pruniflorone T

• 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 T
• 英文别名: 7-Hydroxy-12-methoxy-15,15-dimethyl-13-(3-methylbut-2-enyl)-2,14-dioxapentacyclo[11.4.1.01,10.03,8.012,16]octadeca-3,5,7,10-tetraene-9,18-dione；7-hydroxy-12-methoxy-15,15-dimethyl-13-(3-methylbut-2-enyl)-2,14-dioxapentacyclo[11.4.1.01,10.03,8.012,16]octadeca-3,5,7,10-tetraene-9,18-dione
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: AVKWWEJYPMZXJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  pruniflorone T 在 Chiral Pack AD-H 作用下， 生成 (+)-pruniflorone T 、 (-)-pruniflorone T
  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

文献信息

• Three Types of Cytotoxic Natural Caged-Scaffolds: Pure Enantiomers or Partial Racemates
  作者：Nawong Boonnak、Suchada Chantrapromma、Hoong-Kun Fun、Supreeya Yuenyongsawad、Brian O. Patrick、Wisanu Maneerat、David E. Williams、Raymond J. Andersen

  DOI：10.1021/np400996k

  日期：2014.7.25

  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.