trans-resveratrol-4’-sulfate

• 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: trans-resveratrol-4’-sulfate
• 英文别名: trans-resveratrol-4′-sulfate；resveratrol-4′-O-sulfate；E-resveratrol-4'-sulfate ester；trans-resveratrol-4'-O-sulfate；trans-resveratrol-4'-sulfate；resveratrol 4'-O-sulfate；trans-Resveratrol 4'-sulfate；[4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenyl] hydrogen sulfate
• 化学式: C₁₄H₁₂O₆S
• 分子量: 308.312
• InChiKey: KOTTWDFKZULRPN-OWOJBTEDSA-N

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：

  trans-resveratrol-4’-sulfate 在 potassium carbonate 作用下， 以 水 为溶剂， 以0.025 g的产率得到resveratrol potassium 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：

  [4-[(E)-2-[3,5-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]ethenyl]phenyl] hydrogen sulfate 在 甲醇 、 potassium fluoride 作用下， 反应 12.0h， 生成 trans-resveratrol-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

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。
• ——
  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
• GLYCAN THERAPEUTICS AND RELATED METHODS THEREOF
  申请人：Kaleido Biosciences, Inc.

  公开号：EP3354282A1

  公开（公告）日：2018-08-01

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。
• 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。
• 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.