Sugita M, Fujii H, Dulaney J T, Inagaki F, Suzuki M, Suzuki A, Ohta S
Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Japan.
Biochim Biophys Acta. 1995 Dec 7;1259(3):220-6. doi: 10.1016/0005-2760(95)00168-9.
The novel amphoteric glycosphingolipids containing a choline phosphate were purified from whole tissues of the earthworm, Pheretima hilgendorfi. Their chemical structures were completely characterized as cholinephosphoryl-->6(Man alpha 1-4)Gal beta 1-6Gal beta 1-1Cer (cholinephosphorylmannosylneogalabiaosylceramide, named PGL3a) and cholinephosphoryl-->6Gal beta 1-6Gal beta 1-6Gal beta 1-1Cer (cholinephosphorylneogalatriaosylceramide, named PGL3b) by compositional sugar, fatty acid and sphingoid analyses, hydrogen fluoride degradation, partial acid hydrolysis, methylation analysis, exoglycosidase degradation, proton magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. The ceramide moieties of these lipids consisted of 22:0, 23:0 and 24:0 acids as major fatty acids, and branched octadeca- and nonadeca-4-sphingenines and octadeca-4-sphingenine as main sphingoids. Since the oligosaccharides and the ceramide moieties of PGL3a and PGL3b were identical with those of neutral glycosphingolipids found in this organism, the biosynthesis of the amphoteric glycolipids may occur by the addition of a choline phosphate residue to the corresponding neutral glycolipids, Man alpha 1-4Gal beta 1-6Gal beta 1-1Cer or Gal beta 1-6Gal beta 1-6Gal beta 1-1Cer.
从参环毛蚓的全组织中纯化出了含有磷酸胆碱的新型两性糖鞘脂。通过组成糖、脂肪酸和鞘氨醇分析、氟化氢降解、部分酸水解、甲基化分析、外切糖苷酶降解、质子磁共振波谱和快原子轰击质谱，其化学结构被完全表征为胆碱磷酸酯→6(甘露糖α1-4)半乳糖β1-6半乳糖β1-1神经酰胺（胆碱磷酸酯甘露糖基新加拉比糖基神经酰胺，命名为PGL3a）和胆碱磷酸酯→6半乳糖β1-6半乳糖β1-6半乳糖β1-1神经酰胺（胆碱磷酸酯新加拉三糖基神经酰胺，命名为PGL3b）。这些脂质的神经酰胺部分由22:0、23:0和24:0酸作为主要脂肪酸，以及支链十八碳和十九碳-4-鞘氨醇和十八碳-4-鞘氨醇作为主要鞘氨醇组成。由于PGL3a和PGL3b的寡糖和神经酰胺部分与在该生物体中发现的中性糖鞘脂的相同，两性糖脂的生物合成可能是通过向相应的中性糖鞘脂，即甘露糖α1-4半乳糖β1-6半乳糖β1-1神经酰胺或半乳糖β1-6半乳糖β1-6半乳糖β1-1神经酰胺添加一个磷酸胆碱残基而发生的。
