Journal of Chemical Ecology

, Volume 22, Issue 12, pp 2331–2340 | Cite as

3-Methyl-α-himachalene: Proposed structure for novel homosesquiterpene sex pheromone ofLutzomyia longipalpis (diptera: Psychodidae) from Jacobina, Brazil

  • J. G. C. Hamilton
  • G. W. Dawson
  • J. A. Pickett
Article

Abstract

The principal behaviorally active volatile component (ca. 90% +) of the sex pheromone glands ofLutzomyia longipalpis from Jacobina. Brazil, has been isolated and characterized as a novel homosesquiterpene with the structure 3-methyl-α-himachalene (C16H26). A minor component (ca. 10%) of the gland extract has also been identified as the sesquiterpeneα-himachalene (C15H24). This work confirms that there are at least 3 members of theL. longipalpis species complex.

Key Words

Sex pheromone tergal gland Lutzomyia longipalpis 3-methyl-α-himachalene homosesquiterpene mass spectrometry high-performance liquid chromatography nuclear magnetic resonance 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adam, W., Chan, Y., Cremer, D., Gauss, J., Scheutzow, D., andSchindler, M. 1987. Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations.J. Org. Chem. 52:2800–2803.CrossRefGoogle Scholar
  2. Boland, W., andGäbler, A. 1989. Biosynthesis of homoterpenes in higher plants.Helv. Chim. Acta. 72:247–253.CrossRefGoogle Scholar
  3. Donath, J., andBoland, W. 1994. Biosynthesis of acyclic homoterpenes in higher plants parallels steroid hormone metabolism.J. Plant Physiol. 143:473–478.Google Scholar
  4. Dougherty, M. J., Guerin, P., andWard, R. D. 1995. Identification of oviposition attractants for the sandflyLutzomyia longipalpis (Diptera: Psychodidae) in volatiles of faeces from vertebrates.Physiol. Entomol. 20:23–32.Google Scholar
  5. Dugdale, J. S. 1990. Reassessment ofCtenopseustis Meyrick andPlanotortrix Dugdale with descriptions of two new genera (Lepidoptera: Tortricidae).N.Z. J. Zool. 17:437–465.Google Scholar
  6. Hamilton, J. G. C., andWard, R. D. 1991. Gas chromatographic analysis ofLutzomyia longipalpis tergal pheromone gland extract.Parassitologia 33 (Suppl 1):283–289.PubMedGoogle Scholar
  7. Hamilton, J. G. C., andWard, R. D. 1994. Chemical analysis of a putative sex pheromone fromLutzomyia pessoai (Diptera:Psychodidae).Ann. Trop. Med. Parasitol. 88(4):405–412.PubMedGoogle Scholar
  8. Hamilton, J. G. C., Doughtery, M. J., andWard, R. D. 1994. Isolation and identification of sex pheromone activity in components of tergal gland extract ofLutzomyia longipalpis (Diptera:Psychodidae) from North East Brazil.J. Chem. Ecol. 20(1):141–151.CrossRefGoogle Scholar
  9. Hamilton, J. G. C., Dawson, G. W., andPickett, J. A. 1996a. 9-Methylgermacrene-B: proposed structure for the novel homosesquiterpene sex pheromone ofLutzomyia longipalpis (Diptera:Psychodidae) from Lapinha, Brazil.J. Chem. Ecol. 22(8):1477–1492.CrossRefGoogle Scholar
  10. Hamilton, J. G. C., Ward, R. D., Doughtery, M. J., Ponce, C., Ponce, E., Noyes, H., andZeledon, R. 1996b. Comparison of terpene components in extracts ofLutzomyia longipalpis (Diptera: Psychodidae) from areas of visceral and atypical cutaneous leishmaniasis in Honduras and Costa Rica.Ann. Trop. Med. Parasitol. 90(5):533–541.PubMedGoogle Scholar
  11. Krishna Rao, G. S., Dev, S., andGuha, P. C. 1952. Studies in sesquiterpenes. Part XII. Sesquiterpenes of the essential oil from the wood of the Himalayan deodar.J. Indian Chem. Soc. 29(10):721–730.Google Scholar
