Novel 18β-glycyrrhetinic acid amide derivatives show dual-acting capabilities for controlling plant bacterial diseases through ROS-mediated antibacterial efficiency and activating plant defense responses

Song, Ying‐Lian; LIU, Hong-wu; YANG, Yi-hong; HE, Jing-jing; Yang, Binxin; Yang, Lin-Li; Zhou, Xiang; LIU, Li-wei; WANG, Pei-yi; Yang, Song

doi:10.1016/j.jia.2022.10.009

Cited by 14 publications

(6 citation statements)

References 44 publications

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“…Generally, the target compounds were evaluated for their preliminary in vitro bioactivities against three devastating phytopathogenic bacteria ( Xoo , Xac and Psa ) via the turbidimetric test [ 39 , 40 , 41 , 42 ]. The commonly used bactericides bismerthiazol ( BT ) and thiodiazole copper ( TC ) ( Figure 2 ) were chosen as positive controls [ 43 , 44 ].…”

Section: Resultsmentioning

confidence: 99%

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Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents

Liu

Yang

et al. 2023

Molecules

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Imidazole alkaloids, a common class of five-membered aromatic heterocyclic compounds, exist widely in plants, animals and marine organisms. Because of imidazole’s extensive and excellent biological and pharmacological activities, it has always been a topic of major interest for researchers and has been widely used as an active moiety in search of bioactive molecules. To find more efficient antibacterial compounds, a series of novel imidazole-fragment-decorated 2-(pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized based on our previous works via the active substructure splicing principle, and their bioactivities were systematically evaluated both in vitro and in vivo. The bioassays showed that some of the target compounds displayed excellent in vitro antibacterial activity toward three virulent phytopathogenic bacteria, including Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac) and Pseudomonas syringae pv. actinidiae (Psa), affording the lowest EC50 values of 7.40 (7c), 5.44 (9a) and 12.85 (9a) μg/mL, respectively. Meanwhile, compound 7c possessed good in vivo protective and curative activities to manage rice bacterial leaf blight at 200 μg/mL, with control efficacies of 47.34% and 41.18%, respectively. Furthermore, compound 9a showed commendable in vivo protective and curative activities to manage kiwifruit bacterial canker at 200 μg/mL, with control efficacies of 46.05% and 32.89%, respectively, which were much better than those of the commercial bactericide TC (31.58% and 17.11%, respectively). In addition, the antibacterial mechanism suggested that these new types of title compounds could negatively impact the cell membranes of phytopathogenic bacteria cells and cause the leakage of the intracellular component, thereby leading to the killing of bacteria. All these findings confirm that novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles containing an imidazole fragment are promising lead compounds for discovering new bactericidal agents.

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Section: Resultsmentioning

confidence: 99%

“…The in vitro bioassays against three phytopathogenic bacteria Xoo , Xac and Psa , in vivo pot experiment for managing rice bacterial leaf blight and SEM imaging experiment were according to our reported methods [ 39 , 40 , 41 , 42 ]. All the detailed descriptions are displayed in Supplementary Materials .…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents

Liu

Yang

et al. 2023

Molecules

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“…Studies on Xanthomonas oryzae pv. oryzae and SiHa cells have shown that Enoxolone and its derivatives can cause excessive production and accumulation of intracellular ROS and thus induce apoptosis (Lee et al, 2008 ; Song et al, 2022 ). Enoxolone may also exhibit antibacterial activity against Staphylococcus aureus by affecting carbohydrate and amino acid metabolism (Oyama et al, 2016 ).…”

Section: Discussionmentioning

confidence: 99%

Identification of TonB-dependent siderophore receptor inhibitors against Flavobacterium columnare using a structure-based high-throughput virtual screening method

Li,

Chen,

et al. 2024

Front. Microbiol.

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TonB-dependent siderophore receptors play a critical transport role for Flavobacterium columnare virulence formation and growth, and have become valuable targets for the development of novel antimicrobial agents. Traditional Chinese medicine has demonstrated notable efficacy in the treatment of fish diseases and includes potential antibacterial agents. Herein, we performed molecular docking-based virtual screening to discover novel TonB-dependent siderophore receptor inhibitors from traditional Chinese medicine and provide information for developing novel antibacterial agents. Firstly, we efficiently obtained 11 potential inhibitors with desirable drug-like characteristics from thousands of compounds in the TCM library based on virtual screening and property prediction. The antibacterial activity of Enoxolone, along with its interaction characteristics, were determined via an MIC assay and molecular dynamic simulation. Transcriptional profiling, along with validation experiments, subsequently revealed that an insufficient uptake of iron ions by bacteria upon binding to the TonB-dependent siderophore receptors is the antibacterial mechanism of Enoxolone. Finally, Enoxolone's acceptable toxicity was illustrated through immersion experiments. In summary, we have used virtual screening techniques for the first time in the development of antimicrobial agents in aquaculture. Through this process, we have identified Enoxolone as a promising compound targeting the TonB-dependent siderophore receptor of F. columnare. In addition, our findings will provide new ideas for the advancement of innovative antimicrobial medications in aquaculture.

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“…Chemical antibacterial agents have been widely used since the 1960s and remain a major pathogen control method in current agriculture. However, the irregular use of traditional chemical antibacterial agents including bismerthiazol (BT) and thiodiazole copper (TC) increases the resistance of plant pathogens, reducing the control efficiency of these agents, which are also toxic for humans and the environment [ 9 , 10 ]. Therefore, it is urgent to develop new, low-risk, green agrochemicals with high efficiency and high selectivity to manage plant diseases, thereby improving production levels and meeting the population’s needs.…”

Section: Introductionmentioning

confidence: 99%

Novel Sulfonamide Derivatives Containing a Piperidine Moiety as New Bactericide Leads for Managing Plant Bacterial Diseases

Xie

Long

Gao

et al. 2023

IJMS

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Plant bacterial diseases are an intractable problem due to the fact that phytopathogens have acquired strong resistances for traditional pesticides, resulting in restricting the quality and yield of agricultural products around the world. To develop new agrochemical alternatives, we prepared a novel series of sulfanilamide derivatives containing piperidine fragments and assessed their antibacterial potency. The bioassay results revealed that most molecules displayed excellent in vitro antibacterial potency towards Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac). In particular, molecule C4 exhibited outstanding inhibitory activity toward Xoo with EC50 value of 2.02 µg mL−1, which was significantly better than those of the commercial agents bismerthiazol (EC50 = 42.38 µg mL−1) and thiodiazole copper (EC50 = 64.50 µg mL−1). A series of biochemical assays confirmed that compound C4 interacted with dihydropteroate synthase, and irreversibly damaged the cell membrane. In vivo assays showed that the molecule C4 presented acceptable curative and protection activities of 34.78% and 39.83%, respectively, at 200 µg mL−1, which were greater than those of thiodiazole and bismerthiazol. This study highlights the valuable insights for the excavation and development of new bactericides that can concurrently target dihydropteroate synthase and bacterial cell membranes.

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Novel 18β-glycyrrhetinic acid amide derivatives show dual-acting capabilities for controlling plant bacterial diseases through ROS-mediated antibacterial efficiency and activating plant defense responses

Cited by 14 publications

References 44 publications

Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents

Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents

Identification of TonB-dependent siderophore receptor inhibitors against Flavobacterium columnare using a structure-based high-throughput virtual screening method

Novel Sulfonamide Derivatives Containing a Piperidine Moiety as New Bactericide Leads for Managing Plant Bacterial Diseases

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