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Q4951 Sigma

Quercetin

≥95% (HPLC), solid

Synonym: 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one, 3,3′,4′,5,6-Pentahydroxyflavone, Quercetin-3-O-rhamnoside

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Description

Biochem/physiol Actions

Quercetin is a flavonoid with anticancer activity. Quercetin is a mitochondrial ATPase and phosphodiesterase inhibitor. It Inhibits PI3-kinase activity and slightly inhibits PIP kinase activity. Quercetin has antiproliferative effects on cancer cell lines, reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle. Quercetin may also inhibit fatty acid synthase activity.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
25
Safety Statements (Europe) 
45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
LK8750000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Phosphorylation is a ubiquitous cellular regulatory mechanism that mediates signal transduction pathways, which carry signals from the cell surface to the nucleus or cytoplasm, by altering the activi...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Diseases, Inflammation, Metabolism, Neurodegenerative Diseases, Phosphorylations, Transduction

Fatty Acid Synthesis and Metabolism in Cancer Cells

Proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sour...
Keywords: Apoptosis, Biofiles, Cancer, Carboxylations, Catalysis, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Oxidations, PAGE, Phosphorylations

The Role of Inflammation in Neurodegeneration

It is well established that the brain can sense and react to peripheral insults through the rapid induction of fever and other neuroendocrine changes in response to events such as infection and tissu...
Scott Hauser, Technology Transfer Specialist, Sigma® Life Science
Biofiles, Vol. 8, No. 19
Keywords: Adhesion, Biofiles, Central Nervous System, Diseases, Events, Gene expression, Inflammation, Neurodegenerative Diseases, Reductions, Type

Peer-Reviewed Papers

References

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Quercetin and endurance exercise capacity: a systematic review and meta-analysis. Kressler J, Millard-Stafford M, and Warren GL Med. Sci Sports Exerc. 43(12), 2396-404, (2011)

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Quercetin acutely relaxes airway smooth muscle and potentiates β-agonist-induced relaxation via dual phosphodiesterase inhibition of PLCβ and PDE4. Townsend EA and Emala CW Am. J. Physiol. Lung Cell. Mol. Physiol. 305(5), L396-403, (2013)

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Therapeutic potential of quercetin to decrease blood pressure: review of efficacy and mechanisms. Larson AJ, Symons JD, and Jalili T Adv. Nutr. 3(1), 39-46, (2012)

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Quercetin as a systemic chemopreventative agent: structural and functional mechanisms. Mendoza EE and Burd R Mini Rev. Med. Chem. 11(14), 1216-21, (2011)

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Quercetin transiently increases energy expenditure but persistently decreases circulating markers of inflammation in C57BL/6J mice fed a high-fat diet. Stewart LK Metabolism 57(7 Suppl 1), S39-46, (2008)

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Chemical constituents of Tilia taquetii leaves and their inhibition of MMP-1 expression and elastase activities. Kim SY, Kim JE, Bu HJ, et al. Nat. Prod. Commun. 9(12), 1683-5, (2014)

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A dietary pattern rich in lignans, quercetin and resveratrol decreases the risk of oesophageal cancer. Lin Y, Yngve A, Lagergren J, et al. Br. J. Nutr. 112(12), 2002-9, (2014)

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Induction of Nur77 by hyperoside inhibits vascular smooth muscle cell proliferation and neointimal formation. Huo Y, Yi B, Chen M, et al. Biochem. Pharmacol. 92(4), 590-8, (2014)

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Membrane dipole modifiers modulate single-length nystatin channels via reducing elastic stress in the vicinity of the lipid mouth of a pore. Chulkov EG, Schagina LV, and Ostroumova OS Biochim. Biophys. Acta 1848(1 Pt A), 192-9, (2015)

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Buckwheat achenes antioxidant profile modulates Aspergillus flavus growth and aflatoxin production. Chitarrini G, Nobili C, Pinzari F, et al. Int. J. Food Microbiol. 189, 1-10, (2014)

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Protective effect of quercetin on lipopolysaccharide-induced acute lung injury in mice by inhibiting inflammatory cell influx. Wang L, Chen J, Wang B, et al. Exp. Biol. Med. (Maywood.) 239(12), 1653-62, (2014)

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Orally active osteoanabolic agent GTDF binds to adiponectin receptors, with a preference for AdipoR1, induces adiponectin-associated signaling, and improves metabolic health in a rodent model of diabetes. Singh AK, Joharapurkar AA, Khan MP, et al. Diabetes 63(10), 3530-44, (2014)

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Glucuronidation does not suppress the estrogenic activity of quercetin in yeast and human breast cancer cell model systems. Ruotolo R, Calani L, Brighenti F, et al. Arch. Biochem. Biophys. 559, 62-7, (2014)

