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The Structure Determination of Oligosaccharide Chains in Naturally Occurring Compounds by 1D-SEMDY and NOE Difference Spectroscopy in Rotating Frame
Miao Zhenchun,Feng Rui,Zhou Yongxin,Wei Feng
Author NameAffiliation
Miao Zhenchun Institute of Pharmacology and Toxicology,Acadey of Military Medical Sciences,Beijing 100850 
Feng Rui Institute of Pharmacology and Toxicology,Acadey of Military Medical Sciences,Beijing 100850 
Zhou Yongxin Institute of Pharmacology and Toxicology,Acadey of Military Medical Sciences,Beijing 100850 
Wei Feng School of Pharmaceutical Sciences,Beijing Medical University,Beijing 100083 
Abstract:
Two new saponins containing five sugars have been isolated from the ethanol extract of the root of Dipsocus japonicus and their structures established as(3-O-α-L-rhammopyranosyl(1→3)- α-D-glycopyranosyl(1→3)-α-L-rhammopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin-28-O-α-D-glycopranoside(1)and3-O-α-D--glycopyranosyl(1→4)] α-L-rhamnopyranosyl(1→3)]- α-D-glycopyranosyl(1→3)- α-L[WTBZ]-rhamnopyranosyl(1→2)- α-L-arabinopyranosyl-oleanoic acid(2).Two new NMR techniques,1D-SEMDY and NOE difference spectroscopy in rotating frame have been successfully used to determine the chemical structure of oligosaccharide chains of the saponins.The results obtained showed that the sites of glycosylation and the sequence of sugars in the saponins can be determined unambiguously and total assignment of severely overlapping pro~ton resonance of sugar residues were achieved,without having recourse to chemical degration or modification.
Key words:  Dipsocus japonicus,Structural determination of oligosaccharide chains,ROE difference spectroscopy,1D-SEMDY
FundProject:国家自然科学基金资助项目(No.29805004)
一维SEMDY和旋转坐标NOE差谱NMR新技术用于天然化合物中寡糖的结构研究
缪振春,冯锐,周永新,魏锋
摘要:
报告从日本续断根部的乙醇提取物中分得二个新的五糖三萜皂甙,应用一维SEMDY和旋转坐标NOE差谱等NMR新技术互相配合的方法对它们的结构进行了研究,确定为:3-O-α-L-吡喃鼠李糖(1→3)-β-D-吡喃葡萄糖(1→3)-α-L-吡喃鼠李糖(1→2)-α-L-吡喃阿拉伯糖-常春藤甙元-28-O-β-吡喃葡萄糖酯甙(1),和3-O-[β-D-吡喃葡萄糖(1→4)] [α-L-吡喃鼠李糖(1→3)]-β-D-吡喃葡萄糖(1→3)-α-L-吡喃鼠李糖(1→2)-α-L-吡喃阿拉伯糖-齐墩果酸(2)·结果表明,
关键词:  糖链结构测定  旋转坐标系NOE差谱  一维SEMDY谱  日本续断  三萜皂甙
DOI:10.1088/1674-0068/13/3/312-320
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