Reactive oxygen species scavenging activity of flavone glycosides from Melilotus neapolitana.
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.
Fiorentino
Antonio
A
Dipartimento di Scienze della Vita, Seconda Università degli Studi di Napoli, I-81100 Caserta, Italy. antonio.fiorentino@unina2.it
D'Abrosca
Brigida
B
Pacifico
Severina
S
Golino
Annunziata
A
Mastellone
Claudio
C
Oriano
Palma
P
Monaco
Pietro
P
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D047309:Flavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D044948:Flavonols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D044949:Kaempferols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D029903:Melilotus / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D011794:Quercetin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017382:Reactive Oxygen Species / Q000378:metabolism*; D012431:Rutin / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
C523694:7-O-glucopyranosyloxy-4',5-dihydroxy-3-(O-rhamnopyranosyl-(1-6)-3-O-glucopyranosyloxy)flavone; D000975:Antioxidants; D004187:Disaccharides; D047309:Flavones; D005419:Flavonoids; D044948:Flavonols; D016166:Free Radical Scavengers; D006027:Glycosides; D044949:Kaempferols; D009005:Monosaccharides; D010936:Plant Extracts; D017382:Reactive Oxygen Species; C515815:isorhamnetin 3-O-rutinoside; C511963:kaempferol-3-O-glucoside; C016527:isoquercitrin; C492687:kaempferol-3-O-rutinoside; D012431:Rutin; C006552:kaempferol; D011794:Quercetin; C432511:isorhamnetin 3-O-glucoside