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

Abstract

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

CLC Number:

TQ35
TQ465

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.

Figures/Tables 2

References 20

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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

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The Antibacterial Activity and Mechanism of Hydronopyl Quaternary Ammonium Compounds

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