Ecdysone

Last updated
Ecdysone
Ecdysone.svg
Ecdysone 3D ball.png
Names
IUPAC name
(22R)-2β,3β,14α,22,25-Pentahydroxy-5β-cholest-7-en-6-one
Systematic IUPAC name
(1R,3aS,5aR,7R,8S,9aR,9bR,11aR)-1-[(2S,3R)-3,6-Dihydroxy-6-methylheptan-2-yl]-3a,7,8-trihydroxy-9a,11a-dimethyl-1,2,3,3a,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-5H-cyclopenta[a]phenanthren-5-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.692 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: UPEZCKBFRMILAV-JMZLNJERSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ecdysone is a[ clarification needed ] prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. [1] It is of steroidal structure. 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. [2] [3] In Drosophila melanogaster , an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires. 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. [4]

Contents

Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. [5] Some phytoecdysteroids may be bioactive in human contexts such as n ecdysteroid precursor from Stachyurus himalaicus , which exhibits cytotoxicity [6] Ecdysones from insects have also exhibited antioxidant properties on lipid peroxidation. [7] . Ecdysteroids are also found in the purport adaptogen Cordyceps militaris [ citation needed ].

Tebufenozide, sold under the Bayer trademark MIMIC, [8] has ecdysteroid activity although it bears little resemblance to the ecdysteroids. [9]

See also

References

  1. ↑ Ishimoto, Hiroshi; Kitamoto, Toshihiro (May 2010). The steroid molting hormone Ecdysone regulates sleep in adult Drosophila melanogaster. pp. 269–281.
  2. ↑ Hoffmeister, Hans; Rufer, Clemens; Ammon, Helmut (February 1, 1965). "Ausscheidung von Ecdyson bei Insekten" [Excretion of Ecdysone by Insects]. Zeitschrift für Naturforschung B. 20 (2): 130–133. doi: 10.1515/znb-1965-0207 . PMID   14345159. S2CID   95079385. Physiologisch-Chemisches Institut der Universität Marburg/Lahn.
  3. ↑ Karlson, P; Hoffmeister, H (March, 1963). On the biogenesis of ecdyson. I. Conversion of cholesterol into ecdyson. Hoppe Seylers Z Physiol Chem., 331, 289–300. In German. PMID 1396254
  4. ↑ Syed, Mubarak Hussain; Mark, Brandon; Doe, Chris Q. (2017). "Steroid hormone induction of temporal gene expression in Drosophila brain neuroblasts generates neuronal and glial diversity". eLife. 6. doi: 10.7554/eLife.26287 . PMC   5403213 . PMID   28394252.
  5. ↑ 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. PMC   11337386 . PMID   11529504. S2CID   8496934.
  6. ↑ Wang YS, Yang JH, Luo SD, Zhang HB, Li L, New Cytotoxic Steroid from Stachyurus himalaicus var. himalaicus. Molecules. 2007;12(3):536-42
  7. ↑ Kuzmenko AI, Niki E, Noguchi N (2001). "New functions of 20-hydroxyecdysone in lipid peroxidation". Journal of Oleo Science. 50 (6): 497–506. doi: 10.5650/jos.50.497 .
  8. ↑ apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"
  9. ↑ Carlson, Glenn R. (2000). "Tebufenozide: A Novel Caterpillar Control Agent with Unusually High Target Selectivity". Green Chemical Syntheses and Processes. ACS Symposium Series. Vol. 767. pp. 8–17. doi:10.1021/bk-2000-0767.ch002. ISBN   978-0-8412-3678-3.
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