Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 20-Hydroxyecdysone: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

| verifiedrevid = 477215829

| IUPAC_name = (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one

| image = 20-Hydroxyecdysone.svg

| alt = Skeletal formula of 20-hydroxyecdysone

| width = 260

| image2 = 20-Hydroxyecdysone 3D ball.png

| alt2 = Ball-and-stick model of the 20-hydroxyecdysone molecule

<!--Clinical data-->| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = [[Dietary supplement]] (as a botanical substance)

| legal_status =

<!--Pharmacokinetic data-->| bioavailability =

| protein_bound =

| metabolism = [[Liver|Hepatic]]

| excretion = [[Urine|Urinary]]:?%

<!--Identifiers-->| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 5289-74-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 779A7KPL0Y

| ATC_prefix =

| ATC_suffix =

| PubChem = 5459840

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4573597

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16587

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 224128

<!--Chemical data-->| C = 27

| H = 44

| O = 7

| smiles = O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NKDFYOWSKOHCCO-YPVLXUMRSA-N

'''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 various plants, including ''[[Cyanotis|Cyanotis vaga]]'', ''[[Ajuga turkestanica]]'' and ''[[Rhaponticum carthamoides]]'', its purpose is presumably to disrupt the [[developmental biology|development]] and [[reproduction]] of insect pests. In arthropods, 20-hydroxyecdysone acts through the [[ecdysone receptor]]. Although mammals 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 humans, it is hypothesized to bind to the [[estrogen receptor beta]] (ERβ) protein-coding gene.<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 | display-authors = 6 | 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 | hdl-access = free | hdl = 11573/1291269 }}</ref>

==Sources in arthropods==

The primary sources of 20-hydroxyecdysone in larvae are the [[prothoracic gland]], ring gland, gut, and [[fat body|fat bodies]]. These tissues convert dietary [[cholesterol]] into the mature forms of the hormone 20-hydroxyecdysone.<ref>{{cite journal | vauthors = Thummel CS, Chory J | title = Steroid signaling in plants and insects--common themes, different pathways | journal = Genes & Development | volume = 16 | issue = 24 | pages = 3113–29 | date = December 2002 | pmid = 12502734 | doi = 10.1101/gad.1042102 | url = http://www.genesdev.org/cgi/reprint/16/24/3113 | doi-access = free }}</ref> 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.<ref>{{cite journal | vauthors = Handler AM | title = Ecdysteroid titers during pupal and adult development in Drosophila melanogaster | journal = Developmental Biology | volume = 93 | issue = 1 | pages = 73–82 | date = September 1982 | pmid = 6813165 | doi = 10.1016/0012-1606(82)90240-8 }}</ref> 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 loop| feedback mechanism]].{{cn|date=September 2024}}

==Ecdysteroid activity in arthropods==

{{unreferenced |section|date=September 2024}}

In insects, an [[ecdysteroid]] is a type of [[steroid hormone]] derived from enzymatic modification of cholesterol by [[p450]] enzymes. 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 membrane]]s and permeate the tissues of an organism. Indeed, the [[ecdysone receptor]] is an [[intracellular]] [[protein]].

==In humans and other mammals==

===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.<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 | display-authors = 6 | 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 | hdl-access = free | hdl = 11573/1291269 }}</ref> The study, funded by the [[World Anti-Doping Agency]], demonstrated a significant [[dose response |dose-responsive]] anabolic effect. Other studies have elucidated the mechanism of action of 20-hydroxyecdysone on human [[muscle cell]]s, which appears to involve relatively selective activation of the beta form of the estrogen receptor (ERβ),<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> known to result in [[muscle hypertrophy]].<ref>{{cite web |title=Ecdysterone: Definition, Benefits, & Side Effects |url=https://turkesterone.com/pages/ecdysterone |website=Turkesterone.com}}</ref>{{Promotional source|date=September 2023}}

===Use as research tool===

20-Hydroxyecdysone and other ecdysteroids are used in biochemistry research as [[inducer]]s 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.<ref>{{cite journal | vauthors = Saez E, Nelson MC, Eshelman B, Banayo E, Koder A, Cho GJ, Evans RM | title = Identification of ligands and coligands for the ecdysone-regulated gene switch | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 97 | issue = 26 | pages = 14512–7 | date = December 2000 | pmid = 11114195 | pmc = 18950 | doi = 10.1073/pnas.260499497 | url = http://www.pnas.org/cgi/reprint/97/26/14512.pdf | bibcode = 2000PNAS...9714512S | doi-access = free }}</ref>

In 2024, the [[Food and Drug Administration]] approved a study on the efficacy of BIO101 (20-hydroxyecdysone) in treating [[obesity]], focusing on muscle strength improvement in the [[lower limb]]s.<ref>{{Cite web |last=Sharma |first=Soumya |date=2024-07-12 |title=FDA approves Biophytis' Phase II OBA obesity study |url=https://www.clinicaltrialsarena.com/news/us-fda-biophytis-obesity-study/ |access-date=2024-07-13 |website=Clinical Trials Arena |language=en-US}}</ref>

==External links==

* [https://ecdybase.org/ Ecdybase], The Ecdysone Handbook - a free online ecdysteroids database

== References ==

{{reflist}}

{{DEFAULTSORT:Hydroxyecdysone, 20-}}

[[Category:Insect hormones]]

[[Category:Primary alcohols]]

[[Category:Sterols]]

[[Category:Tertiary alcohols]]