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Food Chemistry
Volume 136, Issue 2, 15 January 2013, Pages 650-658
Synthesis of quinoline derivatives of tetrahydrocurcumin and
zingerone and evaluation of their antioxidant and antibacterial
attributes
J.R. Manjunatha a, c, B.K. Bettadaiah a, c, P.S. Negi b, c, P. Srinivas a, c
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https://doi.org/10.1016/j.foodchem.2012.08.052 Get rights and content
Abstract
Tetrahydrocurcumin (THC, 1) and zingerone (2) are biologically active molecules originating
from the important spices turmeric and ginger, respectively. Novel quinoline derivatives of THC
and zingerone have been synthesised by an efficient protocol involving their reaction with
substituted 2-aminobenzophenones and 2-aminoacetophenone. Radical-scavenging activities
(RSA) of THC, zingerone and their quinoline derivatives were evaluated. The amino-substituted
quinoline derivative of THC, 1e, showed antioxidant activity superior to those of 1 and 1a.
Derivatives 1b, 1c, 1d and 1f exhibited relatively lower RSA at equimolar concentrations (∼50–
55 μmol). A similar trend was also seen in zingerone (2) and its derivatives (2a–2e), with 2e
displaying the best RSA. Derivatives of THC (1a–1f) showed stronger antimicrobial activity than
THC (1) against Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Yersinia enterocolitica. Also,
derivatives of zingerone (2b–2e) exhibited lower minimum inhibitory concentrations (MIC) values
than zingerone (2) and its derivative, 2a for both Gram-positive and Gram-negative bacteria. The
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molecules may have potential pharmacological applications.
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Highlights
► Novel quinoline derivatives of THC and zingerone have been synthesised. ► The amino-
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substituted quinoline derivatives of THC and zingerone showed best RSA. ► Quinoline
derivatives of THC and zingerone showed strong antimicrobial activity. ► The molecules may
have possible pharmacological applications.
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Keywords
Quinolines; Tetrahydrocurcumin; Zingerone; Friedlander reaction; Radical scavenging
activity; Antibacterial action
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Copyright © 2012 Elsevier Ltd. All rights reserved.
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