Σφακιανάκης Αλέξανδρος
ΩτοΡινοΛαρυγγολόγος
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The dietary intake of flavonoids reduces the risk of developing certain types of cancers.Anticancer and preventive effects against prostate,colorectal,breast,thyroid,lung,and ovarian cancers,Flavonoids include the following subfamilies: flavones, flavanols, isoflavones, flavonols, flavanones, and flavanonols, which differ in their ring substituents and extent of saturation.............................................................................................................................Silymarin, genistein, quercetin, daidzein, luteolin, kaempferol, apigenin, and epigallocatechin 3-gallate.Their chemopreventive efficacy is mediated by inhibiting the development of new cancer cells;preventing carcinogens from reaching their activation sites; and decreasing the toxicity of certain compounds by inhibiting their metabolism.The molecular mechanisms by which flavonoids produce their anticancer and preventive effects include (1) induction of apoptosis ; (2) cell cycle arrest at G1


Flavonoids present in foods were considered non-absorbable because they are bound to sugars as beta-glycosides. However, we found that human absorption of the quercetin glycosides from onions (52%) is far better than that of the pure aglycone (24%). Flavonol glycosides might contribute to the antioxidant defences of blood. Dietary flavonols and flavones probably do not explain the cancer-protective effect of vegetables and fruits; a protective effect against cardiovascular disease is not conclusive.Flavonoids and their polymers constitute a large class of food constituents, many of which alter metabolic processes and have a positive impact on health. Flavonoids are a subclass of polyphenols. They generally consist of two aromatic rings, each containing at least one hydroxyl, which are connected through a three-carbon "bridge" and become part of a six-member heterocyclic ring. The flavonoids are further divided into subclasses based on the connection of an aromatic ring to the heterocyclic ring, as well as the oxidation state and functional groups of the heterocyclic ring. Within each subclass, individual compounds are characterized by specific hydroxylation and conjugation patterns. Many flavonoids in foods also occur as large molecules (tannins). These include condensed tannins (proanthocyanidins), derived tannins and hydrolysable tannins. For proanthocyanidins, three subclasses (15 characterized) have been identified in foods. Monomers are connected through specific carbon-carbon and ether linkages to form polymers. Derived tannins are formed during food handling and processing, and found primarily in black and oolong teas. Flavonoids are widely distributed in nature, albeit not uniformly. As a result, specific groups of foods are often rich sources of one or more subclasses of these polyphenols. The polyphenolic structure of flavonoids and tannins renders them quite sensitive to oxidative enzymes and cooking conditions. Scientists in several countries have estimated intakes of a few subclasses of flavonoids from limited food composition databases. These observations suggest large differences in consumption, due in part to cultural and food preferences among populations of each country.

Flavonoids (specifically flavanoids such as the catechins) are "the most common group of polyphenoliccompounds in the human diet and are found ubiquitously in plants".[6] Flavonols, the original bioflavonoids such as quercetin, are also found ubiquitously, but in lesser quantities. 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. Foods with a high flavonoid content include parsley,[7] onions,[7] blueberries and other berries,[7] black tea,[7] green tea and oolong tea,[7] bananas, all citrus fruits, Ginkgo biloba, red wine, sea-buckthorns, anddark chocolate (with a cocoa content of 70% or greater). Further information on dietary sources of flavonoids can be obtained from the US Department of Agriculture flavonoid database.[7]





Flavonoid

From Wikipedia, the free encyclopedia
Molecular structure of theflavone backbone (2-phenyl-1,4-benzopyrone)
Isoflavan structure
Neoflavonoids structure

Flavonoids (or bioflavonoids) (from the Latin word flavus meaning yellow, their color in nature) are a class ofplant and fungus secondary metabolites.

Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and heterocyclic ring (C). This carbon structure can be abbreviated C6-C3-C6. According to the IUPACnomenclature,[1][2] they can be classified into:

The three flavonoid classes above are all ketone-containing compounds, and as such, are anthoxanthins (flavonesand 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. The three cycle or heterocycles in the flavonoid backbone are generally called ring A, B and C. Ring A usually shows a phloroglucinol substitution pattern.

