Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids

• Main Authors: Jacqueline Leßig, Jürgen Schiller, Jürgen Arnhold, Beate Fuchs
• Format: Article
• Language: English
• Published: Elsevier 2007-07-01
• Series: Journal of Lipid Research
• Subjects: 31P nuclear magnetic resonance; matrix-assisted laser desorption and ionization time-of-flight mass spectrometry; lysophosphatidylcholine
• Online Access: http://www.sciencedirect.com/science/article/pii/S0022227520425593
• ISSN: 0022-2275

The myeloperoxidase-derived metabolite hypochlorous acid (HOCl) promotes the selective cleavage of plasmalogens into chloro fatty aldehydes and 1-lysophosphatidylcholine (LPC). The subsequent conversion of the initially generated LPC was investigated in plasmalogen samples in dependence on the fatty acid residue in the sn-2 position by matrix-assisted laser desorption and ionization time-of-flight mass spectrometry and 31P NMR spectroscopy. Plasmalogens containing an oleic acid residue in the sn-2 position are converted by moderate amounts of HOCl primarily to 1-lyso-2-oleoyl-sn-glycero-3-phosphocholine and at increased HOCl concentrations to the corresponding chlorohydrin species. In contrast, plasmalogens containing highly unsaturated docosahexaenoic acid yield upon HOCl treatment 1-lyso-2-docosahexaenoyl-glycerophosphocholine and glycerophosphocholine. The formation of the latter product denotes a novel pathway for the action of HOCl on plasmalogens.