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New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights

Akhtar, Muhammad Nadim and Lam, Kok Wai and Abas, Faridah and Maulidiani, and Ahmad, Syahida and Shah, Syed Adnan Ali and Atta-ur-Rahman, and Choudhary, Muhammad Iqbal and Lajis, Md. Nordin (2011) New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights. Bioorganic & Medicinal Chemistry Letters, 21 (13). pp. 4097-4103. ISSN 0960-894X; ESSN: 1464-3405

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Abstract

Bioassay-guided extraction of the stem bark of Knema laurina showed the acetylcholinesterase (AChE) inhibitory activity of DCM and hexane fractions. Further repeated column chromatography of hexane and DCM fractions resulted in the isolation and purification of five alkenyl phenol and salicylic acid derivatives. New compounds, (+)-2-hydroxy-6-(10'-hydroxypentadec-8'(E)-enyl)benzoic acid (1) and 3-pentadec-10'(Z)-enylphenol (2), along with known 3-heptadec-10'(Z)-enylphenol (3), 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid (4), and 2-hydroxy 6-(10'(Z)-heptadecenyl)benzoic acid (5) were isolated from the stem bark of this plant. Compounds (1-5) were tested for their acetylcholinesterase inhibitory activity. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and chemical derivatizations. Compound 5 showed strong acetylcholinesterase inhibitory activity with IC(50) of 0.573 ± 0.0260 μM. Docking studies of compound 5 indicated that the phenolic compound with an elongated side chain could possibly penetrate deep into the active site of the enzyme and arrange itself through π-π interaction, H-bonding, and hydrophobic contacts with some critical residues along the complex geometry of the active gorge.

Item Type:Article
Keyword:Knema laurina; Myristicaceae; Acetylcholinesterase inhibition; Alkyl resorcinol; Molecular docking
Faculty or Institute:Institute of Bioscience
Faculty of Biotechnology and Biomolecular Sciences
Faculty of Food Science and Technology
Faculty of Science
Publisher:Elsevier
DOI Number:10.1016/j.bmcl.2011.04.065
Altmetrics:http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1016/j.bmcl.2011.04.065
ID Code:24120
Deposited By: Nur Farahin Ramli
Deposited On:23 Oct 2013 16:42
Last Modified:28 Apr 2016 13:25

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