3-O-β-D-xylopyranosylstrophanthidin

• 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-xylopyranosylstrophanthidin
• 英文别名: 5,14-dihydroxy-19-oxo-3β-β-D-xylopyranosyloxy-5β,14β-card-20(22)-enolide；5,14-Dihydroxy-19-oxo-3β-β-D-xylopyranosyloxy-5β,14β-card-20(22)-enolid；(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• 化学式: C₂₈H₄₀O₁₀
• 分子量: 536.62
• InChiKey: XMNREHIXCIWCGI-OIAVFDJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  38
• 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-xylopyranosylstrophanthidin 在 盐酸 、 (-)-α-methylbenzylamine 、 sodium cyanoborohydride 、 乙酸酐 作用下， 以 甲醇 、 水 、 吡啶 为溶剂， 反应 3.0h， 生成 D-吡喃木糖
  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
• 作为产物：
  描述：

  毒毛旋花子苷元 在 甲醇 、 碘 、 barium methoxide 、 magnesium sulfate 、 silver carbonate 作用下， 生成 3-O-β-D-xylopyranosylstrophanthidin
  参考文献：
  名称：

  SYNTHETIC GLYCOSIDES OF STROPHANTHIDIN

  摘要：

  DOI：

  10.1021/jo01190a007

文献信息

• SYNTHETIC GLYCOSIDES OF STROPHANTHIDIN
  作者：FREDERICK C. UHLE、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01190a007

  日期：1943.3
• 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.