Article

Phenolic composition of fruits from different cultivars of red and black raspberries grown in Poland

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Abstract

Fruits of 11 varieties of Rubus idaeus and 1 variety of Rubus occidentalis cultivated in Poland, were analyzed in terms of phenolic composition. The qualitative and quantitative determination of phenolics was performed by means of HPLC-DAD coupled with ESI–MS detector. Quantitative determination of anthocyanins, revealed significant differences in the levels of major anthocyanins in most red raspberry varieties, of which cyanidin 3-O-sophoroside was the most prevalent one. Black raspberries displayed 4–11 times more anthocyanin content compared to red raspberries, with the dominating anthocyanins being cyanidin 3-O-rutinoside and cyanidin 3-O-xylosyl-rutinoside. Sanguiin H-6 was the main ellagitannin identified in all varieties, with ‘Beskid’, ‘Laszka’, ‘Polana’ and ‘Litacz’ standing out as the richest sources of sanguiin H-6. Ellagic acid was at similar, low concentrations, with the highest levels observed in ‘Willamette’. A number of other compounds belonging to flavonols, flavan-3-ols and phenolic acids, were found at much lower levels than anthocyanins and ellagitannins, with the presence of procyanidins B1 and B2 being reported for the first time in the fruits of black raspberries. Data obtained on the variation in content of major and minor phenolic compounds between raspberry varieties highlights the most valuable cultivars to be used as a dietary source of phenolic compounds.

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... Wild berries are well-known sources of bioactive compounds, mainly phenolics, synthesized by the plant secondary metabolism [1][2][3]. Such native chemicals play a crucial role in the prevention of a wide range of chronic and degenerative diseases [4,5]. ...
... More in detail, the phenolic composition of R. occidentalis berries has been poorly described in the literature, since, to our knowledge, only three studies have been published thus far [2,15,16], while a few more studies have been performed on R. idaeus fruits [2,[17][18][19][20][21][22][23]. Some of these studies have been performed using liquid chromatography (LC) coupled with diode array detection and single quadrupole mass spectrometry through a selected ion monitoring approach, highlighting the occurrence of anthocyanins (i.e., cyanidin and pelargonidin derivatives) [2,19] and 32 compounds belonging to phenolic acids, flavanols, flavonols, ellagic acid and its derivatives and ellagitannins [2]. ...
... More in detail, the phenolic composition of R. occidentalis berries has been poorly described in the literature, since, to our knowledge, only three studies have been published thus far [2,15,16], while a few more studies have been performed on R. idaeus fruits [2,[17][18][19][20][21][22][23]. Some of these studies have been performed using liquid chromatography (LC) coupled with diode array detection and single quadrupole mass spectrometry through a selected ion monitoring approach, highlighting the occurrence of anthocyanins (i.e., cyanidin and pelargonidin derivatives) [2,19] and 32 compounds belonging to phenolic acids, flavanols, flavonols, ellagic acid and its derivatives and ellagitannins [2]. ...
Article
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This study provided a detailed profiling of the antioxidant and bioactive compounds occurring in three varieties of Rubus idaeus L. fruits (“Fall Gold”, “Glen Ample” and “Tulameen”) compared to Rubus occidentalis L. black raspberry (“Jewel” cultivar), adopting a comprehensive untargeted metabolomics approach developed with UHPLC analysis coupled with quadrupole/time-of-flight high resolution mass spectrometry, using the SWATH® acquisition protocol. The feature selection and annotation workflow, applied to the analysis of raspberry extracts in both polarities, allowed identifying 68 bioactive compounds mainly belonging to the classes of (poly)phenolic compounds. Interestingly, some of these identifications (e.g., ferulic acid glycosides and the ellagitannin-like nobotanin/malabathrin) represent the first report in raspberry fruits. Principal component analysis made possible highlighting the features more related to the expression of a genotype effect within the R. idaeus species or between the two raspberry species herein investigated. Overall, flavanols were the most discriminating features for the Fall Gold variety, whereas ellagitannins and flavonol glycosides represent more distinctive metabolic traits in Glen Ample and Tulameen fruits. Moreover, R. occidentalis Jewel variety was strongly characterized by the occurrence of anthocyanins, such as cyanidin, pelargonidin and delphinidin glycosides.
... Raspberry (Rubus idaeus L.) is an important berry crop for both the fresh and the processing market. In addition to vitamins and minerals, a diverse range of polyphenols are present in the berries, including flavonoids such as anthocyanins, flavonols and flavanols, ellagitannins and ellagic acid derivatives (Wang et al., 2009;Veberic et al., 2015;Kula et al., 2016;Sójka et al., 2016). ...
... Although genetic predisposition is the major factors influencing fruit quality (Milivojevic et al., 2011;Kula et al., 2016), different agricultural practices (Qiu et al., 2016;Palonen et al., 2017), fruit maturity (Stavang et al., 2015) and environmental conditions can also affect berry metabolite amounts and composition (Anttonen and Karjalainen, 2005;Remberg et al., 2010;Mazur et al., 2014a,b). Raspberries, like some other berries, ripen successively and are harvested over a period of a few weeks. ...
... content in various investigated red fruited cultivars ranged around 30 mg 100 g -1 FW (Remberg et al., 2010;Mazur et al., 2014a,b), although higher contents have also been reported (Bobinaitė et al., 2012). As noted previously, anthocyanins mainly consisted of cyanidin, followed by pelargonidin-based pigments (Veberic et al., 2015;Kula et al., 2016), while peonidin glycosides (detected only in the minor contents) have not previously been identified in raspberries. Interaction between sampling date and treatment in total anthocyanins was shown only for cv. ...
Article
High temperature stress, which has been occurring more often in recent years, usually coincides with the flowering of primocane raspberries and causes a negative effect on fruit quality parameters. One of the methods of delaying raspberry flowering and fruit development to avoid high summer temperatures is tipping the young primocanes. The aim of the study was to investigate how this practice affects the fruit characteristics and primary and secondary metabolites of two primocane raspberry cultivars (‘Amira’ and ‘Polka’). For this purpose, we performed primocane tipping on two different dates in late spring and analyzed the berries from three subsequent sampling dates. High performance liquid chromatography-mass spectrometry (HPLC-MS) analyses were used for the identification and quantification of individual phenolic compounds and HPLC analyses for individual sugars and organic acids. Primocane tipping had great influence on the beginning of the harvest season of both cultivars. The impact on fruit yield was insignificant. Sampling date had a greater influence on fruit metabolite contents than did different treatments, with cultivar ‘Polka’ showing a greater response to primocane tipping than cultivar 'Amira'. Based on primary and secondary metabolites, it is difficult to say which treatment provided the best results, since dissimilar patterns were shown at different sampling dates and between cultivars. With negligible differences in fruit quality, primocane tipping was shown to be a good cultivation practice for delaying the production season of raspberries.
... 28 Table 3 displays features that were identified using these methods, all of which have been previously reported in BRBs. 29 Catechin and epicatechin are isomeric flavan-3-ols, and their levels have been shown to decline over storage in other products such as apple juice, 30 and a variety of blueberry products. 31 B-type procyanidins are oligomers of catechin and/ or epicatechin linked by C-C bonds, and have also been reported to be unstable over storage. ...
... 32 PA is a B-ring cleavage product of cyanidin-based anthocyanins that can form as a result of heating or storage, but is also present in fresh BRBs. 29,33 ...
Article
Pre-clinical and clinical studies suggest black raspberries (BRBs) may inhibit the development of oral cancer. Lyophilized BRB powder is commonly used in these studies, but processed BRB products are more often consumed. The objective of this work was to understand how storage conditions influence the phytochemical profile and anti-proliferative activity of a BRB nectar beverage. Untargeted UHPLC-Q-TOF-MS based metabolomics analyses demonstrated that large chemical variation was introduced by storage above -20 C over 60 days. However, minimal change in anti-proliferative activity was observed when stored nectar extracts were applied to SCC-83-01-82 premalignant oral epithelial cells. As proof of concept, cyanidin-3-O¬-rutinoside and its degradation product, protocatechuic acid, were administered in different ratios maintaining an equimolar dose, and anti-proliferative activity was maintained. This study shows the utility of metabolomics to profile global chemical changes in foods, while demonstrating that isolated phytochemicals do not explain the complete bioactivity of a complex food product.
... Gallic acid and salicylic acid (and its glucoside) are hydroxybenzoic acids, which have been previously reported in BRBs (Kula, Majdan, Głód, & Krauze-Baranowska, 2016;Paudel et al., 2013). Coumaric acid, caffeic acid, and their glycosides are hydroxycinnamic acids that have also been previously reported in BRBs (Paudel et al., 2013). ...
... B-type procyanidins are oligomers of catechin and/or epicatechin, and have been previously documented in BRBs (Kula et al., 2016). The potential bioactive properties of these compounds are thought to be primarily mediated through products of microbial catabolism (Monagas et al., 2010). ...
Article
Clinical and laboratory studies have implicated black raspberries (BRBs) and their associated phytochemicals in the modulation of several chronic diseases. Most research on the health benefits of BRBs is conducted using freeze-dried or otherwise minimally processed products, yet BRBs are typically consumed as thermally processed goods like jams and syrups. The objective of this work was to profile the chemical changes that result from thermal processing of BRB powder into a nectar beverage. Using an untargeted UHPLC-QTOF-MS metabolomics approach, key degradation products of anthocyanins were identified along with several other proposed phenolic degradants. The effects of processing on other key BRB compound groups, including ellagitannins, are also discussed. This work demonstrates the utility of an untargeted metabolomics approach in describing the chemistry of complex food systems and provides a foundation for future research on the impact of processing on BRB product bioactivity.
