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Food Chemistry 175 (2015) 556–567

*

 Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Department of Applied hemistry and

 !cology, Franje "uhaca #$, %& '($$$ Osijek, roatia

a r t i c l e i n f o

Article history: Received 1 !ly 201" Received in revised form # $ecem%er 201" Acce&ted " $ecem%er 201" Availa%le online 11$ecem%er 201"

'eyords: oly&henols *i&ids roteins Car%ohydrates Association ith &oly&henols +ealth

a % s t r a c t

oly&henols are secondary meta%olites in &lants, investi-ated intensively %eca!se of their &otential &osi. tive effects on h!manhealth/ heir %ioavaila%ility and mechanism of &ositive effects have %een st!died, in vitro and in vivo/ *ately, a hi-h n!m%er of st!dies taes into acco!nt the interactions of &oly&henols ith com&o!nds &resent in foods, lie car%ohydrates, &roteins or li&ids,

 %eca!se these food constit!ents can have si-nificant effects on the activity of &henolic com&o!nds/ his &a&er revies theinteractions %eteen &henolic com&o!nds and li&ids, car%ohydrates and &roteins and their im&act on &oly&henol activity/

201" 3lsevier *td/ All ri-hts reserved/

Contents1/ 4ntrod!ction / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / /

/ / / / / / / / / / / / / 556 2/ henoliccom&o!nds / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / /

/ / / / 557 #/ lants microstr!ct!re and localiation of &henoliccom&o!nds/ / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / 55 "/ 4nteractions %eteen

 &oly&henols and other com&le8 molec!les / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / 55 "/1/4nteractions ith li&ids/ / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / /

/ / / / / 559 "/2/ 4nteractions ith &roteins / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / 560 "/#/

4nteractions ith car%ohydrates/ / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / // / / / / 56# 5/ Concl!sions/ / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / /

/ / / / / / / / / / / / / / / / / / / / / / 565

Acnoled-ements / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / // / / / / / / / / / / 565

References / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / / // / / / / / / / / / / 565

1. Introduction

lant foods contain com&onents im&ortant for h!man develo&. ment and health, lie vitamins, &roteins, and minerals/henolic com&o!nds are &lant secondary meta%olites %!t they are also an im&ortant &art of &lant foods/ hey are %ein- idelyst!died d!e to &otential &ositive effects of &oly&henol.rich foods/ oly&henols have shon vario!s &ositive %ioactivities, lieanticarcino-enic

 &ro&erties (ellion et al/, 2010)/ he &oly&henol infl!ence on car. diovasc!lar health and cancer as revieed %y +ollman et al/(2011)/ ;n the other hand, some activities of &oly&henols are %ein- reassessed, s!ch as their direct antio8idant activities inside

the or-anism and the %iolo-ical relevance of antio8idant activities in cardiovasc!lar disease &rotection (+ollman et al/, 2011)/ 4tis increasin-ly em&hasied that there are m!lti&le %ioactivities of &oly&henols in the h!man or-anism that are im&ortant to !nder.stand, s!ch as the role of their meta%olites, the effects on the mod.

*

el/:

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Revie 4nteractions of &oly&henols ith car%ohydrates, li&ids and &roteins

*idi>a ao%e 

Contents lists available at ScienceDirect

Food Chemistry journal homepage: www.elsevier.com/locate/foodchem

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4n order to have effects ithin the h!man or-anism, &henolic com&o!nds sho!ld %e released d!rin- di-estion and thena%sor%ed in the -!t in a certain amo!nt (arada @ A-!ilera, 2007)/ hat is hy their %ioaccessi%ility and %ioavaila%ility ares!%>ects of vari. o!s st!dies and revies (Adam et al/, 2002= $!arte @ Farah, 2011= Banach, illiamson, Borand, Dcal%ert, @REmEsy, 2005= Derra et al/, 2010)/ ioaccessi%ility is defined as the amo!nt of an in-ested com&o!nd that is availa%le for a%sor&tion in the -!t (alafo8.Carlos, Ayala.avala, @ Gonale.A-!ilar, 2011)/ he F$A has defined %ioavaila%ility as the rateand e8tent to hich the active s!%stances or thera&e!tic moieties contained in a dr!- are a%sor%ed and %ecome availa%le at the

site of action (arada @ A-!ilera, 2007)/Hario!s st!dies deal ith the determination of ho m!ch of the &oly&henols can %e a%sor%ed into the circ!lation system after 

they -et into the %ody (Adam et al/, 2002= Derra et al/, 2010)/ 3vidences s!--est that &oly&henols are a%sor%ed in a relatively loamo!nt/ he a%sor&tion of isoflavones and -allic acid is the %est, folloed %y catechins, flavanones, and I!ercetin -l!cosides/roanthocyani. dins, -alloylated tea catechins and anthocyanins are the least ell a%sor%ed (Banach et al/, 2005)/ Je evidenceoffers some ne vies on the %ioavaila%ility/ Can et al/ (201#) st!died the %io. availa%ility of 1#C

5

la%eled cyanidin.#.-l!coside, %y collectin- %lood, !rine, %reath and fecal sam&les from h!man vol!nteers/he res!lts shoed that anthocyanins are more %ioavaila%le than &revio!sly &erceived (12/# K 1/#L) and that their meta%olitesare &resent in the circ!lation for 6" h after in-estion/ rocyanidins are a%!ndant in many foods lie a&&les, %erries, and n!ts, andare therefore cons!med re-!larly %y many &eo&le/ Recent findin-s offers some additional !nderstandin- of the %ioavaila%ilitysince it as shon that not only ty&e dimers %!t also A ty&e dimers are %ioavaila%le (A&&eldoorn, Hincen, Gr!&&en, @

