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Receptor chirality and behavioral specificity of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), for its pheromone, (+)-grandisol

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Abstract

Electrophysiological recordings from antennal olfactory receptors and field behavioral experiments showed both male and female boll weevils,Anthonomus grandis Boh. (Coleoptera: Curculionidae), to respond specifically to (+)-grandisol, an enantiomer of compound I of the boll weevil aggregation pheromone. Single-cell recordings revealed antennal olfactory neurons in both male and female weevils keyed to (+)-grandisol. Electroantennograms in response to serial dilutions of the grandisol enaniiomers showed a threshold 100 to 1000 times lower for (+)-grandisol relative to its antipode. In field behavioral experiments, both sexes were significantly more attracted to (+)-grandisol in combination with the three other pheromone components than the combination with (−)-grandisol. When (−)-grandisol was placed with the (+)-enantiomer at equal dosages, a slight although statistically insignificant inhibition occurred. Subsequent field tests showed that the low level of attraction exhibited by (−)-grandisol in combination with the other three pheromone components could be attributed to the other three components alone. These results are in contrast with an earlier study, which found (−)-grandisol to be as attractive as the (+)-enantiomer.

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References

  • Birch, M.C., Light, D.M., andMori, K. 1977. Selective inhibition of response ofIps pini to its pheromone by the (S)-(−)-enantiomer of ipsenol.Nature 270:738–739.

    Google Scholar 

  • Birch, M.C., Light, D.M., Wood, D.L., Browne, L.E., Silverstein, R.M., Bergot, B.J., Ohloff, G., West, J.R., andYoung, J.D. 1980. Pheromonal attraction and allomonal interruption ofIps pini in California by the enantiomers of ipsdienol.J. Chem. Ecol. 6:703–717.

    Google Scholar 

  • Boeckh, J. 1962. Elektrophysiologische Untersuchungen an einzelnen Geruchs-Rezeptoren auf den Antennen des Totengrabers (Necrophorus, Coleoptera).Z. Vergl. Physiol. 46:212–248.

    Google Scholar 

  • Booth, D.C., Phillips, T.W., Claesson, A., Silverstein, R.M., Lamer, G.N., andWest, J.R. 1983. Aggregation pheromone components of two species ofPissodes weevils (Coleoptera: Curculionidae): Isolation, identification, and field activity.J. Chem. Ecol. 9:1–12.

    Google Scholar 

  • Borden, J.H., Chong, L., Mcclean, J.A., Slessor, K.M., andMori, K. 1976.Gnathotrichus sulcatus: Synergistic response to enantiomers of the aggregation pheromone sulcatol.Science 192:894–896.

    Google Scholar 

  • Borden, J.H., Handley, J.R., Mclean, J.A., Silverstein, R.M., Chong, L., Slessor, K.M., Johnston, B.D., andSchuler, H.R. 1980. Enantiomer-based specificity in pheromone communication by two sympatricGnathotrichus species (Coleoptera: Scolytidae).J. Chem. Ecol. 6:445–456.

    Google Scholar 

  • Dickens, J.C. 1979. Electrophysiological investigations of olfaction in bark beetles.Mitt. Schweiz. Entomol. Ges. 52:203–216.

    Google Scholar 

  • Dickens, J.C. 1981. Behavioural and electrophysiological responses of the bark beetle,Ips typographus, to potential pheromone components.Physiol. Entomol. 6:251–261.

    Google Scholar 

  • Dickens, J.C. 1984. Olfaction in the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae): Electroantennogram studies.J. Chem. Ecol. 10:1759–1785.

    Google Scholar 

  • Dickens, J.C., andBoldt, P.E. 1985. Electroantennogram responses ofTrirhabda bacharides (Weber) Coleoptera: Chrysomelidae) to plant volatiles.J. Chem. Ecol. 11:767–779.

    Google Scholar 

  • Dickens, J.C., andMoorman, E.E. 1987. Role of host plant and sensory environment in maturation of olfactory receptor system of the boll weevil,Anthonomus grandis.Neurosci. Abstr. 13:82.

