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Membrane lipids protected from oxidation by red wine tannins A

Biochimiexxx(2014)1e9

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Biochimie

journalhomepage:www.elsevie

Membrane lipids protected from oxidation by red wine tannins A

http://www.wendangxiazai.com/locate/biochi

Researchpaper

Membranelipidsprotectedfromoxidationbyredwinetannins:AprotonNMRstudy

lienL.Furlana,1,2,Marie-LiseJobina,1,Se bastienBuchouxb,AxelleGre larda,Aure

ana,*ErickJ.Dufourca,JulieGe

ab

InstituteofChemistryandBiologyofMembranesandNano-objects,UMR5248,CNRS,UniversityofBordeaux,IPB,F-33600Pessac,France

Unit edeG enieEnzymatiqueetCellulaire,FRE3580,CNRS,Universit edePicardieJulesVerne,F-80039AmiensCedex,France

articleinfo

Articlehistory:

Received30May2014Accepted8July2014AvailableonlinexxxKeywords:

Lipidoxidation

Antioxidantef ciencyTannins

MembranelocationNMR

Moleculardynamics

abstract

Dietarypolyphenolswidespreadinvegetablesandbeverageslikeredwineandteahavebeenreportedtopossessantioxidantpropertiesthatcouldhavepositiveeffectsonhumanhealth.Inthisstudy,wepro-poseanewinsituandnon-invasivemethodbasedonprotonliquid-statenuclearmagneticresonance(NMR)todeterminetheantioxidantef ciencyofredwinetanninsonatwice-unsaturatedphospholipid,1,2-dilinoleoyl-sn-glycero-3-phosphocholine(DLiPC),embeddedinamembranemodel.Fourtanninswerestudied:(þ)-catechin(C),(À)-epicatechin(EC),(À)-epicatechingallate(ECG),and(À)-epi-gallocatechingallate(EGCG).Thelipiddegradationkineticswasdeterminedbymeasuringthelossofthebis-allylicprotonsduringoxidationinducedbyaradicalinitiator,2,20-Azobis(2-methylpropionamidine)dihydrochloride(AAPH).Theantioxidantef ciency,i.e.theabilityoftanninstoslowdownthelipidoxidationrate,wasshowntobehigherforgalloylatedtannins,ECGandEGCG.Furthermore,themixtureoffourtanninswasmoreef cientthanthemosteffectivetannin,EGCG,demonstratingasynergisticeffect.Tobetterunderstandtheantioxidantactionmechanismofpolyphenolsonlipidmembranes,thetanninlocationwasinvestigatedbyNMRandmoleculardynamics.Acorrelationbetweenantioxidantactionoftanninsandtheirlocationatthemembraneinterface(insertedattheglycerolbackbonelevel)couldthusbeestablished.

©2014ElsevierMassonSAS.Allrightsreserved.

1.Introduction

Oxidationoflipidscomposingbiologicalmembranesandlipo-proteinsiscausedbyanexcessoffreeradicalsincludingreactive

Abbreviations:AAPH,2,20-Azobis(2-methylpropionamidine)dihydrochloride;AOE,antioxidantef ciency;C,(þ)-catechin;ATB,automatedtopologybuilder;DCPC,1,2-dicaproyl-sn-glycero-3-phosphocholine;DLiPC,1,2-dilinoleoyl-sn-glyc-ero-3-phosphocholine;DMPC,1,2-dimyristoyl-sn-glycero-3-phosphocholine;EC,(À)-epicatechin;ECG,(À)-epicatechingallate;EGCG,(À)-epigallocatechingallate;HAT,hydrogen-atomtransfer;HPLC,high-performanceliquidchromatography;Kow,octanolewaterpartitioncoef cient;MAS,magicanglespinning;MD,molec-ulardynamics;MLV,multilamellarvesicles;NMR,nuclearmagneticresonance;POPC,1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine;PUFA,polyunsaturatedfattyacids;ROS,reactiveoxygenspecies;SET,single-electrontransfer;TMSP,so-dium3-trimethylsilyl-2,2,3,3-2H4-propionate.

*Correspondingauthor.Tel.:þ33(0)540006835.

an).E-mailaddress:j.gean@cbmn.u-bordeaux.fr(J.Ge

1

Authorscontributedequallytothiswork.2 lienFurlan,Unite deGe nieEnzymatiqueetCellulaire,FREPresentaddress:Aure

dePicardieJulesVerne,33rueSaint-Leu,80039Amiens3580CNRS,Universite

Cedex,

Membrane lipids protected from oxidation by red wine tannins A

France.

http://www.wendangxiazai.com/10.1016/j.biochi.2014.07.008

0300-9084/©2014ElsevierMassonSAS.Allrightsreserved.

oxygenspecies(ROS)naturallyproducedbythehumanbodydur-ingthenormalmetabolismofdioxygen[1].To ghtROS,thehumanmetabolismhasdevelopeddefensivemechanisms:enzymaticsystems(suchassuperoxidedismutase,glutathioneperoxidase,glutathionereductase,andcatalase)andendogenouschemicalantioxidants(e.g.glutathione,coenzymeQ,vitaminE…).However,whenthelatterbecomeinef cient,oxidativestresshappens,i.e.,animbalancebetweenantioxidantsandROSmayoccur.Lipidsthatplaycrucialphysiologicalroles,withproteins,carbohydratesandnucleicacids,arethemaintargetsoffreeradicals.Thus,lipidoxidationbyinducingirreversiblecellandlipoproteindamagesarestronglysuspectedtoplayaroleinmanyhumanpathologiessuchascancers,cardiovasculardiseases,neurodegenerativediseasesandin ammatorydisorders[2,3].Onepossiblemannertocoun-teractthelipidoxidationanddeleteriouseffectsoffreeradicalswouldbetoconsumeexogenousantioxidants.Amongthemostef cient,polyphenoliccompoundswiththeirmanyhydroxyl-substitutedaromaticringsarepotentiallypromising.Presentinvegetables,highquantitiesofpolyphenolsarefoundinredwineandblackteaintheformofcondensedtannins,i.e.,polymersof3-

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