title: Conversion of aristolochic acid I into aristolic acid by reaction with cysteine and glutathione: biological implications.
abstract: 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.
authors.affiliation: Department of Biological Sciences, Florida International University, 11200 Southwest 8th Street, Miami, FL 33199, United States. priestap@fiu.edu.
authors.forename: Horacio A
authors.initials: HA
authors.lastname: Priestap
authors.forename: Manuel A
authors.initials: MA
authors.lastname: Barbieri
mesh_terms: D030022:Aristolochia / Q000737:chemistry*; D034341:Aristolochic Acids / Q000737:chemistry* / Q000494:pharmacology*; D002273:Carcinogens / Q000494:pharmacology; D003545:Cysteine / Q000737:chemistry* / Q000494:pharmacology; D005978:Glutathione / Q000737:chemistry* / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007668:Kidney / Q000473:pathology; D015394:Molecular Structure; D013696:Temperature
chemical_list: D034341:Aristolochic Acids; D002273:Carcinogens; C018834:aristolic acid; C000228:aristolochic acid I; D005978:Glutathione; D003545:Cysteine