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Sumalarins D–G (1 – 4), four previously undescribed curvularin derivatives, along with two known related metabolites, curvularin (5) and dehydrocurvularin (6), were isolated and identified from the mangrove-derived fungus Penicillium sumatrense MA-325. Among them, sumalarin D (1) represents a unique example of curvularin derivative featuring a 5-methylfuran-2-yl-methyl group. Their structures were elucidated based on analysis of NMR and MS data as well as comparison of ECD spectra and quantum chemical calculations of NMR, and compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1 , 2 , 5 , and 6 are active against aquatic pathogenic bacteria Vibrio alginolyticus and V. harveyi with MIC values ranging from 4 to 64 μ g/mL, while compound 6 is cytotoxic against tumor cell lines 5673, HCT 116, 786-O, and Hela with IC 50 values of 3.5, 10.6, 10.9, and 14.9 μ M, respectively. Sumalarin D (1), the first curvularin featuring a unique 5-methylfuran-2-yl-methyl group at C-4, along with three curvularin congeners, were identified from the mangrove-derived Penicillium sumatrense MA-325. [Display omitted] • Four previously undescribed curvularins were isolated from mangrove-derived Penicillium sumatrense. • Sumalarin D (1) is the first curvularin featuring a unique 5-methylfuran-2-yl-methyl group at C-4. • ECD and DP4+ calculation and X-ray diffraction were used for structure determination. • Dehydrocurvularin (6) exhibited potent cytotoxic activities against a panel of tumor cell lines. [ABSTRACT FROM AUTHOR]