Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils
The emphasis of the present work was to investigate the photochemical conversion of trans- to cis-zearalenone in edible oils under real-life conditions. For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by 1H NMR, X-ray crystall...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2012-11, Vol.60 (47), p.11733-11740 |
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| container_issue | 47 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Köppen, Robert Riedel, Juliane Proske, Matthias Drzymala, Sarah Rasenko, Tatjana Durmaz, Vedat Weber, Marcus Koch, Matthias |
| description | The emphasis of the present work was to investigate the photochemical conversion of trans- to cis-zearalenone in edible oils under real-life conditions. For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by 1H NMR, X-ray crystallography, HPLC fluorescence and mass spectrometric detection. In a sample survey of 12 edible oils (9 corn oils, 3 hempseed oils) from local supermarkets all corn oils contained trans-zearalenone (median 194 μg/kg), but no cis-zearalenone was detected. For alteration studies trans-zearalenone contaminated corn oils were exposed to sunlight over 4 and 30 weeks, revealing an obvious shift toward cis-zearalenone up to a cis/trans ratio of 9:1 by storage in colorless glass bottles. Irradiation experiments of trans-zearalenone in different organic solvents confirmed the preferred formation of cis-zearalenone possibly caused by entropic effects rather than by enthalpic entities as investigated by quantum chemical and classical force field simulations. |
| doi_str_mv | 10.1021/jf3037775 |
| format | Article |
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For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by 1H NMR, X-ray crystallography, HPLC fluorescence and mass spectrometric detection. In a sample survey of 12 edible oils (9 corn oils, 3 hempseed oils) from local supermarkets all corn oils contained trans-zearalenone (median 194 μg/kg), but no cis-zearalenone was detected. For alteration studies trans-zearalenone contaminated corn oils were exposed to sunlight over 4 and 30 weeks, revealing an obvious shift toward cis-zearalenone up to a cis/trans ratio of 9:1 by storage in colorless glass bottles. Irradiation experiments of trans-zearalenone in different organic solvents confirmed the preferred formation of cis-zearalenone possibly caused by entropic effects rather than by enthalpic entities as investigated by quantum chemical and classical force field simulations.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf3037775</identifier><identifier>PMID: 23157684</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; bottles ; Cannabis ; corn oil ; Corn Oil - chemistry ; Drug Stability ; Fat industries ; fluorescence ; Food industries ; Food toxicology ; Fundamental and applied biological sciences. Psychology ; glass ; high performance liquid chromatography ; irradiation ; Isomerism ; mass spectrometry ; nuclear magnetic resonance spectroscopy ; Photochemistry ; Plant Oils - chemistry ; Seeds - chemistry ; solvents ; Sunlight ; supermarkets ; surveys ; X-ray diffraction ; zearalenone ; Zearalenone - analysis ; Zearalenone - chemistry</subject><ispartof>Journal of agricultural and food chemistry, 2012-11, Vol.60 (47), p.11733-11740</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a369t-9bb5c565e222c327f5a14523b7eb5faad87984474ce0d1ae6ad45370ac4e1483</citedby><cites>FETCH-LOGICAL-a369t-9bb5c565e222c327f5a14523b7eb5faad87984474ce0d1ae6ad45370ac4e1483</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/jf3037775$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf3037775$$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=26674204$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23157684$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Köppen, Robert</creatorcontrib><creatorcontrib>Riedel, Juliane</creatorcontrib><creatorcontrib>Proske, Matthias</creatorcontrib><creatorcontrib>Drzymala, Sarah</creatorcontrib><creatorcontrib>Rasenko, Tatjana</creatorcontrib><creatorcontrib>Durmaz, Vedat</creatorcontrib><creatorcontrib>Weber, Marcus</creatorcontrib><creatorcontrib>Koch, Matthias</creatorcontrib><title>Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The emphasis of the present work was to investigate the photochemical conversion of trans- to cis-zearalenone in edible oils under real-life conditions. For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by 1H NMR, X-ray crystallography, HPLC fluorescence and mass spectrometric detection. In a sample survey of 12 edible oils (9 corn oils, 3 hempseed oils) from local supermarkets all corn oils contained trans-zearalenone (median 194 μg/kg), but no cis-zearalenone was detected. For alteration studies trans-zearalenone contaminated corn oils were exposed to sunlight over 4 and 30 weeks, revealing an obvious shift toward cis-zearalenone up to a cis/trans ratio of 9:1 by storage in colorless glass bottles. Irradiation experiments of trans-zearalenone in different organic solvents confirmed the preferred formation of cis-zearalenone possibly caused by entropic effects rather than by enthalpic entities as investigated by quantum chemical and classical force field simulations.