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Chemical study of the secondary metabolites of a deep-sea-derived fungus <i>Aspergillus sydowii</i> MCCC 3A00324 led to the isolation of eleven compounds (<b>1</b>–<b>11</b>), including one novel (<b>1</b>) and one new (<b>2</b>) osmane-related monoterpenoids and two undescribed polyketides (<b>3</b> and <b>4</b>). The structures of the metabolites were determined by comprehensive analyses of the NMR and HRESIMS spectra, in association with quantum chemical calculations of the ¹³C NMR, ECD, and specific rotation data for the configurational assignment. Compound <b>1</b> possessed a novel monoterpenoid skeleton, biogenetically probably derived from the osmane-type monoperpenoid after the cyclopentane ring cleavage and oxidation reactions. Additionally, compound <b>3</b> was the first example of the <i>α</i>-pyrone derivatives bearing two phenyl units at C-3 and C-5, respectively. The anti-inflammatory activities of <b>1</b>–<b>11</b> were tested. As a result, compound <b>6</b> showed potent inhibitory nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells with an inhibition rate of 94.4% at the concentration of 10 µM. In addition, a plausible biosynthetic pathway for <b>1</b> and <b>2</b> was also proposed.