白藜芦醇-3-O-硫酸盐(反式) | 553662-69-4

• 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: 白藜芦醇-3-O-硫酸盐(反式)
• 英文名称: Resveratrol 3-O-sulfate
• 英文别名: resveratrol‐3‐sulfate；trans-resveratrol 3'-O-sulfate；E-resveratrol-3-sulfate ester；trans-resveratrol-3-O-sulfate；trans-resveratrol-3-sulfate；Resveratrol-3-O-sulfate；[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl] hydrogen sulfate
• CAS: 553662-69-4
• 化学式: C₁₄H₁₂O₆S
• 分子量: 308.312
• InChiKey: DULQFFCIVGYOFH-OWOJBTEDSA-N

物化性质

• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 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：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  白藜芦醇-3-O-硫酸盐(反式) 在 potassium carbonate 作用下， 以 水 为溶剂， 以0.01 g的产率得到resveratrol-3-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 甲醇 、 potassium fluoride 作用下， 反应 12.0h， 生成 白藜芦醇-3-O-硫酸盐(反式)
  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

• SILYLATED DERIVATIVES OF RESERVATROL AND THE USE THEREOF IN NEURODEGENERATIVE, NEUROLOGICAL OR INFLAMMATORY DISEASES
  申请人：Consejo Superior De Investigaciones Científicas

  公开号：US20190284213A1

  公开（公告）日：2019-09-19

  The present invention relates to a group of compounds derived from resveratrol having as substituents at least one silyl group which, in turn, can be substituted by different groups. The invention also relates to the therapeutic use of these compounds in inflammatory, neurological, and neurodegenerative diseases.

  本发明涉及一组从白藜芦醇衍生的化合物，其取代基至少为一个硅烷基，该硅烷基又可以被不同的基团取代。该发明还涉及这些化合物在炎症性、神经系统和神经退行性疾病中的治疗用途。
• 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。
• ——
  作者：Chongwoo Yu、Young Geun Shin、Anita Chow、Yongmei Li、Jerome W. Kosmeder、Yong Sup Lee、Wendy H. Hirschelman、John M. Pezzuto、Rajendra G. Mehta、Richard B. van Breemen

  DOI：10.1023/a:1021414129280

  日期：——

  investigated. METHODS The in vitro experiments included incubation with human liver microsomes, human hepatocytes, and rat hepatocytes and the in vivo studies included oral or intraperitoneal administration of resveratrol to rats and mice. Methanol extracts of rat urine, mouse serum, human hepatocytes, rat hepatocytes, and human liver microsomes were analyzed for resveratrol metabolites using reversed-phase

  目的白藜芦醇是一种存在于葡萄，葡萄酒，花生和蔓越莓中的酚类植物抗毒素，据报道具有抗癌，抗氧化，植物雌激素和心脏保护作用。由于对该潜在重要化合物的代谢知之甚少，因此研究了反式白藜芦醇的体外和体内代谢。方法体外实验包括与人肝微粒体，人肝细胞和大鼠肝细胞一起孵育，体内研究包括对大鼠和小鼠口服或腹膜内给予白藜芦醇。大鼠尿液，小鼠血清，人肝细胞，大鼠肝细胞的甲醇提取物，使用反相高效液相色谱，在线紫外光电二极管阵列检测和质谱检测（LC-DAD-MS和LC-UV-MS-MS）分析人肝微粒体中白藜芦醇代谢物。紫外光电二极管阵列分析有助于白藜芦醇及其代谢物的顺式和反式异构体的鉴定。负离子电喷雾质谱分析提供了白藜芦醇代谢物的分子量确认，而串联质谱分析则可以获取结构信息。结果在微粒体温育中未检测到白藜芦醇代谢物，在任何样品中均未观察到I相代谢物，例如氧化，还原或水解。然而，在大鼠尿液，小鼠血清中以及与大鼠和人类
• PHILLYGENOL SULPHATE AND DERIVATIVE THEREOF, AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：Fu, Li

  公开号：EP3072895A1

  公开（公告）日：2016-09-28

  The present invention provides a forsythiaside sulfate derivatives as represented by the following formula, the preparation method and antiviral application thereof:

  本发明提供了由下式表示的连翘苷硫酸盐衍生物及其制备方法和抗病毒应用：
• Antioxidative stress compositions, methods of preparing and uses thereof
  申请人：Pezzuto John Michael

  公开号：US10413524B2

  公开（公告）日：2019-09-17

  Antioxidative stress compositions, methods of using antioxidative stress composition and methods of preparing antioxidative stress composition compositions are described. The antioxidative stress compositions may be chemopreventive and/or immunomodulatory. Resveratrol, genistein, ellagic acid, curcumin and quercetin may be included in the antioxidative stress composition compositions individually or in any combination.

  描述了抗氧化应激组合物、使用抗氧化应激组合物的方法和制备抗氧化应激组合物的方法。抗氧化应激组合物可以具有化学预防和/或免疫调节作用。白藜芦醇、染料木素、鞣花酸、姜黄素和槲皮素可单独或以任何组合形式加入抗氧化应激组合物中。