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1.
Molecules ; 29(13)2024 Jul 02.
Artigo em Inglês | MEDLINE | ID: mdl-38999100

RESUMO

Plant diseases caused by pathogenic fungi seriously affect the yield and quality of crops, cause huge economic losses, and pose a considerable threat to global food security. Phenylpyrrole analogues were designed and synthesized based on alkaloid lycogalic acid. All target compounds were characterized by 1H NMR, 13C NMR, and HRMS. Their antifungal activities against seven kinds of phytopathogenic fungi were evaluated. The results revealed that most compounds had broad-spectrum fungicidal activities at 50 µg/mL; 14 compounds displayed more than 60% fungicidal activities against Rhizoctonia cerealis and Sclerotinia sclerotiorum, and in particular, the fungicidal activities of compounds 8g and 8h against Rhizoctonia cerealis were more than 90%, which could be further developed as lead agents for water-soluble fungicides. The molecular docking results indicate that compounds 8g and 8h can interact with 14α-demethylase (RcCYP51) through hydrogen bonding with strong affinity.


Assuntos
Alcaloides , Antifúngicos , Desenho de Fármacos , Simulação de Acoplamento Molecular , Pirróis , Rhizoctonia , Antifúngicos/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Pirróis/química , Pirróis/farmacologia , Pirróis/síntese química , Alcaloides/química , Alcaloides/farmacologia , Alcaloides/síntese química , Rhizoctonia/efeitos dos fármacos , Relação Estrutura-Atividade , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ascomicetos/efeitos dos fármacos
2.
J Agric Food Chem ; 72(28): 15474-15486, 2024 Jul 17.
Artigo em Inglês | MEDLINE | ID: mdl-38949855

RESUMO

Corn ear rot and fumonisin caused by Fusarium verticillioides pose a serious threat to food security. To find more highly active fungicidal and antitoxic candidates with structure diversity based on naturally occurring lead xanthatin, a series of novel spiropiperidinyl-α-methylene-γ-butyrolactones were rationally designed and synthesized. The in vitro bioassay results indicated that compound 7c showed broad-spectrum in vitro activity with EC50 values falling from 3.51 to 24.10 µg/mL against Rhizoctonia solani and Alternaria solani, which was more active than the positive controls xanthatin and oxathiapiprolin. In addition, compound 7c also showed good antitoxic efficacy against fumonisin with a 48% inhibition rate even at a concentration of 20 µg/mL. Fluorescence quenching and the molecular docking validated both 7c and oxathiapiprolin targeting at FvoshC. RNA sequencing analysis discovered that FUM gene cluster and protein processing in endoplasmic reticulum were downregulated. Our studies have discovered spiropiperidinyl-α-methylene-γ-butyrolactone as a novel FvoshC target-based scaffold for fungicide lead with antitoxin activity.


Assuntos
Alternaria , Fungicidas Industriais , Fusarium , Simulação de Acoplamento Molecular , Rhizoctonia , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Alternaria/efeitos dos fármacos , Fusarium/efeitos dos fármacos , Rhizoctonia/efeitos dos fármacos , Relação Estrutura-Atividade , Doenças das Plantas/microbiologia , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Proteínas Fúngicas/química , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Receptores de Esteroides/metabolismo , Receptores de Esteroides/genética , Receptores de Esteroides/química , Descoberta de Drogas , Zea mays/química , Zea mays/microbiologia , Estrutura Molecular
3.
Molecules ; 29(11)2024 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-38893377

RESUMO

Plant pathogenic fungi pose a major threat to global food security, ecosystem services, and human livelihoods. Effective and broad-spectrum fungicides are needed to combat these pathogens. In this study, a novel antifungal 2-oxyacetate hydrazide quinoxaline scaffold as a simple analogue was designed and synthesized. Their antifungal activities were evaluated against Botrytis cinerea (B. cinerea), Altemaria solani (A. solani), Gibberella zeae (G. zeae), Rhizoctonia solani (R. solani), Colletotrichum orbiculare (C. orbiculare), and Alternaria alternata (A. alternata). These results demonstrated that most compounds exhibited remarkable inhibitory activities and possessed better efficacy than ridylbacterin, such as compound 15 (EC50 = 0.87 µg/mL against G. zeae, EC50 = 1.01 µg/mL against C. orbiculare) and compound 1 (EC50 = 1.54 µg/mL against A. alternata, EC50 = 0.20 µg/mL against R. solani). The 3D-QSAR analysis of quinoxaline-2-oxyacetate hydrazide derivatives has provided new insights into the design and optimization of novel antifungal drug molecules based on quinoxaline.


