Suffolk, sir Robert Tresilian,
chiefe iustice of Englande, to answere Thomas of Woodstock,
duke of Gloucester, Richard, erle of Arondel, Thomas, erle of
Derby, and Thomas erle of Nottyngham, vpon certaine articles
of high treason, which these lordes did charge them with. And
for as much as none of these appered, it was ordeyned by the
whole assent of the parliament that they shoulde be banished
for euer: and their landes and goodes, moueable and
vnmouable, to be forfeit and seased into the kinge’s hand, the
landes entayled onely except.
Shortly after this, was founde Robert Tresilian, chiefe
iustice, lurkyng in a poticarie’s house at Westmynster, and
there founde the meanes to have spyes daylie vpon the lordes
what was done in the parliament: for all the dayes of his lyfe
he was craftie, but at the last his craft turned to hys
destruction: for he was discouered by his owne seruant, and
so taken and brought to the duke of Gloucester, and the same
daye had to the Towre, and from thence drawen to Tyborne,
and there hanged.
The morow after, syr Nicholas Pembroke, which afore had
been maior of the citie of London, against the citezen’s will,
was brought foorth. Grafton.
This man (Tresilian) had disfigured himselfe, as if he had
beene a poore weake man, in a frize coat, all old and torne,
and had artificially made himselfe a long beard, such as they
called a Paris beard, and had defiled his face, to the end he
might not be knowen but by his speach. Stowe.
[141] Tharchbyshop of Yorke was also of our band, 1578.
[142] See Statutes at large, temp. Rich. II. viz. 11. c. I. II. III.
20. c. VI. and 31. c. XII. XIII.
[143] State, 1559.
[144] Judge. 1578.
[145] To dye there as. 1578.
[146] The fickle fee of fraud. 1578.
[147] Ye iudges now liuing. 1578.
[148] Fye on stynkyng lucre, of all vnryght the lure, Ye judges
and ye justicers let my most iust punicion. 1559, 63.
[149] Al pure. 1578. Still pure. N.
[150] What glory is more greater in sight of God. 1578.
[151] By the pathes of equytie. 1559, 63.
[152] And truely. 1578.
[153] Alwayes. 1559, 63.
[154] Lawes for to scan. N.
[155] Reward. 1559, 63. That justice may take place without
reward. 1578.
[156] Take. 1559, 63.
[157] The righteous. 1578. The most iust. N.
[158] Of mortals displeasure. N.
[159] Closde. 1578.
[160] Worldly hyre. 1559, 63. Way not this worldly mucke.
1578.
[161]
If som in latter dayes, had called vnto mynde,

The fatall fall of vs for wrestynge of the right,
The statutes of this land they should not haue defynde
So wylfully and wittingly agaynst the sentence quyte:
But though thei skaped paine, the faut was nothing light,
Let them that cum hereafter both that and this compare,
And waying well the ende, they will I trust beware. 1559,
63.
[162] George Ferrers. These initials first added, 1571.

[163] This. 1559, 63. 71.
[164] When finished was this tragedy. 1578.
[165] Syr Roger Mortimer, earle of March, and heyre
apparaunt of England, whose. 1578.
[166] Purposed matter. 1578.
[167] Of these great infortunes, and as they be more auncient
in tyme, so to place their seuerall plaintes. 1578.
[168] Two earles of the name of Mortimer. 1578.
[169] One hanged in. 1559, 63.
[170] In the tyme of king Edward. 1578.
[171] Another in Richard the seconde’s time, slayne in Ireland.
1578.
[172] Fauours. 1578.
[173] Personage of the earle Mortimer, called Roger, who full
of bloudye woundes. 1578.
[174] To Baldwin, in this wise. 1578.
[175] The dates added 1571—Fabian has given a summary of
the life of the second Roger Mortimer, and upon which the
poet relied, as of 1387, but the death of Mortimer happened
about 1398.
[176] On. 1578.
[177] Thred, vntimely death dyd reele. 1578.
[178] Brought from boote to extreme bale. 1578.
[179]
——the queene so much was stir’d,

As for his sake from honour she did scale. 1578.
[180] Merye gale. 1559, 63.

[181]
And whilest fortune blew on this pleasaunt gale,

Heauing him high on her triumphall arch,
By meane of her hee was made earle of March. 1578.
[182] Breded. 1559, 63.

