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

• Shibata Shoji

• Nakahara Motoko

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).

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 11 (3), 372-378, 1963

  The Pharmaceutical Society of Japan

Keywords

• Drug Discovery
• General Chemistry
• General Medicine

Details

• CRID: 1390282679141231616
• NII Article ID: 110003619091
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.11.372
• COI: 1:CAS:528:DyaF3sXktlGmt7g%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/11/3/11_3_372/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1964071998
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed