Accepted Manuscript Antioxidant property and storage stability of quince juice phenolic compounds Aneta Wojdyło, Mirosława Teleszko, Jan Oszmiański PII: DOI: Reference:

S0308-8146(13)01813-X http://dx.doi.org/10.1016/j.foodchem.2013.11.124 FOCH 15075

To appear in:

Food Chemistry

Received Date: Revised Date: Accepted Date:

23 September 2013 20 November 2013 22 November 2013

Please cite this article as: Wojdyło, A., Teleszko, M., Oszmiański, J., Antioxidant property and storage stability of quince juice phenolic compounds, Food Chemistry (2013), doi: http://dx.doi.org/10.1016/j.foodchem.2013.11.124

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Antioxidant property and storage stability of quince juice phenolic compounds

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Aneta Wojdyło*, Mirosława Teleszko, Jan OszmiaĔski

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Wroclaw University of Environmental and Life Science; Department of Fruit and Vegetable

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Technology, 37/41 ChełmoĔskiego Street, 51-630 Wroclaw, Poland.

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tel (+48) 71-3205 7706;

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e-mail:[email protected]

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Abstract

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The aim of this study was to characterize, in depth, 11 quince cultivars to provide data for their

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industrial processing into high-quality juices. Polyphenolic composition analyses (identification and

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quantification), soluble fraction of procyanidins, antioxidant capacity assays and cluster analysis were

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measured. A total of 17 kinds of polyphenolic compounds were the following in the juices: before and

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after 6 month of storage time at 4 and 30oC. Large variations in polyphenolic compounds content were

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found as affected by quince cultivar. The total phenolics determined by UPLC ranged from 4045 mg

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to 721 mg/100 mL of juices, and was high correlated with antioxidant activity. During 6 months of

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storage a significant change was observed in the content of polyphenols, especially in procyanidins

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(37 and 55%, respectively). This result may be useful for the juice industry as a starting point for the

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development of tasty quince juices with high levels of bioactive compounds.

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Key words: Cydonia oblonga Miller; juices; UPLC, phenolic compounds, flavan-3-ols, mDP, stability,

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ABTS, FRAP, DPPH

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1. Introduction

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Fruits and vegetables are rich sources of vitamins, particularly vitamins A and C, and excellent

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sources of fiber. In addition, they contain some calories, and are naturally low in fat. An increased

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consumption of fruits and vegetables has been associated with protection against various diseases,

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including cancers as well as cardiovascular and cerebrovascular diseases (Guthrie & Kurowska, 2001).

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This association is often attributed to the antioxidants present in fruits and vegetables, such as vitamins

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C and E, carotenoids, phenolic acids, and flavonoids, which prevent free radical damage (du Toit,

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Volsteedt & Apostolides, 2001).

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Fruits of quince (Cydonia oblonga Miller) are a valuable source of compounds with health-

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promoting properties. They are also a good source of natural antioxidant substances, namely

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polyphenols, which have been reported to yield many health benefits (Carvalho et al., 2010;

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Magalhăes et al., 2009). Quince polyphenols include flavonoids (flavan-3-ols and flavonols) and

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hydroxycinnamic acids. Among these compounds, special interest has been focused on flavonols

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which are responsible for the color of fruits, and proanthocyanidins due to their strong antioxidant

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activity (Wojdyło, Figiel, Lech, Nowicka & OszmiaĔski, 2013; Silva et al., 2004). Although quince

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fruit is not edible raw because of its hardness, bitterness, and astringency it is used to make jams,

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marmalades and jellies, as well as quince puddings. Dried quince can also be used as an ingredient of

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traditional Iranian foods.

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This study investigates fruits commonly grown and approved in many countries, e.g. in

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Turkey, Portugal, and Spain (Schirmer et al., 2000). The mean world production of quince of the last

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10 year (1998–2008) is estimated at 510,000 t (FAO, 2010). Its predisposition to turning brown and

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decay is a limiting factor in the long-term storage of this fruit (Gunes et al., 2008). However, in Poland

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the cultivation and processing of quince fruits are still marginal. There are only few plantation and

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processing plants that use quince fruits for the production of dried material to be used an additive to

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fruit teas. The other part of quince processing in Poland involves home-made production of liquors

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and jams. Nowadays consumers are becoming more aware of the contribution of diet to their health

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and, therefore, are willing to buy foods rich in bioactive compounds with high quality (Mena et al.,

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2010). These properties can vary depending on genotypic effects, environmental conditions, cultural

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practices and industrialization process (Schwartz et al., 2009). Because of this vast number of factors,

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which may affect consumer acceptance, it is important to consider not only bioactive compounds or

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antioxidant capacity of quince fruits, but also other compounds or characteristics that might take part

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in the productive process of juices or other quince derivate products, such as phenolic compounds and

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antioxidant activity. Therefore the aim of this study was to characterize, in depth, quince cultivars to

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provide data for their industrial processing into high-quality juices that are richer in bioactive

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compounds and more attractive than the available commercial products. Polyphenolic composition

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analyses (identification and quantification) and antioxidant capacity assays were carried out.

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2. Materials and methods 2.1. Chemicals

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1,1-Diphenyl-2-picrylhydrazyl radical (DPPH); 2,2ƍ-azinobis(3-ethylbenzothiazoline-6-sulfonic acid

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(ABTS); 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox); 2,4,6-tri(2-pyridyl)-s-

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triazine (TPTZ); acetic acid; phloroglucinol and methanol were purchased from Sigma-Aldrich

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(Steinheim, Germany). (−)-Epicatechin, (+)-catechin, quercetin, kaempferol-3-O-glucoside, and

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procyanidins B1, B2 and C1 were purchased from Extrasynthese (Lyon, France). Chlorogenic acid,

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neochlorogenic acid, cryptochlorogenic acid, and 3,5-dicaffeoylquinic acid were purchased from

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TRANS MIT GmbH (Giessen, Germany). Acetonitrile for UPLC (Gradien grade) and ascorbic acid

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were from Merck (Darmstadt, Germany). UPLC grade water, prepared by using an HLP SMART

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1000s system (Hydrolab, GdaĔsk, Poland), was additionally filtered through a 0.22 ȝm membrane

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filter immediately before use.

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2.2. Plant material

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Eleven different quince (Cydonia obolonga Miller) cultivars: ‘Akademiczeskaja’, ‘Bereczki’, ‘Cezar’,

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‘Darunok Onuk’, ‘Kaszczenko 18’, ‘Leskovaþ’, ‘Marija’, ‘Portugesicka’, ‘PóĨna Rejmana’, ’Uspiech’,

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‘Wołgogradzkaja Aromatnaja’, and one genotype ‘S1’ were obtained from 10-years-old tree and hand-

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harvested at optimum ripeness (the degree of ripeness was determined on the basis of fruit colouring,

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separability, and change of fruit peel from a lanuginous to waxy condition) in October 2011. The fruit

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were harvested in the Nursery Farm Radwan-Pytlewski Piotr from Miedniewice (52°09’N 20°30’E).

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2.3. Preparation of quince juices on a laboratory scale

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Quince (6 kg) were ground using a Thermomix (Wuppertal, Vorwerk, Germany) laboratory mill

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during 20 s with inhibitor of oxidation (rhubarb juice; 2.5%, v/v). After ground mash was pressed in a

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laboratory hydraulic press (SRSE; Warsaw, Poland), and then juices were heated in Thermomix to 90

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o

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cooled to 20 oC. Two replicates of quince juice preparation were carried out. Directly after processing

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and 6 months of storage at 4 and 30 oC the juices were subjected to analyses.

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2.4. Identification of polyphenols by the LC-PDA-MS method

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Identification and quantification of polyphenols of quince juice was carried out using an Acquity

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ultraperformance LC system equipped with a photodiode detector (PDA; UPLC)) with binary solvent

90

manager (Waters Corp., Milford, MA, USA) series with a mass detector G2 QTof Micro mass

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spectrometer (Waters, Manchester, UK) equipped with an electrospray ionization (ESI) source

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operating in negative and positive modes. Separations of polyphenols were carried out using a UPLC

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BEH C18 column (1.7 ȝm, 2.1 × 50 mm; Waters Corp., Milford, MA, USA) at 30 °C.

