Synthesis of antibiofilm (1R,4S)-(-)-fenchone derivatives to control Pseudomonas syringae pv. tomato
文献类型: 外文期刊
作者: Wang, Delong 1 ; Li, Yunpeng 1 ; Li, Linjing 1 ; Chen, Yizhe 1 ; Min, Shuoling 1 ; Wang, Yong 2 ; Feng, Juntao 2 ; Zhou, Jianbo 1 ; Zhang, Zhijia 1 ; Fang, Yali 1 ;
作者机构: 1.Shanxi Agr Univ, Coll Plant Protect, Shanxi Key Lab Integrated Pest Management Agr, Taiyuan 030031, Shanxi, Peoples R China
2.Northwest A&F Univ, Coll Plant Protect, State Key Lab Crop Stress Biol Arid Areas, Key Lab Plant Protect Resources & Pest Management,, Yangling 712100, Shaanxi, Peoples R China
关键词: (1R,4S)-(-)-fenchone; semisynthetic derivatives; antibiofilm activity; Pseudomonas syringae pv tomato; synergistic effects
期刊名称:PEST MANAGEMENT SCIENCE ( 影响因子:3.8; 五年影响因子:4.3 )
ISSN: 1526-498X
年卷期: 2025 年 81 卷 3 期
页码:
收录情况: SCI
摘要: BACKGROUND: Biofilm plays a crucial role in Pseudomonas syringae pv. tomato (Pst) infection. We identified (1R,4S)-(-)-fenchone (FCH) as the most potent antibiofilm agent against Pst among 39 essential oil compounds. Subsequently, we synthesized a series of FCH oxime ester and acylhydrazine derivatives to explore more potent derivatives. RESULTS: II3 was screened out as the most potent derivative, exhibiting a minimal biofilm inhibitory concentration of 60 mu g mL-1 and a lowest concentration with maximal biofilm inhibition (LCMBI) of 200 mu g mL(-1), lower than those of FCH (80 and 500 mu g mL(-1), respectively). II3 and FCH showed minimum inhibitory concentration values >1000 mu g mL(-1) and similar maximal biofilm inhibition extents of 48.7% and 49.5% at their respective LCMBIs, respectively. Meanwhile, neither of them influenced cell viability or the activity of metabolic enzymes at their respective LCMBIs. II3 at its LCMBI significantly reduced biofilm thickness, extracellular polysaccharide content, and pectinase and cellulase production indices. In vivo assay results indicated that II3 could preventatively reduce the bacterial contents in tomato leaves at its LCMBI, and when combined with kasugamycin (KSG) (10 mu g mL(-1)), II3 achieved the same level of bacterial reduction as the sole application of KSG (70 mu g mL(-1)), thereby reducing the required dosage of KSG. Mechanistic studies demonstrated that II3 can down-regulate biofilm-related genes and inhibit PsyR/PsyI quorum sensing system, which differs from the bactericidal mechanisms. CONCLUSION: These results underscore the potential of II3 as an antibiofilm agent for the control of Pst or FCH as a promising natural candidate for future in-depth optimization. (c) 2024 Society of Chemical Industry.
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