Journal of Chemical Ecology

, Volume 5, Issue 5, pp 727–735 | Cite as

Iridodials and nepetalactone in the defensive secretion of the coconut stick insects,Graeffea crouani

  • Roger M. Smith
  • Joseph J. Brophy
  • G. W. K. Cavill
  • Noel W. Davies


The defensive secretion of the coconut stick insect,Graeffea crouani Le Guillou (Phasmatodea: Phasmatidae) from the Pacific Islands has, as major constituents:trans,trans- andtrans,cis-iridodials and nepetalactone.Cis,trans-iridodial is a minor constituent. A minor iridoid has yet to be identified. Male and female insects yield the same constituents.

Key words

Coconut stick insect defensive secretion Graeffea crouani iridodial nepetalactone gas chromatography-mass spectrometry Phasmatodea Phasmatidae 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Bates, R.B., andSigel, C.W. 1963. Terpenoids.Cis,trans- andtrans,cis-nepetalactones.Experientia 19:564–565.Google Scholar
  2. Bates, R.B., Eisenbraun, E.J., andMcelvain, S.M. 1958. The configurations of the nepetalactones and related compounds.J. Am. Chem. Soc. 80:3420–3424.Google Scholar
  3. Bellas, T.E., Brown, W.V., andMoore, B.P. 1974. The alkaloid actinidine and plausible precursors in defensive secretions of rove beetles.J. Insect Physiol. 20:277–280.Google Scholar
  4. Bowden, K., Heilbron, I.M., Jones, E.R.H., andWeedon, B.C.L. 1946. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols.J. Chem. Soc. 1946:39–45.Google Scholar
  5. Cavill, G.W.K. 1969. Insect terpenoids and nepetalactone, pp. 203–238,in W.I. Taylor, and A.R. Battersby (eds.) Cyclopentanoid Terpene Derivatives. Marcel Dekker, New York.Google Scholar
  6. Cavill, G.W.K., andFord, D.L. 1960. The chemistry of ants III. Structure and reactions of iridodial.Aust. J. Chem. 13:296–310.Google Scholar
  7. Cavill, G.W.K., andRobertson, P.L. 1965. Ant venoms, attractants and repellents.Science 149:1337–1345.Google Scholar
  8. Cavill, G.W.K., Ford, D.L., andLocksley, H.D. 1956. The chemistry of ants. I. Terpenoid constituents of someIridomyrmex species.Aust. J. Chem. 9:288–293.Google Scholar
  9. Cavill, G.W.K., Houghton, E., McDonald, F.J., andWilliams, P.J. 1976. Isolation and characterization of dolichodial and related compounds from the Argentine ant,Iridomyrmex humilis. Insect Biochem. 6:483–490.Google Scholar
  10. Clark, K.J., Fray, G.I., Jaeger, R.H., andRobinson, R. 1959. Synthesis ofd- andl-isoiridomyrmecin and related compounds.Tetrahedron 6:217–224.Google Scholar
  11. Dumbleton, L.J. 1954. A list of insect pests recorded in South Pacific territories. South Pacific Commission Technical Paper 79, Noumea, New Caledonia, pp. 68, 103.Google Scholar
  12. Eisner, T. 1964. Catnip: Its raison d'être.Science 146:1318–1320.PubMedGoogle Scholar
  13. Fish, L.J., andPattenden, G. 1975. Iridodial, and a new alkanone, 4-methylhexan-3-one in the defensive secretion of the beetle.Staphylinus olens. J. Insect Physiol. 21:741–744.Google Scholar
  14. McElvain, S.M., andEisenbraun, E.J. 1955. The constituents of the volatile oil of catnip. III. The structure of nepetalic acid and related compounds.J. Am. Chem. Soc. 77:1599–1605.Google Scholar
  15. McGurk, D.J., Frost, J., Waller, G.R., Eisenbraun, E.J., Vick, K., Drew, W.A., andYoung, J. 1968. Iridodial isomer variation in dolichoderine ants.J. Insect Physiol. 14:841–845.Google Scholar
  16. Meinwald, J., 1954. The structure of nepetalactone.Chem. Ind. 1954:488.Google Scholar
  17. Meinwald, J., Chadha, M.S., Hurst, J.J., andEisner, T. 1962. Defense mechanisms of arthropods—IX. Anisomorphal, the secretion of a phasmid insect.Tetrahedron Lett. 1962:29–33.Google Scholar
  18. Pagnoni, U.M., Pinetti, A., Trave, R., andGaranti, L., 1976. Monoterpenes ofTeucrium marum.Aust. J. Chem. 29:1375–1381.Google Scholar
  19. Regnier, F.E. 1972. Semiochemicals, pp. 723–734, G.R. Waller (ed.). Biochemical Applications of Mass Spectrometry. Wiley-Interscience, New York.Google Scholar
  20. Swaine, G. 1971. Agricultural Zoology in Fiji. H.M.S.O. London, p. 80.Google Scholar
  21. Vidari, G., De Bernardi, M., Pavan, M., andRagozzino, L. 1973. Rose oxide and iridodial fromAromia moschata L. (Coleoptera: Cerambycidae)Tetrahedron Lett. 1973:4065–4068.Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • Roger M. Smith
    • 1
  • Joseph J. Brophy
    • 2
  • G. W. K. Cavill
    • 2
  • Noel W. Davies
    • 2
  1. 1.School of Natural ResourcesUniversity of the South PacificSuva
  2. 2.School of ChemistryUniversity of New South WalesKensingtonAustralia

Personalised recommendations