Warren C D, Daniel P F, Bugge B, Evans J E, James L F, Jeanloz R W
Department of Biological Chemistry, Harvard Medical School, Boston, Massachusetts.
J Biol Chem. 1988 Oct 15;263(29):15041-9.
Eleven oligosaccharides were purified form the urine of sheep with swainsonine toxicosis induced by the feeding of Astragalus lentiginosus. Oligosaccharides were extracted by charcoal adsorption, chromatographed on Bio-Gel P-2, and partially fractionated by preparative-layer chromatography. Separation into individual compounds was completed by semi-preparative high pressure liquid chromatography. Structures were determined by a combination of high pressure liquid chromatography and exo- and endo- glycosidase action, methanolysis followed by gas-liquid chromatography, methylation analysis, and high resolution nuclear magnetic resonance spectroscopy. Two homologous series of oligosaccharides were identified: (a) alpha-D-Manp-(1----6)-beta-D-Manp-(1----4)-D-GlcpNAc, alpha-D-Manp(1----3)-[alpha-D-Manp-(1----6)]-beta-D-Manp+ ++-(1----4)-D-GlcpNAc, alpha-D-Manp-(1----2)-alpha-D-Manp(1----3)-[alpha-D-Manp+ ++-(1----6)]-beta-D-Manp-(1----4)-D-GlcpNAc, and alpha-D-Manp-(1----2)-alpha-D-Manp-(1----2)-alpha-D-Manp+ ++-(1----3)-[alpha- D-Manp-(1----6)]-beta-D-Manp-(1----4)-D-GlcpNAc (minor series); (b) alpha-D-Manp-(1----6)-beta-D-Manp-(1----4)-beta-D-GlcpNAc- (1----4)-D-GlcpNAc, alpha-D-Manp-(1----3)-[alpha-D-Manp-(1----6)]-beta-D-Manp -(1----4)-beta-D-GlcpNAc-(1----4)-D-GlcpNAc, alpha-D-Manp(1----3)-alpha-D-Manp-(1----6)-beta-D-Manp -(1----4)-beta-D-GlcpNAc- (1----4)-D-GlcpNAc, alpha-D-Manp-(1----6)-alpha-D-Manp-(1----6)-beta-D-Manp++ +-(1----4)-beta-D-GlcpNAc - (1----4)-D-GlcpNAc, alpha-D-Manp-(1----3)-alpha-D-Manp-(1----6)-[alpha-D-Manp -(1----3)]-beta-D- Manp-(1----4)-beta-D-GlcpNAc-(1----4)-D-GlcpNAc, alpha-D-Manp-(1----3)-[alpha-D-Manp-(1----6)]-alpha-D-Man p-(1----6)-beta-D- Manp-(1----4)-beta-D-GlcpNAc-(1----4)-D-GlcpNAc, and alpha-D-Manp-(1----3)-[alpha-D-Manp-(1----6)]-alpha-D-Man p-(1----6)- [alpha-D-Manp-(1----3)]-beta-D-Manp-(1----4)-beta-D-GlcpNAc- (1----4)-D- GlcpNAc (major series).
从饲喂斑纹黄芪诱导苦马豆素中毒的绵羊尿液中纯化出11种寡糖。寡糖通过活性炭吸附提取，在Bio-Gel P-2上进行色谱分析，并通过制备层色谱进行部分分离。通过半制备高压液相色谱完成分离成单个化合物。通过高压液相色谱与外切和内切糖苷酶作用、甲醇解后气液色谱、甲基化分析和高分辨率核磁共振光谱相结合来确定结构。鉴定出两个寡糖同源系列：(a)α-D-甘露糖-(1→6)-β-D-甘露糖-(1→4)-D-葡萄糖胺，α-D-甘露糖(1→3)-[α-D-甘露糖-(1→6)]-β-D-甘露糖+(++)-(1→4)-D-葡萄糖胺，α-D-甘露糖-(1→2)-α-D-甘露糖(1→3)-[α-D-甘露糖+(++)-(1→6)]-β-D-甘露糖-(1→4)-D-葡萄糖胺，以及α-D-甘露糖-(1→2)-α-D-甘露糖-(1→2)-α-D-甘露糖+(++)-(1→3)-[α-D-甘露糖-(1→6)]-β-D-甘露糖-(1→4)-D-葡萄糖胺（次要系列）；(b)α-D-甘露糖-(1→6)-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，α-D-甘露糖-(1→3)-[α-D-甘露糖-(1→6)]-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，α-D-甘露糖(1→3)-α-D-甘露糖-(1→6)-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，α-D-甘露糖-(1→6)-α-D-甘露糖-(1→6)-β-D-甘露糖+(++)-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，α-D-甘露糖-(1→3)-α-D-甘露糖-(1→6)-[α-D-甘露糖-(1→3)]-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，α-D-甘露糖-(1→3)-[α-D-甘露糖-(1→6)]-α-D-甘露糖-(1→6)-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺，以及α-D-甘露糖-(1→3)-[α-D-甘露糖-(1→6)]-α-D-甘露糖-(1→6)-[α-D-甘露糖-(1→3)]-β-D-甘露糖-(1→4)-β-D-葡萄糖胺-(1→4)-D-葡萄糖胺（主要系列）。
