The first chemical investigation of the endophytic fungus Penicillium tropicum isolated from leaves of Sapium ellipticum afforded a new cyclohexapeptide, penitropeptide (1), and a new polyketide, penitropone (2) , in addition to two known compounds, 6-hydroxy-8-methoxy-3S,5-dimethyl-3,4-isocoumarin (3) and adametizine B (4). Their structures were unambiguously elucidated on the basis of 1D and 2D NMR spectroscopy as well as mass spectrometry, and by comparison with the literature. The absolute configurations of these two new compounds 1 and 2 were determined by Marfey's method and X-ray single crystal diffraction, respectively. All isolated compounds were tested for their cytotoxic and antibacterial activities. However, none of them showed significant activity.