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Xenobiotica
the fate of foreign compounds in biological systems
Volume 35, 2005 - Issue 2
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Research Article

Glucuronidation of bioflavonoids by human UGT1A10: structure–function relationships

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Pages 117-129 | Received 27 Sep 2004, Published online: 22 Sep 2008

References

  • Awad HM, Boersma MG, Boeren S, Van Bladeren PJ, Vervoort J, Rietjens IM. 2001. Structure—activity study on the quinone/quinone methide chemistry of flavonoids. Chemical Research in Toxicology 14:398–408.
  • Basu NK, Ciotti M, Hwang MS, Kole L, Mitra PS, Cho JW, Owens IS. 2004a. Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. Journal of Biological Chemistry 279:1429–1441.
  • Basu NK, Kubota S, Meselhy MR, Ciotti M, Chowdhury B, Hartori M, Owens IS. 2004b. Gastrointestinally-distributed UDP-glucuronosyltransferaselAl O which metabolizes estrogens and nonsteroidal anti-inflammatory drugs depends upon phosphorylation. Journal of Biological Chemistry 279:28320–28329.
  • Boersma MG, Van der WH, Bogaards J, Boeren S, Vervoort J, Cnubben NH, Van Iersel ML, Van Bladeren PJ, Rietjens IM. 2002. Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. Chemical Research in Toxicology 15:662–670.
  • Dekermendjian K, Kahnberg P, Witt MR, Sterner O, Nielsen M, Liljefors T. 1999. Structure—activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABA(A) receptor complex. Journal of Medicinal Chemistry 42:4343–4350.
  • Dutton G. 1980. Glucuronidation of drugs and other compounds. Boca Raton: CRC Press.
  • Edenharder R, Von P, Rauscher R. 1993. Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo [4,54] quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutation Research 287:261–274.
  • Forkmann G, Martens S. 2001. Metabolic engineering and applications of flavonoids. Current Opinion in Biotechnology 12:155–160.
  • Gong QH, Cho JW, Huang T, Potter C, Gholami N, Basu NK, Kubota S, Carvalho S, Pennington MW, Owens IS, Popescu NC. 2001. Thirteen UDPglucuronosyltransferase genes are encoded at the human UGT1 gene complex locus. Pharmacogenetics 11:357–368.
  • Hobbs S, Jitrapakdee S, Wallace JC. 1998. Development of a bicistronic vector driven by the human polypeptide chain elongation factor lalpha promoter for creation of stable mammalian cell lines that express very high levels of recombinant proteins. Biochemical and Biophysical Research Communications 252:368–372.
  • Huang X, Liu T, Gu J, Luo X, Ji R, Cao Y, Xue H, Wong JT, Wong BL, Pei G, Jiang H, Chen K. 2001.3D-QSAR model of flavonoids binding at benzodiazepine site in GABAA receptors. Journal of Medicinal Chemistry 44:1883–1891.
  • Kaur C, Kapoor HC. 2001. Antioxidants in fruits and vegetables — the millennium's health. International Journal of Food Science and Technology 36:703–725.
  • Mackenzie PI, Owens IS, Burchell B, Bock KW, Bairoch A, Belanger A, Fournel-Gigleux S, Green M, Hum DW, Iyanagi T, Lancet D, Louisot P, Magdalou J, Chowdhury JR, Ritter JK, Schachter H, Tephly TR, Tipton KF, Nebert DW. 1997. The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7:255–269.
  • Meech R, Mackenzie PI. 1998. Determinants of UDP glucuronosyltransferase membrane association and residency in the endoplasmic reticulum. Archives of Biochemistry and Biophysics 356:77–85.
  • Mojarrabi B, Mackenzie PI. 1997. The human UDP glucuronosyltransferase, UGT1A10, glucuronidates mycophenolic acid. Biochemical and Biophysical Research Communications 238:775–778.
  • Mojarrabi B, Mackenzie PI. 1998. Characterization of two UDP glucuronosyltransferases that are predominantly expressed in human colon. Biochemical and Biophysical Research Communications 247:704–709.
  • Mojarrabi B, Butler R, Mackenzie PI. 1996. cDNA cloning and characterization of the human UDP glucuronosyltransferase, UGT1A3. Biochemical and Biophysical Research Communications 225:785–790.
  • Rice-Evans C. 2001. Flavonoid antioxidants. Current Medicinal Chemistry 8:797–807.
  • Smith PA, Sorich MJ, McKinnon RA, Miners JO. 2003. Pharmacophore and quantitative structure-activity relationship modeling: complementary approaches for the rationalization and prediction of UDP-glucuronosyl-transferase 1A4 substrate selectivity. Journal of Medicinal Chemistry 46:1617–1626.
  • Sorich MJ, Smith PA, McKinnon RA, Miners JO. 2002. Pharmacophore and quantitative structure activity relationship modelling of UDP-glucuronosyltransferase 1A1 (UGT1A1) substrates. Pharmacogenetics 12:635–645.
  • Sugatani J, Yamakawa K, Tonda E, Nishitani S, Yoshinari K, Degawa M, Abe I, Noguchi H, Miwa M. 2004. The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics. Biochemical Pharmacology 67:989–1000.
  • Sugimura T, Wakabayashi K, Nakagama H, Nagao M. 2004. Heterocyclic amines: Mutagens/carcinogens produced during cooking of meat and fish. Cancer Science 95:290–299.
  • Tukey RH, Strassburg CP. 2001. Genetic multiplicity of the human UDP-glucuronosyltransferases and regulation in the gastrointestinal tract. Molecular Pharmacology 59:405–414.
  • Walle T. 2004. Absorption and metabolism of flavonoids. Free Radical Biology and Medicine 36:829–837.
  • Walle UK, Walle T. 2002. Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids - structural requirements. Drug Metabolism and Disposition 30:564–569.
  • Williams RJ, Spencer JP, Rice-Evans C. 2004. Flavonoids: antioxidants or signalling molecules? Free Radical Biology and Medicine 36:838–849.
  • Yang CS, Landau JM, Huang MT, Newmark HL. 2001. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annual Review of Nutrition 21:381–406.
  • Young IS, Woodside JV. 2001. Antioxidants in health and disease. Journal of Clinical Pathology 54:176–186.
  • Yueh MF, Huang YH, Hiller A, Chen S, Nguyen N, Tukey RH. 2003. Involvement of the xenobiotic response element (XRE) in Ah receptor-mediated induction of human UDP-glucuronosyltransferase 1A1. Journal of Biological Chemistry 278:15001–15006.
  • Zhang HY, Sun YM, Wang XL. 2003. Substituent effects on O-H bond dissociation enthalpies and ionization potentials of catechols: a DFT study and its implications in the rational design of phenolic antioxidants and elucidation of structure-activity relationships for flavonoid antioxidants. Chemistry 9:502–508.

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