表茶黄棓灵3-O-没食子酸酯 | 102067-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 表茶黄棓灵3-O-没食子酸酯
• 英文名称: epitheaflagallin 3-O-gallate
• 英文别名: [(2R,3R)-5,7-dihydroxy-2-(2,3,4,6-tetrahydroxy-5-oxobenzo[7]annulen-8-yl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 102067-92-5
• 化学式: C₂₇H₂₀O₁₃
• 分子量: 552.448
• InChiKey: CMGRMMSVGCHWOK-FQRUVTKNSA-N

物化性质

• 沸点：
  1073.4±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  235
• 氢给体数：
  9
• 氢受体数：
  13

制备方法与用途

生物活性方面，Epitheaflagallin 3-O-没食子酸是红茶中的一种次要多酚。这种化合物在体内和体外显示出多种生理功能，包括抗氧化活性、胰脂肪酶抑制作用、山梨糖链球菌糖基转移酶抑制以及对基质金属蛋白酶-1 和-3 的抑制作用，并且还能抑制人牙龈成纤维细胞的合成。

反应信息

• 作为反应物：
  描述：

  表茶黄棓灵3-O-没食子酸酯 在 单宁酶 、 碳酸氢钠 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 0.84h， 生成 purpurogallin carboxylic acid
  参考文献：
  名称：

  Tannins and related compounds. XXXVI. Isolation and structures of theaflagallins, new red pigments from black tea.

  摘要：

  对黑茶多酚的化学分析导致了三种新红色颜料的分离，分别是木韵鞣酸3-O-鞣酸盐（1）、表木韵鞣酸（2）和木韵鞣酸（3），以及已知的茶黄素4-7。茶黄素1-3的结构是基于光谱和化学数据确定的，属于通过没食子酸和所谓的没食子儿茶素的氧化缩合形成的非凡的苯并特罗醇。

  DOI：

  10.1248/cpb.34.61
• 作为产物：
  描述：

  没食子酸 、 (-)-表没食子儿茶素没食子酸酯 在 phosphate-citrate buffer 、 双氧水 、 horseradish peroxidase 作用下， 以 水 、 丙酮 为溶剂， 反应 0.75h， 以300 mg的产率得到表茶黄棓灵3-O-没食子酸酯
  参考文献：
  名称：

  Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

  摘要：

  Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.024

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。
• Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities
  作者：Shengmin Sang、Joshua D Lambert、Shiying Tian、Jungil Hong、Zhe Hou、Jae-He Ryu、Ruth E Stark、Robert T Rosen、Mou-Tuan Huang、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/j.bmc.2003.10.024

  日期：2004.1

  Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. (C) 2003 Elsevier Ltd. All rights reserved.
• Tannins and related compounds. XXXVI. Isolation and structures of theaflagallins, new red pigments from black tea.
  作者：GEN-ICHIRO NONAKA、FUMIO HASHIMOTO、ITSUO NISHIOKA

  DOI：10.1248/cpb.34.61

  日期：——

  A chemical examination of black tea polyphenols had led to the isolation of three new red pigments, spitheaflagallin 3-O-gallate (1), epitheaflagallin (2) and theaflagallin (3), together with the known theaflavins 4-7. The structures of the theaflagallins 1-3 have been determined on the basis of spectroscopic and chemical data as unusual benzotropolones formed by oxidative condensation of gallic acid and so-called gallocatechins.

  对黑茶多酚的化学分析导致了三种新红色颜料的分离，分别是木韵鞣酸3-O-鞣酸盐（1）、表木韵鞣酸（2）和木韵鞣酸（3），以及已知的茶黄素4-7。茶黄素1-3的结构是基于光谱和化学数据确定的，属于通过没食子酸和所谓的没食子儿茶素的氧化缩合形成的非凡的苯并特罗醇。