Flavonoid
From Wikipedia, the free encyclopedia
The term flavonoid refers to a class of plant secondary metabolites. According to the IUPAC nomenclature, they can be classified into:
- flavonoids, derived from the 2-phenylchromone (2-phenyl-1,4-benzopyrone) structure
- isoflavonoids, derived from the 3-phenylchromone (3-phenyl-1,4-benzopyrone) structure
- neoflavonoids, derived from the 4-phenylcoumarine (4-phenyl-1,2-benzopyrone) structure.
Flavonoids are most commonly known for their antioxidant activity. Flavonoids are also commonly referred to as bioflavonoids in the media – these terms are equivalent and interchangeable, since all flavonoids are biological in origin.
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[edit] Biosynthesis
Flavonoids are synthesized by the phenylpropanoid pathway in which the amino acid phenylalanine is used to produce 4-coumaryl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones. Ring-closure of these compounds results in the familiar form of flavonoids, a three-ringed structure (polyphenols). 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.
[edit] 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 found in high concentrations in butterflies and moths sequestered from dietary intake at the larval stage and then stored in adult tissues.
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[1] , anti-microbial and anti-cancer activity. In addition, flavonoids act as powerful antioxidants, protecting against oxidative and free radical damage.
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 vitamins.
[edit] Important flavonoids
[edit] Quercetin
Quercetin is a flavonoid and more specifically a flavonol (see below), that constitutes the aglycone of the glycoside rutin. In studies, quercetin is found to be the most active of the flavonoids, 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, it inhibits both the production and release of histamine and other allergic/inflammatory mediators. In addition, it exerts potent antioxidant activity and vitamin C-sparing action.
[edit] Epicatechin
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.[2]
[edit] 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.
[edit] Important dietary sources
Good sources of flavonoids include all citrus fruits, berries, onions, parsley, legumes, green tea, red wine, seabuckthorn, and dark chocolate (that with a cocoa content of seventy percent or greater).
[edit] Citrus
The citrus bioflavonoids include hesperidin, quercetin, rutin (a sugar of quercetin), and 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 (Spedding et al. 1989). 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.
[edit] Green Tea
Green tea polyphenols are potent antioxidant compounds that have demonstrated greater antioxidant protection than vitamins C and E. Green tea may also increase the activity of antioxidant enzymes. Green tea polyphenols may inhibit cancer by blocking the formation of cancer-causing compounds and suppressing the activation of carcinogens. The major polyphenols in green tea are flavonoids (catechin, epicatechin, epicatechin gallate, epigallocatechin gallate(EGCG), and proanthocyanidins).
Though both green tea and black tea are derived from the same plant (Camellia sinensis), they possess different antioxidants. In producing black tea the leaves are allowed to oxidize, during which enzymes present in the tea convert many polyphenols to larger molecules with different biological effects. However, green tea is produced by lightly steaming the fresh-cut leaf, which inactivates these enzymes, and oxidation does not occur.
[edit] Availability through microorganisms
A number of recent research articles have demonstrated the efficient production of flavonoid molecules from recombinant microorganisms. Such an approach opens the possibility of readily producing these compounds using renewable feedstocks and thus increasing the availability of rare flavonoid molecules for human and animal feed through dietary supplements. [1] [2] [3] [4] [5] [6] [7].
[edit] 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 6 subgroups[3]:
- Flavones use the 2-phenyl-4H-1-benzopyran-4-one skeleton:
- Examples: Luteolin, Apigenin, Tangeritin
- Flavonols use the 3-hydroxy-2-phenyl-4H-1-benzopyran-4-one skeleton:
- Examples: Quercetin, Kaempferol, Myricetin, Isorhamnetin, Pachypodol, Rhamnazin
- Flavanones use the 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one skeleton:
- Examples: Hesperetin, Naringenin, Eriodictyol
- Flavan-3-ols use the 2,3-dihydro-3-hydroxy-2-phenyl-benzopyran 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))
- Isoflavones use the 3-phenyl-4H-1-benzopyran-4-one skeleton:
- Anthocyanidins.
- Examples: Cyanidin, Delphinidin, Malvidin, Pelargonidin, Peonidin, Petunidin
[edit] See also
[edit] References
- ^ 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. Retrieved on 2006-08-30.
- ^ J. Agric.Food Chem. (2003) 51:7292-7295 Lee et al.
- ^ http://www.ars.usda.gov/is/np/phenolics/illus/phenfig4.htm
- Balch, J. F., & Balch, P. A. (2000). Prescription for Nutritional Healing. New York: Avery, Penguin Putnam Inc.
- Murray, M. T. (1996). Encyclopedia of Nutritional Supplements. Roseville: Prima Publishing.
- Spedding, G., Ratty, A., Middleton, E. Jr. (1989). Inhibition of reverse transcriptases by flavonoids. Antiviral Res 12 (2), 99-110. PMID 2480745
