Quercetin 3-Glucoside Protects Neuroblastoma (SH-SY5Y) Cells in Vitro against Oxidative Damage by Inducing Sterol Regulatory Element-binding Protein-2-mediated Cholesterol Biosynthesis

Soundararajan, Ramani; Wishart, Alexander D.; Rupasinghe, H.P. Vasantha; Arcellana‐Panlilio, Mayi; Nelson, Carolanne M.; Mayne, Michael; Robertson, George S.

doi:10.1074/jbc.m703583200

Cited by 60 publications

(55 citation statements)

References 69 publications

(46 reference statements)

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“…To confirm efficiency of transfection, SH-SY5Y were transiently transfected using 4 mg pEGFP (Clontech, Mountain View, CA, USA), and the percentage of cells expressing green fluorescent protein was determined counting at least 100 cells by direct fluorescence microscopy. The transfection efficiency measured in these control experiments using Lipofectamine 2000 was 37%, consistent with the effective use of this reagent to study membrane-associated transporters and neurodegenerative disease in SH-SY5Y cells by other investigators (32)(33)(34)(35)(36)(37)(38). To further confirm functional expression of wild-type Fpn and the H32R mutant, transfection experiments in HEK293T cells were also carried out.…”

Section: Cell Culture and Expression Of Fpn And Flatiron Mutantmentioning

confidence: 89%

Ferroportin deficiency impairs manganese metabolism in flatiron mice

Seo

Wessling‐Resnick

2015

FASEB j.

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We examined the physiologic role of ferroportin (Fpn) in manganese (Mn) export using flatiron (ffe/+) mice, a genetic model of Fpn deficiency. Blood (0.0123 vs. 0.0107 mg/kg; P = 0.0003), hepatic (1.06 vs. 0.96 mg/kg; P = 0.0125), and bile Mn levels (79 vs. 38 mg/kg; P = 0.0204) were reduced in ffe/+ mice compared to +/+ controls. Erythrocyte Mn-superoxide dismutase was also reduced at 6 (0.154 vs. 0.096, P = 0.0101), 9 (0.131 vs. 0.089, P = 0.0162), and 16 weeks of age (0.170 vs. 0.090 units/mg protein/min; P < 0.0001). 54 Mn uptake after intragastric gavage was markedly reduced in ffe/+ mice (0.0187 vs. 0.0066% dose; P = 0.0243), while clearance of injected isotope was similar in ffe/+ and +/+ mice. These values were compared to intestinal absorption of 59 Fe, which was significantly reduced in ffe/+ mice (8.751 vs. 3.978% dose; P = 0.0458). The influence of the ffe mutation was examined in dopaminergic SH-SY5Y cells and human embryonic HEK293T cells. While expression of wild-type Fpn reversed Mn-induced cytotoxicity, ffe mutant H32R failed to confer protection. These combined results demonstrate that Fpn plays a central role in Mn transport and that flatiron mice provide an excellent genetic model to explore the role of this exporter in Mn homeostasis.-Seo, Y. A., Wessling-Resnick, M. Ferroportin deficiency impairs manganese metabolism in flatiron mice. FASEB J. 29, 2726-2733 (2015). www.fasebj.org

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Section: Cell Culture and Expression Of Fpn And Flatiron Mutantmentioning

confidence: 89%

Ferroportin deficiency impairs manganese metabolism in flatiron mice

Seo

Wessling‐Resnick

2015

FASEB j.

