(20R,22R)-22-[(β-D-glucopyranosyl)oxy]-3β,14α,20-trihydoxy-5α-cholestan-6-one | 1442015-34-0

• 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: (20R,22R)-22-[(β-D-glucopyranosyl)oxy]-3β,14α,20-trihydoxy-5α-cholestan-6-one
• 英文别名: (3S,5S,8R,9S,10R,13R,14R,17S)-3,14-dihydroxy-17-[(2R,3R)-2-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 1442015-34-0
• 化学式: C₃₃H₅₆O₁₀
• 分子量: 612.802
• InChiKey: MHCBXDNDYHFGFZ-MJZCNFJZSA-N

物化性质

• 沸点：
  775.6±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (20R,22R)-22-[(β-D-glucopyranosyl)oxy]-3β,14α,20-trihydoxy-5α-cholestan-6-one 在 alpha-L-rhamnosidase 作用下， 以 aq. acetate buffer 为溶剂， 反应 432.0h， 以2.8 mg的产率得到tenuifoliol
  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

文献信息

• Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities
  作者：Yukiko Matsuo、Daisuke Shinoda、Aina Nakamaru、Yoshihiro Mimaki

  DOI：10.1016/j.steroids.2013.02.012

  日期：2013.7

  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.