(-)-epicatechin benzylthioether | 213007-61-5

• 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: (-)-epicatechin benzylthioether
• 英文别名: epicatechin 4-benzyl thioether；epicatechin 4-benzylthioether；epicatechin benzylthioether；4-benzylthioepicatechin；benzylthioepicatechin；epicatechin-benzylthio ether；(2R,3S)-4-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 213007-61-5
• 化学式: C₂₂H₂₀O₆S
• 分子量: 412.463
• InChiKey: YYEFTOIQHQHUQZ-UGGDCYSXSA-N

物化性质

• 沸点：
  707.7±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-epicatechin benzylthioether 生成 马萘雌酮
  参考文献：
  名称：

  HUANG, QING;ZHANG, BEN;ZHANG, HONG-YAN;LI, CHAO-SHENG;LU, LIN;NONAKA, GEN+, XUASYUEH SYUEHBAO, 48,(1990) N, S. 825-829

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol 、 苄硫醇 生成 (-)-epicatechin benzylthioether
  参考文献：
  名称：

  HUANG, QING;ZHANG, BEN;ZHANG, HONG-YAN;LI, CHAO-SHENG;LU, LIN;NONAKA, GEN+, XUASYUEH SYUEHBAO, 48,(1990) N, S. 825-829

  摘要：

  DOI：

文献信息

• Polyphenolic compounds from Croton lechleri
  作者：Y. Cai、F.J. Evans、M.F. Roberts、J.D. Phillipson、M.H. Zenk、Y.Y. Gleba

  DOI：10.1016/0031-9422(91)85063-6

  日期：1991.1

  The blood-red sap of Croton lechleri was found to contain proanthocyanidins as major constituents which accounted for up to 90% of the dried weight. In addition to (+)-catechin, (−)-epicatechin, (+)-gallocatechin, (−)-epigallocatechin and dimeric procyanidins B-1 and B-4, five novel dimers and trimers were isolated and characterized as catechin-(4α→8)- epigallocatechin, gallocatechin-(4α→8)-epicatechin

  巴豆的血红色汁液被发现含有原花青素作为主要成分，占干重的 90%。除了 (+)-儿茶素、(-)-表儿茶素、(+)-没食子儿茶素、(-)-表没食子儿茶素和二聚体原花青素 B-1 和 B-4 外，还分离了五种新型二聚体和三聚体，并将其表征为儿茶素-( 4α→8)-表没食子儿茶素、没食子儿茶素-(4α→8)-表儿茶素、没食子儿茶素-(4α→6)-表没食子儿茶素、儿茶素-(4α→8)-没食子儿茶素-(4α→8)-没食子儿茶素和没食子儿茶素-(4α→) 8)-没食子儿茶素-(4α→8)-表没食子儿茶素。还获得了更高的低聚物。已开发出一种将化学降解与 1 H NMR 光谱相结合的新程序，用于测定低聚/聚合原花色素的组成和分子大小。树液低聚物的平均聚合度分别为 4,5-6 和 6-7，Mr 高达 2130。各种黄烷的存在清楚地表明了低聚物的异质性。 3-ols 作为扩展和终端单元。在低聚物中观察到异常高含量的没食子儿茶素和表没食子儿茶素。
• Synthesis of dimeric, trimeric, tetrameric pentameric, and higher oligomeric epicatechin-derived procyanidins having 4beta,8-interflavan linkages and their use to inhibit cancer cell growth through cell cycle arrest
  申请人：——

  公开号：US20040116718A1

  公开（公告）日：2004-06-17

  Various processes are disclosed for preparing protected epicatechin oligomers having (4&bgr;,8)-interflavan linkages. In one process, a tetra-O-protected epicatechin monomer or oligomer is coupled with a protected, C-4 activated epicatechin monomer in the presence of an acidic clay such as a mortmorillonite clay. In another process, a 5,7,3′,4′-benzyl protected or a 3-acetyl-, 5,7,3′,4′-benzyl protected epicatechin or catechin monomer or oligomer is reacted with 3-O-acetyl-4-[(2-benzothiazolyl)thio]-5,7,3′,4′-tetra-O-benzylepicatechin in the presence of silver tetrafluoroborate. In another process, two 5,7,3′,4′-benzyl protected epicatechin monomers activated with 2-(benzothiazolyl)thio groups at the C-4 positions are cross-coupled in the presence of silver tetrofluoroborate. A process is also disclosed for reacting an unprotected epicatechin or catechin monomer with 4-(benzylthio) epicatechin or catechin. The use of naturally-derived and synthetically-prepared procyanidin (4&bgr;,8) 4 -pentamers to treat cancer is also disclosed.