Assuntos
Antifúngicos , Testes de Sensibilidade Microbiana , Relação Quantitativa Estrutura-Atividade , Quinoxalinas , Antifúngicos/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Quinoxalinas/farmacologia , Quinoxalinas/química , Quinoxalinas/síntese química , Desenho de Fármacos , Alternaria/efeitos dos fármacos , Rhizoctonia/efeitos dos fármacos , Botrytis/efeitos dos fármacos , Estrutura Molecular , Colletotrichum/efeitos dos fármacos , Gibberella/efeitos dos fármacos
4.
PLoS One ; 19(6): e0304817, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38889131

RESUMO

Rice (Oryza sativa) stands as a crucial staple food worldwide, especially in Bangladesh, where it ranks as the third-largest producer. However, intensified cultivation has made high-yielding rice varieties susceptible to various biotic stresses, notably sheath blight caused by Rhizoctonia solani, which inflicts significant yield losses annually. Traditional fungicides, though effective, pose environmental and health risks. To address this, nanotechnology emerges as a promising avenue, leveraging the antimicrobial properties of nanoparticles like silver nanoparticles (AgNPs). This study explored the green synthesis of AgNPs using Ipomoea carnea leaf extract and silver nitrate (AgNO3), and also examined their efficacy against sheath blight disease in rice. The biosynthesized AgNPs were characterized through various analytical techniques such as UV-vis spectrophotometer, X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FTIR), Particle size analyzer, Zeta potential, Scanning Electron Microscope (SEM), Field Emission Scanning Electron Microscope (FESEM), Transmission Electron Microscope (TEM) for confirming their successful production and crystalline nature of nanoparticles. The results of UV-visible spectrophotometers revealed an absorption peak ranging from 421 to 434 nm, validated the synthesis of AgNPs in the solution. XRD, DLS, and TEM estimated AgNPs sizes were ~45 nm, 66.2nm, and 46.38 to 73.81 nm, respectively. SEM and FESEM demonstrated that the synthesized AgNPs were spherical in shape. In vitro assays demonstrated the significant inhibitory effects of AgNPs on mycelial growth of Rhizoctonia solani, particularly at higher concentrations and pH levels. Further greenhouse and field experiments validated the antifungal efficacy of AgNPs against sheath blight disease in rice, exhibiting comparable effectiveness to commercial fungicides. The findings highlight the potential of AgNPs as a sustainable and effective alternative for managing rice sheath blight disease, offering a safer solution amidst environmental concerns associated with conventional fungicides.


Assuntos
Química Verde , Nanopartículas Metálicas , Oryza , Doenças das Plantas , Rhizoctonia , Prata , Rhizoctonia/efeitos dos fármacos , Oryza/microbiologia , Prata/química , Prata/farmacologia , Nanopartículas Metálicas/química , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Difração de Raios X , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química
5.
Curr Microbiol ; 81(7): 207, 2024 Jun 04.
Artigo em Inglês | MEDLINE | ID: mdl-38831110

RESUMO

The current study aimed to evaluate the plant growth-promoting (PGP) potential of endophytic strain Bacillus subtilis KU21 isolated from the roots of Rosmarinus officinalis. The strain exhibited multiple traits of plant growth promotion viz., phosphate (P) solubilization, nitrogen fixation, indole-3-acetic acid (IAA), siderophore, hydrogen cyanide (HCN), lytic enzymes production, and 1-aminocyclopropane-1-carboxylate (ACC) deaminase activity. The isolate also exhibited antagonistic activity against phytopathogenic fungi, i.e., Fusarium oxysporum, Fusarium graminiarum, and Rhizoctonia solani. The P-solubilization activity of B. subtilis KU21 was further elucidated via detection of glucose dehydrogenase (gdh) gene involved in the production of gluconic acid which is responsible for P-solubilization. Further, B. subtilis KU21 was evaluated for in vivo growth promotion studies of tomato (test crop) under net house conditions. A remarkable increase in seed germination, plant growth parameters, nutrient acquisition, and soil quality parameters (NPK) was observed in B. subtilis KU21-treated plants over untreated control. Hence, the proposed module could be recommended for sustainable tomato production in the Northwest Himalayan region without compromising soil health and fertility.


Assuntos
Bacillus subtilis , Endófitos , Raízes de Plantas , Rosmarinus , Bacillus subtilis/genética , Bacillus subtilis/crescimento & desenvolvimento , Bacillus subtilis/isolamento & purificação , Bacillus subtilis/metabolismo , Endófitos/isolamento & purificação , Endófitos/metabolismo , Endófitos/genética , Endófitos/classificação , Rosmarinus/química , Rosmarinus/microbiologia , Raízes de Plantas/microbiologia , Raízes de Plantas/crescimento & desenvolvimento , Solanum lycopersicum/microbiologia , Solanum lycopersicum/crescimento & desenvolvimento , Fusarium/crescimento & desenvolvimento , Fusarium/genética , Fusarium/metabolismo , Microbiologia do Solo , Desenvolvimento Vegetal , Germinação , Ácidos Indolacéticos/metabolismo , Rhizoctonia/crescimento & desenvolvimento , Rhizoctonia/efeitos dos fármacos , Fixação de Nitrogênio , Fosfatos/metabolismo
6.
Pestic Biochem Physiol ; 202: 105956, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38879338

RESUMO

Pepper southern blight, caused by Sclerotium rolfsii, is a devastating soil-borne disease resulting in significant loss to pepper, Capsicum annuum L. production. Here, we isolated an antagonistic bacterial strain XQ-29 with antifungal activity against S. rolfsii from rhizospheric soil of pepper. Combining the morphological and biochemical characteristics with the 16S rDNA sequencing, XQ-29 was identified as Streptomyces griseoaurantiacus. It exhibited an inhibition of 96.83% against S. rolfsii and displayed significant inhibitory effects on Botrytis cinerea, Phytophthora capsica and Rhizoctonia solani. Furthermore, XQ-29 significantly reduced the pepper southern blight by 100% and 70.42% during seedling and growth stages, respectively. The antifungal mechanism involved altering the mycelial morphology, disrupting cell wall and membrane integrity, accompanied by accumulation of reactive oxygen species and lipid peroxidation in S. rolfsii mycelia. Furthermore, XQ-29 promoted growth and stimulated resistance of pepper plants by increasing defense-related enzyme activities and upregulating defense-related genes. Correspondingly, XQ-29 harbors numerous functional biosynthesis gene clusters in its genome, including those for siderophores and melanin production. The metabolic constituents present in the ethyl acetate extracts, which exhibited an EC50 value of 85.48 ± 1.62 µg/mL, were identified using LC-MS. Overall, XQ-29 demonstrates significant potential as a biocontrol agent against southern blight disease.


