Inhibition of glucose intestinal absorption by kaempferol 3-O-α-rhamnoside purified from Bauhinia megalandra leaves

Rodríguez, Patricia Álvarez; González-Mujica, Freddy; Bermúdez, Jairo; Hasegawa, Masahisa

doi:10.1016/j.fitote.2010.08.007

Cited by 25 publications

(19 citation statements)

References 9 publications

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“…The 1 H NMR and 13 C NMR (Table 3) spectra of compound 2 and compound 4 were compared with the data of known compounds and showed a typical flavonol pattern with a kaempferol aglycon. Compared with the known literature, the structure of compound 2 was determined as kaempferol 3-O-α-L-rhamnoside (afzelin) [30], [34]–[35]. Compound 4 gives the molecular formula C 21 H 20 O 11 , ESI-MS m/z: 447.20 [M-H] − .…”

Section: Resultsmentioning

confidence: 99%

“…In literatures, rutin, hyperoside and quercetin were reported to have antioxidant, chelation, anti-carcinogenic, cardio protective, bacterio static, and secretory properties [40], [45]. Afzelin (kaempferol 3-O-α-L-rhamnoside) is a competitive inhibitor of intestinal SGLT1 cotransporter, and it is very effective in reduction of glucose intestinal absorption [35]. Quercitrin (quercetin 3-O-α-L-rhamnoside) is a well-known flavonoid with anti-diarrhoeic activity, sedative activity, anti-inflammatory effect and antifungal activity [32], [46].…”

Section: Discussionmentioning

confidence: 99%

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Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

et al. 2014

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Nine flavonoids were isolated and characterized from the leaves of Zanthoxylum bungeanum. Their structures were elucidated by spectroscopic techniques as quercetin (1), afzelin (2), quercitrin (3), trifolin (4), quercetin-3-O-β-D-glucoside (5), isorhamnetin 3-O-α-L-rhamnoside (6), hyperoside (7), vitexin (8) and rutin (9). All compounds were isolated from the leaves of Z. bungeanum for the first time. Five compounds (2, 4, 5, 6 and 8) were found for the first time in the genus Zanthoxylum. To learn the mechanisms underlying its health benefits, in vitro (DPPH, ABTS, FRAP and lipid peroxidation inhibition assays) and in vivo (protective effect on Escherichia coli under peroxide stress) antioxidant activities of the nine flavonoids were measured. Quercetin and quercetin glycosides (compounds 1, 3, 5, 7, 9) showed the highest antioxidant activity. Structure-activity relationships indicated that the -OH in 4′ position on the B ring and the -OH in 7 position on the A ring possessed high antioxidant activity; B ring and/or A ring with adjacent -OH groups could greatly increase their antioxidant ability. Also, due to the different structures of various flavonoids, they will certainly exhibit different antioxidant capacity when the reactions occur in solution or in oil-in-water emulsion. These findings suggest that Z. bungeanum leaves may have health benefits when consumed. It could become a useful supplement for pharmaceutical products and functional food ingredients in both nutraceutical and food industries as a potential source of natural antioxidants.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

et al. 2014

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“…By comparison of the spectroscopic data and physicochemical properties with those reported in the literature, the known compounds were identified to be aceriphyllic acid B ( 5 ) , (+)‐eudesmin ( 6 ) , epieudesmin ( 7 ) , afzelin (=kaempferol‐3‐ O ‐ α ‐ l ‐rhamnoside, 8 ) , kaempferol‐3‐ O ‐ α ‐ l ‐rhamnoside‐7‐ O ‐ β ‐ d ‐glucoside ( 9 ) , quercetin‐3‐ O ‐ β ‐ d ‐glucopyranosyl(1 → 2)‐ β ‐ d ‐glucopyranoside ( 10 ) , quercetin‐3‐ O ‐ β ‐ d ‐glucopyranosyl (1 → 2)‐ β ‐ d ‐galactopyranoside ( 11 ) , (2 R ,3 R )‐epigallocatechin‐3‐ O ‐(4‐hydroxybenzoate) ( 12 ) , orcinol glucoside ( 13 ) , 2‐[4‐(3‐hydroxypropyl)‐2‐(methoxyphenoxy)]propane‐1,3‐diol ( 14 ) , (3 S ,5 R ,6 R ,7 E ,9 S )‐3,5,6,9‐tetrahydroxy‐7‐megastigmene ( 15 ) , ficusic acid ( 16 ) , and 1‐ O ‐(9 Z ,12 Z ,15 Z ‐octadecatrienoyl)glycerol ( 17 ) . The above known compounds were all obtained from this plant for the first time.…”

