鲑鱼肾脏中的独特二唾液酸神经节苷脂：V3αFuc、IV3βGalNAc、II3(αNeuAc)2-Gg4Cer及其4-O-乙酰基-N-乙酰神经氨酸类似物的表征

Unique disialosyl gangliosides from salmon kidney: characterization of V3alphaFuc, IV3betaGalNAc, II3(alphaNeuAc)2-Gg4Cer and its analogue with 4-O-acetyl-N-acetylneuraminic acid.

作者信息

Niimura Yukio, Ishizuka Ineo

机构信息

Research Center of Biomedical Analysis and Radioisotope, Teikyo, Tokyo, Japan.

出版信息

Glycoconj J. 2006 Nov;23(7-8):489-99. doi: 10.1007/s10719-006-6562-1.

DOI:10.1007/s10719-006-6562-1

PMID:17006641

Abstract

Four unidentified acidic glycolipids (X3-X6) were isolated from the kidney of the Pacific salmon on an anion exchange column and by high performance liquid chromatography using a silica bead (Iatrobeads) column. Based on methylation analysis, chemical and enzymatic degradation, proton nuclear magnetic resonance spectroscopy and mass spectrometry, the glycon structure of X5 and X6 was identified as a unique disialosyl fucosyl-N-acetylgalactosaminyl ganglio-N-tetraose:Fucalpha3GalNAcbeta3Galbeta3GalNAcbeta4[NeuAcalpha8NeuAcalpha3] Galbeta4Glcbeta1Cer. NMR showed that X3 and X4 were analogues of X5 and X6 and contained O-acetyl groups on C4 of the outer N-acetylneuraminic acid, first disialosyl gangliosides containing 4-O-acetyl-N-acetylneuraminic acid. The ceramides of X3 and X5 contained predominantly C24: 1, and X4 and X6 contained saturated fatty acids (C14: 0, C16: 0 and C18: 0), whereas the long chain base was exclusively sphingenine. The concentrations of X3 and X4 were 0.13 and 0.16 nmol/g of kidney respectively and those of X5 and X6, were 0.07 nmol/g each.

摘要

从太平洋鲑鱼的肾脏中，通过阴离子交换柱和使用硅胶珠（Iatrobeads）柱的高效液相色谱法，分离出了四种未鉴定的酸性糖脂（X3 - X6）。基于甲基化分析、化学和酶促降解、质子核磁共振光谱和质谱分析，确定了X5和X6的糖基结构为一种独特的二唾液酸岩藻糖基 - N - 乙酰半乳糖胺基神经节 - N - 四糖：Fucα3GalNAcβ3Galβ3GalNAcβ4[NeuAcα8NeuAcα3]Galβ4Glcβ1Cer。核磁共振显示X3和X4是X5和X6的类似物，并且在外层N - 乙酰神经氨酸的C4位含有O - 乙酰基，这是首次发现的含有4 - O - 乙酰基 - N - 乙酰神经氨酸的二唾液酸神经节苷脂。X3和X5的神经酰胺主要含有C24:1，而X4和X6含有饱和脂肪酸（C14:0、C16:0和C18:0），而长链碱基仅为鞘氨醇。X3和X4在肾脏中的浓度分别为0.13和0.16 nmol/g，X5和X6的浓度均为0.07 nmol/g。