[183] Pride folly breeds in. N.
[184] Hym, 1559, 63.
[185] For where he somwhat hauty was before. 1559, 63.
[186]
Whence pryde out sprang, as doth appeare by manye,

Whom soden hap, aduaunceth in excesse,
Among thousandes, scarse shal you fynde anye,
Which in high wealth that humor can suppresse,
As in this earle playne proofe did wel expresse:
For whereas hee too loftye was before,
His new degree hath made him now much more. 1578.
[187] Ne recks. N.
[188] Respecting none saue only the queene mother. 1578.
[189] Which moued malice to foulder. 1578.
[190] Which deepe in hate, before. 1578.
[191] Th’one as well as th’other. N.
[192] They did the earle attaynt. 1578. He was soone attaint.
N.
[193] Such crimes as hidden lay before. 1578.
[194] For hydden hate. 1578. For enuy still. N.
[195] Biddes small faultes to make more bad. 1578.
[196]
Causing the king to yelde vnto the Scot,

Townes that his father, but late afore had got. 1578.
[197] Had, wanting, in 1559, 63. N.

[198] Yeuen to the Scots for brybes and priuie gayne. 1578.
[199] That by. 1578.
[200] Most, wanting. 1559, 63, 71. N. Most cruelly. 1578.
[201] And last of all by pyllage. 1578.
[202] Had spoyld. 1578.
[203] Dampned he was. 1578.
[204] Syr Roger Mortymer was accused before the lordys of
the parlyament of these artycles with other; whereof v. I fynde
expressyd. And firste was layed vnto his charge that by his
meaneys syr Edwarde of Carnaruan, by mooste tyrannouse
deth, in the castell of Barkley, was murderyd; secondaryly, that
to the kynge’s great dyshonoure and dammage, the Scottys,
by his meanys and treason, escapyd from the kyng at the
parke on Stanhope, whiche then shuld haue fallen in the
kynge’s daunger, ne had been the fauoure by the sayde Roger
to them than shewyd; thyrdely, to hym was layed, that he, for
execucion of the sayd treason, receyued of the capytane of
the sayd Scottis, namyd syr Iamys Dowglas, great summys of
money, and also for lyke mede he had, to the kynge’s great
dyshonoure and hurte of his realme, concludyd a peace
atwene the kynge and the Scottis, and causyd to be delyuered
vnto theym the charter or endenture called Ragman, with
many other thynges, to the Scottys great aduauntage and
impouerysshynge of this realme of Englande. Fourtlye, was
layed to hym, that where by synystre and vnlefull meanys,
contrary the kynge’s pleasure and wyll, or assent of the lordys
of the kynge’s counceyll, he had gotten into his possessyon
moche of the kynge’s treasoure, he vnskylfully wasted and
myspent it; by reason whereof the kyng was in necessyte, and
dryuen parforce to assaye his frendys. Fyfthlye, that he also
had enproperyd vnto hym dyuerse wardys belongynge to the
kynge, to his great lucre and the kynge’s great hurt, and that
he was more secret with quene Isabell, the kynge’s mother,
than was to Godde’s pleasure, or the kynge’s honoure: the
whiche artycles, with other agayne hym prouyd, he was, by
auctoryte of the sayde parlyament, iugyd to deth, and vpon
seynt Andrewys euyn next ensuynge, at London, he was
drawyn and hangyd. Fabyan.
[205] My coosins fall might. 1578. My cosin then might. N.
[206] Brybing, adultery and pride. 1578.
[207] I wene. 1578.
[208] ‘Deare,’ omitted. N.
[209] That dyd, 1559.
[210]
——heire of Lyonell,
Of king Edward the third the second sequell. 1578.
The third king Edward’s sonne, as stories tell. N.
[211] Cald. 1578.

[212] By true. 1578.
[213] Of ladies all the. 1578.
[214] Left in me. 1559, 63.
[215]
After whose death I onely stood in plight,

To be next heyre vnto the crowne by right. 1578.
[216] Of the. N.
[217]
Touching the case of my cousin Roger,
(Whose ruful end euen now I did relate)
Was found in tyme an vndue atteindre. 1578.
[218] By lawe eche man of. 1578. By law each one of. N.
[219]
Should be heard speake before his iudgement passe,

That common grace to him denyed was. 1578.
[220] In court of. 1578.

