2-Hydroxy-Succinaldehyde, a Lipid Peroxidation Product Proving that Polyunsaturated Fatty Acids are Able to React with Three Molecules of Oxygen

Abstract

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.

Key Words:

• Lipid peroxidation
• 2-hydroxysuccinaldehyde
• arachidonic acid
• linoleic acid
• linolenic acid