... Raspberries (Rubus idaeus L.) (Fig. 1) and red currant (Ribes rubrum L.) (Fig. 2) are berries widely spread all over Europe [1] and they are known for their food and flavoring qualities alongside with their involvement in preserving human health [2,3], due to their important content of phenolic compounds [4]. ...
... It has been shown that the most health benefits of these berries are related to the content in phenolic compounds [4]. ...
Article
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The extracts obtained from two types of berries: red currant and raspberries, were evaluated for their phenolic content. They were identified and quantified by using an optimized HPLC method. During the analyze several phenolic compounds were found, like: gallic acid, (+)- catechin, syringic acid, cinnamic acid, chlorogenic acid, ferulic acid, rutin and quercetin. The total amount of phenolic compounds analyzed found in red currant was greater than the one found in raspberries, due to the low variety of phenolic compounds extracted. The greatest amount of gallic acid, (+)- catechin, syringic acid, cinnamic acid, chlorogenic acid, ferulic acid and rutin was determined from the extraction of red currant berries and the raspberries extract contained the greatest source of quercetin. This study shows that red currant can provide the highest and most varied content of phenolic compounds from the analyzed berries.
... Red and black raspberry share the same profile of anthocyanins. Their anthocyanins are predominantly cyanidin glycosides (e.g., glucosides, sophorosides, rutinosides, sambubioside, and glucosyl-rutinosides), but they only contain low to trace levels of pelargonidin glycosides (Mazur et al., 2014;Ludwig et al., 2015;Kula et al., 2016). Flavonols in red and black raspberry, as well as in Chinese raspberry, are mainly kaempferol/quercetin glycosides with the glucosides rutinoside and coumaroylglucoside (Kula et al., 2016;Yu et al., 2019). ...
... Their anthocyanins are predominantly cyanidin glycosides (e.g., glucosides, sophorosides, rutinosides, sambubioside, and glucosyl-rutinosides), but they only contain low to trace levels of pelargonidin glycosides (Mazur et al., 2014;Ludwig et al., 2015;Kula et al., 2016). Flavonols in red and black raspberry, as well as in Chinese raspberry, are mainly kaempferol/quercetin glycosides with the glucosides rutinoside and coumaroylglucoside (Kula et al., 2016;Yu et al., 2019). During the process of fruit ripening, the flavonoids dramatically change in composition and content, which is associated with the transformation of fruit pigmentation and flavor. ...
Article
Full-text available
Rubus chingii HU, is a medicinal and nutritious fruit, which is very rich in flavonoids. However, the biosynthesis of its flavonoids is poorly understood. This study examined flavonoids and the genes/proteins at four fruit ripening phases using LC-MS/MS and qPCR. Six major kinds of anthocyanins, primarily consisted of flavanol-anthocyanins, which differed in form or concentration from other Rubus species. In contrast to other known raspberries species, R. chingii had a decline in flavonoids during fruit ripening, which was due to down-regulation of genes and proteins involved in phenylpropanoid and flavonoid biosynthesis. Unexpectedly, anthocyanin also continuously decreased during fruit maturation. This suggests that anthocyanins are not responsible for the fruit’s reddish coloration. Flavanol-anthocyanins were derived from the proanthocyanidin pathway, which consumed two flavonoid units both produced through the same upstream pathway. Their presence indicates a reduction in the potential biosynthesis of anthocyanin production. Also, the constantly low expression of RchANS gene resulted in low levels of anthocyanin biosynthesis. The lack of RchF3′5′H gene/protein hindered the production of delphinidin glycosides. Flavonoids primarily comprising of quercetin/kaempferol-glycosides were predominately located at fruit epidermal-hair and placentae. The proportion of receptacle/drupelets changes with the maturity of the fruit and may be related to a decrease in the content of flavonoids per unit mass as the fruit matures. The profile and biosynthesis of R. chingii flavonoids are unique to Rubus. The unique flavonol pathways of R. chingii could be used to broaden the genetic diversity of raspberry cultivars and to improve their fruit quality.
... The phenolic compound contents of the raspberries growing in different regions were significantly different [24,25]. The content of ferulic acid in raspberry cultivars grown in Turkey was 6.39 mg/g, which was higher than that of raspberry cultivars grown in the Qinghai-Tibetan Plateau region [24]. ...
... The content of quercetin in raspberry cultivars grown in Turkey was 0.35mg/g, and it was found that only Boyne contained quercetin among raspberry cultivars grown in the Qinghai-Tibetan Plateau region. The phenolic compositions of raspberries were quite different between those grown in Poland and the Qinghai-Tibetan Plateau region [25]. In addition, the amount of total phenolic compound in extracts was determined according to the Folin-Ciocalteu's procedure in order to prepare with other studies concerning rasberries from other geographic places. ...
Article
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In this work, an efficient method for the rapid extraction and separation of antioxidant phenols was developed and optimized. The method was then applied to extract and separate nine phenols from 37 varieties of raspberry, in which their antioxidant activities were further investigated. First, the extraction was conducted using ultra-sonication, which was then further separated using reversed-phase high-performance liquid chromatography/ultraviolet (RP-HPLC/UV) analysis. In this step, several key parameters (volume of the extraction reagent, time of extraction, and the temperature of extraction) affecting its efficiency were investigated and optimized using the response surface methodology (RSM) combined with the Box–Behnken design (BBD) so that the optimal conditions were obtained. According to the overall results of the optimization study, the optimal conditions were chosen as follows: volume of extraction reagent = 2.0 mL, time of extraction = 50.0 min, and temperature of extraction = 50 °C. The optimal conditions were then applied to extract nine phenols, including gallic acid, catechin, chlorogenic acid, vanillic acid, syringic acid, cumaric acid, ferulic acid, rosemary acid, and quercetin from 37 raspberry varieties. The extracted phenols were characterized and their antioxidant activities, including DPPH− and ABTS− free radical scavenging and intracellular reactive oxygen species (ROS) activity, using HepG2 cells as the model, were subsequently studied. The findings suggested that although their contents varied among most raspberry varieties, these phenols significantly contributed toward their antioxidant capacity and scavenging intracellular ROS activities. This study provides a scientific and theoretical basis for the selection of raspberry varieties and product development in Qinghai province.
... Spectrofluorimetry is less time-consuming. During HPLC analysis the run time can be from 35 min (Da Silva Pinto et al., 2007;Huerga-González et al., 2015), to 37 (Jimenéz et al., 2017), 40 (Amakura et al., 2000), 45 (Klimczak and Król, 2010) and even to 55 (Kula et al., 2016) or 65 min (Tumbas et al., 2012). In contrast, spectrofluorimetric measurements last a couple of seconds. ...
... The main disadvantage of the herein proposed spectrofluorimetric methodology is quite large consumption of methanol (about 25 mL per -González et al., 2015) or acidified water/acetonitrile (Amakura et al., 2000;Jimenéz et al., 2017;Kula et al., 2016;Tumbas et al., 2012)) could be even higher. As HPLC is a more popular technique than spectrofluorimetry, access to the scientific equipment (spectrofluorimeter) in smaller laboratories may be limited. ...
Article
Ellagic acid is a naturally occurring polyphenol with many verified and alleged bioactivities. This study presents a validated, sensitive and fast spectrofluorimetric method to determine ellagic acid in rose matrix, based on the fluorescence properties of ellagic acid–borax complex in methanolic extract. In the presence of rose matrix, a calibration curve was linear in a wide concentration range from 0.5 nmol/L to 1.0 µmol/L of EA, and the detection and quantification limits of ellagic acid were 34.7 nmol/L and 0.11 µmol/L, respectively. We used the validated method to determine the content of ellagic acid in lyophilized and dried rosehip products available in Poland. The rosehip contains a significant content of ellagic acid (from 32 to 44 μg/g of dried/freeze-dried material). All spectrofluorimetric results were in good agreement with those obtained by liquid chromatography–mass spectrometry with a single quadrupole analyzer used as a reference method.
... Literature data shows the presence of glycoside derivatives of quercetin and kaempferol and a small amount of rutin and myricetin in raspberry fruit. From the group of flavan-3-ols, the presence of catechin, epicatechin, epigallocatechin, and procyanidin B1-B8 and C has been confirmed [22,23]. Among phenolic acids, ellagic acid and gallic acid, as well as smaller amounts of hydroxybenzoic, ferulic, protocatechuic, p-hydroxybenzoic acid, p-coumaric, salicylic, or caffeic acids have been mentioned as components of raspberry fruit [22][23][24]. ...
... From the group of flavan-3-ols, the presence of catechin, epicatechin, epigallocatechin, and procyanidin B1-B8 and C has been confirmed [22,23]. Among phenolic acids, ellagic acid and gallic acid, as well as smaller amounts of hydroxybenzoic, ferulic, protocatechuic, p-hydroxybenzoic acid, p-coumaric, salicylic, or caffeic acids have been mentioned as components of raspberry fruit [22][23][24]. From 27.5 mg/100 g DW of phenolic acids present in red raspberry, about 78% are derivatives of hydroxybenzoic acid-gallic acid and its dimer-ellagic acid [25]. Jakobek et al. identified ellagic acid in concentration 32 µg/g [20]. ...
