Journal of Chemical Ecology

, Volume 27, Issue 12, pp 2397–2423

Male-Specific Sesquiterpenes from Phyllotreta and Aphthona Flea Beetles

  • Robert J. Bartelt
  • Allard A. Cossé
  • Bruce W. Zilkowski
  • David Weisleder
  • Frank A. Momany


It was previously reported that males of the crucifer flea beetle, Phyllotreta cruciferae, feeding on host foliage are attractive to both males and females in the field. Based on this evidence for an aggregation pheromone, volatiles were collected from male and female P. cruciferae feeding on cabbage (Brassica oleracea) and analyzed. For comparison, volatiles were also collected from males and females of three other flea beetle species, Aphthona flava,A. czwalinae, and A. cyparissiae, all feeding on their host, leafy spurge foliage (Euphorbia esula). Six male-specific compounds were isolated from P. cruciferae, and the same compounds plus two additional ones were isolated from males of Aphthona flava,A. czwalinae, and A. cyparissiae. The blends of compounds were relatively consistent within species, but there were characteristic differences between species. Compound structures were studied by mass spectrometry, NMR spectroscopy, UV spectroscopy, polarimetry, chiral and achiral gas chromatography, molecular modeling, and microchemical tests. Three of the compounds were identified as (+)-ar-himachalene; (+)-trans-α-himachalene; (+)-γ-cadinene. Two others were new enantiomers of himachalene hydrocarbons that were previously identified from the fir trees, Abies alba and Abies nordmanniana. Finally, there were two himachalene alcohols and one norsesquiterpene ketone that is a himachalene analog. Only (+)-ar-himachalene and (+)-γ-cadinene are previously known natural products. Electrophysiological activity was demonstrated for five of the compounds. The chemical and electrophysiological patterns are consistent with, but do not prove, a pheromonal function.

