Roquefortine C (1) and 11-bromoroquefortine C (4) were isolated from Penicillium chrysogenum, an endophyte obtained from green leaves of Coffea arabica, during induction experiments by adding halide salts to the culture media. In our studies, 11-bromoroquefortine D and 11-bromo-17-hydroxybromoroquefortine C were identified by LC/HR-MS. It is the first time that bromoroquefortine C and D are described as halogenated natural products. These halo alkaloids were shown to be biosynthesized from brominated tryptophan as the biosynthetic precursor. Cytotoxic and antibiotic assays using roquefortine C and 11-bromoroquefortine C showed that the presence of the 11-Br substituent impairs some biological activities of this alkaloid. © 2014 Verlag Helvetica Chimica Acta AG, Zürich.