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J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M600478-JLR200 on March 29, 2007

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Journal of Lipid Research, Vol. 48, 1316-1324, June 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

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

Jacqueline Leßig, Jürgen Schiller, Jürgen Arnhold and Beate Fuchs1

University of Leipzig, Medical Faculty, Institute of Medical Physics and Biophysics, Leipzig, Germany

Published, JLR Papers in Press, March 29, 2007.

1 To whom correspondence should be addressed. e-mail: beate.fuchs{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 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.

Supplementary key words 31P nuclear magnetic resonance • matrix-assisted laser desorption and ionization time-of-flight mass spectrometry • lysophosphatidylcholine

Abbreviations: 2-D-1-LPC, 1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphocholine; GPC, glycero-1-phosphocholine; HOCl, hypochlorous acid; LPC, lysophosphatidylcholine; 1-M-2-LPC, 1-myristoyl-2-lyso-sn-glycero-3-phosphocholine; 2-O-1-LPC, 1-lyso-2-oleoyl-sn-glycero-3-phosphocholine; OAPCplasm, 1-O-1'-(Z)octadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine; ODPCplasm, 1-O-1'-(Z)octadecenyl-2-docosahexaenoyl-sn-glycero-3-phosphocholine; OOPCplasm, 1-O-1'-(Z)octadecenyl-2-oleoyl-sn-glycero-3-phosphocholine; MALDI-TOF MS, matrix-assisted laser desorption and ionization time-of-flight mass spectrometry; MPO, myeloperoxidase; PNA, p-nitroaniline; ROS, reactive oxygen species


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