Research Information System
Medicinal Chemistry, vol.17, no.5, pp.533-544, 2021 (SCI-Expanded)
Background: Stilbene phytalexis (1,2-diphenyloethylen) and benzamide are beneficial for human health. To increase the stilbene ring activity, a new series of its derivatives containing benzamide structure was synthesized and evaluated for their in vitro antioxidant power. Methods:1H nuclear magnetic resonance, mass spectroscopy, and chromatographic analyses were used to confirm the successful synthesis. The antioxidant properties were determined by the elimination of, HO, DPPH, ABTS+ • • • • Q4 radicals, total antioxidant status (TAS) and the ferric reducing antioxidant activities (TAC) measurements. Results: Stilbenebenzamide compounds showed a wide spectrum of antioxidant ability; however, their total antioxidant power was weaker than those of butylated hydroxytoluene (BHT), ascorbic • • acid, and resveratrol. The highest antiradical activity towards Q4 and HO was shown by the • compounds with structures containing amine group (SBEBA, SBA) ( Q4: 37.7 – 38.0% and 40.8 • – 43.5%, HO: 29.8%, 28.7% inhibition, respectively) at1.25 mM concentration. The antiradical • power of SBEBA (0.29) in DPPH assay was lower than those of resveratrol (1.83), ascorbic acid (3.63) and BHT (4.09). The TAS values of the synthesized compounds ranged from 152.9±5.3 to 240.2±6.7µM trolox equivalent/gram (TE/g) and were much lower than those of BHT (1304±43.0), reservatrol (1360±29.0) and ascorbic acid (2782±39.7) µM TE/g. Similarly, the TAC values ranging from 29.7±0.9 to 41.5±1.6 µM TE were weaker than that of resveratrol (239.2 ±6.7 µM TE/g). Conclusion: The results suggest that the presence of the hydroxyl group in the stilbene ring should be considered in the further design of stilbenebenzamide compounds to enhance their antioxidant activity.