Metabolism of (+)- and (-)-Menthols by CYP2A6 in Human Liver Microsomes

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  • Miyazawa Mitsuo
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Marumoto Shinsuke
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Takahashi Toshiyuki
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Nakahashi Hiroshi
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Haigou Risa
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Nakanishi Kyousuke
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University

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The in vitro metabolism of (+)-(1S,3S,4R) and (-)-(1R,3R,4S)-menthol enantiomers was examined by incubation with human liver microsomes, and the oxidative metabolites thus formed were analyzed using gas chromatography-mass spectrometry (GC-MS). The (+)- and (-)-menthols were found to be oxidized to the respective (+)-(1S,3S,4S)- and (-)-(1R,3R,4R)-trans-p-menthane-3,8-diol derivatives by human liver microsomal P450 enzymes. Cytochrome P450 (CYP) 2A6 was determined to be the major enzyme involved in the hydroxylation of (+)- and (-)-menthols by human liver microsomes on the basis of the following lines of evidence. First, of 11 recombinant human P450 enzymes tested, CYP2A6 catalyzed the oxidation of (+)- and (-)-menthols. Second, oxidation of (+)- and (-)-menthols was inhibited by (+)-menthofuran and anti-CYP2A6 antibody. Finally, (+)- and (-)-menthol activities were found to correlate with contents of CYP2A6 in liver microsomes of 9 human samples.

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