(2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin

• 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: (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin
• 英文别名: prodelphinidin B₂；prodelphinidin B-2；prodelphinidin B2；Proanthocyandin der.；(2R,3R)-2-(3,4,5-trihydroxyphenyl)-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₃₀H₂₆O₁₄
• 分子量: 610.528
• InChiKey: RTEDIEITOBJPNI-PEXYVCJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  261
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin 在 吡啶 、 4-二甲氨基吡啶 作用下， 以16%的产率得到epigallocatechin-(4β->8)-epigallocatechin peracetate
  参考文献：
  名称：

  Syntheses of prodelphinidin B1, B2, and B4 and their antitumor activities against human PC-3 prostate cancer cell lines

  摘要：

  Total synthesis of prodelphinidin B1, B2, and B4 has been accomplished. The key step is Lewis acid-mediated equimolar condensations between an epigallocatechin and/or a gallocatechin nucleophile and an epigallocatechin and/or a gallocatechin electrophile. The antitumor effects of synthetic prodelphinidin B1-B4 against human PC-3 prostate cancer cell lines have been investigated. These compounds showed significant antitumor effects. Their activity seemed to be little bit stronger than EGCG and prodelphinidin B3, known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.113
• 作为产物：
  描述：

  [4,8’]-2,3-cis-3.4-trans:2’,3’-cis-decabenzyloxy-(-)-epigallocatechin-(-)-epigallocatechin 在 Pd(OH)2/C, 20% 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以31%的产率得到(2R,2''R,3R,3''R,4R)-[4,8]-2,3-cis-3,4-trans-(-)-epigallocatechin-(-)-epigallocatechin
  参考文献：
  名称：

  Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities

  摘要：

  原花青素是由低聚黄烷-3-醇单位组成的，存在于各种食品（如水果、蔬菜和饮料）中，是一种具有很强生物活性的化合物。我们研究了原花青素结构中哪种元素主要负责这种功能。在这项研究中，我们阐明了 4-8 缩合二聚体黄烷-3-醇上部单元对酿酒酵母（S. cerevisiae）和宫颈上皮样癌细胞株 HeLa S3 增殖抑制活性的重要性。(-)-表没食子儿茶素-[4,8]-(-)-表没食子儿茶素-3-O-没食子酸酯，以及(+)-儿茶素-[4,8]-(-)-表没食子儿茶素，并进行了结构-活性关系（SAR）研究。 除了对葡萄孢菌的抗菌活性和对 HeLa S3 细胞的增殖抑制活性外，2,2-二苯基-l-苦基肼自由基清除活性与酚羟基数目的相关性较低。根据我们的 SAR 研究结果，我们得出结论：二聚体上部单元的 B 环羟基对于强有效的活性至关重要。

  DOI：

  10.3390/molecules201018870

文献信息

• Myricatin, a galloyl flavanonol sulfate and prodelphinidin gallates from Myrica rubra
  作者：Gen-Ichiro Nonaka、Makiko Muta、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)80097-7

  日期：1983.1
• Tanaka, Takashi; Takahashi, Ryuji; Kouno, Isao, Journal of the Chemical Society. Perkin transactions I, 1994, # 20, p. 3013 - 3022
  作者：Tanaka, Takashi、Takahashi, Ryuji、Kouno, Isao、Nonaka, Gen-ichiro

  DOI：——

  日期：——
• ANTIVIRAL EPICATECHINS, EPICATECHIN OLIGOMERS, OR THIOLATED EPICATECHINS FROM THEOBROMA CACAO FOR TREATMENT OF GENITAL WARTS
  申请人：PRESTON Daniel

