The discovery of paclitaxel1 and camptothecin2 from the endophytes of the higher plants Taxus brevifolia and Nothapodytes foetida, respectively, has generated interest in endophytic fungi as a source of potential drugs. Several genera of endophytes have been identified and many interesting compounds have been isolated from them. The genus Penicillium is typically found as an endophyte which exists in various parts of higher plants3,4 and is also a source of structurally diverse secondary metabolites, that is, polyketides: leptosphaerone C, penicillenone, arugosin I, and 9-demethyl FR-901235;5 tetramic acid derivatives: penicillenols A1, A2, B1, B2, C1, and C2;6 alkaloids: penicidones A–C,3 rhizoctonic acid, asperfumoid, and 3,5-dichloro-p-anisic acid.4 We noted that the crude extracts of Penicillium sp. BCC16054 culture showed antimalarial (with IC50 values of 3.33–3.38 lg/mL) and antitubercular [with minimum inhibitory concentration (MIC) values of 0.122–6.25 lg/ mL] activities. Therefore, chemical investigation of these crude extracts was conducted. Systematic isolation and purification led to five new compounds, penicolinates A–E (1–5), and four known compounds, phenopyrrozin (6), p-hydroxyphenopyrrozin (7), gliotoxin (8), and bisdethiobis(methylthio)gliotoxin (9) (Fig. 1). The biological activities of the isolated compounds were also evaluated.