Docosahexaenoic Acid is More Stable to Oxidation when Located at the sn-2 Position of Triacylglycerol Compared to sn-1(3)
Regio-isomeric effects on the oxidative stability of triacylglycerols (TAG) containing docosahexaenoic acid (DHA) were investigated using two pairs of regio-isomerically pure TAG, namely 1,3-dihexadecanoyl-2-(4,7,10,13,16,19-docosahexaenoyl)glycerol (PDP)/1,2-dihexadecanoyl-3-(4,7,10,13,16,19-docosa...
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| Veröffentlicht in: | Journal of the American Oil Chemists' Society 2008-06, Vol.85 (6), p.543-548 |
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| container_title | Journal of the American Oil Chemists' Society |
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| creator | Wijesundera, Chakra Ceccato, Claudio Watkins, Peter Fagan, Peter Fraser, Benjamin Thienthong, Neeranat Perlmutter, Patrick |
| description | Regio-isomeric effects on the oxidative stability of triacylglycerols (TAG) containing docosahexaenoic acid (DHA) were investigated using two pairs of regio-isomerically pure TAG, namely 1,3-dihexadecanoyl-2-(4,7,10,13,16,19-docosahexaenoyl)glycerol (PDP)/1,2-dihexadecanoyl-3-(4,7,10,13,16,19-docosahexaenoyl)glycerol (PPD) and 1,3-dioctadecenoyl-2-(4,7,10,13,16,19-docosahexaenoyl)glycerol (ODO)/1,2-dioctadecenoyl-3-(4,7,10,13,16,19-docosahexaenoyl)glycerol (OOD) where P, O, and D represent palmitic acid, oleic acid, and DHA respectively. Each pair of regio-isomers was subjected to accelerated auto-oxidation (at 40 or 50 °C inside a dark oven). In each case, the TAG oxidized more slowly when DHA was located at the sn-2 position (PDP and ODO) compared to the sn-1(3) position (PPD and OOD), as evidenced by slower development of peroxide value, slower depletion of DHA, and slower generation of secondary oxidation products propanal and trans, trans-2,4-heptadienal. The positional effect on auto-oxidation was more pronounced when DHA occurred in combination with oleic acid than with palmitic acid. |
| doi_str_mv | 10.1007/s11746-008-1224-z |
| format | Article |
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Each pair of regio-isomers was subjected to accelerated auto-oxidation (at 40 or 50 °C inside a dark oven). In each case, the TAG oxidized more slowly when DHA was located at the sn-2 position (PDP and ODO) compared to the sn-1(3) position (PPD and OOD), as evidenced by slower development of peroxide value, slower depletion of DHA, and slower generation of secondary oxidation products propanal and trans, trans-2,4-heptadienal. The positional effect on auto-oxidation was more pronounced when DHA occurred in combination with oleic acid than with palmitic acid.</description><identifier>ISSN: 0003-021X</identifier><identifier>EISSN: 1558-9331</identifier><identifier>DOI: 10.1007/s11746-008-1224-z</identifier><language>eng</language><publisher>Berlin/Heidelberg: Berlin/Heidelberg : Springer-Verlag</publisher><subject>Agriculture ; Auto‐oxidation ; Biological and medical sciences ; Biomaterials ; Biotechnology ; chemical structure ; Chemicals ; Chemistry ; Chemistry and Materials Science ; dietary fat ; Docosahexaenoic acid ; Fat industries ; Fatty acids ; Fish oils ; Food industries ; Food Science ; Fundamental and applied biological sciences. Psychology ; Industrial Chemistry/Chemical Engineering ; Omega‐3 fatty acid ; Original Paper ; Oxidation ; Oxidative stability ; Regio‐isomer ; structure-activity relationships ; Studies ; Temperature ; Triacylglycerol ; triacylglycerols</subject><ispartof>Journal of the American Oil Chemists' Society, 