表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯 | 83104-87-4

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯
• 中文别名: 表没食子儿茶素3-O-(3-O-甲基)没食子酸酯
• 英文名称: epigallocatechin (3-O-methyl)gallate
• 英文别名: (2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4-dihydroxy-5-methoxybenzoate；(-)-(2R,3R)-5,7-dihydroxy-2-(3',4',5'-trihydroxy-phenyl)chroman-3-yl 3'',4''-dihydroxy-5''-methoxybenzoate；(-)-epigallocatechin 3-O-(3'-O-methyl-gallate)；(-)-epigallocatechin-3-O-(3''-O-methyl)gallate；(-)-epigallocatechin 3-O-(3-O-methyl)-gallate；(-)-epigallocatechin-3-O-(3-O-methyl) gallate；Epigallocatechin 3-O-(3-O-methyl)gallate；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4-dihydroxy-5-methoxybenzoate
• CAS: 83104-87-4
• 化学式: C₂₃H₂₀O₁₁
• 分子量: 472.405
• InChiKey: WVRDOLPMKOCJRJ-DENIHFKCSA-N

物化性质

• 熔点：
  221-223℃(DEC.)
• 沸点：
  856.1±65.0 °C(Predicted)
• 密度：
  1.77
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

安全信息

• 储存条件：
  室温

制备方法与用途

(-)-Epigallocatechin-3-(3''-O-methyl) gallate 是从茶叶中分离出的一种天然产物，具有很强的抗氧化和细胞毒性。这种化合物对大鼠癌细胞显示出较强的细胞毒性作用。

反应信息

• 作为反应物：
  描述：

  (-)-表儿茶素没食子酸酯 、 表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯 在 cocklebur polyphenol oxidase 作用下， 生成 theaflavin 3-O-(3-O-methyl)gallate-3'-gallate
  参考文献：
  名称：

  Determination of Theaflavins Including Methylated Theaflavins in Black Tea Leaves by Solid-Phase Extraction and HPLC Analysis

  摘要：

  A quantitative method for four theaflavins and two methylated theaflavin derivatives in black tea leaves was developed by solid-phase extraction and a high-performance liquid chromatographic method with photodiode array detection. The theaflavins in black tea leaves were extracted three times with 40 vol 50% aqueous ethanol (mg dry tea powder/mL) containing 2% ascorbic acid. The ethanol extracts were diluted 4-fold with distilled water. All diluted extracts were directly applied to the solid-phase C18 cartridge column without concentration. The fraction of theaflavins was obtained by 40% ethanol extraction after rinsing with water followed with 15% ethanol extraction. An aliquot of theaflavins after concentration was injected onto an ODS C-18 reversed-phase column, and four theaflavins and two methylated theaflavins were sufficiently separated by a linear gradient system using distilled water and acetonitrile with 0.5% acetic acid. This analytical method is sensitive for the determination of a small amount of methylated theaflavins, since various interfering substances produced during the fermentation process were eliminated in advance by solid-phase extraction. Using this analytical method, we also demonstrated that methylated theaflavins were easily produced during the manufacture of black tea.

  DOI：

  10.1021/jf070312m
• 作为产物：
  描述：

  (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3',4',5'-tris(benzyloxy)-phenyl]chroman-3-yl 3'',4''-dibenzyloxy-5''-methoxybenzoate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以83%的产率得到表没食子儿茶素 3-O-(3-O-甲基)没食子酸酯
  参考文献：
  名称：

  Regiospecific and enantioselective synthesis of methylated metabolites of tea catechins

  摘要：

  The regiospecific and enantioselective syntheses of various methylated regioisomers of epicatechin gallate (EGC) and epigallocatechin gallate (EGCG) have been achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.010

文献信息

• Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol
  作者：Tomohiro Asakawa、Yusuke Kawabe、Atsushi Yoshida、Yoshiyuki Aihara、Tamiko Manabe、Yoshitsugu Hirose、Asuka Sakurada、Makoto Inai、Yoshitaka Hamashima、Takumi Furuta、Toshiyuki Wakimoto、Toshiyuki Kan

  DOI：10.1038/ja.2016.14

  日期：2016.4

  An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio- and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, that are not readily available from natural sources. In addition, biomimetic synthesis of theaflavins from

