Transport of trans- Tiliroside (kaempferol-3- β -D-(6″- p- coumaroyl-glucopyranoside) and related flavonoids across Caco-2 cells, as a model of absorption and metabolism in the small intestine

Xenobiotica

Volumn 45, Issue 8, 2015, Pages 722-730

  Luo, Zijun ^a,b   Morgan, Michael R A ^b   Day, Andrea J ^b  

^a CAMPDEN BRI   (United Kingdom)

^b UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Bioavailability; coumaroyl glucoside; efflux transporters; flavonoid; flavonol ester; MRP2

Indexed keywords

ASTRAGALIN; FLAVONOID; GLUCOPYRANOSIDE; KAEMPFEROL; MULTIDRUG RESISTANCE ASSOCIATED PROTEIN 2; PARA COUMARIC ACID; RIFAMPICIN; TILIROSIDE; UNCLASSIFIED DRUG; 4-COUMARIC ACID; CARRIER PROTEIN; COUMARIC ACID; KAEMPFEROL DERIVATIVE; MULTIDRUG RESISTANCE PROTEIN;

ARTICLE; CACO 2 CELL LINE; CELL METABOLISM; CELL TRANSPORT; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INTESTINE ABSORPTION; ION MONITORING; MOLECULAR WEIGHT; PH; SMALL INTESTINE; ULTRAVIOLET SPECTROSCOPY; BIOAVAILABILITY; METABOLISM; TIME FACTOR; TRANSPORT AT THE CELLULAR LEVEL;

BIOLOGICAL AVAILABILITY; BIOLOGICAL TRANSPORT; CACO-2 CELLS; COUMARIC ACIDS; FLAVONOIDS; HUMANS; INTESTINAL ABSORPTION; INTESTINE, SMALL; KAEMPFEROLS; MEMBRANE TRANSPORT PROTEINS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; P-GLYCOPROTEIN; TIME FACTORS;

EID: 84938848834     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2015.1007492     Document Type: Article

References (33)

