Journal of Chemical Ecology

, Volume 17, Issue 3, pp 663–685 | Cite as

Identification and preparation of antiinsectan dienols fromDipterocarpus kerrii tree resins

  • David P. Richardson
  • Adam C. Messer
  • Blair A. Newton
  • Neal I. Lindeman


Originally isolated fromDipterocarpus kerrii, the two previously uncharacterized sesquiterpenes,1 and20, were synthesized from α-gurjunene. A novel process involvingm-chloroperoxybenzoic acid oxidation ofα-gurjunene produced20 in one step. Spectroscopic studies determined that the diene moiety in20 is nonconjugated and also found the C-4 tertiary alcohol center to have theα-configuration, while the other stereocenters have configurations matching the corresponding centers inα-gurjunene. Bioassays with termites demonstrated that20 was more toxic than1, resulting in a 50% mortality in seven days when offered toNeotermes ?dalbergiae on filter papers. The chemicals appear to result from biotransformation ofα-gurjunene. In view of its similarity to the known sesquiterpeneγ-gurjunene, we suggest that20 be referred to asγ-gurjunenol.

Key words

Dipterocarpus kerrii sesquiterpenes chemical synthesis dienol tropical biology termiticide Neotermes α-gurjunene γ-gurjunene γ-gurjunenol bioassay stereochemistry 


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  1. Cais, M. 1964. Conjugated dienes, pp. 955–1024,in S. Patai (ed.). The Chemistry of Functional Groups; The Chemistry of Alkenes. Interscience Publishers, London.Google Scholar
  2. Curran, D.P., Jacobs, P.B., Elliott, R.L., andKim, B.H. 1987. Total synthesis of (−)-specionin.J. Am. Chem. Soc. 109:5280–5282.Google Scholar
  3. Ehret, C., andOurisson, G. 1969. Leγ-gurjunene, structure et configuration. Isomerisation de l'αgurjunene.Tetrahedron 25:1785–1799.Google Scholar
  4. Harborne, J.B. 1982. Plant toxins and their effects on animals, pp. 66–97,in Introduction to Ecological Biochemistry, 2nd ed. Academic Press, New York.Google Scholar
  5. Henbest, H.B., andWilson, R.A.L. 1957. Aspects of stereochemistry. Part I. Stereospecificity in formation of epoxides from cyclic allylic alcohols.J. Chem. Soc. pp. 1958–1965.Google Scholar
  6. Langenheim, J.H. 1990. Plant resins.Am. Sci. 78:16–24.Google Scholar
  7. Messer, A.C. 1990. Chemical ecology in an Indonesian context. University Microfilms, Ann Arbor, Michigan.Google Scholar
  8. Messer, A.C., McCormick, K., Sunjaya, Hagedorn, H., Tumbel, F., andMeinwald, J. 1990. Defensive role of tropical tree resins: Antitermitic sesquiterpenes from Asian Dipterocarpaceae.J. Chem. Ecol. 16:3333–3352.Google Scholar
  9. Newton, B.A. 1989. Synthesis of Anti-insectan Sesquiterpenes. Senior honors thesis. Department of Chemistry, Williams College, Williamstown, Massachusetts.Google Scholar
  10. Noirot, C., andNoirot, T.C. 1969. The digestive system, pp. 49–84,in K. Krishna and F.M. Weesner (eds.). Biology of Termites. Academic Press, New York.Google Scholar
  11. Palmade, M.,Pesnelle, P.,Streith, J., andOurisson, G. 1963. L'α-gurjunene. I. Structure et stereochimie.Bull. Soc. Chim. Fr. pp. 1950–1959.Google Scholar
  12. Pesnelle, P., andOurisson, G. 1965. Hydroboration of α-gurjunene. A rational correlation with cyclocolorenone.J. Org. Chem. 30:1743–1747.Google Scholar
  13. Richardson, D.P., Messer, A.C., Greenberg, S., Hagedorn, H.H., andMeinwald, J. 1989. Defensive sesquiterpenoids from a dipterocarp (Dipterocarpus kerrii).J. Chem. Ecol. 15:731–747.Google Scholar
  14. Still, W.C., Kahn, M., andMitra, A. 1978. Rapid chromatographic technique for preparative separations with moderate resolution.J. Org. Chem. 43:2923–2925.Google Scholar
  15. Streith, J., andOurisson, G. 1963. L'α-gurjunene. II. Quelques reactions de l'α-gurjunene.Bull. Soc. Chim. Fr. pp. 1960–1965.Google Scholar
  16. Tanaka, S., Yamamoto, H., Nozaki, H., Sharpless, K.B., Michaelson, R.C., andCutting, J.D. 1974. Stereoselective epoxidations of acyclic allylic alcohols by transition metal-hydroperoxide reagents. Synthesis ofdl-C18 Cecropia juvenile hormone from farnesol.J. Am. Chem. Soc. 96:5254–5255.PubMedGoogle Scholar
  17. Velleman, P. 1989. Data Desk. Odesta Press, Northbrook, Illinois.Google Scholar
  18. Whitesides, T.H., andNeilan, J.P. 1976. Thermolysis of diene iron tricarbonyl complexes,cistrans Isomerization and hydrogen scrambling reactions in cyclic and acyclic complexes.J. Am. Chem. Soc. 98:63–73.Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • David P. Richardson
    • 1
  • Adam C. Messer
    • 2
  • Blair A. Newton
    • 1
  • Neal I. Lindeman
    • 1
  1. 1.Department of ChemistryWilliams CollegeWilliamstown
  2. 2.School of Food and Nutritional ScienceUniversity of ShizuokaShizuokaJapan

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