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Fundamentals of Flavonoids
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CHAPTER 5
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PHYTOCHEMISTRY,
PHARMACOLOGY, AND
APPLICATIONS OF
PHYTOECDYSTEROIDS
CONTENTS
5.1. Introduction .................................................................................... 136
5.2. Distribution of Phytoecdysteroids .................................................... 137
5.3. Diversity of Phytoecdysteroids ........................................................137
5.4. Biosyntheses of Phytoecdysteroids ..................................................144
5.5. Functions of Phytoecdysteroids ....................................................... 147
5.6. Agrochemical Applications ............................................................. 149
5.7. Medical Applications ...................................................................... 154
5.8. Pharmacology of Phytoecdysteroids ................................................ 163
References .............................................................................................170
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Natural Compounds: An Introduction
5.1. INTRODUCTION
Ecdysteroids (also known as ecdysones) are the cluster of natural
polyhydroxysteroids existent in animals (zooecdysteroids) and plants
(phytoecdysteroids). Some ecdysteroids, like ecdysone, ajugasterone C, and
20-hydroxyecdysone (ecdysterone), can generally be found in animals and
plants. The phytoecdysteroid profile changes in composition and amount
amongst plant species but is also dependent on plant organs, habitat season,
and origin.
Karlson et al. (1965) elucidated the chemical structure of a-ecdysone
by chemical transformations and physiochemical studies, and its
stereochemical structure was elucidated by Huber and Hoppe (1965) with
the help of X-ray analysis. Closely associated molecules were found in
species of the plant soon thereafter. Galbraith and Horn (1966) separated
ecdysterone, a phytoecdysone having insect-molting properties from a fern
Polypodium elatus. At the same time, Nakanishi et al. (1966) recognized
ponasterone from one more gymnosperm, known as, Podocarpus nakaii.
Jizba et al. (1967) separated crustecdysone from the Polypodium vulgare,
while Takemoto et al. (1967) removed insect-molding substances from the
mulberry leaves. These discoveries triggered further struggles to examine
the dispersal of ecdysones in the plants. They were also found in the red
algae which comprise closely associated pinnasterols, and in fungi. Lafont
and Dinan (2003) made the compilation of literature for the selection of
species of plant, among several others algae, vascular plants, and fungi. In
the start, the emphasis was on the detection of probable natural antitumoral
agents, but soon, the objective stimulated from human therapy to insecticidal
activity. As the molecules hindered insect reproduction and development,
there was a chance for the development of the novel category of natural
pesticides as a substitute for purely chemical agents. Conversely, the
difculty of these molecules makes them challenging to synthesize. They
can penetrate hardly in the living insects, and their stability is restricted in
the natural environment. Till now, none of the natural ecdysteroids have
made their way into pest control (Fukuzawa et al., 1981).
This chapter provides a review of the biodiversity of the phytoecdysteroids,
the feasible biosynthetic pathways of the molecules, and the postulated
functions of this category of inferior metabolites for humans and plants.
Phytochemistry, Pharmacology, and Applications of Phytoecdysteroids
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5.2. DISTRIBUTION OF PHYTOECDYSTEROIDS
Ecdybase is a brilliant resource for biological and chemical data for literature
data and ecdysteroid analogs on the existence of phytoecdysteroids in the
plants. Ecdysteroids appear to befall not only in an extensive diversity
of species but as a broad diversity of structures. Conjugates of glucosylferulate are among the novel classes of conjugates found in Microsporum
membranifolium. The question arises whether the phytoecdysteroids
are produced by the species of the plants themselves or whether the
phytoecdysteroids are taken up and consequently modified by species such
as fungi (Purser and Baker, 1994; Postnikov, 1995).
One more question is associated with the capability of a larger class
of plants to produce ecdysteroids. In the start, ferns were considered to be
the species demonstrative for the synthesis of ecdysteroids, but this was
because of the large number of ferns curtained. Ecdysteroids were also
discovered in species such as Arabidopsis thaliana, originally thought of
as ecdysteroid negative. The real concept is that some plant families do not
comprise ecdysteroid species inside their members. Some of the species
comprise huge amounts of phytoecdysteroids, but generally, the content of
steroids in plants is usually in the order 0.01 to 0.1% of the dry weight of
the plant. There may be an association between the absence or presence
of phytoecdysteroids and the taxonomic position of the plant species, e.g.,
within the family of Chenopodiaceae and inside the genus Silene.
Thus, it has been recommended that ecdysteroids might be taken as a
sign for taxonomic purposes, yet when uctuations because of organ type,
geographical location, and season might be the confounding factors. The
absence or presence of phytoecdysteroids might be helpful in the taxonomic
study of the mushrooms (e.g., Tapinella and Paxillus). The existence of
phytoecdysteroids in fragments of the higher plants has usually been
related to their survival struggles. For annual plants dependent on wind
pollinating, this gives the meaning that ecdysteroids will be existent in the
pollen-comprising parts, the young leaves, and the seeds (Sláma et al., 1996;
Kholodova, 2001).
5.3. DIVERSITY OF PHYTOECDYSTEROIDS
Numerous large-scale assessments have been carried out in the past,
producing hundreds of the phytoecdysteroid structures. Imai et al. (1969)
conducted the 1
st
survey on 1,056 varied well-identified species. They
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Natural Compounds: An Introduction
recognized ecdysteroids in 61 out of all species. Hikino et al. (1973) focused
their struggles on Japanese ferns. Their selection was centered on less
particular biological activity testing. This might be the justification for a
high number of positives: 170 out of 283 species tested presented positive
reactions (Kholodova, 2001; Palli et al., 2005).
The results of these selections are integrated into the Ecdybase (www.
ecdybase.org): ecdysteroid agonist along with antagonist comprising plants
is recorded. In July 2012, this database comprised 463 ecdysteroids. Apart
from geographical distribution, the ecological distribution has also been
concentrated. The hunt for phytoecdysteroids in the large diversity of plant
species stays the research target. Publications regarding the isolation of novel
entities or identied ecdysteroids in recently examined species of plant are
published in a large diversity of scientic journals. Some recent examples
are included here. Limnanthes alba is a developed oilseed crop and initiated
from southern Oregon. 20-hydroxyecdysone, Ecdysone, muristerone A, and
ponasterone A were recognized by LC-MS/MS in the seeds of a plant by
Stevens et al. (2008). Ecdysteroids were reported from the other species
of Limnanthaceae, more predominantly Limnanthes bakeri, L. occosa, L.
douglasii, L. Montana, and L. gracilis. Some of the other plant genera such
as Ajuga have been mainly studied as the rich source of structurally diverse
phytoecdysteroids. Castro et al. (2008) separated 3 novel phytoecdysteroids
from the Ajuga macrosperma var. breviora roots: breviorasterone and
ajugacetalsterones C and D. Another novel phytoecdysteroid, ajugatide E,
was separated from Ajuga taiwanensis. Novel compounds reptanslactone
B, reptanslactone A, and the sendreisterone were separated from Ajuga
reptans along with the known breviorasterone and dehydroprecyasterone.
20-hydroxyecdysone is also present in Ajuga remota. Ajuga remota is
utilized as an herbal medication against malaria in the state of Kenya (Figure
5.1) (Brekhman and Dardymov, 1969; Tavva et al., 2007a).
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