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Ali MY, Jannat S, Jung HA, et al. Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis. Asian Pac J Trop Med. 2016;9(2):103-11doi: 10.1016/j.apjtm.2016.01.014.
Ali, M. Y., Jannat, S., Jung, H. A., Choi, R. J., Roy, A., & Choi, J. S. (2016). Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis. Asian Pacific journal of tropical medicine, 9(2), 103-11. https://doi.org/10.1016/j.apjtm.2016.01.014
Ali, Md Yousof, et al. "Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis." Asian Pacific journal of tropical medicine vol. 9,2 (2016): 103-11. doi: https://doi.org/10.1016/j.apjtm.2016.01.014
Ali MY, Jannat S, Jung HA, Choi RJ, Roy A, Choi JS. Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis. Asian Pac J Trop Med. 2016 Feb;9(2):103-11. doi: 10.1016/j.apjtm.2016.01.014. Epub 2016 Jan 11. PMID: 26919937.
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Asian Pac J Trop Med. 2016 Feb;9(2):103-11. doi: 10.1016/j.apjtm.2016.01.014. Epub 2016 Jan 11.

Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis.

Asian Pacific journal of tropical medicine

Md Yousof Ali, Susoma Jannat, Hyun Ah Jung, Ran Joo Choi, Anupom Roy, Jae Sue Choi

Affiliations

  1. Department of Food and Life Science, Pukyong National University, Busan 608-737, Republic of Korea.
  2. Department of Food Science and Human Nutrition, Chonbuk National University, Jeonju 561-756, Republic of Korea. Electronic address: [email protected].
  3. Angiogenesis & Chinese Medicine Laboratory, Department of Pharmacology, University of Cambridge, Cambridge, UK.
  4. Department of Food and Life Science, Pukyong National University, Busan 608-737, Republic of Korea. Electronic address: [email protected].

PMID: 26919937 DOI: 10.1016/j.apjtm.2016.01.014

Abstract

OBJECTIVE: To use structure-activity analysis to study the anti-Alzheimer's disease (anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaris, along with one purchased coumarin (daphnetin).

METHODS: Umbelliferone, umbelliferone 6-carboxylic acid, scopoletin, isoscopoletin, 7-methoxy coumarin, scoparone, scopolin, and esculetin have been previously isolated; however 2'-isopropyl psoralene was isolated from Angelica decursiva for the first time to evaluate their inhibitory effects against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-site amyloid precursor protein cleaving enzyme 1 (BACE1) enzyme activity. We scrutinized the potentials of coumarins as cholinesterase and BACE1 inhibitors via enzyme kinetics and molecular docking simulation.

RESULTS: Among the test compounds, umbelliferone 6-carboxylic acid, esculetin and daphnetin exhibited potent inhibitory activity against AChE, BChE and BACE1. Both esculetin and daphnetin have a catechol group and exhibit significant anti-AD activity against AChE and BChE. In contrast, presence of a sugar moiety and methoxylation markedly reduced the anti-AD activity of the coumarins investigated in this study. With respect to BACE1 inhibition, umbelliferone 6-carboxylic acid, esculetin and daphnetin contained carboxyl or catechol groups, which significantly contributed to their anti-AD activities. To further investigate these results, we generated a 3D structure of BACE1 using Autodock 4.2 and simulated binding of umbelliferone 6-carboxylic acid, esculetin and daphnetin. Docking simulations showed that different residues of BACE1 interacted with hydroxyl and carboxylic groups, and the binding energies of umbelliferone 6-carboxylic acid, esculetin and daphnetin were negative (-4.58, -6.25 and -6.37 kcal/mol respectively).

CONCLUSIONS: Taken together, our results suggest that umbelliferone 6-carboxylic acid, esculetin and daphnetin have anti-AD effects by inhibiting AChE, BChE and BACE1, which might be useful against AD.

Copyright © 2016 Hainan Medical College. Production and hosting by Elsevier B.V. All rights reserved.

Keywords: BACE1; Cholinesterase; Coumarins; Daphnetin; Esculetin; Umbelliferone 6-carboxylic acid

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