Synthesis, characterization, and functional properties of chlorophylls, pheophytins, and Zn-pheophytins

[Display omitted] •Chlorophylls and their derivatives, pheophytins and Zn-pheophytins, were identified.•Among pigments evaluated, Zn-pheophytins had the highest antioxidant activity.•First study on the anti-inflammatory capacity of Zn-pheophytins.•Zn-pheophytins remarkably suppressed the inflammatory responses of macrophages. The aims of this study were to synthesize chlorophyll derivatives, pheophytins and Zn-pheophytins, from chlorophylls extracted from spinach, characterize them, and evaluate their antioxidant and anti-inflammatory activities. The chlorophylls isolated from spinach were identified by means of FT-IR and NMR spectroscopies. The synthesis of pheophytins and Zn-pheophytins was confirmed by UV–Vis spectral analyses. The antioxidant activity of chlorophylls, pheophytins, and Zn-pheophytins was studied. The results revealed that the Zn-pheophytins showed the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene bleaching activities, followed by chlorophylls and pheophytins. Additionally, Zn-pheophytins showed substantial inhibitory activity against lipopolysaccharide (LPS)-induced NO production in RAW 264.7 cells. Furthermore, Zn-pheophytins remarkably suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) in RAW 264.7 cells and showed no cytotoxicity. Our findings indicated that Zn-pheophytins have strong antioxidant and anti-inflammatory properties and can therefore be a potential source of bioactive compounds for nutraceutical, cosmetic, and pharmaceutical applications.