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A new α-pyrone derivative1, along with four known congeners 2, 3, 4 and 5, were isolated from the solid-substrate fermentation medium of the endophytic fungus Pestalotiopsis microspore isolated from the branch of Taxus chinensis. Their structures and relative configurations were elucidated by extensive spectroscopic analysis. The cytotoxic activities of the isolated α-pyrone derivatives against two tumor cell lines as well as compound 1 ’ s antimicrobial activity against three bacteria and three plant-pathogenic strains were evaluated. No antimicrobial activity was observed for compound 1. The cytotoxicity against Caski and He L a tumor cell lines w as insignificant. To our surprise, the known compound 4 showed significant gibberellin synergistic activity towards Distylium chinense seeds.