37 テルペノイド配糖体の^<13>C-NMRの研究とその薬用ニンジン関連植物サポニン類研究への応用

概要

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The assignments of ^<13>C NMR signals of Ginseng sapogenins, (I, II) and their related dammarane type triterpenes were substantiated with the aid of the shift derivative and deuterated compounds (Table I). It was demonstrated that the intramolecular hydrogen bonding between the 12β- and the 20-tert-hydroxyl groups has remarkable effect on the chemical shifts of 17C, 20C, 21C, and 22C signals and ^<13>C NMR is highly useful in differentiation between the C-20 epimeric pair of the triterpenes of such a type (Table II). Several aliphatic β-glucosides including β-D- and β-L-glucosides of cholestanol and dammarenediol-I were prepared. The shifts of ^<13>C resonances around the glucosyl linkage from the corresponding positions in the spectra of methyl β-D-glucoside and the aglycone-alcohols were investigated. It was found that the magnitudes of the signal-shifts of the anomeric carbon (1'C) of the sugar and α- and β-carbons of aglycone-alcohols depend significantly upon the stereo-structures of the hydroxyl group of the aglycones as shown in Table III. On the basis of the present results, the structures of the glycosides of roots, leaves, and buds-flowers of Panax spp. were elucidated mainly by ^<13>C NMR spectroscopy.
天然有機化合物討論会の論文
1976-09-20