+ollman, 2009)/ Dt!dy has shon that the dose of &oly&henol in-ested has im&or. tant im&act in the %ioavaila%ility/ Jamely,hi-her doses can sho different effects than loer doses of in-ested &oly&henols/ D&ecif. ically, it as shon that chloro-enicacid from coffee had red!ced %ioavaila%ility in h!mans hen in-ested in hi-her doses (Dtalmach, illiamson, @ Croier, 201")/Boreover, it has %ecome clear that n!trients lie &roteins, car%ohydrates and li&ids that s!r. ro!nd &oly&henols inside the-astrointestinal tract, have a -reat im&act on the %ioaccessi%ility and %ioavaila%ility of &oly&henols/ 4ndeed, many s!ch n!trientshave a very com&le8, &oro!s str!ct!re hich tra& &oly&henols and, as a conseI!ence, chan-e their avail. a%ility for a%sor&tion/Dt!dies cond!cted in recent years have shon the im&ortance of these interactions (Chanteranne et al/, 200= Dchramm et al/,200#)/ Boreover, these interactions ith n!trients co!ld -ive &oly&henols a very different role/ hey co!ld &rotect &oly&henolsfrom o8idation d!rin- their &assa-e thro!-h the -astrointestinal tract and deliver them to the colon more intact/ +ere they can %emeta%olied !nder the infl!ence of microflora/ Recent st!dies descri%e the role of dietary %ioactive com&o!nds, intestinalmicro%iota and &oly&henol meta%olites (Bac$onald @ a-ner, 2012= !ohy, Conterno, Ges&erotti, @ Hiola, 2012)/ F!r.thermore, it is s!--ested that a &ositive, antio8idant environment co!ld %e created in the -astrointestinal tract, %y the delivery andrelease of &oly&henols/ here &oly&henols, as antio8idant com. &o!nds, can &rotect n!trients as &roteins, li&ids and vitamins,from o8idation/ 4n addition to these mentioned activities, they also can interact ith &roteins &rod!cin- &rotein &reci&itation andloss of n!tritional val!e, enymatic activity, and other %iolo-ical effects (omMs.ar%erMn @ AndrEs.*ac!eva, 2012)/ 4t has

 %ecome increas. in-ly clear that &oly&henols have many &otential %ioactivities in the h!man %ody hich are affected %yinteractions of &oly&henols ith other macromolec!les (*e o!rvellec @ Renard, 2012)/

4nteractions %eteen &oly&henols and molec!les from food ere mostly %ased on different non.covalent hydro&ho%ic

 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- ..- 

interactions (N!sel, Avci, @ 3rdem, 2010)/ +ydro-en %onds are also im&ortant as in the case of interactions %eteen &oly&henols and &roteins (Fraier et al/, 2010= Dh&i-elman, 4sraeli, @ *ivney, 2010), and &oly&henols and car%ohydrates (Da!ra.Cali8to, 2011)/ he interaction %eteen &roteins and &lant &henols can lead to covalent %onds as ell ('roll, Rael, @ Rohn,200#)/ he conditions for formin- covalent %onds are the ca&a%ility of &henols to form I!inone or semi.I!inone radicals (in ato.ste& reaction)/ he reaction &roceeds ith &olymeriation ('roll et al/, 200#)/

his &a&er revies the recent literat!re a%o!t the interactions %eteen &henolic com&o!nds and other molec!les &resent infood (&roteins, car%ohydrates, and li&ids), the nat!re of these interac. tions and their si-nificance/

2. Phenolic compounds

A hi-h n!m%er of com&o!nds %elon- to the -ro!& of &henolics (&henolic acids, aceto&henones, &henylacetic acid,hydro8ycin. namic acids, co!marins, na&hthoI!inones, 8anthones, stil%enes, flavonoids) (Croier, a-anath, @ Clifford, 2009)/he most im&or. tant ones occ!rrin- in &lants are flavonoids, &henolic acids, stil%. enes and li-nans (Croier et al/, 2009)/ heir chemical str!ct!re is more or less com&le8 and can vary from very sim&le molec!les to very com&le8 ones/

Flavonoids, as one of the lar-est -ro!& of &henolic com&o!nds, can %e f!rther classified into several s!%cate-ories lie

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com&o!nds ith the environment/ !t even those ith a sim&ler str!ct!re are

and n!trients can also come into contactith each often associated ith s!-ar !nits hich a-ain increases the n!m.

other hich ena%le vario!s interactions, &ossi%lechemical %ond. %er of hydro8yl -ro!&s and raises the &ossi%ility to interact ith

in-, and entra&ment of smaller molec!les into &oro!sstr!ct!re the environment/ heir str!ct!re, the arran-ement of hydro8yl

of %i--er molec!les/ hese interactions co!ld affect %ioaccessi%ili. -ro!&s, the &lanarity of molec!les, the arran-ement of s!-ar !nits

ty, %ioavaila%ility and %ioactivities of &henoliccom&o!nds/ and many other factors &lay im&ortant roles in the activity of &lant

Dome food matrices enhance the accessi%ility of &oly&henols as &henolics in the h!man %ody/

in the case of nat!ral almond sin here &oly&henols are more accessi%le than from %lanched sins &rod!ced %y the almond #/lants microstr!ct!re and localiation of &henolic

ind!stry (Bandalari et al/, 2010)/ A st!dy on h!mans

has shon com&o!nds

that the %ioavaila%ility of chloro-enic acids from coffee can %e im&aired %y a matri8 consistin- of coffee and mil (sim!ltaneo!s4n order to !nderstand interactions that can occ!r %eteen

cons!m&tion of coffee and mil) ($!arte @ Farah,2011)/ Bil &oly&henols and other food in-redients, it is im&ortant to !nder.

affects the a%sor&tion of cocoa &oly&henols, %!taccordin- to some stand the %asic str!ct!re of &lant foods/

st!dies the a%sor&tion as decreased hile in other itincreased/ lant foods &rod!ced %y nat!re, are -enerally or-anied from

his controversy as e8&lained %y the im&act of &oly&henol con. molec!les into assem%lies and or-anelles that can create cells

centration ($el Rio, or-es, @ Croier, 2010)/ Bilco!ld interfere and tiss!es (arada @ A-!ilera, 2007)/ Jat!ral str!ct!res of fr!its

ith the a%sor&tion in the case of loer &oly&henolconcentration and ve-eta%les consist of hydrated cells s!rro!nded %y the cell

hile it co!ld have only minimal im&act if the &oly&henol concen. all (arada @ A-!ilera, 2007) ith n!cle!s, cyto&lasm and &lasma

tration is hi-h ($el Rio et al/, 2010)/ A food matri8 caninfl!ence mem%rane located ithin the cells= and a lar-e central vac!ole in

vario!s %ioactivities of &oly&henols/ Cinnamon e8tract &oly&he. the cyto&lasm/ hat str!ct!re at a micro level is already reco-nied

nols can %e incor&orated into defatted soy flo!r/oly&henols from as a very im&ortant for the %ioactivities of many com&o!nds/

that &rotein rich matri8 still shoed antidia%etic effects inanimal Jamely, a %i- &art of food cons!m&tion is of &lant foods that

st!dies (Chen- et al/, 2012)/ All these descri%ed matri8effects, have had minor &rocessin- or no &rocessin- at all/ Do at the

shon to &otentially infl!ence &oly&henol %ioactivities, co!ld %e moment of eatin-, the microstr!ct!re is in its nat!ral ori-inal form/

