20-Hydroxyecdysone: Difference between revisions

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
VisualWikitext
imported>Mfernflower
No edit summary
 
+alternative name
 
Line 29: Line 29:
| metabolism        = [[Liver|Hepatic]]{{cn|date=June 2025}}
| metabolism        = [[Liver|Hepatic]]{{cn|date=June 2025}}
| elimination_half-life = 4-9 hours{{cn|date=June 2025}}
| elimination_half-life = 4-9 hours{{cn|date=June 2025}}
| excretion          = [[Urine|Urinary]]:?%
| excretion          =  


<!--Identifiers-->
<!--Identifiers-->
| synonyms          = BIO101
| synonyms          = BIO101, Ecdysterone
| CAS_number_Ref    = {{cascite|changed|??}}
| CAS_number_Ref    = {{cascite|changed|??}}
| CAS_number        = 5289-74-7
| CAS_number        = 5289-74-7
Line 60: Line 60:
}}
}}


'''20-Hydroxyecdysone''' ('''ecdysterone''' or '''20E''') is a naturally occurring [[ecdysteroid]] [[hormone]] which controls the [[ecdysis]] (moulting) and [[metamorphosis]] of [[arthropods]]. It is therefore one of the most common moulting hormones in insects, crabs, etc. A [[phytoecdysteroid]] produced by and extracted from various plants, including ''[[Cyanotis|Cyanotis vaga]]'', ''[[Ajuga turkestanica]]'' and ''[[Rhaponticum carthamoides]]'', it is belived to be a [[plant defense against herbivory]] that disrupts the [[reproduction]] of insect pests. In arthropods, 20-hydroxyecdysone acts through the [[ecdysone receptor]]. Although mammals (including humans) lack this [[Receptor (biochemistry)|receptor]], 20-hydroxyecdysone affects [[mammalian]] biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In mammals, it is hypothesized to bind to the [[estrogen receptor beta]] (ERβ) protein..<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | bibcode = 2019ArTox..93.1807I | hdl-access = free | hdl = 11573/1291269 }}</ref>
'''20-Hydroxyecdysone''' ('''ecdysterone''' or '''20E''') is a naturally occurring [[ecdysteroid]] [[hormone]] which controls the [[ecdysis]] (moulting) and [[metamorphosis]] of [[arthropods]]. It is therefore one of the most common moulting hormones in insects, crabs, etc. A [[phytoecdysteroid]] produced by and extracted from various plants, including ''[[Cyanotis]] vaga'', ''[[Ajuga turkestanica]]'' and ''[[Rhaponticum carthamoides]]'', it is thought to be a [[plant defense against herbivory]] that disrupts the [[reproduction]] of insect pests. In arthropods, 20-hydroxyecdysone acts through the [[ecdysone receptor]]. Although mammals (including humans) lack this [[Receptor (biochemistry)|receptor]], 20-hydroxyecdysone affects [[mammalian]] biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In mammals, it is hypothesized to bind to the [[estrogen receptor beta]] (ERβ) protein.<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | bibcode = 2019ArTox..93.1807I | hdl-access = free | hdl = 11573/1291269 }}</ref>


==Sources in arthropods==
==Sources in arthropods==
Line 74: Line 74:


