5-O-(p-coumaroyl)shikimic acid | 196496-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-O-(p-coumaroyl)shikimic acid
• 英文别名: 5-O-p-coumaroyl shikimic acid；p-coumaroyl 5-O-shikimate；(3R,4R,5R)-3,4-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexene-1-carboxylic acid
• CAS: 196496-50-1
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: GVECSFFLZYNEBO-PDXJTRCTSA-N

物化性质

• 沸点：
  611.6±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-香豆酸 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 5-O-(p-coumaroyl)shikimic acid
  参考文献：
  名称：

  Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase

  摘要：

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.

  DOI：

  10.1021/jm9607360

文献信息

• Partial purification and properties of p-hydroxycinnamoyl-CoA: Shikimate-p-hydroxycinnamoyl transferase from higher plants
  作者：Bernhard Ulbrich、Meinhart H. Zenk

  DOI：10.1016/s0031-9422(00)83782-6

  日期：——

  Abstract The partial purification and characterization of p -hydroxycinnamoyl-CoA: shikimate- p -hydroxycinnamoyl transferase (CST) from cell suspension cultures of Cichorium endivia is reported. The enzyme has been purified 126-fold and shows an absolute specificity for p -coumaroyl-CoA and shikimic acid. The product of the enzyme reaction has been identified as 5- O - p -coumaroyl shikimic acid.

  摘要 报道了从菊苣的细胞悬浮培养物中部分纯化和表征对羟基肉桂酰辅酶 A：莽草酸对羟基肉桂酰转移酶 (CST)。该酶已被纯化 126 倍，并显示出对香豆酰辅酶 A 和莽草酸的绝对特异性。酶反应的产物已被鉴定为 5-O-p-香豆酰基莽草酸。还发现了 CST 活性在各种植物细胞悬浮培养物和完整植物中的广泛分布。
• Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase
  作者：Horst Hemmerle、Hans-Joerg Burger、Peter Below、Gerrit Schubert、Robert Rippel、Peter W. Schindler、Erich Paulus、Andreas W. Herling

  DOI：10.1021/jm9607360

  日期：1997.1.1

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.