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Quercetin
IUPAC name	2-(3,4-dihydroxyphenyl)- 3,5,7-trihydroxy-4H-chromen-4-one
Identifiers
CAS number	[117-39-5]
PubChem	5280343
SMILES	Oc1cc(O)c2C(=O)C(O)= C(Oc2c1)c3ccc(O)c(O)c3
Properties
Molecular formula	C15H10O7
Molar mass	302.236 g/mol
Density	1.799 g/cm3
Melting point	316 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Quercetin is a flavonoid and, to be more specific, a flavonol. It 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. Quercetin is classified as IARC group 3 (no evidence of carcinogenicity in humans).

Occurrence

Quercetin is a naturally-occurring polar auxin transport inhibitor.^{citation needed}

Foods rich in quercetin include capers (1800mg/kg)^[1], lovage (1700mg/kg), apples (440mg/kg), tea (Camellia sinensis), onions, especially in red onions (higher concentrations of quercetin occur in the outermost rings^[2]), red grapes, citrus fruits, broccoli and other leafy green vegetables, cherries, and a number of berries including raspberry, bog whortleberry (158 mg/kg, fresh weight), lingonberry (cultivated 74mg/kg, wild 146 mg/kg), cranberry (cultivated 83 mg/kg, wild 121 mg/kg), chokeberry (89 mg/kg), sweet rowan (85 mg/kg), rowanberry (63 mg/kg), sea buckthorn berry (62 mg/kg), crowberry (cultivated 53mg/kg, wild 56 mg/kg),^[3] and the fruit of the prickly pear cactus. A recent study found that organically grown tomatoes had 79% more quercetin than "conventionally grown".^[4]

A study^[5] by the University of Queensland, Australia, has also indicated the presence of quercetin in varieties of honey, including honey derived from eucalyptus and tea tree flowers.^[6]

Medicinal properties

Quercetin is found to be the most active of the flavonoids in studies,^{citation needed} and many medicinal plants owe much of their activity to their high quercetin content. Quercetin has demonstrated significant anti-inflammatory activity because of direct inhibition of several initial processes of inflammation.^[7] For example, it inhibits both the manufacture and release of histamine and other allergic/inflammatory mediators. In addition, it exerts potent antioxidant activity and vitamin C-sparing action^{citation needed}.

Quercetin also shows anti-tumour properties. A study in the British Journal of Cancer showed that, when treated with a combination of quercetin and ultrasound at 20 kHz for 1 minute duration, skin and prostate cancers show a 90% mortality within 48 hours with no visible mortality of normal cells.^[8] Note that ultrasound also promotes topical absorption by up to 1,000 times making the use of topical quercetin and ultrasound wands an interesting proposition.

Recent studies have supported that quercetin can help men with chronic prostatitis, and both men and women with interstitial cystitis, possibly because of its action as a mast cell inhibitor.^[9]

Quercetin may have positive effects in combating or helping to prevent cancer, prostatitis, heart disease, cataracts, allergies/inflammations, and respiratory diseases such as bronchitis and asthma^{citation needed}. It also has been claimed to have antidepressant properties, however any claim of quercetin action against neurological diseases should be treated with skepticism due to the fact that quercitin is a neurotoxin in vitro.^[10]

It also may be found in dietary supplements.

An 8-year study found that three flavonols — kaempferol, quercetin, and myricetin — were associated with a reduced risk of pancreatic cancer of 23 percent.^[11]

Drug interactions

Quercetin is contraindicated with some antibiotics; it may interact with fluoroquinolones (a type of medicinal antibiotic), as quercetin competitively binds to bacterial DNA gyrase. Whether this inhibits or enhances the effect of fluoroquinolones is not entirely clear.^[12]

Quercetin is also a potent inhibitor of CYP3A4, an enzyme that breaks down most drugs in the body.^[13] As such, quercetin would be expected to increase serum levels, and therefore effects, of drugs metabolized by this enzyme.

