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To discover the new medical entity from edible marine algae, our continuously natural product investigation focused on endophytes from marine macroalgae <i>Grateloupia</i> sp. Two new azaphilones, 8a-<i>epi</i>-hypocrellone A (<b>1</b>), 8a-<i>epi</i>-eupenicilazaphilone C (<b>2</b>), together with five known azaphilones, hypocrellone A (<b>3</b>), eupenicilazaphilone C (<b>4</b>), ((1<i>E</i>,3<i>E</i>)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde (<b>5</b>), sclerotiorin (<b>6</b>), and isochromophilone IV (<b>7</b>) were isolated from the alga-derived fungus <i>Penicillium sclerotiorum</i>. The structures of isolated azaphilones (<b>1</b>–<b>7</b>) were elucidated by spectrometric identification, especially HRESIMS, CD, and NMR data analyses. Concerning bioactivity, cytotoxic, anti-inflammatory, and anti-fibrosis activities of those isolates were evaluated. As a result, compound <b>1</b> showed selective toxicity toward neuroblastoma cell line SH-SY5Y among seven cancer and one fibroblast cell lines. 20 μM of compounds <b>1</b>, <b>3</b>, and <b>7</b> inhibited the TNF-α-induced NFκB phosphorylation but did not change the NFκB activity. Compounds <b>2</b> and <b>6</b> respectively promoted and inhibited SMAD-mediated transcriptional activities stimulated by TGF-β.