Sex pheromone of Glossina tachinoides: isolation, identification, and synthesis
1998
Carlson, D.A. | Offor, I.I. | El Messoussi, S. | Matsuyama, K. | Mori, K. | Jallon, J.M.
Study of lipids from male and female laboratory-reared flies led to the demonstration of a potent contact sex stimulant in extracts and cuticular hydrocarbons of the female tsetse fly Glossina tachinoides (Westwood) against conspecific males. Thin-layer and column chromatography indicated that extracts contained hydrocarbons and saponifiable lipids. Biological activity was found in the alkanes from females, including prominent branched-chain alkanes that were detected by gas chromatography (GC). The alkanes were separated and collected by preparative gas chromatography (GC), and only the 37-carbon region showed biological activity. GC-mass spectrometry showed the major peak contained a mixture of isomeric 11,23-, 13,25- plus a minor amount of 11,21-dimethylheptatriacontane. Two racemic isomers were synthesized, and bioassays showed that the greatest activity was possessed by the 11,23- isomer with somewhat less activity in 13,25-dimethyl heptatriacontane. Dose-response data showed ED50 at 5 micrograms per decoy with solvent-washed males, nonspecific females, or corks as decoys. These alkanes released sexual activity in males that comprised most of the behaviors released by a female fly of the same species.
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