Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome

An antifungal substance active against Colletotrichum orbiculare (Berk & Mont) Arx was isolated from the methanol extracts of Asarum sieboldii (Miq) Maek rhizomes. High-resolution MS, NMR and UV spectral data confirmed that the antifungal substance is kakuol, 2-hydroxy-4,5-methylenedioxypropiophenone. Colletotrichum orbiculare was most sensitive to kakuol, with MIC of 10 mu g ml(-1). Kakuol also completely inhibited the mycelial growth of Botrytis cinerea Pers ex Fr and Cladosporium cucumerinum Ellis & Arthur at 50 mu g ml(-1) and 30 mu g ml(-1), respectively. However, no antimicrobial activity was found against yeast and bacteria even at 100 mu g ml(-1). Kakuol exhibited a protective activity against the development of anthracnose disease on cucumber plants. The control efficacy of kakuol against the anthracnose disease was in general somewhat less than that of the commercial fungicide chlorothalonil. This is the first report to demonstrate in vitro and in vivo antifungal activity of kakuol against C orbiculare infection. (c) 2005 Society of Chemical Industry.