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Ecdysone

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Ecdysone
Skeletal formula of ecdysone
Ball-and-stick model of the ecdysone molecule
Names
IUPAC name
(22R)-2β,3β,14α,22,25-pentahydroxy-5β-cholest-7-en-6-one
Systematic 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.692 Edit this at Wikidata
  • 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 checkY
    Key: UPEZCKBFRMILAV-JMZLNJERSA-N checkY
  • 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
  • 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
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).
checkY verify (what is checkY☒N ?)

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 the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly.[1] Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects.[2]

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.[3]

Tebufenozide, sold under the Bayer trademark MIMIC,[4] has ecdysteroid activity although its chemical structure has little resemblance to the ecdysteroids.[citation needed]

See also

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

Notes

  1. ^ . doi:10.7554/eLife.26287. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)CS1 maint: unflagged free DOI (link)
  2. ^ Dinan L, Savchenko T, Whiting P (2001). "On the distribution of phytoecdysteroids in plants". Cellular and Molecular Life Sciences. 58 (8): 1121–1132. doi:10.1007/PL00000926. PMID 11529504.
  3. ^ Wang YS, Yang JH, Luo SD, Zhang HB, Li L, Molecules. 2007;12(3):536-42
  4. ^ apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"
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