Hypocrellutins A–C (1–3), 2- and 4-pyridone alkaloids, were isolated from cultures of the scale-insect pathogenic fungus Hypocrella discoidea BCC 71382. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of hypocrellutin B (2) was determined by ECD calculation. Their plausibly biosynthetic pathways are proposed. All isolated compounds were inactive in the antifungal, antimalarial, antitubercular, and cytotoxic activity assays. Herein the isolation and structure elucidation of 2- and 4-pyridone alkaloids, hypocrellutins A–C (1–3), together with the known anthraquinone dimer, (+)-rugulosin (4) (Fig. 1).