Quercetin



Quercetin
IUPAC name 3,3',4',5,7-pentahydroxy-2-phenylchromen-4-one
Identifiers
CAS number 117-39-5
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 disclaimer and references

Quercetin is a flavonol.

Chemical structure

It is the rhamnose and rutinose, respectively.

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 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 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.[3]

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].

Occurrence

Foods rich in quercetin include capers (1800mg/kg)[4], prickly pear cactus. A recent study found that organically grown tomatoes had 79% more quercetin than conventionally grown.[7]

A study[8] 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.[9]

In plants, it is a naturally-occurring polar auxin transport inhibitor.

It also may be found in dietary supplements.

Drug interactions

Quercetin is contraindicated with antibiotics; it may interact with gyrase. Whether this inhibits or enhances the effect of fluoroquinolones is not entirely clear.[10]

Quercetin is also a potent inhibitor of drugs in the body.[11]

See also

  • Phytonutrients

References

  1. ^ BBC Onions 'cut heart disease risk' 4 November 2007
  2. ^ (2005) "Induction of cancer-specific cytotoxicity towards human prostate and skin cells using quercetin and ultrasound". British Journal of Cancer 92 (3): 499-502. doi:10.1038/sj.bjc.6602364. Retrieved on 2007-5-19.
  3. ^ Shoskes, DA et al (1999). "Quercetin in men with category III chronic prostatitis: a preliminary prospective, double-blind, placebo-controlled trial.". Urology. 54 (6).
  4. ^ USDA Database for the Flavonoid Content of Selected Foods
  5. ^ Crystal Smith, Kevin A. Lombard, Ellen B. Peffley, Weixin Liu (2003). "Genetic Analysis of Quercetin in Onion (Allium cepa L.) Lady Raider". The Texas Journal of Agriculture and Natural Resource 16: 24-28. Agriculture Consortium of Texas.
  6. ^ 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. Retrieved on 2007-06-13.
  7. ^ 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+.
  8. ^ Honey Research Unit
  9. ^ honey fingerprinting
  10. ^ 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.
  11. ^ 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.
 
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