Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides
Model reactions between the polysaccharide amylose and the polyphenol (−)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putat...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2007-11, Vol.55 (23), p.9685-9697 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Stark, Timo Keller, Daniela Wenker, Kerstin Hillmann, Hedda Hofmann, Thomas |
| description | Model reactions between the polysaccharide amylose and the polyphenol (−)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (−)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (−)-epicatechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)- O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, and (−)-epicatechin-6/8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 µmol of flavan-3-ol-6-C-β-d-glucopyranoside, flavan-3-ol-8-C-β-d-glucopyranoside, and flavan-3-ol-6-C,8-C-β-d-glucopyranoside were per mmol (−)-epicatechin when reacted with amylose. |
| doi_str_mv | 10.1021/jf0719508 |
| format | Article |
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To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (−)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (−)-epicatechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)- O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, and (−)-epicatechin-6/8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 µmol of flavan-3-ol-6-C-β-d-glucopyranoside, flavan-3-ol-8-C-β-d-glucopyranoside, and flavan-3-ol-6-C,8-C-β-d-glucopyranoside were per mmol (−)-epicatechin when reacted with amylose.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0719508</identifier><identifier>PMID: 17929894</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>(−)-catechin-8-C-β-d-maltopyranoside ; amylose ; Amylose - chemistry ; Biological and medical sciences ; C-glycosylation ; catechin ; Catechin - chemistry ; chemical structure ; Cross-Linking Reagents ; cross-links ; epicatechin ; Flavan-3-ol ; flavan-3-ol-C-glucosides ; flavanols ; Flavonoids - chemistry ; Food Chem/Biochem ; Food industries ; Fundamental and applied biological sciences. Psychology ; Glucosides - analysis ; Glycosylation ; Indicator Dilution Techniques ; oligosaccharides ; Oligosaccharides - chemistry ; polysaccharides ; Polysaccharides - chemistry ; starch ; Starch and starchy product industries</subject><ispartof>Journal of agricultural and food chemistry, 2007-11, Vol.55 (23), p.9685-9697</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-1c62fbfd66bb8daa8a38f7d1eff4f5dfe82e586375866a4f593b2282a40519223</citedby><cites>FETCH-LOGICAL-a405t-1c62fbfd66bb8daa8a38f7d1eff4f5dfe82e586375866a4f593b2282a40519223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf0719508$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0719508$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19241270$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17929894$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Stark, Timo</creatorcontrib><creatorcontrib>Keller, Daniela</creatorcontrib><creatorcontrib>Wenker, Kerstin</creatorcontrib><creatorcontrib>Hillmann, Hedda</creatorcontrib><creatorcontrib>Hofmann, Thomas</creatorcontrib><title>Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Model reactions between the polysaccharide amylose and the polyphenol (−)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (−)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (−)-epicatechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)- O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, and (−)-epicatechin-6/8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 µmol of flavan-3-ol-6-C-β-d-glucopyranoside, flavan-3-ol-8-C-β-d-glucopyranoside, and flavan-3-ol-6-C,8-C-β-d-glucopyranoside were per mmol (−)-epicatechin when reacted with amylose.</description><subject>(−)-catechin-8-C-β-d-maltopyranoside</subject><subject>amylose</subject><subject>Amylose - chemistry</subject><subject>Biological and medical sciences</subject><subject>C-glycosylation</subject><subject>catechin</subject><subject>Catechin - chemistry</subject><subject>chemical structure</subject><subject>Cross-Linking Reagents</subject><subject>cross-links</subject><subject>epicatechin</subject><subject>Flavan-3-ol</subject><subject>flavan-3-ol-C-glucosides</subject><subject>flavanols</subject><subject>Flavonoids - chemistry</subject><subject>Food Chem/Biochem</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glucosides - analysis</subject><subject>Glycosylation</subject><subject>Indicator Dilution Techniques</subject><subject>oligosaccharides</subject><subject>Oligosaccharides - chemistry</subject><subject>polysaccharides</subject><subject>Polysaccharides - chemistry</subject><subject>starch</subject><subject>Starch and starchy product