Roles of human CYP2A6 and rat CYP2B1 in the oxidation of (+)-fenchol by liver microsomes

References

• Galli CL, Galli G, Tragni E, Caruso D, Fiecchi A. Quantitative analysis of alpha, beta-thujone, pulegone, safrole, coumarin and beta-asarone in alcoholic beverages by selected-ion monitoring. Journal of Applied Toxicology 1984; 4: 273–276
   PubMed Web of Science ®Google Scholar
• Gonzalez FJ. The molecular biology of cytochrome P450s. Pharmacology Review 1989; 40: 243–288
   Web of Science ®Google Scholar
• Guengerich FP. Analysis and characterization of enzymes. Principles and methods of toxicology, AW Hayes. Gillette Co., Boston, MA 1994; 1259–1313, USA
   Google Scholar
• Khojasteh-Bakht SC, Koenigs LL, Peter RM, Trager WF, Nelsn SD. (R)-(+) menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metabolism and Disposition 1998; 26: 701–704
   PubMed Web of Science ®Google Scholar
• Maurel P. Cytochromes P450. Metabolic and toxicological aspects, C Ioannides. CRC Press, Boca Raton, FL 1996; 241–270, The CYP3 family,USA
   Google Scholar
• Miyazawa M, Gyoubu K. Metabolism of (+)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. Biological and Pharmaceutical Bulletin 2006; 29: 2354–2358
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Gyoubu K. Metabolism of (−)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. Xenobiotica 2007; 37: 194–204
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Kyousuke N. Biotransformation of (−)-menthone by human liver microsomes. Bioscience Biotechnology and Biochemistry 2006; 168: 1–3
   Google Scholar
• Miyazawa M, Miyamoto Y. Biotransformation of (+)-(1R,2S)-fenchol by the larvae of common cutworm (Spodoptera litura). Tetrahedron 2004; 60: 3091–3096
   Web of Science ®Google Scholar
• Miyazawa M, Shindo M, Shimada T. Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Drug Metabolism and Disposition 2001a; 29: 200–205
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Shindo M, Shimada T. Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, the monoterpene cyclic ether, by rat and human liver microsomes. Xenobiotica 2001b; 31: 713–723
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Shindo M, Shimada T. Sex differences in the metabolism of (+)- and (−)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome P450 enzymes in rat liver microsomes. Chemical Research in Toxicology 2002a; 15: 15–20
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Shindo M, Shimada T. Metabolism of (+)- and (−)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Drug Metabolism and Disposition 2002b; 30: 602–607
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Sugie A, Shimada T. Roles of human CYP2A6 and 2B6 and rat CYP2C11 and 2B1 in the 10-hydroxylation of (−)-verbenone by liver microsomes. Drug Metabolism and Disposition 2003a; 31: 1049–1053
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Sugie A, Shimada T. High-performance liquid chromatographic method for the determination of (−)-verbenone 10-hydroxylation catalysed by rat liver microsomes. Journal of Chromatography B 2003b; 793: 291–296
   PubMed Web of Science ®Google Scholar
• Miyazawa M, Sugie A, Shindo M. Biotransformation of (−)-verbenone by human ligand ver microsomes. Bioscience Biotechnology and Biochemistry 2002c; 66: 2458–2460
   PubMed Web of Science ®Google Scholar
• Pelkonen O, Rautio A, Raunio H, Pasanen M. CYP2A6: A human coumarin 7-hydroxylase. Toxicology 2000; 144: 139–147
   PubMed Web of Science ®Google Scholar
• Shimada T, Inoue K, Suzuki Y, Kawai T, Azuma E, Nakajima T, Shindo M, Kurose K, Sugie A, Yamagishi Y, et al. Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice. Carcinogenesis 2002a; 23: 1199–1207
   PubMed Web of Science ®Google Scholar
• Shimada T, Shindo M, Miyazawa M. Species differences in the metabolism of (+) and (−)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, henoba, dogs, monkeys and humans. Drug Metabolism and Pharmacokinetics 2002b; 17: 507–515
   PubMedGoogle Scholar
• Shimada T, Tsumura F, Yamazaki H. Prediction of human liver microsomal oxidations of 7-ethoxycoumarin and chlorzoxazone using kinetic parameters of recombinant cytochrome P450 enzymes. Drug Metabolism and Disposition 1999; 27: 1274–1280
   PubMed Web of Science ®Google Scholar
• Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology Experimental Therapeutics 1994; 270: 414–423
   PubMed Web of Science ®Google Scholar
• Yamazaki H, Hiroki S, Urano T, Inoue K, Shimada T. Effects of roxithromycin, erythromycin and troleandomycin on their N-demethylation by rat and human cytochrome P450 enzymes. Xenobiotica 1996; 26: 1143–1153
   PubMed Web of Science ®Google Scholar
• Yamazaki H, Mimura M, Sugahara C, Shimada T. Catalytic roles of rat and human cytochrome P450 2A enzymes in testosterone 7- and coumarin 7-hydroxylations. Biochemistry and Pharmacology 1994; 48: 1524–1527
   PubMed Web of Science ®Google Scholar
• Yun CH, Shimada T, Guengerich FP. Purification and characterization of human liver microsomal cytochrome P-450 2A6. Molecular Pharmacology 1991; 40: 679–685
   PubMed Web of Science ®Google Scholar