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).