Article
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In this study, the antioxidative and anti-inflammatory potential of crude extracts (CE), anthocyanin-rich fractions (ARF), and phenolic fractions (PF) from raspberry (R) and raspberry juice (J) were evaluated. The antioxidant properties were evaluated with three complementary assays: DPPH radical scavenging activity, chelating Fe(II) power, and ferric reducing power. The highest antioxidant activity was determined for the crude extract from raspberry pulp (RCE) in the case of all methods used. The anti-inflammatory activity was demonstrated by inhibitory effect on lipoxygenase (LOX) and cyclooxygenase-2 (COX-2) activity in vitro. The highest efficiency in inhibiting the activity of both enzymes was exhibited by RCE, 0.79 and 0.59 mg FW/mL, respectively. In turn, JARF had the lowest ability to inhibit LOX (EC50 = 4.5 mg FW/mL) and JPF caused the lowest COX-2 inhibition (1.75 mg FW/mL). Additionally, we have performed a pilot study of in vitro cytotoxic activity using two human leukemia cell lines: J45 and HL60. All examined extracts inhibited the viability of J45 cells more effectively than HL60. The highest cytotoxic effect was observed in the J45.01 cell line after exposure to RCE (EC50 = 0.0375 mg FW/mL).
... Their anthocyanins are predominantly cyanidin glycosides (e.g. glucosides, sophorosides, rutinosides, sambubioside and glucosyl-rutinosides), but they only contain low to trace levels of pelargonidin glycosides (Kula et al. 2016;Ludwig et al. 2015;Mazur et al. 2014). Black raspberry has up to ve-fold greater anthocyanin content than red raspberry (Krauze- Baranowska et al. 2014). ...
... Black raspberry has up to ve-fold greater anthocyanin content than red raspberry (Krauze- Baranowska et al. 2014). Flavonols in red and black raspberry are mainly kaempferol/quercetin glycosides with glucosides, rutinoside and coumaroylglucoside (Kula et al. 2016). Moreover, agricultural technologies, elicitors, stimulating agents and plant activators, have been applied to increase Rubus avonoid content (Jin et al. 2012). ...
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Rubus chingii , is a red-fruited species of Rubus native to China, which is a popular and nutritious fruit in China. However, change in flavonoid composition and content during fruit maturation is poorly understood. This study examined flavonoids and the genes/proteins during four fruit ripening phases using LC-MS/MS. As a result, six major kinds of anthocyanins were first identified in R. chingii , which primarily consisted of flavanol-anthocyanins, are new to Rubus . Apart from anthocyanins, concentrations of fruit flavonoids were much higher than most berries including raspberries, and it is this that contributes to their high phenolic concentrations and antioxidant capabilities. In contrast to other known raspberries, R. chingii had a decline in flavonoids during fruit maturation, which was due to down-regulation of genes/proteins involved in phenylpropanoid and flavonoid biosynthesis. Surprisingly, anthocyanin continuously decreased during fruit coloration. This suggests that anthocyanins are not responsible for the fruit’s reddish coloration. The biosynthesis of these flavanol-anthocyanins consumed two flavonoid units both produced through the same upstream pathway. Their presence indicates a reduction in the potential biosynthesis of anthocyanin production. Also, the constantly low expression of RcANS gene down-regulated overall anthocyanin biosynthesis. The lack of RcF3’5’H gene/protein hindered the production of delphinidin glycosides. Flavonoids primarily comprising of quercetin/kaempferol-glycosides were predominately located at fruit epidermal-hair and placentae. The profile and biosynthesis of R. chingii flavonoids are unique to Rubus . It could be used to broaden the genetic base of raspberry cultivars and to improve their fruit quality.
... In raspberries, the major anthocyanins were different according to the species, for example, cyanidin-3-sophoroside (41.2-62 mg/100 g fw) and cyanidin-3-glucoside (10.1-15.2 mg/100 g fw) for red raspberry (R. idaeus) (Krauze- Baranowska et al., 2014;Mazur et al., 2014;Stavang et al., 2015) and cyanidin-3-rutinoside (30.9-250 mg/100 g fw) for black raspberry (R. occidentalis) (Kim et al., 2011;Krauze-Baranowska et al., 2014;Kula, Majdan, Głod, & Krauze-Baranowska, 2016;Tulio et al., 2008). Cyanidin-3-O-sambubioside, cyanidin-3-xyloside, cyanidin-3-dioxaloyl-glucoside, cyanidin-3-O-(2G-xylosyl-rutinoside), cyanidin-3-xylrutinoside, cyanidin-3-glucosyl-rutinoside, cyanidin-3-sophoroside, cyanidin-3-malonyl-glucoside, and pelargonidin-3-rutinoside occurred in different proportions (Jakobek et al., 2009; The fruits can be divided into three groups based on the types of aglycones of their anthocyanins: the cyanidin/peonidin group, the pelargonidin group, and the multiple anthocyanins group. ...
Article
Rubus L. (Rosaceae) berries have received worldwide attention, mainly for their nutritional and bioactive value. The raspberries and blackberries of this genus contain nutrients and bioactive compounds such as vitamins, minerals, proteins, sugars, and polyphenols. This review summarizes available data on the physical-chemical characteristics, nutritional composition, biologically active compounds, and biological activities of Rubus raspberries (Rubus idaeus L., R. ellipticus Smith, R. niveus Thunb., R. coreanus Miquel and R. occidentalis L.) and blackberries (R. ulmifolius Schott, R. fruticosus L., R. adenotrichus Schltdl., R. glaucus Benth). The composition and the antioxidant, anti-inflammatory, chemopreventive, and antimicrobial activities, as well as the positive effects on blood lipids and atherosclerosis of the Rubus berries showed that these fruits are important sources of biologically active compounds, and their biological effects suggest potential uses for human health.
... Polymeric forms of ellagic acid with low molecular weight ( < 950 g/ mol) as pedunculagin (compound 3) and casuarictin/potentillin (compound 4), are often in Rubus fruits and have been shown as potential secondary metabolites with free-radical scavenging, lipoperoxidative, and anti-inflammatory activities [7,28]. Other macromolecular ETs, as sanguiin H-2, H-10 and H-6/lambertianin A (compounds 6, 9 and 11, respectively), were reported previously in other Rubus species, but this is the first report of sanguiin H-10 in Rubus fruits, since only has been recorded in other aerial parts of these plants [15,28,29]. Lambertianin B (compound 7), was detected easily in both Rubus species, but lambertianin C is a molecule relatively heavy, and its presence was inferred thought its molecular moiety. ...
Article
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Tannins are phenolics found in fruits such as wild Rubus berries. The aim of this study was to determine the profile by LC–ESI–MS/MS and NMR, antioxidant capacity (AOX) of the tannins in two Mexican wild blackberries. Fractions rich in tannins (FRT) were isolated using different solvents and chromatographic resins. The LC–ESI–MS/MS and NMR results showed that catechin and epicatechin (m/z 289⁻¹), which are precursors of proanthocyanidins, as well as other six oligomeric forms of ellagitannins (m/z 301⁻¹) were found in R. liebmannii, whereas in R. palmeri, only ellagitannins were found, highlighting oligomeric forms of lambertianins and sanguiins (m/z 783⁻¹ to 1869⁻¹). The purification pathway made it possible to increase the AOX 19.7 times from fruits to FRT showing strong positive correlations (R² > 0.9) with total phenolic content. This study provided a good assessment of the tannin composition of wild blackberries from the Northwest of Mexico and their bioactivity as a potential edible source.
... The quantitative and qualitative compositions of raspberry metabolites depend on genotype, fruit maturity, natural and climatic conditions, and growing technology (Kula et al., 2016;Palonen et al., 2017;Akimov et al., 2020;. In 2018, global raspberry production reached 870 209 tons in an area of 124 971 ha; Russia was the leading raspberry producer, supplying 19% of the global total (FAOSTAT, 2020). ...
Article
The biochemical compounds of red raspberry (Rubus idaeus L.) fruits cultivated with conventional growing technology and on a nutrient substrate were studied during 2019–2020 at the Federal Horticultural Research Center for Breeding, Agrotechnology and Nursery, Moscow, Russia. The antioxidant activity, phenolic compounds, and ash constituents of the fruits and the metabolites of the alcoholic extract of the raspberries were determined. The effect of growing technologies, i.e., conventional vs. nutrient substrate, on the accumulation of macro- and microelements in raspberry fruits was established. In red raspberries grown on nutrient substrate, the antioxidant activity decreased by 25 times (aqueous extract) and 1.5 times (alcoholic extract). The K and Na contents and Se contents of red raspberries grown on nutrient substrate were 1.5 and 3 times higher than those of raspberries of grown with conventional technology. Raspberries grown with conventional technology contained 2 times more Ca, Ni, and Mn and 7.4 times more Fe than raspberries grown on nutrient substrate. The total amount of elements in raspberries grown through soilless cultivation was 5.5% higher than that in berries grown conventionally. A total of 48 compounds were identified in the alcoholic extracts, and only 29 substances were found in berries grown on a nutrient substrate. Sugar and citric acid constituted the largest share of red raspberry components. Fructose and turanose disaccharide synthesis in raspberries grown on nutrient substrate was 20% higher than that in conventionally grown raspberries. A total of 48 organic compounds with different biological activities were identified. They included five substances with antimicrobial activity, three phenolic substances, eight organic acids, four sugar acids, nine amino acids, and 19 sugars and their derivatives. At the same time, 42 compounds were found in raspberries grown with traditional technology, and 21 compounds were identified in raspberry fruits grown on nutrient substrate. Three fatty acids, namely, ɑ-linoleic acid (polyunsaturated omega-6 fatty acid), palmitic acid, and stearic acid (saturated fatty acid), along with cinnamic acid, shikimic acid, and chrysin were found in berries grown conventionally.
