23-O-acetylsilybin | 871249-25-1

• 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: 23-O-acetylsilybin
• 英文别名: 23-O-acetylsilibinin
• CAS: 871249-25-1
• 化学式: C₂₇H₂₄O₁₁
• 分子量: 524.481
• InChiKey: LEPZHZTYJGBLEL-XKPIBKDSSA-N

物化性质

• 沸点：
  775.7±60.0 °C(Predicted)
• 密度：
  1.477±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  38.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  161.21
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  23-O-acetylsilybin 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 50.17h， 生成 23-O-acetylhydnocarpin D
  参考文献：
  名称：

  Hydnocarpin型黄酮木聚糖：对金黄色葡萄球菌生物膜形成的半合成和抑制作用。

  摘要：

  开发并优化了一种新的，高效的，通用的蛇皮草型黄酮木聚糖半合成法，从而实现了按克规模生产的hydnocarpin D（2）。此外，光学纯的木犀草异构体[（10 R，11 R）-木犀草素（1a），（10 R，11 R）-木犀草素D（2a）和（10 S，11 S）-木犀草素D（2b）的合成）]以及异羟卡巴汀（8）的合成，是首次使用这种新方法实现的。合成基于乳蓟中容易获得的黄酮木聚糖的两步转化（水飞蓟），从商用的提取水飞蓟素隔离访问。第一步依靠使用Vilsmeier-Haack试剂对二氢黄酮型前体的C-3羟基进行区域选择性甲酰化，然后在第二步中用三乙胺消除甲酸。合成的化合物是金黄色葡萄球菌生物膜形成的有效抑制剂，其中（10 S，11 S）-hydnocarpin D（2b）是最有效的抑制剂。此外，测试了葡萄糖对生物膜形成的影响，并且葡萄糖降低了2b的生物膜抑制活性。此外，2b增加了葡萄球菌的敏感性。金黄色

  DOI：

  10.1021/acs.jnatprod.5b00430
• 作为产物：
  描述：

  水飞蓟素A,B 、 乙酸酐 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以60%的产率得到23-O-acetylsilybin
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of Silybin Diastereoisomers

  摘要：

  In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transcsterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.

  DOI：

  10.1021/np900758d

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.