升麻素苷H-1 | 163046-73-9

• 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
• 中文名称: 升麻素苷H-1
• 中文别名: 升麻苷H1
• 英文名称: cimicifugoside H-1
• 英文别名: Cimicifugoside H1；(1S,3R,6S,8R,12R,15R,16R,18S)-15-[(2R)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-oxobutan-2-yl]-18-hydroxy-7,7,12,16-tetramethyl-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadec-10-en-14-one
• CAS: 163046-73-9
• 化学式: C₃₅H₅₂O₉
• 分子量: 616.792
• InChiKey: PYBFXJMIKJNNAJ-GLWILYKISA-N

物化性质

• 熔点：
  260-262℃
• 密度：
  1.31±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  9

制备方法与用途

生物活性方面，Cimicifugoside H-1 是一种环甾烷醇木糖苷，作为 C. foetida L.C 的主要成分被提取出来。研究显示，Cimicifugoside H-1 可以抑制骨吸收并减少卵巢切除术引起的骨质流失。

反应信息

• 作为反应物：
  描述：

  升麻素苷H-1 在 Na₂HPO₄-0.1 M citric acid buffer 作用下， 以 乙醇 、 水 为溶剂， 反应 168.0h， 以115 mg的产率得到cimicidanol
  参考文献：
  名称：

  Studies on the Chinese Crude Drug "Shoma." IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1, H-2 and H-5, from Cimicifuga Rhizome.

  摘要：

  Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262°C, [α]D -43.5°, cimicifugoside H-2 (2), C35H54O10, mp 227-229°C, [α]D -38.8°, and cimicifugoside H-5 (3), C35H52O10, mp 262-264°C, [α]D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24, 25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.

  DOI：

  10.1248/cpb.43.771

文献信息

• Studies on the Chinese Crude Drug "Shoma." IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1, H-2 and H-5, from Cimicifuga Rhizome.
  作者：Mamoru KOEDA、Yoshinobu AOKI、Nobuko SAKURAI、Masahiro NAGAI

  DOI：10.1248/cpb.43.771

  日期：——

  Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262°C, [α]D -43.5°, cimicifugoside H-2 (2), C35H54O10, mp 227-229°C, [α]D -38.8°, and cimicifugoside H-5 (3), C35H52O10, mp 262-264°C, [α]D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24, 25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.