Metabolism of (+)-Terpinen-4-ol by Cytochrome P450 Enzymes in Human Liver Microsomes
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- Haigou Risa
- Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
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- Miyazawa Mitsuo
- Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
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We examined the in vitro metabolism of (+)-terpinen-4-ol by human liver microsomes and recombinant enzymes. The biotransformation of (+)-terpinen-4-ol was investigated by gas chromatography-mass spectrometry (GC-MS). (+)-Terpinen-4-ol was found to be oxidized to (+)-(1R,2S,4S)-1,2-epoxy-p-menthan-4-ol, (+)-(1S,2R,4S)-1,2-epoxy-p-menthan-4-ol, and (4S)-p-menth-1-en-4,8-diol by human liver microsomal P450 enzymes. The identities of (+)-terpinen-4-ol metabolites were determined through the relative abundance of mass fragments and retention times on GC-MS. Of 11 recombinant human P450 enzymes tested, CYP1A2, CYP2A6, and CYP3A4 were found to catalyze the oxidation of (+)-terpinen-4-ol. Based on several lines of evidence, CYP2A6 and CYP3A4 were determined to be major enzymes involved in the oxidation of (+)-terpinen-4-ol by human liver microsomes. First, of the 11 recombinant human P450 enzymes tested, CYP1A2, CYP2A6 and CYP3A4 catalyzed oxidation of (+)-terpinen-4-ol. Second, oxidation of (+)-terpinen-4-ol was inhibited by (+)-menthofuran and ketoconazole, inhibitors known to be specific for these enzymes. Finally, there was a good correlation between CYP2A6 and CYP3A4 activities and (+)-terpinen-4-ol oxidation activities in the 10 human liver microsomes.
収録刊行物
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- Journal of Oleo Science
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Journal of Oleo Science 61 (1), 35-43, 2012
公益社団法人 日本油化学会
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詳細情報 詳細情報について
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- CRID
- 1390282679068396288
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- NII論文ID
- 130001882204
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- NII書誌ID
- AA11503337
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- ISSN
- 13473352
- 13458957
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- NDL書誌ID
- 023353805
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
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