gallocatechin-(4α->8)-catechin

• 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: 3-O-galloylprocyanidin B-3；procyanidin B3 3-O-gallate；procyanidin B3-3-O-gallate；[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• 化学式: C₃₇H₃₀O₁₆
• 分子量: 730.636
• InChiKey: BXWABJPTCUDBMM-UDGCLMCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  288
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  gallocatechin-(4α->8)-catechin 在 单宁酶 作用下， 以 水 为溶剂， 反应 6.0h， 以20 mg的产率得到没食子酸
  参考文献：
  名称：

  7-O-Galloyl-(+)-catechin and 3-O-galloylprocyanidin B-3 from Sanguisorba officinalis

  摘要：

  DOI：

  10.1016/0031-9422(83)80168-x
• 作为产物：
  描述：

  [4,8’]-2,3-trans-3.4-trans:2’,3’-trans-octabenzyloxy-(+)-catechin-3-(tribenzyloxy)gall 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 以78%的产率得到gallocatechin-(4α->8)-catechin
  参考文献：
  名称：

  Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor

  摘要：

  A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3" position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3"-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3"-di-O-gallate), the 3,3"-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase a with IC50 value of 0.26 muM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.048

文献信息

• Stereoselective synthesis of procyanidin B3-3-O-gallate and 3,3″-di-O-gallate, and their abilities as antioxidant and DNA polymerase inhibitor
  作者：Akiko Saito、Mana Emoto、Akira Tanaka、Yuki Doi、Kazuaki Shoji、Yoshiyuki Mizushina、Hiroshi Ikawa、Hiromi Yoshida、Nobuyasu Matsuura、Noriyuki Nakajima

  DOI：10.1016/j.tet.2004.10.048

  日期：2004.12

  A simple method for the synthesis of procyanidin B3 substituted with a galloyl group at the 3 and 3" position is described. Condensation of a benzylated catechin-3-O-gallate electrophile with a nucleophile, catechin and catechin-3-O-gallate, proceeded smoothly and stereoselectively to afford the corresponding dimer gallates, procyanidin B3-3-O-gallate and procyanidin B3-3,3"-di-O-gallate, in good yields. Further, their antioxidant activities on UV-induced lipid peroxide formation, DPPH radical scavenging activity and inhibitory activity of DNA polymerase were also investigated. Among three procyanidin B3 congeners (procyanidin B3, 3-O-gallate and 3,3"-di-O-gallate), the 3,3"-di-O-gallate derivative showed the strongest antioxidant and radical scavenging activity. Interestingly, the 3-O-gallate derivative was the strongest inhibitor of mammalian DNA polymerase a with IC50 value of 0.26 muM, although it showed the weakest antioxidant and radical scavenging activity. It became apparent that the presence of a galloyl group at the C-3 position in the proanthocyanidin oligomer was very important for biological activity, however, the antioxidant activity of these compounds was not parallel to the DNA polymerase inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.
• Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities
  作者：Manato Suda、Miyuki Katoh、Kazuya Toda、Kiriko Matsumoto、Koichiro Kawaguchi、Sei-ichi Kawahara、Yasunao Hattori、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.bmcl.2013.06.061

  日期：2013.9

  Synthesis of procyanidin B2 and B3 gallate derivatives, 3-O-gallate, 3 ''-O-gallate, and 3,3 ''-di-O-gallate, were synthesized using equimolar condensation mediated by Yb(OTf)(3). Synthesized compounds showed significant antitumor effects against human prostate PC-3 cell lines. Their activities were weaker than well-known EGCG and prodelphinidin B3. (C) 2013 Elsevier Ltd. All rights reserved.
• 7-O-Galloyl-(+)-catechin and 3-O-galloylprocyanidin B-3 from Sanguisorba officinalis
  作者：Takashi Tanaka、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(83)80168-x

  日期：1983.1