Quercétine

==Nom de la substance==
quercétine (= quercétol), 3,3',4',5,7-pentahydroxyflavone
==Famille moléculaire==
Flavonoïde (flavonol) ubiquitaire
==Source végétale==
* Câpres, livèche (jusqu’à 180 mg/100 g), oignon jaune et rouge (20 mg/100 g), pomme (4 mg/100 g), myrtille, canneberge, groseille, théier (thé vert), chou vert frisé, luzerne, haricots verts, poivre vert, vin rouge, abricots, cerises, poires, prunes, fraises, brocolis, tomates, laitue, fruits de sureau noir (42 mg/100 g), Lippia graveolens, chocolat noir (25 mg/100 g) (Phenol-explorer)
==Propriétés==
* Antioxydant Boots AW, Haenen GR, Bast A. Health effects of quercetin: from antioxidant to nutraceutical. Eur J Pharmacol. 2008 May 13;585(2-3):325-37. doi: 10.1016/j.ejphar.2008.03.008. PMID 18417116, protecteur vasculaire Bischoff SC. Quercetin: potentials in the prevention and therapy of disease. Curr Opin Clin Nutr Metab Care. 2008 Nov;11(6):733-40. doi: 10.1097/MCO.0b013e32831394b8. PMID 18827577
* Inhibition de l'agrégation plaquettaire, vasorelaxant Dong, X.; Wang, Y.; Liu, T.; Wu, P.; Gao, J.; Xu, J.; Yang, B.; Hu, Y. Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR) Studies. Molecules 2011, 16, 8257-8272., relaxant artériel Saponara S, Sgaragli G, and Fusi F. Quercetin as a novel activator of L-type Ca2+ channels in rat tail artery smooth muscle cells. Br J Pharmacol. 2002 April; 135(7): 1819–1827. PMCID: PMC1573296 
* Anti-hypertenseur Abigail J. Larson, J. David Symons,Thunder Jalili. Therapeutic Potential of Quercetin to Decrease Blood Pressure: Review of Efficacy and Mechanisms. Adv Nutr. 2012 January; 3(1): 39–46. doi: 10.3945/an.111.001271 PMCID: PMC3262612 texte intégral, Perez-Vizcaino F, Duarte J, Jimenez R, Santos-Buelga C, Osuna A. Antihypertensive effects of the flavonoid quercetin. Pharmacol Rep. 2009 Jan-Feb;61(1):67-75. PMID 19307694, surtout par certains dérivés (acide quercétine-3-glucuronique) B.W. Nileeka Balasuriya, H.P. Vasantha Rupasinghe. Plant flavonoids as angiotensin converting enzyme inhibitors in regulation of hypertension. Functional Foods in Health and Disease 2011; 5:172-188. 
* Néphroprotecteur chez le rat Faddah LM, Abdel Baky NA, Al-Rasheed NM, Al-Rasheed NM, Fatani AJ, Atteya M. Role of quercetin and arginine in ameliorating nano zinc oxide-induced nephrotoxicity in rats. BMC Complement Altern Med. 2012 May 2;12:60. doi: 10.1186/1472-6882-12-60. PMID 22551254, protège de la néphrotoxicité de la gentamicine Abdel-Raheem IT, Abdel-Ghany AA, Mohamed GA. Protective effect of quercetin against gentamicin-induced nephrotoxicity in rats. Biol Pharm Bull. 2009 Jan;32(1):61-7. PMID 19122282
* Neuroprotecteur, diminue la neuro-inflammation par action sur les cellules microgliales Benameur T, Soleti R, Porro C. The Potential Neuroprotective Role of Free and Encapsulated Quercetin Mediated by miRNA against Neurological Diseases. Nutrients. 2021; 13(4):1318. https://doi.org/10.3390/nu13041318
