In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i>
The aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (<b>2</b>–<b>9</b>) and to evaluate mycelial growth activity of hybrid molecules against two strains of <i>Monilinia fructicola</i>, as well as their toxicity. Di...
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MDPI AG
2021-07-01
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| author | Katy Díaz Enrique Werner Ximena Besoain Susana Flores Viviana Donoso Bastian Said Nelson Caro Ernesto Vega Iván Montenegro Alejandro Madrid |
| author_facet | Katy Díaz Enrique Werner Ximena Besoain Susana Flores Viviana Donoso Bastian Said Nelson Caro Ernesto Vega Iván Montenegro Alejandro Madrid |
| author_sort | Katy Díaz |
| collection | DOAJ |
| description | The aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (<b>2</b>–<b>9</b>) and to evaluate mycelial growth activity of hybrid molecules against two strains of <i>Monilinia fructicola</i>, as well as their toxicity. Dihydrocarvone-hybrid derivatives have been synthesized under sonication conditions and characterized by FTIR, NMR, and HRMS. Antifungal efficacy against both strains of <i>M. fructicola</i> was determined by half maximal effective concentration (EC<sub>50</sub>) and toxicity using the brine shrimp lethality test (BSLT). Among the synthesized compounds, <b>7</b> and <b>8</b> showed the best activity against both strains of <i>M. fructicola</i> with EC<sub>50</sub> values of 148.1 and 145.9 µg/mL for strain 1 and 18.1 and 15.7 µg/mL for strain 2, respectively, compared to BC 1000<sup>®</sup> (commercial organic fungicide) but lower than Mystic<sup>®</sup> 520 SC. However, these compounds showed low toxicity values, 910 and 890 µg/mL, respectively, compared to Mystic<sup>®</sup> 520 SC, which was highly toxic. Based on the results, these hybrid compounds could be considered for the development of more active, less toxic, and environmentally friendly antifungal agents against phytopathogenic fungi. |
| first_indexed | 2024-03-10T09:48:17Z |
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| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-03-10T09:48:17Z |
| publishDate | 2021-07-01 |
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| record_format | Article |
| series | Antibiotics |
| spelling | doaj.art-bfc3b1c426f543d3828bc58f21c5de1e2023-11-22T03:03:40ZengMDPI AGAntibiotics2079-63822021-07-0110781810.3390/antibiotics10070818In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i>Katy Díaz0Enrique Werner1Ximena Besoain2Susana Flores3Viviana Donoso4Bastian Said5Nelson Caro6Ernesto Vega7Iván Montenegro8Alejandro Madrid9Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso 2340000, ChileDepartamento de Ciencias Básicas, Campus Fernando May, Universidad del Bío-Bío, Avda. Andrés Bello 720, Casilla 447, Chillán 3780000, ChileEscuela de Agronomía, Pontificia Universidad Católica de Valparaíso, San Francisco s/n La Palma, Quillota 2260000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, 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), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileDepartamento de Química, Universidad Técnica Federico Santa María, Av. Santa María 6400, Santiago 7630000, ChileCentro de Investigación Australbiotech, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, ChileDepartamento Laboratorios y Estaciones Cuarentenarias, Servicio Agrícola y Ganadero, Ruta 68 # (Km. 12), Pudahuel 9020000, ChileEscuela de Obstetricia y Puericultura, Facultad de Medicina, Universidad de Valparaíso, Angamos 655, Reñaca 2520000, ChileLaboratorio de Productos Naturales y Síntesis Orgánica (LPNSO), Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, ChileThe aim of this study was to synthesize a series of novel and known dihydrocarvone-hybrid derivatives (<b>2</b>–<b>9</b>) and to evaluate mycelial growth activity of hybrid molecules against two strains of <i>Monilinia fructicola</i>, as well as their toxicity. Dihydrocarvone-hybrid derivatives have been synthesized under sonication conditions and characterized by FTIR, NMR, and HRMS. Antifungal efficacy against both strains of <i>M. fructicola</i> was determined by half maximal effective concentration (EC<sub>50</sub>) and toxicity using the brine shrimp lethality test (BSLT). Among the synthesized compounds, <b>7</b> and <b>8</b> showed the best activity against both strains of <i>M. fructicola</i> with EC<sub>50</sub> values of 148.1 and 145.9 µg/mL for strain 1 and 18.1 and 15.7 µg/mL for strain 2, respectively, compared to BC 1000<sup>®</sup> (commercial organic fungicide) but lower than Mystic<sup>®</sup> 520 SC. However, these compounds showed low toxicity values, 910 and 890 µg/mL, respectively, compared to Mystic<sup>®</sup> 520 SC, which was highly toxic. Based on the results, these hybrid compounds could be considered for the development of more active, less toxic, and environmentally friendly antifungal agents against phytopathogenic fungi.https://www.mdpi.com/2079-6382/10/7/818dihydrocarvone<i>Monilinia fructicola</i>hybrid compounds |
| spellingShingle | Katy Díaz Enrique Werner Ximena Besoain Susana Flores Viviana Donoso Bastian Said Nelson Caro Ernesto Vega Iván Montenegro Alejandro Madrid In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> Antibiotics dihydrocarvone <i>Monilinia fructicola</i> hybrid compounds |
| title | In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> |
| title_full | In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> |
| title_fullStr | In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> |
| title_full_unstemmed | In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> |
| title_short | In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against <i>Monilinia fructicola</i> |
| title_sort | in vitro antifungal activity and toxicity of dihydrocarvone hybrid derivatives against i monilinia fructicola i |
| topic | dihydrocarvone <i>Monilinia fructicola</i> hybrid compounds |
| url | https://www.mdpi.com/2079-6382/10/7/818 |
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