theasinensin A | 89064-31-3

• 物质功能分类: 天然产物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: theasinensin A
• 英文别名: [(2R,3R)-2-[2-[6-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-2,3,4-trihydroxyphenyl]-3,4,5-trihydroxyphenyl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 89064-31-3
• 化学式: C₄₄H₃₄O₂₂
• 分子量: 914.741
• InChiKey: YUULFXAQUWEYNP-GXAWFILRSA-N

物化性质

• 沸点：
  1340.0±65.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  66
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  395
• 氢给体数：
  16
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  theasinensin A 在 单宁酶 作用下， 以 水 为溶剂， 反应 1.0h， 以12 mg的产率得到没食子酸
  参考文献：
  名称：

  Nonaka, Gen-Ichiro; Kawahara, Osamu; Nishioka, Itsuo, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 11, p. 3906 - 3914

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-表没食子儿茶素没食子酸酯 在 Japanese pear fruit homogenate 作用下， 以 水 为溶剂， 反应 2.25h， 生成 theasinensin A
  参考文献：
  名称：

  Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation–reduction dismutation of dehydrotheasinensin A

  摘要：

  Theasinensins A and D are B,B'-linked dimers of (-)-epigallocatechin 3-O-gallate connected through R and S biphenyl bonds, respectively, and are major constituents of black tea. Enzymatic oxidation of epigallocatechin 3-O-gallate produced dehydrotheasinensin A, and the structure was shown to be equivalent to an o-quinone of theasinensin A. When the aqueous solution of dehydrotheasinensin A was heated, theasinensin D was produced along with galloyl oolongtheanin. On the other hand, dehydrotheasinensin A was converted to theasinensins A and D along with oxidation products in phosphate buffer at pH 6.8 at room temperature. The results strongly suggested that theasinensins in black tea were produced by oxidation-reduction dismutation of dehydrotheasinensin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.08.025

文献信息

• Structures of two new oxidation products of green tea polyphenols generated by model tea fermentation
  作者：Takashi Tanaka、Chie Mine、Isao Kouno

  DOI：10.1016/s0040-4020(02)01061-x

  日期：2002.10

  To clarify the oxidation mechanism of green tea catechins during tea fermentation, pure catechins were oxidized with a catechin-free homogenate of tea leaf. Oxidation of a mixture of (−)-epicatechin and (−)-epigallocatechin yielded a new metabolite, named dehydrotheaflavin, produced by the oxidation of a benzotropolone moiety of the black tea pigment theaflavin. Similar oxidation of a mixture of (−)-epicatechin

  为了阐明绿茶儿茶素在茶发酵过程中的氧化机理，纯净的儿茶素被无叶茶素的匀浆茶叶氧化。（-）-表儿茶素和（-）-表没食子儿茶素混合物的氧化产生了一种新的代谢产物，称为脱氢茶黄素，它是由红茶色素茶黄素的苯并二氢马酚酮部分氧化而成的。（-）-表儿茶素和（-）-表没食子儿素3- O-没食子酸酯的混合物的类似氧化产生了新的（-）-表没食子儿茶素3- O-没食子酸酯的二聚体，其是通过两个邻苯三酚环的氧化和环加成产生的。 。通过分光光度法确定结构，并提出了形成产物的氧化机理。
• Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid
  作者：Takuya Shii、Makoto Miyamoto、Yosuke Matsuo、Takashi Tanaka、Isao Kouno

  DOI：10.1248/cpb.59.1183

  日期：——

  Chromatographic separation of black tea polyphenols is too difficult to supply sufficient quantities of pure compounds for biological experiments. Thus, facile methods to prepare black tea constituents were desired. Treatment of epigallocatechin gallate with copper(II) chloride efficiently afforded an unstable quinone dimer, dehydrotheasinensin A, and subsequent treatment with ascorbic acid stereoselectively

