cairicoside C | 1467762-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cairicoside C
• 英文别名: cairicoside A；[(2S,3S,4S,5R,6S)-5-hydroxy-2-methyl-6-[(2S,3S,4R,5R,6S)-2-methyl-5-[(2S)-2-methylbutanoyl]oxy-6-[[(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]oxy-4-[(E)-3-phenylprop-2-enoyl]oxyoxan-3-yl] (2S)-2-methylbutanoate
• CAS: 1467762-15-7
• 化学式: C₆₅H₁₀₂O₂₆
• 分子量: 1299.51
• InChiKey: SLEISTDUFHIYMA-OXJTUTBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  91.0
• 可旋转键数：
  20.0
• 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 C 、 sodium methylate 在 potassium hydroxide 作用下， 反应 2.08h， 生成 (S)-2-甲基丁酸甲酯 、 Methyl cinnamate
  参考文献：
  名称：

  Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity

  摘要：

  从毛苕子的气生部分分离出了六种五糖树脂苷，其中包括四种新的酰化五糖树脂苷，即毛苕子苷 I-IV（1-4）以及两种已知化合物毛苕子苷 A（5）和毛苕子苷 C（6）。这些化合物的结构是通过光谱（包括二维核磁共振）和化学方法确定的。这六种化合物的核心是辛酸 A，它们的酯化位点相同，只是取代基不同。在 1-4 号化合物中，琼脂酮的内酯化位点与第二个糖分子的 C-2 键相连，而在 5-6 号化合物中则与 C-3 键相连。化合物 1 和 5、4 和 6 是两对异构体。1-6 中的琼脂酮的绝对构型是 (11S)-hydroxyhexadecanoic acid（贾拉皮诺酸），这是用莫舍尔法确定的。评估了化合物 1-4 对α-葡萄糖苷酶的抑制活性，结果均显示出抑制活性。

  DOI：

  10.3390/molecules20046601

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.
• Four New Pentasaccharide Resin Glycosides from Ipomoea cairica with Strong α-Glucosidase Inhibitory Activity
  作者：Jie-Tao Pan、Bang-Wei Yu、Yong-Qin Yin、Jie-Hong Li、Li Wang、Li-Bing Guo、Zhi-Bin Shen

  DOI：10.3390/molecules20046601

  日期：——

  Six pentasaccharide resin glycosides from Ipomoea cairica, including four new acylated pentasaccharide resin glycosides, namely cairicoside I–IV (1–4) and the two known compounds cairicoside A (5) and cairicoside C (6), were isolated from the aerial parts of Ipomoea cairica. Their structures were established by a combination of spectroscopic, including two dimensional (2D) NMR and chemical methods. The core of the six compounds was simonic acid A, and they were esterfied the same sites, just differing in the substituent groups. The lactonization site of the aglycone was bonded to the second saccharide moiety at C-2 in 1–4, and at C-3 in 5–6. Compounds 1 and 5, 4 and 6 were two pairs of isomers. The absolute configuration of the aglycone in 1–6 which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid) was established by Mosher’s method. Compounds 1–4 have been evaluated for inhibitory activity against α-glucosidase, which all showed inhibitory activities.

  从毛苕子的气生部分分离出了六种五糖树脂苷，其中包括四种新的酰化五糖树脂苷，即毛苕子苷 I-IV（1-4）以及两种已知化合物毛苕子苷 A（5）和毛苕子苷 C（6）。这些化合物的结构是通过光谱（包括二维核磁共振）和化学方法确定的。这六种化合物的核心是辛酸 A，它们的酯化位点相同，只是取代基不同。在 1-4 号化合物中，琼脂酮的内酯化位点与第二个糖分子的 C-2 键相连，而在 5-6 号化合物中则与 C-3 键相连。化合物 1 和 5、4 和 6 是两对异构体。1-6 中的琼脂酮的绝对构型是 (11S)-hydroxyhexadecanoic acid（贾拉皮诺酸），这是用莫舍尔法确定的。评估了化合物 1-4 对α-葡萄糖苷酶的抑制活性，结果均显示出抑制活性。