sesquiterpene himachalene cadinene flea beetle Aphthona Phyllotreta Chrysomelidae Alticinae 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. ANDERSEN, N. H., BISSONETTE, P., LIU, C.-B., SHUNK, B., OTHA, Y., TSENG, C.-L. W., MOORE, A., and HUNECK, S. 1977. Sesquiterpenes of nine European liverworts from the genera, Anastrepta, Bazzania, Jungermannia, Lepisozia, and Scapania. Phytochemistry 16:1731–1751.Google Scholar
  2. ARNETT, R. H., JR. 1993. American Insects: A Handbook of the Insects of America North of Mexico. Sandhill Crane Press, Gainesville, Florida.Google Scholar
  3. BORROR, D. J. and DELONG, D. M. 1964. An Introduction to the Study of Insects, rev. ed. Holt, Rinehart, and Winston, New York.Google Scholar
  4. BURKHARDT, G., REICHLING, J., MARTIN, R., and BECKER, H. 1986. Terpene hydrocarbons in Pimpinella anisum L. Pharm. Weekbl. Sci. Ed. 8:190–193.Google Scholar
  5. CANE, D. E., RAWLINGS, B. J., and YANG, C.-C. 1987. Isolation of (–)-γ-cadinene and aristolochene from Aspergillus terreus. J. Antibiot. 9:1331–1334.Google Scholar
  6. COSSé, A. A. and BARTELT, R. J. 2000. Male-produced aggregation pheromone of Colopterus truncatus: Structure, electrophysiological and behavioral activity. J. Chem. Ecol. 26:1735–1748.Google Scholar
  7. DEWAR, M. J. S., ZOEBISCH, E. G., HEALEY, E. F., and STEWART, J. J. P. 1985. AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107:3902–3909.Google Scholar
  8. GASSMANN, A., SCHROEDER, D., MAW, E., and SOMMER, G. 1996. Biology, ecology, and host specificity of European Aphthona spp. (Coleoptera, Chrysomelidae) used as biocontrol agents for leafy spurge, Euphorbia esula (Euphorbiaceae), in North America. Biol. Control 6:105–113.Google Scholar
  9. HAMILTON, J. G. C., DAWSON, G. W., and PICKETT, J. A. 1996. 3-Methyl-α-himachalene: Proposed structure for novel homosesquiterpene sex pheromone of Lutzomyia longipalpis (Diptera: Psychodidae) from Jacobina, Brazil. J. Chem. Ecol. 22:2331–2340.Google Scholar
  10. HEATH, R. R. and SONNET, P. E. 1980. Technique for in situ coating of AgC onto silica gel in HPLC columns for the separation of geometrical isomers. J. Liq. Chromatogr. 3:1129–1135.Google Scholar
  11. JOSEPH, T. C. and DEV, S. 1968a. Studies in sesquiterpenes. XXIX. Structure of himachalenes. Tetrahedron 24:3809–3827.Google Scholar
  12. JOSEPH, T. C. and DEV, S. 1968b. Studies in sesquiterpenes. XXXI. The absolute stereochemistry of himachalenes. Tetrahedron 24:3841–3852.Google Scholar
  13. JOSEPH, T. C. and DEV, S. 1968c. Studies in sesquiterpenes. XXXII. Structure of himachalene monohydrochloride and the preparation of trans-himachalenes. Tetrahedron 24:3853–3859.Google Scholar
  14. KHAN, V. A. and PENTEGOVA, V. A. 1988. Volatile components of the oleoresin of Abies alba. Chem. Nat. Comp. 1988:162–166.Google Scholar
  15. KHAN, V. A., TKACHEV, A. V., and PENTEGOVA, V. A. 1989. New sesquiterpenoids from the oleoresin of Abies alba. Chem. Nat. Comp. 1989:606–611.Google Scholar
  16. LAMB, R. J. 1989. Entomology of oilseed Brassica crops. Annu. Rev. Entomol. 34:211–229.Google Scholar
  17. LESAGE, L. and PAQUIN, P. 1996. Identification keys for Aphthona flea beetles (Coleoptera: Chrysomelidae) introduced in Canada for the control of spurge (Euphorbia spp, Euphorbiaceae). Can. Entomol. 128:593–603.Google Scholar
  18. MCDANIEL, B., CLAY, S. H., and SCHOLES, C. 1992. Morphology of three imported Aphthona flea beetles used as biological control agents of leafy spurge. Publication TB 98, Agricultural Experiment Station, South Dakota State University, Brookings, South Dakota.Google Scholar
  19. MEHTA, G. and SINGH, B. P. 1977. Terpenes and related systems. 16. Fate of representative bicyclic sesquiterpenes in strong acid medium: A general rearrangement of hydroazulene sesquiterpenes to decalin types. J. Org. Chem. 42:632–638.Google Scholar
  20. PANDY, R. C. and DEV, S. 1968. Studies in sesquiterpenes. XXX. Synthesis of ar-himachalene and himachalanes. Tetrahedron 24:3829–3839.Google Scholar
  21. PENG, C. and WEISS, M. J. 1992. Evidence of an aggregation pheromone in the flea beetle, Phyllotreta cruciferae (Goeze) (Coleoptera: Chrysomelidae). J. Chem. Ecol. 18:875–884.Google Scholar
  22. PENG, C., BARTELT, R. J., and WEISS, M. J. 1999. Male crucifer flea beetles produce an aggregation pheromone. Physiol. Entomol. 24:98–99.Google Scholar
  23. SONNET, P. E. 1974. cis-Olefins from the Wittig reaction. Org. Prep. Proc. Int. 6:269–273.Google Scholar
  24. VIG, O. P., CHUGH, O. P., and MATTA, K. L. 1970. Terpenoids LIII. Synthesis of (±)-γ-cadinene. Indian J. Chem. 8:29–32.Google Scholar
  25. WILEY. 1995, Wiley. Specral Library, 6th ed. [CD-ROM]. John Wiley & Sons, New York.Google Scholar
  26. WILLIAMS, M. A., and FLEMING, I. 1980. Spectroscopic Methods in Organic Chemistry, 3rd ed. McGraw-Hill, London.Google Scholar
  27. ZHANG, Z.-Q., and MCEVOY, P. B. 1994. Attraction of Longitarsus jacobaeae males to cues associated with conspecific females (Coleoptera: Chrysomelidae). Environ. Entomol. 23:732–737.Google Scholar

Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • Robert J. Bartelt
    • 1
  • Allard A. Cossé
    • 1
  • Bruce W. Zilkowski
    • 1
  • David Weisleder
    • 1
  • Frank A. Momany
    • 1
  1. 1.USDA Agricultural Research ServiceNational Center for Agricultural Utilization ResearchPeoria

Personalised recommendations