海兔朱丽安娜卵中一种新型膦酰糖鞘脂的结构解析。

Structural elucidation of a novel phosphonoglycosphingolipid in eggs of the sea hare Aplysia juliana.

作者信息

Yamaguchi Y, Ohta M, Hayashi A

机构信息

Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan.

出版信息

Biochim Biophys Acta. 1992 Dec 2;1165(2):160-6.

PMID:1450210

Abstract

A novel phosphonoglycosphingolipid (AJPnGL) was isolated from eggs of the sea hare Aplysia juliana. The structure was determined to be Gal alpha 1-->2Gal beta 1-->4(2-aminoethylphosphonyl-->6)Glc beta 1-->1Cer by FAB/MS, 1H-NMR, hydrogen fluoride degradation, methylation analysis, partial acid hydrolysis and GC analysis of the component sugars, fatty acids and long-chain bases. The ceramide moiety of this lipid consisted of branched nonadeca-4-sphingenine and octadeca-4-sphingenine as main long-chain bases and palmitic acid and stearic acid as major fatty acids. Since the sugar chain (Gal alpha 1-->2Gal beta 1-->4Glc beta 1-->) and the ceramide moiety of AJPnGL were identical with those of the main neutral glycosphingolipid of eggs of A. juliana, the biosynthesis of AJPnGL may occur by the addition of 2-aminoethylphosphonate to the main neutral glycosphingolipid, Gal alpha 1-->2Gal beta 1-->4Glc beta 1-->1Cer.

摘要

从海兔朱莉安娜（Aplysia juliana）的卵中分离出一种新型膦酰糖鞘脂（AJPnGL）。通过快原子轰击质谱（FAB/MS）、1H-核磁共振（1H-NMR）、氟化氢降解、甲基化分析、部分酸水解以及对组成糖类、脂肪酸和长链碱基的气相色谱（GC）分析，确定其结构为Galα1→2Galβ1→4(2-氨乙基膦酰基→6)Glcβ1→1Cer。该脂质的神经酰胺部分由支链的十九碳-4-鞘氨醇和十八碳-4-鞘氨醇作为主要长链碱基，以及棕榈酸和硬脂酸作为主要脂肪酸组成。由于AJPnGL的糖链（Galα1→2Galβ1→4Glcβ1→）和神经酰胺部分与朱莉安娜海兔卵中主要中性糖鞘脂的相同，因此AJPnGL的生物合成可能是通过向主要中性糖鞘脂Galα1→2Galβ1→4Glcβ1→1Cer添加2-氨乙基膦酸酯而发生的。