Antifungal activity and preliminary mechanism of pristimerin against Sclerotinia sclerotiorum

Zhao, Wei; Zhao, Zhuanjun; Ma, Yue; Li, An‐Ping; Zhang, Zhijun; Hu, Yongmei; Zhou, Yong; Wang, Rui; Luo, Xiaoxing; Zhang, Bao‐Qi; Wang, Yuling; Guanfang, Hu; Liu, Ying‐Qian

doi:10.1016/j.indcrop.2022.115124

Cited by 21 publications

(19 citation statements)

References 39 publications

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“…The hyphae of N. oryzae were treated with T 6 and penthiopyrad (0, 10, and 20 mg/L) and incubated for 12, 24, and 36 h. The samples were cleaned with PBS (2 mL × 3), fixed in 4 °C stationary liquid (2.5% glutaraldehyde) for 24 h, and then washed with PBS, ethanol (30%, 50%, 70%, 90%, and 100%), and 100% tert -butanol at 4 °C. After freeze-drying and coating with gold, the samples were observed by SEM …”

Section: Methodsmentioning

confidence: 99%

“…2.3.2. General Procedure for the Synthesis of Compounds T 1 − T 25 . Intermediates B were further reacted with the solvent SOCl 2 according to previously reported work to obtain transition state acyl chlorides, 19,20 which were used directly for the next reaction.…”

Section: Methodsmentioning

confidence: 99%

“…After freeze-drying and coating with gold, the samples were observed by SEM. 25 2.7.2. Morphological Analysis by FM.…”

Section: Morphological Analysis By Semmentioning

confidence: 99%

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Design, Synthesis, and Study of the Dual Action Mode of Novel N-Thienyl-1,5-disubstituted-4-pyrazole Carboxamides against Nigrospora oryzae

Zhang

Zhao

Zheng

et al. 2023

J. Agric. Food Chem.

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Due to the single target but extensive application of commercialized succinate dehydrogenase inhibitors (SDHIs), resistance problems have gradually become apparent in recent years. To solve this problem, a series of novel N-thienyl-1,5-disubstituted-1H-4-pyrazole carboxamide derivatives were designed and synthesized in this work based on the active skeleton 5-trifluoromethyl-4-pyrazole carboxamide. The bioassay results indicated that some target compounds exhibited excellent in vitro antifungal activities against the eight phytopathogenic fungi tested. Among them, the EC50 values of T 4 , T 6 , and T 9 against Nigrospora oryzae were 5.8, 1.9, and 5.5 mg/L, respectively. The in vivo protective and curative activities of 40 mg/L T 6 against rice infected with N. oryzae were 81.5% and 43.0%, respectively. Further studies revealed that T 6 not only significantly inhibited the growth of N. oryzae mycelia but also effectively hindered spore germination and germ tube elongation. Morphological studies using scanning electron microscopy (SEM), fluorescence microscopy (FM), and transmission electron microscopy (TEM) found that T 6 could affect the mycelium membrane integrity by increasing cell membrane permeability and causing peroxidation of cellular lipids, and these results were further verified by measuring the malondialdehyde (MDA) content. The IC50 value of T 6 against succinate dehydrogenase (SDH) was 7.2 mg/L, lower than that of the commercialized SDHI penthiopyrad (3.4 mg/L). Further, ATP content detection and the results after docking T 6 and penthiopyrad suggested that T 6 was a potential SDHI. These studies demonstrated that active compound T 6 could both inhibit the activity of SDH and affect the integrity of the cell membrane at the same time via a dual action mode, which is different from the mode of action of penthiopyrad. Thus, this study provides a new idea for a strategy to delay resistance and diversify the structures of SDHIs.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, and Study of the Dual Action Mode of Novel N-Thienyl-1,5-disubstituted-4-pyrazole Carboxamides against Nigrospora oryzae

Zhang

Zhao

Zheng

et al. 2023

J. Agric. Food Chem.

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“…Morphological changes in the cells after treatment with the compound A26 were observed as described previously. 43 The bacteria were washed three times with phosphate-buffered saline (PBS) to make a final volume of 1 mL, and compounds dissolved in DMSO were added at concentrations of 1/2, 1 and 2 MIC. Bacteria were treated using the same volume of DMSO in 1 mL PBS as a negative control.…”

Section: Scanning Electron Microscopy (Sem) Observationsmentioning

confidence: 99%

Short pathways to highly active antimicrobial: structurally diverse polyamines derivatives from Amino‐Aldehyde condensation strategy

