5-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-7,3′,4′-trihydroxy-4-phenylcoumarin | 1492917-59-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-7,3′,4′-trihydroxy-4-phenylcoumarin
• 英文别名: 4-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
• CAS: 1492917-59-5
• 化学式: C₂₆H₂₈O₁₅
• 分子量: 580.499
• InChiKey: XSUATNGSAZMWRU-ZYAFLGLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-O-[β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl]-7,3′,4′-trihydroxy-4-phenylcoumarin 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 D-木糖 、 葡萄糖
  参考文献：
  名称：

  Development of a UHPLC-PDA Method for the Simultaneous Quantification of 4-Phenylcoumarins and Chlorogenic Acid in Exostema caribaeum Stem Bark

  摘要：

  Potential toxic effects in mice of an infusion prepared from the stem bark of Exostema caribaeum was assessed by means of the Lorke procedure. The preparation was not found to be toxic, with the LD50 value estimated to be more than 5 g/kg. This preparation at 100, 300, and 500 mg/kg also caused a significant hypoglycemic effect and a reduction in the postprandial glycemia peak in both normal OH and nicotinamide/streptozotocin (NA/STZ)-diabetic mice in an oral sucrose tolerance test. Phytochemical analysis of the infusion revealed that the major active principles are 4-phenylcoumarins (2-8) and chlorogenic acid (1). During this process, a new 4-phenylcoumarin was isolated along with several known analogues. The structure of the new compound was established as 5-O-[beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranosyl]-7,3',4'-trihydroxy-4-phenylcoumarin (2) by spectroscopic means. A simple, efficient, fast, and reliable UHPLC-PDA analytical method for quantifying 4-phenylcoumarins and chlorogenic acid (1) was developed and validated. Parameters assessed for the method validation were selectivity, linearity, the limits of detection (LOD) and quantification (LOQ), precision, and accuracy. It was found that all calibration curves showed good linearity (R-2 > 0.9931), within the range of concentrations tested.

  DOI：

  10.1021/np400785z

文献信息

• Development of a UHPLC-PDA Method for the Simultaneous Quantification of 4-Phenylcoumarins and Chlorogenic Acid in <i>Exostema caribaeum</i> Stem Bark
  作者：Araceli Pérez-Vásquez、Erika Castillejos-Ramírez、Sol Cristians、Rachel Mata

  DOI：10.1021/np400785z

  日期：2014.3.28

  Potential toxic effects in mice of an infusion prepared from the stem bark of Exostema caribaeum was assessed by means of the Lorke procedure. The preparation was not found to be toxic, with the LD50 value estimated to be more than 5 g/kg. This preparation at 100, 300, and 500 mg/kg also caused a significant hypoglycemic effect and a reduction in the postprandial glycemia peak in both normal OH and nicotinamide/streptozotocin (NA/STZ)-diabetic mice in an oral sucrose tolerance test. Phytochemical analysis of the infusion revealed that the major active principles are 4-phenylcoumarins (2-8) and chlorogenic acid (1). During this process, a new 4-phenylcoumarin was isolated along with several known analogues. The structure of the new compound was established as 5-O-[beta-D-xylopyranosyl-(1 -> 6)-beta-D-glucopyranosyl]-7,3',4'-trihydroxy-4-phenylcoumarin (2) by spectroscopic means. A simple, efficient, fast, and reliable UHPLC-PDA analytical method for quantifying 4-phenylcoumarins and chlorogenic acid (1) was developed and validated. Parameters assessed for the method validation were selectivity, linearity, the limits of detection (LOD) and quantification (LOQ), precision, and accuracy. It was found that all calibration curves showed good linearity (R-2 > 0.9931), within the range of concentrations tested.