| Summary: | The sponge-derived fungus <i>Penicillium</i> sp. SCSIO41015 cultured on solid rice medium yielded twenty-one compounds (<b>1</b>−<b>21</b>), including two new alkaloids (<b>1</b> and <b>2</b>) and one new pyrone derivative (<b>3</b>). Their structures were elucidated by analysis of 1D/2D NMR data and HR−ESI−MS. Their absolute configurations were established by single-crystal X-ray diffraction analysis and comparison of the experimental with reported specific rotation values. Compound <b>16</b> exhibited selective cytotoxic activity against the human gastric cancer cells MGC803, with IC<sub>50</sub> value of 5.19 μM. Compounds <b>9</b> and <b>18</b> showed weak antibacterial activity against <i>Staphylococcus aureus</i> and <i>Acinetobacter baumannii,</i> respectively, both with MIC values of 57 μg/mL. Furthermore, compound <b>16</b> displayed potent antibacterial activity against <i>S. aureus</i> with an MIC value of 3.75 μg/mL.
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