4'-hydroxy-5,7-dimethoxy-6,3'-diprenylisoflavanquinone | 1346768-10-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4'-hydroxy-5,7-dimethoxy-6,3'-diprenylisoflavanquinone
• 英文别名: licoriquinone A
• CAS: 1346768-10-2
• 化学式: C₂₇H₃₂O₆
• 分子量: 452.547
• InChiKey: IEIFKNNADXZPPK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甘草异黄烷甲 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4'-hydroxy-5,7-dimethoxy-6,3'-diprenylisoflavanquinone
  参考文献：
  名称：

  Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

  摘要：

  Phytochemical investigation of a supercritical fluid extract of Glycyrrhiza uralensis has led to the isolation of 20 known isoflavonoids and coumarins, and glycycarpan (7), a new pterocarpan. The presence of two isoflavan-quinones, licoriquinone A (8) and licoriquinone B (9), in a fraction subjected to gel filtration on Sephadex LH-20 is due to suspected metal-catalyzed oxidative degradation of licoricidin (1) and licorisoflavan A (2). The major compounds in the extract, as well as 8, were evaluated for their ability to inhibit the growth of several major oral pathogens. Compounds 1 and 2 showed the most potent antibacterial activities, causing a marked growth inhibition of the cariogenic species Streptococcus mutans and Streptococcus sobrinus at 10 mu g/mL and the periodontopathogenic species Porphyromonas gingivalis (at 5 mu g/mL) and Prevotella intermedia (at 5 mu g/mL for 1 and 2.5 mu g/mL for 2). Only 1 moderately inhibited growth of Fusobacterium nucleatum at the highest concentration tested (10 mu g/mL).

  DOI：

  10.1021/np2004775

文献信息

• Isoflavonoids and Coumarins from <i>Glycyrrhiza uralensis</i>: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification
  作者：Stefan Gafner、Chantal Bergeron、Jacquelyn R. Villinski、Markus Godejohann、Pavel Kessler、John H. Cardellina、Daneel Ferreira、Karine Feghali、Daniel Grenier

  DOI：10.1021/np2004775

  日期：2011.12.27

  Phytochemical investigation of a supercritical fluid extract of Glycyrrhiza uralensis has led to the isolation of 20 known isoflavonoids and coumarins, and glycycarpan (7), a new pterocarpan. The presence of two isoflavan-quinones, licoriquinone A (8) and licoriquinone B (9), in a fraction subjected to gel filtration on Sephadex LH-20 is due to suspected metal-catalyzed oxidative degradation of licoricidin (1) and licorisoflavan A (2). The major compounds in the extract, as well as 8, were evaluated for their ability to inhibit the growth of several major oral pathogens. Compounds 1 and 2 showed the most potent antibacterial activities, causing a marked growth inhibition of the cariogenic species Streptococcus mutans and Streptococcus sobrinus at 10 mu g/mL and the periodontopathogenic species Porphyromonas gingivalis (at 5 mu g/mL) and Prevotella intermedia (at 5 mu g/mL for 1 and 2.5 mu g/mL for 2). Only 1 moderately inhibited growth of Fusobacterium nucleatum at the highest concentration tested (10 mu g/mL).