(-)-1S,5R,7R,10R-eudesm-4(14)-en-1α,5β-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-1S,5R,7R,10R-eudesm-4(14)-en-1α,5β-diol
• 英文别名: verticillatol；(1S,4aS,6S,8aR)-8a-methyl-4-methylidene-6-propan-2-yl-2,3,5,6,7,8-hexahydro-1H-naphthalene-1,4a-diol
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: CKGNGZNSTIOFOY-XQLPTFJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (-)-1S,5R,7R,10R-eudesm-4(14)-en-1α,5β-diol 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,4aS,6S,8aR)-4a-hydroxy-6-isopropyl-8a-methyl-4-methylene-decahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Natural anti-HIV agents—part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata

  摘要：

  The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC50 value of 16.4 mug/ml (42.7 muM), while the known lignan 3 was inactive up to a concentration of 20 mug/ml (48.3 muM). Compound I demonstrated weak activity with an IC50 value of 34.5 mug/ml (144.7 muM) while being devoid of cytotoxicity at 20 mug/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00454-x

文献信息

• Natural anti-HIV agents—part I: (+)-demethoxyepiexcelsin and verticillatol from Litsea verticillata
  作者：Vu Dinh Hoang、Ghee Teng Tan、Hong-Jie Zhang、Pamela A Tamez、Nguyen Van Hung、Nguyen Manh Cuong、D.Doel Soejarto、Harry H.S Fong、John M Pezzuto

  DOI：10.1016/s0031-9422(01)00454-x

  日期：2002.2

  The eudesmane sesquiterpenoid, verticillatol (1), as well as the lignan, (+)-5'-demethoxyepiexcelsin (2), and a known lignan, epiexcelsin (3), were isolated from Litsea verticillata Hance. Lignan 2 showed moderate anti-HIV activity with an IC50 value of 16.4 mug/ml (42.7 muM), while the known lignan 3 was inactive up to a concentration of 20 mug/ml (48.3 muM). Compound I demonstrated weak activity with an IC50 value of 34.5 mug/ml (144.7 muM) while being devoid of cytotoxicity at 20 mug/ml. The structures were elucidated by 1D and 2D NMR spectroscopy, and the absolute configuration of the new sesquiterpenoid was determined by the generation of Mosher esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

表征谱图