4-{(E)-2-[3,5-二(磺基氧基)苯基]乙烯基}苯基氢硫酸盐 | 858187-22-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-{(E)-2-[3,5-二(磺基氧基)苯基]乙烯基}苯基氢硫酸盐
• 英文名称: E-resveratrol-3,4’,5-trisulfate ester
• 英文别名: Trans resveratrol-3,4',5-trisulfate；[4-[(E)-2-(3,5-disulfooxyphenyl)ethenyl]phenyl] hydrogen sulfate
• CAS: 858187-22-1
• 化学式: C₁₄H₁₂O₁₂S₃
• 分子量: 468.44
• InChiKey: PTXZZWAYVALFLP-OWOJBTEDSA-N

物化性质

• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  216
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-{(E)-2-[3,5-二(磺基氧基)苯基]乙烯基}苯基氢硫酸盐 在 potassium carbonate 作用下， 以 水 为溶剂， 以0.054 g的产率得到resveratrol tripotassium 3,5,4'-sulfate
  参考文献：
  名称：

  Selective Synthesis and Biological Evaluation of Sulfate-Conjugated Resveratrol Metabolites

  摘要：

  Five resveratrol sulfate metabolites were synthesized and assessed for activities known to be mediated by resveratrol: inhibition of tumor necrosis factor (TNF)alpha induced NF kappa B activity, cylcooxygenases (COX-1 and COX-2), aromatase, nitric oxide production in endotoxin-stimulated macrophages, proliferation of KB or MCF7 cells, induction of quinone reductase I (QRI), accumulation in the sub-G, phase of the cell cycle, and quenching of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical. Two metabolites showed activity in these assays; the 3-sulfate exhibited QRI induction, DPPH free radical scavenging, and COX-1 and COX-2 inhibitory activities and the 4'-sulfate inhibited NF kappa B induction, as well as COX-1 and COX-2 activities. Resveratrol and its 3'-sulfate and 4-sulfate inhibit NO production by NO scavenging and down-regulation of iNOS expression in RAW 264.7 cells. Resveratrol sulfates displayed low antiproliferative activity and negligible uptake in MCF7 cells.

  DOI：

  10.1021/jm100274c
• 作为产物：
  描述：

  白藜芦醇 在 三甲基铵三氧化硫共聚物 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成 4-{(E)-2-[3,5-二(磺基氧基)苯基]乙烯基}苯基氢硫酸盐
  参考文献：
  名称：

  Selective Synthesis and Biological Evaluation of Sulfate-Conjugated Resveratrol Metabolites

  摘要：

  Five resveratrol sulfate metabolites were synthesized and assessed for activities known to be mediated by resveratrol: inhibition of tumor necrosis factor (TNF)alpha induced NF kappa B activity, cylcooxygenases (COX-1 and COX-2), aromatase, nitric oxide production in endotoxin-stimulated macrophages, proliferation of KB or MCF7 cells, induction of quinone reductase I (QRI), accumulation in the sub-G, phase of the cell cycle, and quenching of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical. Two metabolites showed activity in these assays; the 3-sulfate exhibited QRI induction, DPPH free radical scavenging, and COX-1 and COX-2 inhibitory activities and the 4'-sulfate inhibited NF kappa B induction, as well as COX-1 and COX-2 activities. Resveratrol and its 3'-sulfate and 4-sulfate inhibit NO production by NO scavenging and down-regulation of iNOS expression in RAW 264.7 cells. Resveratrol sulfates displayed low antiproliferative activity and negligible uptake in MCF7 cells.

  DOI：

  10.1021/jm100274c

文献信息

• Enzymatic Sulfation of Phenolic Hydroxy Groups of Various Plant Metabolites by an Arylsulfotransferase
  作者：Michael A. van der Horst、Aloysius F. Hartog、Rabab El Morabet、Arthur Marais、Menzo Kircz、Ron Wever

  DOI：10.1002/ejoc.201402875

  日期：2015.1

  The bacterial arylsulfate sulfotransferase (AST) from Desulfitobacterium hafniense was used as a catalytic tool to derivatize poorly sol. arom. compds. (polyphenols)​. As examples, we sulfated the natural occurring compds. p-​coumaric acid, 6-​hydroxyflavone, resveratrol, phloretin, and quercetin, using p-​nitrophenylsulfate as the sulfate donor. The water-​sol. sulfate esters were purified and characterized

  来自 Desulfitobacterium hafniense 的细菌芳基硫酸盐磺基转移酶 (AST) 被用作催化工具来衍生较差的溶胶。芳香。化合物。（多酚）。例如，我们将天然存在的化合物硫酸化。对香豆酸、6-羟基黄酮、白藜芦醇、根皮素和槲皮素，使用对硝基苯硫酸盐作为硫酸盐供体。水溶胶。硫酸酯被纯化和表征。根据化合物的性质，可以逐步引入一个或多个硫酸根基团。白藜芦醇的硫酸化作用产生两种不同的单硫酸盐（4'-和 3- 硫酸盐），即 3, 4'- 二硫酸盐和 3, 5, 4'- 三硫酸盐。根皮素的硫酸化产生单硫酸盐（4'- 硫酸盐）和二硫酸盐（4, 4'- 二硫酸盐）。虽然槲皮素有五个可以被硫酸化的羟基，令人惊讶的是，该酶系统主要仅在 4' 位催化硫酸化。这种简单的酶促一步硫酸化方法易于使用，并且生产方便简单。硫酸化化合物。与改善 soly。
• Sulfation made easy: A new versatile donor for enzymatic sulfation by a bacterial arylsulfotransferase
  作者：Aloysius F. Hartog、Ron Wever

  DOI：10.1016/j.molcatb.2016.04.007

  日期：2016.7

  An efficient and versatile donor for the sulfation by a bacterial arylsulfotransferase of various phenolic acceptor molecules is reported. Most studies in the past used toxic p-nitrophenyl sulfate as a sulfate donor for sulfation by this enzyme. However both the donor and p-nitrophenol are difficult to remove from the sulfated products. This new donor N-hydroxysuccinimide sulfate is easy to synthesize and has the advantage that at pH values above 7 it hydrolyzes to N-hydroxysuccinimide which is a safe compound and can easily be removed. As examples we demonstrated the formation of sulfated resveratrol and synthesized efficiently 3-sulfo-17-beta-estradiol and bisphenol A bisulfate. It is likely that many other phenolic compounds are sulfated using this donor. (C) 2016 Elsevier B.V. All rights reserved.