2-O-galloyl 6-O-(S)-brevifolincarboxyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-O-galloyl 6-O-(S)-brevifolincarboxyl-α-D-glucopyranoside
• 英文别名: fraxicoumarin
• 化学式: C₂₆H₂₂O₁₇
• 分子量: 606.45
• InChiKey: WNJFQMVOSIPCKD-NWMXVWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  43.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  291.18
• 氢给体数：
  9.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2-O-galloyl 6-O-(S)-brevifolincarboxyl-α-D-glucopyranoside 在 盐酸 、 吡啶 、 L-半胱氨酸甲酯盐酸盐 、 三甲基硅咪唑 作用下， 以 水 为溶剂， 反应 4.5h， 生成 葡萄糖
  参考文献：
  名称：

  Anti-inflammatory isocoumarins from the bark of Fraxinus chinensis subsp. rhynchophylla

  摘要：

  A new isocoumarin (1) named fraxicoumarin was isolated from the bark of Fraxinus chinensis subsp. rhynchophylla along with three known compounds (2-4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The anti-inflammatory effects of the isolated compounds (1-4) on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells were evaluated in vitro. Of the compounds tested, compounds 1 and 3 inhibited LPS-induced nitric oxide (NO) production in RAW 264.7 cells. Consistent with these findings, they also suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in RAW 264.7 cells.

  DOI：

  10.1080/14786419.2020.1715401

文献信息

• Anti-inflammatory isocoumarins from the bark of <i>Fraxinus chinensis</i> subsp. <i>rhynchophylla</i>
  作者：Beom Zoo Lee、Chan-Sik Kim、Soon-Kyu Jeong、Sulhae Lee、Ik Soo Lee、KwangWon Hong

  DOI：10.1080/14786419.2020.1715401

  日期：2021.11.17

  A new isocoumarin (1) named fraxicoumarin was isolated from the bark of Fraxinus chinensis subsp. rhynchophylla along with three known compounds (2-4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The anti-inflammatory effects of the isolated compounds (1-4) on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells were evaluated in vitro. Of the compounds tested, compounds 1 and 3 inhibited LPS-induced nitric oxide (NO) production in RAW 264.7 cells. Consistent with these findings, they also suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in RAW 264.7 cells.