|CAS number||, 6151-25-3 (Quercetin dihydrate)|
|Jmol-3D images||Image 1|
|Molar mass||302.236 g/mol|
|Appearance||yellow crystalline powder|
|Melting point||316 °C|
|Solubility in water||Practically insoluble in water; soluble in aqueous alkaline solutions|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Quercetin //, a flavonol, is a flavonoid, in other words, a plant pigment with a molecular structure like or derived from flavone. It is found in fruits, vegetables, leaves and grains. It can be used as an ingredient in supplements, beverages, or foods.
- 1 Occurrence
- 2 Metabolism
- 3 Effects of consumption by humans and other animals
- 4 Preliminary research
- 5 Drug interactions
- 6 See also
- 7 References
- 8 External links
Quercetin is a flavonoid widely distributed in nature. The name has been used since 1857, and is derived from quercetum (oak forest), after Quercus. It is a naturally occurring polar auxin transport inhibitor.
|Foods containing quercetin||Quercetin (mg/100g of edible portion)|
|dock like sorrel||86|
|Hungarian wax pepper||51|
|sea buckthorn berry||8|
|prickly pear cactus fruits||5|
|apples, Red Delicious||4|
|tea, black or green Camellia sinensis||2|
In red onions, higher concentrations of quercetin occur in the outermost rings and in the part closest to the root, the latter being the part of the plant with the highest concentration. One study found that organically grown tomatoes had 79% more quercetin than chemically grown fruit. Quercetin is present in various kinds of honey from different plant sources.
Phenylalanine is converted to 4-coumaroyl-CoA in a series of steps known as the general phenylpropanoid pathway using phenylalanine ammonia-lyase, cinnamate-4-hydroxylase, and 4-coumaroyl-CoA-ligase. 4-Coumaroyl-CoA is added to three molecules of malonyl-CoA to form tetrahydroxychalcone using 7,2’-dihydroxy-4’-methoxyisoflavanol synthase. Tetrahydroxychalcone is then converted into naringenin using chalcone isomerase. Naringenin is then converted into eriodictyol using flavanoid 3’-hydroxylase. Eriodictyol is then converted into dihydroquercetin with flavanone 3-hydroxylase, which is then converted into quercetin using flavonol synthase.
Quercetin release in the rutin degradation pathway
Quercetin 3-O-sulfate is a human plasma quercetin metabolite.
Quercetin is the aglycone form of a number of other flavonoid glycosides, such as rutin and quercitrin, found in citrus fruit, buckwheat and onions. Quercetin forms the glycosides quercitrin and rutin together with rhamnose and rutinose, respectively. Likewise guaijaverin is the 3-O-arabinoside, hyperoside is the 3-O-galactoside, isoquercitin is the 3-O-glucoside and spiraeoside is the 4'-O-glucoside. CTN-986 is a quercetin derivative found in cottonseeds and cottonseed oil. Miquelianin is the quercetin 3-o-β-d-glucuronopyranoside.
Effects of consumption by humans and other animals
Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. In a bioavailability study in rats, radiolabelled quercetin-4'-glucoside was converted to phenolic acids as it passed through the gastrointestinal tract, producing compounds not monitored in previous animal studies of aglycone quercetin. All but 4% was recovered within 72 hours (69% in urine), indicating low retention and high excretion, a characteristic of ingested polyphenols. Quercetin may also induce insulin secretion by activation of L-type calcium channels in the pancreatic β-cells. Quercetin has not been confirmed scientifically as a specific therapeutic for any condition nor approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin.
Quercetin has demonstrated significant anti-inflammatory activity in mouse models of asthma because of direct inhibition of several initial processes of inflammation.
Laboratory studies have investigated Quercetin's potential for use in anti-cancer applications. The American Cancer Society says while quercetin "has been promoted as being effective against a wide variety of diseases, including cancer," and "some early lab results appear promising, as of yet there is no reliable clinical evidence that quercetin can prevent or treat cancer in humans." In the amounts consumed in a healthy diet, quercetin "is unlikely to cause any major problems or benefits."
