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Nine new azaphilones, including penicilazaphilones I–N (<b>1</b>, <b>2</b> and <b>6</b>–<b>9</b>), <i>epi</i>-geumsanol D (<b>3</b>) and penidioxolanes C (<b>4</b>) and D (<b>5</b>) were isolated from the culture of the marine-derived fungus <i>Penicillium sclerotiorum</i> E23Y-1A. The structures of the isolates were deduced from extensive spectroscopic data (1D and 2D NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), and electronic circular dichroism (ECD) calculations. All the azaphilones from <i>P. sclerotiorum</i> E23Y-1A were tested for their anti-inflammatory and antitumor activities. Penicilazaphilone N (<b>9</b>) showed moderate anti-inflammatory activity with an IC₅₀ value of 22.63 ± 2.95 μM, whereas penidioxolane C (<b>4</b>) exhibited moderate inhibition against human myeloid leukemia cells (K562), human liver cancer cells (BEL-7402), human gastric cancer cells (SGC-7901), human non-small cell lung cancer cells (A549), and human hela cervical cancer cells, with IC₅₀ values of 23.94 ± 0.11, 60.66 ± 0.13, 46.17 ± 0.17, 60.16 ± 0.26, and 59.30 ± 0.60 μM, respectively.