Ecdysone
Precursor of an insect hormone
Ecdysone
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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.020.692
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
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
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
C27 H44 O6
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).
Chemical compound
Ecdysone is a[clarification needed ] prohormone of the major insect molting hormone 20-hydroxyecdysone , secreted from the prothoracic glands . 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.[ 1] [ 2] 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.[ 3]
Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants ) against herbivorous insects.[ 4] These phytoecdysteroids have been reputed to have medicinal value. They are part of herbal adaptogenic remedies like Cordyceps , yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties[ 5] as well as antioxidant properties on lipid peroxidation .[ 6]
Tebufenozide , sold under the Bayer trademark MIMIC,[ 7] has ecdysteroid activity although its chemical structure has little resemblance to the ecdysteroids.[ 8]
See also
References
^ 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.
^ 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
^ 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 .
^ 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 .
^ Wang YS, Yang JH, Luo SD, Zhang HB, Li L, Molecules. 2007;12(3):536-42
^ 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 .
^ apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"
^ 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 .
External links
Ecdybase , The Ecdysone Handbook - a free online ecdysteroids database