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Registro Completo |
Biblioteca(s): |
Biblioteca Rui Tendinha. |
Data corrente: |
05/07/2020 |
Data da última atualização: |
05/07/2020 |
Tipo da produção científica: |
Artigo em Periódico Indexado |
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. |
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. |
Título: |
Synthesis of eugenol derivatives and evaluation of their antifungal activity against Fusarium solani f. sp. piperis. |
Ano de publicação: |
2020 |
Fonte/Imprenta: |
Current Pharmaceutical Design, v. 26, p. 1-11, 2020. |
Idioma: |
Inglês |
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 |
Thesagro: |
Doença de planta; Fungo; Fusarium; Fusarium solani; Pimenta; Pimenta do reino; Pimenta do reino preta. |
Thesaurus NAL: |
Antifungal; Cytotoxicity; Eugenol derivatives; Piper nigrum. |
Categoria do assunto: |
H Saúde e Patologia |
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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Registros recuperados : 9 | |
1. | | SILVA, I. R.; LEMOS, J. P.; ROCHA, T. T. T. da; SANTOS, E. P. dos; LIMA, I. de M. Produtividade do feijão-comum (Phaseolus vulgaris L.), submetido a diferentes bioestimulantes e doses de N- ureia In: ENCONTRO LATINO AMERICANO DE INICIACAO CIENTIFICA, 25.; ENCONTRO LATINO AMERICANO DE POS GRADUACAO, 21., 2023, Sao Jose dos Campos, SP. Ciencia, saude e tecnologia: agentes de transformacao e conscientizacao da sociedade . Sao Jose dos Campos: UNIVAP, 2021.Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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2. | | SANTOS, E. P. dos; LIMA, I. de M.; CALENTE, L.; SILVA, A. L.; SILVA, I. R. da.; ROCHA, T. T. T. da. Caracterização izoenzimática e incidência de populações de Meloidogyne spp. em pimenteira-do-reino cultivadas nos municípios da microrregião do rio doce capixaba. In: SIMPÓSIO INCAPER PESQUISA, 1. , Vitória, ES. Caracterização izoenzimática e incidência de populações de Meloidogyne spp. em pimenteira-do-reino cultivadas nos municípios da microrregião do rio doce capixaba. Editores, Andre Guarçoni Martins ... [et al]., Vitória, ES : Incaper, 2022. Anais... Vitória, ES : Incaper, p. 54, 2022.Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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3. | | LIMA, I. de M.; VENTURA, J. A.; COSTA, H.; SILVA, I. R.; SANTOS, E. P. dos; ROCHA, T. T. T. da Fitonematoides : coleta e envio de amostras nematológicas. Vitória, ES : Incaper, 2022. (Incaper, Documentos, 294). Folder.Biblioteca(s): Biblioteca Rui Tendinha. |
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4. | | SANTOS, E. P. dos; COSTA, N. S.; ARPINI, B. da S.; ROCHA, T. T. T. da; SILVA, I. R.; LIMA, I. de M. Efeito de Meloidogyne javanica no desenvolvimento de plantas de pimenta-do-reino (Piper nigrum L.). In: ENCONTRO LATINO AMERICANO DE INICIACAO CIENTIFICA, 25.; ENCONTRO LATINO AMERICANO DE POS GRADUACAO, 21., 2023, São José dos Campos, SP. Ciencia, saude e tecnologia: agentes de transformacao e conscientizacao da sociedade . São José dos Campos: UNIVAP, 2021.Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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5. | | ROCHA, T. T. T. da; SILVA, I. R. da; SANTOS, E. P. dos; SILVA, A.. L.; CALENTE, L.; LIMA, I. de M. Cultivos precedentes em áreas de produção de Café Conilon no norte e noroeste do Estado do Espírito Santo. In: SIMPÓSIO INCAPER PESQUISA, 1. , Vitória, ES. Cultivos precedentes em áreas de produção de Café Conilon no norte e noroeste do Estado do Espírito Santo. Editores, Andre Guarçoni Martins ... [et al]., Vitória, ES : Incaper, 2022. Anais... Vitória, ES : Incaper, p. 21, 2022.Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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6. | | LIMA, I. de M.; VENTURA, J. A.; COSTA, H.; SILVA, I.R.; SANTOS, E. P. dos; ROCHA, T. T. T. da Nematoides : um risco para a cafeicultura do Espírito Santo. Vitória, ES : Incaper, 2022. (Incaper, Documentos, 292). Folder.Biblioteca(s): Biblioteca Rui Tendinha. |
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7. | | SILVA, I. R.; ANGELI, L. C. F.; ARAÚJO, K. de S.; ROCHA, T. T. T. da; BEIRAL, G. N.; LIMA, I. de M. Resistência de clones elites de cafeeiro conilon (seleção 2022) a Meloidogyne incógnita. In: SIMPÓSIO INCAPER PESQUISA, 3. , Vitória, ES. Resistência de clones elites de cafeeiro conilon (seleção 2022) a Meloidogyne incógnita. Editores, Andréa Ferreira da Costa, Marlon Dutra Degli Esposti e Renato Corrêa Taques. Vitória, ES : Incaper, p. 47, 2024. p. 47Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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8. | | SILVA, R. S.; ANGELI, L. C. F.; ARAÚJO, K. de S.; ROCHA, T. T. T. da; MOURÃO, T. S.; LIMA, I. de M. Resistência de clones elites de cafeeiro conilon (seleção 2022) à Meloidogyne Paranaensis. In: SIMPÓSIO INCAPER PESQUISA, 3. , Vitória, ES. Resistência de clones elites de cafeeiro conilon (seleção 2022) à Meloidogyne Paranaensis. Editores, Andréa Ferreira da Costa, Marlon Dutra Degli Esposti e Renato Corrêa Taques. Vitória, ES : Incaper, p. 46, 2024. p. 46Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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9. | | ROCHA, T. T. T. da; CARVALHO, A. J. E. de; LEMOS, J. P.; SILVA, I. R. da; SANTOS, E. P. dos; LIMA, I. de M. Resposta do sistema radicular do feijoeiro-comum à inoculação alternativa com estirpes rizobianas. In: ENCONTRO LATINO AMERICANO DE INICIACAO CIENTIFICA, 25.; ENCONTRO LATINO AMERICANO DE POS GRADUACAO, 21., 2023, São José dos Campos, SP. Ciencia, saude e tecnologia: agentes de transformacao e conscientizacao da sociedade . São José dos Campos: UNIVAP, 2021.Tipo: Publicação em Anais de Congresso |
Biblioteca(s): Biblioteca Rui Tendinha. |
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Registros recuperados : 9 | |
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