Phenolic compounds in natural black Spanish olive varieties

There is increasing interest in olive phenolic compounds because of their biological properties as well as their contribution to the colour, taste and shelf life of olive products. Phenolic compounds in natural black Spanish olives are characterised by HPLC-UV and HPLC-MS. Hydroxytyrosol-4-#-D-glucoside has been identified as the major phenolic compound in natural black olives. A qualitative and quantitative study of phenolic substances such as hydroxytyrosol, salidroside, tyrosol, verbascoside, luteolin-7-glucoside, rutin, demethyloleuropein and oleuropein has been carried out. Traces of other phenolic compounds such as catechol, vanillic acid, apigenin-7-rutinoside and ligustroside have also been found by mass spectroscopy. Secoiridoid aglycons, the main phenolic compounds in olive oil, were not detected in olive flesh except the dialdehydic form of elenolic acid linked to hydroxytyrosol (HyEDA), particularly in the Arbequina olive variety and only traces were detected in other varieties. Among anthocyanins, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were the only anthocyanin compounds detected in all the varieties studied. The UV and MS spectra of several unknown phenolic compounds have also been described.     

ANTHOCYANIN PIGMENTS OF SOUR CHERRIES

Fresh fruits of tart cherries (Prunus cerasus L. var. Montmorency) were extracted with acidic methanol. The anthocyanin pigments were isolated and purified by conventional paper chromatography. They were identified by spectral and R_f data and by acid hydrolysis. The pigments were cy anidin-3-glucosylrutinoside, cyanidin-3-glucosylsambubioside, cyani-din-3-sophoroside, cyanidin-3-rutinoside, cyanidin-3-glucoside and peoni-din-3-rutinoside. No free cyanidin or peonidin was found. Cyanidin-3-glucosylsambubioside, reported in cherries for the first time, was also found in the varieties of English Morello, Early Richmond and Meteor     

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.     

Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins

Berberis boliviana Lechler is a member of the Berberidaceae family that has a small edible red-purple berry. The plant is native to the Peruvian Andes and contains high amounts of anthocyanin pigments. The monomeric anthocyanin content, determined by a pH-differential method, was 7/100 g of seedless berries. Pigments were characterised by HPLC coupled to a photodiode array (PDA) and mass spectrophotometer (MS) detectors. Five aglycones and ten anthocyanins were found and identified as petunidin-3-glucoside (24.4%), delphinidin-3-glucoside (24.1%), malvidin-3-glucoside (22.1%), cyanidin-3-glucoside (10.2%), petunidin-3-rutinoside (7.15%), malvidin-3-rutinoside (4.9%), cyanidin-3-rutinoside (3.8%), delphinidin-3-rutinoside (2.6%), peonidin-3-glucoside (1.1%), and peonidin-3-rutinoside (0.9%).     

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.     

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.     

Phenolic Analyses of Haskap Berries (Lonicera caerulea L.): Spectrophotometry Versus High Performance Liquid Chromatography

Haskap berries (Lonicera caerulea L.) are known for their high phenolics, anthocyanins, and antioxidant potential. The data on the phenolic profile of these fruits are lacking. In this study, the phenolic profiles of three haskap varieties; tundra, berry blue, and indigo gem grown in Nova Scotia, Canada were investigated for the first time using spectrophotometery and high-performance liquid chromatography. Berries were analyzed for total phenolic content/total reducing capacity, total anthocyanin content, and antioxidant potential (2,2-diphenyl-1-picrylhydrazyl radical scavenging activity). The total reducing capacity, total anthocyanin content, and 2,2-diphenyl-1-picrylhydrazyl values were 6.17–8.42 mg gallic acid equivalents/gram fresh weight, 4.49–6.97 mg cyanidin-3-glucoside equivalents/gram fresh weight, and 78.70–89.55%, respectively. The extracts were analyzed by reversed-phase diode array detector–high-performance liquid chromatography through a gradient elution using Synergi 4 µm Max-RP C12 column and the chromatograms were acquired at 520, 360, and 320 nm for athocyanins, flavonoids, and free phenolic acids, respectively. The identified anthocyanins were cyanidin-3-glucoside (82.81–91.99% of the total anthocyanins), cyanidin 3,5-di-glucoside (2.31–4.27%), cyanidin-3-rutinoside (1.54–9.20%), peonidin-3-O-glucoside (0.75–3.44%), and pelargonidin-3-glucoside (0.77–2.98%). Other flavonoids (quercetin-3-β-D-glucoside and quercetin-3-rutinoside) and free phenolic acids (chlorogenic and neochlorogenic) were also quantified.     

Products of Thermal Degradation of the Anthocyanins Cyanidin-3-glucoside,Cyanidin-3-rutinoside and Cyanidin-3-sophoroside

During thermal degradation of anthocyanins, cyanidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3-sophoroside, at 98 °C in model systems of pH = 1, 2.5 3.5 and 4.5, seven compounds were isolated by means of paper chromatography. Among them quercetin, phloroglucin-aldehyde and protocatechuic acid were identified.     