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Samples (5 ȝL) were injected, and elution was completed within 15 min using a sequence of elution

95

modes: linear gradients and isocratic. The flow rate was 0.45 mL/min. The mobile phase was

96

composed of solvent A (4.5% formic acid) and solvent B (100% of acetonitrile). The program began

97

with isocratic elution with 99% A (0−1 min), and then a linear gradient was used until 12 min,

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lowering A to 0%; from 12.5 to 13.5 min, returned to the initial composition (99% A); and then held

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constant to re-equilibrate the column. Analysis was carried out using full scan, data-dependent MS

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scanning from m/z 100 to 1000. The mass tolerance was 0.001 Da, and the resolution was 5.000.

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Leucine enkephalin was used as the mass reference compound at a concentration of 500 pg/ȝL at a

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flow rate of 2 ȝL/min, and the [M − H]− ion at 554.2615 Da was detected over 15 min of analysis

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during ESI-MS accurate mass experiments, which was permanently introduced via the LockSpray

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channel using a Hamilton pump. The lock mass correction was ±1.000 for Mass Window. The mass

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spectrometer was operated in a negative ion mode and set to the base peak intensity (BPI)

106

chromatograms and scaled to 12400 counts per second (cps) (=100%). The optimized MS conditions

107

were as follows: capillary voltage of 2500 V, cone voltage of 30 V, source temperature of 100 °C,

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desolvation temperature of 300 °C, and desolvation gas (nitrogen) flow rate of 300 L/h. Collision-

C for 4 min, hot fillet at 0.08 L glass jars, immediately inverted for 10 min to sterilize the lids, and

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induced fragmentation experiments were performed using argon as collision gas, with voltage ramping

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cycles from 0.3 to 2 V. The characterization of the single components was carried out via the retention

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time and the accurate molecular masses. Hydroxycinnamic acid, flavan-3-ols and flavonols compound

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was optimized to its estimated molecular mass [M − H]− in the negative mode before and after

113

fragmentation. The data obtained from LC-MS were subsequently entered into MassLynx 4.0

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ChromaLynx Application Manager software. On the basis of these data the software is able to scan

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different samples for the characterized substances.

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2.5. Determination of polyphenols by UPLC coupled to PDA and FL detector

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The analysis of polyphenolic compounds was carried out on a UPLC system Acquity (Waters Corp.,

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Milford, MA, USA) consisting of a binary solvent manager, sample manager, PDA (model Ȝe), and

119

fluorescence detector (FL). Empower 3 software was used for chromatographic data collection and

120

integration of chromatograms. The UPLC analyses were performed on a BEH Shield C18 analytical

121

column (2.1 mm × 50 mm; 1.7 ȝm). The flow rate was 0.45 mL/min with the flow rate was 0.45

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mL/min. A partial loop injection mode with a needle overfill was set up, enabling 5 ȝL injection

123

volumes when a 10 ȝL injection loop was used. Acetonitrile (100%) was used as a strong wash solvent

124

and acetonitrile in water (10%, v/v) as a weak wash solvent. All determination were done in triplicate.

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2.6. Analysis of polyphenol compounds

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Five millilitres of the juices were centrifuged for 10 min at 15000g at 4 °C. The analytical column was

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kept at 30 °C by column oven, whereas the samples were kept at 4 °C. The mobile phase was

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composed of solvent A (4.5% formic acid) and solvent B (acetonitrile). Elution was as follows: 0−5

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min, linear gradient from 1 to 25% B; 5.0−6.5 min, linear gradient from 25 to 100%; 6.5−7.5 min,

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column washing; and reconditioning for 0.5 min. PDA spectra were measured over the wavelength

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range of 200−600 nm in steps of 2 nm. The runs were monitored at the following wavelengths: flavan-

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3-ols at 280 nm, hydroxycinnamates at 320 nm, and flavonol glycosides at 360 nm. Retention times

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(Rt) and spectra were compared with those of pure standards. Calibration curves at concentrations

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ranging from 0.05 to 5 mg/mL (r2 ” 0.9998) were made from (−)-epicatechin, (+)-catechin,

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procyanidins B2 and C1, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, quercetin,

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and kaempferol 3-O-glucoside as standards. p-Coumarylquinic acid was expressed as p-coumaric acid,

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and quercetin and kampferol derivatives were expressed as quercetin and kaempferol-3-O-glucoside,

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respectively. The results was expressed as milligrams per 100 mL.

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2.7. Analysis of polymeric proanthocyanidins by phloroglucinolysis method

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Direct phloroglucinolysis of freeze-dried quince varieties was performed as described previously

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Wojdyło, OszmiaĔski & Bielicki (2013). Portions (0.5 mL) were precisely measured into 2 mL

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Eppendorf vials and freeze-dried (24h; Alpha 1-4 LSC; Martin Christ GmbH, Osterode am Harz,

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Germany), then 0.8 mL of the methanolic solution of phloroglucinol (75 g/L) and ascorbic acid (15

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g/L) was added. After the addition of 0.4 mL of methanolic HCl (0.3 mol/L), the vials were closed and

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incubated for 30 min at 50 °C with continuous vortexing using a thermo shaker (TS-100; BIOSAN.

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Lithuania). The reaction was stopped by placing the vials in an ice bath with drawing 0.5 mL of the

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reaction medium and diluting with 0.5 mL of 0.2 mol/L sodium acetate buffer. Next the vials were

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cooled in ice water and centrifuged immediately at 20000 g for 10 min at 4 °C. The analytical column

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was kept at 15 °C by column oven, whereas the samples were kept at 4 °C. The mobile phase was

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composed of solvent A (2.5% acetic acid) and solvent B (acetonitrile). Elution was as follows: 0−0.6

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min, isocratic 2% B; 0.6−2.17 min, linear gradient from 2 to 3% B; 2.17−3.22 min, linear gradient

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from 3 to 10% B; 3.22−5.00 min, linear gradient from 10 to 15% B; 5.00−6.00 min, column washing;

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and reconditioning for 1.50 min. The fluorescence detection was recorded at an excitation wavelength

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of 278 nm and an emission wavelength of 360 nm. The calibration curves, which were based on peak

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area, were established using (+)-catechin, (−)-epicatechin, and procyanidin B1 after phloroglucinol

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reaction as (+)-catechin- and (−)-epicatechin−phloroglucinol adduct standards. The average degree of

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polymerization was calculated as the molar ratio of all the flavan-3-ol units (phloroglucinol adducts +

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terminal units) to (−)-epicatechin and (+)-catechin, which correspond to terminal units. The results

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were expressed as milligrams per 100 ml.

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2.8. Isolation of soluble fractions

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Juice polysaccharides were isolated by alcoholic precipitation. Ten milliliters of juice were mixed with

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50 mL of 96% ethanol. The mixture was thoroughly stirred for 5 min and stored for 24 h at 4 oC. After

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centrifugation (4200 g for 10 min, at 4 oC). the supernatant was discarded. The residue obtained was

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freeze-dried, and finally weighed as a soluble fraction. Direct phloroglucinolysis of freeze-dried

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quince juice soluble precipitates was performed as described above.

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2.9. Analysis of antioxidant activity

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The ABTS•+ scavenging activity and the total antioxidant potential of the sample was determined

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using a ferric reducing ability of plasma (FRAP) assay were determined according to the method

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described previously by Wojdyło, OszmiaĔski & Bielicki (2013). For all analyses, a standard curve

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was prepared using different concentrations of Trolox. All determinations were performed in triplicate

171

using a Shimadzu UV-2401 PC spectrophotometer (Kyoto, Japan). The results were corrected for

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dilution and expressed in micromoles Trolox per 100 mL.

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2.10. Statistical analysis

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Results were presented as mean ± standard deviation of two independent determinations. All statistical

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analyses were performed with Statistica version 10.0 (StatSoft, Krakow, Poland). One-way analysis of

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variance (ANOVA) by Duncan’s test was used to compare the mean values. Differences were

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considered to be significant at p < 0.05. Cluster analysis was applied to the standardized data to obtain

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hierarchical associations employing Euclidean distance and Ward’s method as dissimilarity measure

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and amalgamation rule, respectively.

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3. Results and discussion

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3.1.

