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Absolute Configuration of Anabasine from Messor and Aphaenogaster Ants

Research paper by Sabine Leclercq, Sebastien Charles, Desire Daloze, Jean-Claude Braekman, Serge Aron, Jacques M. Pasteels

Indexed on: 01 May '01Published on: 01 May '01Published in: Journal of Chemical Ecology



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.