Serum IgE levels are highly elevated in eczema patients, and virtually all eczema patients are positive for allergy testing. Excessive histamine release can be minimized by the use of antioxidants. Quercetin has been shown to be effective in reducing IgE levels in rodent models.
Quercetin has been reported to be of use in alleviating symptoms of pollinosis. An enzymatically modified derivative was found to alleviate ocular but not nasal symptoms of pollinosis.
A study with rats showed that quercetin effectively reduced immediate-release niacin (vitamin B3) flush, in part by means of reducing prostaglandin D2 production. A pilot clinical study of four humans gave preliminary data supporting this.
Quercetin has been shown to increase energy expenditure in rats, but only for short periods (fewer than 8 weeks). Effects of quercetin on exercise tolerance in mice have been associated with increased mitochondrial biogenesis. In mice, an oral quercetin dose of 12.5 to 25 mg/kg increased gene expression of mitochondrial biomarkers and improved exercise endurance.
Supplements of quercetin with vitamin C and niacin does not cause any significant difference in body mass or composition and has no significant effect on inflammatory markers, diagnostic blood chemistries, blood pressure, and blood lipid profiles.
Possibly an active component of heather (Calluna vulgaris), quercetin was suspected from a bioassay test on crude extracts to selectively inhibit monoamine oxidase, possibly indicating pharmacological properties.
Quercetin is contraindicated with some antibiotics; it may interact with fluoroquinolones (an antibiotic), as quercetin competitively binds to bacterial DNA gyrase. Whether this inhibits or enhances the effect of fluoroquinolones is not certain.
AHFS Drug Information (2010) identifies quercetin as an inhibitor of CYP2C8, and specifically names it as a drug with potential to have harmful interactions with taxol/paclitaxel. As paclitaxel is metabolized primarily by CYP2C8, its bioavailability may be increased unpredictably, potentially leading to harmful side-effects.
Quercetin is described as an inhibitor of CYP2C9. Quercetin is an inhibitor and inducer of CYP3A4 (in other words, it reduces the enzyme's activity in the short term, but the body responds by producing more of it). CYP2C9 and CYP3A4 are members of the cytochrome P450 mixed-function oxidase system, and as such are enzymes involved in the metabolism of xenobiotics in the body. In either case, quercetin may alter serum levels and, therefore, effects of drugs metabolized by these enzymes.
- Quercetin dihydrate safety sheet on http://www.pvp.com.br (English)
- "Flavenoid". WordNet. Princeton University.
- "Quercetin". Merriam-Webster.
- "Quercitin (biochemistry)". Encyclopædia Britannica.
- Fischer C, Speth V, Fleig-Eberenz S, Neuhaus G (October 1997). "Induction of Zygotic Polyembryos in Wheat: Influence of Auxin Polar Transport". Plant Cell 9 (10): 1767–80. doi:10.1105/tpc.9.10.1767. PMC 157020. PMID 12237347.
- "USDA Database for the Flavonoid Content of Selected Foods, Release 3.1". U.S. Department of Agriculture. 2013.
- "Dill weed, fresh". Merschat family website.
- Justesen U, Knuthsen P (May 2001). "Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes". Food Chemistry 73 (2): 245–50. doi:10.1016/S0308-8146(01)00114-5.
- "USDA Database for the Flavonoid Content of Selected Foods, Release 3". U.S. Department of Agriculture. 2011.
- "Food Nutrition Facts: Buckwheat". Merschat family website.
- Smith C, Lombard KA, Peffley EB, Liu W (2003). "Genetic Analysis of Quercetin in Onion (Allium cepa L.) Lady Raider". The Texas Journal of Agriculture and Natural Resource (Agriculture Consortium of Texas) 16: 24–8. Archived from the original on February 25, 2007.
- Mitchell AE, Hong YJ, Koh E, Barrett DM, Bryant DE, Denison RF, Kaffka S (July 2007). "Ten-year comparison of the influence of organic and conventional crop management practices on the content of flavonoids in tomatoes". J. Agric. Food Chem. 55 (15): 6154–9. doi:10.1021/jf070344. PMID 17590007.
