SYAUP–CN–26 applies its antifungal activity against Botrytis cinerea by disrupting mitochondrial structure and function

Feng, Tingyue; Li, Jialun; Sun, Mingfan; Peng, Jingnan; Li, Xinghai; Qi, Zhiqiu

doi:10.1016/j.biochi.2020.07.012

Cited by 6 publications

(5 citation statements)

References 36 publications

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“…The changes in mitochondrial number, size, and structure can be caused by a variety of pathogenic factors. The abnormal mitochondrial expression suggests that the target compounds E1 and boscalid have some effect on respiration or energy synthesis in the fungus. − …”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and Action Mechanism of Pyrazole-4-carboxamide Derivatives Containing Oxime Ether Active Fragment As Succinate Dehydrogenase Inhibitors

Chai,

Wang,

Yue

et al. 2024

J. Agric. Food Chem.

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The dearomatization at the hydrophobic tail of the boscalid was carried out to construct a series of novel pyrazole-4-carboxamide derivatives containing an oxime ether fragment. By using fungicide-likeness analyses and virtual screening, 24 target compounds with theoretical strong inhibitory effects against fungal succinate dehydrogenase (SDH) were designed and synthesized. Antifungal bioassays showed that the target compound E1 could selectively inhibit the in vitro growth of R. solani, with the EC50 value of 1.1 μg/mL that was superior to that of the agricultural fungicide boscalid (2.2 μg/mL). The observations by scanning electron microscopy (SEM) and transmission electron microscopy (TEM) demonstrated that E1 could reduce mycelial density and significantly increase the mitochondrial number in mycelia cytoplasm, which was similar to the phenomenon treated with boscalid. Enzyme activity assay showed that the E1 had the significant inhibitory effect against the SDH from R. solani, with the IC50 value of 3.3 μM that was superior to that of boscalid (7.9 μM). The mode of action of the target compound E1 with SDH was further analyzed by molecular docking and molecular dynamics simulation studies. Among them, the number of hydrogen bonds was significantly more in the SDH-E1 complex than that in the SDH-boscalid complex. This research on the dearomatization strategy of the benzene ring for constructing pyrazole-4-carboxamides containing an oxime ether fragment provides a unique thought to design new antifungal drugs targeting SDH.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and Action Mechanism of Pyrazole-4-carboxamide Derivatives Containing Oxime Ether Active Fragment As Succinate Dehydrogenase Inhibitors

Chai,

Wang,

Yue

et al. 2024

J. Agric. Food Chem.

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“…The inhibition rates at 50, 25, 10, 5, and 2.5 µg/mL are shown in Table S1 . B. cinerea is a ubiquitous pathogenic fungus that can infect a wide range of commercial crops and cause important economic losses [ 17 ]. The mechanism of isoxanthohumol on B. cinerea remains largely unclear, so it is important to determine the mechanism of action of isoxanthohumol against B. cinerea .…”

Section: Resultsmentioning

confidence: 99%

“…In general, the respiration of pathogenic fungi functions by absorbing oxygen to release energy, some of which is stored as ATP. In addition, respiratory metabolism can improve the vitality of pathogenic fungi [ 17 ]. The effect of isoxanthohumol on cell respiration is shown in Figure 9 D. The isoxanthohumol decreased the respiration of B. cinerea in a concentration-dependent manner.…”

Section: Resultsmentioning

confidence: 99%

The Antifungal Mechanism of Isoxanthohumol from Humulus lupulus Linn.

Yan

et al. 2021

IJMS

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Humulus lupulus Linn. is a traditional medicinal and edible plant with several biological properties. The aims of this work were: (1) to evaluate the in vitro antifungal activity of H. lupulus ethanolic extract; (2) to study the in vitro and in vivo antifungal activity of isoxanthohumol, an isoprene flavonoid from H. lupulus, against Botrytis cinerea; and (3) to explore the antifungal mechanism of isoxanthohumol on B. cinerea. The present data revealed that the ethanolic extract of H. lupulus exhibited moderate antifungal activity against the five tested phytopathogenic fungi in vitro, and isoxanthohumol showed highly significant antifungal activity against B. cinerea, with an EC50 value of 4.32 µg/mL. Meanwhile, it exhibited moderate to excellent protective and curative efficacies in vivo. The results of morphologic observation, RNA-seq, and physiological indicators revealed that the antifungal mechanism of isoxanthohumol is mainly related to metabolism; it affected the carbohydrate metabolic process, destroyed the tricarboxylic acid (TCA) cycle, and hindered the generation of ATP by inhibiting respiration. Further studies indicated that isoxanthohumol caused membrane lipid peroxidation, thus accelerating the death of B. cinerea. This study demonstrates that isoxanthohumol can be used as a potential botanical fungicide for the management of phytopathogenic fungi.

