Synthesis of Schiff Base Metal Derivatives of Apigenin and Their Antioxidant Activity
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Abstract:
Apigenin (AP) is a natural antioxidant possessing multiple biological activities, but has some limitations such as low efficacy and low utilization. To better develop and utilize AP, its structure was modified. The Schiff-base derivatives of AP ([Co(C22H16O4N)2(H2O)2]?8H2O and [Zn(C22H16O4N)2(H2O)2]?4H2O) were synthesized, and characterized by ultraviolet (UV), infrared (IR), differential scanning calorimetry (DSC)-derivative thermograms (DTG), and other spectroscopic methods. Through the salicylic acid method and the pyrogallic acid-nitroblue tetrazolium (NBT) method, the in vitro superoxide radical and hydroxyl radical scavenging activities of AP and its Schiff-base derivatives were evaluated. Structural characterization showed that two Schiff-base derivatives of AP, [Co(C22H16O4N)2(H2O)2]?8H2O and [Zn(C22H16O4N)2(H2O)2]?4H2O, were successfully prepared. The half-maximal inhibitory concentration (IC50) values of AP, [CoL2], and [ZnL2] on scavenging hydroxyl radical were 880.65 ± 46.52 μg/mL, 517.12 ± 16.36 μg/mL, and 633.62 ± 18.95 μg/mL, respectively. The IC50 values of AP, [CoL2], and [ZnL2] on scavenging superoxide radical were 116.30 ± 3.94 μg/mL, 61.13 ± 0.05 μg/mL, and 48.56 ± 0.32 μg/mL, respectively. Two novel Schiff-base complexes of AP, [Co(C22H16O4N)2(H2O)2]?8H2O and [Zn(C22H16O4N)2(H2O)2]?4H2O, possessed stronger antioxidant activity than AP, which might be a new antioxidant food additive. This research provided a theoretical basis for AP development during future studies on antioxidants.