65 ガガイモ科植物成分の研究 : コンズランゴ皮中の抗腫瘍性配糖体の分離と構造

概要

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The crude drug Condurango Cortex, the bark of Marsdenia cundurango Reich. has been used as an aromatic bitter stomachic and also used against cancer. We report herein that six new antitumor active glycosides: condurangoglycoside -A_0(8), -C_0(9), -B_0(10), -D_0(11), 20-O-methyl-condurangoglycoside-D_0(12) and 20-iso-O-methyl-condurangoglycoside-D_0(13), were isolated from this drug by effective use of HPLC systems. Mild acid hydrolysis and ^<13>C-NMR spectra suggested that the sugar moieties of those glycosides were identical. The sugar linkage was determined as β-D-glucosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allosyl-(1→4)-β-D-oleandrosyl-β-D-cymarosyl-(1→3)-aglycone on the bases of ^<13>C-NMR technique and the analyses of the sugar fraction of the hydrolysate. Aglycones of 8 and 9 were identified as condurangogenin-A(14) and -C(22), respectively. Other four glycosides 10 to 13 were convertible to each other under proper conditions. Aglycone fractions from the hydrolysate of 10 to 13 afforded the same mixtures, which were hydrogenated to a compound 26. This compound was also obtained from 23, one of the aglycones by a catalytic hydrogenation. The structure of 26 was assigned by spectroscopy. These results lead to tentative structures of 10 to 13. Antitumor activities and LD_<50> of glycosides 8, 9, 10, and 12 were shown in the table V.
天然有機化合物討論会の論文
1980-09-10