asperolide A | 1356934-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: asperolide A
• 英文别名: (1S,9R,12S,15R,16R)-15-hydroxy-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7,13-triene-4,11-dione
• CAS: 1356934-94-5
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: JYBNWLHGCZDZAC-VWHJJCLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  asperolide A 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 10.0h， 生成 [(1S,9R,12S,15R,16R)-1,12-dimethyl-4,11-dioxo-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7,13-trien-15-yl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Asperolides A–C, Tetranorlabdane Diterpenoids from the Marine Alga-Derived Endophytic Fungus Aspergillus wentii EN-48

  摘要：

  Bioassay-guided fractionation of the culture extract of Aspergillus wentii EN-48, an endophytic fungus isolated from an unidentified marine brown algal species of the genus Sargassum, led to the isolation of three new tetranorlabdane diterpenoids, asperolides A-C (1-3), and five related derivatives (4-8). The structures of these compounds were established on the basis of spectroscopic interpretation, and compound 1 was confirmed by X-ray crystallographic analysis. The absolute configuration of I was determined by application of the modified Mosher's method. An Xray structure for wentilactone B (6) is also reported. Compounds 1-8 were evaluated for cytotoxic and antibacterial activities.

  DOI：

  10.1021/np2006742