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Chemical Profile and Antioxidant Capacities of Tart Cherry Products

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Chemical Profile and Antioxidant Capacities of Tart Cherry Products ARTICLE IN PRESS Food Chemistry xxx (2008) xxx–xxx Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Chemical profile and antioxidant capacities of tart cherry products Ara Kirakosyan *, E.M. Seymour, Daniel E. Urcuyo Llanes, Peter B. Kaufman, Steven F. Bolling Department of Surgery and The Michigan Integrative Medicine Program, University of Michigan, Ann Arbor, MI 48109, USA article info abstract Article history: The levels of anthocyanins and other flavonoids, as well as melatonin, in various tart cherry products (fro- Received 3 July 2008 zen and dried cherries, powders from individually quick frozen (IQF) cherry and juice concentrate) from Received in revised form 30 September two tart cherry cultivars, ‘Montmorency’ and ‘Balaton’ were analysed comparatively by HPLC and electro- 2008 spray mass spectrometry (EMS). Our results show that the major anthocyanin compound in these two Accepted 13 November 2008 tart cherry cultivars is cyanidin 3-glucosylrutinoside, followed by cyanidin 3-rutinoside, cyanydin sop- Available online xxxx horoside, and peonidin 3-glucoside. Studies on antioxidant activities (total antioxidant status assay) of crude extracts of ten tart cherry products show that these products preserve their antioxidant capacities Keywords: after processing and storage. We have also compared the antioxidant activities of several single constit- Prunus cerasus Anthocyanins uents that are present in tart cherry. When TEAC (trolox equivalent antioxidant capacity) values were Phenolics evaluated conceptually against the cherry phytochemical profile, cyanidin and its derivatives were found Antioxidant capacities to be the significant contributors to the antioxidant systems of tart cherries. It was shown that standard compounds with common aglycon moieties show similar antioxidant activities. Ó 2008 Elsevier Ltd. All rights reserved. 1. Introduction The finding that tart cherries contain significant levels of antho- cyanins may also suggest significant antioxidant activity. One of Current animal research suggests that tart cherry consumption the best known properties of anthocyanins, in general, is their may confer multiple health benefits (Seymour et al., 2008). How- strong antioxidant activity in metabolic reactions, due to their abil- ever, there is conflicting information about the phytochemistry of ity to scavenge oxygen free radicals and other reactive species anthocyanins and other flavonoids in different cultivars of tart (ROX). This feature makes anthocyanins a potential tool for use cherry (Prunus cerasus L) and in industrially-processed tart cherry in studies on oxidative stress and its related pathologies. For exam- products, such as dry fruits, powders from individually quick fro- ple, it has been reported in animal studies that tart cherry-enriched zen (IQF) cherry, frozen cherries, juices, and juice concentrates diets reduce oxidative stress and inflammation (Seymour et al., (Blando, Gerardi, & Nicoletti, 2004; Bonerz, Wurth, Dietrich, & Will, 2008). Importantly, these effects were achieved using physiologi- 2007; Chandra, Rana, & Li, 2001; Seeram, Bourquin, & Nair, 2001). cally relevant amounts of the whole fruit (Seymour et al., 2008). As such, it is unknown if these products have similar phytochem- The antioxidant, melatonin (N-acetyl-5-methoxytryptamine), ical profiles. This information is critical in order to facilitate and has been identified in fresh-frozen fruits of ‘Balaton’ and ‘Montmo- validate further studies on the health effects of consumption of tart rency’ tart cherries, suggesting that sufficiently high levels of mel- cherry products. atonin could alter blood levels of this indole and provide protection Recently, tart cherry has had increasing impact upon the edible against oxidative damage (Burkhardt, Tan, Manchester, Hardeland, fruits market, due to the suspected health benefits associated with & Reiter, 2001). regular intake of anthocyanins and related polyphenolics (Beattie, The biological effectiveness of tart cherries may be due to Crozier, & Duthie, 2005; Kim, Heo, Kim, Yang, & Lee, 2005; Piccol- phytochemical interactions which accomplish complementary ef- ella et al., 2008). The major anthocyanins in tart cherries are deriv- fects. Thus, it is not surprising that whole cherry fruit products atives of cyanidin, while in other berries, such as strawberries, or mixtures of tart cherry secondary metabolites could be bio- pelargonidin glycosides predominate. It is noteworthy, however, logically more active than individual components. Such a syner- that anthocyanins may not be stable during processing or storage. gistic effect refers to cases when combinations of