甘草异黄烷甲 | 129314-37-0

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 甘草异黄烷甲
• 英文名称: licorisoflavan A
• 英文别名: 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• CAS: 129314-37-0
• 化学式: C₂₇H₃₄O₅
• 分子量: 438.564
• InChiKey: GDAAEAXMNLVRCZ-SFHVURJKSA-N

物化性质

• 沸点：
  589.2±50.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

甘草异黄烷甲是从植物中提取的成分，也被用作标准品和对照品。

反应信息

• 作为反应物：
  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

• Zeng, Lu; Fukai, Toshio; Nomura, Taro, Heterocycles, 1992, vol. 34, # 9, p. 1813 - 1828
  作者：Zeng, Lu、Fukai, Toshio、Nomura, Taro、Zhang, Ru-Yi、Lou, Zhi-Cen

  DOI：——

  日期：——
• Fukai, Toshio; Nishizawa, Junko; Yokoyama, Masami, Heterocycles, 1993, vol. 36, # 11, p. 2565 - 2576
  作者：Fukai, Toshio、Nishizawa, Junko、Yokoyama, Masami、Nomura, Taro

  DOI：——

  日期：——
• 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).