ARS | Publication request: BIOSYNTHESIS OF THE SOLENOPSINS, VENOM ALKALOIDS OF THE FIRE ANTS

Submitted to: Naturwissenschaften
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 30, 1996
Publication Date: N/A

Interpretive Summary: Ants of the genus Solenopsis (Myrmicinae) and of particular note the red imported fire ant, Solenopsis invicta, secrete a venom consisting of a mixture of 2-methyl-6-alkylpiperidines accompanied in some cases by N-methylated, 1 or side chain unsaturated derivatives. These piperidine alkaloids have been assigned the trivial name solenopsins. These compounds represent the main offensive and defensive weapons of the fire ant and the solenopsins have a wide range of mammalian physiological activities, such as necrosis, mast cell release, and antimicrobial activity. This paper reports our first results on this topic, which clearly demonstrate that cis- and trans-solenopsin A are acetate-derived. These compounds protect the ant from microorganisms in their nests and help them to defend (directly or indirectly through their repellency to non-Solenopsis spp.) and procure resources. Information on the alkaloid biosynthesis could guide us to more effective ant repellents and/or provide clues to the biosynthesis of queen attractant pheromones, which are also produced by the poison gland.

Technical Abstract: Ants of the genus Solenopsis (Myrmicinae) secrete a venom consisting of a mixture of 2-methyl-6alkylpiperidines accompanied in some cases by N-methylated, 1 or side chain unsaturated derivatives. These piperidine alkaloids have been assigned the trivial name solenopsins. The solenopsins differ from each other by the relative configuration of their substituents, the length and the degree of unsaturation of the alkyl chain. The absolute configuration of the trans-alkaloids is always (2R,6R), while that of the cis-alkaloids is (2R, 6S). Although these alkaloids have been the subject of numerous synthetic and biological studies, their biosynthesis remains, however, unknown. The aim of this paper is to report our first results on this topic, which clearly demonstrate that cis- and trans-solenopsin A are acetate-derived.