Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins
Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins
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DOI：
10.1194/jlr.m200467-jlr200
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发表时间：
2003-09-01
影响因子：
6.5
通讯作者：
Abdalla, DSP
中科院分区：
文献类型：
--
作者：
Lima, ES;Di Mascio, P;Abdalla, DSP
一氧化氮（（NO）-N-.）和（NO）-N-。衍生的活性物质（例如，过氧亚硝酸根阴离子、二氧化氮自由基）与含有不饱和脂肪酸的脂质反应生成硝化物质。在目前的工作中，我们合成，表征，并检测到硝酸衍生物的胆固醇亚油酸酯（Ch 18：2）在人血浆和脂蛋白使用高压液相色谱耦合电喷雾串联质谱法。它是由CH 18：2与硝鎓反应合成的。四氟硼酸盐，产生m/z 711的物质，这是胆固醇硝基亚油酸酯（Ch 18：2NO（2））铵加合物的特征。通过使用[N-15]亚硝酸盐确认硝基的存在，其得到具有MA 712的产物，具有与m/z 711相同的色谱和光谱特征。红外光谱（V-max 1549，1374 cm（-1））分析表明，CH 18：2NO（2）中存在C-NO2结构。在正常血脂受试者的人血浆和脂蛋白中发现了m/z为711的稳定产物，其色谱特征和裂解模式与合成标准品相同。这种新的含氮脂质产物在人血浆和脂蛋白中的存在可能代表了（NO）-N-的氧化/硝化作用的潜在指标。或其代谢物在体内脂质氧化过程中发挥作用，在血管疾病中产生代偿性保护机制。
Nitric oxide ((NO)-N-.) and (NO)-N-.-derived reactive species (e.g., peroxynitrite anion, nitrogen dioxide radical) react with lipids containing unsaturated fatty acids to generate nitrated species. In the present work, we synthesized, characterized, and detected a nitrated derivative of cholesteryl linoleate (Ch18:2) in human blood plasma and lipoproteins using a high-pressure liquid chromatography coupled to electrospray ionization tandem mass spectrometry method. It was synthesized by a reaction of Ch18:2 with nitronium. tetrafluoroborate, yielding a species with m/z 711, which is characteristic of the cholesteryl nitrolinoleate (Ch18:2NO(2)) ammonium adduct. The presence of the nitro group was confirmed by using [N-15]nitrite, which gave a product with MA 712, with the same chromatographic and spectrometric characteristics of those of m/z 711. Furthermore, a C-NO2 structure was also demonstrated in Ch18:2NO(2) by infrared analysis (V-max 1549, 1374 cm(-1)). A stable product with m/z of 711, showing the same chromatographic characteristics and fragmentation pattern as those of synthesized standard, was found in human blood plasma and lipoproteins of normolipidemic subjects. The presence of this novel nitrogen-containing lipid product in human plasma and lipoproteins could represent a potential indicator of the oxidative/nitrative roles that (NO)-N-. or its metabolites play during in vivo lipid oxidation, generating a compensatory mechanism of protection in vascular disease.