Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 41, 2011 - Issue 2
314
Views
29
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Metabolism of α-thujone in human hepatic preparations in vitro

, , &
Pages 101-111 | Received 25 Aug 2010, Accepted 27 Sep 2010, Published online: 18 Nov 2010

References

  • Abass K, Reponen P, Jalonen J, Pelkonen O. (2007a). In vitro metabolism and interaction of profenofos by human, mouse and rat liver preparations. Pestic Biochem Physiol 87:238–247.
  • Abass K, Reponen P, Turpeinen M, Jalonen J, Pelkonen O. (2007b). Characterization of diuron N-demethylation by mammalian hepatic microsomes and cDNA-expressed human cytochrome P450 enzymes. Drug Metab Dispos 35:1634–1641.
  • Abelö A, Andersson TB, Antonsson M, Naudot AK, Skånberg I, Weidolf L. (2000). Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes. Drug Metab Dispos 28:966–972.
  • Barter ZE, Bayliss MK, Beaune PH, Boobis AR, Carlile DJ, Edwards RJ, Houston JB, Lake BG, Lipscomb JC, Pelkonen OR, Tucker GT, Rostami-Hodjegan A. (2007). Scaling factors for the extrapolation of in vivo metabolic drug clearance from in vitro data: reaching a consensus on values of human microsomal protein and hepatocellularity per gram of liver. Curr Drug Metab 8:33–45.
  • Bradford MM (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254.
  • Burke MD, Prough RA, Mayer RT. (1977). Characteristics of a microsomal cytochrome P-448-mediated reaction. Ethoxyresorufin O-de-ethylation. Drug Metab Dispos 5:1–8.
  • Dettling A, Grass H, Schuff A, Skopp G, Strohbeck-Kuehner P, Haffner HT. (2004). Absinthe: attention performance and mood under the influence of thujone. J Stud Alcohol 65:573–581.
  • Greenlee WF, Poland A. (1978). An improved assay of 7-ethoxycoumarin O-deethylase activity: induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. J Pharmacol Exp Ther 205:596–605.
  • He X, de Montellano PR. (2004). Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks alpha- and beta-thujone. J Biol Chem 279:39479–39484.
  • Heinemann A, Wischhusen F, Püschel K, Rogiers X. (1999). Standard liver volume in the Caucasian population. Liver Transpl Surg 5:366–368.
  • Höld KM, Sirisoma NS, Ikeda T, Narahashi T, Casida JE. (2000). Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification. Proc Natl Acad Sci USA 97:3826–3831.
  • Höld KM, Sirisoma NS, Casida JE. (2001). Detoxification of alpha- and beta-Thujones (the active ingredients of absinthe): site specificity and species differences in cytochrome P450 oxidation in vitro and in vivo. Chem Res Toxicol 14:589–595.
  • Ishida T, Toyota M, Asakawa Y. (1989). Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Xenobiotica 19:843–855.
  • Jiang Y, He X, Ortiz de Montellano PR. (2006). Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes. Biochemistry 45:533–542.
  • Jiang Y, Ortiz de Montellano PR. (2009). Cooperative effects on radical recombination in CYP3A4-catalyzed oxidation of the radical clock beta-thujone. Chembiochem 10:650–653.
  • Kronbach T, Mathys D, Gut J, Catin T, Meyer UA. (1987). High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Anal Biochem 162:24–32.
  • Kronbach T, Mathys D, Umeno M, Gonzalez FJ, Meyer UA. (1989). Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 36:89–96.
  • Kröner L, Padosch SA, Lachenmeier DW, Madea B. (2005). Untersuchungen zur forensischen relevanz thujonhaltiger spirituosen unter besonderer berücksichtigung toxikologisch-analytischer aspekte. Blutalkohol 42:263–271.
  • Lachenmeier DW, Walch SG, Padosch SA, Kröner LU. (2006). Absinthe–a review. Crit Rev Food Sci Nutr 46:365–377.
  • Li XQ, Björkman A, Andersson TB, Ridderström M, Masimirembwa CM. (2002). Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. J Pharmacol Exp Ther 300:399–407.
  • Pelkonen O, Kaltiala EH, Larmi TK, Kärki NT. (1974). Cytochrome P-450-linked monooxygenase system and drug-induced spectral interactions in human liver microsomes. Chem Biol Interact 9:205–216.
  • Pelkonen O, Turpeinen M. (2007). In vitro-in vivo extrapolation of hepatic clearance: biological tools, scaling factors, model assumptions and correct concentrations. Xenobiotica 37:1066–1089.
  • Peter R, Böcker R, Beaune PH, Iwasaki M, Guengerich FP, Yang CS. (1990). Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chem Res Toxicol 3:566–573.
  • Raunio H, Valtonen J, Honkakoski P, Lang MA, Ståhlberg M, Kairaluoma MA, Rautio A, Pasanen M, Pelkonen O. (1990). Immunochemical detection of human liver cytochrome P450 forms related to phenobarbital-inducible forms in the mouse. Biochem Pharmacol 40:2503–2509.
  • Raunio H, Rautio A, Gullstén H, Pelkonen O. (2001). Polymorphisms of CYP2A6 and its practical consequences. Br J Clin Pharmacol 52:357–363.
  • Rostami-Hodjegan A, Tucker GT. (2007). Simulation and prediction of in vivo drug metabolism in human populations from in vitro data. Nat Rev Drug Discov 6:140–148.
  • Scientific Committee on Food. (2002). Opinion of the Scientific Committee on Food. on Thujone (http://ec.europa.eu/food/fs/sc/scf/out162_en.pdf).
  • Sullivan-Klose TH, Ghanayem BI, Bell DA, Zhang ZY, Kaminsky LS, Shenfield GM, Miners JO, Birkett DJ, Goldstein JA. (1996). The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 6:341–349.
  • Tolonen A, Petsalo A, Turpeinen M, Uusitalo J, Pelkonen O. (2007). In vitro interaction cocktail assay for nine major cytochrome P450 enzymes with 13 probe reactions and a single LC/MSMS run: analytical validation and testing with monoclonal anti-CYP antibodies. J Mass Spectrom 42:960–966.
  • Turpeinen M, Nieminen R, Juntunen T, Taavitsainen P, Raunio H, Pelkonen O. (2004). Selective inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitro. Drug Metab Dispos 32:626–631.
  • Turpeinen M, Uusitalo J, Jouko U, Jalonen J, Jorma J, Pelkonen O, Olavi P. (2005). Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci 24:123–132.
  • Zanger UM, Turpeinen M, Klein K, Schwab M. (2008). Functional pharmacogenetics/genomics of human cytochromes P450 involved in drug biotransformation. Anal Bioanal Chem 392:1093–1108.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.