3,4,5-tri-O-caffeoyl-quinic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5-tri-O-caffeoyl-quinic acid
• 英文别名: 3,4,5-tri-O-caffeoylquinic acid；1,3,5-O-tricaffeoylquinic acid；3,4,5-O-tricaffeoylquinic acid；3,4,5-di-O-caffeoylquinic acid；3,4,5-tri-O-caffeylquinic acid；3,4,5-tricaffeoylquinic acid
• 化学式: C₃₄H₃₀O₁₅
• 分子量: 678.603
• InChiKey: OAFXTKGAKYAFSI-UPHZGLEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  257.81
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  咖啡酸 在 吡啶 、 4-二甲氨基吡啶 、 N,N-二甲基甲酰胺 、 lithium bromide 、 lithium hydroxide 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 3,4,5-tri-O-caffeoyl-quinic acid
  参考文献：
  名称：

  METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID

  摘要：

  提供了一种制造3,4,5-三咖啡酰奎尼酸的方法，该方法可以通过简单操作在短时间内利用廉价原材料和中间化合物高效生产3,4,5-三咖啡酰奎尼酸。该发明的制造3,4,5-三咖啡酰奎尼酸的方法包括至少以下步骤：(1)让由化学式(1)表示的化合物或由化学式(2)表示的化合物与由化学式(4)表示的化合物发生反应；(2)去保护步骤(1)中得到的产物，并生产3,4,5-三咖啡酰奎尼酸。

  公开号：

  US20160023986A1

文献信息

• Structure-Activity Relationship of Caffeoylquinic Acids on the Accelerating Activity on ATP Production
  作者：Yusaku Miyamae、Manami Kurisu、Junkyu Han、Hiroko Isoda、Hideyuki Shigemori

  DOI：10.1248/cpb.59.502

  日期：——

  Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1—42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure–activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.

  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。
• 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.
• METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID
  申请人：FUJIFILM CORPORATION

  公开号：US20160023986A1

  公开（公告）日：2016-01-28

  Provided are a method for manufacturing 3,4,5-tricaffeoylquinic acid, which can produce 3,4,5-tricaffeoylquinic acid with high efficiency by a simple operation in a short process using inexpensive raw materials, and intermediate compounds. The method for manufacturing 3,4,5-tricaffeoylquinic acid of the invention includes at least Step (1) of allowing a compound represented by Formula (1) or a compound represented by Formula (2) to react with a compound represented by Formula (4); and Step (2) of deprotecting the product obtained in Step (1), and producing 3,4,5-tricaffeoylquinic acid:

  提供了一种制造3,4,5-三咖啡酰奎尼酸的方法，该方法可以通过简单操作在短时间内利用廉价原材料和中间化合物高效生产3,4,5-三咖啡酰奎尼酸。该发明的制造3,4,5-三咖啡酰奎尼酸的方法包括至少以下步骤：(1)让由化学式(1)表示的化合物或由化学式(2)表示的化合物与由化学式(4)表示的化合物发生反应；(2)去保护步骤(1)中得到的产物，并生产3,4,5-三咖啡酰奎尼酸。