从黄斑海盘车（Luidia maculata）中分离和鉴定单甲基化GM3型神经节苷脂分子种类及其结构

Isolation and structure of monomethylated GM3-type ganglioside molecular species from the starfish Luidia maculata.

作者信息

Kawatake Satoshi, Inagaki Masanori, Isobe Ryuichi, Miyamoto Tomofumi, Higuchi Ryuichi

机构信息

Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2002 Oct;50(10):1386-9. doi: 10.1248/cpb.50.1386.

DOI:10.1248/cpb.50.1386

PMID:12372870

Abstract

Two monomethylated GM(3)-Type ganglioside molecular species, 1 and 2, have been obtained from the polar lipid fraction of the chloroform/methanol extract of the starfish Luidia maculata. The structures of these gangliosides have been determined on the basis of chemical and spectroscopic evidence as 1-O-[8-O-methyl-(N-acetyl-alpha-D-neuraminosyl)-(2-->3)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranosyl]-ceramide (1) and 1-O-[8-O-methyl-(N-glycolyl-alpha-D-neuraminosyl)-(2-->3)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranosyl]-ceramide (2). The ceramide moieties were composed of heterogeneous unsubstituted fatty acid, 2-hydroxy fatty acid, sphingosine and phytosphingosine units. Compound 1, designated as LMG-3, represents new ganglioside molecular species. Compound 2 was a known ganglioside molecular species.

摘要

从海星黄斑海盘车的氯仿/甲醇提取物的极性脂质部分中获得了两种单甲基化的GM(3)型神经节苷脂分子种类，即1和2。基于化学和光谱证据，已确定这些神经节苷脂的结构分别为1-O-[8-O-甲基-(N-乙酰-α-D-神经氨酰基)-(2→3)-β-D-吡喃半乳糖基-(1→4)-β-D-吡喃葡萄糖基]-神经酰胺(1)和1-O-[8-O-甲基-(N-糖基-α-D-神经氨酰基)-(2→3)-β-D-吡喃半乳糖基-(1→4)-β-D-吡喃葡萄糖基]-神经酰胺(2)。神经酰胺部分由异质的未取代脂肪酸、2-羟基脂肪酸、鞘氨醇和植物鞘氨醇单元组成。化合物1被命名为LMG-3，代表一种新的神经节苷脂分子种类。化合物2是一种已知的神经节苷脂分子种类。