Flavonoids: Wikis

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Molecular structure of the flavone backbone (2-phenyl-1,4-benzopyrone)
Isoflavan structure
Neoflavonoids structure

Flavonoids (or bioflavonoids), also collectively known as Vitamin P and citrin[1], are a class of plant secondary metabolites. According to the IUPAC nomenclature,[2] they can be classified into:

The three flavonoid classes above are all ketone-containing compounds, and as such, are flavonoids and flavonols. This class was the first to be termed "bioflavonoids." The terms flavonoid and bioflavonoid have also been more loosely used to describe non-ketone polyhydroxy polyphenol compounds which are more specifically termed flavanoids, flavan-3-ols, or catechins (although catechins are actually a subgroup of flavanoids).

Contents

Biosynthesis

Biological roles

Flavonoids are widely distributed in plants fulfilling many functions.

Flavonoids are the most important plant pigments for flower coloration producing yellow or red/blue pigmentation in petals. Those colors are a mean to attract pollinator animals.

Flavonoids secreted by the root of their host plant help Rhizobia in the infection stage of their symbiotic relationship with legumes like peas, beans, clover, and soy. Rhizobia living in soil are able to sense the flavonoids and this triggers the secretion of Nod factors, which in turn are recognized by the host plant and can lead to root hair deformation and several cellular responses such as ion fluxes and the formation of a root nodule.

They also protect plants from attacks by microbes, fungi[3] and insects.

Biological activity

Flavonoids (specifically flavanoids such as the catechins) are "the most common group of polyphenolic compounds in the human diet and are found ubiquitously in plants".[4] Flavonols, the original bioflavonoids such as quercetin, are also found ubiquitously, but in lesser quantities. Both sets of compounds have evidence of health-modulating effects in animals which eat them.

The widespread distribution of flavonoids, their variety and their relatively low toxicity compared to other active plant compounds (for instance alkaloids) mean that many animals, including humans, ingest significant quantities in their diet. Flavonoids have been referred to as "nature's biological response modifiers" because of strong experimental evidence of their inherent ability to modify the body's reaction to allergens, viruses, and carcinogens. They show anti-allergic, anti-inflammatory[5] , anti-microbial[6] and anti-cancer activity [7].

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Antioxidant activity

Flavonoids (both flavonols and flavanols) are most commonly known for their antioxidant activity in vitro.

Consumers and food manufacturers have become interested in flavonoids for their possible medicinal properties, especially their putative role in prevention of cancers and cardiovascular diseases. Although physiological evidence is not yet established, the beneficial effects of fruit, vegetables, and tea or even red wine have been attributed to flavonoid compounds rather than to known nutrients and vitamins.[8]

Alternatively, research conducted at the Linus Pauling Institute and evaluated by the European Food Safety Authority indicates that, following dietary intake, flavonoids themselves are of little or no direct antioxidant value.[9][10] As body conditions are unlike controlled test tube conditions, flavonoids and other polyphenols are poorly absorbed (less than 5%), with most of what is absorbed being quickly metabolized and excreted. The increase in antioxidant capacity of blood seen after the consumption of flavonoid-rich foods is not caused directly by flavonoids themselves, but most likely is due to increased uric acid levels that result from metabolism of flavonoids.[11] According to Frei, "we can now follow the activity of flavonoids in the body, and one thing that is clear is that the body sees them as foreign compounds and is trying to get rid of them."

Other health benefits

Cancer

The process of gearing up to get rid of unwanted compounds induces so-called Phase II enzymes that also help to eliminate mutagens and carcinogens, and therefore may be of value in cancer prevention. Flavonoids could also induce mechanisms that help kill cancer cells and inhibit tumor invasion."[11] UCLA cancer researchers have found that study participants who ate foods containing certain flavonoids seemed to be protected from developing lung cancer. Dr. Zuo-Feng Zhang, of the UCLA's Jonsson Cancer Center and a professor of public health and epidemiology at the UCLA School of Public Health said the flavonoids that appeared to be the most protective included catechin, found in strawberries and green and black teas; kaempferol, found in brussel sprouts and apples; and quercetin, found in beans, onions and apples.[12]

Their research also indicated that only small amounts of flavonoids are necessary to see these medical benefits. Taking large dietary supplements provides no extra benefit and may pose some risks.[11]

Diarrhea

A study done at Children's Hospital & Research Center Oakland, in collaboration with scientists at Heinrich Heine University in Germany, has shown that epicatechin, quercetin and luteolin can inhibit the development of fluids that result in diarrhea by targeting the intestinal cystic fibrosis transmembrane conductance regulator Cl– transport inhibiting cAMP-stimulated Cl– secretion in the intestine.[13]

Capillary stabilising agents

Bioflavonoids like rutin, monoxerutin, diosmin, troxerutin and hidrosmin have vasoprotective proprieties.

