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Flavonols, Phenolic Acids and Antioxidant Activity of Some Red Stark,A., A. Nyska,A. Zuckerman, and Z. MadarChanges in intestinal Vincken,J,-P., H. A. Schols, R. J. F. J. )omen,K. Beldnan, R. G. F. Visser, Tunicamuscularis following dietary liber feeding inrats. A morphometric andA. G. J. Voragen'.Pectin - the hairy thing. ln. Voragen, E,H. Schools, studyusing image analysis. Dig Dis Sci 40, 960-966 (1995). andB. t4sser(Eds.): Advances inPectin and Pectinase Research, 4Z-5g. Stark,A., A. Nyska, and Z. Madar. I\4etabolic and morphometric changes KlumerAcademic Publishers, Dortrecht, Niederlande (2003). insmall and large intestine inrats fed high-fiber diets. Toxicol pathol 24, Yoo,S.-H., M. Marshall, A.Hotchkiss, and H. G. Lee: Viscosimetric beha- 166-171(1996). vioursof high-methoxy andlow-methoxy pectin solutions. Food Hydro- Sugawa-Katayama,Y.,and A. ltuza.Morphological changes of smallin- coll20, 62-67 (2005). testinalmucosa inthe rats fed high pectin diets. Oyo Toshitsu Kagaku 3, Zhang,J., and J. fr. Lupton: Dielary fibers stimulate colonic cell prolifera- 335-341(1994) (in Japanisch). tionby different mechanisms atdifferent sites. Nutr Cancer ZZ.26l-276 Tamura,M., and H. SuzukiEffects of pectinon jejunaland ileal mor- (1 994) phologyand ultrastructurein adultmice. Ann Nutr Metab 41, 2SS-259 (1997) Flavonols,Phenolic Acids and Antioxidant Activity of Some Red Fruits LidijaJakobek#, Marijan Seruga, lvana Novak and MailinaMedvidovi6-Kosanovi6 DepartmentofApplied Chemistry and Ecology, Faculty of Food Technology,J J StrossmayerUniversity of0sijek, Kuhaceva 18, HR-31000 0sijek, Croatia Summary schwarzeund rote Johannisbeere) wurde mittelsHPlC-Methode be- Redfruits (blueberry, blackberry, chokeberry, strawberry, red raspberry, stimmt.Die Verbindungen wurden als Aglykon nach der Hydrolyse mit sweetcherry, sour cherry, elderberry, black currant and red currant) were 1,2mol dm 3 HCI analysiert. Injeder Frucht wurden auch die Gesamtpo- analyzedfor flavonols (quercetin, myricetin, and kaempferol), hydroxy- lyphenole(TP) und Gesamtanthocyane (TA)bestimmt TP variierte von cinnamicacids (caffeic, ferulic, p-coumaric acid) and hydroxybenzoic ac- 1763in der Himbeere bis 7194 mg kg r (FW)in der Aronia. TA variierte ids(phydroxybenzoic, ellagic acid) by using HPLC method. Compounds von169 (Erdbeere) bis4069 mg kgr FW (Blaubeere). DieKonzentration 3 wereanalyzed asaglycons after acid hydrolysis with 1.2 mol dm HCl. derFlavonole variierte von 4 mgkgr in der Himbeere bis 183 mg kg r in Eachfruit sample was analyzed for total polyphenols (TP) and total an- derBlaubeere. Die hochsten Konzentrationen anHydroxyzimtsaure wur- thocyanins(TA). TP ranged from 1763 to 7194mg kglfresh weight denin der Blaubeere (92 mg kg 1) und in der schwarzen Johannisbeere (FW)rn red raspberries and chokeberries, respectively. TAranged from (70mg kgr) gefunden und stellten einen bedeutenden Anteil der phe- 169to 4069mg kg, FWin strawberriesand blueberries, respectively. nolein denSuB- und Sauerkirschen dar.Die Ellagsaure-Konzentrati0n Flavonolsvaried from 4 mgkgr in redraspberries to 183 mg kg1 in betrugin der Brombeere 121 mg kgr, in der Erdbeere 4l mg kgrund in blueberries.Hydroxycinnamic acidswere found in relatively high concen- derHimbeere 32 mg kgI. Die starkste antioxidative Aktivitat, die mittels trationsin blueberries(92mg kg1) and in blackcurrant (70 mg kgr) DPPH.und ABTS*-Methoden bestimmt wurde, zeigten Aronia, schwarze andrepresented significant portion in sour and sweet cherry phenolics. The Johannisbeereund Holunderbeere. Dieantioxidative Aktivitat korreliert 1), amountofellagic acid was hrgh in blackberry (121 mg kg strawberry(41 mg bessermit TP als mit TA, mit den Gesamtflavonolen (TF)oder mit der l) kg andred raspberry (32mg kgr) Thestrongest antioxidant activity de- Gesamthydroxyzimtsaure.Eswurde eine lineare Korrelation zwischen terminedby DPPH'and ABTS'- assays showed chokeberry, followed by derantioxidativen Aktivitat der Fr0chte und der Kaffeesaure-, 0uercetin- blueberry,black currant and elderberry. Antioxidant activity correlated undp-Cumarsaure-Konzentration festgestellt. Alle Ergebnisse weisen betterwith TP than with TA, total flavonols (TF), or total hydroxycinnamic daraufhin, dass die Beerenfrlichte undKirschen als eine reiche Ouelle acids.Additionally, linear relationship was observed between antioxidant bioaktiverPolyphenole in der menschlichen Erndhrung dienen konnen. activityof fruitsand c0ntent 0f caffeicacid, quercetin and p-coumaric Aronia,Blaubeere, Holunderbeere undschwarze Johannisbeere haben acid.Overallresults showed that red fruits can serve as good source of diehdchste Anthocyan-, Flavonol-, und Phenolsaure-Konzentration. Sie bioactivepolyphenols inhuman diet, but due to highconcentrations of zeigenauch die stdrkste antioxidative Aktivitiit