Article · Wikipedia archive · Last revised Jun 11, 2026

Ecdysone

Ecdysone is the prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones 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. It causes chromosome puffs 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.

Last revised
Jun 11, 2026
Read time
≈ 3 min
Length
676 w
Citations
14
Source
Wikipedia ↗
Ecdysone
Skeletal formula of ecdysone
source ↗
Ball-and-stick model of the ecdysone molecule
source ↗
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
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 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 the 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.23 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

Ecdysone turns into 20-hydroxyecdysone by the activity of ecdysone 20-monooxygenase,5 which requires molecular oxygen and a reduced hydrogen acceptor (NADPH678).5

Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects.9 Some phytoecdysteroids may be bioactive in human contexts such as n ecdysteroid precursor from Stachyurus himalaicus, which exhibits cytotoxicity 10 Ecdysones from insects have also exhibited antioxidant properties on lipid peroxidation.11 Ecdysteroids are also found in the purport adaptogen Cordyceps militaris .

Tebufenozide, sold under the Bayer trademark MIMIC,12 has ecdysteroid activity although it bears little resemblance to the ecdysteroids.13

See also

See also

References

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. "KEGG PATHWAY: Insect hormone biosynthesis - Reference pathway". www.kegg.jp. Retrieved 2026-05-05.
  6. Johnson, P; Rees, H H (1977-12-15). "The mechanism of C-20 hydroxylation of α-ecdysone in the desert locust, Schistocerca gregaria". Biochemical Journal. 168 (3): 513–520. doi:10.1042/bj1680513. ISSN 0264-6021. PMC 1183799. PMID 606249.
  7. Nigg, H. N.; Svoboda, J. A.; Thompson, M. J.; Dutky, S. R.; Kaplanis, J. N.; Robbins, W. E. (1976-04-01). "Ecdysone 20-hydroxylase from the midgut of the tobacco hornworm (Manduca sexta L.)". Experientia. 32 (4): 438–439. doi:10.1007/BF01920781. ISSN 0014-4754.
  8. Lee Smith, Stan; Bollenbacher, Walter E.; Cooper, David Y.; Schleyer, Heinz; Wielgus, John J.; Gilbert, Lawrence I. (1979-09-01). "Ecdysone 20-monooxygenase: Characterization of an insect cytochrome P-450 dependent steroid hydroxylase". Molecular and Cellular Endocrinology. 15 (3): 111–133. doi:10.1016/0303-7207(79)90033-9. ISSN 0303-7207.
  9. 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.
  10. Wang YS, Yang JH, Luo SD, Zhang HB, Li L, New Cytotoxic Steroid from Stachyurus himalaicus var. himalaicus. Molecules. 2007;12(3):536-42
  11. 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.
  12. apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"
  13. 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