2,3-脱氢水飞蓟宾B | 142796-24-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 2,3-脱氢水飞蓟宾B
• 中文别名: 2,3-脱氢水飞蓟宾B杂质；2,3-脱氢松节蛋白B
• 英文名称: 2,3-dehydrosilybin B
• 英文别名: dehydroisosilybin B；3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
• CAS: 142796-24-5
• 化学式: C₂₅H₂₀O₁₀
• 分子量: 480.428
• InChiKey: BVKQRAYKLBRNIK-RDPSFJRHSA-N

物化性质

• 沸点：
  761.0±60.0 °C(Predicted)
• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2,3-脱氢水飞蓟宾B 在 钾(4-硝基苯基)硫酸盐 、 aryl sulfotransferase from Desulfitobacterium hafniense 作用下， 以 丙酮 为溶剂， 生成 2,3-dehydrosilybin B 20-O-sulfate
  参考文献：
  名称：

  黄酮木脂素和 2,3-脱氢黄酮木脂素的硫酸化代谢物：制备和性质。

  摘要：

  水飞蓟素是从水飞蓟 (Silybum marianum) 果实中提取的提取物，可用于各种食品补充剂中。水飞蓟素黄酮木脂素在哺乳动物中的代谢是复杂的，其代谢物的确切结构仍然部分不清楚，而且标准品也没有商业化。本工作重点是水飞蓟素黄酮木脂素硫酸化代谢物的制备。使用来自哈夫尼脱硫杆菌的芳基磺基转移酶和对硝基苯硫酸盐作为硫酸盐供体制备硫酸化黄酮木脂素，并通过高分辨率质谱（HRMS）和核磁共振（NMR）进行表征。他们的 1,1-二苯基-2-三硝基苯肼 (DPPH)、2,2'-偶氮双-(3-乙基苯并噻唑啉-6-磺酸) (ABTS) 和 N,N-二甲基对苯二胺 (DMPD) 自由基清除; 三价铁 (FRAP) 和 Folin⁻Ciocalteu 试剂 (FCR) 降低活性；抗脂质过氧化潜力；并检查了对核红细胞 2 相关因子 2 (Nrf2) 信号通路的影响。纯水飞蓟宾 A 20-O-硫酸盐、水飞蓟宾 B

  DOI：

  10.3390/ijms19082349
• 作为产物：
  描述：

  silybin B 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以47%的产率得到2,3-脱氢水飞蓟宾B
  参考文献：
  名称：

  水飞蓟宾和异水飞蓟宾碱催化氧化为2,3-脱氢衍生物

  摘要：

  黄酮木聚糖，水飞蓟宾和异水飞蓟宾在碱催化下氧化为相应的2，3-脱氢衍生物的过程已得到研究和优化。测试了各种碱，溶剂和反应条件，以实现最佳收率。还观察到水对反应过程的影响。发现该氧化反应可能是基于（异）水飞蓟宾（或一些中间）分子的歧化，因为该反应也在没有氧的情况下进行。我们在这里首次报告了光学纯的2,3-脱氢异水飞蓟宾A和B的制备。

  DOI：

  10.1016/j.tetlet.2012.11.049

文献信息

• Inhibition of Aβ Amyloid Growth and Toxicity by Silybins: The Crucial Role of Stereochemistry
  作者：Michele. F. M. Sciacca、Valeria Romanucci、Armando Zarrelli、Irene Monaco、Fabio Lolicato、Natalia Spinella、Clelia Galati、Giuseppe Grasso、Luisa D’Urso、Margherita Romeo、Luisa Diomede、Mario Salmona、Corrado Bongiorno、Giovanni Di Fabio、Carmelo La Rosa、Danilo Milardi

  DOI：10.1021/acschemneuro.7b00110

  日期：2017.8.16

  The self-assembling of the amyloid beta (A beta) peptide into neurotoxic aggregates is considered a central event in the pathogenesis of Alzheimer's disease (AD). Based on the "amyloid hypothesis", many efforts have been devoted to designing molecules able to halt disease progression by inhibiting A beta self-assembly. Here, we combine biophysical (ThT assays, TEM and AFM imaging), biochemical (WB and ESI-MS), and computational (all-atom molecular dynamics) techniques to investigate the capacity of four optically pure components of the natural product silymarin (silybin A, silybin B, 2,3-dehydrosilybin A, 2,3-dehydrosilybin B) to inhibit A beta aggregation. Despite TEM analysis demonstrated that all the four investigated flavonoids prevent the formation of mature fibrils, ThT assays, WB and AFM investigations showed that only silybin B was able to halt the growth of small-sized protofibrils thus promoting the formation of large, amorphous aggregates. Molecular dynamics (MD) simulations indicated that silybin B interacts mainly with the C-terminal hydrophobic segment (35)MVGGVV(40) of A beta 40. Consequently to silybin B binding, the peptide conformation remains predominantly unstructured along all the simulations. By contrast, silybin A interacts preferentially with the segments (LVFF20)-L-17 and (27)NKGAI(132) of A beta 40 which shows a high tendency to form bend, turn, and beta-sheet conformation in and around these two domains. Both 2,3-dehydrosilybin enantiomers bind preferentially the segment (LVFF20)-L-17 but lead to the formation of different small-sized, ThT-positive A beta aggregates. Finally, in vivo studies in a transgenic Caenorhabditis elegans strain expressing human A beta indicated that silybin B is the most effective of the four compounds in counteracting A beta proteotoxicity. This study underscores the pivotal role of stereochemistry in determining the neuroprotective potential of silybins and points to silybin B as a promising lead compound for further development in anti-AD therapeutics.
• A Rapid and Simple Chromatographic Separation of Diastereomers of Silibinin and Their Oxidation to Produce 2,3-Dehydrosilybin Enantiomers in an Optically Pure Form
  作者：Giovanni Di Fabio、Valeria Romanucci、Cinzia Di Marino、Lorenzo De Napoli、Armando Zarrelli

  DOI：10.1055/s-0032-1328703

  日期：——

  Silybin A and B were separated from commercial silibinin using the preparative HPLC method. The described method is rapid and effective in obtaining gram-scale amounts of two diastereoisomers with minimal effort. In our approach, silibinin was dissolved in THF (solubility greater than 100 mg/mL), an alternative solvent to H2O or MeOH in which silibinin has a very low solubility (ca 0.05-1.5mg/mL), and then separated into its two components using preparative RP-HPLC. By starting with purified diastereoisomers, it was possible to obtain the two enantiomers of 2,3-dehydrosilybin in good yields and optically pure using an efficient oxidation procedure. All of the purified products were fully characterised using NMR (H-1, C-13), CD, [alpha](D), and ESI MS analyses. The purities of the products, which were evaluated using analytical HPLC, were greater than 98% in all cases.