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1: Proc Natl Acad Sci U S A. 1998 Mar 17;95(6):2733-7.Click here to read Click here to read Links

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

Meinwald J, Huang Q, Vrkoc J, Herath KB, Yang ZC, Schröder F, Attygalle AB, Iyengar VK, Morgan RC, Eisner T.

Department of Chemistry, Cornell University, Ithaca, NY 14853, USA.

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.

PMID: 9501158 [PubMed - indexed for MEDLINE]

PMCID: PMC19637