Wortmannine A (1), a dinor-carbon wortmannin derivative with an unusual five-membered B ring, together with wortmannine B (2), a wortmannin derivative bearing an unusual five-membered B ring and lactam E-ring, and wortmannine C (3), a wortmannin derivative bearing an unusual five-membered B ring and a lactone E-ring, as well as wortmannine D (4), a 4-methyl substituted androstadiene-17-one, were purified from the zeistic culture of Talaromyces wortmannii LGT-4. The structures of 1–4 were elucidated by comprehensive NMR spectroscopy, Mosher's method and single-crystal X-ray crystallography. Additional known compounds (5–8) were also isolated. The isolates were tested for cytotoxic activities and compound 5, entonaemin A, showed anti-HL60 activity with IC50s of 15.0 lM (24 h) and 12.4 lM (48 h).