Submitted on November 1, 2006
Revised on February 6, 2007
Accepted on March 29, 2007
Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids
Jacqueline Leßig, Jürgen Schiller, Jürgen Arnhold, and Beate Fuchs
University of Leipzig, Medical Faculty, Institute of Medical Physics and Biophysics, Leipzig, Sachsen 04107
Corresponding Author: fucb{at}medizin.uni-leipzig.de
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 MALDI-TOF mass spectrometry and 31P NMR spectroscopy. Plasmalogens containing an oleic acid residue in sn-2 position are converted by moderate amounts of HOCl primarily into 1-lyso-2-oleoyl-sn-glycero-3-phosphocholine and at elevated HOCl concentrations into 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 hypochlorous acid on plasmalogens.
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