methyl 3-(β-D-glucopyranosyloxy)-4-hydroxy-5-methoxybenzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 3-(β-D-glucopyranosyloxy)-4-hydroxy-5-methoxybenzoate
• 化学式: C₁₅H₂₀O₁₀
• 分子量: 360.318
• InChiKey: SMSZMLXTMMBDNX-VWKSAYTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.63
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  155.14
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(β-D-glucopyranosyloxy)-4-hydroxy-5-methoxybenzoate 在 盐酸 、 L-半胱氨酸甲酯盐酸盐 作用下， 以 1,4-二氧六环 、 水 、 吡啶 为溶剂， 反应 4.5h， 生成 D-葡萄糖
  参考文献：
  名称：

  Anti-allergic inflammatory components from Sanguisorba officinalis L.

  摘要：

  Sanguisorba officinalis L. was well known as a traditional herbal medicine to treat inflammation and allergic skin diseases. The aim of this research was to identify compounds with anti-allergic inflammatory property. Twenty-five compounds (1-25) were isolated from S.officinalis including two new compounds (1 and 8), and their chemical structures were identified by NMR and ESIMS analysis. Consequently, the anti-allergic inflammatory activities of these isolates were investigated by inhibiting p-hexosaminidase and IL-4 production in PMA/A23187-stimulated RBL-2H3 cells. Compounds 6, 8,13,17-18 and 25 significantly inhibited p-hexosaminidase release and IL-4 production. Additionally, compounds 8, 17 and 25 effectively suppressed the activation of NF-kappa B and NF-kappa B p65 translocation into the nucleus. Anti-inflammatory effects of isolated compounds were evaluated in LPS-stimulated RAW264.7 macrophages, and they showed dramatic inhibition on LPS-induced overproduction of nitric oxide (NO) and TNF-a. Consistently, the protein levels of iNOS and COX-2 were remarkably decreased by the single compounds 8,13 and 25. These results showed that compounds 8,13 and 25 from S.officinalis may have a therapeutic potential for allergic inflammatory diseases.(C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.033