Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes.

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 molecules may have potential pharmacological applications.

journal_name

Food Chem

journal_title

Food chemistry

authors

Manjunatha JR,Bettadaiah BK,Negi PS,Srinivas P

doi

10.1016/j.foodchem.2012.08.052

subject

Has Abstract

pub_date

2013-01-15 00:00:00

pages

650-8

issue

2

eissn

0308-8146

issn

1873-7072

pii

S0308-8146(12)01336-2

journal_volume

136

pub_type

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