Chemical and apoptotic properties of hydroxy-ceramides containing long-chain bases with unusual alkyl chain lengths
Chemical and apoptotic properties of hydroxy-ceramides containing long-chain bases with unusual alkyl chain lengths
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DOI：
10.1093/jb/mvn050
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发表时间：
2008-07-01
影响因子：
2.7
通讯作者：
Hara, Atsushi
中科院分区：
文献类型：
--
作者：
Kyogashima, Mamoru;Tadano-Aritomi, Keiko;Hara, Atsushi
本文采用电喷雾质谱法分析了马肾组织中的四种游离神经酰胺（Cer 1、Cer 2、Cer 3和Cer 4）。Cer 1由（4 E）-鞘氨醇（d18：1）的二羟基长链碱（dLCB）、鞘氨醇和非羟基脂肪酸（NFA）组成; Cer 2由4-羟基鞘氨醇的三羟基LCB（tLCB）、t16：0、t18：0、t19：0和t20：0和NFA组成; Cer 3由dLCB、d16：1、d17：1、d18：1、d19：1和d20：1和羟基FA（HFA）组成; Cer 4由tLCB、t16：0、t17：0、t18：0、t19：1和t20：1组成。0和t20：0，以及HFA。结果表明，所有含有非十八碳长度的LCB（NOD-LCB）的神经酰胺物质都可以归类为羟基神经酰胺，因为这些物质总是由tLCB和/或HFA组成。此外，这些物质往往含有具有较长酰基链的FA，但既不含棕榈酸酯（C16：0）也不含其羟基化形式（C16：0 h）。将这些羟基神经酰胺对肿瘤细胞系的凋亡诱导活性与非羟基神经酰胺dLCB-NFA（Cer 1）的凋亡诱导活性进行比较。单羟基神经酰胺tLCB-NFA（Cer 2）和dLCB-HFA（Cer 3）表现出更强的活性，而二羟基神经酰胺tLCB-HFA（Cer 4）表现出与dLCB-NFA（Cer 1）相似或更弱的活性，这取决于细胞系。
We analysed four types of free ceramides ( Cer 1, Cer 2, Cer 3 and Cer 4) from equine kidneys by electrospray ionization mass spectrometry. Cer 1 was composed of dihydroxy long-chain bases ( dLCBs) of ( 4E)-sphingenine ( d18: 1), sphinganine and non-hydroxy fatty acids ( NFAs); Cer 2 was composed of trihydroxy LCBs ( tLCBs) of 4-hydroxysphinganine, t16:0, t18:0, t19:0 and t20:0, and NFAs; Cer 3 was composed of dLCBs, d16:1, d17:1, d18:1, d19:1 and d20:1, and hydroxy FAs ( HFAs); and Cer 4 was composed of tLCBs, t16:0, t17:0, t18:0, t19:0 and t20:0, and HFAs. The results indicate all ceramide species containing LCBs with non-octadeca lengths ( NOD-LCBs) can be classified into hydroxy-ceramides since these species always consist of tLCBs, and/or HFAs. Furthermore, such species tend to contain FAs with longer acyl chains but contain neither palmitate ( C16:0) nor its hydroxylated form (C16:0h). The apoptosis-inducing activities of these hydroxyl-ceramides towards tumour cell lines were compared with that of non-hydroxy-ceramides, dLCB-NFA (Cer 1). Monohydroxy-ceramides, tLCB-NFA ( Cer 2) and dLCB-HFA ( Cer 3), exhibited stronger activities, whereas dihydroxy-ceramides, tLCB-HFA ( Cer 4), exhibited similar or weaker activity than dLCB-NFA ( Cer 1), depending on cell lines.