theadibenzotropolone A

• 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: theadibenzotropolone A
• 英文别名: [(2R,3R)-5,7-dihydroxy-2-[3,4,6-trihydroxy-5-oxo-1-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-8-yl]-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxy-6-oxo-1-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulene-8-carboxylate
• 化学式: C₅₀H₃₈O₂₁
• 分子量: 974.839
• InChiKey: LEZCABNDEPYEFZ-WCQMIFDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  71
• 可旋转键数：
  6
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  371
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 、 表儿茶素 在 双氧水 、 horseradish peroxidase 作用下， 以 水 、 丙酮 为溶剂， 反应 1.25h， 以120 mg的产率得到茶黄素 3-没食子酸酯
  参考文献：
  名称：

  New dibenzotropolone derivatives characterized from black tea using LC/MS/MS

  摘要：

  Theaflavins and thearubigins are major pigments in black tea, and it is generally accepted that they are produced by oxidation of flavan-3-ols (catechins) during tea fermentation. In the course of studies on the oxidation mechanism of tea polyphenols, especially the formation of thearubigins, a method combining the enzymatic synthesis and LC/ESI-MS/MS analysis was developed to search for new higher molecular weight polymers from black tea. Three new dibenzotropolones, theadibenzotropolone A, B, and C, together with one new tribenzotropolone, theatribenzotropolone A, were formed by the reaction of theaflavins and tea catechins with horseradish peroxidase in the presence of H2O2. The structures of these new benzotropolone derivatives were elucidated on the basis of MS and 2D NMR spectroscopic analyses. The existence of these compounds in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A and B were the first benzotropolone-type trimers of catechins found in the black tea extract. The observation that galloyl ester groups of theaflavins can be oxidized to form di- or tri-benzotropolone skeletons strongly implied that this type of oxidation is an important pathway to extend the molecular size of thearubigins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.027

文献信息

• ANTI-OBESITY AGENT COMPRISING COMPOUND CONTAINING BENZOTROPOLONE RING
  申请人：Fukui Yuko

  公开号：US20120065410A1

  公开（公告）日：2012-03-15

  The object of the present invention is to provide an anti-obesity agent which contains a tea-derived component and which is safe and does not compromise the flavor of foods and beverages. According to the present invention, a safe and palatable anti-obesity agent can be provided by incorporating a benzotropolone ring-containing compound which has tea-derived, high inhibitory activities against lipase and alfa-glucosidase. The anti-obesity agent of the present invention does not compromise the flavor of foods and beverage, has palatability, and can be used in various use applications including foods and beverages intended for health enhancement such as reduction in triglycerides.

  本发明的目的是提供一种抗肥胖剂，其中包含一种来源于茶叶的成分，既安全又不会影响食品和饮料的味道。根据本发明，通过将含苯并环戊酮环的化合物纳入其中，可以提供一种安全而美味的抗肥胖剂，该化合物具有来源于茶叶的高抑制脂肪酶和α-葡萄糖苷酶的活性。本发明的抗肥胖剂不会影响食品和饮料的味道，具有口感，可以用于各种用途，包括旨在提高健康的食品和饮料，如降低三酰甘油。
• Theadibenzotropolone , a new type pigment from enzymatic oxidation of (−)-epicatechin and (−)-epigallocatechin gallate and characterized from black tea using LC/MS/MS
  作者：Shengmin Sang、Shiying Tian、Xiaofeng Meng、Ruth E. Stark、Robert T. Rosen、Chung S. Yang、Chi-Tang Ho

  DOI：10.1016/s0040-4039(02)01707-0

  日期：2002.9

  Theaflavins and thearubigins are major pigments of black tea. In the course of studies on the oxidation mechanism of tea polyphenols, a new type of tea pigment, theadibenzotropolone A, together with theaflavin 3-gallate were formed by the reaction of (-)-epicatechin (EC) and (-)-epigallocatechin gallate (EGCG) with horseradish peroxidase in the presence of H2O2. The structure of theadibenzotropolone A was elucidated on the basis of MS and 2D NMR spectroscopic analyses. The observation that galloyl ester groups of theaflavins can be oxidized to form dibenzotropolone skeletons strongly implied that this type of oxidation as an important pathway to extend the molecular size of thearubigins. The existence of this compound in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A is the first theaflavin type trimer of catechins in black tea. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US8658237B2
  申请人：——

  公开号：US8658237B2

  公开（公告）日：2014-02-25
• US9169231B2
  申请人：——

  公开号：US9169231B2

  公开（公告）日：2015-10-27
• New dibenzotropolone derivatives characterized from black tea using LC/MS/MS
  作者：Shengmin Sang、Shiying Tian、Ruth E Stark、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/j.bmc.2004.03.027

  日期：2004.6

  Theaflavins and thearubigins are major pigments in black tea, and it is generally accepted that they are produced by oxidation of flavan-3-ols (catechins) during tea fermentation. In the course of studies on the oxidation mechanism of tea polyphenols, especially the formation of thearubigins, a method combining the enzymatic synthesis and LC/ESI-MS/MS analysis was developed to search for new higher molecular weight polymers from black tea. Three new dibenzotropolones, theadibenzotropolone A, B, and C, together with one new tribenzotropolone, theatribenzotropolone A, were formed by the reaction of theaflavins and tea catechins with horseradish peroxidase in the presence of H2O2. The structures of these new benzotropolone derivatives were elucidated on the basis of MS and 2D NMR spectroscopic analyses. The existence of these compounds in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A and B were the first benzotropolone-type trimers of catechins found in the black tea extract. The observation that galloyl ester groups of theaflavins can be oxidized to form di- or tri-benzotropolone skeletons strongly implied that this type of oxidation is an important pathway to extend the molecular size of thearubigins. (C) 2004 Elsevier Ltd. All rights reserved.