Ecdysone

Ecdysone

Names
IUPAC name (2S,3R,5R,9R,10R,13R,14S,17R)-17- [(2S,3R)-3,6-dihydroxy-6-methylheptan- 2-yl]-2,3,14-trihydroxy-10,13-dimethyl- 2,3,4,5,9,11,12,15,16,17-decahydro- 1H-cyclopenta[a]phenanthren-6-one
Identifiers
CAS Number	3604-87-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16688 Y
ChemSpider	18130 Y
ECHA InfoCard	100.020.692
PubChem CID	19212
InChI InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1 Y Key: UPEZCKBFRMILAV-JMZLNJERSA-N Y InChI=1/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1 Key: UPEZCKBFRMILAV-JMZLNJERBR
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@H](C)[C@H](O)CCC(O)(C)C)C
Properties
Chemical formula	C27H44O6
Molar mass	464.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. In Drosophila melanogaster, an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in Chris Q. Doe lab have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells^[1]. Ecdysone Ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have been reputed to have medicinal value and are part of herbal adaptogenic remedies like Cordyceps, yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties.^[2] A pesticide sold with the name MIMIC has ecdysteroid activity, although its chemical structure has little resemblance to the ecdysteroids.

See also

• Ecdysone receptor
• PTTH - Metamorphosis Initiator hormone

External links

• Ecdybase, The Ecdysone Handbook - a free online ecdysteroids database

Notes

1. ↑ Syed, Mubarak Hussain; Mark, Brandon; Doe, Chris Q. (10 April 2017). "Steroid hormone induction of temporal gene expression in Drosophila brain neuroblasts generates neuronal and glial diversity". eLife. 6: e26287. ISSN 2050-084X. doi:10.7554/eLife.26287. 
2. ↑ Wang YS, Yang JH, Luo SD, Zhang HB, Li L, Molecules. 2007;12(3):536-42