Biosynthesis[edit]

Main article: Flavonoid biosynthesis

Functions of flavonoids in plants[edit]

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 designed to attract pollinator animals. In higher plants, flavonoids are involved in UV filtration, symbiotic nitrogen fixation and floral pigmentation. They may also act as chemical messengers, physiological regulators, and cell cycle inhibitors. 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. In addition, some flavonoids have inhibitory activity against organisms that cause plant diseases, e.g. Fusarium oxysporum.[3]

Subgroups[edit]

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[4]):

Anthoxanthins[edit]

Anthoxanthins are divided into two groups:[5]

GroupSkeletonExamples
DescriptionFunctional groupsStructural formula
3-hydroxyl2,3-dihydro
Flavone2-phenylchromen-4-one✗✗Flavone skeleton colored.svgLuteolin, Apigenin, Tangeritin
Flavonol
or
3-hydroxyflavone		3-hydroxy-2-phenylchromen-4-one✓✗Flavonol skeleton colored.svgQuercetin, Kaempferol, Myricetin, Fisetin, Galangin,Isorhamnetin, Pachypodol, Rhamnazin,Pyranoflavonols, Furanoflavonols,

Flavanones[edit]

Flavanones

GroupSkeletonExamples
DescriptionFunctional groupsStructural formula
3-hydroxyl2,3-dihydro
Flavanone2,3-dihydro-2-phenylchromen-4-one✗✓Flavanone skeleton colored.svgHesperetin, Naringenin, Eriodictyol,Homoeriodictyol

Flavanonols[edit]

Flavanonols

GroupSkeletonExamples
DescriptionFunctional groupsStructural formula
3-hydroxyl2,3-dihydro
Flavanonol
or
3-Hydroxyflavanone
or
2,3-dihydroflavonol		3-hydroxy-2,3-dihydro-2-phenylchromen-4-one✓✓Flavanonol skeleton colored.svgTaxifolin (orDihydroquercetin),Dihydrokaempferol

Flavans[edit]

Flavan structure

Include flavan-3-ols (flavanols), flavan-4-ols and flavan-3,4-diols.

SkeletonName
Flavan-3olFlavan-3-ol (flavanol)
Flavan-4olFlavan-4-ol
Flavan-3,4-diolFlavan-3,4-diol (leucoanthocyanidin)

Anthocyanidins[edit]

Flavylium skeleton of anthocyanidins

Isoflavonoids[edit]

Dietary sources[edit]

Parsley is a source of flavones.
Blueberries are a source of dietary anthocyanidins.
A variety of flavonoids are found incitrus fruits, including grapefruit.

Flavonoids (specifically flavanoids such as the catechins) are "the most common group of polyphenoliccompounds in the human diet and are found ubiquitously in plants".[6] Flavonols, the original bioflavonoids such as quercetin, are also found ubiquitously, but in lesser quantities. 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. Foods with a high flavonoid content include parsley,[7] onions,[7] blueberries and other berries,[7] black tea,[7] green tea and oolong tea,[7] bananas, all citrus fruits, Ginkgo biloba, red wine, sea-buckthorns, anddark chocolate (with a cocoa content of 70% or greater). Further information on dietary sources of flavonoids can be obtained from the US Department of Agriculture flavonoid database.[7]

Parsley[edit]

Parsley, both fresh and dried, contains flavones.[7]

Blueberries[edit]

Blueberries are a dietary source of anthocyanidins.[7][8]

Black tea[edit]

Black tea is a rich source of dietary flavan-3-ols.[7]

Citrus[edit]

The citrus flavonoids include hesperidin (a glycoside of the flavanone hesperetin), quercitrin, rutin (twoglycosides of the flavonol quercetin), and the flavone tangeritin.