  12. Lane, R. P., Phillips, A., Molyneux, D. H., Procter, G., andWard, R. D. 1985. Chemical analysis of the abdominal glands of two forms ofLutzomyia longipalpis: Site of a possible sex pheromone?Ann. Trop. Med. Parasitol. 79:225–229.PubMedGoogle Scholar
  13. Lanzaro, G. C., Ostovska, K., Herrero, M. V., Lawyer, P. G., andWarburg, A. 1993.Lutzomyia longipalpis is a species complex: Genetic divergence and interspecific hybrid sterility among three populations.Am. J. Trop. Med. Hyg. 48(6):839–847.PubMedGoogle Scholar
  14. Löfstedt, C., Hansson, B. S., Toth, M., Szöcs, G., Buda, V., Bengtsson, M., Ryrholm, N., Svensson, M., andPriesner, E. 1994. Pheromone differences between sibling taxaDiachrysia chrysitis (Linnaeous, 1758) andD. tutti (Kostrowicki, 1961) (Lepidoptera: Noctuidae).J. Chem. Ecol. 20(1):91–109.CrossRefGoogle Scholar
  15. Morton, I. E., andWard, R. D. 1989. Laboratory response of femaleLutzomyia longipalpis sandflies to a host and male pheromone source over distance.Med. Vet. Entomol. 3:219–223.PubMedGoogle Scholar
  16. NIST 1990. Standard Reference Data Base (Version 3.01). Office of the Standard Reference Data Base. National Institute of Standards and Technology, Gaithersburg, Maryland.Google Scholar
  17. Phillips, A., Ward, R. D., Ryan, L., Molyneux, D. H., Lainson, R., andShaw, J. J. 1986. Chemical analysis of compounds extracted from the “tergal” spots ofLutzomyia longipalpis from Brazil.Acta Trop. 43:271–276.PubMedGoogle Scholar
  18. Roelofs, W. L., andCarde, R. T. 1974. Sex pheromones in the reproductive isolation of lepidopterous species, pp. 96–114,in H. C. Birch (ed.). North Holland Publishing, Amsterdam.Google Scholar
  19. Roelofs, W. L., andComeau, A. 1969. Sex pheromone specificity: Taxonomic and evolutionary aspects in Lepidoptera.Science 165:398–400.Google Scholar
  20. Tabacchi, R., Garnero, J., andBuil, P. 1974. Isolement et identification des hydrocarbures sesquiterpéniques de l'huile essentielle de graines d'Anis.Helv. Chim. Acta 57(3):849–851.CrossRefGoogle Scholar
  21. Ward, R. D., Ribeiro, A. L., Ready, P. D., andMurtagh, A. 1983. Reproductive isolation between different forms ofLutzomyia longipalpis (Lutz and Neiva), (Diptera: Psychodidae), the vector ofLeishmania donovani chagasi Cunha and Chagas and its significance to Kalaazar distribution in South America.Mem. Inst. Os. Cruz. 78:269–280.Google Scholar
  22. Ward, R. D., Phillips, A., Burnet, B., andMarcondes, C. B. 1988. TheLutzomyia longipalpis complex: reproduction and distribution, pp. 257–269, M. W. Service (ed.)in Biosystematics of Haematophagous Insects. Systematics Association Special Volume 37. Clarendon Press, Oxford.Google Scholar
  23. Ward, R. D., Morton, I. E., Lancaster, V., Smith, P., andSwift, A. 1989. Bioassays as an indicator of pheromone communication inLutzomyia longipalpis (Diptera: Psychodidae). NATO ASI Series on Leishmaniasis, Zakinthos, Greece, No. 163. Springer, New York, pp. 239–247.Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • J. G. C. Hamilton
    • 1
    • 2
  • G. W. Dawson
    • 2
  • J. A. Pickett
    • 2
  1. 1.Chemical Ecology Group, Centre for Applied Entomology and Parasitology Department of Biological SciencesUniversity of KeeleStaffordshireEngland, UK
  2. 2.Department of Biological and Ecological ChemistryIACR-RothamstedHarpendenEngland, UK

Personalised recommendations