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Five new isocoumarins, phaeosphaerins A–E (<b>1</b>–<b>5</b>), were isolated from the fermentation broth of the marine fungus <i>Phaeosphaeriopsis</i> sp. WP-26, along with one known isocoumarin, 6,8-dihydroxy-7-methoxy-3-methylisocoumarin (<b>6</b>), and two known pimarane-type diterpenes, diaportheins A (<b>7</b>) and B (<b>8</b>). Their structures were elucidated via NMR experiments, X-ray diffraction analysis, and comparison of the experimental and computed ECD curves. Compounds <b>1</b>–<b>7</b> displayed weak neuroprotective effects against H₂O₂-induced damage in SH-SY5Y cells. Moreover, compound <b>8</b> showed cytotoxicity against BEL-7402, SGC-7901, K562, A549, and HL-60 cell lines.