symplocosidin | 76549-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: symplocosidin
• 英文别名: 3’-O-Methylepicatechin；3'-O-methyl (-)-epicatechin；3'-O-methyl-(-)-epicatechin；3'-O-methoxyepicatechin；3'-O-methyl-epicatechin；3'-O-methylepicatechin；(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 76549-34-3
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: NJHJXXLBWQXMRO-CZUORRHYSA-N

物化性质

• 沸点：
  589.9±50.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  symplocosidin 、 6-[[[5-(2,4-二氧代嘧啶-1-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 在 human recombinant uridine 5'-diphosphoglucuronosyltransferase UGT₁A₉ 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 3'-O-methyl-(-)-epicatechin-5-O-glucuronide
  参考文献：
  名称：

  Synthesis and Quantitative Analysis of Plasma-Targeted Metabolites of Catechin and Epicatechin

  摘要：

  Grape seed polyphenolic extract (GSPE) rich in the flavan-3-ols (+)-catechin and (-)-epicatechin beneficially modulates Alzheimer's Disease phenotypes in animal models. The parent molecules in the extract are converted to a series of methylated and glucuronidated derivatives. To fully characterize these metabolites and establish a robust quantitative assay of their levels in biological fluids, we have implemented a partial synthetic approach utilizing chemical methylation followed by enzymatic glucuronidation. Liquid chromatography/time-of-flight mass spectrometry (LC-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy were used to assign unequivocal structures to the compounds. An analytical method using solid-phase extraction and LC-MS/MS in selective reaction monitoring mode (SRM) was validated for their quantitation in plasma. These studies provide a basis for improvements in future work on the bioavailability, metabolism, and mechanism of action of metabolites derived from dietary flavan-3-ols in a range of interventions.

  DOI：

  10.1021/jf505922b
• 作为产物：
  描述：

  symplocoside 以 水 、 xylene 为溶剂， 反应 40.0h， 以230 mg的产率得到symplocosidin
  参考文献：
  名称：

  Symplocoside, a flavanol glycoside from Symplocos uniflora

  摘要：

  DOI：

  10.1016/s0031-9422(00)83821-2

文献信息

• Preparation and Characterization of Catechin Sulfates, Glucuronides, and Methylethers with Metabolic Interest
  作者：Susana González-Manzano、Ana González-Paramás、Celestino Santos-Buelga、Montserrat Dueñas

  DOI：10.1021/jf803140h

  日期：2009.2.25

  for which sufficient amounts of them are required that cannot be obtained by isolation from biological fluids. This paper describes the preparation of the methyl, sulfate, and glucuronide derivatives of catechins using different chemical syntheses and their characterization by HPLC−DAD−ESI/MS. MS2 fragmentation of the compounds was also described that allowed the determination of the location of the different

  儿茶素是许多植物食品中与健康促进有关的主要多酚。在人类有机体中，它们主要代谢为不同的结合物（硫酸盐，葡糖醛酸苷和甲基醚），这些结合物在血浆中进一步发现，将有助于与母体化合物摄入相关的生物学效应。循环代谢物可能具有与原始化合物不同的生物学特性，因此，重要的是评估其活性，为此需要足够量的代谢物，而这些量不能通过从生物体液中分离获得。本文介绍了使用不同化学合成方法制备儿茶素的甲基，硫酸盐和葡萄糖醛酸衍生物，并通过HPLC-DAD-ESI / MS对其进行了表征。MS 2还描述了化合物的断裂，从而可以确定儿茶素糖苷配基上不同取代基的位置。优化的程序允许制备在3'和4'位置缀合的（epi）儿茶素硫酸盐，葡糖醛酸苷和甲基醚，以及在5和7位置缀合的硫酸盐，具有令人满意的收率，可以通过半制备型HPLC进一步分离，考虑到它们在体外/离体测定中的用途。
• Enzymatic <i>O</i>-Methylation of Flavanols Changes Lag Time, Propagation Rate, and Total Oxidation during in Vitro Model Triacylglycerol-Rich Lipoprotein Oxidation
  作者：Jun Yu、Gabe Smith、Heidrun B. Gross、Robert J. Hansen、John Levenberg、Rosemary L. Walzem

  DOI：10.1021/jf060690b

  日期：2006.11.1

  3'-O-Methyl derivatives of flavan-3-ols, (+)-catechin (C), (-)-epicatechin (EC), and (-)-catechin gallate (CG) were prepared enzymatically. Hexanal (EC and CG family, 5 mmol/L) and conjugated diene (C and EC family, 0.25-10 mmol/L) formation following CuSO4-mediated triacylglycerol-rich lipoprotein oxidation was measured. All EC and CG compounds significantly reduced hexanal formation (p < 0.02). O-Methylation

