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Xenobiotica
the fate of foreign compounds in biological systems
Volume 36, 2006 - Issue 5
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Research Article

Methylation protects dietary flavonoids from rapid hepatic metabolism

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Pages 387-397 | Received 13 Jan 2006, Published online: 22 Sep 2008

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Jian-Min Zhou & Ragai K. Ibrahim. (2009) Tricin—a potential multifunctional nutraceutical. Phytochemistry Reviews 9:3, pages 413-424.
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Massimo D’Archivio, Carmelina Filesi, Rosaria Varì, Beatrice Scazzocchio & Roberta Masella. (2010) Bioavailability of the Polyphenols: Status and Controversies. International Journal of Molecular Sciences 11:4, pages 1321-1342.
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Thomas Walle & U Kristina Walle. (2007) Novel methoxylated flavone inhibitors of cytochrome P450 1B1 in SCC-9 human oral cancer cells. Journal of Pharmacy and Pharmacology 59:6, pages 857-862.
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Iain A. Murray, Colin A. Flaveny, Brett C. DiNatale, Chris R. Chairo, Jennifer C. Schroeder, Ann Kusnadi & Gary H. Perdew. (2010) Antagonism of Aryl Hydrocarbon Receptor Signaling by 6,2′,4′-Trimethoxyflavone. Journal of Pharmacology and Experimental Therapeutics 332:1, pages 135-144.
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M. Otto, S. H. Hansen, L. Dalgaard, J. Dubois & L. Badolo. (2007) Development of an in vitro assay for the investigation of metabolism-induced drug hepatotoxicity. Cell Biology and Toxicology 24:1, pages 87-99.
Crossref
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U. Kristina Walle & Thomas Walle. (2007) Bioavailable Flavonoids: Cytochrome P450-Mediated Metabolism of Methoxyflavones. Drug Metabolism and Disposition 35:11, pages 1985-1989.
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Nga Ta & Thomas Walle. (2007) Aromatase inhibition by bioavailable methylated flavones. The Journal of Steroid Biochemistry and Molecular Biology 107:1-2, pages 127-129.
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Petra A. Tsuji & Thomas Walle. (2007) Benzo[a]pyrene-induced cytochrome P450 1A and DNA binding in cultured trout hepatocytes—Inhibition by plant polyphenols. Chemico-Biological Interactions 169:1, pages 25-31.
Crossref
Din Ung & Swati Nagar. (2007) Variable Sulfation of Dietary Polyphenols by Recombinant Human Sulfotransferase (SULT) 1A1 Genetic Variants and SULT1E1. Drug Metabolism and Disposition 35:5, pages 740-746.
Crossref
Thomas Walle, Nga Ta, Toshihiko Kawamori, Xia Wen, Petra A. Tsuji & U. Kristina Walle. (2007) Cancer chemopreventive properties of orally bioavailable flavonoids—Methylated versus unmethylated flavones. Biochemical Pharmacology 73:9, pages 1288-1296.
Crossref
Petra A. Tsuji, Richard N. Winn & Thomas Walle. (2006) Accumulation and metabolism of the anticancer flavonoid 5,7-dimethoxyflavone compared to its unmethylated analog chrysin in the Atlantic killifish. Chemico-Biological Interactions 164:1-2, pages 85-92.
Crossref
Xia Wen & Thomas Walle. (2006) Methylated Flavonoids Have Greatly Improved Intestinal Absorption and Metabolic Stability. Drug Metabolism and Disposition 34:10, pages 1786-1792.
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