Antioxidant activity versus cytotoxic and nuclear factor kappa B regulatory activities on HT-29 cells by natural fruit juices

The antioxidant activity (free radical scavenging ability and lipid oxidation inhibitory activity) and the activity in cell culture [influence on HT-29 human colon cancer cell viability and nuclear factor kappa B (NF-κB) activation] of natural fruit juices from red grape, strawberry, cherry and sour cherry were investigated in vitro. Analysis of polyphenolic composition of fruit juices showed the dominant presence of anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutinoside, peonidin-3-rutinoside, pelargonidin-3-glucoside), anthocyanidins (procyanidins B1, B2 and B3), flavonoids (glucosides of myricetin, quercetin and kaempferol), and phenolic acids (neochlorogenic acid, chlorogenic acid, ellagic acid, p-coumaroylquinic acid) in juices. DPPH test and β-carotene bleaching method indicated that grape, strawberry, cherry and sour cherry natural juices (at the concentration of 2.5%) showed very strong free radical scavenging (75–92%) and antioxidant activity (71–94%). In addition, at the concentration of 0.01% they showed complete inhibition of copper-induced oxidation of human LDL (low density lipoprotein). In contrast, selected fruit juices did not show cytotoxic effects on HT-29 cells and NF-κB inhibitory activity (at the concentrations of 0.5 and 2%). Results of this study showed no correlation between the antioxidant activity of natural fruit juices from red grape, strawberry, cherry and sour cherry and their effect on HT-29 cell viability and NF-κB inhibitory activity.     

Optimised processing technique for colour- and cloud-stable plum juices and stability of bioactive substances

Plum (Prunus domestica) juices were produced from different cultivars with optimised processing technology. High results for dry mass (19–21 °Brix), sugar-free extract (75–105 g/L), total acidity (6–11 g/L), sorbitol (27–52 g/L) and minerals were found. Secondary plant metabolites were present in high amounts as well. By means of HPLC/PDA 1465–2590 mg/L of colourless polyphenols were found. Neochlorogenic acid, chlorogenic acid, (+)-catechin and (−)-epicatechin were the predominant polyphenols. Total anthocyanins were found in amounts of 43–168 mg/L in the fresh juices. They were identified as cyanidin-3-glucoside, cyanidin-3-rutinoside, peonidin-3-glucoside and peonidin-3-rutinoside. A fast decline of the anthocyanin concentrations could be observed during a 6 months storage at 20 °C, which changed the red colour of the juices drastically. Beside high polyphenol concentrations, high antioxidant capacities of the juices were determined as well. The applied processing technology allowed the production of cloud-stable plum nectars.     

Differentiation of raspberry varieties according to anthocyanin composition

 Four Spanish raspberry (Rubus idaeus L.) cultivars, Autumn Bliss, Heritage, Rubi, and Ceva, were studied in order to determine, qualitatively and quantitatively, both anthocyanins and vitamin C composition, owing to their significance as dietary compounds with antioxidant activity and also to the relation with color quality. Raspberry anthocyanin composition, determined by HPLC and GC-MS, was characteristic to each cultivar. The higher anthocyanin content expressed as cyanidin-3-glucoside was found in the late cultivars, Rubi (96.08 mg/100 g f.w.) and Ceva (122.88 mg/100 g f.w.). Three cultivars showed cyanidin-3-sophoroside (63.86–21.91 mg/100 g f.w.) and cyanidin-3-glucoside (25.12–14.00 mg/100 g f.w.) as the major pigments, while Autumn Bliss had a similar relative amount of cyanidin derivatives, cyanidin-3-rutinoside being the pigment in major concentration (10.53 mg/100 g f.w.). The vitamin C contents were determined by HPLC. The Rubi cultivar showed the highest amount of vitamin C (31.14 mg/100 g f.w.). The organic acids were determined by HPLC as fruit constituents related to color quality. Citric acid was the main non-volatile organic acid (90%) in all raspberry cultivars and the Rubi cultivar showed the highest total non-volatile organic acids content (2003 mg/100 g f.w.). Hunter color CIE values were also determined, showing that Rubi was the reddest raspberry cultivar. Received: 28 May 1998     

Blackberry Juice and Wine: Processing and Storage Effects on Anthocyanin Composition, Color and Appearance

Blackberry wine was made from thawed fruit (Evergreen variety) by fermentation of pulp, depectinized juice, and high-temperature short-time (HTST)-treated and depectinized juice. The effects of fining and storage on pigment composition, color and appearance were investigated. Seven anthocyanin pigments (cyanidin-3-glucoside, cyanidin-3-rutinoside, a xylose-cyanidin derivative, two acylated cyanidin derivatives, cyanidin and a polymeric derivative) were detected in the juices and wines by HPLC. Cyanidin-3-glucoside was highly unstable during fermentation. Haze development and sediment formation occurred, and 85 to 100% of total anthocyanins degraded. Blackberry juice that had been HTST-pasteurized, depectinized and fined produced wine with the most stable color and best appearance after storage.     

