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.
Georg Thieme Verlag KG Stuttgart · New York.
MeSH terms
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Blood Platelets / drug effects
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Dose-Response Relationship, Drug
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Ferns / chemistry*
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Flavonols / chemistry*
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Flavonols / isolation & purification
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Flavonols / pharmacology*
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Glycosides / chemistry
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Glycosides / isolation & purification
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Glycosides / pharmacology
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Humans
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Inhibitory Concentration 50
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Kaempferols / chemistry
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Kaempferols / isolation & purification
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Kaempferols / pharmacology
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Keratinocytes / drug effects
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Plant Components, Aerial / chemistry
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Plant Extracts / chemistry*
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Plant Extracts / isolation & purification
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Plant Extracts / pharmacology
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Plants, Medicinal
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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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Spectrometry, Mass, Electrospray Ionization
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Wound Healing / drug effects*
Substances
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Flavonols
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Glycosides
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Kaempferols
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Plant Extracts
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kaempferol-3-O-((6-caffeoyl)-beta-glucopyranosyl (1-3) alpha-rhamnopyranoside)-7-O-alpha-rhamnopyranoside
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quercetin 3-O-methyl ether
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quercetin-3-O-((6-caffeoyl)-beta-glucopyranosyl-beta-glucopyranosyl (1-3) alpha-rhamnopyranoside)-7-O-alpha-rhamnopyranoside
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kaempferol
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Quercetin