TRICOSENE (7Z)

Description

7(Z)-Tricosene is an unsaturated cuticular hydrocarbon that acts as a pheromone in some insects, including Drosophila. While it is present in both sexes of some Drosophila species, it is abundant in males, but not females, of D. melanogaster and D. sechellia.¹ In these species, 7(Z)-tricosene prevents or reduces male courtship behavior² and increases female sexual receptivity.³ It is absent from virgin D. melanogaster females, but is transferred from males to females during mating.⁴ In addition, mating induces the synthesis of 7(Z)-tricosene by D. melanogaster females, so that it acts as an anti-aphrodisiac in mated females.⁴ 7(Z)-Tricosene is also a minor component of labial gland secretion and cuticle of Bombus spp.^5,6

Definition

ChEBI: (7Z)-tricosene is a tricosene in which the double bond at position 7 has cis-configuration. It has a role as a pheromone and an animal metabolite.

References

1. Coyne, J.A., Crittenden, A.P., and Mah, K. Genetics of a pheromonal difference contributing to reproductive isolation in drosophila Science 265,1461-1464(1994).
2. Svetec, N., and Ferveur, J.F. Social experience and phermonal perception can change male-male interactions in Drosophila melanogaster J. Exp. Biol. 208,891-898(2004).
3. Grillet, M., Dartevelle, L., and Ferveur, J.F. A Drosophila male pheromone affects female sexual receptivity Proc. Biol. Sci. 273,315-323(2006).
4. Scott, D. Sexual mimicry regulates the attractiveness of mated Drosophila melanogaster females Proc. Natl. Acad. Sci. USA 83,8429-8433(1986).
5. Valterová, I., Urbanová, K., Hovorka, O., et al. Composition of the labial gland secretion of the bumblebee males Bombus pomorum Z. Naturforsch. C J. Biosci. 56,430-436(2001).
6. Urbanová, K., Valterová, I., Hovorka, O., et al. Chemotaxonomical characterisation of males of Bombus lucorum (hymenoptera: Apidae) collected in the Czech Republic Eur. J. Entomol. 98,111-115(2001).