Identification of natural epimeric flavanone glycosides by NMR spectroscopy

Maltese, Federica; Erkelens, C.; Kooy, Frank van der; Choi, Young Hae; Verpoorte, Robert

doi:10.1016/j.foodchem.2009.03.023

Cited by 83 publications

(65 citation statements)

References 20 publications

(22 reference statements)

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“…The 13 C NMR also confirmed the compound to be hesperidin. The above physical and spectroscopy data were comparable with those of hesperidin reported in the literature with 2S configuration (Inove et al, 2010;Maltese et al, 2009).…”

Section: Discussionsupporting

confidence: 88%

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Bioassay guided fractionation and identification of active anti-inflammatory constituent fromDelonix elataflowers using RAW 264.7 cells

Saravanan

Ibrahim

David³

et al. 2014

Pharmaceutical Biology

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Context: Delonix elata (L.) Gamble (Fabaceae) has been used in the Indian traditional medicine system to treat rheumatism and inflammation. Aim: To assess the anti-inflammatory effect of Delonix elata flowers and to isolate the active principle. Materials and methods: The prompt anti-inflammatory constituent was isolated from Delonix elata flower extracts using bioassay guided fractionation in liposaccharide (LPS) stimulated RAW 264.7 macrophage cell line. The anti-inflammatory activity of extracts/fractions/subfractions/compounds (10, 25, and 50 mg/ml) was evaluated by estimating the levels of nitric oxide (NO), TNF-a, and IL-1b after 24 h of LPS induction (1 mg/ml). The isolated active compound was subjected to NMR, IR, and UV analyses for structure determination. Results: In an attempt to search for anti-inflammatory constituents, the active pure principle was isolated and crystallized as a white compound from Delonix elata flowers methanol extract. This active compound (50 mg/ml) decreased the release of inflammatory mediators levels such as NO (0.263 ± 0.03 mM), TNFa (160.20 ± 17.57 pg/ml), and IL-1b (285.79 ± 15.16 pg/ml) significantly (p50.05); when compared to the levels of NO (0.774 ± 0.08 mM), TNFa (501.71 ± 25.14 pg/ml), and IL-1b (712.68 ± 52.25 pg/ml) from LPS-stimulated macrophage cells. The active compound was confirmed as hesperidin with NMR, IR, and UV spectroscopy data. This is the first report of this compound from Delonix elata flowers. Conclusion: The findings of the study support the traditional use of Delonix elata flowers to treat inflammation.

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Section: Discussionsupporting

confidence: 88%

“…The NMR, IR, and UV (Figure 4a-e) analysis confirmed the compound to be hesperidin ( Figure 5) (Lin et al, 2007). The spectroscopy data were comparable with those of hesperidin reported in the literature with 2S configuration (Inove et al, 2010;Maltese et al, 2009). This is the first report of this compound from this plant.…”

supporting

confidence: 82%

Bioassay guided fractionation and identification of active anti-inflammatory constituent fromDelonix elataflowers using RAW 264.7 cells

Saravanan

Ibrahim

David³

et al. 2014

Pharmaceutical Biology

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“…Furthermore, the obtained spectral data for the known isolated compounds were consistent with the reported literature; they were unambiguously identified as jatrophadiketone (1) [11], β.sitosterol (2) [12,13], curcuson D (3) [14], curcuson C (4) [14], naringenin (5) [15], β.sitosterol glucoside (6) [16], spruceanol (7) [17], propacin (8) [18,19], cleomiscosin B (9) [18,19], cleomiscosin A (10) [18,19], apigenin (11) [20], uracil (12) [21,22,23], cynaroside (13) [24], linarin (14) [25,26], hovetricoside C (16) [27], N-methyltryptamine (17) [28], N-methyltyramine (19) [29], hordenine (20) [30], hordenine HCL (21) and N-methyltyramine HCL (22) [compounds 21 and 22 were identical to the standard samples (Sigma-Aldrich, USA), as shown by 1 H NMR and TLC. ].…”

Section: Structure Elucidationsupporting

confidence: 84%

Phytochemical and Biological Investigation of <em>Jatropha pelargoniifolia</em> Root Native to the Kingdom of Saudi Arabia