Impact of various factors on the composition and stability of black currant anthocyanins

Nine black currant varieties cultivated in Lithuania were studied. The highest amount of ascorbic acid was established in fresh berries from cv Minaj Smyriov and Kupoliniai: these varieties contained 220.5 and 186.7 mg 100 g⁻¹ of ascorbic acid in berries. The highest amount of anthocyanins was found in cake produced from berries cv Kupoliniai and Kriviai: 14.65 and 15.42 mg g⁻¹, respectively. The major pigment determined in Kupoliniai variety was delphinidin-3-rutinoside; in Ben Lomond, Minaj Smyriov, Kriviai and Gagatai cultivars, cyanidin-3-rutinoside. The composition of the identified pigments was the following: cyanidin-3-rutinoside (33–38%), delphinidin-3-rutinoside (27–34%), cyanidin-3-glucoside (8–10%) and delphinidin-3-glucoside (8–10%). Impact of storage, thermal treatment and addition of sweeteners were studied. Cyanidin-3-rutinoside was the most stable to the effect of thermal treatment at 95 °C, while cyanidin and delphinidin rutinosides were the most stable during storage for 12 months at 8 °C. Fructose has a greater effect on anthocyanin degradation compared with glucose and aspartame.     

Determination of anthocyanins in four Croatian cultivars of sour cherries (Prunus cerasus)

The anthocyanins were characterised and quantified in four cultivars of sour cherries by means of high-performance liquid chromatography and mass spectrometry. Column chromatography on XAD-2 Amberlite was the method used for isolation of anthocyanins. A diode-array detector was employed. For anthocyanins determination was chosen wavelength of 518 nm. Cyanidin-3-glucosylrutinoside and cyanidin-3-rutinoside were major anthocyanins. The total anthocyanin content in sour cherries, (expressed as cyanidin-3-glucosylrutinoside) varied from 2.7 to 28.0 mg/100 g of fresh weight, with the highest content being observed in Oblainska cultivar.     

Antioxidant capacity and anthocyanin profile of sour cherry (Prunus cerasus L.) juice

The antioxidant capacities, total polyphenolic content and monomeric anthocyanin content of eleven types of sour cherry juice obtained from different varieties of sour cherries were investigated. Antioxidant capacity, total polyphenolic content and monomeric anthocyanin contents of the juices were within the ranges 20.0–37.9 mmol/L, 1510–2550 and 350.0–633.5 mg/L, respectively. The main anthocyanin compound in sour cherry juice was cyanidin-3-glucosylrutinoside at concentrations between 140.3 and 320.9 mg/L. Cyanidin-3-glucosylrutinoside was followed by cyanidin-3-rutinoside within a concentration range of 25.5–85.5 mg/L. Cyanidin-3-sophoroside and cyanidin-3-glucoside contents were relatively low (2.6–21.5 and 2.0–9.9 mg/L). Anthocyanin capacity and total polyphenol content were fairly well correlated (r = 0.742, p < 0.01), whereas the correlation between antioxidant capacity and monomeric anthocyanin content was insignificant (r = 0.423, p > 0.05). The correlation between antioxidant capacity – cya-3-glucosylrutinoside (r = 0.606, p < 0.01) and antioxidant capacity – cya-3-rutinoside (r = 0.628, p < 0.01) was significant.     

In vitro absorption and antiproliferative activities of monomeric and polymeric anthocyanin fractions from açai fruit (Euterpe oleracea Mart.)

