7-hydroxy-5-methoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one

• 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: 7-hydroxy-5-methoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• 英文别名: 7-Hydroxy-5-methoxy-8-prenylflavanone；7-Hydroxy-5-methoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: GIJHRPCRRJJXGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  黄腐酚 在 水 、 sodium hydroxide 作用下， 反应 2.0h， 以80%的产率得到7-hydroxy-5-methoxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells

  摘要：

  For the prenylated hops phenols 6- and 8-prenylnaringenin (1 and 2), xanthohumol (3), and isoxanthohuniol (4), a variety of biological activities has been described. In the current study, a transwell based in vitro model using the human intestinal epithelialcell line Caco-2 was developed to assess potential- beneficial-effects of compounds 1-4. on TNF-alpha-induced impairment of tight junction (TJ) permeability. Trans epithelial electrical resistance (TEER) was measured using the, latest cellZScope online monitoring device. TNF-alpha treatment (26 mu g/mL) induced a significant decrease in TEER values (204.71 +/- 4.57 at 72 h) compared to that in control values (245.94 +/- 1.68 at 72 h). To determine preventive effects on TNF-alpha-induced impairment of TJ permeability; 1-4 were added to the apical compartment of CacO-2 monolayers 1 h before TNF-alpha treatment; afterward, TNF-alpha was added to the f-basolateral compartment to induce TJ dysfunction and incubated for a further 72-h. Using this setting, only 1 and 2 prevented epithelial disruption induced by TNF-alpha. To evaluate restorative effects of 1-4, TNF-alpha was added to the basolateral compartment, of Caco,2 celLmonolayers. After 48 h of incubation, 1,-4 were added to the apical side, and TEER values were monitored online for a further 72 h. Under these experimental conditions, only 2 restored TNF-alpha induced barrier dysfunction.

  DOI：

  10.1021/acs.jnatprod.6b00869

文献信息

• Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells
  作者：Sandro Luescher、Corinna Urmann、Veronika Butterweck

  DOI：10.1021/acs.jnatprod.6b00869

  日期：2017.4.28

  For the prenylated hops phenols 6- and 8-prenylnaringenin (1 and 2), xanthohumol (3), and isoxanthohuniol (4), a variety of biological activities has been described. In the current study, a transwell based in vitro model using the human intestinal epithelialcell line Caco-2 was developed to assess potential- beneficial-effects of compounds 1-4. on TNF-alpha-induced impairment of tight junction (TJ) permeability. Trans epithelial electrical resistance (TEER) was measured using the, latest cellZScope online monitoring device. TNF-alpha treatment (26 mu g/mL) induced a significant decrease in TEER values (204.71 +/- 4.57 at 72 h) compared to that in control values (245.94 +/- 1.68 at 72 h). To determine preventive effects on TNF-alpha-induced impairment of TJ permeability; 1-4 were added to the apical compartment of CacO-2 monolayers 1 h before TNF-alpha treatment; afterward, TNF-alpha was added to the f-basolateral compartment to induce TJ dysfunction and incubated for a further 72-h. Using this setting, only 1 and 2 prevented epithelial disruption induced by TNF-alpha. To evaluate restorative effects of 1-4, TNF-alpha was added to the basolateral compartment, of Caco,2 celLmonolayers. After 48 h of incubation, 1,-4 were added to the apical side, and TEER values were monitored online for a further 72 h. Under these experimental conditions, only 2 restored TNF-alpha induced barrier dysfunction.