title: Flavonoid oligoglycosides from Ophioglossum vulgatum L. having wound healing properties.
abstract: Two new glycosylated and acylated flavonols, viz. quercetin-3-O-[(6-caffeoyl)-β-glucopyranosyl (1 → 3) α-rhamnopyranoside]-7-O-α-rhamnopyranoside (2), and kaempferol-3-O-[(6-caffeoyl)-β-glucopyranosyl (1 → 3) α-rhamnopyranoside]-7-O-α-rhamnopyranoside (3), together with the known quercetin-3-O-methyl ether (1), were isolated from the aerial parts of the fern Ophioglossum vulgatum L. Their structures were established by means of 1D and 2D NMR spectra, as well as ESI-MS and ESI-HRMS spectra. Compounds 1-3 were all found to be active in scratch-wound healing assays on keratinocytes, with 3 being the most active one and showing maximum activity at 20 µM.
authors.affiliation: Dipartimento di Scienze ed Innovazione Tecnologica, Università del Piemonte Orientale, Alessandria, Italy. marco.clericuzio@mfn.unipmn.it
authors.forename: Marco
authors.initials: M
authors.lastname: Clericuzio
authors.forename: Stefano
authors.initials: S
authors.lastname: Tinello
authors.forename: Bruno
authors.initials: B
authors.lastname: Burlando
authors.forename: Elia
authors.initials: E
authors.lastname: Ranzato
authors.forename: Simona
authors.initials: S
authors.lastname: Martinotti
authors.forename: Laura
authors.initials: L
authors.lastname: Cornara
authors.forename: Arianna
authors.initials: A
authors.lastname: La Rocca
mesh_terms: D001792:Blood Platelets / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D029624:Ferns / Q000737:chemistry*; D044948:Flavonols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D044949:Kaempferols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015603:Keratinocytes / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D014945:Wound Healing / Q000187:drug effects*
chemical_list: D044948:Flavonols; D006027:Glycosides; D044949:Kaempferols; D010936:Plant Extracts; C579701:kaempferol-3-O-((6-caffeoyl)-beta-glucopyranosyl (1-3) alpha-rhamnopyranoside)-7-O-alpha-rhamnopyranoside; C459210:quercetin 3-O-methyl ether; C579702:quercetin-3-O-((6-caffeoyl)-beta-glucopyranosyl-beta-glucopyranosyl (1-3) alpha-rhamnopyranoside)-7-O-alpha-rhamnopyranoside; C006552:kaempferol; D011794:Quercetin