Selective plasmenylcholine oxidation by hypochlorous acid: formation of lysophosphatidylcholine chlorohydrins
Selective plasmenylcholine oxidation by hypochlorous acid: formation of lysophosphatidylcholine chlorohydrins
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DOI：
10.1016/j.chemphyslip.2006.06.003
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发表时间：
2006-10-01
影响因子：
3.4
通讯作者：
Ford, David A.
中科院分区：
文献类型：
--
作者：
Messner, Maria C.;Albert, Carolyn J.;Ford, David A.
缩醛磷脂 sn-1 乙烯基醚键是活化吞噬细胞产生的次氯酸 (HOCl) 的目标。在本研究中，与纤浆胆碱和磷脂酰胆碱的 sn-2 位脂肪链（sn-2 烯烃）中存在的双键相比，HOCl 对缩醛磷脂 sn-1 乙烯基醚键的攻击被证明是优选的。溶血磷脂酰胆碱 (LPC) 是纤毛胆碱最初 HOCl 攻击的产物，该 LPC 产物中存在的 sn-2 烯键是 HOCl 的次要目标，导致 LPC-氯醇 (ClOH) 的产生。使用 LPC-ClOH 分子离子的碰撞激活解离 (CAD)，以正离子和负离子模式演示了脂肪族 ClOH。此外，与二酰胆碱甘油磷脂相比，HOCl 处理内皮细胞导致缩醛磷脂优先攻击。总而言之，纤浆胆碱比磷脂酰胆碱优先被氧化，并导致 LPC-ClOH 的产生。 (c) 2006 Elsevier Ireland Ltd. 保留所有权利。
The plasmalogen sn-1 vinyl ether bond is targeted by hypochlorous acid (HOCl) produced by activated phagocytes. In the present study, the attack of the plasmalogen sn-1 vinyl ether bond by HOCl is shown to be preferred compared to the attack of double bonds present in the sn-2 position aliphatic chain (sn-2 alkenes) of both plasmenyleholine and phosphatidylcholine. Lysophosphatidylcholine (LPC) is a product from the initial HOCl attack of plasmenylcholine and the sn-2 alkene bonds present in this LPC product are secondary targets of HOCl leading to the production of LPC-chlorohydrins (ClOH). The aliphatic ClOH was demonstrated in both the positive and negative ion mode using collisionally-activated dissociation (CAD) of the molecular ion of LPC-ClOH. Furthermore, HOCl treatment of endothelial cells led to the preferential attack of plasmalogens in comparison to that of diacyl choline glycerophospholipids. Taken together, plasmenylcholine is oxidized preferentially over phosphatidylcholine and leads to the production of LPC-ClOH. (c) 2006 Elsevier Ireland Ltd. All rights reserved.