  使用2-硝基苯磺酸盐（Ns）作为酚的保护基，建立了一种有效且通用的不稳定多酚合成方法。这种方法为区域和立体选择提供了一系列甲基化的儿茶素，例如甲基化的表没食子儿茶素没食子酸酯，而天然来源不易获得。此外，使用Ns保护可从儿茶素仿生合成茶黄素，从而最大程度地减少了氧化过程中富电子芳环的不良副反应，从而能够在一步氧化偶联反应中构建复杂的苯并马酚酮核。这些化合物的可用性将有助于儿茶素的详细结构生物学活性关系研究。
• Purification and characterization of a novel <i>O</i>-methyltransferase from <i>Flammulina velutipes</i>
  作者：Masanobu Kirita、Yoshihisa Tanaka、Motoyuki Tagashira、Tomomasa Kanda、Mari Maeda-Yamamoto

  DOI：10.1080/09168451.2014.912117

  日期：2014.5.4

  An enzyme catalyzing the methylation of phenolic hydroxyl groups in polyphenols was identified from mycelial cultures of edible mushrooms to synthesize O-methylated polyphenols. Enzyme activity was measured to assess whether methyl groups were introduced into (−)-epigallocatechin-3-O-gallate (EGCG) using SAM as a methyl donor, and (−)-epigallocatechin-3-O-(3-O-methyl)-gallate (EGCG3″Me), (−)-epigallocatechin-3-O-(4-O-methyl)-gallate (EGCG4″Me), and (−)-epigallocatechin-3-O-(3,5-O-dimethyl)-gallate (EGCG3″,5″diMe) peaks were detected using crude enzyme preparations from mycelial cultures of Flammulina velutipes. The enzyme was purified using chromatographic and two-dimensional electrophoresis. The purified enzyme was subsequently analyzed on the basis of the partial amino acid sequence using LC–MS/MS. Partial amino acid sequencing identified the 17 and 12 amino acid sequences, VLEVGTLGGYSTTWLAR and TGGIIIVDNVVR. In database searches, these sequences showed high identity with O-methyltransferases from other mushroom species and completely matched 11 of 17 and 9 of 12 amino acids from five other mushroom O-methyltransferases.

  从可食用蘑菇的菌丝培养物中鉴定出一种酶，该酶催化多酚中酚羟基的甲基化，以合成O-甲基化多酚。通过测量酶活性来评估是否使用SAM作为甲基供体将甲基引入(-)-表没食子儿茶素-3-O-没食子儿酸酯（EGCG）中，使用来自FLAa href=https://www.molaid.com/MS_77914 target="_blank">AMmulina velutipes菌丝培养物的粗酶制剂检测到(-)-表没食子儿茶素-3-O-(3-O-甲基)-没食子儿酸酯（EGCG3″Me）、(-)-表没食子儿茶素-3-O-(4-O-甲基)-没食子儿酸酯（EGCG4″Me）和(-)-表没食子儿茶素-3-O-(3,5-O-二甲基)-没食子儿酸酯（EGCG3″,5″diMe）峰。该酶经过层析和二维电泳纯化。随后，通过LC-MS/MS基于部分氨基酸序列对纯化酶进行分析。部分氨基酸测序鉴定出17和12个氨基酸序列，VLEVGTLGGYSTTWLAR和TGGIIIVDNVVR。在数据库搜索中，这些序列显示出与其他蘑菇物种的O-甲基转移酶高度相似，并与其他五种蘑菇O-甲基转移酶中的11个氨基酸和9个氨基酸完全匹配。
• Regioselective synthesis of methylated epigallocatechin gallate via nitrobenzenesulfonyl (Ns) protecting group
  作者：Yoshiyuki Aihara、Atsusi Yoshida、Takumi Furuta、Toshiyuki Wakimoto、Toshifumi Akizawa、Motomi Konishi、Toshiyuki Kan

  DOI：10.1016/j.bmcl.2009.05.111

  日期：2009.8

  Regioselective synthesis of methylated epigallocatechin gallate from epigallocatechin was accomplished using a 2-nitrobenzenesulfonyl (Ns) group as a protecting group for phenols. This methodology provided several methylated catechins, which are naturally scarce catechin derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• JP5965735
  申请人：——

  公开号：——

  公开（公告）日：——
• CATECHOL DERIVATIVES FOR THE TREATMENT OF CANCER
  申请人：The Burnham Institute

  公开号：EP1653943B3

  公开（公告）日：2008-07-30