industries</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0UFv2yAUB3A0bVrTbod9gc2XVtqBjYcNxscparpVUVspaa_oGUPnjJgOkmnepx9RoubSCwj48dD7Q8gHYF-Acfi6cqyGRjD1ikxAcEYFgHpNJiwfUiUknJDTlFaMMSVq9pacQN3wRjXVhFzfhMEO_8Y1bnpTTOmVH01Io8_LMBTBFTOPf3CgJQ0-Fe1Y3Pr-MdACh664C35MaMxPjH1n0zvyxqFP9v1hPiP3s8vl9Dud3179mH6bU6yY2FAwkrvWdVK2reoQFZbK1R1Y5yonOmcVt0LJss6DxLzVlC3niu9uQ8N5eUYu9nWfYvi9tWmj130y1nscbNgmLVWlQNRVhp_30MSQUrROP8V-jXHUwPQuOP0cXLYfD0W37dp2R3lIKoPzA8Bk0LuIg-nT0TW8Al6z7Oje9Wlj_z6fY_ylZZ2b0su7hX6YPVzDcr7QO_9p7x0GjY8x17xfcAbl7rNAivL4MpqkV2Ebh5zuCy38B1xZmFA</recordid><startdate>20071114</startdate><enddate>20071114</enddate><creator>Stark, Timo</creator><creator>Keller, Daniela</creator><creator>Wenker, Kerstin</creator><creator>Hillmann, Hedda</creator><creator>Hofmann, Thomas</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20071114</creationdate><title>Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides</title><author>Stark, Timo ; Keller, Daniela ; Wenker, Kerstin ; Hillmann, Hedda ; Hofmann, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-1c62fbfd66bb8daa8a38f7d1eff4f5dfe82e586375866a4f593b2282a40519223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>(−)-catechin-8-C-β-d-maltopyranoside</topic><topic>amylose</topic><topic>Amylose - chemistry</topic><topic>Biological and medical sciences</topic><topic>C-glycosylation</topic><topic>catechin</topic><topic>Catechin - chemistry</topic><topic>chemical structure</topic><topic>Cross-Linking Reagents</topic><topic>cross-links</topic><topic>epicatechin</topic><topic>Flavan-3-ol</topic><topic>flavan-3-ol-C-glucosides</topic><topic>flavanols</topic><topic>Flavonoids - chemistry</topic><topic>Food Chem/Biochem</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glucosides - analysis</topic><topic>Glycosylation</topic><topic>Indicator Dilution Techniques</topic><topic>oligosaccharides</topic><topic>Oligosaccharides - chemistry</topic><topic>polysaccharides</topic><topic>Polysaccharides - chemistry</topic><topic>starch</topic><topic>Starch and starchy product industries</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stark, Timo</creatorcontrib><creatorcontrib>Keller, Daniela</creatorcontrib><creatorcontrib>Wenker, Kerstin</creatorcontrib><creatorcontrib>Hillmann, Hedda</creatorcontrib><creatorcontrib>Hofmann, Thomas</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stark, Timo</au><au>Keller, Daniela</au><au>Wenker, Kerstin</au><au>Hillmann, Hedda</au><au>Hofmann, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2007-11-14</date><risdate>2007</risdate><volume>55</volume><issue>23</issue><spage>9685</spage><epage>9697</epage><pages>9685-9697</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Model reactions between the polysaccharide amylose and the polyphenol (−)-epicatechin followed by partial enzymatic hydrolysis of the reaction products formed led to the detection of mono- and oligo-C-glucosylated flavan-3-ols by means of LC-MS/MS experiments. To confirm the structure of these putative flavan-3-ol/oligosaccharide conjugates, (−)-epicatechin was reacted with maltose and maltotriose, respectively, giving rise to a series of previously unreported flavan-3-ol/maltose and flavan-3-ol/maltotriose conjugates, namely, (−)-epicatechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, (−)-catechin-8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)- O-α-d-glucopyranoside, (−)-catechin-6-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside, and (−)-epicatechin-6/8-C-β-d-glucopyranosyl-(4→1)-O-α-d-glucopyranosyl-(4→1)-O-α-d-glucopyranoside. Furthermore, quantitative analysis of flavan-3-ol-C-glucosides in an enzymatic total hydrolysate using a newly developed stable isotope dilution assay (SIDA) enabled a first insight into the yield of the formation of polyphenol/polysaccharide cross-links, for example, an amount of 14.0, 9.0, and 0.15 µmol of flavan-3-ol-6-C-β-d-glucopyranoside, flavan-3-ol-8-C-β-d-glucopyranoside, and flavan-3-ol-6-C,8-C-β-d-glucopyranoside were per mmol (−)-epicatechin when reacted with amylose.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17929894</pmid><doi>10.1021/jf0719508</doi><tpages>13</tpages></addata></record> |
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| subjects | (−)-catechin-8-C-β-d-maltopyranoside amylose Amylose - chemistry Biological and medical sciences C-glycosylation catechin Catechin - chemistry chemical structure Cross-Linking Reagents cross-links epicatechin Flavan-3-ol flavan-3-ol-C-glucosides flavanols Flavonoids - chemistry Food Chem/Biochem Food industries Fundamental and applied biological sciences. Psychology Glucosides - analysis Glycosylation Indicator Dilution Techniques oligosaccharides Oligosaccharides - chemistry polysaccharides Polysaccharides - chemistry starch Starch and starchy product industries |
| title | Nonenzymatic C-Glycosylation of Flavan-3-ols by Oligo- and Polysaccharides |
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