|Dombrink Kurtzman, Mary Ann|
Submitted to: Biochemistry and Molecular Biology Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: August 29, 1997
Publication Date: N/A
Technical Abstract: Fumonisins are toxins produced by molds, Fusarium moniliforme and F. proliferatum, found on corn worldwide. AAL-toxin (TA) is a structurally-related mycotoxin produced by tomato pathogen, Alternaria alternata f. sp. lycopersici. Both fumonisin B1 (FB1) and TA toxin have been shown to inhibit ceramide synthase in rat hepatocytes (Merrill et al., Adv. Lipid Res. 26:215-234, 1993) and in microsomal preparations of tomato (Gilchrist et al., Can. J. Botany 73:S459-S467, 1995). Structures of the fumonisins (FB1, FB2, FB3 and FB4), hydrolyzed fumonisins (HFB1, HFB2, HFB3 and HFB4) and TA toxin were generated using the SYBYL molecular modeling program, for use in predicting relative toxicity. Data obtained by molecular modeling indicated that FB1 and TA were more similar to each other than to the other analogs, due to the spatial configuration encompassing the primary amine and a carboxyl ion on the tricarballylic sidechain. Results suggested that conformational analysis can be used to predict reactivity and relative toxicity of structurally related molecules.