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Cholinesterase Enzymes Inhibitors from the Leaves of Rauvolfia Reflexa and Their Molecular Docking Study
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
School of Chemical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia
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
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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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.
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.
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.