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A Study on Synthesis and Antioxidant Activity Comparison of Novel Stilbenebenzamide Compounds

Author(s):

Aleksandra Kładna, Paweł Berczyński, Oya Bozdağ Dündar, Irena Kruk, Beyza Torun and Hassan Y. Aboul-Enein*  

Abstract:


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+ 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 and HO was shown by the compounds with structures containing amine group (SBEBA, SBA) ( : 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 hydroxyl group in stilbene ring should be considered in further design of stilbenebenzamide compounds to enhance their antioxidant activity.

Keywords:

Stilbenebenzamide compounds, radical scavenging activity, TAS, TAC

Affiliation:

Department of History of Medicine and Medical Ethics, Pomeranian Medical University, Rybacka 1, 70-204 Szczecin, Institute of Physics, Faculty of Mechanical Engineering and Mechatronics, West Pomeranian University of Technology in Szczecin, Al. Piastów 48/49, 70-311 Szczecin, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, 06100 Tandoğan , Ankara, Institute of Physics, Faculty of Mechanical Engineering and Mechatronics, West Pomeranian University of Technology in Szczecin, Al. Piastów 48/49, 70-311 Szczecin, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ankara University, 06100 Tandoğan , Ankara, Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12622



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