Volume 91, Issue 6, June (2004), pp. 841-847 © The Author 2004
doi:10.1079/BJN20041123

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

Ilja C. W. Arts¹, Aloys L. A. Sesink², Maria Faassen-Peters³ and Peter C. H. Hollman^1
1RIKILT– Institute of Food Safety, Wageningen University and Research Centre, Wageningen, The Netherlands
²Department. of Pharmacology and Toxicology, Nijmegen Centre for Molecular Life Sciences, Nijmegen, The Netherlands
³Small Animal Research Centre, Wageningen University, Wageningen, The Netherlands

 (Received 22 October 2003–Revised 26 January 2004–Accepted 8 February 2004)

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:
Flavonoid, Quercetin glycoside, Intestinal absorption, Lactase phlorizin hydrolase, Bile

Abbreviations:
AUC, area under the concentration–time curve, LPH, lactase phlorizin hydrolase, Q3arabinoside, quercetin-3-O-α-arabinopyranoside, Q3galactoside, quercetin-3-O-ß-galactoside, Q3glucoside, quercetin-3-O-ß-glucoside, Q3rhamnoside, quercetin-3-O-ß-rhamnoside, Q4′glucoside, quercetin-4′-O-ß-glucoside