cairicoside D | 1467762-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cairicoside D
• 英文别名: [(2S,3R,4R,5S,6S)-5-[(2S,3R,4S,5S,6S)-3-hydroxy-6-methyl-5-[(2S)-2-methylbutanoyl]oxy-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-6-methyl-2-[[(1S,3R,4S,5S,6R,8R,10S,22S,23S,24S,26R)-4,5,26-trihydroxy-6-(hydroxymethyl)-24-methyl-20-oxo-10-pentyl-2,7,9,21,25-pentaoxatricyclo[20.3.1.03,8]hexacosan-23-yl]oxy]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] octanoate
• CAS: 1467762-16-8
• 化学式: C₆₈H₁₀₈O₂₆
• 分子量: 1341.59
• InChiKey: NXLFLRZXGIHFDK-XQTTZVMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  94.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  359.34
• 氢给体数：
  8.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  cairicoside D 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-(+)-2-甲基丁酸 、 辛酸 、 肉桂酸 、 simonic acid A
  参考文献：
  名称：

  Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities

  摘要：

  Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.07.006

文献信息

• Pentasaccharide resin glycosides from Ipomoea cairica and their cytotoxic activities
  作者：Bangwei Yu、Jianguang Luo、Junsong Wang、Dongming Zhang、Shishan Yu、Lingyi Kong

  DOI：10.1016/j.phytochem.2013.07.006

  日期：2013.11

  Six partially acylated pentasaccharide resin glycosides, cairicosides A-F, were isolated from the aerial parts of Ipomoea cairica. These compounds were characterized as a group of macrolactones of simonic acid A, partially acylated with different organic acids. The lactonization site of 11S-hydroxyhexadecanoic acid (jalapinolic acid) was bound to the second saccharide moiety at C-3 in cairicosides A-E, while at C-2 in cairicoside F. Structures were established by spectroscopic and chemical methods. Compounds cairicosides A-E exhibited moderate cytotoxicity against a small panel of human tumor cell lines with IC50 values in the range of 4.28-14.31 mu M. (C) 2013 Elsevier Ltd. All rights reserved.