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Cytotoxic and Antifungal Activity of Chalcones Synthesized from Natural Acetophenone Isolated from Croton anisodontus

2020; Brazilian Society of Chemistry; Volume: 12; Issue: 3 Linguagem: Inglês

10.21577/1984-6835.20200057

1984-6835

Priscila Teixeira da Silva, Layanne Mesquita Albuquerque Lopes, Jayze da Cunha Xavier, Mylena Costa S. de Carvalho, Manoel Odorico de Moraes, Cláudia Pessoa, Francisco Washington Araújo Barros Nepomuceno, Paulo Nogueira Bandeira, Carolina Sidrim de Paula Cavalcante Targino, Alexandre Magno Rodrigues Teixeira, Raquel Oliveira dos Santos Fontenelle, Hélcio Silva dos Santos,

Insect Pest Control Strategies

Resumo: Neste trabalho, oito chalconas foram sintetizadas a partir da 2-hidroxi-3,4,6-trimetoxiacetofenona isolada de Croton anisodontus com benzaldeído e seus derivados, bem como avaliadas suas atividades citotóxica e antifúngica.Chalconas foram sintetizadas pela reação de condensação aldólica de Claisen-Schimdt em meio básico e identificadas por RMN de 1 H e 13 C, IV e EM.O ensaio MTT foi utilizado para determinar a citotoxicidade de todos os compostos sintetizados contra linhas celulares de câncer humano.Os resultados mostraram que % RCV variou de 19,43 ± 1,31 a 75,51 ± 1,84 %.A chalcona (E) -3-(4-fluorofenil) -1-(2-hidroxi-3,4,6-trimetoxifenil) prop-2-en-1-ona demonstrou a atividade mais forte contra células HCT-116 (% RCV = 75,51 ± 1,84).O potencial antifúngico in vitro das chalconas revelou que as chalconas (E)-3-(furan-2-il) -1-(2-hidroxi-3,4,6-trimetoxifenil) prop-2-en-1-ona (CMI 0,625 mg/mL contra C. albicans LABMIC 0105) e (E) -1-(2-hidroxi-3,4,6-trimetoxifenil) -3-(4-metoxifenil) prop-2-en-1-ona (CMI 0,312 mg / mL contra C. albicans LABMIC 0107) foram consideradas como chalconas de melhor inibição fúngica.A avaliação sinérgica in vitro mostrou que a união entre a anfotericina B e a chalcona (E) -1-(2-hidroxi-3,4,6-trimetoxifenil)-3-(4-metoxifenil) prop-2-en-1-ona mostrou efeito sinérgico contra C. albicans LABMIC 0105 (IFIC = 0,124) e efeito indiferente contra C. albicans LABMIC 0107 (IFIC = 1,0072), para cinética da morte, apenas o tratamento com a chalcona (E)-1-(2-hidroxi -3,4,6-trimetoxifenil)-3-(4-metoxifenil) prop-2-en-1-ona contra LABMIC 0107 foi capaz de promover a redução de células fúngicas entre os períodos de 4 a 8 h e inibição de 100 % a partir daí , semelhante ao mecanismo de ação da anfotericina B.In this work, eight chalcones were synthesized from the 2-hydroxy-3,4,6trimethoxyacetophenone isolated from Croton anisodontus with benzaldehyde and its derivatives as well as evaluated its cytotoxic and antifungal activities.Chalcones were synthesized by the Claisen-Schimdt aldol condensation reaction in basic medium and identified by 1 H and 13 C NMR, IR and MS.The MTT assay was used to determine the cytotoxicity of all synthetized compounds against human cancer cell lines.The results showed that the % RCV varied from 19.43 ± 1.31 to 75.51 ± 1.84 %.The chalcone (E)-3-(4-fluorophenyl)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)prop-2-en-1-one demonstrated the strongest activity against HCT-116 cells (% RCV = 75.51± 1.84).The in vitro antifungal potential of the chalcones showed that chalcones (E)-3-(furan-2-yl)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)prop-2-en-1-one (MIC 0.62 mg/mL against C. albicans LABMIC 0105) and (E)-1-(2-hydroxy-3,4,6trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (MIC 0.31 mg/mL against C. albicans LABMIC 0107) were considered as chalcones of better fungal inhibition.The synergistic evaluation in vitro showed that the union between Amphotericin B and chalcone (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one showed an synergistic effect against C. albicans LABMIC 0105 (IFIC = 0.124) and indifferent effect against C. albicans LABMIC 0107 (IFIC = 1.0072), for kinetics of fungal death, only treatment with chalcone (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4methoxyphenyl)prop-2-en-1-one against LABMIC 0107 was able to promote reduction of fungal cells between the periods of 4 to 8 h and 100 % inhibition thereafter, resembling the mechanism of action of Amphotericin B.