pruniflorone U

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: pruniflorone U
• 英文别名: Methyl 7-hydroxy-15,15-dimethyl-17-(3-methylbut-2-enyl)-9,12-dioxo-2,16-dioxatetracyclo[8.7.0.01,14.03,8]heptadeca-3,5,7,10-tetraene-17-carboxylate；methyl 7-hydroxy-15,15-dimethyl-17-(3-methylbut-2-enyl)-9,12-dioxo-2,16-dioxatetracyclo[8.7.0.01,14.03,8]heptadeca-3,5,7,10-tetraene-17-carboxylate
• 化学式: C₂₄H₂₆O₇
• 分子量: 426.466
• InChiKey: DPUFUNVIVYLFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pruniflorone U 在 Chiral Pack AD-H 作用下， 生成 (+)-pruniflorone U 、 (-)-pruniflorone U
  参考文献：
  名称：

  Three Types of Cytotoxic Natural Caged-Scaffolds: Pure Enantiomers or Partial Racemates

  摘要：

  Two rare new natural products, the neocaged-xanthone pruniflorone T (1) and the rearranged caged-xanthone pruniflorone U (3), and the known caged-xanthone cochinchnione C (2) were isolated from the roots of Cratoxylum formosum ssp. pruniflorum. The unique structures of 1-3 were determined by analysis of NMR and X-ray diffraction data. The X-ray data of 1-3 revealed that they all exist with both enantiomers in their crystal packing. Separation of 1-3 by chiral HPLC led to the isolation of three pairs of enantiomers, (-)-1/(+)-1, (-)-2/(+)-2, and (-)-3/(+)-3, and their absolute configurations were determined by analysis of single-crystal X-ray diffraction and ECD spectroscopic data. A 1:1 mixture of 1 and 3 showed potent in vitro cytotoxicity against an MCF-7 human breast cancer cell line with an IC50 value of 0.11 mu g/mL.

  DOI：

  10.1021/np400996k