DOSY NMR applied to analysis of flavonoid glycosides from <i>Bidens sulphurea</i>

Rodrigues, Edilene Delphino; Silva, Denise Brentan; Oliveira, Dionéia Camilo Rodrigues de; Silva, Gil Valdo José da

doi:10.1002/mrc.2516

Cited by 35 publications

(25 citation statements)

References 65 publications

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“…3), characterized by the 1 H-NMR data (Tables 1, S1 and S2 in supplementary data). The 1 H-NMR spectra of 1, 2, 4, and 12-17 showed typical signals for the flavonol kaempferol moiety, 9,10 a meta-coupled AX system for H-6 and 13,14 On the basis of these analyses and in comparison to the reference data, compounds 6, 7, 9, 11-13, 15, 17, and 18 were identified as quercetin-3-O-b-D-galactopyranoside (6), 13,16 14 3-O-a-L-arabinopyranoside (15), 13 and 3-O-a-L-rhamnopyranoside (17), 13 and apigenin 4¢-O-b-D-glucopyranoside (18). 12 Compounds 8 (Table 1).…”

Section: Resultsmentioning

confidence: 93%

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Lin¹,

Tsai²,

Lee³

2011

J Chinese Chemical Soc

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Section: Resultsmentioning

confidence: 93%

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Lin¹,

Tsai²,

Lee³

2011

J Chinese Chemical Soc

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“…Using NMR, ESI-MS, and UV spectral analyses, the compounds in profile peaks from Figure 1A were identified as: guaijaverin (quercetin-3- O -α-arabinoside, peak 1 ) [32]; quercetin (peak 2 ) [33]; quercitrin (quercetin-3- O -α-rhamnoside, peak 3 ) [34]; isoquercitrin (quercetin-3- O -β-glucoside, peak 4a ); and hyperin (quercetin-3- O -galactoside, peak 4b ) [35]. Figure 2 shows the chemical structure of these compounds, and Table 1 shows their corresponding HPLC-DAD and ESI-MS data.…”

Section: Resultsmentioning

confidence: 99%

Quercetin and quercetin 3-O-glycosides from Bauhinia longifolia (Bong.) Steud. show anti-Mayaro virus activity

et al. 2014

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BackgroundThe arthropod-borne Mayaro virus (MAYV) causes ‘Mayaro fever’, a disease of medical significance, primarily affecting individuals in permanent contact with forested areas in tropical South America. Recently, MAYV has attracted attention due to its likely urbanization. Currently, there are no licensed drugs against most mosquito-transmitted viruses. Here, we investigated the in vitro anti-MAYV activity of the flavonoids quercetin and its derivatives from the Brazilian shrub Bauhinia longifolia (Bong.) Steud.MethodsFlavonoids were purified by chromatographic fractionation from leaf extracts of B. longifolia and chemically identified as quercetin and quercetin glycosides using spectroscopic techniques. Cytotoxicity of purified flavonoids and of EtOAc- and n-BuOH-containing flavonoid mixtures was measured by the dye-uptake assay while their antiviral activity was evaluated by a virus yield inhibition assay.ResultsThe following flavonoids were purified from B. longifolia leaves: non-glycosylated quercetin and its glycosides guaijaverin, quercitrin, isoquercitrin, and hyperin. EtOAc and n-BuOH fractions containing these flavonoids demonstrated the highest antiviral activity of all tested substances, while quercetin had the highest antiviral activity amongst purified flavonoids. Quercetin, EtOAc, or n-BuOH fractions inhibited MAYV production by more than 90% at 25 μg/mL, displaying a stronger antiviral effect than the licensed antiviral ribavirin. A mixture of the isomers isoquercitrin and hyperin had a modest antiviral effect (IC90 = 104.9), while guaijaverin and quercitrin did not show significant antiviral activity.ConclusionsB. longifolia is a good source of flavonoids with anti-Mayaro virus activity. This is the first report of the activity of quercetin and its derivatives against an alphavirus.

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“…Diffusion-order spectroscopy (DOSY) is a powerful tool in the direct analysis of mixtures, which has been successfully applied in flavonoid analytics. (Rodrigues, da Silva, Denise Brentan, de Oliveira, Dionéia Camilo Rodrigues, & da Silva, Gil Valdo José, 2009) Recently, various additives, like polyethylenglycol (PEG) or sodium dodecyl sulfate (SDS) have been used to improve resolution in these DOSY measurements of flavonoid containing mixtures. (Kavakka, Parviainen, Wähälä, Kilpeläinen, & Heikkinen, 2010) Compared to direct HPLC-NMR hyphenation off-line techniques usually provide higher quality of NMR spectra and allow by multiple trapping an increase in analyte amounts.…”

Section: Introductionmentioning

confidence: 99%

Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments

et al. 2017

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We present a standardized, straightforward and efficient approach applicable in routine analysis of flavonoids combining sensitive NMR and HPLC experiments. The determination of the relative configuration of sugar moieties usually requires the acquisition of C NMR shift values. We use a combination of HPLC and sensitive NMR experiments (1D-proton, 2D-HSQC) for the unique identification of known flavones, flavanones, flavonols and their glycosides. Owing to their broad range of polarity, we developed HPLC and UHPLC methods (HO/MeOH/MeCN/HCOOH) which we applied and validated by analyzing 46 common flavones and flavanones and exemplified for four plant extracts. A searchable data base is provided with full data comprising complete proton and carbon resonance assignments, expansions of HSQC-spectra, HPLC parameters (retention time, relative retention factor), UV/Vis and mass spectral data of all compounds, which enables a rapid identification and routine analysis of flavones and flavanones from plant extracts and other products in nutrition and food chemistry.

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DOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea

Cited by 35 publications

References 65 publications

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Quercetin and quercetin 3-O-glycosides from Bauhinia longifolia (Bong.) Steud. show anti-Mayaro virus activity

Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments

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