Abstract
The structural relationships between the cuticular hydrocarbons and the contact sex pheromone of the female German cockroach,Blattella germanica, were investigated. Cuticular hexane extracts were separated into hydrocarbon and ketone fractions by TLC or silicic acid column chromatography. The ketone fraction (which contains the major contact sex pheromone component) was analyzed by GC-MS before and after reduction to ydrocarbon. In addition to 3,11-dimethyl-2-nonacosanone, 3,11-dimethyl-2-heptacosanone was also identified. Females have the 3,11- and 3,9-dimethyl C27 and C29 alkanes, but only the 3,11- isomer of the dimethylketones. Inddition to the hydrocarbon components previously reported, a number of new components were characterized. Although the ratios of cuticular hydrocarbons differ among nymphs, adult males, and adult females, they have qualitatively identical hydrocarbon profiles, suggesting that the production of the contact sex pheromone results from the sex-specific oxidation of 3,11-imethylalkanes to pheromone components by the female.
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Ahmad, S., Kirkland, K.E., andBlomquist, G.J. 1987. Evidence for a sex pheromone metabolizing cytochrome P-450 mono-oxygenase in the housefly,Musca domestica L.Arch. Insect Biochem. Physiol. 6:121–140.
Augustynowicz, M., Malinski, E., Warnke, Z., Szafranek, J., andNawrot, J. 1987. Cuticular hydrocarbons of the German cockroach,Blattella germanica L.Comp. Biochem. Physiol. 86B:519–523.
Blomquist, G.J., Chu, A.J., Nelson, J.H., andPomonis, J.G. 1980. Incorporation of [2,3-13C]succinate into methyl-branched alkanes in a termite.Arch. Biochem. Biophys. 204:648–650.
Blomquist, G.J., Nelson, D.R., andDerenobales, M. 1987. Chemistry, biochemistry and physiology of Insect articular lipids.Arch. Insect Biochem. Physiol. 6:227–265.
Chu, A.J., andBlomquist, G.J. 1980. Biosynthesis of hydrocarbons in insects: Succinate is a precursor of the methyl branched alkanes.Arch. Biochem. Biophys. 201:304–312.
Dillwith, J.W., Nelson, J.H., Pomonis, J.G., Nelson, D.R., andBlomquist, G.J. 1982. A13C NMR study of methyl-branched hydrocarbon biosynthesis in the housefly.J. Biol. Chem. 257:11305–11314.
Halarnkar, P.P., Nelson, J.H., Heisler, C.R., andBlomquist, G.J. 1985. Metabolism of propionate to acetate in the cockroachPeriplaneta americana.Arch. Biochem. Biophys. 236:526–534.
Howard, R.W., andBlomquist, G.J. 1982. Chemical ecology and biochemistry of insect hydrocarbons.Annu. Rev. Entomol. 27:149–172.
Howard, R.W., Mcdaniel, C.A., andBlomquist, G.J. 1978. Cuticular hydrocarbons of the eastern subterranean termite,Reticulitermes flavipes (Kollar) (Isoptera: Rhinotermitidae).J. Chem. Ecol. 4:233–245.
Huano-Minlon. 1946. A simple modification of the Wolff-Kishner reduction.J. Am. Chem. Soc. 68:2487–2488.
Kasang, G. 1974. Biosynthesis of the sex pheromone disparlure by olefin-epoxide conversion.Naturwissenschaften 61:130–131.
Nelson, D.R., Fatland, C.L., Howard, R.W., Mcdaniel, C.A., andBlomquist, G.J. 1980. Re-analysis of the cuticular methylalkanes ofSolenopsis invicta andS. richten.Insect Biochem. 10:409–418.
Nelson, D.R., Dillwith, J.W., andBlomquist, G.J. 1981. Cuticular hydrocarbons of the house fly,Musca domestica.Insect Biochem. 11:187–197.
Nishida, R., andFukami, H. 1983. Female sex pheromone of the German cockroach,Blattella germanica.Mem. Coll. Agric., Kyoto Univ. 122:1–24.
Nishida, R., Fukami, H., andIshii, S. 1974. Sex pheromone of the German cockroach (Blattellagermanica L.) responsible formale wing-raising: 3,11-Dimethyl-2-nonacosanone.Experientia 30:978–979.
Prestwich, G. 1987. Chemical studies of pheromone reception and catabolism, pp. 473–527,in G.D. Prestwich and G.J. Blomquist (eds.). Pheromone Biochemistry. Academic Press, New York.
Roth, L.M., andWillis, E.R. 1952. A study of cockroach behavior.Am. Midl. Nat. 47:65–129.
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Jurenka, R.A., Schal, C., Burns, E. et al. Structural correlation between cuticular hydrocarbons and female contact sex pheromone of German cockroachBlattella germanica (L.). J Chem Ecol 15, 939–949 (1989). https://doi.org/10.1007/BF01015189
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DOI: https://doi.org/10.1007/BF01015189