MIRASORVONE - A MASKED 20-KETOPREGNANE FROM THE DEFENSIVE SECRETION OF A DIVING BEETLE (THERMONECTUS-MARMORATUS)

Authors
MEINWALD J HUANG Q VRKOC J HERATH KB YANG ZC SCHRODER F ATTYGALLE AB IYENGAR VK MORGAN RC EISNER T
Citation
J. Meinwald et al., MIRASORVONE - A MASKED 20-KETOPREGNANE FROM THE DEFENSIVE SECRETION OF A DIVING BEETLE (THERMONECTUS-MARMORATUS), Proceedings of the National Academy of Sciences of the United Statesof America, 95(6), 1998, pp. 2733-2737
Citations number
22
Categorie Soggetti
Multidisciplinary Sciences
Journal title
Proceedings of the National Academy of Sciences of the United Statesof America → ACNP
ISSN journal
00278424
Volume
95
Issue
6
Year of publication
1998
Pages
2733 - 2737
Database
ISI
SICI code
0027-8424(1998)95:6<2733:M-AM2F>2.0.ZU;2-J
Abstract
The sunburst diving beetle, Thermonectus marmoratus, ejects a milky fl uid from its prothoracic defensive glands when disturbed. Two major vo latile components of this secretion are steroids; cybisterone (structu re 7) constitutes about 20% of the volatiles, and a new steroid, miras orvone, about 50%. Mirasorvone is assigned an 18-oxygenated pregnane s tructure (structure 9) an the basis of extensive spectroscopic data. A lthough no 18-oxygenated steroid has been described previously from an insect source, a closely related hormone with mineralocorticoid activ ity, 18-hydroxydeoxycorticosterone (structure 13), has been isolated f rom the adrenal glands of rats.