Wine[edit]

Main article: Polyphenols in wine

Cocoa[edit]

Main article: Health effects of chocolate

Flavonoids exist naturally in cocoa, but because they can be bitter, they are often removed from chocolate, even dark chocolate.[9] Although flavonoids are present in milk chocolate, milk may interfere with their absorption;[10][11] however this conclusion has been questioned.[12]

Peanut[edit]

Peanut (red) skin contains significant polyphenol content, including flavonoids.[13][14]

Food sourceFlavonesFlavonolsFlavanones
Red onion04 - 1000
Parsley, fresh24 - 6348 - 100
Thyme, fresh5600
Lemon juice, fresh00 - 22 - 175

[15]

Dietary intake[edit]

Mean flavonoid intake in mg/d per country, the pie charts show the relative contribution of different types of flavonoids.[16]

Food composition data for flavonoids were provided by the USDA database on flavonoids.[7] In the United States NHANES survey, mean flavonoid intake was 190 mg/d in adults, with flavan-3-ols as the main contributor.[17] In the European Union, based on data from EFSA, mean flavonoid intake was 140 mg/d, although there were considerable differences between individual countries.[16]

Data is based on mean flavonoid intake of all countries included in the 2011 EFSA Comprehensive European Food Consumption Database.[16]

The main type of flavonoids consumed in the EU and USA were flavan-3-ols, mainly from tea, while intake of other flavonoids was considerably lower.[16][17]

Research[edit]

Though there is ongoing research into the potential health benefits of individual flavonoids, neither theFood and Drug Administration (FDA) nor the European Food Safety Authority (EFSA) has approved any health claim for flavonoids or approved any flavonoids as pharmaceutical drugs.[18][19][20] Moreover, several companies have been cautioned by the FDA over misleading health claims.[21][22][23][24]

In vitro[edit]

Flavonoids have been shown to have a wide range of biological and pharmacological activities in in vitrostudies. Examples include anti-allergic,[25] anti-inflammatory,[25][26] antioxidant,[26] anti-microbial(antibacterial,[27][28] antifungal,[29][30] and antiviral[29][30]), anti-cancer,[26][31] and anti-diarrheal activities.[32]Flavonoids have also been shown to inhibit topoisomerase enzymes[33][34] and to induce DNA mutations in the mixed-lineage leukemia (MLL) gene in in vitro studies.[35] However, in most of the above cases no follow up in vivo or clinical research has been performed, leaving it impossible to say if these activities have any beneficial or detrimental effect on human health. Biological and pharmacological activities which have been investigated in greater depth are described below.

Antioxidant[edit]

Research at the Linus Pauling Institute and the European Food Safety Authority shows that flavonoids are poorly absorbed in the human body (less than 5%), with most of what is absorbed being quickly metabolized and excreted.[20][36][37] These findings suggest that flavonoids have negligible systemic antioxidant activity, and that the increase in antioxidant capacity of blood seen after consumption of flavonoid-rich foods is not caused directly by flavonoids, but is due to production of uric acid resulting from flavonoid depolymerizationand excretion.[38]

Inflammation[edit]

Inflammation has been implicated as a possible origin of numerous local and systemic diseases, such ascancer,[39] cardiovascular disorders,[40] diabetes mellitus,[41] and celiac disease.[42]

Preliminary studies indicate that flavonoids may affect anti-inflammatory mechanisms via their ability to inhibit reactive oxygen or nitrogen compounds.[43] Flavonoids have also been proposed to inhibit the pro-inflammatory activity of enzymes involved in free radical production, such as cyclooxygenase, lipoxygenaseor inducible nitric oxide synthase,[43][44] and to modify intracellular signaling pathways in immune cells,[43] or in brain cells after a stroke.[45]

Procyanidins, a class of flavonoids, have been shown in preliminary research to have anti-inflammatory mechanisms including modulation of thearachidonic acid pathway, inhibition of gene transcription, expression and activity of inflammatory enzymes, as well as secretion of anti-inflammatory mediators.[46]

Cancer[edit]

Clinical studies investigating the relationship between flavonoid consumption and cancer prevention/development are conflicting for most types of cancer, probably because most studies are retrospective in design and use a small sample size.[47] Two apparent exceptions are gastric carcinomaand smoking-related cancers. Dietary flavonoid intake is associated with reduced gastric carcinoma risk in women,[48] and reduced aerodigestive tract cancer risk in smokers.[49]

Cardiovascular diseases[edit]

Among the most intensively studied of general human disorders possibly affected by dietary flavonoids, preliminary cardiovascular diseaseresearch has revealed the following mechanisms under investigation in patients or normal subjects:[50][51][52][53][54]

Listed on the clinical trial registry of the US National Institutes of Health (July 2016) are 48 human studies completed or underway to study the dietary effects of plant flavonoids on cardiovascular diseases.[55]

However, population-based studies have failed to show a strong beneficial effect[56] which might be due to the considerably lower intake in the habitual diet of those investigated.

