theaflavate C | 1013313-02-4

• 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: theaflavate C
• 英文别名: [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 1-[(2R,3R)-3-[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-carbonyl]oxy-5,7-dihydroxy-3,4-dihydro-2H-chromen-2-yl]-3,4,6-trihydroxy-5-oxobenzo[7]annulene-8-carboxylate
• CAS: 1013313-02-4
• 化学式: C₆₄H₄₆O₂₈
• 分子量: 1263.05
• InChiKey: SYOQUYKXHCPYEY-BFFJVZHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  92
• 可旋转键数：
  12
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  485
• 氢给体数：
  17
• 氢受体数：
  28

反应信息

• 作为产物：
  描述：

  (-)-表儿茶素没食子酸酯 在 Japanese pear homogenate 作用下， 以 水 为溶剂， 反应 6.0h， 以712 mg的产率得到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：

  Structures of Epicatechin Gallate Trimer and Tetramer Produced by Enzymatic Oxidation

  摘要：

  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。

  DOI：

  10.1248/cpb.55.1768

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。