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

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 H-1 and C-13 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-(4-methoxyphenyl)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.