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Phytoecdysteroids_rklein

Phytoecdysteroids_rklein

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Published by Robyn Klein
Phytoecdysteroids are a class of compounds made by plants that defend against plant-eating insects.
Phytoecdysteroids are a class of compounds made by plants that defend against plant-eating insects.

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Published by: Robyn Klein on Jul 17, 2012
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Journal of the American Herbalists Guil
Fall/Winter 2004 
AH
A western herbalist andmedical botanist, RobynKlein currently teachescourses at Montana StateUniversity: HerbalMedicine, HerbalMedicine Laboratory,Medicinal Plants ofMontana, MedicalBotany, Flowering Plantsof the Northern RockyMountains, and Plants,People, and Health.Robyn’s graduate projectfocused on thephylogenetic analysis ofadaptogenic plants andtheir secondarycompounds.
Phytoecdysteroids 
by Robyn Klein, RH (AHG), MS, Medical Botanist 
Introduction
Plants have survived assaults from organisms andenvironmental stress for millennia. They have done soby various mechanisms including physical barriers suchas thorns and thick cuticles, and by synthesizing anarray of defense chemicals as well as other growth anddefense mechanisms. Protective mechanisms used byanimals and humans are often similar in strategy andcomplementary in the substances used for protection.Phytoecdysteroids are a class of chemicals that plantssynthesize for defense against phytophagous (plant-eating) insects. These compounds are exact replicas of ecdysteroids, hormones used by the arthropod (insect)and crustacean (crab/lobster) families in the moltingprocess known as ecdysis. Insects that ingestphytoecdysteroids and have not adapted to this defenseare subject to serious adverse effects, including reducedweight, molting disruption, and/or mortality (Dinan2001). Since 1966, when phytoecdysteroids werediscovered in plants, they have been shown to stimulatethe synthesis of proteins in animals and humans, and tohave adaptogenic, antimutagenic, hypocholesterolemic,immunostimulating, nutritive, and tonic properties(Kholodova 2001; Lafont and Dinan 2003). This paperreviews the importance of phytoecdysteroids as a class of plant compounds responsible for some tonic andadaptogenic effects in medicinal plants.
Chemistry of phytoecdysteroids
The two most common hormones found in insects arethe ecdysteroid, 20E-hydroxyecdysone (ecdysone) andthe sesquiterpene, juvenile hormone (Figure 1). Theyare usually accompanied by a number of other minorecdysteroids. For example, the silkworm,
 Bombxy mori
L., has been found to contain at least 19 ecdysteroids(Kamba et al., 1994).Chemically, phytoecdysteroids are classed astriterpenoids, the group of compounds that includestriterpene saponins, phytosterols, and phytoecdysteroids(Figure 2).Plants synthesize phytoecdysteroids from mevalonicacid in the mevalonate pathway of the plant cell usingacetyl-CoA as a precursor (Figure 3). Animals andhumans also synthesize some of the same products fromthe mevalonate pathway, such as ubiquinone andsterols. They cannot, however, synthesize ecdysteroids.Over 250 ecdysteroid analogs have been identifiedso far in plants, and it has been theorized that there areover 1,000 possible structures which might occur innature (Dinan 2001). There is evidence that most plantsretain the genetic capacity to produce ecdysteroids, buttheir expression is turned off (Dinan et al. 2001a). Thequestion remains whether the capacity to synthesizeecdysteroids is genetically or environmentally induced.Either way, it may be possible to alter the expression of genes as a way to increase the amount of phytoecdysteroids in plants to increase protection of 
Figure 1.The most common insect hormones,20E-hydroxyecdysone (ecdysone) and juvenile hormone.
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    M    A    T    E    R    I    A    M    E    D    I    C    A
AH
Fall/Winter 2004 
Journal of the American Herbalists Guil
