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Two new tetracyclic polyketides with a spirocenter, simplicilones A (<b>1</b>) and B (<b>2</b>) were isolated from the broth-culture of the endophytic fungus <i>Simplicillium</i><i>subtropicum</i> (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant <i>Duguetia staudtii</i> (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC₅₀) = 25 µg/mL for <b>1</b>, 29 µg/mL for <b>2</b>), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.