Musca domestica pheromone

One of the sex pheromone components of the housefly, Musca domestica, is Z9-21 H that is found on the cuticular surface of the fly. This compound is formed by the elongation of Z9-18 CoA using malonyl-CoA and NADPH to Z15-24 CoA which is decarboxylated to form Z9-21 Hc (Fig. 3) [78-80]. Other pheromone components include an epoxide and ketone that are produced from Z9-21 Hc by a cytochrome P450 [81,82] and methyl-branched alkanes that are produced by the substitution of methylmalonyl-CoA in place of malonyl-CoA at specific points during chain elongation [83,84]. A novel microsomal fatty acid synthase is involved in production of methyl-branched alkanes in most insects [85-87]. This fatty acid synthase is different from the ubiquitous soluble fatty acid synthase that produces saturated straight chain fatty acids in that it is found in the microsomes and prefers methylmalonyl-CoA. The amino acids valine and isoleucine can provide the carbon skeletons for methylmalonyl-CoA as well as propionate [83]. 

A number of insect sex pheromones are long-chain internal olefins or their epoxides and can be prepared via metathesis reactions, for example the reaction of dec-l-ene with pentadec-l-ene to give tricos-9-ene, the cis isomer of which is a sex pheromone of the housefly (Musca domestica)173.174. see ajso Kiipper and Streck175,176. 

Adams T. S. and Holt G. G. (1987) Effect of pheromone components when applied to different models on male sexual behavior in the housefly, Musca domestica. J. Insect Physiol. 33, 9-18. 

Blomquist G. J., Adams T. S., Halamkar P. P., Gu P., Mackay M. E. and Brown L. (1992) Ecdysteroid induction of sex pheromone biosynthesis in the housefly, Musca domestica. Are other factors involved J. Insect Physiol. 38, 309-318. 

Blomquist G. J., Tillman J. A., Reed J. R., Gu P., Vanderwel D., Choi S. and Reitz R. C. (1995) Regulation of enzymatic activity involved in sex pheromone production in the housefly, Musca domestica. Insect Biochem. Molec. Biol. 25, 751-757. 

Dillwith J. W. and Blomquist G. J. (1982) Site of sex pheromone biosynthesis in the female housefly, Musca domestica. Experientia 38, 471—473. 

Schal C., Sevala V., Capurro M. D. L., Snyder T. E., Blomquist G. J. and Bagneres A.-G. (2001) Tissue distribution and lipophorin transport of hydrocarbon and sex pheromones in the house fly, Musca domestica. 11 pages J. Insect Sci 1, 12. Available onhne insectscience.org/1.12. 

A number of studies since 1980 have concentrated on the search for a sex pheromone analogous to Muscalure, the first contact pheromone discovered in mature Musca domestica females (Carlson et al., 1971). Other hydrocarbons have been described in various Diptera (Carlson et al., 1978 Blomquist and Jackson, 1979 El Messoussi et al., 1994 Blomquist, Chapter 8, in this volume). In all cases, a cuticular hydrocarbon with low or no volatility and high abundance was necessary, but not sufficient for a response. Its action could be checked only... 

Mpuru S., Blomquist G. J., Schal C., Roux M., Kuenzli M., Dusticier G., Clement J-L. and Bagneres A-G. (2001) Effect of age and sex on the production of internal and external hydrocarbons and pheromones in the housefly, Musca domestica. Insect Biochem. Mol. Biol. 31, 139-155. 

Blomquist, G.J. (2003). Ecdysteroid regulation of pheromone production in the housefly, Musca domestica. In Insect Pheromone Biochemistry and Molecular Biology, ed. G.J. Blomquist and R.G. Vogt. London Elsevier, pp. 231-252. 

Figure 4.2 Pheromone hydrocarbon biosynthesis in Drosophila melanogaster (left) and Musca domestica (right). The steps within a grey background occur only in mature females.

Diptera. Cuticular hydrocarbons derived from females have been reported to function as short range sex attractants for all the species of flies that have been examined. (Zj-9-Tricosene was identified as the sex pheromone of the house fly, Musca domestica, whereas C27 and C29 cuticular monoolefins were only weakly active (42). Furthermore, (Z)-9-tricosene was reported to function as a sexual excitant as well, since the incidence of copulatory attempts by male flies was reported to be increased in the presence of this compound. It was subsequently suggested that (Z)-9-heneicosene was an orientation pheromone for male flies, and a 7 3 ratio of the C23 and C21 alkenes was optimal in terms of orientation and mating behavior (43). However, neither hydrocarbon increased the attraction of male flies to moving dummies (44), and it was eventually concluded that these long-chain (zj-9-alkenes functioned primarily as psychedelics with regard to visually stimulated sex attraction and aggregation (45). 

The utility of this new procedure has been demonstrated by the synthesis of mus-calure, the sex pheromone of the house fly Musca domestica) (Eq. 68)I22) and dis-parlure, the sex pheromone of the Gypsy moth (Porthetria dispar L.)123), and the sex attractant of soybean loopers (Pseudoplusia includens)124>. 

Some insects use hydrocarbons as sex pheromones. For example, the housefly, Musca domestica, uses a mixture including (Z) -9-tricosene, the corresponding epoxide and ketone, and several methyl alkanes (2iI). The tricosene is derived by chain elongation of oleic acid, and the epoxide and ketone are made from it. The methyl alkanes are made de novo from acetate and propionate, with one propionate unit per molecule supplying the branch carbon. Propionate can arise from the degradation of valine or isoleucine, but not from succinate, although succinate may serve as an acetate precursor. 

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