(11S)-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-[2-O-(trans-cinnamoyl)-4-O-(2S-methylbutanoyl)-α-L-rhamnopyranosyl-(1→4)]-O-(2-O-n-decanoyl)-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside-(1,3''-lactone) | 1467762-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (11S)-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-[2-O-(trans-cinnamoyl)-4-O-(2S-methylbutanoyl)-α-L-rhamnopyranosyl-(1→4)]-O-(2-O-n-decanoyl)-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside-(1,3''-lactone)
• 英文别名: cairicoside B；[(2S,3R,4R,5S,6S)-5-[(2S,3R,4R,5R,6S)-4-hydroxy-6-methyl-5-[(2S)-2-methylbutanoyl]oxy-3-[(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] decanoate
• CAS: 1467762-14-6
• 化学式: C₇₀H₁₁₂O₂₆
• 分子量: 1369.64
• InChiKey: QNBZCRURDRRBSU-FOFOWZNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  96.0
• 可旋转键数：
  26.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (11S)-jalapinolic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-[2-O-(trans-cinnamoyl)-4-O-(2S-methylbutanoyl)-α-L-rhamnopyranosyl-(1→4)]-O-(2-O-n-decanoyl)-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside-(1,3''-lactone) 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 、 正癸酸 、 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