7-O-dihydroferuloylsilibinin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 7-O-dihydroferuloylsilibinin
• 英文别名: [(2R,3R)-3,5-dihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-4-oxo-2,3-dihydrochromen-7-yl] 3-(4-hydroxy-3-methoxyphenyl)propanoate
• 化学式: C₃₅H₃₂O₁₃
• 分子量: 660.631
• InChiKey: ATCXMJZJFUFCBK-UNRARQKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  191
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  水飞蓟素A,B 、 3-(4-羟基-3-甲氧基苯基)丙酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 1.0h， 以18%的产率得到7-O-dihydroferuloylsilibinin
  参考文献：
  名称：

  Regioselective synthesis of 7-O-esters of the flavonolignan silibinin and SARs lead to compounds with overadditive neuroprotective effects

  摘要：

  A series of neuroprotective hybrid compounds was synthesized by conjugation of the flavonolignan silibinin with natural phenolic acids, such as ferulic, cinnamic and syringic acid. Selective 7-O-esterfication without protection groups was achieved by applying the respective acyl chlorides. Sixteen compounds were obtained and SARs were established by evaluating antioxidative properties in the physicochemical FRAP assay, as well as in a cell-based neuroprotection assay using murine hippocampal HT-22 cells. Despite weak activities in the FRAP assay, esters of the alpha,beta-unsaturated acids showed pronounced overadditive effects at low concentrations greatly exceeding the effects of equimolar mixtures of silibinin and the respective acids in the neuroprotection assay. Cinnamic and ferulic acid esters (5a and 6a) also showed overadditive effects regarding inhibition of microglial activation, PC12 cell differentiation, in vitro ischemia as well as anti-aggregating abilities against A beta 42 peptide and tau protein. Remarkably, the esters of ferulic acid with silybin A and silybin B (11a and 11b) showed a moderate but significant difference in both neuroprotection and in their anti-aggregating capacities. The results demonstrate that non-toxic natural antioxidants can be regioselectively connected as esters with medium-term stability exhibiting very pronounced overadditive effects in a portfolio of biological assays. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.036

文献信息

• Regioselective synthesis of 7-O-esters of the flavonolignan silibinin and SARs lead to compounds with overadditive neuroprotective effects
  作者：Simon Schramm、Guozheng Huang、Sandra Gunesch、Florian Lang、Judit Roa、Petra Högger、Raimon Sabaté、Pamela Maher、Michael Decker

  DOI：10.1016/j.ejmech.2018.01.036

  日期：2018.2

  A series of neuroprotective hybrid compounds was synthesized by conjugation of the flavonolignan silibinin with natural phenolic acids, such as ferulic, cinnamic and syringic acid. Selective 7-O-esterfication without protection groups was achieved by applying the respective acyl chlorides. Sixteen compounds were obtained and SARs were established by evaluating antioxidative properties in the physicochemical FRAP assay, as well as in a cell-based neuroprotection assay using murine hippocampal HT-22 cells. Despite weak activities in the FRAP assay, esters of the alpha,beta-unsaturated acids showed pronounced overadditive effects at low concentrations greatly exceeding the effects of equimolar mixtures of silibinin and the respective acids in the neuroprotection assay. Cinnamic and ferulic acid esters (5a and 6a) also showed overadditive effects regarding inhibition of microglial activation, PC12 cell differentiation, in vitro ischemia as well as anti-aggregating abilities against A beta 42 peptide and tau protein. Remarkably, the esters of ferulic acid with silybin A and silybin B (11a and 11b) showed a moderate but significant difference in both neuroprotection and in their anti-aggregating capacities. The results demonstrate that non-toxic natural antioxidants can be regioselectively connected as esters with medium-term stability exhibiting very pronounced overadditive effects in a portfolio of biological assays. (C) 2018 Elsevier Masson SAS. All rights reserved.