Identification of phenolic compounds in quince juices

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The identification of polyphenolic compounds in quince juices was conducted with the use of

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the LC-MS-QT system and respective results were presented in Table 1. In total, 17 polyphenolic

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compounds found in quince juices were identified and presented. The phenolic compounds were

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identified by comparing the UV−vis spectra, Ȝmax, MS spectra, and retention times to those of available

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standards. The following compounds were identified in the juices: six flavan-3-ols ((−)-epicatechin,

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procyanidin B2, procyanidin dimers and trimers), five hydroxycinnamates as derivatives of

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caffeoylquinic and p-coumaroylquinic acid, and six flavonols as kaempferol and quercetin derivatives.

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3.2.

Quantification of phenolic compounds in quince juice

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The major polyphenolic groups in quince were flavan-3-ols (polymeric procyanidins) >

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hydroxycinnamic acids • flavonols. Types and contents of polyphenolic compounds detected in these

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quince juices were similar to results of previous studies with different quince cultivars (Wojdyło,

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OszmiaĔski & Bielicki, 2013; Silva et al., 2002). The total phenolics determined by UPLC ranged

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from 4045 mg to 721 mg/100 mL of juices. Juices prepared from ‘Uspiech’. ‘Portugesica’,

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‘Kaszczenko 18’ and ‘Bereczki’ cultivars were characterized by higher contents of phenolic

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compounds compared to the other analyzed juices. Juices prepared from ‘S1’, ‘PóĨna Rejmana’ and

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‘Wołgogradzka Aromatnaja’ cultivars were characterized by the lowest contents of phenolics. Flavan-

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3-ols, hydroxycinnamic acid and flavonols represented respectively 63%, 36% and 1% of total

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polyphenols in quince juices, however their contents were strongly cultivar-dependent. As presented in

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Table 2, juices with a low content of phenolic compounds were characterized by a higher

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concentration of hydroxycinnamic acid than flavan-3-ols. However compared to apple juice prepared

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from ‘Šampion’ cultivars (Kolniak-Ostek, OszmiaĔski & Wojdyło 2013), the analyzed quince juices

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had more phenolic compounds, especially flavan-3-ols and hydroxycinnamic acid. Also OszmiaĔski,

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Wojdyło & Kolniak (2011) in the study of cloudy apple juice, determined the concentration of

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polyphenolic compounds in the range from 472 to 1044 mg/L. According to Wolfe, Wu & Liu (2003),

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the content of polyphenolic compounds in apple juices can be affected by the maturity and cultivar of

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fruit and - to the greatest extent - by the production process. During the production of juice, a part of

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polyphenolic compounds undergo the process of enzymatic oxidation to quinones. The extent of

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transformation depends on the activity of the polyphenol oxidase enzyme (PPO) in a particular

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cultivar. As presented in a previous work (Wojdyło, OszmiaĔski, & Bielicki 2013), quince fruits

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possess high PPO activity, which is higher than that reported for apple fruits. A low content of

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polyphenolics in the juice was evidenced by the high activity of PPO in fruits, the juice had been made

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of. Therefore the production process of these juices requires the use of some antioxidants, i.e. ascorbic

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acid or rhubarb juices (OszmiaĔski Wolniak, Wojdyło & Wawer, 2007; Wojdyło, OszmiaĔski &

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Bober, 2008). However during the manufacturing process, a part of polyphenolic compounds remains

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in pomace, which can affect fruit maturity. Progressive ripening process determines the loosening of

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cell walls and increases their fragmentation. This results in a reduction of polyphenolic compounds

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bound to cell walls and intensified migration of polyphenolics to juice during pressing.

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A high concentration of procyanidins in quince fruits and juices may explain their slight astringency

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and bitterness, typical of cider apples. Bitterness and astringency depend on the flavanol contents,

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their mean degree of polymerization (mDP), and the residual pectin (Vidal et al., 2004). Flavan-3-ols

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(monomer, dimmer, and polymeric proanthocyanidins) are the major class of quince polyphenols in

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juices (Table 2). The highest contents of flavon-3-ol compounds in the analyzed juices were reported

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for polymeric proanthocyanidins (26-77%), followed by dimmer and monomer procyanidins (8-25%).

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The high content of these compounds was measured in ‘Uspiech’ (3105 mg/100 mL) > ‘Portugesica’

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(2612 mg/100 mL) > ‘Kaszczenko 18’ (1952.6 g/100 mL) and ‘Bereczki’ (1608 mg/100 mL) quince

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juices. In the remaining investigated juices the content of flavan-3-ols was bellow 1000 mg in 100 mL

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of juices. (−)-Epicatechin was the main monomeric procyanidin, with concentrations ranging from

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30.3 mg in ‘PóĨna Rejmana’ to 63.5 mg/100 mL in ‘Uspiech’ juices. The concentration of (+)-catechin

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was lower than that of (-)-epicatechin and was from 1.15 mg in ‘PóĨna Rejmana’ to 4.5 mg in

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‘Akademiczeskaja’ juices. In turn, the average concentration of procyanidin monomers and trimers

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was equal for procyanidins B1 - 17.8 mg, B2 - 78.9 mg, and C1 - 94.8 mg/100 mL in quince juices.

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The average concentrations for dessert apple monomers and dimmers (procyanidins B2) ranged

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between 11.6 and 209.5 mg and between 38.8 and 162.2 mg/100 g, respectively, whereas the content

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of (+)-catechin was lower (0.5−3.4 mg/100 g) (Vrhovsek, Rigo, Tonon, Mattivi, 2004).

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The mean degree of polymerization (mDP; number of flavan-3-ol units) affects the

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physicochemical properties of procyanidins (Le Bourvellec, Picot & Renard, 2006; Hamauzu, Yasui,

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Inno, Kume & Omanyuda, 2005) The mDP of the polymeric fraction in quince fruit was from 8.3 to

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11.2; thus on average it accounted for 9.7 (Wojdyło, OszmiaĔski, Bielicki, 2013), but in quince juices

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it was from 2.5 to 13.5. The highest mDP was determined in the following juices: ‘Portugesica’,

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‘Bereczki’, and ‘Kaszczenko 18’, and the lowest one in: ‘S1’, ‘PóĨna Rejmana’, ‘Wołgogradzkaja

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Aromatnaja’, ‘Cezar’ and ‘Danurok Onuku’. The mean degree of polymerization of clear, cloudy and

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puree strawberry juices was 2.6, 3.7 and 4.1, respectively (OszmiaĔski & Wojdyło, 2009a), whilst for

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blackcurrant juice it was 8.9 and for apple juices made of ‘Shampion’ and ‘Idared cultivars it was 3.0

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and 2.8, respectively (OszmiaĔski & Wojdyło, 2009b).

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Large variations in hydroxycinnamic acid content were found as affected by quince cultivar.

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Juice from ‘Akademiczeskaja’ cv. contained only 260 mg/100 mL of total hydroxycinnamic acid,

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while in juice from ‘Portugesica’ cv. the respective value was at 685 mg/100 mL. In most cases, the

249

main acid of the hydroxycinnamic acids group was chlorogenic acid and its derivatives rather than p-

250

coumaroylquinic acid and its derivatives. The chlorogenic acids group was represented by:

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chlorogenic > neochlorogenic > cryptochlorogenic acid > 3,5-di-caffeoylquinc acid and derivative of

252

chlorogenic acid, whereas the p-coumaroylquinic group was represented by 4-O-p-coumaroylquinic

253

acid and its derivatives. Silva et al. (2004) reported that chlorogenic acid was the most abundant

254

phenolic in pulp and peel. Chlorogenic acid was found to be the major phenolic compound (40-56%)

255

in all quince juices, except for the juice prepared from ‘Akademiczeskaja’ cv. In ‘Akademiczeskaja’

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juices neocholorogenic acid constituted 50% and chlorogenic acid only 15% of total phenolic acids

257

(Table 2). In the other juices the concentration of these major compounds ranged from 98.0 (‘S1’

258

juice) to 169 mg/100 mL (‘Uspiech’ juice) for neochlorgoenic acid and from 132 (‘Wolgogradzka

259

Aromatnaja’ juice) to 321 mg/100 mL (‘Portugesica’ juice) for chlorogenic acid. The highest

260

concentration of cryptochlorogenic acid was found in ‘Portugesica’ juice (41.6 mg/100 mL) with

261

levels as low as 26 mg/100 mL occurring in several juices. Finally, the concentration of 3,5-di-

262

caffeoylquinic acid was below 8.1 mg/100 mL (Table 2).

263

Flavonols are mainly located in the peel of quince fruits, hence their percentage in the total

264

content of polyphenols measured in quince juices is low. The importance of flavonols in juices lies in

265

their health properties and their contribution to color via the phenomenon of copigmentation. Marks,

266

Mullen & Crozier (2007) and Silva et al. (2004) concluded that quince peel had a higher antioxidant

267

activity than pulp. The six flavonols found in the juices represented less than 2% of the total phenolics.

268

Of the six flavonols, quercetin-3-O-glucoside was found in higher concentrations ranging from 6.4

269

mg/100 mL in ‘Wolgogradzkaja Aromatnaja’ juice to 16.0 mg/100 mL in ‘Marija’ juice. Contents of

270

the remaining flavonols, quercetin-3-O-galactoside, kaempferol-3-O-galactoside and –glucoside were

271

below 4 mg/100 mL, and these of p-coumaroyl-acylated quercetin and kaempferol, were below 1

272

mg/100 mL of juices. However acylated by p-coumaroyl flavonols were not detected in some juices,

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i.e. ‘Kaszczenko 18’ and ‘Uspiech’. This suggests that current methods used to produce juices do not

274

yield an efficient extraction of the phenolics from peel. Previous studies have shown that pomace –

275

being the waste product from apple juice making – contains high levels of phenolics and has a high

276

antioxidant activity (OszmiaĔski, Wojdyło & Kolniak, 2011), again indicating that processing

277

adaptations could produce juices with higher levels of phenolics.

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3.3.

Quantity of polyphenols after storage

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During 6 months of storage at 4 and 30oC, a significant change was observed in the content of

280

polyphenols, especially in procyanidins (Table 3). After storage, the content of total polyphenols was

281

decreasing successively in all quince juices. The levels of total phenolics were declining maximally to

282

15 and 37 % during storage at 4oC and at 30oC, respectively. The content of polymeric procyanidins

283

was observed to decrease more rapidly than the content of other phenolic compounds, especially when

284

samples of juices were stored at 30o C. During 6 months of storage, the quince juice samples showed a

285

55% and 37% decline in the content of these compounds at 30oC at 4oC, respectively. Juices produced

286

from quince cultivars: ‘Akademiczeskaja’, ‘Kaszczenko 18’, ‘Portugesica’ and ‘Uspiech’ were

287

characterized by lesser degradation of flavan-3-ols composition, especially of polymeric procyanidins

288

compared to the other juices. Probably these procyanidins bonded to macromolecules, such as

289

proteins, and formed a precipitate during storage. More research is needed, however, to identify the

290

mechanism(s) responsible for the losses of the procyanidins during storage of juices (Guyot,

291

Bourvellec, Marnet, & Drilleau, 2002; Le Bourvellec, Bouchet & Renard, 2005). Similar behavior of

292

procyanidin monomers, dimers and trimers was described by OszmiaĔski, Wojdyło & Kolniak (2011)

293

for apple juices stored over 6 months at 30 o C (they were extensively degraded) and by Brownmiller,

294

Howard & Prior (2009) for processed blueberry products. Additionally, a higher content of monomeric

295

and dimeric flavan-3-ols was observed after storage especially in the samples stored at 30oC. The

296

higher content of these compounds was due to the depolymerization effect of proanthocyanidins in

297

quince juices and their conversion into elementary units. A similar effect has previously been observed

298

in drying sour cherry for monomeric and polymeric procyanidins (Wojdyło, Figiel, Lech, Nowicka &

299

OszmiaĔski, in press), and in blueberry products (Brownmiller, Howard & Prior, 2009). The degree of

300

polymerization of procyanidin after storage at 4oC was by 5% higher than before storage (Table 3). A

301

similar effect was observed previously by OszmiaĔski & Wojdyło (2009 a, b). Other determined

302

polyphenolic compounds were more stable than procyanidins. During storage at 4 oC no significant

303

changes were observed in concentrations of hydroxycinnamates and quercetin glycosides. Spanos,

304

Wrolstad & Heatherbell (1990) reported that 9-month storage of apple juice concentrates at 25 oC

305

resulted in 36% degradation of hydroxycinnamates, 60% degradation of flavonols, and total loss of

306

procyanidins. In turn 6 months of storage at 30 oC caused maximally 26% degradation of chlorogenic

307

acid and 18% degradation of phloretin-2-O-glucoside in apple purees (OszmiaĔski, Wolniak, Wojdyło

308

& Wawer, 2007).

309

3.4.

Procyanidins in soluble fractions of quince juices

310

For the first time the procyanidins were analyzed by direct phloroglucinolysis in soluble

311

precipitate from quince juices and presented in Table 4. Determination of procyanidins content is

312

problematic because they often occur as complex mixtures, which makes their separation difficult. In

313

spite of the strong interaction of polyphenols and polysaccharides, we were able to analytically

314

characterize the polyphenolic constituents in the low-cloudy quince juices. Recent studies

315

demonstrated that apple cell walls had the capacity to bind apple procyanidins and that this retention

316

depended upon compositional and structural parameters such as: stereochemistry, conformational

317

flexibility, molecular weight, and procyanidin concentrations (Le Bourvellec, Bouchet & Renard,

318

2005; Renard, Baron, Guyot & Drilleau, 2001). They also showed that during apple pressing

319

procyanidins were transferred from fruit vacuoles to juice (Le Bourvellec, Le Quere, Sanoner, Guyot

320

& Drilleau, 2004). Procyanidins mainly bind to pectin compared to other cell wall compounds and can

321

form bridges between readily soluble pectin and insoluble protopectin (Arranz, Saura-Calixto, Shaha

322

& Kroon, 2009). The highest contents of procyanidins and mDP in soluble fractions were observed in

323

the ‘Uspiech’ and ‘Portugesica’ juices (Table 4), likewise their contents measured directly in juices

324

(Table 2). The juices made from ‘Cezar’, ‘Wołgogradzkaja Aromatnaja’ and ‘S1’ cultivars were

325

characterized by the lowest content and mDP of procyanidins. However the mDP of procyanidins after

326

sedimentation was 3-5 times higher than that determined in quince juices. This result is in agreement

327

with the findings reported in other work which demonstrated that the amounts of procyanidins bound

328

to polysaccharides increased with the initial concentration of procyanidins and with mDP

329

(OszmiaĔski, Wojdyło & Kolniak, 2009c). As suggested by Le Bourvellec, Le Quere, Sanoner, Guyot,

330

& Drilleau (2004), higher polymers were bound selectively to procyanidin mixtures, and apple

331

procyanidins were selectively retained by apple cell walls, all the more that the degree of their

332

depolymerization was increasing (Le Bourvellec, Le Quere, Sanoner, Guyot & Drilleau, 2004). In

333

turn, Renard, Baron, Guyot & Drilleau (2001) suggested that apple procyanidins, especially those with

334

higher mDP (>8), rapidly bound with cell material which allowed obtaining a high quantity of

335

sediment (namely precipitated sediment).

336

3.5. Antioxidant capacity of quince juices and its changes during storage

337

On the basis of data presented in Table 5, cultivar had a significant influence on antioxidant

338

capacities of quince juices measured as free radical-scavenging activity (ABTS+• and DPPH•

339

methods) and ferric-reducing Fe+3 capacity by FRAP method. The antioxidant capacity measured by

340

DPPH• scavenging ranged from 2.2 to 7.2 mM Trolox/ 100 mL, that measured by the ABTS+• method

341

ranged from 7.8 to 10.8 mM Trolox/100 mL, and the ability to reduce Fe+3 to Fe+2 ranged from 0.2 to

342

3.0 mM Trolox/ 100 mL. The higher antioxidant capacity measured by all these methods was reported

343

for the following juices: ‘Uspiech’, ‘PóĨna Rejmana’, ‘Kaszczenko 18’ and ‘Marija’. The measured

344

value of the antioxidant capacity was strongly dependent on the polyphenolic content. When different

345

assays were compared, FRAP showed lower values than both ABTS+ and DPPH which presented

346

alike levels. This might be explained by a poor correlation (r=0.567) established between FRAP and

347

TPC, which is in accordance with previous reports (Guendez, Kallithraka, Makris & Kefalas, 2005).