Anthocyanin Pigment Composition of Blackberries

ABSTRACT: The anthocyanin pigments in 51 blackberry samples were isolated and characterized by highperformance liquid chromatography (HPLC) with UV-visible detection, electrospray mass spectroscopy (ESMS), and hydrolysis and saponification reactions. Five pigments were detected: cyanidin-3-glucoside, cyanidin-3-rutinoside, cyanidin-3-xyloside, cyanidin-3-glucoside acylated with malonic acid, and an unidentified acylated derivative of cyanidin-3-glucoside. Four different quantitative patterns were evident among the cultivars and selections. Total anthocyanin content ranged from 70.3 to 201 mg/100 g with a mean of 137 mg/100 g. Ten commercial blackberry juice concentrate samples were analyzed. Total anthocyanin ranged from 12.3 to 107 mg/100 g on a single-strength juice basis, and 1 sample had an atypical profile.     

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.     

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%.     

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.     

芙蓉李果实成熟期间的综合品质评价指标筛选与表观预测模型构建

科学评价芙蓉李果实成熟期间的营养品质。方法 以福建省主栽品种芙蓉李为研究对象,对其成熟期间果糖、葡萄糖、蔗糖、苹果酸、奎尼酸、琥珀酸、柠檬酸、富马酸、矢车菊素-3-芸香糖苷、矢车菊素-3-葡萄糖苷、多酚、黄酮、类胡萝卜素等13个品质指标进行分析和综合评价。结果 芙蓉李成熟期间,各品质指标的含量变化存在显著差异（P＜0.05）,综合运用相关分析、因子分析、绝对因子分析-多元线性回归（Absolute Principal Component Scores-Multiple Linear Regression,APCS-MLR）分析筛选可反映芙蓉李综合品质的主要指标。因子分析提取出三个主因子,贡献率分别为52.68%、23.47%、11.65%,累计贡献率为87.79%。综合APCS-MLR等数理统计分析,主因子1主要对果糖、矢车菊素-3-芸香糖苷、矢车菊素-3-葡萄糖苷贡献较大,贡献率分别为53.00%、73.85%、55.54%;主因子2主要对蔗糖、富马酸、果糖、柠檬酸的贡献率较大,分别为28.26%、18.70%、16.14%、15.59%;主因子3主要对多酚（29.13%）和黄酮（28.28%）有较大贡献率;选取三个主因子总贡献率高于60%的果糖、葡萄糖、矢车菊素-3-芸香糖苷、矢车菊素-3-葡萄糖苷作为综合品质评价的主要指标。分别对已筛选出的4个主要评价指标与色度值L*、a*、b*、c*、h°进行多元线性逐步回归分析,建立4个主要指标与色度值的表观预测模型,各模型均具有较好的拟合度,预测值与实测值的均方根误差较小;进一步验证结果表明,通过色度值对4个指标的预测具有较高的可靠性和准确性。结论 本研究筛选出的主要指标及预测模型可更加简单、便捷地评价芙蓉李期间的综合品质。     

Analytical characterization and the impact of ageing on anthocyanin composition and degradation in juices from five sour cherry cultivars

Five different sour cherry cultivars were processed to sour cherry juices in order to analyze their composition and the impact of storage on anthocyanin composition. Regarding primary juice parameters all cultivars showed high dry masses (13.8–17.2° Brix) and sugar free extracts (59.4–74.3 g/L). Anthocyanins were identified as cyanidin-3-(2^G-glucosylrutinoside), cyanidin-3-(2^G-xylosylrutinoside), cyanidin-3-sophoroside, cyanidin-3-glucoside, cyanidin-3-rutinoside, and peonidin-3-rutinoside. Besides the original anthocyanins, 5-carboxypyrano-anthocyanins occurred as new reaction products during storage. HPLC-MSⁿ experiments revealed, that a further ageing pigment was probably resulting from the reaction of an original anthocyanin with acetaldehyde. A significant decline of the original anthocyanin concentrations could be observed (70–75%) during 6 months of storage at 20 °C. Degradation kinetics of anthocyanins were calculated taking the reaction rate as first order. Colourless polyphenol concentrations and antioxidant capacities (TEAC) of the juices were not affected during storage.     

Anthocyanin fingerprinting of true bokbunja (Rubus coreanus Miq.) fruit

The interest in black raspberry products has been increasing due to its flavor and potential health benefits. While black raspberries grown in North America are Rubus occidentalis, there has been some confusion regarding the identity of black raspberry grown in Korea (known as bokbunja; Rubus coreanus). As such, there is a need to define the anthocyanin profile of R. coreanus fruit collected from a verified source. We analyzed three genotypes of bokbunja fruit for anthocyanin profiles. While each varied in its anthocyanin proportions and total concentration, bokbunja fruit contained three anthocyanins: cyanidin-3-glucoside, cyanidin-3-rutinoside, and pelargonidin-3-glucoside, and lacked the xylose containing glycosides characteristic of R. occidentalis: cyanidin-3-sambubioside, and cyanidin-3-xylosylrutinoside. Due to mix-ups of bokbunja identity, research claiming to be conducted on bokbunja fruit requires confirmation that the fruit was sourced from a correctly identified plant. The distinct anthocyanin profiles between the two species can be used to confirm plant identity.     