[221] His atteindre appering erroneous. 1578.
[222]
A president worthy, in record left,

Lorde’s lygnes to saue, by lawless meanes bereft. 1578.
[223] While fortune vnto me her grace did deigne. N.

[224] The. 1559, 63.
[225] Looser. N.
[226]
Whyle fortune thus did frendly me receyue,

Rychard the king, that second was by name,
Hauing none heire after him to reigne. 1578.
[227] That vnderstoode my bent. 1578.

[228]
And me to serue was euery manne’s entent,

With all that wyt or cunning could inuent. 1578.
[229] In hope. 1578.

[230] Chaunge their hue. 1578.
[231] For whiles fortune so luld. 1578.
[232] Dame. 1578.
[233] To dash me downe. 1578.
[234] Irish kernes. 1578.
[235]
My landes of Vlster vniustly to bereaue,

Which my mother for heritage did me leaue. 1578.
[236] Whom I did not regard. N.

[237]
The wylder sort, whom I did least regard,

And therfore the rechlesse manne’s reward. 1578.
[238] By auctoryte of the same parliament [in 1585-6] syr

Roger Mortymer, erle of the Marche, and sone and heyre vnto
syr Edmunde Mortymer, (and of dame Phylyp, eldest daughter
and heyer vnto syr Lyonell, the seconde sone of Edwarde the
thyrde) was soone after proclaymyd heyer paraunt vnto the
crowne of Englande; the which syr Roger shortly after sayled
into Irelande; there to pacyfye his lordeshyp of Wulstyr, whiche
he was lorde of by his foresayde mother: but whyle he was
there occupyed abowte the same, the wylde Irysshe came
vpon in noumbre, and slewe hym and moche of his company,
Fabyan.
[239] Nor helpe of frendes. 1578.
[240] Or. 1578.
[241] No law of armes they know. 1578.
[242] No foes. N.
[243] Their booty chiefe, they coumpt a dead man’s heade.
1578.
[244]
Their chiefest boote is th’aduersarie’s head,

They end not warre till th’enemie be dead. N.
[245] Their foes when they doe faine. N.

[246]
Nor yet presume to make their match amisse,
Had I not so done, I had not come to this. 1578.
——I had been left aliue. N.
[247]
At naught I set a sort of naked men,

And much the lesse, seeming to flye away,
One man me thought was good ynough for ten,
Making small account of number more or lesse,
Madnesse it is in war to goo by gesse. 1578.
[248]
See here the stay of pompe and highe estate,

The feeble hold of this vncerteyn lyfe. 1578.
[249] Hauing fayre fruict by my belooued wyfe. 1578. Syr

