dehydrotheaninensin A | 625371-09-7

• 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: dehydrotheaninensin A
• 英文别名: dehydrotheasinensin A；[(2R,3R)-2-[(1S,9R)-3-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-5,6,9,13,13-pentahydroxy-10-oxo-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,11-tetraen-12-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 625371-09-7
• 化学式: C₄₄H₃₄O₂₃
• 分子量: 930.74
• InChiKey: KPKMVAXGUFNBJP-NDFXFREXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  67
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  401
• 氢给体数：
  15
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  dehydrotheaninensin A 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Isolation of key intermediates during formation of oolongtheanins

  摘要：

  Oolongtheanin-3'-O-gallate (2b) was obtained by treatment of (-)-EGCg (1d) with CuCl2. This transformation was achieved over three steps, with the isolation of two intermediates; their chemical structures were determined through derivatization reactions, MS, and 1D/2D NMR techniques. One intermediate was identified as dehydrotheasinensin A (3); the other was identified as the novel dimer pro-oolongtheanin-3'-O-gallate (6). Compound 3 was converted to 6 by heating in aprotic solvent, and compound 6 was converted to 2b by addition of water. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.069
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 氧气 、 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 dehydrotheaninensin A
  参考文献：
  名称：

  由表没食子儿茶素没食子酸酯通过氯化铜（II）和抗坏血酸处理来仿制一锅法制备红茶多酚茶碱菌素A。

  摘要：

  红茶多酚的色谱分离太困难了，无法为生物学实验提供足够量的纯化合物。因此，需要用于制备红茶成分的简便方法。用氯化铜（II）处理表没食子儿茶素没食子酸酯有效地得到了不稳定的醌二聚体，脱氢鞘氨醇苷A，随后用抗坏血酸立体选择性地产生了鞘氨醇苷A。后者是具有R-联苯键的二聚体，后者是一种主要的多酚。红茶。该方法比酶制剂更简单，更有效。

  DOI：

  10.1248/cpb.59.1183

文献信息

• Synthesis of oolongtheanins and their inhibitory activity on micellar cholesterol solubility in vitro
  作者：Kazuki Ogawa、Sayumi Hirose、Hitomi Yamamoto、Masaya Shimada、Satoshi Nagaoka、Emiko Yanase

  DOI：10.1016/j.bmcl.2015.01.002

  日期：2015.2

  The synthesis of oolongtheanins (1a-d) was accomplished from EGC and/or EGCg in three steps. Oolongtheanin-3'-O-gallate (1b) showed more potent inhibitory activity on micellar cholesterol solubility than did EGCg. (C) 2015 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.