Chromenone and quinolinone derivatives as potent antioxidant agents
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The antioxidant activity (AOA) of three different classes of phenolic compounds viz chromen-2-ones, chromen-4-ones, and quinolin-2-ones was systematically studied using DPPH, ABTS, FRAP, and in vitro lipid peroxidation inhibition assays. The effect of incorporation of hydrophobic group on AOA was also studied. In DPPH, ABTS, and FRAP assays, the highest AOA was registered for the dihydroxy chromenones among all the phenolic derivatives. Presence of alkyl group led to reduction in AOA in the above three assays. However, in lipid peroxidation inhibition assay for selected compounds, incorporation of alkyl group led to enhancement in AOA. The AOA of few compounds was observed to be more than three times higher in comparison to standard “Trolox” in lipid peroxidation inhibitory assay.
KeywordsAntioxidant activity Chromen-2-ones Chromen-4-ones Quinolin-2-ones Lipid peroxidation inhibitory activity
We thank University of Delhi, Defence Research Development Organization (DRDO, India), Indo-German Science and Technology Center (IGSTC), and Council of Scientific and Industrial Research (CSIR) for financial support. The award of Junior/Senior Research Fellowships (JRF/SRF) by CSIR (to KC), University Grants Commission (to AKS at Delhi University) and by DRDO (to DAJ) is gratefully acknowledged.
- Abeer A, Mohsen D (2012) Nonclassical biological activities of quinolone derivatives. J Pharm Pharm Sci 15:52–72Google Scholar
- Chand K, Tiwari RK, Kumar S, Shirazi AN, Sharma S, Van der Eycken E, Parmar VS, Parang K, Sharma SK (2014) Synthesis, antiproliferative, and c-Src inhibitory activities of 4-oxo-4H-1-benzopyran derivatives. J Het Chem. doi: 10.1002/jhet.2106
- Kathuria A, Jalal S, Tiwari R, Shirazi AN, Gupta S, Kumar S, Parang K, Sharma SK (2011) Substituted coumarin derivatives: synthesis and evaluation of antiproliferative and Src kinase inhibitory activities. Chem Biol Interface 1:279–296Google Scholar
- Khan KM, Ahmad A, Ambreen N, Amyn A, Perveen S, Khan SA, Choudhary MI (2009) Schiff bases of 3-formylchromones as antibacterial, antifungal, and phytotoxic agents. Lett Drug Des Discov 6:363–373Google Scholar
- Kumar A, Singh BK, Tyagi R, Jain SK, Sharma SK, Prasad AK, Raj HG, Rastogi RC, Watterson AC, Parmar VS (2005) Comparison of the specificites of acetoxy derivatives of 4-methylcoumarin and 4-phenylcoumarin to acetoxycoumarins: protein transacetylase. Bioorg Med Chem 13:4300–4305CrossRefPubMedGoogle Scholar
- Kumar S, Singh BK, Pandey AK, Kumar A, Sharma SK, Raj HG, Prasad AK, Van der Eycken E, Parmar VS, Ghosh B (2007) A chromone analog inhibits TNF-alpha induced expression of cell adhesion molecules on human endothelial cells via blocking NF-kappaB activation. Bioorg Med Chem 15:2952–2962CrossRefPubMedGoogle Scholar
- Malhotra S, Shakya G, Kumar A, Vanhoecke BW, Cholli AL, Raj HG, Saso L, Ghosh B, Bracke ME, Prasad AK, Biswal S, Parmar VS (2008) Antioxidant, antiinflammatory and antiinvasive activities of biopolyphenolics. Arkivoc 6:119–139Google Scholar
- Raj HG, Parmar VS, Jain SC, Goel S, Poonam Himanshu, Malhotra S, Singh A, Olsen CE, Wengel J (1998) Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: dioxygenated 4-methyl coumarins as superb antioxidant and radical scavenging agents. Bioorg Med Chem 6:833–839CrossRefPubMedGoogle Scholar
- Raj HG, Parmar VS, Jain SC, Priyadarsini KI, Mittal JP, Goel S, Das SK, Sharma SK, Olsen CE, Wengel J (1999) Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 5: pulse radiolysis studies on the antioxidant action of 7,8-diacetoxy-4-methylcoumarin. Bioorg Med Chem 7:2091–2094CrossRefPubMedGoogle Scholar