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A systematic chemical investigation of the deep-sea-derived fungus <i>Penicillium solitum</i> MCCC 3A00215 resulted in the isolation of one novel polyketide (<b>1</b>), two new alkaloids (<b>2</b> and <b>3</b>), and 22 known (<b>4</b>–<b>2</b><b>5</b>) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (<b>13</b>) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC₅₀ values of around 20 μM. Moreover, <b>13</b> displayed potent in vitro anti-food allergic activity with an IC₅₀ value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (<b>9</b>) and penicopeptide A (<b>10</b>) showed moderate effects (IC₅₀ = 50 and 58 μM, respectively).