Quantitative regioselectivity of glucuronidation of quercetin by recombinant UDP-glucuronosyltransferases 1A9 and 1A3 using enzymatic kinetic parameters

References

• Auger C, Teissedre PL, Gerain P, Lequeux N, Bornet A, Serisier S, Besancon P, Caporiccio B, Cristol JP, Rouanet JM. Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation. Journal of Agricultural and Food Chemistry 2005; 53: 2015–2021
   PubMed Web of Science ®Google Scholar
• Benito S, Buxaderas S, Mitjavila MT. Flavonoid metabolites and susceptibility of rat lipoproteins to oxidation. American Journal of Physiology. Heart and circulation physiology 2004; 287: H2819–H2824
   PubMed Web of Science ®Google Scholar
• Boersma MG, Van derWoude H, Bogaards J, Boeren S, Vervoort J, Cnubben NH, Van Iersel ML, Van Bladeren PJ, Rietjens IM. Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. Chemical Research in Toxicology 2002; 15: 662–670
   PubMed Web of Science ®Google Scholar
• Chen YK, Li X, Chen SQ, Zeng S. Heterologous expression of active human uridine diphosphate glucuronosyltransferase 1A3 in Chinese hamster lung cells. World Journal of Gastroenterology 2005; 11: 118–121
   PubMed Web of Science ®Google Scholar
• Cheng ZQ, Radominska-Pandya A, Tephly TR. Cloning and expression of human UDP-glucuronosyltransferase (UGT) 1A8. Archives of Biochemistry and Biophysics 1998; 356: 301–305
   PubMed Web of Science ®Google Scholar
• Cheng ZQ, Radominska-Pandya A, Tephly TR. Studies on the substrate specificity of human intestinal UDP-glucuronosyltransferases 1A8 and 1A10. Drug Metabolism and Disposition 1999; 27: 1165–1170
   PubMed Web of Science ®Google Scholar
• Choi JA, Kim JY, Lee JY, Kang CM, Kwon HJ, Yoo YD, Kim TW, Lee YS, Lee SJ. Induction of cell cycle arrest and apoptosis in human breast cancer cells by quercetin. International Journal of Oncology 2001; 19: 837–844
   PubMed Web of Science ®Google Scholar
• Day AJ, Bao Y, Morgan MR, Williamson G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radical Biology and Medicine 2000; 29: 1234–1243
   PubMed Web of Science ®Google Scholar
• Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR. Glucuronidation of amines and other xenobiotics catalysed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metabolism and Disposition 1998; 26: 507–512
   PubMed Web of Science ®Google Scholar
• Janisch KM, Williamson G, Needs P, Plumb GW. Properties of quercetin conjugates: Modulation of LDL oxidation and binding to human serum albumin. Free Radical Research 2004; 38: 877–884
   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
• Li XM, Li X, Chen SQ, Zeng S. Construction of pcDNA3. 1-UDPGT1A9 expression plasmid and establishment of its transgenic cell line. Chinese Journal of Pharmacology and Toxicology 2004; 8: 115–120
   Google Scholar
• Miners JO, Smith PA, Sorich MJ, McKinnon RA, Mackenzie PI. Predicting human drug glucuronidation parameters: Application of in vitro and in silico modeling approaches. Annual Review of Pharmacology and Toxicology 2004; 44: 1–25
   PubMed Web of Science ®Google Scholar
• Moon JH, Tsushida T, Nakahara K, Terao J. Identification of quercetin 3-O-beta-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Free Radical Biology and Medicine 2001; 30: 1274–1285
   PubMed Web of Science ®Google Scholar
• Morand C, Crespy V, Manach C, Besson C, Demigne C, Remesy C. Plasma metabolites of quercetin and their antioxidant properties. American Journal of Physiology 1998; 275: R212–R219
   PubMed Web of Science ®Google Scholar
• Morikawa K, Nonaka M, Narahara M, Torii I, Kawaguchi K, Yoshikawa T, Kumazawa Y, Morikawa S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. Life Sciences 2003; 74: 709–721
   PubMed Web of Science ®Google Scholar
• O'Leary KA, Day AJ, Needs PW, Sly WS, O'Brien NM, Williamson G. Flavonoid glucuronides are substrates for human liver beta-glucuronidase. FEBS Letters 2001; 503: 103–106
   PubMed Web of Science ®Google Scholar
• Oliveira EJ, Watson DG. In vitro glucuronidation of kaempferol and quercetin by human UGT-1A9 microsomes. FEBS Letters 2000; 471: 1–6
   PubMed Web of Science ®Google Scholar
• Qian MR, Chen SQ, Li X, Zeng S. Cloning and expression of human UDP-glucuronosyltransferase 1A4 in Bac-to-Bac system. Biochemical and Biophysical Research Communications 2004; 319: 386–392
   PubMed Web of Science ®Google Scholar
• Silva MM, Santos MR, Caroco G, Rocha R, Justino G, Mira L. Structure–antioxidant activity relationships of flavonoids: A re-examination. Free Radical Research 2002; 36: 1219–1227
   PubMed Web of Science ®Google Scholar
• Singh A, Naidu PS, Kulkarni SK. Reversal of aging and chronic ethanol-induced cognitive dysfunction by quercetin a bioflavonoid. Free Radical Research 2003; 37: 1245–1252
   PubMed Web of Science ®Google Scholar
• Spencer JP, Chowrimootoo G, Choudhury G, Debnam ES, Srai SK, Rice-Evans C. The small intestine can both absorb and glucuronidate luminal flavonoids. FEBS Letters 1999; 458: 224–230
   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
• Wittig J, Herderich M, Graefe EU, Veit M. Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry. Journal of Chromatography B, Biomedical Sciences and Applications 2001; 753: 237–243
   PubMed Web of Science ®Google Scholar
• UV spectra of flavone and flavonol. The manual for identification of flavonoids, RS Xu, BN Zhou, BP Ying, JS Liu, XG He, GW Qin, GF Zeng. Science, Beijing 1981; 399–517
   Google Scholar
• Yamamoto N, Moon JH, Tsushida T, Nagao A, Terao J. Inhibitory effect of quercetin metabolites and their related derivatives on copper ion-induced lipid peroxidation in human low-density lipoprotein. Archives of Biochemistry and Biophysics 1999; 372: 347–354
   PubMed Web of Science ®Google Scholar
• Yoshizumi M, Tsuchiya K, Suzaki Y, Kirima K, Kyaw M, Moon JH, Terao J, Tamaki T. Quercetin glucuronide prevents VSMC hypertrophy by angiotensin II via the inhibition of JNK and AP-1 signaling pathway. Biochemical and Biophysical Research Communications 2002; 293: 1458–1465
   PubMed Web of Science ®Google Scholar
• Zheng SL, Qian MR, Li X, Chen SQ, Zeng S. Expression of human UGT1A6 in insect cell with baculovirus expression system. Chinese Journal of Pharmacology and Toxicology 2004; 18: 444–448
   Google Scholar