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 &artially ca!sed %y interactions %eteen &oly&henolsand other he di-estion %e-ins in the mo!th, here chan-es in microstr!c.

molec!les from food/ t!re start ha&&enin-/ Basticationres!lts in the r!&t!re of some cells, hich allos &henolic com&o!nds and other n!trients to %e released in the environment(adayachee et al/, 2012a,

"/ 4nteractions %eteen &oly&henols and othercom&le8 2012%)/ 4n &rocessed &rod!cts, the chan-es in the microstr!ct!re

molec!les %e-in already d!rin- the &rocessin- (arada@ A-!ilera, 2007)/ 4n any of these cases, nat!ral &lant food, &rocessed food or any other 

*i&ids, &roteins and car%ohydrates are com&o!ndsoften fo!nd matri8, hen the r!&t!re of microstr!ct!ral elements starts, &he.

in the environment s!rro!ndin- &henolic com&o!nds/hey can nolic com&o!nds can &otentially %e released to-ether ith other 

come into contact ith &henolic com&o!nds andinteract ith n!trients and %ecome availa%le for a%sor&tion/ hese &henolic

them/

a%le 1 4nteractions %eteen &oly&henols and li&ids, and their effects/

oly&henol tested *i&id model 3ffects Reference

4nfl!ence on em!lsion &ro&erties Green and %lac tea &oly&henols Bodel em!lsion (olive oil,

 &hos&hatidylcholine and %ile salt)

Dhishi!ra et al/ (2006)

*i&ase activity inhi%ition A&&le &oly&henol e8tract and

 &rocyanidins

. 4ncreased dro&let sie and decreased s&ecific s!rface area of 

olive.oil em!lsion

D!-iyama et al/ (2007) lac tea &oly&henol e8tract and

 &olymeried &oly&henol fraction

".Bethyl!m%elliferyl oleate . 4nhi%ition of li&ase activity (hi-her &olymeriation de-ree of 

 &rocyanidins – hi-her inhi%ition)

Ochiyama et al/ (2011)

Lipid oxidation inhibition and interaction with lipase peroxidation products Quercetin, rutin, (+)catechin,

caffeic acid, chloro-enic acid, #,".dihydro8y%eoic acid

*i&id em!lsion (corn oil, cholic acid,

. 4nhi%ition of li&ase activity, s!&&ression of the increase in rat cholesteryl oleate, ater)

 &lasma tri-lyceride, s!&&ression of the increase in %ody ei-ht and liver li&id content

*orrain et al/ (2010)

P!ercetin, r!tin, chloro-enic

acid

Bodel em!lsion D!nfloer oil,

. P!ercetin, r!tin, (

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 %etter inhi%itors of li&id o8idation than a.toco&herol or ascor%ic or e-- yol &hos&holi&ids

acid Bodel em!lsion (s!nfloer oil

. P!ercetin, r!tin, chloro-enic acid hi-hly inhi%ited metmyo-lo.

*orrain et al/ (2012) sta%ilied %y %ovine ser!m al%!min

 %in.initiated li&id o8idation or e-- yol &hos&holi&ids

. P!ercetin inhi%ited nonheme iron.initiated &rocesses Red ine4n vivo st!dy dar t!rey meat

Goreli et al/ (201#) c!tlets

$i-esti%ility of &oly&henols Cocoa &oly&henols Cocoa liI!or (50L fat content), cocoa

 &oder (15L fat content)

. Com%ination of red ine and meat &revented &ost&randial mod.

ification of *$* %y li&id &ero8idation &rod!cts . ossi%le mechanism: antio8idant &ro&erties of red ine &oly. &henols in thestomach, interaction ith li&id &ero8idation &rod. !cts ithin the -astrointestinal tract, delayin- of fat a%sor&tion

;rte-a, Re-!ant, Romero, Bacia, and Botilva (2009)

3nca&s!lation P!ercetin (PC), (Q).

e&i-allocatechin -allate ((Q). 3GCG)

. Fat content enhanced the di-esti%ility of some &oly&henols, es&ecially &rocyanidins, d!rin- d!odenal di-estion/ D!--estion isthe interaction %eteen fat and &oly&henols

*i&id nanoca&s!les (*JC) (*a%rafac,

. *i&id nanoca&s!les can %e !sed as a flavonoid delivery carriers arras et al/ (2009) Dol!tol,hos&holi&on)

..3 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- 

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lipase 4*(* 5nteractions 6ith lipids

activity and fat a%sor&tion/ ;ther st!dies also s!&&orted the inhi%ition of the li&ase activity and fat a%sor&tion &rocess %yoly&henols can interact ith li&ids from food so!rces (a%le 1

 &oly&henolic com&o!nds/ Ochiyama et al/ (2011) havest!died and Fi-/ 1)/ Dome st!dies have shon the &otential role of these

the infl!ence of %lac tea &oly&henols on diet.ind!cedo%esity in interactions in the fat a%sor&tion &rocess (Dhishi!ra, 'hohar, @

rats/ hey have shon that %lac tea &oly&henolsinhi%ited the B!rray, 2006= Ochiyama, ani-!chi, Daa, Noshida, @ Na>ima,

li&ase activity and conseI!ently inhi%ited intestinalli&id a%sor&. 2011) hich mi-ht have &ositive effects on health/

tion/ F!rthermore, they have shon that %lac tea &oly&henols $ietary fats -o thro!-h a di-estion &rocess that starts ith mas.

s!&&ressed the increase of tri-lyceride levels in the rat &lasma/ tication in hich li&ids are transformed into em!lsions/ After that

D!-iyama et al/ (2007) have st!died effects of a&&le

 &oly&henols they travel to the stomach and d!oden!m/ 4nside the -astrointes.

and &rocyanidins on the li&ase activity (in vitro) andtri-lyceride tinal tract, em!lsions are e8&osed to the s!rface.active com&o.

a%sor&tion (on mice and h!mans)/ Accordin- to theirres!lts, a&&le nents hich hel& in em!lsification/ F!rthermore, the li&ase

 &oly&henols and &rocyanidins also inhi%ited li&aseactivity and tri. carries o!t a &rocess of li&olysis, a %readon of li&ids into smaller 

-lyceride a%sor&tion/ &articles hich can then %ea%sor%ed (Dhishi!ra et al/, 2006)/ D&e.

