Journal of Chemical Ecology

, Volume 27, Issue 5, pp 945–952 | Cite as

Absolute Configuration of Anabasine from Messor and Aphaenogaster Ants

  • Sabine Leclercq
  • Sebastien Charles
  • Desire Daloze
  • Jean-Claude Braekman
  • Serge Aron
  • Jacques M. Pasteels
Article

Abstract

A method has been developed to assign the absolute configuration and enantiomeric excess of anabasine based on small amounts of material (in the microgram range), by derivatization with (+)-menthylchloroformate followed by capillary GC analysis of the resulting carbamate(s). This method was applied to three samples of anabasine isolated from Messor and Aphaenogaster ants. In Messor sanctus, only (2′S)-anabasine was present, whereas in Aphaenogaster subterranea and A. miamiana (2′S)-anabasine was determined to have an ee of 78 and 24%, respectively.

Alkaloids anabasine ants Messor Aphaenogaster absolute configuration 

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REFERENCES

  1. ARMSTRONG, D. W., LI, W., STALCUP, A. M., SECOR, H. V., IZAC, R. R., and SEEMAN, J. I. 1990. Capillary gas chromatographic separation of enantiomers with stable dipentyl-?-, ß-and ?-cyclodextrin-derivatized stationary phases. Anal. Chim. Acta 234:365-380.Google Scholar
  2. ATTYGALLE, A. B., KERN, F., HUANG, Q., and MEINWALD, J. 1998. Trail pheromone of the myrmicine ant Aphaenogaster rudis (Hymenoptera: Formicidae). Naturwissenschaften 85:38-41.Google Scholar
  3. BOLTON, B. 1995. A New General Catalogue of the Ants of the World. Harvard University Press, Cambridge, Massachusetts.Google Scholar
  4. BRAND, J. M., and MPURU, S. P. 1993. Dufour's gland and poison gland chemistry of the myrmicine ant, Messor capensis (Mayr). J. Chem. Ecol. 19:1315-1321.Google Scholar
  5. COLL, M., HEFETZ, A., and LLOYD, H. A. 1987. Adnexal glands chemistry of Messor ebeninus Forel (Formicidae: Myrmicinae). Z. Naturforsch. 42c:1027-1029.Google Scholar
  6. DEO, N. M., and CROOKS, P. A. 1996. Regioselective alkylation of N-(diphenylmethylidine)-3-(aminomethyl)pyridine: A simple route to minor tobacco alkaloids and related compounds. Tetrahedron Lett. 37:1137-1140.Google Scholar
  7. FOREL, A. 1890. Fourmis de Tunisie et de l'Algérie orientale récoltées et décrites par Aug. Forel Ann. Soc. Entomol. Belg. 34:61-76.Google Scholar
  8. JACKSON, B. D., WRIGHT, P. J., and MORGAN, E. D. 1989. 3-Ethyl-2,5-dimethylpyrazine, a component of the trail pheromone of the ant Messor bouvieri. Experientia 45:487-489.Google Scholar
  9. KEM, W. R. 1988. Pyridine alkaloid distribution in the hoplonemertines. Hydrobiologia 156:145-151.Google Scholar
  10. LECLERCQ, S., THIRIONET, I., BROEDERS, F., DALOZE, D., Van DER MEER, R., and BRAEKMAN, J. C. 1994. Absolute configuration of the solenopsins, venom alkaloids of the fire ants. Tetrahedron 28:8465-8478.Google Scholar
  11. LEETE, E. 1983. “Biosynthesis and metabolism of the tobacco alkaloids.” pp. 85-152, in S.W. Pelletier (ed.). Alkaloids. Chemical and Biological Perspectives, Vol. 1. John Wiley, New York.Google Scholar
  12. LUKES, R., AROJAN, A. A., KOVAR, J., and BLAHA, K. 1962. Zur Konfiguration Stickstoffhaltiger Verbindungen XV. Bestimmung der absolute Konfiguration von Anabasin und Anatabin. Collect. Czech. Chem. Commun. 27:751-756.Google Scholar
  13. PFRENGLE, W., and KUNZ H. 1989. Hetero-Diels-Alder reactions on a carbohydrate template: Stereoselective synthesis of (S)-anabasin. J. Org. Chem. 54:4261-4263.Google Scholar
  14. WHEELER, J. W., OLUBAJO, O., STORM, C. B., and DUFFIELD, R. M. 1981. Anabaseine: Venom alkaloid of Aphaenogaster ants. Science 211:1051-1052.Google Scholar
  15. YANG, C. M., and TANNER, D. D. 1997. A simple synthesis of (±)-1,2,3,6-tetrahydro-2,30-bipyridine (anatabine) and (±)-3-(2-piperidinyl)pyridine (anabasine) from lithium aluminium hydride and pyridine. Can. J. Chem. 75:616-620.Google Scholar

Copyright information

© Plenum Publishing Corporation 2001

Authors and Affiliations

  • Sabine Leclercq
    • 1
  • Sebastien Charles
    • 1
  • Desire Daloze
    • 1
  • Jean-Claude Braekman
    • 1
  • Serge Aron
    • 2
    • 3
  • Jacques M. Pasteels
    • 2
    • 3
  1. 1.Department of Organic ChemistryLaboratory of Bio-organic Chemistry
  2. 2.Laboratory of Cellular and Animal Biology
  3. 3.Free University of BrusselsBrusselsBelgium

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