Copigmentation between malvidin-3-glucoside and some wine constituents and its importance to colour expression in red wine
Thermodynamic parameters for intermolecular copigmentation interactions involving malvidin-3-glucoside were determined by UV/visible spectroscopy at wine pH (pH 3.6). These included association constants, enthalpy and entropy changes, which were measured for chlorogenic acid, caffeic acid, quercetin...
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| Veröffentlicht in: | Food chemistry 2011-03, Vol.125 (1), p.106-115 |
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| creator | Lambert, Stephanie G. Asenstorfer, Robert E. Williamson, Natalie M. Iland, Patrick G. Jones, Graham P. |
| description | Thermodynamic parameters for intermolecular copigmentation interactions involving malvidin-3-glucoside were determined by UV/visible spectroscopy at wine pH (pH 3.6). These included association constants, enthalpy and entropy changes, which were measured for chlorogenic acid, caffeic acid, quercetin, quercetin-3-glucoside, (−)-epicatechin, (+)-catechin, procyanidin dimer and seed tannin. Quercetin produced the strongest copigment (
K
CP
=
2900
±
1300), whilst the addition of glucose at position 3 (quercetin-3-glucoside) reduced its effect by almost 10-fold. Malvidin-3-glucoside self-association (
K
D
=
3300
±
300
mol
−1
l) was thermodynamically favoured over intermolecular interaction with any of the copigments tested. No colour enhancement due to self-association was observed for malvidin-3-glucoside-derived pigments that cannot enter hydration reactions. In addition, malvidin-3-(6-
O-
p-coumaryl)glucoside did not show colour enhancement suggesting that the
p-coumaryl group prevents self-association. The malvidin-3-glucoside circular dichroism (CD) spectrum was not affected by indicated changes in malvidin-3-glucoside concentration. These observations demonstrate that self-association of malvidin-3-glucoside is more important than copigmentation in young red wine. |
| doi_str_mv | 10.1016/j.foodchem.2010.08.045 |
| format | Article |
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K
CP
=
2900
±
1300), whilst the addition of glucose at position 3 (quercetin-3-glucoside) reduced its effect by almost 10-fold. Malvidin-3-glucoside self-association (
K
D
=
3300
±
300
mol
−1
l) was thermodynamically favoured over intermolecular interaction with any of the copigments tested. No colour enhancement due to self-association was observed for malvidin-3-glucoside-derived pigments that cannot enter hydration reactions. In addition, malvidin-3-(6-
O-
p-coumaryl)glucoside did not show colour enhancement suggesting that the
p-coumaryl group prevents self-association. The malvidin-3-glucoside circular dichroism (CD) spectrum was not affected by indicated changes in malvidin-3-glucoside concentration. These observations demonstrate that self-association of malvidin-3-glucoside is more important than copigmentation in young red wine.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2010.08.045</identifier><identifier>CODEN: FOCHDJ</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>anthocyanins ; Biological and medical sciences ; caffeic acid ; catechin ; chlorogenic acid ; color ; epicatechin ; Fermented food industries ; Flavan-3-ols ; Flavonols ; food composition ; Food industries ; Fundamental and applied biological sciences. Psychology ; grape seeds ; Intermolecular copigmentation ; Malvidin-3-glucoside ; phytochemicals ; plant pigments ; quercetin ; red wines ; Seed tannin ; Self-association ; tannins ; UV/visible spectroscopy ; Vitaceae ; wine grapes ; Wines and vinegars</subject><ispartof>Food chemistry, 2011-03, Vol.125 (1), p.106-115</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c399t-2cdfbd4fba7cf38353d752d7c9546e7c923563894a8ae6288bd2156d31a765723</citedby><cites>FETCH-LOGICAL-c399t-2cdfbd4fba7cf38353d752d7c9546e7c923563894a8ae6288bd2156d31a765723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.foodchem.2010.08.045$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23822859$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Lambert, Stephanie G.