Synthesis of mono-ketone curcumin analogs from 3-benzyloxybenzaldehyde and their activity assay as inhibitor of α-amylase

Huda, Muhammad Badrul and Astuti, Endang and Raharjo, Tri Joko (2021) Synthesis of mono-ketone curcumin analogs from 3-benzyloxybenzaldehyde and their activity assay as inhibitor of α-amylase. Key Engineering Materials, 884. 304 – 311. ISSN 10139826

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Abstract

Synthesis, characterization, and biological evaluation of mono-ketone curcumin analogs as an inhibitor of α-amylase enzyme have been conducted. This research was initiated by synthesizing 3-benzyloxybenzaldehyde from 3-hydroxybenzaldehyde using benzyl chloride, potassium iodide, and potassium carbonate in dimethylformamide under reflux condition for an hour. Synthesis of monoketone curcumin analogs was performed through Claisen-Schmidt reaction by refluxing 3- benzyloxybenzaldehyde with acetone (analog A), cyclopentanone (analog B), and cyclohexanone (analog C) using potassium hydroxide 5 as a catalyst for an hour. The structures of the products were elucidated by FTIR, MS/MS, 1H-NMR, and 13C-NMR. Mono-ketone curcumin analogs were evaluated for their activity assay towards inhibition of α-amylase enzyme. The inhibition type of mono-ketone curcumin analogs was also investigated. The inhibition results of monoketone curcumin analogs were compared to acarbose as a positive control. The results showed that 3- benzyloxybenzaldehyde and mono-ketone curcumin analogs (A, B, and C) yielded in 90.2, 89.7, 97.4, and 94.6, respectively. The inhibitory activity of curcumin analog C was higher than the acarbose and other curcumin analogs (A and B). The inhibition types of mono-ketone curcumin analogs (A, B, and C) and acarbose were considered as uncompetitive inhibitors. © 2021 Trans Tech Publications Ltd, Switzerland.

Item Type: Article
Additional Information: Cited by: 0
Uncontrolled Keywords: Acetone; Chlorine compounds; Dimethylformamide; Enzyme inhibition; Potassium chloride; Potassium hydroxide; Potassium iodide; Activity assays; Alpha amylase; Benzyl chlorides; Biological evaluation; Cyclohexanones; Cyclopentanone; Inhibitory activity; Reflux conditions; Amylases
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Mathematics and Natural Sciences > Chemistry Department
Depositing User: Sri JUNANDI
Date Deposited: 07 Oct 2024 00:16
Last Modified: 07 Oct 2024 00:16
URI: https://ir.lib.ugm.ac.id/id/eprint/8698

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