3',5,7-trihydroxyflavone | 72472-92-5

• 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: 3',5,7-trihydroxyflavone
• 英文别名: 5,7-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one；5,7-dihydroxy-2-(3-hydroxyphenyl)chromen-4-one
• CAS: 72472-92-5
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: BEXPKGWBRBLIIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 氢溴酸 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 丙酮 为溶剂， 反应 40.0h， 生成 3',5,7-trihydroxyflavone
  参考文献：
  名称：

  Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

  摘要：

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

  DOI：

  10.1016/j.ejmech.2020.112754

文献信息

• Cleavage of Methyl Ethers of Flavones by Chloroaluminate Ionic Liquid
  作者：Tao Liu、Yongzhou Hu

  DOI：10.1081/scc-200028625

  日期：2004.1

  A new o-demethylation method of a series of mono-, di-, trimethoxy-flavones using a chloroalununate ionic liquid-[BMIM] [Al2Cl7] in dichloromethane is described. The desired products were obtained in moderate to good yields.
• Modulation of human neutrophils' oxidative burst by flavonoids
  作者：Daniela Ribeiro、Marisa Freitas、Sara M. Tomé、Artur M.S. Silva、Graça Porto、Eduarda Fernandes

  DOI：10.1016/j.ejmech.2013.06.019

  日期：2013.9

  Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study, we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ring was evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst. (C) 2013 Elsevier Masson SAS. All rights reserved.
• v. Kostanecki; Steuermann, Chemische Berichte, 1901, vol. 34, p. 111
  作者：v. Kostanecki、Steuermann

  DOI：——

  日期：——
• Shaw; Simpson, 1952, p. 5027,5030
  作者：Shaw、Simpson

  DOI：——

  日期：——
• v. Kostanecki; Steuermann, Chemische Berichte, 1901, vol. 34, p. 112
  作者：v. Kostanecki、Steuermann

  DOI：——

  日期：——