{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,11]],"date-time":"2026-07-11T04:34:39Z","timestamp":1783744479900,"version":"3.55.0"},"reference-count":43,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2010,11,3]],"date-time":"2010-11-03T00:00:00Z","timestamp":1288742400000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"German Federal Ministry of Education and Research","award":["BMBF 0313848 A\/B"],"award-info":[{"award-number":["BMBF 0313848 A\/B"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecular Nutrition Food Res"],"published-print":{"date-parts":[[2010,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In order to study the human intestinal transit of flavan\u20103\u2010ol <jats:italic>C<\/jats:italic>\u2010glycosides, several <jats:italic>C<\/jats:italic>\u2010glycosyl derivatives were prepared by non\u2010enzymatic reaction of (+)\u2010catechin with \u03b1\u2010<jats:sc>D<\/jats:sc>\u2010glucose, \u03b1\u2010<jats:sc>D<\/jats:sc>\u2010galactose and \u03b1\u2010<jats:sc>D<\/jats:sc>\u2010rhamnose, respectively. In contrast to literature data, we propose that the reaction mechanism proceeds in analogy to the rearrangement of flavan\u20103\u2010ols during epimerization under alkaline conditions. Four of the 12 synthesized flavan\u20103\u2010ol <jats:italic>C<\/jats:italic>\u2010glycosides were incubated under aerobic conditions at 37\u00b0C using saliva (2\u2009min) and simulated gastric juice (3\u2009h). To simulate human intestine, the <jats:italic>C<\/jats:italic>\u2010glycosides were also incubated under anaerobic conditions at 37\u00b0C both in human ileostomy fluid (10\u2009h) and colostomy fluid (24\u2009h), respectively. The flavan\u20103\u2010ol <jats:italic>C<\/jats:italic>\u2010glycosides under study, <jats:italic>i.e.<\/jats:italic> (+)\u2010epicatechin 8\u2010<jats:italic>C<\/jats:italic>\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranoside (1a), (+)\u2010epicatechin 6\u2010<jats:italic>C<\/jats:italic>\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranoside (1d), (+)\u2010catechin 6\u2010<jats:italic>C<\/jats:italic>\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010galactopyranoside (2b), (+)\u2010catechin 6\u2010<jats:italic>C<\/jats:italic>\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010rhamnopyranoside (3b) were analyzed in the incubation samples by HPLC\u2010DAD and HPLC\u2010DAD\u2010MS\/MS. They were found to be stable in the course of incubation in saliva, simulated gastric juice and ileostomy fluid and underwent degradation in colostomy fluid. While the 6\u2010<jats:italic>C<\/jats:italic>\u2010\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010glucopyranoside 1d was completely metabolized between 2 and 4\u2009h, decomposition of the 6\u2010<jats:italic>C\u2010<\/jats:italic>\u03b2\u2010<jats:sc>D<\/jats:sc>\u2010galactopyranoside 2b reached only 16\u00b12% within 4\u2009h of incubation. Linear degradation rates of 1d and 2b in colostomy fluid differed significantly. As microbial metabolism of flavan\u20103\u2010ols is known not to be influenced by the stereochemistry of the aglycon, varying degradation rates are ascribed to the effect of the sugar moiety. Based on these results we assume that flavan\u20103\u2010ol <jats:italic>C<\/jats:italic>\u2010glycosides pass through the upper gastrointestinal tract (oral cavity, stomach and small intestine) unmodified and are then metabolized by the colonic microflora.<\/jats:p>","DOI":"10.1002\/mnfr.201000003","type":"journal-article","created":{"date-parts":[[2010,5,12]],"date-time":"2010-05-12T19:14:23Z","timestamp":1273691663000},"page":"1546-1555","source":"Crossref","is-referenced-by-count":17,"title":["Flavan\u20103\u2010ol <i>C<\/i>\u2010glycosides \u2013 Preparation and model experiments mimicking their human intestinal 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