In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus

Xenobiotica

Volumn 30, Issue 3, 2000, Pages 235-251

  Henderson, M C ^a   Miranda, C L ^a   Stevens, J F ^a   Deinzer, M L ^a   Buhler, D R ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHOXYCOUMARIN DEETHYLASE; CARCINOGEN; CHALCONE DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 3A4; FLAVONOID;

ANGIOSPERM; ARTICLE; CHEMICAL STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; NONHUMAN; PROTEIN BINDING;

HUMULUS; HUMULUS LUPULUS; MAGNOLIOPHYTA;

EID: 0034027685     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982500237631     Document Type: Article

References (44)

1. 1. Proceedings of the National Academy of Sciences, USA, 87, 4790-4793.
2. Aponso, L., Miranda, C. L., Stevens, J. F., Deinzer, M. L. and Buhler, D. R., 1998, Induction of quinone reductase by flavonoids from hops (Humulus lupulus) in cultured mouse hepatoma (Hepa 1c1c7) cells. Toxicological Sciences, 42, 185.
3. Arimoto-Kobayashi, S., Sugiyama, C., Harada, N., Takeuchi, M., Takemura, M. and Hayatsu, H., 1999, Inhibitory effects of beer and other alcoholic beverages on mutagenesis and DNA adduct formation induced by several carcinogens. Journal of Agricultural and Food Chemistry, 47, 221-230.
4. Bohm, B. A., 1993, The minor flavonoids. In J. B. Harborne (ed.), The Flavonoids (New York: Chapman & Hall), pp. 387-440.
5. Chang, T. K. H., Gonzalez, F. J. and Waxman, D. J., 1994, Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human P450. Archives of Biochemistry and Biophysics, 311, 437-442.
6. Code, E. L., Crespi, C. L., Penman, B. W., Gonzalez, F. J., Chang, T. K. and Waxman, D. J., 1997, Human cytochrome P4502B6: interindividual hepatic expression, substrate specificity, and role in procarcinogen activation. Drug Metabolism and Disposition, 25, 985-993.
7. Edenharder, R., Rauscher, R. and Platt, K. L., 1997, The inhibition by flavonoids of 2-amino-3-methylimidazo[4,5-f]quinoline metabolic activation to a mutagen: a structure - activity relationship study. Mutation Research, 379, 21-32.
8. 1 oxidation by human cDNA-expressed and human liver microsomal cytochromes P450 1A2 and 3A4. Toxicology and Applied Pharmacology, 141, 595-606.
9. Gonzalez, F. J. and Gelboin, H. V., 1994, Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metabolism Reviews, 26, 165-183.
10. Guengerich, F. P., 1989, Analysis and characterization of enzymes. In A. Wallace Hayes (ed.), Principles and Methods of Toxicology, 2nd edn, pp. 777-813.
11. Guengerich, F. P., 1995, Human cytochrome P450 enzymes. In P. R. Ortiz de Montellano (ed.), Cytochrome P450: Structure, Mechanism, and Biochemistry, 2nd edn (New York: Plenum), pp. 473-535.
12. Guengerich, F. P. and Kim, D. H., 1990, In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis, 11, 2275-2279.
13. Guengerich, F. P., Martin, M. V., Beaune, P. H., Kremers, P., Wolff, T. and Waxman, D. J., 1986, Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. Journal of Biological Chemistry, 261, 5051-5060.
14. Guengerich, F. P. and Shimada, T., 1991, Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chemical Research in Toxicology, 4, 391-407.
15. Guengerich, F. P., Shimada, T., Raney, K. D., Yun, C. H., Meyer, D. J., Ketterer, B., Harris, T. M., Groopman, J. D. and Kadlubar, F. F., 1992, Elucidation of the catalytic specificities of human cytochrome P450 and glutathione S-transferase enzymes and relevance to molecular epidemiology. Environmental Health Perspectives, 98, 75-80.
16. Guengerich, F. P., Shimada, T., Yun, C. H., Yamazaki, H., Raney, K. D., Thier, R., Coles, B. and Harris, T. M., 1994, Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Environmental Health Perspectives, 102 (suppl. 9), 49-53.
17. Henderson, M. C., Miranda, C. L., Stevens, J. F., Deinzer, M. L. and Buhler, D. R., 1998, In vitro inhibition of carcinogen metabolism by flavonoids from hops (Humulus lupulus) in various species. Toxicological Science, 42, 185.
18. Liu, G., Gelboin, H. V. and Myers, M. J., 1991, Role of cytochrome P450 1A2 in acetanilide 4-hydroxylation as determined with cDNA expression and monoclonal antibodies. Archives of Biochemistry and Biophysics, 284, 400-406.
19. 1 metabolism. Carcinogenesis, 18, 1729-1738.
20. Middleton, E. Jr and Kandaswami, C., 1994, The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In J. B. Harborne (ed.), The Flavonoids (New York: Chapman & Hall), pp. 619-652.
