Defensive Steroids from a Carrion Beetle (Silpha Americana)

Overview

Journal Experientia

Specialty Science

Date 1985 Apr 15

PMID 3987876

Citations 8

Authors

J Meinwald

B Roach

K Hicks

D Alsop

T Eisner

Affiliations

Soon will be listed here.

Abstract

The defensive anal effluent discharged by Silpha americana in response to disturbance contains a mixture of steroids stemming from a glandular annex of the rectum. The compounds have been characterized as 15 beta-hydroxyprogesterone (1, principal component), 5 beta-pregnan-15 beta-ol-3,20-dione (2), 5 beta-pregnan-3 alpha, 15 beta-diol-20-one (3), 5 beta-pregnan-7 beta, 15 beta-diol-3,20-dione (4), 5 beta-pregnan-3 alpha, 7 beta, 15 beta-triol-20-one (5), 5 beta-pregnan-16 alpha-ol-3,20-dione (6), and 5 beta-pregnan-3 alpha, 16 alpha-diol-20-one (7), none previously found in insects. Bioassays with jumping spiders showed compounds 1 and 6 to be feeding deterrents at the 1 microgram level.

Citing Articles

Defensive steroids from a carrion beetle (Silpha novaboracensis).

Meinwald J, Roach B, Eisner T J Chem Ecol. 2013; 13(1):35-8.

PMID: 24301357 DOI: 10.1007/BF01020349.

Secondary metabolites released by the burying beetle Nicrophorus vespilloides: chemical analyses and possible ecological functions.

Degenkolb T, During R, Vilcinskas A J Chem Ecol. 2011; 37(7):724-35.

PMID: 21667150 DOI: 10.1007/s10886-011-9978-4.

Ethyl 4-methyl heptanoate: a male-produced pheromone of Nicrophorus vespilloides.

Haberer W, Schmitt T, Peschke K, Schreier P, Muller J J Chem Ecol. 2007; 34(1):94-8.

PMID: 18080163 DOI: 10.1007/s10886-007-9406-y.

Presence of immunoreactive corticotropin-releasing hormone and cortisol molecules in invertebrate haemocytes and lower and higher vertebrate thymus.

Ottaviani E, Franchini A, Franceschi C Histochem J. 1999; 30(2):61-7.

PMID: 10192545 DOI: 10.1023/a:1003270614163.

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

Meinwald J, Huang Q, Vrkoc J, Herath K, Yang Z, Schroder F Proc Natl Acad Sci U S A. 1998; 95(6):2733-7.

PMID: 9501158 PMC: 19637. DOI: 10.1073/pnas.95.6.2733.

References

Eisner T, Wiemer D, Haynes L, Meinwald J . Lucibufagins: Defensive steroids from the fireflies Photinus ignitus and P. marginellus (Coleoptera: Lampyridae). Proc Natl Acad Sci U S A. 1978; 75(2):905-8. PMC: 411366. DOI: 10.1073/pnas.75.2.905. View

Eisner T, Hill D, Goetz M, Jain S, Alsop D, Camazine S . Antifeedant action ofZ-dihydromatricaria acid from soldier beetles (Chauliognathus spp.). J Chem Ecol. 2014; 7(6):1149-58. DOI: 10.1007/BF00987634. View

Pasteels J, Daloze D . Cardiac glycosides in the defensive secretion of chrysomelid beetles: evidence for their production by the insects. Science. 1977; 197(4298):70-2. DOI: 10.1126/science.867051. View