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Free Radical Oxidation of 15-(S)-hydroxyeicosatetraenoic Acid With the Fenton Reagent: Characterization of an Epoxy-Alcohol and Cytotoxic 4-hydroxy-2E-nonenal From the Heptatrienyl Radical Pathway

Free Radical Oxidation of 15-(S)-hydroxyeicosatetraenoic Acid With the Fenton Reagent: Characterization of an Epoxy-Alcohol and Cytotoxic 4-hydroxy-2E-nonenal From the Heptatrienyl Radical Pathway

P Manini, S Briganti, C Fabbri, M Picardo, A Napolitano, M d'Ischia

Chem Phys Lipids. 2006 Jul;142(1-2):14-22.

PMID: 16581048

Abstract:

The oxidation of (5Z,8Z,11Z,13E,15S)-15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-(S)-HETE, 1a) with the Fenton reagent (Fe2+/EDTA/H2O2) was investigated. In phosphate buffer, pH 7.4, the reaction proceeded with 75% substrate consumption after 1 h to give a mixture of products, one of which was identified as (2E,4S)-4-hydroxy-2-nonenal (3a, 18% yield). Methylation of the mixture with diazomethane allowed isolation of another main product which could be identified as methyl (5Z,8Z,13E)-11,12-trans-epoxy-15-hydroxy-5,8,13-eicosatrienoate (2a methyl ester, 8% yield). A similar oxidation carried out on (15-(2)H)-15-HETE (1b) indicated complete retention of the label in 2b methyl ester and 3b, consistent with an oxidation pathway involving as the primary event H-atom abstraction at C-10. Overall, these results support the recently proposed role of 1a as a potential precursor of the cytotoxic gamma-hydroxyalkenal 3a and disclose a hitherto unrecognized interconnection between 1a and the epoxy-alcohol 2a, previously implicated only in the metabolic transformations of the 15-hydroperoxy derivative of arachidonic acid.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP70981963	15(S)-Hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid		70981-96-3	Price

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