Hostname: page-component-5db58dd55d-m58mf Total loading time: 0 Render date: 2026-06-06T01:21:46.800Z Has data issue: false hasContentIssue false
  • English
  • Français

The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides

Published online by Cambridge University Press:  09 March 2007

Ilja C. W. Arts ,
Aloys L. A. Sesink ,
Maria Faassen-Peters  and
Peter C. H. Hollman
Ilja C. W. Arts*
Affiliation:
RIKILT– Institute of Food Safety, Wageningen University and Research Centre, Wageningen, The Netherlands
Aloys L. A. Sesink
Affiliation:
Department. of Pharmacology and Toxicology, Nijmegen Centre for Molecular Life Sciences, Nijmegen, The Netherlands
Maria Faassen-Peters
Affiliation:
Small Animal Research Centre, Wageningen University, Wageningen, The Netherlands
Peter C. H. Hollman
Affiliation:
RIKILT– Institute of Food Safety, Wageningen University and Research Centre, Wageningen, The Netherlands
*
*Corresponding author: Dr Ilja C. W. Arts, fax +31 317 417717, email ilja.arts@wur.nl
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the 'Save PDF' action button.

Quercetin is an important dietary flavonoid with putative beneficial effects in the prevention of cancer and CVD. The in vivo bioactivity of quercetin depends on its bioavailability, which varies widely between foods. We used an in situ rat intestinal perfusion model to study whether differential small intestinal hydrolysis of the sugar moiety of five naturally occurring quercetin glycosides determines the small intestinal uptake and subsequent biliary excretion of quercetin. After 30 min perfusion, a decrease of intact quercetin glycoside in perfusate was observed for quercetin-3-O-ß-glucoside (20·9 (sem 1·4) μmol/l) and quercetin-4′-O-ß-glucoside (23·5 (sem 1·6) μmol/l), but not of quercetin-3-O-ß-galactoside, quercetin-3-O-ß-rhamnoside and quercetin-3-O-α-arabinopyranoside. Appearance of free quercetin in perfusate and conjugated quercetin metabolites (quercetin, isorhamnetin, and tamarixetin) in portal and peripheral plasma and bile were also significantly greater after treatment with quercetin-3-O-ß-glucoside or quercetin-4′-O-ß-glucoside compared with any of the other glycosides. Thus, the type of sugar moiety is a major determinant of the small intestinal absorption of quercetin glycosides, but the position (3 or 4′) of the glucose moiety does not further influence absorption. The poor bioavailability of important dietary quercetin glycosides has implications for their in vivo bioactivities.

Keywords

FlavonoidQuercetin glycosideIntestinal absorptionLactase phlorizin hydrolaseBile

Information

Type
Research Article
Information
British Journal of Nutrition , Volume 91 , Issue 6 , June 2004 , pp. 841 - 847
Copyright
Copyright © The Nutrition Society 2004

