Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase

References

• AXELROD, J., 1966, Methylation reactions in the formation and metabolism of catecholamines and other biogenic amines. Pharmacological Reviews, 18, 95–113.
   PubMed Web of Science ®Google Scholar
• AXELROD, J. and TOMCHICK, R., 1958, Enzymatic 0-methylation of epinephrine and other catechols. Journal of Biological Chemistry, 233, 702–705.
   PubMed Web of Science ®Google Scholar
• BALENTINE, D. A., 1992, Manufacturing and chemistry of tea. In C. T. Ho, M. T. Huang and C. Y. Lee (eds), Phenolic Compounds in Food and their Effects on Health I (Washington, DC: American Chemical Society Press), pp. 102–117.
   Google Scholar
• CREVELING, C. R., DELGARD, N., Sciumizu, H. and DALY, J. W., 1970, Catechol 0-methyltransferase. 3. m- and p-O-methylation of catecholamines and their metabolites. Molecular Pharmacology, 6, 691–696.
   PubMed Web of Science ®Google Scholar
• CREVELING, C. R., MORRIS, N., ONG, H. H. and DALY, J. W., 1972, Catechol 0-methyltransferase. IV. Factors affecting m- and p-methylation of substituted catechols. Molecular Pharmacology, 8, 398–409.
   PubMed Web of Science ®Google Scholar
• GULDBERG, H. C. and MARSDEN, C. A., 1975, Catechol-O-methyltransferase: Pharmacological aspects and physiological role. Pharmacological Reviews, 27, 135–206.
   PubMed Web of Science ®Google Scholar
• HACKETT, A. M. and GRIFFITHS, L. A., 1981, The metabolism and excretion of 3-0-methyl-(±)-catechin in the rat, mouse, and marmoset. Drug Metabolism and Disposition, 9, 54–59.
   PubMed Web of Science ®Google Scholar
• HACKETT, A. M., SHAW, I. C. and GRITHS, L. A., 1982, 3'-0-methyl-(±)-catechin glucuronide and 3'-0-methyl-(±)-catechin sulphate: new urinary metabolites of (±)-catechin in the rat and the marmoset. Experientia, 38, 538–540.
   PubMedGoogle Scholar
• KUHNLE, G., SPENCER, J. P. E., SCHROETER, H., SHENOY, B., DEBNAM, E. S., SRI, S. K. S., RICE-EVANS, C. and HAHN, U., 2000, Epicatechin and catechin are 0-methylated and glucuronidated in the small intestine. Biochemical and Biophysical Research Communications, 277, 507–512.
   Google Scholar
• LEE, M.-J., WANG, Z.-Y., Li, H., CHEN, L., SUN, Y., GOBBO, S., BALENTINE, D. A. and YANG, C. S., 1995, Analysis of plasma and urinary tea polyphenols in human subjects. Cancer Epidemiology, Biomarker, and Prevention, 4, 393–399.
   Google Scholar
• Li, C., LEE, M. J., SHENG, S., MENG, X., PRABHU, S., WINNIK, B., HUANG, B., CHUNG, J. Y., YAN, S., Ho, C. T. and YANG, C. S., 2000, Structural identification of two metabolites of catechins and their kinetics in human urine and blood after tea ingestion. Chemical Research in Toxicology, 13, 177–184.
   PubMed Web of Science ®Google Scholar
• LIEHR, J. G., 2000, Is estradiol a genotoxic mutagenic carcinogen? Endocrine Reviews, 21, 40–54.
   Google Scholar
• PISITUUA, M. K. and TERAO, J., 1998, Accumulation of (—)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues. Journal of Nutrition, 128, 1172–1178.
   PubMedGoogle Scholar
• SANO, M., SUZUKI, M., MIYASE, T., YOSHINO, K. and MAEDA-YAMAMOTO, M., 1999, Novel antiallergic catechin derivatives isolated from oolong tea. Journal of Agricultural and Food Chemistry, 47, 1906–1 910.
