含氢化诺卜基的季铵盐化合物的抑菌活性及其机理研究

doi:10.3969/j.issn.0253-2417.2023.04.004

林产化学与工业 ›› 2023, Vol. 43 ›› Issue (4): 25-30.doi: 10.3969/j.issn.0253-2417.2023.04.004

含氢化诺卜基的季铵盐化合物的抑菌活性及其机理研究

丁清颖¹, 昌家宇¹, 肖转泉², 范国荣¹, 王宗德¹, 陈尚钘¹^,*()

1. 江西农业大学林学院；国家林业草原木本香料(华东)工程技术研究中心；国家林业草原/江西省樟树工程技术研究中心，江西南昌 330045
2. 江西师范大学化学化工学院，江西南昌 330022

收稿日期:2022-04-08 出版日期:2023-08-28 发布日期:2023-08-26
通讯作者: 陈尚钘 E-mail:csxing@126.com
作者简介:陈尚钘，教授，博士，博士生导师，研究领域为芳香植物精油；E-mail：csxing@126.com
丁清颖(1999—)，女，江西九江人，硕士生，研究方向：芳香植物精油的利用
基金资助:
江西省重点研发计划资助项目(20192ACB60011);江西省“千人计划”首批培养类科技创新高端人才项目(JXSQ2019201016);江西省重大科技研发专项(20203ABC28W016)

The Antibacterial Activity and Mechanism of Hydronopyl Quaternary Ammonium Compounds

Qingying DING¹, Jiayu CHANG¹, Zhuanquan XIAO², Guorong FAN¹, Zongde WANG¹, Shangxing CHEN¹^,*()

1. College of Forestry, Jiangxi Agricultural University; East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration; Camphor Engineering Research Center of NFGA/Jiangxi Province, Nanchang 330045, China
2. College of Chemical, Jiangxi Normal University, Nanchang 330022, China

Received:2022-04-08 Online:2023-08-28 Published:2023-08-26
Contact: Shangxing CHEN E-mail:csxing@126.com

摘要/Abstract

摘要：

以松节油主要成分之一的β-蒎烯为原料合成得到含单氢化诺卜基的单季铵盐(1~13)、含双氢化诺卜基的单季铵盐(14~18)及含双氢化诺卜基的对称型双子季铵盐(19~36)共36个季铵盐类化合物，采用96孔板法，以刃天青作显色剂，以硫酸卡那霉素为阳性对照，测试了化合物对大肠杆菌、恶臭假单胞菌、金黄色葡萄球菌和枯草芽孢杆菌等4种有害细菌的最小抑菌浓度(MIC值)。结果表明：36个季铵盐化合物的抑菌活性都明显优于原料β-蒎烯和关键中间体氢化诺卜醇；分子中含有氢化诺卜基与长碳链烷基的单季铵盐(10~11)、含有双氢化诺卜基的单季铵盐(14~18)以及含有双氢化诺卜基的对称型双子季铵盐(19~36)的抑菌活性均较高，但大多数化合物的MIC值都高于硫酸卡那霉素的MIC值(对恶臭假单胞菌的MIC值为10 mg/L，对另3种菌的MIC值为5 mg/L)；而双氢化诺卜基二甲基溴化铵(14)对恶臭假单胞菌的MIC值为1.25 mg/L、对金黄色葡萄球菌和枯草芽孢杆菌的MIC值均为2.5 mg/L，双氢化诺卜基二乙基溴化铵(16)对恶臭假单胞菌的MIC值为2.5 mg/L，均低于阳性对照硫酸卡那霉素的MIC值。此外，初步的抗菌机理研究显示：化合物14可以增加恶臭假单胞菌的细胞膜通透性，使相对电导率明显增加；同时抑制其ATP酶活性，这些氢化诺卜基季铵盐类化合物有望作为潜在的抗菌剂。

关键词: 氢化诺卜基, 季铵盐, 细菌, 抑菌活性, 抑菌机理

Abstract:

