In this study, the inhibitory potential of bacterial neuraminidase (NA) was observed on the leaves of Epimedium koreanum Nakai, which is a popular ingredient in traditional herbal medicine. This study attempted to isolate the relevant, responsible metabolites and elucidate their inhibition mechanism. The methanol extraction process yielded eight flavonoids (1⁻8), of which compounds 7 and 8 were new compounds named koreanoside F and koreanoside G, respectively. All the compounds (1⁻8) showed a significant inhibition to bacterial NA with IC₅₀ values of 0.17⁻106.3 µM. In particular, the prenyl group on the flavonoids played a critical role in bacterial NA inhibition. Epimedokoreanin B (compound 1, IC₅₀ = 0.17 µM) with two prenyl groups on C8 and C5' of luteolin was 500 times more effective than luteolin (IC₅₀ = 85.6 µM). A similar trend was observed on compound 2 (IC₅₀ = 0.68 µM) versus dihydrokaempferol (IC₅₀ = 500.4 µM) and compound 3 (IC₅₀ = 12.6 µM) versus apigenin (IC₅₀ = 107.5 µM). Kinetic parameters (K_m, V_max, and K_ik/K_iv) evaluated that all the compounds apart from compound 5 showed noncompetitive inhibition. Compound 5 was proven to be a mixed type inhibitor. In an enzyme binding affinity experiment using fluorescence, affinity constants (K_SV) were tightly related to inhibitory activities.

Hong Min Choi

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