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Highly glycosylated flavonoids from the pods of Bobgunnia madagascariensis

Highly glycosylated flavonoids from the pods of Bobgunnia madagascariensis

Stevenson, Philip C. ORCID: 0000-0002-0736-3619, Nyirenda, Stephen P. and Veitch, Nigel C. (2010) Highly glycosylated flavonoids from the pods of Bobgunnia madagascariensis. Tetrahedron Letters, 51 (36). pp. 4727-4730. ISSN 0040-4039 (doi:10.1016/j.tetlet.2010.07.013)

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Abstract

Methanolic extracts of the pods of Bobgunnia madagascariensis (Leguminosae) yielded four pentaglycosylated flavonoids, including the 3-O-α-l-rhamnopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[α-l-rhamnopyranosyl(1→6)]-β-d-glucopyranoside-7-O-α-l-rhamnopyranosides of 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one (kaempferol) and 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-4H-benzopyran-4-one (quercetin), which were characterized by a novel O-linked branched tetrasaccharide. Spectroscopic and chemical methods were used to determine the structures of the latter, which co-occurred with the corresponding β-d-galactopyranosyl isomers, and two saponins. Conformational isomerism of quercetin 3-O-α-l-rhamnopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[α-l-rhamnopyranosyl(1→6)]-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside was detected in solution by NMR, a phenomenon previously associated only with C-glycosylflavonoids

Item Type: Article
Uncontrolled Keywords: bobgunnia, swartzia, tribe Swartzieae, Leguminosae, flavonol pentaglycosides, saponins
Subjects: Q Science > Q Science (General)
S Agriculture > S Agriculture (General)
Q Science > QD Chemistry
Faculty / Department / Research Group: Faculty of Engineering & Science > Natural Resources Institute
Faculty of Engineering & Science > Natural Resources Institute > Agriculture, Health & Environment Department
Related URLs:
Last Modified: 17 Jul 2012 09:36
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/3780

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