Formation of lysophospholipids from unsaturated phosphatidylcholines under the influence of hypochlorous acid

被引:79
作者
Arnhold, J
Osipov, AN
Spalteholz, H
Panasenko, OM
Schiller, J
机构
[1] Univ Leipzig, Dept Med, Inst Med Phys & Biophys, D-04103 Leipzig, Germany
[2] Russian State Med Univ, Dept Biophys, Moscow 117437, Russia
[3] Res Inst Physicochem Med, Moscow, Russia
来源
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS | 2002年 / 1572卷 / 01期
基金
俄罗斯基础研究基金会;
关键词
MALDI-TOF MS; P-31 NMR spectroscopy; unsaturated phosphatidylcholines; lysophosphatidylcholines; chlorohydrins; hypochlorous acid;
D O I
10.1016/S0304-4165(02)00271-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The formation of lysophosphatidylcholines from unsaturated phosphatidylcholines upon treatment with hypochlorous acid was evaluated by means of MALDI-TOF mass spectrometry and P-31 NMR spectroscopy. With an increasing number of double bonds in a fatty acid residue, the yield of lysophosphatidylcholines with a saturated fatty acid residue increased considerably in comparison to the total amount of higher molecular weight products like chlorohydrins and glycols. High amounts of lysophosphatidylcholines were formed from phospholipids containing arachidonic or docosahexaenoic acid residues. In phospholipids with monounsaturated fatty acid residues, the position of the double bond did not influence the yield of lyso-products. Besides the exclusive formation of chlorohydrin and glycol, hypochlorous acid caused the cleavage of the unsaturated fatty acid residue independent of its location at the first or second position of the glycerol backbone. In contrast, strong alkaline conditions, i.e. saponification led also to a hydrolysis of the saturated fatty acid residue from phosphatidylcholines. It is concluded that both MALDI-TOF mass spectrometry and P-31 NMR spectroscopy are able to detect the formation of lysophosphatidylcholines. We conclude also that the formation of lysophospholipids from unsaturated phosphatidylcholines by hypochlorous acid can be relevant in vivo under acute inflammatory conditions. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:91 / 100
页数:10
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