Twelve new tanzawaic acid derivatives, penitanzacids A-F (<b>1-6</b>), and G-J (<b>9-12</b>), and hatsusamides C-D (<b>13-14</b>), together with two revised structures [tanzawaic acids I-J (<b>7-8</b>)] and three known compounds (<b>15-17</b>) were isolated from the deep-sea-derived fungus <i>Penicillium</i> 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 (<b>10-12</b>) represent the first examples of this family with a <i>C</i><sub>3</sub> side chain and support the proposed biosynthetic pathway in which the side chain is connected to the decalin backbone. Hatsusamides C-D (<b>13-14</b>) have a hybrid skeleton formed by linking a tanzawaic acid and a diketopiperazine through an ester bond. Compounds <b>13</b> and <b>14</b> exhibit weak cytotoxicity against the A549 cell line.