Phenolic composition and in vitro antioxidant capacity of South African plums (Prunus salicina Lindl.)

Venter, Alet (2013-03)

Thesis (MSc Food Sc)--Stellenbosch University, 2013.

Thesis

ENGLISH ABSTRACT: Phenolic compounds of the types present in plums have been found to exhibit health-promoting properties associated with their antioxidant capacity. Fruits with red peel and/or flesh are thus sought-after for their high antioxidant levels. In the current study South African plum (Prunus salicina Lindl.) cultivars and selections, harvested during two consecutive fruit seasons, were compared in terms of general fruit attributes (colour, firmness, °Brix, pH, titratable acidity), phenolic composition and antioxidant capacity. The effect of season and a commercial cold storage and ripening regime was also investigated. A reversed-phase high-performance liquid chromatography-diode-array-fluorescence detection (HPLC-DAD-FLD) method suitable for use with mass spectrometry (MS) detection, was optimised for separation and identification of phenolic compounds from four phenolic groups (phenolic acids, anthocyanins, flavan-3-ols and flavonols) in six South African plum cultivars and five selections. Parameters that were optimised include the mobile phases, analysis temperature and gradient program. Good stability, linearity and inter- and intra-day precision were obtained. Identification of compounds was based on comparison of retention times, UV-Vis spectra and mass fragments with available authentic phenolic standards and/or literature data. The optimised method allowed identification or tentative identification of twenty-four phenolic compounds, including cyanidin-3-O-glycosides, quercetin glycosides, monomeric, dimeric and trimeric flavan-3-ols, and hydroxycinnamic acids. An on-line ABTS•+ (2,2ʹ-azinobis-(3-ethyl-benzothiazoline-6-sulfonic acid)) antioxidant assay, performed for qualitative evaluation of the antioxidant response of individual phenolic compounds, indicated the flavan-3-ols as major antioxidants in plums. Eighteen phenolic compounds were quantified, including anthocyanins and flavonol glycosides, flavan-3-ols (monomers and dimers) and hydroxycinnamic acids. Phenolic composition differed greatly between cultivars and selections. Cyanidin-3-O-glucoside was the predominant anthocyanin in plums with red peel and/or flesh, followed by cyanidin-3-O-rutinoside. Cyanidin-3-O-galactoside was present only in the cultivar Laetitia (red peel, yellow flesh). The ripe fruit of Ruby Red and PR04-19, both with red peel and flesh, had the highest anthocyanin content for the first and second harvest season, respectively. Neochlorogenic acid and quercetin-3-O-glucoside were the major phenolic acid and flavonol, respectively. Chlorogenic acid, 3-O-p-coumaroylquinic acid and several quercetin-glycosides and -diglycosides were also present in some cultivars and selections. Procyanidin B1 was the flavan-3-ol present in the highest concentration in the majority of cultivars and selections and its content correlated with the (+)-catechin content, while the same was observed for procyanidin B2 and (-)-epicatechin. The effect of cold storage and ripening on fruit attributes differed greatly between cultivars and selections. The increase and decrease in pH and titratable acidity, respectively, were as expected for ripe fruit as opposed to unripe fruit. Ripe fruit had higher a*-values and lower L*-values. The cold storage and ripening regime had no significant effect on total polyphenol and total flavan-3-ol content of the cultivars and selections, but the anthocyanin content increased in some cases. In terms of in vitro antioxidant capacity, the selections PR04-32 and PR04-35, both with red peel and flesh, had the highest antioxidant capacity, irrespective of assay. Sapphire (red peel, yellow flesh), with the lowest total polyphenol content, also had the lowest antioxidant capacity in the ORAC and FRAP assays. Both the total polyphenol and flavan-3-ol contents correlated significantly to antioxidant capacity, irrespective of assay.

