Highly glycosylated flavonols with an O-linked branched pentasaccharide from Iberis saxatilis (Brassicaceae).

Abstract:

:Four flavonol glycosides isolated from non-flowering leafy shoots of Iberis saxatilis (Brassicaceae) were characterised by spectroscopic and chemical methods as saxatilisins A-D, the 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside, 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside, 3-O-(6-O-E-sinapoyl)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside, and 3-O-(6-O-E-feruloyl)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside of isorhamnetin (3,5,7,4'-tetrahydroxy-3'-methoxyflavone), respectively. Analysis of (2)J(HC) correlations detected with the H2BC (heteronuclear two-bond correlation) pulse sequence aided the unambiguous assignment of glycosidic resonances in the (1)H and (13)C NMR spectra of these compounds. Saxatilisins A, C, and D, are the first flavonol glycosides to be described with a pentasaccharide chain at a single glycosylation site. Several pentaglycosides of kaempferol and quercetin, tentatively assigned as saxatilisin analogues from LC-MS/MS analyses, were present as minor constituents of the extracts.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Prescott TA,Kite GC,Porter EA,Veitch NC

doi

10.1016/j.phytochem.2012.12.009

subject

Has Abstract

pub_date

2013-04-01 00:00:00

pages

85-91

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(12)00531-6

journal_volume

88

pub_type

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