Anthocyanins are among the most important and widely consumed natural pigments in foods, and have attracted increased attention as natural food colourants and potent bioactive agents. However, anthocyanins are generally unstable and may undergo chemical changes that include oxidative and polymerisation reactions during processing and storage. The role of anthocyanin polymerisation reactions on in vitro intestinal absorption and anti-cancer properties has not been assessed. This study investigated the chemical composition, antioxidant properties, antiproliferative activity, and in vitro absorption of monomeric and polymeric anthocyanin fractions from açai fruit (Euterpe oleracea Mart.). Cyanidin-3-rutinoside (58.5 ± 4.6%) and cyanidin-3-glucoside (41.5 ± 1.1%) were the predominant compounds found in monomeric fractions, while a mixture of anthocyanin adducts were found in polymeric fractions and characterised using HPLC–ESI-MSⁿ analyses. Monomeric fractions (0.5–100 μg cyanidin-3-glucoside equivalents/ml) inhibited HT-29 colon cancer cell proliferation by up to 95.2% while polymeric anthocyanin fractions (0.5–100 μg cyanidin-3-glucoside equivalents/ml) induced up to 92.3% inhibition. In vitro absorption trials using Caco-2 intestinal cell monolayers demonstrated that cyanidin-3-glucoside and cyanidin-3-rutinoside were similarly transported from the apical to the basolateral side of the cell monolayers (0.5–4.9% efficiency), while no polymeric anthocyanins were transported following incubation for up to 2 h. The addition of polymeric anthocyanin fractions also decreased monomeric anthocyanin transport by up to 40.3 ± 2.8%. Results from this study provide novel information regarding the relative size, absorption, and bioactive properties of anthocyanin monomers and polymer adducts.     

Identification of anthocyanins and distribution of flavonoids in tamarillo fruit (Cyphomandra betaceae (Cav.) Sendt.)

The major tamarillo (Cyphomandra betaceae) anthocyanin pigments were isolated and identified as pelargonidin-3-rutinoside, pelargonidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3-glucoside, delphinidin-3-rutinoside and delphinidin-3-glucoside. The intense purple-coloured jelly surrounding the seeds contained the greatest concentration of anthocyanins, delphinidin-3-rutinoside being the major pigment. Flavones, flavonols and leucoanthocyanins were also present in this material. The yellow-coloured flesh contained flavones and low concentration of anthocyanins. The major anthocyanin of the skins is cyanidin-3-rutinoside; flavones and leucoanthocyanins are also present. It is suggested that the presence of leucoanthocyanins in pigment extracts induced degradation of anthocyanins during isolation and purification.     

Isolation and identification of 5-carboxy-pyranoanthocyanins in beverages from cherry (Prunus cerasus L.)

Novel pyranoanthocyanins were identified by HPLC–ESI-MSⁿ in fermented and unfermented fruit juices from cherry (Prunus cerasus L.). The two major compounds, namely 5-carboxy-pyranocyanidin 3-O-(2^G-glucosylrutinoside) and 5-carboxy-pyranocyanidin 3-O-rutinoside were isolated by a combination of high-speed countercurrent chromatography with semi-preparative HPLC. Their structures were fully elucidated by means of NMR spectroscopy and mass spectrometry. As minor compounds 5-carboxy-pyranocyanidin 3-glucoside, 5-carboxy-pyranopeonidin-3-glucoside, and 5-carboxy-pyranopeonidin 3-rutinoside could be identified.These compounds are formed during storage of the juice through the reaction of pyruvic acid with the respective genuine anthocyanins.Industrial relevanceFor the consumers the color of fruit juices is one of the most important quality markers. However due to a fast degradation of anthocyanins, changes in color from purple/red hues to orange/brown hues can be observed during storage. The main objective of this study was the isolation, structural characterization and evaluation of pigments that are formed during aging of fruit juices. Pyranoanthocyanins were reported to possess a color stabilizing effect. In the present study it could be demonstrated that the color contribution of these newly formed pigments to the overall color of fruit juice was overestimated. Instead, the formation of polymeric pigments yields the highest impact (> 80%) on the color of aged fruit juices.     

Anthocyanin and Polyphenolic Composition of Fresh and Processed Cherries

ABSTRACT: The distribution of anthocyanin pigments and polyphenolics in 1 sour cherry ( Prunus cerasus ) and 3 sweet cherry ( Prunus avium ) cultivars was determined by high-performance liquid chromatography with diode array detection. Changes during frozen storage, canning, and brining were also monitored. Sweet cherry cultivars differed qualitatively with respect to the minor anthocyanins. Hydroxycinnamates are the major class of polyphenolics in sweet cherries, whereas flavanols are in the majority in Montmorency cherries. Hydroxycinnamates were greatly affected by processing and storage, whereas flavonol glycosides were quite stable. Half of the anthocyanins and polyphenolics were transferred to the syrup with canning, and nearly all were transferred to brine during brining.     

