(+)-ailanthoidiol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (+)-ailanthoidiol
• 英文别名: Ailanthoidiol；4-[4-[(E)-3-hydroxyprop-1-enyl]phenoxy]-2-methylbutan-1-ol
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: VMNOPCJJVMEHIS-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  月桂酰氯 、 (+)-ailanthoidiol 以 吡啶 为溶剂， 反应 6.0h， 以14 mg的产率得到(+)-ailanthoidiol didodecanoate
  参考文献：
  名称：

  Enhancing activity of antibiotics against Staphylococcus aureus: Zanthoxylum capense constituents and derivatives

  摘要：

  Six compounds (1-6), isolated from the methanol extract of the roots of the African medicinal plant Zanthoxylum capense Thunb. (Rutaceae), and seven ester derivatives (7-13) were evaluated for their antibacterial activities and modulatory effects on the MIC of antibiotics (erythromycin, oxacillin, and tetracycline) and ethidium bromide (EtBr) against a Staphylococcus aureus reference strain (ATCC 6538). Using the same model, compounds 1-13 were also assessed for their potential as efflux pump inhibitors by a fluorometric assay that measures the accumulation of the broad range efflux pump substrate EtBr. Compounds 8 and 11 were further evaluated for their antibacterial, modulatory and EtBr accumulation effects against four additional S. aureus strains, which included two clinical methicillin-resistant S. aureus (MRSA) strains. Compounds (1-13) have not shown antibacterial activity at the concentration ranges tested. When evaluated against S. (wrens ATCC 6538, oxychelerythrine (1) a benzophenanthridine alkaloid, showed the highest modulatory activity enhancing the susceptibility of this strain to all the tested antibiotics from two to four-fold. Ailanthoidiol diacetate (8) and ailanthoidiol di-2-ethylbutanoate (11) were also good modulators when combined with EtBr, increasing the bacteria susceptibility by four and two-fold, respectively. In the EtBr accumulation assay, using ATCC 6533 strain, the phenylpropanoid (+)-ailanthoidiol (6) and most of its ester derivatives (8 11) exhibited higher activity than the positive control verapamil. The highest effects were found for compounds Sand 11 that also increased the accumulation of EtBr, using S:. (wrens ATCC 25923 as model. Furthermore, both compounds (8, 11) were able to enhance the ciprofloxacin activity against the MRSA clinical strains tested, causing a reduction of the antibiotic MIC values from two to four-fold. The EtBr accumulation assay revealed that this modulation activity was not due to an inhibition of efflux pumps mechanism.These results suggested that Z. capense constituents may be valuable as leads for restoring antibiotic activity against MRSA strains. (C) 2015 Elsevier GmbH. All rights reserved.

  DOI：

  10.1016/j.phymed.2015.02.003