4nvesti-ations s!--est that interactions %eteenli&ids and cific em!lsion &ro&erties lie dro&let sie and s!rface area are

 &oly&henols have only a small infl!ence on the &oly&henol acces. im&ortant for the li&ase activity (Dhishi!ra et al/, 2006)/ herefore,

si%ility for a%sor&tion/ For instance, Dchramm et al/(200#) st!died any molec!le hich mi-ht act on em!lsion &ro&erties or li&ase

the food effects (meals rich in li&ids, &roteins,car%ohydrates) on activity co!ld &otentially chan-e and affect the fat a%sor&tion &ro.

the a%sor&tion of cocoa flavanols in h!mans/ heyfo!nd that li&ids cess/ Jamely, molec!les s!rro!ndin- em!lsions co!ld %e fo!nd

from the meal (s!ch as mil, %!tter) had only minimaleffects on inside of the oil dro&let, in the ater &hase that s!rro!nds the

flavanol a%sor&tion/ oil dro&let or in the interfacialre-ion/ his &artitionin- is mostly

;n the other hand, hen li&ids interact ith &oly&henols, they determined %y the &olarity of molec!les/ Jon&olar molec!les can

can ca&t!re &oly&henols and &rotect them in their &assa-e %e fo!nd in the li&id &hase, &olar molec!les in the aI!eo!s &hase

thro!-h the -astrointestinal tract/ 4n this ay li&idsmi-ht hel& and am&hi&hilic molec!les at the interface of these to re-ions/

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di-estion, in sie and decreased s!rface area)/ 4t as s!--ested that the condi.

rats/ he addition of red ine com&letely &revented*$* (lo den. tions of increased dro&let sie co!ld ca!se the decrease in the

sity li&o&rotein) modifications %y li&id &ero8idation &rod!cts/ A

Polyphenol- lipid interac on

emulsifica on

polyphenol process

bioavailability and bioaccessibility

lipase ac vity

polyphenol- carbohydrate interac on

polyphenol delivery to lower parts of gastrointes nal tract

astringency

fat absorp on

protein structure process

and uality

interac on of 

inhibi on of lipid

polyphenol- protein

protein diges on

carbohydrates with polyphenol-protein o!ida on

interac on

comple!es

en"yme ac vity

polyphenol delivery

polyphenol bioac vity

to lower parts of gastrointes nal tract

polyphenol delivery to lower parts of gastrointes nal tract

microencapsula on of polyphenols into coa ng material

Fi-/ 1/ he conseI!ences of the interactions %eteen &oly&henols and li&ids, &roteins, and car%ohydrates/

 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- ..7

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 &ossi%le mechanism co!ld come from ine &oly&henols and their antio8idant &ro&erties/ Another s!--ested mechanism asinter. action %eteen &oly&henols and li&id &ero8idation &rod!cts/ he delay of the fat a%sor&tion &rocess ca!sed %y li&id– 

 &oly&henol interactions as also s!--ested/ ;ther st!dies have also shon the inhi%ition of li&id o8idation %y &oly&henols(I!ercetin, r!tin, (

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 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- .1(

a%le 2 4nteractions %eteen &oly&henols and &roteins and their effects/

oly&henol tested rotein model 3ffects References

!ttachment, the in"luence o" pol#phenol structure and other "actors on the interaction $rape seed proc#anidins a

!m#lase, prolinerich

 &roteins, %ovine ser!m al%!min

. rocyanidin a%ility to %ind &roteins increased ith molec!lar 

ei-ht of &rocyanidins

de Freitas and Bate!s (2001)

oly&henols Byo-lo%in . o., &.+ydro8y&henols, &.I!inone, -allic acid had hi-h reactiv.

ity and ca!sed str!ct!ral chan-es in myo-lo%in

'roll and Rael (2001) Chloro-enic acid, caffeic acid, -allic acid, flavone, a&i-enin, aem&ferol, I!ercetin, myricetin

Doy &roteins . he derivatiation is infl!enced %y the n!m%er and &osition of 

;+ -ro!&s on &henolic molec!les

Rael et al/ (2002) Green tea flavonoids Bil &roteins . +ydro&ho%ic %ondin- N!sel et al/

(2010) Gra&e seed &roanthocyanidins, mimosa 5.deo8y &roanthocyanidins, sor-h!m &rocyanidins

Gelatin . +ydro-en %ondin- Fraier et al/

(2010) (Q).3&i-allocatechin.#.-allate %.*acto-lo%!lin (*G) . +eated *G %inds &oly&henol ith hi-her affinity than does

the native &rotein

Dh&i-elman et al/ (2010) (

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001) Chloro-enic acid, m., o., &.dihydro8y%enene,

 &.%enoI!inone

a.Chymotry&sin . 3nyme inhi%ition de&ended on the reactivity of &henols and

de-ree of &olymeriation

Rohn et al/ (200#)

In"luence on the protein structure, %ualit# and di&estibilit# m, o, p'ih#drox#benenes, "erulic acid, &allic

acid

*ysoyme . Red!ction of lysine and try&to&han resid!es

. $erivatives – sol!%ility decreased over &+ ran-e, hydro&ho.

 %icity increased, isoelectric &oint shifted to loer &+

Rael et al/ (2001)

oly&henols Byo-lo%in . 3nymatic di-estion of derivatied myo-lo%in as affected 'roll @ Rael,

2001 Chloro-enic acid, caffeic acid, -allic acid, flavone, a&i-enin, aem&ferol, I!ercetin, myricetin

Doy &roteins . 4nteraction res!lted in %locin- of some amino acids (lysine,

try&to&han)

Rael et al/ (2002) Chloro-enic acid %.*acto-lo%!lin . he di-esti%ility of hey &rotein is diminished

. ;%served effect is not so distinct d!e to the hi-h n!tritional

I!ality of hey &roteins

ete et al/ (2005)

Chloro-enic acid, I!ercetin Doy &rotein . Rats fed ith soy &rotein derivatives shoed an increase

e8cretion of fecal and !rinary nitro-en . r!e nitro-en di-esti%ility, %iolo-ical val!e, net &rotein !tili.

ation ere affected

Rohn et al/ (2006)

Catechin, e&icatechin, e&i-allocatechin,

e&icatechin -allate, e&i-allocatechin -allate

 %.Casein . he slodon of &rotein adsor&tion A-!iE.E-hin

et al/ (200)

4nfl!ence on enyme activity m., o., &.$ihydro8y%enenes, fer!lic acid, -allic

acid

*ysoyme . he &e&tic di-estion of the derivatied lysoyme as affected Rael et al/

(2

001) Caffeic, chloro-enic, fer!lic, -allic acid, m., o., &.dihydro8y%enenes, I!inic acid, &. %enoI!inone

a.Amylase, try&sin, lysoyme

. he enyme activity inhi%ition de&ended on the reactivity of &henolic and related s!%stances, and on the s!%strate a&&lied

Rohn et al/ (2002)

Chloro-enic acid, m., o., &.dihydro8y%enene, &.

 %enoI!inone

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a.Chymotry&sin . 3nyme activity affected

. +ydrolysis of food &roteins as sloed don . he affinity of enyme to s!%strates decreased

Rohn et al/ (200#)

Gra&e seed &rocyanidins a.Amylase . 4nhi%ition of enyme activity as related ith the de-ree of 

 &olymeriation of &rocyanidins

GonUalves et al/ (2011%)

Astrin-ency rocyanidin dimer and trimer, (Q).e&icatechin ;.

-allate, 2.#00.;.-allate

a.Amylase, &roline.rich &roteins (R)

. (

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Arts et al/ (2002) (Q).3&i-allocatechin.#.-allate (3GCG) %.*acto-lo%!lin . Com&le8 &rotected 3GCG a-ainst o8idativede-radation Dh&i-elman

etal/ (2010) ea &oly&henols %.*acto-lo%!lin (*G)

caseinomacro&e&tide (CB)

. oly&henols retain their anti&roliferative activity ithin thecom&le8es ith *G and CB

Hon Dtasesi et al/ (2012)

connected to the &revention of dental caries/ Jamely, some f!nc. tions of a.amylase can lead to the formation of dental &laI!eand dental caries (Rael, Frey, Beidtner, @ 'roll, 2006)/ y inhi%. itin- its activity, &oly&henols.a.amylase associations co!ldhave &ositive effects in &reventin- the formation of caries/ Dince &oly. &henols can %ind to lysoyme, they can decrease its lyticactivity (Rael et al/, 2001)/ Rohn et al/ (2002) also demonstrated the enyme activity inhi%ition %y &oly&henols/ he activity of a.chy. motry&sin as inhi%ited after the interaction ith &oly&henols (Rohn, Rael, ollen%er-er, @ 'roll, 200#)/ As aconseI!ence, the hydrolysis of food &roteins as sloer and the affinity to the s!%strate declined (Rohn et al/, 200#)/

Dome st!dies e8amined the infl!ence of &oly&henol–&rotein interactions on &oly&henol %ioavaila%ility/ 3arlier st!diesdescri%ed minimal effects/ Dchramm et al/ (200#) shoed that there as only a minimal effect of &roteins from meals on &henolic

com&o!nd a%sor&tion (cocoa catechins) (in a st!dy cond!cted on h!mans)/ Also in a st!dy cond!cted in vivo, on h!manvol!nteers, Han het +of, 'ivits, eststrate, and i>%!r- (199) shoed that mil added to -reen and %lac tea did not infl!encethe %ioavail. a%ility of catechins/ Bore recent st!dies descri%e &ositive or ne-a. tive effects/ $!arte and Farah (2011) s!--estedthat the interactions %eteen mil constit!ents and &oly&henols from cof. fee may &rod!ce a ne-ative effect on coffee &oly&henol

 %ioavail. a%ility, in h!mans/ Ri%nicy et al/ (201") st!died the %ioavaila%ility of &oly&henols from Artemisia drac!nc!l!s */ inmice, in the form of e8tract or in a com&le8 ith soy &roteins/ he res!lts shoed that &oly&henols sor%ed to soy &rotein isolateere more %ioavaila%le and %ioaccessi%le/

F!rthermore, st!dies s!--ested additional &ositive effects of &oly&henol–&rotein interactions/ Jamely, &oly&henols co!ld %edelivered to loer &arts of the -astrointestinal tract d!e to &oly. &henol–&rotein interactions/ Certain &roteins carryin-

 &oly&henols ere even called nanovehicles (Dh&i-elman et al/, 2010)/ Dto>adinovic et al/ (201#) also s!--ested &roteins as -oodcarriers of &oly&henols in the -astrointestinal tract/ hese com&le8es co!ld sho several effects on the &oly&henol activity/ heymi-ht &rotect &oly&henols a-ainst o8idative de-radation as it as fo!nd for (Q)e&i-allocatechin.#.-allate in com&le8 ith heated

 %.lacto-lo%.

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!lin (Dh&i-elman et al/, 2010)/ hen %o!nd to &roteins, &oly&he. nols co!ld &reserve their anti.&roliferative activity hich asfo!nd for -reen tea &oly&henols (Hon Dtasesi et al/, 2012)/ ;n the other hand, the association %eteen &oly&henols and

 &roteins co!ld affect the antio8idant activity of &oly&henols as it as fo!nd for associations created %eteen &oly&henols andmil &roteins, in vitro (+asni et al/, 2011)/ 4n fact, d!e to the &rotein–&oly&henol interactions, the antio8idant activity of 

 &oly&henols as mased (Arts et al/, 2002)/

Dt!dies disc!ssed here have shon that &oly&henol–&rotein interactions mi-ht infl!ence astrin-ency sensation in the mo!th/

he %iolo-ical activity of &roteins is also affected/ y %indin- to &roteins, &oly&henols mi-ht &otentially affect the availa%ility of certain amino acids and also chan-e the &rotein str!ct!re hich co!ld affect the f!nctionality and di-esti%ility of &roteins/ +o.ever, the stren-th of this effect co!ld de&end on the n!tritional I!ality of &roteins themselves/ oly&henols can interact ithenymes and chan-e their enymatic activity, hich co!ld have vario!s conseI!ences/ Dome of them are &ositive, as in the caseof the inhi%ition of a.amylase activity hich co!ld %e connected to the &revention of dental cavities/ 4n the case of di-estiveenyme inhi%ition, interactions co!ld lead to the infl!ence on the di-estion &rocess/ rotein–&oly&henol interactions mi-htinfl!ence &oly&he. nols as ell/ 4n the &resence of &roteins, some &oly&henol activities co!ld %e mased, lie their antio8idantactivity/ Dt!dies have also s!--ested the &ossi%le infl!ence of &rotein–&oly&henol interac. tions on the &oly&henol %ioavaila%ility/;n the other hand, d!e to &oly&henol–&rotein interactions, &roteins co!ld %e carriers of &oly. &henols thro!-h the -astrointestinaltract and &rotect them from o8idation reactions/

4*'* 5nteractions 6ith car+ohydrates

A lar-e %ody of evidence has %een shon for the interaction %eteen &oly&henols and car%ohydrates (a%le #, and Fi-/ 1)/

Car. %ohydrates can interact ith &oly&henols (*e o!rvellec, G!yot, @ Renard, 2009= adayachee et al/, 2012a, 2012%=einen et al/, 201"= Rosa, $!fo!r, *!llien.ellerin, @ Bicard, 201#), and it has %een shon that these interactions have asi-nificant role in the h!man %ody/ 4n addition, several revie &a&ers have recently %een &!%lished hich &artic!larly em&hasiethe im&ortance of the interaction of &oly&henols ith dietary fi%er (Bac$onald @ a-ner, 2012= alafo8.Carlos et al/, 2011=Da!ra.Cali8to, 2011= !ohy et al/, 2012)/

4nteractions of &oly&henols ith car%ohydrates ere mainly investi-ated e8&erimentally in vitro/ oly&henol interact ithvar. io!s car%ohydrates ori-inated from the cell all lie &ectin, cell!. lose or dietary fi%ers (*e o!rvellec et al/, 2009=adayachee et al/, 2012a, 2012%)/ 4t as fo!nd that &rocyanidins %o!nd to cell all car%ohydrates (*e o!rvellec, o!chet, @Renard, 2005= *e o!rvellec et al/, 2009)/ Dt!dies also hi-hli-hted the increase of the interaction ith the increased de-ree of 

 &olymeriation of &rocyanidins and &ercent of -alloylation (a!tista.;rtTn, Cano. *ech!-a, R!i.GarcTa, @ GSme.laa, 201"=*e o!rvellec et al/, 2005= atrelot, *e o!rvellec, 4m%erty, @ Renard, 201#)/ F!rther. more, hi-h affinities of &rocyanidins for 

 &ectin ere shon (*e o!rvellec et al/, 2005, 2009= atrelot et al/, 201#), hich as e8&lained %y the formation of 

hydro&ho%ic &ocets a%le to enca&. s!late &rocyanidins (*e o!rvellec et al/, 2005)/ ocets or cavities in car%ohydratemolec!les ere hi-hli-hted as im&ortant in the interaction %eteen cyanidin.#.;.-l!coside and %.cyclode8trin (Fernandes et al/,201")/ adayachee et al/ (2012a, 2012%) st!died interactions of anthocyanins and &henolic acids ith &lant cell all com&onents(cell!lose and &ectin), in vitro/ Cell all com&o. nents interacted ith %oth anthocyanins and &henolic acids (adayachee et al/,2012a, 2012%)/

 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- .1'

he reason for these interactions co!ld %e the formation of ea %onds (+.%onds and hydro&ho%ic interaction) %eteen &oly. &henols and cell all com&onents/ +ydro-en %onds are formed %eteen hydro8yl -ro!&s of &oly&henols and o8y-en atoms of the -lycosidic lina-es of &olysaccharides/ Covalent %onds can %e formed %eteen &henolic acids and &olysaccharides/ Com&le8

 &or. o!s str!ct!re and s!rface &ro&erties of cell alls can also %e im&ortant (Fernandes et al/, 201"= *e o!rvellec et al/, 2005=Da!ra.Cali8to, 2011)/ an-, *i!, Chen, and hao (201#) st!died the im&ortance of the &oly&henol str!ct!re for %indin- ith

 &oly. saccharides/ hey s!--ested that hydro8ylation (three or less ;+ -ro!&s) of flavonoids and -alloylation of catechins

im&roved the adsor&tion into oat %.-l!can/ Bethylation or metho8ylation of &henolic acids loered the adsor&tion/ Glycosylatione8erted com. &licated infl!ences (an- et al/, 201#)/

ConseI!ences of these interactions co!ld %e m!lti&le/ First of all there is an infl!ence on the %ioavaila%ility of &henoliccom&o!nds/ Dome st!dies shoed that the %ioavaila%ility decreases d!e to the formation of associations of car%ohydrates and

 &oly&henols, hich act!ally ca&t!re &oly&henols into their str!ct!re/ Adam et al/ (2002) cond!cted a st!dy on a rat model,investi-atin- fer!lic acid %ioavaila%ility from s!&&lemented diets or from a com&le8 cereal matri8 (hole and hite flo!rs)/ 4tas fo!nd that the cereal matri8 limited fer!lic acid %ioavaila%ility/ he reason for this may %e fer!. lic acid association ith thefi%er fraction thro!-h cross.linin- ith ara%ino8ylans and li-nins/ 4ndeed, some later st!dies shoed that fer!lic acid can %emore availa%le hen %ran str!ct!re is r!&. t!red hich res!lts in the release of &henolic acids (einen et al/, 201"= Rosa, A!ra,

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ro%a%ly most of the &oly&henols that reach the colon are &oly. &henols hich are not a%sor%ed in the !&&er &arts of the-astroin. testinal tract and &oly&henols associated ith dietary fi%er (alafo8.Carlos et al/, 2011= Da!ra.Cali8to, 2011)/ $ietaryfi%ers can act as an entra&&in- matri8 and restrict the diff!sion of the enymes to their s!%strate hich may allo &oly&henols to

 %e car. ried to the colon (alafo8.Carlos et al/, 2011)/ 4n fact, recent find. in-s confirm that the fi%ers have a role as a carrier of dietary antio8idants to the colon (Da!ra.Cali8to, 2011)/ +ere they can enco!ra-e the -roth of %eneficial %acteria and inhi%it the-roth of &atho-enic %acteria (Da!ra.Cali8to, 2011)/ he infl!ence of hole &lant foods, &oly&henols and fi%ers on the h!man

intestinal.14 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- 

a%le # 4nteractions %eteen &oly&henols and car%ohydrates and their effects/

oly&henol tested Car%ohydrate model 3ffects References

Attachment, the infl!ence of &oly&henol str!ct!re and other &arameters on the interaction rocyanidins Cell all material(CB) . 4nteraction increased ith the molec!lar ei-ht of 

 &rocyanidins . 4nteraction decreased ith dryin- of CB (d!e to decrease

of CB &orosity)

*e o!rvellec et al/ (2005)

A&&le &oly&henols (&rocyanidins) Cell alls from a&&les . rocyanidins mainly %o!nd to &ectins *e

o!rvellec et al/ (2009) roanthocyanidins 4nsol!%le cell all material

(CB)

. 4nteraction as more related ith the &roanthocyanidin

molec!lar mass than the L of -alloylation

a!tista. ;rtTn et al/ (201") henolic acids from &!r&le carrot >!ice

concentrate

acterial cell!lose and cell!lose.&ectin com&osites

. !re cell!lose a%sor%ed more &henolic acids in the first ho!r, %!t after several days cell!lose and cell!lose.&ectin com. &le8esa%sor%ed similar levels of &henolic acids . 4ndivid!al &henolic acids %indin-= caffeic acid V chloro-enic

acid V fer!lic acid

adayachee et al/ (2012a)

Anthocyanins from &!r&le carrot >!ice

concentrate

acterial cell!lose and cell!lose.&ectin com&osites

. 4nteraction in to sta-es (ra&id initial sta-e, slo additional

sta-e) . indin- of acylated and non.acylated anthocyanins – similar 

 &attern . 4onic interactions ith &ectin and hydro&ho%ic ith

cell!lose

adayachee et al/ (2012%)

2# Flavonoids (flavones, flavonols, flavanones, isoflavones, flavanols)1# &henolic acids (hydro8ycinnamic and hydro8y%enoicacid)

;at %.-l!can . Adsor&tion ca&acities amon- flavonoid isomers:

flavonol V flavone V flavanone V isoflavone . Bethylation or metho8ylation of &henolic acids loered the

adsor&tion ca&acities . 3sterification of -allic acid eaened the adsor&tion ca&acity . o.Co!maric acid had hi-her adsor&tionca&acity than &. and

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m.co!maric acid . Galloylation im&roved the adsor&tion ca&acities of catechins

an- et al/ (201#)

Cyanidin.#.;.-l!coside %.Cyclode8trin (%.C$) . yranic C rin- as incl!ded inside the %.C$ cavity, rin- lies

on the &lane of the ider rim of %.C$

Fernandes et al/ (201")

In"luence on the pol#phenol bioaailabilit# *erulic acid !nimal stud# rats "ed with

vario!s heat flo!r 

. he cereal matri8 a&&ears to limit fer!lic acid %ioavaila%ility . Bost liely, the ca!se for this is fer!lic acid association ith

the fi%er fraction

Adam et al/ (2002)

Gra&e seed &rocyanidin e8tract Commercial cereal %ased food . A%sor&tion of dimer and trimer &rocyanidins is re&ressed %y

the &resence of car%ohydrate rich food . he !&tae of monomeric &rocyanidins is enhanced

Derra et al/ (2010)

4nfl!ence on the &oly&henol–&rotein com&le8es rocyanidin–try&sin com&le8es oly-alact!ronic acid, ara%ic

-!m, &ectin, 8anthan -!m

. Car%ohydrates &revented the association of &rocyanidin # and try&sin %y a com&etition mechanism (ionic character ofcar%ohydrates and the a%ility to enca&s!late &rocyanidins as cr!cial) . A--re-ation inhi%ition= 8antan -!m V &oly-alact!ronic

acid V ara%ic -!m ) &ectin

GonUalves et al/ (2011a)

Dalivary &rotein-ra&e seed &rocyanidin oly-alact!ronic acid (G),

ara%ic -!m (AG), &ectin

. ectin inhi%ited interaction %eteen &oly&henols and &ro.

teins the most, folloed %y AG and G . G and &ectin – mechanism incl!ded the formation of a ter.

nary com&le8 &rotein&oly&henolcar%ohydrate . AG – mechanism is a com&etition ith &roteins for tannin

 %indin- . +ydro&hilic and hydro&ho%ic interactions are im&ortant

Doares et al/ (2012a)

4nfl!ence on the car%ohydrate fermentation Fer!lic acid Ara%yno8ylanoli-osaccharides

(AW;D)

. o!nd and free fer!lic cid inhi%ited AW;D fermentation . o!nd fer!lic acid &ro%a%ly sterically hinders enyme

activity

Dnelders et al/ (201")

micro%iome as descri%ed %y !ohy et al/ (2012)/ 4t as also shon that &oly&henols can %e released from these matri8es and

meta%olied (Jordl!nd et al/, 2012= Rosa, A!ra, et al/, 201#= Da!ra.Cali8to, 2011)/ he str!ct!re of &oly&henols and the foodmatri8 can affect the &rocess of micro%ial de-radation (Jordl!nd et al/, 2012= Rosa, A!ra, et al/, 201#)/ For e8am&le, it asshon that dry fermentation of rye, heat, and oat %rans, hich lead to the de-radation of the cell all str!ct!re, enhances therelease of &henolic acids and the accessi%ility of micro%es to dietary fi%er and %o!nd &henolic acids/ his increased theconversion of &oly. &henols to meta%olites (Jordl!nd et al/, 2012)/ he enymatic dis. inte-ration of heat ale!rone alsoenhanced the formation of 

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 &oly&henolic meta%olites (Rosa, A!ra, et al/, 201#)/ Beta%olites can have some other &ositive infl!ence (Da!ra.Cali8to, 2011)/heir common activities are anti%acterial activities, anti.inflammatory activities, deto8ification &rocesses and &hytoestro-enicactivities (!ohy et al/, 2012)/ Bost of the &ositive role relates to the &rotec. tion a-ainst the ris of develo&ment of colorectalcancer (Bac$onald @ a-ner, 2012)/ Bac$onald and a-ner (2012) con. cl!ded that dietary %ioactive com&o!nds and their intestinal mic. ro%iota create a com&le8 milie! that directly affects the carcino-enic events of the colon/ 4t as also shon that

 &oly&he. nolic cata%olites are a%le to co!nteract to ey feat!res of dia%etic com&lications in vitro (&rotein -lycation and

ne!rode-eneration) (Herelloni et al/, 2011)/ 4n addition, &oly&henols associated ith dietary fi%ers can enhance the e8cretion of li&ids, &rotein, ater, and total fecal o!t&!t= they can have &ositive effects on li&id meta%olism, total cholesterol, *$*.cholesteroland triacyl-lyce. rides= and they can increase the antio8idant activity in the lar-e intestine (Da!ra.Cali8to, 2011)/

4nteractions %eteen car%ohydrates and &oly&henols can %e !sed for microenca&s!lation hich incl!des the entra&ment of theactive in-redient in coatin- material/ 4n that ay the active in-redient is isolated (&rotected) from the environment !ntil itsrelease/ Green tea &oly&henols can %e enca&s!lated on maltode8. trin as a coatin- material (!n-, Deon-, 'im, Byon-, @ Chan-,201#)/ D!ch microenca&s!lated -reen tea e8tracts can %e more effective at alleviatin- cardiovasc!lar ris than non.enca&s!lated-reen tea e8tracts (!n- et al/, 201#)/

Another im&ortant interaction of car%ohydrates is their interac. tion ith &oly&henol–&rotein com&le8es/ Jamely, &oly&henolscan create com&le8es ith &roteins (as mentioned) hich can affect n!tritional I!ality of &roteins/ F!rthermore, &oly&henol– salivary &rotein com&le8es are im&ortant for astrin-ency sensation of ines/ oly&henols interact also ith enymes hichres!lts in the inhi%ition of their enymatic activity/ Car%ohydrates hich are often &resent in food to-ether ith &oly&henols, can

interr!&t &oly&henol–&rotein com&le8es/ Car%ohydrates &oly-alact!ronic acid, ara%ic -!m, &ectin and 8anthan &revented theassociation of &rocyanidin # and try&sin (GonUalves, Bate!s, @ de Freitas, 2011a)/ Ara%ic -!m, &ectin and &oly-alact!ronicacid &revented association %eteen salivary &rotein and -ra&e seed &rocyanidins (Doares, Bate!s, @ de Freitas, 2012a)/ heinterr!&tion of &oly&he. nol–&rotein association %y car%ohydrates can &revent some of the ne-ative effects of these com&le8es,s!ch as enyme activity inhi. %ition, or they can infl!ence the &erceived astrin-ency of some food &rod!cts/

F!rthermore, interactions %eteen car%ohydrates and &oly&he. nols can affect car%ohydrate fermentation/ o!nd and freefer!lic acid inhi%ited ara%ino8ylanoli-osaccharides fermentation &ro%a. %ly %y sterically hinderin- the enyme activity (Dnelderset al/, 201")/

he st!dies disc!ssed here shoed that &oly&henolic com. &o!nds have the &ossi%ility to %ind to car%ohydrates/ his is veryim&ortant for their %ioaccessi%ility and %ioavaila%ility in the h!man or-anism/ Jamely, the association ith car%ohydrates maesthe &oly&henols %ioaccessi%le in the colon after they have %een e8&osed to enymes and microor-anisms and released/ Released

 &oly&henols may %e %ioaccessi%le in the colon and can even %e meta%olied %y the action of nat!rally &resent microor. -anisms/

he role of their meta%olites is still !nder the investi-a. tion %!t there is more and more evidence s!--estin- their vario!s &ositive effects/ he fact that &oly&henols react ith car%o. hydrates as !sed for the creation of car%ohydrate carriers of &oly. &henols thro!-h the -astrointestinal tract/ 4nteractions %eteen &oly&henols and car%ohydrates can infl!ence the car%ohydratefermentation/

 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- .1.

. Conclusions

An increasin- n!m%er of st!dies have shon that interactions of &oly&henols ith molec!les from foods (li&ids, &roteins,car%o. hydrates) can have a si-nificant im&act on the fate and role of &oly. &henols in the %ody/ Dince &oly&henols are introd!cedinto the %ody alon- ith other food in-redients, they come into contact ith them and react ith li&ids, &roteins, andcar%ohydrates/ he %indin- is mostly hydro&ho%ic, altho!-h hydro-en %onds and covalent %onds can %e created too, and vario!sassociations can %e formed/ heir %ioactivities can %e different than activities of any of these com&o!nds individ!ally/ *i&id– 

 &oly&henol com&le8es may ca!se a decrease in the li&id a%sor&tion/ 4n addition, access of free radicals to li&id molec!les can %e

hindered %y the &resence of &oly&henols in li&id molec!les, hich may res!lt in red!ced li&id o8idation and, conseI!ently, inred!ced occ!rrence of harmf!l li&id o8idation &rod!cts/ rotein–&oly&henol associations mi-ht infl!ence astrin-ency sensation,

 %iolo-ical activities of &roteins, the availa%ility of certain amino acids or even the di-esti%ility of &roteins/ 3nyme activityinhi%ition is also a conseI!ence of these interactions/ ;ne se-ment of interactions %eteen &oly&henols and other molec!les ass!--ested to %e very im&ortant/ hat is their delivery to the lar-e intestine here they can %e released and sho vario!s &ositiveeffects, lie the creation of antio8idative environment, the enco!ra-ement of -roth of %eneficial %acteria and the inhi%ition of the -roth of &atho-enic %acteria/ 4n addition, &ositive effects of their meta%olites are also s!--ested/ his as &artic!larlyreco-nied in the case of interactions of &oly&henols ith car%ohydrates/ 4t as also s!--ested that interactions of &oly. &henolsith li&ids, &roteins and car%ohydrates co!ld affect &oly. &henol %ioaccessi%ility and %ioavaila%ility/

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he a%ility of macromolec!les lie li&ids, &roteins and car%ohy. drates to act as carriers of &oly&henols thro!-h the di-estivetract is &artic!larly reco-nied/ Boreover, created associations may also &rotect &oly&henols from o8idative de-radation/

4t is clear that interaction %eteen &oly&henols and food in-re. dients are very im&ortant and that they infl!ence on o!r !nder.standin- of &oly&henols/ Bost of st!dies s!--ested &ositive effects of interactions hich can ha&&en %eteen &oly&henols andother food in-redients/ ;ne &art of st!dies deals ith the e8&lanation of &ossi%le n!tritional val!e decrease d!e to interac. tions(interactions ith &roteins and enymes)/ F!t!re st!dies sho!ld tae into acco!nt interactions %eteen &oly&henols and other 

com&o!nds %eca!se their contact is inevita%le/ 4t %ecomes more a&&arent that it mi-ht %e &ossi%le to e8&lain &oly&henol %en.eficial effects %y investi-atin- these com&le8 reactions and their conseI!ences/

!cnowled&ements

he or as s!&&orted %y a Grant from the Jational Fo!nda. tion for Dcience, +i-her 3d!cation and echnolo-ical$evelo&ment of the Re&!%lic of Croatia (0.190.2011)/ he a!thor ishes to than rof/ Francisco A/ omMs.ar%erMn and rof/Barina +einon. en for their advices/ D&ecial thans to rof/ Andre R/ arron/

-e"erences

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9611/

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.11 )* Jako+ek Food hemistry (-. /#$(.0 ..12.1- 

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4nteractions %eteen &oly&henols and macromolec!les: P!antification methods and mechanisms/ Critical Revies in FoodDcience and J!trition, 52, 21#–2"/ *orrain, /, $an-les, ;/, Genot, C/, @ $!fo!r, C/ (2010)/ Chemical modelin- of heme.ind!ced li&id o8idation in -astric conditions and inhi%ition %y dietary &oly&henols/ o!rnal of A-ric!lt!ral and Food Chemistry,5, 676–6#/ *orrain, /, $an-les, ;/, *oonis, B/, Armand, B/, @ $!fo!r, C/ (2012)/ $ietary iron. initiated li&id o8idation andits inhi%ition %y &oly&henols in -astric conditions/ o!rnal of A-ric!lt!ral and Food Chemistry, 60, 907"–901/ Bac$onald, R/D/, @ a-ner, '/ (2012)/ 4nfl!ence of dietary &hytochemicals and micro%iota on colon cancer ris/ o!rnal of A-ric!lt!ral and

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