Antifungal activities of coumarins isolated from Angelica gigas and Angelica dahurica against Plant pathogenic fungi

In order to search potent antifungal substances from domestic plants, 40 plants cultivated in Korea were collected. After extracting with methanol (MeOH) and concentrating to dryness, the MeOH extracts were screened for in vivo antifungal activity against six plant diseases at a concentration of . Fourteen extracts showed disease-controlling activity more than 90% against at least one of the 6 plant diseases tested; eight, seven, and three extracts controlled more than 90% the development of rice blast, tomato late blight, and wheat leaf rust, respectively. However, none of the extracts exhibited in vivo antifungal activity more than 90% against rice sheath blight, tomato gray mold, and barley powdery mildew. From the MeOH extracts of Angelica gigas and A. dahurica showing potent controlling activity against rice blast, 1 and 2 antifungal substances, respectively, were isolated by solvent partitioning and column chromatography. The three compounds were identified to be coumarins, namely, decursin, imperatorin, and isoimperatorin, by mass spectrometry and NMR spectroscopy. They were examined for in vitro and in vivo antifungal activities together with umbelliferone (7-bydroxycournarin) and scopoletin (6-methoxy-7-hydroxycoumarin) containing a free hydroxyl group at position 7 to investigate the structure-activity relationship. In vitro, most of 50% growth inhibitory concentrations () were over , indicating that they have relatively weak antifungal activity. The antifungal activity of decursin and scopoletin, containing cyclic alkoxy groups instead of free hydroxyl group at position 7, was stronger than umbelliferone and scopoletin. Especially, decursin and imperatorin showed potent antifungal activities against Pythium ultimum and Magnaporthe grisea, respectively, with values less than . In vivo, decursin and imperatorin showed potent antifungal activity against rice blast, whereas other coumarins hardly controlled the development of 6 plant diseases tested. These results suggest that the antifungal activity of 7-hydroxycoumarin derivative is substantially increased when the hydroxyl group at position 7 is protected by a stable cyclic alkoxy grouping.