* Anticancéreux Jae-Hoon Jeong, Jee Young An, Yong Tae Kwon, Juong G. Rhee, and Yong J. Lee. Effects of low dose quercetin: Cancer cell-specific inhibition of cell cycle progression. J Cell Biochem. 2009 January 1; 106(1): 73–82. http://www.ncbi.nlm.nih.gov:80/pmc/articles/PMC2736626/?tool=pmcentrez, Jones D J L, Lamb J H, Verschoyle R D, Howells L M, Butterworth M, Lim C K, Ferry D, Farmer P B, Gescher A J. Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. Br J Cancer. 2004 September 13; 91(6): 1213–1219., avec activité immunostimulante Yu CS, Lai KC, Yang JS, Chiang JH, Lu CC, Wu CL, Lin JP, Liao CL, Tang NY, Wood WG, Chung JG. Quercetin inhibited murine leukemia WEHI-3 cells in vivo and promoted immune response. Phytother Res. 2010 Feb;24(2):163-8. PMID 19449452 et inducteur d'apoptose Young-Ho Kim, Dae-Hee Lee, Jae-Hoon Jeong, Zong Sheng Guo, and Yong J. Lee. Quercetin augments TRAIL-induced apoptotic death: involvement of the ERK signal transduction pathway. Biochem Pharmacol. 2008 May 15; 75(10): 1946–1958. http://www.ncbi.nlm.nih.gov:80/pmc/articles/PMC2430102/?tool=pmcentrez, Xiao D, Zhu SP, Gu ZL. Quercetin induced apoptosis in human leukemia HL-60 cells. Zhongguo Yao Li Xue Bao. 1997 May;18(3):280-3. PMID 10072952 avec activité sur les protéines de choc HSP (heat shock proteins) hsp27 et hsp70 Rong Y, Yang EB, Zhang K, Mack P. Quercetin-induced apoptosis in the monoblastoid cell line U937 in vitro and the regulation of heat shock proteins expression. Anticancer Res. 2000 Nov-Dec;20(6B):4339-45. PMID 11205268, Wei YQ, Zhao X, Kariya Y, Fukata H, Teshigawara K, Uchida A. Induction of apoptosis by quercetin: involvement of heat shock protein. Cancer Res. 1994 Sep 15;54(18):4952-7. PMID 8069862
* Activité antitumorale vis-à-vis du cancer de la prostate Nair HK, Rao KVK, Aalinkeel R, Mahajan S, Chawda R, Schwartz SA. Inhibition of Prostate Cancer Cell Colony Formation by the Flavonoid Quercetin Correlates with Modulation of Specific Regulatory Genes. Clin Diagn Lab Immunol. 2004 January; 11(1): 63–69. PMCID: PMC321331 et de certaines cellules cancéreuses mammaires Carli CB, de Matos DC, Lopes FC, Maia DC, Dias MB, Sannomiya M, Rodrigues CM, Andreo MA, Vilegas W, Colombo LL, Carlos IZ. Isolated flavonoids against mammary tumour cells LM2. Z Naturforsch C. 2009 Jan-Feb;64(1-2):32-6. PMID 19323263
* Prévention de la toxicité cardiaque de la doxorubicine, avec resvératrol Cote B, Carlson LJ, Rao DA, Alani AW4. Combinatorial resveratrol and quercetin polymeric micelles mitigate doxorubicin induced cardiotoxicity in vitro and in vivo. J Control Release. 2015 Jul 6;213:128-133. doi: 10.1016/j.jconrel.2015.06.040. PMID 26160305
* Protection vis-à-vis de l'inflammation gastrique associée à l'infection à Helicobacter pylori par activité sur p38MAPK, BCL-2, BAX. Zhang S, Huang J, Xie X, He Y, Mo F, Luo Z. Quercetin from Polygonum capitatum Protects against Gastric Inflammation and Apoptosis Associated with Helicobacter pylori Infection by Affecting the Levels of p38MAPK, BCL-2 and BAX. Molecules. 2017 May 6;22(5). pii: E744. doi: 10.3390/molecules22050744. PMID 28481232
* Augmente l'activité antitoxique du foie
* Antidiabétique Vessal, M., Hemmati, M., & Vasei, M. (2003). Antidiabetic effects of quercetin in streptozocin-induced diabetic rats. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 135C(3), 357–364. https://doi.org/10.1016/s1532-0456(03)00140-6. PMID 12927910