  酶法制备黄烷-3-醇，（+）-儿茶素（C），（-）-表儿茶素（EC）和（-）-儿茶素没食子酸酯（CG）的3'-O-甲基衍生物。测量了在CuSO4介导的富含三酰基甘油的脂蛋白氧化后形成的己醛（EC和CG家族，5 mmol / L）和共轭二烯（C和EC家族，0.25-10 mmol / L）。所有的EC和CG化合物均显着降低了己醛的形成（p <0.02）。O-甲基化提高了CG（极性更大）的能力，同时降低了EC（极性较小）限制己醛形成的能力。3'-O-甲基EC抑制EC形成的能力比EC低18％（p <0.001）和4'-O-甲基65％（p <0.001）。> 1 micromol / L时，所有EC和C化合物的滞后时间均显着增加。母体化合物比代谢物（增加1.5倍）更有效（增加4倍以上）。母体化合物不影响繁殖速率（DeltaOD / min）。在> 1 mmol / L时，O-甲基化的EC和C将传播减少20-40％（p
• [EN] METHODS AND COMPOSITIONS FOR TREATMENT OF ISCHEMIC CONDITIONS AND CONDITIONS RELATED TO MITOCHONDRIAL FUNCTION<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR LE TRAITEMENT D'ÉTATS ISCHÉMIQUES ET D'ÉTATS ASSOCIÉS À UNE FONCTION MITOCHONDRIALE
  申请人：CARDERO THERAPEUTICS INC

  公开号：WO2010121232A1

  公开（公告）日：2010-10-21

  The present invention relates to compositions and methods for prophylactic and/or therapeutic treatment of conditions related to mitochondrial function. In various aspects, the present invention comprises administering one or more compounds selected from the group consisting of epicatechin, an epicatechin derivative, catechin, a catechin derivative, nicorandil, and a nicorandil derivative in an amount effective to stimulate mitochondrial function in cells. The methods and compositions described herein provide for reducing infarct size in the heart following permanent ischemia or ischemia /reperfusion (IR) event or method for delaying, attenuating or preventing adverse cardiac remodeling, and can assist in prevention of impaired mitochondria biogenesis and thus prevention of the consequences of impaired mitochondrial biogenesis in various diseases and conditions, as well as provide for the active therapy of mitochondrial depletion that may have already occurred.

  本发明涉及与线粒体功能相关的疾病的预防和/或治疗的组合物和方法。在各个方面上，本发明包括在有效剂量下给予来自以下化合物组合中的一个或多个化合物，其中所述化合物组合包括表儿茶素，表儿茶素衍生物，儿茶素，儿茶素衍生物，尼可地尔和尼可地尔衍生物，以刺激细胞的线粒体功能。本文所描述的方法和组合物可减小心脏在永久性缺血或缺血/再灌注（IR）事件后的梗死面积，或者延迟，减轻或预防不良心脏重构，并可帮助预防受损线粒体生物发生，从而预防各种疾病和情况中受损线粒体生物发生的后果，同时也可提供已经发生的线粒体耗竭的积极治疗。
• Boosting immunity
  申请人：Schmitz H. Harold

  公开号：US20080090898A1

  公开（公告）日：2008-04-17

  The invention relates to compositions, and methods of use thereof, for boosting immunity, e.g. innate immunity, in a subject in need thereof comprising administering to the subject certain polyphenols such as flavanols, procyanidins, or pharmaceutically acceptable salts or derivatives thereof.

  本发明涉及一种用于增强免疫力的组合物及其使用方法，例如增强天然免疫力，适用于需要该类增强免疫力的受试者。该组合物包括给受试者注射一定的多酚类物质，例如黄烷醇、原花青素或药学上可接受的其盐或衍生物。
• Compositions and methods of use of derivatized flavanols
  申请人：Kwik-Uribe L. Catherine

  公开号：US20060293259A1

  公开（公告）日：2006-12-28

  The invention relates to compositions containing derivatized flavanols such as methylated flavanols, and methods of use thereof for prophylactic or therapeutic treatment of a human or a veterinary animal for example as anti-platelet agents.

  本发明涉及含有衍生化黄烷醇的组合物，例如甲基化黄烷醇，以及其用于预防或治疗人类或兽医动物的方法，例如作为抗血小板剂的用途。