Skip to main content
Log in

Variation of enantiomeric composition of α-pinene in norway spruce,Picea abies, and its influence on production of verbenol isomers byIps typographus in the field

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

The enantiomeric composition of α-pinene in individual Norway spruce trees [Picea abies (L.) Karst.] was determined on a chiral GC column after stereoselective hydroboration-oxidation followed by a reaction with isopropyl isocyanate to form the carbamate derivative. The enantiomeric composition varied considerably between trees of different genetic origin. There was a strong correlation between the chirality of α-pinene in host spruce trees and thecis/trans ratio of verbenols found in the hindguts of the bark beetleIps typographus (L.) infesting the trees.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Birgersson, G., Schlyter, F., Löfqvist, J., andBeroström, G. 1984. Quantitative variation of pheromone components in spruce bark beetleIps typographus from different attack phases.J. Chem. Ecol. 10:1029–1055.

    Google Scholar 

  • Birgersson, G.,Schlyter, F.,Bergström, G., andLöfqvist, J. 1988. Individual variation in the aggregation pheromone content of the spruce bark beetle,Ips typographus.J. Chem. Ecol. Submitted.

  • Brändström, A., Junggren, U., andLamm, B. 1972. An improved method for the preparation of solutions of diborane.Tetrahedron Lett. 31:3173–3176.

    Google Scholar 

  • Byers, J.A. 1981. Pheromone biosynthesis in the bark beetle,Ips paraconfusus, during feeding or exposure to vapours of host plant precursors.Insect Biochem. 11:563–569.

    Google Scholar 

  • Comyns, A.E., andLucas, H.J. 1957. Coordination of silver ion with unsaturated compounds. IX. Solid complexes of silver salts with cyclohexene, α-pinene and β-pinene.J. Am. Chem. Soc. 79:4339–4341.

    Google Scholar 

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

    Google Scholar 

  • Juvonen, S. 1966. Über die Terpenbiosynthese inPinus silvestris.Acta Bot. Fenn. 71:5–92.

    Google Scholar 

  • Klimetzek, D., andFrancke, W. 1980. Relationship between the enantiomeric composition of α-pinene in host trees and the production of verbenols inIps species.Experentia 36:1343–1345.

    Google Scholar 

  • König, A.W., Francke, W., andBenecke, I. 1982. Gas Chromatographic enantiomer separation of chiral alcohols.J. Chromatogr. 239:227–231.

    Google Scholar 

  • Koscielski, T., Sybilska, D., andJurczak, J. 1983. Separation of α-pinene and β-pinene into enantiomers in gas-liquid chromatography systems via cyclodextrin inclusions complex.J. Chromatogr. 280:131–134.

    Google Scholar 

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

    Google Scholar 

  • Kruse, K., Francke, W., andKönig, W.A. 1979. Gas Chromatographic separation of chiral alcohols, amino alcohols and amines.J. Chromatogr. 170:423–429.

    Google Scholar 

  • Lindström, M.,Norin, T., andRoeraade, J. 1987. Gas Chromatographic separation of monoterpene hydrocarbon enantiomers using α-cyclodextrin and formamide/water as stationary phase.J. Chromatogr. Submitted.

  • Mirov, N.T. 1961. Composition of gum turpentines of pines. U.S. Department of Agriculture, Technical bullentin No. 1239. ([α]D values from Beilsteins Handbuch der Organischen Chemie, Vierte Auflage, 1922, Band 5, page 146.)

  • Renwick, A.A., Hughes, P.R., andKrull, J.S. 1976. Selective production ofcis and trans-verbenol from (−)-α- and (+)-β-pinene by a bark beetle.Science 191:199–201.

    Google Scholar 

  • Rudloff, E. Von. 1967. Chemosystematic studies in the genusPicea (Pinaceae). I. Introduction.Can. J. Bot., 45(6):891–901.

    Google Scholar 

  • Schlyter, F., Birgersson, G., Byers, J.A., Löfqvist, J., andBergström, G. 1987. Field responce of the spruce bark beetle,Ips typographus, to aggregation pheromone candidates.J. Chem. Ecol. 13:701–716.

    Google Scholar 

  • Schurig, V., Leyrer, U., andWeber, R. 1985. The use of glass and fused silica open tubular columns for the separation of structural, configurai and optical isomers by selective complexation GC: sec-alcohols and ketones.HRC & CC 8:459–464.

    Google Scholar 

  • Silverstein, R.M., Rodin, J.O., andWood, D.L. 1966. Sex attractants in frass produced by maleIps confusus in Ponderosa pine.Science 154:509–510.

    Google Scholar 

  • Zweifel, G., andBrown, H.C. 1964. Hydroboration of terpenes II. The hydroboration of α- pinene and β-pinene-the absolute configuration of the dialkyborane from the hydroboration of α-pinene.J. Am. Chem. Soc. 86:393–397.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Coleoptera; Scolytidae.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lindström, M., Norin, T., Birgersson, G. et al. Variation of enantiomeric composition of α-pinene in norway spruce,Picea abies, and its influence on production of verbenol isomers byIps typographus in the field. J Chem Ecol 15, 541–548 (1989). https://doi.org/10.1007/BF01014699

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01014699

Key words

Navigation