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JOURNALOFFOODCOMPOSITIONANDANALYSIS JournalofFoodCompositionandAnalysis19(2006)S66…S73CriticalReviewFlavanonesinoranges,tangerines(mandarins),tangors,andtangelos:acompilationandreviewofthedatafromtheanalyticalliteratureJuliaJ.Peterson,JohannaT.Dwyer,GaryR.Beecher Correspondingauthor.TuftsUniversitySchoolofNutritionScienceandPolicy,40WebsterAv,Beverly,MA01915-2137,U.S.A.Tel.:+19789270414;fax:+16176368325.E-mailaddress:Julia.Peterson@tufts.edu(J.J.Peterson). Inaddition,severalhybridshaveatangerineforoneparentandatangerinehybrid,usuallyatangor,astheotherparent.Thesourorangeisusuallyeateninmarmaladesratherthanraw.ItsgeneraltaxonisCitrusaurantiumrelatedtaxonsareC.bergamiaC.myrtifoliaFig.2showsthecitrus”avanoneglycosidesandaglycones.Allorange-typecitrusfruitscontainthe”avanoneaglyconeshesperetinandnaringenin,buttheyrarelyoccurasfreeaglyconesinthefruititself.Thedominant”avanoneglycosidesinsweetorangesC.sinensis)arehesperidinandnarirutin,whereasinsouroranges(C.aurantium)thetwopredominant”avanoneglycosidesareneohesperidinandnaringin.Themajordifferencebetweenthe”avanoneglycosidesofsweetandsourorangesisintheirsugarmoieties,whichin”uencetaste.Thesugarrutinose(6--L-rhamnosyl--D-glucose)causesthe”avanoneshesperidinandnarirutintohaveaneutraltasteandisrelativelyhighinsweetoranges,tangerines,andtangors.Thesugarneohesperidose(2--L-rhamnosyl--D-glucose)ishighintangelosandsourorangesandimpartsatangyorbittertastetotheglycosidesneohesperidinandnaringin.Thegoalsofthisstudyweretocompileanalyticdataofacceptablequalityfromthescienti“cliteratureandpresentvaluesonthe”avanonesinorangetypecitrusfruitsforaprovisional”avonoidfoodcompositiontable.Asimilartreatmentofgrapefruit,lemonsandlimesispresentedinthisjournalissue(Petersonetal.,20062.MaterialsandmethodsTherelevantfoodcompositionanalyticalliteraturewassearchedusingmethodspreviouslydescribedforarticlesdatedfrom1968to1998andsubsequentlyabstractedPetersonandDwyer,2000).Anadditionaltwoarticlesfrom2000wereprovidedthroughourcollaborationwiththeUnitedStatesDepartmentofAgricultureNutrientDataLaboratory.Inall,weobtained125articlesjustoncitrus.Therewereveryfewcitationsfor”avonoidclassesandcompoundsotherthan”avanones.Therewassomedataonsweetorangesfor”avonols(Berhowetal.,1998Carerietal.,2000Drawertetal.,1980a,bHertogetal.,Justesenetal.,1998Nogataetal.,1994),”avones(hydroxy”avones„Berhowetal.,1998Carerietal.,2000Hertogetal.,1993Justesenetal.,1998Nogataetal.,;methoxy”avones„Nogataetal.,1994Pupinetal.,RouseffandTing1979Sendraetal.,1988Veldhuisetal.,1970)andanthocyanins(Rapisardaetal.,),andnonefor”avan-3-olsoriso”avonoids.Basedonourpreliminarydatacollection,total”avonoidsforsweetorangeswere19.6mgaglycones/100gediblefruitorjuiceand”avanoneswere95%ofthosemeasured.Fortangerines,total”avonoidswere26.4mgaglycones/100gediblefruitorjuiceand”avanoneswerealso96%ofthetotal”avonoidsmeasured.Anthocyaninsarefoundinbloodorangesandtheonlyquantitativestudyobtainedfoundtheyaveraged7mgaglycones/100gediblefruitorjuice(Rapisardaetal.,1994).Althoughcitrus”avonoiddataon”avanones,”avones,”avonolsandanthocyaninswerecompiled,thisarticlewillfocusonthe”avanonesastheyarethemajorclassof”avonoidspresentincitrus.ArticlesontheothercompoundsareplannedfortheSothattheliteraturewouldbethoroughlysearched,”avanonecompoundsincitruswerelistedindividually.Twenty-threearticles,whichreportedvaluesonthesecompounds,wereusedforthisstudy.Studieson12”avanoneglycosideswerefound.Eightcompoundswerecomposedofonlyfouraglyconeswithglycosidesformedbyeitherthesugarrutinoseorneohesperidose.RelativelyARTICLEINPRESS