Hydroxyecdysone

Description

20-Hydroxyecdysone (also known as Ecdysterone) is a hormone-like substance widely found in animals and plants, with a steroid ring at the core of its structure. It has the function of promoting arthropod molting and protecting plants from insects. Studies have shown that when used as a supplement, ecdysterone has a positive effect on human measurements and performance parameters, and is included in the World Anti-Doping Agency's banned list, but it has recently been found that there is a lack of scientific evidence to support WADA's ban on this substance.

Chemical Properties

White or off-white powder, odorless, hygroscopic, the color gradually becomes darker when exposed to light. Soluble in ethanol, slightly soluble in acetone, slightly soluble in hot water, ethyl acetate, chloroform, almost insoluble in ether, derived from Leulu, Achyranthes bidentata, Cyanotis, arachnoidea, Pfaffia glomerata.

Uses

20-Hydroxyecdysone has been used:
in Leibovitz′s dissecting medium for culturing sorting zone and neuropil-associated glia and antennal lobes of Manduca sexta
in Schneider′s medium to reproduce ex-vivo imaginal disc eversion
as a supplement in Mcl8 medium for culturing Drosophila wing imaginal discs
as an insect molting hormone

Definition

ChEBI: 20-hydroxyecdysone is an ecdysteroid that is ecdysone substituted by a hydroxy group at position 20. It has a role as a plant metabolite and an animal metabolite. It is a 20-hydroxy steroid, an ecdysteroid, a 14alpha-hydroxy steroid, a 3beta-sterol, a 2beta-hydroxy steroid, a 22-hydroxy steroid, a 25-hydroxy steroid and a phytoecdysteroid. It is functionally related to an ecdysone.

Biochem/physiol Actions

20-Hydroxyecdysone is an ecdysteroid hormone that plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression involved in molting and metamorphosis. It acts through a heterodimeric receptor comprising the ecdysone receptor and the ultraspiracle proteins (USP).

storage

+4°C

Purification Methods

Crystallise -ecdyson from water, tetrahydrofuran/pet ether, MeOH and EtOAc after chromatographic purification. It has max (EtOH) at 240nm ( 12,670 M-1cm-1). [Also IR & NMR: Hüppi & Siddall J Am Chem Soc 89 6799 1967, Kametani et al. Tetrahedron Lett 21 4855 1980, Beilstein 8 IV 343.]