The Effect of 3′,4′-Methylenedioxychalcone Derivatives on Mycelial Growth and Conidial Germination of Monilinia fructicola: An In Silico and In Vitro Study

Catalina Ferreira, Valentina Silva, Evelyn Muñoz, Gissella Valle, Manuel Martínez-Lobos, Francisca Valdés, Katy Díaz, Iván Montenegro, Patricio Godoy, Nelson Caro and Alejandro Madrid ()
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Catalina Ferreira: Laboratorio 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
Valentina Silva: Laboratorio 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
Evelyn Muñoz: Laboratorio 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
Gissella Valle: Laboratorio 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
Manuel Martínez-Lobos: Laboratorio 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
Francisca Valdés: Laboratorio 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
Katy Díaz: Laboratorio de Pruebas Biológicas, Departamento de Química, Universidad Técnica Federico Santa María, Av. España N1680, Valparaíso 2340000, Chile
Iván Montenegro: Center of Interdisciplinary Biomedical and Engineering Research for Health (MEDING), Escuela de Obstetricia y Puericultura, Facultad de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca 2520000, Chile
Patricio Godoy: Instituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, Chile
Nelson Caro: Centro de Investigación Austral Biotech, Facultad de Ciencias, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, Chile
Alejandro Madrid: Laboratorio 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

Agriculture, 2025, vol. 15, issue 9, 1-12

Abstract: Monilinia fructicola 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 M. fructicola . Additionally, a molecular docking study and the prediction of lipophilicity were carried out to investigate their chemical behavior. The results showed that compound F exhibited the most potent antifungal activity, with EC 50 and MIC values of 20.61 µg/mL and <10 µg/mL for mycelial growth and conidial germination, respectively, presenting an adequate lipophilicity (Log p 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 F 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.

Keywords: chalcones; brown rot; antifungal activity; molecular docking (search for similar items in EconPapers)
JEL-codes: Q1 Q10 Q11 Q12 Q13 Q14 Q15 Q16 Q17 Q18 (search for similar items in EconPapers)
Date: 2025
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