Sugita M, Fujii H, Inagaki F, Suzuki M, Hayata C, Hori T
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Japan.
J Biol Chem. 1992 Nov 5;267(31):22595-8.
A novel series of glycosphingolipids containing choline phosphate has been demonstrated in whole tissues of the earthworm, Pheretima hilgendorfi. The thin layer chromatographic pattern of the total polar glycolipids revealed the presence of more than three components with positive reactions toward orcinol-sulfuric acid (sugar), molybdate (phosphate), and Dragendorff's (choline) spray reagents. Two of these polar glycolipids (PGL1 and PGL2) were purified by the use of successive column chromatography on QAE-Sephadex A-25 and silicic acid (Iatrobeads) and detected during elution by the presence of galactose-bound choline phosphate. The structural elucidation of the oligosaccharide moieties was performed by compositional sugar analysis, hydrogen fluoride degradation, proton magnetic resonance spectroscopy, fast atom bombardment mass spectrometry, and methylation analysis. Thus, the structures of PGL1 and PGL2 were deduced to be as follows: cholinephosphoryl-->6Gal beta 1-1Cer and cholinephosphoryl-->6Gal beta 1-6Gal beta 1-1Cer. Although the oligosaccharide structures of both PGL1 and PGL2 have previously been found in other organisms, the presence of a choline phosphate group as an oligosaccharide substituent is the first finding in nature. The main molecular species of the ceramide moieties were composed of beheninyl- and lignocerinyloctadecasphingenines and their nonadecasphingenine homologues.
在参环毛蚓的全组织中已证实存在一系列新的含磷酸胆碱的糖鞘脂。总极性糖脂的薄层色谱图谱显示，有三种以上的成分对间苯二酚 - 硫酸（糖）、钼酸盐（磷酸盐）和碘化铋钾（胆碱）喷雾试剂呈阳性反应。其中两种极性糖脂（PGL1和PGL2）通过在QAE - 葡聚糖A - 25和硅酸（Iatrobeads）上连续柱色谱法纯化，并在洗脱过程中通过结合半乳糖的磷酸胆碱的存在进行检测。寡糖部分的结构解析通过组成糖分析、氟化氢降解、质子磁共振光谱、快原子轰击质谱和甲基化分析进行。因此，PGL1和PGL2的结构推断如下：胆碱磷酸酯→6Galβ1 - 1Cer和胆碱磷酸酯→6Galβ1 - 6Galβ1 - 1Cer。尽管PGL1和PGL2的寡糖结构先前已在其他生物体中发现，但磷酸胆碱基团作为寡糖取代基的存在是自然界中的首次发现。神经酰胺部分的主要分子种类由山嵛酰 - 和木蜡酰十八碳鞘氨醇及其十九碳鞘氨醇同系物组成。