  公开号：US20110218241A1

  公开（公告）日：2011-09-08

  Epicatechins, Epicatechin Oligomers, or Thiolated Epicatechins are applied (A) directly to a genital wart in the form of a cream, ointment, paste or solution, (B) directly to the genital wart wherein such cream, ointment, paste or solution contains as an additional active ingredient a skin permeabilizing agent, (C) following electrosurgical resection or removal of the genital wart in such form of a cream, ointment, paste or solution, (D) following chemical resection or extirpation of the genital wart in such form, (E) following surgical resection or removal of the genital wart in such form, wherein said Epicatechins, Epicatechin Oligomers, or Thiolated Epicatechins both provide antiviral activity against multiple strains of human papilloma virus (HPV) and promote healing following resection polymers contained in a vehicle. Disclosed are the compositions, therapeutical kits containing such composition, methods of treatment using such composition, and methods of enhancing the stability of such composition.
• EPICATECHIN COMPOSITIONS AND METHODS
  申请人：PRESTON Daniel

  公开号：US20110280933A1

  公开（公告）日：2011-11-17

  Provided herein are methods and compositions for treating a subject who has pulmonary damage or an injury caused by or who is at risk for an injury caused by an anti-vesicant agent. The compositions comprise cacao extracts that include a mixture of epicatechin and one or more epicatechin oligomers and a pharmaceutically acceptable carrier. Also provided are methods for fermenting cacao to enhance epicatechin and antioxidant content.
• Structure–Activity Relationship of Oligomeric Flavan-3-ols: Importance of the Upper-Unit B-ring Hydroxyl Groups in the Dimeric Structure for Strong Activities
  作者：Yoshitomo Hamada、Syota Takano、Yoshihiro Ayano、Masahiro Tokunaga、Takahiro Koashi、Syuhei Okamoto、Syoma Doi、Masahiko Ishida、Takashi Kawasaki、Masahiro Hamada、Noriyuki Nakajima、Akiko Saito

  DOI：10.3390/molecules201018870

  日期：——

  Proanthocyanidins, which are composed of oligomeric flavan-3-ol units, are contained in various foodstuffs (e.g., fruits, vegetables, and drinks) and are strongly biologically active compounds. We investigated which element of the proanthocyanidin structure is primarily responsible for this functionality. In this study, we elucidate the importance of the upper-unit of 4–8 condensed dimeric flavan-3-ols for antimicrobial activity against Saccharomyces cerevisiae (S. cerevisiae) and cervical epithelioid carcinoma cell line HeLa S3 proliferation inhibitory activity. To clarify the important constituent unit of proanthocyanidin, we synthesized four dimeric compounds, (−)-epigallocatechin-[4,8]-(+)-catechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin, (−)-epigallocatechin-[4,8]-(−)-epigallocatechin-3-O-gallate, and (+)-catechin-[4,8]-(−)-epigallocatechin and performed structure–activity relationship (SAR) studies. In addition to antimicrobial activity against S. cerevisiae and proliferation inhibitory activity on HeLa S3 cells, the correlation of 2,2-diphenyl-l-picrylhydrazyl radical scavenging activity with the number of phenolic hydroxyl groups was low. On the basis of the results of our SAR studies, we concluded that B-ring hydroxyl groups of the upper-unit of the dimer are crucially important for strong and effective activity.

  原花青素是由低聚黄烷-3-醇单位组成的，存在于各种食品（如水果、蔬菜和饮料）中，是一种具有很强生物活性的化合物。我们研究了原花青素结构中哪种元素主要负责这种功能。在这项研究中，我们阐明了 4-8 缩合二聚体黄烷-3-醇上部单元对酿酒酵母（S. cerevisiae）和宫颈上皮样癌细胞株 HeLa S3 增殖抑制活性的重要性。(-)-表没食子儿茶素-[4,8]-(-)-表没食子儿茶素-3-O-没食子酸酯，以及(+)-儿茶素-[4,8]-(-)-表没食子儿茶素，并进行了结构-活性关系（SAR）研究。 除了对葡萄孢菌的抗菌活性和对 HeLa S3 细胞的增殖抑制活性外，2,2-二苯基-l-苦基肼自由基清除活性与酚羟基数目的相关性较低。根据我们的 SAR 研究结果，我们得出结论：二聚体上部单元的 B 环羟基对于强有效的活性至关重要。