Article

Journal of Chemical Ecology

, Volume 27, Issue 5, pp 945-952

Absolute Configuration of Anabasine from Messor and Aphaenogaster Ants

  • Sabine LeclercqAffiliated withDepartment of Organic Chemistry, Laboratory of Bio-organic Chemistry
  • , Sebastien CharlesAffiliated withDepartment of Organic Chemistry, Laboratory of Bio-organic Chemistry
  • , Desire DalozeAffiliated withDepartment of Organic Chemistry, Laboratory of Bio-organic Chemistry
  • , Jean-Claude BraekmanAffiliated withDepartment of Organic Chemistry, Laboratory of Bio-organic Chemistry
  • , Serge AronAffiliated withLaboratory of Cellular and Animal BiologyFree University of Brussels
  • , Jacques M. PasteelsAffiliated withLaboratory of Cellular and Animal BiologyFree University of Brussels

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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