5,7-dihydroxy-6-prenoxyflavone | 1020254-49-2

• 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: 5,7-dihydroxy-6-prenoxyflavone
• 英文别名: Bai-C5；5,7-Dihydroxy-6-(3-methylbut-2-enoxy)-2-phenylchromen-4-one
• CAS: 1020254-49-2
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: XFNOIFYDSURNCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  黄芩素 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 5,7-dihydroxy-6-prenoxyflavone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel C(6) Modified Baicalein Derivatives as Antioxidative Agents

  摘要：

  Baicalein, one of the major flavones, was found to be responsible for the antioxidative activity of the traditional Chinese medicinal herb Huang-Qin (Scutellaria baicalensis Georgi), which is widely used as an antioxidative, anti-inflammatory, and antitumor agent. The hydroxyl group of the A ring of the baicalein was alkylated at position 6 with terpenoids such as prenyl, geranyl, and farnesyl groups, and - their free radical scavenging activities and glutathione (GSH) depletion capacities were examined. Their free radical scavenging activity was measured according to the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(.+)) scavenging method. Baicalein and newly synthesized baicalein derivatives were found to be good free radical scavengers. Flow cytometrical method was employed to measure the intracellular antioxidative activity and GSH depletion capacity of these derivatives in human acute monocytic leukemia cell line (THP-1). It was also found that baicalein and its derivatives could decrease the levels of exogenous cumene hydroperoxide and H2O2 in THP-1 cells. These compounds also could significantly inhibit the intracellular GSH depletion induced by cumene hydroperoxide in THP-1 cells. The production of cumene hydroperoxide-induced Bax, a pro-apoptotic related protein, could also be inhibited by baicalein and its derivatives. These results suggested that baicalein and its derivatives could be beneficial to human health.

  DOI：

  10.1021/jf073224a