</creatorcontrib><creatorcontrib>Asenstorfer, Robert E.</creatorcontrib><creatorcontrib>Williamson, Natalie M.</creatorcontrib><creatorcontrib>Iland, Patrick G.</creatorcontrib><creatorcontrib>Jones, Graham P.</creatorcontrib><title>Copigmentation between malvidin-3-glucoside and some wine constituents and its importance to colour expression in red wine</title><title>Food chemistry</title><description>Thermodynamic parameters for intermolecular copigmentation interactions involving malvidin-3-glucoside were determined by UV/visible spectroscopy at wine pH (pH 3.6). These included association constants, enthalpy and entropy changes, which were measured for chlorogenic acid, caffeic acid, quercetin, quercetin-3-glucoside, (−)-epicatechin, (+)-catechin, procyanidin dimer and seed tannin. Quercetin produced the strongest copigment (
K
CP
=
2900
±
1300), whilst the addition of glucose at position 3 (quercetin-3-glucoside) reduced its effect by almost 10-fold. Malvidin-3-glucoside self-association (
K
D
=
3300
±
300
mol
−1
l) was thermodynamically favoured over intermolecular interaction with any of the copigments tested. No colour enhancement due to self-association was observed for malvidin-3-glucoside-derived pigments that cannot enter hydration reactions. In addition, malvidin-3-(6-
O-
p-coumaryl)glucoside did not show colour enhancement suggesting that the
p-coumaryl group prevents self-association. The malvidin-3-glucoside circular dichroism (CD) spectrum was not affected by indicated changes in malvidin-3-glucoside concentration. These observations demonstrate that self-association of malvidin-3-glucoside is more important than copigmentation in young red wine.</description><subject>anthocyanins</subject><subject>Biological and medical sciences</subject><subject>caffeic acid</subject><subject>catechin</subject><subject>chlorogenic acid</subject><subject>color</subject><subject>epicatechin</subject><subject>Fermented food industries</subject><subject>Flavan-3-ols</subject><subject>Flavonols</subject><subject>food composition</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>grape seeds</subject><subject>Intermolecular copigmentation</subject><subject>Malvidin-3-glucoside</subject><subject>phytochemicals</subject><subject>plant pigments</subject><subject>quercetin</subject><subject>red wines</subject><subject>Seed tannin</subject><subject>Self-association</subject><subject>tannins</subject><subject>UV/visible spectroscopy</subject><subject>Vitaceae</subject><subject>wine grapes</subject><subject>Wines and vinegars</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkM2OFCEUhYnRxHb0FZSNiZtq-Sl-aqfpjM4kk7jQWRMabrV0qqAEakZ9eunp0a0bTgLfPZd8CL2mZEsJle-P2zEl777DvGWkXRK9Jb14gjZUK94pothTtCGc6E7TXj5HL0o5EkIaqzfo9y4t4TBDrLaGFPEe6j1AxLOd7oIPsePdYVpdKsEDttHjkmbA9yECdimWGuraZsvDU2gZ5iXlaqMDXFNDprRmDD-XDKWc-kPEGfxDwUv0bLRTgVePeYFuP11-2111N18-X-8-3nSOD0PtmPPj3vfj3io3cs0F90owr9wgegktGBeS66G32oJkWu89o0J6Tq2SQjF-gd6de5ecfqxQqplDcTBNNkJai6FKaMa1ZLyh8oy6nErJMJolh9nmX4YSc5JtjuavbHOSbYg2TXYbfPu4wxZnpzE3A6H8m271jGkxNO7NmRttMvaQG3P7tRVxQod29qoRH84ENCV3AbIpLkDz6UMGV41P4X-f-QP49KPy</recordid><startdate>20110301</startdate><enddate>20110301</enddate><creator>Lambert, Stephanie G.</creator><creator>Asenstorfer, Robert E.</creator><creator>Williamson, Natalie M.</creator><creator>Iland, Patrick G.</creator><creator>Jones, Graham P.