2-Hydroxy-succinaldehyde, a lipid peroxidation product proving that polyunsaturated fatty acids are able to react with three molecules of oxygen.
2-Hydroxy-succinaldehyde was detected by a GC/MS analysis of trapped aldehydic compounds obtained after Fe2+/ascorbate lipid peroxidation of arachidonic acid. Precursor molecules of aldehydes are hydroperoxy compounds. Thus the generation of the two aldehydic groups in 2-hydroxysuccinaldehyde requires a precursor molecule with two hydroperoxy groups. The hydroxy group in 2-position is generated by a third hydroperoxidation reaction. The detection of 2-hydroxysuccinaldehyde--although found only in traces--is the first example for triple dioxigenation of unsaturated fatty acid. Linolenic acid produces 2-hydroxysuccinaldehyde in much lower amounts than arachidonic acid. A similar oxidation of linoleic acid was not observed.
Mlakar
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A
Lehrstuhl für Organische Chemie I, Universität Bayreuth, NWI, Bayreuth, Germany.
Spiteller
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G
D000447:Aldehydes / Q000032:analysis*; D016718:Arachidonic Acid / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry*; D015227:Lipid Peroxidation; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D013386:Succinates / Q000032:analysis; D017962:alpha-Linolenic Acid / Q000737:chemistry*
C105896:2-hydroxysuccinaldehyde; D000447:Aldehydes; D008041:Linoleic Acids; D013386:Succinates; D017962:alpha-Linolenic Acid; D016718:Arachidonic Acid; D019787:Linoleic Acid; D010100:Oxygen