MK571 inhibits phase-2 conjugation of flavonols by Caco-2/TC7 cells, but does not specifically inhibit their apical efflux

Biochemical Pharmacology

Volumn 95, Issue 3, 2015, Pages 193-200

  Barrington, Robert D ^a   Needs, Paul W ^a   Williamson, Gary ^b   Kroon, Paul A ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

^b UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Caco 2 TC7; Flavonoids; Flavonols; MK571; Multidrug resistance protein 2; Phase 2 conjugation

Indexed keywords

FLAVONOL DERIVATIVE; PROPIONIC ACID DERIVATIVE; QUINOLINE DERIVATIVE; VERLUKAST;

CACO 2 CELL LINE; HUMAN; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; FLAVONOLS; HUMANS; PROPIONATES; QUINOLINES;

EID: 84937762222     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2015.03.005     Document Type: Article

References (44)

1. C. Manach, G. Williamson, C. Morland, A. Scalbert, and C. Remesy Bioavailability and bioefficiency of polyphenols in humans I. Review of 97 bioavailability studies Am. J. Clin. Nutr. 81 1 2005 230S 242S
2. W. Hollands, B.M. Brett, J.R. Dainty, B. Teucher, and P.A. Kroon Urinary excretion of strawberry anthocyanins is dose dependent for physiological oral doses of fresh fruit Mol. Nutr. Food Res. 52 10 2008 1097 1105
3. G.M. Brett, W. Hollands, P.W. Needs, B. Teucher, J.R. Dainty, J.S. Brodbelt, and P.A. Kroon Absorption, metabolism and excretion of flavanones from single portions of orange fruit and juice and effects on anthropometric variables and contraceptive pill use on flavanone excretion Br. J. Nutr. 101 5 2009 664 675
4. S. Saha, W. Hollands, P.W. Needs, L.M. Ostertag, B. de Roos, and P.A. Kroon Human O-sulfated metabolites of (-)-epicatechin and methyl-(-)-epicatechin are poor substrates for commercial aryl-sulfatases: implications for studies concerned with quantifying bioavailability Pharm. Res. 65 6 2012 592 602
5. P.C. Hollman, J.M. van Trijp, M.S. van der Gaag, M.J. Mengelers, J.H. de Vries, and M.B. Katan Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man FEBS Lett. 418 1-2 1997 152 156
6. S.E. Nielsen, V. Breinholt, U. Justesen, C. Cornett, and L.O. Dragsted Human absorption and excretion of flavonoids after broccoli consumption Cancer Lett. 114 1997 173 174
7. M.S. Dupont, A.J. Day, R.N. Bennett, F.A. Mellom, and P.A. Kroon Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide in humans Eur. J. Clin. Nutr. 58 6 2004 947 954
8. C. Manach, C. Morland, O. Texier, M.L. Favier, G. Agulio, C. Demigne, F. Regerat, and C. Remesy Quercetin metabolism in plasma of rats fed diets containing rutin and quercetin J. Nutr. 125 7 1995 1911 1922
9. C. Morand, C. Manach, V. Crespy, and C. Remesy Quercetin 3-O-Beta glucoside is better absorbed than other forms and is not present in rat plasma Free Radic. Res. 33 5 2000 667 676
10. M. Carbonaro, and G. Grant Absorption of quercetin and rutin in rat small intestine Ann. Nutr. Metab. 49 3 2005 178 182
11. A.B. Graf, C. Ameho, G.G. Dolnikowski, P.E. Milbury, C. Chen, and J.B. Blumberg Rat gastrointestinal tissues metabolise quercetin J. Nutr. 136 2006 39 44
12. A.J. Day, Y. Bao, M.R. Morgan, and G. Williamson Conjugation position of quercetin glucuronides and effect on biological activity Free Radic. Biol. Med. 29 2000 1234 1243
13. K. Nemeth, G.W. Plumb, J. Berrin, N. Juge, R. Jacob, H.Y. Naim, G. Williamson, D.M. Swallow, and P.A. Kroon Deglycosylation by small intestinal epithelial cell β-glucosidase is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans Eur. J. Nutr. 42 1 2003 29 42
