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Nine new secondary metabolites, including six isocoumarin analogues, 7-hydroxyoospolactone ( 1 ), 7-methoxyoospolactone ( 2 ), 7-methoxy-9-hydroxyoospolactone ( 3 ), 10-acetoxy-9-hydroxyoospolactone ( 4 ), 6-dehydroxysescandelin ( 5 ), parapholactone ( 6 ), and three compounds with a rare skeleton of isocoumarin coupled with phenylethylamine, namely paraphamide A ( 12 ), paraphamide B ( 13 ), and paraphamide C ( 14 ), together with five known compounds, oospolactone ( 7 ), 8- O -methyloospolactone ( 8 ), 10-hydroxyoospolactone ( 9 ), 9,10-dihydroxyoospolactone ( 10 ), and oospoglycol ( 11 ), were isolated and identified from the marine-derived fungus Paraphoma sp. CUGBMF180003. Their chemical structures were determined using spectroscopic data, including HRESIMS and 1D and 2D NMR techniques. Furthermore, the stereogenic carbons in 5 and 14 were determined by comparing the experimental and calculated electronic circular dichroism (ECD) spectra. The carbon skeleton of 12 - 14 was identified as the first example of isocoumarin coupled with phenylethylamine derivatives. All of these compounds were examined for antimicrobial activities against Candida albicans and Staphylococcus aureus. Both 1 and 6 showed antibacterial activity against S. aureus with MIC values of 12.5 μg/mL.

New Isocoumarin Analogues from the Marine-Derived Fungus Paraphoma sp. CUGBMF180003