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Antagonistic role of natural compounds in mTOR-mediated metabolic reprogramming. Cerella C, Gaigneaux A, Dicato M, et al. Cancer Lett. 356(2 Pt A), 251-62, (2015)

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[Chemical constituents from Commelina communis]. Yuan HE, Zhou XD, Meng LJ, et al. Zhongguo Zhong Yao Za Zhi 38(19), 3304-8, (2013)

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[Determination of taxifolin in Polygonum orientale of different storage period]. Tan YN, Tong MM, Zhang YY, et al. Zhongguo Zhong Yao Za Zhi 38(17), 2779-81, (2013)

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A moderate protective effect of quercetin against γ-irradiation- and storage-induced oxidative damage in red blood cells for transfusion. Zbikowska HM, Antosik A, Szejk M, et al. Int. J. Radiat. Biol. 90(12), 1201-10, (2014)

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Quercetin: a pleiotropic kinase inhibitor against cancer. Russo GL, Russo M, Spagnuolo C, et al. Cancer Treat. Res. 159, 185-205, (2014)

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[Quercetin regulates cell cycle-related gene expression in a model of glucose-oxygen deprivation in astrocytes]. Yao F, Zhang L, Yuan Z, et al. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi 29(9), 910-3, (2013)

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Induction of G2/M phase arrest and apoptosis by the flavonoid tamarixetin on human leukemia cells. Nicolini F, Burmistrova O, Marrero MT, et al. Mol. Carcinog. 53(12), 939-50, (2014)

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Inhibition of mTOR signaling by quercetin in cancer treatment and prevention. Bruning A Anticancer Agents Med. Chem. 13(7), 1025-31, (2013)

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[Progress of mechanism studies on quercetin for preventing and treating neurodegenerative diseases]. Shi Y and Liang XC Zhongguo Zhong Xi Yi Jie He Za Zhi 32(10), 1432-5, (2012)

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[Antihypertensive and neuroprotective activity of quercetin and its derivatives]. Rogovskiĭ VS, Shimanovskiĭ NL, and Matiushin AI Eksp. Klin. Farmakol. 75(9), 37-41, (2012)

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Quercetin. Monograph. Kelly GS Altern. Med. Rev. 16(2), 172-94, (2011)

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Pharmacology in health food: metabolism of quercetin in vivo and its protective effect against arteriosclerosis. Ishizawa K, Yoshizumi M, Kawai Y, et al. J. Pharmacol. Sci. 115(4), 466-70, (2011)

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The role of quercetin, flavonols and flavones in modulating inflammatory cell function. Chirumbolo S Inflamm. Allergy Drug Targets 9(4), 263-85, (2010)

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Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. Kang J, Kim E, Kim W, et al. J. Biol. Chem. 288(38), 27343-57, (2013)

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The flavonoid quercetin in disease prevention and therapy: facts and fancies. Russo M, Spagnuolo C, Tedesco I, et al. Biochem. Pharmacol. 83(1), 6-15, (2012)

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Life or death: neuroprotective and anticancer effects of quercetin. Dajas F J. Ethnopharmacol. 143(2), 383-96, (2012)

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Exploiting tyrosinase expression and activity in melanocytic tumors: quercetin and the central role of p53. Vargas AJ, Sittadjody S, Thangasamy T, et al. Integr. Cancer Ther. 10(4), 328-40, (2011)

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Bioavailability of quercetin: problems and promises. Cai X, Fang Z, Dou J, et al. Curr. Med. Chem. 20(20), 2572-82, (2013)

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Quercetin in hypoxia-induced oxidative stress: novel target for neuroprotection. Pandey AK, Patnaik R, Muresanu DF, et al. Int. Rev. Neurobiol. 102, 107-46, (2012)

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Eye lens in aging and diabetes: effect of quercetin. Stefek M and Karasu C Rejuvenation Res. 14(5), 525-34, (2011)

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Quercetin glucosides promote ischemia-induced angiogenesis, but do not promote tumor growth. Sumi M, Tateishi N, Shibata H, et al. Life Sci. 93(22), 814-9, (2013)

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Conjugated quercetin glucuronides as bioactive metabolites and precursors of aglycone in vivo. Terao J, Murota K, and Kawai Y Food Funct. 2(1), 11-7, (2011)

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Structure and function of the peanut panallergen Ara h 8. Hurlburt BK, Offermann LR, McBride JK, et al. J. Biol. Chem. 288(52), 36890-901, (2013)

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Molecular aspects on the interaction of quercetin and its metal complexes with DNA. Dolatabadi JE Int. J. Biol. Macromol. 48(2), 227-33, (2011)

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Genetic dissection of gamma-secretase-dependent and -independent functions of presenilin in regulating neuronal cell cycle and cell death. Kallhoff-Munoz V J. Neurosci. 28(44), 11421-31, (2008)

