Abstract
The synthesis of derivatives of 4-Methylumbelliferone (4-MUs), which are structurally interesting antioxidants, was performed in this study. The modification of 4-Methylumbelliferone (4-MU) by different reaction steps was performed to yield the target compounds, the 4-MUs. The 4-MUs were characterized by different spectroscopic techniques (Fourier transform infrared; FT-IR and Nuclear magnetic resonance; NMR) and micro-elemental analysis (CHNS). The in vitro antioxidant activity of the 4-MUs was evaluated in terms of their free radical scavenging activities against 2,2-diphenyl-1-picrylhydrazyl (DPPH), Nitric oxide radical scavenging activity assay, chelating activity and their (FRAP) ferric-reducing antioxidant power, which were compared with a standard antioxidant. Our results reveal that the 4-MUs exhibit excellent radical scavenging activities. The antioxidant mechanisms of the 4-MUs were also studied. Density Function Theory (DFT)-based quantum chemical studies were performed with the basis set at 3-21G. Molecular models of the synthesized compounds were studied to understand the antioxidant activity. The electron levels, namely HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), for these synthesized antioxidants were also studied.
Highlights
Umbelliferone derivatives (Us) are a family of coumarins that are recognized to have antiinflammatory, antithrombotic, enzyme inhibitor and antioxidant properties [1,2,3,4]
The potency of various substituents on Us as antioxidants were deeply investigated by researchers, who found that the number and nature of the hydroxyl, methoxy or methyl substituents as electron-donating groups are the most important factors responsible for adjusting the antioxidant activities of Us
Coumarins inhibit the proliferation of various tumor cell lines, they retard the development of renal and prostate-carcinoma [10,11,12], in addition to prevent the repetition of melanoma [13]; Umbeliferons show cytotoxic impacts against the lung-carcinoma cell lines [14,15,16]
Summary
Umbelliferone derivatives (Us) are a family of coumarins that are recognized to have antiinflammatory, antithrombotic, enzyme inhibitor and antioxidant properties [1,2,3,4]. Coumarins inhibit the proliferation of various tumor cell lines, they retard the development of renal and prostate-carcinoma [10,11,12], in addition to prevent the repetition of melanoma [13]; Umbeliferons show cytotoxic impacts against the lung-carcinoma cell lines [14,15,16]. PLOS ONE | DOI:10.1371/journal.pone.0156625 May 31, 2016
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