Identification of the peroxidation products of 13-hydroxy-gamma-linolenate and 15-hydroxyarachidonate: mechanistic studies on the formation of leukotriene-like diols.

Rector CL, Stec DF, Brash AR, Porter NA
Chem Res Toxicol. 2007 20 (11): 1582-93

PMID: 17907784 · DOI:10.1021/tx700120r

Monohydroxy-gamma-linolenates and arachidonates were oxidized in the presence of alpha-tocopherol and free radical initiators at 37 degrees C. The dihydroxylinolenate products were analyzed and identified by use of a combination of liquid chromatography, mass spectrometry, and NMR techniques. A mechanism for the formation of the dihydroxylinolenates is proposed based on product analysis of oxidations using varied concentrations of alpha-tocopherol. The mechanism for monohydroxyarachidonate oxidation is the same as that of monohydroxylinolenates. However, arachidonate diol analysis is more complicated because of the formation of additional regioisomers that are a result of the parent arachidonate possessing multiple bisallylic hydrogens.

MeSH Terms (8)

Arachidonic Acids Chromatography, High Pressure Liquid Leukotrienes Linoleic Acids Lipid Peroxidation Magnetic Resonance Spectroscopy Mass Spectrometry Oxidation-Reduction

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