- Petrus K, Schwartz H, Sontag G (June 2011). "Analysis of flavonoids in honey by HPLC coupled with coulometric electrode array detection and electrospray ionization mass spectrometry". Anal Bioanal Chem 400 (8): 2555–63. doi:10.1007/s00216-010-4614-7. PMID 21229237.
- Winkel-Shirley B (June 2001). "Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology". Plant Physiol. 126 (2): 485–93. doi:10.1104/pp.126.2.485. PMC 1540115. PMID 11402179.
- quercitrinase on www.brenda-enzymes.org
- Tranchimand S, Brouant P, Iacazio G (November 2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation 21 (6): 833–59. doi:10.1007/s10532-010-9359-7. PMID 20419500.
- Juergenliemk G, Boje K, Huewel S, Lohmann C, Galla HJ, Nahrstedt A (November 2003). "In vitro studies indicate that miquelianin (quercetin 3-o-β-d-glucuronopyranoside) is able to reach the CNS from the small intestine". Planta Med. 69 (11): 1013–7. doi:10.1055/s-2003-45148. PMID 14735439.
- Mullen W, Rouanet JM, Auger C, Teissèdre PL, Caldwell ST, Hartley RC, Lean ME, Edwards CA, Crozier A (December 2008). "Bioavailability of [2-(14)C]quercetin-4'-glucoside in rats". J. Agric. Food Chem. 56 (24): 12127–37. doi:10.1021/jf802754s. PMID 19053221.
- Bardy G, Virsolvy A, Quignard JF, Ravier MA, Bertrand G, Dalle S, Cros G, Magous R, Richard S, Oiry C (July 2013). "Quercetin induces insulin secretion by direct activation of L-type calcium channels in pancreatic beta cells". Br. J. Pharmacol. 169 (5): 1102–13. doi:10.1111/bph.12194. PMC 3696332. PMID 23530660.
- US FDA, Center for Food Safety and Nutrition, Qualified Health Claims Subject to Enforcement Discretion, April 2007 [dead link]
- Wu LL, Yang XB, Huang ZM, Liu HZ, Wu GX (March 2007). "In vivo and in vitro antiviral activity of hyperoside extracted from Abelmoschus manihot (L) medik". Acta Pharmacol. Sin. 28 (3): 404–9. doi:10.1111/j.1745-7254.2007.00510.x. PMID 17303004.
- Pisonero-Vaquero S (Mar 2014). "Modulation of PI3K-LXRα-dependent lipogenesis mediated by oxidative/nitrosative stress contributes to inhibition of HCV replication by quercetin.". Lab Invest. 94 (3): 262–274. PMID 24492281.
- Yu YB, Miyashiro H, Nakamura N, Hattori M, Park JC (July 2007). "Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV-1 viral enzymes". Arch. Pharm. Res. 30 (7): 820–6. doi:10.1007/BF02978831. PMID 17703732.
- Spedding G, Ratty A, Middleton E (September 1989). "Inhibition of reverse transcriptases by flavonoids". Antiviral Res. 12 (2): 99–110. doi:10.1016/0166-3542(89)90073-9. PMID 2480745.
- "Asthma". University of Maryland Medical Center. 2013-06-21.
- 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 (March 2009). "Quercetin regulates Th1/Th2 balance in a murine model of asthma". Int. Immunopharmacol. 9 (3): 261–7. doi:10.1016/j.intimp.2008.10.021. PMID 19061976.
- Verschoyle RD, Steward WP, Gescher AJ (2007). "Putative cancer chemopreventive agents of dietary origin-how safe are they?". Nutr Cancer 59 (2): 152–62. doi:10.1080/01635580701458186. PMID 18001209.
- Rietjens IM, Boersma MG, van der Woude H, Jeurissen SM, Schutte ME, Alink GM (July 2005). "Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk". Mutat. Res. 574 (1–2): 124–38. doi:10.1016/j.mrfmmm.2005.01.028. PMID 15914212.
