Secondary metabolites from Aspergillus terreus F6-3, a marine fungus associated with Johnius belengerii

Two new terrein derivatives asperterreinones A-B (1-2), one new octahydrocoumarin derivative (+/-)-asperterreinin A (6), along with seventeen known compounds, were isolated from Aspergillus terreus F6-3, a marine fungus associated with Johnius belengerii. The structures of 1, 2, and 6 were established on the basis of 1D and 2D NMR, mass spectroscopy, comparative electronic circular dichroism (ECD) spectra analysis, density functional theory calculation of C-13 NMR, and DP4+ probability analysis. Among all the isolates, eurylene (7), a constituent of the Malaysian medicinal plant Eurycoma longifolia, was obtained from a microbial source for first time. In the in vitro bioassay, 11 and 13 showed potent inhibitory activity against the Escherichia coli beta-glucuronidase (EcGUS) with IC50 values of 27.75 +/- 0.73 and 17.73 +/- 0.81 mu M, respectively. It was the first time that questinol (11) and (+/-)-aspertertone B (13) were reported as potent EcGUS inhibitors.