Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes |
| |
Authors: | JR Manjunatha BK Bettadaiah PS Negi P Srinivas |
| |
Affiliation: | 1. Department of Plantation Products, Spices and Flavour Technology, Central Food Technological Research Institute, Mysore 570 020, India;2. Department of Human Resource Development, Central Food Technological Research Institute, Mysore 570 020, India;3. Council of Scientific and Industrial Research, New Delhi, India |
| |
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. |
| |
Keywords: | Quinolines Tetrahydrocurcumin Zingerone Friedlander reaction Radical scavenging activity Antibacterial action |
本文献已被 ScienceDirect 等数据库收录! |
|