Roger had issu Edmunde, and Roger, Anne, Alys, and
Elanoure. Fabyan.
[250] Cavil. The “Ca.” was first affixed in 1571, and is repeated
in all the subsequent editions, except that of 1578, where
there appears “T. Ch.” the supposed signature of Thomas
Churchyard. As from that edition we shall have to notice,
presently, another similar alteration, it makes it doubtful
whether the same can be considered a misprint, though it
does not appear in the enumeration of his own pieces made
by Churchyard. See Bibliographia Poetica. Since this note was
printed the claim of ‘Master Chaloner’ to this signature has
been discovered. See postea, p. 53, n. 1.
[251] Was, omitted. 1578.
[252] Not to be treated of, 1559, 63.
[253] In the seuententh yere (1394) came oute of Scotlonde
certayne lordes into Englonde, to gete worshypp by fayte of
armes. The earl of Morris chalenged the erle marchall of
Englonde to juste wyth hym on horsbacke wyth sharpe
speres. And soo they roode togyder certayne courses, but not
the full chalenge. For the Scottyshe erle was caste bothe
horse and man, and two of his rybbes broken wyth the same
fall, and soo borne home into his inne. And anone after was
caryed homeward in a lytier. And at Yorke he deyed. Syre
Wyllyam Darell banerer of Scotlonde, and syre Pyers
Courteney the kynge’s banerer of Englonde roode togyder
certayne courses of warre hitte and assayed. The Scottisshe
knyghte seenge that he myghte not haue the better, yaue it
ouer: and wold noo more of the chalenge. Thenne one
Cokburne, squyer of Scotlond, and syre Nicholl Hauberk,
roode fyue courses, and at euery course the Scot was caste
bothe horse and man. Polychronicon.
[254] And whan thys ryall maryage was done and fynysshed
kynge Rycharde wyth dame Isabel his quene came into
Englonde. And the mayre of London, with all his brethren,
wyth grete multytude of the comyns of the cyte and the
craftes, receyuyd hym worshypfully at Blackheth, and brought
hym to Saynt Georges barre. And there taking their leue, the
kyng and quene roode to Kenignton. And after that wythin a
whyle the quene came to the toure of London, at whose
comyng was moche harme doo, for on London bridge were ix
persones thrust to deth, of whom the priour of typre was one.
Polychronicon. The prior of Tiptor, in Essex, was one. Stowe.
[255] Muche myndyng, 1559, 63.
[256] Date, added. 1571.
[257] Is stablysht. 1559, 63. Who stablisht is in state, seeming.
1578.
[258] Turne thine eare to. 1578.
[259] Prest in presence on fortune to. 1578.
[260] Of the. 1559, 63.
[261] Who by discent was of the. 1578.
[262] Nought. N.
[263] Before, eyther since. 1559. Or since. N.
[264] Most false fayth. 1578.
[265] Marcht. N.
[266] Thus hoysted high on fortune’s whyrling wheele. 1578.
[267] For whan fortune’s flud ran with. 1559, 63.
[268] I beynge a duke discended of kinges. 1559, 63.
[269] In. 1559, 63.
[270] Esperaunce. 1559, 63, 71. Assurance. 1578.
[271] All, omitted. N.
[272] To appoynt. 1559, 63.
[273] And for to settle others in their place. N.
[274] So, omitted. N.
[275] On a bell. N.
[276] Or. 1559, 63.
[277] Haply, omitted. N.
[278] For doyng on. 1559, 63. On, omitted. N.
[279] A sore checke. 1559, 63. I vnaduised caught a cruell
checke. N.
[280] Renown’d. N.
[281] For the tale of the rats, whence originates the proverbial
observation, “Who shall bell the cat?” see the vision of Pierce
the Plowman, by Crowley, ed. 1550, fol. iii. by Dr. Whitaker,
1813, p. 9.
[282] Expound. N.
[283] To curb. N.
[284] ’Bout. N.
[285] T’obay. N.
[286] It fits not a subiect t’haue. N.
[287] Thys by wurde. 1559, 63.
[288] And, omitted. N.
[289] Erle. 1559, 63.
[290] We by our power did call a parlament. N.
[291] With our. N.
[292] Playnely we depriued him of. 1559, 63.
[293] T’vnderstand. N.
[294] Thus wrought. 1578.
[295] By subiectes thus in bondage to bee brought. 1578.
[296] His. 1559, 63.
[297] Former cause of rancour to. 1578.
[298] Accoumpt. 1578.
[299] Were by me. 1559, 63.
[300] In the twentyest yere kynge Rycharde dide holde a grete
feeste at Westmestre. Att whyche feest aryued the souldyours
that hadde kepte Breste, and satte att dyner in the halle. And
after dyner the duke of Glocestre sayd to the kynge: “Syre,
haue ye not seen those fellowes that sate at dyner in your
halle.” And the kinge demaunded who they were. And he
sayde: “Thyse ben your folke that haue serued you, and ben
come from Breste. And now wote not what to doo, and haue
ben euyl payed.” Thenne the kynge sayde that they sholde be
payed. Thenne answered the duke of Gloucetre in a grete
furye: “Syre, ye oughte fyrste to put your body in deuoyre to
gete a towne, or a castell by fayte of warre vpon youre
enmyes, er ye sholde selle or delyuer ony townes that your
predecessours, kynges of Englonde, haue goten and
conquered.” To the whyche the kynge answerde ryght angrely:
“How saye ye that?” Thenne the duke his vncle sayd it
agayne. Thenne the kynge beganne to wexe wrothe, and
sayd: “Wene ye that I be a marchaunte or a foole to sell my
londe. By saynt Iohnne Baptyst naye: but trouthe it is that our
cosyn of Brytayne hath rendred and payd to vs the somme
that my predecessours had lent vppon the sayd towne of
Breste, and syth he hath payd, it is reason that this towne be
delyuered to hym agayne.” Thus beganne the wrath bitwene
the kynge and his vncle. Polychronicon.
[301] To claime entertainment the town beyng solde. 1559, 63.
To clayme their wages. 1578.
[302]
Of hate in hys hert hourded a tresure. 1559, 63.