14. Y. Liu, and M. Hu Absorption and metabolism of flavonoids in the Caco-2 cell culture model and a perfused rat intestinal model Drug Metab. Dispos. 30 4 2002 370 377
15. J.A. Boutin, F. Meunier, P.H. Lambert, P. Hennig, D. Bertin, B. Serkiz, and J.P. Volland In vivo and in vitro glucuronidation of the flavonoids diosmetrin in rats Drug Metab. Dispos. 21 6 1993 1157 1166
16. J.P. Spencer, G. Chowrimootoo, R. Choudhury, E.S. Debnam, S.K. Srai, and C. Rice-Evans The small intestine can both absorb and glucuronidate luminal flavonoids FEBS Lett. 458 2 1999 224 230
17. J.B. Vaidyanathan, and T. Walle Glucuronidation and sulfation of the tea flavonoid (-)-epicatechin by the human and rat enzymes Drug Metab Dispos. 30 8 2002 897 903
18. J.D. Lambert, M. Lee, H. Lu, X. Meng, J.J.J. Hong, D.S. Seril, M.G. Sturgill, and C.S. Yang Epigallocatechin-3-gallate is absorbed but extensively glucuronidated following oral administration to mice J. Nutr. 133 2003 4172 4177
19. R. Barrington, G. Williamson, R.N. Bennett, B.D. Davis, J.S. Brodbelt, and P.A. Kroon Absorption, conjugation and efflux of the flavonoids, kaemferol and galangin, using the intestinal Caco-2/TC7 cell model J. Funct. Foods 1 1 2008 74 87
20. S. Tribola, F. Lodi, C. Connor, S. Suri, V.G. Wilson, M.A. Taylor, P.W. Needs, P.A. Kroon, and D.A. Hughes Comparative effects of quercetin and its predominant human metabolites on adhesion molecule expression in activated human vascular endothelial cells Atherosclerosis 197 1 2008 50 56
21. M.S. Winterbone, S. Tribolo, P.W. Needs, P.A. Kroon, and D.A. Hughes Physiologically relevant metabolites of quercetin have no effect on adhesion molecule or chemokine expression in human vascular smooth muscle cells Atherosclerosis 202 2 2009 431 438
22. W.M. Loke, J.M. Proudfoot, A.J. McKinley, P.W. Needs, P.A. Kroon, J.M. Hodgson, and K.D. Croft Quercetin and its in vivo metabolites inhibit neutrophil-mediated low-density;opoprotein oxidation J. Agric. Food Chem. 56 10 2008 3609 3615
23. W.M. Loke, J.M. Proudfoot, S. Stewart, A.J. McKinlay, P.W. Needs, P.A. Kroon, J.M. Hodgson, and K.D. Croft Metabolic transformation has a profound effect on anti-inflammatory activity of flavonoids such as quercetin: lack of association between antioxidant and lipoxygenase inhibitory activity Biochem. Pharmacol. 75 5 2008 1045 1053
24. S. Suri, M.A. Taylor, A. Verity, S. Tribola, P.W. Needs, P.A. Kroon, D.A. Hughes, and V.G. Wilson A comparative study of the effects of quercetin and its glucuronide and sulfate metabolites on human neutrophil function in vitro Biochem. Pharmacol. 76 5 2008 645 653
25. F. Lodi, M.S. Winterbone, S. Tribolo, P.W. Needs, D.A. Hughes, and P.A. Kroon Human quercetin conjugated metabolites attenuate TNF-α-induced changes in vasomodulatory molecules in an HUASMCs/HUVECs co-culture model Planta Med. 78 14 2012 1571 1573
26. M.N. Chabane, A. Al Ahmad, J. Peluso, C.D. Muller, and G. Ubeaud Quercetin and naringenin transport across human intestinal Caco-2 cells J. Pharm. Pharmacol. 61 11 2009 1473 1483
27. X. Tian, X. Yang, K. Wang, and X. Yang The efflux of flavonoids morin, isorhamnetin-3-O-rutinoside and diosmetin-7-O-β-D-xylopyranosyl-(1-6)-β-D-glucopyranoside in the human intestinal cell line Caco-2 Pharm. Res. 23 8 2006 1721 1728
28. U.K. Walle, A. Galijatovic, and T. Walle Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2 Biochem. Pharmacol. 58 1999 431 438
