Inhibition of human catechol-O-methyltransferase (COMT)-mediated O-methylation of catechol estrogens by major polyphenolic components present in coffee

Journal of Steroid Biochemistry and Molecular Biology

Volumn 113, Issue 1-2, 2009, Pages 65-74

  Zhu, Bao Ting ^a   Wang, Pan ^a   Nagai, Mime ^a   Wen, Yujing ^a   Bai, Hyoung Woo ^a  

^a Shimane University School of Medicine   (United States)

Author keywords

2 Hydroxyestradiol; 4 Hydroxyestradiol; Catechol estrogens; Catechol O methyltransferase (COMT); Coffee polyphenols; Computational modeling; Enzyme inhibition; Estrogen metabolism; Liver; Placenta

Indexed keywords

2 HYDROXYESTRADIOL; 4 HYDROXYESTRADIOL; CAFFEIC ACID; CAFFEIC ACID PHENETHYL ESTER; CATECHOL ESTROGEN; CATECHOL METHYLTRANSFERASE; CHLOROGENIC ACID; POLYPHENOL;

ARTICLE; CATALYSIS; COFFEE; COMPUTER MODEL; CONTROLLED STUDY; CYTOSOL; ENZYME INHIBITION; ENZYME KINETICS; FEMALE; HUMAN; HUMAN TISSUE; IN VITRO STUDY; METHYLATION; MOLECULAR MODEL;

ADULT; BIOCATALYSIS; CAFFEIC ACIDS; CATECHOL O-METHYLTRANSFERASE; CHLOROGENIC ACID; COFFEE; COMPUTATIONAL BIOLOGY; CYTOSOL; ESTROGENS, CATECHOL; FEMALE; FLAVONOIDS; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; LIVER; METHYLATION; MODELS, MOLECULAR; PHENOLS; PHENYLETHYL ALCOHOL; PLACENTA; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY;

EID: 59849118023     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2008.11.011     Document Type: Article

References (33)

