resveratrol potassium 4'-sulfate | 1228999-20-9

• 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: resveratrol potassium 4'-sulfate
• 英文别名: resveratrol-4’-sulfate；potassium;3-hydroxy-5-[(E)-2-(4-sulfooxyphenyl)ethenyl]phenolate
• CAS: 1228999-20-9
• 化学式: C₁₄H₁₁O₆S*K
• 分子量: 346.402
• InChiKey: DBEZAQWZIMHBRG-TYYBGVCCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.89
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene 在 potassium fluoride 、 三甲基铵三氧化硫共聚物 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.33h， 生成 resveratrol potassium 4'-sulfate
  参考文献：
  名称：

  葡萄糖基和酰基白藜芦醇前药和白藜芦醇硫酸盐代谢产物的细胞毒，抗血管生成和抗端粒酶活性

  摘要：

  改善白藜芦醇活性：与白藜芦醇本身相比，糖基化白藜芦醇前药和硫酸白藜芦醇代谢物显示出改善的抗增殖和抗血管生成活性。这些结果表明白藜芦醇衍生物是潜在的药物，并证实硫酸白藜芦醇代谢物有助于母体化合物观察到的体内生物活性。

  DOI：

  10.1002/cbic.201600084

文献信息

• 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.
• Cytotoxic, Antiangiogenic and Antitelomerase Activity of Glucosyl- and Acyl- Resveratrol Prodrugs and Resveratrol Sulfate Metabolites
  作者：Eva Falomir、Ricardo Lucas、Pablo Peñalver、Rosa Martí-Centelles、Alexia Dupont、Alberto Zafra-Gómez、Miguel Carda、Juan C. Morales

  DOI：10.1002/cbic.201600084

  日期：2016.7.15

  Improved resveratrol activity: Glucosylated resveratrol prodrugs and resveratrol sulfate metabolites show improved anti‐proliferative and anti‐angiogenic activity in comparison to resveratrol itself. These results suggest resveratrol derivatives as potential drugs and confirm that resveratrol sulfate metabolites contribute to the in vivo biological activity observed for the parent compound.

  改善白藜芦醇活性：与白藜芦醇本身相比，糖基化白藜芦醇前药和硫酸白藜芦醇代谢物显示出改善的抗增殖和抗血管生成活性。这些结果表明白藜芦醇衍生物是潜在的药物，并证实硫酸白藜芦醇代谢物有助于母体化合物观察到的体内生物活性。