Diterpene quinone tanshinone IIA selectively inhibits mouse and human cytochrome P4501A2

Xenobiotica

Volumn 33, Issue 6, 2003, Pages 603-613

  Ueng, Yune Fang ^a   Kuo, Ya Hui ^b   Peng, Hsiao Chi ^a   Chen, Ta Liang ^d   Jan, Woan Ching ^d   Guengerich, F Peter ^c   Lin, Yun Lian ^a  

^a NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^b NATIONAL YANG MING UNIVERSITY   (Taiwan)

^c VANDERBILT UNIVERSITY   (United States)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLCHOLANTHRENE; 7 METHOXYRESORUFIN DEMETHYLASE; BENZO[A]PYRENE; CRYPTOTANSHINONE; CYTOCHROME P450 1A; CYTOCHROME P450 1A2; CYTOCHROME P450 INHIBITOR; DIMETHYLNITROSAMINE; DITERPENE; ETHOXYRESORUFIN; ETHOXYRESORUFIN DEETHYLASE; METHOXYRESORUFIN; MICROSOME ENZYME; NIFEDIPINE; QUINONE DERIVATIVE; RESORUFIN DERIVATIVE; TANSHINONE; TANSHINONE I; TOLBUTAMIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BACTERIAL MEMBRANE; BINDING KINETICS; COMPETITIVE INHIBITION; CONTROLLED STUDY; DEMETHYLATION; DISSOCIATION CONSTANT; DRUG EFFECT; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN TISSUE; HYDROXYLATION; IC 50; INHIBITION KINETICS; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; SALVIA MILTIORRHIZA; TANSHINONE IIA; XENOBIOTIC METABOLISM;

ALGORITHMS; ANIMALS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; DITERPENES; ENZYME INHIBITORS; HUMANS; KINETICS; MALE; MICE; MICE, INBRED C57BL; MICROSOMES, LIVER; OXIDATION-REDUCTION; PHENANTHRENES; SALVIA;

ANIMALIA; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; SALVIA; SALVIA MILTIORRHIZA;

EID: 0038772403     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/0049825031000105769     Document Type: Article

References (31)