In this work, we adopted β-pinene, which was one of the main components of turpentine oil, to synthesize 36 quaternary ammonium compounds including hydronopyl monoquaternary ammonium salts(1-13), dihydronopyl monoquaternary ammonium salts(14-18) and symmetric dihydronopyl bis-quaternary ammonium salts(19-36). The minimum inhibitory concentrations(MIC) of these compounds against four harmful bacteria such as Escherichia coli, Pseudomonas putida, Staphylococcus aureus and Bacillus subtilis were tested by 96-well microtiter plates, using resazurin as chromogenic agent and kanamycin sulfate as the positive control. The results showed that the antibacterial activities of the synthesized quaternary ammonium compounds were significantly higher than that of the starting material β-pinene and the critical intermediate hydronol. The monoquaternary ammonium salts with hydronopyl and long carbon chain alkyl(10-11), the monoquaternary ammonium salts with dihydronopyl(14-18), and the symmetric dihydronopyl bis-quaternary ammonium salts(19-36) had high antibacterial activity, while the MIC values of most quaternary ammonium compounds were higher than those of kanamycin sulfate(the MIC values against P. putida and the other three bacteria are 10 mg/L and 5 mg/L, respectively). The MIC values of dihydronobuyl dimethyl ammonium bromide(14) against P. putida, S. aureus and B. subtilis were 1.25 mg/L, 2.5 mg/L, 2.5 mg/L, respectively, and the MIC value of dihydronobuyl diethyl ammonium bromide(16) against P. putida was 2.5 mg/L, which was lower than the MIC value of the positive control kanamycin sulfate. Furthermore, the preliminary antibacterial mechanism studies revealed that compound 14 increased the permeability of P. putida cell membranes, resulting in a significant increase in relative conductivity, and at the same time, inhibiting its ATP activity. These hydronopyl quaternary ammonium compounds were expected to be used as potential antimicrobial agents.

Key words: hydronopyl, quaternary ammonium salt, bacteria, antibacterial activity, antibacterial mechanism

中图分类号:

TQ35
TQ465

丁清颖, 昌家宇, 肖转泉, 范国荣, 王宗德, 陈尚钘. 含氢化诺卜基的季铵盐化合物的抑菌活性及其机理研究[J]. 林产化学与工业, 2023, 43(4): 25-30.

Qingying DING, Jiayu CHANG, Zhuanquan XIAO, Guorong FAN, Zongde WANG, Shangxing CHEN. The Antibacterial Activity and Mechanism of Hydronopyl Quaternary Ammonium Compounds[J]. Chemistry and Industry of Forest Products, 2023, 43(4): 25-30.

图/表 2

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含氢化诺卜基的季铵盐化合物的抑菌活性及其机理研究

The Antibacterial Activity and Mechanism of Hydronopyl Quaternary Ammonium Compounds

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化合物 compound	大肠杆菌 E.coli	恶臭假单胞菌 P.putida	金黄色葡萄球菌 S.aureus	枯草芽孢杆菌 B.subtilis
1	320	320	640	640
2	320	320	640	320
3	160	80	40	160
4	160	160	160	320
5	2 560	640	160	640
6	640	1 280	1 280	320
7	2 560	1 280	2 560	640
8	160	640	320	640
9	640	320	320	320
10	10	10	10	80
11	10	10	10	10
12	1 280	320	320	1 280
13	640	160	160	320
14	5	1.25	2.5	2.5
15	20	80	80	5
16	10	2.5	5	5
17	80	80	80	80
18	20	20	5	40
19	40	20	40	40
20	160	40	10	5
21	320	80	80	320
22	160	40	20	80
23	80	20	10	80
24	80	160	80	80
25	40	40	20	20
26	20	20	20	20
27	20	20	80	40
28	40	40	40	40
29	80	20	40	40
30	40	40	40	40
31	20	20	10	10
32	20	20	20	20
33	5	10	10	5
34	20	20	80	80
35	80	20	40	80
36	10	10	80	160
β-蒎烯 β-pinene	—	—	—	—
氢化诺卜醇 hydronol	10 240	2 560	10 240	2 560
链霉素 streptomycin	320	2 560	1 280	2 560
硫酸卡那霉素 kanamycin sulfate	5	10	5	5