Title: Studies on the Constituents of Japanese and Chinese Crude Drugs. VIII. Paeoniflorin, A Glucoside of Chinese Paeony Root. (1).
Abstract: An amorphous glucoside, named paeoniflorin, which was isolated from the roots of Paeonia albiflora PALLAS yielded crystalline tetraacetate, C31H36O15, and pentaacetate, C33H38O16. Alkaline hydrolysis showed that paeoniflorin possesses a benzoyl group. On treatment with lithium aluminium hydride, the acetates afforded product A, C16H24O10. Methylation of paeoniflorin tetraacetate yielded a methyl ether, C32H38O15 (product E acetate). By the action of lithium aluminium hydride, the product E acetate was converted into product F, C17H26O10. On treatment with sulfuric acid, the product F was hydrolyzed to yield an amorphous aglycone (aglycone F) liberating D-glucose. Oxidation of the aglycone F with cromium trioxide afforded a yellow crystalline quinonic compound (aglycone H), C10H10O4. The nuclear magnetic resonance spectral analysis of aglycone H leucodimethyl ether showed that it should be represented as 2-(4-methyl-2, 5-dimethoxyphenyl) or 2-(3-methyl-2, 5-dimethoxyphenyl) propionic acid. Paeoniflorin was shown to be D-glucoside of benzoylated C10-compound (C10H14O5).