Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C‐6 Position

Abstract

Several synthetic approaches (aminomethylation, alkylation, condensation, etc.) have been used to synthesize derivatives based on the sesamol (1), natural phenol. The set of methods, including the study of antioxidant activity (AOA) by the ability to inhibit the initiated oxidation of animal lipids, radical scavenging activity, Fe2+‐chelation ability, as well as a comparative assessment of membrane‐protective activity under the conditions of H2O2‐induced hemolysis of mice red blood cells (RBCs), was used to analyze the antioxidant potential of the synthesized compounds. The synthesized derivatives have demonstrated different activity in the listed test systems, and we have identified compounds which appear to be most promising for a detailed study of their pharmacological properties.

Novel Mannich Bases of α‐Mangostin Bearing Methoxyphenyl Moieties with Antioxidant and Membrane‐protective activity

“…RSA determination was based on the ability of derivatives 1 – 6 to neutralize the DPPH radical, and TAA determination was based on the reduction of Mo(VI) to Mo(V) at acidic medium with formation of a colored phosphomolybdenum complex. The study demonstrated that α‐mangostin ( 1 ) functionalization increases the RSA of its derivatives 2 – 6 by a factor of 2.4–3.6 ( p =0.021), which is consistent with our previous findings for aminomethyl derivatives of xanthones [7b] and sesamol [7d] . Compounds 2 – 5 containing methoxyphenyl fragments were more active than derivative 6 ( p =0.004).…”

“…The difference in the prooxidant and antioxidant properties of various free radical modulators may be due to the experimental model, the primary target of the oxidation inducer, the presence of catalytic metal ions, and the antioxidant/oxidation substrate concentration ratio [15d,e,23] . This finding was corroborated in a number of our previous studies on biological activity of other compounds, such as allylpolyalkoxybenzenes, [9] curcumin, [24] and sesamol‐based methylenebisphenol [7d] …”

“…We compared the AOA of α‐mangostin ( 1 ) and its derivatives 2 – 6 using different test systems, including cell‐based system, all of which have been successfully used in previous studies [7a,b,d,9,13] . One of the methods used to assess the AOA of chemical compounds and different extracts is oxidative hemolysis of mammalian RBCs.…”