und k0nnen aus diesem anthocyanins,flavonols, phenolic acids and strong antioxidant activity, Grundeals gute Rohstoff-Kandidaten inder Produktion von funktionellen chokeberry,blueberry, elderberry and black currant can be regarded as Lebensmittelneingesetzt werden. goodcandidates fornutritional supplement formulations. Zusammenfassung Keywords:Red fruits, berries, flavonols, phenolic acids, antioxidant ac- tivity DieKonzentration derFlavonole (Quercetin, Myricetin, und Kaempferol), / roteFrLichte, BeerenfrLichte, Flavonole, Phenolcarbonsauren, anti- der Hydroxyzimtsaure(Kaffeesdure, Ferulasdure und p-Cumarsdure)oxidativeAktivitat undder Hydroxybenzoesaure (p-Hydroxybenzoesaure undEllagsaure) ausroten Fruchten (StlB-und Sauerkirschen), sowie aus Beerenfrlrch- ten(Blaubeere, * Brombeere,Aronja, Erdbeere, Himbeere, Holunderbeere, E-mail:[email protected], Tel.:+385-31 -224-300, Fax: +385-31-207-l l5 DeulscheLebensmittel-Rundschau r 103.Jahrgang, HeftB, 2007 0riginalarbeitenr369 rotenoids,are responsiblefor beneficialeffects of diet rich in fruits and vegetableson human healthl2'rer. R2 Becauseof the positiveeffects of fruits polyphenolson hu- man health,the interestin consumingfruits and their prod- R3 ucts is growing. In order to fully understandthe roles of fruit'spolyphenols, further studies are needed. As a first step o it is importantto determinethe distributionof polyphenols in fruits rich in polyphenols,and to investigateantioxidant Flavonols Hydroxycinnamic acids data will enableevaluation of MyricetinR,=R.=R,-OH p-Coumaric acid R=H activityof thosefruits. These =R,=OH, QuercetinR R.=H Caffeic acid R=OH fruits as a sourceof polyphenolsin diet. Furthermore,they Ferulic acid R=OCH, KacmpferolR,= OH. R,=R,= H can be the basisfor further studiesof effectsof individual polyphenolson fruit's antioxidantactivity. Epidemiological OH studieswill help in understandingthe relationbetween the A," intakeof fruit'spolyphenols and the risk of developingvari- ll-l H ous diseases.lVith that kind of knowledgeit will be pos- Y sibleto chooseraw materialsfor preparationof functional o4ott foodsrvith betterbiological activity. the contentof in- p-Hydroxybenzoicacid Ellagic acid The aim of this study was to determine llydroxybenzoic acids dividual flavonols (quercetin,myricetin, kaempferol) and phenolicacids (p-coumaric, caffeic, ferulic, p-hydroxyben- Fig1 Structuresofaglycons offlavonols and phenolic acids zoic, ellagicacid) presentin various red fruits (blueberry, blackberry',chokeberry, strawberry, rerl raspberry' sweet ^herry, Introduction sour ,.\erry,elderberry, bl:ck c,,,rai:t and rcd cur- rant) by using high performanceliquid chromatography Flavonols(Fig. 1) belongto the largegroup of polyphenolic (HPLC) equippedwith a photodiodearray detector(PDA) con'rpounds.They contain a common molecularstructure in order to examinethe distributionof thesepolyphenols in that consistsof the tricyclicCo-C,-Co "flavon skeleton"and red fruits. Additionall.v,a concentrationof total polyphe- are widespreadin plants where they occur r'rsuallyas O- nols and total anthocyaninswas measured'Antioxidant glvcosides.Although over 200 flavonolaglycons have been :lctivity of red fruits was determinedby using DPPH and identifiedin plants,only four of these'quercetin, kaemp- ABTS assays.The existenceof possiblecorrelation between ferol, myricetinand isorhamnetin,are common in fruitsl'. total or individualpolyphenols and antioxidantactivity of Phenolicacids (Fig. 1) (hydroxycinnamicand hydroxvben- fruits was examinedas well. zoic acids)belong to the group of pol,vphenoliccompounds aswell, and occurin fruits as esters,glycosides and amides. The most common hydroxycinnamicacids are p-coumaric, Materialsand methods caffeicand ferulic acid, while the correspondinghydroxy- benzoicacids are p-hydroxybenzoic,gallic, ellagic,3,4-di- Chemicals hydroxybenzoic,vanillic, and syringicacidr-1). 4-hydroxybenzoicacid, ellagic acid, caffeic acid, ferulic acid, In the last few decadesflavonols and phenolic acids,are p-coumaricacid, myricetin, quercetin dihydrate, kaempferol, -azino- studiedintensively because of their potent positiverole in 2,2-diphenyl-1-picrylhydrazylradical (DPPH'), 2,2' humanhealth. Flavonols, phenolic acids and otherpolyphe- bis(3 -ethyl benzothiazoline-6-sulfonic acid)diammonium salt - -2, -tetramethylchro- nois are potent antioridants,free radical scavengers'jrand (ABTS ) and Trolox (( = ) 6-hydroxy 5,7,8 metal chelators;they exhibit various physiologicalactivi- mane-2-carboxylicacid) rvere purchasedfrom Sigma-Al- tiesincluding anti-inflammatory, anti-allergic, anti-carcino- dricb (St. Louis, MO, USA). Methanol (HPLC grade)was gcr.ric,anti-arthritic activitiesr'6-n). They may havea positive obtainedfrom Merck (Darmstadt,Germany); o-phosphoric role in clecreasingthe risk of
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