Acetyl Shengmanol, a Possible Parental Triterpene Acetate of Cimigenol and Cimigol from Cimicifuga japonica
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概要
- 論文の詳細を見る
A new triterpene glycoside (I) named acetyl shengmanol xyloside, mp 280-281°, [α]^<27>_D-23.7°, which was isolated from the underground part of Gimicifga japonica, yielded an amorphous aglycone (XII) on enzymatic hydrolysis. The peracetate of I afforded mainly 25-O-methylcimigenol (IV) along with cimigenol (V) and isodahurinol (VI) on acidic hydrolysis, while I gave cimigol xyloside (III), mp 297-299°, on alkaline treatment. The degradation of I with meta-periodate-cyclohexylamine gave an aldehyde-carboxylic acid, methyl ester of which has structure (IX). From chemical and spectral evidence, the structure of acetyl shengmanol (XII) was proposed to be (23R, 24S)-24,25-epoxy-3β, 15ξ-dihydroxy-23-acetoxy-9,19-cyclolanost-16-one. I is so unstable that it is readily convertible to cimigol xyloside (III) on alkaline treatment and to cimigenol (V) during acid hydrolysis. XII seems to be a precursor of cimigenol and cimigol in C. japonica. The mechanism of transformation of XII to V and VII was discussed.
- 公益社団法人日本薬学会の論文
- 1976-12-25
著者
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永井 正博
星薬科大学
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井上 隆夫
Hoshi College of Pharmacy
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永井 正博
Hoshi College of Pharmacy
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永井 正博
星薬大
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桜井 信子
Hoshi College of Pharmacy
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