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Structure and Physiological Activity of Glycolipids from Amphibias

两栖类糖脂的结构和生理活性

基本信息

批准号：
02640425
负责人：
IZUMI Shunsuke
金额：
$ 1.34万
依托单位：
HIROSHIMA UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1990
资助国家：
日本
起止时间：
1990 至 1992
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-02640425/
关键词：
Amphibias Brain Glycolipids Bullfrog Gangliosides Cerebrosides 悩組織イオン透過性イモリ絶対構造

项目摘要

The structures of three ganglioside isolated from bullfrog (Rana catesbeiana) brain tissue have been established as disialosylgangliotetraosylceramide (I11^6NeuAclV^3NeuAc-GgOse_4Cer), trisialosvlgangliotetraosvlceramide (I11^6NeuAclV^3(NeuAc)_2-GgOse_4Cer), and tertasialosylgangliotetraosylceramide (I11^6(NeuAc)_2lV^3(NeuAc)_2-GgOse_4Cer) by NMR and mass spectral measurements. A similar distribution of these gangliosides was seen among hemisphere, dienecephalon and mixed tissue from the optic lobe, cerebellum and medulla oblongata of the brain. The brain tissues of Rana nigromaculata and Rhacophorus arboreus also included the same gangliosides as those of bullfrog.On the other hand, twelve cerebrosides were isolated from the brain tissues of the bullfrog and they were characterized as 1-omicron-beta-D-galactopyranosyl ceramides. On the basis of chemical and spectral evidence, the ceramide parts of six of them were found to be composed of a sphingosine as a long-chain base and six fatty acids consisting of C_<18:0>, C_<22:1> and C_<24:1> acids and their 2-hydroxy derivatives. The ceramide parts of the others were found to be composed of a dihydrosphingosine and the six fatty acids. The configurations at C-2 and C-3 of the two long-chain bases were determined to be S and R, respectively, on the basis of the NMR spectra of their acetates and the exciton chirality of the benzoate-benzamide derivatives. Furthermore, the chiral center of the three 2-hydroxy fatty acids was determined to be R in all cases by means of CD measurements. A different distribution of the cerebroside was seen among the hemisphere, dienecephalon and mixed tissue from the optic lobe, cerebellum and medulla oblongata of the brain.

从牛蛙脑组织中分离得到三种神经节苷脂，经核磁共振和质谱测定，其结构分别为二唾液酸神经节苷脂四糖神经酰胺（I11^6 NeuAclV ^3 NeuAc-GgOse_4Cer）、三唾液酸神经节苷脂四糖神经酰胺（I11^6NeuAclV^3（NeuAc）_2-GgOse_4Cer）和四唾液酸神经节苷脂四糖神经酰胺（I11^6（NeuAc）_21V^3（NeuAc）_2-GgOse_4Cer）。这些神经节苷脂在大脑的视叶、小脑和延髓的半球、间脑和混合组织中也有类似的分布。黑斑蛙和树蛙脑组织中也含有与牛蛙相同的神经节苷脂，而牛蛙脑组织中分离到12种神经节苷脂，经鉴定为1-omicron-beta-D-galactopyranosyl神经酰胺。根据化学和光谱证据，发现其中六个化合物的神经酰胺部分是由一个长链的鞘氨醇碱和六个脂肪酸组成的，这些脂肪酸包括C_<18:0>、C_<22:1>和C_<24:1>酸及其2-羟基衍生物。其他的神经酰胺部分被发现由二氢鞘氨醇和六种脂肪酸组成。根据乙酸酯的核磁共振谱和苯甲酸酯-苯甲酰胺衍生物的激子手性，确定这两种长链碱基的C-2和C-3构型分别为S和R。此外，在所有情况下，通过CD测量确定三种2-羟基脂肪酸的手性中心为R。在视叶、小脑和延髓的半球、间脑和混合组织中，双侧皮质的分布不同。