</description><subject>Biological and medical sciences</subject><subject>bottles</subject><subject>Cannabis</subject><subject>corn oil</subject><subject>Corn Oil - chemistry</subject><subject>Drug Stability</subject><subject>Fat industries</subject><subject>fluorescence</subject><subject>Food industries</subject><subject>Food toxicology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glass</subject><subject>high performance liquid chromatography</subject><subject>irradiation</subject><subject>Isomerism</subject><subject>mass spectrometry</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Photochemistry</subject><subject>Plant Oils - chemistry</subject><subject>Seeds - chemistry</subject><subject>solvents</subject><subject>Sunlight</subject><subject>supermarkets</subject><subject>surveys</subject><subject>X-ray diffraction</subject><subject>zearalenone</subject><subject>Zearalenone - analysis</subject><subject>Zearalenone - chemistry</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>eNpt0D9P3TAUh2GrKoJbYOgXaLNUKkPg-F-cjAjRgoQEVWFhiU6ck-KrxKZ2MtBPj9G9hYXJkv3oJ-tl7DOHYw6Cn6wHCdIYoz-wFdcCSs15_ZGtID-Wta74HvuU0hoAam1gl-0JybWparVidzcPYQ72gSZncSzmiD6VJ9al8jKFiaL7h7MLvkDfF78W9LObNxdhKO4JI47kg6fC-eK8d91IxbUb0wHbGXBMdLg999ntj_Pbs4vy6vrn5dnpVYmyauay6TptdaVJCGGlMINGrrSQnaFOD4h9bZpaKaMsQc-RKuyVlgbQKuKqlvvs-2b2MYa_C6W5nVyyNI7oKSyp5UKAaZSsVKZHG2pjSCnS0D5GN2F8ajm0LxHb14jZftnOLt1E_av8Xy2Db1uAKVcbcrRc7M1VlVECXtzXjRswtPgnZnP3WwBXAJw3WjZvS2hTuw5L9DnXO196BsmvjaU</recordid><startdate>20121128</startdate><enddate>20121128</enddate><creator>Köppen, Robert</creator><creator>Riedel, Juliane</creator><creator>Proske, Matthias</creator><creator>Drzymala, Sarah</creator><creator>Rasenko, Tatjana</creator><creator>Durmaz, Vedat</creator><creator>Weber, Marcus</creator><creator>Koch, Matthias</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>20121128</creationdate><title>Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils</title><author>Köppen, Robert ; Riedel, Juliane ; Proske, Matthias ; Drzymala, Sarah ; Rasenko, Tatjana ; Durmaz, Vedat ; Weber, Marcus ; Koch, Matthias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a369t-9bb5c565e222c327f5a14523b7eb5faad87984474ce0d1ae6ad45370ac4e1483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Biological and medical sciences</topic><topic>bottles</topic><topic>Cannabis</topic><topic>corn oil</topic><topic>Corn Oil - chemistry</topic><topic>Drug Stability</topic><topic>Fat industries</topic><topic>fluorescence</topic><topic>Food industries</topic><topic>Food toxicology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glass</topic><topic>high performance liquid chromatography</topic><topic>irradiation</topic><topic>Isomerism</topic><topic>mass spectrometry</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Photochemistry</topic><topic>Plant Oils - chemistry</topic><topic>Seeds - chemistry</topic><topic>solvents</topic><topic>Sunlight</topic><topic>supermarkets</topic><topic>surveys</topic><topic>X-ray diffraction</topic><topic>zearalenone</topic><topic>Zearalenone - analysis</topic><topic>Zearalenone - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Köppen, Robert</creatorcontrib><creatorcontrib>Riedel, Juliane</creatorcontrib><creatorcontrib>Proske, Matthias</creatorcontrib><creatorcontrib>Drzymala, Sarah</creatorcontrib><creatorcontrib>Rasenko, Tatjana</creatorcontrib><creatorcontrib>Durmaz, Vedat</creatorcontrib><creatorcontrib>Weber, Marcus</creatorcontrib><creatorcontrib>Koch, Matthias</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>Köppen, Robert</au><au>Riedel, Juliane</au><au>Proske, Matthias</au><au>Drzymala, Sarah</au><au>Rasenko, Tatjana</au><au>Durmaz, Vedat</au><au>Weber, Marcus</au><au>Koch, Matthias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2012-11-28</date><risdate>2012</risdate><volume>60</volume><issue>47</issue><spage>11733</spage><epage>11740</epage><pages>11733-11740</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The emphasis of the present work was to investigate the photochemical conversion of trans- to cis-zearalenone in edible oils under real-life conditions. For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by 1H NMR, X-ray crystallography, HPLC fluorescence and mass spectrometric detection. In a sample survey of 12 edible oils (9 corn oils, 3 hempseed oils) from local supermarkets all corn oils contained trans-zearalenone (median 194 μg/kg), but no cis-zearalenone was detected. For alteration studies trans-zearalenone contaminated corn oils were exposed to sunlight over 4 and 30 weeks, revealing an obvious shift toward cis-zearalenone up to a cis/trans ratio of 9:1 by storage in colorless glass bottles. Irradiation experiments of trans-zearalenone in different organic solvents confirmed the preferred formation of cis-zearalenone possibly caused by entropic effects rather than by enthalpic entities as investigated by quantum chemical and classical force field simulations.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>23157684</pmid><doi>10.1021/jf3037775</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2012-11, Vol.60 (47), p.11733-11740 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Biological and medical sciences bottles Cannabis corn oil Corn Oil - chemistry Drug Stability Fat industries fluorescence Food industries Food toxicology Fundamental and applied biological sciences. Psychology glass high performance liquid chromatography irradiation Isomerism mass spectrometry nuclear magnetic resonance spectroscopy Photochemistry Plant Oils - chemistry Seeds - chemistry solvents Sunlight supermarkets surveys X-ray diffraction zearalenone Zearalenone - analysis Zearalenone - chemistry |
| title | Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils |
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