AFRIKAANSE OPSOMMING: Fenoliese verbindings, soos teenwoordig in pruime, is bekend vir hul gesondheidsbevorderende eienskappe wat geassosieer word met antioksidant kapasiteit. Vrugte met ‘n rooi skil en/of vleis is veral gesog as gevolg van hul hoë antioksidant aktiwiteit. Met hierdie studie is Suid-Afrikaanse pruim (Prunus salicina Lindl.) kultivars en seleksies, geoes tydens twee opeenvolgende seisoene, vergelyk in terme van algemene vrug einskappe (kleur, fermheid, °Brix, pH en titreerbare suurheid), fenoliese samestelling en antioksidant kapasiteit. Die effek van ‘n kommersiële koelopberging en rypwording prosedure is ook ondersoek. ‘n Omgekeerde-fase hoë-druk vloeistof chromatografie (HPLC) metode met diode-opstelling en fluoressensie deteksie, maar wat ook geskik is vir massa spektrometrie (MS), is geoptimiseer om fenoliese verbindings te skei en te identifiseer in Suid-Afrikaanse pruime. Verbindings van vier fenoliese groepe (fenoliese sure, antosianiene, flavan-3-ole en flavonole) wat in ses kultivars en vyf seleksies voorgekom het, is ondersoek. Die vloeistof fases, skeidingstemperatuur en gradiënt van die metode is geoptimiseer. Goeie resultate vir stabiliteit, lineariteit en inter- en intra-dag akkuraatheid is verkry. Verbindings is geïdentifiseer deur vergelyking van retensie tye, UV-Vis spektra en massa fragmente met dié van egte fenoliese standaarde en/of met literatuur data. Vier-en-twintig fenoliese verbindings is geïdentifiseer of voorlopig geïdentifiseer, insluitende sianidien- en kwersetien glikosiede, flavan-3-ol monomere, dimere en trimere, en hidroksikaneelsure. ‘n Aanlyn ABTS•+ (2,2 ʹ-azino-di-(3-etielbensotialosien-sulfoon suur) radikaal katioon blussingstoets is gebruik om die antioksidant reaksie van individuele polifenole op ‘n kwalitatiewe wyse te evalueer en flavan-3-ole is as hoof antioksidante in pruime aangetoon. Kwantifisering van agtien verbindings, insluitende antosianiene, flavonol glikosiede, flavan-3-ole (monomere en dimere) en hidroksikaneelsure, was moontlik met hierdie geoptimiseerde metode. Die fenoliese samestelling het aansienlik verskil tussen kultivars en seleksies. Sianidien-3-O-glukosied was die hoof antosianien in pruime met ‘n rooi skil en/of vleis, gevolg deur sianidien-3-O-rutinosied. Sianidien-3-O-galaktosied het slegs in Laetitia (rooi skil en geel vleis) voorgekom. Ryp vrugte van Ruby Red en PR04-19, beide met rooi skil en vleis, het onderskeidelik die hoogste antosianieninhoud gehad met die eerste en tweede seisoen se oeste. Neochlorogeniese suur en kwersetien-3-O-glukosied was die hoof fenoliese suur en flavon-3-ol, onderskeidelik. Chlorogeniese suur, 3-O-p-kumarienkwiniensuur en verskeie kwersetien glikosiede en diglikosiede was teenwoordig in sekere kultivars/seleksies. Die flavan-3-ol, prosianidien B1, was teenwoordig in die hoogste konsentrasie in die meerderheid kultivars/seleksies. Die prosianidien B1 inhoud het met die (+)-katekien inhoud gekorreleer, terwyl dieselfde gevind is vir prosianidien B2 en (-)-epikatekien. Die effek van koelopberging en rypwording op die algemene vrug einskappe het tussen kultivars en seleksies verskil. Die pH en titreerbare suurheid het onderskeidelik toegeneem en afgeneem, soos verwag is vir ryp vrugte teenoor onryp vrugte. Ryp vrugte het hoër a*-waardes en laer L*-waardes getoon. Koelopberging en rypwording het geen beduidende effek op die totale polifenol- en totale flavan-3-ol inhoud gehad nie, maar die antosianieninhoud het vir sommige kultivars en seleksies toegeneem. In terme van in vitro antioksidant kapasiteit het die seleksies PR04-32 en PR04-35, beide met rooi skil en vleis, die hoogste antioksidant kapasiteit getoon, ongeag die antioksidant toets wat gebruik is. Sapphire (rooi skil en geel vleis) het die laagste totale polifenolinhoud gehad, asook die laagste antioksidant kapasiteit soos bepaal deur die ORAC en FRAP toetse. Beide die totale polifenol- en flavan-3-ol inhoud het beduidend met die antioksidant kapasiteit korreleer, ongeag van die toets wat gebruik is.

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