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Four new indole-diterpenoids, named penerpenes K-N (<b>1</b>–<b>4</b>), along with twelve known ones (<b>5</b>–<b>16</b>), were isolated from the fermentation broth produced by adding L-tryptophan to the culture medium of the marine-derived fungus <i>Penicillium</i> sp. KFD28. The structures of the new compounds were elucidated extensively by 1D and 2D NMR, HRESIMS data spectroscopic analyses and ECD calculations. Compound <b>4</b> represents the second example of paxilline-type indole diterpene bearing a 1,3-dioxepane ring. Three compounds (<b>4</b>, <b>9,</b> and <b>15</b>) were cytotoxic to cancer cell lines, of which compound <b>9</b> was the most active and showed cytotoxic activity against the human liver cancer cell line BeL-7402 with an IC₅₀ value of 5.3 μM. Moreover, six compounds (<b>5</b>, <b>7</b>, <b>10</b>, <b>12</b>, <b>14</b>, and <b>15</b>) showed antibacterial activities against <i>Staphylococcus aureus</i> ATCC 6538 and <i>Bacillus subtilis</i> ATCC 6633.