ABSTRACT
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 ß-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.
Subject(s)
Chlorophyll/chemistry , Pheophytins/chemistry , Plant Extracts/chemistry , Spinacia oleracea/chemistry , Animals , Anti-Inflammatory Agents/chemical synthesis , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Antioxidants/chemical synthesis , Antioxidants/chemistry , Antioxidants/pharmacology , Chlorophyll/chemical synthesis , Chlorophyll/pharmacology , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/enzymology , Macrophages/metabolism , Mice , Nitric Oxide/metabolism , Nitric Oxide Synthase Type II/genetics , Nitric Oxide Synthase Type II/metabolism , Pheophytins/chemical synthesis , Pheophytins/pharmacology , Plant Extracts/pharmacology , Spectroscopy, Fourier Transform Infrared , Zinc/chemistry , beta Carotene/chemistryABSTRACT
A new phaeophytin, ligulariaphytin A, together with five known phaeophytins, were isolated from the aerial parts of Ligularia knorringiana. The structure of ligulariaphytin A was elucidated as 13¹-hydroxy-13¹,13²-peroxyphaeophorbide A ethyl ester, and the five known compounds were identified as 13²-hydroxyphaeophorbide A ethyl ester, 17³-ethoxyphaeophorbide A, phaeophytin B, phaeophytin A, and phaeophorbide B ethyl ester, respectively, based on spectroscopic analysis and by comparison of their spectral data with those reported previously in the literature. All compounds were evaluated for their in vitro cytotoxic activities against cultured Hela cell, and were found to show only very weak cytotoxicity.
