Conversion of aristolochic acid I into aristolic acid by reaction with cysteine and glutathione: biological implications.

Department of Biological Sciences, Florida International University, 11200 Southwest 8th Street, Miami, FL 33199, United States. priestap@fiu.edu.

Journal of natural products 2013 May 24

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Aristolochic acid I (AA-I), naturally occurring in Aristolochia plants, is a potent nephrotoxin and carcinogen. Here we report that AA-I suffers hydrogenolysis with loss of the nitro group by reaction with cysteine or glutathione to give aristolic acid. Since the reaction can proceed in aqueous solutions at pH 7.0 and 37 °C, it is inferred that it may also occur in biological systems and contribute to the nephrotoxic effects induced by AA-I.

Citation

Horacio A Priestap, Manuel A Barbieri. Conversion of aristolochic acid I into aristolic acid by reaction with cysteine and glutathione: biological implications. Journal of natural products. 2013 May 24;76(5):965-8