Abstract
Stegobinone, (2S, 3R, 1′R)-2,3,-dihy dro-2,3,5-trimethyl-6-(1′-methyl-2′-oxobutyl)-4H-pyran-4-one, the sex pheromone of drugstore beetles (Stegobium paniceum L.), elicited the pheromonal response from the males of the species in our bioassay system; however, the synthesized diastereomeric mixture of this compound was actually inactive to the males. Although the stegobinone isolated from the beetles of this species had significant activity, its enantiomeric [(±)-2S,3R,1′S-] and diatereomeric [(±)-2S,3S,1′RS-] isomers were inactive. Adding the (±)-2S,3R,1′S isomer to stegobinone significantly reduced the male response. Furthermore, the activity of Stegobinone vanished on keeping it at room temperature for two weeks. In such a stored stegobinone sample, the presence of 2S,3R,1′S isomer, the inhibitory component, was confirmed. This isomer might be produced by C-1′ epimerization during storage.
Similar content being viewed by others
References
Ansell, M.J., Hassner, A., andBurkholder, W.E. 1979. The synthesis of the drugstore beetle pheromone (stegobinone).Tetrahedron Lett. 1979:2497–2498.
Azab, A.K. 1954. Observations on the biological races ofstegobium paniceum L.Bull. Soc. Found Ier Entomol. 38:59–80.
Hoffmann, R.W., Ladner, W., Steinbach, K., Massa, W., Schmidt, R. andSnatzke, G. 1981. Absolute Konfiguration von Stegobinone.Chem. Ber. 114:2786–2801.
Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F., andBurkholder, W.E. 1975. Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle,Stegobium paniceum (Coleoptera: Anobiidae).J. Chem. Encol. 1:413–422.
Kuwahara, Y., Fukami, H., Howard, R., Ishii, S., Matsumura, F., andBurkholder, W.E. 1978. Chemical studies on the Anobiidae: Sex pheromone of the drugstore beetle,Stegobium paniceum (L.) (Coleoptera).Tetrahedron 34:1769–1774.
Mori, K., andEbata, T. 1986.Tetrahedron. In press.
Mori, M., Mochizuki, K., Kohno, M., Chuman, T., Ohnishi, A., Watanabe, H., andMori, K. 1985. Inhibitory action of (4S,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone.J. Chem. Ecol. 12:83–89.
Ono, M., Ohnishi, I., Kuwahara, Y., Chuman, T., andKato, K. 1983. Synthesis of (+)-2,3-cis-stegobinone, (+)-cis-2,3-dihydro-2,3,5-trimethyl-6-(1-methyl-2-oxobutyl)-4H-pyran-4-one, the sex pheromone of drugstore beetle.Agric. Biol. Chem. 47:1933–1934.
Tumlinson, J.H., Kleim, 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.
Ward, J.P. 1981. Mating behavior and the mechanism of male orientation in the anobiid bread beetle,Stegobium paniceum.Physiol. Entomol. 6:213–217.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kodama, H., Mochizuki, K., Kohno, M. et al. Inhibition of male response of drugstore beetles to stegobinone by its isomer. J Chem Ecol 13, 1859–1869 (1987). https://doi.org/10.1007/BF01013235
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01013235