Assuntos
Botrytis , Capsicum , Doenças das Plantas , Rhizoctonia , Streptomyces , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Capsicum/microbiologia , Streptomyces/genética , Streptomyces/fisiologia , Botrytis/efeitos dos fármacos , Botrytis/fisiologia , Rhizoctonia/fisiologia , Rhizoctonia/efeitos dos fármacos , Basidiomycota/fisiologia , Phytophthora/fisiologia , Phytophthora/efeitos dos fármacos , Agentes de Controle Biológico/farmacologia , Antifúngicos/farmacologia
7.
Sci Rep ; 14(1): 13580, 2024 06 12.
Artigo em Inglês | MEDLINE | ID: mdl-38866928

RESUMO

Rhizoctonia solani, the causal agent of banded leaf and sheath blight (BL&SB), poses a significant threat to maize and various crops globally. The increasing concerns surrounding the environmental and health impacts of chemical fungicides have encouraged intensified concern in the development of biological control agents (BCAs) as eco-friendly alternatives. In this study, we explored the potential of 22 rhizobacteria strains (AS1-AS22) isolates, recovered from the grasslands of the Pithoragarh region in the Central Himalayas, as effective BCAs against BL&SB disease. Among these strains, two Pseudomonas isolates, AS19 and AS21, exhibited pronounced inhibition of fungal mycelium growth in vitro, with respective inhibition rates of 57.04% and 54.15% in cell cultures and 66.56% and 65.60% in cell-free culture filtrates. Additionally, both strains demonstrated effective suppression of sclerotium growth. The strains AS19 and AS21 were identified as Pseudomonas sp. by 16S rDNA phylogeny and deposited under accession numbers NAIMCC-B-02303 and NAIMCC-B-02304, respectively. Further investigations revealed the mechanisms of action of AS19 and AS21, demonstrating their ability to induce systemic resistance (ISR) and exhibit broad-spectrum antifungal activity against Alternaria triticina, Bipolaris sorokiniana, Rhizoctonia maydis, and Fusarium oxysporum f. sp. lentis. Pot trials demonstrated significant reductions in BL&SB disease incidence (DI) following foliar applications of AS19 and AS21, with reductions ranging from 25 to 38.33% compared to control treatments. Scanning electron microscopy revealed substantial degradation of fungal mycelium by the strains, accompanied by the production of hydrolytic enzymes. These findings suggest the potential of Pseudomonas strains AS19 and AS21 as promising BCAs against BL&SB and other fungal pathogens. However, further field trials are warranted to validate their efficacy under natural conditions and elucidate the specific bacterial metabolites responsible for inducing systemic resistance. This study contributes to the advancement of sustainable disease management strategies and emphasizes the potential of Pseudomonas strains AS19 and AS21 in combating BL&SB and other fungal diseases affecting agricultural crops.


Assuntos
Doenças das Plantas , Pseudomonas , Rhizoctonia , Zea mays , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Zea mays/microbiologia , Pseudomonas/metabolismo , Rhizoctonia/fisiologia , Rhizoctonia/efeitos dos fármacos , Folhas de Planta/microbiologia , Agentes de Controle Biológico , Controle Biológico de Vetores/métodos , Antibiose , Filogenia
8.
J Agric Food Chem ; 72(26): 14535-14546, 2024 Jul 03.
Artigo em Inglês | MEDLINE | ID: mdl-38906830

RESUMO

The development of new fungicide molecules is a crucial task for agricultural chemists to enhance the effectiveness of fungicides in agricultural production. In this study, a series of novel fluoroalkenyl modified succinate dehydrogenase inhibitors were synthesized and evaluated for their antifungal activities against eight fungi. The results from the in vitro antifungal assay demonstrated that compound 34 exhibited superior activity against Rhizoctonia solani with an EC50 value of 0.04 µM, outperforming commercial fluxapyroxad (EC50 = 0.18 µM) and boscalid (EC50 = 3.07 µM). Furthermore, compound 34 showed similar effects to fluxapyroxad on other pathogenic fungi such as Sclerotinia sclerotiorum (EC50 = 1.13 µM), Monilinia fructicola (EC50 = 1.61 µM), Botrytis cinerea (EC50 = 1.21 µM), and also demonstrated protective and curative efficacies in vivo on rapeseed leaves and tomato fruits. Enzyme activity experiments and protein-ligand interaction analysis by surface plasmon resonance revealed that compound 34 had a stronger inhibitory effect on succinate dehydrogenase compared to fluxapyroxad. Additionally, molecular docking and DFT calculation confirmed that the fluoroalkenyl unit in compound 34 could enhance its binding capacity with the target protein through p-π conjugation and hydrogen bond interactions.


