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PHYTOECDYSTEROIDS:
ISOLATION AND BIOLOGICAL
APPLICATIONS
Phytoecdysteroids are a class of chemicals that plant
synthesize 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 molting process known as
ecdysis. Insects that ingest phytoecdysteroids and have not
adapted to this defense are subject to serious adverse effects,
including reduced weight, molting disruption, and/or
mortality.
Phytoecdysteroids are distributed
throughout the plant kingdom, with approximately 6% of all
plants surveyed containing detectable levels of ecdysteroids
Chemistry of Phytoecdysteroids
Chemically, phytoecdysteroids are classed as triterpenoids,
the group of compounds that includes triterpene saponins,
phytosterols, and phytoecdysteroids. Ecdysteroids are polar
steroids, almost sugar-like in their solubility properties
While mammalian steroid hormones
have more variable structures, they universally lack the
polyhydroxylated side chain characteristic of ecdysteroids
and are therefore more lipophilic.
Unlike invertebrates, which are unable to synthesize ecdysteroids
and must consume dietary phytosterols that are then
converted into ecdysteroids, plants can completely produce
ecdysteroids from mevalonic acid and cholesterol.
The sterol structure is modified to produce ecdysteroids.
The trans A/B ring juncture in sterols is converted to a cis
A/B ring juncture in ecdysteroids, and a 7-en-6-one
chromophore and a 14 a-hydroxy group are added .
Additional hydroxylations at C2, C20,
C22, and C25 are required to produce the most common
phytoecdysteroid, 20-hydroxyecdysone (20HE).
Plant Families with Known
Ecdysteroids
Among plant species highest in phytoecdysteroids is
spinach (Spinacia oleracea L., Chenopodiaceae) containing
50 ug/g fresh weight. Other examples
are: ajugasterone in Ajuga L., Lamiaceae and Vitex L.,
Verbenaceae; leuzeasterone in Leuzea carthamoides (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; ecdysterone and
inokosterone in Achyranthes bidentata Blume,
Amaranthaceae. polypodine B in Leuzea
carthamoides and ecdysterone, ajugasterone
C, ajugasterone C-20, 22- monoacetonide in Rhaponticum
uniflorum (L.) DC., Asteraceae
Unified isolation scheme for phytoecdysteroids. Al2O3 column
chromatography on alumina; silica (column chromatography on silica);
DCCC droplet countercurrent chromatography; HPLC high performance
liquid chromatography; PTLC preparative thin-layer chromatography on
silica; LH-20 column chromatography on Sephadex LH-20; Crys
crystallization; m.liquid using the mother liquid for further isolation; 20E
20-hydroxyecdysone; 2d 2-deoxy; Ac acetate; Bz benzoate.
Importance of
Phytoecdysteroi
ds for
Plants and
Animals
◦ The two most common hormones found in insects are the
ecdysteroid, 20E hydroxyecdysone (ecdysone) and the
sesquiterpene, juvenile hormone. They are usually
accompanied by a number of other minor ecdysteroids. The
application of very low doses has proven beneficial to improve
the synchrony of development and yield of certain
commercially important arthropods.
◦ The most extensively studied examples are
silk moths (especially Bombyx mori), where protocols have
been developed for the preparation of ecdysteroid containing
extracts from native plants and application to the food plant
(Morus spp.) at particular stages of development, which result
in more synchronous cocoon formation and higher yields of
silk per cocoon .
◦ Benefits may also
accrue from the use of low doses of ecdysteroids in apiculture
and aquaculture
Pharmaceutical Applications
The effects of ecdysteroids /phytoecdysteroids are varied
and can be divided and briefly summarized as follows.
 Anabolic agents:,
 Adaptogenic agents:,
 Anti-diabetic agents:,
 Hypocholesterolaemic agents,
 Wound-healing, Immunoprotective agents,
 Toxicity:
Conclusion
In view of the above wide-ranging and largely positive
effects, it is perhaps not surprising that several food companies
are showing interest in adding ecdysteroid-containing plant
materials or extracts into food products as a way of enhancing
health claims and profit margins. For example, in France at the
moment, quinoa (Chenopodium quinoa) is appearing in a very
wide range of nutritional products, from pasta, biscuits, and
bread to chocolate, drinks, and baby food.
Rhizomata cum radicibus Leuzeae
Leuzea carthamoides (Wilid.)DC.
