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Four novel, rare carbon-bridged citrinin dimers, namely dicitrinones G–J (<b>1</b>–<b>4</b>), and five known analogs (<b>5</b>–<b>9</b>) were isolated from the starfish-derived fungus <i>Penicillium</i> sp. GGF 16-1-2. Their structures were elucidated by extensive spectroscopic analysis and quantum chemical calculations. Compounds <b>1</b>–<b>9</b> exhibited strong antifungal activities against <i>Colletotrichum gloeosporioides</i> with LD₅₀ values from 0.61 μg/mL to 16.14 μg/mL. Meanwhile, all compounds were evaluated for their cytotoxic activities against human pancreatic cancer BXPC-3 and PANC-1 cell lines; as a result, compound <b>1</b> showed more significant cytotoxicities than the positive control against both cell lines. In addition, based on the analyses of the protein-protein interaction (PPI) network and Western blot, <b>1</b> could induce apoptosis by activating caspase 3 proteins (CASP3).