  揭示了多种制备具有（4'，8）-交互缬氨酸连接的受保护表儿茶素寡聚物的过程。在一种过程中，通过在存在酸性粘土（如蒙脱石粘土）的情况下，将四重受保护的表儿茶素单体或寡聚体与受保护的C-4活化的表儿茶素单体偶联。在另一种过程中，通过在存在四氟硼酸银的情况下，将5,7,3′,4′-苄基保护或3-乙酰基-，5,7,3′,4′-苄基保护的表儿茶素或儿茶素单体或寡聚体与3-O-乙酰基-4-[（2-苯并噻唑基）硫]-5,7,3′,4′-四重苄基表儿茶素反应。在另一种过程中，两个在C-4位置激活了2-（苯并噻唑基）硫基团的5,7,3′,4′-苄基保护表儿茶素单体交叉偶联，在四氟硼酸银的存在下。还揭示了一种过程，用于将未受保护的表儿茶素或儿茶素单体与4-（苄硫基）表儿茶素或儿茶素反应。还揭示了使用天然衍生和合成制备的（4'，8）4-五聚体前花青素来治疗癌症。
• Polyphenols from peanut skins and their free radical-scavenging effects
  作者：Hongxiang Lou、Huiqing Yuan、Bin Ma、Dongmei Ren、Mei Ji、Syuichi Oka

  DOI：10.1016/j.phytochem.2004.06.026

  日期：2004.8

  catalyzed degradation, their structures were determined to be epicatechin-(2beta-->O -->7, 4beta -->6)-[epicatechin-(4beta-->8)]-catechin (1), epicatechin-(2beta-->O -->7, 4beta-->8) epicatechin-(4beta-->8)-catechin-(4alpha-->8)-epicatechin (2), and procyanidins B2 (3), B3 (4) and B4 (5). The absolute configuration of the new compounds was determined from their circular dichroism curves and the (1)H NMR spectra

  花生皮水溶性部分的分离导致了五种原花色素的分离。基于光谱研究和部分酸催化降解，它们的结构被确定为表儿茶素-(2beta-->O -->7, 4beta -->6)-[epicatechin-(4beta-->8)]-catechin (1), 表儿茶素-(2beta-->O -->7, 4beta-->8) 表儿茶素-(4beta-->8)-儿茶素-(4alpha-->8)-表儿茶素 (2), 和原花青素B2 (3)、B3 (4) 和 B4 (5)。新化合物的绝对构型是由它们的圆二色性曲线和 (1) H NMR 光谱确定的，在手性二铑配合物（四氢二铑）存在下通过硫解降解 1 和 2 形成的 flavan-3-ols (R)-(三氟甲基)苯乙酸酯)。
• Anticancer activities of proanthocyanidins from the plant Urceola huaitingii and their synergistic effects in combination with chemotherapeutics
  作者：Ru-Jian Yu、Hai-Bin Liu、Yang Yu、Lu Liang、Rui Xu、Chun Liang、Jin-Shan Tang、Xin-Sheng Yao

  DOI：10.1016/j.fitote.2016.05.015

  日期：2016.7

  Determination of the absolute configuration of proanthocyanidins were discussed, which suggested that positive Δε values at 245nm can be applied to determine the absolute configuration of them. In addition, anticancer activities of proanthocyanidins (1-9) and their synergistic anticancer effects in combination with chemotherapeutics were evaluated. The results showed that some proanthocyanidins, especially

  对怀氏灰熊草茎的植物化学研究导致分离出九种原花色素（1-9），其中包括一种新化合物（9）。通过UV，（HR）ESI-MS，1D-，2D-NMR和CD光谱结合化学衍生化确定其化学结构。讨论了原花色素的绝对构型的确定，这表明在245nm处的正Δε值可用于确定它们的绝对构型。此外，还评估了原花青素（1-9）的抗癌活性及其协同化学疗法的协同抗癌作用。结果表明，一些原花青素，特别是具有两个双黄酮间键的化合物7，
• Biotransformation of procyanidins by a purified fungal dioxygenase: Identification and characterization of the products using mass spectrometry
  作者：Krishnankutty Roopesh、Sylvain Guyot、Abdulhameed Sabu、M. Haridas、Perraud Gaime Isabelle、Sevastianos Roussos、Christopher Augur

  DOI：10.1016/j.procbio.2010.02.019

  日期：2010.6

  Procyanidins commonly known as condensed tannins are a type of polyphenol with wide abundance naturally. They are commonly known as potent anti-oxidants with powerful free radical scavenging activity as well as anti-tumor-promoting activity. Little is known about the enzymatic mechanisms/pathways involved in the microbial biotransformation of these polyphenolic molecules. The extracellular enzyme, dioxygenase produced by Aspergillus fumigatus was used as in vitro tools to study the degradation pathway of a model procyanidin dimer, namely procyanidin B2. The enzyme was purified to homogeneity by a two step process of anion-exchange chromatography coupled with FPLC followed by gel-filtration chromatography coupled with HPLC and the molecular mass estimated. In addition, the different biotransformed products resulted from the dioxygenase action on P82 were purified using Reversed-Phase-High Performance Liquid Chromatography prior to their identification and characterization by structural elucidation using Electrospray Ionization-Mass Spectrometry. Subsequently, the mechanism of dioxygenase action on procyanidin dimer was defined. (C) 2010 Elsevier Ltd. All rights reserved.