- van der Woude H, Alink GM, van Rossum BE, Walle K, van Steeg H, Walle T, Rietjens IM (December 2005). "Formation of transient covalent protein and DNA adducts by quercetin in cells with and without oxidative enzyme activity". Chem. Res. Toxicol. 18 (12): 1907–16. doi:10.1021/tx050201m. PMID 16359181.
- Neuhouser ML (2004). "Dietary flavonoids and cancer risk: evidence from human population studies". Nutr Cancer 50 (1): 1–7. doi:10.1207/s15327914nc5001_1. PMID 15572291.
- Murakami A, Ashida H, Terao J (October 2008). "Multitargeted cancer prevention by quercetin". Cancer Lett. 269 (2): 315–25. doi:10.1016/j.canlet.2008.03.046. PMID 18467024.
- Nöthlings U, Murphy SP, Wilkens LR, Henderson BE, Kolonel LN (October 2007). "Flavonols and pancreatic cancer risk: the multiethnic cohort study". Am. J. Epidemiol. 166 (8): 924–31. doi:10.1093/aje/kwm172. PMID 17690219.
- Paliwal S, Sundaram J, Mitragotri S (February 2005). "Induction of cancer-specific cytotoxicity towards human prostate and skin cells using quercetin and ultrasound". Br. J. Cancer 92 (3): 499–502. doi:10.1038/sj.bjc.6602364. PMC 2362095. PMID 15685239.
- Xavier CP, Lima CF, Rohde M, Pereira-Wilson C (December 2011). "Quercetin enhances 5-fluorouracil-induced apoptosis in MSI colorectal cancer cells through p53 modulation". Cancer Chemother. Pharmacol. 68 (6): 1449–57. doi:10.1007/s00280-011-1641-9. PMID 21479885.
- American Cancer Society, Quercetin
- Jung, Min Kyung; Hur, Dae Young; Song, Seok Bean; Park, Yoorim; Kim, Tae Sung; Bang, Sa Ik; Kim, Seonghan; Song, Hyun Keun; Park, Hyunjeong; Cho, Dae Ho (2010). "Tannic Acid and Quercetin Display a Therapeutic Effect in Atopic Dermatitis via Suppression of Angiogenesis and TARC Expression in Nc/Nga Mice". Journal of Investigative Dermatology 130 (5): 1459–63. doi:10.1038/jid.2009.401. PMID 20054339.
- Stewart LK, Soileau JL, Ribnicky D, Wang ZQ, Raskin I, Poulev A, Majewski M, Cefalu WT, Gettys TW (July 2008). "Quercetin transiently increases energy expenditure but persistently decreases circulating markers of inflammation in C57BL/6J mice fed a high-fat diet". Metab. Clin. Exp. 57 (7 Suppl 1): S39–46. doi:10.1016/j.metabol.2008.03.003. PMC 2596873. PMID 18555853.
- Davis JM, Murphy EA, Carmichael MD, Davis B (April 2009). "Quercetin increases brain and muscle mitochondrial biogenesis and exercise tolerance". Am. J. Physiol. Regul. Integr. Comp. Physiol. 296 (4): R1071–7. doi:10.1152/ajpregu.90925.2008. PMID 19211721.
- Phys Ed: Is Quercetin Really a Wonder Sports Supplement? By Gretchen Reynolds. New York Times, October 7, 2009. Review of the research.
- Balabolkin II, Gordeeva GF, Fuseva ED, Dzhunelov AB, Kalugina OL, Khamidova MM (1992). "Primenenie vitaminov pri allergicheskikh zabolevaniiakh u deteĭ" [Use of vitamins in allergic illnesses in children]. Vopr. Med. Khim. (in Russian) 38 (5): 36–40. PMID 1492394.
