Abstract
Responses to enantiomers of (Z)- and (E)-trogodermal (14-methyl-8-hexadecenal) suggest that fourTrogoderma species utilize the (R)-(−) configuration at C-14. Removal of the C-14 methyl branch decreased the response. These results demonstrate the high specificity associated with the configuration at a chiral center, or the methyl branch, distant in terms of numbers of bonds from a functional group.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Cassidy, R.F., Jr., 1978. PhD dissertation, SUNY College of Environmental Science and Forestry, Syracuse, New York.
Cross, J.H., Byler, R.C., Cassidy, R.F., Jr., Silverstein, R.M., Greenblatt, R.E., Burkholder, W.E., Levinson, A.R., andLevinson, H.Z. 1976. Porapak Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal, sex pheromone components, from the females of four species ofTrogoderma (Coleoptera: Dermestidae).J. Chem. Ecol. 2:457–468.
Cross, J.H., Byler, R.C., Silverstein, R.M., Greenblatt, R.E., Gorman, J.E., andBurkholder, W.E. 1977. Sex pheromone components and calling behavior of the female dermestid beetle,Trogoderma variabile Ballion (Coleoptera: Dermestidae).J. Chem. Ecol. 3:115–125.
Greenblatt, R.E., Burkholder, W.E., Cross, J.H., Cassidy, R.F., Jr., Silverstein, R.M., Levinson, A.R., andLevinson, H.Z. 1977. Chemical basis for interspecific responses to sex pheromones ofTrogoderma species (Coleoptera: Dermestidae).J. Chem. Ecol. 3:337–347.
Levinson, A.R., Levinson, H.Z., Schweiger, H., Cassidy, R.F., Jr., andSilverstein, R.M. 1978. Olfactory behavior and receptor potentials of the khapra beetleTrogoderma granarium (Coleoptera: Dermestidae) induced by the major components of its sex pheromone, certain analogues, and fatty acid esters.J. Chem. Ecol. 4:95–108.
Mori, K. 1973. Absolute configuration of (−)-14-methyl-cis-8-hexadecen-1-ol and methyl (−)-14-methyl-cis-8-hexenoate.Tetrahedron Lett. 39:3869–3872.
Mori, K., Suguro, T., andUchida, M. 1978. Synthesis of optically active forms of (Z)-14-methylhexadec-8-enal the pheromone of female dermestid beetle.Tetrahedron 34:3119–3123.
Rodin, J.O., Silverstein, R.M., Burkholder, W.E., andGorman, J.E. 1969. Sex attractant of female dermestid beetleTrogoderma inclusum.Science 165:904–906.
Rossi, R., andCarpita, A. 1977. Insect pheromones. Synthesis of chiral sex pheromone components of several species ofTrogoderma (Coleoptera: Dermestidae).Tetrahedron 33:2447–2450.
Rossi, R., andNiccoli, A. 1978. Relationship between chirality and biological activity. Biological response ofTrogoderma granarium to optically active synthetic sex attractants.Naturwissenschaften 65:259–269.
Shapas, T.J., andBurkholder, W.E. 1978. Patterns of sex pheromone release from adult females, and effects of air velocity and pheromone release rates on theoretical communication distances inTrogoderma glabrum.J. Chem. Ecol. 4:395–408.
Silverstein, R.M. 1979. Enantiomeric composition and bioactivity of chiral semiochemicals in insects, pp. 133–146,in F. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier/North Holland, Amsterdam.
Suguro, T., andMori, K. 1979. Synthesis of optically active forms of (E-14-methyl-8-hexadecenal).Agric. Biol. Chem. 43:409–410.
Author information
Authors and Affiliations
Additional information
Coleoptera: Dermestidae.
Rights and permissions
About this article
Cite this article
Silverstein, R.M., Cassidy, R.F., Burkholder, W.E. et al. Perception byTrogoderma species of chirality and methyl branching at a site far removed from a functional group in a pheromone component. J Chem Ecol 6, 911–917 (1980). https://doi.org/10.1007/BF00990475
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00990475