Antibacterial and antioxidant screening of semi-synthetic naringin based hydrazone and oxime derivatives

Background: The semi-synthesis of drugs from natural products is still limited and complicated. Recently, there has been compelling global need to develop novel and potential antibacterial and antioxidant agents. Objectives: The current study aimed at semi-synthesizing new derivatives from naringin, to verify their chemical structures and assess their antibacterial and antioxidant potentials. Methods: The semi-synthesis of naringin was conducted in the presence of hydrazone and oxime derivatives in acidic solution, while elemental and spectral analytical methods were used to verify the chemical structures of the semi-synthesized molecules. Also, to assess their antibacterial activity, the micro-broth dilution method with different American type culture collection (ATCC) strains as Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, and clinical isolate methicillin-resistant Staphylococcus aureus (MRSA) were utilized. Moreover, 2, 2-Diphenyl-1-Picrylhydrazyl (DPPH) was used to assess the antioxidant activity of the derived compounds. Results: Three new hydrazone and oxime compounds were semi-synthesized from naringin and their chemical structures were identified by¹³C NMR, IR, MS, and¹H NMR. Among the semi-synthesized compounds, the (2a) molecule showed the best antibacterial activity with a minimum inhibitory concentration (MIC) value of 62.5 µg/mL. Also, this compound exhibited the best antioxidant activity with IC₅₀ 3.7 µg/mL, in comparison with the other studied samples. Conclusions: Hydrazone (2a) compound could be used as a potent antioxidant and bacterial agent. Further studies are required to investigate other therapeutic effects of the (2a) molecule.