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Structures and biological activities of novel phosphonoglycosphingolipids.

新型磷酸鞘糖脂的结构和生物活性。

基本信息

批准号：
62480450
负责人：
SATAKE Mei
金额：
$ 4.42万
依托单位：
Niigata University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (B)
财政年份：
1987
资助国家：
日本
起止时间：
1987 至 1988
项目状态：
已结题

项目摘要

In the present study, chemical structure and histohogical localization of a major phosphonoglycosphingolipid of nerve fibes of Aplysia kurodai, a sea gastropod, were identified.1. Chemical structure of FGL-IIb: The complete structure was determined as 3,4-0-(1-carboxy-ethylidene)Ga1 1 3GalNAc 1 3[Fuc 1 2](2-aminoethylphosphony1 6)Ga1 1 4Glc 1 1-ceramide using GC-MS, NMR and chemical methods including permethylation etc. This is the first pyruvate containing sphingolipid so far reported in the animal. The basic structure of FGL-IIb is the same with that reported by us for the three major phosphonoglycosphingolipids of the skin of Aplysia, namely N-Ac galactosaminyl 1 3lactosy1-1 ceramide. Pyruvate in the molecule may make FGL-IIb more acidic than other phosphonoglycosphingolipids identified by us.2. Tissue distribution of FGL-IIb and immunochemically related glycolipids: Anti FGL-IIb antiserum was raised in the rabbit and this polyclonal antiserum was used for immunochemical and immunohistochemical studies with HRP staining. Narve bundles in the nerve fibers, ganglia and skin were stained. Other components including nerve cell bodies and neuropil were not stained at all. The reactivity of FGL-IIb to the antiserum was abolished by esterification of FGL-IIb and the lost activity was recovered by saponifiction. This indicates that free carboxyl of the pyruvic acid of FGL-IIb is responsible for the antigenicity of FGL-IIb.Besides FGL-IIb, other phosphonoglycosphingolipids identified in the nerve fiber of Aplysia as FGL-I, FGL-IIa, FGL-V and F-9 were also stained with the antiserum on TIC indicating that these glycolipids share the same epitope with FGL-IIb against the antibody. Pretreatment of tissues with chloroform-methanol mixture completely abolished the staining of nerve bundles.These results reveal that only the nerve bundles in Aplysia tissues contain very acidic glycolipids as FGL-IIb, indicating some neurobiological significances of these glycolipids.

本研究对黑台黑鲷神经纤维中一种主要的磷酸鞘糖脂的化学结构和组织学定位进行了研究. FGL-IIb的化学结构：经GC-MS、NMR和全甲基化等化学方法测定，其结构为3，4-O-（1-羧基亚乙基）Ga 113 GalNAc 13 [Fuc 12]（2-氨乙基膦酰基）Ga 114 Glc 11-神经酰胺。FGL-Ⅱ b的基本结构与我们报道的三种主要膦酰鞘脂的结构相同，即N-Ac半乳糖胺1 - 3乳糖基1 -1神经酰胺。分子中的丙酮酸可能使FGL-IIb比我们鉴定的其他膦酰鞘糖脂酸性更强。FGL-IIb和免疫化学相关糖脂的组织分布：在家兔中产生抗FGL-IIb抗血清，并将该多克隆抗血清用于HRP染色的免疫化学和免疫组织化学研究。神经纤维、神经节和皮肤中的神经束被染色。其他成分，包括神经细胞体和神经胶质细胞，根本没有染色。FGL-Ⅱ b与抗血清的反应性可通过酯化作用消除，失去的活性可通过皂化作用恢复。这表明FGL-IIb的丙酮酸中的游离羧基是FGL-IIb的抗原性的原因。除FGL-IIb外，海兔神经纤维中鉴定的其他磷酸糖鞘脂FGL-I、FGL-IIa、FGL-V和F-9也与抗血清在TIC上染色，表明这些糖脂与FGL-IIb具有相同的抗抗体表位。用氯仿-甲醇混合物预处理组织可完全消除神经束的染色，这些结果表明，只有在失智症组织中的神经束含有酸性很强的糖脂FGL-Ⅱ b，表明这些糖脂具有一定的神经生物学意义。