Citation

Pasteels JM, Daloze D, Boeve JL. J. Chem. Ecol. 1989; 15(5): 1501-1511.

Affiliation

Laboratoire de Biologie Animale et Cellulaire, Université libre de Bruxelles-CP 160, Avenue F.D. Roosevelt 50, 1050, Brussels, Belgium.

Copyright

(Copyright © 1989, Holtzbrinck Springer Nature Publishing Group)

DOI

10.1007/BF01012379

PMID

24272094

Abstract

The Dufour gland ofCrematogaster scutellaris stores a mixture of long-chain primary acetates bearing a cross-conjugated dienone (Scheme 1, la-c). The poison gland contains two highly active enzymes: an acetate esterase and an alcohol oxidase. During venom emission, the constituents of both glands mix and accumulate on the sting, where the formation of the highly electrophilic aldehydes (Scheme 1, 2a-c) from their acetate precursors is initiated. Acetic acid, produced during the reaction, acts as alarm pheromone. The toxicity of the acetates (Scheme 1, la-c) and of the crude secretion has been assessed by topical application onMyrmica rubra. The acetatecontaining secretion from the Dufour gland was less toxic than the enzymatically altered secretion that was rich in aldehydes. The production of acids (Scheme 1, 3a-c) was an artifact resulting from the nonenzymatic oxidation of the unstable aldehydes.

Language: en