20-Hydroxyecdysone

Chemical compound June 2025 vanc 6 changed 477215829 (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one 20-Hydroxyecdysone.svg skin-invert-image Skeletal formula of 20-hydroxyecdysone 260 20-Hydroxyecdysone 3D ball.png bg-transparent Ball-and-stick model of the 20-hydroxyecdysone molecule unknown OTC Not a regulated substance in general Oral HepaticJune 2025 4-9 hoursJune 2025 BIO101, Ecdysterone changed ?? 5289-74-7 correct FDA 779A7KPL0Y 5459840 correct drugbank correct chemspider 4573597 correct EBI 16587 correct EBI 224128 27 44 7 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 correct chemspider 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 correct chemspider 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. Also 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. Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK 163166547 Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans Archives of Toxicology 93 7 1807–1816 July 2019 31123801 10.1007/s00204-019-02490-x 2019ArTox..93.1807I free 11573/1291269 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. Thummel CS, Chory J Steroid signaling in plants and insects--common themes, different pathways Genes & Development 16 24 3113–29 December 2002 12502734 10.1101/gad.1042102 http://www.genesdev.org/cgi/reprint/16/24/3113 free 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. Handler AM Ecdysteroid titers during pupal and adult development in Drosophila melanogaster Developmental Biology 93 1 73–82 September 1982 6813165 10.1016/0012-1606(82)90240-8 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.September 2024 Ecdysteroid activity in arthropods In insects, an ecdysteroid is a type of steroid hormone derived from enzymatic modification of cholesterol by p450 enzymes. Kamiyama T, Niwa R Transcriptional Regulators of Ecdysteroid Biosynthetic Enzymes and Their Roles in Insect Development Frontiers in Physiology 13 823418 2022 35211033 8863297 10.3389/fphys.2022.823418 free 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. Riddiford LM, Cherbas P, Truman JW Ecdysone receptors and their biological actions 60 1–73 2000 11037621 10.1016/S0083-6729(00)60016-X 978-0-12-709860-9 Vitamins & Hormones 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. Saez E, Nelson MC, Eshelman B, Banayo E, Koder A, Cho GJ, Evans RM Identification of ligands and coligands for the ecdysone-regulated gene switch Proceedings of the National Academy of Sciences of the United States of America 97 26 14512–7 December 2000 11114195 18950 10.1073/pnas.260499497 http://www.pnas.org/cgi/reprint/97/26/14512.pdf 2000PNAS...9714512S free 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. Cohen PA, Sharfstein J, Kamugisha A, Vanhee C Analysis of Ingredients of Supplements in the National Institutes of Health Supplement Database Marketed as Containing a Novel Alternative to Anabolic Steroids JAMA Network Open 3 4 e202818 April 2020 32293681 10.1001/jamanetworkopen.2020.2818 free 7160690 Although a number of early studies supported the anabolic effects of 20-hydroxyecdysone, Simakin SY The Combined Use of Ecdisten and the Product'Bodrost'during Training in Cyclical Types of Sport. Scientific Sports Bulletin 1988 2 Gadzhieva RM, Portugalov SN, Paniushkin VV, Kondrat'eva II [A comparative study of the anabolic action of ecdysten, leveton and Prime Plus, preparations of plant origin.] Eksperimental'naia i Klinicheskaia Farmakologiia 1995 58 5 46–8 8704590 Báthori M, Tóth N, Hunyadi A, Márki A, Zádor E Phytoecdysteroids and anabolic-androgenic steroids--structure and effects on humans Current Medicinal Chemistry 15 1 75–91 2008 18220764 10.2174/092986708783330674 http://publicatio.bibl.u-szeged.hu/10883/1/2008_Bathori_et_al._CMC_u.pdf Smetanin BY The influence of preparations of plant origin on physical work capacity. The Russian Ministry of Public Health 1986 Fadeev BG Comments on the Results of Retibol in the Practice of Athletic Training and Rehabilitation Natural Sports Research Institute Azizov AP, Seĭfulla RD, Ankudinova IA, Kondrat'eva II, Borisova IG [The effect of the antioxidants elton and leveton on the physical work capacity of athletes] ru Eksperimental'naia i Klinicheskaia Farmakologiia 61 1 60–2 1998 9575416 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. Wilborn CD, Taylor LW, Campbell BI, Kerksick C, Rasmussen CJ, Greenwood M, Kreider RB Effects of methoxyisoflavone, ecdysterone, and sulfo-polysaccharide supplementation on training adaptations in resistance-trained males Journal of the International Society of Sports Nutrition 3 2 19–27 December 2006 19 18500969 2129166 10.1186/1550-2783-3-2-19 free 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. Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, Kazlauskas R, Goebel C, Botrè F, Diel P, Parr MK 163166547 Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans Archives of Toxicology 93 7 1807–1816 July 2019 31123801 10.1007/s00204-019-02490-x 2019ArTox..93.1807I free 11573/1291269 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. Parr MK, Zhao P, Haupt O, Ngueu ST, Hengevoss J, Fritzemeier KH, Piechotta M, Schlörer N, Muhn P, Zheng WY, Xie MY, Diel P Estrogen receptor beta is involved in skeletal muscle hypertrophy induced by the phytoecdysteroid ecdysterone Molecular Nutrition & Food Research 58 9 1861–72 September 2014 24974955 10.1002/mnfr.201300806 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. Sharma S 2024-07-12 FDA approves Biophytis' Phase II OBA obesity study https://www.clinicaltrialsarena.com/news/us-fda-biophytis-obesity-study/ 2024-07-13 Clinical Trials Arena en-US References External links Ecdybase, The Ecdysone Handbook - a free online ecdysteroids database Category:Insect hormones Category:Primary alcohols Category:Sterols Category:Tertiary alcohols