Ecdysone

{{Short description|Precursor of an insect hormone}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 461092187

| ImageFile = Ecdysone.svg

| ImageClass = skin-invert

| ImageSize = 240

| ImageAlt = Skeletal formula of ecdysone

| ImageFile1 = Ecdysone 3D ball.png

| ImageSize1 = 240

| ImageAlt1 = Ball-and-stick model of the ecdysone molecule

| IUPACName = (22R)-2β,3β,14α,22,25-Pentahydroxy-5β-cholest-7-en-6-one

| SystematicName = (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

| OtherNames =

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 18130

| 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

| InChIKey = UPEZCKBFRMILAV-JMZLNJERBR

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UPEZCKBFRMILAV-JMZLNJERSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 3604-87-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RH692X7B7B

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 549300

| PubChem = 19212

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16688

| 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

}}

| Section2 = {{Chembox Properties

| Formula = C₂₇H₄₄O₆

| MolarMass = 464.63 g/mol

| Appearance =

| Density =

| MeltingPt =

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| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

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Ecdysone is a{{clarify|reason=the?|date=October 2022}} 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.{{cite journal | id=Physiologisch-Chemisches Institut der Universität Marburg/Lahn | volume=20 | pages=130–133 | first3=Helmut | last3=Ammon | first2=Clemens | first1=Hans | last2=Rufer | last1=Hoffmeister | journal=Zeitschrift für Naturforschung B | date=February 1, 1965 | pmid=14345159 | doi=10.1515/znb-1965-0207 | title=Ausscheidung von Ecdyson bei Insekten | issue=2 | s2cid=95079385 | trans-title=Excretion of Ecdysone by Insects| doi-access=free }}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 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.{{cite journal |doi=10.7554/eLife.26287 |pmid=28394252 |pmc=5403213 |title=Steroid hormone induction of temporal gene expression in Drosophila brain neuroblasts generates neuronal and glial diversity |journal=eLife |volume=6 |year=2017 |last1=Syed |first1=Mubarak Hussain |last2=Mark |first2=Brandon |last3=Doe |first3=Chris Q. |doi-access=free }}

Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects.{{ cite journal | vauthors = Dinan L, Savchenko T, Whiting P | title = On the distribution of phytoecdysteroids in plants | journal = Cellular and Molecular Life Sciences | year = 2001 | volume = 58 | issue = 8 | pages = 1121–1132 | doi = 10.1007/PL00000926 | pmid = 11529504 | pmc = 11337386 | s2cid = 8496934 }} 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 propertiesWang YS, Yang JH, Luo SD, Zhang HB, Li L, [https://www.mdpi.org/molecules/papers/12030536.pdf New Cytotoxic Steroid from Stachyurus himalaicus var. himalaicus]. Molecules. 2007;12(3):536-42 as well as antioxidant properties on lipid peroxidation.{{cite journal | vauthors = Kuzmenko AI, Niki E, Noguchi N | title = New functions of 20-hydroxyecdysone in lipid peroxidation | journal = Journal of Oleo Science | volume = 50 | issue = 6 | pages = 497–506 | year = 2001 | doi = 10.5650/jos.50.497 | url = https://www.jstage.jst.go.jp/article/jos/50/6/50_6_497/_pdf | doi-access = free }}

Tebufenozide, sold under the Bayer trademark MIMIC,[https://apvma.gov.au/node/14051 apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"] has ecdysteroid activity although it bears little resemblance to the ecdysteroids.{{Cite book | doi = 10.1021/bk-2000-0767.ch002 | chapter = Tebufenozide: A Novel Caterpillar Control Agent with Unusually High Target Selectivity | title = Green Chemical Syntheses and Processes | series = ACS Symposium Series | date = 2000 | last1 = Carlson | first1 = Glenn R. | volume = 767 | pages = 8–17 | isbn = 978-0-8412-3678-3 }}