Important flavonoids

Quercetin

Quercetin

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. It may also help to prevent some types of cancer, however currently there is more research needed in this area.

Epicatechin

Epicatechin (EC)

Epicatechin improves blood flow and thus seems good for cardiac health. Cocoa, the major ingredient of dark chocolate, contains relatively high amounts of epicatechin and has been found to have nearly twice the antioxidant content of red wine and up to three times that of green tea in in-vitro tests.[14][15] But in the test outlined above it now appears the beneficial antioxidant effects are minimal as the antioxidants are rapidly excreted from the body.

Important dietary sources

Good sources of flavonoids include all citrus fruits, berries, ginkgo biloba, onions[16][17], parsley[18], (particularly red onion[19]) pulses[20], tea (especially white and green tea), red wine, seabuckthorn, and dark chocolate (with a cocoa content of seventy percent or greater).

Citrus

A variety of flavonoids are found in citrus fruits, including grapefruit.

The citrus bioflavonoids include hesperidin (a glycoside of the flavanone hesperetin), quercitrin, rutin (two glycosides of the flavonol quercetin), and the flavone tangeritin. In addition to possessing antioxidant activity and an ability to increase intracellular levels of vitamin C, rutin and hesperidin exert beneficial effects on capillary permeability and blood flow. They also exhibit some of the anti-allergy and anti-inflammatory benefits of quercetin. Quercetin can also inhibit reverse transcriptase, part of the replication process of retroviruses.[21] The therapeutical relevance of this inhibition has not been established. Hydroxyethylrutosides (HER) have been used in the treatment of capillary permeability, easy bruising, hemorrhoids, and varicose veins.

Tea

Bai Hao Yinzhen from Fuding in Fujian Province, widely considered[citation needed] the best grade of white tea

Green tea flavonoids are potent antioxidant compounds, thought to reduce incidence of cancer and heart disease. The major flavonoids in green tea are the kaempferol and catechins (catechin, epicatechin, epicatechin gallate (ECG), and epigallocatechin gallate (EGCG)).

In producing teas such as oolong tea and black tea, the leaves are allowed to oxidize, during which enzymes present in the tea convert some or all of the catechins to larger molecules[citation needed]. However, green tea is produced by steaming the fresh-cut leaf, which inactivates these enzymes, and oxidation does not significantly occur. White tea is the least processed of teas and is shown[citation needed] to present the highest amount of catechins known to occur in camellia sinensis.

Wine

Grape skins contain significant amounts of flavonoids as well as other polyphenols[22]. Both red and white wine contain flavonoids; however, since red wine is produced by fermentation in the presence of the grape skins, red wine has been observed to contain higher levels of flavonoids, and other polyphenolics such as resveratrol.

Dark chocolate

Flavonoids exist naturally in cacao, but because they can be bitter, they are often removed from chocolate, even the dark variety.[23] While the flavonoids are present in milk chocolate, studies have shown that they are not as readily taken up by the body; nor are they easily taken up when dark chocolate is consumed alongside milk.[24]

Subgroups

Over 5000 naturally occurring flavonoids have been characterized from various plants. They have been classified according to their chemical structure, and are usually subdivided into the following subgroups (for further reading see [25]):

Flavones

Flavones are divided into four groups:[26]

