Biosynthesis of the Solenopsins, Venom Alkaloids of the Fire Ants

摘要

Ants of the genus Solenopsis (Myrmicinae) secrete a venom consisting of a mixture of 2-methyl-6-alkylpiperidines accompanied in some cases by N-methylated, imino, or side-chain-unsaturat-ed derivatives. These piperidine alkaloids have been assigned the trivial name solenopsins by MacConnell et al. The solenopsins (Fig. 1) differ from each other by the relative configuration of their substituents, the length, and 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 dem- onstrate that cis- and trans-solenopsin A (1 and 4) are acetate-derived.