A chemical investigation of the rice fermentation by the saprophytic fungus Neohelicosporium griseum, isolated from decayed wood, yielded vertixanthone (1), diaportheone A (2), 1,3,6,8-tetrahydroxyanthraquinone (3), lecanoric acid (4), decarboxycitrinone (5), 6,8-dihydroxy-4-hydroxymethyl-3,5-dimethyl-isochromen-1-one (6), decarboxyhydroxycitrinone (7), and ergosterin (8). The 1D and 2D NMR character of compound 1 in DMSO-d6 was described in detail for the first time. An investigation of the antimicrobial activities of the isolated compounds revealed moderate activity of compounds 1–4 against Pseudomonas aeruginosa, and weak activity of compound 3 against Staphylococcus aureus. An in-vitro cytotoxic test showed that compounds 1, 3, and 4 had cytotoxic activity against HELA cell lines, with respective IC50 values of 30.8, 13.7, and 14.1 µM. Compounds 1, 3, and 4 also showed significant cytotoxicity against A549 cell lines, with respective IC50 values of 24.7, 7.4, and 10.3 µM.