Abstract
By adding the effects of a series of the stereoisomers to the pheromonal activity of serricornin, (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone, the sex pheromone of the cigarette beetleLasioderma serricorne (F.) was investigated. The experiments using synthetic enantiomeric mixtures and optically active stereoisomers showed that the (4S,6S,7R)-isomer inhibited significantly the pheromonal activity of serricornin.
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Chuman, T., Kato, K., andNoguchi, M. 1979. Synthesis of (±)-serricornin, 4,6-dimethyl-7-hydroxy-nonan-3-one, a sex pheromone of cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 43:2005.
Chuman, T., Kohno, M., Kato, K., Noguchi, M., Nomi, H., andMori, K. 1981. Stereoselective synthesis oferythro-serricornin, (4R,6R,7S)- and (4S,6R,7S)-4,6-dimethyl-7-hydroxynonan-3-one, stereoisomers of the sex pheromone of cigarette beetle.Agric. Biol. Chem. 45:2019–2023.
Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Ono, M., Onishi, I., andKato, K. 1982a. The pheromone activity of (±)-serricornin for male cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 46:593–595.
Chuman, T., Mochizuki, K., Mori, M., Kohno, M., Kato, K., Nomi, H., andMori, K. 1982b. Behavioral and electroantennogram responses of male cigarette beetle (Lasioderma serricorne F.) to optically active serricornins.Agric. Biol. Chem. 46:3109–3112.
Coffelt, J.A., andBurkholder, W.E. 1972. Reproductive biology of the cigarette beetle,Lasioderma serricorne: Quantitative laboratory bioassay of the female sex pheromone from females of different ages.Ann. Entomol. Soc. Am. 65:447–450.
Klimetzek, D., Loskant, G., Vité, J.P., andMori, K. 1976. Disparlure: Differences in pheromone perception between gypsy moth and nun moth.Naturwissenschaften 63:581–582.
Mochizuki, K., Chuman, T., Mori, M., Kohno, M., andKato, K. 1984. Activity of stereoisomers of serricornin, sex pheromone of the cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 48:2833–2834.
Mori, K., andWatanabe, H. 1985. A new synthesis of serriconin [(4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetles.Tetrahedron 41:3423–3428.
Mori, M., Chuman, T., Kohno, M., Kato, K., andNoguchi, M. 1982a. Absolute stereochemistry of serricornin, the sex pheromone of cigarette beetle, as determined by synthesis of its (4S,6R,7R) isomer.Tetrahedron Lett, 23:667–670.
Mori, M., Chuman, T., andKato, K. 1982b. A stereoselective synthesis of “natural” (4S,6S,7S)-serricornin, the sex pheromone of cigarette beetle, from levoglucosenone.Tetrahedron Lett. 23:4593–4596.
Mori, M., Chuman, T., Kato, K., andMori, K. 1984a. Studies on the synthesis of serricornin. Abstract of papers, 45th Symposium on Synthetic Organic Chemistry, The Society of Synthetic Organic Chemistry of Japan, Tokyo 1984, p. 101.
Mori, M., Chuman, T., andKato, K. 1984b. Cyclic hemiacetal and acyclic chain—the two forms of serricornin.Tetrahedron Lett. 25:2553–2556.
Ono, M., Onishi, I., Chuman, T., Kohno, M., andKato, K. 1980. A novel synthesis of (±)-serricornin 4,6-dimethyl-7-hydroxy-nonan-3-one the sex pheromone of cigarette beetle (Lasioderma serricorne F.).Agric. Biol. Chem. 44:2259–2260.
Tumlinson, J.H., Klein, M.G., Doolittle, R.E., Ladd, T.L., andProveaux, A.T. 1977. Identification of the female Japanese beetle sex pheromone: Inhibition of male response by an enantiomer.Science 197:789–792.
Vite, J.P., Klimetzek, D., Loskant, G., Hedden, R., andMori, K. 1976. Chirality of insect pheromones: Response interruption by inactive antipodes.Naturwissenschaften 63:582–583.
Yamada, M., Saito, T., Kataoiri, K., Iwaki, K., andMarumo, S. 1976. Electroantennogram and behavioral responses of the gypsy moth to enantiomers of disparlure and itstrans analogs.J. Insect Physiol. 22:755–761.
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Mori, M., Mochizuki, K., Kohno, M. et al. Inhibitory action of (4S,6S,7R)-isomer to pheromonal activity of serricornin, (4S,6S,7S)-7-Hydroxy-4,6-dimethyl-3-nonanone. J Chem Ecol 12, 83–89 (1986). https://doi.org/10.1007/BF01045592
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DOI: https://doi.org/10.1007/BF01045592