Eco-Friendly Crop Protection: <i>Argyrantemum frutescens</i>, a Source of Biofungicides
Eduardo Hernández-Álvarez | Samuel Rodríguez-Sabina | Noelia Labrador-García | Javier Hernández Pérez | Carolina P. Reyes | María Ángeles Llaría-López | Ignacio A. Jiménez | Isabel L. Bazzocchi
Plant-derived biopesticides are emerging as a promising and popular alternative for promoting cleaner and safer agricultural practices. The present work aims to explore <i>Argyranthemum frutescens</i> (<i>Asteraceae</i>) as a source of botanical pesticides and to validate this through a cultivation process. To this task, a bioassay-guided fractionation of the ethanolic root extracts from both wild and cultivated <i>A. frutescens</i> on phytopathogenic fungi of <i>Botrytis cinerea</i>, <i>Fusarium oxysporum</i>, and <i>Alternaria alternata</i> was conducted. This approach led to the identification of polyacetylenes with higher potency than commercial fungicides. Specifically, compounds <b>3</b> (capillin) and <b>5</b> (frutescinone) showed more than 90% growth inhibition at 0.05 mg/mL concentration on <i>B. cinerea</i>, while compounds <b>2</b> (capillinol) and <b>3</b> were also more active than positive controls, Fosbel-Plus and Azoxystrobin, against <i>F. oxysporum</i>. The structures of the isolated polyacetylenes (<b>1</b>–<b>6</b>, <b>9</b>, and <b>10</b>) and alkamides (<b>7</b>, <b>8</b>, and <b>11</b>) were determined through spectroscopic analysis, and the absolute configuration of stereocenter C1 of compounds <b>1</b>, <b>2</b>, <b>4</b> and <b>9</b> was determined by NMR-spectroscopy with (<i>R</i>)-(-)-α-methoxy-phenylacetic as a chiral derivatizing agent, and biogenetic considerations. Overall, this study supports the potential of polyacetylenes as promising agrochemical lead compounds against phytopathogens, and validates <i>A. frutescens</i> cultivation as a viable source of biopesticides.
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