E-resveratrol-3,4’-disulfate ester | 858187-20-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: E-resveratrol-3,4’-disulfate ester
• 英文别名: resveratrol-3-O-4'-O-disulfate；resveratrol 3,4'-disulfate；trans-Resveratrol 3,4'-disulfate；[3-hydroxy-5-[(E)-2-(4-sulfooxyphenyl)ethenyl]phenyl] hydrogen sulfate
• CAS: 858187-20-9
• 化学式: C₁₄H₁₂O₉S₂
• 分子量: 388.376
• InChiKey: DHYDAGFKCXRMSL-OWOJBTEDSA-N

物化性质

• 密度：
  1.740±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  E-resveratrol-3,4’-disulfate ester 在 potassium carbonate 作用下， 以 水 为溶剂， 以0.015 g的产率得到resveratrol dipotassium 3,4'-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：

  在 potassium fluoride 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 E-resveratrol-3,4’-disulfate ester
  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。
• Soluble polyphenols: Synthesis and bioavailability of 3,4′,5-tri(α-d-glucose-3-O-succinyl) resveratrol
  作者：Lucia Biasutto、Ester Marotta、Alice Bradaschia、Mauro Fallica、Andrea Mattarei、Spiridione Garbisa、Mario Zoratti、Cristina Paradisi

  DOI：10.1016/j.bmcl.2009.09.114

  日期：2009.12

  We report the development of a chemical modification method of general applicability to polyphenols, which increases solubility to influence absorption. Glucosyl groups were added to the resveratrol kernel via a succinate linker, yielding 3,4',5-tri-(alpha-D-glucose-3-O-succinyl) resveratrol. The construct was only slowly hydrolyzed in acid and at pH 6.8, but it was destroyed by blood esterases in less than 1 h. In rats its administration resulted in a blood concentration versus time curve shifted to longer times in comparison to resveratrol, a useful modulation of pharmacokinetics. The area-under-curve parameter and the metabolite mix were similar to those of resveratrol. The method may be advantageously employed to solubilize other polyphenols and to make them more palatable. (C) 2009 Elsevier Ltd. All rights reserved.
• Selective Synthesis and Biological Evaluation of Sulfate-Conjugated Resveratrol Metabolites
  作者：Juma Hoshino、Eun-Jung Park、Tamara P. Kondratyuk、Laura Marler、John M. Pezzuto、Richard B. van Breemen、Shunyan Mo、Yongchao Li、Mark Cushman

  DOI：10.1021/jm100274c

  日期：2010.7.8

  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.