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FlavonoidFrom Wikipedia, the free encyclopediaTen thingsyou didn't know about Wikipedia

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Molecular structure of the flavonebackbone (2phenyl!,"ben#opyrone$

%he term flavonoidrefers to a class ofplantsecondary metabolites& 'ccording

to the )*'+nomenclature,!-they can be classified into:

flavonoids, derived from 2phenylchromen"one(2phenyl!,"ben#opyrone$

structure

isoflavonoids, derived from .phenylchromen"one(.phenyl!,"

ben#opyrone$ structure

neoflavonoids, derived from "phenylcoumarine("phenyl!,2ben#opyrone$

structure&

Flavonoids are most commonly kno/n for their antio0idantactivity& 1o/ever,

it is no/ kno/n that the health benefits they provide against cancer and heartdisease are the result of other mechanisms&2-Flavonoids are also commonly

referred to as bioflavonoidsin the media the terms are e3uivalent and

interchangeable, for flavonoids are biological in origin&

BiosynthesisFlavonoids are synthesi#ed by thephenylpropanoidmetabolic path/ayin

/hich the amino acidphenylalanineis used to produce "coumaroyl+o'& %his

can be combined /ith malonyl+o'to yield the true backbone of flavonoids, a

group of compounds called chalcones/hich contain t/ophenylrings (see

polyphenols)& +on4ugate ringclosure of chalcones results in the familiar form of

flavonoids, the threeringed structure of a flavone& %he metabolic path/ay

continues through a series of en#ymatic modifications to yield flavanones5

dihydroflavonols5 anthocyanins& 'long this path/ay many products can be

formed, including the flavonols, flavan.ols, proanthocyanidins (tannins$ and a

host of other polyphenolics&

Biological effectsFlavonoids are /idely distributed in plants fulfilling many functions including

producing yello/ or red6bluepigmentationin flo/ers and protection from attack

by microbesand insects& %he /idespread distribution of flavonoids, their variety

and their relatively lo/ to0icitycompared to other active plant compounds(for

instance alkaloids$ mean that many animals, including humans, ingest significant

3uantities in their diet& Flavonoids have been referred to as 7nature8s biologicalresponse modifiers7 because of strong e0perimental evidence of their inherent

ability to modify the body8s reaction to allergens, viruses, and carcinogens& %hey

sho/ antiallergic, antiinflammatory .-, antimicrobial and anticanceractivity&

+onsumers and food manufacturers have become interested in flavonoids for

their medicinal properties, especially their potential role in the prevention of

cancers and cardiovascular disease& %he beneficial effects of fruit, vegetables,

and tea or even red /ine have been attributed to flavonoid compounds rather

than to kno/n nutrientsand vitamins&

Health benefit not due to direct antioxidant value

!
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n 299, research conducted at the;inus *auling nstituteand published in

Free Radical Biology and Medicineindicates that inside the human body,

flavonoids themselves are of little or no direct antio0idant value& )nlike in the

controlled conditions of a test tube, flavonoids are poorly absorbed by the human

body (less than


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red /ineand up to three times that of green teain invitro tests&ut in the

test outlined above it no/ appears the beneficial antio0idant effects are minimal

as the antio0idants are rapidly e0creted from the body&

ligomeric proanthocyanidins

*roanthocyanidinse0tracts demonstrate a /ide range of pharmacologicalactivity& %heir effects include increasing intracellularvitamin +levels,

decreasing capillary permeability and fragility, scavenging o0idants 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.*arts of this article or section are no longer up to date&*lease update the article to reflect recent events, and remove this template

