Sakurai N, Koeda M, Inoue T, Nagai M
Faculty of Pharmaceutical Science, Hoshi University, Tokyo, Japan.
Chem Pharm Bull (Tokyo). 1994 Jan;42(1):48-51. doi: 10.1248/cpb.42.48.
Two new triterpenol glycosides were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae): 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside (1), C43H70O16, mp 222-223 degrees C, [alpha]D +21.0 degrees and 3-xylosyl-24-O-acetylhydroshengmanol 15-glucoside (2), C43H70O16, mp 208-210 degrees C, [alpha]D +9.5 degrees. On acidic hydrolysis, 1 afforded cimigenol (3) as an aglycone, and glucose and arabinose as sugars. On enzymatic hydrolysis with molsin, 1 afforded 24-O-acetylhydroshengmanol 15-O-glucoside (4). On the basis of chemical and spectral data, the structure of 1 was proposed to be (23R,24S)-24-acetoxy-3-O-alpha-L-arabinopyranosyloxy-16,23-e poxy-9,19- 15-O-beta-D-glucopyranoside. The other glycoside (2) showed, in its 13C-NMR spectrum, a pattern of chemical shifts very similar to that of 1. On acidic hydrolysis, 2 afforded cimigenol (3), xylose and glucose. On enzymatic hydrolysis with molsin, 2 afforded 4. From these results, the structure of 2 was proposed to be (23R,24S)-24-acetoxy-3-O-beta-D-xylopyranosyloxy-16,23-epoxy -9,19-cyclolanostane-15 alpha,16 xi,25-triol 15-O-beta-D-glucopyranoside.
3 - 阿拉伯糖基 - 24 - O - 乙酰氢化升麻醇15 - 葡萄糖苷（1），C43H70O16，熔点222 - 223℃，[α]D +21.0°；以及3 - 木糖基 - 24 - O - 乙酰氢化升麻醇15 - 葡萄糖苷（2），C43H70O16，熔点208 - 210℃，[α]D +9.5°。酸性水解时，1产生升麻醇（3）作为苷元，以及葡萄糖和阿拉伯糖作为糖类。用莫辛酶水解时，1产生24 - O - 乙酰氢化升麻醇15 - O - 葡萄糖苷（4）。基于化学和光谱数据，1的结构被推测为(23R,24S)-24 - 乙酰氧基 - 3 - O - α - L - 阿拉伯吡喃糖氧基 - 16,23 - 环氧 - 9,19 - 环羊毛甾烷 - 15 - O - β - D - 葡萄糖吡喃糖苷。另一种糖苷（2）在其13C - NMR光谱中显示出与1非常相似的化学位移模式。酸性水解时，2产生升麻醇（3）、木糖和葡萄糖。用莫辛酶水解时，2产生4。根据这些结果，2的结构被推测为(23R,24S)-24 - 乙酰氧基 - 3 - O - β - D - 木糖吡喃糖氧基 - 16,23 - 环氧 - 9,19 - 环羊毛甾烷 - 15α,16ξ,25 - 三醇15 - O - β - D - 葡萄糖吡喃糖苷。
