Abstract: A new benzoic acid derivative, spinulacid (1), together with six known compounds ascomindone A (2), ascomindone C (3), monomethylsulochrin (4), barceloneic acid A (5), flufuran (6), and 5-hydroxymethyl-furaldehyde (7) were obtained from the rice fermentation extract of an endophytic fungus Penicillium spinulosum isolated from Emmenopterys henryi Oliv. by various chromatographic techniques. Their structures were elucidated by the analysis of NMR data, MS and comparison with literature. The biological activity results showed that compounds 1, 2, 5, and 6 exhibited significant proangiogenic activity in transgenic zebrafish at concentrations of 20 and 40 μmol·L^-1 (the animal experiment was approved by the Animal Ethical and Welfare Committee of Biology Institute, Shandong Academy of Science, the approval number is SWS20240611). Compounds 1 and 4 displayed moderate or strong antifungal activity against phytopathogen Fusarium graminearum with minimum inhibitory concentration (MIC) values of 12.5, and 6.25 μg·mL^-1, respectively. Besides, compound 4 was also found to show obvious antibacterial activity against Staphylococcus aureus and Erwinia carotovora with MIC values of 6.25 and 12.5 μg·mL^-1, respectively.