title: Mirasorvone: a masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus).
abstract: The sunburst diving beetle, Thermonectus marmoratus, ejects a milky fluid from its prothoracic defensive glands when disturbed. Two major volatile components of this secretion are steroids; cybisterone (structure 7) constitutes about 20% of the volatiles, and a new steroid, mirasorvone, about 50%. Mirasorvone is assigned an 18-oxygenated pregnane structure (structure 9) on the basis of extensive spectroscopic data. Although no 18-oxygenated steroid has been described previously from an insect source, a closely related hormone with mineralocorticoid activity, 18-hydroxydeoxycorticosterone (structure 13), has been isolated from the adrenal glands of rats.
authors.affiliation: Department of Chemistry, Cornell University, Ithaca, NY 14853, USA.
authors.forename: J
authors.initials: J
authors.lastname: Meinwald
authors.forename: Q
authors.initials: Q
authors.lastname: Huang
authors.forename: J
authors.initials: J
authors.lastname: Vrkoc
authors.forename: K B
authors.initials: KB
authors.lastname: Herath
authors.forename: Z C
authors.initials: ZC
authors.lastname: Yang
authors.forename: F
authors.initials: F
authors.lastname: Schröder
authors.forename: A B
authors.initials: AB
authors.lastname: Attygalle
authors.forename: V K
authors.initials: VK
authors.lastname: Iyengar
authors.forename: R C
authors.initials: RC
authors.lastname: Morgan
authors.forename: T
authors.initials: T
authors.lastname: Eisner
mesh_terms: D000818:Animals; D001522:Behavior, Animal; D012634:Bodily Secretions / Q000737:chemistry; D001517:Coleoptera / Q000737:chemistry*; D003900:Desoxycorticosterone / Q000031:analogs & derivatives; D008401:Gas Chromatography-Mass Spectrometry; D011278:Pregnanes / Q000737:chemistry*
chemical_list: D011278:Pregnanes; C111233:mirasorvone; C042509:18-hydroxydeoxycorticosterone; D003900:Desoxycorticosterone