A. Visconti et M. Solfrizzo, ISOLATION, CHARACTERIZATION, AND BIOLOGICAL-ACTIVITY OF VISOLTRICIN, A NOVEL METABOLITE OF FUSARIUM-TRICINCTUM, Journal of agricultural and food chemistry, 42(1), 1994, pp. 195-199
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.