Assuntos
Desenho de Fármacos , Inibidores Enzimáticos , Proteínas Fúngicas , Fungicidas Industriais , Rhizoctonia , Succinato Desidrogenase , Succinato Desidrogenase/antagonistas & inibidores , Succinato Desidrogenase/química , Succinato Desidrogenase/metabolismo , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Rhizoctonia/efeitos dos fármacos , Rhizoctonia/enzimologia , Relação Estrutura-Atividade , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/síntese química , Proteínas Fúngicas/antagonistas & inibidores , Proteínas Fúngicas/química , Proteínas Fúngicas/metabolismo , Doenças das Plantas/microbiologia , Simulação de Acoplamento Molecular , Botrytis/efeitos dos fármacos , Botrytis/enzimologia , Ascomicetos/efeitos dos fármacos , Ascomicetos/enzimologia , Solanum lycopersicum/microbiologia , Solanum lycopersicum/química , Estrutura Molecular
9.
PLoS One ; 19(6): e0302440, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38870165

RESUMO

Rhizoctonia solani, the causative agent of sheath blight disease in rice, poses a significant threat to agricultural productivity. Traditional management approaches involving chemical fungicides have been effective but come with detrimental consequences for the ecosystem. This study aimed to investigate sustainable alternatives in the form of antifungal peptides derived from Solanaceous plant species as potential agents against R. solani. Peptide extracts were obtained using an optimized antimicrobial peptide (AMP) extraction method and desalted using the solid-phase extraction technique. The antifungal potential of peptide-rich extracts from Solanum tuberosum and Capsicum annum was assessed through in vitro tests employing the agar well diffusion method. Furthermore, peptide-protein docking analysis was performed on HPEPDOCK and HDOCK server; and molecular dynamics simulations (MDS) of 100 ns period were performed using the Gromacs 2020.4. The results demonstrated significant inhibition zones for both extracts at concentrations of 100 mg/mL. Additionally, the extracts of Solanum tuberosum and Capsicum annum had minimum inhibitory concentrations of 50 mg/mL and 25 mg/mL, respectively with minimum fungicidal concentrations of 25 mg/mL. Insights into the potential mechanisms of key peptides inhibiting R. solani targets were gleaned from in-silico studies. Notably, certain AMPs exhibited favorable free energy of binding against pathogenicity-related targets, including histone demethylase, sortin nexin, and squalene synthase, in protein-peptide docking simulations. Extended molecular dynamics simulations lasting 100 ns and MM-PBSA calculations were performed on select protein-peptide complexes. AMP10 displayed the most favorable binding free energy against all target proteins, with AMP3, AMP12b, AMP6, and AMP15 also exhibiting promising results against specific targets of R. solani. These findings underscore the potential of peptide extracts from S. tuberosum and C. annum as effective antifungal agents against rice sheath blight caused by R. solani.


Assuntos
Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Oryza , Doenças das Plantas , Rhizoctonia , Oryza/microbiologia , Doenças das Plantas/microbiologia , Rhizoctonia/efeitos dos fármacos , Peptídeos Antimicrobianos/farmacologia , Peptídeos Antimicrobianos/química , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Solanum tuberosum/microbiologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Solanaceae/química , Testes de Sensibilidade Microbiana , Simulação por Computador , Capsicum/microbiologia , Capsicum/química
10.
J Hazard Mater ; 474: 134807, 2024 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-38850939

RESUMO

Nanocrop protectants have attracted much attention as sustainable platforms for controlling pests and diseases and improving crop nutrition. Here, we reported the fungicidal activity and disease inhibition potential of pectin-coated metal-iron organic framework nanoparticles (Fe-MOF-PT NPs) against rice stripe blight (RSB). An in vitro bacterial inhibition assay showed that Fe-MOF-PT NPs (80 mg/L) significantly inhibited mycelial growth and nucleus formation. The Fe-MOF-PT NPs adsorbed to the surface of mycelia and induced toxicity by disrupting cell membranes, mitochondria, and DNA. The results of a nontargeted metabolomics analysis showed that the metabolites of amino acids and their metabolites, heterocyclic compounds, fatty acids, and nucleotides and their metabolites were significantly downregulated after treatment with 80 mg/L NPs. The difference in metabolite abundance between the CK and Fe-MOF-PT NPs (80 mg/L) treatment groups was mainly related to nucleotide metabolism, pyrimidine metabolism, purine metabolism, fatty acid metabolism, and amino acid metabolism. The results of the greenhouse experiment showed that Fe-MOF-PT NPs improved rice resistance to R. solani by inhibiting mycelial invasion, enhancing antioxidant enzyme activities, activating the jasmonic acid signaling pathway, and enhancing photosynthesis. These findings indicate the great potential of Fe-MOF-PT NPs as a new RSB disease management strategy and provide new insights into plant fungal disease management.


