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Open AccessArticle

Bakkenolides and Caffeoylquinic Acids from the Aerial Portion of Petasites japonicus and Their Bacterial Neuraminidase Inhibition Ability

1
Plant Resource Industry Division, Forest Plant Industry Department, Baekdudaegan National Arboretum, Bonghwa-gun 26209, Korea
2
Department of Bioscience and Biotechnology, Konkuk University, Gwangjin-gu, Seoul 05029, Korea
3
Division of Applied Life Science, Gyeongsang National University, Jinju 52828, Korea
*
Author to whom correspondence should be addressed.
Biomolecules 2020, 10(6), 888; https://doi.org/10.3390/biom10060888
Received: 21 April 2020 / Revised: 3 June 2020 / Accepted: 8 June 2020 / Published: 10 June 2020
Petasites japonicus have been used since a long time in folk medicine to treat diseases including plague, pestilential fever, allergy, and inflammation in East Asia and European countries. Bioactive compounds that may prevent and treat infectious diseases are identified based on their ability to inhibit bacterial neuraminidase (NA). We aimed to isolate and identify bioactive compounds from leaves and stems of P. japonicas (PJA) and elucidate their mechanisms of NA inhibition. Key bioactive compounds of PJA responsible for NA inhibition were isolated using column chromatography, their chemical structures revealed using 1 H NMR, 13 C NMR, DEPT, and HMBC, and identified to be bakkenolide B (1), bakkenolide D (2), 1,5-di-O-caffeoylquinic acid (3), and 5-O-caffeoylquinic acid (4). Of these, 3 exhibited the most potent NA inhibitory activity (IC50 = 2.3 ± 0.4 μM). Enzyme kinetic studies revealed that 3 and 4 were competitive inhibitors, whereas 2 exhibited non-competitive inhibition. Furthermore, a molecular docking simulation revealed the binding affinity of these compounds to NA and their mechanism of inhibition. Negative-binding energies indicated high proximity of these compounds to the active site and allosteric sites of NA. Therefore, PJA has the potential to be further developed as an antibacterial agent for use against diseases associated with NA. View Full-Text
Keywords: bacterial neuraminidase inhibitors; bakkenolides; caffeoylquinic acid; Petasites japonicus plant extract; competitive inhibition; non-competitive inhibition bacterial neuraminidase inhibitors; bakkenolides; caffeoylquinic acid; Petasites japonicus plant extract; competitive inhibition; non-competitive inhibition
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MDPI and ACS Style

Woo, H.S.; Shin, K.-C.; Kim, J.Y.; Kim, Y.-S.; Ban, Y.J.; Oh, Y.J.; Cho, H.J.; Oh, D.-K.; Kim, D.W. Bakkenolides and Caffeoylquinic Acids from the Aerial Portion of Petasites japonicus and Their Bacterial Neuraminidase Inhibition Ability. Biomolecules 2020, 10, 888.

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