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 and characterisation of anthocyanins in the antioxidant activity-containing fraction of Liriope platyphylla fruits

The objective of this study was to investigate antioxidant activities and anthocyanin profiles in the fruits of Liriope platyphylla, where these are considered functional substances in Korea. The acidic methanol extract of this species exhibited potent antioxidant activities, showing 83.9% DPPH scavenging activity and 92.5% ABTS scavenging activity at a concentration of 0.5 mg/ml. Moreover, anthocyanins were identified by reversed-phase C₁₈ column chromatography, NMR spectroscopy, and HPLC-DAD-ESI/MS analysis. Seven anthocyanins were characterised, including delphinidin-3-O-glucoside (1), delphinidin-3-O-rutinoside (2), cyanidin-3-O-glucoside (3), petunidin-3-O-glucoside (4), petunidin-3-O-rutinoside (5), malvidin-3-O-glucoside (6), and malvidin-3-O-rutinoside (7). Among these, petunidin-3-O-rutinoside (5) (7302.2 μg/g) and malvidin-3-O-rutinoside (7) (5776.1 μg/g) were the predominant anthocyanins, whereas the least prevalent anthocyanin was found to be cyanidin-3-O-glucoside (3) (64.9 μg/g). Therefore, our results suggest that strong antioxidant activities of the acidic methanol extract of L. platyphylla fruits are correlated with high anthocyanin contents, particularly the petunidin-3-O-rutinoside (5) and malvidin-3-O-rutinoside (7).     

Selection of elderberry (<Emphasis Type="Italic">Sambucus nigra</Emphasis> L.) genotypes best suited for the preparation of juice

Experiments with elderberry genotypes, ripening stage and pectinolysis were carried out in order to investigate the possibility to improve different quality characteristics of elderberry juice. Raw juice was processed using either an optimised method with respect to enzyme concentration and treatment time or produced directly without any enzymatic treatment. Neochlorogenic acid, chlorogenic acid, cyanidin-3-sambubioside-5-glucoside, cyanidin-3,5-diglucoside, cyanidin-3-sambubioside, cyanidin-3-glucoside, quercetin-3-rutinoside (rutin) and quercetin-3-glucoside (isoquercitrin) were identified in the raw juice by liquid chromatography-mass spectrometry (LC-MS) and quantified by high-performance liquid chromatography-diode array detection (HPLC-DAD). The content of phenolic acids and flavonoids in elderberries were shown to be affected by berry development stage at harvest (ripening stage). Furthermore, a considerable variation in juice yield and physicochemical properties such as turbidity, soluble solids, titratable acidity, and content of phenolic acids and flavonoids was found between juices processed from elderberries by pectinolysis of different elderberry genotypes. Pectinolysis appeared not to have any major effect on juice yield and the content of phenolic acids and flavonoids in the juice compared to non-enzymatic processed juice. Factor analysis revealed correlations among quality characteristics such as soluble solids, titratable acidity, turbidity, and content of phenolic acids and flavonoids and it is shown that these correlations may be useful for the selection of elderberry genotypes best suited for the preparation of juice.     

Dietary supplementation with purified mulberry (Morus australis Poir) anthocyanins suppresses body weight gain in high-fat diet fed C57BL/6 mice

We present our experiment about adding anthocyanins to the daily food of mice. Three kinds of anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutinoside and pelargonidin-3-glucoside) purified from Chinese mulberry (Morus australis Poir) were evaluated for suppressing body weight gain of the male C57BL/6 mice fed with high-fat diet (HFD). The results from a 12-week experiment show that consumption of purified mulberry anthocyanins (MACN) of 40 or 200 mg/kg can significantly inhibit body weight gain, reduce the resistance to insulin, lower the size of adipocytes, attenuate lipid accumulation and decrease the leptin secretion. Thus, dietary supplementation with MACN can protect against body weight gain of the diet-induced obese mice.     

Discolouration of raw and cooked coloured fleshed potatoes differing in anthocyanins and polyphenols content

Despite variations in the content of polyphenols, the tested potato varieties with red and purple flesh contained similar amounts of anthocyanins. Potatoes of the red-fleshed HBr variety were distinguished by a significant content of pelargonidin-3-feruloylrutinoside-5-glucoside, and those of the purple-fleshed Vitelotte variety were characterised by a significant cyanidin-3-rutinoside content. Immediately after cutting, raw potatoes with red flesh showed a small share of yellow (b* parameter) and double the share of red (a*) as compared to purple-fleshed tubers. A reduction in the share of red dye was observed in purple- and red-fleshed potatoes except Vitelotte and Rosalinde tubers, at both 1 and 4 h after being cut. The flesh colour of cooked potatoes was characterised by low susceptibility to darkening, and purple-fleshed tubers were more saturated by chroma than tubers of red-fleshed varieties.