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Alluis, Bertrand; Perol, N.; Hajji, Hakima El; Dangles, Olivier

doi:10.1002/(sici)1522-2675(20000216)83:2<428::aid-hlca428>3.3.co;2-a

Cited by 6 publications

(21 citation statements)

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“…The chemical synthesis of water-soluble derivatives of rutin, as reported by Alluis et al, 16 is based on the introduction of sulfate and carboxylate groups on the sugar moiety of rutin, with the aim being to increase rutin's water solubility. There were condition variations in the Alluis study, including: solvent (pyridine and DMF) and temperature (range 0-70 °C) variations, catalyst (4-dimethylaminopyridine-DMAP) and succinic-anhydride or SO 3 variations, and pyridine-concentration variations (an excess of 3 at 6 moles with respect to rutin).…”

Section: Results and Discussion Determination Of Synthesis And Solubimentioning

confidence: 99%

“…In addition, this compound was separated and isolated, and we followed the standardized procedures of preparative paper chromatography, as mentioned by Siegelman and as opposed to the chromatography on C 18 silica gel implemented by Alluis et al. 16 In this current experiment, the NMR technique ( 13 C-NMR and 1 H-NMR spectra) was used to identify the structure of compound 2 and to confirm the efficacy of separation using the paper-chromatography method. Analysis was conducted by means of analytical data (according to the experimental description of derivative 2).…”

Section: Results and Discussion Determination Of Synthesis And Solubimentioning

confidence: 99%

“…13,14 The use of rutin is relatively limited due to its low water solubility (0.125 g/L), 15 which is what led to our research group's desire to increase the solubility of a rutin derivative (as synthesized by introducing carboxylate groups on rutin's sugar moiety, by means of a modification of the method developed by Alluis et al). 16 Moreover, we took into consideration the influence of the chemical modification via evaluation in vitro of two model procedures: antiradical capacity by luminol/AAPH system and antioxidant activity by lipid peroxidation in brain homogenate.…”

Section: Introductionmentioning

confidence: 99%

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The synthesis of a water-soluble derivative of rutin as an antiradical agent

Pedriali¹,

Fernandes²,

Bernusso³

et al. 2008

Quím. Nova

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Recebido em 13/6/07; aceito em 20/6/08; publicado na web em 31/10/08The purpose of this study was to synthesize a water-soluble derivative of rutin (compound 2) by introducing carboxylate groups on rutin's sugar moiety. The rutin derivative showed an almost 100-fold solubility increase in water. The antiradical capacity of compound 2 was evaluated using the luminol/AAPH system, and the derivative's activity was 1.5 times greater than that of Trolox ® . Despite the derivative's high solubility in water (log P = -1.13), lipid peroxidation of brain homogenate membranes was very efficiently inhibited (inhibition values were only 19% lower than the inhibition values of rutin).

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Section: Results and Discussion Determination Of Synthesis And Solubimentioning

confidence: 99%

Section: Results and Discussion Determination Of Synthesis And Solubimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The synthesis of a water-soluble derivative of rutin as an antiradical agent

Pedriali¹,

Fernandes²,

Bernusso³

et al. 2008

Quím. Nova

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“…The partial or total succinylation of flavonoid sugar moieties has been shown to be a very efficient way to increase the water solubility of flavonoids for application as colour enhancers [12]. The reaction is regioselective for the sugar OH groups and does not even require the preliminary protection of the aglycone OH groups.…”

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confidence: 99%

“…afforded the 6-O-acyl derivative as the only product (Scheme 1). The low yield (16%) suggests that the steric hindrance exerted by the aglycone on the sugar moiety is (12). The signals of some aglycone protons in 12 are significantly shielded with respect to the corresponding signals in non-acylated 9 (À 0.11 and À 0.32 ppm for HÀC(6) and HÀC(8), resp.).…”

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confidence: 99%

Quercetin (=2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1- benzopyran-4-one) Glycosides and Sulfates: Chemical Synthesis, Complexation, and Antioxidant Properties

Alluis

Dangles

2001

HCA

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Glycosides, acylated glycosides, and sulfates of quercetin ( 3,3',4',5,7-pentahydroxyflavone; 1), which is, together with its derivatives, among the most common polyphenols found in plants and in the human diet, were prepared and quantitatively investigated for their ability to bind metal ions (Al III , Fe II , Fe III ), enhance and vary natural colours (anthocyanin copigmentation), and trap potentially damaging radicals (antioxidant activity).Introduction. ± Flavonoids and other polyphenols are ubiquitous secondary metabolites in plants [1] which, as food components, enjoy increasing interest from researchers, food manufacturers, and consumers. Indeed, polyphenol-rich diets (e.g., the regular consumption of fruits, vegetables, red wine, and tea) have been repeatedly correlated with a low risk of developing cardiovascular diseases and cancers [2], the two major causes of mortality in occidental countries. Because of their antioxidant properties and their ability to bind to a wide range of proteins including enzymes [1] [3], polyphenols may be partially responsible for these protective effects.Besides phenolic acids (benzoic and cinnamic acid derivatives), flavonols (3-hydroxyflavones) are one of the main classes of dietary polyphenols [1]. Their antioxidant properties essentially stem from their ability to trap reactive O-species (ROS) and bind transition-metal ions, which, if not suitably complexed, could enter redox cycles that produce ROS [3]. This work focuses on quercetin (3,3',4',5,7-pentahydroxyflavone; 1), the most representative dietary flavonol (abundant in onions, apples, and tea) and a potent antioxidant. In most naturally occurring flavonols, at least one of the OH groups of the polyphenolic nucleus (aglycone) is glycosylated by monoand oligosaccharides involving neutral sugars such as d-glucose, d-galactose, lrhamnose, and d-xylose. Quercetin b-d-glucopyranosides are particularly interesting because their biodisposability, irrespective of the location of the sugar moiety on the polyphenolic nucleus, is better than that of quercetin and other quercetin glycosides, possibly as a consequence of a facilitated intestinal absorption via glucose transporters [4]. Moreover, quercetin sulfates deserve particular attention, not only because of their natural occurrence [1] [5], but also because the quercetin conjugates found in the plasma of human volunteers after consumption of a meal rich in plant products are actually glucuronides and sulfates [6].

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Physicochemical Studies of New Anthocyano‐Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C‐Glycosidic Ellagitannins on Wine Color

et al. 2009

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Keywords: Natural products / Dyes/Pigments / Anthocyanins / Polyphenols / Ellagitannins Kinetic and thermodynamic UV/Vis and structural NMR spectroscopic investigations on the anthocyano-ellagitannin hybrid 1-deoxyvescalagin-(1βǞ8)-oenin revealed that its enhanced color stability relative to that of the red-colored pigment oenin and resulting bathochromism can be rationalized in terms of an intramolecular π-stacking between the grape-

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Cited by 6 publications

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The synthesis of a water-soluble derivative of rutin as an antiradical agent

The synthesis of a water-soluble derivative of rutin as an antiradical agent

Quercetin (=2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1- benzopyran-4-one) Glycosides and Sulfates: Chemical Synthesis, Complexation, and Antioxidant Properties

Physicochemical Studies of New Anthocyano‐Ellagitannin Hybrid Pigments: About the Origin of the Influence of Oak C‐Glycosidic Ellagitannins on Wine Color

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