Common Namespecies namevariety Sour Orangeaurantium BloodDoblefina,Malta, Moro,Sanguinello Pera, Shamouti NavelLane's Late,Navel, Thomson,Washington ValenciaHart's Late,Valencia Late Sweet Orangesinensis Tangorreticulata X sinensis CommonCravo, Dancy,Satsuma Ambersweet, Tangerinereticulata Honeybell, K-Early,Minneola, Seminole grapefruit or pummeloX paradisi or grandis Lowest flavanone content and similarcompoundsRange 19-25 mg aglycones /100 g Highest flavanone content g a y cones /100 g Moderate flavanone content g a y cones /100 g Fig.1.Relationshipsbetweentaxonomicclassi“cationsand”avanonecontentoforangesandnearrelativesinthegenusCitrus.J.J.Petersonetal./JournalofFoodCompositionandAnalysis19(2006)S66–S73 abundantdatawereavailablefortheseeight”avanoneglycosides(didymin,eriocitrin,hesperidin,narirutin,nar-ingin,neoeriocitrin,neohesperidin,andponcirin)(Fig.2Fourotherminor”avanoneswerenotconsideredfurther[naringin-4-glucoside,naringin-6-malonate(closedform),naringin-6-malonate(openform),narirutin-4-glucoside]becauseonlyonestudy(Berhowetal.,1998)wasavailableonthesecompounds.Thequalityofthe”avanoneanalyticaldatawasassessedusingthecriteriaforevaluatingfoodcompositiondatathatwereoriginallydevelopedandusedincompilingUnitedStatesDepartmentofAgriculture(USDA)foodcomposi-tiontables(Holdenetal.,2002Mangelsetal.,1993).Thebasicideasofthissystemwereusedtomakethedecisionsabouttheinclusionorexclusionofthedatasourcesinconsultationwithcollaboratorsfamiliarwiththechemistryandfoodscienceofcitrus.The“vequalityassessmentcriteria(numberofsamples,samplehandling,samplingplan,analyticalmethod,andanalyticalqualitycontrol)wereutilizedandappliedtoeachcitrusdatapointintheanalyticalliteraturethatcouldbeidenti“edforthe”avonoidsincitrus.Withrespecttotheevaluationofthenumberofsamplesadatapointwastakentobeeachanalyticalvaluethatwasreported,usuallyameanofduplicateortriplicateanalyticalvalues,butoccasionallyasingleanalyticalvalue.Eachdatapointwastreatedasanof1andnoweightingfactorwasappliedtoadjustforthenumberofsamplesincluded.Datapointsdescribedasnotdetectedwereassignedavalueofzero.BasedonstatisticalanalysesMangelsetal.,1993),tracevalueswereassignedtobe71%ofthelimitofquanti“cationforthemethodused.Thedatawereplacedinastandardizedformatwithrespecttotaxons(genus,species).Allvarietieswereveri“edusingGermplasmResourcesInformationNetwork(GRIN),EvaluerGerer,Informatiser,Diffuser(EGID),andothertaxonomicsources(Purdue,USDA,andAustralia).Inaddition,listsofcommercialcultivarsandvarietieswereobtainedusingtwosources,FreshCitrusWardowskietal.,1986)andFloridaCitrusVarietiesTuckeretal.,1998).Tangerinehybridswhereoneparentwasatangerineandtheotherparentwasatangerinehybrid(tangor,tangelo,etc.)wereconsideredtangerines.Informationwasinsuf“cienttoclassifycertainvarietiesARTICLEINPRESS