Endophytes are prolific producers of privileged secondary metabolites with diverse therapeutic potential, although their anticancer and antimicrobial potential still have a room for further investigation. Herein, seven known secondary metabolites namely, arugosin C (1), ergosterol (2), iso-emericellin (3), sterigmatocystin (4), dihydrosterigmatocystin (5), versicolorin B (6), and diorcinol (7) were isolated from the rice culture of<em>Aspergillus sp.</em>retrieved from<em>Tecoma stans</em>(L.) Juss. ex Kunth leaves. Their anticancer and antimicrobial activities were evaluated in MTT and agar well diffusion assays, respectively. The cytotoxicity results showed that metabolite<bold>3</bold>displayed the best viability inhibition on the MCF-7 breast cancer cells with IC₅₀= 225.21 µM, while<bold>5</bold>on the HepG2 hepatocellular carcinoma cells with IC₅₀= 161.81 µM.<bold>5</bold>demonstrated a 60% apoptotic mode of cell death which is virtually correlated to its high docking affinity to Hsp90 ATP binding cleft (binding score −8.4 Kcal/mol). On the other side, metabolites<bold>4</bold>and<bold>5</bold>displayed promising antimicrobial activity especially on<em>Pseudomonas aeruginosa</em>with MIC = 125 μg/ml. The observed effect may be likely related to their excellent<em>in silico</em>inhibition of the bacterial DNA-gyrase kinase domain (binding score −10.28 Kcal/mol). To the best of our knowledge, this study is the first to report the promising cytotoxic and antibacterial activities of metabolites 3, 4, and 5 which needs further investigation and renovation to therapeutic leads.