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Open AccessArticle

Inhibition of Butyrylcholinesterase and Human Monoamine Oxidase-B by the Coumarin Glycyrol and Liquiritigenin Isolated from Glycyrrhiza uralensis

1
Department of Pharmacy, and Research Institute of Life Pharmaceutical Sciences, Sunchon National University, Suncheon 57922, Korea
2
Department of Predictive Toxicology, Korea Institute of Toxicology, Daejeon 34114, Korea
3
National Institute for Korean Medicine Development, Gyeongsan 38540, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Maria João Matos
Molecules 2020, 25(17), 3896; https://doi.org/10.3390/molecules25173896
Received: 11 August 2020 / Revised: 25 August 2020 / Accepted: 25 August 2020 / Published: 26 August 2020
(This article belongs to the Special Issue Coumarin and Its Derivatives)
Eight compounds were isolated from the roots of Glycyrrhiza uralensis and tested for cholinesterase (ChE) and monoamine oxidase (MAO) inhibitory activities. The coumarin glycyrol (GC) effectively inhibited butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) with IC50 values of 7.22 and 14.77 µM, respectively, and also moderately inhibited MAO-B (29.48 µM). Six of the other seven compounds only weakly inhibited AChE and BChE, whereas liquiritin apioside moderately inhibited AChE (IC50 = 36.68 µM). Liquiritigenin (LG) potently inhibited MAO-B (IC50 = 0.098 µM) and MAO-A (IC50 = 0.27 µM), and liquiritin, a glycoside of LG, weakly inhibited MAO-B (>40 µM). GC was a reversible, noncompetitive inhibitor of BChE with a Ki value of 4.47 µM, and LG was a reversible competitive inhibitor of MAO-B with a Ki value of 0.024 µM. Docking simulations showed that the binding affinity of GC for BChE (−7.8 kcal/mol) was greater than its affinity for AChE (−7.1 kcal/mol), and suggested that GC interacted with BChE at Thr284 and Val288 by hydrogen bonds (distances: 2.42 and 1.92 Å, respectively) beyond the ligand binding site of BChE, but that GC did not form hydrogen bond with AChE. The binding affinity of LG for MAO-B (−8.8 kcal/mol) was greater than its affinity for MAO-A (−7.9 kcal/mol). These findings suggest GC and LG should be considered promising compounds for the treatment of Alzheimer’s disease with multi-targeting activities. View Full-Text
Keywords: Glycyrrhiza uralensis; glycyrol; liquiritigenin; cholinesterases; human monoamine oxidases; kinetics; docking simulation Glycyrrhiza uralensis; glycyrol; liquiritigenin; cholinesterases; human monoamine oxidases; kinetics; docking simulation
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MDPI and ACS Style

Jeong, G.S.; Kang, M.-G.; Lee, J.Y.; Lee, S.R.; Park, D.; Cho, M.; Kim, H. Inhibition of Butyrylcholinesterase and Human Monoamine Oxidase-B by the Coumarin Glycyrol and Liquiritigenin Isolated from Glycyrrhiza uralensis. Molecules 2020, 25, 3896. https://doi.org/10.3390/molecules25173896

AMA Style

Jeong GS, Kang M-G, Lee JY, Lee SR, Park D, Cho M, Kim H. Inhibition of Butyrylcholinesterase and Human Monoamine Oxidase-B by the Coumarin Glycyrol and Liquiritigenin Isolated from Glycyrrhiza uralensis. Molecules. 2020; 25(17):3896. https://doi.org/10.3390/molecules25173896

Chicago/Turabian Style

Jeong, Geum S.; Kang, Myung-Gyun; Lee, Joon Y.; Lee, Sang R.; Park, Daeui; Cho, MyoungLae; Kim, Hoon. 2020. "Inhibition of Butyrylcholinesterase and Human Monoamine Oxidase-B by the Coumarin Glycyrol and Liquiritigenin Isolated from Glycyrrhiza uralensis" Molecules 25, no. 17: 3896. https://doi.org/10.3390/molecules25173896

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