aspergiolide A

• 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: aspergiolide A
• 英文别名: 16-(2,4-dihydroxy-6-methylbenzoyl)-4,6,10-trihydroxy-12-methyl-14-oxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9,11,13(17)-heptaene-8,15-dione
• 化学式: C₂₅H₁₆O₉
• 分子量: 460.397
• InChiKey: XDYWIHGBFULPRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  sodium acetate 在 growing cultures of Aspergillus glaucus 作用下， 反应 48.0h， 生成 aspergiolide A
  参考文献：
  名称：

  Biosynthesis of aspergiolide A, a novel antitumor compound by a marine-derived fungus Aspergillus glaucus via the polyketide pathway

  摘要：

  Aspergiolide A, a novel antitumor compound, was produced by a marine-derived filamentous fungus Aspergillus glaucus. The biosynthesis of it was unambiguously determined by feeding experiments using [1-C-13]sodium acetate, [2-C-13]sodium acetate, and [1,2-C-13(2)]sodium acetate precursors followed by C-13 NMR spectroscopic investigation of the isolated products. Analysis of the patterns of C-13-enrichment revealed that all 25 carbon atoms in skeleton of aspergiolide A were derived from labeled acetate. And among them, 12 carbon atoms were labeled from the carboxylic group of acetate, while the other 13 carbon atoms were labeled from the methylic group of acetate. Besides, the labeling pattern of [1,2-C-13(2)]sodium, acetate feeding experiment demonstrated that 12 intact acetate units were incorporated in aspergiolide A by polyketide pathway. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.094