Studies on the Constituents of Japanese and Chinese Crude Drugs. XII. Panaxadiol, A Sapogenin of Ginseng Roots. (2).

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概要

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• The treatment of panaxanolone acetate with caustic alkali showed that it possesses a less-hindered stereochemical structure. The Dreiding Model suggested three possible less-hindered structures for panaxanolone which included trans C/D 17α-H system (X), cis C/D 17β-H system both chair (Y') and boat (Z') C-ring (Fig. 1). The infrared spectral analysis showed that the hydroxyl at the 12-position of panaxadiol (12β-OH) as well as that of 12-epi-panaxadiol (12α-OH) are hydrogen-bonded with the oxygen of trimethyltetrahydropyrane ring attached at C_<(17)>. Moreover, the atomic distance between 12-OH and tetrahydropyrane ring oxygen is shown by the Dreiding Model as being much closer in the case of 12β-OH than 12α-OH, which is proved by the resistance of panaxadiol against acetylation at 12-OH. This can only be explained by the stereochemical system of cis C (chair)/D, 12β-OH, 17β-H for panaxadiol (II), and cis C (boat)/D, 12α-OH, 17β-H for 12-epi-panaxadiol (III).

• 社団法人日本薬学会の論文
• 1963-06-25

著者

• 柴田 承二

  Meiji College of Pharmacy

• 石井 達郎

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 田中 治

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address) Pharmaceutical Institute Sc

• 柴田 承二

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 永井 正博

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 柴田 承二

  明治薬科大学

• 永井 正博

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Addresses)hoshi College Of Pharmacy

• 柴田 承二

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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