* Inhibiteur de la lipase pancréatique, potentielle action dans la prise de poids Martinez-Gonzalez, A. I., Alvarez-Parrilla, E., Díaz-Sánchez, Á. G., de la Rosa, L. A., Núñez-Gastélum, J. A., Vazquez-Flores, A. A., & Gonzalez-Aguilar, G. A. (2017). In vitro Inhibition of Pancreatic Lipase by Polyphenols: A Kinetic, Fluorescence Spectroscopy and Molecular Docking Study. Food technology and biotechnology, 55(4), 519–530. https://doi.org/10.17113/ftb.55.04.17.5138
* Anti-inflammatoire Nair MP, Mahajan S, Reynolds JL., Ravikumar A, Nair H, Schwartz SA., Kandaswami C. The Flavonoid Quercetin Inhibits Proinflammatory Cytokine (Tumor Necrosis Factor Alpha) Gene Expression in Normal Peripheral Blood Mononuclear Cells via Modulation of the NF-κβ System. Clin Vaccine Immunol. 2006 March; 13(3): 319–328. PMCID: PMC1391952, Guardia T, Rotelli AE, Juarez AO, Pelzer LE. Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Farmaco. 2001 Sep;56(9):683-7. PMID 11680812, Rotelli AE, Guardia T, Juárez AO, de la Rocha NE, Pelzer LE. Comparative study of flavonoids in experimental models of inflammation. Pharmacol Res. 2003 Dec;48(6):601-6. PMID 14527825
* Anti-allergique Farideh Shishehbor, Lotfollah Behroo, Mehri Ghafouriyan Broujerdnia, Forough Namjoyan, Seiyed-Mahmoud Latifi. Quercetin Effectively Quells Peanut-Induced Anaphylactic Reactions in the Peanut Sensitized Rats. Iran J Allergy Asthma Immunol March 2010; 9(1): 27-34 , Mlcek J, Jurikova T, Skrovankova S, Sochor J. Quercetin and Its Anti-Allergic Immune Response. Molecules. 2016 May 12;21(5). pii: E623. doi: 10.3390/molecules21050623. PMID 27187333, inhibition de la dégranulation des mastocytes, avec un effet préventif Weng Z, Zhang B, Asadi S, Sismanopoulos N, Butcher A, Fu X, Katsarou-Katsari A, Antoniou C, Theoharides TC. Quercetin is more effective than cromolyn in blocking human mast cell cytokine release and inhibits contact dermatitis and photosensitivity in humans. PLoS One. 2012;7(3):e33805. PMID 22470478, diminution de l'inflammation liée aux éosinophiles (comme l'isoquercitrine Rogerio AP, Kanashiro A, Fontanari C, da Silva EV, Lucisano-Valim YM, Soares EG, Faccioli LH. Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma. Inflamm Res. 2007 Oct;56(10):402-8. PMID 18026696, régule la balance Th1/Th2 Park HJ, Lee CM, Jung ID, Lee JS, Jeong YI, Chang JH, Chun SH, Kim MJ, Choi IW, Ahn SC, Shin YK, Yeom SR, Park YM. Quercetin regulates Th1/Th2 balance in a murine model of asthma. Int Immunopharmacol. 2009 Mar;9(3):261-7. doi: 10.1016/j.intimp.2008.10.021. PMID 19061976
* Antiviral (réduction dose-dépendante de l'infectivité, diminue la réplication intracellulaire) Kaul TN, Middleton E Jr, Ogra PL. Antiviral effect of flavonoids on human viruses. J Med Virol. 1985 Jan;15(1):71-9. PMID 2981979