See also

• Phytonutrients
• Quercetin 2,3-dioxygenase
• Quercetin 3-O-methyltransferase
• Flavonol 3-sulfotransferase
• Quercetin-3-sulfate 3'-sulfotransferase
• Quercetin-3-sulfate 4'-sulfotransferase
• Quercetin-3,3'-bissulfate 7-sulfotransferase
• Phenolic compounds in wine

References

1. ^ USDA Database for the Flavonoid Content of Selected Foods
2. ^ Crystal Smith, Kevin A. Lombard, Ellen B. Peffley, Weixin Liu (2003). "Genetic Analysis of Quercetin in Onion (Allium cepa L.) Lady Raider" (^{dead link}). The Texas Journal of Agriculture and Natural Resource 16: 24–28. Agriculture Consortium of Texas. 
3. ^ Sari H. Häkkinen et al (1999). "Content of the Flavonols Quercetin, Myricetin, and Kaempferol in 25 Edible Berries". Journal of Agricultural and Food Chemistry 47 (6): 2274–2279. doi:10.1021/jf9811065. PMID 10794622. 
4. ^ A. E. Mitchell, Y. J. Hong, E. Koh, D. M. Barrett, D. E. Bryant, R. F. Denison and S. Kaffka (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): 6154–6159. doi:10.1021/jf070344 (inactive 2008-06-23). 
5. ^ Honey Research Unit
6. ^ honey fingerprinting
7. ^ BBC Onions 'cut heart disease risk' 4 November 2007
8. ^ Paliwal, S (2005). "Induction of cancer-specific cytotoxicity towards human prostate and skin cells using quercetin and ultrasound" (abstract). British Journal of Cancer 92 (3): 499–502. doi:10.1038/sj.bjc.6602364. Retrieved on 2007-05-19. 
9. ^ Shoskes, DA et al (1999). "Quercetin in men with category III chronic prostatitis: a preliminary prospective, double-blind, placebo-controlled trial". Urology. 54 (6): 960–3. doi:10.1016/S0090-4295(99)00358-1. PMID 10604689. 
10. ^ Ossola, B (2008). "Paradoxical co-existence of protective and toxic effects of quercetin in the same in vitro neurodegeneration model". European Journal of Pharmaceutical Sciences 34 (1): S33. doi:10.1016/j.ejps.2008.02.088. 
11. ^ Ute Nöthlings, Suzanne P. Murphy, Lynne R. Wilkens, Brian E. Henderson3 and Laurence N. Kolonel (2007). "Flavonols and Pancreatic Cancer Risk". American Journal of Epidemiology 166 (8): 924–931. doi:10.1093/aje/kwm172. PMID 17690219. 
12. ^ Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF. 'A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. PMID 8718602.
13. ^ Su-Lan Hsiu; Yu-Chi Hou; Yao-Horng Wang; Chih-Wan Tsao; Sheng-Fang Sue; and Pei-Dawn L. Chao (6 December 2002). "Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats". Life Sciences 72 (3): 227–235. doi:10.1016/S0024-3205(02)02235-X. 

External links

• UMM Quercetin Info Page (University of Maryland Medical Center Website)
• Eyes right for a cup of tea UK Institute of Food Research article on how quercetin can help prevent cataracts.
• Plant foods for health protection article by the Institute of Food Research (Norwich, United Kingdom)
• Scanning Electron Micrograph image of quercetin crystals derived from onion
• Possible Interactions with: Quercetin Quercetin might enhance the effects of two chemotherapy medications
• Quercetin Info from the Cedars-Sinai Medical Center, Los Angeles.
• "Genetic Analysis of Quercetin in Onion (Allium cepa L.)" article from The Texas Journal of Agriculture and Natural Resource 16:24-28 (2003).
• "Ten-Year Comparison of the Influence of Organic and Conventional Crop Management Practices on the Content of Flavonoids in Tomatoes" article at American Chemical Society website (originally published 23 June 2007).
• "An apple a day could help protect against brain-cell damage" article at Cornell University website (originally published 2 December 2004).

Wikipedia content modification information:

• This page was last modified on 9 October 2008, at 23:47.

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