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Synthesis of Eugenol Derivatives and Evaluation of their Antifungal Activity Against Fusarium solani f. sp. piperis.
Maximino, Sarah C; Dutra, Jessyca A P; Rodrigues, Ricardo P; Gonçalves, Rita C R; Morais, Pedro A B; Ventura, José A; Schuenck, Ricardo P; Júnior, Valdemar Lacerda; Kitagawa, Rodrigo R; S Borges, Warley.
Afiliación
  • Maximino SC; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • Dutra JAP; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • Rodrigues RP; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • Gonçalves RCR; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • Morais PAB; Department of Chemistry and Physics, Exact, Natural and Health Sciences Center, Federal University of Espírito Santo, Alto Universitário, s/n, Guararema, Alegre, ES, Brazil.
  • Ventura JA; Capixaba Institute for Research, Technical Assistance and Rural Extension, Rua Afonso Sarlo 160, Bento Ferreira, 29052-010, Vitória, ES, Brazil.
  • Schuenck RP; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • Júnior VL; Department of Chemistry, Exact Sciences Center, Federal University of Espírito Santo, Avenida Fernando Ferrari 514, Goiabeiras, 29075-910, Vitória, ES, Brazil.
  • Kitagawa RR; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
  • S Borges W; Graduate Program of Pharmaceutical Sciences, Health Sciences Center, Federal University of Espírito Santo, Avenida Marechal Campos 1468, Maruípe, 29047-105,Vitória, ES, Brazil.
Curr Pharm Des ; 26(14): 1532-1542, 2020.
Article en En | MEDLINE | ID: mdl-32242782
BACKGROUND: Fusarium solani f. sp. piperis is a phytopathogen that causes one of the most destructive diseases in black pepper crops, resulting in significant economic and crop production losses. Consequently, the control of this fungal disease is a matter of current and relevant interest in agriculture. OBJECTIVE: The objective was to synthesize eugenol derivatives with antifungal activity. METHODS: In this study, using bimolecular nucleophilic substitution and click chemistry approaches, four new and three known eugenol derivatives were obtained. The eugenol derivatives were characterized and their antifungal and cytotoxic effects were evaluated. RESULTS: Eugenol derivative 4 (2-(4-allyl-2-methoxyphenoxy)-3-chloronaphthalene-1,4-dione) was the most active against F. solani f. sp. piperis and showed acceptable cytotoxicity. Compound 4 was two-fold more effective than tebuconazole in an antifungal assay and presented similar cytotoxicity in macrophages. The in silico study of ß-glucosidase suggests a potential interaction of 4 with amino acid residues by a cation-π interaction with residue Arg177 followed by a hydrogen bond with Glu596, indicating an important role in the interactions with 4, justifying the antifungal action of this compound. In addition, the cytotoxicity after metabolism was evaluated as a mimic assay with the S9 fraction in HepG2 cells. Compound 4 demonstrated maintenance of cytotoxicity, showing IC50 values of 11.18 ± 0.5 and 9.04 ± 0.2 µg mL-1 without and with the S9 fraction, respectively. In contrast, eugenol (257.9 ± 0.4 and 133.5 ± 0.8 µg mL-1), tebuconazole (34.94 ± 0.2 and 26.76 ± 0.17 µg mL-1) and especially carbendazim (251.0 ± 0.30 and 34.7 ± 0.10 µg mL-1) showed greater cytotoxicity after hepatic biotransformation. CONCLUSION: The results suggest that 4 is a potential candidate for use in the design of new and effective compounds that could control this pathogen.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Eugenol / Fusarium / Antifúngicos Idioma: En Revista: Curr Pharm Des Asunto de la revista: FARMACIA Año: 2020 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Emiratos Árabes Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Eugenol / Fusarium / Antifúngicos Idioma: En Revista: Curr Pharm Des Asunto de la revista: FARMACIA Año: 2020 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Emiratos Árabes Unidos