methyl ester of simonic acid A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl ester of simonic acid A
• 英文别名: simonic acid A methyl ester；methyl (11S)-11-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6S)-3-hydroxy-6-methyl-4,5-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexadecanoate
• 化学式: C₄₇H₈₄O₂₄
• 分子量: 1033.17
• InChiKey: IQALYZUDJSRPPK-SFADJBRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  71
• 可旋转键数：
  26
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  361
• 氢给体数：
  12
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  methyl ester of simonic acid A 在 硫酸 作用下， 生成 (S)-methyl 11-hydroxyhexadecanoate
  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
• 作为产物：
  描述：

  cairicoside E 在 硫酸 、 potassium hydroxide 作用下， 反应 2.0h， 生成 methyl ester of 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

• Resin Glycosides. XV. Simonins I-V, Ether-Soluble Resin Glycosides (Jalapins) from the Roots of Ipomoea batatas (cv. Simon).
  作者：Naoki NODA、Shigenori YODA、Toshio KAWASAKI、Kazumoto MIYAHARA

  DOI：10.1248/cpb.40.3163

  日期：——

  Five new ether-soluble resin glycosides (jalapins), simonins I-V, have been isolated from the roots of Ipomoea batatas and characterized on the bases of chemical and spectral data. Simonim I is the first example of resin glycoside with aromatic acid (trans-cinnamic acid) as a component organic acid.

  从甘薯（Ipomoea batatas）的根部分离出五种新的醚溶性树脂糖苷（jalapins），即西蒙尼糖苷I-V，并基于化学和光谱数据对其进行了表征。西蒙尼糖苷I是首个以芳香酸（反式肉桂酸）作为组分有机酸的树脂糖苷实例。
• 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.