11(R)-hydroxy-12(20)-en-knightol acetate | 1393916-19-2

• 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: 11(R)-hydroxy-12(20)-en-knightol acetate
• 英文别名: [(1R,4E,7S,11R,14R)-11-hydroxy-14-methyl-10-methylidene-7-prop-1-en-2-yl-15-oxabicyclo[12.1.0]pentadec-4-en-4-yl]methyl acetate
• CAS: 1393916-19-2
• 化学式: C₂₂H₃₄O₄
• 分子量: 362.51
• InChiKey: PQTMOQSFGGWIEJ-XTZZMDRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 11(R)-hydroxy-12(20)-en-knightol acetate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Disruption in Quorum-Sensing Systems and Bacterial Biofilm Inhibition by Cembranoid Diterpenes Isolated from the Octocoral Eunicea knighti

  摘要：

  Three new cembranoid diterpenes, knightine (1), 11(R)-hydroxy-12(20)-en-knightal (2), and 11(R)-hydroxy-12(20)-en-knightol acetate (3), were isolated as minor constituents of the Caribbean gorgonian Eunicea knighti, along with the known cembranoids 4-8. The stereostructures of the new compounds were determined by detailed spectroscopic analyses and a combination of chemical transformations and modified Mosher's methods. All isolated cembranoids were tested against fouling using a quorum-sensing inhibition (QSI) assay and a biofilm inhibition test. Compounds 2, 3, and 6 disrupted QS systems at lower concentrations than kojic acid and Cu2O, and in most cases cembranoids 1-8 showed bacterial biofilm inhibition at lower concentrations than kojic acid.

  DOI：

  10.1021/np300313k

文献信息

• Disruption in Quorum-Sensing Systems and Bacterial Biofilm Inhibition by Cembranoid Diterpenes Isolated from the Octocoral <i>Eunicea knighti</i>
  作者：Edisson Tello、Leonardo Castellanos、Catalina Arévalo-Ferro、Carmenza Duque

  DOI：10.1021/np300313k

  日期：2012.9.28

  Three new cembranoid diterpenes, knightine (1), 11(R)-hydroxy-12(20)-en-knightal (2), and 11(R)-hydroxy-12(20)-en-knightol acetate (3), were isolated as minor constituents of the Caribbean gorgonian Eunicea knighti, along with the known cembranoids 4-8. The stereostructures of the new compounds were determined by detailed spectroscopic analyses and a combination of chemical transformations and modified Mosher's methods. All isolated cembranoids were tested against fouling using a quorum-sensing inhibition (QSI) assay and a biofilm inhibition test. Compounds 2, 3, and 6 disrupted QS systems at lower concentrations than kojic acid and Cu2O, and in most cases cembranoids 1-8 showed bacterial biofilm inhibition at lower concentrations than kojic acid.