Semissíntese e avaliação antifúngica contra Fusarium solani f. sp. piperis de derivados do eugenol
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Data
2020-03-03
Autores
Maximino, Sarah Canal
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Universidade Federal do Espírito Santo
Resumo
Black pepper (Piper nigrum L.) has a high economic and export power due to the various forms of commercialization and the wide applicability of its essential oil. Meanwhile, Fusarium solani f. sp. piperis, a phytopathogen, is responsible for causing fusariosis, a disease that destroys black pepper crops, causing great economic losses and agricultural production. Currently, to control this fungus, a triazole agrochemical, tebuconazole, is used in plantations. However, the excessive use of tebuconazole causes damage to plantations, the environment and human health, making it necessary to use more efficient substances, with low cost and that do not cause harm to man. Eugenol, a major compound present in clove essential oil, has several activities and a high fungicidal potential and is a viable alternative in the search for more effective and safer substances. For this purpose, eugenol derivatives (3, 4, 5, 6 and 7) were synthesized in the presence of potassium carbonate, in acetone, and commercial functionalized bromides, via bimolecular nucleophilic substitution synthesis. The eugenol derivatives (8 and 9) were obtained via cycloaddition azido-alkaline catalyzed by Cu (I) (CuAAC) in the presence of copper sulfate and sodium ascorbate, in dimethylformamide and microwave irradiation. The antifungal potential was evaluated by the broth microdilution assay standardized by the CLSI M38-A2 standard. Compound (6) was the most active against F. solani f. sp. piperis, being twice as effective as tebuconazole, with CFM of 50 µg mL-1. In the evaluation of the cytotoxic profile in macrophages, the compound (6) presented cytotoxicity similar to tebuconazole, however after exposure to a metabolizing system (fraction S9) that mimics the hepatic metabolism, the compound (6) demonstrated maintenance of cytotoxicity with IC50 values of 11.18 ± 0.5 µg mL-1 and 9.04 ± 0.2 µg mL-1 without and with the S9 fraction, respectively, with no statistical significance. Therefore, Compound (6) shows to be a promising antifungal against this pathogen.
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Eugenol , Fusarium solani f. sp. piperis , Atividade antifúngica , Triazol , Antifungal activity , Triazole , Química orgânica , Síntese orgânica , Fungos