20-Hydroxyecdysone

Biological Activity

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. 20-Hydroxyecdysone is also found most abundantly in plant species and has anabolic effects in vertebrates, i.e. increasing muscle size without androgen influence. 20-Hydroxyecdysone is produced from ecdysone (E) by the action of a P450 monooxygenase that hydroxylates E at carbon 20. When shade (shd, Drosophila P450 enzyme) is transfected into Drosophila S2 cells, extensive conversion of ecdysone (E) to 20-Hydroxyecdysone is observed. 20-Hydroxyecdysone regulates gene expression by binding to a nuclear receptor heterodimer, consisting of the ecdysone receptor (EcR) and ultraspiracle proteins (USP), which are orthologs of the vertebrate LXR and RXR receptors, respectively. Genes regulated by 20-Hydroxyecdysone, and dependent on EcR, account for many transcripts that are significantly up- or downregulated at puparium formation. 20-Hydroxyecdysone plays a key role in insect development, cell proliferaton, growth and apoptosis by controlling gene expression. 20-Hydroxyecdysone may protect PC12 cells against CoCl2-induced cell injury by inhibiting ROS production and modulating components of the mitochondrial apoptosis pathway. Many genes regulated by 20-Hydroxyecdysone in Kc167 cells are not regulated by 20-Hydroxyecdysone in salivary glands of wandering 3rd instar larvae, and 20-Hydroxyecdysone-induced levels of EcR isoforms EcR-RA, ER-RC, and EcR-RD/E differ between Kc cells and salivary glands suggesting a possible cause for the observed differences in 20-Hydroxyecdysone-regulated gene transcription between the two cell types. 20-Hydroxyecdysone is a potential fibrosis antagonist for renal proximal tubule cells through suppressing post-receptor signaling of TGF-β1 and restoring tubule epithelial character by blocking the expression of Snail.

Product Citations

• 

  BMC Biol. 2024 Mar 6;22(1):54.

  A CTL − Lys immune function maintains insect metamorphosis by preventing gut bacterial dysbiosis and limiting opportunistic infections
  20-Hydroxyecdysone purchased from AbMole

Chemical Information

Molecular Weight	480.63
Formula	C27H44O7
CAS Number	5289-74-7
Solubility (25°C)	DMSO 76 mg/mL
Storage	-20°C, protect from light, sealed

Conversion of different model animals based on BSA (PMID: 27057123)

Species	Mouse	Rat	Rabbit	Guinea pig	Hamster	Dog
Weight (kg)	0.02	0.15	1.8	0.4	0.08	10
Body Surface Area (m2)	0.007	0.025	0.15	0.05	0.02	0.5
Km factor	3	6	12	8	5	20

Animal A (mg/kg) = Animal B (mg/kg) multiplied by	Animal B Km
	Animal A Km

For example, to modify the dose of Compound A used for a mouse (20 mg/kg) to a dose based on the BSA for a rat, multiply 20 mg/kg by the K_m factor for a mouse and then divide by the K_m factor for a rat. This calculation results in a rat equivalent dose for Compound A of 10 mg/kg.

References

[1] Suning Liu, et al. Proc Natl Acad Sci U S A. Antagonistic actions of juvenile hormone and 20-hydroxyecdysone within the ring gland determine developmental transitions in Drosophila

[2] Xiao-Fan Zhao. G protein-coupled receptors function as cell membrane receptors for the steroid hormone 20-hydroxyecdysone

[3] Xiaoli Jin, et al. 20-Hydroxyecdysone-responsive microRNAs of insects

[4] Jariya Buniam, et al. 20-Hydroxyecdysone ameliorates metabolic and cardiovascular dysfunction in high-fat-high-fructose-fed ovariectomized rats

[5] Eduard Isenmann, et al. Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans

[6] V V Volodin, et al. [20-Hydroxyecdysone--plant adaptogen: an anabolic effect, possible use in sports nutrition]