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Quercetin suppresses cyclooxygenase-2 expression and angiogenesis through inactivation of P300 signaling. Xiao X, Shi D, Liu L, et al. PLoS ONE 6(8), e22934, (2011)

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Quercetin ameliorates tunicamycin-induced endoplasmic reticulum stress in endothelial cells. Suganya N, Bhakkiyalakshmi E, Suriyanarayanan S, et al. Cell Prolif. 47(3), 231-40, (2014)

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Isoquercitrin and polyphosphate co-enhance mineralization of human osteoblast-like SaOS-2 cells via separate activation of two RUNX2 cofactors AFT6 and Ets1. Wang X, Schröder HC, Feng Q, et al. Biochem. Pharmacol. 89(3), 413-21, (2014)

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Quercetin suppresses invasion and migration of H-Ras-transformed MCF10A human epithelial cells by inhibiting phosphatidylinositol 3-kinase. Song NR, Chung MY, Kang NJ, et al. Food Chem. 142, 66-71, (2014)

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Identification of regioisomers of methylated kaempferol and quercetin by ultra high performance liquid chromatography quadrupole time-of-flight (UHPLC-QTOF) tandem mass spectrometry combined with diagnostic fragmentation pattern analysis. Ma C, Lv H, Zhang X, et al. Anal. Chim. Acta 795, 15-24, (2013)

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Dietary polyphenols in cancer prevention: the example of the flavonoid quercetin in leukemia. Spagnuolo C, Russo M, Bilotto S, et al. Ann. N. Y. Acad. Sci. 1259, 95-103, (2012)

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Quercitrin and taxifolin stimulate osteoblast differentiation in MC3T3-E1 cells and inhibit osteoclastogenesis in RAW 264.7 cells. Satué M, Arriero Mdel M, Monjo M, et al. Biochem. Pharmacol. 86(10), 1476-86, (2013)

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Combining molecular docking and 3-D pharmacophore generation to enclose the in vivo antigenotoxic activity of naturally occurring aromatic compounds: myricetin, quercetin, rutin, and rosmarinic acid. Mladenović M, Matić S, Stanić S, et al. Biochem. Pharmacol. 86(9), 1376-96, (2013)

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A physiologically based kinetic (PBK) model describing plasma concentrations of quercetin and its metabolites in rats. Boonpawa R, Spenkelink A, Rietjens IM, et al. Biochem. Pharmacol. 89(2), 287-99, (2014)

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Prenylation enhances quercetin uptake and reduces efflux in Caco-2 cells and enhances tissue accumulation in mice fed long-term. Mukai R, Fujikura Y, Murota K, et al. J. Nutr. 143(10), 1558-64, (2013)

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Rapid method for the simultaneous determination of flavonol aglycones in food using u-HPLC coupled with heating block acidic hydrolysis. Shim YS, Kim S, Seo D, et al. J. AOAC Int. 96(5), 1059-64, (2013)

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Silencing of Hsp27 and Hsp72 in glioma cells as a tool for programmed cell death induction upon temozolomide and quercetin treatment. Jakubowicz-Gil J, Langner E, Bądziul D, et al. Toxicol. Appl. Pharmacol. 273(3), 580-9, (2013)

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Carbon monoxide alleviates ethanol-induced oxidative damage and inflammatory stress through activating p38 MAPK pathway. Li Y, Gao C, Shi Y, et al. Toxicol. Appl. Pharmacol. 273(1), 53-8, (2013)

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Thermally accelerated oxidative degradation of quercetin using continuous flow kinetic electrospray-ion trap-time of flight mass spectrometry. Barnes JS, Foss FW, and Schug KA J. Am. Soc. Mass Spectrom. 24(10), 1513-22, (2013)

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X-ray crystal structure of a xanthine oxidase complex with the flavonoid inhibitor quercetin. Cao H, Pauff JM, and Hille R J. Nat. Prod. 77(7), 1693-9, (2014)

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Induction of hepatic apolipoprotein A-I gene expression by the isoflavones quercetin and isoquercetrin. Haas MJ, Onstead-Haas LM, Szafran-Swietlik A, et al. Life Sci. 110(1), 8-14, (2014)

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RyR3 in situ regulation by Ca(2+) and quercetin and the RyR3-mediated Ca(2+) release flux in intact Jurkat cells. Baran I and Ganea C Arch. Biochem. Biophys. 540(1-2), 145-59, (2013)

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A new perspective on the quercetin paradox in male reproductive dysfunction. Ranawat P, Pathak CM, and Khanduja KL Phytother Res. 27(6), 802-10, (2013)

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Specific localization of quercetin-3-O-glucuronide in human brain. Ishisaka A, Mukai R, Terao J, et al. Arch. Biochem. Biophys. 557, 11-7, (2014)