Fulfyld his hart with hate. 1578.
[303] Nor. 1559, 63.

[304] But frendship fayned, in proofe is found vnsure. 1578.
[305] With long sicknesse diseased very sore. 1578.
[306] I was confedered before. 1578.
[307] Such aduauntage. 1578.
[308] Eame. This word is used repeatedly in the legends by
Ferrers. In the above passage it means uncle. It was also a
term for a gossip, compeer, or friend.
[309] To goe before. 1578.
[310] Preparedst a playne waye. 1578.
[311] What measure to others we awarde. 1578.
[312] The initials of George Ferrers, first added, 1571.
[313] This. 1559, 63, 71.
[314] Tragedy of the Lord Mowbray, the chief wurker of the
duke’s distruction, 1559, 63.
[315] To the state of a duke, added. 1571.
[316] Lykely. 1559, 63.
[317] Marke, I will shew thee how I swerued. 1559, 63.
[318] A vertuous mynde. 1559, 63.
[319] The herte to evyll to enclyne. 1559, 63.
[320] Kynde. 1559, 63.
[321] I thanke her, was to me so kynde. 1559, 63.
[322] Neyther of vs was muche to other holde. 1559, 63.
[323] Misprinted ‘thought’ by Higgins and Niccols.
[324] Wrong’d. N.
[325] Of England. 1578.
[326] Bad officers. N.
[327] Afore had. N.
[328] Aye seeks. N.
[329] The kinge’s fauour. 1578.
[330] Pryde prouoketh to. 1578.
[331] To poll and oppresse. 1578.
[332] And still. N.
[333] Him to. N.
[334] For pryde prickt me first my prince to flatter. 1578.
[335] Who so euer. 1578.
[336] Nere. N.
[337] Because of holdes beyond the sea that he solde. 1578.
[338] My. 1559, 63.
[339] Though vnto all these ils I were a frend. N.
[340] The duke of Gloucester for me did send. N.
[341] From place. 1578.
[342] Bewrayed the king. 1559, 63, 71, 78.
[343] At Arundell was a counseylle of certayne lordes: as the
duke of Gloucetre, tharchebysshop of Caunterbury, the erles
of Arundeel, Warwyck, and Marchall, and other, for to
refourme the rule abowte the kynge. Whyche lordes promysed
eche to abyde by other and soo departed. And anone after the
erle Marchall, whiche was captayne of Calays, bewrayed and
lete the kyng haue knowleche of all theyr counseylle:
wherupon the xxv daye of August, the duke of Glocetre was
arested at Plassheye in Estsex, and brought to the toure of
London. And from thence sent to Caleys and there murthred
and slayne wyth out processe of lawe or justyce.
Polychronicon.
[344] Earle. 1559, 63.
[345] It out. 1559, 63, 71.
[346] The palme represse. N.
[347] Earle. 1559, 63.
[348] Earle. 1559, 63.
[349] Manteyneth. 1559, 63.
[350] An. N.
[351] Earle. 1559, 63.
[352] Warly. 1559, 63.
[353] Misprinted, brest. 1587.
[354] In the same yere (1398) fel a great debate and
dyssencyon bytwene the duke of Herforde, erle of Derby, on
that one partye, and the duke of Norfolke, erle marchall, on
that other partye. In soo moche that they waged battaylle and
caste downe their gloues whiche were take vppe before the
kynge and ensealed, and the day and place assigned at
Couentree. To whyche place the kinge came, the duke of
Lancastre, and other lordes. And whan both partyes were in
the feelde redy for to fyghte, the kyng toke the matere in his
owne honde: and forthwyth he exyled and banysshed the
duke of Herforde for ten yeres, and the duke of Norfolke for
euermore. The duke of Norfolke deyed at Venyse.
Polychronicon.
[355] Doubtfull. 1578.
[356] That. N.
[357] Shame. N.
[358] Are iust to. 1578.
[359] Is. 1559, 63.
[360] Herewyth. 1559, 63, 71, 78.
[361] Which made them thinke mee worse then any feende.
1578.
[362] For other griefe. 1578.
[363] I parted thence and. 1578.
[364] The duke of Norffolke whiche supposed to haue been
borne out by the kynge, was sore repentant of his enterprise,
and departed sorowfully out of the realme into Almaine, and at
the laste came to Venice, where he for thoughte and
melancolye deceassed. Hall.
[365] More pleasure and reliefe. 1578.
[366] Which was not longe. 1578.
[367] Loo! thus his glory grewe great, by my dispite. 1578.
[368] So enuy euer, her hatred doth acquite. 1578.
[369]
Sorrowe and false shame,

Whereby her foes do shine in higher fame. 1578.
[370] Running. 1559.

