Molecules 2013, 18(4), 3779-3788; doi:10.3390/molecules18043779
Article

Cholinesterase Enzymes Inhibitors from the Leaves of Rauvolfia Reflexa and Their Molecular Docking Study

1 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia 2 School of Chemical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia 3 School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia
* Author to whom correspondence should be addressed.
Received: 19 February 2013; in revised form: 19 March 2013 / Accepted: 20 March 2013 / Published: 25 March 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract: Plants of the Apocynaceae family have been traditionally used in the treatment of age-related brain disorders. Rauvolfia reflexa, a member of the family, has been used as an antidote for poisons and to treat malaria. The dichloromethane, ethanol and methanol extracts from the leaves of Rauvolfia reflexa showed potential acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities, with IC50 values in the 8.49 to 52.23 g/mL range. Further cholinesterase inhibitory-guided isolation of these extracts afforded four bioactive compounds, namely: (E)-3-(3,4,5-trimethoxyphenyl)acrylic acid (1), (E)-methyl 3-(4-hydroxy-3,5-dimethoxyphenyl) acrylate (2), 17-methoxycarbonyl-14-heptadecaenyl-4-hydroxy-3-methoxycinnamate (3) and 1,2,3,4-tetrahydro-1-oxo-β-carboline (4). The isolated compounds showed moderate cholinesterase inhibitory activity compared to the reference standard, physostigmine. Compounds 1 and 2 showed the highest inhibitory activity against AChE (IC50 = 60.17 µM) and BChE (IC50 = 61.72 µM), respectively. Despite having similar molecular weight, compounds 1 and 2 were structurally different according to their chemical substitution patterns, leading to their different enzyme inhibition selectivity. Compound 2 was more selective against BChE, whereas compound 1 was a selective inhibitor of AChE. Molecular docking revealed that both compounds 1 and 2 were inserted, but not deeply into the active site of the cholinesterase enzymes.
Keywords: Apocynaceae; Rauvolfia reflexa; acetylcholinesterase; butyrylcholinesterase; molecular docking

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MDPI and ACS Style

Fadaeinasab, M.; Hadi, A.H.A.; Kia, Y.; Basiri, A.; Murugaiyah, V. Cholinesterase Enzymes Inhibitors from the Leaves of Rauvolfia Reflexa and Their Molecular Docking Study. Molecules 2013, 18, 3779-3788.

AMA Style

Fadaeinasab M, Hadi AHA, Kia Y, Basiri A, Murugaiyah V. Cholinesterase Enzymes Inhibitors from the Leaves of Rauvolfia Reflexa and Their Molecular Docking Study. Molecules. 2013; 18(4):3779-3788.

Chicago/Turabian Style

Fadaeinasab, Mehran; Hadi, A. H.A.; Kia, Yalda; Basiri, Alireza; Murugaiyah, Vikneswaran. 2013. "Cholinesterase Enzymes Inhibitors from the Leaves of Rauvolfia Reflexa and Their Molecular Docking Study." Molecules 18, no. 4: 3779-3788.

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