Cyclopenta[b]benzofurans from Aglaia species with pronounced antifungal activity against rice blast fungus (Pyricularia grisea).
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.
Engelmeier
D
D
Comparative Phytochemistry Department, Institute of Botany, University of Vienna, Rennweg 14, A-1030 Vienna, Austria.
Hadacek
F
F
Pacher
T
T
Vajrodaya
S
S
Greger
H
H
D000528:Alternaria / Q000187:drug effects; D000935:Antifungal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005670:Fusarium / Q000187:drug effects; D020082:Magnaporthe / Q000187:drug effects* / Q000472:pathogenicity; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012275:Oryza / Q000382:microbiology*; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D001572:Benzofurans