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

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

doi:10.1073/pnas.95.6.2733

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

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

Department of Chemistry and Chemical Biology

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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.

Original language	English
Pages (from-to)	2733-2737
Number of pages	5
Journal	Proceedings of the National Academy of Sciences of the United States of America
Volume	95
Issue number	6
DOIs	https://doi.org/10.1073/pnas.95.6.2733
State	Published - 17 Mar 1998

Keywords

Dytiscidae
Hemiketal
Steroids

Access to Document

10.1073/pnas.95.6.2733

Cite this

Meinwald, J., Huang, Q., Vrkoč, J., Herath, K. B., Yang, Z. C., Schröder, F., Attygalle, A. B., Iyengar, V. K., Morgan, R. C., & Eisner, T. (1998). 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 States of America, 95(6), 2733-2737. https://doi.org/10.1073/pnas.95.6.2733

@article{29ba6296581c41f4be59071f5f804839,

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

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.",

keywords = "Dytiscidae, Hemiketal, Steroids",

author = "Jerrold Meinwald and Qing Huang and Jan Vrko{\v c} and Herath, \{Kithsiri B.\} and Yang, \{Zhi Cai\} and Frank Schr{\"o}der and Attygalle, \{Athula B.\} and Iyengar, \{Vikram K.\} and Morgan, \{Randy C.\} and Thomas Eisner",

year = "1998",

month = mar,

day = "17",

doi = "10.1073/pnas.95.6.2733",

language = "English",

volume = "95",

pages = "2733--2737",

number = "6",

}

Meinwald, J, Huang, Q, Vrkoč, J, Herath, KB, Yang, ZC, Schröder, F, Attygalle, AB, Iyengar, VK, Morgan, RC & Eisner, T 1998, '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 States of America, vol. 95, no. 6, pp. 2733-2737. https://doi.org/10.1073/pnas.95.6.2733

TY - JOUR

T1 - Mirasorvone

T2 - A masked 20-ketopregnane from the defensive secretion of a diving beetle (Thermonectus marmoratus)

AU - Meinwald, Jerrold

AU - Huang, Qing

AU - Vrkoč, Jan

AU - Herath, Kithsiri B.

AU - Yang, Zhi Cai

AU - Schröder, Frank

AU - Attygalle, Athula B.

AU - Iyengar, Vikram K.

AU - Morgan, Randy C.

AU - Eisner, Thomas

PY - 1998/3/17

Y1 - 1998/3/17

N2 - 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.

AB - 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.

KW - Dytiscidae

KW - Hemiketal

KW - Steroids

UR - https://www.scopus.com/pages/publications/13144282734

UR - https://www.scopus.com/pages/publications/13144282734#tab=citedBy

U2 - 10.1073/pnas.95.6.2733

DO - 10.1073/pnas.95.6.2733

M3 - Article

C2 - 9501158

AN - SCOPUS:13144282734

SN - 0027-8424

VL - 95

SP - 2733

EP - 2737

JO - Proceedings of the National Academy of Sciences of the United States of America

JF - Proceedings of the National Academy of Sciences of the United States of America

IS - 6

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this