Development of a Flow-Injection ESR System for Evaluating the Lipophilic Alkoxyl Radical Eliminating Capacities (L-AREC) of Tocopherol Analogues and Unsaturated Fatty Acids
A new lipophilic spin-trapping flow-injection electron spin resonance (LFI-ESR) system was developed for quantitative detection of DMPO spin-adduct of alkoxyl radical (RO•), which was produced by thermal decomposition of an azo-initiator (AIBN) in ethyl acetate at 70 °C. The 50% and 75% inhibition d...
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creator | Sakurai, Yasuhiro Yamaguchi, Tomoko Ando, Kai Kuwabara, Keiko Nakajima, Hiroki Morimoto, Chie Yoshikawa, Shinichi Niwa, Masumi Miyake, Yusuke Kanaori, Kenji Nakajima, Akira Tajima, Kunihiko |
description | A new lipophilic spin-trapping flow-injection electron spin resonance (LFI-ESR) system was developed for quantitative detection of DMPO spin-adduct of alkoxyl radical (RO•), which was produced by thermal decomposition of an azo-initiator (AIBN) in ethyl acetate at 70 °C. The 50% and 75% inhibition dose (ID50 and ID75) of a series of lipophilic antioxidants, such as tocopherol derivatives (αToc, βToc, γToc, δToc, Toc, αTocM, βTocM, γTocM, TocM, TRX, and 7TocM), a lipophilic phenol (BHT), and unsaturated fatty acids (Ole, Lin, and Lic), were determined by monitoring the ESR signal intensity of the DMPO spin-adducts of RO• radical (DMPO/OR). On the basis of the observed ID50 and ID75 values, the lipophilic alkoxyl radical eliminating capacities (L-AREC) of these lipophilic antioxidants were determined using TRX as a standard. The evaluated L-AREC values are directly connected to the second order rate constants for the RO• radical induced hydrogen atom abstractions from the hydroxyl groups of the phenolic antioxidants, as well as from the allylic methylene groups of unsaturated fatty acids. The L-AREC values estimated by LFI-ESR method are concluded to be a practical and reliable indicator that reflect the inhibiting abilities of lipophilic antioxidants towards the radical chain reaction involved in the autoxidation processes of unsaturated fatty acids. |
doi_str_mv | 10.1246/bcsj.20190059 |
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The 50% and 75% inhibition dose (ID50 and ID75) of a series of lipophilic antioxidants, such as tocopherol derivatives (αToc, βToc, γToc, δToc, Toc, αTocM, βTocM, γTocM, TocM, TRX, and 7TocM), a lipophilic phenol (BHT), and unsaturated fatty acids (Ole, Lin, and Lic), were determined by monitoring the ESR signal intensity of the DMPO spin-adducts of RO• radical (DMPO/OR). On the basis of the observed ID50 and ID75 values, the lipophilic alkoxyl radical eliminating capacities (L-AREC) of these lipophilic antioxidants were determined using TRX as a standard. The evaluated L-AREC values are directly connected to the second order rate constants for the RO• radical induced hydrogen atom abstractions from the hydroxyl groups of the phenolic antioxidants, as well as from the allylic methylene groups of unsaturated fatty acids. The L-AREC values estimated by LFI-ESR method are concluded to be a practical and reliable indicator that reflect the inhibiting abilities of lipophilic antioxidants towards the radical chain reaction involved in the autoxidation processes of unsaturated fatty acids.</description><identifier>ISSN: 0009-2673</identifier><identifier>EISSN: 1348-0634</identifier><identifier>DOI: 10.1246/bcsj.20190059</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><subject>Adducts ; Antioxidants ; Autoxidation ; Electron paramagnetic resonance ; Electron spin ; Ethyl acetate ; Fatty acids ; Hydroxyl groups ; Rate constants ; Signal monitoring ; Spin resonance ; Thermal decomposition ; Tocopherol</subject><ispartof>Bulletin of the Chemical Society of Japan, 2019-07, Vol.92 (7), p.1218-1225</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Chemical Society of Japan 