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 | Acesso ao texto completo restrito à biblioteca da Biblioteca Rui Tendinha. Para informações adicionais entre em contato com biblioteca@incaper.es.gov.br. |
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Registro Completo |
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Biblioteca(s): |
Biblioteca Rui Tendinha. |
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Data corrente: |
05/07/2020 |
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Data da última atualização: |
05/07/2020 |
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Tipo da produção científica: |
Artigo em Periódico Indexado |
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Circulação/Nível: |
A - 1 |
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Autoria: |
MAXIMINO, S. C.; DUTRA, J. A. P.; RODRIGUES, R. P.; GONÇALVES, R. de C. R.; MORAIS, P. A. B.; VENTURA, J. A.; SCHUENCK, R. P.; LACERDA JÚNIOR, V.; KITAGAWA, R. R.; BORGES, W. de S. |
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Afiliação: |
Sarah C. Maximino; Jessyca Aparecida Paes Dutra; Ricardo Pereira Rodrigues; Rita de Cássia Ribeiro Gonçalves; Pedro Alves Bezerra de Morais; Jose Aires Ventura, Incaper; Ricardo Pinto Schuenck; Valdemar Lacerda Júnior; Rodrigo Rezende Kitagawa; Warley de Souza Borges. |
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Título: |
Synthesis of eugenol derivatives and evaluation of their antifungal activity against Fusarium solani f. sp. piperis. |
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Ano de publicação: |
2020 |
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Fonte/Imprenta: |
Current Pharmaceutical Design, v. 26, p. 1-11, 2020. |
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Idioma: |
Inglês |
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Conteúdo: |
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 β-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. MenosBackground: 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 β-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... Mostrar Tudo |
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Thesagro: |
Doença de planta; Fungo; Fusarium; Fusarium solani; Pimenta; Pimenta do reino; Pimenta do reino preta. |
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Thesaurus NAL: |
Antifungal; Cytotoxicity; Eugenol derivatives; Piper nigrum. |
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Categoria do assunto: |
H Saúde e Patologia |
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Marc: |
LEADER 03014naa a2200361 a 4500
001 1022236
005 2020-07-05
008 2020 bl uuuu u00u1 u #d
100 1 $aMAXIMINO, S. C.
245 $aSynthesis of eugenol derivatives and evaluation of their antifungal activity against Fusarium solani f. sp. piperis.$h[electronic resource]
260 $c2020
520 $aBackground: 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 β-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.
650 $aAntifungal
650 $aCytotoxicity
650 $aEugenol derivatives
650 $aPiper nigrum
650 $aDoença de planta
650 $aFungo
650 $aFusarium
650 $aFusarium solani
650 $aPimenta
650 $aPimenta do reino
650 $aPimenta do reino preta
700 1 $aDUTRA, J. A. P.
700 1 $aRODRIGUES, R. P.
700 1 $aGONÇALVES, R. de C. R.
700 1 $aMORAIS, P. A. B.
700 1 $aVENTURA, J. A.
700 1 $aSCHUENCK, R. P.
700 1 $aLACERDA JÚNIOR, V.
700 1 $aKITAGAWA, R. R.
700 1 $aBORGES, W. de S.
773 $tCurrent Pharmaceutical Design$gv. 26, p. 1-11, 2020.
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