Genotoxicity of fungal metabolites related to aflatoxin B1 biosynthesis.
The genotoxicity of several anthraquinone compounds metabolically related to aflatoxin B1 was examined by means of the hepatocyte primary culture (HPC)/DNA repair test and the Salmonella microsome mutagenesis test, and compared to versicolorins A and B which are potent mutagenic and genotoxic intermediates of the aflatoxin biosynthetic pathway. 6,8-O-Dimethyl-versicolorins A, B and 6-deoxyversicolorin A were found to be strongly mutagenic and genotoxic. Genotoxicity of versicolorin A and 6,8-O-dimethylversicolorin A was stronger than that of versicolorin B and 6,8-O-dimethylversicolorin B, respectively, in the HPC/DNA repair test. Nidurufin and norsolorinic acid, which do not possess a bisfuran ring, exhibited questionable activities for mutagenicity and no genotoxicity. It is suspected that 6,8-O-dimethylversicolorins A, B and 6-deoxyversicolorin A as well as versicolorins A and B are genotoxic carcinogens.
D016604:Aflatoxin B1; D000348:Aflatoxins / Q000096:biosynthesis* / Q000633:toxicity; D000818:Animals; D000880:Anthraquinones / Q000378:metabolism / Q000633:toxicity*; D001230:Aspergillus / Q000378:metabolism*; D001711:Biotransformation; D002478:Cells, Cultured; D004260:DNA Repair / Q000187:drug effects*; D008099:Liver / Q000166:cytology / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D009152:Mutagenicity Tests; D009153:Mutagens; D051381:Rats; D011912:Rats, Inbred ACI; D012486:Salmonella typhimurium / Q000235:genetics
D000348:Aflatoxins; D000880:Anthraquinones; D009153:Mutagens; D016604:Aflatoxin B1; C029826:versicolorin A; C029827:versicolorin C