1-1-diphenyl-2-picrylhydrazyl and quercetagetin

Large amounts of citrus by-products are released from juice-processing plants every year. Most bioactive compounds are found in the peel and inner white pulp. Flavonoids are a widely distributed group of bioactive compounds. The methanolic extract of citrus peel powder has been shown to possess strong antioxidant activity. Therefore the aim of this study was to isolate the major antioxidant flavonoid compound from Citrus unshiu (satsuma) peel as citrus by-product and evaluate its antioxidant activity.. The major flavonoid isolated from C. unshiu peel was identified as quercetagetin. The structure of the compound was determined by tandem mass spectrometry and ultraviolet spectroscopy. Its antioxidant activity was assessed by assays of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, hydroxyl radical and intracellular reactive oxygen species (ROS) scavenging and DNA damage inhibition. Quercetagetin showed strong DPPH radical-scavenging activity (IC₅₀ 7.89 µmol L⁻¹) but much lower hydroxyl radical-scavenging activity (IC₅₀ 203.82 µmol L⁻¹). Furthermore, it significantly reduced ROS in Vero cells and showed a strong protective effect against hydrogen peroxide-induced DNA damage.. The results of this study suggest that quercetagetin could be used in the functional food, cosmetic and pharmaceutical industries.

Topics: Animals; Antioxidants; Biphenyl Compounds; Chlorocebus aethiops; Chromones; Citrus; DNA Damage; Flavones; Flavonoids; Fruit; Hydrogen Peroxide; Hydroxyl Radical; Picrates; Plant Extracts; Reactive Oxygen Species; Vero Cells; Waste Products

The fractionation of a methanolic extract of Tagetes maxima guided for antioxidant activity resulted in the isolation of three acylated quercetagetin glycosides, quercetagetin-7-O-(6-O-caffeoyl-beta-D-glucopyranoside), quercetagetin-7-O-(6-O-p-coumaroyl-beta-D-glucopyranoside) and quercetagetin-7-O-(6-O-galloyl-beta-D-glucopyranoside), as well as four known flavonoid glycosides. The structural elucidation was accomplished by spectroscopic methods (ESI-MS/MS and NMR). The antioxidant activity of fractions and isolated compounds was determined by checking the scavenging activity against three different radicals: 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH*), hydroxyl (*OH), and superoxide (O2*-). The three isolated compounds exhibited a high radical scavenging activity in comparison with reference compounds.

Topics: Acylation; Biphenyl Compounds; Chromones; Flavones; Free Radical Scavengers; Free Radicals; Glycosides; Hydrazines; Magnetic Resonance Spectroscopy; Molecular Structure; Picrates; Plant Components, Aerial; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; Tagetes