Long chain electrophilic contact poisons from the Dufours…来自的长链亲电接触毒药.pdfVIP

Long chain electrophilic contact poisons from the Dufours gland of the ant Crematogaster scutellaris (Hymenoptera, Myrmicinae) D. DALOZE,J. C. BRAEKMAN,P. VANHECKE,J. L. BOEVB,AND J. M. PASTEELS Collectifde Bio-ecologie, Faculte des Sciences, C.P. 160, UniversiteLibre de Bruxelles, Av. F. D. Roosevelt 50, B - 1050 Bruxelles, Belgium Received July 25, 1986 D. DALOZE,J. C. BRAEKMAN,P. VANHECKE,J. L. BOEVB,and J. M. PASTEELS.Can. J. Chem. 65,432 (1987). The Dufours gland secretion of C. scutellaris contains a series of C23long chain derivatives characterized by the presence of a cross-conjugated dienone linked to either a primary acetate, an aldehyde, or a carboxylic acid function. These compounds 6 further differ from each other by the degree of unsaturation and (or) the position of an isolated double bond in the carbon atom 1 chain. A combination of spectroscopic data and chemical degradations led to structures la-c, 2a-c, and 5a-c for the major / 5 2 components of the secretion. The highly electrophilic character of these compounds accounts for their efficiency as contact / 2 poisons. 0 n o B D. DALOZE,J. C. BRAEKMAN,P. VANHECKE,J. L. BOEVBet J. M. PASTEELS.Can. J. Chem. 65,432 (1987). I L La dcrttion de la glande de Dufour de C. scutellaris contient une strie de dCrivCs a longue ch