    Google Scholar 

  • Dickens, J.C., Payne, T.L., Ryker, L.C., andRudinsky, J.A. 1984. Single-cell responses of the Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae), to pheromones and host odors.J. Chem. Ecol. 10:583–599.

    Google Scholar 

  • Dickens, J.C., Payne, T.L., Ryker, L.C., andRudinsky, J.A. 1985. Multiple acceptors for pheromonal enantiomers on single olfactory cells in the Douglas-fir beetle,Dendroctonus pseudotsugae Hopk. (Coleoptera: Scolytidae).J. Chem. Ecol. 11:1359–1370.

    Google Scholar 

  • Dickens, J.C., Eischen, F.A., andDietz, A. 1986. Olfactory perception of the sex attractant pheromone of the greater wax moth,Galleria mellonella L. (Lepidoptera: Pyralidae), by the honey bee,Apis mellifera L. (Hymenoptera: Apidae).J. Entomol. Sci. 21:349–354.

    Google Scholar 

  • Glancey, B.M., andDickens, J.C. 1988. Behavioral and electrophysiological studies with live larvae and larval rinses of the red imported fire ant,Solenopsis invicta Buren (Hymenoptera: Formicidae).J. Chem. Ecol. 14:463–473.

    Google Scholar 

  • Harking, C.M., andMori, K. 1977.Pityokteines curvidens Germ. (Coleoptera: Scolytidae): Aggregation in response to optically pure ipsenol.Z. Angew. Entomol. 83:327–329.

    Google Scholar 

  • Hedden, R.L., Vite, J.P., andMori, K. 1976. Synergistic effect of a pheromone and a kairomone on host selection and colonization byIps avulsus.Nature 221:696–697.

    Google Scholar 

  • Iwaki, S., Marumo, S., Saito, T., Yamada, M., andKatagiri, K. 1974. Synthesis and activity of optically active disparlure.J. Am. Chern. Soc. 96:7842–7844.

    Google Scholar 

  • Klimetzek, D., Loskant, G., Vite, J.P., andMori, K. 1976. Disparlure: Differences in pheromone perception between gypsy moth and nun moth.Naturwissenschaften 63:581.

    Google Scholar 

  • Kodama, H., Mochizuki, K., Kohno, M., Ohnishi, A., andKuwahara, Y. 1987. Inhibition of male response of drugstore beetles to stegobinone by its isomer.J. Chem. Ecol. 13:1859–1869.

    Google Scholar 

  • Krawielitzki, S., Klimetzek, D., Bakke, A., Vite, J.P., andMori, K. 1977. Field and laboratory response ofIps typographus to optically pure pheromonal components.Z. Angew. Entomol. 83:300–302.

    Google Scholar 

  • Lanier, G.N., Claesson, A., Stewart, T., Piston, J.J., andSilverstein, R.M. 1980.Ips pini: The basis for interpopulational differences in pheromone biology.J. Chem. Ecol. 6:677–687.

    Google Scholar 

  • Lensky, Y., andBlum, M.S. 1974. Chirality in insect chemoreceptors.Life Sci. 14:2045–2049.

    Google Scholar 

  • Levinson, H.Z., andMori, K. 1980. Pheromone activity of chiral isomers of trogodermal for male Khapra beetle.Naturwissenschaften 67:148.

    Google Scholar 

  • Light, D.M., andBirch, M.C. 1979. Inhibition of the attractive pheromone response inIps paraconfusus by (R)-(−)-ipsdienol.Naturwissenschaften 66:159–160.

    Google Scholar 

  • Light, D.M., Jang, E.G., andDickens, J.C. 1988. Electroantennogram responses of the Mediterranean fruit fly,Ceratitis capitata, to a spectrum of plant volatiles.J. Chem. Ecol. 14:159–180.

    Google Scholar 

  • Miller, J.R., Mori, K., andRoelofs, W.L. 1977. Gypsy moth field trapping and electroantennogram studies with pheromone enantiomers.J. Insect Physiol. 23:1447–1453.

