Abstract
Diterpene resin acids are major constituents of conifer oleoresin and play important roles in tree defense against insects and microbial pathogens. The tricyclic C-20 carboxylic acids are generally classified into two groups, the abietanes and the pimaranes. The abietanes have conjugated double bonds and exhibit characteristic UV spectra. Here, we report the analysis of abietanes by reversed-phase high-performance liquid chromatography using multiwavelength detection to optimize quantification of underivatized abietic, neoabietic, palustric, levopimaric, and dehydroabietic acids. The utility of the method is demonstrated with methanol extracts of white spruce (Picea glauca) phloem, and representative concentrations are reported.
Similar content being viewed by others
References
Berenbaum, M. 1985. Brementown revisited: Interactions among allelochemicals in plants. Rec. Adv. Phytochem. 19:139–169.
Björkman, C. and Gref, R. 1993. Survival of pine sawflies in cocoon stage in relation to resin acid content of larval food. J. Chem. Ecol. 19:2881–2890.
Franich, R. A. and Gadgil, P. D. 1983. Fungistatic effects of Pinus radiata needle epicuticular fatty and resin acids on Dothistroma pini. Physiol. Plant Pathol. 23:183–195.
Gref, R. 1987. Resin acids and resistance of Pinus sylvestris to Melampsora pinitorqua. Eur. J. For. Pathol. 17:227–230.
Gref, R. and Ericsson, A. 1985. Wound-induced changes of resin acid concentrations in living bark of Scots pine seedlings. Can. J. For. Res. 15:92–96.
Joye, N. M. and Lawrence, R. V. 1967. Resin acid composition of pine oleoresins. J. Chem. Eng. Data 12:279–282.
Kopper, B. J., Illman, B. L., Kersten, P. J., Klepzig, K. D., and Raffa, K. F. 2005. Effects of diterpene acids on components of a conifer bark beetle–fungal interaction: Tolerance by Ips pini and sensitivity by its associate Ophiostoma ips. Environ. Entomol. 34:486–493.
Larsson, S., Björkman, C., and Gref, R. 1986. Responses of Neodiprion sertifer (Hym., Diprionidae) larvae to variation in needle resin acid concentration in Scots pine. Oecologia 70:77–84.
Latorre, A., Rigol, A., Lacorte, S., and Barcelo, D. 2003. Comparison of gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry for the determination of fatty and resin acids in paper mill process waters. J. Chromatogr. A 991:205–215.
Lee, B. L., Ong, H. Y., Koh, D., and Ong, C. N. 1994. High-performance liquid chromatographic method for determination of dehydroabietic and abietic acids, the skin sensitizers in bindi adhesive. J. Chromatogr. A 685:263–269.
Lee, B. L., Koh, D., Ong, H. Y., and Ong, C. N. 1997. High-performance liquid chromatographic determination of dehydroabietic and abietic acids in traditional Chinese medications. J. Chromatogr. A 763:221–226.
McMartin, D. W., Peru, K. M., Headley, J. V., Winkler, M., and Gillies J. A. 2002. Evaluation of liquid chromatography-negative ion electrospray mass spectrometry for the determination of selected resin acids in river water. J. Chromatogr. A 952:289–293.
Rigol, A., Latorre, A., Lacorte, S., and Barcelo, D. 2003. Direct determination of resin and fatty acids in process waters of paper industries by liquid chromatography/mass spectrometry. J. Mass Spectrom. 38:417–426.
Tomlin, E. S., Antonejevic, E., Alfaro, R. I., and Borden, J. H. 2000. Changes in volatile terpene and diterpene resin acid composition of resistant and susceptible white spruce leaders exposed to simulated white pine weevil damage. Tree Physiol. 20:1087–1095.
Volkman, J. K., Holdsworth, D. G., and Richardson, D. E. 1993. Determination of resin acids by gas chromatography and high-performance liquid chromatography in paper mill effluent, river waters and sediments from the upper Derwent Estuary, Tasmania. J. Chromatogr. 643:209–219.
Wagner, M. R., Benjamin, D. M., Clancy, K. M., and Schuh, B. A. 1983. Influence of diterpene resin acids on feeding and growth of larch sawfly, Pristiphora erichsonii (Hartig). J. Chem. Ecol. 9:119–127.
Zinkel, D. F. and Engler, C. C. 1977. Gas–liquid chromatography of resin acid esters. J. Chromatogr. 136:245–252.
Acknowledgements
This work was supported in part by USDA-NRI WIS04746, NSF DEB-0314215, McIntire-Stennis, and the University of Wisconsin College of Agricultural & Life Sciences.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kersten, P.J., Kopper, B.J., Raffa, K.F. et al. Rapid Analysis of Abietanes in Conifers. J Chem Ecol 32, 2679–2685 (2006). https://doi.org/10.1007/s10886-006-9191-z
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10886-006-9191-z