Fast Identification of Radical Scavengers from Securigera varia by Combining 13C-NMR-Based Dereplication to Bioactivity-Guided Fractionation
| Autor: | Dominique Harakat, Jean-Hugues Renault, Jane Hubert, Coralie Janin, Jean-Marc Nuzillard, Pacôme Sientzoff, Abdulmagid Alabdul Magid, Laurence Voutquenne-Nazabadioko |
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| Přispěvatelé: | Chimie des Substances Naturelles (ICMRCSN), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
DPPH
Isoorientin Isovitexin Pharmaceutical Science Hyperoside Centrifugation [CHIM.THER]Chemical Sciences/Medicinal Chemistry Chemical Fractionation Antioxidants Article Analytical Chemistry S. varia lcsh:QD241-441 chemistry.chemical_compound Securigera varia Picrates lcsh:Organic chemistry Drug Discovery Physical and Theoretical Chemistry Carbon-13 Magnetic Resonance Spectroscopy Chromatography biology Organic Chemistry Biphenyl Compounds Fabaceae Free Radical Scavengers [SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics biology.organism_classification dereplication 13C-NMR Biphenyl compound Molecular Weight chemistry Chemistry (miscellaneous) Apigenin flavonoids Molecular Medicine Astragalin centrifugal partition extraction |
| Zdroj: | Molecules, Vol 20, Iss 8, Pp 14970-14984 (2015) Molecules Molecules, MDPI, 2015, 20 (8), pp.14970-14984. ⟨10.3390/molecules200814970⟩ Volume 20 Issue 8 Pages 14970-14984 |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules200814970⟩ |
| Popis: | International audience; 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% |
| Databáze: | OpenAIRE |
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