(7'R,8S,8'S)-8,8'-dimethyl-3',4,4',5-tetramethoxy-2,7'-cyclolignan-8-ol | 1255789-15-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (7'R,8S,8'S)-8,8'-dimethyl-3',4,4',5-tetramethoxy-2,7'-cyclolignan-8-ol
• 英文别名: (2S,3S,4R)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-1H-naphthalen-2-ol
• CAS: 1255789-15-1
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: BXRCKMALLHPXEJ-QYDGOFIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (±)-isogalbulin 在 Beauveria bassiana ATCC 7159 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 480.0h， 以0.7 mg的产率得到(7'R,8S,8'S)-8,8'-dimethyl-3',4,4',5-tetramethoxy-2,7'-cyclolignan-8-ol
  参考文献：
  名称：

  Microbial Transformations of Aryltetralone and Aryltetralin Lignans by Cunninghamella echinulata and Beauveria bassiana

  摘要：

  Microbiological transformation of the aryltetralone lignan (-)-8'-epi-aristoligone (1) with Cunninghamella echinulata ATCC 10028B afforded two known natural lignans, (-)-holostyligone (3) and (-)-arisantetralone (4). Incubation of the aryltetralin lignan (-)-isogalbulin (2), obtained by chemical transformation of 1, with C. echinulata ATCC 10028B afforded the known lignan aryltetralol (5) and seven new metabolites, (-)-8-hydroxylsogalbulin (6), (-)-7-methoxyisogalbulin (7), (-)-4'-O-demethyl-8-hydroxyisogalbulin (8), (-)-7-methoxy-8-hydroxyisogalbulin (9), (-)4'-O-demethyl-7-methoxyisogalbulin (10), (-)-4',5-O-didemethylcyclogalgravin (11), and (-)-4'-O-demethylcyclogal-gravin (12). When 2 was subjected to biotransformation with Beauveria bassiana ATCC 7159, (-)-8-hydroxyisogalbulin (6) was the only isolable product. The structures of all new compounds were established by detailed analysis of their spectroscopic data.

  DOI：

  10.1021/np100607s

文献信息

• Microbial Transformations of Aryltetralone and Aryltetralin Lignans by <i>Cunninghamella echinulata</i> and <i>Beauveria bassiana</i>
  作者：Gisele B. Messiano、E. M. Kithsiri Wijeratne、Lucia M. X. Lopes、A. A. Leslie Gunatilaka

  DOI：10.1021/np100607s

  日期：2010.11.29

  Microbiological transformation of the aryltetralone lignan (-)-8'-epi-aristoligone (1) with Cunninghamella echinulata ATCC 10028B afforded two known natural lignans, (-)-holostyligone (3) and (-)-arisantetralone (4). Incubation of the aryltetralin lignan (-)-isogalbulin (2), obtained by chemical transformation of 1, with C. echinulata ATCC 10028B afforded the known lignan aryltetralol (5) and seven new metabolites, (-)-8-hydroxylsogalbulin (6), (-)-7-methoxyisogalbulin (7), (-)-4'-O-demethyl-8-hydroxyisogalbulin (8), (-)-7-methoxy-8-hydroxyisogalbulin (9), (-)4'-O-demethyl-7-methoxyisogalbulin (10), (-)-4',5-O-didemethylcyclogalgravin (11), and (-)-4'-O-demethylcyclogal-gravin (12). When 2 was subjected to biotransformation with Beauveria bassiana ATCC 7159, (-)-8-hydroxyisogalbulin (6) was the only isolable product. The structures of all new compounds were established by detailed analysis of their spectroscopic data.