vanillyl alcohol 4-O-β-D-(6'-O-galloyl) glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: vanillyl alcohol 4-O-β-D-(6'-O-galloyl) glucopyranoside
• 英文别名: 4-hydroxymethyl-2-methoxyphenol-1-O-β-D-(6'-O-galloyl)glucoside；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• 化学式: C₂₁H₂₄O₁₂
• 分子量: 468.414
• InChiKey: NOAUBCDANOKMMU-PEVLUNPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  vanillyl alcohol 4-O-β-D-(6'-O-galloyl) glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 D-古洛糖
  参考文献：
  名称：

  Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling

  摘要：

  The phenolic content of the ethanol extract of the stem bark of the Brazilian plant Schinopsis brasiliensis Engl. (Anacardiaceae) has been evaluated together with the antioxidant activity. The good antioxidant activity exhibited in the Trolox Equivalent Antioxidant Capacity (TEAC) assay (TEAC value = 3.04 mg/mL) encouraged us to investigate its constituents. An analytical approach based on LC-ESIMSn was applied to rapidly obtain a metabolite profile of the ethanol extract of the stem bark of S. brasiliensis. Sixteen phenolic compounds, among which five galloyl derivatives, never reported before, have been isolated and their structures have been unambiguously elucidated by extensive spectroscopic methods, including 1D (H-1, C-13, TOCSY) and 2D (DQF-COSY, HMBC, and HSQC) NMR experiments. Moreover, the antioxidant activity of all the isolated compounds was evaluated, along with the cytotoxicity against the cancer cell lines A549 (human alveolar basal carcinoma) and Hela (human epitheloid cervix carcinoma). The previously undescribed compounds exhibited a high free-radical-scavenging activity, in the range of 1.10 -1.86 mM.None of the tested compounds, in a range of concentrations between 12.5 and 100 mu M, caused a significant reduction of the cell number. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2017.04.008

文献信息

• Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling
  作者：Clisiane Carla de Souza Santos、Milena Masullo、Antonietta Cerulli、Angela Mari、Charles Dos Santos Estevam、Cosimo Pizza、Sonia Piacente

  DOI：10.1016/j.phytochem.2017.04.008

  日期：2017.8

  The phenolic content of the ethanol extract of the stem bark of the Brazilian plant Schinopsis brasiliensis Engl. (Anacardiaceae) has been evaluated together with the antioxidant activity. The good antioxidant activity exhibited in the Trolox Equivalent Antioxidant Capacity (TEAC) assay (TEAC value = 3.04 mg/mL) encouraged us to investigate its constituents. An analytical approach based on LC-ESIMSn was applied to rapidly obtain a metabolite profile of the ethanol extract of the stem bark of S. brasiliensis. Sixteen phenolic compounds, among which five galloyl derivatives, never reported before, have been isolated and their structures have been unambiguously elucidated by extensive spectroscopic methods, including 1D (H-1, C-13, TOCSY) and 2D (DQF-COSY, HMBC, and HSQC) NMR experiments. Moreover, the antioxidant activity of all the isolated compounds was evaluated, along with the cytotoxicity against the cancer cell lines A549 (human alveolar basal carcinoma) and Hela (human epitheloid cervix carcinoma). The previously undescribed compounds exhibited a high free-radical-scavenging activity, in the range of 1.10 -1.86 mM.None of the tested compounds, in a range of concentrations between 12.5 and 100 mu M, caused a significant reduction of the cell number. (C) 2017 Elsevier Ltd. All rights reserved.