3-O-β-D-quinovopyranosylstrophanthidin | 73208-83-0

• 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: 3-O-β-D-quinovopyranosylstrophanthidin
• 英文别名: (3I(2),5I(2))-3-[(6-Deoxy-I(2)-D-glucopyranosyl)oxy]-5,14-dihydroxy-19-oxocard-20(22)-enolide；(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• CAS: 73208-83-0
• 化学式: C₂₉H₄₂O₁₀
• 分子量: 550.646
• InChiKey: HULMNSIAKWANQO-IPCPLCPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-β-D-quinovopyranosylstrophanthidin 在 盐酸 、 (-)-α-methylbenzylamine 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 、 吡啶 为溶剂， 反应 3.0h， 生成 6-deoxy-D-glucose
  参考文献：
  名称：

  Cardenolides from Saussurea stella with Cytotoxicity toward Cancer Cells

  摘要：

  Three new cardenolides, 3-O-beta-D-fucopyranosylstrophanthidin (1), 3-O-beta-D-quinovopyranosylperiplogenin (2), and 3-O-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosylcannogenin (3), together with seven known cardenolides (4-10), were isolated from a cytotoxic ethanol extract of the whole dried plants of Saussurea stella. The structures of these compounds were established by spectroscopic and chemical methods. When the cytotoxicity of compounds 2-10 toward Bel-7402 human hepatoma cells and BGC-823 human gastric cancer cells was evaluated, all compounds showed IC50 values of <1 mu M for both cell lines. This is the first report of cardenolides occurring in a species of the family Asteraceae.

  DOI：

  10.1021/np070150o

文献信息

• Cardenolides from <i>Saussurea stella</i> with Cytotoxicity toward Cancer Cells
  作者：Tian-Min Wang、Toshinari Hojo、Fu-Xiang Ran、Ru-Feng Wang、Rui-Qing Wang、Hu-Biao Chen、Jing-Rong Cui、Ming-Ying Shang、Shao-Qing Cai

  DOI：10.1021/np070150o

  日期：2007.9.1

  Three new cardenolides, 3-O-beta-D-fucopyranosylstrophanthidin (1), 3-O-beta-D-quinovopyranosylperiplogenin (2), and 3-O-beta-D-glucopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosylcannogenin (3), together with seven known cardenolides (4-10), were isolated from a cytotoxic ethanol extract of the whole dried plants of Saussurea stella. The structures of these compounds were established by spectroscopic and chemical methods. When the cytotoxicity of compounds 2-10 toward Bel-7402 human hepatoma cells and BGC-823 human gastric cancer cells was evaluated, all compounds showed IC50 values of <1 mu M for both cell lines. This is the first report of cardenolides occurring in a species of the family Asteraceae.