Huang Yanqun, Huo Shangchao, Mo Junming, Huang Daozhan
School of Materials and Environment, Guangxi Minzu University, Nanning 530105, China.
School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530008, China.
ACS Omega. 2023 Sep 18;8(38):34687-34697. doi: 10.1021/acsomega.3c03599. eCollection 2023 Sep 26.
A series of novel quaternary ammonium salts (QASs) (-) comprising a camphene moiety were synthesized for the first time. Fourteen examples were prepared from camphene through Prins reaction, halogenation, and quaternarization, successively. The structures of the synthesized QASs were analyzed by Fourier transform infrared spectroscopy, H NMR, C NMR and high-resolution mass spectrometry. Surface-active properties, emulsifying abilities, and foaming properties of the investigated compounds were then studied. The antimicrobial activities of these QASs against Gram-positive bacteria ( and ), Gram-negative bacteria ( and ), and fungi species (, , and ) were determined by the microdilution method. The results showed that the chemical structural factors, including types of substitutes and alkyl chain length, might be correlated with the lipid-water partition coefficient (cLog ), which played a critical role in the antimicrobial process. Compounds with alkyl chain lengths () in the range of 10-14 were relatively more active, while compounds bearing pyridinium, benzyl, methylimidazolium groups, or varied alkyl chain lengths ( < 5 and > 16) were almost inactive. Compound possessing a dodecyl group exhibited the most effective and broad-spectrum antimicrobial activity against almost all tested bacteria and fungi with the minimal inhibitory concentration values ranging from 0.24 to 0.98 μg/mL.
首次合成了一系列含有莰烯部分的新型季铵盐（QASs）（-）。通过莰烯依次经普林斯反应、卤化和季铵化反应制备了14个实例。通过傅里叶变换红外光谱、氢核磁共振、碳核磁共振和高分辨率质谱对合成的QASs的结构进行了分析。然后研究了所研究化合物的表面活性、乳化能力和发泡性能。通过微量稀释法测定了这些QASs对革兰氏阳性菌（和）、革兰氏阴性菌（和）以及真菌物种（、和）的抗菌活性。结果表明，包括取代基类型和烷基链长度在内的化学结构因素可能与脂水分配系数（cLog）相关，脂水分配系数在抗菌过程中起关键作用。烷基链长度（）在10 - 14范围内的化合物相对更具活性，而带有吡啶鎓、苄基、甲基咪唑鎓基团或不同烷基链长度（<5和>16）的化合物几乎没有活性。具有十二烷基的化合物对几乎所有测试的细菌和真菌表现出最有效和广谱的抗菌活性，最小抑菌浓度值范围为0.24至0.98μg/mL。