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“…This action is mediated by numerous mechanisms including the follow ing: Protecting the cell membrane by inhibiting LDH efflux [34] ; maintaining erythrocyte deformability, which plays an essential role in circulatory system by preventing vascular diseases [35] ; accumulating in the arterial wall and preventing hyperlipidemia [36] ; inhibiting fatty acid formation resulting from lipid peroxidation [37] ; protecting neural cells against oxidative stress induced by H2O2 by Orfali GC et al . Isoquercitrin in cancer decreasing lipid peroxidation and increasing cellular chole sterol concentrations [38] ; reducing glutathione depletion and decreasing catalase and glutathione peroxidase 1 activities [39] ; ROS and nitritescavenging activities [40] ; and by regulating the oxidative complex NADPH and NO production [41] , lipidlowering activities in hepatocytes [42] , induction of apolipoprotein AI gene expression [43] , and free radical scavenging [4464] .…”

Section: Effects Of Iq In Cancermentioning

confidence: 99%

Review of anticancer mechanisms of isoquercitin

Orfali¹,

Duarte²,

Bonadio³

et al. 2016

WJCO

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This review was based on a literature search of PubMed and Scielo databases using the keywords "quercetin, rutin, isoquercitrin, isoquercitin (IQ), quercetin-3-glucoside, bioavailability, flavonols and favonoids, and cancer" and combinations of all the words. We collected relevant scientific publications from 1990 to 2015 about the absorption, bioavailability, chemoprevention activity, and treatment effects as well as the underlying anticancer mechanisms of isoquercitin. Flavonoids are a group of polyphenolic compounds widely distributed throughout the plant kingdom. The subclass of flavonols receives special attention owing to their health benefits. The main components of this class are quercetin, rutin, and IQ, which is a flavonoid and although mostly found as a glycoside, is an aglycone (lacks a glycoside side chain). This compound presents similar therapeutic profiles to quercetin but with superior bioavailability, resulting in increased efficacy compared to the aglycone form. IQ has therapeutic applications owing to its wide range of pharmacological effects including antioxidant, antiproliferative, anti-inflammatory, anti-hypertensive, and anti-diabetic. The protective effects of IQ in cancer may be due to actions on lipid peroxidation. In addition, the antitumor effect of IQ and its underlying mechanism are related to interactions with Wnt signaling pathway, mixed-lineage protein kinase 3, mitogen-activated protein kinase, apoptotic pathways, as well proinflammatory protein signaling. This review contributed to clarifying the mechanisms of absorption, metabolism, and actions of IQ and isoquercitrin in cancer.

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Section: Introductionmentioning

confidence: 99%

“…22: 2856-2871, August 2010, www.plantcell.org 2010 American Society of Plant Biologists et al, 2003. Importantly, the bioactivities of these compounds are greatly modulated by their glycon structures (Jü rgenliemk et al, 2003;Soundararajan et al, 2008).Glycosylation of flavonoids in plant cells usually takes place in a regio-(or position-)specific manner after the completion of aglycon biosynthesis (Heller and Forkmann, 1994), providing a basis for the structural diversification of these important metabolites. Glycosylation is catalyzed by glycosyltransferases (UGTs), which generally catalyze transfer of the glycosyl group from nucleoside diphosphate-activated sugars (e.g., UDP-sugars) to (A) Grapes (cv Cabernet Sauvignon) at a vineyard in the TOMI NO OKA Winery, Yamanashi Prefecture, Japan.…”

mentioning

confidence: 99%

“…Moreover, they also have important biomedical activities. The activities that are unique to flavonol glycosides and are not associated with the aglycon forms include the following: the cytoprotective effects of quercetin 3-O-glucoside (isoquercitrin) by induction of cholesterol biosynthesis (Soundararajan et al, 2008), antiatherosclerotic activity of quercetin glucuronides that are specifically incorporated by macrophages (Kawai et al, 2008), and antidepressant effects of quercetin 3-O-glucuronide (miquelianin), quercetin 3-O-glucoside, and quercetin 3-Ogalactoside (hyperoside) (Butterweck et al, 2000; 1 Address correspondence to nakayama@seika.che.tohoku.ac.jp. The author responsible for distribution of materials integral to the findings presented in this article in accordance with the policy described in the Instructions to Authors (www.plantcell.org) is: Toru Nakayama (nakayama@seika.che.tohoku.ac.jp).…”

