Phytochemical investigation of the roots of Ventilago denticulata afforded three previously undescribed metabolites, a pyranonaphthoquinone derivative dimer, ventilanone W (1), and two naphthalene derivatives, ventilagodenins C (2) and D (3), together with sixteen known compounds (4-19). The structures were established by IR, one-dimensional (1H,13C, and DEPTQ-135) and two-dimensional (HSQC, COSY, NOESY, and HMBC) NMR, and high-resolution mass spectrometry. The structure of 1 was further confirmed by single-crystal X-ray diffraction. Selected isolates were assessed for in vitro cytotoxicity against HeLa, A549, and MCF-7 cell lines using the MTT assay. Compound 2 showed moderate cytotoxicity, with IC50 values of 28.54 ± 0.45, 25.56 ± 0.71, and 30.57 ± 0.54 µM, respectively, while 8 exhibited moderate activity, with IC50 values of 32.97 ± 0.44, 21.28 ± 0.13, and 12.17 ± 0.10 µM, respectively. These results enrich the phytochemical profile of V. denticulata and highlight 2 and 8 as bioactive constituents.