This study aimed to determine the health-promoting properties of sweet pepper by comparing the activity of fractions with variable lipophilicity. Fractions from red pericarp: aqueous (F1), 40% MeOH (F2), and 70% MeOH (F3) were analyzed for antiradical activity (with DPPH• and ABTS+•), and the contents of total phenolic compounds (TP), flavonoids (TF), and dihydroxycinnamic acids (TDHCA). The anticancer potential of the fractions was evaluated in vitro using different cancer cell lines: human colorectal carcinoma (HCT116) and PC-3 (prostate cancer cell). Fibroblast-like cells of L929 obtained from subcutaneous adipose tissue of mouse were used as normal cells. The highest content of TP, TF, and TDHCA along with the strongest antiradical activity was observed for fraction F2, while the strongest anticancer properties against PC-3 were observed in fraction F3. Fraction F3 primarily contained capsianoside derivatives, which had been isolated through chromatographic methods and identified by spectral methods. These analyses helped in identifying 8 compounds, including 3 new compounds.