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Journal of Chemical Ecology

, Volume 14, Issue 3, pp 743–751 | Cite as

Geranium defensive agents. III. Structural determination and biosynthetic considerations of anacardic acids of geranium

  • Donald S. Walters
  • Robert Minard
  • Richard Craig
  • Ralph O. Mumma
Article

Abstract

Ozonolysis, dithioether derivatization, and EI and CI mass spectrometry were used to establish the location of the double bond in the side chain of the two major anacardic acids in geranium (Pelargonium hortorum) trichome exudate. The point of unsaturation was shown to be between C-5 and C-6 counting from the methyl end of the side chain, contradicting the earlier hypothesis that the olefmic bond was probably at the 9–10 position based upon expected biosynthetic considerations. The two major components are thus 6-[(Z)-10′-pentadecenyl]salicylic acid (C22H34O3) and 6-[(Z)-12′-heptadecenyl] salicylic acid (C24H38O3). This may indicate that the precursor of these anacardic acids is a saturated fatty acid since the location of a double bond at the 5–6 position is unusual among the unsaturated fatty acids. Capillary GLC and HPLC of the trichome exudate indicated the presence of small amounts of other anacardic acid analogs possessing such features as odd numbers of carbon atoms and saturated side chains.

Key words

Trichome geraniums Pelargonium defensive agents anacardic acids double-bond location insect resistance 

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References

  1. Buser, H., Arn, H., Guerin, P., andRauscher, S. 1983. Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts.Anal. Chem. 55:818–822.Google Scholar
  2. Craig, R.,Mumma, R. O.,Gerhold, D. L.,Winner, B. L., andSnetsinger, R. 1986. Genetic control of a biochemical mechanism for mite resistance in geraniums, p. 168in M.B. Green and P.A. Hedin (eds.) Natural Resistance of Plants to Pests: Role of Allelochemicals. American Chemical Society Symposium Series 296, Washington, D.C.Google Scholar
  3. Geissman, T. A. 1963. The biosynthesis of phenolic plant products, pp. 563–616in Peter Bernfield (ed.). Biogenesis of Natural Compounds. Macmillan, New York.Google Scholar
  4. Gellerman, J. L., andSchlenk, H. 1968. Methods for isolation and determination of anacardic acids.Anal. Chem. 40(4):739–743.Google Scholar
  5. Gerhold, D. L., Craig, R., andMumma, R. O. 1984. Analysis of trichome exudate from mite resistant geraniums.J. Chem, Ecol. 10(5):713–722.Google Scholar
  6. Stark, R. S. 1975. Morphological and biochemical factors relating to spider mite resistance in the geranium. PhD thesis. Pennsylvania State University, University Park, Pennsylvania.Google Scholar
  7. Stein, R. A., andNicolaides, N. 1962. Structure determination of methyl esters of unsaturated fatty acids by gas liquid chromatography of the aldehydes formed by triphenyl phosphine reduction of the ozonides.J. Lipid Res. 3(4):476–478.Google Scholar
  8. Tyman, J. H. P., Tychopoulos, V., andChan, P. 1984. Quantitative analysis of natural nut-shell liquid (Anacardium occidentale) by high performance liquid chromatography.J. Chromatogr. 303:151–163.Google Scholar
  9. Yalpani, M., andTyman, J. H. P. 1983. The phenolic acids ofPistachia vera.Phytochemistry 22(10):2263–2266.Google Scholar

Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • Donald S. Walters
    • 1
  • Robert Minard
    • 2
  • Richard Craig
    • 3
  • Ralph O. Mumma
    • 1
  1. 1.Pesticide Research Laboratory and Graduate Study Center Department of EntomologyThe Pennsylvania State UniversityUniversity Park
  2. 2.Pesticide Research Laboratory and Graduate Study Center Department of ChemistryThe Pennsylvania State UniversityUniversity Park
  3. 3.Pesticide Research Laboratory and Graduate Study Center Department of HorticultureThe Pennsylvania State UniversityUniversity Park

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