[(2R,3R)-2-[2-[3-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-1-hydroxyphenazin-2-yl]-3,4,5-trihydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

• 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: [(2R,3R)-2-[2-[3-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-1-hydroxyphenazin-2-yl]-3,4,5-trihydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₅₀H₃₆N₂O₂₀
• 分子量: 984.837
• InChiKey: CUANLYWDTIMKKD-HIEUYNPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  72
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  380
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 Japanese pear fruit homogenate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.25h， 生成 [(2R,3R)-2-[2-[3-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-1-hydroxyphenazin-2-yl]-3,4,5-trihydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation–reduction dismutation of dehydrotheasinensin A

  摘要：

  Theasinensins A and D are B,B'-linked dimers of (-)-epigallocatechin 3-O-gallate connected through R and S biphenyl bonds, respectively, and are major constituents of black tea. Enzymatic oxidation of epigallocatechin 3-O-gallate produced dehydrotheasinensin A, and the structure was shown to be equivalent to an o-quinone of theasinensin A. When the aqueous solution of dehydrotheasinensin A was heated, theasinensin D was produced along with galloyl oolongtheanin. On the other hand, dehydrotheasinensin A was converted to theasinensins A and D along with oxidation products in phosphate buffer at pH 6.8 at room temperature. The results strongly suggested that theasinensins in black tea were produced by oxidation-reduction dismutation of dehydrotheasinensin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.025

文献信息

• Efficient Synthesis of Theaflavin 3-Gallate by a Tyrosinase-Catalyzed Reaction with (−)-Epicatechin and (−)-Epigallocatechin Gallate in a 1-Octanol/Buffer Biphasic System
  作者：Asako Narai-Kanayama、Yoshinori Uekusa、Fumiyuki Kiuchi、Tsutomu Nakayama

  DOI：10.1021/acs.jafc.8b05971

  日期：2018.12.26

  tyrosinase-catalyzed synthetic reaction with (−)-epicatechin and (−)-epigallocatechin gallate. When the enzymatic reaction proceeded in a buffer solution, oxidized (−)-epigallocatechin gallate was preferentially used for self-dimerization. However, self-dimerization was suppressed in the octanol phase, allowing oxidized (−)-epigallocatechin gallate to participate in coupling with (−)-epicatechin quinone, leading

  茶黄素是红茶中的橙红色色素，由于其促进健康的作用而引起了人们的关注。然而，他们的合成制备方法，其中邻苯二酚型儿茶素的酶促氧化，随后由苯醌诱导的选择性结合的邻苯二酚和邻苯三酚型儿茶素的氧化二聚化，仅提供了低产率。在本研究中，我们发现1-辛醇/缓冲液双相系统在酪氨酸酶催化的（-）-表儿茶素和（-）-表没食子儿茶素没食子酸酯的合成反应中提高了茶黄素3-没食子酸酯的收率。当酶反应在缓冲溶液中进行时，氧化的（-）-表没食子儿茶素没食子酸酯优先用于自二聚。但是，在辛醇相中自二聚被抑制，使氧化的（-）-表没食子儿茶素没食子酸酯参与与（-）-表儿茶素醌的偶合，导致茶黄素3-没食子酸酯的有效生产。此外，茶黄素3-没食子酸酯在辛醇相中的优先定位阻止了（-）-表儿茶素-醌诱导的降解。
• Oxidative coupling of the pyrogallol B-ring with a galloyl group during enzymatic oxidation of epigallocatechin 3-O-gallate
  作者：Yan Li、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.phytochem.2007.01.005

  日期：2007.4

  In order to clarify the mechanism for formation of catechin oligomers during the fermentation stage of black tea manufacture, epigallocatechin-3-O-gallate, the most abundant tea flavanol in fresh tea leaves, was enzymatically oxidized and the resulting unstable quinone metabolites were converted to phenazine derivatives by treatment with o-phenylenediamine. In addition to formation of monomeric and dimeric derivatives, four trimeric derivatives were isolated whose structures were determined by application of spectroscopic methods. The derivatives differed from each other in the location of the phenazine moieties and in the atropisomerism of the biphenyl bond. The results suggested that oxidative coupling of the galloyl group with the B-ring proceeds by a quinone dimerization mechanism similar to that for production of theasinensins. (C) 2007 Elsevier Ltd. All rights reserved.
• Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation–reduction dismutation of dehydrotheasinensin A
  作者：Takashi Tanaka、Sayaka Watarumi、Yosuke Matsuo、Midori Kamei、Isao Kouno

  DOI：10.1016/j.tet.2003.08.025

  日期：2003.9

  Theasinensins A and D are B,B'-linked dimers of (-)-epigallocatechin 3-O-gallate connected through R and S biphenyl bonds, respectively, and are major constituents of black tea. Enzymatic oxidation of epigallocatechin 3-O-gallate produced dehydrotheasinensin A, and the structure was shown to be equivalent to an o-quinone of theasinensin A. When the aqueous solution of dehydrotheasinensin A was heated, theasinensin D was produced along with galloyl oolongtheanin. On the other hand, dehydrotheasinensin A was converted to theasinensins A and D along with oxidation products in phosphate buffer at pH 6.8 at room temperature. The results strongly suggested that theasinensins in black tea were produced by oxidation-reduction dismutation of dehydrotheasinensin. (C) 2003 Elsevier Ltd. All rights reserved.