Proceedings of the International Symposium on Natural Antioxidants Molecular Mechanisms and Health Effects Copyright © 1996 AOCS Press Proceedings of the International Symposium on Natural Antioxi- dants Molecular Mechanisms and Health Effects Editors Lester Packer Maret G. Traber Wenjuan Xin Champaign, Illinois Copyright © 1996 AOCS Press AOCSMissionStatement Tobeaforumfortheexchangeofideas,information,andexperienceamongthosewithaprofessional interestinthescienceandtechnologyoffats,oils,andrelatedsubstancesinwaysthatpromotepersonal excellenceandprovidehighstandardsofquality. AOCSBooksandSpecialPublicationsCommittee E.Perkins,chairperson,UniversityofIllinois,Urbana,Illinois J.Bauer,TexasA&MUniversity,CollegeStation,Texas N.A.M.Eskin,UniversityofManitoba,Winnipeg,Manitoba W.Farr,OwensboroGrainCo.,Owensboro,Kentucky T.Foglia,USDA—ERRC,Philadelphia,Pennsylvania L.Johnson,IowaStateUniversity,Ames,IA Y.-S.Huang,RossLaboratories,Columbus,Ohio J.Lynn,LeverBrothersCo.,Edgewater,NewJersey G.Maerker,Oreland,Pennsylvania M.Mossoba,FoodandDrugAdministration,Washington,D.C. G.Nelson,WesternRegionalResearchCenter,SanFrancisco,California F.Orthoefer,Stuttgart,Arkansas J.Rattray,UniversityofGuelph,Guelph,Ontario A.Sinclair,DeakinUniversity,Geelong,Victoria,Australia G.Szajer,AkzoChemicals,DobbsFerry,NewYork B.Szuhaj,CentralSoyaCo.,Inc.,FortWayne,Indiana L.Witting,StateCollege,Pennsylvania Copyright©1996byAOCSPress.Allrightsreserved.Nopartofthisbookmaybereproducedortrans- mittedinanyformorbyanymeanswithoutwrittenpermissionofthepublisher. Thepaperusedinthisbookisacid-freeandfallswithintheguidelinesestablishedtoensurepermanence anddurability. LibraryofCongressCataloging-in-PublicationData InternationalSymposiumonNaturalAntioxidants(1995:Peiking, China) ProceedingsoftheInternationalSymposiumonNaturalAntioxidants molecularmechanismsandhealtheffects/editors,LesterPacker, MaretTraber,WenjuanXin. p.cm. Includesbibliographicalreferencesandindex. ISBN0-935315-69-1(alk.paper) 1.Antioxidants—Therapeuticuse—Congresses.2.Naturopathy- -Congresses.I.Packer,Lester.II.Traber,Maret.III.Xin,Wenjuan.IV.Title. RM666.A5551581995 (cid:1) 615 .7—dc20 96-15468 CIP PrintedintheUnitedStatesofAmericawithvegetableoil-basedinks. 009998979654321 Copyright © 1996 AOCS Press Preface TheInternationalSymposiumonNaturalAntioxidants:MolecularMechanismsand HealthEffectswasheldduringJune20–24,1995inBeijing,China.Thissymposium wassponsoredbyUNESCO-MCBN;CommitteeforFreeRadicalBiologyandMed- icine;BiophysicalSociety(China);InternationalSocietyforFreeRadicalResearch; Institute of Biophysics,Academia Sinica;The International Union of Biochemistry andMolecularBiology;InternationalSocietyforFreeRadicalResearchAsia;Inter- national Union for Pure andApplied Biophysics, and Oxygen Club of California (USA).340scholarsfrommorethan20countriesparticipatedinthesymposium. Traditionallynaturalantioxidantsfromherbsandfoodshaveplayedveryimpor- tantrolesinmedicineandhealthprotection.Inrecentyears,greatprogresshasbeen achievedinstudiesontheeffectsandmechanismsofnaturalantioxidants,aswellas ontherelationshipbetweenantioxidantsandhumanhealth.Butthemolecularmech- anismsofnaturalantioxidantshaveyettobedeeplyinvestigated.Theacademicdis- cussionatthissymposiumhaveprovidedfurtherinsightintotheeffectsandmechanics of antioxidants; these may contribute to human health and the improvement of the lifestyleofmankind. Atotalof341paperswerereceived,4PlenaryLecturesweredeliveredand178 scholarsgavetheirreportsinsessionsincludingherbalsourcesandfoods;identifica- tion,characterizationandapplicationofantioxidants;chemicalandbiochemicaland biophysicalmechanismsofantioxidants;effectsofantioxidantsoncellregulationand transcellular signalling; the relation of antioxidants with NO and oxygen free radi- cals;theapplicationofantioxidantsinischemia-reperfusioninjury,inflammation,can- cer,aging,cardioandvasculardiseases;seleniumandthiolantioxidants,etc. Many good results were presented in this symposium. Participants exchanged livelyandfriendlyideasinvarioussessionsandinroundtablediscussions. Webelievethatthissymposiumhasenhancedthecooperationbetweenscientists ofvariouscountriesandacceleratedthedevelopmentofstudiesoffreeradicalsand antioxidants. We would like to express our thanks to all the participants and to the authors whosepapershavebeencollectedinthisbook.Theirenthusiasticcontributionshave madethewholesymposiumsuccessful. Wewouldalsoliketoexpressoursincerethankstothemanyorganizationsthat providedsupport:UNESCO-MCBNGlobalNetworkofMolecularandCellBiology; A.O.A.JapanCo.,Ltd.;BeckmanInstruments-GreaterChina;SolvayPharma-LTM, France;TheInternationalUnionofBiochemistryandMolecularBiology(IUBMB); UnileverResearch,US;NationalNaturalScienceFoundationofChina;International UnionforPureandAppliedBiophysics(IUPAB);ChineseAcademyofSciences;The Chinese Society of Biochemistry and Molecular Biology; Biophysical Society of China;Neo-LifeGoldenGroup;AmericanOilChemists’Society;Colgate-Palmolive; IPSENInstitute;DiamiteCorporation(USA);China v Copyright © 1996 AOCS Press vi Preface NationalTobacco Corp., Beijing Branch; MACOMAIncorporated Japan; Chengdu ShuyangPharmaceuticalFactory,China;LanzhouShijinNaturalHealthyFoodCo., LTD,China;BectonDickinson,Inc;TianbaoBranchoftheTiantaiPharmaceuticals Factory, Zhejiang, China; Xiamen Qiran Health Care Product Limited Co., China; Nanjing Jiancheng Biotechnological Institute, China; Biotechnology Company of HebeiUniversity,China;KanChiMedicalCo.,Ltd. LesterPacker MaretG.Traber W.Xin Copyright © 1996 AOCS Press Contents Preface................................................................................................v Introduction Chapter1 DynamicsofAntioxidationbyPhenolicAntioxidants:Physiochemi- .................... calIssues........................................................................ 1 E.Niki,N.Noguchi,M.Iwatsuki,andY.Kato ..... Chapter2 AntioxidantDefensesinBiologicalSystems:AnOverview........ 9 L.Packer .... Chapter3 AntioxidantsfromTraditionalChineseHerbs......................... ....24 G.Liu .... Chapter4 TheRoleofXanthineOxidaseinDisease........................... .......33 C.R.Stevens,T.Sahinoglu,B.Bhatt,N.N.Ali,andD.R.Blake HerbalSourcesandFoods Chapter5 AntioxidantDefensesofTJ-960,AJapaneseHerbalMedicine, ..... AgainstFreeRadical-InducedNeuronalCellDamage............ ..45 A.Mori,H.Hamada,H.Ohyama,M.Hiramatsu, andS.Shinohara .. Chapter6 AgingandHerbalAntioxidants................................................... ..54 M.Hiramatsu,M.Komatsu,andY.Ueda Chapter7 TheAntioxidativeandAntitumorEffectsofPhenylpropanoidGlyco- .......... sidesfromPedicularis....................................................... ....64 R.L.Zheng,andZ.J.Jia Fructus Chapter8 TheAntioxidantandAntistressActivitiesoftheExtractof Momordicae ............. ...................................................................... ..71 X.Wang,J.Liu,M.Sanada,S.Okada,andA.Mori Chapter9 AntioxidizingandRadioprotectiveMechanismsofHydroxycin- ...........82 namicAcidDerivatives:PulseRadiolysisandESRStudies S.D.Yao,J.S.Zhang,andN.Y.Lin Chapter10 ExtractsofSomeIndianPlantswithPotentAntioxidantProperties ............... ......................................................................................... ..90 G.Maulik,V.E.Kagan,S.Pakrashi,N.Maulik,andD.K.Das Chapter11 Anti-inflammatoryAntioxidantsfromMedicinalGingers:New ComplexCurcuminoidsfromZingiberCassumunar......................99 T.Masuda,andA.Jitoe Chapter12 EffectsofBio-Normalizer(ANaturalJapaneseFoodSupplement) onOxygenRadicalandTumorNecrosisFactorProductionbyMon- ................................... cytesandMacrophages............................. ..109 J.A.Osato,L.G.Korkina,E.Mikhal’chik,andI.B.Afanas’ev vii Copyright © 1996 AOCS Press viii Contents IdentificationandCharacterizationofAntioxidants Chapter13 ChemicalStudiesofNaturalAntioxidantsfromTraditionalChinese ............... Medicines................................................................... .....117 L.-N.Li Chapter14 StudiesofAntioxidantActivitybyMeasuringChemiluminescence ................................... Kinetics..................................................... ..125 Y.A.Vladimirov Chapter15 AnInVitroSystemforEvaluationofOxidativeStressandEffects ............... ofAntioxidants............................................................... .145 J.Clausen Chapter16 AntioxidantFunctionofCarnosine,aNaturalHistidine-Containing ..................... Dipeptide.................................................................. .155 C.K.Chow,V.L.Tatum,C.C.Yeh,M.Maynard,W.Ibrahim,G. Bruckner,G.A.Boissonneault,andC.B.Hong ApplicationofAntioxidants Chapter17 EffectofVitaminEStatusonRedBloodCellProcoagulantActivity b ................... in-Thalassemia/HbEDisease ............................ ......162 S. Kasemsant,andP.Wilairat Chapter18 ProtectiveEffectofVitaminEandZinconExperimentalHepatitis ............... ....................................................................................... ...167 C. Rendun,H.X.Ming,andH.H.Long C - Chapter19 ardiovascularEffectsofGinsenosidesandTheirNitricOxide Mediated Antioxidant Action .........................................................179 X. Chen AlliumSativum é Chapter20 Influenceof Linn onOxidativeStressStatus:A .... ClinicalInvestigation............................................................. ...188 W.G.Siems,T.Scherat,H.Behrend,R.Brenke,M.Jakstadt,E. Con radi,andT.Grune Chapter21 AntioxidantSynergismandMutualProtectionofβ-Caroteneand Vi taminEintheInhibitionofRadicalInitiatedPeroxidationof ............................. LinoleicAcidinMicelles................................ .196 Z.-L. Liu, Z.-L. Li,L-P.Ma,andY.-C.Liu Ginkgobiloba Chapter22 InhibitionofPreretinalProliferationby ExtractEGb 761andSuperoxideDismutaseinanExperimentalModelofTrac- .............. tionalRetinalDetachment.............................................. 210 M.Ettaiche,C.Baudouina,F.Imbert,M.T.Droy-Lefaix,P.Gastaud, andP.Lapalus Copyright © 1996 AOCS Press Contents ix ThiolAntioxidants Chapter23 CellRegulationbyThiolAntioxidantsfromGlutathionetoLipoate ................ toAnetholeDithiolethione........................................... 223 L.Packer .. Chapter24 AnetholeDithiolethione:ResearchOverviewandPerspectives. 236 M.O.Christen ... Chapter25 MechanismsofChemoprotectionby1,2-Dithiole-3-Thiones... 243 T.W.Kensler,T.Primiano,T.R.Sutter,P.A.Egner,P.M.Dolan,J.D. Groopman,T.J.Curphey,andB.D.Roebuck of Dry Mouth in Chapter26 EffectofAnetholeDithiolethioneintheTreatment ö ................................. Sj gren’sSyndromeandSialadenosis......... .251 S.Wang,X.Z.Zhu,andH.Dong in the Chapter27 RandomizedControlledTrialofAnetholeDithiolethione .................. TreatmentofAntipsychotic-InducedXerostomia..... ..254 J.Zhongfu,L.Dao,L.Ruiming,andL.Shicheng Metallothionein Antioxidant Chapter28 CanMetallothioneinBeUsedasaPotential ..................... Medicine?.................................................................. 261 X.Fang,W.Wang,andJ.Wu Chapter29 MetallothioneinProtectionofCerebralCortexCellsAgainstHy- .... poxicDamage........................................................................... .272 W.Benjie,L.Jingfen,andY.Guifen Chapter30 EffectsofAntagonismandCytoprotectiveEffectsofMetalloth- ............... ionein........................................................................... ...278 S.Cheng.Y.Huaa,Z.Yang,X.Yue,andJ.Zhou by Metallothionein Chapter31 ThymineRadiationDamageandItsModification ........................... ....................286 ........................................................ . X.Fang,J.Wu,andG.Wei CellRegulationandTranscellularSignalling Chapter32 EffectofVitaminETreatmentontheDevelopment ..... ofAtherosclerosis..................................................................... 294 Ö Ö ç Ö ü N.K. zer, .Sirik i,T.San, .G zel,andA.Azzi Chapter33 SignalTransductionandOncogeneExpressionMediated byReactiveOxygenSpecies.........................................................303 J.K.Lin,S.F.Lee,Y.T.Huang,andS.Y.Lin-Shiau Chapter34 FibroblastProlylHydroxylaseModulatedbySignallingPathways .............320 InvolvingPolyADP-Ribosylation..................................... J.J.Qian,andR.S.Bhatnager Copyright © 1996 AOCS Press x Contents Chapter35 ElevationofMacrophageSeGSHPxGeneExpression ... ...... andPreventionFromItsFormationofFoamCell........... ... 339 Z.Mei,C.Yuan,L.Shangxi,G.Zhigang,L.Ning,andL.Jun Chapter36 Modulationoftheβ-Receptor-AdenylylCyclaseSystembyOxygen Radicals:RelationshiptotheVitaminEConcentration..............352 I.Schimke,A.Haberland,L.Will-Shahab,andG.Baumann ReactiveOxygenSpecies,NitricOxide,andAntioxidants Chapter37 Inactivationofα-1-ProteinaseInhibitorbytheSimultaneousGener- ............... ationofNitricOxideandSuperoxide........................... .359 Z.Zhang,E.R.Frears,D.R.Blake,andP.G.Winyard Chapter38 MetabolismofProteinBoundReactiveSpeciesFormedbyRadical ............ Damage........................................................................... ..367 S.Fu,S.Gebicki,W.Jessup,J.M.Gebicki,andR.T.Dean Chapter39 ChinoninCanScavengeNOFreeRadicalsandProtecttheMy- ......... ocardiumAgainstIschemia-ReperfusionInjury................ ..378 B.-L.Zhao,J.-G.Shen,M.Li,Q.Wan,M.-F.Li,andW.-J.Xin GreenTea Chapter40 StudyonAntimutagenicityandAnticarcinogenicityofGreenTea .......... Epicatechins-NaturalFreeRadicalScavenger.................. .392 S.J.Cheng S Chapter41 A tudyontheEffectsofGreenTeaPolyphenolsonLipidFree Rad ... . ... icals. .................................................................................. .397 W.Xin,H.Shi,F.Yang,B.Zhao,andJ.Hou Ginkgo ..... Chapter42 EGb761andReperfusionInjuryoftheRetina....................... 413 M.T.Droy-Lefaix,J.M.Menerath,E.Szabo-Tosaki, B.Bonhomme,andM.Doly InVitro InSitu: Chapter43 MitochondrialOxidative-Phosphorylation and Ef- .... fectsofEGb761....................................................................... 417 K.Willet,O.Detry,A.Evens,M.T.Droy-Lefaix,andF.E.Sluse GinkgoBiloba Myo- Chapter44 ExtractProtectsUltrastructureofHypoxic in Elderly Rats ....... cardium ....................................................... ...424 K.Welt,F.Fitzl,andL.Schaffranietz Ginkgobiloba Chapter45 Preventionby ExtractofAge-AssociatedImpairment ....................... ofBrainMitochondria.......................................... .434 á á ó ía J.Sastre,R.Pl ,G.Juan,A.Mill n,F.V.Pallard ,J.Garc dela ó í M. Asunci n,J.A.Martn,E.O’Connor, T.Droy-Lefaix,andJ.Viсa Copyright © 1996 AOCS Press Contents xi GinkgoBiloba Chapter46 Effectsof Extract(EGb761)onFreeRadical-In- ...... ducedDamageintheBrain................................................ .....444 F.Clostre Ginkgobiloba Chapter47 InhibitoryEffectsof Extract(EGB761)onOxygen FreeRadicals,NitricOxide,andMyocardialInjuryinIsolatedIs- .................... chemic-ReperfusionHearts....................................... 453 J.-G.Shen,B.-L.Zhao,M.-F.Li,Q.Wan,andW.-J.Xin Ginkgobiloba Chapter48 ExtractProtectsEnzymeActivitesintheHypoxic ............... RatMyocardium........................................................... .466 K.Punkt,K.Welt,andL.Schaffranietz Ginkgobiloba Chapter49 AntioxidantPropertiesof ExtractEGB761andClini- ........ calImplications.................................................................... .472 L.Packer,L.Marcocci,N.Haramaki,H.Kobuchi,Y.Christen, andM.T.Droy-Lefaix Chapter50 EGB761InhibitionofNuetrophilFunctionsandAdhesiontoEn- ......... dotheliumActivatedbyOxygenFreeRadicals................... 488 C.Pasquier,C.Babin-Chevaye,andC.Marquetty Ginkgobiloba Chapter51 ScavengingEffectsof L.andHawthornLeaveson ........... OxygenFreeRadicalsandTheirAntioxidantAction..... ..499 P.L.Huang,andZ.H.Zeng Ginkgobiloba Chapter52 ExtractProtectionofBrainNeuronsfromDamage ................ InducedbyFreeRadicals........................................... ..506 Y.Ni,B.Zhao,J.Hou,andW.Xin Chemical,Biochemical,andBiophysicalMechanisms Chapter53 Co-ExistenceofReactiveOxygenCyclewithQ-CycleinRespira- toryChain:AHypothesisforGeneration,PartitioningandFunction- ........................... ingofSuperoxideinMitochondria.................... 513 S.-S.Liu,andJ.-P.Huang Chapter54 MitochondrialRespiratoryChain:ASelf-DefenseSystemAgainst .............. OxygenToxicity.............................................................. 530 X.Jian-Xing,L.Xun,Z.Yi-xin,andS.He-yong Chapter55 ScavengingEffectsofBaicalinanditsCopper,ZincComplexeson ....... SuperoxideRadicalsandPeroxynitrite.................................. 540 H.Shi,B.Zhao,andW.Xin Chapter56 KineticStudyofFree-RadicalScavengingActionofFlavonoidsin ......................................5 AqueousTritonX-100MicellarSolution 57 K.Mukai,W.Oka,Y.Egawa,S.-I.Nagaoka,andJ.Terao .... Chapter57 SuperoxideAnionToxicity:AMechanismStudy.............. ......569 Q.H.Luo,W.Qian,andJ.Wang Copyright © 1996 AOCS Press