===Use as supplement===
===Use as supplement===
20-Hydroxyecdysone and other ecdysteroids are marketed as ingredients in [[nutritional supplement]]s for various sports, particularly [[bodybuilding]].<ref>{{cite journal | vauthors = Cohen PA, Sharfstein J, Kamugisha A, Vanhee C | title = Analysis of Ingredients of Supplements in the National Institutes of Health Supplement Database Marketed as Containing a Novel Alternative to Anabolic Steroids | journal = JAMA Network Open | volume = 3 | issue = 4 | pages = e202818 | date = April 2020 | pmid = 32293681 | doi = 10.1001/jamanetworkopen.2020.2818 | pmc = 7160690 }}</ref> Although a number of early studies supported the anabolic effects of 20-hydroxyecdysone,<ref>{{cite journal | vauthors = Simakin SY | title = The Combined Use of Ecdisten and the Product'Bodrost'during Training in Cyclical Types of Sport. | journal = Scientific Sports Bulletin | date = 1988 | pages = 2 }}</ref><ref>{{cite journal | vauthors = Gadzhieva RM, Portugalov SN, Paniushkin VV, Kondrat'eva II | title = [A comparative study of the anabolic action of ecdysten, leveton and Prime Plus, preparations of plant origin.] | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | date = 1995 | volume = 58 | issue = 5 | pages = 46–8 | pmid = 8704590 }}</ref><ref name="pmid18220764">{{cite journal | vauthors = Báthori M, Tóth N, Hunyadi A, Márki A, Zádor E | title = Phytoecdysteroids and anabolic-androgenic steroids--structure and effects on humans | journal = Current Medicinal Chemistry | volume = 15 | issue = 1 | pages = 75–91 | date = 2008 | pmid = 18220764 | doi = 10.2174/092986708783330674 | url = http://publicatio.bibl.u-szeged.hu/10883/1/2008_Bathori_et_al._CMC_u.pdf }}</ref><ref>{{cite report | vauthors = Smetanin BY | title = The influence of preparations of plant origin on physical work capacity. | publisher = The Russian Ministry of Public Health | date = 1986 }}</ref><ref>{{cite report | vauthors = Fadeev BG | title = Comments on the Results of Retibol in the Practice of Athletic Training and Rehabilitation | publisher = Natural Sports Research Institute }}</ref><ref name="pmid9575416">{{cite journal | vauthors = Azizov AP, Seĭfulla RD, Ankudinova IA, Kondrat'eva II, Borisova IG | title = [The effect of the antioxidants elton and leveton on the physical work capacity of athletes] | language = ru | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 61 | issue = 1 | pages = 60–2 | date = 1998 | pmid = 9575416 }}</ref> a 2006 study concluded that the use of 30&nbsp;mg per day of 20-hydroxyecdysone administered orally did not significantly affect [[anabolic]] or [[catabolic]] responses to [[resistance training]], [[body composition]], or training adaptations.<ref>{{cite journal | vauthors = Wilborn CD, Taylor LW, Campbell BI, Kerksick C, Rasmussen CJ, Greenwood M, Kreider RB | title = Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males | journal = Journal of the International Society of Sports Nutrition | volume = 3 | issue = 2 | pages = 19–27 | date = December 2006 | pmid = 18500969 | pmc = 2129166 | doi = 10.1186/1550-2783-3-2-19 | doi-access = free }}</ref> However, a 2019 study found significantly higher increases in [[muscle mass]] and [[1RM|one-repetition]] [[bench press]] performance in participants dosed with ecdysterone. The study, funded by the [[World Anti-Doping Agency]], demonstrated a significant [[dose response |dose-responsive]] anabolic effect.<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | bibcode = 2019ArTox..93.1807I | hdl-access = free | hdl = 11573/1291269 }}</ref> Other studies have elucidated the mechanism of action of 20-hydroxyecdysone on human [[muscle cell]]s, which appears to involve relatively selective activation of [[estrogen receptor beta]] (ERβ), known to result in [[muscle hypertrophy]].<ref name="pmid24974955">{{cite journal | vauthors = Parr MK, Zhao P, Haupt O, Ngueu ST, Hengevoss J, Fritzemeier KH, Piechotta M, Schlörer N, Muhn P, Zheng WY, Xie MY, Diel P | title = Estrogen receptor beta is involved in skeletal muscle hypertrophy induced by the phytoecdysteroid ecdysterone | journal = Molecular Nutrition & Food Research | volume = 58 | issue = 9 | pages = 1861–72 | date = September 2014 | pmid = 24974955 | doi = 10.1002/mnfr.201300806 }}</ref> It has recently been identified as a [[Mas receptor]] agonist as well.