Aati¹,

Gamal²,

Kayser³

2018

Preprint

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Extensive phytochemical and chromatographic analysis of different root fractions of Jatropha pelargoniifolia Courb. (Euphorbiaceae) resulted in the isolation and identification of 22 distinct secondary metabolite compounds. Two new compounds, 6-hydroxy-8-methoxycoumarin-7-O-β-D-glycopyranoside and (3-(2-(methylamino) ethyl)-1H-indol-2-yl) methanol, were isolated and identified for the first time from a natural source. In addition, other known compounds, such as hovetricoside C and Nmethyltryptamine were isolated from Euphorbiaceae, and hordenine, Nmethyltyramine, their salts, cynaroside and linarin were identified in Jatropha spp. for the first time. Some isolated metabolites, such as β-sitosterol, β-sitosterol glucoside, curcusons D and C, naringenin, apigenin, cleomiscosins B and A, spruceanol, propacin, jatrophadiketone, and uracil were previously identified in various Jatropha species. The structures of the isolated compounds were determined using different spectroscopic techniques. The anti-inflammatory, antinociceptive, antipyretic, and antioxidant activities were evaluated for some adequately available isolated compounds. Compounds showed significant antinociceptive activity compared with the standard analgesic drug indomethacin. The edema size was significantly reduced (p< 0.05-0.001) in the animals treated with low doses (5 and 10 mg/kg) of the isolated compounds compared with those treated with a high dose (100 mg/kg) of standard anti-inflammatory drug (phenylbutazone). Furthermore, all tested compounds showed a significant (p< 0.05-0.001) reduction in the rectal temperature of hyper-thermic mice.

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“…However, the (2S)-isoform tends to convert to the (2R)-form, reaching an approximate epimeric ratio of about 3:2 at fruit/plant maturity. This is attributed to the fact that plants metabolites are produced in a stereospecific way because of the involvement of enzymes (Maltese et al 2009). Moreover, the relative percentage of (2S)-naringin to (2R)-naringin undergoes a marked change with increasing maturity, as it was shown in Citrus grandis.…”

Section: Structural Elucidation Of the Isolated Compoundsmentioning

confidence: 99%

Phytochemical analysis with the antioxidant and aldose reductase inhibitory capacities of Tephrosia humilis aerial parts’ extracts

Plioukas

Gabrieli

Lazari

et al. 2015

Natural Product Research

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The aerial parts of Tephrosia humilis were tested about their antioxidant potential, their ability to inhibit the aldose/aldehyde reductase enzymes and their phenolic content. The plant material was exhaustively extracted with petroleum ether, dichloromethane and methanol, consecutively. The concentrated methanol extract was re-extracted, successively, with diethyl ether, ethyl acetate and n-butanol. All extracts showed significant antioxidant capacity, but the most effective was the ethyl acetate extract. As about the aldose reductase inhibition, all fractions, except the aqueous, were strong inhibitors of the enzyme, with the n-butanolic and ethyl acetate fractions to inhibit the enzyme above 75%. These findings provide support to the ethnopharmacological usage of the plant as antioxidant and validate its potential to act against the long-term diabetic complications. The phytochemical analysis showed the presence of 1,4-dihydroxy-3,4-(epoxyethano)-5-cyclohexene(1), cleroindicin E(2), lupeol(3), methyl p-coumarate(4), methyl 4-hydroxybenzoate(5), prunin(6), 5,7,2',5'-tetrahydroxyflavanone 7-rutinoside(7), protocatechuic acid(8), luteolin 7-glucoside(9), apigenin(10), naringin(11), rhoifolin(12) and luteolin 7-glucuronate(13).

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Identification of natural epimeric flavanone glycosides by NMR spectroscopy

Cited by 83 publications

References 20 publications

Bioassay guided fractionation and identification of active anti-inflammatory constituent fromDelonix elataflowers using RAW 264.7 cells

Bioassay guided fractionation and identification of active anti-inflammatory constituent fromDelonix elataflowers using RAW 264.7 cells

Phytochemical and Biological Investigation of <em>Jatropha pelargoniifolia</em> Root Native to the Kingdom of Saudi Arabia

Phytochemical analysis with the antioxidant and aldose reductase inhibitory capacities of Tephrosia humilis aerial parts’ extracts

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