Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry
Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions we...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2012-09, Vol.60 (36), p.9261-9272 |
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| container_issue | 36 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Huvaere, Kevin Sinnaeve, Bart Van Bocxlaer, Jan Skibsted, Leif H |
| description | Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC–MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity. |
| doi_str_mv | 10.1021/jf301823h |
| format | Article |
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Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf301823h</identifier><identifier>PMID: 22889117</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>antioxidant activity ; apigenin ; aqueous solutions ; astringency ; Biological and medical sciences ; catechin ; cations ; color ; Dimerization ; Flavins - chemistry ; Flavonoids - chemistry ; Food industries ; foods ; Fundamental and applied biological sciences. Psychology ; kaempferol ; luteolin ; mass spectrometry ; Mass Spectrometry - methods ; Molecular Structure ; monitoring ; naringenin ; phenols ; quercetin ; riboflavin ; rutin ; Spectrometry, Mass, Electrospray Ionization - methods ; taxifolin</subject><ispartof>Journal of agricultural and food chemistry, 2012-09, Vol.60 (36), p.9261-9272</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a369t-ce8412a7a7928b8bd605565a6e1a2f63b475b1a799edd46f0021d0cd4b88989c3</citedby><cites>FETCH-LOGICAL-a369t-ce8412a7a7928b8bd605565a6e1a2f63b475b1a799edd46f0021d0cd4b88989c3</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/jf301823h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf301823h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>309,310,314,776,780,785,786,2752,23909,23910,25118,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26425052$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22889117$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huvaere, Kevin</creatorcontrib><creatorcontrib>Sinnaeve, Bart</creatorcontrib><creatorcontrib>Van Bocxlaer, Jan</creatorcontrib><creatorcontrib>Skibsted, Leif H</creatorcontrib><title>Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC–MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.</description><subject>antioxidant activity</subject><subject>apigenin</subject><subject>aqueous solutions</subject><subject>astringency</subject><subject>Biological and medical sciences</subject><subject>catechin</subject><subject>cations</subject><subject>color</subject><subject>Dimerization</subject><subject>Flavins - chemistry</subject><subject>Flavonoids - chemistry</subject><subject>Food industries</subject><subject>foods</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>kaempferol</subject><subject>luteolin</subject><subject>mass spectrometry</subject><subject>Mass Spectrometry - methods</subject><subject>Molecular Structure</subject><subject>monitoring</subject><subject>naringenin</subject><subject>phenols</subject><subject>quercetin</subject><subject>riboflavin</subject><subject>rutin</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><subject>taxifolin</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFOGzEQBmALgSCFHniB4gtSe1jq8a693t4QhYIUhESaA6fVrNdLHW3Wqe2g5u3rNGly4TSH-fRr5ifkHNgVMA5fZ13OQPH81wEZgeAsEwDqkIxYWmZKSDghH0KYMcaUKNkxOeFcqQqgHJGXux7f3OBsS78b1NG-YbRuoK6jt3-0jaalk4jR0LWzQ_hGn_-xRB7dYKPzdnilzYo-Ygh0sjA6ejc30a_OyFGHfTAft_OUTO9uf97cZ-OnHw831-MMc1nFTBtVAMcSy4qrRjWtZEJIgdIA8k7mTVGKBtK2Mm1byG79U8t0WzTpBVXp_JR83uQuvPu9NCHWcxu06XscjFuGGlhe5YUEKRP9sqHauxC86eqFt3P0q4TqdZP1rslkP21jl83ctDv5v7oELrcAg8a-8zhoG_ZOFlwwwZO72LgOXY2vPpnphDMoGAOoCsn3SahDPXNLP6S-3jnpLw5Mj6w</recordid><startdate>20120912</startdate><enddate>20120912</enddate><creator>Huvaere, Kevin</creator><creator>Sinnaeve, Bart</creator><creator>Van Bocxlaer, Jan</creator><creator>Skibsted, Leif H</creator><general>American Chemical Society</general><scope>FBQ</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>20120912</creationdate><title>Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry</title><author>Huvaere, Kevin ; Sinnaeve, Bart ; Van Bocxlaer, Jan ; Skibsted, Leif H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a369t-ce8412a7a7928b8bd605565a6e1a2f63b475b1a799edd46f0021d0cd4b88989c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>antioxidant activity</topic><topic>apigenin</topic><topic>aqueous solutions</topic><topic>astringency</topic><topic>Biological and medical sciences</topic><topic>catechin</topic><topic>cations</topic><topic>color</topic><topic>Dimerization</topic><topic>Flavins - chemistry</topic><topic>Flavonoids - chemistry</topic><topic>Food industries</topic><topic>foods</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>kaempferol</topic><topic>luteolin</topic><topic>mass spectrometry</topic><topic>Mass Spectrometry - methods</topic><topic>Molecular Structure</topic><topic>monitoring</topic><topic>naringenin</topic><topic>phenols</topic><topic>quercetin</topic><topic>riboflavin</topic><topic>rutin</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><topic>taxifolin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huvaere, Kevin</creatorcontrib><creatorcontrib>Sinnaeve, Bart</creatorcontrib><creatorcontrib>Van Bocxlaer, Jan</creatorcontrib><creatorcontrib>Skibsted, Leif H</creatorcontrib><collection>AGRIS</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>Huvaere, Kevin</au><au>Sinnaeve, Bart</au><au>Van Bocxlaer, Jan</au><au>Skibsted, Leif H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2012-09-12</date><risdate>2012</risdate><volume>60</volume><issue>36</issue><spage>9261</spage><epage>9272</epage><pages>9261-9272</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC–MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22889117</pmid><doi>10.1021/jf301823h</doi><tpages>12</tpages></addata></record> |
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| subjects | antioxidant activity apigenin aqueous solutions astringency Biological and medical sciences catechin cations color Dimerization Flavins - chemistry Flavonoids - chemistry Food industries foods Fundamental and applied biological sciences. Psychology kaempferol luteolin mass spectrometry Mass Spectrometry - methods Molecular Structure monitoring naringenin phenols quercetin riboflavin rutin Spectrometry, Mass, Electrospray Ionization - methods taxifolin |
| title | Flavonoid Deactivation of Excited State Flavins: Reaction Monitoring by Mass Spectrometry |
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