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-85b1f4306fbf3a75ee08d0f587f1797b5a5801a863cc62ee12f7323daa283fef3</citedby><cites>FETCH-LOGICAL-c316t-85b1f4306fbf3a75ee08d0f587f1797b5a5801a863cc62ee12f7323daa283fef3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Sakurai, Yasuhiro</creatorcontrib><creatorcontrib>Yamaguchi, Tomoko</creatorcontrib><creatorcontrib>Ando, Kai</creatorcontrib><creatorcontrib>Kuwabara, Keiko</creatorcontrib><creatorcontrib>Nakajima, Hiroki</creatorcontrib><creatorcontrib>Morimoto, Chie</creatorcontrib><creatorcontrib>Yoshikawa, Shinichi</creatorcontrib><creatorcontrib>Niwa, Masumi</creatorcontrib><creatorcontrib>Miyake, Yusuke</creatorcontrib><creatorcontrib>Kanaori, Kenji</creatorcontrib><creatorcontrib>Nakajima, Akira</creatorcontrib><creatorcontrib>Tajima, Kunihiko</creatorcontrib><title>Development of a Flow-Injection ESR System for Evaluating the Lipophilic Alkoxyl Radical Eliminating Capacities (L-AREC) of Tocopherol Analogues and Unsaturated Fatty Acids</title><title>Bulletin of the Chemical Society of Japan</title><description>A new lipophilic spin-trapping flow-injection electron spin resonance (LFI-ESR) system was developed for quantitative detection of DMPO spin-adduct of alkoxyl radical (RO•), which was produced by thermal decomposition of an azo-initiator (AIBN) in ethyl acetate at 70 °C. The 50% and 75% inhibition dose (ID50 and ID75) of a series of lipophilic antioxidants, such as tocopherol derivatives (αToc, βToc, γToc, δToc, Toc, αTocM, βTocM, γTocM, TocM, TRX, and 7TocM), a lipophilic phenol (BHT), and unsaturated fatty acids (Ole, Lin, and Lic), were determined by monitoring the ESR signal intensity of the DMPO spin-adducts of RO• radical (DMPO/OR). On the basis of the observed ID50 and ID75 values, the lipophilic alkoxyl radical eliminating capacities (L-AREC) of these lipophilic antioxidants were determined using TRX as a standard. The evaluated L-AREC values are directly connected to the second order rate constants for the RO• radical induced hydrogen atom abstractions from the hydroxyl groups of the phenolic antioxidants, as well as from the allylic methylene groups of unsaturated fatty acids. The L-AREC values estimated by LFI-ESR method are concluded to be a practical and reliable indicator that reflect the inhibiting abilities of lipophilic antioxidants towards the radical chain reaction involved in the autoxidation processes of unsaturated fatty acids.</description><subject>Adducts</subject><subject>Antioxidants</subject><subject>Autoxidation</subject><subject>Electron paramagnetic resonance</subject><subject>Electron spin</subject><subject>Ethyl acetate</subject><subject>Fatty acids</subject><subject>Hydroxyl groups</subject><subject>Rate constants</subject><subject>Signal monitoring</subject><subject>Spin resonance</subject><subject>Thermal decomposition</subject><subject>Tocopherol</subject><issn>0009-2673</issn><issn>1348-0634</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNptkc1v1DAQxS0EUpeWY--WuMAhxR_55BYtWai0UqVte45mnXHXwbFD7C3kf-KPJKst4sJpNNLvzRu9R8g1ZzdcpPmnvQr9jWC8YiyrXpEVl2mZsFymr8mKMVYlIi_kBXkbQr-sZZZWK_L7Cz6j9eOALlKvKdCN9T-TW9ejisY72tzv6P0cIg5U-4k2z2CPEI17ovGAdGtGPx6MNYrW9rv_NVu6g84osLSxZjDujK5hBGWiwUA_bJN616w_nswevFrUOHlLawfWPx0XAFxHH12AeJwgYkc3EONMa2W6cEXeaLAB373MS_K4aR7W35Lt3dfbdb1NlOR5TMpsz3UqWa73WkKRIbKyYzorC82LqthnkJWMQ5lLpXKByIUupJAdgCilRi0vyfvz3XHyP5afYtv747R8GFohclFksmLFQiVnSk0-hAl1O05mgGluOWtPhbSnQtq_hSz85xf-gMMpouCVwTj3Szjun8P_xX8AUWaUdw</recordid><startdate>20190715</startdate><enddate>20190715</enddate><creator>Sakurai, Yasuhiro</creator><creator>Yamaguchi, Tomoko</creator><creator>Ando, Kai</creator><creator>Kuwabara, Keiko</creator><creator>Nakajima, Hiroki</creator><creator>Morimoto, Chie</creator><creator>Yoshikawa, Shinichi</creator><creator>Niwa, Masumi</creator><creator>Miyake, Yusuke</creator><creator>Kanaori, Kenji</creator><creator>Nakajima, Akira</creator><creator>Tajima, Kunihiko</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20190715</creationdate><title>Development of a Flow-Injection ESR System for Evaluating the Lipophilic Alkoxyl Radical Eliminating Capacities (L-AREC) of Tocopherol Analogues and Unsaturated Fatty Acids</title><author>Sakurai, Yasuhiro ; Yamaguchi, Tomoko ; Ando, Kai ; Kuwabara, Keiko ; Nakajima, Hiroki ; Morimoto, Chie ; Yoshikawa, Shinichi ; Niwa, Masumi ; Miyake, Yusuke ; Kanaori, Kenji ; Nakajima, Akira ; Tajima, Kunihiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-85b1f4306fbf3a75ee08d0f587f1797b5a5801a863cc62ee12f7323daa283fef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Adducts</topic><topic>Antioxidants</topic><topic>Autoxidation</topic><topic>Electron paramagnetic resonance</topic><topic>Electron spin</topic><topic>Ethyl acetate</topic><topic>Fatty acids</topic><topic>Hydroxyl groups</topic><topic>Rate constants</topic><topic>Signal monitoring</topic><topic>Spin resonance</topic><topic>Thermal decomposition</topic><topic>Tocopherol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sakurai, Yasuhiro</creatorcontrib><creatorcontrib>Yamaguchi, Tomoko</creatorcontrib><creatorcontrib>Ando, Kai</creatorcontrib><creatorcontrib>Kuwabara, Keiko</creatorcontrib><creatorcontrib>Nakajima, Hiroki</creatorcontrib><creatorcontrib>Morimoto, Chie</creatorcontrib><creatorcontrib>Yoshikawa, Shinichi</creatorcontrib><creatorcontrib>Niwa, Masumi</creatorcontrib><creatorcontrib>Miyake, Yusuke</creatorcontrib><creatorcontrib>Kanaori, Kenji</creatorcontrib><creatorcontrib>Nakajima, Akira</creatorcontrib><creatorcontrib>Tajima, Kunihiko</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Bulletin of the Chemical Society of Japan</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sakurai, Yasuhiro</au><au>Yamaguchi, Tomoko</au><au>Ando, Kai</au><au>Kuwabara, Keiko</au><au>Nakajima, Hiroki</au><au>Morimoto, Chie</au><au>Yoshikawa, Shinichi</au><au>Niwa, Masumi</au><au>Miyake, Yusuke</au><au>Kanaori, Kenji</au><au>Nakajima, Akira</au><au>Tajima, Kunihiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Development of a Flow-Injection ESR System for Evaluating the Lipophilic Alkoxyl Radical Eliminating Capacities (L-AREC) of Tocopherol Analogues and Unsaturated Fatty Acids</atitle><jtitle>Bulletin of the Chemical Society of Japan</jtitle><date>2019-07-15</date><risdate>2019</risdate><volume>92</volume><issue>7</issue><spage>1218</spage><epage>1225</epage><pages>1218-1225</pages><issn>0009-2673</issn><eissn>1348-0634</eissn><abstract>A new lipophilic spin-trapping flow-injection electron spin resonance (LFI-ESR) system was developed for quantitative detection of DMPO spin-adduct of alkoxyl radical (RO•), which was produced by thermal decomposition of an azo-initiator (AIBN) in ethyl acetate at 70 °C. The 50% and 75% inhibition dose (ID50 and ID75) of a series of lipophilic antioxidants, such as tocopherol derivatives (αToc, βToc, γToc, δToc, Toc, αTocM, βTocM, γTocM, TocM, TRX, and 7TocM), a lipophilic phenol (BHT), and unsaturated fatty acids (Ole, Lin, and Lic), were determined by monitoring the ESR signal intensity of the DMPO spin-adducts of RO• radical (DMPO/OR). On the basis of the observed ID50 and ID75 values, the lipophilic alkoxyl radical eliminating capacities (L-AREC) of these lipophilic antioxidants were determined using TRX as a standard. The evaluated L-AREC values are directly connected to the second order rate constants for the RO• radical induced hydrogen atom abstractions from the hydroxyl groups of the phenolic antioxidants, as well as from the allylic methylene groups of unsaturated fatty acids. The L-AREC values estimated by LFI-ESR method are concluded to be a practical and reliable indicator that reflect the inhibiting abilities of lipophilic antioxidants towards the radical chain reaction involved in the autoxidation processes of unsaturated fatty acids.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/bcsj.20190059</doi><tpages>8</tpages></addata></record> |
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subjects | Adducts Antioxidants Autoxidation Electron paramagnetic resonance Electron spin Ethyl acetate Fatty acids Hydroxyl groups Rate constants Signal monitoring Spin resonance Thermal decomposition Tocopherol |
title | Development of a Flow-Injection ESR System for Evaluating the Lipophilic Alkoxyl Radical Eliminating Capacities (L-AREC) of Tocopherol Analogues and Unsaturated Fatty Acids |
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