neotheaflavin 3-gallate

• 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: neotheaflavin 3-gallate
• 英文别名: LDN-0098009；[(2R,3R)-5,7-dihydroxy-2-[3,4,6-trihydroxy-5-oxo-1-[(2R,3S)-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-trihydroxybenzoate
• 化学式: C₃₆H₂₈O₁₆
• 分子量: 716.609
• InChiKey: KMJPKUVSXFVQGZ-AGTQRKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  52
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  284
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  表儿茶素 、 neotheaflavin 3-gallate 在 双氧水 、 horseradish peroxidase 作用下， 以 水 、 丙酮 为溶剂， 以35 mg的产率得到theadibenzotropolone C
  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
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 、 儿茶提取物 在 herseradish peroxidase 双氧水 作用下， 以 丙酮 为溶剂， 反应 0.75h， 生成 neotheaflavin 3-gallate
  参考文献：
  名称：

  Benzotropolone derivatives and modulation of inflammatory response

  摘要：

  本发明提供了一种由通式表示的新型苯并三酮衍生物： 包括新茶黄素B和EGCGCa。本发明的苯并三酮衍生物是有效的抗氧化剂和抗炎药物。本发明还提供了一种高产率合成苯并三酮化合物的新方法，以及使用含有苯并三酮的化合物治疗炎症症状的方法。

  公开号：

  US20050049284A1

文献信息

• Benzotropolone derivatives and modulation of inflammatory response
  申请人：Ho Chi-Tang

  公开号：US20050049284A1

  公开（公告）日：2005-03-03

  The present invention provides novel benzotropolone derivatives represented by the general formula: including neotheaflavate B and EGCGCa. The benzotropolone derivatives of the present invention are effective antioxidant and anti-inflammatory agents. The present invention also provides novel method of synthesizing benzotropolone compounds in high yields and method of treating inflammatory conditions using benzotropolone containing compounds.

  本发明提供了一种由通式表示的新型苯并三酮衍生物： 包括新茶黄素B和EGCGCa。本发明的苯并三酮衍生物是有效的抗氧化剂和抗炎药物。本发明还提供了一种高产率合成苯并三酮化合物的新方法，以及使用含有苯并三酮的化合物治疗炎症症状的方法。
• 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.
• 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.
• α-Glucosidase Inhibitory Profile of Catechins and Theaflavins
  作者：Toshiro Matsui、Takashi Tanaka、Satomi Tamura、Asami Toshima、Kei Tamaya、Yuji Miyata、Kazunari Tanaka、Kiyoshi Matsumoto

  DOI：10.1021/jf0627672

  日期：2007.1.1

  To clarify the postprandial glucose suppression effect of flavonoids, the inhibitory effects of catechins and theaflavins against alpha-glucosidase (AGH) were examined in this study. It was initially demonstrated that theaflavins and catechins preferentially inhibited maltase rather than sucrase in an immobilized AGH inhibitory assay system. For the maltase inhibitory effects of theaflavins, the effects were observed in descending order of potency of theaflavin (TF)-3-O-gallate (Gal) > TF-3,3'-di-O-Gal > TF-3'-O-Gal > TF. This suggests that the AGH inhibition induced by theaflavins is closely associated with the presence of a free hydroxyl group at the 3'-position of TF as well as the esterification of TF with a mono-Gal group. In addition, the R-configuration at the 3'-position of TF-3-O-Gal showed a higher inhibitory activity than the S-configuration. As a result of a single oral administration of maltose (2 g/kg) in rats, a significant reduction in blood glucose level was observed at a dose of 10 mg/kg of TF-3-O-Gal, demonstrating for the first time that TF-3-O-Gal can suppress glucose production from maltose through inhibition of AGH in the gut.