... HHDP-glucose, besides some ellagic acid conjugates in the form of pentosides, methyl pentosides and acetyl pentosides (Gülçin et al., 2011;Krauze-Baranowska et al., 2014;Kula et al., 2016). ...
Article
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This work aimed to evaluate the colour and sensory properties of jelly gums made with fruits and herbs. The colour was measured by a colorimeter in the Hunter lab coordinates (L*, a* and b*). Sensory evaluation comprised preference tests and profile analysis. The results showed that the colour of gums with blueberry was considerably different than other fruits (strawberry and raspberry).
... Lyophilized red raspberry pomace powdered (50 g) was extracted three times using 300 mL of acidic methanol by 0.1% formic acid in a sonication bath 70% power, 25°C, 10 min (Kq-600DE, Kunshan Ultrasonic Instruments Co., Ltd, China). The combined extracts were followed by centrifugation (20 min, 5000 rpm, Allergra X-30R Centrifuge, Beckman Coulter, U.S.A) (Kula, Majdan, Głód, & Krauze-Baranowska, 2016). The combined extracts were evaporated and subjected into AB-8 macroporous resin column followed by ethyl acetate separation to purify anthocyanins extract from sugar, protein, and lipophilic fraction, and then the extracts were lyophilized to get a fine powder (Gras, Bogner, Carle, & Schweiggert, 2016). ...
Article
This work aims to investigate the effect of desolvation on the stability and bioavailability of nanoparticles of β-lactoglobulin (β-Lg) and anthocyanins (AC) extracted from red raspberry pomace. Interactions between the substrates were also studied using multispectral approaches. β-Lg-nanoparticles were fabricated via heat treatment at 85 °C for 30 min before initiating the desolvation method at pH 7. This method generated monodisperse particles, nano-scale size of β-Lg, and AC-β-Lg ranged from 129.13 to 351.85 nm with square morphology obtained by SEM. The AC extract was encapsulated successfully during desolvation process into β-Lg-nanoparticles with encapsulation efficiency (EE %) of ∼77%. Results also showed that AC (from 1 to 13 × 10⁻⁴ M) quenched the fluorescence intensity of de-solvated β-Lg estimated to be 98%, and a binding among them occurred with a Ka-value of 7.59 × 10⁸ M⁻¹ at 25 oC. Addition of AC also gradually increased the antioxidant activity of β-Lg-nanoparticles with values of 82.51% at the highest AC-concentration (13 × 10⁻⁴ M) loaded on β-Lg-nanoparticles. AC-loaded β-Lg nanoparticles was more stable in mouth (pH 6.8), simulated gastric (SG, pH 2), and simulated intestinal (SI, pH 6.9) by showing high retention rate (%) than that of AC unencapsulated. Overall, de-solvated-β-Lg increased the heat-stability and bioavailability of AC, which could be further utilized in various food and pharmaceutical matrices. These findings recommend that β-Lg nanoparticles could be appropriated as delivery systems for anthocyanins.
... Fleshy fruits, a rich source of bioactive components, such as ascorbate (vitamin C), terpenoids and polyphenols, are considered to have one the highest antioxidant capacity of commonly eaten foods (Halvorsen et al. 2006). Polyphenol content and composition can vary substantially between fleshyfruit varieties Miladinović et al. 2014;Kula et al. 2016), different cultivation conditions (Josuttis et al. 2013;Vagiri et al. 2013;Mazur et al. 2014), harvest times and as a result of different post-harvest factors (Kårlund et al. 2014;Stavang et al. 2015), but particularly between species (Moyer et al. 2001;McDougall et al. 2008;Ruiz et al. 2010;Marhuenda et al. 2016). Furthermore, plant polyphenols are increasingly being associated with putative bioactivities offering protection against several cardiovascular (Goszcz et al. 2015) and neurological diseases (Figueira et al. 2017). ...
Article
BACterial Hosts for production of Bioactive phenolics from bERRY fruits (BacHBerry) was a three-year project funded by the Seventh Framework Programme (FP7) of the European Union that ran between November 2013 and October 2016. The overall aim of the project was to establish a sustainable and economically-feasible strategy for the production of novel high-value phenolic compounds isolated from berry fruits using bacterial platforms. The project aimed at covering all stages of the discovery and pre-commercialization process, including berry collection, screening and characterization of their bioactive components, identification and functional characterization of the corresponding biosynthetic pathways, and construction of Gram-positive bacterial cell factories producing phenolic compounds. Further activities included optimization of polyphenol extraction methods from bacterial cultures, scale-up of production by fermentation up to pilot scale, as well as societal and economic analyses of the processes. This review article summarizes some of the key findings obtained throughout the duration of the project.
... Fleshy fruits, a rich source of bioactive components, such as ascorbate (vitamin C), terpenoids and polyphenols, are considered to have one the highest antioxidant capacity of commonly eaten foods (Halvorsen et al. 2006). Polyphenol content and composition can vary substantially between fleshyfruit varieties Miladinović et al. 2014;Kula et al. 2016), different cultivation conditions (Josuttis et al. 2013;Vagiri et al. 2013;Mazur et al. 2014), harvest times and as a result of different post-harvest factors (Kårlund et al. 2014;Stavang et al. 2015), but particularly between species (Moyer et al. 2001;McDougall et al. 2008;Ruiz et al. 2010;Marhuenda et al. 2016). Furthermore, plant polyphenols are increasingly being associated with putative bioactivities offering protection against several cardiovascular (Goszcz et al. 2015) and neurological diseases (Figueira et al. 2017). ...
Article
Full-text available
BACterial Hosts for production of Bioactive phenolics from bERRY fruits (BacHBerry) was a 3-year project funded by the Seventh Framework Programme (FP7) of the European Union that ran between November 2013 and October 2016. The overall aim of the project was to establish a sustainable and economically-feasible strategy for the production of novel high-value phenolic compounds isolated from berry fruits using bacterial platforms. The project aimed at covering all stages of the discovery and pre-commercialization process, including berry collection, screening and characterization of their bioactive components, identification and functional characterization of the corresponding biosynthetic pathways, and construction of Gram-positive bacterial cell factories producing phenolic compounds. Further activities included optimization of polyphenol extraction methods from bacterial cultures, scale-up of production by fermentation up to pilot scale, as well as societal and economic analyses of the processes. This review article summarizes some of the key findings obtained throughout the duration of the project.
... Raspberry is extremely rich in nutrients and contains all the essential vitamins and minerals (C, E, K, B3, folic acid, pantothenic acid, Fe, Mg, P, K, Zn, Cu, Mn). Kula et al., (2016) indicate an increase in demand for products rich in polyphenols. In this respect, it is necessary to investigate the differences in the chemical structure of different varieties of raspberries to identify those with the highest levels of beneficial compounds. ...
... These fruits are known for their antitumoral, antibacterial, anti-inflammatory and antioxidant activities (Bowen-Forbes et al., 2010;de Souza et al., 2014;Sariburun et al., 2010) due to their content in phenolic compounds such as anthocyanins, ellagitannins, a wide variety of quercetin and kaempferol-based flavonol conjugates, phenolic acids and vitamin C (Bobinait et al., 2012;Bowen-Forbes et al., 2010;Diaconeasa et al., 2014;Kula et al., 2016;Mullen et al., 2002;Sariburun et al., 2010), among other beneficial nutrients including essential minerals, dietary fibre, potassium and fatty acids. ...
Article
E-beam irradiation was studied as a post-harvest treatment for red raspberries (Rubus idaeus L.). Microbial inactivation (natural microbiota and potential pathogenic bacteria) and bioactive properties (phenolic content, vitamin C content and antioxidant activity and cytotoxicity) of these fruits were evaluated before and after irradiation and during storage of 14 days at 4°C. A reduction of 2 log CFU/g of mesophilic bacteria and 3 log CFU/g on filamentous fungi, and no detection of foodborne inoculated pathogens (3 log CFU/g) was achieved with an e-beam treatment at 3 kGy and during 7 days of refrigerated storage. Regarding bioactive properties, the results suggested that irradiation could preserve the phenolic content and antioxidant activity of raspberries through 7 days of cold storage, even though a decrease of 80% on ascorbic acid concentration was observed. Furthermore, no in vitro inhibitory effect on human cells lines was observed for the extracts from e-beam-treated raspberries. The overall results suggested that use of e-beam irradiation as post-harvest treatment of raspberries as an emergent, clean and environmental friendly process to extend the shelf-life of this fruit with safety and preservation of bioactivity. Industrial Relevance Red raspberries are known to demonstrate high bioactivity that could be beneficial to human health, but are highly perishable and often associated with foodborne outbreaks, which makes its safety and commercialization a challenge. The use of a terminal control such as irradiation might reduce the burden of disease transmission and extend the quality of fresh red raspberries. The present research indicated that e-beam irradiation can be used as post-harvest treatment of raspberries, guarantying its safety and quality with the add-value of shelf-life extension.
... Fleshy fruits, a rich source of bioactive components, such as ascorbate (vitamin C), terpenoids and polyphenols, are considered to have one the highest antioxidant capacity of commonly eaten foods (Halvorsen et al. 2006). Polyphenol content and composition can vary substantially between fleshyfruit varieties Miladinović et al. 2014;Kula et al. 2016), different cultivation conditions (Josuttis et al. 2013;Vagiri et al. 2013;Mazur et al. 2014), harvest times and as a result of different post-harvest factors (Kårlund et al. 2014;Stavang et al. 2015), but particularly between species (Moyer et al. 2001;McDougall et al. 2008;Ruiz et al. 2010;Marhuenda et al. 2016). Furthermore, plant polyphenols are increasingly being associated with putative bioactivities offering protection against several cardiovascular (Goszcz et al. 2015) and neurological diseases (Figueira et al. 2017). ...
Chapter
Berries are rich resources of secondary metabolites, particularly known for diverse phenolic compounds. These highly bioactive compounds can be developed into novel nutraceutical and pharmaceutical products, as well as high-added-value natural food additives. Compounds extracted from berries have, e.g., been used as colorants (e.g., anthocyanins) [1]. Meanwhile, some phenolics present in berries are of high added value due to their potential to develop into anticancer drugs (e.g., phenolic acids, flavonols, and flavanols) [2]. The antioxidation properties from berries also make them attractive research subject to develop more efficient nutraceutical products than the current crude extraction formulas (e.g., NutriPhy® Bilberry 100 from Chr. Hansen) [3, 4]. To exploit the full potential of the phenolic molecules from berries, a number of research projects have been conducted ranging from identification of bioactive compounds and elucidation of metabolic pathways (metabolic engineering them into suitable industrial production host cells) to eventually commercial production [3, 5–12].
... Moreover, the main anthocyanins in raspberries may differ according to the species. Stavang et al. [47] described cyanidin-3-sophoroside and cyanidin-3-glucoside in red raspberry, and Kula et al. [48] identified cyanidin-3-rutinoside in black raspberry (Rubus occidentalis). ...
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Red raspberries (Rubus idaeus L.) are increasingly popular foods in contemporary diets due to their freshness, nutritional value and health claims. Among the existing cultivars, “Kweli” is one of the most productive and widely cultivated. In this study, the nutritional value and chemical composition of “Kweli” red raspberry were characterized by the official method of food analysis and chromatographic techniques, and its antioxidant and antimicrobial activities were tested against biological/biochemical oxidizable substrates and foodborne bacteria and fungi strains, respectively. Carbohydrates (including fructose and glucose, 14.3 and 12.6 g/100 g dw, respectively), proteins (6.8 g/100 g dw), and ashes (3.90 g/100 g dw) were major constituents. The fat content was quite low and constituted mainly by unsaturated fatty acids (58.3%), with a predominance of oleic acid. Fresh red raspberry also contained high levels of citric (2.7 g/100 g) and ascorbic (17 mg/100 g) acids. The anthocyanins (4.51 mg/g extract) cyanidin-O-hexoside and mostly cyanidin-O-sophoroside were identified in the red raspberry hydroethanolic extract, which was able to inhibit thiobarbituric acid reactive substances (TBARS) formation (EC50 of 122 µg/mL), oxidative hemolysis (IC50 of 298 µg/mL), and β-carotene bleaching (EC50 of 18.7 µg/mL). In turn, the extract was more effective than the food additive E224 against Bacillus cereus. All these results highlighted the nutritional quality of “Kweli” red raspberry and showed some compositional differences in relation to other cultivars. Therefore, its inclusion in a daily diet can be helpful to obtain nutrients and antioxidants and bring health benefits.
... In addition, a total of three proanthocyanidins were detected here, namely, procyanidin A3, procyanidin B2, and procyanidin B3. Unlike the red raspberry cultivar "Heritage" harvested in Northern China and Poland (Kula, Majdan, Głód, & Krauze-Baranowska, 2016), procyanidin B1 was not detected here, whereas procyanidin B2 and procyanidin B3 were abundant in this study. The proanthocyanidin profile can presumably be influenced by the production area and planting patterns. ...
Article
Most studies on health-promoting attributes of red raspberries have been conducted using extracts or freeze-dried powders instead of commercially processed products. This work aimed to trace the alterations of phenolic compounds in HHP-and HTST-treated juices. In total, 151 phenolic compounds were identified: 13 and 26 differential phenolics were discriminated in HHP-and HTST-treated juices, respectively. The alterations of phenolic compounds could be related to the increased oxidative stress derived from the indirect oxidation and thermal degradation. HTST processing promoted the release of free phenolic acids from their conjugated forms, while HHP processing could maximize the flavonol glycosides. Furthermore, morin was observed with a 7400-fold increase in HTST-treated juice, indicating the potential use for juice authenticity. Generally, HHP processing showed less impact on phenolic profiles in comparison with HTST processing. These findings provide novel insights into the impacts of sterilization processes on phenolic compounds in red raspberries.
... Pomace was lyophilized and powder (50g) was extracted three times using 300 mL of methanol acidified by 0.1 % formic acid in a sonication bath (25 °C, 10 min). The combined extracts were then centrifuged (20 min, 50 0 0 rpm, Allergra X-30R Centrifuge) [40] . The supernatant was evaporated and purified through AB-8 macroporous resin column followed by ethyl acetate separation to purify the AC from sugar, protein, and lipophilic fraction, and then the extracts were lyophilized to get a fine powder [41] . ...
Article
This study aims to investigate the preparation, characterization, interaction binding, and application of β-Lactoglobulin (β-Lg) based nanoparticles for encapsulation of anthocyanins (AC) extracted from red raspberry pomace, systematically. We used anti-solvent method that is common for nano particle preparation of water-soluble proteins. Nanoparticles were fabricated by dissolving β-Lg in an alkaline base at pH 7 and heat treatment 85 °C with the aid of anti-solvent process using N-(3 dimethylaminopropyl)-N-ethyl carbodiimide hydrochloride (EDC) as a cross-linking, then AC was loaded on β-Lg nanoparticles using citrate buffer pH 3. The results showed that the mean particle size of β-Lg and AC-β-Lg ranged from 199 to 172 nm with a semi-spherical morphology revealed by scanning electron microscopy (SEM). Interaction results showed that AC (1, 2, 4, 6 and 8 × 10⁻⁴ M) quenched the fluorescence intensity of β-Lg by 97%, and binding occurred with a Ka value of 9.39 × 10² M⁻¹ at 298 K via electrostatic forces. The β-Lg nanoparticles enhanced the bioavailability of AC was 22 %, which is higher than unencapsulated AC. Furthermore, the AC-loaded β-Lg nanoparticles were more stable in mouth (pH 6.8), simulated gastric (SG, pH 2), and simulated intestinal (SI, pH 6.9) by showing high retention rate (%) than free AC extract. These results may contribute to a better understanding of the improvement of AC bioavailability using β-Lg-nanoparticles.
... It was found that raspberry fruit are characterized by a high-level accumulation of polyphenolic compounds from 142 to 758 mg/100g in terms of gallic acid. The main representatives of phenolic compounds in raspberry fruit are ellagic acid, gallic acid, caffeic acid, epicatechin, quercetin, lambertianin, kempferol [11,12]. In addition, raspberries tend to accumulate such important polyphenolic compounds as anthocyanins due to their presence the fruit have P-vitaminous and antioxidant properties and they are suitable for freezing and technological processing. ...
Article
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Raspberry is a crop, characterized by a valuable chemical composition, which determines the wide spectrum of its utilization not only as a fresh fruit, but also as a plant raw material for the food industry. The purpose of the paper is to make an integrated assessment for the fruit of promising raspberry varieties from genetic pool of FSSI “I.V. Michurin FSC” for nutrient and biologically active substances content and mineral elements. The object of investigation was 18 raspberry fruit varieties. The varieties are promising for cultivation in the Central Black Soil region of Russia. Chemical analyses of fruit were carried out with the use of spectrophotometric, chromatographic (HPLC), atomic absorption methods. As it was found, the significant variation in chemical composition indicators turned to be dependent on varietal features. The raspberry fruit accumulated 2.9–3.9% of dietary fibre, 0.34–1.3% of protein, 13.6–31.1 mg/100g of vitamin C, 0.2–83.6 mg/100g of anthocyanins, 0.14–0.90 mg/100g of niacin, 0.1–0.9 mg/100g of resveratrol, 0.2–3.1 mg/100g of piceid, 118.8–388.0 mg/100g of potassium, 0.29–0.97 mg/100g of iron. A high level accumulation of ascorbic acid was found in Gerakl, Evrazia, Zhar-ptitsa, Peresvet varieties; anthocyanins–in Evrazia, Gerakl, Polka, Rubinovoe ozherel’e; resveratrol and piceid–in “Zhelty gigant” and “Rubinovoe ozherel’e” varieties. The studied varieties are recommended as edible fresh fruit and for the consumption in the frozen form. Preventive food production is also appropriate.
... Medicinal food are gaining significance in mainstream healthcare as greater number of people look for relatively safe remedies and approaches to healthcare (Xiao et al., 2016;Chen et al., 2017a,b;Xiao, 2017;Vinayagam et al., 2017). Raspberry (Rubus coreanus Miq.), which is known to contain powerful natural antioxidants, is widely cultivated and consumed worldwide (ref) (Tsai et al., 2017;Garcia et al., 2017;Kula et al., 2016;Pavlovic et al., 2016;Kresty et al., 2016;Luo et al., 2016;Galli et al., 2016). In Korea, raspberries are not only consumed fresh, but also frozen and after processing into juice, jam, ice cream and wine (Hager et al., 2008). ...
Article
Raspberry seed is a massive byproduct of raspberry juice and wine but usually discarded. The present study employed a microwave-assisted method for extraction of raspberry seed oil (RSO). The results revealed that omega-6 fatty acids (linoleic acid and γ-linolenic acid) were the major constituents in RSO. Cellular antioxidant enzyme activity such as superoxide dismutase (SOD), glutathione peroxidase (GPx), and catalase (CAT) were investigated in HepG2 cells treated with RSO. Induction of the synthesis of several antioxidants in H2O2-exposed HepG2 cells was found. RSO increased the enzyme activity of SOD, CAT, and GPx in H2O2-exposed HepG2. Furthermore, RSO inhibited the phosphorylation of upstream mitogen-activated protein kinases (MAPK) such as c-Jun N-terminal kinase (c-JNK) and extracellular signal-regulated kinase (ERK). Taken together, the possible mechanisms to increase antioxidant enzyme activities in HepG2 may through the suppression of ERK and JNK phosphorylation. Raspberry seed oil exhibited good effects on the activities of the intracellular antioxidant enzymes and seems to protect the liver from oxidative stress through the inhibition of MAPKs.
... The presence of cyanidin-based glycosides in blackberry extracts was also confirmed by several authors. 11,[24][25][26] Antioxidant Activity ...
Article
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The presented study was aimed at exploring the bioactive properties (antioxidant, antimicrobial and food preserving) and chemical composition of R. discolor fruits collected from 2 geographically distinct wild-growing populations and extracted by using different solvents (methanol, ethanol, acetone and water). The total phenol (TPC), flavonoid (TFC) and anthocyanin (TAC) content varied from 52.7 to 186.8 mg GAE/g, 3.5 to 7.0 mg QE/g and 11.1 to 28.2 mg/g dry weight (dw), respectively. HPLC-DAD analysis identified cyanidin-3-glucoside (Cy-3-Glu) as the dominant anthocyanin that ranged in concentration from 18.4 to 32.2 mg/g dw. The acetone extract revealed the highest antioxidant activity through the ferric reducing antioxidant power (FRAP), total reducing power (TRC) and ß-carotene bleaching in vitro methods. The examined extracts showed antimicrobial activity, being more effective against Gram-positive (G +) than Gram-negative (G-) bacteria. Furthermore, Candida glabrata was the most susceptible among the pathogenic yeasts. The ethanol fruit extract was the most active against Listeria monocytogenes and thus chosen for incorporation in yoghurt and further analyses regarding its food preserving properties, which confirmed its efficacy towards this food-borne pathogen. Additionally, panelists gave high marks to the novel product regarding color, taste, texture flavor and overall acceptance. The obtained results indicated that R. discolor fruit extracts exhibits notable bioactivity and might therefore be considered as a good platform for the development of new preparations to be used in the food industry.
... Following, by concentration were phenolic acids, mainly ellagic, gallic, and chlorogenic acids; and at lower concentration p-coumaric, caffeic, hydroxybenzoic, and protocatechuic acids. To a lesser extent, flavonols were also identified (kaempferol, rutin, and quercetin); all these compounds have been reported as characteristic phenolics of red raspberry [47][48][49]. ...
Article
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Raspberries are important sources of bioactive compounds, whose synthesis is influenced by the fertilization system and the maturity stage. This study evaluated the effect of organic and conventional fertilization systems on raspberries at three maturity stages, pink, ripe, and overripe. Physicochemical characteristics, bioactive compounds (phenolic profile, vitamin C), antioxidant capacity (DPPH, FRAP, TEAC, and ORAC), phenolic-associated enzyme, phenylalanine ammonia lyase (PAL), and antioxidant enzymes (SOD, CAT, GPx, and APX) were evaluated. The physicochemical determination of the fruit did not reveal differences between fertilization systems. Regarding bioactive compounds, higher content of anthocyanins was found in organic raspberries at all maturity stages. Organic fertilization increased the content of ellagic acid and gallic acid at all stages of maturity. Higher content of caffeic, hydroxybenzoic, protocatechuic acid, and vitamin C was observed in organic raspberry at the overripe stage. Raspberries grown with organic fertilization exhibited higher values of antioxidant capacity by the DPPH, FRAP, and TEAC methods at all maturity stages. Raspberries under organic fertilization showed significantly greater activity of CAT, SOD, APX, GPX, and PAL. The present study suggests that organic fertilization induces oxidative stress causing an increase in antioxidant defense mechanisms, enhancing bioactive compound production, and improving antioxidant capacity in raspberries.
Article
In order to explore the influence of high hydrostatic pressure (HHP) on the quality of red raspberry wine, HHP technology was used to hold the red raspberry wine under the conditions of 200~600 MPa for 5 min/20℃, compared with the red raspberry wine without HHP treatment. Then the changes in aroma components, ellagic acid content, alcohol conten, colony‐forming unit and sensory quality of red raspberry wine under different HHP conditions were evaluated. The results showed that HHP affected the aroma components of red raspberry wine. Principal component analysis showed that HHP treatment greatly affected the characteristic constituents of alcohols and esters. Simultaneously, it changed the content and composition of phenolic substances in red raspberry wine. For example, ellagic acid content was 35.15 mg/L at 400 MPa, which was 3 times higher than of normal pressure. No significant difference was found about the alcohol content of the wine subjected to HHP treatment within 400 MPa. However, the alcohol content decreased if it was higher than 400 MPa. In addition, HHP technology could eliminate the microorganisms. This research provides theoretical foundation for the HHP technology usage to red raspberry wine.
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Tannins are a group of polyphenolic compounds synthesized and accumulated by higher plants as secondary metabolites. They are divided into hydrolysable tannins and proanthocyanidins and are found in many plant tissues in which they occur in diverse structures and amounts. This review provides a brief background on tannin distribution in plants, and summarizes the current literature on tannins in strawberries, raspberries, blueberries, currently the most commonly cultivated and consumed berries, and chokeberries, which have become popular in the last decades. The effects of processing and storage on tannin composition and levels in processed products are also provided.
Article
Subcritical water extraction (SWE) was investigated as an economical, green and sustainable extraction process of anthocyanin from raspberry. The critical extraction characteristics that influence SWE process were examined and optimized by response surface methodology (RSM) coupled with Box-Behnken design (BBD) and the content of anthocyanin was high to 8.15mg/g with optimization extraction conditions. Additional, the determination and semi-quantitative analysis of individual anthocyanin from raspberry has been investigated by high-performance liquid chromatography with diode array detector (HPLC–DAD) combined with Ultra Performance Liquid Chromatography-Triple-Time of Flight Mass Spectrometer (UPLC-Triple-TOF/MS). On this basis, the antioxidant activity of anthocyanin extracted by SWE was obviously superior to that from conventional extraction according to DPPH-radical scavenging activity and ABTS-radical scavenging activity. The extraction efficient and antioxidant activity of anthocyanin from raspberry from SWE were significantly higher than that from hot water extraction or methanol extraction.
Article
Rubus chingii, is widely distributed in many Asian countries and well known for its medicinal and dietary properties. Diversity of fruit color in raspberry has been attributed to the presence of either anthocyanins or carotenoids. In this study, we investigated anthocyanins and carotenoids, and their biosynthesis by LC-MS/MS. Six anthocyanins mainly consisted of flavanol-anthocyanins while five carotenoids mainly consisted of β-citraurin esters. Flavanol-anthocyanins were produced from an offshoot of the anthocyanin biosynthesis, which started with biosynthesis of flavanols and anthocyanidin by leucoanthocyanidin reductase (LAR)/anthocyanidin reductase (ANR) and anthocyanidin synthase (ANS/LDOX) respectively. β-citraurin esters were produced from cleavage of zeaxanthin and esterification by organic acid, which was an offshoot of the carotenoid biosynthesis. The offshoot started with biosynthesis of zeaxanthin and β-citraurin by carotene β-hydroxylase (CHYB/LUT5) and carotenoid cleavage dioxygenase (CCD) respectively. During fruit ripening, biosynthesis of flavanols and anthocyanins was down-regulated by genes/proteins involved in phenylpropanoid and flavonoid biosynthesis, while biosynthesis of β-citraurin esters was up-regulated by imbalanced expression of genes/proteins involved in β,β-ring and β, ε-ring hydroxylation. Thus, β-citraurin esters, instead of anthocyanins imparted reddish color to the ripe fruit. These pigments and their biosynthesis in R. chingii are totally different from what occurs in other raspberry species.
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Antioxidants from natural sources, such as vegetables and fruits, are attracting more and more interest. In this work, we evaluated the antioxidant potential of Folium Artemisia Argyi, a traditional Chinese herb medicine and food supplement. The total phenolic content, total flavonoid content, and antioxidant ability of the crude extracts and fractions obtained from consecutively partition of n-hexane, ethyl acetate, and n-butanol were measured and compared. Ethyl acetate fraction shows the highest total phenolic and flavonoid contents and highest antioxidant capability with regard to DPPH, ABTS, superoxide anion free radical scavenging ability, and ferric-reducing antioxidant power. In addition, the potential antioxidant components were screened by DPPH-UHPLC-MS experiments and subsequently characterized by using high-resolution tandem mass spectrometry. This work finally identified 45 antioxidants, including organic acids, phenolic compounds, flavonoids, and methoxylated flavonoids. The results suggested that Folium Artemisiae Argyi is a potential inexpensive resource of natural antioxidants.
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Chinese raspberry ( Rubus chingii Hu) is a fruit valued for its health benefits, which is indigenous to China.
Article
The breeding of raspberries (Rubus idaeus L.) and blackberries (R. fruticosus Agg.) has shifted in focus toward traits associated with the sensory qualities and potential health benefits of the fruit, and Rubus wild species have attracted a great deal of attention as new sources of genetic diversity. In this study, the anthocyanin and polyphenol contents and compositions, and three types of antioxidant capacities were compared in mature fruits including raspberries, blackberries, and Japanese wild Rubus species. ‘Blackcap’ black raspberry showed the significantly highest values of total anthocyanin content and total polyphenol content among 12 Rubus species or cultivars. Cyanidin-3-xylosyl-rutinoside was contained only in black raspberries, and was characteristic anthocyanin in Rubus species. R. croceacanthus H. Lév., a Japanese wild species that is adapted to warm regions, had a deep red fruit color, and had the highest total anthocyanin and total polyphenol contents among the four Japanese wild species examined. As for the antioxidant capacities, the highest values were observed in ‘Blackcap’ among 12 Rubus species. Furthermore, a high positive correlation was shown between total anthocyanin or total polyphenol content and antioxidant capacities. In particular, black raspberries and blackberries contained high concentrations of rutin. Thus, rutin might contribute to the high antioxidant capacities in these cultivars.
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This study aims to develop nutraceutical beverages containing food processing by-products in their formulation, and determine the opinion of consumers. This is done by testing whether they know that the main ingredients of the product are by-products, performing an overall acceptability test of the developed beverages, and evaluating the emotions induced by the newly developed beverages for consumers. The main ingredients used for the preparation of added-value beverages were fermented milk permeate (containing galactooligosaccharides), extruded and fermented wheat bran (WB) (containing ≥6.0 log10 CFU g−1 viable antimicrobial properties showing lactic acid bacteria (LAB) strains), and different fruit/berry by-products (FBB) (as a source of compounds showing antioxidant properties). The definition of the quantities of bioactive ingredients was based on the overall acceptability of the prepared beverages, as well as on emotions induced in consumers by the tested beverages. Functional properties of the developed beverages were proofed by the evaluation of their antimicrobial and antioxidant properties, as well as viable LAB count during storage. Desirable changes in extruded and fermented WB were obtained: Fermentation reduced sugar concentration and pH in samples with predominant lactic acid isomer L(+). In addition, the viable LAB count in the substrate was higher than 6.0 log10 CFU g−1, and no enterobacteria remained. By comparing the overall acceptability of the beverages enriched with WB, the highest overall acceptability was shown for the samples prepared with 10 g of the extruded and fermented WB (7.9 points). FBB showed desirable antimicrobial activity: Shepherd inhibited—2, sea buckthorn—3, blueberries—5, and raspberries—7 pathogens from the 10 tested. Comparing different beverage groups prepared with different types of FBB, in most cases (except sea buckthorn), by increasing FBB content the beverages overall acceptability was increased, and the highest score (on average, 9.5 points) was obtained for the samples prepared with 5.0 and 7.5 g of blueberries FBB. Moreover, a very strong positive correlation (r = 0.8525) was found between overall acceptability and emotion “happy” induced in consumers by the prepared beverages enriched with extruded and fermented WB and FBB. By comparing the samples prepared with the addition of WB with samples prepared with WB and FBB, it was observed that most FBB increased total phenolic compounds (TPC) content (on average, by 9.0%), except in the case of samples prepared with sea buckthorn. A very high positive correlation (r = 0.9919) was established between TPC and antioxidant activity. Finally, it can be stated that the newly developed nutraceutical beverages were acceptable for consumers, induced positive emotions, and possessed desirable antimicrobial and antioxidant properties, while being prepared in a sustainable and environmentally friendly manner.
Article
Rubi Fructus, a common traditional Chinese medicine, is abundant in phenolic components with pharmacodynamical effect. An efficient and rapid ball mill‐assisted vortex‐enhanced matrix solid‐phase dispersion method was developed for the simultaneous quantification of five phenols (ellagic acid, kaempferol‐3‐O‐rutinoside, astragalin, tiliroside, and kaempferol) in Rubi Fructus by high‐performance liquid chromatography. The introduction of the ball mill instrument realized the automation of the first step of matrix solid‐phase dispersion. Several extraction parameters were evaluated, and the best extraction conditions were optimized by response surface methodology. The method exhibited a good linearity for the five compounds (r2 > 0.999). The recoveries of the five target analytes in Rubi Fructus ranged from 98.7% to 102% (RSD≤3.92%) under the optimized conditions: Al‐SBA‐15 as a dispersant, sample/dispersant ratio of 1:3, ball milling time as 2 min, vibration frequency of the ball mill as 1300 rpm, 1.4 mL methanol as eluent and vortex time as 3 min. Consequently, the established ball mill‐assisted vortex‐enhanced matrix solid‐phase dispersion combined with HPLC could be applied to extract and analyze the target phenolic compounds in Rubi Fructus samples.
Chapter
In recent years raspberry fruit breeding has shifted its focus from traits associated with agronomic performance towards those associated with fruit sensory quality (Jennings et al. 2016) and potential health benefits (Mazzoni et al. 2016). Simultaneously, significant advancements have been made in raspberry genetics and genomics as well as analytical chemistry in soft fruit. These new tools are generating knowledge that has the capacity to significantly accelerate the development of new varieties that meet consumer expectations in terms of sensory experience and health benefits of fruit consumption. Significant research in recent years has identified the environmental, biochemical and genetic controls underlying the accumulation of specific compounds in raspberry fruit. Furthermore, increasing information is becoming available regarding the mechanisms of action of specific phytochemicals in relation to human health outcomes. This information is now providing the underpinning science for the development of new cultivars. In this chapter, we outline current understanding of the biosynthetic pathways associated with the accumulation of significant fruit phytochemicals and describe what is presently known regarding the influence of crop genetics and the growing environment on the accumulation of specific phytochemicals. Finally we outline the latest knowledge regarding how fruit phytochemicals modulate human health outcomes. It is anticipated that the work outlined here will guide molecular breeding targets for future crop improvement.
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This volume of the International Journal of Pharmacology, Phytochemistry and Ethnomedicine outlines the latest scientific findings dealt with evaluation of the neuropharmacological activities of Wild Indigo (Baptisia australis R.Br.) roots methanol extract; estimation of the antioxidant capabilities of Dennettia tripetala Baker f. fruits in preventing liver and kidney damage in rats influenced by one dose of Carbon tetrachloride; investigation of the content of phenol compounds and flavonoids obtained from “Chemlali” olive leaf (Olea europaea L.) collected in Algeria with following assessment in vitro antioxidant and antimicrobial activities of the phenolic extracts as well as analysis of the amount of phenolic compounds in red currant (Ribes rubrum L.) berries and raspberries (Rubus idaeus L.) by an optimized HPLC method; study of different dietary sources of non-starch polysaccharides impact on growth traits, physiological and immune responses and also gene expression of intestinal GLUT2 in chickens; exploration of the range of physiological parameters in experimental breast cancer induced by intermammary administration of N-Methyl-N-Nitrosourea in Wistar rats; examination of the effects of D-002 (beeswax alcohols) on the esophageal histological changes in rats with duodeno-esophageal reflux esophagitis. In addition several reviews are delivered in this volume. First mini-review observes the herbicide Atrazine disruptive influence on human metabolism, reproduction, immune system, cell division. The second review is devoted to the standard pharmacological approaches and alternative medicine for prevention of chemotherapy-induced peripheral neuropathy. The last mini-review shows recent discoveries of flavonoids and diarylheptanoids for the treatment of neurodegenerative diseases
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Until today, numerous studies evaluated the topic of anthocyanins and various types of cancer, regarding the anthocyanins’ preventative and inhibitory effects, underlying molecular mechanisms, and such. However, there is no targeted review available regarding the anticarcinogenic effects of dietary anthocyanins on skin cancers. If diagnosed at the early stages, the survival rate of skin cancer is quite high. Nevertheless, the metastatic form has a short prognosis. In fact, the incidence of melanoma skin cancer, the type with high mortality, has increased exponentially over the last 30 years, causing the majority of skin cancer deaths. Malignant melanoma is considered a highly destructive type of skin cancer due to its particular capacity to grow and spread faster than any other type of cancers. Plants, in general, have been used in disease treatment for a long time, and medicinal plants are commonly a part of anticancer drugs on the market. Accordingly, this work primarily aims to emphasize the most recent improvements on the anticarcinogenic effects of anthocyanins from different plant sources, with an in-depth emphasis on melanoma skin cancer. We also briefly summarized the anthocyanin chemistry, their rich dietary sources in flowers, fruits, and vegetables, as well as their associated potential health benefits. Additionally, the importance of anthocyanins in topical applications such as their use in cosmetics is also given.