  红茶多酚的色谱分离太困难了，无法为生物学实验提供足够量的纯化合物。因此，需要用于制备红茶成分的简便方法。用氯化铜（II）处理表没食子儿茶素没食子酸酯有效地得到了不稳定的醌二聚体，脱氢鞘氨醇苷A，随后用抗坏血酸立体选择性地产生了鞘氨醇苷A。后者是具有R-联苯键的二聚体，后者是一种主要的多酚。红茶。该方法比酶制剂更简单，更有效。
• 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。
• NOVEL EPIGALLOCATECHIN GALLATE TRIMER AND ALPHA-GLUCOSIDASE INHIBITOR CONTAINING EPIGALLOCATECHIN GALLATE POLYMER
  申请人：Fukui Yuko

  公开号：US20110172300A1

  公开（公告）日：2011-07-14

  The present invention provides an α-glucosidase inhibitor containing a novel epigallocatechin gallate trimer and an epigallocatechin gallate polymer. Decomposition of starch derived from a meal and sugar derived from a polysaccharide can be suppressed by α-glucosidase inhibitory action, thus suppressing absorption. A food and drink excellent in α-glucosidase inhibitory action for suppressing sugar absorption and further for preventing diabetes for a long time can be provided by adding the α-glucosidase inhibitor to a food and drink.

  本发明提供了一种含有新型表没食子酸儿茶素三聚体和表没食子酸儿茶素聚合物的α-葡萄糖苷酶抑制剂。通过α-葡萄糖苷酶抑制作用，可以抑制来源于餐食的淀粉和多糖分解产生的糖的吸收，从而达到抑制吸收的目的。将α-葡萄糖苷酶抑制剂添加到食品和饮料中，可以提供具有优异α-葡萄糖苷酶抑制作用的食品和饮料，进而长期预防糖尿病的发生。
• Theasinensin A, a Tea Polyphenol Formed from (-)-Epigallocatechin Gallate, Suppresses Antibiotic Resistance of Methicillin-Resistant<i>Staphylococcus aureus</i>
  作者：Hatano, Tsutomu、Kusuda, Miwako、Hori, Mami、Shiota, Sumiko、Tsuchiya, Tomofusa、Yoshida, Takashi

  DOI：10.1055/s-2003-45142

  日期：2003.11

  When (-)-epigallocatechin gallate (EGCG), the main constituent of tea polyphenols, was kept in a neutral buffer, it decomposed rapidly to give theasinensin A as the major product. Theasinensin A suppressed the oxacillin resistance of methicillin-resistant Staphylococcus aureus (MRSA). In the presence of theasinensin A (3.5 × 10 - 5 M), the minimum inhibitory concentrations (MICs) of oxacillin decreased from 256 or 64 μg/mL to 4 μg/mL for the MRSA strains used. The presence of this compound (3.5 × 10 - 5 M) also decreased the MIC of other β-lactam (penicillin G, from 32 μg/mL to 0.125 - 0.5 μg/mL; ampicillin, from 16 - 32 μg/mL to 0.5 - 1 μg/mL) and aminoglycoside (streptomycin, from 4 - 16 μg/mL to 0.125 - 4 μg/mL) antibiotics for the MRSA strains.

  茶多酚的主要成分(-)-表没食子儿茶素没食子酸酯（EGCG）在中性缓冲液中迅速分解，生成的主要产物是茶黄素 A。Theasinensin A 可抑制耐甲氧西林金黄色葡萄球菌（MRSA）对奥沙西林的耐药性。在 Theasinensin A（3.5 × 10 - 5 M）的存在下，对于所用的 MRSA 菌株，奥沙西林的最小抑菌浓度（MICs）从 256 或 64 μg/mL 降至 4 μg/mL 。该化合物（3.5 × 10 - 5 M）的存在还降低了其他 δ-内酰胺类药物（青霉素 G，从 32 δ¼g/mL 降至 0.125 - 0.5 μg/mL；氨苄西林从 16 - 32 μg/mL降至 0.5 - 1 μg/mL）和氨基糖苷类（链霉素从 4 - 16 μg/mL降至 0.125 - 4 μg/mL）抗生素对 MRSA 菌株的 MIC。