** Inhibition de la réplication de rhinovirus Ganesan S, Faris AN, Comstock AT, Wang Q, Nanua S, Hershenson MB, Sajjan US. Quercetin inhibits rhinovirus replication in vitro and in vivo. Antiviral Res. 2012 Jun;94(3):258-71. doi: 10.1016/j.antiviral.2012.03.005. PMID 22465313
** Prophylaxie de la grippe par la quercétine Wu W, Li R, Li X, He J, Jiang S, Liu S, Yang J. Quercetin as an Antiviral Agent Inhibits Influenza A Virus (IAV) Entry. Viruses. 2015 Dec 25;8(1). pii: E6. doi: 10.3390/v8010006. PMID 26712783 ou ses dérivés (quercétine-3-O-α-L-rhamnopyranoside) Mehrbod P, Abdalla MA, Fotouhi F, Heidarzadeh M, Aro AO, Eloff JN, McGaw LJ, Fasina FO. Immunomodulatory properties of quercetin-3-O-α-L-rhamnopyranoside from Rapanea melanophloeos against influenza a virus. BMC Complement Altern Med. 2018 Jun 15;18(1):184. doi: 10.1186/s12906-018-2246-1. PMID 29903008, Choi HJ1, Song JH, Kwon DH. Quercetin 3-rhamnoside exerts antiinfluenza A virus activity in mice. Phytother Res. 2012 Mar;26(3):462-4. doi: 10.1002/ptr.3529. PMID 21728202, s'oppose aux effets pro-oxydants induits par le virus grippal Nile SH, Kim DH, Nile A, Park GS, Gansukh E, Kai G. Probing the effect of quercetin 3-glucoside from Dianthus superbus L against influenza virus infection- In vitro and in silico biochemical and toxicological screening. Food Chem Toxicol. 2020 Jan;135:110985. doi: 10.1016/j.fct.2019.110985. PMID 31765700, une thérapie antioxydante pourrait constituer une prévention des complications graves associées à la grippe Uchide N, Toyoda H. Antioxidant therapy as a potential approach to severe influenza-associated complications. Molecules. 2011 Feb 28;16(3):2032-52. doi: 10.3390/molecules16032032. PMID 21358592
** Inhibition in vitro de la pénétration du virus Ebola par la quercétine-3-O-glucoside Qiu X, Kroeker A, He S, Kozak R, Audet J, Mbikay M, Chrétien M. Prophylactic Efficacy of Quercetin 3-β-O-d-Glucoside against Ebola Virus Infection. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5182-8. doi: 10.1128/AAC.00307-16. Print 2016 Sep. PMID 27297486
** Activité antivirale vis-à-vis du virus Zika Wong G, He S, Siragam V, Bi Y, Mbikay M, Chretien M, Qiu X. Antiviral activity of quercetin-3-β-O-D-glucoside against Zika virus infection. Virol Sin. 2017 Dec;32(6):545-547. doi: 10.1007/s12250-017-4057-9. PMID 28884445, du virus de l’hépatite B Cheng Z, Sun G, Guo W, Huang Y, Sun W, Zhao F, Hu K. Inhibition of hepatitis B virus replication by quercetin in human hepatoma cell lines. Virol Sin. 2015 Aug;30(4):261-8. doi: 10.1007/s12250-015-3584-5. PMID 26268473, de l’hépatite C Rojas Á, Del Campo JA, Clement S, Lemasson M, García-Valdecasas M, Gil-Gómez A, Ranchal I, Bartosch B, Bautista JD, Rosenberg AR, Negro F, Romero-Gómez M. Effect of Quercetin on Hepatitis C Virus Life Cycle: From Viral to Host Targets. Sci Rep. 2016 Aug 22;6:31777. doi: 10.1038/srep31777. PMID 27546480, d'Epstein-Barr virus EBV et antitumoral contre le carcinome gastrique humain Lee M, Son M, Ryu E, Shin YS, Kim JG, Kang BW, Cho H, Kang H. Quercetin-induced apoptosis prevents EBV infection. Oncotarget. 