Eight new polyketides, including three dimeric benzophenones, named dipleosporones A-C (1-3), three benzophenones (4-6), one xanthone (7), and one phenylbenzoate (8), along with seven known polyketides (9-15) were isolated from the fungus Pleosporales sp. YY-4. The structures of the new compounds were established on the basis of spectroscopic methods, including high-resolution electrospray ionization mass spectrometry and one- and two-dimensional nuclear magnetic resonance. This is the first report of a benzophenone dimer connection via a C bridge from natural sources. An anti-inflammatory assay indicated that the dimeric benzophenones (1-3) inhibited lipopolysaccharide-induced NO production in RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values ranging from 8.8 to 18.1 μM, being more potent than the positive control, dexamethasone (IC50 = 22.2 μM).