Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products
To determine the antioxidant mechanism of food phenolics against the oxidation of food components, the reaction of carnosic acid, an antioxidative constituent of the popular herbs sage and rosemary, was investigated in the presence of ethyl linoleate and the radical oxidation initiator 2,2‘-azobis(2...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2001-11, Vol.49 (11), p.5560-5565 |
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| container_issue | 11 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 49 |
| creator | Masuda, Toshiya Inaba, Yuzuru Takeda, Yoshio |
| description | To determine the antioxidant mechanism of food phenolics against the oxidation of food components, the reaction of carnosic acid, an antioxidative constituent of the popular herbs sage and rosemary, was investigated in the presence of ethyl linoleate and the radical oxidation initiator 2,2‘-azobis(2,4-dimethylvaleronitrile). During this process, carnosic acid was oxidized to an o-quinone and a hydroxy p-quinone, the chemical structures of which were confirmed by physical and chemical techniques. From a quantitative time course analysis of the production of these quinones, an antioxidant mechanism of carnosic acid is proposed, consisting of the oxidative coupling reaction with the peroxyl radical at the 12- or 14-position of carnosic acid and subsequent degradation reactions. Keywords: Carnosic aid; antioxidant mechanism; radical termination; sage; Labiatae; o-quinone |
| doi_str_mv | 10.1021/jf010693i |
| format | Article |
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During this process, carnosic acid was oxidized to an o-quinone and a hydroxy p-quinone, the chemical structures of which were confirmed by physical and chemical techniques. From a quantitative time course analysis of the production of these quinones, an antioxidant mechanism of carnosic acid is proposed, consisting of the oxidative coupling reaction with the peroxyl radical at the 12- or 14-position of carnosic acid and subsequent degradation reactions. 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Agric. Food Chem</addtitle><description>To determine the antioxidant mechanism of food phenolics against the oxidation of food components, the reaction of carnosic acid, an antioxidative constituent of the popular herbs sage and rosemary, was investigated in the presence of ethyl linoleate and the radical oxidation initiator 2,2‘-azobis(2,4-dimethylvaleronitrile). During this process, carnosic acid was oxidized to an o-quinone and a hydroxy p-quinone, the chemical structures of which were confirmed by physical and chemical techniques. From a quantitative time course analysis of the production of these quinones, an antioxidant mechanism of carnosic acid is proposed, consisting of the oxidative coupling reaction with the peroxyl radical at the 12- or 14-position of carnosic acid and subsequent degradation reactions. 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Psychology</subject><subject>General aspects</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - pharmacology</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9OGzEQBnCrKiop7aEvgPbSSj0sjL3rP-EWIlqQQkEilXqqNbG9wmGzpvauoLde-5p9EhwSkUtPlmZ-88n6CPlA4YgCo8fLBiiIceVfkRHlDEpOqXpNRpCXpeKC7pO3KS0BQHEJb8g-pZLWlYAR-Tnpeh8evcWuLy6ducXOp1URmmKKsQvJm2JivD359-dvcdPHwfRDxLa4sC7fNd5gvu7WfP4Qiqt1zvPgOgabbXpH9hpsk3u_fQ_I9y9n8-l5Obv6ejGdzEqsa96XiokalVX1wlLJWIWOiTG3zMmF4gtplBLohAAhUUmbce2EBDAIDpSVtjognza59zH8Glzq9con49oWOxeGpHPomAleZfh5A00MKUXX6PvoVxh_awp6XaZ-KTPbw23osFg5u5Pb9jL4uAWYDLZNxM74tHN1DqpYnV25cT717vFlj_FOC1lJrufXN_p0CqeXsx9z_W2XiybpZRhil7v7zwefAM7Gl68</recordid><startdate>20011101</startdate><enddate>20011101</enddate><creator>Masuda, Toshiya</creator><creator>Inaba, Yuzuru</creator><creator>Takeda, Yoshio</creator><general>American Chemical Society</general><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>7X8</scope></search><sort><creationdate>20011101</creationdate><title>Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products</title><author>Masuda, Toshiya ; Inaba, Yuzuru ; Takeda, Yoshio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-8264a8d84bd17223ae2695d2e7b85b7c886ae66067a87d2644e6700ca0e08d7d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Acetylation</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - pharmacology</topic><topic>Diterpenes, Abietane</topic><topic>Food additives</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Masuda, Toshiya</creatorcontrib><creatorcontrib>Inaba, Yuzuru</creatorcontrib><creatorcontrib>Takeda, Yoshio</creatorcontrib><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>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Masuda, Toshiya</au><au>Inaba, Yuzuru</au><au>Takeda, Yoshio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2001-11-01</date><risdate>2001</risdate><volume>49</volume><issue>11</issue><spage>5560</spage><epage>5565</epage><pages>5560-5565</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>To determine the antioxidant mechanism of food phenolics against the oxidation of food components, the reaction of carnosic acid, an antioxidative constituent of the popular herbs sage and rosemary, was investigated in the presence of ethyl linoleate and the radical oxidation initiator 2,2‘-azobis(2,4-dimethylvaleronitrile). During this process, carnosic acid was oxidized to an o-quinone and a hydroxy p-quinone, the chemical structures of which were confirmed by physical and chemical techniques. 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| ispartof | Journal of agricultural and food chemistry, 2001-11, Vol.49 (11), p.5560-5565 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Acetylation Antioxidants - chemistry Antioxidants - pharmacology Biological and medical sciences Chromatography, High Pressure Liquid Diterpenes - chemistry Diterpenes - pharmacology Diterpenes, Abietane Food additives Food industries Fundamental and applied biological sciences. Psychology General aspects Molecular Structure Oxidation-Reduction Plant Extracts - chemistry Plant Extracts - pharmacology |
| title | Antioxidant Mechanism of Carnosic Acid: Structural Identification of Two Oxidation Products |
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