1,4,5-O-tricaffeoylquinic acid | 1073897-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4,5-O-tricaffeoylquinic acid
• 英文别名: 1,4,5-tri-O-caffeoylquinic acid；1,4,5-tri-CQA；(1R,3R,4S,5R)-1,3,4-tris[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-5-hydroxycyclohexane-1-carboxylic acid
• CAS: 1073897-83-2
• 化学式: C₃₄H₃₀O₁₅
• 分子量: 678.603
• InChiKey: ZDYRXGIWSQSHSO-YNCKJNTPSA-N

物化性质

• 沸点：
  947.3±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  258
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  咖啡酸 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 水 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 288.0h， 生成 1,4,5-O-tricaffeoylquinic acid
  参考文献：
  名称：

  Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production

  摘要：

  咖啡酰奎宁酸（CQA）是一种酚丙烷类化合物，具有多种生物活性，如抗氧化、抗菌、抗癌、抗组胺和其他生物效应。我们之前报道过，3,5-二-O-咖啡酰奎宁酸抑制了淀粉样蛋白β1—42引起的人类神经母细胞瘤SH-SY5Y细胞的细胞毒性，并提高了糖酵解酶的mRNA表达水平和细胞内ATP水平。为了研究结构—活性关系对ATP生产加速活性的影响，我们合成了1,4,5-三-O-咖啡酰奎宁酸、4,5-二-O-咖啡酰奎宁酸、3,4,5-三-O-咖啡酰奎宁酸及其他衍生物。此外，我们评估了用每种CQA衍生物处理的SH-SY5Y细胞的细胞内ATP水平。结果显示，3,4,5-三-O-咖啡酰奎宁酸在测试化合物中对于ATP生产的加速活性最高。研究表明，结合在奎宁酸上的咖啡酰基团对活性至关重要，结合到奎宁酸上的咖啡酰基团越多，ATP生产的加速活性就越高。

  DOI：

  10.1248/cpb.59.502

文献信息

• Characterization and Quantification of Hydroxycinnamate Derivatives in Stevia rebaudiana Leaves by LC-MS^<i>n</i>
  作者：Hande Karaköse、Rakesh Jaiswal、Nikolai Kuhnert

  DOI：10.1021/jf202185m

  日期：2011.9.28

  Stevia rebaudiana leaves are used as a zero-calorie natural sweetener in a variety of food products in Asian countries, especially in Japan. In this study, the hydroxycinnamate derivatives of S. rebaudiana have been investigated qualitatively and quantitatively by LC-MSn. Twenty-four hydroxycinnainic acid derivatives of quinic and shikimic acid were detected, and 19 of them were successfully characterized to regioisomeric levels; 23 are reported for the first time from this source. These comprise three monocaffeoylquinic acids (M-r 354), seven dicaffeoylquinic acids (M-r 516), one p-coumaroylquinic acid (M-r 338), one feruloylquinic acid (M-r 368), two caffeoyl-feruloylquinic acids (M-r 530), three caffeoylshildmic acids (M-r 336), and two tricaffeoylquinic acids (M-r 678). Cis isomers of di- and tricaffeoylquinic acids were observed as well. Three tricaffeoylquinic acids identified in stevia leaves are reported for the first time in nature. These phenolic compounds identified in stevia might affect the organoleptic properties and add additional beneficial health effects to stevia-based products.