3,5-dicaffeoylquinic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dicaffeoylquinic acid
• 英文别名: isochlorogenic acid A；(3R,5R)-3,5-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
• 化学式: C₂₅H₂₄O₁₂
• 分子量: 516.458
• InChiKey: KRZBCHWVBQOTNZ-ZYCLUUQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  211
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  乙醇 、 3,5-dicaffeoylquinic acid 在 p-toluenesulfonate 作用下， 反应 2.0h， 生成 3,5-ethyl dicaeoylquinic acid
  参考文献：
  名称：

  3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-Leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects

  摘要：

  An aqueous ethanol extract of Artemisia argyi inhibited the aminoacylation activity of LeuRS from Giardia lamblia (GlLeuRS). The bioassay-guided fractionation of the extract led to the isolation of 3,5-dicaffeoylquinic acid (1), with an IC50 of 5.82 mu g/mL. The ester derivatives of 1 were also found to possess strong anti-GlLeuRS effects, with IC50 values of 1.79, 5.51 and 2.56 mu g/mL respectively. Anti-giardial assay showed that the derivatives, especially 3,5-dicaffeoylquinic acid propyl ester (4) (IC50 =4.62 mu g/mL), were effective at killing G. lamblia. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2012.05.016

文献信息

• 3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-Leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects
  作者：Yan-Hong Zhang、Mei-Qin Xue、Yuan-Chao Bai、Hui-Hui Yuan、Hong-Li Zhao、Min-Bo Lan

  DOI：10.1016/j.fitote.2012.05.016

  日期：2012.10

  An aqueous ethanol extract of Artemisia argyi inhibited the aminoacylation activity of LeuRS from Giardia lamblia (GlLeuRS). The bioassay-guided fractionation of the extract led to the isolation of 3,5-dicaffeoylquinic acid (1), with an IC50 of 5.82 mu g/mL. The ester derivatives of 1 were also found to possess strong anti-GlLeuRS effects, with IC50 values of 1.79, 5.51 and 2.56 mu g/mL respectively. Anti-giardial assay showed that the derivatives, especially 3,5-dicaffeoylquinic acid propyl ester (4) (IC50 =4.62 mu g/mL), were effective at killing G. lamblia. (C) 2012 Elsevier B.V. All rights reserved.