curcumin and quinoline

Topics: Antineoplastic Agents; Apoptosis; Cell Cycle Checkpoints; Cell Line, Tumor; Cell Proliferation; Curcumin; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Quinolines; Structure-Activity Relationship

A series of 2-arylethenyl-N-methylquinolinium derivatives were designed and synthesized based on our previous research of 2-arylethenylquinoline analogues as multifunctional agents for the treatment of Alzheimer's disease (AD) (Eur. J. Med. Chem. 2015, 89, 349-361). The results of in vitro biological activity evaluation, including β-amyloid (Aβ) aggregation inhibition, cholinesterase inhibition, and antioxidant activity, showed that introduction of N-methyl in quinoline ring significantly improved the anti-AD potential of compounds. The optimal compound, compound a12, dramatically attenuated the cell death of glutamate-induced HT22 cells by preventing the generation of ROS and increasing the level of GSH. Most importantly, intragastric administration of a12•HAc was well tolerated at doses up to 2000 mg/kg and could traverse blood-brain barrier.

Topics: Alzheimer Disease; Amyloid beta-Peptides; Antioxidants; Blood-Brain Barrier; Cell Death; Cell Line; Cholinesterase Inhibitors; Drug Design; Glutathione; Humans; Quinolines; Reactive Oxygen Species

Topics: Antineoplastic Agents; Benzopyrans; Binding Sites; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HEK293 Cells; Humans; MCF-7 Cells; Molecular Docking Simulation; Molecular Structure; Piperazine; Piperazines; Proto-Oncogene Proteins c-bcl-2; Pyrimidines; Quinolines; Structure-Activity Relationship

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.

Topics: Anti-Bacterial Agents; Antioxidants; Bacteria; Curcumin; Guaiacol; Quinolines

In an investigation of the mutagenic activity of two extracts from rhizomes of Curcuma zedoaria (the mathanolic, CME, and the aqueous, CAE) and antimutagenic activity against mutagens, either 2-amino-3-methylimidazo (4,5-f) quinoline (IQ) or 4-nitroquinoline-N-oxide (4-NQO), in dosages of 1-50 microg/plate was assayed by using Salmonella typhimurium TA97, TA98, TA100, and TA102 strains. We found that the two extracts showed no mutagenicity when tested with all the tester strains either with or without the S9 mix. Moreover, the two extracts, particularly CME, presented a greater antimutagenicity than CAE did either in IQ or 4-NQO mutagens. However, the inhibition effect on lipid peroxidation was similar with both extracts. The amount of major antioxidants beta-carotene, ascorbic acid, and total polyphenols present in both CME and CAE were similar between each other. In contrast, the content of cucuminoids (44.3 mg/g extract) in CME were only found in small amounts in CAE (0.09 mg/g extract). Consequently, although both of the extracts showed similar antioxidant effects, the curcuminoids, which seem to be the main active principles from this plant, were suggested to play a pivotal role in antimutagenic activity.

Topics: Antimutagenic Agents; beta Carotene; Curcuma; Flavonoids; Phenols; Plant Extracts; Polyphenols; Quinolines; Salmonella typhimurium