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Genotoxicity of fungal metabolites related to aflatoxin B1 biosynthesis
Abstract:
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.
Insights
Several anthraquinone compounds, including 6,8-O-dimethyl-versicolorins and 6-deoxyversicolorin A, show strong mutagenic and genotoxic effects. These compounds, related to aflatoxin B1, are suspected genotoxic carcinogens.
Area of Science:
- Toxicology
- Molecular Biology
- Organic Chemistry
Background:
- Aflatoxin B1 is a potent mycotoxin with known mutagenic and genotoxic properties.
- Metabolites and related compounds of aflatoxin B1 require investigation for their toxicological profiles.
- Understanding the genotoxicity of anthraquinone derivatives is crucial for risk assessment.
Purpose of the Study:
- To evaluate the genotoxicity and mutagenicity of specific anthraquinone compounds related to aflatoxin B1.
- To compare the genotoxic potential of these compounds with known aflatoxin biosynthetic pathway intermediates, versicolorins A and B.
- To identify structural features contributing to the genotoxicity of these compounds.
Main Methods:
- Hepatocyte primary culture (HPC)/DNA repair test was employed to assess genotoxicity.
- Salmonella microsome mutagenesis assay (Ames test) was utilized to determine mutagenicity.
- Comparative analysis of genotoxic and mutagenic activities was performed.
Main Results:
- 6,8-O-Dimethyl-versicolorins A and B, and 6-deoxyversicolorin A demonstrated significant mutagenic and genotoxic activities.
- Versicolorin A and 6,8-O-dimethyl-versicolorin A exhibited greater genotoxicity than versicolorin B and 6,8-O-dimethylversicolorin B, respectively, in the HPC/DNA repair test.
- Nidurufin and norsolorinic acid, lacking a bisfuran ring, showed minimal mutagenicity and no genotoxicity.
Conclusions:
- The tested 6,8-O-dimethyl-versicolorins and 6-deoxyversicolorin A are potent mutagens and genotoxins.
- Versicolorins A and B, along with their dimethylated derivatives, are suspected genotoxic carcinogens.
- The presence of the bisfuran ring may be important for the genotoxic activity of these anthraquinone compounds.