1. Zhu B.T., and Conney A.H. Is 2-methoxyestradiol an endogenous estrogen metabolite that inhibits mammary carcinogenesis?. Cancer Res. 58 (1998) 2269-2277
2. Pribluda V.S., Gubish Jr. E.R., Lavallee T.M., Treston A., Swartz G.M., and Green S.J. 2-Methoxyestradiol: an endogenous antiangiogenic and antiproliferative drug candidate. Cancer Metastasis Rev. 19 (2000) 173-179
3. Axelrod J., and Tomchick R. Enzymatic O-methylation of epinephrine and other catechols. J. Biol. Chem. 233 (1958) 702-705
4. Axelrod J. Methylation reactions in the formation and metabolism of catecholamines and other biogenic amines. Pharmacol. Rev. 18 (1966) 95-113
5. Lautala P., Ulmanen I., and Taskinen J. Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. Mol. Pharmacol. 59 (2001) 393-402
6. Bai H.W., Shim J.Y., and Zhu B.T. Biochemical and molecular modeling studies of the O-methylation of various endogenous and exogenous catechol substrates catalyzed by recombinant human soluble and membrane-bound catechol-O-methyltransferases. Chem. Res. Toxicol. 20 (2007) 1409-1425
7. Zhu B.T. Catechol-O-methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: importance in pathophysiology and pathogenesis. Curr. Drug Metab. 3 (2002) 321-349
8. Zhu B.T., Ezell E.L., and Liehr J.G. Catechol-O-methyltransferase-catalyzed O-methylation of mutagenic flavonoids: metabolic inactivation as possible reason for their lack of carcinogenicity in vivo. J. Biol. Chem. 269 (1994) 292-299
9. Zhu B.T., Patel U.K., Cai M.X., and Conney A.H. Metabolic O-methylation of tea polyphenols catalyzed by human placental cytosolic catechol-O-methyltransferase. Drug Metab. Dispos. 28 (2000) 1024-1030
10. Zhu B.T., Patel U.K., Cai M.X., Lee A.J., and Conney A.H. Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase. Xenobiotica 31 (2001) 879-890
11. Zhu B.T., and Liehr J.G. Quercetin increases the severity of estradiol-induced tumorigenesis in hamster kidney. Toxicol. Appl. Pharmacol. 125 (1994) 149-158
12. Zhu B.T., and Liehr J.G. Inhibition of catechol O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin: possible role in estradiol-induced tumorigenesis. J. Biol. Chem. 271 (1996) 1357-1363
13. Nagai M., Conney A.H., and Zhu B.T. Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. Drug Metab. Dispos. 32 (2004) 497-504
14. Zhu B.T., Shim J.Y., Nagai M., and Bai H.W. Molecular mechanism for the high-potency inhibition of human catechol-O-methyltransferase by (-)-epigallocatechin-3-O-gallate. Xenobiotica 38 (2008) 130-146
15. Chen D., Wang C.Y., Lambert J.D., Ai N., Welsh W.J., and Yang C.S. Inhibition of human liver catechol-O-methyltransferase by tea catechins and their metabolites: structure-activity relationship and molecular-modeling studies. Biochem. Pharmacol. 69 (2005) 1523-1531
16. Lu H., Meng X., and Yang C.S. Enzymology of methylation of tea catechins and inhibition of catechol-O-methyltransferase by (-)-epigallocatechin gallate. Drug Metab. Dispos. 31 (2003) 572-579
17. Ueland P.M. Pharmacological and biochemical aspects of S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase. Pharmacol. Rev. 34 (1982) 223-253
18. Monteiro M., Farah A., Perrone D., Trugo L.C., and Donangelo C. Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J. Nutr. 137 (2007) 2196-2201
19. Lafay S., Morand C., Manach C., Besson C., and Scalbert A. Absorption and metabolism of caffeic acid and chlorogenic acid in the small intestine of rats. Br. J. Nutr. 96 (2006) 39-46
20. Olthof M.R., Hollman P.C., and Katan M.B. Chlorogenic acid and caffeic acid are absorbed in humans. J. Nutr. 131 (2001) 66-71
21. Azuma K., Ippoushi K., Nakayama M., Ito H., Higashio H., and Terao J. Absorption of chlorogenic acid and caffeic acid in rats after oral administration. J. Agric. Food Chem. 48 (2000) 5496-5500
22. Lavigne J.A., Helzlsouer K.J., Huang H.Y., Strickland P.T., Bell D.A., Selmin O., Watson M.A., Hoffman S., Comstock G.W., and Yager J.D. Cancer Res. 57 (1997) 5493-5497
23. Thompson P.A., Shields P.G., Freudenheim J.L., Stone A., Vena J.E., Marshall J.R., Graham S., Laughlin R., Nemoto T., Kadlubar F.F., and Ambrosone C.B. Genetic polymorphisms in catechol-O-methyltransferase, menopausal status, and breast cancer risk. Cancer Res. 58 (1998) 2107-2110
24. Huang C.S., Chern H.D., Chang K.J., Cheng C.W., Hsu S.M., and Shen C.Y. Breast cancer risk associated with genotype polymorphism of the estrogen-metabolizing genes CYP17, CYP1A1, and COMT: a multigenic study on cancer susceptibility. Cancer Res. 59 (1999) 4870-4875
25. Yim D.S., Parkb S.K., Yoo K.Y., Yoon K.S., Chung H.H., Kang H.L., Ahn S.H., Noh D.Y., Choe K.J., Jang I.J., Shin S.G., Strickland P.T., Hirvonen A., and Kang D. Relationship between the Val158Met polymorphism of catechol O-methyl transferase and breast cancer. Pharmacogenetics 11 (2001) 279-286
26. Wen W., Cai Q., Shu X.O., Cheng J.R., Parl F., Pierce L., Gao Y.T., and Zheng W. Cytochrome P450 1B1 and catechol-O-methyltransferase genetic polymorphisms and breast cancer risk in Chinese women: results from the shanghai breast cancer study and a meta-analysis. Cancer Epidemiol. Biomarkers Prev. 14 (2005) 329-335
27. Mitrunen K., Jourenkova N., Kataja V., Eskelinen M., Kosma V.M., Benhamou S., Kang D., Vainio H., Uusitupa M., and Hirvonen A. Polymorphic catechol-O-methyltransferase gene and breast cancer risk. Cancer Epidemiol. Biomarkers Prev. 10 (2001) 635-640
28. Goodman J.E., Lavigne J.A., Wu K., Helzlsouer K.J., Strickland P.T., Selhub J., and Yager J.D. COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk. Carcinogenesis 22 (2001) 1661-1665
29. Liehr J.G. Is estradiol a genotoxic mutagenic carcinogen?. Endocr. Rev. 21 (2000) 40-54
30. Cavalieri E., Frenkel K., Liehr J.G., Rogan E., and Roy D. Estrogens as endogenous genotoxic agents-DNA adducts and mutations. J. Natl. Cancer Inst. Monogr. 27 (2000) 75-93
31. Zhu B.T., and Conney A.H. Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis 19 (1998) 1-27
32. S.A. Park, H.K. Na, E.H. Kim, Y.N. Cha, Y.J. Surh, 4-Hydroxyestradiol induces anchorage-independent growth of human mammary epithelial cells via activation of IκB kinase: potential role of ROS. Cancer Res. (2008) (Epub ahead of print).
33. Deschner E.E., Ruperto J., Wong G., and Newmark H.L. Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis 12 (1991) 1193-1196