Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells
Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells
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DOI：
10.1042/bj20031307
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发表时间：
2004-03-01
影响因子：
4.1
通讯作者：
Yamamoto, K
中科院分区：
文献类型：
--
作者：
Aoki, K;Uchiyama, R;Yamamoto, K
新型ZGL（两性离子鞘糖脂）已在丝状真菌（枝顶孢属（Acremonium sp.））的菌丝体中发现并提取。与土壤隔离。五个ZGL通过糖组成分析、甲基化分析、高碘酸盐氧化、基质辅助激光解吸电离飞行时间质谱、H-1-NMR光谱和快原子轰击质谱对ZGL 1-ZGL 5进行结构鉴定。GlcN（α 1 -2）Ins 1-P-1Cer（ZGL 1），人（α 1 -6）GlcN（α 1 -2）Ins1-P-1Cer（ZGL 2），人（α 1 -6）人（α 1 -6）GlcN（alpha1-2）Ins1-P-1Cer（ZGL3），PC --> 6Man（α 1 -6）GlcN（α 1 -2）Ins 1-P- 1Cer（ZGL 4）和PC -> 6 Man（α 1 -6）Man（α 1 -6）GlcN（α 1 -2）Ins 1-P-1Cer（ZGL 5）（其中Cer是神经酰胺，PC是磷酸胆碱）。此外，一种酸性鞘糖脂，这是ZGL的前体，也被表征为肌醇磷酸神经酰胺。ZGL的核心结构GlcN（alpha 1 -2）Ins 1-P与其他真菌中发现的那些结构（例如Man（alpha 1 -2）Ins 1-P和Man（alpha 1 -6）Ins 1-P）相当不同。有趣的是，ZGL 4和ZGL 5的末端甘露糖残基进一步用PC基团修饰。先前在任何生物体中均未报道含有PC的糖基肌醇-磷酸神经酰胺的存在。ZGL和酸性鞘糖脂两者的神经酰胺成分基本上相同，并且由作为唯一鞘氨醇碱的4-羟基十八碳精氨醇（植物鞘氨醇）和作为主要脂肪酸的2-羟基二十四烷酸（> 90%）组成。发现ZGL在培养的水稻细胞的悬浮液中引起细胞死亡。ZGL的细胞死亡诱导活性可能是由于Man（α 1 -6）GlcN的特征性聚糖部分，并且含有PC的ZGL具有高活性。本研究首次证明真菌糖基肌醇磷酸神经酰胺诱导培养的水稻细胞死亡。
Novel ZGLs (zwitterionic glycosphingolipids) have been found in and extracted from the mycelia of filamentous fungi (Acremonium sp.) isolated from soil. Five ZGLs (ZGL1-ZGL5) were structurally elucidated by sugar compositional analysis, methylation analysis, periodate oxidation, matrix-assisted laser-desorption ionization-time-of-flight MS, H-1-NMR spectroscopy and fast-atom bombardment MS. Their chemical structures were as follows: GlcN(alpha1-2)Ins1-P-1Cer (ZGL1), Man(alpha1-6) GlcN(alpha1-2)Ins1-P-1Cer (ZGL2), Man(alpha1-6)Man(alpha1-6)GlcN (alpha1-2)Ins1-P-1Cer (ZGL3), PC --> 6Man(alpha1-6)GlcN(alpha1-2)Ins1-P- 1Cer (ZGL4), and PC --> 6Man(alpha1-6)Man(alpha1-6)GlcN(alpha1-2) Ins1-P-1Cer (ZGL5) (where Cer is ceramide and PC is phosphocholine). In addition, one acidic glycosphingolipid, which was the precursor of ZGLs, was also characterized as inositol-phosphoceramide. The core structure of the ZGLs, GlcN(alpha1-2)lns1-P, is rather different from those found in other fungi, such as Man(alpha1-2)Ins1-P and Man(alpha1-6)Ins1-P. Interestingly, the terminal mannose residue of ZGL4 and ZGL5 was modified further with a PC group. The presence of PC-containing glycosylinositol-phosphoceramides has not been reported previously in any organism. The ceramide constituents of both ZGLs and acidic glycosphingolipid were essentially the same, and consisted of a 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid base and 2-hydroxytetracosanoic acid (> 90%) as the major fatty acid. ZGLs were found to cause cell death in suspensions of cultured rice cells. The cell death-inducing activity of ZGLs is probably due to the characteristic glycan moiety of Man(alpha1-6)GlcN, and PC-containing ZGLs had high activity. This study is the first to demonstrate that fungal glycosylinositol-phosphoceramides induce cell death in cultured rice cells.