炭素-13核磁気共鳴の配糖体の化学構造研究への応用 : Panax(ニンジン)属植物のサポニン及び甘味植物配糖体研究を中心として

抄録

For the purpose of the development of modern procedures of glycoside-chemistry, a number of anomeric pairs of D-glucopyranosides, D-mannopyranosides, L-rhamnopyranosides and L-arabinopyranosides of a variety of aliphatic alcohols and carboxylic acids were synthesized. For these glycosides together with the known natural glycosides, carbon signal displacements of both aglycone- and sugar-moieties on glycoside formation, "glycosylation shift" were studied. The exceptional glycosylation shifts for glycosides of relatively hindered aglycone alcohols and carboxylic acids as well as 2-linked glycosides were discussed under the stereochemical consideration. It was also revealed that ¹³C-nuclear magnetic resonance spectrometry is a valuable tool for the determination of anomeric configuration of mannosides and rhamnosides. In the application of these results, structures of a number of dammarane-saponins of Ginseng and the related Panax species, natural sweet glycosides and glycoside of oriental medicinal plants have been elucidated.