Flavonol monoglycosides isolated from the antiviral fractions ofPersea americana (Lauraceae) leaf infusion

Almeida, Ana Paula de; Miranda, Mauro Sayão de; Simoni, Isabela Cristina; Wigg, M.D.; Lagrota, M. H. C.; Costa, Sônia Soares

doi:10.1002/(sici)1099-1573(199812)12:8<562::aid-ptr356>3.0.co;2-6

Cited by 97 publications

(59 citation statements)

References 7 publications

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“…The glycosides were identified based on the characteristic NMR signals. The analysis of the NMR data and comparison with those reported in the literature led to the structural assignments of the compounds as quercetin-3-O-b-D-glucopyranoside (4) (Gudej 2003;Kim et al 2006), kaempferol-3-O-a-L-rhamnopyranoside (5) (de Almeida et al 1998), quercetin-3-O-a-L-rhamnopyranoside (quercetrin) (6) and quercetin-3-O-b-Darabinopyranoside (7) (Gudej 2003;Kim 2006) (Figure 1). This is also the first report of the isolation of these compounds from this plant species.…”

Section: Resultsmentioning

confidence: 99%

Modulation of intracellular expression of IFNγ and IL-2 in culture of splenic T lymphocytes by some flavonoid glycosides ofAlchornea floribunda

Okoye

Odimegwu

Nworu

et al. 2016

Pharmaceutical Biology

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Context Alchornea floribunda Mü ll. Arg. (Euphorbiaceae) leaves are widely used in ethnomedicine for the management of rheumatism, arthritis and toothache. Objective In this study, flavonoid glycosides isolated from Alchornea floribunda were screened for their effect on the intracellular expression of interferon-gamma (IFNg) and interleukin-2 (IL-2) type-1 cytokines. Materials and methods Chromatographic purification of the ethyl acetate fraction of the methanol leaf extract led to the isolation of seven flavonoid glycosides (1-7). Their structures were elucidated by 1D and 2D nuclear magnetic resonance and mass spectrometry. Splenocytes were treated with graded concentrations of the compounds (6.25-25 mg/mL) and incubated for 24 h. Thereafter, their effect on the expression of IFNg and IL-2 by CD4 + and CD8 + T-lymphocytes was evaluated using intracellular cytokine staining and FACS analysis. Results Compounds 1-7 (6.25-25 mg/mL) caused the up-regulation of activated CD8 + (57.85-72.45% versus 57.85% for untreated control) and, to a lesser extent, activated CD4 + (3.21-7.21% versus 2.75% for the untreated control) T-lymphocytes that were both largely interferon-gammareleasing in treated mouse T lymphocytes relative to untreated control. FACS data analysis showed that stimulation with all the compounds increased the proportion of CD8 + /IFNg + and CD4 +

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Section: Resultsmentioning

confidence: 99%

Modulation of intracellular expression of IFNγ and IL-2 in culture of splenic T lymphocytes by some flavonoid glycosides ofAlchornea floribunda

Okoye

Odimegwu

Nworu

et al. 2016

Pharmaceutical Biology

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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: 99%

“…4) showed the correlations of furanosyl moiety. 21 The rha C-2² signal, assigned at d 79.4 by the analysis of the COSY and HSQC data, was downfield shifted by 7.1 ppm comparing to that in the 1-substituted rhamnosyl group (d C-2 72.3), 13 suggesting an apiosyl- (Fig. 4), supporting the a-L-arabinofuranosyl moiety and the sugar linkage.…”

Section: Resultsmentioning

confidence: 99%

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Lin¹,

Tsai²,

Lee³

2011

J Chinese Chemical Soc

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“…The structures of isolated compounds were identified by a combination of spectroscopic methods (MS, 1 D NMR and 2D NMR) and comparisons with the literature data as a mixture of quercetin 3-β-Ogalactopyranoside or hyperoside (1) and quercetin 3-β-Oglucopyranoside or isoquercitrin (1:1) (2) (Almeida et al, 1998;Costa et al, 2007;Ohguchi et al, 2010), quercetin 3-O-α-rhamnoside or quercitrin (3) (Zhong et al, 1997), luteolin 6-C-β-glucopyranoside or orientin (4) (Li et al, 2009), apigenin-6-C-glucoside or isovitexin (5) (Leong et al, 2010), kaempferol 3-O-α-rhamnoside (6) (Fossen et al, 1999) and lupenone (7) (Prachayasittikul et al, 2010), respectively. Characterization of the sugar moieties from the mixture of quercetin 3-β-galactopyranoside (1) and quercetin 3-β-glucopyranoside (2) was performed according Cota et al 2008b.…”

Section: Resultsmentioning

confidence: 90%

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

Cota¹,

Siqueira²,

Oliveira³

et al. 2012

Rev. bras. farmacogn.

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Abstract:Many phenolic compounds such as xanthones, quinones and coumarins have been isolated from Kielmeyera species; however the presence of flavonoids have been showed in other genera in the Calophylleae tribe as Caraipa, Mesua and Calophyllum. Six known glycosidic flavonoids: quercetin 3-β-O-galactopyranoside (1), quercetin 3-β-O-glucopyranoside (2), quercetin 3-O-α-rhamnoside (3), luteolin 6-C-β-glucopyranoside (4), isovitexin (5), kaempferol 3-O-α-rhamnoside (6) and one triterpene, lupenone (7) were isolated, for the first time, from organic crude extract of Kielmeyera variabilis Mart. & Zucc., Calophyllaceae, leaves. The crude organic extract from K. variabilis leaves exhibited 95% of leishmanidal activity at 20 µg/mL on amastigote-like form of Leishmania (Leishmania) amazonensis in vitro model and only compound 3 showed 40-45% of growth inhibition at concentration ranging from 0.78 to 20 µg/mL. In addition, quercetin 3-O-α-rhamnoside (quercitrin) was found to be the major metabolite. Our results and previous reports suggest that synergistic effects of flavonoid glycosides are the cause of significant leishmanidal activity of the crude organic extract from K. variabilis leaves.

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Flavonol monoglycosides isolated from the antiviral fractions ofPersea americana (Lauraceae) leaf infusion

Cited by 97 publications

References 7 publications

Modulation of intracellular expression of IFNγ and IL-2 in culture of splenic T lymphocytes by some flavonoid glycosides ofAlchornea floribunda

Modulation of intracellular expression of IFNγ and IL-2 in culture of splenic T lymphocytes by some flavonoid glycosides ofAlchornea floribunda

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Chemical constituents and leishmanicidal activity from leaves of Kielmeyera variabilis

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