2-(4-hydroxy-3-methoxyphenyl)ethyl β-D-galactopyranoside | 850232-24-5

• 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-methoxyphenyl)ethyl β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[2-(4-hydroxy-3-methoxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 850232-24-5
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: CGDVBCBYNROVPI-GZBLMMOJSA-N

物化性质

• 沸点：
  566.5±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(4-Benzyloxy-3-bromophenyl)-1-ethanol 在 5%-palladium/activated carbon 、 氢气 、 sodium methylate 、 silver carbonate 、 copper(I) bromide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 2-(4-hydroxy-3-methoxyphenyl)ethyl β-D-galactopyranoside
  参考文献：
  名称：

  Zheng, Cheng; Guo, Yibing; Meng, Ying, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 5, p. 654 - 664

  摘要：

  DOI：

文献信息

• The influence of the carbohydrate anomeric linkage on the free radical scavenging activity of enzymatically-synthesized phenolic glycosides
  作者：Jorge A. González-Ríos、José Pedraza-Chaverri、Omar N. Medina-Campos、Miguel Reina、Yanet Romero、Ana Martínez、Agustín López-Munguía、Edmundo Castillo

  DOI：10.1039/c6ra06572d

  日期：——

  Phenolic glycosides, widely recognized for their nutraceutical properties exist in nature as α- and β-glycosides. Interestingly, the β-phenolic glycosides are the predominant form in natural products. In this work, the pure α- and β-glucosides and galactosides of homovanillyl alcohol (HVA) were enzymatically synthesized. Their free radical scavenger (FRS) activity was evaluated using the DPPH˙ endpoint

  在自然界中，众所周知的酚醛糖苷以α-和β-糖苷的形式存在。有趣的是，β-酚苷是天然产物中的主要形式。在这项工作中，酶法合成了纯香草醛醇（HVA）的α-和β-葡萄糖苷和半乳糖苷。使用DPPH˙终点分析法评估了它们的自由基清除剂（FRS）活性。根据EC 50值，所有糖苷均比相应的糖苷配基更好的FRS，β-端基异构体的EC 50值较低。相反，DPPH 3动力学分析表明，HVA-糖苷配体比糖苷具有更高的反应性。基于EC 50的分析和动力学行为表明，尽管在动力学上HVA-糖苷配基是更好的自由基清除剂，但是糖苷化使得HVA-糖苷配基对于长期反应更稳定。对α-和β-HVA糖苷的分子静电势和构象分析表明，β-HVA糖苷比相应的α-端基异构体是更好的自由基清除剂。实际上，β-HVA糖苷的较高柔韧性允许暴露有利于其FRS能力的有利带负电荷的区域。
• Free radical scavenging and hepatoprotective effects of salidroside analogs on CCl4-induced cytotoxicity in LO2 cells
  作者：Yibing Guo、Cheng Zheng、Wen Xu、Yongxing Si、Sufeng Dou、Yumin Yang

  DOI：10.1007/s00044-012-0247-z

  日期：2013.5

  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.