1. Artursson P, Karlsson J. (1991). Correlation between oral-drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-5.
2. Barrington R, Williamson G, Bennett RN, et al. (2009). Absorption, conjugation and efflux of the flavonoids, kaempferol and galangin, using the intestinal CaCo-2/TC7 cell model. J Funct Foods 1:74-87.
3. Behrens I, Pena AIV, Alonso MJ, Kissel T. (2002). Comparative uptake studies of bioadhesive and non-bioadhesive nanoparticles in human intestinal cell lines and rats: the effect of mucus on particle adsorption and transport. Pharm Res 19:1185-93.
4. Chantret I, Rodolosse A, Barbat A, et al. (1994). Differential expression of sucrose-isomaltase in clones isolated from early and late passages of the cell-line Caco-2-evidence for glucose-dependent negative regulation. J Cell Sci 107:213-25.
5. Chen J, Lu YH, Wei DZ, Zhou XL. (2009). Establishment of a fingerprint of raspberries by LC. Chromatographia 70:981-5.
6. Day AJ, Bao YP, Morgan MRA, Williamson G. (2000). Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med 29:1234-43.
7. Day AJ, DuPont MS, Ridley S, et al. (1998). Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity. FEBS Lett 436:71-5.
8. Day AJ, Gee JM, DuPont MS, et al. (2003). Absorption of quercetin-3-glucoside and quercetin-40-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. Biochem Pharmacol 65:1199-206.
9. DuPont MS, Day AJ, Bennett RN, et al. (2004). Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans. Eur J Clin Nutr 58:947-54.
10. Hunter J, Jepson MA, Tsuruo T, et al. (1993). Functional expression of P-glycoprotein in apical membranes of human intestinal Caco-2 cells kinetics of vinblastine secretion and interaction with modulators. J Biol Chem 268:14991-7.
11. Irvine JD, Takahashi L, Lockhart K, et al. (1999). MDCK (madin-darby canine kidney) cells: a tool for membrane permeability screening. J Pharm Sci 88:28-33.
12. Itoh T, Ninomiya M, Yasuda M, et al. (2009). Inhibitory effects of flavonoids isolated from Fragaria ananassa Duch on IgE-mediated degranulation in rat basophilic leukemia RBL-2H3. Bioorg Med Chem 17:5374-9.
13. Karamanos NK, Syrokou A, Vanky P, et al. (1994) Determination of 24 Variously sulfated galactosaminoglycan-And hyaluronan-derived disaccharides by high-performance liquid chromatography. Anal Biochem 221:189-99.
14. Konishi Y, Kobayashi S. (2004). Transepithelial transport of chlorogenic acid, caffeic acid, and their colonic metabolites in intestinal Caco-2 cell monolayers. J Agric Food Chem 52:2518-26.
15. Konishi Y, Shimizu M. (2003). Transepithelial transport of ferulic acid by monocarboxylic acid transporter in Caco-2 cell monolayers. Biosci Biotechnol Biochem 67:856-62.
16. Kumarasamy Y, Cox PJ, Jaspars M, et al. (2003). Bioactive flavonoid glycosides from the seeds of Rosa canina. Pharm Biol 41:237-42.
17. Leitão GG, Soares SSV, Brito TDM, Delle MF. (2000). Kaempferol glycosides from Siparuna apiosyce. Phytochemistry 55:679-82.
18. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23:3-25.
19. Luo Z, Murray BS, Yusoff A, et al. (2011). Particle-stabilizing effects of flavonoids at the oil-water interface. J Agric Food Chem 59:2636-45.
20. Matsson P, Pedersen JM, Norinder U, et al. (2009). Identification of novel specific and general inhibitors of the three major human ATPbinding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharm Res 26:1816-31.
21. Matsuda H, Ninomiya K, Shimoda H, Yoshikawa M. (2002). Hepatoprotective principles from the flowers of Tilia argentea (Linden): structure requirements of tiliroside and mechanisms of action. Bioorg Med Chem 10:707-12.
22. Maubon N, Le Vee M, Fossati L, et al. (2007). Analysis of drug transporter expression in human intestinal Caco-2 cells by real-time PCR. Fundam Clin Pharmacol 21:659-63.
23. Németh K, Plumb GW, Berrin JG, et al. (2003). Deglycosylation by small intestinal epithelial cell beta-glucosidases is a critical step in the absorption and metabolism of dietary flavonoid glycosides in humans. Eur J Nutr 42:29-42.
24. Ninomiya K, Matsuda H, Kubo M, et al. (2007). Potent anti-obese principle from Rosa canina: Structure requirements and mode of action of trans-tiliroside. Bioorg Med Chem Lett 17:3059-64.
25. Nowak R. (2003). Separation and quantification of tiliroside from plant extracts by SPE/RP-HPLC. Pharm Biol 41:627-30.
26. O'Leary KA, Day AJ, Needs PW, et al. (2003). Metabolism of quercetin-7-And quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem Pharmacol 65:479-91.
27. Polli JE, Balakrishnan A, Seo PR. (2004). Human intestinal cellular characteristics and drug permeability. In: Lu DR, Oie S, eds. Cellular drug delivery principles and practice. New Jersey: Humana Press Inc, 163-80.
28. Poquet L, Clifford MN, Williamson G. (2008). Transport and metabolism of ferulic acid through the colonic epithelium. Drug Metab Dispos 36:190-7.
29. Sala A, Recio MC, Schinella GR, et al. (2003). Assessment of the antiinflammatory activity and free radical scavenger activity of tiliroside. Eur J Pharmacol 461:53-61.
30. Schipper NGM, Varum KM, Stenberg P, et al. (1999). Chitosans as absorption enhancers of poorly absorbable drugs 3: Influence of mucus on absorption enhancement. Eur J Pharm Sci 8:335-43.
31. Walgren RA, Karnaky KJ, Lindenmayer GE, Walle T. (2000). Efflux of dietary flavonoid quercetin 40-beta-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance-Associated protein-2. J Pharmacol Exp Ther 294:830-6.
32. Walgren RA, Walle UK, Walle T. (1998). Transport of quercetin and its glucosides across human intestinal epithelial Caco-2 cells. Biochem Pharmacol 55:1721-7.
33. Williamson G, Manach C. (2005). Bioavailability and bioefficacy of polyphenols in human. II. Review of 93 intervention studies. Am J Clin Nutr 81:243S-55S.