Antibacterial and Antioxidant Screening of Semi-Synthetic Naringin Based Hydrazone and Oxime Derivatives

Abstract

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 by 13 C NMR, IR, MS, and 1 H 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.

Phenolic Content and Antioxidant and Antimicrobial Activities of Malva sylvestris L., Malva oxyloba Boiss., Malva parviflora L., and Malva aegyptia L. Leaves Extract

“…e available reports suggest that the overuse of the antiseptic in house and hospitals also contributed to the increase in the resistance of bacteria. However, if the patients with bacterial infection, that is, resistance to antibiotics, did not receive effective treatment may lead to long-term infections that may result in high mortality as was observed in the patients with pneumococcal infections and typhoid fever [3].…”

Potential application of green extracts rich in phenolics for innovative functional foods: natural deep eutectic solvents as media for isolation of biocompounds from berries

“…aureus and MRSA, which could be related to the higher naringin concentration, as several studies have reported its inhibitory effect against these strains. 72,73 The extracts E5 and E12 showed similar activity against B. subtilis , E. coli , S. typhimurium and P. aeruginosa , and both have high levels of malvidin-3- O -glucoside, but to our knowledge, there are no reports on the antimicrobial activity of this anthocyanin. The conventional blueberry extract showed the potential to inhibit only Gram-positive bacteria such as B. cereus .…”

Glechoma curviflora Volatile Oil from Palestine: Chemical Composition and Neuroprotective, Antimicrobial, and Cyclooxygenase Inhibitory Activities

“…The worldwide evolution of antimicrobial resistance, in addition to the scarcity of novel antibiotic medications, represents a serious public health concern. That means the go-back to a preantibiotic epoch in which infectious diseases caused by multiple-resistant microbial pathogens are uncontrollable [ 29 ]. It is well documented that EOs displayed a comparable antimicrobial effect against the tested antibiotic-resistant and antibiotic-susceptible strains; therefore, it could be presumed that the EOs mechanism of action is unlike that from the used antibacterial and antifungal drugs [ 11 ].…”