β-(4-hydroxyphenyl)ethyl α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-(4-hydroxyphenyl)ethyl α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: ILRCGYURZSFMEG-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 生成 β-(4-hydroxyphenyl)ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro

  摘要：

  The study focused on protective potential of phytochemicals applicable in prevention and health protection is of great importance. Various structures of these compounds and a wide range of their biological activities have inspired organic chemists to sythesize their effective analogues in order to further increase their efficacy.The aims of our study were (i) to synthesize phenylethanoid glycopyranosides: salidroside (SALI - tyrosol beta-Dglucopyranoside), tyrosol beta-D-galactopyranoside (TYBGAL), tyrosol alpha-D-galactopyranoside (TYAGAL), tyrosol alpha-D-mannopyranoside (TYAMAN), hydroxytyrosol alpha-D-mannopyranoside (HOTAMA), homosyringyl beta-D-glucopyranoside (HSYGLU), hydroxytyrosol beta-D-xylopyranoside (HOTXYL) and hydroxysalidroside (HOSALI); (ii) to determine their antioxidant capacities (cell-free approaches); (iii) to evaluate their cytotoxicity (MTT test), protectivity against hydrogen peroxide (H2O2; comet assay) and effect on the intracellular glutathione level (iGSH; flow cytometry) in experimental system utilizing human hepatoma HepG2 cells.HOSALI, HOTAMA, HOTXYL and HSYGLU manifested the highest antioxidant capacity in cell-free assays and they were most active in protection of HepG2 cells against H2O2. On the other hand, pre-treatment of HepG2 cells with SALI had protective effects even though SALT displayed almost no activity in cell-free assays.Differences in the efficacy of the analogues revealed that structures of their molecules in terms of aglycone combined with sugar moiety affect their activities.

  DOI：

  10.1016/j.tiv.2019.104646