29. R.A. Walgren, K. Karnaky, G.E. Lindenmayer, and T. Walle Efflux of dietary flavonoid quercetin 4′-β-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance protein-2 J. Pharmacol. Exp. Ther. 294 2000 830 836
30. R.A. Walgren, J. Lin, R.K. Kinne, and T. Walle Cellular uptake of dietary flavonoid quercetin-4′-β-glucoside by sodium-dependent SGLT1 J. Pharmacol. Exp. Ther. 294 2000 837 843
31. C. Henry, X. Vitrac, A. Decendit, R. Ennamany, S. Krisa, and J. Merillon Cellular uptake and efflux of trans-piceid and its aglycone trans-resveratrol on the apical membrane of human intestinal Caco-2 cells J. Agric. Food Chem. 53 2005 798 803
32. G. Williamson, I. Aeberli, L. Miguet, Z. Zhang, M. Sanchez, V. Crespy, D. Barron, P. Needs, P.A. Kroon, H. Glavinas, P.m. Krajcsi, and M. Grigorow Interaction of positional isomers of quercetin glucuronides with the transporter ABCC2 (cMOAT MRP2) Drug Metab. Dispos. 35 8 2007 1262 1268
33. A.L. Sesink, I.C. Arts, V.C. de Boer, P. Breedfield, J.H. Schellens, P.C. Hollman, and F.G. Russel Breast cancer resistance protein(Bcrp1/Abcg2) limits net intestinal uptake of quercetin in rats by fascilitating apical efflux of glucuronides Mol. Pharmacol. 67 6 2005 1999 2006
34. R.J. Leatherbarrow GraFit version 4.0 Data Analysis and Graphics Program for the IBM PC 1998 Publisher: Erithacus Software Staines, UK
35. L. Zhang, Y. Zheng, M.S.S. Chow, and Z. Zuo Investigation of intestinal absorption and disposition of green tea catechins by Caco-2 monolayer model Int. J. Pharm. 287 1-2 2004 1 12
36. J.B. Vaidyanathan, and T. Walle Transport and metabolism of the tea flavonoid (-)-epicatechin by the human intestinal cell line Caco-2 Pharm. Res. 18 1 2001 1420 1425
37. W. Meinl, B. Ebert, H. Glatt, and A. Lampen Sulfotransferase forms expressed in human intestinal Caco-2 and TC7 cells ay varying stages of differentiation and role in benzo[a]pyrene metabolism Drug Metab. Dispos. 36 2 2008 276 283
38. P.A. Munzel, S. Schmohl, H. Heel, K. Kalberer, B.S. Bock-Hennig, and K.W. Bock Induction of human UDP glucuronosyltransferase (UGT1A6UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8 tetrahydrodibenzo-p-dioxin in Caco-2 cells Drug Metab. Dispos. 27 5 1999 569 573
39. M. Hu, J. Chen, and H. Lin Metabolism of flavonoids via enteric recycling: mechanistic studies of disposition of apigenin in the Caco-2 cell culture model J. Pharmacol. Exp. Ther. 307 1 2003 314 321
40. I. Leier, G. Jedlitschky, U. Buchholz, S.P. Cole, R.G. Deeley, and D. Keppler The MRP gene encodes an ATP-dependent export pump for leukotriene C4 and structurally related conjugates J. Biol. Chem. 269 45 1994 27807 27810
41. M. Yamazaki, B. Li, S.W. Louie, N.T. Pudvah, R. Stocco, W. Wong, M. Abramovitz, A. Demartis, R. Laufer, J.H. Hochman, T. Preuksaritanont, and J.H. Lin Effets of fibrates on human organic anaion-transporting polypeptide 1B1-, myltidrug resistance protein2- and P-glycoprotein-mediated transport Xenobiotica 37 7 2005 737 753
42. G. Reid, P. Wielinga, N. Zelcer, M. De Haas, L. Van Deemter, J. Wijnholds, J. Balzarini, and P. Borst Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5 Mol. Pharmacol. 63 5 2003 1094 1103
43. K. Letschert, H. Faulstich, D. Keller, and D. Keppler Molecular characterizaton and inhibition of amanitin uptake into human hepatocytes Toxicol. Sci. 91 1 2006 140 149
44. W. Brand, P.A. van der Wel, M.J. Rein, D. Barron, G. Williamson, P.J. van Bladeren, and I.M. Rietjens Metabolism and transport of the citrus flavonoid hesperetin in Caco-2 cell monolayers Drug Metab. Dispos. 36 9 2008 1794 1802