2015 May 20;6(14):12603-24. PMID 26059439
** La quercétine ou des dérivés ont un effet inhibiteur de protéases chez les Coronavirus MERS-Cov Jo S, Kim H, Kim S, Shin DH, Kim MS. Characteristics of flavonoids as potent MERS-CoV 3C-like protease inhibitors. Chem Biol Drug Des. 2019 Dec;94(6):2023-2030. doi: 10.1111/cbdd.13604. PMID 31436895, et d'autres souches comme celles responsables de SRAS Park HR, Yoon H, Kim MK, Lee SD, Chong Y. Synthesis and antiviral evaluation of 7-O-arylmethylquercetin derivatives against SARS-associated coronavirus (SCV) and hepatitis C virus (HCV). Arch Pharm Res. 2012 Jan;35(1):77-85. doi: 10.1007/s12272-012-0108-9. PMID 22297745
** Une supplémentation en quercétine (500 mg), vitamine C (500 mg) et bromélaïne (50 mg) semble protectrice en prévention de la COVID-19 chez les professionnels de santé Arslan, Bengu and Ucuncu Ergun, Nurcan and Topuz, Seyma and Yilmaz Semerci, Seda and Suner, Nurettin and Kocatas, Ali and Onal, Hasan, Synergistic Effect of Quercetin and Vitamin C Against COVID-19: Is a Possible Guard for Front Liners. Posted: 16 Nov 2020. Available at SSRN: https://ssrn.com/abstract=3682517 or http://dx.doi.org/10.2139/ssrn.3682517
** La quercétine atténue la progression de la maladie pulmonaire induite par le rhinovirus dans un modèle murin de BPCO Farazuddin M, Mishra R, Jing Y, Srivastava V, Comstock AT, Sajjan US. Quercetin prevents rhinovirus-induced progression of lung disease in mice with COPD phenotype. PLoS One. 2018 Jul 5;13(7):e0199612. doi: 10.1371/journal.pone.0199612. eCollection 2018. PMID 29975735
** Actif in vitro contre le virus de la dengue Zandi K, Teoh BT, Sam SS, Wong PF, Mustafa MR, Abubakar S. Antiviral activity of four types of bioflavonoid against dengue virus type-2. Virol J. 2011 Dec 28;8:560. doi: 10.1186/1743-422X-8-560. PMID 22201648
* Antibactérien et antifongique surtout par certains dérivés (quercétine-3,7-O-α-l-dirhamnoside) Berrin Özc ̧elik, Ilkay Orhan, Gülnur Toker. Antiviral and Antimicrobial Assessment of Some Selected Flavonoids. Z. Naturforsch. 61c, 632Ð638 (2006)
* Propriétés pseudo-oestrogéniques, inhibition de la perte osseuse et stimulation de la formation osseuse, par inhibition de l'activité des ostéoclastes et stimulation de l'activité des ostéoblastes PROUILLET Christophe. Evaluation des effets biochimiques de la quercétine et du kaempférol, principaux flavonols alimentaires, sur l'activité des cellules osseuses, 2002,
Faculté de Pharmacie d'Amiens, article dans Aprifel 2010 
* Effet anti-abortif par activité immunologique Wang X, Ma A, Shi W, Geng M, Zhong X, Zhao Y. Quercetin and Bornyl Acetate Regulate T-Lymphocyte Subsets and INF-γ/IL-4 Ratio In Utero in Pregnant Mice. Evid Based Complement Alternat Med. 2011;2011:745262. PMID 20981318 Texte intégral : 
* La quercétine joue un rôle synergique :
** Elle renforce l’effet antidépresseur du millepertuis, l’association de quercétine et d’extrait d'Hypericum perforatum possède un effet antidépresseur synergique Liu, J., Fang, Y., Wei, Z., Yang, X., & ZENG, L. (2013). Synergic antidepressive effect of quercetin and Hypericum perforatum extract in mice. Journal of Zhejiang University (Medical Science), 42(6), 615-619.
** Elle amplifie nettement ses propriétés anti-inflammatoires lorsqu’elle est associée à l’astragaline, un autre flavonoïde, présent dans les feuilles de mûrier Morus alba Mok, J. Y., Jeong, S. I., Kim, J. H., & Jang, S. I. (2011). Synergic Effect of Quercetin and Astragalin from Mulberry Leaves on Ani-inflammation. Journal of Physiology & Pathology in Korean Medicine, 25(5), 830-836.
