ISOLATION, CHARACTERIZATION, AND BIOLOGICAL-ACTIVITY OF VISOLTRICIN, A NOVEL METABOLITE OF FUSARIUM-TRICINCTUM

A novel compound, trivially named visoltricin, has been isolated from cultures of Fusarium tricinctum on corn. Its structure has been establ ished by chemical reactions and spectroscopic methods (UV, IR, MS, H-1 NMR, and C-13 NMR) as l-4-(3-methyl-2-butenyl)imidazol-5-yl]-2-propen oic acid methyl ester (molecular formula C13H18N2O2; molecular weight 234.297). It is the first imidazole derivative produced by a Fusarium species. About 30% of the tested isolates (33) of F.tricinctum from va rious substrates and geographic areas produced visoltricin when grown on corn. None of the 14 isolates tested from the United States produce d the compound. Visoltricin was toxic to Artemia salina larvae (LD(50) = 8.5 x 10-(7)M) and cytotoxic (IG(50) < 10(-5) M) to 6 human tumor c ell lines (of 60 lines tested). Visoltricin induced on rabbit eye an i nteresting miotic effect which has been correlated to the anticholines terase activity shown by the compound against human serum and pure enz ymes.