Studies on the Constituents of Japanese and Chinese Crude Drugs. VIII. Paeoniflorin, A Glucoside of Chinese Paeony Root. (1).

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概要

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• An amorphous glucoside, named paeoniflorin, which was isolated from the roots of Paeonia albiflora PALLAS yielded crystalline tetraacetate, C_<31>H_<36>O_<15>, and pentaacetate, C_<33>H_<38>O_<16>. Alkaline hydrolysis showed that paeoniflorin possesses a benzoyl group. On treatment with lithium aluminium hydride, the acetates afforded product A, C_<16>H_<24>O_<10>. Methylation of paeoniflorin tetraacetate yielded a methyl ether, C_<32>H_<38>O_<15> (product E acetate). By the action of lithium aluminium hydride, the product E acetate was converted into product F, C_<17>H_<26>O_<10>. 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), C_<10>H_<10>O_4. 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 C_<10>-compound (C_<10>H_<14>O_5).

• 1963-03-25

著者

• 柴田 承二

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 中原 素子

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)department Of Chemistry Toky

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