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Two new prenylated indole alkaloids, 17-epi-notoamides Q and M (1and 2), and two new phenyl ether derivatives, cordyols D and E (9and 13), together with 10 known compounds (3–8, 10–12, 14) were isolated from a marine-derived Aspergillussp. fungus. Among them, 1/5and 2/4were pairs of epimers. The planar structures and absolute configurations of the new compounds were determined by extensive NMR spectroscopic data as well as CD spectra. The absolute configuration of 3was confirmed by single-crystal X-ray diffraction analysis for the first time. All isolated metabolites (1–14) and eight synthetic phenyl ether derivatives (12a, 14a–14g) were evaluated for their antibacterial activities in vitro. The polybromide phenyl ether 14gshowed pronounced antibacterial activity against Staphylococcus epidermidiswith an MIC value of 0.556 μM, stronger than that of the positive control ciprofloxacin (MIC = 3.13 μM).

Ten new fungal metabolites, including three hydroisocoumarins, penicimarins A–C (1–3), three isocoumarins, penicimarins D–F (6–8), and four benzofurans, penicifurans A–D (11–14), together with four known isocoumarin derivatives (4, 5, 9, 10), were obtained from the sponge-derived fungus Penicilliumsp. MWZ14-4, collected from the South China Sea. Their planar structures and relative configurations were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1–4were assigned by the modified Mosher’s method and TDDFT ECD calculations together with comparison of their CD spectra. Compound 1represents a rare naturally occurring isocoumarin derivative with 4-substitution, but no substituent at the 3-position. These compounds were evaluated for antibacterial activities and cytotoxic activities in vitro. Among them, penicifuran A (11) exhibited inhibitory activity against Staphylococcus albuswith an MIC value of 3.13 μM.