21. Miranda, C. L. Stevens, J. F., Helmrich, A., Henderson, M. C., Rodriguez, R. J., Yang, Y.-H., Deinzer, M. L., Barnes, D. W. and Buhler, D. R., 1999, Anti-proliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food and Chemical Toxicology, 37, 271-285.
22. Mukhtar, H. and Ahmad, N., 1999, Cancer chemoprevention: future holds in multiple agents. Toxicology and Applied Pharmacology, 158, 207-210.
23. Newton, D. J., Wang, R. W. and Lu, A. Y. H., 1995, Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metabolism and Disposition, 23, 154-158.
24. Obermeier, M. T., White, R. E. and Yang, C. S., 1995, Effects of bioflavonoids on hepatic P450 activities. Xenobiotica, 25, 575-584.
25. Penman, B. W., Chen, L., Gelboin, H. V., Gonzalez, F. J. and Crespi, C. L., 1994, Development of a human lymphoblastoid cell line constitutively expressing human CYP1A1 cDNA: substrate specificity with model substrates and promutagens. Carcinogenesis, 15, 1931-1937.
26. Peter, R., Bocker, R. G., 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-450 IIE1. Chemical Research in Toxicology, 3, 566-573.
27. Pezzuto, J. M., 1997, Plant-derived anticancer agents. Biochemical Pharmacology, 53, 121-133.
28. Pohl, R. J. and Fouts, J. R., 1980, A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Annals of Biochemistry, 107, 150-155.
29. Shimada, T., Hayes, C. L., Yamazaki, H., Amin, S., Hecht, S. S., Guengerich, F. P. and Sutter, T. R., 1996, Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1. Cancer Research, 56, 2979-2984.
30. Shou, M., Korzekwa, K. R., Crespi, C. L., Gonzalez, F. J. and Gelboin, H. V., 1994, The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of the benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Molecular Carcinogenesis, 10, 159-168.
31. Shou, M., Korzekwa, K. R., Krausz, K. W., Buters, J. T., Grogan, J., Goldfarb, I., Hardwick, J. P., Gonzalez, F. J. and Gelboin, H. V., 1996b, Specificity of cDNA-expressed human and rodent cytochrome P450 in the oxidative metabolism of the potent carcinogen 7,12-dimethybenz[a]anthracene. Molecular Carcinogenesis, 17, 241-249.
32. Shou, M., Krausz, K. W., Gonzalez, F. J. and Gelboin, H. V., 1996a, Metabolic activation of the potent carcinogen dibenzo[a,l]pyrene by human recombinant cytochromes P450, lung and liver microsomes. Carcinogenesis, 17, 2429-2433.
33. Shou, M., Krausz, K. W., Gonzalez, F. J. and Gelboin, H. V., 1996c, Metabolic activation of the potent carcinogen dibenzo[a,h]anthracene by cDNA-expressed human cytochromes P450. Archives of Biochemistry and Biophysics, 328, 201-207.
34. Siess, M.-H., Leclerc, J., Canivenc-Lavier, M.-C., Rat, P. and Suschetet, M., 1995, Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicology and Applied Pharmacology, 130, 73-78.
35. Stevens, J. F., Ivancic, M., Hsu, V. L. and Deinzer, M. L., 1997, Prenylflavonoids from Humulus lupulus. Phytochemistry, 44, 1575-1585.
36. Stevens, J. F., Miranda, C. L., Buhler, D. R. and Deinzer, M. L, 1998, Chemistry and biology of hop flavonoids. Journal of the American Society of Brewing Chemistry, 56, 136-145.
37. Stevens, J. F., Taylor, A. W. and Deinzer, M. L., 1999a, Quantitative analysis of xanthohumol and related flavonoids in hops and beer by liquid chromatography tandem mass spectrometry. Journal of Chromatography, A832, 97-107.
38. Stevens, J. F. Taylor, A. W., Clawson, J. E. and Deinzer, M. L., 1999b, Fate of xanthohumol and related prenylflavonoids from hops to beer. Journal of Agricultural and Food Chemistry, 47, 2421-2428.
39. 1-exo-epoxide. Drug Metabolism and Disposition, 22, 392-399.
40. Tassaneeyakul, W., Birkett, D. J., Veronese, M. E., McManus, M. E., Tukey, R. H., Quattrochi, L. C., Gelboin, H. V. and Miners, J. O., 1993, Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. Journal of Pharmacology and Experimental Therapeutics, 265, 401-407.
41. Tsyrlov, I. B., Mikhailenko, V. M. and Gelboin, H. V., 1994, Isozyme-and species-specific susceptibility of cDNA-expressed CYP1A P-450s to different flavonoids. Biochimica et Biophysica Acta, 1205, 325-335.
42. Wattenburg, L. W., 1983, Inhibition of neoplasia by minor dietary constituents. Cancer Research, 26, 1520-1526.
43. Yilmazer, M., Stevens, J. F., Deinzer, M. L. and Buhler, D. R., 1999, In vitro biotransformation of xanthohumol by rat liver microsomes. Toxicological Sciences, 48, 223.
44. Zhao, K., Surray, S., Davies, D. S., Boobis, A. R. and Goodersham, N. J., 1994, Metabolism of the food derived mutagen and carcinogen 2-amino-1-methyl 6-phenylimidazo(4,5-b)pyridine (Ph1P) by human liver microsomes. Carcinogenesis, 15, 1285-1288.