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“…According to 2.5, the treated solutions were incubated (25 °C, 120 r/min) for 24 h. The TG contents were determined by a microplate reader using commercially available kits (Solarbio, Beijing, China), following the manufacturer’s instructions. The absorbance was measured at 420 nm [ 26 ].…”

Section: Methodsmentioning

confidence: 99%

“…SYAUP-CN-26 (used in this study), chemically named (1 S , 2 R -((3-bromophenethyl)amino)- N -(4-chloro-2-(trifluoromethyl)phenyl)cyclohexane-1-sulfonamide), is a cycloalkyl compound containing one sulfonyl group with significant activity against B. cinerea [ 22 , 23 , 24 , 25 ] ( Figure 1 ). A previous study reported that SYAUP-CN-26 could affect the mitochondrial and cell membrane’s structure and function of B. cinerea [ 25 , 26 ]. Meanwhile, cross-resistance between SYAUP-CN-26 and procymidone was observed against the sensitivity of B. cinerea strains ( Table S1 , Table S2 and Figure S1 in Supplementary Material), indicating that SYAUP-CN-26 might possess a similar action mechanism as procymidone against B. cinerea , and procymidone would lead to lipid peroxidation, inhibit triglyceride synthesis and mycelial growth, and damage the cell membrane.…”

Section: Introductionmentioning

confidence: 99%

Preliminary Study of Resistance Mechanism of Botrytis cinerea to SYAUP-CN-26

Wang¹,

Zhang²,

Zhu³

et al. 2022

Molecules

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SYAUP-CN-26 (1S, 2R-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl) cyclohexane-1-sulfonamide) is a novel sulfonamide compound with excellent activity against Botrytis cinerea. The present study sought to explore the mutant of B.cinerea resistant to SYAUP-CN-26 using SYAUP-CN-26 plates. Moreover, the cell membrane functions of B.cinerea, histidine kinase activity, relative conductivity, triglyceride, and cell membrane structure were determined, and the target gene histidine kinase Bos1 (AF396827.2) of procymidone was amplified and sequenced. The results showed that compared to the sensitive strain, the cell membrane permeability, triglyceride, and histidine kinase activity of the resistant strain showed significant changes. The relative conductivity of the sensitive strain increased by 6.95% and 9.61%, while the relative conductivity of the resistant strain increased by 0.23% and 1.76% with 26.785 µg/mL (EC95) and 79.754 µg/mL (MIC) of SYAUP-CN-26 treatment. The triglyceride inhibition rate of the resistant strain was 23.49% and 37.80%, which was 0.23% and 1.76% higher than the sensitive strain. Compared to the sensitive strain, the histidine kinase activity of the resistant strain was increased by 23.07% and 35.61%, respectively. SYAUP-CN-26 significantly damaged the cell membrane structure of the sensitive strain. The sequencing of the Bos1 gene of the sensitive and resistant strains indicated that SYAUP-CN-26 resistance was associated with a single point mutation (P348L) in the Bos1 gene. Therefore, it was inferred that the mutant of B.cinerea resistant to SYAUP-CN-26 might be regulated by the Bos1 gene. This study will provide a theoretical basis for further research and development of sulfonamide compounds for B. cinerea and new agents for the prevention and control of resistant B. cinerea.

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SYAUP–CN–26 applies its antifungal activity against Botrytis cinerea by disrupting mitochondrial structure and function

Cited by 6 publications

References 36 publications

Design, Synthesis, Antifungal Activity, and Action Mechanism of Pyrazole-4-carboxamide Derivatives Containing Oxime Ether Active Fragment As Succinate Dehydrogenase Inhibitors

Design, Synthesis, Antifungal Activity, and Action Mechanism of Pyrazole-4-carboxamide Derivatives Containing Oxime Ether Active Fragment As Succinate Dehydrogenase Inhibitors

The Antifungal Mechanism of Isoxanthohumol from Humulus lupulus Linn.

Preliminary Study of Resistance Mechanism of Botrytis cinerea to SYAUP-CN-26

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