Biosynthesis of tetraponerine-8, a defence alkaloid of the ant Tetraponera sp.

Abstract

The administration of sodium [1- 14 C] and [2- 14 C] acetate, L-[U- 14 C] glutamic acid, γ-amino [U- 14 C] butyric acid, L-[U- 14 C] ornithine hydrochloride, and [1,4- 14 C] putrescine dihydrochloride to Tetraponera sp. ants resulted in the formation, for each feeding experiment, of labelled tetraponerine-8 (2). The distribution of radioactivity into 2 was established by chemical degradation. The results obtained favor the hypothesis that the pyrrolidine ring of tetraponerine-8 is derived from L-glutamic acid via L-ornithine and putrescine, while the 12-carbon chain is derived from the combination of six acetate units.