/hen finished&

Bood sources of flavonoids include allcitrusfruits, berries, onions,parsley,

legumes, green tea,red /ine, seabuckthorn, and dark chocolate(that /ith a

cocoacontent of seventy percent or greater$&

!itrus%he citrus bioflavonoids includehesperidin,3uercetin,rutin(a glycosideof

3uercetin$, and tangeritin& n addition to possessing antio0idant activity and an

ability to increase intracellular levels of vitamin +, rutin andhesperidine0ert

beneficial effects on capillarypermeability andblood flo/& %hey also e0hibit

some of the antiallergy and antiinflammatory benefits of 3uercetin& Cuercetincan also inhibit reverse transcriptase,part of the replication process of

retroviruses&-%he therapeutical relevance of this inhibition has not been

established& 1ydro0yethylrutosides(1D@$ have been used in the treatment of

capillary permeability, easybruising,hemorrhoids, and varicose veins&

Tea Breen teaflavonoids are potentantio0idantcompounds, thought to reduce

incidence of cancer and heart disease& %he ma4or flavonoids in green tea are the

catechins(catechin, epicatechin, epicatechin gallate, and epigallocatechin gallate

(DB+B$$&

n producing teas such as oolong teaandblack tea, the leaves are allo/ed to

o0idi#e, during /hich en#ymespresent in the tea convert some or all of thecatechins to larger molecules& White teais the least processed of teas and is

sho/n to present the highest amount of catechins kno/n to occur in camellia

sinensis&1o/ever, green tea is produced by steaming the freshcut leaf, /hich

inactivates these en#ymes, and o0idation does not significantly occur&

"ineBrape skins contain significant amounts of flavonoids as /ell as other

polyphenols-& >oth red and /hite /ine contain flavonoids, ho/ever, since red

/ine is produced by fermentation in the presence of the grape skins, red /ine has

been observed to contain higher levels of flavonoids, and other polyphenolics

such as resveratrol&

.
http://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Flavonoid#_note-1%23_note-1http://en.wikipedia.org/wiki/Flavonoid#_note-bbc1%23_note-bbc1http://en.wikipedia.org/wiki/Flavonoid#_note-bbc1%23_note-bbc1http://en.wikipedia.org/wiki/Oligomeric_proanthocyanidinhttp://en.wikipedia.org/wiki/Oligomeric_proanthocyanidinhttp://en.wikipedia.org/wiki/Intracellularhttp://en.wikipedia.org/wiki/Vitamin_Chttp://en.wikipedia.org/wiki/Collagenhttp://en.wikipedia.org/wiki/Citrushttp://en.wikipedia.org/wiki/Citrushttp://en.wikipedia.org/wiki/Citrushttp://en.wikipedia.org/wiki/Onionhttp://en.wikipedia.org/wiki/Onionhttp://en.wikipedia.org/wiki/Parsleyhttp://en.wikipedia.org/wiki/Legumehttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Seabuckthornhttp://en.wikipedia.org/wiki/Dark_chocolatehttp://en.wikipedia.org/wiki/Cocoahttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Quercetinhttp://en.wikipedia.org/wiki/Quercetinhttp://en.wikipedia.org/wiki/Quercetinhttp://en.wikipedia.org/wiki/Rutinhttp://en.wikipedia.org/wiki/Glycosidehttp://en.wikipedia.org/wiki/Glycosidehttp://en.wikipedia.org/wiki/Tangeritinhttp://en.wikipedia.org/wiki/Vitamin_Chttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Capillaryhttp://en.wikipedia.org/wiki/Blood_flowhttp://en.wikipedia.org/wiki/Reverse_transcriptasehttp://en.wikipedia.org/wiki/Reverse_transcriptasehttp://en.wikipedia.org/wiki/Retrovirushttp://en.wikipedia.org/wiki/Flavonoid#_note-2%23_note-2http://en.wikipedia.org/wiki/Flavonoid#_note-2%23_note-2http://en.wikipedia.org/w/index.php?title=Hydroxyethylrutoside&action=edithttp://en.wikipedia.org/wiki/Bruisinghttp://en.wikipedia.org/wiki/Bruisinghttp://en.wikipedia.org/wiki/Hemorrhoidhttp://en.wikipedia.org/wiki/Varicose_veinshttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Catechinhttp://en.wikipedia.org/wiki/Epigallocatechin_gallatehttp://en.wikipedia.org/wiki/Oolong_teahttp://en.wikipedia.org/wiki/Black_teahttp://en.wikipedia.org/wiki/Oxidationhttp://en.wikipedia.org/wiki/Enzymehttp://en.wikipedia.org/wiki/White_teahttp://en.wikipedia.org/wiki/Camellia_sinensishttp://en.wikipedia.org/wiki/Camellia_sinensishttp://en.wikipedia.org/wiki/Leafhttp://en.wikipedia.org/wiki/Flavonoid#_note-3%23_note-3http://en.wikipedia.org/wiki/Resveratrolhttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Flavonoid#_note-1%23_note-1http://en.wikipedia.org/wiki/Flavonoid#_note-bbc1%23_note-bbc1http://en.wikipedia.org/wiki/Oligomeric_proanthocyanidinhttp://en.wikipedia.org/wiki/Intracellularhttp://en.wikipedia.org/wiki/Vitamin_Chttp://en.wikipedia.org/wiki/Collagenhttp://en.wikipedia.org/wiki/Citrushttp://en.wikipedia.org/wiki/Onionhttp://en.wikipedia.org/wiki/Parsleyhttp://en.wikipedia.org/wiki/Legumehttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Red_winehttp://en.wikipedia.org/wiki/Seabuckthornhttp://en.wikipedia.org/wiki/Dark_chocolatehttp://en.wikipedia.org/wiki/Cocoahttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Quercetinhttp://en.wikipedia.org/wiki/Rutinhttp://en.wikipedia.org/wiki/Glycosidehttp://en.wikipedia.org/wiki/Tangeritinhttp://en.wikipedia.org/wiki/Vitamin_Chttp://en.wikipedia.org/wiki/Hesperidinhttp://en.wikipedia.org/wiki/Capillaryhttp://en.wikipedia.org/wiki/Blood_flowhttp://en.wikipedia.org/wiki/Reverse_transcriptasehttp://en.wikipedia.org/wiki/Retrovirushttp://en.wikipedia.org/wiki/Flavonoid#_note-2%23_note-2http://en.wikipedia.org/w/index.php?title=Hydroxyethylrutoside&action=edithttp://en.wikipedia.org/wiki/Bruisinghttp://en.wikipedia.org/wiki/Hemorrhoidhttp://en.wikipedia.org/wiki/Varicose_veinshttp://en.wikipedia.org/wiki/Green_teahttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Catechinhttp://en.wikipedia.org/wiki/Epigallocatechin_gallatehttp://en.wikipedia.org/wiki/Oolong_teahttp://en.wikipedia.org/wiki/Black_teahttp://en.wikipedia.org/wiki/Oxidationhttp://en.wikipedia.org/wiki/Enzymehttp://en.wikipedia.org/wiki/White_teahttp://en.wikipedia.org/wiki/Camellia_sinensishttp://en.wikipedia.org/wiki/Camellia_sinensishttp://en.wikipedia.org/wiki/Leafhttp://en.wikipedia.org/wiki/Flavonoid#_note-3%23_note-3http://en.wikipedia.org/wiki/Resveratrol


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#ubgroupsAver


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*%herapeutic potential of inhibition of the IF> path/ay in the treatment of

inflammation and cancer& aaoto and *aynor +,- (.)/ +#0 "" 1ournal of

2linical 3nvestigation& @etrieved on 299E9.9&

*Lchuier, Ma0imilianN 1elmut Lies, >eate llek, and 1orst Fischer (Actober

299

*1/ang D, Haneko M, Ahnishi P, 1orinouchi L&7roduction of plant"specific flavanones by %scherichia coli containing an artificial gene cluster8'ppl

Dnviron Microbiol& 299. MayNEG(alch, *& '& (2999$& *rescription for Iutritional 1ealing& Ie/

Pork: 'very, *enguin *utnam nc&

Murray, M& %& (!GGE$& Dncyclopedia of Iutritional Lupplements& @oseville:

*rima *ublishing&

External lin-s )L' atabase of Flavonoid content of food(pdf$

Flavonoids (chemistry$

Flavonoids (chemistry$+ornell ne/s on +ocoa

' ark +hocolate a ay Heeps the octor '/ay

'ntio0idant in Breen %ea may fight 'l#heimer8sDB+B

%herapeutic potential of the IFk> path/ay in the treatment of inflammatory

disorders

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