Influence of Epicatechin Reactions on the Mechanisms of Maillard Product Formation in Low Moisture Model Systems
The influence of the polyphenolic compound epicatechin on Maillard chemistry was investigated under simulated roast conditions (10% moisture at 220 °C for 10 min). Quantitative gas chromatography (GC) analysis indicated that the addition of epicatechin to glucose or fructose/glycine model systems si...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2007-01, Vol.55 (2), p.414-420 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Totlani, Vandana M Peterson, Devin G |
| description | The influence of the polyphenolic compound epicatechin on Maillard chemistry was investigated under simulated roast conditions (10% moisture at 220 °C for 10 min). Quantitative gas chromatography (GC) analysis indicated that the addition of epicatechin to glucose or fructose/glycine model systems significantly reduced the generation of hydroxyacetone, 2-methylpyrazine, 2,3,5-trimethylpyrazine, furfural, 2-acetylfuran, 5-methylfurfural, 2(5H)-furanone, 2-acetylpyrrole, and furfuryl alcohol. These analytes were reported to be primarily generated from intact C2, C3, C4, C5, and C6 sugar fragments based on gas chromatography/mass spectrometry quantitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine model system. Liquid chromatography/mass spectrometry qualitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine/epicatechin model systems confirmed epicatechin reacted with Maillard reactants in the model systems; two main reaction products were reported, epicatechin−C5 and −C6 sugar fragment adducts. In addition, LC/MS analysis of a model system consisting of only 3-deoxy-2-hexosulose and epicatechin identified 3-deoxy-2-hexosulose as a precursor of the epicatechin−C5 and −C6 sugar fragment adducts reaction products. These results imply that epicatechin quenched 3-deoxy-2-hexosulose (a key source C6 to C1 sugar fragments) and consequently inhibited Maillard product formation. Keywords: Epicatechin; glycation; Maillard reaction; 3-deoxy-2-hexosulose; inhibit; carbonyl trapping |
| doi_str_mv | 10.1021/jf0617521 |
| format | Article |
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Quantitative gas chromatography (GC) analysis indicated that the addition of epicatechin to glucose or fructose/glycine model systems significantly reduced the generation of hydroxyacetone, 2-methylpyrazine, 2,3,5-trimethylpyrazine, furfural, 2-acetylfuran, 5-methylfurfural, 2(5H)-furanone, 2-acetylpyrrole, and furfuryl alcohol. These analytes were reported to be primarily generated from intact C2, C3, C4, C5, and C6 sugar fragments based on gas chromatography/mass spectrometry quantitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine model system. Liquid chromatography/mass spectrometry qualitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine/epicatechin model systems confirmed epicatechin reacted with Maillard reactants in the model systems; two main reaction products were reported, epicatechin−C5 and −C6 sugar fragment adducts. In addition, LC/MS analysis of a model system consisting of only 3-deoxy-2-hexosulose and epicatechin identified 3-deoxy-2-hexosulose as a precursor of the epicatechin−C5 and −C6 sugar fragment adducts reaction products. These results imply that epicatechin quenched 3-deoxy-2-hexosulose (a key source C6 to C1 sugar fragments) and consequently inhibited Maillard product formation. Keywords: Epicatechin; glycation; Maillard reaction; 3-deoxy-2-hexosulose; inhibit; carbonyl trapping</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0617521</identifier><identifier>PMID: 17227073</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Catechin - chemistry ; Chromatography, Gas ; Chromatography, Liquid ; cooking ; epicatechin ; food chemistry ; Food industries ; fructose ; Fructose - chemistry ; Fundamental and applied biological sciences. Psychology ; glucose ; Glucose - chemistry ; glycine (amino acid) ; Glycine - chemistry ; Maillard Reaction ; Maillard reaction products ; Mass Spectrometry ; Models, Chemical ; roasting ; Water - analysis</subject><ispartof>Journal of agricultural and food chemistry, 2007-01, Vol.55 (2), p.414-420</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a436t-66c5088ccbedc3c7733a26b5d45e5035c6378f46ed293d6ee6ca66c99175567d3</citedby><cites>FETCH-LOGICAL-a436t-66c5088ccbedc3c7733a26b5d45e5035c6378f46ed293d6ee6ca66c99175567d3</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/jf0617521$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0617521$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18469349$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17227073$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Totlani, Vandana M</creatorcontrib><creatorcontrib>Peterson, Devin G</creatorcontrib><title>Influence of Epicatechin Reactions on the Mechanisms of Maillard Product Formation in Low Moisture Model Systems</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The influence of the polyphenolic compound epicatechin on Maillard chemistry was investigated under simulated roast conditions (10% moisture at 220 °C for 10 min). Quantitative gas chromatography (GC) analysis indicated that the addition of epicatechin to glucose or fructose/glycine model systems significantly reduced the generation of hydroxyacetone, 2-methylpyrazine, 2,3,5-trimethylpyrazine, furfural, 2-acetylfuran, 5-methylfurfural, 2(5H)-furanone, 2-acetylpyrrole, and furfuryl alcohol. These analytes were reported to be primarily generated from intact C2, C3, C4, C5, and C6 sugar fragments based on gas chromatography/mass spectrometry quantitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine model system. Liquid chromatography/mass spectrometry qualitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine/epicatechin model systems confirmed epicatechin reacted with Maillard reactants in the model systems; two main reaction products were reported, epicatechin−C5 and −C6 sugar fragment adducts. In addition, LC/MS analysis of a model system consisting of only 3-deoxy-2-hexosulose and epicatechin identified 3-deoxy-2-hexosulose as a precursor of the epicatechin−C5 and −C6 sugar fragment adducts reaction products. These results imply that epicatechin quenched 3-deoxy-2-hexosulose (a key source C6 to C1 sugar fragments) and consequently inhibited Maillard product formation. Keywords: Epicatechin; glycation; Maillard reaction; 3-deoxy-2-hexosulose; inhibit; carbonyl trapping</description><subject>Biological and medical sciences</subject><subject>Catechin - chemistry</subject><subject>Chromatography, Gas</subject><subject>Chromatography, Liquid</subject><subject>cooking</subject><subject>epicatechin</subject><subject>food chemistry</subject><subject>Food industries</subject><subject>fructose</subject><subject>Fructose - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glucose</subject><subject>Glucose - chemistry</subject><subject>glycine (amino acid)</subject><subject>Glycine - chemistry</subject><subject>Maillard Reaction</subject><subject>Maillard reaction products</subject><subject>Mass Spectrometry</subject><subject>Models, Chemical</subject><subject>roasting</subject><subject>Water - analysis</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>eNqF0UFv0zAUB3ALMbEyOPAFwBeQdgg827GdHKdpg00tDLqdLdd5YSmJXexEsG-Pq1brBWknS_bv_2y_R8gbBh8ZcPZp3YJiWnL2jMyY5FBIxqrnZAb5sKikYsfkZUprAKikhhfkmGnONWgxI5sr3_YTeoc0tPRi0zk7orvvPP2B1o1d8IkGT8d7pIu8b32XhrSlC9v1vY0NvYmhmdxIL0Mc7DZAc3ge_tBF6NI4xRwMDfZ0-ZBGHNIrctTaPuHr_XpC7i4vbs-_FPNvn6_Oz-aFLYUaC6WchKpyboWNE05rISxXK9mUEiUI6ZTQVVsqbHgtGoWonM2Zus59kEo34oR82NXdxPB7wjSaoUsO85s9hikZVdWcKSifhByEBl5u4ekOuhhSitiaTewGGx8MA7Odg3mcQ7Zv90Wn1YDNQe4bn8H7PbDJ2b6N1rsuHVxVqlqUdXbFzuVe4t_Hcxt_GaWFlub2Zmm-L-b8K8hrw7N_t_OtDcb-jLnm3ZIDEwC6ZLKUh5utS2YdpujzGP7zhX-dIbMi</recordid><startdate>20070124</startdate><enddate>20070124</enddate><creator>Totlani, Vandana M</creator><creator>Peterson, Devin G</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>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070124</creationdate><title>Influence