(3-O-feruloyl-4-O-sinapoyl)-β-D-fructofuranosyl-(2→1)-(6-O-sinapoyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3-O-feruloyl-4-O-sinapoyl)-β-D-fructofuranosyl-(2→1)-(6-O-sinapoyl)-α-D-glucopyranoside
• 英文别名: raphasativuside A；[(2S,3S,4R,5R)-4-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₄₄H₅₀O₂₂
• 分子量: 930.868
• InChiKey: ZFUNZIPOLRYQON-CTDLUVRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  315
• 氢给体数：
  8
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (3-O-feruloyl-4-O-sinapoyl)-β-D-fructofuranosyl-(2→1)-(6-O-sinapoyl)-α-D-glucopyranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl (E)-sinapate 、 阿魏酸甲酯 、 蔗糖
  参考文献：
  名称：

  Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus

  摘要：

  A bioassay-guided fractionation and chemical investigation of the MeOH extract of Raphanus sativus seeds resulted in the isolation and identification of eight phenylpropanoid sucrosides (1-8) including two new compounds, named raphasativuside A and B (1-2) from the most active CHCl3-soluble fraction. The structures of these new compounds were elucidated through spectral analysis, including extensive 2D-NMR data, and chemical reaction experiments. We evaluated the anti-inflammatory effects of 1-8 in lipopolysaccharide (LPS)-stimulated murine microglia BV2 cells. Compounds 2 and 5 exhibited significant inhibitory effect on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 21.63 and 26.96 mu M, respectively. All isolates were also evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 1-7 showed consistent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values of 6.71-27.92 mu M. Additionally, the free-radical scavenging activity of 1-8 was assessed using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay where compounds 1, 3, and 4 scavenged DPPH radical strongly with IC50 values of 23.05, 27.10, and 29.63 mu g/mL, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.001

文献信息

• Anti-inflammatory and antitumor phenylpropanoid sucrosides from the seeds of Raphanus sativus
  作者：Ki Hyun Kim、Chung Sub Kim、Yong Joo Park、Eunjung Moon、Sang Un Choi、Jei Hyun Lee、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1016/j.bmcl.2014.11.001

  日期：2015.1

  A bioassay-guided fractionation and chemical investigation of the MeOH extract of Raphanus sativus seeds resulted in the isolation and identification of eight phenylpropanoid sucrosides (1-8) including two new compounds, named raphasativuside A and B (1-2) from the most active CHCl3-soluble fraction. The structures of these new compounds were elucidated through spectral analysis, including extensive 2D-NMR data, and chemical reaction experiments. We evaluated the anti-inflammatory effects of 1-8 in lipopolysaccharide (LPS)-stimulated murine microglia BV2 cells. Compounds 2 and 5 exhibited significant inhibitory effect on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 21.63 and 26.96 mu M, respectively. All isolates were also evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 1-7 showed consistent cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines with IC50 values of 6.71-27.92 mu M. Additionally, the free-radical scavenging activity of 1-8 was assessed using the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay where compounds 1, 3, and 4 scavenged DPPH radical strongly with IC50 values of 23.05, 27.10, and 29.63 mu g/mL, respectively. (C) 2014 Elsevier Ltd. All rights reserved.