Hypochlorous acid-mediated generation of glycerophosphocholine from unsaturated plasmalogen glycerophosphocholine lipids.
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 (31)P 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.
Lessig
Jacqueline
J
University of Leipzig, Medical Faculty, Institute of Medical Physics and Biophysics, Leipzig, Germany.
Schiller
Jürgen
J
Arnhold
Jürgen
J
Fuchs
Beate
B
D005997:Glycerylphosphorylcholine / Q000737:chemistry*; D006997:Hypochlorous Acid / Q000737:chemistry*; D008244:Lysophosphatidylcholines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010759:Phosphorus Isotopes / Q000737:chemistry; D010955:Plasmalogens / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D008244:Lysophosphatidylcholines; D010759:Phosphorus Isotopes; D010955:Plasmalogens; D005997:Glycerylphosphorylcholine; D006997:Hypochlorous Acid