2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl β-D-glucopyranoside | 1350703-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl β-D-glucopyranoside
• 英文别名: β-(4-hydroxy-3,5-dimethoxyphenyl)ethyl β-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-[2-(4-hydroxy-3,5-dimethoxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1350703-34-2
• 化学式: C₁₆H₂₄O₉
• 分子量: 360.361
• InChiKey: YLUWATMQOJRAQZ-YMILTQATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酰溴葡糖 在 5%-palladium/activated carbon 、 氢气 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl β-D-glucopyranoside
  参考文献：
  名称：

  Free radical scavenging and hepatoprotective effects of salidroside analogs on CCl4-induced cytotoxicity in LO2 cells

  摘要：

  Salidroside, a phenylpropanoid glycoside isolated from a traditional Chinese medicinal plant Rhodiola rosea L. displays a broad spectrum of pharmacological properties. It has been found to play a hepatoprotective role in liver diseases through inhibiting apoptosis of hepatocytes and proliferation of hepatic stellate cells, decreasing serum aminotransferase, reversing hepatic fibrosis, and improving liver function. In this study as an ongoing study on the discovery and development of new hepatoprotective agents, about 12 novel glycosides were synthesized, and 2,2-diphenyl-1-picrylhydrazyl radical scavenge activity of each glycoside was evaluated. 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-glucopyranoside (4g) and 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-galactopyranoside (4h) exhibited significant activity prior to salidroside with an IC50 value of 38.05 and 35.85 mu M, respectively. The hepatoprotective effect of compounds 4g and 4h on CCl4-induced cytotoxicity in LO2 cells was assessed for further research.2-(3,4,5-Trihydroxyphenyl)ethyl beta-d-glucopyranoside (4g) and 2-(3,4,5-trihydroxyphenyl)ethyl beta-d-galactopyranoside (4h) exhibited significant hepatoprotective activity prior to salidroside.

  DOI：

  10.1007/s00044-012-0247-z

文献信息

• Zheng, Cheng; Guo, Yibing; Meng, Ying, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 5, p. 654 - 664
  作者：Zheng, Cheng、Guo, Yibing、Meng, Ying、Dou, Sufeng、Shao, Jian、Yang, Yumin

  DOI：——

  日期：——
• Comparative study of relationship between structure of phenylethanoid glycopyranosides and their activities using cell-free assays and human cells cultured in vitro
  作者：Eva Horvathova、Maria Mastihubova、Elena Karnisova Potocka、Peter Kis、Eliska Galova、Andrea Sevcovicova、Martina Klapakova、Luba Hunakova、Vladimir Mastihuba

  DOI：10.1016/j.tiv.2019.104646

  日期：2019.12

  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.