licorisoflavan C | 1551035-46-1

• 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: licorisoflavan C
• 英文别名: 8-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2,2-dimethylchromen-5-ol
• CAS: 1551035-46-1
• 化学式: C₂₆H₃₀O₅
• 分子量: 422.521
• InChiKey: NPCBOHBGCANYKG-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘草西定 在 palladium dichloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以5.2 mg的产率得到licorisoflavan C
  参考文献：
  名称：

  Pyrano-isoflavans from Glycyrrhiza uralensis with Antibacterial Activity against Streptococcus mutans and Porphyromonas gingivalis

  摘要：

  Continuing investigation of fractions from a supercritical fluid extract of Chinese licorice (Glycyrrhiza uralensis) roots has led to the isolation of 12 phenolic compounds, of which seven were described previously from this extract. In addition to these seven metabolites, four known components, 1-methoxyerythrabyssin II (4), 6,8-diprenylgenistein, gancaonin G (5), and isoglycyrol (6), and one new isoflavan, licorisoflavan C (7), were characterized from this material for the first time. Treatment of licoricidin (1) with palladium chloride afforded larger amounts of 7 and also yielded two new isoflavans, licorisoflavan D (8), which was subsequently detected in the licorice extract, and licorisoflavan E (9). Compounds 1-9 were evaluated for their antibacterial activities against the cariogenic Streptococcus mutans and the periodontopathogenic Porphyromonas gingivalis. Licoricidin (1), licorisoflavan A (2), and 7-9 showed antibacterial activity against P. gingivalis (MICs of 1.56-12.5 mu g/mL). The most potent activity against S. mutans was obtained with 7 (MIC of 6.25 mu g/mL), followed by 1 and 9 (MIC of 12.5 mu g/mL). This study provides further evidence for the therapeutic potential of licorice extracts for the treatment and prevention of oral infections.

  DOI：

  10.1021/np400788r

文献信息

• Pyrano-isoflavans from <i>Glycyrrhiza uralensis</i> with Antibacterial Activity against <i>Streptococcus mutans</i> and <i>Porphyromonas gingivalis</i>
  作者：Jacquelyn R. Villinski、Chantal Bergeron、Joseph C. Cannistra、James B. Gloer、Christina M. Coleman、Daneel Ferreira、Jabrane Azelmat、Daniel Grenier、Stefan Gafner

  DOI：10.1021/np400788r

  日期：2014.3.28

  Continuing investigation of fractions from a supercritical fluid extract of Chinese licorice (Glycyrrhiza uralensis) roots has led to the isolation of 12 phenolic compounds, of which seven were described previously from this extract. In addition to these seven metabolites, four known components, 1-methoxyerythrabyssin II (4), 6,8-diprenylgenistein, gancaonin G (5), and isoglycyrol (6), and one new isoflavan, licorisoflavan C (7), were characterized from this material for the first time. Treatment of licoricidin (1) with palladium chloride afforded larger amounts of 7 and also yielded two new isoflavans, licorisoflavan D (8), which was subsequently detected in the licorice extract, and licorisoflavan E (9). Compounds 1-9 were evaluated for their antibacterial activities against the cariogenic Streptococcus mutans and the periodontopathogenic Porphyromonas gingivalis. Licoricidin (1), licorisoflavan A (2), and 7-9 showed antibacterial activity against P. gingivalis (MICs of 1.56-12.5 mu g/mL). The most potent activity against S. mutans was obtained with 7 (MIC of 6.25 mu g/mL), followed by 1 and 9 (MIC of 12.5 mu g/mL). This study provides further evidence for the therapeutic potential of licorice extracts for the treatment and prevention of oral infections.