- Hirano T, Kawai M, Arimitsu J, Ogawa M, Kuwahara Y, Hagihara K, Shima Y, Narazaki M, Ogata A, Koyanagi M, Kai T, Shimizu R, Moriwaki M, Suzuki Y, Ogino S, Kawase I, Tanaka T (September 2009). "Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis". Allergol Int 58 (3): 373–82. doi:10.2332/allergolint.08-OA-0070. PMID 19454839.
- Kawai M, Hirano T, Arimitsu J, Higa S, Kuwahara Y, Hagihara K, Shima Y, Narazaki M, Ogata A, Koyanagi M, Kai T, Shimizu R, Moriwaki M, Suzuki Y, Ogino S, Kawase I, Tanaka T (2009). "Effect of enzymatically modified isoquercitrin, a flavonoid, on symptoms of Japanese cedar pollinosis: a randomized double-blind placebo-controlled trial". Int. Arch. Allergy Immunol. 149 (4): 359–68. doi:10.1159/000205582. PMID 19295240.
- Mainardi T, Kapoor S, Bielory L (February 2009). "Complementary and alternative medicine: herbs, phytochemicals and vitamins and their immunologic effects". J. Allergy Clin. Immunol. 123 (2): 283–94; quiz 295–6. doi:10.1016/j.jaci.2008.12.023. PMID 19203652.
- Quercetin, University of Maryland Medical Center, http://www.umm.edu/altmed/articles/quercetin-000322.htm
- Shaik YB, Castellani ML, Perrella A, Conti F, Salini V, Tete S, Madhappan B, Vecchiet J, De Lutiis MA, Caraffa A, Cerulli G (2006). "Role of quercetin (a natural herbal compound) in allergy and inflammation". J. Biol. Regul. Homeost. Agents 20 (3–4): 47–52. PMID 18187018.
- Papaliodis D, Boucher W, Kempuraj D, Theoharides TC (2008). "The flavonoid luteolin inhibits niacin-induced flush". Brit J Pharmacol 153 (7): 1382–87. doi:10.1038/sj.bjp.0707668. PMC 2437911. PMID 18223672.
- Kalogeromitros D, Makris M, Chliva C, Aggelides X, Kempuraj D, Theoharides TC (2008). "A quercetin containing supplement reduces niacin-induced flush in humans". Int J Immunopathol Pharmacol 21 (3): 509–14. PMID 18831918.
- Hong Lei, Jing Luo, Li Tong, Li-qin Peng, Yao Qi, Zhi-guang Jia, Qun Wei (2011). "Quercetin binds to calcineurin at a similar region to cyclosporin A and tacrolimus". Food Chemistry 127 (3): 1169–74. doi:10.1016/j.foodchem.2011.01.119.
- Lucas HJ, Brauch CM, Settas L, Theoharides TC (2006). "Fibromyalgia--new concepts of pathogenesis and treatment". Int J Immunopathol Pharmacol 19 (1): 5–10. PMID 16569342.
- Edwards RL, Lyon T, Litwin SE, Rabovsky A, Symons JD, Jalili T (November 2007). "Quercetin reduces blood pressure in hypertensive subjects". J. Nutr. 137 (11): 2405–11. PMID 17951477.
- Egert S, Bosy-Westphal A, Seiberl J, Kürbitz C, Settler U, Plachta-Danielzik S, Wagner AE, Frank J, Schrezenmeir J, Rimbach G, Wolffram S, Müller MJ (October 2009). "Quercetin reduces systolic blood pressure and plasma oxidised low-density lipoprotein concentrations in overweight subjects with a high-cardiovascular disease risk phenotype: a double-blinded, placebo-controlled cross-over study". Br. J. Nutr. 102 (7): 1065–74. doi:10.1017/S0007114509359127. PMID 19402938.
- Yang JY, Della-Fera MA, Rayalam S, Ambati S, Hartzell DL, Park HJ, Baile CA (May 2008). "Enhanced inhibition of adipogenesis and induction of apoptosis in 3T3-L1 adipocytes with combinations of resveratrol and quercetin". Life Sci. 82 (19–20): 1032–9. doi:10.1016/j.lfs.2008.03.003. PMID 18433793.