Effects of pectolytic enzyme treatments on anthocyanins in raspberry juice

Raspberry juices treated with two commercial pectinase preparations lost almost 20% of their total anthocyanin pigments; losses were related to both concentration of enzyme and time of treatment. Analysis of individual anthocyanins showed differences between the enzymes. Ultrazyme reduced all components in similar proportions, whereas Pectinex apparently also converted cyanidin-3-sophoroside and cyanidin-3-glucosylrutinoside into cyanidin-3-glucoside and cyanidin-3-rutinoside respectively, presumably by hydrolysis of β1–2 glucosidic bonds by glucosidase present in the Pectinex.     

Effect of ripeness and postharvest storage on the evolution of colour and anthocyanins in cherries (Prunus avium L.)

The relationship between colour parameters and anthocyanins of four sweet cherry cultivars, Burlat, Saco, Summit and Van was studied. The colour (L^∗, a^∗, b^∗, chroma and hue angle parameters) and anthocyanins were analysed during two different years at two different ripening stages (partially ripe, and ripe, respectively). The cherries were analysed at harvest and after storage at 1.5 ± 0.5 °C and 15 ± 5 °C for 30 and 6 days, respectively. The colour was measured by tristimulus colourimetry (CIELAB system) directly on the fruits, while anthocyanins were quantified by HPLC-DAD analysis on methanolic extracts of freeze-dried samples of the fresh cherries and on the differently stored cherries. L^∗, chroma, and hue angle values were always lower for the ripe than for the partially ripe cherries. All of the cultivars were found to contain cyanidin-3-rutinoside and cyanidin-3-glucoside as the major anthocyanins. The total anthocyanin content in fruits of the different cultivars varied in the order Burlat > Saco > Van > Summit. The concentration of anthocyanins increased at both temperatures of storage in both ripe and partially ripe cherries, but the extent of increase varied among cultivars. Cherries stored at 15 ± 5 °C showed higher reduction of L^∗, chroma and hue angle than fruits stored at 1.5 ± 0.5 °C. L^∗, a^∗, b^∗, chroma and hue angle correlated negatively (P < 0.001) with the total anthocyanins levels, but not with the total phenols. These results show that chromatic functions of chroma and hue correlate closely with the evolution of colour and anthocyanins levels during storage of sweet cherries and indicate that colour measurements can be used to monitor pigment evolution and anthocyanin contents of cherries (and vice versa).     

Storage Changes in Anthocyanin Content of Red Raspberry Juice Concentrate

Anthocyanins from red raspberry juice concentrates were extracted with acidified ethanol and methanol and separated by high performance liquid chromatography. Six anthocyanin peaks were identified as cyanidin-3-sophoroside (cy-3-sop), cyanidin-3-glucorutinoside (cy-3-glru), cyanidin-3-glucoside (cy-3-gl), cyanidin-3-rutinoside (cy-3-ru), pelargonidin-3-sophoroside (pg-3-sop), and pelargonidin-3-glu-corutinoside (pg-3-glru). Relative proportions of individual anthocyanins were determined by comparing peak areas. The proportions of cy-3-sop, cy-3-glru and cy-3-gl in particular changed greatly on storage for 3 mo at + 20°C. Minor changes occurred when the raspberry juice concentrate was stored at ?20°C.     

Degradation of anthocyanins in sour cherry and pomegranate juices by hydrogen peroxide in the presence of added ascorbic acid

Effects of hydrogen peroxide in the presence of ascorbic acid on the degradation of sour cherry and pomegranate juice anthocyanins were studied at three H₂O₂ concentrations (4.65, 6.98 and 9.31 mmol l⁻¹) and two ascorbic acid concentrations (60 and 80 mg l⁻¹) at 20 °C. Degradation of anthocyanins by H₂O₂ was fitted to first-order reaction kinetics in sour cherry and pomegranate juices. A similar degradation pattern was found at the 60 and 80 mg ascorbic acid levels for pomegranate juice. Degradation of sour cherry anthocyanins at the 60 mg ascorbic acid level was fitted to a second-order reaction kinetic, whereas it was a first-order reaction kinetic after a lag period occurred at the 80 mg level. Ascorbic acid, at 80 mg l⁻¹, markedly accelerated the degradation of anthocyanins in sour cherry juice at all the H₂O₂ concentrations studied. In contrast, ascorbic acid, at both 60 and 80 mg l⁻¹, protected the anthocyanins from the degradation by H₂O₂ in pomegranate juice.     