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Deubiquitination and stabilization of T-bet by USP10. Pan L, Chen Z, Wang L, et al. Biochem. Biophys. Res. Commun. 449(3), 289-94, (2014)

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Retinal neuroprotective effects of quercetin in streptozotocin-induced diabetic rats. Kumar B, Gupta SK, Nag TC, et al. Exp. Eye Res. 125, 193-202, (2014)

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Effects of quercetin on hemoglobin-dependent redox reactions: relationship to iron-overload rat liver injury. Lu NH, Chen C, He YJ, et al. J. Asian Nat. Prod. Res. 15(12), 1265-76, (2013)

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Two new constituents from Erigeron breviscapus. Li J and Yu DQ J. Asian Nat. Prod. Res. 15(9), 969-73, (2013)

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Neural cell activation by phenolic compounds from the Siberian larch (Larix sibirica). Loers G, Yashunsky DV, Nifantiev NE, et al. J. Nat. Prod. 77(7), 1554-61, (2014)

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Protective effect of quercetin on hyperglycemia, oxidative stress and DNA damage in alloxan induced type 2 diabetic mice. Alam MM, Meerza D, and Naseem I Life Sci. 109(1), 8-14, (2014)

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Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β₂-adrenergic signaling. Yamazaki S, Miyoshi N, Kawabata K, et al. Arch. Biochem. Biophys. 557, 18-27, (2014)

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The effects of quercetin dietary supplementation on broiler growth performance, meat quality, and oxidative stability. Goliomytis M, Tsoureki D, Simitzis PE, et al. Poult. Sci. 93(8), 1957-62, (2014)

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Novel insights into the antiproliferative effects and synergism of quercetin and menadione in human leukemia Jurkat T cells. Baran I, Ionescu D, Filippi A, et al. Leuk. Res. 38(7), 836-49, (2014)

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Determination of kaempferol and quercetin in Xindakang tablet by β-cyclodextrin modified micellar electrokinetic capillary chromatography. Lu Y, Wang D, Ning Z, et al. Pak. J. Pharm. Sci. 27(3), 487-90, (2014)

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Heart protective effects and mechanism of quercetin preconditioning on anti-myocardial ischemia reperfusion (IR) injuries in rats. Liu H, Guo X, Chu Y, et al. Gene 545(1), 149-55, (2014)

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Comparison of counter-current chromatography and preparative high performance liquid chromatography applied to separating minor impurities in drug preparations. Li S, Wang W, Tang H, et al. J. Chromatogr. A 1344, 51-8, (2014)

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A lucid build-up of nanostructured curcumin, quercetin and their interaction with DNA. Rajasekaran M and Annaraj J J. Nanosci. Nanotechnol. 14(7), 4874-9, (2014)

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Neuroprotective role of quercetin in locomotor activities and cholinergic neurotransmission in rats experimentally demyelinated with ethidium bromide. Beckmann DV, Carvalho FB, Mazzanti CM, et al. Life Sci. 103(2), 79-87, (2014)

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Osteogenic differentiation of adipose-derived stem cells promoted by quercetin. Zhou C and Lin Y Cell Prolif. 47(2), 124-32, (2014)

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Dietary flavonoids from modified apple reduce inflammation markers and modulate gut microbiota in mice. Espley RV, Butts CA, Laing WA, et al. J. Nutr. 144(2), 146-54, (2014)

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Isorhamnetin protects against oxidative stress by activating Nrf2 and inducing the expression of its target genes. Yang JH, Shin BY, Han JY, et al. Toxicol. Appl. Pharmacol. 274(2), 293-301, (2014)

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Quercetin modulates OTA-induced oxidative stress and redox signalling in HepG2 cells - up regulation of Nrf2 expression and down regulation of NF-κB and COX-2. Ramyaa P, Krishnaswamy R, and Padma VV Biochim. Biophys. Acta 1840(1), 681-92, (2014)

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An assay for pro-oxidant reactivity based on phenoxyl radicals generated by laccase. Moţ AC, Coman C, Miron C, et al. Food Chem. 143, 214-22, (2014)

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Stability of canola oil encapsulated by co-extrusion technology: effect of quercetin addition to alginate shell or oil core. Waterhouse GI, Wang W, and Sun-Waterhouse D Food Chem. 142, 27-38, (2014)

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Characteristics of quercetin interactions with liposomal and vacuolar membranes. Pawlikowska-Pawlęga B, Dziubińska H, Król E, et al. Biochim. Biophys. Acta 1838(1 Pt B), 254-65, (2014)

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The roles of endoplasmic reticulum stress and mitochondrial apoptotic signaling pathway in quercetin-mediated cell death of human prostate cancer PC-3 cells. Liu KC, Yen CY, Wu RS, et al. Environ. Toxicol. 29(4), 428-39, (2014)

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