Section: Resultsmentioning

confidence: 96%

Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

Xiong

Liu

et al. 2016

Chemistry & Biodiversity

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Four new (1 - 4) and thirteen known (5 - 17) compounds were isolated from a rare cliff plant, Oresitrophe rupifraga. Based on spectroscopic evidence, the new structures were established to be [(2S,3R,4R)-4-(4-methoxybenzyl)-2-(4-methoxyphenyl)-tetrahydrofuran-3-yl]methanol (1), (3α)-23-(acetyloxy)-3-hydroxyolean-12-en-29-oic acid (2), 3α,23-(isopropylidenedioxy)olean-12-en-29-oic acid (3, artifact of isolation), and (3β,15β)-3-hydroxycholest-5-en-15-yl β-d-glucopyranoside (4), respectively. Among the isolates, compounds 1, 4, epieudesmin (7), and 1-O-(9Z,12Z,15Z-octadecatrienoyl)glycerol (17) were found to show significant antineuroinflammatory effects by inhibiting the NO production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells, with IC50 values of 7.21, 9.39, 4.96, and 8.51 μm, respectively.

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“…The different cell types used might be the explanation for the inconsistency in the effects of quercetin found in these 2 studies. Kaempferol‐3‐O‐rhamnoside inhibited intestinal glucose consumption (Rodriguez and others ), and the flavonols kaempferol 3‐O‐neohesperidoside and kaempferitrin were reported as functioning through mimicking the action of insulin, which promoted glucose uptake in cultured muscle cells (Jorge and others ; Yamasaki and others ). Kaempferol and quercetin significantly improved insulin‐stimulated glucose uptake in mature 3T3‐L1 adipocytes, by acting as a weak partial agonists of PPARγ (Fang and others ).…”

Section: Resultsmentioning

confidence: 99%

Bioassay‐Based Isolation and Identification of Phenolics from Sweet Cherry That Promote Active Glucose Consumption by HepG2 Cells

Cao

Liu

et al. 2015

Journal of Food Science

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A variety of phenolics had been found to be functional in promoting cellular glucose consumption that is important for blood glucose regulation. Sweet cherry (Prunus avium) is rich in such kinds of phenolics, including hydrocinnamic acids, anthocyanins, flavonols, and flavan-3-ols. Furthermore, a sweet cherry phenolics-rich extract (PRE) was found to be effective in promoting HepG2 glucose consumption. Seventeen components were preliminarily identified by HPLC-ESI-MS, including 9 hydrocinnamic acids, 4 anthocyanins, 3 flavonols, and 1 flavan-3-ol. To investigate the cellular glucose consumption-promotion activity of different phneolics subclasses, the phenolics were further fractionated into an anthocyanin-rich fraction (ARF), hydrocinnamic acid-rich fraction (HRF), and flavonol-rich fraction (FRF) through liquid-liquid extraction and mix-mode cation-exchange solid-phase extraction. The 3 fractions promoted HepG2 glucose consumption to different levels, with the promotion effects of HRF and FRF stronger than that of the ARF. The results provide guidance on the use of sweet cherry as a functional fruit.

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Inhibition of glucose intestinal absorption by kaempferol 3-O-α-rhamnoside purified from Bauhinia megalandra leaves

Cited by 25 publications

References 9 publications

Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

Purification and Characterization of Flavonoids from the Leaves of Zanthoxylum bungeanum and Correlation between Their Structure and Antioxidant Activity

Chemical Constituents of the Rare Cliff Plant Oresitrophe rupifraga and Their Antineuroinflammatory Activity

Bioassay‐Based Isolation and Identification of Phenolics from Sweet Cherry That Promote Active Glucose Consumption by HepG2 Cells

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