Phytochemical investigations of the CH2Cl2/MeOH (1:1) extract of air-dried aerial parts of Chiliadenus montanus afforded seven methoxylated flavonoids (1-7), three of them were isolated for the first time from the genus (1-3). Structures were established by spectroscopic methods, including HREIMS, 1H, 13C, DEPT, 1H-1H COSY, HMQC and HMBC NMR analyses. In the present study, three of the isolated compounds were tested for the ability to induce NAD(P)H:quinoneoxidoreductase 1 (NQO1) using a quantitative bioassay in a murine hepatoma cell line. Compound 1 revealed dose-dependent NQO1 inducing properties with a concentration that doubled the specific enzyme activity by 2-fold (CD value) of 7.0 μM, and a magnitude of induction of 3.3-fold at the highest concentration tested (100 μM).