* La quercétine intervient dans la photo protection chez les végétaux Dobrikova AG, Apostolova EL. Damage and protection of the photosynthetic apparatus from UV-B radiation. II. Effect of quercetin at different pH. J Plant Physiol. 2015 Jul 20;184:98-105. doi: 10.1016/j.jplph.2015.06.008. PMID 26282614
* Des composés nouveaux, synthétisés à partir de la quercétine-3-β-galactoside, sont des inhibiteurs efficaces de la protéase 3CL du coronavirus du SARS (SARS-CoV 3CL pro ), et pourraient être développés comme des médicaments pour le SRAS Lili Chen, Jian Li, Cheng Luo, Hong Liu, Weijun Xu, Gang Chen, Oi Wah Liew, Weiliang Zhu, Chum Mok Puah, Xu Shen, Hualiang Jiang. Binding interaction of quercetin-3-β-galactoside and its synthetic derivatives with SARS-CoV 3CLpro: Structure–activity relationship studies reveal salient pharmacophore features. Bioorganic & Medicinal Chemistry, Volume 14, Issue 24, 2006, Pages 8295-8306, https://doi.org/10.1016/j.bmc.2006.09.014.
==Effet thérapeutique==
* Diminution du risque coronarien et cérébro-vasculaire
* Prévention de la prise de poids Nishimura, M., Muro, T., Kobori, M., & Nishihira, J. (2019). Effect of Daily Ingestion of Quercetin-Rich Onion Powder for 12 Weeks on Visceral Fat: A Randomised, Double-Blind, Placebo-Controlled, Parallel-Group Study. Nutrients, 12(1), 91. https://doi.org/10.3390/nu12010091 PMID 31905615
* Effet favorable dans la ménopause
* Préventif du cancer
* Peut agir dans l'obésité
==Effets indésirables==
* Effets sur les cytochromes P450 :
** In vitro, la quercétine est un puissant inhibiteur compétitif du CYP1A2, du CYP2C9, du CYP2C19 et du CYP3A4 et un inhibiteur compétitif modéré du CYP2D6 Rastogi, H. and Jana, S. (2014), Evaluation of Inhibitory Effects of Caffeic acid and Quercetin on Human Liver Cytochrome P450 Activities, Phytother. Res., 28, pages 1873– 1878, doi: 10.1002/ptr.5220
* Sa consommation peut donc augmenter sélectivement la concentration sanguine en médicaments, lorsqu'ils sont métabolisés par ces cytochromes
==Bibliographie==
* Winit Choiprasert, Nathupakorn Dechsupa, Suchart Kothan, Manuel Garrigos, Samlee Mankhetkorn. Quercetin, Quercetrin Except Rutin Potentially Increased Pirarubicin Cytotoxicity by Non-Competitively Inhibiting the P-Glycoprotein-and MRP1 Function in Living K562/adr and GLC4/adr Cells. American Journal of Pharmacology and Toxicology 5 (1): 24-33, 2010 
* Zhou W, Kallifatidis G, Baumann B, Rausch V, Mattern J, Gladkich J, Giese N, Moldenhauer G, Wirth T, Büchler MW, Salnikov AV, Herr I. Dietary polyphenol quercetin targets pancreatic cancer stem cells. Int J Oncol. 2010 Sep;37(3):551-61. PMID 20664924
* Bittencourt T ,Komoto T ,Massaroto B ,Miranda C ,Beleboni R ,Marins M ,Fachin A. Trans-chalcone and quercetin down-regulate fatty acid synthase gene expression and reduce ergosterol content in the human pathogenic dermatophyte Trichophyton rubrum. BMC Complementary and Alternative Medicine, 2013, 13:229 (17 September 2013) Abstract Provisional PDF
* http://fr.wikipedia.org/wiki/Querc%C3%A9tine#cite_note-USDA-1
Catégorie:principes actifs