Assuntos
Ferro , Estruturas Metalorgânicas , Oryza , Pectinas , Doenças das Plantas , Rhizoctonia , Oryza/metabolismo , Oryza/efeitos dos fármacos , Oryza/microbiologia , Rhizoctonia/efeitos dos fármacos , Doenças das Plantas/prevenção & controle , Doenças das Plantas/microbiologia , Ferro/química , Ferro/metabolismo , Pectinas/química , Pectinas/farmacologia , Estruturas Metalorgânicas/química , Estruturas Metalorgânicas/farmacologia , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/toxicidade , Nanopartículas Metálicas/química , Nanopartículas Metálicas/toxicidade , Resistência à Doença/efeitos dos fármacos
11.
J Agric Food Chem ; 72(23): 12915-12924, 2024 Jun 12.
Artigo em Inglês | MEDLINE | ID: mdl-38807027

RESUMO

Plant pathogenic fungi pose a significant threat to agricultural production, necessitating the development of new and more effective fungicides. The ring replacement strategy has emerged as a highly successful approach in molecular design. In this study, we employed the ring replacement strategy to successfully design and synthesize 32 novel hydrazide derivatives containing diverse heterocycles, such as thiazole, isoxazole, pyrazole, thiadiazole, 1,3,4-oxadiazole, 1,2,4-oxadiazole, thiophene, pyridine, and pyrazine. Their antifungal activities were evaluated in vitro and in vivo. Bioassay results revealed that most of the title compounds displayed remarkable antifungal activities in vitro against four tested phytopathogenic fungi, including Fusarium graminearum, Botrytis cinerea, Sclerotinia sclerotiorum, and Rhizoctonia solani. Especially, compound 5aa displayed a broad spectrum of antifungal activity against F. graminearum, B. cinerea, S. sclerotiorum, and R. solani, with the corresponding EC50 values of 0.12, 4.48, 0.33, and 0.15 µg/mL, respectively. In the antifungal growth assay, compound 5aa displayed a protection efficacy of 75.5% against Fusarium head blight (FHB) at a concentration of 200 µg/mL. In another in vivo antifungal activity evaluation, compound 5aa exhibited a noteworthy protective efficacy of 92.0% against rape Sclerotinia rot (RSR) at a concentration of 100 µg/mL, which was comparable to the positive control tebuconazole (97.5%). The existing results suggest that compound 5aa has a broad-spectrum antifungal activity. Electron microscopy observations showed that compound 5aa might cause mycelial abnormalities and organelle damage in F. graminearum. Moreover, in the in vitro enzyme assay, we found that the target compounds 5aa, 5ab, and 5ca displayed significant inhibitory effects toward succinate dehydrogenase, with the corresponding IC50 values of 1.62, 1.74, and 1.96 µM, respectively, which were superior to that of boscalid (IC50 = 2.38 µM). Additionally, molecular docking and molecular dynamics simulation results revealed that compounds 5aa, 5ab, and 5ca have the capacity to bind in the active pocket of succinate dehydrogenase (SDH), establishing hydrogen-bonding interactions with neighboring amino acid residues.


Assuntos
Ascomicetos , Botrytis , Desenho de Fármacos , Fungicidas Industriais , Fusarium , Doenças das Plantas , Rhizoctonia , Succinato Desidrogenase , Succinato Desidrogenase/antagonistas & inibidores , Fusarium/efeitos dos fármacos , Fusarium/crescimento & desenvolvimento , Fungicidas Industriais/farmacologia , Fungicidas Industriais/síntese química , Fungicidas Industriais/química , Relação Estrutura-Atividade , Ascomicetos/efeitos dos fármacos , Botrytis/efeitos dos fármacos , Botrytis/crescimento & desenvolvimento , Rhizoctonia/efeitos dos fármacos , Doenças das Plantas/microbiologia , Simulação de Acoplamento Molecular , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/síntese química , Proteínas Fúngicas/antagonistas & inibidores , Proteínas Fúngicas/química , Proteínas Fúngicas/metabolismo , Testes de Sensibilidade Microbiana , Hidrazinas/farmacologia , Hidrazinas/química , Hidrazinas/síntese química , Estrutura Molecular , Compostos Heterocíclicos/farmacologia , Compostos Heterocíclicos/química , Compostos Heterocíclicos/síntese química
12.
J Agric Food Chem ; 72(22): 12415-12424, 2024 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-38779960

RESUMO

A series of novel 2-Ar-1,2,3-triazole derivatives were designed and synthesized based on our previously discovered active compound 6d against Rhizoctonia solani. Most of these compounds exhibited good antifungal activity against R. solani at a concentration of 25 µg/mL. Based on the results of biological activity, we established a three-dimensional quantitative structure-activity relationship (3D-QSAR) model that guided the synthesis of compound 7y. Compound 7y exhibited superior activity against R. solani (EC50 = 0.47 µg/mL) compared to the positive controls hymexazol (EC50 = 12.80 µg/mL) and tebuconazole (EC50 = 0.87 µg/mL). Furthermore, compound 7y demonstrated better protective activity than the aforementioned two commercial fungicides in both detached leaf assays and greenhouse experiments, achieving 56.21% and 65.75% protective efficacy, respectively, at a concentration of 100 µg/mL. The ergosterol content was determined and molecular docking was performed to explore the mechanism of these active molecules. DFT calculation and MEP analysis were performed to illustrate the results of this study. These results suggest that compound 7y could serve as a novel 2-Ar-1,2,3-triazole lead compound for controlling R. solani.


