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Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic Acid)

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Title: Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic Acid)
Authors: Manini, P.1, Camera, E.2, Picardo, M.2, Napolitano, A.1 alesnapo@unina.it, d’Ischia, M.1
Source: Chemistry & Physics of Lipids. Apr2005, Vol. 134 Issue 2, p161-171. 11p.
Subjects: Oxidation, Acids, Linoleic acid, Essential fatty acids
Abstract: Abstract: The reaction of (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (1a), one of the major peroxidation products of linoleic acid and an important physiological mediator, with the Fenton reagent (Fe2+/EDTA/H2O2) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with >80% substrate consumption after 4h to give a defined pattern of products, the major of which were isolated as methyl esters and were subjected to complete spectral characterization. The less polar product was identified as (9Z,11E)-13-oxo-9,11-octadecadienoate (2) methyl ester (40% yield). Based on 2D NMR analysis the other two major products were formulated as (11E)-9,10-epoxy-13-hydroxy-11-octadecenoate (3) methyl ester (15% yield) and (10E)-9-hydroxy-13-oxo-10-octadecenoate (4) methyl ester (10% yield). Mechanistic experiments, including deuterium labeling, were consistent with a free radical oxidation pathway involving as the primary event H-atom abstraction at C-13, as inferred from loss of the original S configuration in the reaction products. Overall, these results provide the first insight into the products formed by oxidation of 1a with the Fenton reagent, and hint at novel formation pathways of the hydroxyepoxide 3 and hydroxyketone 4 of potential (patho)physiological relevance in settings of oxidative stress. [Copyright &y& Elsevier]
Copyright of Chemistry & Physics of Lipids is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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An: 17576094
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  Data: Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E-octadecadienoic Acid)
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  Data: <searchLink fieldCode="AR" term="%22Manini%2C+P%2E%22">Manini, P.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Camera%2C+E%2E%22">Camera, E.</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Picardo%2C+M%2E%22">Picardo, M.</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Napolitano%2C+A%2E%22">Napolitano, A.</searchLink><relatesTo>1</relatesTo><i> alesnapo@unina.it</i><br /><searchLink fieldCode="AR" term="%22d’Ischia%2C+M%2E%22">d’Ischia, M.</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Chemistry+%26+Physics+of+Lipids%22">Chemistry & Physics of Lipids</searchLink>. Apr2005, Vol. 134 Issue 2, p161-171. 11p.
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  Data: <searchLink fieldCode="DE" term="%22Oxidation%22">Oxidation</searchLink><br /><searchLink fieldCode="DE" term="%22Acids%22">Acids</searchLink><br /><searchLink fieldCode="DE" term="%22Linoleic+acid%22">Linoleic acid</searchLink><br /><searchLink fieldCode="DE" term="%22Essential+fatty+acids%22">Essential fatty acids</searchLink>
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  Data: Abstract: The reaction of (13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid (1a), one of the major peroxidation products of linoleic acid and an important physiological mediator, with the Fenton reagent (Fe2+/EDTA/H2O2) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with >80% substrate consumption after 4h to give a defined pattern of products, the major of which were isolated as methyl esters and were subjected to complete spectral characterization. The less polar product was identified as (9Z,11E)-13-oxo-9,11-octadecadienoate (2) methyl ester (40% yield). Based on 2D NMR analysis the other two major products were formulated as (11E)-9,10-epoxy-13-hydroxy-11-octadecenoate (3) methyl ester (15% yield) and (10E)-9-hydroxy-13-oxo-10-octadecenoate (4) methyl ester (10% yield). Mechanistic experiments, including deuterium labeling, were consistent with a free radical oxidation pathway involving as the primary event H-atom abstraction at C-13, as inferred from loss of the original S configuration in the reaction products. Overall, these results provide the first insight into the products formed by oxidation of 1a with the Fenton reagent, and hint at novel formation pathways of the hydroxyepoxide 3 and hydroxyketone 4 of potential (patho)physiological relevance in settings of oxidative stress. [Copyright &y& Elsevier]
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  Data: <i>Copyright of Chemistry & Physics of Lipids is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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              Text: Apr2005
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