348

Worthy of mentioning is the contribution of each bioactive compound to the antioxidant capacity

349

assays. When the contents of polyphenolic compounds were individually correlated with ABTS+•,

350

DPPH•, and FRAP (more than r=0.879), no significant correlations (r=0.452) were reported for total

351

polymeric procyanidins. With regard to hydroxycinnamic acids, their contents were strongly correlated

352

with the antioxidant capacity, except for DPPH• assay where only a low correlation was observed. It is

353

likely that the effective, low molecular weight antioxidants (chlorogenic acid, (−)-epicatechin)

354

participate in the first stage of the reaction with the radical. The polymerized procyanidins are mainly

355

responsible for the antioxidant capacity when the measurements are done after 10 min or later

356

(OszmiaĔski, Wolniak, Wojdyło & Wawer, 2007).

357

Regarding changes over the storage period, there were no significant differences between the

358

two studied temperatures. The antioxidant capacity was rather constant and did not exceed 30% losses

359

at 4 o C and 43% at 30 oC. Similar effects were observed by Gironés-Vilaplana, Mena, García-Viguera

360

& Moreno (2012) and OszmiaĔski, Wojdyło & Kolniak (2011).

361

3.6.

Cluster analysis

362

Results of cluster analysis conducted for the analyzed quince juices are presented in

363

dendrograms in Figure 1. Two clusters were identified in juices as follows: cluster A including

364

‘Akademiczeskaja’. ‘Leskovac’. ‘Cezar’. ‘Danurok Onuku’, ‘Marija’, ‘Wołgogradzkaja Aromatnaja’,

365

‘PóĨna Rejmana’ and ‘S1’ cultivars, and cluster B consisting of ‘Bereczki’, ‘Kaszczenko 18’,

366

‘Portugesica’ and ‘Uspiech’ cultivars. It is interesting to note that ‘Uspiech’, ‘Kaszczenko 18’ and

367

‘PóĨna Rejmana’ juices were in separate clusters despite having a similar level of phenolic compounds

368

(especially proanthocyanidins) and the antioxidant capacity of quince juice materials.

369

These observations suggest that juices made of the cultivars from cluster A would present similar

370

polyphenolic profiles between themselves but different from the other juices made of the cultivars

371

belonging to cluster B. This fact was not possible to be observed from the traditional quince juices

372

classification in technological groups by measuring the content of total polyphenols. In juices from

373

‘Cezar’, ‘Danuron Onuku’,

374

present low or intermediate polyphenol concentrations. What is more, these cultivars were

375

characterized by a high activity of polyphenoloxidase (PPO) compared to other cultivars (Wojdyło,

376

OszmiaĔski & Bielicki, 2013). Therefore, concentrations of polyphenols in their juices are relatively

377

lower than those in the other cultivars and more similar to non-bitter cultivars that are not so sensitive

378

to oxidation.

379

4. Conclusion

Marija’ and ‘Wolgogradzkaja Aromatnaja’ cultivars, these cultivars

380

The results included in this manuscript characterized and compared the polyphenolic

381

compounds and antioxidant activity of quince juices produced from different cultivars widely grown

382

in Poland. Juices produced from quince cultivars showed a wide range of variations in the chemical

383

parameters investigated. Contents of phenolic compounds in the analyzed juices was higher than in

384

commonly consumed apple juices, hence quince fruits seem an interesting alternative for the food

385

industry. However, not all cultivars examined allowed producing juices with high contents of

386

biologically-active compounds. Although ‘Uspiech’, ‘PóĨna Rejmana’, ‘Kaszczenko 18’ and ‘Marija’

387

juices were rich in bioactive compounds, especially polymeric proanthocyanidins, that were

388

characterized by a high antioxidative activity. In contrast to these juices, ‘Akademiczeskaja’ juice

389

showed other proportion of main groups of polyphenols than the remaining juices.

390

Furthermore, sensory assessment of the analyzed juices is needed as its effect could trigger an

391

increasing interest in quince fruits and their potential application for juice production. This

392

information may be useful for the juice industry as a starting point for the development of tasty quince

393

juices with high levels of bioactive compounds.

394

Acknowledgements

395

This work was supported by the Polish Ministry of Science and Higher Education. Project N N312

396

199935 (2008-2011). The authors wish to thank ElĪbiecie Buckiej and Marii Bortkiewicz for technical

397

assistance. We thank Piotr Radwan-Pytlewski for plant materials.

398

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Table 1

Retention time (Rt), Ȝmax and MS/MS fragmentation data of major phenolic compounds detected in quince juice

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

Name

Rt (min)

Ȝmax (nm)

Neochlorogenic acid 4-O-p-Coumaroylquinic acid Procyanidin dimer Chlorogenic acid Procyanidin B2 Cryptochlorogenic acid (-)-Epicatechin p-Coumaroylquinic acid derivatives Quercetin-3-O-galactoside Quercetin-3-O-rutinoside Quercetin-3-O-glucoside Kaempferol-3-O-galactoside 3,5-di-Caffeoylquinic acid Kaempferol-3-O-rutinoside Kaempferol-3-O-glucoside Quercetin glucoside acylated by p-coumaric acid Kaempferol glucoside acylated by p-coumaric acid

2.31 3.13 3.41 3.48 3.73 3.86 4.61 4.73 7.12 7.24 7.38 8.04 8.21 8.35 8.54 10.83 12.08

325 309 278 325 278 325 278 310 243; 352 243; 352 243; 352 264; 345 326 264; 345 264; 345 242; 352 265. 345

MS [M-H](m/z) 353 337 577 353 577 353 289 337 463 609 463 447 515 593 447 609 593

MS/MS [M-H](m/z) 191 173/136 289 191 289 173 245 136 300 301 300 284 353/136/182 285 285 463/301/136 285

Table 2 Effect of different cultivars on the polyphenolic compounds (mg/100 mL) of quince juices immediately after processing

Compoun ds C

Juice variety ‘Akademiczeskaja’

‘Bereczki’

‘Danurok Onuku’

‘Cezar’

‘Kaszczenko 18’

‘Leskowaþ’

‘Marija’

‘Portugesicka’

‘PóĨna Rejmana’

‘S1’

‘Wołgogradzkaja Aromatnaja’

‘Uspiech’

