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Five new compounds, eupatodibenzofuran A (<b>1</b>), eupatodibenzofuran B (<b>2</b>), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (<b>3</b>), eupatofortunone (<b>4</b>), and eupatodithiecine (<b>5</b>), have been isolated from the aerial part of <i>Eupatorium fortunei</i>, together with 11 known compounds (<b>6</b>‒<b>16</b>). Compounds <b>1</b> and <b>2</b> featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[<i>b</i>,<i>d</i>]furan-2-yl)ethenone. Among the isolates, compound <b>1</b> exhibited potent inhibitory activity with IC₅₀ values of 5.95 ± 0.89 and 5.55 ± 0.23 μM, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound <b>1</b> (5 μM) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound <b>1</b> markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways.