gallocatechin-(4α->8)-catechin | 78392-25-3

• 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: gallocatechin-(4α->8)-catechin
• 英文别名: gallocatechin-(4α-8)-catechin；prodelphinidin B3；(+)-Gallocatechin-(4alpha->8)-(+)-catechin；(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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
• CAS: 78392-25-3
• 化学式: C₃₀H₂₆O₁₃
• 分子量: 594.529
• InChiKey: ZYDDITZPGFXQSD-SMSOEIQDSA-N

物化性质

• 沸点：
  909.0±65.0 °C(Predicted)
• 密度：
  1.761±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  43
• 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：
  241
• 氢给体数：
  11
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  gallocatechin-(4α->8)-catechin 生成 Gallocatechin-(4α->8)-catechin peracetate
  参考文献：
  名称：

  PETEREIT, FRANK;KOLODZIEJ, HERBERT;NAHRSTEDT, ADOLF, PHYTOCHEMISTRY, 30,(1991) N, C. 981-985

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-8-[(2R,3S,4S)-3-hydroxy-5,7-bis(phenylmethoxy)-2-[3,4,5-tris(phenylmethoxy)phenyl]-3,4-dihydro-2H-chromen-4-yl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以96%的产率得到gallocatechin-(4α->8)-catechin
  参考文献：
  名称：

  Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation

  摘要：

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.087

文献信息

• Characterization and trypsin inhibitor activity of proanthocyanidins from Vicia faba
  作者：Johannes P.F.G. Helsper、Johanna M. Hoogendijk、Arend van Norel、Herbert Kolodziej

  DOI：10.1016/0031-9422(91)80011-o

  日期：1993.11

  and B-4, and the prodelphinidins gallocatechin-(4α,8)-catechin, gallocatechin-(4α,8)-epicatechin and gallocatechin-(4α,8)-epigallocatechin have been isolated from the testa of faba beans and characterized by means of spectroscopic methods. Proanthocyanidin samples were compared for their trypsin inhibitory activity. The results suggest that the degree of polymerization, the number of phenolic hydroxyl

  摘要 在一项化学研究中，表儿茶素、表没食子儿茶素、原花青素 B-1、B-3 和 B-4，以及原飞燕草素没食子儿茶素-(4α,8)-儿茶素、没食子儿茶素-(4α,8)-表儿茶素和没食子儿茶素-(4α ,8)-表没食子儿茶素已从蚕豆的种皮中分离出来，并通过光谱方法进行了表征。比较原花青素样品的胰蛋白酶抑制活性。结果表明聚合度、酚羟基数量和组成单元的2,3-立体化学显着影响抑制强度。
• PETEREIT, FRANK;KOLODZIEJ, HERBERT;NAHRSTEDT, ADOLF, PHYTOCHEMISTRY, 30,(1991) N, C. 981-985
  作者：PETEREIT, FRANK、KOLODZIEJ, HERBERT、NAHRSTEDT, ADOLF

  DOI：——

  日期：——
• Syntheses of prodelphinidin B3 and C2, and their antitumor activities through cell cycle arrest and caspase-3 activation
  作者：Wataru Fujii、Kazuya Toda、Koichiro Kawaguchi、Sei-ichi Kawahara、Miyuki Katoh、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tet.2013.02.087

  日期：2013.4

  Total synthesis of prodelphinidin B3 and C2 have been accomplished. The key step is Lewis acid-mediated equimolar condensations between a catechin and/or gallocatechin nucleophile and a gallocatechin electrophile. The antitumor effects of synthetic prodelphidin B3 and C2 against PC-3 prostate cancer cell lines have been investigated. Both compounds showed significant antitumor effects. Their activity was almost the same as that of EGCG, a known antitumor agent. (C) 2013 Elsevier Ltd. All rights reserved.