mean

4.5±1.1a

3.2±0.5c

3.4±0.7c

1.5±0.4e

3.6±0.1bc

2.3±0.3d

4.0±0.6b

4.0±0.5b

1.2±0.1e

3.0±0.2c

3.7±0.1bc

2.1±0.4d

3.0

19.5±0.8c

25.2±0.5b

18.2±1.2cd

23.6±0.5b

14.2±0.8e

3.8±0.1g

20.5±1.3b

37.2±1.6a

23.0±0.6b

15.5±1.4e

3.1±0.4g

9.9±1.1f

17.8

E

42.3±1.2de

37.4±2.1f

48.3±2.5d

57.1±3.1b

54.4±2.2c

33.8±1.2f

41.7±2.1e

54.1±1.9c

30.3±2.0g

32.2±1.5g

63.5±1.0a

45.0±2.1d

45.0

PB2

72.0±1.4de

65.2±1.5e

138±3a

110±3bc

64.1±3.1ef

68.1±2.6e

76.7±1.1d

80.6±2.6d

0.0±0h

56.9±2.6g

103.±4.5c

112±4.1b

78.9

PC1

96.4±4.2e

73.3±2.7f

93.4±3.5e

79.0±2.7f

121±5b

56.0±1.8h

117±2.4c

119±1c

68.6±1.4fg

113±1cd

140±1a

60.4±2.1g

94.8

PP

802±21ef

1608±34d

541±18g

526±25g

1953±46c

897±26e

479±19i

2612±35b

148±10k

225±10j

3105±23.5a

550±12h

1120

NhA

131±2.4d

162.8±4.5c

167.5±2.7c

114.3±1.9g

129±3.0f

127±2.5f

138±3.6d

176.2±2.5b

118.3±1.6g

98.0±2.8h

169.1±3.1a

130.2±2.8d

138

4-pCA

32.9±2.5e

62.8±3.5b

78.8±1.6a

31.3±2.6e

40.1±2.6d

34.2±2.4e

52.1±1.9c

62.6±2.6b

33.2±1.8e

29.3±1.6f

55.9±2.0c

26.3±1.0

44.9

CA

15.4±1.3e

30.1±1.3b

38.8±2.4a

11.5±1.5g

16.7±2.4d

16.0±2.1de

17.5±1.4d

26.5±1.5c

39.1±2.6a

14.9±1.1f

23.9±0.9c

14.4±1.1f

22.1

dChA

38.9±2.1h

286±4c

253±3d

220±3e

301±3b

256±6d

264±3d

321±2a

197±5f

226±3e

279±3c

132±2g

231

ChA

12.7±1.2e

35.2±1.3b

21.1±2.1d

20.7±1.1d

27.5±2.7c

28.0±1.5c

33.1±1.1b

41.6±2.4a

20.4±2.4d

26.5±1.1c

40.1±1.3a

6.5±2.1

26.1

d pCA

22.5±0.3e

53.7±1.2b

66.5±1.3a

25.7±2.1d

16.2±2.1f

27.5±1.6d

26.6±2.5d

52.2±2.8b

23.0±1.4e

18.2±2.0f

33.7±1.3c

20.6±0.9e

32.2

3,5-CA

6.5±0.2b

4.4±0.3d

6.7±0.5b

4.1±0.1de

4.0±0.2de

4.6±0.1d

4.7±0.3d

5.0±0.4c

3.4±0.3f

4.7±0.2d

8.1±0.4a

2.3±0.1g

4.9

QR

1.6±0.3c

1.9±0.1b

0.9±0.1d

2.0±0.2b

1.8±0.3b

2.8±0.3a

1.3±0.2c

1.6±0.4c

2.7±0.3a

1.5±0.4c

1.8±0.2bc

2.0±0.3b

1.8

QG

12.9±1.9c

14.2±0.6b

16.0±0.9a

11.0±1.1d

15.1±0.6a

11.3±0.9d

16.0±1.3a

14.6±0.5b

9.5±0.9e

7.6±0.1f

11.7±1.2d

6.3±0.5g

12.2

KG

2.3±0.2bc

2.5±0.3b

2.0±0.2c

1.7±0.2d

2.0±0.3c

2.0±0.0c

2.9±0.1a

2.4±0.2b

1.2±0.0e

0.9±0.0f

1.7±0.3d

0.7±0.1g

1.9

KR

3.0±0.2b

3.1±0.3b

2.4±0.2c

1.8±0.3cd

2.1±0.1c

2.0±0.1c

3.9±0.2a

4.1±0.3a

1.7±0.2cd

1.5±0.4d

1.7±0.2cd

0.5±0.0e

2.3

Qp-CA

0.0±0.0c

0.4±0.0a

0.0±0.0c

0.1±0.0c

0.0±0.0c

0.3±0.0a

0.1±0.0c

0.0±0.0c

0.2±0.0b

0.0±0.0c

0.0±0.0c

0.3±0.1a

0.1

KpCA

0.4±0.1c

0.0±0.0d

0.1±0.0d

0.1±0.0d

0.0±0.0d

0.2±0.0cd

0.8±0.1b

1.0±0.2a

0.1±0.0d

0.2±0.0cd

0.0±0.0d

0.1±0.0d

0.2

1317

2469

1496

1241

2766

1572

1300

3615

721

874

4045

1122

1878

PB1

Ȉ TP

*C- (+)-catechin; PB1- procyanidin B1; E- (−)-epicatechin; PB2- procyanidin B2; PC1- procyanidin C1; PP- polymeric procyanidins; NhA - neochlorogenic acid; 4-pCA- 4-p-coumaroyloquinic acid; CA- cryptochlorogenic acid; dChA - derivative of chlorogenic acid; ChA - chlorogenic acid; d pCA – derivative of p-coumaroyloquinic acid; 3,5-CA- 3,5-dicaffeoylquinic acid; QR quercetin-3-O-rutinoside; QG - quercetin-3-O-galactoside; KR - kaempferol-3-O-rutinoside; KG- quercetin-3-O-galactoside; Qp-CA – quercetin glucoside acylated by p-coumaric acid; KpCA kaempferol glucoside acylated by p-coumaric acid; Ȉ TP- sum of the determined phenolics.

**Values are means standard deviation, n = 2; ***mean values within a row with different letters are significantly different at p < 0.05.

Table 3 Effect of different cultivars on the polyphenolic compounds (mg/100 mlL of quince juices after storage 6 month at 4 oC

‘Akademiczeskaja’ C

mean

Juice variety

Components ‘Bereczki’

‘Cezar’

‘Danurok Onuku’

‘Kaszczenko 18’

‘Leskowaþ’

‘Marija’

‘Portugesicka’

‘PóĨna Rejmana’

‘S1’

‘Uspiech’

‘Wołgogradzkaja Aromatnaja’

