baicalein 6-O-α-D-glucoside

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: baicalein 6-O-α-D-glucoside
• 英文别名: 5,7-dihydroxy-2-phenyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: WTYYPLMAODUDGW-GHNMMOQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  黄芩素 、 蔗糖 在 Deinococcus geothermalis recombinant amylosucrase 作用下， 以 aq. buffer 为溶剂， 反应 12.5h， 生成 baicalein 6-O-α-D-glucoside
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel baicalein glycoside as an anti-inflammatory agent

  摘要：

  Baicalein-6-alpha-glucoside (BG), a glycosylated derivative of baicalein, was synthesized by using sucrose and the amylosucrase of Deinococcus geothermalis and tested for its solubility, chemical stability, and anti-inflammatory activity. BC was 26.3 times more soluble than baicalein and highly stable in buffered solutions and Dulbecco's modified Eagle medium containing 10% fetal bovine serum. BC treatment decreased the production of nitric oxide in RAW 264.7 cells treated with lipopolysaccharide (LPS). Luciferase reporter assays, western blots, reverse transcription-polymerase chain reaction, and flow cyLorneLric analyses indicated that BG activated nuclear factor erythroid 2-related factor 2 (Nrf2), an antioxidant transcription factor that confers protection from various inflammatory diseases, induced Nrf2-dependent gene expression, and suppressed the production of reactive oxygen species elicited by [PS more effectively than baicalein. Cellular uptake of BC assessed by confocal microscopy and HPLC analysis of the cell free extracts of RAW 264.7 cells demonstrated that BC was gradually converted to baicalein inside the cells. These results explain that glycosylaLion increased the bioavailabilify of baicalein by helping to protect this vital molecule from chemical or enzymatic oxidation. Therefore, BC, a glycosylated derivative of baicalein, can be an alternative to baicalein as a therapeutic drug. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2014.10.013