Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes

Xenobiotica

Volumn 41, Issue 12, 2011, Pages 1056-1062

  Miyazawa, M ^a   Haigou, R ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

( ) Terpinen 4 ol; CYP2A6; Human; Microsomes; P450; Terpene

Indexed keywords

1,2 EPOXY P MENTHAN 4 OL; ALPHA NAPHTHOFLAVONE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 3A4; DRUG METABOLITE; KETOCONAZOLE; MENTHOFURAN; TERPINEN 4 OL; UNCLASSIFIED DRUG;

ARTICLE; DRUG OXIDATION; DRUG SYNTHESIS; ENZYME ASSAY; LIVER MICROSOME METABOLISM; MASS FRAGMENTOGRAPHY;

BIOCATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; KINETICS; MICROSOMES, LIVER; MODELS, BIOLOGICAL; OXIDATION-REDUCTION; RECOMBINANT PROTEINS; TERPENES;

EID: 80655128413     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2011.596230     Document Type: Article

References (21)

1. Abraham WR, Stumpf B, Kieslich K. (1986). Microbial transformations of terpenoids with 1-p-menthene skeleton. Appl Microbiol Biotechnol 24:24-30. (Pubitemid 16120217)
2. Annarica C, Annarita S, Laura T, Stefania M, Manuela M, Marisa C, Giuseppe S, Francesca M, Giuseppe A, Agnese M. (2004). Terpinen-4-ol, the main component of Melaleuca alternifolia (tea tree) oil inhibits the in vitro growth of human melanoma cells. J Invest Dermatol 122:349-360.
3. Bourrié M, Meunier V, Berger Y, Fabre G. (1996). Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ter 277:321-332. (Pubitemid 27169077)
4. Gonzalez FJ. (1988). Te molecular biology of cytochrome P450s. Pharmacol Rev 40:243-288.
5. Guengerich FP. (1992). Human cytochrome P-450 enzymes. Life Sci 50:1471-1478.
6. Guengerich FP, Shimada T. (1991). Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem Res Toxicol 4:391-407.
7. Hammer KA, Carson C F, Riley T V. (2003). Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil. J Appl Microbiol 95:853-860. (Pubitemid 37186670)
8. Hamrouni SI, Emna M, Touraya C, Aidi WW, Elyes KM, Brahim M. (2009). Efect of growth stage on the content and composition of the essential oil and phenolic fraction of sweet marjoram (Origanum majorana L.). Ind Crops Prod 30:395-402.
9. Hart PH, Brand C, Carson CF, Riley T V, Prager RH, Finlay-Jones JJ. (2000). Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses infammatory mediator production by activated human monocytes. Infamm Res 49:619-626.
10. Khojasteh-Bakht SC, Chen W, Koenigs LL, Peter RM, Nelson SD. (1999). Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide. Drug Metab Dispos 27:574-580. (Pubitemid 29214468)
11. Khojasteh-Bakht SC, Koenigs LL, Peter RM, Trager WF, Nelson SD. (1998). (R)-(+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab Dispos 26:701-704. (Pubitemid 28345854)
12. Miyazawa M, Gyoubu K. (2007). Metabolism of (-)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes. Xenobiotica 37:194-204.
13. Miyazawa M, Kumagae S. (2001). Biotransformation of (R)-and (S)-terpinen-4-ol by the larvae of common cutworm (Spodoptera litura). J Agric Food Chem 49:4312-4314. (Pubitemid 32896429)
14. Miyazawa M, Marumoto S, Takahashi T, Nakahashi H, Haigou R, Nakanishi K. (2011). Metabolism of (+)-and (-)-menthols by CYP2A6 in human liver microsomes. J Oleo Sci 60:127-132.
15. Miyazawa M, Shindo M, Shimada T. (2001a). 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 Metab Dispos 29:200-205. (Pubitemid 32112936)
16. Miyazawa M, Shindo M, Shimada T. (2001b). Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes. Xenobiotica 31:713-723. (Pubitemid 33001095)
17. Miyazawa M, Shindo M, Shimada T. (2002). Metabolism of (+)-and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Drug Metab Dispos 30:602-607. (Pubitemid 34456985)
18. Pongprayoon U, Soontornsaratune P, Jarikasem S, Sematong T, Wasuwat S, Claeson P. (1997). Topical antiinflammatory activity of the major lipophilic constituents of the rhizome of Zingiber cassumunar. Part 1. The essential oil. Phytomedicine 3:319-322.
19. Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. (1994). 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. J Pharmacol Exp Ter 270:414-423. (Pubitemid 24229655)
20. Soo CU, Young PE, Sook DM, Seok PB, Keehyuk K, Hyun KK. 2003. Tight-binding inhibition by α-naphthofavone of human cytochrome P450 1A2. Biochim Biophys Acta 1648:195-202.
21. Tomassen D, Slattery JT, Nelson SD. (1988). Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. J Pharmacol Exp Ter 244:825-829. (Pubitemid 18090093)