5.2±0.3a

2.8±0.1e

3.8±0.4c

2.1±0.6f

3.0±0.1d

2.2±0.0f

4.1±0.4c

4.7±0.2b

2.1±0.4f

3.1±0.1d

3.3±0.2d

2.6±0.2e

3.3

PB1

10.5±1.1e

19.8±2.4b

13.6±1.2d

13.9±1.1d

20.5±3.3b

11.5±1.1e

3.9±0.7f

27.2±2.6a

14.4±1.0c

15.4±2.6c

3.5±0.8f

12.9±1.1d

13.9

E

26.4±2.3c

22.7±1.4d

28.9±3.1c

42.1±4.7a

34.0±1.4b

22.9±2.4d

26.6±1.2c

36.4±3.1b

11.7±1.0e

10.2±0.8e

36.6±2.7b

25.3±2.2c

27.0

PB2

56.3±4.2g

60.7±4.3f

109.1±3.1a

99.1±5.6b

59.2±2.1fg

59.6±1.0f

64.7±0.8f

75.5±3.2e

1.0±0.5h

35.8±1.1

91.7±2.5c

85.1±3.4d

66.5

PC1

86.6±2.1e

124±2bc

88. 2±4.2e

73.7±1.1f

137±4a

52.0±2.1g

113±4c

102±4d

91.2±2.6e

108±2c

130±3a

79±2f

98.6

739±5ef

1476±6d

565±10f

507±7f

1781±29c

823±11e

519±20f

2505±26b

142±9h

200±10h

2731±29a

406±32g

1032

127±2c

161±1b

165±3b

113±8d

127±3c

125±1c

136±3c

173±6a

130±3c

97.1±3.6e

164±5b

127±4c

137

4-pCA

31.7±3.5d

59.5±2.1b

77.3±3.6a

30.0±1.4d

37.4±2.0d

32.9±0.9d

49.5±3.3c

60.5±1.5b

38.3±1.8d

27.8±2.0e

49.2±1.0c

25.7±2.5e

43.3

CA

16.0±1.0d

31.0±2.1b

39.6±2.4a

12.2±1.4e

16.9±0.7d

16.3±1.4d

18.0±1.2d

27.5±2.0b

11.9±1.0e

14.4±2.5e

25.1±1.1c

14.4±0.9e

20.3

dChA

28.0±2.4g

281±1b

251±2c

216±2e

300±5b

253±7c

259±2c

320±4a

212±3d

222±3de

271±2b

126±1.6f

250.9

ChA

41.1±1.1a

36.2±2.1b

23.1±1.3cd

19.8±1.1e

27.4±2.5c

26.7±3.2c

32.5±1.0b

40.3±1.6a

23.0±0.9cd

26.7±2.4c

38.8±1.1a

6.1±1.0f

28.5

d pCA

34.1±2.4d

55.7±1.6b

66.4±2.5a

25.9±1.0e

14.8±0.9g

25.6±1.3e

25.4±2.3e

49.7±1.6c

24.6±2.1e

18.2±3.9f

31.4±1.9d

19.7±1.3f

32.6

3.5-CA

6.6±1.2b

4.1±1.0c

6.4±0.1b

3.9±0.9c

4.3±0.2c

4.7±0.5c

4.9±0.7c

4.5±0.0c

3.9±0.3c

4.3±0.1c

7.4±0.2a

2.2±0.0d

4.8

QR

2.2±0.1c

1.9±0.2c

2.1±0.0c

2.6±0.1b

2.0±0.1c

1.6±0.1d

2.0±0.2c

1.8±0.1cd

2.0±0.2c

1.2±0.1e

2.0±0.2c

3.0±0.3a

2.0

QG

12.5±1.2c

16.6±1.1a

13.8±0.9b

11.7±0.4d

12.6±1.1c

7.4±1.3d

13.9±0.2b

15.0±1.3a

11.1±1.1d

16.1±2.1a

6.3±0.6d

12.1±0.9c

12.4

KG

1.8±0.5bc

3.1±0.8a

2.3±0.4b

1.9±0.6bc

2.1±0.4b

0.8±0.1d

2.1±0.3b

2.0±0.4b

1.7±0.5c

1.7±0.4c

0.7±0.1d

2.9±0.3a

1.9

KR

1.7±0.3c

3.9±0.1a

2.8±0.2b

1.8±0.4c

2.8±0.1b

1.3±0.1d

3.8±0.2a

1.9±0.2c

1.8±0.3c

2.2±0.4bc

0.5±0.0d

2.4±0.1bc

2.2

Qp-CA

0.3±0.0a

0.0±0.0c

0.0±0.0c

0.3±0.1a

0.4±0.0a

0.2±0.0b

0.0±0.0c

0.0±0.0c

0.2±0.0b

0.0±0.0c

0.3±0.0a

0.2±0.0b

0.2

KpCA

0.1±0.0d

0.5±0.1b

0.3±0.0bc

0.2±0.0c

0.0±0.0

0.2±0.0c

0.9±0.2a

0.1±0.0d

0.1±0.0d

0.4±0.0b

0.1±0.0d

0.2±0.0c

0.3

1227

2360

1460

1177

252

1468

1279

3446

724

804

3593

953

1778

PP NhA

Ȉ TP

*C- (+)-catechin; PB1- procyanidin B1; E- (−)-epicatechin; PB2- procyanidin B2; PC1- procyanidin C1; PP- polymeric procyanidins; NhA - neochlorogenic acid; 4-pCA- 4-pcoumaroyloquinic acid; CA- cryptochlorogenic acid; dChA - derivative of chlorogenic acid; ChA - chlorogenic acid; d pCA – derivative of p-coumaroyloquinic acid; 3,5-CA- 3,5dicaffeoylquinic acid; QR - quercetin-3-O-rutinoside; QG - quercetin-3-O-galactoside; KR - kaempferol-3-O-rutinoside; KG- quercetin-3-O-galactoside; Qp-CA – quercetin glucoside acylated by p-coumaric acid; KpCA - kaempferol glucoside acylated by p-coumaric acid; Ȉ TP- sum of the determined phenolics. **Values are means standard deviation, n = 2; ***mean values within a row with different letters are significantly different at p < 0.05.

Table 3 continued Effect of different cultivars on the polyphenolic compounds (mg/100 mL) of quince juices after storage 6 month at 30 oC Juice variety

Compounds ‘Akademiczeskaja’ C

‘Bereczki’

‘Cezar’

‘Danurok Onuku’

‘Kaszczenko 18’

‘Leskowaþ’

mean

‘Marija’

‘Portugesicka’

‘PóĨna Rejmana’

‘S1’

‘Uspiech’

‘Wołgogradzkaja Aromatnaja’

4.5±0.5b

4.0±1.0c

4.9±0.7b

9.5±0.8a

3.4±0.4cd

3.5±0.2cd

5.3±0.7b

3.6±0.2cd

1.8±0.7f

9.3±0.2a

2.5±0.3e

2.9±0.5d

4.6

PB1

56.9±4.5a

29.5±1.7c

50.2±2.6a

23.6±2.8d

32.0±2.5c

52.8±3.2a

47.4±1.8b

17.3±0.8e

11.4±2.6f

25.2±1.7d

25.2±2.0d

56.3±3.3a

35.7

E

23.3±2.3b

10.4±1.6cd

41.5±0.9a

15.9±1.1c

6.5±0.8e

1.9±0.5f

9.3±1.1d

11.9±0.3cd

5.9±0.6e

9.7±0.2c

24.6±1.1b

25.0±1.9b

15.5

PB2

47.8±3.5a

19.3±1.1cd

25.1±2.3c

37.4±1.1b

50.7±3.4a

21.0±1.0cd

24.4±1.7c

37.1±2.0b

0.0±0.0e

17.1±1.1

36.4±0.9b

26.7±1.1c

28.6

PC1

77.8±1.4c

89.1±2.8bc

98.8±1.1b

62.2±2.9d

109.3±1.1a

32.6±0.9e

107.8±9.0a

94.1±2.7b

6.4±0.8f

97.4±3.0b

107.3±2.6a

44.6±1.1e

77.3

541±26f

1112±34d

421±13g

391±22gh

1341±36c

630±22e

361±11h

1685±32b

151.±11j

141±8j

2219±42a

228±12i

768

114±1d

145±6b

152±7a

100±5e

109±1de

113±3d

124±2d

153±2a

130±3c

84±6f

144±5b

114±7d

124

4-pCA

28.4±1.0d

50.7±2.5b

65.5±3.6a

26.3±2.8e

31.4±2.9d

25.4±2.1e

44.5±2.2c

53.1±2.1b

26.6±1.4e

24.9±0.9e

44.7±2.2c

21.5±1.4f

36.9

CA

40.0±2.1c

60.9±1.3ab

69.8±5.3a

28.7±1.2d

39.3±3.3c

36.8±4.6c

40.9±1.1c

61.0±2.5ab

14.4±1.1e

33.2±3.2c

51.7±0.9b

40.5±3.3c

43.1

dChA

26.1±2.1g

253±5b

229±2d

196±3e

268±3b

232±3c

239±4c

285±3a

132±3f

207±6de

238±2d

111±7f

221

ChA

37.8±1.1a

32.4±0.9b

20.8±2.0d

19.1±1.4de

22.3±2.1d

26.1±1.1c

30.3±2.5b

35.1±2.5a

5.6±0.5f

24.6±1.1c

34.9±2.5a

5.3±0.5f

24.5

d pCA

28.1±2.1d

44.2±2.6b

57.6±3.6a

24.0±2.2e

12.8±1.9g

23.5±2.0e

21.5±1.6e

37.3±3.8c

19.7±2.0f

17.3±4.1f

24.2±2.9e

17.0±1.0f

27.3

3,5-CA

5.4±0.6a

2.6±0.4cd

5.1±0.6a

2.9±0.3c

2.4±0.2d

3.9±0.6b

4.4±0.1b

3.2±0.0c

2.3±0.3d

3.5±0.2c

4.4±0.7b

2.2±0.1d

3.5

QR

2.5±0.1b

2.5±0.3b

2.3±0.1bc

3.0±0.4a

2.7±0.2b

2.1±0.7c

2.4±0.2bc

2.1±0.1c

2.0±0.3c

2.2±0.5c

2.2±0.1c

3.1±0.3a

2.4

QG

10.6±3.1c

14.6±1.1a

11.6±1.5b

9.6±0.9c

10.9±1.3c

6.9±0.4d

11.5±0.1b

11.9±.11b

11.0±1.4b

13.8±0.7a

6.2±0.3d

10.8±1.0c

10.8

KG

1.1±0.0c

2.2±0.2a

1.4±0.0c

1.3±0.1c

1.4±0.9c

0.6±0.2d

1.3±0.3c

1.2±0.1c

1.7±0.5b

1.3±0.0c

0.6±0.1d

1.9±0.3a

1.3

KR

1.3±0.1d

3.3±0.2a

2.5±0.1b

1.7±0.6c

2.4±0.3b

1.3±0.1d

3.1±0.3a

1.6±0.5c

1.8±0.1c

2.4±0.0b

0.5±0.0e

2.1±0.2b

2.0

Qp-CA

0.3±0.0a

0.0±0.0c

0.1±0.0c

0.2±0.0b

0.0±0.0c

0.4±0.1a

0.0±0.0c

0.1±0.0c

0.1±0.0c

0.5±0.0a

0.3±0.0b

0.3±0.1b

0.2

KpCA

0.2±0.1c

0.5±0.1a

0.2±0.0c

0.2±0.0c

0.4±0.1a

0.2±0.0c

0.6±0.1a

0.0±0.0d

0.1±0.0c

0.1±0.0c

0.3±0.1b

0.3±0.0b

0.3

1047

1877

1259

952

2046

1213

1079

2493

525

715

2967

712

1427

PP NhA

Ȉ TP

*C- (+)-catechin; PB1- procyanidin B1; E- (−)-epicatechin; PB2- procyanidin B2; PC1- procyanidin C1; PP- polymeric procyanidins; NhA - neochlorogenic acid; 4-pCA- 4-pcoumaroyloquinic acid; CA- cryptochlorogenic acid; dChA - derivative of chlorogenic acid; ChA - chlorogenic acid; d pCA – derivative of p-coumaroyloquinic acid; 3,5-CA- 3,5dicaffeoylquinic acid; QR - quercetin-3-O-rutinoside; QG - quercetin-3-O-galactoside; KR - kaempferol-3-O-rutinoside; KG- quercetin-3-O-galactoside; Qp-CA – quercetin glucoside acylated by p-coumaric acid; KpCA - kaempferol glucoside acylated by p-coumaric acid; Ȉ TP- sum of the determined phenolics. **Values are means standard deviation, n = 2; ***mean values within a row with different letters are significantly different at p < 0.05.

