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Determination of the multifaceted activity of selected flavone C-monoglucosides, namely orientin (OR), homoorientin (hOR), vitexin (VT), and isovitexin (iVT) in comparison to quercetin (Q) was addressed. Their antioxidant activity was characterized by the peak oxidation potentials (${\mathrm{E}}_{\mathrm{p}\mathrm{a}}$) provided by the differential pulse voltammetry (DPV) method, whereas their inhibitory activity towards angiotensin converting enzyme (ACE), acetylcholinesterase (AChE), and advanced glycation end-products (AGEs) formation was measured in a model system. The relationship between the multifaceted activity of flavone C-monoglucosides and their ${\mathrm{E}}_{\mathrm{p}\mathrm{a}}$ was evaluated. The rank of the antioxidant activity in comparison to quercetin was Q > hOR ≈ OR > iVT ≈ VT, whereas the order of the ACE inhibitory activity was Q > hOR > OR > VT > iVT. The correlation between IC₅₀ for ACE inhibition and E_pa values was r = 0.787. This finding was confirmed by the negative correlation between ACE inhibitory activity and antioxidant activity of these compounds (r = −0.838). The order of the AChE enzyme inhibitory activity was hOR > OR > iVT > VT > Q, whereas the rank of anti-AGEs activity was hOR > OR > iVT > Q > VT > AG (aminoquanidine), and the weak positive correlation between IC₅₀ and E_pa was noted (r = 0.546 for BSA (bovine serum albumin)/glucose system and r = 0.580 for BSA/methylglyoxal system). In contrast, the anti-AGEs activity was negatively correlated with IC₅₀ values for ACE inhibition (r = −0.669), whereas no correlation was found between the ACE and AChE inhibitory activities. The results expand our knowledge of the multifaceted activity of flavone C-monoglucosides. Full article