Abstract
Securigera varia (Fabaceae) is a common herbaceous perennial plant widely growing in Europe and Asia and purposely established for erosion control, roadside planting, and soil rehabilitation. The aim of this study was to determine the radical scavenging activity of a crude methanol extract of S. varia aerial parts by using the free radical DPPH (1,1-diphenyl-2-picrylhydrazyl) and to rapidly identify the compounds involved in this activity. The crude extract was initially separated in five fractions on Diaion HP20 resin and the most active part was fractionated by Centrifugal Partition Extraction (CPE). Known compounds were directly identified by a 13C-NMR-based dereplication method. Semi-preparative high performance liquid chromatography purification experiments were further performed to identify unknown or minor active compounds. As a result, one new (13) and twelve known flavonoid glycosides together with three nitropropanoylglucopyranoses were isolated, including astragalin (1), kaempferol-3-O-(6-O-acetyl)-β-d-glucopyranoside (2), kaempferol-3,4′-di-O-β-d-glucopyranoside (3), trifolin (4), isoquercitrin (5), hyperoside (6), isovitexin (7), isoorientin (8), isovitexin 4′-O-β-d-glucopyranoside (9), apigenin 7-O-β-d-glucuronopyranoside (10), luteolin 7-O-β-d-glucuronopyranoside (11), apigenin 7-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucuronopyranoside (12), apigenin 7-O-β-d-glucopyranosyl-(1→2)-β-d-glucuronopyranoside (13), 6-O-(3-nitropropanoyl)-β-d-glucopyranoside (14), coronillin (16) and coronarian (15). 120 mg of the most active compound isoorientin against the free radical DPPH was recovered by CPE with an HPLC purity of 99%.
Highlights
In recent years, one area which attracted a great deal of attention is the possible therapeutic use of antioxidants to control degenerative diseases associated with marked oxidative damage [1,2]
Fraction C was further subjected to Centrifugal Partition Extraction (CPE) fractionation and a 13C-NMR-based dereplication method was applied to identify the major known compounds responsible for this radical scavenging activity
The biphasic solvent system composed of Methyl tert-butyl ether (MtBE)/MeCN/water (3:3:4, v/v) in CPE was used in the ascending mode to recover moderately polar compounds such as flavonoid derivatives from 1.8 g of fraction C
Summary
One area which attracted a great deal of attention is the possible therapeutic use of antioxidants to control degenerative diseases associated with marked oxidative damage [1,2]. The aim of this study was to evaluate the radical scavenging activity of a crude methanol extract of S. varia aerial parts by using the stable free radical DPPH (1,1-diphenyl-2-picrylhydrazyl) and to rapidly identify the compounds responsible for the observed activity. For this purpose, the crude extract was initially separated in five fractions on Diaion HP20 resin and the most active one was fractionated by Centrifugal Partition Extraction (CPE). This method consists in 13C-NMR analyses of the fraction series, automatic collection and binning of 13C signals across spectra and hierarchical clustering analysis (HCA)
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