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

References

• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Chen J, Lu YH, Wei DZ, Zhou XL. (2009). Establishment of a fingerprint of raspberries by LC. Chromatographia 70:981–5
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Day AJ, Gee JM, DuPont MS, et al. (2003). Absorption of quercetin-3-glucoside and quercetin-4′-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter. Biochem Pharmacol 65:1199–206
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Kumarasamy Y, Cox PJ, Jaspars M, et al. (2003). Bioactive flavonoid glycosides from the seeds of Rosa canina. Pharm Biol 41:237–42
   Web of Science ®Google Scholar
• Leitão GG, Soares SSV, Brito TDM, Delle MF. (2000). Kaempferol glycosides from Siparuna apiosyce. Phytochemistry 55:679–82
   PubMed Web of Science ®Google Scholar
• 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
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Matsson P, Pedersen JM, Norinder U, et al. (2009). Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharm Res 26:1816–31
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Nowak R. (2003). Separation and quantification of tiliroside from plant extracts by SPE/RP-HPLC. Pharm Biol 41:627–30
   Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Polli JE, Balakrishnan A, Seo PR. (2004). Human intestinal cellular characteristics and drug permeability. In: Lu DR, Øie S, eds. Cellular drug delivery principles and practice. New Jersey: Humana Press Inc, 163–80
   Google Scholar
• Poquet L, Clifford MN, Williamson G. (2008). Transport and metabolism of ferulic acid through the colonic epithelium. Drug Metab Dispos 36:190–7
   PubMed Web of Science ®Google Scholar
• Sala A, Recio MC, Schinella GR, et al. (2003). Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. Eur J Pharmacol 461:53–61
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Walgren RA, Karnaky KJ, Lindenmayer GE, Walle T. (2000). Efflux of dietary flavonoid quercetin 4′-beta-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance-associated protein-2. J Pharmacol Exp Ther 294:830–6
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar