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.     

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%.     

Antioxidant assessment of an anthocyanin-enriched blackberry extract

Gel filtration of black berry (Rubus fruticosus sp) ethanolic extracts was employed to obtain an anthocyanin-enriched extract. The anthocyanin profile identified cyanidin-3-glucoside as the primary (e.g., 90% of total) anthocyanin present in blackberry. Gel filtration of crude extracts resulted in a 20-fold increase in total anthocyanin content, with no change in the proportion of cyanidin-3-glucoside. Antioxidant activities of both the crude and anthocyanin-enriched blackberry extracts were determined using cell-free (ORAC) and cell-based (INT-407 intracellular) antioxidant assays. Antioxidant activity, assessed by the ORAC assay, indicated a 7-fold increase in activity for the anthocyanin-enriched fraction. Similar results were obtained for the anthocyanin-enriched extract using the intracellular antioxidant assay with INT-407 cells. Our results indicate that the anthocyanin content, and more specifically the presence of cyanidin-3-glucoside, in blackberry, contributes a major part of the antioxidant ability to suppress both peroxyl radical-induced chemical and intracellular oxidation.     

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     

Direct Acylation of Cyanidin-3-Glucoside with Lauric Acid in Blueberry and Its Stability Analysis

Cyanidin-3-glucoside is an anthocyanin that is abundant in blueberry. Lauric acid was used as the acyl donor in the acylation of cyanidin-3-glucoside. Preparative high performance liquid chromatography was used to separate and purify the acylated cyanidin-3-glucoside, the acylated rate was 30.78%. Fourier transform infrared spectroscopy and liquid chromatography mass spectrometry were used to confirm the basic structure of cyanidin-3-glucoside. Lauric acid was combined with cyanidin-3-glucoside. Lauric acid reacted with the glucoside’s primary hydroxyl group and removed a molecule of water, thereby resulting in the obtained structure. The compositions of the unacylated cyanidin-3-glucoside and acylated cyanidin-3-glucoside were compared under different temperatures and under illumination. The effects of different concentrations of additive compounds on the stability of acylated cyanidin-3-glucoside were compared. Stability of acylated cyanidin-3-glucoside was obviously higher than that of the unacylated cyanidin-3-glucoside because of the higher stability of the ester group than the hydroxyl group. The primary hydroxyl esterification of glucoside improved cyanidin-3-glucoside.     

Anti-oxidative analysis,and identification and quantification of anthocyanin pigments in different coloured rice

Anthocyanin pigments in coloured rice cultivars were isolated and identified using high-performance liquid chromatography techniques. Two black rice cultivars (Asamurasaki, Okunomurasaki) contained three major anthocyanins: cyanidin-3-glucoside, peonidin-3-glucoside and malvidin. Chinakuromai (black) rice additionally contained a fourth anthocyanin, petunidin-3-glucoside. Four red rice cultivars contained only malvidin. The total anthocyanin content varied greatly among black rice cultivars (79.5–473.7 mg/100 g), but was lower in red rice (7.9–34.4 mg/100 g). Total phenolic content was similar between red (460.32–725.69 mg/100 g) and black (417.11–687.24 mg/100 g) rice. The oxygen radical absorbing capacity was ranked as follows: red (69.91–130.32 μmol Trolox/g) > black (55.49–64.85 μmol Trolox/g) > green (35.32 μmol Trolox/g) > white (21.81 μmol Trolox/g) rice. The antioxidant capacity resulted mainly from the seed capsule, not the endosperm. The anthocyanin pigments contributed little to the total antioxidant capacity of red (0.03–0.1%) and black (0.5–2.5%) rice cultivars. Hence, the antioxidant capacity is derived mainly from other phenolic compounds.     

Red Raspberry Juice and Wine: Effect of Processing and Storage on Anthocyanin Pigment Composition, Color and Appearance

Red raspberry wine was made from thawed fruit by fermentation of pulp, depectínized juice, and pasteurized depectinized juice. The influences of fining and storage were also investigated. The anthocyanin pigment profiles of the samples were determined by high performance liquid chromatography (HPLC), and additional color indices by spectrophotometry and Hunter colorimetry. Anthocyanin pigments degraded mainly during fermentation, with total losses after storage of at least 50%. Cyanidin-3-glucoside was the most unstable anthocyanin, disappearing completely during fermentation; cyanidin-3-sopho-roside (the major anthocyanin) was the most stable pigment. Pasteurized, depectinized wine that had undergone fining, had the most stable color and best appearance after storage.     

HPLC法测定桃不同品种果实中花色苷组成和含量

目的： 用高效液相色谱法测定桃不同品种果实中花色苷组成和含量。方法： 色谱柱为C1 8柱(150mm×4.6mm,5μm),流动相为乙腈：4%磷酸溶液(V/V=12:88,pH2),检测波长520nm,流速0.8mL/min,进样量20μL,柱温30℃。结果：桃3个品种果实中主要含有1种花色苷：花青素-3-葡萄糖苷,花青素-3-葡萄糖苷在0.4～100μg/mL内线性关系良好(R=0.9992),低、中、高质量浓度的平均回收率为85.7%、89.4%、91.2%。红、黄、白肉桃果肉中的花青素-3-葡萄糖含量分别为103.7、30.6、21.5mg/kg。结论：本方法操作简单,结果准确可靠,重复性好,可作为桃果实中花青素-3-葡萄糖苷的定量分析方法。     

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%).     

桑椹汁乙醇发酵过程中主要成分和功能成分的动态变化

以桑椹原果汁为主要原料,对其乙醇发酵过程中的糖度、酸度、酒精度、花青素和白藜芦醇等主要参数和功能成分的动态变化进行了观察。结果表明,在桑椹果汁的发酵过程中,糖度不断下降,乙醇含量不断上升;发酵醪中的可滴定酸含量呈现出上升趋势,后期挥发酸含量上升,而pH则先降后升;花青素含量不断下降,其中以矢车菊-3-葡萄糖苷下降最为显著。而白藜芦醇则随着发酵的进行逐渐上升,在乙醇发酵后期下降至发酵前水平。说明在发酵过程中,除了糖类转化为乙醇外,发酵醪中的有机酸种类和组成比例发生了变化,花青素不断发生聚集沉淀和/或降解,而白藜芦醇含量也受到多种因素的影响而发生变化。     

Characterization of Red Radish Anthocyanins

Red radish (Raphanus sativus L.) anthocyanins were extracted from liquid nitrogen powdered epidermal tissue using acetone, partitioned with chloroform and isolated using C-18 resin. The monomeric anthocyanin content, determined by pH-differential, was 154 ± 13 mg/100g epidermal tissue (pelargonidin-glucoside basis). Thermal processing of radishes showed that the pigments were stable to heat. Four major pigments were identified by Mass Spectroscopy, HPLC, and spectral analyses as pelargonidin-3-sophoroside-5-glucoside derivatives. The two major pigments were acylated with malonic acid and either ferulic or p-coumaric acid. The two other pigments were acylated with only ferulic or p-coumaric acid. Acylation increased pigment resistance to acid hydrolysis.     

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.     

Production of Anthocyanin from Strawberry Cell Suspension Cultures; Effects of Sugar and Nitrogen

Production of anthocyanins was investigated, controlling sugar concentration and ratio of ammonium: nitrate in culture medium of strawberry, Fragaria ananassa cv Shikinari. Anthocyanins were produced under 8000 lux for 2 wk using calli derived from suspension cultures of leaf tissues. Yield was greatest in modified LS medium containing 5% sucrose (W/V), a ratio of NH⁺₃ (2 mM):NO^?₃ (28mM), 2,4-dichlorophenoxyacetic acid and benzyladenine. Total anthocyanin was about 15 mg/100 mL of culture medium, almost six times greater than that in MS medium. Effects of sugars were also studied using eight sugars. Cell growth and anthocyanin accumulation were enhanced by glucose, sucrose, and fructose, but anthocyanin compositions were not affected. Major anthocyanins were peonindin-3-glucoside and cyanidin-3-glucoside. Peonidin-3-glucoside increased with an increase in the NH⁺₄ NO^?₃ ratio at nitrogen concentration 30 mM, while that of cyanidin-3-glucoside changed vice versa.     

Anthocyanin Pigment Composition of Red-fleshed Potatoes

Red potatoes ( Solanum tuberosum and S. stenotomum ) were evaluated as potential sources for natural red colorants. Qualitative anthocyanin composition, pigment content and phenolic composition were screened on 33 cultivars. Monomeric anthocyanin content, determined by pH differential, ranged from 2 to 40 mg/100g tuber fresh weight. Two breeding clones, NDOP5847–1 and NDC4069–4, showed anthocyanin content >35 mg/100g. Anthocyanin composition was characterized by HPLC, spectral analyses and mass spectroscopy (MS). All red potato samples showed similar pigment profiles, with pelargonidin-3-rutinoside-5-glucoside acylated with p -coumaric acid being the major anthocyanin (ca 70%). Anthocyanin content and profiles of epidermal tissue and flesh were compared for NDC4069–4. The presence of glycoalkaloids in color extracts was detected by MS. Some red-fleshed potatoes may be good potential sources of food colorants.     

蔓越莓花色苷的组成鉴定及抗氧化能力

对蔓越莓花色苷的组成进行鉴定,并对其抗氧化能力进行测定。采用pH示差法测定花色苷提取量,超高压辅助提取蔓越莓花色苷含量为（75.49±0.43）mg/100?g,常规溶剂提取蔓越莓花色苷含量为（67.31±1.08）mg/100?g,蔓越莓中总花色苷含量为（79.52±0.50）mg/100?g;选择AB-8大孔树脂对蔓越莓花色苷粗提物进行纯化,冻干粉中花色苷含量从（46.10±0.92）mg/g提高到（309.26±2.37）mg/g。通过测定1,1-二苯基-2-三硝基苯肼自由基清除率、2,2’-联氮基-双-（3-乙基苯并噻唑啉-6-磺酸）二铵盐自由基清除能力和总抗氧化能力,比较蔓越莓花色苷与VC的抗氧化能力。结果表明：同质量浓度条件下,蔓越莓花色苷的抗氧化能力强于VC。通过高效液相色谱-质谱联用技术在蔓越莓中鉴定出7?种花色苷：芍药素-3,5-二己糖苷、矢车菊素-3-半乳糖苷、矢车菊素-3-葡萄糖苷、矢车菊素-3-阿拉伯糖苷、芍药素-3-半乳糖苷、芍药素-3-葡萄糖苷、芍药素-3-阿拉伯糖苷,其中芍药素-3,5-二己糖苷首次在蔓越莓中被鉴定出。     

ANTHOCYANINS OF BEAUTY SEEDLESS GRAPES

Beauty Seedless grape pigments were isolated and identified by chromatographic, spectral and chemical properties. The pigments were identified as delphinidin-3-glucoside, petunidin-3-glucoside, malvidin-3-glucoside, peonidin-3-glucoside, malvidin-3-glucoside acylated with caffeic acid and malvidin-3-glucoside acylated with p-coumaric acid. Beauty Seedless grapes contained 62 mg anthocyanins per 100g fresh grapes and malvidin derivatives accounted for 73% of the total anthocyanins.     

Lingonberry (Vaccinium vitis-idaea L.) grown in the Pacific Northwest of North America: Anthocyanin and free amino acid composition

Lingonberries and their products are popular and generally accessible in Europe, though in the US they are uncommon and considered a minor berry/fruit crop. The on-going interest in potential health benefits from berry consumption has heightened interest in broadening the selection of berry/fruit crops in the US. This study measured total phenolics, total tannins, complete anthocyanin content, and total (and individual) free amino acid composition for each of five lingonberry cultivars. Cultivars Ida, Koralle, Linnea, Sanna, and Sussi were grown in Oregon, USA, and had only been evaluated previously for their horticultural traits. All five cultivars contained the three anticipated anthocyanins (by HPLC): cyanidin-3-galactoside (main anthocyanin found in these berries), cyanidin-3-glucoside, and cyanidin-3-arabinoside. These lingonberries’ total anthocyanin content ranged from 27.4 (‘Linnea’) to 52.6 (‘Ida’) mg/100 g fw. They contained 22 free amino acids (FFAs) and total FAAs ranged from 28.92 (‘Sanna’) to 70.38 (‘Koralle’) mg/100 g fw. Asparagine (ASN) was the leading FAA (22–34% of the total FAAs) for all five cultivars. This is the first report on lingonberry FAA content.     

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.     

Dosage response of atherosclerotic lesions to dietary cholesterol in rabbits

Litsea garciae, known locally in Sabah, Malaysia as Pengolaban, is an underutilized edible fruit endemic to Borneo. This study was conducted to determine the antioxidant activity and total phenolic, total flavonoid, and total anthocyanin contents of different parts (i.e., flesh, stem cap, and seed) of the fruits. All samples were freezedried and extracted using 80% methanol and distilled water. For 80% methanol extract, stem cap of pengolaban displayed the highest free radical scavenging activity and ferric reducing activities as compared to other parts of the fruit. Total phenolic and total flavonoid content were highest in stem cap with the values of 8.29±0.70 mg gallic acid equivalents/g and 6.90±0.61 mg rutin equivalents/g, respectively. Total anthocyanin content was highest in flesh of the fruit with the value of 4.12±0.10 mg cyanidin-3-glucoside equivalents/100 g. The same trend of antioxidant and phytochemical content were also observed in the distilled water extract. These findings suggested that pengolaban has an acceptable high amount of phytochemicals which has a potential as natural antioxidant that can contribute to human health.     

Anthocyanin Composition of Red Raspberry Juice: Influences of Cultivar, Processing, and Environmental Factors

The anthocyanin and anthocyanidin pigment profiles of 46 authentic red raspberry juice samples were determined by HPLC. Total anthocyanin pigment content and percent polymeric color were also determined. This generated a database incorporating influences of cultivar, geographic origin, maturity, processing, and mold contamination. Cultivars exhibited characteristic patterns distinguished by quantitative rather than qualitative differences. Total pigment ranged from 4 to 1,102 mg/L. Commercial red raspberry juice concentrates (14) were also analyzed. Two were shown to be adulterated because of the presence of delphinidin glycosides. Three samples contained high amounts of polymerized pigments, indicating a history of processing or storage abuse.