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Open AccessArticle

Effectiveness of Prenyl Group on Flavonoids from Epimedium koreanum Nakai on Bacterial Neuraminidase Inhibition

Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University, Jinju 52828, Korea
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Author to whom correspondence should be addressed.
Academic Editor: Tiziano Tuccinardi
Molecules 2019, 24(2), 317; https://doi.org/10.3390/molecules24020317
Received: 24 December 2018 / Revised: 12 January 2019 / Accepted: 13 January 2019 / Published: 16 January 2019
(This article belongs to the Special Issue Trends in the Development of Enzyme Inhibitors)
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 (18), of which compounds 7 and 8 were new compounds named koreanoside F and koreanoside G, respectively. All the compounds (18) 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 (Km, Vmax, and Kik/Kiv) 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 (KSV) were tightly related to inhibitory activities. View Full-Text
Keywords: Epimedium koreanum Nakai; koreanoside F; koreanoside G; bacterial neuraminidase; binding affinity Epimedium koreanum Nakai; koreanoside F; koreanoside G; bacterial neuraminidase; binding affinity
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MDPI and ACS Style

Choi, H.M.; Kim, J.Y.; Li, Z.P.; Jenis, J.; Ban, Y.J.; Baiseitova, A.; Park, K.H. Effectiveness of Prenyl Group on Flavonoids from Epimedium koreanum Nakai on Bacterial Neuraminidase Inhibition. Molecules 2019, 24, 317.

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