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07-SEPTEMBER-2008 03:17:44 - Flavonoid Redirected from Flavonoids Molecular structure of the flavone backbone 2-phenyl-1,4-benzopyrone Molecular structure of the flavone backbone 2-phenyl-1,4-benzopyrone The term flavonoid or bioflavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature,1 they can be classified into: flavonoids, derived from 2-phenylchromen-4-one 2-phenyl-1,4-benzopyrone structure isoflavonoids, derived from 3-phenylchromen-4-one 3-phenyl-1,4-benzopyrone structure neoflavonoids, derived from 4-phenylcoumarine 4-phenyl-1,2-benzopyrone structure. Flavonoids are most commonly known for their antioxidant activity. However, it is now known that the health benefits they provide against cancer and heart disease are the result of other mechanisms.23 Flavonoids are also commonly referred to as bioflavonoids in the media - the terms are largely equivalent and interchangeable, for most flavonoids are biological in origin. Contents 1 Biosynthesis 2 Biological effects 2.1 Health benefits aside from antioxidant values 2.1.1 Diarrhea 3 Important flavonoids 3.1 Quercetin 3.2 Epicatechin 3.3 Oligomeric proanthocyanidins 4 Important dietary sources 4.1 Citrus 4.2 Ginkgo 4.3 Tea 4.4 Wine 4.5 Dark chocolate 5 Subgroups 5.1 Flavones 5.2 Isoflavones 5.3 Flavan-3-ols and Anthocyanidins 6 Availability through microorganisms 7 See also 8 References 9 External links Biosynthesis Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA3. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings see polyphenols. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins tannins and a host of other polyphenolics. Biological effects Flavonoids are widely distributed in plants fulfilling many functions including producing yellow or red/blue pigmentation in flowers and protection from attack by microbes and insects. 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-inflammatory4 , anti-microbial5 and anti-cancer activity. Consumers and food manufacturers have become interested in flavonoids for their medicinal properties, especially their potential role in the prevention of cancers and cardiovascular disease. The beneficial effects of fruit, vegetables, and tea or even red wine have been attributed to flavonoid compounds rather than to known nutrients and vitaminscitation needed. Health benefits aside from antioxidant values In 2007, research conducted at the Linus Pauling Institute and published in Free Radical Biology and Medicine indicates that inside the human body, flavonoids themselves are of little or no direct antioxidant value.6 Unlike in the controlled conditions of a test tube, flavonoids are poorly absorbed by the human body less than 5%, and most of what is absorbed is quickly metabolized and excreted from the body. The huge increase in antioxidant capacity of blood seen after the consumption of flavonoid-rich foods is not caused directly by the flavonoids themselves, but most likely is due to increased uric acid levels that result from expelling flavonoids from the body.2 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. But this process of gearing up to get rid of unwanted compounds is inducing so-called Phase II enzymes that also help 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.2 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.2 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.7 Important flavonoids This article or section needs to be updated. Please update the article to reflect recent events / newly available information, and remove this template when finished. Quercetin Main article: quercetin Quercetin Quercetin Quercetin is a flavonoid and, to be more specific, a flavonol see below, that constitutes the aglycone of the glycosides rutin and quercitrin. In studies, quercetin is found to be the most active of the flavonoids,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. For example, quercetin inhibits both the production and release of histamine and other allergic/inflammatory mediators.citation needed In addition, it exerts potent antioxidant activity and vitamin C-sparing action. It may also help to prevent some types of cancer. Quercetin can be found in the herbal products based on Hawthorn, which are used for acute symptoms of congestive heart failure.citation needed One study that people who ate quercetin-rich foods at least four times a week, on average, were 51% less likely to have lung cancer than those who ate none.citation needed Epicatechin Epicatechin EC 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.8 9 But in the test outlined above it now appears the beneficial antioxidant effects are minimal as the antioxidants are rapidly excreted from the body. Oligomeric proanthocyanidins Proanthocyanidins extracts demonstrate a wide range of pharmacological activity. Their effects include increasing intracellular vitamin C levels, decreasing capillary permeability and fragility, scavenging oxidants and free radicals, and inhibiting destruction of collagen, the most abundant protein in the body. Important dietary sources This article or section needs to be updated. Please update the article to reflect recent events / newly available information, and remove this template when finished. Good sources of flavonoids include all citrus fruits, berries, ginkgo biloba, onions1011, parsley12, pulses13, tea especially white and green tea, red wine, seabuckthorn, and dark chocolate with a cocoa content of seventy percent or greater. Citrus Grapefruit, a type of Citrus Grapefruit, a type of Citrus 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.14 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. Ginkgo Leaf extract from the Ginkgo tree is widely marketed as an herbal supplement. The active ingredients are flavoglycosides. Tea Bai Hao Yinzhen from Fuding in Fujian Province, widely considered the best grade of white tea Bai Hao Yinzhen from Fuding in Fujian Province, widely considered 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, 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. 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 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 polyphenols15. 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 Flavanoids exist naturally in cacao, but because they can be bitter, they are often removed from chocolate, even the dark variety16. 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 3: Flavones Flavones are divided into four groups:17 Group Skeleton Examples Description Functional groups Structural formula 3-hydroxyl 2,3-dihydro Flavone 2-phenylchromen-4-one Image:Flavone_skeleton_colored.svg Luteolin, Apigenin, Tangeritin Flavonol or 3-hydroxyflavone 3-hydroxy-2-phenylchromen-4-one Image:Flavonol_skeleton_colored.svg Quercetin, Kaempferol, Myricetin, Fisetin, Isorhamnetin, Pachypodol, Rhamnazin Flavanone 2,3-dihydro-2-phenylchromen-4-one Image: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 Image:Flavanonol_skeleton_colored.svg Taxifolin or Dihydroquercetin, Dihydrokaempferol Isoflavones Isoflavones Isoflavones use the 3-phenylchromen-4-one skeleton with no hydroxyl group substitution on carbon at position 2. Examples: Genistein, Daidzein, Glycitein Flavan-3-ols and Anthocyanidins Flavan-3-ols also known as Flavanols Flavan-3-ols use the 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Examples: Catechins Catechin C, Gallocatechin GC, Catechin 3-gallate Cg, Gallocatechin 3-gallate GCg, Epicatechins Epicatechin EC, Epigallocatechin EGC, Epicatechin 3-gallate ECg, Epigallocatechin 3-gallate EGCg Anthocyanidins Anthocyanidins are the aglycones of anthocyanins. Anthocyanidins use the flavylium 2-phenylchromenylium ion skeleton Examples: Cyanidin, Delphinidin, Malvidin, Pelargonidin, Peonidin, Petunidin Availability through microorganisms A number of recent research articles have demonstrated the efficient production of flavonoid molecules from genetically-engineered microorganisms1819. See also Phytochemistry Phytoalexin References ^ Flavonoids isoflavonoids and neoflavonoids., IUPAC Compendium of Chemical Terminology ^ a b c d Studies force new view on biology of flavonoids, by David Stauth, EurekAlert!. Adapted from a news release issued by Oregon State University. URL accessed . ^ a b c Ververidis Filippos; 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. ^ 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. ^ 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. ^ 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. ^ Schuier, Maximilian; Helmut Sies, Beate Illek, and Horst Fischer October 2005. Cocoa-Related Flavonoids Inhibit CFTR-Mediated Chloride Transport across T84 Human Colon Epithelia PDF. Journal of Nutrition 135 10. ^ J. Agric.Food Chem. 2003 51: Lee et al. ^ Cocoa nutrient for 'lethal ills'. BBC News. ^ 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. ^ Slimestad R, Fossen T, VÃ¥gen IM. 2007 Onions: a source of unique dietary flavonoids. J Agric Food Chem. 2007 Dec 12;5525:10067-80. Epub 2007 Nov 13. PMID 17997520 ^ Justesen, U., and Knuthsen, P. Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes. Food Chem., 2001, 73, 245-250. PMID 11192169 ^ Ewald, C., Fjelkner-Modig, S., Johansson, K., Sjöholm, I., and Ã…kesson. B. Effect of processing on major flavonoids in processed onions, green beans, and peas. Food Chem., 1999, 64, 231-235. ^ Spedding, G., Ratty, A., Middleton, E. Jr. 1989 Inhibition of reverse transcriptases by flavonoids. Antiviral Res 12 2, 99-110. PMID ^ James A. Kennedy, Mark A. Matthews, and Andrew L. Waterhouse, Effect of Maturity and Vine Water Status on Grape Skin and Wine Flavonoids Am. J. Enol. Vitic. 53:4: abstract ^ orial. 'The devil in the dark chocolate.' The Lancet. 2007; 370:2070 1 ^ Phenolics:figure 4 ^ Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S. Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Appl Environ Microbiol. 2003 May;695: PMID ^ Ververidis Filippos; 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. External links USDA Database of Flavonoid content of food pdf Flavonoids chemistry Flavonoids chemistry Cornell news on Cocoa A Dark Chocolate a Day Keeps the Doctor Away Antioxidant in Green Tea may fight Alzheimer's-EGCG Therapeutic potential of the NF-kB pathway in the treatment of inflammatory disorders v d e Types of Phenylpropanoids Phenylpropanoids Cinnamic acids Cinnamaldehydes Monolignols Coumarins Flavonoids Stilbenoids Furanocoumarin Lignans Lignins Suberins v d e Types of Flavonoids Flavones: Apigenin | Luteolin | Tangeritin Synthetics: Diosmin | Flavoxate Isoflavones: Biochanin A | Coumestrol | Daidzein | Daidzin | Formononetin | Genistein | Puerarin Flavonols: Fisetin | Isorhamnetin | Kaempferol | Myricetin | Pachypodol | Quercetin | Rhamnazin Flavanones: Eriodictyol | Hesperetin | Homoeriodictyol | Naringenin 3-Hydroxyflavanones: Dihydrokaempferol | Dihydroquercetin Flavan-3-ols: Catechins | Epicatechins | Epigallocatechin Anthocyanidins: Cyanidin | Delphinidin | Malvidin | Pelargonidin | Peonidin | Petunidin Misc: List of phytochemicals and foods in which they are prominent Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Flavonoid Categories: Flavonoids | Nutrients | Nutrition | Dietary antioxidantsHidden categories: All articles with statements | Articles with statements since May 2008 | articles in need of updating Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Català Česky Dansk Deutsch Español Esperanto Français Italiano Lietuvių Magyar Nederlands 日本語 Polski Português Română РуÑ?Ñ?кий SlovenÄ?ina SlovenÅ¡Ä?ina Suomi Svenska ä¸æ–‡ This page was last modified on 22 August 2008, at 08:59
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