References

Arts, ICW, Venema, DP & Hollman, PCH (2003) Quantitative determination of flavonols in plant foods and biological fluids. In Methods in Polyphenol Analysis, pp.214–228 [Santos-Buelga, C, Williamson, G, editors]. Cambridge: The Royal Society of Chemistry.Google Scholar
Crespy, V, Morand, C, Besson, C, Manach, C, Demigne, C & Remesy, C (2001) Comparison of the intestinal absorption of quercetin, phloretin and their glucosides in rats. J Nutr 131, 2109–2114.CrossRefGoogle ScholarPubMed
Day, AJ, Bao, YP, Morgan, MRA & Williamson, G (2000 a) Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med 29, 1234–1243.CrossRefGoogle ScholarPubMed
Day, AJ, Canada, FJ, Diaz, JC, Kroon, PA, Mclauchlan, R, Faulds, CB, Plumb, GW, Morgan, MRA & Williamson, G (2000 b) Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett 468, 166–170.CrossRefGoogle ScholarPubMed
Day, AJ, Gee, JM, DuPont, MS, Johnson, IT & Williamson, G (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, 1199–1206.CrossRefGoogle ScholarPubMed
Day, AJ & Williamson, G (2001) Biomarkers for exposure to dietary flavonoids: a review of the current evidence for identification of quercetin glycosides in plasma. Br J Nutr 86 Suppl 1105–110.CrossRefGoogle ScholarPubMed
Felgines, C, Texier, O, Morand, C, Manach, C, Scalbert, A, Regerat, F & Remesy, C (2000) Bioavailability of the flavanone naringenin and its glycosides in rats. Am J Physiol Gastrointest Liver Physiol 279, G1148–G1154.CrossRefGoogle ScholarPubMed
Gee, JM, DuPont, MS, Day, AJ, Plumb, GW, Williamson, G & Johnson, IT (2000) Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J Nutr 130, 2765–2771.CrossRefGoogle ScholarPubMed
Graefe, EU, Wittig, J, Mueller, S, Riethling, AK, Uehleke, B, Drewelow, B, Pforte, H, Jacobasch, G, Derendorf, H & Veit, M (2001) Pharmacokinetics and bioavailability of quercetin glycosides in humans. J Clin Pharmacol 41, 492–499.CrossRefGoogle ScholarPubMed
Hertog, MGL, Hollman, PCH, Katan, MB & Kromhout, D (1993) Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr Cancer 20 21–29.CrossRefGoogle ScholarPubMed
Hollman, PC, Buijsman, MN, Van Gameren, Y, Cnossen, EP, de Vries, JH & Katan, MB (1999) The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radic Res 31, 569–573.CrossRefGoogle Scholar
Hollman, PCH & Arts, ICW (2000) Flavonols, flavones and flavanols – nature, occurrence and dietary burden. J Sci Food Agric 80, 1081–1093.3.0.CO;2-G>CrossRefGoogle Scholar
Hollman, PCH, Van Trijp, JMP, Buysman, MNCP, van der Gaag, MS, Mengelers, MJB, de Vries, JHM & Katan, MB (1997) Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett 418, 152–156.CrossRefGoogle ScholarPubMed
Lommen, A, Godejohann, M, Venema, DP, Hollman, PCH & Spraul, M (2000) Application of directly coupled LC–NMR–MS for the identification and confirmation of quercetin glycosides and phloretin glycosides in apple peel. Anal Chem 72, 1793–1797.CrossRefGoogle Scholar
Manach, C, Morand, C, Crespy, V, Demigne, C, Texier, O, Regerat, F & Remesy, C (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 426, 331–336.CrossRefGoogle ScholarPubMed
Manach, C, Texier, O, Regerat, F, Agullo, G, Demigne, C & Remesy, C (1996) Dietary quercetin is recovered in rat plasma as conjugated derivatives of isorhamnetin and quercetin. J Nutr Biochem 7, 375–380.CrossRefGoogle Scholar
Morand, C, Manach, C, Crespy, V & Remesy, C (2000) Quercetin 3- O -beta-glucoside is better absorbed than other quercetin forms and is not present in rat plasma. Free Radic Res 33, 667–676.CrossRefGoogle Scholar
Németh, K, Plumb, GW, Berrin, JG, Juge, N, Jacob, R, Naim, HY, Williamson, G, Swallow, DM & Kroon, PA (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.CrossRefGoogle ScholarPubMed
Nijveldt, RJ, Van Nood, E, Van Hoorn, DEC, Boelens, PG, Van Norren, K & Van Leeuwen, PAM (2001) Flavonoids: a review of probable mechanisms of action and potential applications. Am J Clin Nutr 74, 418–425.CrossRefGoogle ScholarPubMed
Olthof, MR, Hollman, PCH, Vree, TB & Katan, MB (2000) Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. J Nutr 130, 1200–1203.CrossRefGoogle Scholar
Rice-Evans, CA, Miller, NJ & Paganga, G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20, 933–956.CrossRefGoogle ScholarPubMed
Sesink, ALA, Arts, ICW, Faassen-Peters, M & Hollman, PCH (2003) Intestinal uptake of quercetin-3-glucoside in rats involves hydrolysis by lactase phlorizin hydrolase. J Nutr 133, 773–776.CrossRefGoogle ScholarPubMed
Spencer, JP, Chowrimootoo, G, Choudhury, R, Debnam, ES, Srai, SK & Rice-Evans, C (1999) The small intestine can both absorb and glucuronidate luminal flavonoids. FEBS Lett 458, 224–230.CrossRefGoogle ScholarPubMed
Stahl, W, van den Berg, H & Arthur, J (2002) Bioavailability and metabolism. Mol Aspects Med 23, 39–100.CrossRefGoogle ScholarPubMed
Verhoeyen, ME, Bovy, A, Collins, G, Muir, S, Robinson, S, de Vos, CH & Colliver, S (2002) Increasing antioxidant levels in tomatoes through modification of the flavonoid biosynthetic pathway. J Exp Bot 53, 2099–2106.CrossRefGoogle ScholarPubMed
Wong, DWS & Robertson, GH (2003) Alpha-amylases. In Handbook of Food Enzymology, pp. 707–718 [Whitaker, JR, Voragen, AGJ, Wong, DWS, editor]. New York: Marcel Dekker, Inc.Google Scholar
Zubik, L & Meydani, M (2003) Bioavailability of soybean isoflavones from aglycone and glucoside forms in American women. Am J Clin Nutr 77, 1459–1465.CrossRefGoogle ScholarPubMed