Antibacterial[edit]

Flavonoids have been shown to have (a) direct antibacterial activity, (b) synergistic activity with antibiotics, and (c) the ability to suppress bacterialvirulence factors in numerous in vitro and a limited number of in vivo studies.[27][57] Noteworthy among the in vivo studies[58][59][60] is the finding that oral quercetin protects guinea pigs against the Group 1 carcinogen Helicobacter pylori.[60] Researchers from the European Prospective Investigation into Cancer and Nutrition have speculated this may be one reason why dietary flavonoid intake is associated with reduced gastric carcinoma risk in European women.[61] Additional in vivo and clinical research is needed to determine if flavonoids could be used as pharmaceutical drugs for the treatment of bacterial infection, or whether dietary flavonoid intake offers any protection against infection.

Synthesis, detection, quantification, and semi-synthetic alterations[edit]

Color spectrum[edit]

Flavonoid synthesis in plants is induced by light color spectrums at both high and low energy radiations. Low energy radiations are accepted byphytochrome, while high energy radiations are accepted by carotenoids, flavins, cryptochromes in addition to phytochromes. Thephotomorphogenic process of phytochome-mediated flavonoid biosynthesis has been observed in Amaranthus, barley, maize, Sorghum and turnip. Red light promotes flavonoid synthesis.[62]

Availability through microorganisms[edit]

Several recent research articles have demonstrated the efficient production of flavonoid molecules from genetically engineered microorganisms.[63][64][65]

Tests for detection[edit]

Shinoda test

Four pieces of magnesium filings are added to the ethanolic extract followed by few drops of concentrated hydrochloric acid. A pink or red colour indicates the presence of flavonoid.[66] Colours varying from orange to red indicated flavones, red to crimson indicated flavonoids, crimson to magenta indicated flavonones.

Sodium hydroxide test

About 5 mg of the compound is dissolved in water, warmed and filtered. 10% aqueous sodium hydroxide is added to 2 ml of this solution. This produces a yellow coloration. A change in color from yellow to colorless on addition of dilute hydrochloric acid is an indication for the presence of flavonoids.[67]

p-Dimethylaminocinnamaldehyde test

A colorimetric assay based upon the reaction of A-rings with the chromogen p-dimethylaminocinnamaldehyde (DMACA) has been developed for flavanoids in beer that can be compared with the vanillin procedure.[68]

Quantification[edit]

Lamaison and Carnet have designed a test for the determination of the total flavonoid content of a sample (AlCI3 method). After proper mixing of the sample and the reagent, the mixture is incubated for 10 minutes at ambient temperature and the absorbance of the solution is read at 440 nm. Flavonoid content is expressed in mg/g of quercetin.[69]

Semi-synthetic alterations[edit]

Immobilized Candida antarctica lipase can be used to catalyze the regioselective acylation of flavonoids.[70]

See also[edit]

References[edit]

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Further reading[edit]

  • Andersen, Ø.M. / Markham, K.R. (2006). Flavonoids: Chemistry, Biochemistry and Applications. CRC Press. ISBN 978-0-8493-2021-7
  • Grotewold, Erich (2007). The Science of Flavonoids. Springer. ISBN 978-0-387-74550-3
  • Comparative Biochemistry of the Flavonoids, by J.B. Harborne, 1967 (Google Books)
  • The systematic identification of flavonoids, by T.J. Mabry, K.R. Markham and M.B. Thomas, 1970, doi:10.1016/0022-2860(71)87109-0

External links[edit]

Databases[edit]


Alexandros Sfakianakis
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