2008-06, Vol.85 (6), p.543-548</ispartof><rights>AOCS 2008</rights><rights>2008 American Oil Chemists' Society (AOCS)</rights><rights>2008 INIST-CNRS</rights><rights>Copyright AOCS Press Jun 2008</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4833-6b0e20a84d2a87caf340cd74e95a79d88e437cbeae86f7be8b8d939ca7274da43</citedby><cites>FETCH-LOGICAL-c4833-6b0e20a84d2a87caf340cd74e95a79d88e437cbeae86f7be8b8d939ca7274da43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11746-008-1224-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11746-008-1224-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,41469,42538,45555,45556,51300</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20353602$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Wijesundera, Chakra</creatorcontrib><creatorcontrib>Ceccato, Claudio</creatorcontrib><creatorcontrib>Watkins, Peter</creatorcontrib><creatorcontrib>Fagan, Peter</creatorcontrib><creatorcontrib>Fraser, Benjamin</creatorcontrib><creatorcontrib>Thienthong, Neeranat</creatorcontrib><creatorcontrib>Perlmutter, Patrick</creatorcontrib><title>Docosahexaenoic Acid is More Stable to Oxidation when Located at the sn-2 Position of Triacylglycerol Compared to sn-1(3)</title><title>Journal of the American Oil Chemists' Society</title><addtitle>J Am Oil Chem Soc</addtitle><description>Regio-isomeric effects on the oxidative stability of triacylglycerols (TAG) containing docosahexaenoic acid (DHA) were investigated using two pairs of regio-isomerically pure TAG, namely 1,3-dihexadecanoyl-2-(4,7,10,13,16,19-docosahexaenoyl)glycerol (PDP)/1,2-dihexadecanoyl-3-(4,7,10,13,16,19-docosahexaenoyl)glycerol (PPD) and 1,3-dioctadecenoyl-2-(4,7,10,13,16,19-docosahexaenoyl)glycerol (ODO)/1,2-dioctadecenoyl-3-(4,7,10,13,16,19-docosahexaenoyl)glycerol (OOD) where P, O, and D represent palmitic acid, oleic acid, and DHA respectively. Each pair of regio-isomers was subjected to accelerated auto-oxidation (at 40 or 50 °C inside a dark oven). In each case, the TAG oxidized more slowly when DHA was located at the sn-2 position (PDP and ODO) compared to the sn-1(3) position (PPD and OOD), as evidenced by slower development of peroxide value, slower depletion of DHA, and slower generation of secondary oxidation products propanal and trans, trans-2,4-heptadienal. The positional effect on auto-oxidation was more pronounced when DHA occurred in combination with oleic acid than with palmitic acid.</description><subject>Agriculture</subject><subject>Auto‐oxidation</subject><subject>Biological and medical sciences</subject><subject>Biomaterials</subject><subject>Biotechnology</subject><subject>chemical structure</subject><subject>Chemicals</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>dietary fat</subject><subject>Docosahexaenoic acid</subject><subject>Fat industries</subject><subject>Fatty acids</subject><subject>Fish oils</subject><subject>Food industries</subject><subject>Food Science</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Omega‐3 fatty acid</subject><subject>Original Paper</subject><subject>Oxidation</subject><subject>Oxidative stability</subject><subject>Regio‐isomer</subject><subject>structure-activity