(25R)-3β-[(O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-26-[(β-D-glucopyranosyl)oxy]-5α-cholestane-6,22-dione | 1442015-26-0

• 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: (25R)-3β-[(O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-26-[(β-D-glucopyranosyl)oxy]-5α-cholestane-6,22-dione
• 英文别名: (3S,5S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S,6R)-6-methyl-3-oxo-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 1442015-26-0
• 化学式: C₄₅H₇₄O₁₉
• 分子量: 919.071
• InChiKey: ANFYYRJTBHYHAW-WVMHRXRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  312
• 氢给体数：
  11
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (25R)-3β-[(O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-26-[(β-D-glucopyranosyl)oxy]-5α-cholestane-6,22-dione 在 alpha-L-rhamnosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 432.0h， 以0.8 mg的产率得到(3S,5S,8S,9S,10R,13S,14S,17R)-3-Hydroxy-17-((1S,5R)-6-hydroxy-1,5-dimethyl-2-oxo-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities

  摘要：

  Steroidal glycosides (1-18), including 10 new compounds (1-10), were isolated from the bulbs of Fritillaria meleagris (Liliaceae). The structures of the new compounds were determined by two-dimensional (2D) NMR analysis, and by hydrolytic cleavage followed by spectroscopic and chromatographic analysis. The isolated compounds and their aglycones were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells. Morphological observation and flow cytometry analysis showed that 5 beta-spirostanol glycoside (2) and a cholestane derivative (17a) induced apoptotic cell death in HL-60 cells through different mechanisms of action. Furthermore, the (22R)-spirosolanol glycoside (11) selectively induced apoptosis in A549 cells without affecting the caspase-3 activity level. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.012