The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study
<i>Monilinia fructicola</i> causes brown rot on a wide variety of stone fruits, causing several losses in the field and during storage of fruits. Due to the diverse biological activity of chalcones and their derivatives, they have emerged as a promising alternative for controlling phytop...
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2025-05-01
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| author | Catalina Ferreira Valentina Silva Evelyn Muñoz Gissella Valle Manuel Martínez-Lobos Francisca Valdés Katy Díaz Iván Montenegro Patricio Godoy Nelson Caro Alejandro Madrid |
| author_facet | Catalina Ferreira Valentina Silva Evelyn Muñoz Gissella Valle Manuel Martínez-Lobos Francisca Valdés Katy Díaz Iván Montenegro Patricio Godoy Nelson Caro Alejandro Madrid |
| author_sort | Catalina Ferreira |
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| description | <i>Monilinia fructicola</i> causes brown rot on a wide variety of stone fruits, causing several losses in the field and during storage of fruits. Due to the diverse biological activity of chalcones and their derivatives, they have emerged as a promising alternative for controlling phytopathogenic fungi. The aim of this study was to synthesize 3′,4′-methylenedioxychalcone derivatives and evaluate their in vitro inhibitory effect on mycelial growth and the conidial germination of <i>M. fructicola</i>. Additionally, a molecular docking study and the prediction of lipophilicity were carried out to investigate their chemical behavior. The results showed that compound <b>F</b> exhibited the most potent antifungal activity, with EC<sub>50</sub> and MIC values of 20.61 µg/mL and <10 µg/mL for mycelial growth and conidial germination, respectively, presenting an adequate lipophilicity (Log <i>p</i> values = 2.79), which would allow proper diffusion through the fungal cell membrane. The in silico study revealed a great number of interactions between compound <b>F</b> and the different active sites of the succinate dehydrogenase enzyme, suggesting a favorable interaction with a binding energy score value of −6.9 kcal/mol, similar to CBE, the native ligand of this enzyme. These types of compounds could provide preventive protection in various stone and other crops. |
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| institution | Kabale University |
| issn | 2077-0472 |
| language | English |
| publishDate | 2025-05-01 |
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| series | Agriculture |
| spelling | doaj-art-1d85f9efb1b448db94f330c9b937aaf22025-08-20T03:52:56ZengMDPI AGAgriculture2077-04722025-05-0115998310.3390/agriculture15090983The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro StudyCatalina Ferreira0Valentina Silva1Evelyn Muñoz2Gissella Valle3Manuel Martínez-Lobos4Francisca Valdés5Katy Díaz6Iván Montenegro7Patricio Godoy8Nelson Caro9Alejandro Madrid10Laboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileLaboratorio de Pruebas Biológicas, Departamento de Química, Universidad Técnica Federico Santa María, Av. España N1680, Valparaíso 2340000, ChileCenter of Interdisciplinary Biomedical and Engineering Research for Health (MEDING), Escuela de Obstetricia y Puericultura, Facultad de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca 2520000, ChileInstituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, ChileCentro de Investigación Austral Biotech, Facultad de Ciencias, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile<i>Monilinia fructicola</i> causes brown rot on a wide variety of stone fruits, causing several losses in the field and during storage of fruits. Due to the diverse biological activity of chalcones and their derivatives, they have emerged as a promising alternative for controlling phytopathogenic fungi. The aim of this study was to synthesize 3′,4′-methylenedioxychalcone derivatives and evaluate their in vitro inhibitory effect on mycelial growth and the conidial germination of <i>M. fructicola</i>. Additionally, a molecular docking study and the prediction of lipophilicity were carried out to investigate their chemical behavior. The results showed that compound <b>F</b> exhibited the most potent antifungal activity, with EC<sub>50</sub> and MIC values of 20.61 µg/mL and <10 µg/mL for mycelial growth and conidial germination, respectively, presenting an adequate lipophilicity (Log <i>p</i> values = 2.79), which would allow proper diffusion through the fungal cell membrane. The in silico study revealed a great number of interactions between compound <b>F</b> and the different active sites of the succinate dehydrogenase enzyme, suggesting a favorable interaction with a binding energy score value of −6.9 kcal/mol, similar to CBE, the native ligand of this enzyme. These types of compounds could provide preventive protection in various stone and other crops.https://www.mdpi.com/2077-0472/15/9/983chalconesbrown rotantifungal activitymolecular docking |
| spellingShingle | Catalina Ferreira Valentina Silva Evelyn Muñoz Gissella Valle Manuel Martínez-Lobos Francisca Valdés Katy Díaz Iván Montenegro Patricio Godoy Nelson Caro Alejandro Madrid The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study Agriculture chalcones brown rot antifungal activity molecular docking |
| title | The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study |
| title_full | The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study |
| title_fullStr | The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study |
| title_full_unstemmed | The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study |
| title_short | The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of <i>Monilinia fructicola</i>: An In Silico and In Vitro Study |
| title_sort | effect of 3 4 methylenedioxychalcone derivatives on mycelial growth and conidial germination of i monilinia fructicola i an in silico and in vitro study |
| topic | chalcones brown rot antifungal activity molecular docking |
| url | https://www.mdpi.com/2077-0472/15/9/983 |
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