20-Hydroxyecdysone and other ecdysteroids are marketed as ingredients in [[nutritional supplement]]s for various sports, particularly [[bodybuilding]].<ref>{{cite journal | vauthors = Cohen PA, Sharfstein J, Kamugisha A, Vanhee C | title = Analysis of Ingredients of Supplements in the National Institutes of Health Supplement Database Marketed as Containing a Novel Alternative to Anabolic Steroids | journal = JAMA Network Open | volume = 3 | issue = 4 | pages = e202818 | date = April 2020 | pmid = 32293681 | doi = 10.1001/jamanetworkopen.2020.2818 | pmc = 7160690 }}</ref> Although a number of early studies supported the anabolic effects of 20-hydroxyecdysone,<ref>{{cite journal | vauthors = Simakin SY | title = The Combined Use of Ecdisten and the Product'Bodrost'during Training in Cyclical Types of Sport. | journal = Scientific Sports Bulletin | date = 1988 | pages = 2 }}</ref><ref>{{cite journal | vauthors = Gadzhieva RM, Portugalov SN, Paniushkin VV, Kondrat'eva II | title = [A comparative study of the anabolic action of ecdysten, leveton and Prime Plus, preparations of plant origin.] | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | date = 1995 | volume = 58 | issue = 5 | pages = 46–8 | pmid = 8704590 }}</ref><ref name="pmid18220764">{{cite journal | vauthors = Báthori M, Tóth N, Hunyadi A, Márki A, Zádor E | title = Phytoecdysteroids and anabolic-androgenic steroids--structure and effects on humans | journal = Current Medicinal Chemistry | volume = 15 | issue = 1 | pages = 75–91 | date = 2008 | pmid = 18220764 | doi = 10.2174/092986708783330674 | url = http://publicatio.bibl.u-szeged.hu/10883/1/2008_Bathori_et_al._CMC_u.pdf }}</ref><ref>{{cite report | vauthors = Smetanin BY | title = The influence of preparations of plant origin on physical work capacity. | publisher = The Russian Ministry of Public Health | date = 1986 }}</ref><ref>{{cite report | vauthors = Fadeev BG | title = Comments on the Results of Retibol in the Practice of Athletic Training and Rehabilitation | publisher = Natural Sports Research Institute }}</ref><ref name="pmid9575416">{{cite journal | vauthors = Azizov AP, Seĭfulla RD, Ankudinova IA, Kondrat'eva II, Borisova IG | title = [The effect of the antioxidants elton and leveton on the physical work capacity of athletes] | language = ru | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 61 | issue = 1 | pages = 60–2 | date = 1998 | pmid = 9575416 }}</ref> a 2006 study concluded that the use of 30&nbsp;mg per day of 20-hydroxyecdysone administered orally did not significantly affect [[anabolic]] or [[catabolic]] responses to [[resistance training]], [[body composition]], or training adaptations.<ref>{{cite journal | vauthors = Wilborn CD, Taylor LW, Campbell BI, Kerksick C, Rasmussen CJ, Greenwood M, Kreider RB | title = Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males | journal = Journal of the International Society of Sports Nutrition | volume = 3 | issue = 2 | pages = 19–27 | date = December 2006 | pmid = 18500969 | pmc = 2129166 | doi = 10.1186/1550-2783-3-2-19 | doi-access = free }}</ref> However, a 2019 study found significantly higher increases in [[muscle mass]] and [[1RM|one-repetition]] [[bench press]] performance in participants dosed with ecdysterone. The study, funded by the [[World Anti-Doping Agency]], demonstrated a significant [[dose response |dose-responsive]] anabolic effect.<ref>{{cite journal | vauthors = Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK | s2cid = 163166547 | title = Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans | journal = Archives of Toxicology | volume = 93 | issue = 7 | pages = 1807–1816 | date = July 2019 | pmid = 31123801 | doi = 10.1007/s00204-019-02490-x | bibcode = 2019ArTox..93.1807I | hdl-access = free | hdl = 11573/1291269 }}</ref> Other studies have elucidated the mechanism of action of 20-hydroxyecdysone on human [[muscle cell]]s, which appears to involve relatively selective activation of [[estrogen receptor beta]] (ERβ), known to result in [[muscle hypertrophy]].<ref name="pmid24974955">{{cite journal | vauthors = Parr MK, Zhao P, Haupt O, Ngueu ST, Hengevoss J, Fritzemeier KH, Piechotta M, Schlörer N, Muhn P, Zheng WY, Xie MY, Diel P | title = Estrogen receptor beta is involved in skeletal muscle hypertrophy induced by the phytoecdysteroid ecdysterone | journal = Molecular Nutrition & Food Research | volume = 58 | issue = 9 | pages = 1861–72 | date = September 2014 | pmid = 24974955 | doi = 10.1002/mnfr.201300806 }}</ref> It has recently been identified as a [[MAS1]] agonist as well.