relationships</subject><subject>Studies</subject><subject>Temperature</subject><subject>Triacylglycerol</subject><subject>triacylglycerols</subject><issn>0003-021X</issn><issn>1558-9331</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNqFkF1rFDEUhgdRcG39AV4ZBMFexOZrJpnLZWtVWNnCtuBdOJM5s5synazJlHb665s6Re_0Khx4njcvb1G84-wzZ0yfJs61qihjhnIhFH14USx4WRpaS8lfFgvGmKRM8J-vizcpXefTSFEuiuksuJBgj_eAQ_COLJ1viU_kR4hItiM0PZIxkM29b2H0YSB3exzIOjgYsSUwknGPJA1UkIuQ_G8idOQyenBTv-snhzH0ZBVuDhCzkKMyzD_Jk-PiVQd9wrfP71Fxdf7lcvWNrjdfv6-Wa-qUkZJWDUPBwKhWgNEOOqmYa7XCugRdt8agkto1CGiqTjdoGtPWsnaghVYtKHlUfJhzDzH8usU02utwG4f8pRW6ZLVRlc4QnyEXQ0oRO3uI_gbiZDmzTwPbeWCbd7NPA9uH7Hx8DobkoO8iDM6nP6JgspQVE5nTM3fne5z-H2yXm9WWlUpmU8xmytKww_i3-r9qvZ-lDoKFXcyVrraCcZmZupJSyEduSaUO</recordid><startdate>200806</startdate><enddate>200806</enddate><creator>Wijesundera, Chakra</creator><creator>Ceccato, Claudio</creator><creator>Watkins, Peter</creator><creator>Fagan, Peter</creator><creator>Fraser, Benjamin</creator><creator>Thienthong, Neeranat</creator><creator>Perlmutter, Patrick</creator><general>Berlin/Heidelberg : Springer-Verlag</general><general>Springer-Verlag</general><general>Springer</general><general>Springer Nature B.V</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>4T-</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AO</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M2P</scope><scope>MBDVC</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope></search><sort><creationdate>200806</creationdate><title>Docosahexaenoic Acid is More Stable to Oxidation when Located at the sn-2 Position of Triacylglycerol Compared to sn-1(3)</title><author>Wijesundera, Chakra ; Ceccato, Claudio ; Watkins, Peter ; Fagan, Peter ; Fraser, Benjamin ; Thienthong, Neeranat ; Perlmutter, Patrick</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4833-6b0e20a84d2a87caf340cd74e95a79d88e437cbeae86f7be8b8d939ca7274da43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Agriculture</topic><topic>Auto‐oxidation</topic><topic>Biological and medical sciences</topic><topic>Biomaterials</topic><topic>Biotechnology</topic><topic>chemical structure</topic><topic>Chemicals</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>dietary fat</topic><topic>Docosahexaenoic acid</topic><topic>Fat industries</topic><topic>Fatty acids</topic><topic>Fish oils</topic><topic>Food industries</topic><topic>Food Science</topic><topic>Fundamental and applied biological sciences. 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Each pair of regio-isomers was subjected to accelerated auto-oxidation (at 40 or 50 °C inside a dark oven). In each case, the TAG oxidized more slowly when DHA was located at the sn-2 position (PDP and ODO) compared to the sn-1(3) position (PPD and OOD), as evidenced by slower development of peroxide value, slower depletion of DHA, and slower generation of secondary oxidation products propanal and trans, trans-2,4-heptadienal. The positional effect on auto-oxidation was more pronounced when DHA occurred in combination with oleic acid than with palmitic acid.</abstract><cop>Berlin/Heidelberg</cop><pub>Berlin/Heidelberg : Springer-Verlag</pub><doi>10.1007/s11746-008-1224-z</doi><tpages>6</tpages></addata></record> |
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| subjects | Agriculture Auto‐oxidation Biological and medical sciences Biomaterials Biotechnology chemical structure Chemicals Chemistry Chemistry and Materials Science dietary fat Docosahexaenoic acid Fat industries Fatty acids Fish oils Food industries Food Science Fundamental and applied biological sciences. Psychology Industrial Chemistry/Chemical Engineering Omega‐3 fatty acid Original Paper Oxidation Oxidative stability Regio‐isomer structure-activity relationships Studies Temperature Triacylglycerol triacylglycerols |
| title | Docosahexaenoic Acid is More Stable to Oxidation when Located at the sn-2 Position of Triacylglycerol Compared to sn-1(3) |
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