title: Flavoalkaloids and Flavonoids from Astragalus monspessulanus.
abstract: A new flavonol tetraglycoside, quercetin-3-O-[α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranosyl]-7-O-β-D-glucopyranoside (1), and two new flavonol alkaloids, N-(8-methylquercetin-3-O-[α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranosyl])-3-hydroxypiperidin-2-one (2) and N-(8-methylkaempferol-3-O-[α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranosyl])-3-hydroxypiperidin-2-one (3), were isolated from the aerial parts of Astragalus monspessulanus ssp. monspessulanus. Two rare flavonoids with an unusual 3-hydroxy-3-methylglutaric acid moiety, quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-[6-O-(3-hydroxy-3-methylglutaryl)-β-D-galactopyranoside (4) and kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-[6-O-(3-hydroxy-3-methylglutaryl)-β-D-galactopyranoside (5), were isolated from the aerial parts of A. monspessulanus ssp. illyricus. In addition, the eight known flavonoids alangiflavoside (6), alcesefoliside (7), mauritianin (8), quercetin-3-β-robinobioside (9), cosmosine (10), apigenin-4'-O-glucoside (11), trifolin (12), and rutin (13) were isolated from aerial parts of A. monspessulanus ssp. monspessulanus. Their structures were elucidated via NMR and HRESIMS data. In a model that tested t-BuOOH-induced oxidative stress on isolated rat hepatocytes, flavonoids 1-13 had statistically significant cytoprotective activity similar to that of silymarin, tested at 60 μg/mL. The most prominent effects were observed for flavonoids 1, 4, 7, and 12.
authors.forename: Ilina
authors.initials: I
authors.lastname: Krasteva
authors.forename: Viktor
authors.initials: V
authors.lastname: Bratkov
authors.affiliation: Institute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz , Universitätsplatz 4, A-8010 Graz, Austria.
authors.forename: Franz
authors.initials: F
authors.lastname: Bucar
authors.affiliation: Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, University of Graz , Universitätsplatz 1, A-8010 Graz, Austria.
authors.forename: Olaf
authors.initials: O
authors.lastname: Kunert
authors.affiliation: Institute of Forensic Medicine, Medical University of Graz , Universitätsplatz 4, A-8010 Graz, Austria.
authors.forename: Manfred
authors.initials: M
authors.lastname: Kollroser
authors.forename: Magdalena
authors.initials: M
authors.lastname: Kondeva-Burdina
authors.forename: Iliana
authors.initials: I
authors.lastname: Ionkova
mesh_terms: D000818:Animals; D027883:Astragalus Plant / Q000737:chemistry*; D002031:Bulgaria; D019610:Cytoprotection; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D044948:Flavonols / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D035261:Plant Components, Aerial / Q000737:chemistry; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism
chemical_list: D005419:Flavonoids; D044948:Flavonols; D005960:Glucosides; D011794:Quercetin