Preparation and characterization of acid dehydration products of aflatoxicol

Treatment of aflatoxicol with acid resulted in the formation of dehydrated derivatives with the 2,3 double bond either hydrated or unaffected. Chromatographic and physicochemical analyses of the purified derivatives revealed that hydration of the 2,3 double bond of aflatoxicol with simultaneous dehydration occurred when sulfuric acid was used. When a weaker acid such as chloroacetic acid was used, no hydration occurred, and 2 isomeric forms of the dehydrated aflatoxicol were obtained. Chicken embryo assay and the Ames test revealed that dehydrated aflatoxicols were much less toxic and mutagenic than aflatoxicol. A mechanism for the dehydration of aflatoxicol is proposed.