Chemical investigation of an insect pathogenic enterobacterium, Photorhabdus temperata SN259, led to the isolation and identification of seven metabolites, which include three new compounds, 3-hydroxy-2-isopropyl-5-phenethylphenyl carbamate, 1, 2-(1-hydroxypropan-2-yl)-5-[2-phenylethyl]benzene-1,3-diol, 2, 2-(1-hydroxypropan-2-yl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol, 3, and four known metabolites (4-7). Their structures were elucidated on the basis of MS and NMR data and by comparison with those reported previously. The activities of compounds 1-7 were evaluated against four phytopathogenic fungi (Pythium aphanidermatum, Rhizoctonia solani Kuhn, Exserohilum turcicum, and Fusarium oxysporum). In an agar medium assay, compounds 1 and 7 showed strong inhibition against P. aphanidermatum with EC50 values of 2.8 and 2.7 μg/mL, respectively. By comparing the structure of compounds 1-7, we deduced that the acylamino group in compound 1 and the isopropyl group in compound 7 contribute to the inhibitory activity.
Keywords: Exserohilum turcicum; Fusarium oxysporum; Photorhabdus temperata SN259; Pythium aphanidermatum; Rhizoctonia solani Kuhn; antifungal activity; stilbene derivatives.