- Kurin E, Atanasov AG, Donath O, Heiss EH, Dirsch VM, Nagy M (May 2012). "Synergy study of the inhibitory potential of red wine polyphenols on vascular smooth muscle cell proliferation". Planta Med. 78 (8): 772–8. doi:10.1055/s-0031-1298440. PMID 22499559.
- Knab AM, Shanely RA, Jin F, Austin MD, Sha W, Nieman DC (June 2011). "Quercetin with vitamin C and niacin does not affect body mass or composition". Appl Physiol Nutr Metab 36 (3): 331–8. doi:10.1139/h11-015. PMID 21574787.
- Knab AM, Shanely RA, Henson DA, Jin F, Heinz SA, Austin MD, Nieman DC (April 2011). "Influence of quercetin supplementation on disease risk factors in community-dwelling adults". J Am Diet Assoc 111 (4): 542–9. doi:10.1016/j.jada.2011.01.013. PMID 21443986.
- Saaby L, Rasmussen HB, Jäger AK (January 2009). "MAO-A inhibitory activity of quercetin from Calluna vulgaris (L.) Hull". J Ethnopharmacol 121 (1): 178–81. doi:10.1016/j.jep.2008.10.012. PMID 19013512.
- Shoskes DA, Zeitlin SI, Shahed A, Rajfer J (1999). "Quercetin in men with category III chronic prostatitis: a preliminary prospective, double-blind, placebo-controlled trial". Urology (Dec): 960–3.
- Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF (1995). "A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase". Adv. Exp. Med. Biol. 390: 59–69. doi:10.1007/978-1-4757-9203-4_5. PMID 8718602.
- Bun SS, Ciccolini J, Bun H, Aubert C, Catalin J (June 2003). "Drug interactions of paclitaxel metabolism in human liver microsomes". J Chemother 15 (3): 266–74. doi:10.1179/joc.2003.15.3.266. PMID 12868554.
- Bun SS, Giacometti S, Fanciullino R, Ciccolini J, Bun H, Aubert C (July 2005). "Effect of several compounds on biliary excretion of paclitaxel and its metabolites in guinea-pigs". Anticancer Drugs 16 (6): 675–82. doi:10.1097/00001813-200507000-00013. PMID 15930897.
- Si Dayong, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition 37 (3): 629–634. doi:10.1124/dmd.108.023416. PMID 19074529.
- Hsiu SL, Hou YC, Wang YH, Tsao CW, Su SF, Chao PD (December 2002). "Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats". Life Sci. 72 (3): 227–35. doi:10.1016/S0024-3205(02)02235-X. PMID 12427482.
- Raucy JL (May 2003). "Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products". Drug Metab. Dispos. 31 (5): 533–9. doi:10.1124/dmd.31.5.533. PMID 12695340.
- UMM Complementary and Alternative Medicine Guide: Quercetin (University of Maryland Medical Center Website)
- Russo, Maria; Spagnuolo, Carmela; Tedesco, Idolo; Bilotto, Stefania; Russo, Gian Luigi (2012). "The flavonoid quercetin in disease prevention and therapy: Facts and fancies". Biochemical Pharmacology 83 (1): 6–15. doi:10.1016/j.bcp.2011.08.010. PMID 21856292.
- Loke, Wai Mun; Hodgson, Jonathan M; Proudfoot, Julie M; McKinley, Allan J; Puddey, Ian B; Croft, Kevin D (2008). "Pure dietary flavonoids quercetin and (−)-epicatechin augment nitric oxide products and reduce endothelin-1 acutely in healthy men". The American Journal of Clinical Nutrition 88 (4): 1018–25. PMID 18842789.
- Murota, Kaeko; Terao, Junji (2003). "Antioxidative flavonoid quercetin: Implication of its intestinal absorption and metabolism". Archives of Biochemistry and Biophysics 417 (1): 12–7. doi:10.1016/S0003-9861(03)00284-4. PMID 12921774.