stelleralide E

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: stelleralide E
• 英文别名: [(1R,2S,4R,5R,6S,7S,9R,10R,11S,14R,15R,16S,26S)-10-hydroxy-14,16-dimethyl-9-[[(9Z,12Z)-octadeca-9,12-dienoyl]oxymethyl]-12-oxo-4-prop-1-en-2-yl-8,13,25,27,28,29-hexaoxaoctacyclo[13.10.1.14,24.15,24.111,14.01,6.07,9.011,26]nonacosan-2-yl]methyl benzoate
• 化学式: C₅₅H₇₆O₁₂
• 分子量: 929.201
• InChiKey: KAFWUIZOXLARTI-SBNPMHCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  67
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  stelleralide E 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z,Z)-9,12-十八烷二烯酸二聚物
  参考文献：
  名称：

  Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

  摘要：

  Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D-J, 1-7) and 12 known (8-19) daphnane diterpenoids. The structures and relative configurations of 1-7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1 alpha-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06-1.1 nM and selectivity index values of more than 10 000.

  DOI：

  10.1021/acs.jnatprod.5b00660

文献信息

• Stelleralides D–J and Anti-HIV Daphnane Diterpenes from <i>Stellera chamaejasme</i>
  作者：Min Yan、Yan Lu、Chin-Ho Chen、Yu Zhao、Kuo-Hsiung Lee、Dao-Feng Chen

  DOI：10.1021/acs.jnatprod.5b00660

  日期：2015.11.25

  Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D-J, 1-7) and 12 known (8-19) daphnane diterpenoids. The structures and relative configurations of 1-7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1 alpha-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06-1.1 nM and selectivity index values of more than 10 000.