Twelve new tanzawaic acid derivatives, penitanzacids A-F (1-6), and G-J (9-12), and hatsusamides C-D (13-14), together with two revised structures [tanzawaic acids I-J (7-8)] and three known compounds (15-17) were isolated from the deep-sea-derived fungus Penicillium sp. KWF32. Their structures including absolute configurations were elucidated by spectroscopic data analysis, HRESIMS data, modified Mosher's method, chemical degradation studies, ECD calculations, single crystal X-ray diffraction, and biogenic considerations in comparison with reported known analogues. Penitanzacids H-J (10-12) represent the first examples of this family with a C3 side chain and support the proposed biosynthetic pathway in which the side chain is connected to the decalin backbone. Hatsusamides C-D (13-14) have a hybrid skeleton formed by linking a tanzawaic acid and a diketopiperazine through an ester bond. Compounds 13 and 14 exhibit weak cytotoxicity against the A549 cell line.