indioside H | 1365309-14-3

• 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: indioside H
• 英文别名: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'S,6S,7R,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 1365309-14-3
• 化学式: C₃₉H₆₂O₁₂
• 分子量: 722.914
• InChiKey: HDXIQHTUNGFJIC-QGNVFQJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  51
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  indioside H 、 乙酸酐 在 盐酸 、 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 生成 Quinovose tetraacetate
  参考文献：
  名称：

  Indiosides G–K: Steroidal Glycosides with Cytotoxic and Anti-inflammatory Activities from Solanum violaceum

  摘要：

  Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons. The structures of the new compounds, were elucidated using 1D and 2D spectroscopic techniques and acid hydrolysis. Compounds 2, 3, and 7-9 exhibited cytotoxic activity against six human cancer cell lines (HepG2, Hep3B, A549, Ca9-22, MDA-MB-231, and MCF-7) with IC50 values of 1.83-8.04 mu g/mL. Steroidal saponins, 3, 8, and 9, showed inhibitory effects on superoxide anion generatiom with IC50 values of 2.84 +/- 0.18, 0.62 +/- 0.03, and 1.62 +/- 0.59 mu g/mL, respectively. Saponins 8 and 9 also inhibited elastase release with IC50 values of 111.05 +/- 7.37 and 4.04 +/- 0.51 mu g/mL, respectively. Structure-activity relationship correlations of these compounds with respect to cytotoxic and anti-inflammatory effects are discussed.

  DOI：

  10.1021/np200877u

文献信息

• Indiosides G–K: Steroidal Glycosides with Cytotoxic and Anti-inflammatory Activities from <i>Solanum violaceum</i>
  作者：Chiao-Ting Yen、Chia-Lin Lee、Fang-Rong Chang、Tsong-Long Hwang、Hsin-Fu Yen、Chao-Jung Chen、Shu-Li Chen、Yang-Chang Wu

  DOI：10.1021/np200877u

  日期：2012.4.27

  Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons. The structures of the new compounds, were elucidated using 1D and 2D spectroscopic techniques and acid hydrolysis. Compounds 2, 3, and 7-9 exhibited cytotoxic activity against six human cancer cell lines (HepG2, Hep3B, A549, Ca9-22, MDA-MB-231, and MCF-7) with IC50 values of 1.83-8.04 mu g/mL. Steroidal saponins, 3, 8, and 9, showed inhibitory effects on superoxide anion generatiom with IC50 values of 2.84 +/- 0.18, 0.62 +/- 0.03, and 1.62 +/- 0.59 mu g/mL, respectively. Saponins 8 and 9 also inhibited elastase release with IC50 values of 111.05 +/- 7.37 and 4.04 +/- 0.51 mu g/mL, respectively. Structure-activity relationship correlations of these compounds with respect to cytotoxic and anti-inflammatory effects are discussed.