Ophiocerol, a novel macrocylic neolignan from the aquatic fungus Ophioceras dolichostomum YMF1.00988

From cultural filtrates of the freshwater fungus Ophioceras dolichostomum YMF1.00988 a novel neolignan with an unprecedented dibenzo-1,6-dioxacyclodecane carbon skeleton, ophiocerol (1), was isolated, and the known compounds isoamericanoic acid A (2) and caffeic acid (3) were identified. The structure of the novel compound was determined by interpretation of its spectroscopic data, including 1D and 2D, (1)H and (13)C NMR (COSY, HMQC, HMBC, NOESY), and MS. Compounds 1-3 were assayed for their nematicidal activity against Bursaphelenchus xylophilus as well as their antifungal activity against several plant pathogen fungi.