(±)-penifupyrone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (±)-penifupyrone
• 英文别名: penifupyrone；(+/-)-Penifupyrone；methyl 3,5-dimethoxy-2-(5-methyl-7-oxo-5,6-dihydrofuro[3,2-b]pyran-3-carbonyl)benzoate
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: BLDKOKNYBYRQGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (±)-penifupyrone 在 Chiralpak AY-H 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 S-penifupyrone 、 R-penifupyrone
  参考文献：
  名称：

  Polyketides with α-Glucosidase Inhibitory Activity from a Mangrove Endophytic Fungus, Penicillium sp. HN29-3B1

  摘要：

  Five new compounds, pinazaphilones A and B (1, 2), two phenolic compounds (4, 5), and penicidone D (6), together with the known Sch 1385568 (3), (+/-)-penifupyrone (7), 3-O-methylfunicone (8), 5-methylbenzene-1,3-diol (9), and 2,4-dihydroxy-6-methylbenzoic acid (10) were obtained from the culture of the endophytic fungus Penicillium sp. HN29-3B1, which was isolated from a fresh branch of the mangrove plant Cerbera manghas collected from the South China Sea. Their structures were determined by analysis of ID and 2D NMR and mass spectroscopic data. Structures of compounds 4 and 7 were further confirmed by a single-crystal X-ray diffraction experiment using Cu K alpha radiation. The absolute configurations of compounds 1-3 were assigned by quantum chemical calculations of the electronic circular dichroic spectra. Compounds 2, 3, 5, and 7 inhibited alpha-glucosidase with IC50 values of 28.0, 16.6, 2.2, and 14.4 mu M, respectively, and are thus more potent than the positive control, acarbose.

  DOI：

  10.1021/np500885f