Oxidative metabolism of the alkaloid rutaecarpine by human cytochrome P450

Drug Metabolism and Disposition

Volumn 34, Issue 5, 2006, Pages 821-827

  Ueng, Yune Fang ^a,b,c   Don, Ming Jaw ^a   Jan, Woan Ching ^b,d   Wang, Shu Yun ^a   Ho, Li Kang ^b   Chen, Chieh Fu ^a,b,e  

^a NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^b NATIONAL YANG MING UNIVERSITY   (Taiwan)

^c TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^d NURSING AND MANAGEMENT COLLEGE   (Taiwan)

^e Qing Dao University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

10 HYDROXYRUTAECARPINE; 11 HYDROXYRUTAECARPINE; 12 HYDROXYRUTAECARPINE; 3 HYDROXYRUTAECARPINE; ALKALOID DERIVATIVE; ALPHA NAPHTHOFLAVONE; CYTOCHROME P450; CYTOCHROME P450 1A; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 INHIBITOR; DRUG METABOLITE; KETOCONAZOLE; QUINIDINE; RECOMBINANT ENZYME; RUTAECARPINE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; BACTERIUM; CATALYSIS; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; HUMAN; HUMAN TISSUE; IC 50; LIVER MICROSOME; PRIORITY JOURNAL;

ALKALOIDS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; ESCHERICHIA COLI; HUMANS; HYDROXYLATION; ISOENZYMES; KINETICS; MICROSOMES, LIVER; OXIDATION-REDUCTION; PROTEIN BINDING;

BACTERIA (MICROORGANISMS); EVODIA RUTAECARPA;

EID: 33645822532     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.105.007849     Document Type: Article

References (30)

1. Balawin SJ, Bloomer JC, Smith GJ, Ayrton AD, Clarke SE, and Chenery RJ (1995) Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica 25:261-270.
2. Bergman J and Bergman S (1985) Studies of rutaecarpine and related quinazolinocarboline alkaloids. J Org Chem 50:1246-1255.
3. Bourrie M, Meunier V, Berger Y, and Fabre G (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277:321-332.
4. Chang TKH, Gonzalez FJ, and Waxman DJ (1994) Evaluation of triacetyloleandomycin, -naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch Biochem Biophys 311:437-442.
5. Chen CF, Chiou WF, Chou CJ, Liao JF, Lin LC, Wang GJ, and Ueng YF (2002) Pharmacological effects of Evodia rutaecarpa and its bioactive components. Chin Pharm J 54:419-435.
6. Dey A, Jones JE, and Nebert DW (1999) Tissue- and cell type-specific expression of cytochrome P450 1A1 and cytochrome P450 1A2 mRNA in the mouse localized in situ hybridization. Biochem Pharmacol 58:525-537.
7. Ding X and Kaminsky LS (2003) Human extrahepatic cytochrome P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol 43:149-173.
8. Don MJ, Lewis DFV, Wang SY, Tsai MW, and Ueng YF (2003) Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2 and CYP1B1. Bioorg Med Chem Lett 13:2535-2538.
9. Duggleby RG (1994) Product inhibition of reversible enzyme-catalysed reactions. Biochim Biophys Acta 1209:238-240.
10. Guengerich FP (1994) Preparation of microsomal and cytosolic fractions, in Principles and Methods of Toxicology, 3rd ed (Hayes AW ed) pp 1267-1268, Raven Press, New York.
11. Guengerich FP (1995) Human cytochrome P450 enzymes, in Cytochrome P450 (Ortiz de Montellano PR ed) pp 473-535, Plenum Press, New York.
12. Hasler JA, Estabrook R, Murray M, Pikuleva I, Watreman M, Capdevila J, Holla V, Helvig C, Falck JR, Farrell G, et al. (1999) Human cytochrome P450. Mol Aspect Med 20:1-137.
13. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254.
14. Lasker JM, Wester MR, Aramsombatdee E, and Raucy JL (1998) Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin and omeprazole hydroxylations. Arch Biochem Biophys 353:16-28.
15. Lee SK, Kim NH, Lee J, Kim DH, Lee ES, Choi HG, Chang HW, Jahng Y, and Jeong TC (2004) Induction of cytochrome P450s by rutaecarpine and metabolism of rutaecarpine by cytochrome P450s. Planta Med 70:753-757.
16. Liao JF, Chen CF, and Chow SY (1981) Pharmacological studies of Chinese herbs. 9. Pharmacological effects of Evodiae fructus. J Formosan Med Assoc 79:30-38.
17. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, and Shou M (2001) Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos 29:368-374.
18. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
19. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemeprotein nature. J Biol Chem 239:2370-2379.
20. Parikh A, Gillam EMJ, and Guengerich FP (1997) Drug metabolism by Escherichia coli expressing human cytochrome P450. Nat Biotech 15:784-788.
21. Pohl RJ and Fouts JR (1980) A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal Biochem 107:150-155.
22. Sheu JR (1999) Pharmacological effects of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa. Cardiovasc Drug Rev 17:237-245.
23. Shimada T, Yamazaki H, Mimura M, Inui Y, and 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 Ther 270:414-423.
24. Tang W and Eisenbrand G (1992) Evodia rutaecarpa (Juss) Benth, in Chinese Drugs of Plant Origin (Tang W and Eisenbrand G eds) pp 509-514, Springer-Verlag, Berlin.
25. Ueng YF, Don MJ, Peng HC, Wang SY, Wang JJ, and Chen CF (2002a) Effects of Wu-chu-yu tang and its component herbs on drug-metabolizing enzymes. Jpn J Pharmacol 89:267-273.
26. Ueng YF, Jan WC, Lin LC, Chen TL, Guengerich FP, and Chen CF (2002b) The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug Metab Dispos 30:349-353.
27. Ueng YF and Wang SY (2003) The herbal preparation Wu-chu-yu-tang enhances the excretion of the CYP1A2 substrate caffeine in mice. J Chin Med 14:175-181.
28. Ueng YF, Yu HJ, Lee CH, Peng C, Jan WC, Ho LK, Chen CF, and Don MJ (2005) Identification of microsomal oxidation metabolites of rutaecarpine, a main active alkaloid of the medicinal herb Evodia rutaecarpa. J Chromatogr A 1076:103-109.
29. Waxman DJ (1999) P450 gene induction by structurally diverse xenochemicals: central role of nuclear receptor CAR, PXR, and PPAR. Arch Biochem Biophys 369:11-23.
30. Waxman DJ and Azaroff L (1992) Phenobarbital induction of cytochrome P-450 gene expression. Biochem J 281:577-592.