Submitted to: Journal of Chemical Ecology
Publication Type: Peer reviewed journal
Publication Acceptance Date: 4/14/2003
Publication Date: 8/1/2003
Citation: MEEPAGALA, K.M., KUHAJEK, J.M., STURTZ, G.D., WEDGE, D.E. VULGARONE B, THE ANTIFUNGAL CONSTITUENT IN THE STEAM-DISTILLED FRACTION OF ARTEMISIA DOUGLASIANA. JOURNAL OF CHEMICAL ECOLOGY. 2003. v.29(8). p. 1771-1780. Interpretive Summary: As part of our continuing search for natural product-based agrochemicals, we screened the steam-distilled oil of the aerial parts of Artemisia douglasiana, a plant in the family Asteraceae. The preliminary results showed the presence of antifungal activity against plant pathogenic fungi that cause Anthrcnose disease in strawberry. We isolated and identified the active compound as vulgarone B. This is the first report of the antifungal activity of vulgarone B.
Technical Abstract: The steam-distilled fraction of the aerial parts of Artemisia douglasiana was tested for activity against strawberry plant pathogenic fungi Botrytis cinerea, Colletotrichum acutatum, C. fragariae, C. gloeosporioides. Bioautography on silica TLC plates demonstrated the presence of antifungal activity of the steam distillate. The antifungal compound, Vulgarone B was isolated by bioassay-guided fractionation and chromatographic techniques and identified by NMR and GC-MS. In addition, the antifungal activity of vulgarone B and verbenone, and their corresponding alcohols were tested by bioautography and microtiter assay. Structure-activity studies revealed that the alpha, beta-unsaturated carbonyl functionality is a prerequisite for the antifungal activity of these mono and sesquiterpene ketones. This is the first report of antifungal activity of vulgarone B.