[371] T. Ch. This signature first added in the edition of 1571,
and has been uniformly believed to mean Thomas
Churchyard. However, it may be more confidently assigned to
Master Chaloner, i. e. Sir Thomas Chaloner.—In the British
Museum there is a fragment of the original edition of the Mirror
for Magistrates, as printed in folio, during the reign of Queen
Mary, and suppressed, as already noticed, by the Lord
Chancellor. The fragment consists of two leaves, and which,
unfortunately, are duplicates, commencing with the
interlocutory matter before the legend of Owen Glendower,
and ends with the eighteenth stanza of the same legend. It
begins “Whan Master Chaloner had ended thys so eloquent a
tragedy,” and therefore appears conclusive that the above was
written by Thomas Chaloner, and that the legend of Richard
the Second, by Ferrers, which now follows, was first written for
the edition of 1559.
When the legend of Jane Shore was added in 1563,
Baldwin says: “This was so well lyked, that all together
exhorted me instantly to procure Maister Churchyarde to
vndertake and to penne as manye moe of the remaynder as
myght by any meanes be attaynted at his handes:” which
compliment proves that the author was a new candidate, and
upon the signatures being first added in 1571, we find his
name affixed to “Shore’s Wife,” in full, Tho. Churchyarde, to
distinguish it from the above abbreviation for Thomas
Chaloner.
[372] About the feeste of seynt Bartholmew fell dyscension
and discorde atwene the duke of Herforde and the duke of
Norfolke, wherefore the duke of Herforde accusyd that other
that he had taken iiii M. marke of the kynge’s, of suche money
as he shulde therewith haue wagyd certeyne sowdyours at
Calays, he lefte vndon, and toke the same money to his owne
vse. But another wryter sayeth, that as the sayd ii dukys rode
vpon a tyme from the parlyament towarde theyr lodgynges,
the duke of Norfolke sayde vnto that other: “Sir, see you not
howe varyable the kynge is in his wordis, and how shamefully
he puttyth his lordes and kynnes folkys to deth, and other
exylyth and holdyth in pryson; wherfore full necessary it is to
kepe, and not for to truste moche in his wordis, for with out
dowte in tyme to come, he wyll by such lyke meanys bryng vs
vnto lyke deth and distruction.” Of which wordys the sayd duke
of Herforde accusyd that other vnto the kynge; wherefore
eyther wagyd batayle, &c. Fabyan.
[373] For where as maister Hall, whom in thys storye we
chiefely folowed, making Mowbray accuser and Boleynbroke
appellant, mayster Fabyan reporteth the matter quite contrary,
and that by the reporte of good authours, makyng
Boleynbroke the accuser, and Mowbray the appellant. Which
matter, &c. 1559, 63.
[374] Recordes of the parliament. 1578.
[375] We referre to the determinacion of the haroldes, or such
as may cum by the recordes and registers of these doynges,
contented in the mean whyle with the best allowed iudgement
and which maketh most for. 1559, 63.
[376] Richard the 2. 1578.
[377] I woulde (quoth one of the cumpany) gladly say
sumwhat for king Richarde. But his personage is so sore
intangled as I thynke fewe benefices be at this daye, for after
hys imprisonment, his brother. 1559, 63.
[378] King, omitted. 1559, 63.
[379] Thinke. 1559, 63, 71, 78.
[380] In the kinge’s behalf. 1559, 63.
[381] See him all. 1559, 63.
[382] Vpon a beere in. 1578.
[383] Makyng his mone in thys sort. 1559, 63.
[384] From his seat, and miserably murdred in prison. 1559,
63.
[385] Vertue to folow and vyces to keepe vnder. 1578.
[386] Boast of high byrth, sword, scepter, ne mace. 1578.
[387] Rayne do drops of thunder. 1578.
[388] Let kinges therfore the lawes of God embrace. 1578.
[389] That vayne delightes. 1578.
[390] Do gase vpon me. 1559, 63.
[391] Lyeth, for whom none late myght rout. 1559, 63.
[392] Princes. 1578.
[393] Loute. 1559, 63, 71. Dead and least dread, to graue is
caryed out. 1578.
[394] But earth and clay. 1578.
[395]
Behold the woundes his body all about,

Who liuing here, thought, 1578.
[396] Wilt nowe declare. 1571, 78.