crops and to provide raw material to produce dietarysupplements (Dinan et al 2001a).Ecdysteroids are polar steroids, almost sugar-like intheir solubility properties (Gilbert et al. 2002). Whilemammalian steroid hormones have more variablestructures, they universally lack the polyhydroxylatedside chain characteristic of ecdysteroids and aretherefore more lipophilic (Gilbert et al. 2002).Most phytoecdysteroids possess a cholest-7-en-6-one carbon skeleton (C27), derived biosyntheticallyfrom cholesterol and phytosterols, often with a hydroxylgroup in the 14·-position (Bathori 2002). The carbonnumber can vary between C19-C29 (sometimes C30)(Lafont 1997). Although variation in the steroid ringstructure is not substantial, significant variation lies inthe number, position and orientation of the hydroxylgroups and the conjugating moieties linked throughthese. The commonly hydroxylated sites are the 2‚-, 3‚-,14·-, 20R- and 22R- positions, which together give riseto the highly biologically active ponasterone A (25-deoxy-20-hydroxyecdysone) (Dinan 2001).
Plant families with known ecdysteroids
Approximately 6% of all plant species synthesizephytoecdysteroids (Dinan 2001). Phytoecdysteroidlevels in plants are usually found to be 0.1% or less of their dry weight and have been isolated from all parts of plants in much higher amounts than those present inarthropods (Dinan 2001). Low concentrations of various
CYTOSOL
CHLOROPLAST
acetyl-CoAtriterpenes C30sesquiterpenes C15phytosterolsphytoecdysteroldsIPP
Mevalonale pathwaydeoxyxylulosepathway
pyruvatemonoterpenes C10diterpenes C20phytols C45tetraterpenes C40IPP
Figure 3.Biosyntheticpathway ofphytoecdysteroids in theplant cell.Figure 2.Molecularstructure of triterpenoidsaponins,phytosterols,and phytoecdysteroids.
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Journal of the American Herbalists Guil
Fall/Winter 2004 
AH
phytoecdysteroids deter some insects (2-25 ppm), whileother insects are resistant to very high concentrations(400-1000 ppm). It appears ecdysteroid concentrationsare highest in tissues which are most important for thesurvival of the plant and that these levels changethroughout plant development. The most commonphytoecdysteroid found in plants is ecdysone (20E-hydroxyecdysone) (Dinan 2001).While most plant families have at least some speciesthat accumulate ecdysteroids, less than 2% of the world’sflora has been investigated for the presence of ecdysteroids (Dinan et al. 2001a, Dinan et al. 2002)(Table 1). One can search for presence of ecdysteroids inplants at www.ecdybase.org. See also Dinan (2004) for acompilation of ecdysteroids found in vascular plants,algae, fungi and non-arthropod invertebrates.Among plant species highest in phytoecdysteroids isspinach (
Spinacia oleracea
L., Chenopodiaceae)containing 50 ug/g fresh weight (Grebenok et al.1994).Other examples are: ajugasterone in
 Ajuga
L., Lamiaceaeand Vitex L., Verbenaceae; leuzeasterone in
 Leuzeacarthamoides
(syn.
 Rhaponticum carthamoides
(Willd.)Iljin, Asteraceae); 2-deoxy-20-hydroxyecdysone 3-glucoside and 3-epi-2-deoxy-20-hydroxyecdysone in
Tinospora cordifolia
(Willd.) Miers, Menispermaceae(Garcia et al. 1989, Song et al.1991); ecdysterone andinokosterone in
 Achyranthes bidentata
Blume,Amaranthaceae (Gao et al.2000); polypodine B in
 Leuzea carthamoides
(Pis et al., 1994); and ecdysterone,ajugasterone C, ajugasterone C-20, 22- monoacetonidein
 Rhaponticum uniflorum
(L.) DC., Asteraceae (Zhanget al. 2002).
Adaptogenic activity
The term adaptogen, coined by Lazarev in 1958, has nocorrelation in modern pharmacology although scientific
Phytoecdysteroids 
Asteraceae
Centaurea L
.Sarker et al 1997Asteraceae
Leuzea carthamoides* 
Lafont et al 2004Asteraceae
Serratula coronata L.* 
Dinan 2001Asteraceae
Rhaponticum uniflorum 
Zhang et al 2002Amaranthaceae
Achyranthes bidentata*, A. aspera L.
Gao et al.2000,Lafont et al 2004Amaranthaceae
Cyathula achyranthoides 
(Kunth) Moq.,C.
officinalis 
K.C.KuanLafont et al.2004Amaranthaceae
Gomphrena L.
Savchenko et al.1998Amaranthaceae
Pfaffia paniculata 
(Mart.) Kuntze*,
P. iresinoides 
(Kunth) SprengLeBizec et al.1997Caryophyllaceae
Silene L.
Zibareva et al.2002Chenopodiaceaemany speciesDinan et al.1998Commelinaceae
Cyanotis somaliensis 
C.B.ClarkeLafont et al.2004Lamiaceae
Lamium L.
Savchenko et al.2001Lamiaceae
Ajuga turkestanica 
(Regel) Briq.Syrov et al.2001Liliaceaemany speciesDinan et al.2001bMenispermaceae
Tinospora cordifolia* 
Song et al.1991Plumbaginaceae
Limonium 
Mill.Whiting et al.1998Polypodiaceae
Polypodium vulgare L.
,P.
aurea 
L.,P.
glycyrrhiza 
D.C.EatonLafont et al.2004Ranunculaceaemany speciesDinan et al.,2002
Family Genus/Species Citation(s
Table 1.Some plantfamilies and speciescontainingphytoecdysteroids.Starred(*) species are recognizedas adaptogens.

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