Assuntos
Desenho de Fármacos , Fungicidas Industriais , Simulação de Acoplamento Molecular , Doenças das Plantas , Relação Quantitativa Estrutura-Atividade , Rhizoctonia , Triazóis , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Triazóis/química , Triazóis/farmacologia , Triazóis/síntese química , Rhizoctonia/efeitos dos fármacos , Rhizoctonia/crescimento & desenvolvimento , Doenças das Plantas/microbiologia , Estrutura Molecular , Hidrazinas/química , Hidrazinas/farmacologia
13.
Molecules ; 29(10)2024 May 12.
Artigo em Inglês | MEDLINE | ID: mdl-38792143

RESUMO

Strigolactones (SLs) have potential to be used in sustainable agriculture to mitigate various stresses that plants have to deal with. The natural SLs, as well as the synthetic analogs, are difficult to obtain in sufficient amounts for practical applications. At the same time, fluorescent SLs would be useful for the mechanistic understanding of their effects based on bio-imaging or spectroscopic techniques. In this study, new fluorescent SL mimics containing a substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive furan-2-one moiety were prepared. The structural, spectroscopic, and biological activity of the new SL mimics on phytopathogens were investigated and compared with previously synthetized fluorescent SL mimics. The chemical group at the C-6 position of the naphthalimide ring influences the fluorescence parameters. All SL mimics showed effects similar to GR24 on phytopathogens, indicating their suitability for practical applications. The pattern of the biological activity depended on the fungal species, SL mimic and concentration, and hyphal order. This dependence is probably related to the specificity of each fungal receptor-SL mimic interaction, which will have to be analyzed in-depth. Based on the biological properties and spectroscopic particularities, one SL mimic could be a good candidate for microscopic and spectroscopic investigations.


Assuntos
Lactonas , Naftalimidas , Naftalimidas/química , Naftalimidas/síntese química , Naftalimidas/farmacologia , Lactonas/química , Lactonas/farmacologia , Lactonas/síntese química , Estrutura Molecular , Ascomicetos , Corantes Fluorescentes/química , Corantes Fluorescentes/síntese química , Rhizoctonia/efeitos dos fármacos , Compostos Heterocíclicos com 3 Anéis
14.
J Agric Food Chem ; 72(21): 11938-11948, 2024 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-38752540

RESUMO

The pursuit of new succinate dehydrogenase (SDH) inhibitors is a leading edge in fungicide research and development. The use of 3D quantitative structure-activity relationship (3D-QSAR) models significantly enhances the development of compounds with potent antifungal properties. In this study, we leveraged the natural product coumarin as a molecular scaffold to synthesize 74 novel 3-coumarin hydrazide derivatives. Notably, compounds 4ap (0.28 µg/mL), 6ae (0.32 µg/mL), and 6ah (0.48 µg/mL) exhibited exceptional in vitro effectiveness against Rhizoctonia solani, outperforming the commonly used fungicide boscalid (0.52 µg/mL). Furthermore, compounds 4ak (0.88 µg/mL), 6ae (0.61 µg/mL), 6ah (0.65 µg/mL), and 6ak (1.11 µg/mL) showed significant activity against Colletotrichum orbiculare, surpassing both the SDHI fungicide boscalid (43.45 µg/mL) and the broad-spectrum fungicide carbendazim (2.15 µg/mL). Molecular docking studies and SDH enzyme assays indicate that compound 4ah may serve as a promising SDHI fungicide. Our ongoing research aims to refine this 3D-QSAR model further, enhance molecular design, and conduct additional bioactivity assays.


Assuntos
Cumarínicos , Fungicidas Industriais , Relação Quantitativa Estrutura-Atividade , Rhizoctonia , Succinato Desidrogenase , Cumarínicos/química , Cumarínicos/farmacologia , Cumarínicos/síntese química , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Rhizoctonia/efeitos dos fármacos , Succinato Desidrogenase/antagonistas & inibidores , Succinato Desidrogenase/metabolismo , Colletotrichum/efeitos dos fármacos , Estrutura Molecular , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/síntese química , Proteínas Fúngicas/antagonistas & inibidores , Proteínas Fúngicas/química , Proteínas Fúngicas/metabolismo , Hidrazinas/química , Hidrazinas/farmacologia , Hidrazinas/síntese química , Simulação de Acoplamento Molecular , Halogenação , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/síntese química
15.
J Agric Food Chem ; 72(21): 11990-12002, 2024 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-38757490

RESUMO

The main challenge in the development of agrochemicals is the lack of new leads and/or targets. It is critical to discover new molecular targets and their corresponding ligands. YZK-C22, which contains a 1,2,3-thiadiazol-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole skeleton, is a fungicide lead compound with broad-spectrum fungicidal activity. Previous studies suggested that the [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole scaffold exhibited good antifungal activity. Inspired by this, a series of pyrrolo[2,3-d]thiazole derivatives were designed and synthesized through a bioisosteric strategy. Compounds C1, C9, and C20 were found to be more active against Rhizoctonia solani than the positive control YZK-C22. More than half of the target compounds provided favorable activity against Botrytis cinerea, where the EC50 values of compounds C4, C6, C8, C10, and C20 varied from 1.17 to 1.77 µg/mL. Surface plasmon resonance and molecular docking suggested that in vitro potent compounds C9 and C20 have a new mode of action instead of acting as pyruvate kinase inhibitors. Transcriptome analysis revealed that compound C20 can impact the tryptophan metabolic pathway, cutin, suberin, and wax biosynthesis of B. cinerea. Overall, pyrrolo[2,3-d]thiazole is discovered as a new fungicidal lead structure with a potential new mode of action for further exploration.