Group Skeleton Examples
Description Functional groups Structural formula
3-hydroxyl 2,3-dihydro
Flavone 2-phenylchromen-4-one Flavone skeleton colored.svg Luteolin, Apigenin, Tangeritin
Flavonol
or
3-hydroxyflavone
3-hydroxy-2-phenylchromen-4-one Flavonol skeleton colored.svg Quercetin, Kaempferol, Myricetin, Fisetin, Isorhamnetin, Pachypodol, Rhamnazin
Flavanone 2,3-dihydro-2-phenylchromen-4-one Flavanone skeleton colored.svg Hesperetin, Naringenin, Eriodictyol, Homoeriodictyol
Flavanonol
or
3-Hydroxyflavanone
or
2,3-dihydroflavonol
3-hydroxy-2,3-dihydro-2-phenylchromen-4-one Flavanonol skeleton colored.svg Taxifolin (or Dihydroquercetin), Dihydrokaempferol

Isoflavones

Flavan-3-ols, Flavan-4-ols, Flavan-3,4-diols, and proanthocyanidins

Flavan structure

Derivatives of flavan.

Skeleton Name
Flavan-3ol Flavan-3-ol
Flavan-4ol Flavan-4-ol
Flavan-3,4-diol Flavan-3,4-diol (leucoanthocyanidin)

Anthocyanidins

Flavylium skeleton of anthocyanidins

Availability through microorganisms

Several recent research articles have demonstrated the efficient production of flavonoid molecules from genetically-engineered microorganisms[27][28][29].

