Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemical Studies on the Oriental Plant Drugs. XXVIII. Saponins and Sapogenins of Ginseng : Stereochemistry of the Sapogenin of Ginsenosides-Rb1, -Rb2 and -Rc
MASAHIRO NAGAITOSHIO ANDONOBUTOSHI TANAKAOSAMU TANAKASHOJI SHIBATA
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1972 Volume 20 Issue 6 Pages 1212-1216

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Abstract

The sapogenin of Ginseng saponins, ginsenosides-Rb1, -Rb2 and -Rc, was once reported to be protopanaxadiol (III). But it was found recently that dammarane type triperpenes with hydroxyl or methoxyl group at C(12) and C(20) give an equilibrated mixture of epimeric compounds at C(20). On mild hydrolysis of the saponins 20-epi-protopanaxadiol has been obtained as the genuine sapogenin for which the name of 20 (S)-protopanaxadiol (V) is proposed. The prosapogenin (XI), which was obtained by the partial hydrolysis of the above mentioned three saponins is found to be 3-O-(2β-D-glucopyranosyl-β-D-glucopyranosyl)-20 (R)-protopanaxadiol. The remaining glycosidic linkage in ginsenosides-Rb1, -Rb2 and -Rc should be located at C(20)-OH.

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© The Pharmaceutical Society of Japan
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