=== Drug development ===
=== Drug development ===

Latest revision as of 19:30, 25 June 2025

Template:Short description Template:MCN Template:Cs1 config Template:Drugbox

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. A phytoecdysteroid produced by and extracted from various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides, it is thought to be a plant defense against herbivory that disrupts the reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals (including humans) lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In mammals, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein.[1]

Sources in arthropods

The primary sources of 20-hydroxyecdysone in larvae are the prothoracic gland, ring gland, gut, and fat bodies. These tissues convert dietary cholesterol into the mature forms of the hormone 20-hydroxyecdysone.[2] For the most part, these glandular tissues are lost in the adult, with exception of the fat body, which is retained as a sheath of lipid tissue surrounding the brain and organs of the abdomen. In the adult female, the ovary is a substantial source of 20-hydroxyecdysone production.[3] Adult males are left with, so far as is currently known, one source of 20-hydroxyecdysone, which is the fat body tissue. These hormone-producing tissues express the ecdysone receptor throughout development, possibly indicating a functional feedback mechanism.Script error: No such module "Unsubst".

Ecdysteroid activity in arthropods

In insects, an ecdysteroid is a type of steroid hormone derived from enzymatic modification of cholesterol by p450 enzymes.[4] This occurs by a mechanism similar to steroid synthesis in vertebrates. Ecdysone and 20-hydroxyecdysone regulate larval molts, onset of puparium formation, and metamorphosis. As these hormones are hydrophobic, they traverse lipid membranes and permeate the tissues of an organism. Indeed, the ecdysone receptor is an intracellular protein.[5]

In humans and other mammals

Use as research tool

20-Hydroxyecdysone and other ecdysteroids are used in biochemistry research as inducers in transgenic animals, whereby a new gene is introduced into an animal so that its expression is under the control of an introduced ecdysone receptor. Adding or removing ecdysteroids from the animal's diet then gives a convenient way to turn the inserted gene on or off. At usual doses, 20-hydroxyecdysone appears to have little or no effect on animals that do not have extra genes inserted. Given its high oral bioavailability, therefore, it is useful for determining whether the transgene has been taken up effectively.[6] However, studies mentioned below show that 20E is not totally inert in non-transgenic mammals.

Use as supplement

20-Hydroxyecdysone and other ecdysteroids are marketed as ingredients in nutritional supplements for various sports, particularly bodybuilding.[7] Although a number of early studies supported the anabolic effects of 20-hydroxyecdysone,[8][9][10][11][12][13] a 2006 study concluded that the use of 30 mg per day of 20-hydroxyecdysone administered orally did not significantly affect anabolic or catabolic responses to resistance training, body composition, or training adaptations.[14] However, a 2019 study found significantly higher increases in muscle mass and one-repetition bench press performance in participants dosed with ecdysterone. The study, funded by the World Anti-Doping Agency, demonstrated a significant dose-responsive anabolic effect.[15] Other studies have elucidated the mechanism of action of 20-hydroxyecdysone on human muscle cells, which appears to involve relatively selective activation of estrogen receptor beta (ERβ), known to result in muscle hypertrophy.[16] It has recently been identified as a MAS1 agonist as well.

Drug development

In 2024, the Food and Drug Administration approved a study on the efficacy of 20-hydroxyecdysone in treating obesity, focusing on muscle strength improvement in the lower limbs.[17]

References

Template:Reflist

External links

  • Ecdybase, The Ecdysone Handbook - a free online ecdysteroids database
  1. ↑ Script error: No such module "Citation/CS1".
  2. ↑ Script error: No such module "Citation/CS1".
  3. ↑ Script error: No such module "Citation/CS1".
  4. ↑ Script error: No such module "Citation/CS1".
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Template:Cite report
  12. ↑ Template:Cite report
  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Script error: No such module "Citation/CS1".
  17. ↑ Script error: No such module "citation/CS1".
Retrieved from "http://debianws.lexgopc.com/wiki143/index.php?title=20-Hydroxyecdysone&oldid=2039383"