</creator><general>Elsevier Ltd</general><general>[Amsterdam]: Elsevier Science</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U7</scope><scope>C1K</scope></search><sort><creationdate>20110301</creationdate><title>Copigmentation between malvidin-3-glucoside and some wine constituents and its importance to colour expression in red wine</title><author>Lambert, Stephanie G. ; Asenstorfer, Robert E. ; Williamson, Natalie M. ; Iland, Patrick G. ; Jones, Graham P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c399t-2cdfbd4fba7cf38353d752d7c9546e7c923563894a8ae6288bd2156d31a765723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>anthocyanins</topic><topic>Biological and medical sciences</topic><topic>caffeic acid</topic><topic>catechin</topic><topic>chlorogenic acid</topic><topic>color</topic><topic>epicatechin</topic><topic>Fermented food industries</topic><topic>Flavan-3-ols</topic><topic>Flavonols</topic><topic>food composition</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>grape seeds</topic><topic>Intermolecular copigmentation</topic><topic>Malvidin-3-glucoside</topic><topic>phytochemicals</topic><topic>plant pigments</topic><topic>quercetin</topic><topic>red wines</topic><topic>Seed tannin</topic><topic>Self-association</topic><topic>tannins</topic><topic>UV/visible spectroscopy</topic><topic>Vitaceae</topic><topic>wine grapes</topic><topic>Wines and vinegars</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lambert, Stephanie G.</creatorcontrib><creatorcontrib>Asenstorfer, Robert E.</creatorcontrib><creatorcontrib>Williamson, Natalie M.</creatorcontrib><creatorcontrib>Iland, Patrick G.</creatorcontrib><creatorcontrib>Jones, Graham P.</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lambert, Stephanie G.</au><au>Asenstorfer, Robert E.</au><au>Williamson, Natalie M.</au><au>Iland, Patrick G.</au><au>Jones, Graham P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copigmentation between malvidin-3-glucoside and some wine constituents and its importance to colour expression in red wine</atitle><jtitle>Food chemistry</jtitle><date>2011-03-01</date><risdate>2011</risdate><volume>125</volume><issue>1</issue><spage>106</spage><epage>115</epage><pages>106-115</pages><issn>0308-8146</issn><eissn>1873-7072</eissn><coden>FOCHDJ</coden><abstract>Thermodynamic parameters for intermolecular copigmentation interactions involving malvidin-3-glucoside were determined by UV/visible spectroscopy at wine pH (pH 3.6). These included association constants, enthalpy and entropy changes, which were measured for chlorogenic acid, caffeic acid, quercetin, quercetin-3-glucoside, (−)-epicatechin, (+)-catechin, procyanidin dimer and seed tannin. Quercetin produced the strongest copigment (
K
CP
=
2900
±
1300), whilst the addition of glucose at position 3 (quercetin-3-glucoside) reduced its effect by almost 10-fold. Malvidin-3-glucoside self-association (
K
D
=
3300
±
300
mol
−1
l) was thermodynamically favoured over intermolecular interaction with any of the copigments tested. No colour enhancement due to self-association was observed for malvidin-3-glucoside-derived pigments that cannot enter hydration reactions. In addition, malvidin-3-(6-
O-
p-coumaryl)glucoside did not show colour enhancement suggesting that the
p-coumaryl group prevents self-association. The malvidin-3-glucoside circular dichroism (CD) spectrum was not affected by indicated changes in malvidin-3-glucoside concentration. These observations demonstrate that self-association of malvidin-3-glucoside is more important than copigmentation in young red wine.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.foodchem.2010.08.045</doi><tpages>10</tpages></addata></record> |
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| ispartof | Food chemistry, 2011-03, Vol.125 (1), p.106-115 |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings |
| subjects | anthocyanins Biological and medical sciences caffeic acid catechin chlorogenic acid color epicatechin Fermented food industries Flavan-3-ols Flavonols food composition Food industries Fundamental and applied biological sciences. Psychology grape seeds Intermolecular copigmentation Malvidin-3-glucoside phytochemicals plant pigments quercetin red wines Seed tannin Self-association tannins UV/visible spectroscopy Vitaceae wine grapes Wines and vinegars |
| title | Copigmentation between malvidin-3-glucoside and some wine constituents and its importance to colour expression in red wine |
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