Assuntos
Botrytis , Fungicidas Industriais , Rhizoctonia , Tiazóis , Triptofano , Ceras , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Rhizoctonia/efeitos dos fármacos , Botrytis/efeitos dos fármacos , Tiazóis/farmacologia , Tiazóis/química , Tiazóis/metabolismo , Triptofano/metabolismo , Triptofano/química , Ceras/química , Ceras/metabolismo , Relação Estrutura-Atividade , Redes e Vias Metabólicas/efeitos dos fármacos , Simulação de Acoplamento Molecular , Pirróis/farmacologia , Pirróis/química , Pirróis/metabolismo , Doenças das Plantas/microbiologia , Estrutura Molecular
16.
J Agric Food Chem ; 72(21): 12260-12269, 2024 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-38759097

RESUMO

Thirty-four new pyrido[4,3-d]pyrimidine analogs were designed, synthesized, and characterized. The crystal structures for compounds 2c and 4f were measured by means of X-ray diffraction of single crystals. The bioassay results showed that most target compounds exhibited good fungicidal activities against Pyricularia oryzae, Rhizoctonia cerealis, Sclerotinia sclerotiorum, Botrytis cinerea, and Penicillium italicum at 16 µg/mL. Compounds 2l, 2m, 4f, and 4g possessed better fungicidal activities than the commercial fungicide epoxiconazole against B. cinerea. Their half maximal effective concentration (EC50) values were 0.191, 0.487, 0.369, 0.586, and 0.670 µg/mL, respectively. Furthermore, the inhibitory activities of the bioactive compounds were determined against sterol 14α-demethylase (CYP51). The results displayed that they had prominent activities. Compounds 2l, 2m, 4f, and 4g also showed better inhibitory activities than epoxiconazole against CYP51. Their half maximal inhibitory concentration (IC50) values were 0.219, 0.602, 0.422, 0.726, and 0.802 µg/mL, respectively. The results of molecular dynamics (MD) simulations exhibited that compounds 2l and 4f possessed a stronger affinity to CYP51 than epoxiconazole.


Assuntos
Inibidores de 14-alfa Desmetilase , Ascomicetos , Desenho de Fármacos , Proteínas Fúngicas , Fungicidas Industriais , Pirimidinas , Rhizoctonia , Esterol 14-Desmetilase , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Pirimidinas/química , Pirimidinas/farmacologia , Pirimidinas/síntese química , Esterol 14-Desmetilase/química , Esterol 14-Desmetilase/metabolismo , Relação Estrutura-Atividade , Rhizoctonia/efeitos dos fármacos , Inibidores de 14-alfa Desmetilase/farmacologia , Inibidores de 14-alfa Desmetilase/química , Inibidores de 14-alfa Desmetilase/síntese química , Proteínas Fúngicas/química , Proteínas Fúngicas/antagonistas & inibidores , Ascomicetos/efeitos dos fármacos , Ascomicetos/enzimologia , Modelos Moleculares , Botrytis/efeitos dos fármacos , Penicillium/efeitos dos fármacos , Penicillium/enzimologia , Estrutura Molecular , Simulação de Acoplamento Molecular
17.
ACS Nano ; 18(20): 13084-13097, 2024 May 21.
Artigo em Inglês | MEDLINE | ID: mdl-38727520

RESUMO

In the current work, the foliar application of selenium nanomaterials (Se0 NMs) suppressed sheath blight in rice (Oryza sativa). The beneficial effects were nanoscale specific and concentration dependent. Specifically, foliar amendment of 5 mg/L Se0 NMs decreased the disease severity by 68.8% in Rhizoctonia solani-infected rice; this level of control was 1.57- and 2.20-fold greater than that of the Se ions with equivalent Se mass and a commercially available pesticide (Thifluzamide). Mechanistically, (1) the controlled release ability of Se0 NMs enabled a wider safe concentration range and greater bioavailability to Se0 NMs, and (2) transcriptomic and metabolomic analyses demonstrated that Se0 NMs simultaneously promoted the salicylic acid- and jasmonic-acid-dependent acquired disease resistance pathways, antioxidative system, and flavonoid biosynthesis. Additionally, Se0 NMs improved rice yield by 31.1%, increased the nutritional quality by 6.4-7.2%, enhanced organic Se content by 44.8%, and decreased arsenic and cadmium contents by 38.7 and 42.1%, respectively, in grains as compared with infected controls. Human simulated gastrointestinal tract model results showed that the application of Se0 NMs enhanced the bioaccessibility of Se in grains by 22.0% and decreased the bioaccessibility of As and Cd in grains by 20.3 and 13.4%, respectively. These findings demonstrate that Se0 NMs can serve as an effective and sustainable strategy to increase food quality and security.


Assuntos
Nanoestruturas , Oryza , Doenças das Plantas , Rhizoctonia , Selênio , Oryza/microbiologia , Oryza/metabolismo , Oryza/efeitos dos fármacos , Selênio/farmacologia , Selênio/química , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Humanos , Rhizoctonia/efeitos dos fármacos , Nanoestruturas/química , Valor Nutritivo , Resistência à Doença/efeitos dos fármacos
18.
Sci Rep ; 14(1): 11228, 2024 05 16.
Artigo em Inglês | MEDLINE | ID: mdl-38755187