[397] My vicious story, 1559, 63.
[398] They kepe not, doutles say I dare. 1559, 63.
[399] Tyll the one. 1559, 63.
[400] Without respect of. 1578.
[401]
I am a kynge that ruled all by lust,

That forced not of vertue, right. 1559, 63.
[402] But alway put false flatterers most in trust, 1559, 63.
In false flatterers reposinge all my trust. 1578.
[403] Embracinge sutch. 1578.
[404] Fro counsell sage I did alwayes withdrawe. 1578.
[405]
By faythfull counsayle passing not a strawe;

What pleasure prickt, that thought I to be iust:
I set my minde, to feede, to spoyle, to iust. 1559, 63.
[406] Of God or man I stoode no wise in awe. 1578.

[407] More. 1578.
[408]
And to augment my lecherous minde that must

To Venus’ pleasures alway be in awe. 1563.
The edition of 1559 reads “and all to augment,” &c.

[409] Which to mayntayne I gathered heapes of golde. 1578.

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Progress in the Chemistry of Organic

Natural Products 112 A. Douglas

Progress in the Chemistry of Organic Natural Products

Progress in the Chemistry of Organic Natural Products

Progress in the Chemistry of Organic Natural Products

Progress in the Chemistry of Organic Natural Products

Total Synthesis of Natural Products At the Frontiers of

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Studies in Natural Products Chemistry Volume 43 First

Studies in Natural Products Chemistry Volume 46 1st

A. Douglas Kinghorn · Heinz Falk ·

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Psacalium decompositum (Gray) Rob. ex Brett.

Psacalium decompositum (Gray) (Asteraceae) is a shrub that is native to northern

2 (cacalol) 3 (cacalone) 4 (cacalol acetate) 5 (methyl cacalol)

role in the inhibition of oxygen evolution in photosynthesis. Therefore, two synthetic

6 (sinapyl alcohol) 7 (4-hydroxybenzoic acid) 8 (3,5,6,7,8-pentahydroxyflavone)

Isohexenylnaphthazarins (alkannin and shikonin derivatives) are found in the root

Fig. 6 Isohexenylnaphthazarins released from the roots of Echium spp.

10 R = COCH3 (acetylalkannin) 12 R = COCH=C(CH3)2 (dimethylacrylalkannin)

Euphorbia himalayensis (Klotzsch) Boiss.

Euphorbia himalayensis is a noxious weed to livestock and humans, in addition to

13 (4-O-[ß-D-xylopyranosyl]-3,3'-di-O-methylellagic acid) 14 (3,3'-di-O-methylellagic acid)

Fig. 7 Possible allelochemicals from root exudates of E. himalayensis

Mucuna pruriens (L.) DC.

Plate 5 Fabaceae. Trifolium pratense. Photograph courtesy Ivar Leidus (https://reativecommons.

Fig. 9 Allelochemicals identiﬁed in Trifolium pratense

form of this compound, hydrojuglone (21), is abundant—especially in the leaves,

Plate 7 Poaceae. Avena

Li and co-workers [66] investigated whether the phenomenon of rice allelopathy

Phragmites australis (Cav.) Trin. ex Steud.

Secale cereale L. (rye)

Fig. 11 Benzoxazinoids found in rye and other cereal plants

Fig. 12 Allelochemical pathway of benzoxazinoids released by S. cereale on A. fatua. Reprinted

Fig. 13 Main allelochemical O

Sorghum bicolor (L.) Moench

Triticum aestivum L. (wheat)

Solanum lycopersicum (Plate 8), commonly known as tomato, is an important

Fig. 14 Allelochemical released from the roots of S. lycopersicum

phytotoxicity of 30 was tested on L. sativa, E. crus-galli, and L. perenne and the

Cunninghamia lanceolata (Lamb.) Hook.

Chinese ﬁr (Cunninghamia lanceolata) (Plate 9) is a subtropical coniferous tree

Fig. 15 Allelochemical described from the root exudates of Chinese ﬁr

with Mitrephora macclurei Weeras. & R. M. K. Saunders and Eucalyptus decipiens