Cyclopenta[b]benzofurans from Aglaia species with pronounced antifungal activity against rice blast fungus (Pyricularia grisea).

Abstract

Eight flavaglines, six cyclopenta[b]benzofurans, a cyclopenta[bc]benzopyran, and a benzo[b]oxepine, together with an aromatic butyrolactone were isolated from Aglaia odorata, A. elaeagnoidea, and A. edulis (Meliaceae) and tested against the three plant pathogens Pyricularia grisea, Fusarium avenaceum, and Alternaria citri for antifungal properties. Using the microdilution technique linked with digital image analysis of germ tubes, the benzofurans displayed strong activity, whereas the benzopyran, benzoxepine, and butyrolactone were inactive at the highest concentration tested. P. grisea, responsible for rice blast disease, was the most susceptible fungus against all benzofurans, with rocaglaol as the most active derivative. Based on EC(50), EC(90), and MIC values, the antifungal activity of rocaglaol was clearly higher than of the reference compounds, blasticidin S and Benlate.