theacitrin C | 1281964-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: theacitrin C
• 英文别名: theacitrin A 3-O-gallate；[(2R,3R)-2-[8a-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3a,5,7-trihydroxy-3,4,6-trioxo-8bH-cyclopenta[a]inden-1-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 1281964-69-9
• 化学式: C₄₄H₃₂O₂₂
• 分子量: 912.725
• InChiKey: QEYQVVWKYDOOSW-BGKQLBNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  66
• 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：
  385
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  theacitrin C 在 水 、 三氟乙酸 作用下， 反应 1.0h， 以68%的产率得到theacitrinin A
  参考文献：
  名称：

  Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate

  摘要：

  Black tea is rich in polyphenols and has been shown to have various health benefits: however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7-tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.058
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 碳酸氢钠 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 0.25h， 以4.48 mg的产率得到dehydrotheasinensin A
  参考文献：
  名称：

  Reactive oxygen species scavenging activities and inhibition on DNA oxidative damage of dimeric compounds from the oxidation of (−)-epigallocatechin-3-O-gallate

  摘要：

  The dimeric catechins dehydrotheasinensin A (2) and theacitrin C (3) were prepared from the oxidation of (-)-epigallocatechin-3-O-gallate (EGCG, 1), and their antioxidant activity was investigated using a chemiluminescence (CL) method in vitro Both compounds showed significant inhibitory effects on reactive oxygen species (O-2(-), H2O2 and center dot OH) and DNA oxidative damage, with 2 being more potent than 3 and EGCG itself. (C) 2009 Elsevier B V All rights reserved

  DOI：

  10.1016/j.fitote.2009.09.004

文献信息

• Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate
  作者：Yosuke Matsuo、Yan Li、Sayaka Watarumi、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.tet.2011.01.058

  日期：2011.3

  Black tea is rich in polyphenols and has been shown to have various health benefits: however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7-tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates. (C) 2011 Elsevier Ltd. All rights reserved.
• Reactive oxygen species scavenging activities and inhibition on DNA oxidative damage of dimeric compounds from the oxidation of (−)-epigallocatechin-3-O-gallate
  作者：Xiangyang Qi

  DOI：10.1016/j.fitote.2009.09.004

  日期：2010.4

  The dimeric catechins dehydrotheasinensin A (2) and theacitrin C (3) were prepared from the oxidation of (-)-epigallocatechin-3-O-gallate (EGCG, 1), and their antioxidant activity was investigated using a chemiluminescence (CL) method in vitro Both compounds showed significant inhibitory effects on reactive oxygen species (O-2(-), H2O2 and center dot OH) and DNA oxidative damage, with 2 being more potent than 3 and EGCG itself. (C) 2009 Elsevier B V All rights reserved