Flavonoids in three olive (Olea europaea) fruit varieties during maturation

The objective of the present paper was the characterisation of olive fruit varieties through the formation and variation during maturation of their flavonols, flavones and anthocyanins. An olive variety with a constant cyanidin-3-rutinoside:cyanidin-3-glucoside ratio of 1 exhibited lower contents of luteolin-7-glucoside and quercetin-3-rutinoside than varieties in which the only anthocyanin detected was cyanidin-3-rutinoside.     

Quantitative changes in anthocyanin pigments of lychee fruit during refrigerated storage

Changes in cyanidin-3-glucoside, cyanidin-3-rutinoside, malvidin-3-acetylglucoside, total anthocyanins, percent polymeric color and browning indexes in stored lychee (Litchi chinensis Sonn.) fruits were determined. Total anthocyanin content declined from 1·77 to 0·73 mg/g fresh weight, and individual anthocyanins also decreased throughout the 48-day storage period. Decline in anthocyanins was accompanied by an increase in browning. Polymeric pigments also gradually increased from 20·9 to 53%.     

HPLC-MS/MS法测定甜樱桃花色苷与非花色苷酚的组成与含量

应用高效液相色谱-质谱联用技术测定甜樱桃‘雷尼’、‘红艳’、‘红灯’3个品种的花色苷与非花色苷酚的组成与含量。花色苷的检测条件为:色谱柱Kromasil 100-5C18柱(250 mm×4.6 mm,6.5μm),流动相为水-甲酸-乙腈溶液,梯度洗脱,进样量30μL,流速1.00 m L/min,柱温50℃,检测波长525 nm;非花色苷酚的检测条件为:色谱柱Zorbax SB-C18(50 mm×3.0 mm,1.8μm),流动相为1%乙酸-1%乙酸-乙腈溶液,梯度洗脱,进样量2μL,流速1.00 m L/min,柱温25℃,检测波长280 nm。结果表明,3个品种共检测到9种花色苷,主要为花青素-3-芸香糖苷和花青素-3-葡萄糖苷,其在‘红艳’果皮、‘雷尼’果皮、‘红灯’果皮、‘红灯’果肉中的含量分别为5.21、2.51、75.70、7.40 mg/g和0.09、0.07、3.57、0.34 mg/g。非花色苷酚类化合物检测出了芦丁与山柰酚-3-芸香糖苷这2种化合物,其在‘红艳’果皮、‘雷尼’果皮、‘红灯’果皮中的含量分别为0.30、0.63、0.74 mg/g和1.17、2.91、2.37 mg/g。     

The effects of six phenolic acids and tannic acid on colour stability and the anthocyanin content of mulberry juice during refrigerated storage

Six phenolic acids and tannic acid are added to fresh mulberry juice to enhance the colour. Effects of these copigments on colour stability and the anthocyanin content of mulberry juice are investigated while being stored at 4 °C for 30 days. Results suggest that the addition of the copigments markedly increases the maximum absorbance of mulberry juice. Cyanidin-3-glucoside is the major anthocyanin, followed by cyanidin-3-rutinoside. Furthermore, the retention rate of the total anthocyanin, cyanidin-3-rutinoside and cyanidin-3-rutinoside increases after the addition of all copigments. The effect of ferulic acid on the stability of total anthocyanin, cyanidin-3-glucoside and cyanidin-3-rutinoside in mulberry juice is the best, 89.52%, 86.90% and 94.46% respectively (66.56%, 62.58% and 73.60% in the control group). Researchers recommend the addition of ferulic acid, p-coumaric acid and caffeic acid – all of which belong to the hydroxycinnamic acid group, to the mulberry juice to enhance the colour stability and anthocyanin content.     

Chemical profile and antioxidant capacities of tart cherry products

The levels of anthocyanins and other flavonoids, as well as melatonin, in various tart cherry products (frozen and dried cherries, powders from individually quick frozen (IQF) cherry and juice concentrate) from two tart cherry cultivars, ‘Montmorency’ and ‘Balaton’ were analysed comparatively by HPLC and electrospray mass spectrometry (EMS). Our results show that the major anthocyanin compound in these two tart cherry cultivars is cyanidin 3-glucosylrutinoside, followed by cyanidin 3-rutinoside, cyanydin sophoroside, 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 after processing and storage. We have also compared the antioxidant activities of several single constituents that are present in tart cherry. When TEAC (trolox equivalent antioxidant capacity) values were evaluated conceptually against the cherry phytochemical profile, cyanidin and its derivatives were found 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.