Hesperidinsweet oranges,tangerines, tangorsOHOHOHOHOHDidyminIsosakuranetin 7-O-rutinoside, Neoponcirin Narirutinsweet oranges, tangerines, tangors Neohesperidinsour oranges,Isosakuranetin 7-O-neohesperidosideNeoeriocitrinsour orangesNaringinsour oranges,AglyconesOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOCH HesperetinOCH3IsosakuranetinEriodictyolNaringeninOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOHOH CrutinoseSugarsH CH CH CH CH CH COCHOCHOCHOCH H CH CH C Fig.2.Citrus”avanoneaglyconesandglycosides.StructuresfromHarborneandBaxter(1999).Structurenumbersforglycosidesaredidymin„1123,eriocitrin„1200,hesperidin„1207,narirutin„1111,naringin„1112,neoeriocitrin„1201,neohesperidin„1208,andponcirin„1124. http://www.ars-grin.gov/cgi-bin/npgs/html/taxgenform.plhttp://www.corse.inra.fr/sra/egide.htmhttp://www.hort.purdue.edu/newcrop/morton/http://www.ars.usda.gov/ls/np/phenolics/ap1/ca-I.htmhttp://www.sardi.sa.gov.au/hort/cit_page/cit_var.htmJ.J.Petersonetal./JournalofFoodCompositionandAnalysis19(2006)S66–S73 (includingsambokan,shunko-kan,tengu,ujuikitsuandaKoreantangerine)intoclassesorsubclassesoforangetypecitrus;therefore,dataconcerningthemwerenotincluded.samplehandling,mostsampleswereeithercommer-cialandrefrigeratedorfrozenuntilanalysisorfreshfruitwereprocessedinthelaboratorypriortoanalysis.Withtheexceptionofonearticlethatusedgaschromatography,theanalyticmethodologyusedingeneratingthesedatawasallhigh-performanceliquidchromatography(HPLC).ValuesdeterminedbytheDavismethod,aspectrophotometricmethodthatmeasurestotal”avanones,werenotused.Dataforeachoftheeight”avanoneglycosidesineachorangetypecitrusgroupwerereviewedanddescriptivestatisticswerecalculated.Analyticalqualitycontrolalsoreviewed.Olderarticlestendedtobelessexplicitinthementionofthesedetailsinpartperhapsbecauseatthetimesuchdetailswereunderstoodasstandardoperatingprocedure.Newerarticlestendedtobemoredetailed.Dataonjuiceandfruitwereseparatedfromvaluesprovidedforthepeelorothercitrusproducts.Allcitrus”avonoiddatawereconvertedfromtheiroriginalunitstomg/100gbyusingBrixdatatoobtainthedensityorbyemployingtheUSDAstandarddensityof1.045forfreshlysqueezedand1.052forcommerciallyprocessedorangejuice.Allglycosideswereconvertedtomg/100gaglycones.Datawereaggregatedtaxonomically(e.g.,byspeciesandhybrid)into“veorangetypes(sourorange,sweetorange,tangerine,tangelo,tangor)foreachoftheeight”avanoneglycosidesstudied.Descriptivestatisticswerecalculatedasaglycones,meansofall”avanoneaglyconesweresummedforeachorangetype,andboxplotsoneachtypewereproduced(Table1).Outlyingvalueswereexaminedandallwerejudgedtobewithinthenormallimitsofenviron-mentalvariabilityandincludedintheanalysis.Afterexaminationofthedegreetowhichsweetoranges,tangerinesandtangorshadsimilar”avanonepro“lesandlevels,thedatapointsforthesecitrusfruitswereaggre-gated;themeanofeach”avanoneandthetotal”avanonesaregiveninTable2Althoughnotconsideredhere,includedinourdatabaseareextractionprocess,fruitportion,geographiclocation,dateofharvest,andadditionalmethoddata.3.ResultsTable1providestotal”avanonecontentoftheindividual”avanonecompoundsfororangesandnearrelatives(tangerines,tangors,andtangelos).Atleasttwoarticlesforeach”avanonecompoundinsweetorangeswerefound(exceptponcirinthathadtwotangerinearticles).Hesperidinhad18articlesforsweetoranges.Therewerenosigni“cantdifferencesbetweenthefoursubclassesofsweetorangesforhesperidinandnarirutin.Comparisonofjuice(handandcommercial)andfruit(pulpandvesicle)revealednostatisticallysigni“cantdifferenceamonganyofthesefornarirutin.Therewasaslightlysigni“cantdifferenceforhesperidinbutonlybetweenjuicesqueezedbyhandandthewholefruit(bothpulpandvesicle).Therewasnostatisticaldifferencebetweencommercialjuicesandjuicessqueezedbyhandandbetweencommercialjuicesandwholefruit(bothpulpandvesicle)forhesperidin.Orangesandtheirnearrelativesdifferedintwocharacteristicsofpossiblehealthsigni“cance;theirindivi-dual”avanonepro“lesandtheamountoftotal”avanonesprovided.Insweetoranges,tangerinesandtangors,the”avanoneglycosidepatternconsistedpredominantlyofhesperidinandnarirutin.Insouroranges,naringin,neoeriocitrin,andneohesperidinpredominated.Tangeloscontainedsomeofalloftheseglycosidesbutneohesperidinpredominated.Table2presentsacomparisonofthe”avanonecontentoftheseorangetypecitrusfruits.Sweetorangeswerethelowestintotal”avanones(summedmeans)at17mgtotal”avanoneaglycones/100gediblefruitorjuicewhereastangerinesandtangorsaveragedslightly,butnotsigni“-cantly,higheramounts(23and25mgaglycones/100gediblefruitorjuicerespectively).Allofthesevarietiesprovidedsimilartypesof”avanones.Tangerinesaveragedthemosthesperidinat19mg(11.6SD(standarddeviation))aglycone/gediblefruitorjuicewhilesweetorangesandtangorseachaveraged15mg(7or8SDrespectively)aglycone/100gediblefruitorjuicehesperidin,adifferencethatwasnotstatisticallysigni“cant.Tangorsweresigni“cantlyhigherinnarirutin(7mgaglycone/100gediblefruitorjuice,2.7SD)thanoranges(2mgaglycone/100gediblefruitorjuice,1.3SD,ortangerines(3mgaglycone/100gediblefruitorjuice,2.8SD,Sourorangesweredistinctfromsweetoranges,tanger-ines,andtangorsinanumberofrespects.Theywerehighinnaringin(19mgaglycone/100gediblefruitorjuice,8.7SD),neoeriocitrin(14mgaglycone/100gediblefruitorjuice,4.9SD),andneohesperidin(11mgaglycone/100gediblefruitorjuice,5.4SD)butdevoidofhesperidin.Theyalsohadthehighestoverallmeantotal”avanonecontent(summedmeans)48mgaglycone/100gediblefruitorjuice.Tangeloswereclosertosourorangesintheamountsof”avanonestheycontained,rankingsecondintotal”avanones(summedmeans)(30mgaglycones/100gediblefruitorjuice)ofalltheorangesandtheirnearrelatives.Intheir”avanonepro“les,tangeloswerehighestinneohesperidin(14mgaglycone/100gediblefruitorjuice,23.8SD),followedbynaringin(6mgaglycone/100gediblefruitandjuice,11.7SD),hesperidin(4mgaglycone/100gediblefruitandjuice,2.9SD)andnarirutin(2mgaglycone/100gediblefruitorjuice,SD)andweresigni“cantlydifferentfromsweetand/orsourorangesforthesefourcompounds.4.DiscussionThisdatabaseprovidesinformationonmorevarietiesofcitrusandmore”avanonecompoundsthanhaveARTICLEINPRESSJ.J.Petersonetal./JournalofFoodCompositionandAnalysis19(2006)S66–S73 