Sterigmatocystin

Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses. Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins, and consists of a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor. It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive until recently, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. A number of closely related compounds such as o-methyl sterigmatocystin are known, and some may also occur naturally. Sterigmatocystin forms pale yellow needles and that are readily soluble in methanol, ethanol, acetonitrile, benzene, and chloroform. Sterigmatocystin reacts with a hot solution of potassium hydroxide and ethanol and is easily methylated by methyl iodide. Treatment with ethanol in acid produces dihydroethoxysterigmatocystin. The toxic effects of sterigmatocystin are much the same as those of aflatoxin B1. It is thus considered as a potent carcinogen, mutagen, and teratogen. It is less acutely toxic to rodents and monkeys but appears to be slightly more toxic to zebra fish. The LD50 in mice is in excess of 800 mg/kg. The 10-day LD50 in Wistar rats is 166 mg/kg in males, 120 mg/kg in females, and 60-65 mg/kg for ip. administration in males. The ip. 10-day LD50 for vervet monkeys is 32 mg/kg.