    Google Scholar 

  • Mitchell, E.B.,Hardee, D.D., andDavich, T.B. 1976. In-field boll weevil trap. U.S. Patent No. 3,949,515.

  • Mori, K. 1984. The significance of chirality: methods for determining absolute configuration and optical purity of pheromones and related compounds, pp. 323–370,in H.E. Hummel and T.A. Miller (eds.). Techniques in Pheromone Research. Springer Verlag, New York.

    Google Scholar 

  • Mori, K., andMiyake, M. 1987. A new synthesis of both the enantiomers of grandisol, the boll weevil pheromone.Tetrahedron 43:2229–2239.

    Google Scholar 

  • Mori, K., Tamada, S., andHedin, P.A. 1978. (−)-Grandisol, the antipode of the boll weevil pheromone, is biologically active.Naturwissenschaften 65:653–654.

    Google Scholar 

  • Mori, K., Masuda, S., andSuguro, T. 1981. Stereocontrolled synthesis of all the possible stereoisomers of 3,11-dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one. The female sex pheromone of the German cockroach.Tetrahedron 37:1329–1340.

    Google Scholar 

  • Mustaparta, H., Angst, M.E., andLanier, G.N. 1980. Receptor discrimination of enantiomers of the aggregation pheromone ipsdienol in two species ofIps.J. Chem. Ecol. 6:689–701.

    Google Scholar 

  • Oakley, B., andSchafer, R. 1978. Experimental Neurobiology. The University of Michigan Press, Ann Arbor, xii + 367 pp.

    Google Scholar 

  • Ostle, B. 1963. Statistics in Research. Iowa State University Press, Ames, Iowa, xv + 585 pp.

    Google Scholar 

  • Payne, T.L., Richerson, J.V., Dickens, J.C., West, J.R., Mori, K., Berisford, C.W., Hedden, R.L., Vite, J.P., andBlum, M.S. 1982. Southern pine beetle: Olfactory receptor and behavior discrimination of enantiomers of the attractant pheromone frontalin.J. Chem. Ecol. 8:873–881.

    Google Scholar 

  • Silverstein, R.M. 1979. Enantiomeric composition and bioactivity of chiral semiochemicals in insects, pp. 133–146,in F. J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier/North-Holland Biomédical Press, Amsterdam.

    Google Scholar 

  • Tumlinson, J.H., Hardee, D.D., Gueldner, R.C., Thompson, A.C., Hedin, P.A., andMinyard, J.P. 1969. Sex pheromones produced by male boll weevil: Isolation, identification, and synthesis.Science 166:1010–1012.

    Google Scholar 

  • Vité, J.P., Hedden, R.L., andMori, K. 1976a. Ips grandicollis: Field response to optically pure pheromone.Naturwissenschaften 64:43.

    Google Scholar 

  • Vite, J.P., Klimetzek, D., Loskant, G., Hedden, R., andMori, K. 1976b. Chirality of insect pheromones: Response interruption by inactive antipodes.Naturwissenschaften 12:582–583.

    Google Scholar 

  • Wood, D.L., Browne, L.E., Ewing, B., Lindahl, K., Bedard, W.D., Tilden, P.E., Mori, K., Pitman, G.B., andHughes, P.R. 1976. Western pine beetle: Specificity among enantiomers of male and female components of an attractant pheromone.Science 192:896–898.

    Google Scholar 

  • Yamada, M., Saito, T., Katagiri, K., Iwaki, S., andMarumo, S. 1976. Electroantennogram and behavioural responses of the gypsy moth to enantiomers of disparlure and itstrans analogues.J. Insect Physiol. 22:755–761.

    Google Scholar 

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Dickens, J.C., Mori, K. Receptor chirality and behavioral specificity of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), for its pheromone, (+)-grandisol. J Chem Ecol 15, 517–528 (1989). https://doi.org/10.1007/BF01014697

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