   Google Scholar
• SUGANUMA, M., OKABE, S., ONIYAMA, M., TADA, Y., Pro, H. and FUJIKI, H., 1998, Wide distribution of [31-1](—)-epigallocatechin gallate, a cancer preventive tea polyphenol, in mouse tissue. Carcinogenesis, 19, 1771–1776.
   PubMed Web of Science ®Google Scholar
• THAKKER, D. R. and CREVELING, C. R., 1990, 0-methylation. In G. J. Mulder (ed.), Conjugation Reactions in Drug Metabolism (London: Taylor & Francis), pp. 193–232.
   Google Scholar
• UELAND, P. M., 1982, Pharmacological and biochemical aspects of S-adenosylhomocysteine and S-adenosylhomo cysteine hydrolase. Pharmacological Reviews, 34, 223–253.
   PubMed Web of Science ®Google Scholar
• UNNO, T., KONDO, K., ITAKURA, H. and TAKEO, T., 1996, Analysis of (—)-epigallocatechin gallate in human serum obtained after ingesting green tea. Bioscience, Biotechnology and Biochemistry, 60, 2066–2068.
   PubMed Web of Science ®Google Scholar
• VAN HET HOF, K. H., KIVITS, G. A. A., WESTSTRATE, J. A. and TIJBURG, L. B. M., 1998, Bioavailability of catechins from tea: the effect of milk. European Journal of Clinical Nutrition, 52, 356–359.
   Google Scholar
• WAGNER, J., CLAVERIE, N. and DANZINM, C., 1984, A rapid high-performance liquid chromatographic procedure for the simultaneous determination of methionine, ethionine, S-adenosylmethionine, S-adenosylethionine, and the natural polyamines in rat tissues. Analytical Biochemistry, 140, 108–116.
   PubMed Web of Science ®Google Scholar
• YANG, C. S., CHEN, L., LEE, M.-J., BALENTINE, D., Kuo, M. C. and SCHANTZ, S. P., 1998, Blood and urine levels of tea catechins after ingestion of different amounts of green tea by human volunteers. Cancer Epidemiology, Biomarkers and Prevention, 7, 351–354.
   Google Scholar
• Zuu, B. T. and CONNEY, A. H., 1998, Is 2-methoxyestradiol an endogenous estrogen metabolite that inhibits mammary carcinogenesis? Cancer Research, 58, 2269–2277.
   Google Scholar
• Zim, B. T., EZELL, E. L. and LIEHR, J. G., 1994, Catechol-O-methyltransferase-catalyzed 0-methylation of mutagenic flavonoids: metabolic inactivation as possible reason for their lack of carcinogenicity in vivo. Journal of Biological Chemistry, 269, 292–299.
   PubMedGoogle Scholar
• Znu, B. T. and LIEHR, J. G., 1994, Quercetin increases the severity of estradiol-induced tumorigenesis in hamster kidney. Toxicology and Applied Pharmacology, 125, 149–158.
   PubMedGoogle Scholar
• Zim, B. T. and LIEHR, J. G., 1996, Inhibition of catechol-O-methyltransferase-catalyzed 0-methylation of 2- and 4-hydroxyestradiol by quercetin. Journal of Biological Chemistry, 271, 1367–1363.
   Google Scholar
• Zim, B. T., PATEL, U. K., CAI, M. X. and CONNEY, A. H., 2000, 0-Methylation of tea polyphenols catalysed by human placental cytosolic catechol-O-methyltransferase. Drug Metabolism and Disposition, 28, 1024–1030.
   PubMedGoogle Scholar
• ZHU, B. T., TANEJA, N., LODER, D. P., BALENTINE, D. A. and CONNEY, A. H., 1998, Effects of tea polyphenols and flavonoids on liver microsomal glucuronidation of estradiol and estrone. You mat of Steroid Biochemistry and Molecular Biology, 64, 207–215.
   PubMed Web of Science ®Google Scholar