See also

References

  1. ^ http://dictionary.reference.com/browse/vitamin+p
  2. ^ Flavonoids (isoflavonoids and neoflavonoids)., IUPAC Compendium of Chemical Terminology
  3. ^ [http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B8JGN-4RPW61B-2&_user=10&_coverDate=04%2F15%2F2008&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=739d5f51f1bb8fb59557acdde30e8787 Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity Francesco Galeotti, Elisa Barile, Paolo Curir, Marcello Dolcia and Virginia Lanzotti, Phytochemistry Letters, Volume 1, Issue 1, 15 April 2008, Pages 44-48, doi:10.1016/j.phytol.2007.10.001]
  4. ^ Spencer, J. P. E. (May 2008). "Flavonoids: modulators of brain function?". The British journal of nutrition 99 E Suppl 1: ES60–ES77. doi:10.1017/S0007114508965776. ISSN 0007-1145. PMID 18503736.  edit
  5. ^ "Therapeutic potential of inhibition of the NF-κB pathway in the treatment of inflammation and cancer". Yamamoto and Gaynor 107 (2): 135 -- Journal of Clinical Investigation. http://www.jci.org/cgi/content/full/107/2/135?ijkey=a1e09ce2dbca283cec170598f2410b15d5f4304f&keytype2=tf_ipsecsha. 
  6. ^ Cushnie TPT, Lamb AJ (2005). "Antimicrobial activity of flavonoids". International Journal of Antimicrobial Agents 26 (5): 343–356. doi:10.1016/j.ijantimicag.2005.09.002. PMID 16323269. 
  7. ^ de Sousa RR, Queiroz KC, Souza AC, Gurgueira SA, Augusto AC, Miranda MA, Peppelenbosch MP, Ferreira CV, Aoyama H. (2007). "Phosphoprotein levels, MAPK activities and NFkappaB expression are affected by fisetin". J Enzyme Inhib Med Chem 22 (4): 439–444. doi:10.1080/14756360601162063. PMID 17847710. 
  8. ^ Félicien Breton (2008). "Health benefits of oligomeric proanthocyanidins". http://www.frenchscout.com/polyphenols#procyanidins. 
  9. ^ Lotito SB, Frei B (2006). "Consumption of flavonoid-rich foods and increased plasma antioxidant capacity in humans: cause, consequence, or epiphenomenon?". Free Radic. Biol. Med. 41 (12): 1727–46. doi:10.1016/j.freeradbiomed.2006.04.033. PMID 17157175. 
  10. ^ Scientific Opinion on the substantiation of health claims related to various food(s)/food constituent(s) and protection of cells from premature aging, antioxidant activity, antioxidant content and antioxidant properties, and protection of DNA, proteins and lipids from oxidative damage pursuant to Article 13(1) of Regulation (EC) No 1924/20061, EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA)2, 3 European Food Safety Authority (EFSA), Parma, Italy, EFSA Journal 2010; 8(2):1489
  11. ^ a b c "Studies force new view on biology of flavonoids", by David Stauth, EurekAlert!. Adapted from a news release issued by Oregon State University. URL accessed .
  12. ^ UCLA news May 2008 - Fruits, vegetables, teas may protect smokers from lung cancer
  13. ^ Schuier M, Sies H, Illek B, Fischer H (1 October 2005). "Cocoa-related flavonoids inhibit CFTR-mediated chloride transport across T84 human colon epithelia". J. Nutr. 135 (10): 2320–5. PMID 16177189. http://jn.nutrition.org/cgi/reprint/135/10/2320. 
  14. ^ Lee KW, Kim YJ, Lee HJ, Lee CY (December 2003). "Cocoa has more phenolic phytochemicals and a higher antioxidant capacity than teas and red wine". J. Agric. Food Chem. 51 (25): 7292–5. doi:10.1021/jf0344385. PMID 14640573. 
  15. ^ "Cocoa nutrient for 'lethal ills'". BBC News. http://news.bbc.co.uk/2/hi/health/.stm. 
  16. ^ Tsushida T., Suzuki, M. (1996) Content of flavonol glucosides and some properties of enzymes metabolizing the glucosides in onion. J. Jap. Soc. Food Sci. Technol., 43, 642-649.
  17. ^ Slimestad R, Fossen T, Vågen IM (December 2007). "Onions: a source of unique dietary flavonoids". J. Agric. Food Chem. 55 (25): 10067–80. doi:10.1021/jf0712503. PMID 17997520. 
  18. ^ Justesen U, Knuthsen P (2001). "Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes". Food Chem. 73: 245–50. doi:10.1016/S0308-8146(01)00114-5. 
  19. ^ http://www3.interscience.wiley.com/journal/118909668/abstract?CRETRY=1&SRETRY=0
  20. ^ Ewald C, Fjelkner-Modig S, Johansson K, Sjöholm I, Åkesson B (1999). "Effect of processing on major flavonoids in processed onions, green beans, and peas". Food Chem. 64: 231–5. doi:10.1016/S0308-8146(98)00136-8. 
  21. ^ 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. 
  22. ^ Kennedy JA, Matthews MA, Waterhouse AL (2002). "Effect of Maturity and Vine Water Status on Grape Skin and Wine Flavonoids". Am. J. Enol. Vitic. 53 (4): 268–74. http://www.ajevonline.org/cgi/content/abstract/53/4/268. 
  23. ^ The Lancet, (December 2007). "The devil in the dark chocolate". Lancet 370 (9605): 2070. doi:10.1016/S0140-6736(07)61873-X. PMID 18156011. http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(07)61873-X. 
  24. ^ Serafini et al; Bugianesi, Rossana; Maiani, Giuseppe; Valtuena, Silvia; De Santis, Simone; Crozier, Alan (August 2003). "Plasma antioxidants from chocolate". Nature 424: 1013. doi:10.1038/4241013a. http://www.nature.com/nature/journal/v424/n6952/full/4241013a.html. 
  25. ^ Ververidis Filippos, F; Trantas Emmanouil, Douglas Carl, Vollmer Guenter, Kretzschmar Georg, Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal 2 (10): 1214. doi:10.1002/biot.200700084. PMID 17935117. 
  26. ^ Phenolics:figure 4
  27. ^ Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S (May 2003). "Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster". Appl. Environ. Microbiol. 69 (5): 2699–706. doi:10.1128/AEM.69.5.2699-2706.2003. PMID 12732539. PMC 154558. http://aem.asm.org/cgi/pmidlookup?view=long&pmid=12732539. 
  28. ^ Trantas Emmanouil; Panopoulos Nickolas, Ververidis Filippos (2009). "Metabolic engineering of the complete pathway leading to heterologous biosynthesis of various flavonoids and stilbenoids in Saccharomyces cerevisiae". Metabolic Engineering 11: 355-366. doi:10.1016/j.ymben.2009.07.004. 
  29. ^ Ververidis Filippos, F; Trantas Emmanouil, Douglas Carl, Vollmer Guenter, Kretzschmar Georg, Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part II: Reconstruction of multienzyme pathways in plants and microbes". Biotechnology Journal 2 (10): 1235. doi:10.1002/biot.200700184. PMID 17935118. 

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