45 Cimicifugosideの構造

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概要

• 論文の詳細を見る

• During the course of work on the constituents of Cimicifuga app., a new triterpenoid xyloside cimicifugoside (I), m.p. 237-238, C_<37>H_<54>O_<11>, has been obtained from the rhizomes of Cimicifuga simplex (Japanese name "sarashina shoma"). I is hydrolyzed with 50% acetic acid, 1% oxalic acid, or sodium periodate giving xylose, cimicifugenin A (III), and others. According to NMR and IR spectra of I and cimicifugoside tetra-acetate (II), which is obtained by complete acetylation of I, it is shown that I has a cyclopropane ring, an acetoxyl group, a double band, and a hemiacetal. The substance III yields the acetate (IV) and the benzoate (V) on acylation, the γ-lactone (VI) on oxidation with pyridine-CrO_3, the methyl ether (VII) on treatment with dil. methanolic HCl, and the deacetyl compound (VIII) on hydrolysis with 5% NaOH. Oxidation of VIII with pyridine-CrO_3 gives the α,β-unsaturated ketone (IX). These chemical properties suggest partial structures A-E for III. The comparison of the data of III with those reported for acetyl acteol (XVIII) shows that III has the same spiroketal structure as the latter (XVIII). On the basis of the above results, the structure III is proposed for cimicifugenin A. Deduction of the structure III for the hydrolyzed product of I, the chemical and physico-chemical properties of I and III, and mechanistic considerations in the transformation from I to III lead to the structure I for cimicifugoside.

• 天然有機化合物討論会の論文
• 1967-09-25

著者

• 草野 源次郎

  東北大薬

• 松本 祥子

  東北大薬

• 竹本 常松

  東北大薬

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