Flavonoid

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Molecular structure of the flavone backbone (2phenyl!,"ben#opyrone$
%he term flavonoid refers to a class of plant secondary 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 antio0idant activity& 1o/ever,
it is no/ kno/n that the health benefits they provide against cancer and heart
disease are the result of other mechanisms&
,2-
Flavonoids are also commonly
referred to as bioflavonoids in the media 2 the terms are e3uivalent and
interchangeable, for flavonoids are biological in origin&
Biosynthesis
Flavonoids are synthesi#ed by the phenylpropanoid metabolic path/ay in
/hich the amino acid phenylalanine is 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/o phenyl rings (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 flavanones 5
dihydroflavonols 5 anthocyanins& 'long this path/ay many products can be
formed, including the flavonols, flavan.ols, proanthocyanidins (tannins$ and a
host of other polyphenolics&
Biological effects
Flavonoids are /idely distributed in plants fulfilling many functions including
producing yello/ or red6blue pigmentation in flo/ers and protection from attack
by microbes and insects& %he /idespread distribution of flavonoids, their variety
and their relatively lo/ to0icity compared 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 biological
response 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 anticancer activity&
+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 nutrients and vitamins&
Health benefit not due to direct antioxidant value
!
(n 299:, research conducted at the ;inus *auling (nstitute and published in
Free Radical Biology and Medicine indicates 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 <=$, and most of /hat is absorbed is 3uickly metaboli#ed and
e0creted from the body&
%he huge increase in antio0idant capacity of blood seen after the consumption
of flavonoidrich foods is not caused directly by the flavonoids themselves, but
most likely is due to increased uric acid levels that result from e0pelling
flavonoids from the body&
,2-
'ccording to Frei, 7/e can no/ follo/ the activity
of flavonoids in the body, and one thing that is clear is that the body sees them as
foreign compounds and is trying to get rid of them& >ut this process of gearing
up to get rid of un/anted compounds is inducing socalled *hase (( en#ymes that
also help eliminate mutagens and carcinogens, and therefore may be of value in
cancer prevention&&& Flavonoids could also induce mechanisms that help kill
cancer cells and inhibit tumor invasion&7
,2-
%heir research also indicated that only small amounts of flavonoids are
necessary to see these medical benefits& %aking large dietary supplements
provides no e0tra benefit and may pose some risks&
,2-
Diarrhea
' study done at +hildren8s 1ospital ? @esearch +enter Aakland, in
collaboration /ith scientists at 1einrich 1eine )niversity in Bermany, has
sho/n that epicatechin, 3uercetin and luteolin can inhibit the development of
fluids that result in diarrhea by targeting the intestinal cystic fibrosis
transmembrane conductance regulator +l2 transport inhibiting c'M*stimulated
+l2 secretion in the intestine&
,"-
Important flavonoids
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*lease update the article to reflect recent events, and remove this template
/hen finished&
Quercetin
Cuercetin is a flavonoid and more specifically a flavonol (see belo/$, that
constitutes the aglycone of the glycoside rutin& (n studies, 3uercetin is found to
be the most active of the flavonoids, and many medicinal plants o/e much of
their activity to their high 3uercetin content& Cuercetin has demonstrated
significant antiinflammatory activity because of direct inhibition of several
initial processes of inflammation& For e0ample, it inhibits both the production
and release of histamine and other allergic6inflammatory mediators& (n addition,
it e0erts potent antio0idant activity and vitamin +sparing action& (t has been
found to be anticancer& uercetin can be found in the herbal products based on
1a/thorn /hich are used for acute symptoms of +ongestive 1eart Failure&
Epicatechin
Dpicatechin improves blood flo/ and thus seems good for cardiac health&
+ocoa, the ma4or ingredient of dark chocolate, contains relatively high amounts
of epicatechin and has been found to have nearly t/ice the antio0idant content of
2
red /ine and up to three times that of green tea in invitro tests&
,<-

