Abstract
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 heptatria-contane. Dose–response data showed ED50 at 5 μg 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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Carlson, D. A., and Langley, P. A. 1986. Tsetse alkenes: Appearance of novel sex–specific compounds as an effect of mating. J. Insect Physiol. 32:781–790.
Carlson, D. A., Langley, P. A., and Huyton, P. M. 1978. Sex pheromone of the tsetse fly: Isolation, identification and synthesis of contact aphrodisiacs. Science 201:750–753.
Carlson, D. A., Nelson, D. R., Langley, P. A., Coates, T. W., Davis, T. L., and Leegwater–Vander Linden, M. 1984. Contact sex pheromone in the tsetse fly Glossina pallidipes (Austen): Identification and synthesis. J. Chem. Ecol. 10:429–450.
Carlson, D. A., Milstrey, S. K., and Narang, S. K. 1993. Genetic classification of the tsetse flies using cuticular hydrocarbons. Bull. Entomol. Soc. 83:507–515.
El Messoussi, S. 1988. Mise en evidence et caracterisation d'une pheromone aphrodisiaque de l'espece Glossina tachinoides (Diptera: Glossinidae). These de Diplome de Doctorat. Université de Paris VII.
El Messoussi, S, Wicker, C., Arienti, M., Carlson, D. A., and Jallon, J.–M. 1994. Hydrocarbons in species recognition of insects, pp. 277–287, in D. L. Hawksworth (ed.). The Identification and Characterization of Pest Organisms. CAB International, Wallingford, UK.
Eitre, L. S. 1964. The Kovats retention index system. Anal. Chem. 36:31A–40A.
Huyton, P. M., Langley, P. A., Carlson, D. A., and Schwartz, M. 1980. Specificity of contact sex pheromones in tsetse flies, Glossina spp. Physiol. Entomol. 5:253–264.
Kuwahara, K., and Mori, K. 1983. Synthesis of all three stereoisomers of 13,23–dimethylpentatriacontane, the sex pheromone of the tsetse fly, Glossina pallidipes. Agric. Biol. Chem. 47:2599–2606.
Langley, P. A., Pimley, R. W., and Carlson, D. A. 1975. Sex recognition pheromone in the tsetse fly, Glossina morsitans. Nature 254:51–53.
Langley, P. A., Huyton, P. M., and Carlson, D. A. 1987. Sex pheromone perception by males of the tsetse fly, Glossina morsitans. J. Insect Physiol. 33:981–986.
Matsuyama, K., and Mori, K. 1994. Synthesis of a stereoisomeric mixture of 13,25–, 11,21–and 11,23–dimethylheptatriacontane, the contact sex pheromone of the tsetse fly, Glossina tachinoides. Biotechnol. Biochem. 58:539–543.
McDowell, P. G., Hassanali, A., and Dransfield, R. 1985. Activity of the diastereomers of 13,23–dimethylpentatriacontane, the sex pheromone of Glossina pallidipes, and comparison with the natural pheromone. Physiol. Entomol. 10:183–190.
Nelson, D. R., and Carlson, D. A. 1986. Cuticular hydrocarbons of the tsetse flies Glossina morsitans, G. austeni and G. pallidipes. Insect Biochem. 16:403–416.
Nelson, D. R., Carlson, D. A., and Fatland, C. L. 1988. Cuticular hydrocarbons of the tsetse flies, II: G. p. palpalis, G. p. gambiensis, G. fuscipes, G. tachinoides, and G. brevipalpis. J. Chem. Ecol. 14:963–987.
Offor, I. I., Carlson, D. A., Gadzama, N. M., and Bozimo, H. T. 1981. Sex recognition pheromone in the West African tsetse fly, Glossina palpalis palpalis (Robineau–Desvoides) Insect Sci. Appl. 1:417–420.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Carlson, D.A., Offor, I.I., El Messoussi, S. et al. Sex Pheromone of Glossina tachinoides: Isolation, Identification, and Synthesis. J Chem Ecol 24, 1563–1575 (1998). https://doi.org/10.1023/A:1020967918594
Issue Date:
DOI: https://doi.org/10.1023/A:1020967918594