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confidence: 99%

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Functional Differentiation of the Glycosyltransferases That Contribute to the Chemical Diversity of Bioactive Flavonol Glycosides in Grapevines (Vitis vinifera)

et al. 2010

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We identified two glycosyltransferases that contribute to the structural diversification of flavonol glycosides in grapevine (Vitis vinifera): glycosyltransferase 5 (Vv GT5) and Vv GT6. Biochemical analyses showed that Vv GT5 is a UDP-glucuronic acid:flavonol-3-O-glucuronosyltransferase (GAT), and Vv GT6 is a bifunctional UDP-glucose/UDP-galactose:flavonol-3-Oglucosyltransferase/galactosyltransferase. The Vv GT5 and Vv GT6 genes have very high sequence similarity (91%) and are located in tandem on chromosome 11, suggesting that one of these genes arose from the other by gene duplication. Both of these enzymes were expressed in accordance with flavonol synthase gene expression and flavonoid distribution patterns in this plant, corroborating their significance in flavonol glycoside biosynthesis. The determinant of the specificity of Vv GT5 for UDP-glucuronic acid was found to be Arg-140, which corresponded to none of the determinants previously identified for other plant GATs in primary structures, providing another example of convergent evolution of plant GAT. We also analyzed the determinants of the sugar donor specificity of Vv GT6. Gln-373 and Pro-19 were found to play important roles in the bifunctional specificity of the enzyme. The results presented here suggest that the sugar donor specificities of these Vv GTs could be determined by a limited number of amino acid substitutions in the primary structures of protein duplicates, illustrating the plasticity of plant glycosyltransferases in acquiring new sugar donor specificities. INTRODUCTIONGrapevine (Vitis vinifera) ( Figure 1A) has been one of the most important fruit crops from the beginning of human civilization (McGovern et al., 1997). Dietary intake of grapevine-based products results in diverse biological effects that are beneficial to human health, in part due to polyphenols, such as flavonoids (e.g., flavonols, proanthocyanidins, and anthocyanins) (Renaud and de Lorgeril, 1992;Corder et al., 2001Corder et al., , 2006Baur et al., 2006). Flavonols, such as kaempferol, quercetin, and isorhamnetin, are an important class of bioactive flavonoids, which are most abundant as their 3-O-glycosides (i.e., glucoside, glucuronoside, galactoside, and rutinoside) in the berries, seeds, and leaves of grapevine (Hmamouchi et al., 1996;Castillo-Munoz et al., 2009).In this plant, biosynthesis of flavonol glycosides primarily serves to protect the plant from excess UV light (Price et al., 1995;Matus et al., 2009). Flavonol aglycons are biosynthesized from dihydroflavonols by the action of flavonol synthase (Vv FLS), a 2-oxoglutarate-dependent dioxygenase, which is temporally regulated by an R2R3-Myb transcription factor, Vv MYBF1 (Fujita et al., 2006;Czemmel et al., 2009). Subsequently, glycosylation of flavonols enhances their water solubility, such that high concentrations of flavonols can accumulate in plant cells.From a food chemistry perspective, flavonol glycosides define the color of wine grapes and products by acting as copigments (Yoshitama et al., 1992;Boulto...

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Quercetin 3-Glucoside Protects Neuroblastoma (SH-SY5Y) Cells in Vitro against Oxidative Damage by Inducing Sterol Regulatory Element-binding Protein-2-mediated Cholesterol Biosynthesis

Cited by 60 publications

References 69 publications

Ferroportin deficiency impairs manganese metabolism in flatiron mice

Ferroportin deficiency impairs manganese metabolism in flatiron mice

Review of anticancer mechanisms of isoquercitin

Functional Differentiation of the Glycosyltransferases That Contribute to the Chemical Diversity of Bioactive Flavonol Glycosides in Grapevines (Vitis vinifera)

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