cimigenol 3-O-β-D-xylopyranoside | 27994-11-2

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: cimigenol 3-O-β-D-xylopyranoside
• 英文别名: cimigenol xyloside
• CAS: 27994-11-2；62498-89-9；70518-90-0
• 化学式: C₃₅H₅₆O₉
• 分子量: 620.824
• InChiKey: BTPYUWOBZFGKAI-KCTCWXRRSA-N

物化性质

• 熔点：
  269-271 °C
• 沸点：
  740.3±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  44.0
• 可旋转键数：
  3.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138.07
• 氢给体数：
  5.0
• 氢受体数：
  9.0

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Cimigenoside 是升麻属中的有效成分。

化学性质 

类白色结晶体，可溶于甲醇、乙醇、DMSO等有机溶剂，来源于铁破锣根茎。

用途 

升麻醇-3-O-β-D-吡喃木糖苷具有清热解毒的作用。

用途 

用于含量测定/鉴定/药理实验等。
药理药效:清热解毒。

反应信息

• 作为产物：
  描述：

  24-O-acetylhydroshengmanol 3-[beta]-D-xylopyranoside(delta16,17)-enol ether 在 硫酸 、 水 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 cimigenol 3-O-β-D-xylopyranoside
  参考文献：
  名称：

  Studies on the Chinese crude drug "Shoma." V. Structures of 24-O-acetylhydroshengmanol xyloside and 22-hydroxycimigenol xyloside.

  摘要：

  Two new xylosides were isolated from the underground part of Cimicifuga japonica-24-O-acetylhydroshengmanol xyloside (2), C37H60O11, mp 235-237°, [α]22D+6.6°and 22-hydroxycimigenol xyloside (3), C35H56O10·H2O, mp 282-284°, [α]17D+17.7°. The xyloside (2) afforded, on acid hydrolysis in aq. methanol, cimigenol (4) and isodahurinol (5). Enzymatic hydrolysis of 2 afforded its genuine aglycone 24-O-acetylhydroshengmanol (8), C32H52O7, mp 200-202°, [α]26D+9.0°. The xyloside (2) and its genin (8) showed a mutarotation. When treated at room temperature with sulfuric acid in aq. methanol, 2 changed firstly into 25-O-acetylcimigenol xyloside (6) and finally into cimigenol xyloside (7). On the basis of chemical and spectral data, the structure of 24-O-acetylhydroshengmanol xyloside (2) was proposed to be (23R, 24S)-3β, 15α, 16ξ, 25-tetrahydroxy-24-acetoxy-16, 23-epoxy-9, 19-cyclolanostane 3-O-β-D-xylopyranoside. Another glycoside (3) showed, in its 13C-nuclear magnetic resonance (NMR) spectrum, a pattern of chemical shifts very similar to that of cimigenol xyloside (7), but a downfield shift of C-22 by 44.2 ppm was observed, suggesting oxygenation of C-22 in the glycoside (3). The xyloside (3) afforded, on both acidic and enzymatic hydrolyses, its aglycone (13), C30H48O6, mp 274-276°, [α]19D+45.0°. Huang-Minlon reduction of a diketo derivative (15) of 13 provided a didesoxy compound (16), C30H48O4, mp 202.5-203.5°, which was identical with the 3-desoxy derivative of cimigenol. The stereochemistry of the hydroxyl group at C-22 of 13 was assigned as R on the basis of its NMR spectrum. The structure of 22-hydroxycimigenol xyloside (3) was established as (22R)-22-hydroxycimigenol 3-O-β-D-xylopyranoside.

  DOI：

  10.1248/cpb.29.955