Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme

Abstract

The structures of the fumonisins, a family of structurally related mycotoxins isolated from cultures of Fusarium moniliforme, were elucidated by mass spectrometry and ¹H and ¹³C n.m.r. spectroscopy as the diester of propane-1,2,3-tricarboxylic acid and either 2-acetylamino- or 2-amino-12,16-dimethyl-3,5,10,14,15-pentahydroxyicosane as well as in each case the C-10 deoxy analogue; in all cases both the C-14 and C-15 hydroxy groups are involved in ester formation with the terminal carboxy group of propane-1,2,3-tricarboxylic acid.