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Mirasorvone: A masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus)

By Jerrold Meinwald, Qing Huang, Jan Vrkoč, Kithsiri B. Herath, Zhi-Cai Yang, Frank Schröder, Athula B. Attygalle, Vikram K. Iyengar, Randy C. Morgan and Thomas Eisner

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

Topics: Physical Sciences
Publisher: The National Academy of Sciences
Year: 1998
OAI identifier: oai:pubmedcentral.nih.gov:19637
Provided by: PubMed Central
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