Table 4 Effect of different cultivars on the degree polymerization of procyanidins (mDP) of quince juices and sediments immediately after processing and after storage time (6m) at 4 and 30 oC

Juice variety

mDP of juices ‘Akademiczeskaja’

6m at 4 o C

Immediately after processing PP of sediment

mDP of sediment

mDP of juices

6 m at 30o C PP of sediment

mDP of sediment

mDP of juices

PP of sediment

mDP of sediment

6.4±1.1d

7296±130d

16.7±1.3d

16.1±1.2a

7054±132c

11.8±1.3

15.7±2.6a

6113.8±133de

16.4±1.5c

10.8±0.7ab

7897±99cd

10.1±1.4e

11.7±1.3b

7699±90c

10.7±0.9cc

10.4±1.3b

6588.1±101de

10.6±1.2d

‘Cezar’

3.3±0.2e

1902±74f

10.6±0.4e

3.7±0.5d

575±99g

13.8±1.1c

3.8±0.3d

476.8±44h

15.0±2.1c

‘Danurok Onuku’

3.4±0.1e

11027±230b

10.5±0.6e

3.6±0.2d

9606±235c

9.9±0.9d

3.3±0.5de

8224.8±131c

9.4±0.8e

‘Bereczki’

‘Kaszczenko 18’

10.4±0.2ab

9213±100bc

10.4±1.1e

11.1±0.9b

8563±124cd

9.8±1.1d

10.4±1.1b

7884.3±153d

6.0±0.6f

7.1±0.7c

10265.7±214b

27.9±0.4b

7.2±0.2c

9418±242c

20.7±1.2b

7.1±1.4c

8079.4±216c

21.8±2.3b

‘Marija’

4.2±0.3de

8212±68c

15.4±1.1d

4.5±0.1d

7519±158c

11.9±0.3c

4.1±0.9d

6163.9±207e

12.8±1.8d

‘Portugesicka’

11.6±1.2a

15324±121a

15.3±1.2d

12.0±1.2b

14561±148a

9.3±0.9d

9.9±1.0b

12424.9±235a

8.3±0.7e

‘PóĨna Rejmana’

2.7±0.2e

11312±144b

37.7±2.4a

4.1±0.4d

5955±68e

27.3±2.4a

4.2±0.6d

4661.7±99f

32.8±2.8a

‘S1’

2.5±0.1e

4408±75e

21.4±2.1c

2.8±0.2e

1691±143f

24.6±2.1b

3.1±0.2de

1229.9±124g

21.4±1.6b

13.5±1.3a

16828±106a

23.2±0.8c

12.5±0.9b

13516±148b

22.9±1.7b

10.8±1.4b

10034.3±241b

16.1±1.3c

2.8±0.1e

1673±79f

39.4±1.2a

3.0±0.1e

1555±112f

27.7±0.9a

2.7±0.2e

1364.6±165g

22.1±2.5b

‘Leskowaþ’

‘Uspiech’ ‘Wołgogradzkaja Aromatnaja’

*6m: 6 months; **Values are means standard deviation, n = 2; ***mean values within a row with different letters are significantly different at p < 0.05.

Table 5 Effect of different cultivars on the antioxidant activity (mM Trolox/100 mL) of quince juices immediately after processing and after storage time (6 m) at 4 and 30 oC

Immediately after processing

6m at 4 oC

ABTS

ABTS

6m at 30oC

Juice variety DPPH

FRAP

DPPH

FRAP

ABTS

DPPH

FRAP

‘Akademiczeskaja’

8.3±2.3c

3.9±0.5e

0.6±0.2e

8.2±0.4b

3.4±0.3de

0.5±0.0d

8.1±0.3bc

3.1±0.3d

0.5±0.1d

‘Bereczki’

8.4±1.2c

4.6±0.3d

0.7±0.1e

8.6±1.1b

3.8±0.2d

0.7±0.1c

8.0±0.4bc

3.9±0.1cd

0.6±0.0d

‘Cezar’

7.8±1.1cd

2.5±0.2f

0.3±0.0g

7.8±0.5bc

2.2±0.4f

0.3±0.0e

7.7±1.0c

1.8±0.4e

0.2±0.2f

‘Danurok Onuku’

7.8±0.6cd

2.1±0.2f

0.2±0.0g

7.8±0.3bc

1.8±0.1fg

0.2±0.0e

7.7±1.2c

2.0±0.3e

0.2±0.0f

‘Kaszczenko 18’

9.4±1.3b

5.8±0.3bc

1.5±0.1c

8.8±0.8b

4.5±0.0c

1.1±0.3b

8.8±1.6b

3.9±0.4cd

0.9±0.0c

‘Leskowaþ’

8.3±0.1c

3.6±0.2e

0.5±0.0f

8.1±0.2b

2.7±0.4e

0.4±0.1e

8.1±0.4bc

2.9±0.3d

0.4±0.1e

‘Marija’

9.0±0.4b

5.8±0.5bc

1.1±0.2cd

8.9±0.6b

3.9±0.2d

1.2±0.4b

8.8±0.2b

4.4±0.2b

0.9±0.2c

‘Portugesicka’

8.3±1.1c

3.5±0.1e

0.5±0.1f

8.2±0.8b

3.0±0.5e

0.6±0.0cd

8.2±0.0b

3.4±0.2d

0.5±0.0e

‘PóĨna Rejmana’

9.3±1.4b

6.3±1.2b

2.6±0.2b

8.9±0.0b

5.6±0.1b

2.5±0.4a

8.5±0.6b

4.2±0.3b

1.8±0.4b

‘S1’

8.3±0.4c

3.9±0.7e

0.6±0.0f

8.3±1.4b

3.0±0.0e

0.5±0.1d

8.1±0.4bc

3.0±0.1c

0.4±0.0e

10.8±0.1a

7.2±0.8a

3.0±0.3a

10.9±0.9a

5.9±0.2a

2.5±0.5a

10.2±1.1a

6.2±0.2a

2.3±0.4a

8.2±0.8c

3.0±0.3ef

0.4±0.0f

8.0±1.0b

2.2±0.3f

0.3±0.0e

7.9±1.0c

2.7±0.5de

0.3±0.1ef

‘Uspiech’ ‘Wołgogradzkaja Aromatnaja’

* 6m: 6 months; **Values are means standard deviation. n = 2; ***mean values within a row with different letters are significantly different at p < 0.05.

Figure legends

Figure 1 Dendogram of cluser analysis of quince juices accessions

Figure 1

Akademiczeskaja Leskovac Cezar Danurok onuku Marija :RáJRJUDG]NDMD$URPDWQDMD 3yĨQD5HMPDQD S1 Bereczki Kaszczenko Portugesica 8ĞSLHFK

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Highlights x

Eleven quince cv. as a good sources for their industrial processing into high-quality juices.

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The results of ANOVA and cluster analysis indicate that the quality of quince juices was affected by cultivars.

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Flavan-3-ols have the greatest influence on the antioxidant

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Quince juices are richer in bioactive compounds and more attractive than the available other commercial products.

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These results indicate the potential uses some cultivars of quince fruits for juice industry.

Antioxidant property and storage stability of quince juice phenolic compounds.

The aim of this study was to characterise, in depth, 11 quince cultivars to provide data for their industrial processing into high-quality juices. Pol...
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