3-hydroxy-5-methoxybibenzyl-3'-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-hydroxy-5-methoxybibenzyl-3'-O-β-D-glucopyranoside
• 化学式: C₂₁H₂₆O₈
• 分子量: 406.433
• InChiKey: QZILGKAVOXJLRK-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128.84
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-methoxybibenzyl-3'-O-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  Stilbenes from the tubers of Bletilla striata with potential anti-neuroinflammatory activity

  摘要：

  Neuroinflammation are involved in the pathogenesis of many neurodegenerative disorders. In our screening of natural effective neuroinflammatory inhibitors from natural products, stilbenes, such as resveratrol and its analogues, have received considerable attention over the last several decades as anti-neuroinflammatory agents. Then, Bletilla striata attracted our attention due to its abundant stilbenes portion, PE fraction. So, three new stilbenes: dusuanlansin E1 (23a), dusuanlansin E2 (23b), 3-hydroxy-5-methoxybibenzyl-3'-O-beta-D-glucopyrano-side (27), and 30 known stilbene compounds were isolated from B. striata. These structures of the compounds were established on the basis of extensive spectroscopic analysis including 1D and 2D NMR and circular dichroism (CD) data. Furthermore, all the isolated components were tested in vitro for their inhibitory effects on the nitric oxide generation in LPS-stimulated BV2 cells. As a result, compounds 2, 5, 6, 16, 17 can greatly inhibit the NO production without cytotoxicity. In addition, SARs between stilbenes and anti-neuroinflammation effects were discussed briefly. In conclusion, stilbenes were characteristic constituents of the tubers of B. striata with potential anti- neuroinflammatory effects.

  DOI：

  10.1016/j.bioorg.2020.103715

文献信息

• Stilbenes from the tubers of Bletilla striata with potential anti-neuroinflammatory activity
  作者：Di Zhou、Wenhui Chang、Bo Liu、Gang Chen、Yanqiu Yang、Yingtu Hao、Yue Hou、Ning Li

  DOI：10.1016/j.bioorg.2020.103715

  日期：2020.4

  Neuroinflammation are involved in the pathogenesis of many neurodegenerative disorders. In our screening of natural effective neuroinflammatory inhibitors from natural products, stilbenes, such as resveratrol and its analogues, have received considerable attention over the last several decades as anti-neuroinflammatory agents. Then, Bletilla striata attracted our attention due to its abundant stilbenes portion, PE fraction. So, three new stilbenes: dusuanlansin E1 (23a), dusuanlansin E2 (23b), 3-hydroxy-5-methoxybibenzyl-3'-O-beta-D-glucopyrano-side (27), and 30 known stilbene compounds were isolated from B. striata. These structures of the compounds were established on the basis of extensive spectroscopic analysis including 1D and 2D NMR and circular dichroism (CD) data. Furthermore, all the isolated components were tested in vitro for their inhibitory effects on the nitric oxide generation in LPS-stimulated BV2 cells. As a result, compounds 2, 5, 6, 16, 17 can greatly inhibit the NO production without cytotoxicity. In addition, SARs between stilbenes and anti-neuroinflammation effects were discussed briefly. In conclusion, stilbenes were characteristic constituents of the tubers of B. striata with potential anti- neuroinflammatory effects.