| Summary: | Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (<b>1</b>–<b>3</b>), and a drimane sesquiterpenoid astellolide Q (<b>15</b>), together with eleven known compounds (<b>4</b>–<b>14</b>) were isolated from the cultures of the marine-derived fungus <i>Penicillium</i> sp. N-5, while compound <b>14</b> was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra. Hemiacetalmeroterpenoid A (<b>1</b>) possesses a unique and highly congested 6,6,6,6,5,5-hexa-cyclic skeleton. Moreover, the absolute configuration of compound <b>14</b> was also reported for the first time. Compounds <b>1</b>, <b>5</b> and <b>10</b> exhibited significant antimicrobial activities against <i>Penicillium italicum</i> and <i>Colletrichum gloeosporioides</i> with MIC values ranging from 1.56 to 6.25 μg/mL.
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