Methylation protects dietary flavonoids from rapid hepatic metabolism

References

• Abe K, Inoue O, Yumioka E. Biliary excretion of metabolites of baicalin and baicalein in rats. Chemistry and Pharmacology Bulletin (Tokyo) 1990; 38: 209–211
   PubMed Web of Science ®Google Scholar
• Ahmad F, Bakar SA, Ibrahim AZ, Read RW. Constituents of the leaves of Piper caninum. Planta Medica 1997; 63: 193–194
   PubMed Web of Science ®Google Scholar
• Boutin JA, Meunier F, Lambert PH, Hennig P, Bertin D, Serkiz B, Volland JP. In vivo and in vitro glucuronidation of the flavonoid diosmetin in rats. Drug Metabolism and Disposition 1993; 21: 1157–1166
   PubMed Web of Science ®Google Scholar
• Breinholt VM, Rasmussen SE, Brosen K, Friedberg TH. In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s. Pharmacology and Toxicology 2003; 93: 14–22
   PubMedGoogle Scholar
• Budzianowski J, Morozowska M, Wesolowska M. Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures. Phytochemistry 2005; 66: 1033–1039
   PubMed Web of Science ®Google Scholar
• Garcea G, Jones DJ, Singh R, Dennison AR, Farmer PB, Sharma RA, Steward WP, Gescher AJ, Berry DP. Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration. British Journal of Cancer 2004; 90: 1011–1015
   PubMed Web of Science ®Google Scholar
• Haberlein H, Tschiersch KP. On the occurrence of methylated and methoxylated flavonoids in Leptospermum scoparium. Biochemical Systematics and Ecology 1998; 26: 97–103
   Web of Science ®Google Scholar
• Houston JB. Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochemistry and Pharmacology 1994; 47: 1469–1479
   PubMed Web of Science ®Google Scholar
• Hu M, Krausz K, Chen J, Ge X, Li J, Gelboin HL, Gonzalez FJ. Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. Drug Metabolism and Disposition 2003; 31: 924–931
   PubMed Web of Science ®Google Scholar
• Ireson CR, Jones DJ, Orr S, Coughtrie MW, Boocock DJ, Williams ML, Farmer PB, Steward WP, Gescher AJ. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiology and Biomarkers Prevention 2002; 11: 105–111
   PubMed Web of Science ®Google Scholar
• Jones DJ, Lamb JH, Verschoyle RD, Howells LM, Butterworth M, Lim CK, Ferry D, Farmer PB, Gescher AJ. Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. British Journal of Cancer 2004; 91: 1213–1219
   PubMed Web of Science ®Google Scholar
• Kaldas MI, Walle UK, Walle T. Resveratrol transport and metabolism by human intestinal Caco-2 cells. Journal of Pharmacy and Pharmacology 2003; 55: 307–312
   PubMed Web of Science ®Google Scholar
• Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. Journal of Biology and Chemistry 1951; 193: 265–275
   PubMed Web of Science ®Google Scholar
• Manach C, Morand C, Crespy V, Demigne C, Texier O, Regerat F, Remesy C. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Letters 1998; 426: 331–336
   PubMed Web of Science ®Google Scholar
• Manach C, Williamson G, Morand C, Scalbert A, Remesy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. American Journal of Clinical Nutrition 2005; 81: 230S–242S
   PubMed Web of Science ®Google Scholar
• McGinnity DF, Soars MG, Urbanowicz RA, Riley RJ. Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance. Drug Metabolism and Disposition 2004; 32: 1247–1253
   PubMed Web of Science ®Google Scholar
• Obach RS. Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: An examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metabolism and Disposition 1999; 27: 1350–1359
   PubMed Web of Science ®Google Scholar
• Obach RS, Baxter JG, Liston TE, Silber BM, Jones BC, MacIntyre F, Rance DJ, Wastall P. The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data. Journal of Pharmacology and Experimental Therapy 1997; 283: 46–58
   PubMed Web of Science ®Google Scholar
• Otake Y, Walle T. Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9. Drug Metabolism and Disposition 2002; 30: 103–105
   PubMed Web of Science ®Google Scholar
• Otake Y, Hsieh F, Walle T. Glucuronidation versus oxidation of the flavonoid galangin by human liver microsomes and hepatocytes. Drug Metabolism and Disposition 2002; 30: 576–581
   PubMed Web of Science ®Google Scholar
• Segel IH. Enzyme kinetics. Wiley, New York, NY 1975
   Google Scholar
• Soars MG, Burchell B, Riley RJ. In vitro analysis of human drug glucuronidation and prediction of in vivo metabolic clearance. Journal of Pharmacology and Experimental Therapy 2002; 301: 382–390
   PubMed Web of Science ®Google Scholar
• Walle T. Absorption and metabolism of flavonoids. Free Radicals in Biology and Medicine 2004; 36: 829–837
   PubMed Web of Science ®Google Scholar
• Walle T, Hsieh F, DeLegge MH, Oatis JE, Jr, Walle UK. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metabolism and Disposition 2004; 32: 1377–1382
   PubMed Web of Science ®Google Scholar
• Walle T, Otake Y, Brubaker JA, Walle UK, Halushka PV. Disposition and metabolism of the flavonoid chrysin in normal volunteers. British Journal of Clinical Pharmacology 2001; 51: 143–146
   PubMed Web of Science ®Google Scholar
• Walle UK, Galijatovic A, Walle T. Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2. Biochemistry and Pharmacology 1999; 58: 431–438
   PubMed Web of Science ®Google Scholar
• Wen X, Walle T. Preferential induction of CYP1B1 by benzo[a]pyrene in human oral epithelial cells: Impact on DNA adduct formation and prevention by polyphenols. Carcinogenesis 2005; 26: 1774–1781
   PubMed Web of Science ®Google Scholar
• Wen X, Walle UK, Walle T. 5,7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells. Carcinogenesis 2005; 26: 803–809
   PubMed Web of Science ®Google Scholar
• Williamson G, Manach C. Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies. American Journal of Clinical Nutrition 2005; 81: 243S–255S
   PubMed Web of Science ®Google Scholar