,E-
>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
*roanthocyanidins e0tracts demonstrate a /ide range of pharmacological
activity& %heir effects include increasing intracellular vitamin + 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
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*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 all citrus fruits, berries, onions, parsley,
legumes, green tea, red /ine, seabuckthorn, and dark chocolate (that /ith a
cocoa content of seventy percent or greater$&
!itrus
%he citrus bioflavonoids include hesperidin, 3uercetin, rutin (a glycoside of
3uercetin$, and tangeritin& (n addition to possessing antio0idant activity and an
ability to increase intracellular levels of vitamin +, rutin and hesperidin e0ert
beneficial effects on capillary permeability and blood flo/& %hey also e0hibit
some of the antiallergy and antiinflammatory benefits of 3uercetin& Cuercetin
can 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, easy bruising, hemorrhoids, and varicose veins&
Tea
Breen tea flavonoids are potent antio0idant compounds, 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$$&
(n producing teas such as oolong tea and black tea, the leaves are allo/ed to
o0idi#e, during /hich en#ymes present in the tea convert some or all of the
catechins to larger molecules& White tea is the least processed of teas and is
sho/n to present the highest amount of catechins kno/n to occur in camellia
sinensis&1o/ever, green tea is produced by steaming the freshcut leaf, /hich
inactivates these en#ymes, and o0idation does not significantly occur&
"ine
Brape skins contain significant amounts of flavonoids as /ell as other
polyphenols
,F-
& >oth red and /hite /ine contain flavonoids, ho/ever, since red
/ine is produced by fermentation in the presence of the grape skins, red /ine has
been observed to contain higher levels of flavonoids, and other polyphenolics
such as resveratrol&
.
#ubgroups
Aver <999 naturally occurring flavonoids have been characteri#ed from
various plants& %hey have been classified according to their chemical structure,
and are usually subdivided into the follo/ing subgroups:
Flavones
Flavones are divided into four groups:
,G-
Flavones
Flavones use the 2phenylchromen!"one skeleton&
D0amples: ;uteolin, 'pigenin, %angeritin
Flavonols
Flavonols or $%hydroxyflavones use the $%hydroxy2phenylchromen!"one
skeleton&
D0amples: Cuercetin, Haempferol, Myricetin, Fisetin, (sorhamnetin,
*achypodol, @hamna#in
Flavanones
Flavanones use the 2,.dihydro2phenylchromen!"one skeleton&
D0amples: 1esperetin, Iaringenin, Driodictyol
$%Hydroxyflavanones or &'$%dihydroflavonols
$%Hydroxyflavanones use the $%hydroxy2,.dihydro2phenylchromen!"
one skeleton&
D0amples: Jihydro3uercetin, Jihydrokaempferol
Isoflavones
(soflavones
(soflavones use the .phenylchromen!"one skeleton&
D0amples: Benistein, Jaid#ein, Blycitein
Flavan%$%ols and (nthocyanidins
Flavan%$%ols
Flavan#"ols use the 2phenyl.,"dihydro2$chromen#"ol skeleton&
Examples: +atechins (+atechin (+$, Ballocatechin (B+$, +atechin .gallate
(+g$, Ballocatechin .gallate (B+g$$, Dpicatechins (Dpicatechin (D+$,
Dpigallocatechin (DB+$, Dpicatechin .gallate (D+g$, Dpigallocatechin .gallate
(DB+g$$
(nthocyanidins
'nthocyanidins are the aglycones of anthocyanins& 'nthocyanidins use the
flavylium (2phenylchromenylium$ ion skeleton
Examples: +yanidin, Jelphinidin, Malvidin, *elargonidin, *eonidin,
*etunidin
(vailability through microorganisms
' number of recent research articles have demonstrated the efficient
production of flavonoid molecules from geneticallyengineered
microorganisms
,!9-
&
)eferences
* Flavonoids (isoflavonoids and neoflavonoids$&, ()*'+ +ompendium of
+hemical %erminology
K
a

b

c

d
7Ltudies force ne/ vie/ on biology of flavonoids7, by Javid Ltauth,
%urek&lert'& 'dapted from a ne/s release issued by Aregon Ltate )niversity&
)@; accessed 299:9.9E&
"
* %herapeutic potential of inhibition of the IFM> path/ay in the treatment of
inflammation and cancer& (a)a)oto and *aynor +,- (.)/ +#0 "" 1ournal of
2linical 3nvestigation& @etrieved on 299E9F.9&
* Lchuier, Ma0imilianN 1elmut Lies, >eate (llek, and 1orst Fischer (Actober
299<$& 7+ocoa@elated Flavonoids (nhibit +F%@Mediated +hloride %ransport
across %F" 1uman +olon Dpithelia7 (*JF$& 1ournal of 4utrition +$, (!9$: 2.29
2.2<& @etrieved on 299:9<92&
* J& 'gric&Food +hem& (299.$ <!::2G2:2G< ;ee et al&
* +ocoa nutrient for 8lethal ills8& BB2 4ews& @etrieved on 299:9.!!&
* Lpedding, B&, @atty, '&, Middleton, D& Jr& (!GFG$ (nhibition of reverse
transcriptases by flavonoids& &ntiviral Res +& (2$, GG!!9& *M(J 2"F9:"<
* James '& Hennedy, Mark '& Matthe/s, and 'ndre/ ;& Waterhouse, %ffect
of Maturity and 5ine Water 6tatus on *rape 6kin and Wine Flavonoids 'm& J&
Dnol& Oitic& <.:":2EF2:" (2992$ (abstract$
* http:66///&ars&usda&gov6is6np6phenolics6illus6phenfig"&htm
* 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(<$:2EGG:9E *M(J !2:.2<.G
>alch, J& F&, ? >alch, *& '& (2999$& *rescription for Iutritional 1ealing& Ie/
Pork: 'very, *enguin *utnam (nc&
Murray, M& %& (!GGE$& Dncyclopedia of Iutritional Lupplements& @oseville:
*rima *ublishing&
External lin-s
)LJ' Jatabase of Flavonoid content of food (pdf$
Flavonoids (chemistry$
Flavonoids (chemistry$
+ornell ne/s on +ocoa
' Jark +hocolate a Jay Heeps the Joctor '/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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