bioactive As a result, some anthocyanin derivatives may be rapidly formed substances exert effects at target sites that are greater than which may impact bioavailability and bioactivity. the sum of individual components (Cseke et al., 2006; Lila & Ra- skin, 2005). In the present study, we aim to identify and quantify the antho- * Corresponding author. Tel.: +1 734 6154675. cyanins and other flavonoid phytochemicals, as well as melatonin, E-mail address: [email protected] (A. Kirakosyan). in various tart cherry products from two cherry cultivars, namely 0308-8146/$ - see front matter Ó 2008 Elsevier Ltd. All rights reserved. doi:10.1016/j.foodchem.2008.11.042 Please cite this article in press as: Kirakosyan, A., et al. Chemical profile and antioxidant capacities of tart cherry products. Food Chemistry (2008), doi:10.1016/j.foodchem.2008.11.042 ARTICLE IN PRESS 2 A. Kirakosyan et al. / Food Chemistry xxx (2008) xxx–xxx ‘Montmorency’ and ‘Balaton’. Secondly, we aim to determine their 2.5. HPLC analysis respective antioxidant capacities using the common trolox equiva- lent antioxidant capacity (TEAC) assay. An aliquot (10 ll) of the extract was analysed by HPLC. The HPLC conditions were as follows: a Phenomenex LunaTM column 2. Materials and methods (Torrance, CA) (5 micron pore size, C-18, 150 mm  4.60 mm), flow rate of 1 ml per minute, Solvent A = water + 0.1% TFA (trifluoroace- 2.1. Chemicals tic acid); Solvent B = acetonitrile + 0.1% TFA. HPLC running conditions consisted of a gradient: 0-10 min, 8-18% B in A (linear); Solvents employed for extraction and HPLC analysis were ob- 10–18 min, 18–28% B in A (linear); 18–19 min, 28–40% B in A (lin- tained from Fisher Scientific Co., Pittsburgh, PA. Folin-Ciocalteu ear); 19–22 min, 40–60% B in A (linear); 22–23 min, 60–8% B in A phenol reagent, quercetin, kaempferol, melatonin, gallic acid, and (linear); 23–25 min, 8% B in A (isocratic); oven temperature, 40 °C. propyl gallate were purchased from Sigma Chemical Co., St. Louis, The quantitative analysis of each compound in the extracts was MO. Anthocyanins (cyanidin, cyanidin-3-glucoside, cyanidin-3- carried out with a Shimadzu HPLC equipped with a photodiode ar- rutinoside, cyanidin 3-glucosylrutinoside, cyanidin 3-sophoroside, ray detector (SPDM-6A system from Shimadzu, Kyoto, Japan). Each peonidin-3-glucoside, peonidin, and pelargonidin) and other flavo- known anthocyanin in the extracts was analysed quantitatively by noids (isorhamnetin and isorhamnetin-3-rutinoside) were ob- comparison with the corresponding authentic samples. Detection tained from Extrasynthèse (Genay, France) and Polyphenols was set at 520 nm. Laboratories (Sandnes, Norway). HPLC analysis of isorhamnetin, isorhamnetin 3-rutinoside, kaempferol, and quercetin was conducted in the same manner as 2.2. Extraction of anthocyanins and other metabolites reported previously (Kirakosyan et al., 2004). Frozen and dried pitted tart cherries, powders from individually 2.6. Liquid chromatography-mass spectrometry (LC–MS) analysis of quick frozen (IQF) tart cherry and tart cherry juice concentrates anthocyanins were kindly supplied by The Cherry Marketing Institute (CMI) (Lansing, MI). Freeze-dried tart cherry powder (1 g from all prod- An Alliance 2695 HPLC (Waters Corp., Milford, MA) was used to ucts excluding juice concentrate) was extracted with 10 ml meth- generate a binary gradient with 0.05% TFA in water as the aqueous anol/water/acetic acid (85:15:0.5 v/v/v) for anthocyanins and solvent (A) and 0.05% TFA in acetonitrile as the organic modifier 10 ml methanol/water (80:20 v/v) for other flavonoids and melato- (B). Chromatographic separation of anthocyanins was achieved nin in 15 ml screw-cap tubes at 4 °C and placed on a gyrorotary with a Gemini 5 lm C-18 150  2 mm reverse-phase column (Phe- shaker overnight in the dark. The juice concentrate was freeze– nomenex) held at 35 °C, using a flow rate of 0.19 ml/min. The col- dried, after which 1 g dry powder was obtained and extracted as umn was initially equilibrated to 8% B, increased to 18% B over above for the other tart cherry preparations. The samples were 10 min, 28% B over the next 8 min, 40% B for 1 min, 60% B for then vortexed and sonicated. After filtration through a 0.22 lm fil- 3 min, then returned to initial conditions. Effluent from the HPLC ter, the extracts were ready for analysis. column was directed into the electrospray ionisation probe of a TSQ Quantum Ultra AM triple quadrupole mass spectrometer 2.2.1. Fractionation of phenolics using C-18 Sep-Pak cartridges (ThermoFinnigan, San Jose, CA). Positive ions were generated with For easier separation of phenolics, a simple fractionation of tart the following parameters: spray voltage 3000 V, sheath gas 40, aux cherry phenolic extracts was performed using preconditioned C-18 gas 10, and capillary temperature 250 °C. Tube
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