1. ALVARES, A. P. and MANNERING, G. J., 1970, Two substrate kinetics of drug-metabolizing enzyme systems of hepatic microsomes. Molecular Pharmacology, 6, 206-212.
2. CAO, E H., LIU, X. Q., WANG, J. J. and XU, N. F., 1996, Effects of natural antioxidant tanshinone II-A on DNA damage by lipid peroxidation in liver cells. Free Radicals in Biology and Medicine, 20, 801-806.
3. CHEN, C. C., CHEN, H. T., CHEN, Y. P., HSU, H. Y. and HSIEH, T. C., 1986, Iodation of the components of Salviae miltiorrhizae radix and their coronary dilator activities. Taiwan Yao Hsueh Tsa Chih, 38, 226-230.
4. DEY, A., JONES, J. E. and NEBERT, D. W., 1999, Tissue- and cell type-specific expression of cytochrome P450 1A1 and cytochrome P450 1A1 mRNA in the mouse localized in situ hybridization. Biochemical Pharmacology, 58, 525-537.
5. GRADELET, S., ASTROG, P., PINEAU, T., CANIVENC, M. C., SIESS, M. H., LECLREC, J. and LESCA, P., 1997, Ah receptor-dependent CYP1A induction by two carotenoids, canthaxanthin and β-apo-8′-carotenal with no affinity for the TCDD binding site. Biochemical Pharmacology, 54, 307-315.
6. GUENGERICH, F. P., MARTIN, M. V., BEAUNE, P. H., KREMER, P., WOLFF, T. and WAXMAN, D. J., 1986, Characterization of rat and human liver microsomal cytochrome P450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 26, 5051-5060.
7. GUENGERICH, F. P., 1994, Analysis and characterization of enzymes. In A. W. Hayes (ed.), Principles and Methods of Toxicology (New York: Plenum), pp. 1259-1313.
8. GUENGERICH, F. P., 1995, Human cytochrome P450 enzymes. In P. R. Ortiz de Montellano (ed.), Cytochrome P450 (New York: Plenum), pp. 473-535.
9. GUENGERICH, F. P., 1997, Role of cytochrome P450 enzymes in drug-drug interactions. Advances in Pharmacology, 43, 7-35.
10. HONDA, G., KOEZUKA, Y. and TABATA, M., 1988, Isolation of an antidermatophytic substance from the root of Salvia miltiorrhiza. Chemical and Pharmaceutical Bulletin, 36, 408-411.
11. IOANNIDES, C., 2002, Pharmacokinetic interactions between herbal remedies and medicinal drugs. Xenobiotica, 32, 451-478.
12. KANG, B. Y., CHUNG, S. W., KIM, S. H., RYU, S. Y. and KIM, T. S., 2000, Inhibition of interleukin-12 and interferon-γ production in immune cells by tanshinones from Salvia miltiorrhiza. Immunopharmacology, 49, 355-361.
13. LIN, J. H. and LU, A. Y. H., 1998, Inhibition and induction of cytochrome P450 and the clinical implications. Clinical Pharmacokinetics, 35, 361-390.
14. LOWRY, O. H., ROSEBOROUGH, N. J., FARR, A. L. and RANDALL, R. L., 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265-275.
15. NASH, T., 1953, The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal, 55, 416-421.
16. NEBERT, D. W. and GELBOIN, H. V., 1968, Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. 1. Assembly and properties of induced enzyme. Journal of Biological Chemistry, 243, 6242-6249.
17. OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. 1. Evidence for its hemeprotein nature. Journal of Biological Chemistry, 239, 2370-2379.
18. ONITSUKA, M., FUJIU, M., SHINMA, N. and MARUYAMA, H. B., 1983, New platelet aggregation inhibitors from Tan-Shen; radix of Salvia miltiorrhiza Bunge. Chemical and Pharmaceutical Bulletin, 31, 1670-1675.
19. PARIKH, A., GILLAM, E. M. J. and GUENGERICH, F. P., 1997, Drug metabolism by Escherichia coli expressing human cytochrome P450. Natural Biotechnology, 15, 784-788.
20. PETER, R., BÖCKER, R., BEAUNE, P. H., IWASAKI, M., GUENGERICH, F. P. and YANG, C. S., 1990, Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450IIE1. Chemical Research in Toxicology, 3, 566-573.
21. PHILLIPS, A. H. and LANGDON, R. G., 1962, Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. Journal of Biological Chemistry, 237, 2652-2660.
22. POHL, R. J. and FOUTS, J. R., 1980, A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Analytical Biochemistry, 107, 150-155.
23. RYU, S. Y., NO, Z., KIM, S. H. and AHN, J. W., 1997, Two novel abietane diterpenes from Salvia miltiorrhiza. Planta Medica, 63, 44-46.
24. SATO, M., SATO, T., OSE, Y., NAGASE, H., KITO, H. and SAKAI, Y., 1992, Modulating effect of tanshinones on mutagenic activity of Trp-P-1 and benzo(a)pyrene in Salmonella typhimurium. Mutation Research, 265, 149-154.
25. SCHENKMAN, J. B., REMMER, H. and ESTABROOK, R. W., 1967, Spectral studies of drug interaction with hepatic microsomal cytochrome. Molecular Pharmacology, 3, 113-123.
26. SOUČEK, P., 1999, Cytochrome P450 destruction by quinones: comparison of effects in rat and human liver microsomes. Chemical-Biological Interactions, 121, 223-236.
27. UENG, Y. F., JAN, W. C., LIN, L. C., CHEN, T. L., GUENGERICH, F. P. and CHEN, C. F., 2002, The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug Metabolism and Disposition, 30, 349-353.
28. WU, T. W., ZENG, L. H., FUNG, K. P., WU, J., PANG, H., GREY, A. A., WEISEL, R. D. and WANG, J. Y., 1993, Effect of sodium tanshinone IIA sulfonate in the rabbit myocardium and on human cardiomyocytes and vascular endothelial cells. Biochemical Pharmacology, 46, 2327-2332.
29. WU, W. L., CHANG, W. L. and CHEN, C. F., 1991, Cytotoxic activities of tanshinones against human carcinoma cell lines. American Journal of Chinese Medicine, 19, 207-216.
30. YAMAZAKI, H., INOUE, K. and SHIMADA, T., 1998, Roles of two allelic variants (Arg144Cys and ILE359Leu) of cytochrome P450 2C9 in the oxidation of tolbutamide and warfarin by human liver microsomes. Xenobiotica, 28, 103-115.
31. YOON, Y., KIM, Y. O., JEON, W. K., PARK, H. J. and SUNG, H. J., 1999, Tanshinone IIA isolated from Salvia miltiorrhiza BUNGE induced apoptosis in HL60 human premyelocytic leukemia cell line. Journal of Ethanopharmacology, 58, 121-127.