of Epicatechin Reactions on the Mechanisms of Maillard Product Formation in Low Moisture Model Systems</title><author>Totlani, Vandana M ; Peterson, Devin G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-66c5088ccbedc3c7733a26b5d45e5035c6378f46ed293d6ee6ca66c99175567d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Biological and medical sciences</topic><topic>Catechin - chemistry</topic><topic>Chromatography, Gas</topic><topic>Chromatography, Liquid</topic><topic>cooking</topic><topic>epicatechin</topic><topic>food chemistry</topic><topic>Food industries</topic><topic>fructose</topic><topic>Fructose - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glucose</topic><topic>Glucose - chemistry</topic><topic>glycine (amino acid)</topic><topic>Glycine - chemistry</topic><topic>Maillard Reaction</topic><topic>Maillard reaction products</topic><topic>Mass Spectrometry</topic><topic>Models, Chemical</topic><topic>roasting</topic><topic>Water - analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Totlani, Vandana M</creatorcontrib><creatorcontrib>Peterson, Devin G</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>Chemoreception Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</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>Totlani, Vandana M</au><au>Peterson, Devin G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Influence of Epicatechin Reactions on the Mechanisms of Maillard Product Formation in Low Moisture Model Systems</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2007-01-24</date><risdate>2007</risdate><volume>55</volume><issue>2</issue><spage>414</spage><epage>420</epage><pages>414-420</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The influence of the polyphenolic compound epicatechin on Maillard chemistry was investigated under simulated roast conditions (10% moisture at 220 °C for 10 min). Quantitative gas chromatography (GC) analysis indicated that the addition of epicatechin to glucose or fructose/glycine model systems significantly reduced the generation of hydroxyacetone, 2-methylpyrazine, 2,3,5-trimethylpyrazine, furfural, 2-acetylfuran, 5-methylfurfural, 2(5H)-furanone, 2-acetylpyrrole, and furfuryl alcohol. These analytes were reported to be primarily generated from intact C2, C3, C4, C5, and C6 sugar fragments based on gas chromatography/mass spectrometry quantitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine model system. Liquid chromatography/mass spectrometry qualitative isotopomeric analysis of a 1:1 13C6:12C6 hexose sugar/glycine/epicatechin model systems confirmed epicatechin reacted with Maillard reactants in the model systems; two main reaction products were reported, epicatechin−C5 and −C6 sugar fragment adducts. In addition, LC/MS analysis of a model system consisting of only 3-deoxy-2-hexosulose and epicatechin identified 3-deoxy-2-hexosulose as a precursor of the epicatechin−C5 and −C6 sugar fragment adducts reaction products. These results imply that epicatechin quenched 3-deoxy-2-hexosulose (a key source C6 to C1 sugar fragments) and consequently inhibited Maillard product formation. Keywords: Epicatechin; glycation; Maillard reaction; 3-deoxy-2-hexosulose; inhibit; carbonyl trapping</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17227073</pmid><doi>10.1021/jf0617521</doi><tpages>7</tpages></addata></record> |
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| source | ACS Publications; MEDLINE |
| subjects | Biological and medical sciences Catechin - chemistry Chromatography, Gas Chromatography, Liquid cooking epicatechin food chemistry Food industries fructose Fructose - chemistry Fundamental and applied biological sciences. Psychology glucose Glucose - chemistry glycine (amino acid) Glycine - chemistry Maillard Reaction Maillard reaction products Mass Spectrometry Models, Chemical roasting Water - analysis |
| title | Influence of Epicatechin Reactions on the Mechanisms of Maillard Product Formation in Low Moisture Model Systems |
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