Ma,

Zhou,

Wang

et al. 2023

Pest Management Science

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BackgroundChemical fungicides are the mainstay of plant disease control in agricultural production, but there are a very limited number of drugs that can effectively control plant diseases. Two series of secondary amine derivatives were synthesized using the diamine skeleton combined with saturated aromatic and aliphatic aldehydes, and their antibacterial and antifungal activities against plant pathogens were determined. In addition, the antimicrobial mechanism of the highly active compound A26 was preliminarily examined against Xanthomonas oryzae (Xoo).ResultsCompound A26 exhibited the highest antibacterial potency among all the target compounds, with MIC values of 3.12, 3.12, and 12.5 μg/mL against Xoo, Xanthomonas axonopodis pv. Citri (Xac) and Pseudomonas sollamacearum (Ps), respectively. In addition, compound A26 had powerful curative and protective effects against Xoo at 200 μg/mL, and was better than the control agent Xinjunan. Preliminary mechanistic studies showed that compound A26 reduced the bacterial pathogenicity by targeting cell membranes and inhibiting the secretion of extracellular polysaccharides (EPS). Meanwhile, the toxicity of compound A26 to Human Embryonic Kidney 293 cells and Human Liver‐7702 was similar to that of Xinjunan, and it had the moderate toxicity according to the World Health Organization classification standard of oral exogenous toxicity with the LD50 of 245.47 mg/kg.ConclusionSecondary amines have efficient and broad‐spectrum antibacterial activity against plant pathogenic bacteria and are expected to be a new class of candidate compounds for antibacterial drugs.This article is protected by copyright. All rights reserved.

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“…Pyruvate content, ATP content and mitochondrial membrane potential are important indicators of mitochondrial functions. 13,42,43 The pyruvate and ATP content of S. rolfsii mycelia after treatments with butylidenephthalide (0, EC 50 and EC 85 ; www.soci.org K Cui et al…”

Section: Pyruvate Atp Content and Mitochondrial Membrane Potentialmentioning

confidence: 99%

Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii

Cui,

He,

Wang

et al. 2023

Pest Management Science

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BACKGROUNDPeanut stem rot caused by Sclerotium rolfsii is an epidemic disastrous soil‐borne disease. Recently, natural products tend to be safe alternative antifungal agents to combat pathogens.RESULTSThis work determined the preliminary antifungal activity of 29 essential oils against S. rolfsii and found that Ligusticum chuanxiong essential oil (LCEO) showed the best antifungal activity, with an EC50 value of 81.79 mg/L. Sixteen compositions (98.78%) were identified in LCEO by GC‐MS analysis, the major compositions were five phthalides (93.14%). Among these 5 phthalides, butylidenephthalide was the most effective compound against S. rolfsii. Butylidenephthalide not only exhibited favorable in vitro antifungal activity against the mycelial growth, sclerotia production and germination of S. rolfsi, but also presented efficient in vivo efficacy in the control of peanut stem rot. Seven days after application in greenhouse, the protective and curative efficacy of butylidenephthalide at 300 mg/L (52.02%, 44.88%) and LCEO at 1,000 mg/L (49.60%, 44.29%) against S. rolfsii were similar to that of the reference fungicide polyoxin at 300 mg/L (54.61%, 48.28%). Butylidenephthalide also significantly decreased the oxalic acid and polygalacturonase content of S. rolfsii, suggesting a decreased infection ability on plants. Results of biochemical actions indicated that butylidenephthalide did not have any effect on the cell membrane integrity and permeability but significantly decreased nutrient contents, disrupted the mitochondrial membrane, inhibited energy metabolism and induced reactive oxygen species (ROS) accumulation of S. rolfsii.CONCLUSIONOur results could provide an important reference for understanding the application potential and mechanisms of butylidenephthalide in the control of S. rolfsii.This article is protected by copyright. All rights reserved.

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Antifungal activity and preliminary mechanism of pristimerin against Sclerotinia sclerotiorum

Cited by 21 publications

References 39 publications

Design, Synthesis, and Study of the Dual Action Mode of Novel N-Thienyl-1,5-disubstituted-4-pyrazole Carboxamides against Nigrospora oryzae

Design, Synthesis, and Study of the Dual Action Mode of Novel N-Thienyl-1,5-disubstituted-4-pyrazole Carboxamides against Nigrospora oryzae

Short pathways to highly active antimicrobial: structurally diverse polyamines derivatives from Amino‐Aldehyde condensation strategy

Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii

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