gambiriin D | 1578134-37-8

• 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: gambiriin D
• 英文别名: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 1578134-37-8
• 化学式: C₃₀H₂₆O₁₂
• 分子量: 578.529
• InChiKey: SSIKVVLSHPFYLB-KBJUPQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  42
• 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：
  221
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  儿茶提取物 以 水 为溶剂， 反应 3.0h， 以4.3 mg的产率得到gambiriin D
  参考文献：
  名称：

  Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin

  摘要：

  Thermal transformation of the (+)-catechin (1) with heating processing afforded a new oxidation product, gambiriin D (2), along with catechin [6'-8]-catechin (3), and (+)-epicatechin (4). The structure of a new catechin dimer with C-C linkage was determined on the basis of spectroscopic data interpretation. The catechin dimers 2 and 3 exhibited significantly improved inhibitory activities against alpha-glucosidase, with IC50 values of 0.16 +/- 0.2 and 0.14 +/- 0.2 mu M, respectively, when compared to parent (+)-catechin. Kinetic analysis showed that the two effective compounds 2 and 3 have noncompetitive modes of action. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.01.027

文献信息

• Potential α-glucosidase inhibitors from thermal transformation of (+)-catechin
  作者：Taewan Kim、Hyo Jin Choi、Sung-Hwan Eom、Jaemin Lee、Tae Hoon Kim

  DOI：10.1016/j.bmcl.2014.01.027

  日期：2014.3

  Thermal transformation of the (+)-catechin (1) with heating processing afforded a new oxidation product, gambiriin D (2), along with catechin [6'-8]-catechin (3), and (+)-epicatechin (4). The structure of a new catechin dimer with C-C linkage was determined on the basis of spectroscopic data interpretation. The catechin dimers 2 and 3 exhibited significantly improved inhibitory activities against alpha-glucosidase, with IC50 values of 0.16 +/- 0.2 and 0.14 +/- 0.2 mu M, respectively, when compared to parent (+)-catechin. Kinetic analysis showed that the two effective compounds 2 and 3 have noncompetitive modes of action. (C) 2014 Published by Elsevier Ltd.