previouslybeenavailable,andmayfacilitateresearchontheassociationsbetweenintakesandhealth.Sweetoranges,tangerines(mandarins),andtangors(suchasTempleoranges)aresimilarinboththeamountsof”avanonestheycontainandintheirdistinctiveorsignature”avanones„hesperidinandnarirutin,withvirtuallynoneohesperidinornaringin.Becausetheir”avanonecontentwassimilartheywereaggregatedandpresentedtogetherinthis”avanonefoodcompositiontable.Incontrasttothesweetorange(Citrussinensis)anditsrelatives,thesourorange(C.aurantium)wasqualitativelyandquantitativelyseparateanddistinctwithrespecttobothitstotal”avanonecontentand”avanonepro“le.Therefore,itwaslistedseparatelyinthefoodtable.The”avanonecontentoftangeloswasdifferentfromthatofsourandsweetoranges,tangerines,andtangors;itprovidedasmuchneohesperidinbutonlyathirdasmuchnaringinassouroranges.TangeloscontainedthesameamountofnarirutinbutonlyafourthofthehesperidinARTICLEINPRESS Table1Flavanonesinsweetoranges,tangerines,tangors,tangelos,andsourorangesCitrustypeGlycosidesMeanSDMedianRangeSweetorangeDidymin0.450.470.45251,15,17Eriocitrin0.280.400.070.00…1.24281,4,13Hesperidin15.258.2114.192.56…39.261281,2,4,5,6,7,8,9,10,11,12,13,15,17,18,19,14,22Naringin0.170.480.000.00…1.73491,4,5,7,9,12,20,21,22Narirutin2.331.291.940.00…6.871141,2,4,8,9,12,13,15,17,18,19,21Neoeriocitrin0.040.160.000.00…0.75221,12Neohesperidin0.000.010.000.00…0.05371,12,20,21Poncirin0.000.00201Tangerine(Mandarin)Didymin1.111.490.350.00…5.68171,16,17Eriocitrin0.020.040.000.00…0.1051,16Hesperidin19.2611.5919.294.31…47.08171,16,17Naringin0.000.0061,16,23Narirutin2.702.751.210.00…7.70171,16,17Neoeriocitrin0.000.0051,16Neohesperidin0.000.0051,16Poncirin0.000.0051,16TangorDidymin1.771.252.150.00…3.1381,17Eriocitrin1.011.0111Hesperidin15.427.0015.753.79…25.43101,17,21Naringin0.000.0031,21Narirutin7.102.737.163.15…11.17101,17,21Neoeriocitrin0.000.0011Neohesperidin0.000.0031,21Poncirin0.000.0011TangeloDidymin0.600.470.600.00…1.1921Eriocitrin1.692.390.00…3.3821Hesperidin4.212.933.151.04…9.8281,21Naringin5.6011.680.400.00…33.7381,21Narirutin2.421.912.130.45…5.8281,21Neoeriocitrin1.110.131.111.01…1.2021Neohesperidin13.5623.821.910.00…65.0781,21Poncirin0.000.0021SourorangeDidymin2.891.332.891.95…3.8321Eriocitrin0.530.490.600.00…0.9831,14Hesperidin0.000.000.000.00…0.0047101,14,21Naringin18.838.6819.136.10…34.13221,3,14,21Narirutin0.080.130.040.00…0.44101,14,21Neoeriocitrin14.014.8814.808.78…18.4431,14Neohesperidin11.095.4011.521.50…21.25221,3,14,21Poncirin0.000.0021Linesindicatesegregatedspecies.Allamountsareinmgaglycone/100gjuiceorediblefruit(withoutrind,pithandseeds).Berhowetal.(1998BronnerandBeecher(1995Calvaranoetal.(1991Carerietal.(2000Drawertetal.(1980aFisher(1978Fuchs(1994GalensaandHerrmann(1980Gamacheetal.(1993Justesenetal.(1997Justesenetal.(1998MariniandBalestrieri(1995Moulyetal.Moulyetal.(1993Moulyetal.(1997Nogataetal.(1994OogheandDetavernier(1997Oogheetal.(1994Pupinetal.(1998aRouseff(1988Rouseffetal.(1987Wallrauch(1995Yusofetal.(1990)J.J.Petersonetal./JournalofFoodCompositionandAnalysis19(2006)S66–S73 foundinsweetoranges.Thesameamountoftheaglyconeshesperetinandnaringeninwaspresentintheirparent,thetangerine.However,likeitsgrapefruitorpummeloparent,inthetangelo,moreglycosylationofhesperetinandnaringeninwithneohesperidosewasevident(andconse-quentlymoreneohesperidinandnaringinwaspresent),whereastherewaslessglycosylationwithrutinose(andthuslesshesperidinandnarirutin).Moredataareneededtodetermineiftangelosareadistinctandseparateentitywithrespecttotheir”avanonecontent.Table1describesmean”avanonevaluesandnumberofsamplesperdatapointthatwereincludedintheestimates.Sincethepurposeofourstudywastodescribethedifferentpatternsof”avonoidglycosidesinvariouscitrusfruitswereportedglycosides;incontrast,theUSDAfood”avonoiddatabase(USDA,2003)reportedonlyaglycones.Therewerealsootherdifferencesbetweenthetwodatabases.WeincludedHPLCdatafrom1978…1990andsomeGermanarticlesthatwereomittedfromtheUSDAdatabase.Nevertheless,inspiteofthelargernumberofvaluesintheTuftsdatabase,themean”avanonevaluesreportedaresimilartotheUSDAvaluesanddifferedbynomorethan1…3mgformostofthefruits(datanotshown).TheexceptionwastangelosforwhichonlyonearticlewasincludedintheUSDAdatabase(versustwoarticlesinourstudy)andthedifferencewaslarge„89mg.Inconclusion,dataonsweetoranges,tangerines(mandarins)andtangors,whicharesimilarintheir”avanonepro“lesandthequantityof”avanonestheycontain,wereaggregatedandpresentedtogetherinthisprovisionaltableoffood”avanonecomposition.Sourorangesandtangelos,whicharedistinctinboththeir”avanonecontentandthe”avanonecompoundstheycontain,constitutedistinctivecategoriesandwerepre-sentedseparately.AcknowledgementWethankthefollowingresearchsponsors:StateofFlorida,DepartmentofCitrus,DivisionofScienti“cResearch;AmericanInstituteforCancerResearch,Mas-sachusettsDepartmentofPublicHealthsBreastCancerResearchGrantsProgram;TeaCounciloftheU.S.A.;andTuftsUniversitySchoolofNutritionScience&Policy.WearegratefultoPaulJacques,USDAHNRCatTuftsUniversity,WillRand,TuftsUniversitySchoolofMedi-cine,RonaldPrior,USDA-ARS,ArkansasChildrensNutritionCenter,andAJAladesanmi,ObafemiAwolowoUniversity,Nigeria,fortheiradviceandassistance.ThisprojectwasalsofundedwithFederalfundsfromtheUSDepartmentofAgricultureResearchServiceundercon-tractnumber58-1950-4-401attheJeanMayerUSDAHNRConAgingatTuftsUniversity.Thecontentsofthispublicationdonotnecessarilyre”ecttheviewsorpoliciesoftheUSDepartmentofAgriculture,nordoesmentionoftradenames,commercialproducts,ororganizationsimplyendorsementbytheUSgovernment.ARTICLEINPRESS Table2Comparisonofmeansof”avanonesinorangesandtheirnearrelativesmgaglycones/100gjuiceorediblefreshfruitSugarGlycosideAglyconeSweetorangeTangerineTangorAggregateddata,meanTangeloSourorangeRutinoseHesperidinHesperetin151915164NarirutinNaringenin237EriocitrinEriodictyol001021DidyminIsosakuranetin012113Totalaglyconesfromrutinoseglycosidesinmgaglycones/100g1723252094NeohesperidoseNeohesperidinHesperetin0014NaringinNaringenin0NeoeriocitrinEriodictyol0001PoncirinIsosakuranetin000000Totalaglyconesfromneohesperidoseglycosidesinmgaglycones/100g00002144Total”avanones172325203048Allmeansroundedtonearestwholenumbers.Forsweetorange,tangerineandtangoronly.Signi“cantlydifferentfromsweetorange.Signi“cantlydifferentfromtangerine.Signi“cantlydifferentfromtangor.Signi“cantlydifferentfromsourorange.0.001Kruskal…Wallisanalysis.J.J.Petersonetal./JournalofFoodCompositionandAnalysis19(2006)S66–S73 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