7(Z),11(Z)-Pentacosadiene

Description

Unsaturated, long-chain hydrocarbons are found on the cuticles of insects and can act as pheromones. In mature Drosophila melanogaster, certain cuticular hydrocarbons are sexually dimorphic: males synthesize 23- and 25-C monoenes and females produce 27- and 29-C dienes. Each of these lipids plays specific roles in regulating male sexual behavior, with dienes stimulating courtship.¹ 7(Z),11(Z)-Pentacosadiene is a 25-C hydrocarbon that is found in low abundance on cuticles of mature Drosophila females.² Depletion of a female-specific elongase (eloF), which leads to an increase in 7(Z),11(Z)-pentacosadiene along with a parallel decrease in 7,11-nonacosadiene, significantly reduces copulation in Drosophila.³ This raises the possibility that 7(Z),11(Z)-pentacosadiene may act as an anti-aphrodisiac.

References

1. Ferveur, J.-F., and Sureau, G. Simultaneous influences on male courtship of stimulatory and inhibitory pheromones produced by live sex-mosaic Drosophila melanogaster Proc. Biol. Sci. 263(1373),967-973(1996).
2. Siwicki, K.K., Riccio, P., Ladewski, L., et al. The role of cuticular pheromones in courtship conditioning of Drosophila males Learn. Mem. 12(6),636-645(2005).
3. Chertemps, T., Duportets, L., Labuer, C., et al. A female-biased expressed elongase involved in long-chain hydrocarbon biosynthesis and courtship behavior in Drosophila melanogaster Proc. Natl. Acad. Sci. USA 104(11),4273-4278(2007).