Synthesis, Characterization, and Antioxidant Activity of 8-Hydroxygenistein

Abstract

It was reported that 8-hydroxygenistein (8-OHG) was synthesized by methylation, bromination, methoxylation, and demethylation using cheap and readily available biochanin A as raw material. All synthesized products were structurally confirmed by ultra-high-performance liquid chromatography (UHPLC), infrared spectroscopy, mass spectrometry, 1H-nuclear magnetic resonance (NMR), and 13C-NMR. In addition, we examined the antioxidant capacity of 8-OHG using 6 different methods such as 1,1-diphenyl-2-picrylhydrazyl radical scavenging, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) radical (ABTS) scavenging, nitric oxide radical (NO) scavenging, superoxide radical (O2−•) scavenging, reducing power assay, and total antioxidant activity using ascorbic acid (VC) as a positive control. Compared with VC, 8-OHG exhibited higher total antioxidant activity and stronger scavenging activity on ABTS, NO, and O2−•. These results indicate that 8-OHG is an excellent antioxidant agent and may be effective in preventing damage induced by free radical.