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

J Nat Prod. 2013 May 24;76(5):965-8. doi: 10.1021/np300822b. Epub 2013 Apr 24.


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.

MeSH terms

  • Aristolochia / chemistry*
  • Aristolochic Acids / chemistry*
  • Aristolochic Acids / pharmacology*
  • Carcinogens / pharmacology
  • Cysteine / chemistry*
  • Cysteine / pharmacology
  • Glutathione / chemistry*
  • Glutathione / pharmacology
  • Hydrogen-Ion Concentration
  • Kidney / pathology
  • Molecular Structure
  • Temperature


  • Aristolochic Acids
  • Carcinogens
  • aristolic acid
  • aristolochic acid I
  • Glutathione
  • Cysteine