Taxonomic group: fungi / Ascomycota, Basidiomycota, Mucoromycota, Mucoromycota, Mucoromycota, Mucoromycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota (Phylum: Ascomycota, Basidiomycota, Mucoromycota, Mucoromycota, Mucoromycota, Mucoromycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota, Ascomycota)
 
The structure was elucidated in this paper
NCBI PubMed ID: 24704375
Publication DOI: 10.1016/j.ejphar.2014.03.014
Journal NLM ID: 1254354
Publisher: Amsterdam: Elsevier
Correspondence: de Oliveira V <valeriaoliveiraufg.br>
Institutions: Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, Goiânia, Brazil, Laboratório de Bioconversão, Faculdade de Farmácia, Universidad eFederal de Goiás, Setor Universitário,Brazil, Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Setor Universitário, Brazil

In this work we report the vasorelaxant activity of 7-β-O-glycosides obtained with biosynthesis of naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4). These compounds were obtained from naringenin (1) and quercetin (2) glycosylation catalyzed by Beauveria bassiana ATCC 7159. Screening of the best strain as a catalyst for glycosylation was carried out and the reaction conditions established. Cultures were grown in PDSM medium for 7 days at 27 °C. After purification by reverse-phase preparative HPLC, naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4) were identified by (1)H and (13)C NMR. The right position and β-configuration of the glucose was determined through HSQC and HMBC experiments. The vasorelaxation potential of naringenin, quercetin and its glycosylated derivatives was evaluated using isolated aorta in vitro models. Interestingly, results suggest that vasorelaxation properties of naringenin, rutin and its glycosides are due to different pathways.

glycosylation, quercetin, Beauveria bassiana, aorta relaxation, naringenin

Structure type: monomer
Location inside paper: Fig. 1(4)
Trivial name: quercimeritrin
Compound class: glucoside, glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
 
Methods: 13C NMR, 1H NMR, HMBC, HPLC-UV, biological studies
Biological activity: Vascular studies added cumulatively to the bath solution during the sustained contraction induced by phenylephrine, have evoked concentration-dependent relaxation 92.4%, n=5; pD2 3.90 potency in endothelium-denuded aortic rings
Comments, role: in Fig. 1 structures 2 and 3 are swapped, and quercetin is erroneous (lacks meta-OH group at 3')
 
Related record ID(s): 48671, 48906
NCBI Taxonomy refs (TaxIDs): 176275, 5537, 76405, 91625, 64495
Reference(s) to other database(s): PubChem: 5282160
Show glycosyltransferases
 
NMR conditions: in CD3OD        [as TSV]

1H NMR data: present in publication

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