Abstract
One new and six known flavone glycosides were isolated from the MeOH extract of Melilotus neapolitana Ten. The new compound, identified as 7-O-beta-D-glucopyranosyloxy-4',5-dihydroxy-3-[O-alpha-L-rhamnopyranosyl-(1-->6)-3-O-beta-D-glucopyranosyloxy]flavone (1) by 1D and 2D NMR techniques and mass spectra, was isolated along with kaempferol-3-O-rutinoside (2), kaempferol-3-O-glucoside (3), rutin (4), quercetin-3-O-glucoside (5), isorhamnetin-3-O-rutinoside (6), and isorhamnetin-3-O-glucoside (7). The antioxidant and radical scavenging activities of these compounds and the whole crude methanol extract were evaluated. The organic extract can inhibit MDA marker's synthesis by 57%. All the metabolites displayed good reducing power, with the kaempferol (2,3) and isorhamnetin derivatives (6,7) being less active than the corresponding quercetin derivatives 4,5.
MeSH terms
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Antioxidants / chemistry
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Antioxidants / isolation & purification
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Antioxidants / pharmacology*
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Disaccharides / chemistry
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Disaccharides / isolation & purification
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Disaccharides / pharmacology*
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Flavones / chemistry
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Flavones / isolation & purification
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Flavones / pharmacology*
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Flavonoids / chemistry
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Flavonoids / isolation & purification
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Flavonoids / pharmacology
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Flavonols / chemistry
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Flavonols / isolation & purification
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Flavonols / pharmacology
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / isolation & purification
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Free Radical Scavengers / pharmacology*
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / pharmacology*
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Kaempferols / chemistry
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Kaempferols / isolation & purification
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Kaempferols / pharmacology*
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Melilotus / chemistry*
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Monosaccharides / chemistry
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Monosaccharides / isolation & purification
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Monosaccharides / pharmacology*
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Plant Extracts / chemistry
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Plant Extracts / pharmacology*
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Quercetin / analogs & derivatives*
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Quercetin / chemistry
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Quercetin / isolation & purification
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Quercetin / pharmacology
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Reactive Oxygen Species / metabolism*
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Rutin / chemistry
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Rutin / isolation & purification
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Rutin / pharmacology
Substances
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7-O-glucopyranosyloxy-4',5-dihydroxy-3-(O-rhamnopyranosyl-(1-6)-3-O-glucopyranosyloxy)flavone
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Antioxidants
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Disaccharides
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Flavones
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Flavonoids
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Flavonols
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Free Radical Scavengers
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Glycosides
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Kaempferols
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Monosaccharides
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Plant Extracts
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Reactive Oxygen Species
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isorhamnetin 3-O-rutinoside
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kaempferol-3-O-glucoside
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isoquercitrin
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kaempferol-3-O-rutinoside
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Rutin
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kaempferol
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Quercetin
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isorhamnetin 3-O-glucoside