| Summary: | In this study, the antifungal potential of chemical constituents from <i>Piper pesaresanum</i> and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of <i>P. pesaresanum</i>, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi <i>Moniliophthora roreri</i>, <i>Fusarium solani</i> and <i>Phytophthora</i> sp. The chemical study allowed the isolation of three benzoic acid derivatives (<b>1</b>–<b>3</b>), one dihydrochalcone (<b>4</b>) and a mixture of sterols (<b>5</b>–<b>7</b>). Seven derivatives (<b>8</b>–<b>14</b>) were synthesized from the main constituents, of which compounds <b>9</b>, <b>10</b>, <b>12</b> and <b>14</b> are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against <i>M. roreri</i>, of which <b>11</b> (3.0 ± 0.8 µM) was the most active compound with an IC<sub>50</sub> lower compared with positive control Mancozeb<sup>®</sup> (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against <i>F. solani</i> and <i>Phytophthora</i> sp., of which <b>3</b> (32.5 ± 3.3 µM) and <b>4</b> (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.
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