Primary Study on Mode of Action for Macrocyclic Fungicide Candidates (<b>7B3</b>, <b>D1</b>) against Rhizoctonia solani Kühn

Yan, Xiaojing; Liang, Xiaomei; Jin, Shiying; Lv, Jinping; Yu, Chunxin; Qi, Wenyan; Li, Baoju; Yuan, Huizhu; Qi, Shu‐Hua; Shi, Yanxia; Wu, Jianyong; Chen, Fu‐Heng; Wang, Daoquan

doi:10.1021/jf9037369

Cited by 30 publications

(24 citation statements)

References 16 publications

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“…4 ). The blank control mycelia of P. infestans grown in the absence of compound I18 demonstrated some cytological and ultrastructural features, which were typical vegetative hyphae of the genus 42 43 ( Fig. 4A,D ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Cui

et al. 2016

Sci Rep

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A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized using Lawesson’s reagent by an efficient approach under microwave irradiation in good yields. Their structures were characterized by MS, IR, 1H NMR, 13C NMR, and elemental analysis. Their in vitro and in vivo fungicidal activities revealed that the title compounds exhibited considerable activity against five selected fungi, especially to Phytophthora infestans. In order to illustrate the mechanism of title compounds against P. infestans, scanning electron micrographs (SEM) and transmission electron micrographs (TEM) were applied. The morphological and ultrastructural studies demonstrated that compound I18 led to swelling of hyphae, thickening and proliferating multilayer cell walls, excessive septation and accumulation of dense bodies. The bioassay results indicated compound I18 might act on cell wall biosynthesis, and blocked the nutrition transportation and led to cells senescence and death. Meanwhile, compound I18 had broad fungicidal activity against other twenty different kinds of fungi. These results suggested that title compounds were eligible to be development candidates and compound I18 as a promising lead compound was worthy to be further discovery, especially against P. infestans.

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Section: Resultsmentioning

confidence: 99%

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Cui

et al. 2016

Sci Rep

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“…SEM and TEM observations showed that the growth inhibition of Fon in response to myriocin was accompanied by conspicuous morphological and cytological changes, including shrivelled cell surface, condensation of the cytoplasm, appearance of larger vacuoles, and the separation of cell wall and cytoplasm. These effects were similar to those of some antibiotics (Yan et al ., 2010; Zhang et al ., 2013, 2016). In a study, the formation of larger vacuoles has been reported to be closely related to antifungal activity (Thimon et al ., 1995).…”

Section: Discussionmentioning

confidence: 99%

Membrane disruption of Fusarium oxysporum f. sp. niveum induced by myriocin from Bacillus amyloliquefaciens LZN01

Wang

Liu

et al. 2020

Microbial Biotechnology

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Myriocin, which is produced by Bacillus amyloliquefaciens LZN01, can inhibit the growth of Fusarium oxysporum f. sp. niveum (Fon). In the present study, the antifungal mechanism of myriocin against Fon was investigated with a focus on the effects of myriocin on the cell membrane. Myriocin decreased the membrane fluidity and destroyed the membrane integrity of Fon. Significant microscopic morphological changes, including conidial shrinkage, the appearance of larger vacuoles and inhomogeneity of electron density, were observed in myriocin-treated cells. A membrane-targeted mechanism of action was also supported by transcriptomic and proteomic analyses; a total of 560 common differentially expressed genes (DEGs) and 285 common differentially expressed proteins (DEPs) were identified. The DEGs were further verified by using RT-qPCR. The combined analysis between the transcriptome and proteome revealed that the expression of some membrane-related genes and proteins, mainly those related to sphingolipid metabolism, glycerophospholipid metabolism, steroid biosynthesis, ABC transporters and protein processing in the endoplasmic reticulum, was disordered. Myriocin affected the serine palmitoyl transferase (SPT) activity as evidenced through molecular docking. Our results indicate that myriocin has significant antifungal activity owing to its ability to induce membrane damage in Fon.

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“…After treatment with 50 μg/mL 18 for 48 h, R. solani mycelia tips (0.5 cm) were cut, treated with 2.5% of glutaraldehyde at 4 °C, and subsequently fixed with 1% ( w / v ) osmium tetraoxide solution after being rinsed with 0.1 M phosphate buffer (PBS, pH = 7.4) three times. The samples were dehydrated using a series of ethanol solutions (30%, 50%, 70%, 80%, 90%, and 100%), dried at critical point, mounted, gold-sprayed, and then observed under a XL-30-ESEM scanning electron microscope (FEI, Eindhoven, Netherlands) [22].…”

Section: Methodsmentioning

confidence: 99%

Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani

Zhang

Zhu

et al. 2018

IJMS

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Rice sheath blight, caused by Rhizoctonia solani, is a globally important rice disease and the increasing resistance of this pathogen highlights the need for new active compounds against rice sheath blight. In this study, natural β-carboline alkaloids were optimized to obtain a series of 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene derivatives and evaluated for their fungicidal activity and mode of action against R. solani. Of these compounds, 18 exhibited significant in vitro fungicidal activity against R. solani, with an EC50 value of 2.35 μg/mL, and was more active than validamycin A. In vivo bioassay also demonstrated that 18 displayed superior protective and curative activities as compared to validamycin A. Mechanistically, 18 not only induced the loss of mitochondrial membrane potential and accumulation of reactive oxygen species, but also interfered with DNA synthesis. Therefore, compound 18 displayed pronounced in vitro and in vivo fungicidal activity against R. solani and could be used as a potential candidate for the control of rice sheath blight.

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Primary Study on Mode of Action for Macrocyclic Fungicide Candidates (7B3, D1) against Rhizoctonia solani Kühn

Cited by 30 publications

References 16 publications

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Membrane disruption of Fusarium oxysporum f. sp. niveum induced by myriocin from Bacillus amyloliquefaciens LZN01

Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani

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