Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters

Salem, Jamila Hadj; Humeau, Catherine; Chevalot, Isabelle; Harscoat–Schiavo, Christelle; Vanderesse, Régis; Blanchard, Fabrice; Fick, Michel

doi:10.1016/j.procbio.2009.10.012

Cited by 86 publications

(61 citation statements)

References 65 publications

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“…The QE was synthesized by the method described by Salem et al (2010). Novozyme lipase 435 Ò (2.0 g) was added to a flame-dried round bottom flask having 3 Å molecular sieves, followed by the addition of isoquercitrin (0.5 g, 1.077 mol), dry acetone (5 mL) and EPA (1.73 mL, 5.38 mol) under inert conditions.…”

Section: Synthesis Of Epa Esters Of Quercetin-3-o-glucosidementioning

confidence: 99%

Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia

et al. 2015

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Quercetin, a major flavonol, present abundantly in apples and onions, is widely studied for ameliorating metabolic syndrome abnormalities. However, quercetin is mainly present in plant food in the form of quercetin glycosides and has been reported for poor gastrointestinal absorption. The present study was designed with the purpose of imparting a lipophilic property to quercetin-3-O-glucoside (QG) by its acylation with eicosapentaenoic acid (EPA) and to study the influence of eicosapentaenoic acid ester of quercetin-3-O-glucoside (QE) on hyperlipidemia and inflammation in vivo and in vitro. QE was more effective in reducing the production of tumor necrosis factor-alpha (TNF-α), prostaglandin 2 (PGE2), cyclo-oxygenase (COX)-2 levels and nuclear expression of nuclear factor-kappa B (NF-кB) compared to the parent compounds (QG and EPA) and commercial drugs, after lipopolysaccharides (LPS) induced inflammation in THP-1 derived macrophages. Serum high-density lipoprotein (HDL)-cholesterol was significantly higher and hepatic total cholesterol concentration was lower in the rats fed high-fat diet supplemented with QE, compared to the high-fat diet with inflammation (HFL). The serum concentrations of C-reactive protein (CRP), interleukin (IL)-6, and interferon-gamma (IFN-γ) were significantly lower in QE treatment group than HFL group. EPA conjugated flavonol, QE, had significant anti-inflammatory and hypolipidemic properties and may be effective for the treatment of obesity-related disorders.

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Section: Synthesis Of Epa Esters Of Quercetin-3-o-glucosidementioning

confidence: 99%

Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia

et al. 2015

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“…the conversion decreased significantly (50% reduction) when the substrate molar ratio was at three and remained relatively constant at a molar ratio of five. Contrary to this observation, Soultani et al (26) and Salem et al (25) reported significant increase in fatty acid conversion with increasing fatty acid molar ratio. This significant reduction in decanoic acid conversion as a result of increase in molar ratio is postulated to be due to the substrate inhibition.…”

Section: Effect Of Individual Variables On Process Responsesmentioning

confidence: 76%

Lipase-Catalyzed Synthesis of 6-O-D-Glucosyldecanoate inTert-Butanol: Reaction Optimization and Effect of Mixing Power Input

Han

Annuar

Ariffin

et al. 2011

Biotechnology & Biotechnological Equipment

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“…[4][5][6] However, their relatively weak solubility and stability in lipophilic and/or hydrophobic media have been a critical drawback, which restricts their further applications. 7,8 Acylation modication has become an optional way to solve these limitations, and many investigations have reported that the acylated products obviously showed improved stabilities, increased lipophilicity, increased solubilities, altered physical properties as well as enhanced intra-and intermolecular hydrophobic interactions, which were likely a result of the presence of the bulky acyl moiety. [9][10][11][12] These remarkable characteristics have gradually made the acylated glycosides a hot research topic and they are used as desirable candidates in pharmaceutical, food, and cosmetic preparations.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10]13 Recently, biochemical investigations of secondary metabolic pathways have led to the discovery of a large family of acyltransferases named BAHD that catalyse the acyl moiety (acetyl-, malonyl-, tigloyl-, benzoyl-, and hydroxycinnamoyl coenzyme A (CoA) thioesters) transfer reactions to form a diverse group of plant metabolites including small volatile esters, modied anthocyanins, as well as constitutive defense compounds and phytoalexins. 18,19 Structural research has revealed that two conserved motifs belonging to this family include an HXXXDG domain located near the center portion and a DFGWG motif located near the carboxyl terminus, which play important roles in the catalytic processes.…”

Section: Introductionmentioning

confidence: 99%

Identification and functional application of a new malonyltransferase NbMaT1 towards diverse aromatic glycosides from Nicotiana benthamiana

Liu

Wang

et al. 2017

RSC Adv.

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Recently, owing to the important pharmaceutical properties of malonylated glycosides, their chemoenzymatic synthesis using malonyltransferase has received significant attention. In the present study, a new malonyltransferase, NbMaT1, was identified from Nicotiana benthamiana. Extensive enzymatic assays revealed its significant substrate tolerance based on HPLC-UV and HR-MS analyses.Moreover, 16 of the tested glycosides including flavone glycosides, flavonol glycosides, dihydroflavone glycosides, isoflavone glycosides, coumarin glycosides, and phenylethyl chromone glycosides with various sugar moieties (such as glucose, xylose, and galactose) substituted at different positions of their skeleton could be accepted by NbMaT1 to conduct the corresponding malonylation. Among these, enzymatic malonylation of phenylethyl chromone glycosides as well as xylosides and galactosides has rarely been reported earlier. Furthermore, one-pot synthesis using the known malonyl-CoA synthetase MatB and NbMaT1 as well as an unnatural fusion protein MatB-NbMaT1 was designed, which allowed malonic acid to be directly used in the malonylation reaction without the addition of expensive malonyl-CoA. Moreover, a remarkably improved conversion rate was observed for all the tested substrates, with both commercial and industrial application values. The malonylated product of the bioactive flavonoid diglycoside icariin was prepared and NMR spectroscopy revealed that the malonyl group was specifically transferred onto the 6-OH group of the glucose moiety.NbMaT1 was expected to be a universal and effective tool for chemoenzymatic synthesis of diverse bioactive-malonylated glycoside derivatives for drug discovery.

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Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters

Cited by 86 publications

References 65 publications

Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia

Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia

Lipase-Catalyzed Synthesis of 6-O-D-Glucosyldecanoate inTert-Butanol: Reaction Optimization and Effect of Mixing Power Input

Identification and functional application of a new malonyltransferase NbMaT1 towards diverse aromatic glycosides from Nicotiana benthamiana

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