(Rhaponticum carthamoides (Wilid)) Iljin
Asteraceae
Height 0,5-2 m
herbaceous
perennial plant
◦ Chemical constituent
Root and Rhizomes
0,03-0,6 % phytoecddysones (ecdysterone,
inocosterone, integristeron A,B)
essential oils
ascorbic acid, carotins
flavonoids, tannins, phenol
organic acids
inulin
Flowering in
July-
AugustSeed in
August -
September
Use in medicine
Liquid extraction of rhizome and roots – EKDISTEN-
Liquid extraction- nervous system disorder
Mental and physical fatigue
Reduced work capacity
EKDISON 0,005 gr tablet
as general tonic in asthenia, reduced work ability, protein synthesis weakens, infectious diseases,
intoxication, neurosis, neurasthenia, sports (prior to intensive exercise athletes are identified with
protein diet)

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Phytoecdysteroids

  • 2. Phytoecdysteroids are a class of chemicals that plant synthesize 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 molting process known as ecdysis. Insects that ingest phytoecdysteroids and have not adapted to this defense are subject to serious adverse effects, including reduced weight, molting disruption, and/or mortality. Phytoecdysteroids are distributed throughout the plant kingdom, with approximately 6% of all plants surveyed containing detectable levels of ecdysteroids
  • 3. Chemistry of Phytoecdysteroids Chemically, phytoecdysteroids are classed as triterpenoids, the group of compounds that includes triterpene saponins, phytosterols, and phytoecdysteroids. Ecdysteroids are polar steroids, almost sugar-like in their solubility properties
  • 4. While mammalian steroid hormones have more variable structures, they universally lack the polyhydroxylated side chain characteristic of ecdysteroids and are therefore more lipophilic. Unlike invertebrates, which are unable to synthesize ecdysteroids and must consume dietary phytosterols that are then converted into ecdysteroids, plants can completely produce ecdysteroids from mevalonic acid and cholesterol. The sterol structure is modified to produce ecdysteroids. The trans A/B ring juncture in sterols is converted to a cis A/B ring juncture in ecdysteroids, and a 7-en-6-one chromophore and a 14 a-hydroxy group are added . Additional hydroxylations at C2, C20, C22, and C25 are required to produce the most common phytoecdysteroid, 20-hydroxyecdysone (20HE).
  • 5. Plant Families with Known Ecdysteroids Among plant species highest in phytoecdysteroids is spinach (Spinacia oleracea L., Chenopodiaceae) containing 50 ug/g fresh weight. Other examples are: ajugasterone in Ajuga L., Lamiaceae and Vitex L., Verbenaceae; leuzeasterone in Leuzea carthamoides (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; ecdysterone and inokosterone in Achyranthes bidentata Blume, Amaranthaceae. polypodine B in Leuzea carthamoides and ecdysterone, ajugasterone C, ajugasterone C-20, 22- monoacetonide in Rhaponticum uniflorum (L.) DC., Asteraceae
  • 6. Unified isolation scheme for phytoecdysteroids. Al2O3 column chromatography on alumina; silica (column chromatography on silica); DCCC droplet countercurrent chromatography; HPLC high performance liquid chromatography; PTLC preparative thin-layer chromatography on silica; LH-20 column chromatography on Sephadex LH-20; Crys crystallization; m.liquid using the mother liquid for further isolation; 20E 20-hydroxyecdysone; 2d 2-deoxy; Ac acetate; Bz benzoate.
  • 7. Importance of Phytoecdysteroi ds for Plants and Animals ◦ The two most common hormones found in insects are the ecdysteroid, 20E hydroxyecdysone (ecdysone) and the sesquiterpene, juvenile hormone. They are usually accompanied by a number of other minor ecdysteroids. The application of very low doses has proven beneficial to improve the synchrony of development and yield of certain commercially important arthropods. ◦ The most extensively studied examples are silk moths (especially Bombyx mori), where protocols have been developed for the preparation of ecdysteroid containing extracts from native plants and application to the food plant (Morus spp.) at particular stages of development, which result in more synchronous cocoon formation and higher yields of silk per cocoon . ◦ Benefits may also accrue from the use of low doses of ecdysteroids in apiculture and aquaculture
  • 8. Pharmaceutical Applications The effects of ecdysteroids /phytoecdysteroids are varied and can be divided and briefly summarized as follows.  Anabolic agents:,  Adaptogenic agents:,  Anti-diabetic agents:,  Hypocholesterolaemic agents,  Wound-healing, Immunoprotective agents,  Toxicity:
  • 9. Conclusion In view of the above wide-ranging and largely positive effects, it is perhaps not surprising that several food companies are showing interest in adding ecdysteroid-containing plant materials or extracts into food products as a way of enhancing health claims and profit margins. For example, in France at the moment, quinoa (Chenopodium quinoa) is appearing in a very wide range of nutritional products, from pasta, biscuits, and bread to chocolate, drinks, and baby food.
  • 10. Rhizomata cum radicibus Leuzeae Leuzea carthamoides (Wilid.)DC. (Rhaponticum carthamoides (Wilid)) Iljin Asteraceae
  • 11. Height 0,5-2 m herbaceous perennial plant ◦ Chemical constituent Root and Rhizomes 0,03-0,6 % phytoecddysones (ecdysterone, inocosterone, integristeron A,B) essential oils ascorbic acid, carotins flavonoids, tannins, phenol organic acids inulin Flowering in July- AugustSeed in August - September
  • 12. Use in medicine Liquid extraction of rhizome and roots – EKDISTEN- Liquid extraction- nervous system disorder Mental and physical fatigue Reduced work capacity EKDISON 0,005 gr tablet as general tonic in asthenia, reduced work ability, protein synthesis weakens, infectious diseases, intoxication, neurosis, neurasthenia, sports (prior to intensive exercise athletes are identified with protein diet)