Abstract
A method is described for determining the enantiomeric composition of chiral alcohols, lactones, and hydroxy acids in quantities ranging from 25 ng to 10 μg. Derivatization of the substance with chirally pure acetyl lactate, followed by splitless capillary gas chromatography, enables enantiomeric determinations to be made within 1–3% of the actual value. This technique was applied in the determination of semiochemical inIps pini (Say),Apis mellifera (L.), andCryptolestes ferrugineus (Stephens). The results indicate that considerable variability exists within populations of some insects in the composition of their chiral semiochemicals, whereas others produce substances of constant composition.
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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.C. 1980. Pheromone attraction and allomonal interruption ofIps pini in California by the two enantiomers of ipsdienol.J. Chem. Ecol. 6:703–717.
Blum, M.S., Fales, H.M., Tucker, K.W., andCollins, A.M. 1978. Chemistry of the sting apparatus of the worker honeybee.J. Apic. Res. 17:218–221.
Borden, J.H. 1967. Factors influencing the response ofIps confusus (LeConte) (Coleoptera: Scolytidae) to male attractant.Can. Entomol. 99:1164–1193.
Collins, A.M., andBlum, M.S., 1982. Bioassay of compounds derived from the honeybee sting.J. Chem Ecol. 8:463–470.
Doolittle, R.E., andHeath, R.R. 1984. (S)-Tetrahydro-5-oxo-2-furancarboxylic acid: A chiral derivatizing reagent for asymmetric alcohols.J. Org. Chem. 49:5041–5050.
Fish, R.H., Browne, L.E., andBergot, B.J. 1984. Pheromone biosynthetic pathways: Conversion of ipsdienone to (-)-ipsdienol, a mechanism for enantioselective reduction in the male bark beetle,Ips paraconfiisus.J. Chem. Ecol. 10:1057–1064.
Gil-Av, E., andNurok, D. 1974. Resolution of optical isomers by gas chromatography of diastereoisomers.Adv. Chromatogr. 10:99–172.
Johnston, B.D., andSlessor, K.N. 1979. Facile synthesis of the enantiomers of sulcatol.Can. J. Chem. 57:233–235.
Kandil, A.A., andSlessor, K.N. 1983. Enantiomeric synthesis of 9-hydroxy-(E)-2-decenoic acid, a queen honeybee pheromone,Can. J. Chem. 61:1166–1168.
Lanier. G.N., Classon, 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.
Plummer, E.L., Stewart, T.E., Byrne, K., Pearce, G.T., andSilverstein, R.M. 1976. Determination of the enantiomeric composition of several insect pheromone alcohols.J. Chem. Ecol. 2:307–311.
Schurig, V., Weber, R., Nicholson, G.J., Oehlschlager. A.C., Pierce, H.D., Jr., A.M., Borden, J.H., andRyker, L.C. 1983. Enantiomer composition of naturalexo- andendo-brevicomin by complexation gas chromatography/selected ion mass spectrometry.Naturwissenschaften 70:92–93.
Silverstein. R.M., Rodin, J.O., Wood, D.L., andBrowne. L.E. 1966. Identification of two new terpene alcohols from frass produced byIps confums in ponderosa pine.Tetrahedron 22:1929–1936.
Winston, M.L., Slessor, K.N., Smirle, M.J., andKandil, A.A. 1982. The influence of a queenproduced substance, 9HDA, on swarm clustering behavior in the honeybee,Apis mellifera L.J. Chem. Ecol. 8:1283–1288.
Wong, J.W., Verigin, V., Oehlschlager, A.C., Borden, J.H., Pierce. H.D., Jr., Pierce. A.M., andChong, L. 1983. Isolation and identification of two macrolide pheromones from the frass ofCryptolestes ferrugineus (Coleoptera: Cucujidae).J. Chem. Ecol. 9:451–474.
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Slessor, K.N., King, G.G.S., Miller, D.R. et al. Determination of chirality of alcohol or latent alcohol semiochemicals in individual insects. J Chem Ecol 11, 1659–1667 (1985). https://doi.org/10.1007/BF01012119
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DOI: https://doi.org/10.1007/BF01012119