Linked Life Data

10828088

Source:http://linkedlifedata.com/resource/pubmed/id/10828088

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pubmed-article:10828088pubmed:abstractTextPhosphatidylcholines (PCs) with platelet-activating factor (PAF)-like biological activities are known to be generated by fragmentation of the sn-2-esterified polyunsaturated fatty acyl group. The reaction is free radical-mediated and triggered by oxidants such as metal ions, oxyhemoglobin, and organic hydroperoxides. In this study, we characterized the PAF-like phospholipids produced on reaction of PC having a linoleate group with lipoxygenase enzymes at low oxygen concentrations. When the oxidized PCs were analyzed by gas chromatography-mass spectrometry, two types of oxidatively fragmented PC were detected. One PC had an sn-2-short chain saturated or unsaturated acyl group (C(8)-C(13)) with an aldehydic terminal; the abundant species were PCs with C(9) and C(13). The other PC had a short chain saturated acyl group (C(6)-C(9)) with a methyl terminal, and the most predominant species was PC with C(8). When the extracts of oxidation products were subjected to catalytic hydrogenation, PCs having saturated acyl groups (C(6)-C(14)) were detected; the most abundant was C(12) species. The less regiospecific formation of PAF-like lipids suggests that they were generated by oxidative fragmentation of PC hydroperoxides formed by non-stereoselective oxygenation of the alkyl radical of esterified linoleate that escaped from the active centers of lipoxygenases. One of the PAF-like PC with an aldehydic terminal was found to be bioactive; it inhibited the production of nitric oxide induced by lipopolysaccharide and interferon-gamma in vascular smooth muscle cells from rat aorta.lld:pubmed
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pubmed-article:10828088pubmed:authorpubmed-author:YamamotoSSlld:pubmed
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pubmed-article:10828088pubmed:pagination953-62lld:pubmed
pubmed-article:10828088pubmed:dateRevised2006-11-15lld:pubmed
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pubmed-article:10828088pubmed:articleTitleStructural identification of phosphatidylcholines having an oxidatively shortened linoleate residue generated through its oxygenation with soybean or rabbit reticulocyte lipoxygenase.lld:pubmed
pubmed-article:10828088pubmed:affiliationLaboratory of Health Chemistry, School of Medicine, The University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan.lld:pubmed
pubmed-article:10828088pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:10828088pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed
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