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

Meinwald, J; Huang, Q; Vrkoc, J; Herath, K B; Yang, Z C; Schröder, F; Attygalle, A B; Iyengar, V K et al. · Proc Natl Acad Sci U S A · 1998

basic_science · Level V

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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.

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