Mirasorvone: a masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus).
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.
Meinwald
J
J
Department of Chemistry, Cornell University, Ithaca, NY 14853, USA.
Huang
Q
Q
Vrkoc
J
J
Herath
K B
KB
Yang
Z C
ZC
Schröder
F
F
Attygalle
A B
AB
Iyengar
V K
VK
Morgan
R C
RC
Eisner
T
T
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*
D011278:Pregnanes; C111233:mirasorvone; C042509:18-hydroxydeoxycorticosterone; D003900:Desoxycorticosterone