RESUMO

Antimicrobial resistance in fungal pathogens (both human and plant) is increasing alarmingly, leading to massive economic crises. The existing anti-fungal agents are becoming ineffective, and the situation worsens on a logarithmic scale. Novel antifungals from unique natural sources are highly sought to cope sustainably with the situation. Metabolites from endophytic microbes are the best-fitted alternatives in this case. Endophytes are the untapped sources of 'plants' internal microbial population' and are promising sources of effective bio-therapeutic agents. Fungal endophytes were isolated from Tropaeolum majus and checked for antifungal activity against selected plant and human pathogens. Bioactive metabolites were identified through chromatographic techniques. The mode of action of those metabolites was evaluated through various spectroscopic techniques. The production of antifungal metabolite was optimized also. In particular VOCs (volatile organic compounds) of TML9 were tested in vitro for their anti-phytopathogenic activity. Ethyl acetate (EA) extract of cell-free culture components of Colletotrichum aenigma TML3 exhibited broad-spectrum antifungal activity against four species of Candida and the major constituents reported were 6-pentyl-2H-pyran-2-one, 2-Nonanone, 1 propanol 2-amino. The volatile metabolites, trans-ocimene, geraniol, and 4-terpinyl acetate, produced from Curvularia lunata TML9, inhibited the growth of some selected phyto pathogens. EA extract hampered the biofilm formation, minimised the haemolytic effect, and blocked the transformation of Candida albicans (MTCC 4748) from yeast to hyphal form with a Minimum Fungicidal Concentration (MFC) of 200-600 µg mL-1. Central carbohydrate metabolism, ergosterol synthesis, and membrane permeability were adversely affected and caused the lethal leakage of necessary macromolecules of C. albicans. Volatile metabolites inhibited the growth of phytopathogens i.e., Rhizoctonia solani, Alternaria alternata, Botrytis cinerea, Cercospora beticola, Penicillium digitatum, Aspergillus fumigatus, Ceratocystis ulmi, Pythium ultimum up to 89% with an IC50 value of 21.3-69.6 µL 50 mL-1 and caused leakage of soluble proteins and other intracellular molecules. Citrusy sweet odor volatiles of TML9 cultured in wheat-husk minimised the infections of Penicillium digitatum (green mold), in VOC-exposed sweet oranges (Citrus sinensis). Volatile and non-volatile antifungal metabolites of these two T. majus endophytes hold agricultural and pharmaceutical interests. Metabolites of TML3 have strong anti-Candida activity and require further assessment for therapeutic applications. Also, volatile metabolites of TML9 can be further studied as a source of antifungals. The present investigational outcomes bio-prospects the efficacy of fungal endophytes of Garden Nasturtium.


Assuntos
Antifúngicos , Endófitos , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/farmacologia , Compostos Orgânicos Voláteis/química , Antifúngicos/farmacologia , Antifúngicos/química , Endófitos/metabolismo , Endófitos/química , Testes de Sensibilidade Microbiana , Colletotrichum/efeitos dos fármacos , Fungos/efeitos dos fármacos , Alternaria/efeitos dos fármacos , Rhizoctonia/efeitos dos fármacos , Humanos , Candida/efeitos dos fármacos
19.
J Agric Food Chem ; 72(20): 11308-11320, 2024 May 22.
Artigo em Inglês | MEDLINE | ID: mdl-38720452

RESUMO

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.


Assuntos
Desenho de Fármacos , Inibidores Enzimáticos , Fungicidas Industriais , Oximas , Pirazóis , Succinato Desidrogenase , Succinato Desidrogenase/antagonistas & inibidores , Succinato Desidrogenase/química , Succinato Desidrogenase/metabolismo , Pirazóis/química , Pirazóis/farmacologia , Pirazóis/síntese química , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Fungicidas Industriais/síntese química , Relação Estrutura-Atividade , Oximas/química , Oximas/farmacologia , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/síntese química , Proteínas Fúngicas/química , Proteínas Fúngicas/antagonistas & inibidores , Proteínas Fúngicas/metabolismo , Simulação de Acoplamento Molecular , Rhizoctonia/efeitos dos fármacos , Éteres/química , Éteres/farmacologia , Estrutura Molecular
20.
J Agric Food Chem ; 72(20): 11415-11428, 2024 May 22.
Artigo em Inglês | MEDLINE | ID: mdl-38727515

RESUMO

Rice sheath blight, caused by the fungus Rhizoctonia solani, poses a significant threat to rice cultivation globally. This study aimed to investigate the potential mechanisms of action of camphor derivatives against R. solani. Compound 4o exhibited superior fungicidal activities in vitro (EC50 = 6.16 mg/L), and in vivo curative effects (77.5%) at 500 mg/L were significantly (P < 0.01) higher than the positive control validamycin·bacillus (66.1%). Additionally, compound 4o exhibited low cytotoxicity and acute oral toxicity for adult worker honeybees of Apis mellifera L. Mechanistically, compound 4o disrupted mycelial morphology and microstructure, increased cell membrane permeability, and inhibited both PDH and SDH enzyme activities. Molecular docking and molecular dynamics analyses indicated a tight interaction of compound 4o with PDH and SDH active sites. In summary, compound 4o exhibited substantial antifungal efficacy against R. solani, serving as a promising lead compound for further optimization of antifungal agents.


Assuntos
Cânfora , Fungicidas Industriais , Simulação de Acoplamento Molecular , Oryza , Doenças das Plantas , Rhizoctonia , Rhizoctonia/efeitos dos fármacos , Oryza/microbiologia , Doenças das Plantas/microbiologia , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Animais , Cânfora/farmacologia , Cânfora/química , Abelhas/microbiologia , Proteínas Fúngicas/metabolismo , Proteínas Fúngicas/química , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/síntese química , Relação Estrutura-Atividade
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