5H-苯并环庚烯-8-羧酸,1-[(2R,3R)-3,4-二氢-5,7-二羟基-3-[(3,4,5-三羟基苯甲酰)氧代]-2H-1-苯并吡喃-2-基]-3,4,6-三羟基-5-羰基-,(2R,3R)-2-(3,4-二羟基苯基)-3,4-二氢-5,7-二羟基-2H-1-苯并吡喃-3-基酯 | 152542-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5H-苯并环庚烯-8-羧酸,1-[(2R,3R)-3,4-二氢-5,7-二羟基-3-[(3,4,5-三羟基苯甲酰)氧代]-2H-1-苯并吡喃-2-基]-3,4,6-三羟基-5-羰基-,(2R,3R)-2-(3,4-二羟基苯基)-3,4-二氢-5,7-二羟基-2H-1-苯并吡喃-3-基酯
• 英文名称: theaflavate A
• 英文别名: [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,6-trihydroxy-5-oxobenzo[7]annulene-8-carboxylate
• CAS: 152542-70-6
• 化学式: C₄₃H₃₂O₁₉
• 分子量: 852.716
• InChiKey: CTVQUVJPFDHBIP-NBNGAXDASA-N

物化性质

• 沸点：
  1304.1±65.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  331
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  (-)-表儿茶素没食子酸酯 在 herseradish peroxidase 双氧水 作用下， 反应 0.5h， 生成 5H-苯并环庚烯-8-羧酸,1-[(2R,3R)-3,4-二氢-5,7-二羟基-3-[(3,4,5-三羟基苯甲酰)氧代]-2H-1-苯并吡喃-2-基]-3,4,6-三羟基-5-羰基-,(2R,3R)-2-(3,4-二羟基苯基)-3,4-二氢-5,7-二羟基-2H-1-苯并吡喃-3-基酯
  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

• Structures of Epicatechin Gallate Trimer and Tetramer Produced by Enzymatic Oxidation
  作者：Rie Kusano、Takashi Tanaka、Yosuke Matsuo、Isao Kouno

  DOI：10.1248/cpb.55.1768

  日期：——

  During black tea production, catechins and their galloyl esters are enzymatically oxidized to generate a complex mixture of black tea polyphenols. The role of galloyl ester groups in this process has yet to be determined. Enzymatic oxidation of epicatechin 3-O-gallate (1) yielded two new oxidation products, theaflavate C and bistheaflavate A, along with theaflavate A (2), a known dimer of 1 generated by coupling of the B-ring with the galloyl group. Theaflavate C is a trimer of 1 and possesses two benzotropolone moieties generated by the oxidative coupling of the galloyl groups with the catechol B-rings. Bistheaflavate A was found to be a tetramer produced by intermolecular coupling of two benzotropolone moieties of 2. From the structures of the products, it was deduced that oxidative coupling of galloyl groups resulted in extension of the molecular size of the products in catechin oxidation.

  在红茶生产过程中，儿茶素及其五倍子酰酯被酶氧化，生成复杂的红茶多酚混合物。五倍子酰酯基在这一过程中的作用尚未确定。表儿茶素 3-O-没食子酸酯（1）的酶促氧化产生了两种新的氧化产物，即茶黄酸酯 C 和双茶黄酸酯 A，以及茶黄酸酯 A（2），后者是已知的 1 的二聚体，由 B 环与没食子酰基偶联生成。茶黄酸酯 C 是 1 的三聚体，具有两个苯并二氢吡喃酮分子，通过没食子酰基与邻苯二酚 B 环的氧化偶联生成。根据产物的结构推断，儿茶素氧化过程中，五倍子酰基的氧化偶联导致产物的分子尺寸扩大。
• Polymer-Like Polyphenols of Black Tea and Their Lipase and Amylase Inhibitory Activities
  作者：Rie Kusano、Hisashi Andou、Miho Fujieda、Takashi Tanaka、Yosuke Matsuo、Isao Kouno

  DOI：10.1248/cpb.56.266

  日期：——

  Lipase and amylase inhibitory activities of black tea were examined. After solvent partitioning of a black tea extract with the ethyl acetate and n-butanol, the two soluble fractions showed comparable inhibitory activities. Activity in the ethyl acetate fraction was mainly attributable to polyphenols with low-molecular weights, such as theaflavin gallates. On the other hand, the active substance in the n-butanol layer was ascertained to be a polymer-like substance. 1H- and 13C-NMR spectra showed signals arising from the flavan A-ring and galloyl groups, although signals due to flavan B-rings were not detected, suggesting that the polymer-like substances were generated by oxidative condensation of flavan B-rings, a result which was previously deduced from our results of in vitro catechin oxidation experiments. Enzymatic oxidation of epicatechin 3-O-gallate produced a similar polymer-like substance and suggested that condensation between a B-ring and galloyl groups was involved in the polymerization reaction.

  研究了红茶的脂肪酶和淀粉酶抑制活性。红茶提取物经乙酸乙酯和正丁醇溶剂分馏后，两种可溶性馏分显示出相当的抑制活性。乙酸乙酯馏分的活性主要归因于低分子量的茶多酚，如没食子酸茶黄素。另一方面，正丁醇层中的活性物质被确定为聚合物类物质。1H-NMR 和 13C-NMR 光谱显示了由黄烷 A 环和没食子酰基产生的信号，但没有检测到黄烷 B 环产生的信号，这表明聚合物样物质是由黄烷 B 环氧化缩合生成的，这一结果是我们之前根据儿茶素体外氧化实验结果推断出来的。表儿茶素 3-O-没食子酸酯的酶促氧化也产生了类似的聚合物样物质，这表明 B 环和没食子酰基之间的缩合参与了聚合反应。
• 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.
• US8658237B2
  申请人：——

  公开号：US8658237B2

  公开（公告）日：2014-02-25