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Raspberries, derived from different cultivar varieties, are a popular ingredient of everyday diet, and their biological activity is a point of interest for researchers. The ethanol-water extracts from four varieties of red (Rubus idaeus ‘Ljulin’, ‘Veten’, ‘Poranna Rosa’) and black (Rubus occidentalis ‘Litacz’) raspberries were evaluated in the range of their antimicrobial properties as well as phenolic content – sanguiin H-6, free ellagic acid and anthocyanins. The antimicrobial assay was performed with the use of fifteen strains of bacteria, both gram-negative and gram-positive. The antimicrobial activity of the extracts varied and depended on the analysed strain of bacteria and cultivar variety, with the exception of Helicobacter pylori, towards which the extracts displayed the same growth inhibiting activity. Two human pathogens Corynebacterium diphtheriae and Moraxella catarrhalis proved to be the most sensitive to raspberry extracts. Contrary to the extracts, sanguiin H-6 and ellagic acid were only active against eight and nine bacterial strains, respectively. The determined MIC and MBC values of both compounds were several times lower than the tested extracts. The highest sensitivity of Corynebacterium diphtheriae to extracts from both black and red raspberries may be due to its sensitivity to sanguiin H-6 and ellagic acid.
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The mechanism of action of polyphenolic compounds is attributed to their antioxidant, anti-inflammatory, and anti-proliferative properties and their effects on subcellular signal transduction, cell cycle impairment and apoptosis. A raspberry (Rubus idaeus L.) fruit extract contains various antioxidant active compounds, particularly ellagic acid (EA); however the exact intracellular mechanism of their action is not fully understood. The aim of the study was to evaluate the antioxidant effect of raspberry extracts, and that of ellagic acid by assessment of the production of the reactive oxygen species (ROS) by murine macrophage J774 cells. Raspberry extracts and their active compound EA did not affect or had very minor effects on cell viability. No significant difference in the ROS generation in arachidonic acid stimulated macrophages was determined for raspberry extracts and EA whereas in the phorbol-12 myristate-13 acetate model ROS generation was significantly (p < 0.05) reduced. Our observation that raspberry pomace extracts in vitro reduce ROS production in a J774 macrophage culture suggests that raspberry extract and ellagic acid mediated antioxidant effects may be due to the regulation of NADPH oxidase activity.
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Black raspberry ( Rubus occidentalis L.) (BR) fruit extracts with differing compound profiles have shown variable antiproliferative activities against HT-29 colon cancer cell lines. This study used partial least-squares (PLS) regression analysis to develop a high-resolution (1)H NMR-based multivariate statistical model for discerning the biological activity of BR constituents. This model identified specific bioactive compounds and ascertained their relative contribution against cancer cell proliferation. Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were the predominant contributors to the extract bioactivity, but salicylic acid derivatives (e.g., salicylic acid glucosyl ester), quercetin 3-glucoside, quercetin 3-rutinoside, p-coumaric acid, epicatechin, methyl ellagic acid derivatives (e.g., methyl ellagic acetyl pentose), and citric acid derivatives also contributed significantly to the antiproliferative activity of the berry extracts. This approach enabled the identification of new bioactive components in BR fruits and demonstrates the utility of the method for assessing chemopreventive compounds in foods and food products.
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There has been increasing interest in the research on flavonoids from plant sources because of their versatile health benefits reported in various epidemiological studies. Since flavonoids are directly associated with human dietary ingredients and health, there is need to evaluate structure and function relationship. The bioavailability, metabolism, and biological activity of flavonoids depend upon the configuration, total number of hydroxyl groups, and substitution of functional groups about their nuclear structure. Fruits and vegetables are the main dietary sources of flavonoids for humans, along with tea and wine. Most recent researches have focused on the health aspects of flavonoids for humans. Many flavonoids are shown to have antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities, while some flavonoids exhibit potential antiviral activities. In plant systems, flavonoids help in combating oxidative stress and act as growth regulators. For pharmaceutical purposes cost-effective bulk production of different types of flavonoids has been made possible with the help of microbial biotechnology. This review highlights the structural features of flavonoids, their beneficial roles in human health, and significance in plants as well as their microbial production.
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Ellagitannins have shown anti-inflammatory and anti-Helicobacter pylori properties; however, their anti-inflammatory activity at gastric level was not previously investigated. The aim of this research was to evaluate the effects of ellagitannins from Rubus berries on gastric inflammation. Ellagitannin enriched extracts (ETs) were prepared from Rubus fruticosus L. (blackberry) and Rubus idaeus L. (raspberry). The anti-inflammatory activity was tested on gastric cell line AGS stimulated by TNF-α and IL-1β for evaluating the effect on NF-kB driven transcription, nuclear translocation and IL-8 secretion. In vivo the protective effect of ellagitannins was evaluated in a rat model of ethanol-induced gastric lesions. Rats were treated orally for ten days with 20 mg/kg/day of ETs, and ethanol was given one hour before the sacrifice. Gastric mucosa was isolated and used for the determination of IL-8 release, NF-kB nuclear translocation, Trolox equivalents, superoxide dismutase and catalase activities. In vitro, ETs inhibited TNF-α induced NF-kB driven transcription (IC50: 0.67-1.73 µg/mL) and reduced TNF-α-induced NF-kB nuclear translocation (57%-67% at 2 µg/mL). ETs inhibited IL-8 secretion induced by TNF-α and IL-1β at low concentrations (IC50 range of 0.7-4 µg/mL). Sanguiin H-6 and lambertianin C, the major ETs present in the extracts, were found to be responsible, at least in part, for the effect of the mixtures. ETs of blackberry and raspberry decreased Ulcer Index by 88% and 75% respectively and protected from the ethanol induced oxidative stress in rats. CINC-1 (the rat homologue of IL-8) secretion in the gastric mucosa was reduced in the animals receiving blackberry and raspberry ETs. The effect of ETs on CINC-1 was associated to a decrease of NF-κB nuclear translocation in ETs treated animals. The results of the present study report for the first time the preventing effect of ETs in gastric inflammation and support for their use in dietary regimens against peptic ulcer.
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Because of its intense anthocyanin pigments, black raspberry (Rubus occidentalis L.) has a long history of use as a natural colorant and dye. Recent studies showing black raspberries to be a rich source of anthocyanins and other dietary phytochemicals have led to renewed interest in breeding better adapted cultivars that meet the demands of these markets. Anthocyanin content is a critical indicator of fruit quality for fresh and processed markets. Previous studies characterizing black raspberry anthocyanins have focused on existing cultivars comprising a narrow genetic base; however, progress in breeding new cultivars with better adaptability and disease resistance will rely on the use of new germplasm sources. Using high performance liquid chromatography/diode array detector/ion trap mass spectrometer, we examined anthocyanin content and profiles in the juice of fruit from black raspberry seedlings representing 78 wild populations from across the species' native range over a two year period. Anthocyanin profiles were similar to those previously reported, however total anthocyanin content varied widely. Total anthocyanins in individual clones ranged from 39 to 996 mg/100 ml (expressed as cyanidin-3-glucoside) and averaged slightly higher in 2010 than in 2009. Black raspberry cultivars fell in the middle of this range, with individual wild clones ranging from less than one fourth to nearly three times the anthocyanin concentration of the industry standard, 'Munger'. Genetic diversity for anthocyanin content is present in recently collected wild black raspberry germplasm and should be carefully evaluated when using this material for breeding improved cultivars.
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The capabilities of mass spectrometry for microscale determination of anthocyanins were investigated using high-performance liquid chromatography electrospray ionization mass spectrometry (LC-ESI/ MS) and tandem mass spectrometry (MS-MS). Four anthocyanins [cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3–(2G−xylosylrutinoside) and cyanidin 3-rutinoside] were characterized in black raspberry samples by LC-ESI/MS-MS using both positive and negative ion analyses. Quantification of anthocyanins was conducted using ESI/MS-MS with selected reaction monitoring (SRM). Linear responses of several anthocyanins were determined during MS-MS analyses. Detection limits as low as 1 femtomol for most anthocyanins were obtained during ESI/MS-MS. Compared with other quantitative procedures such as high-performance liquid chromatography (HPLC) and ultraviolet/visible spectrophotometry, the current method provides an improved sensitive, specific technique for direct determination of intact anthocyanins. The developed methodology was successfully applied to analysis of trace levels of anthocyanins in human plasma and epithelial cells.
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Two fraction, one containing flavonols, flavan-3-ols, phenolic acids and the other containing anthocyanins, were isolated from Rubus (red raspberry, blackberry) and Prunus (sweet cherry, sour cherry) fruits to study their phenol content by HPLC and antioxidant activity using the DPPH test. Raspberries and blackberries were characterised by catechins and ellagic acid derivatives; sour and sweet cherries by phenolic acids. All fruits had relatively high anthocyanin content. Anthocyanins contributed more to the antioxidant activity of all fruits (∼90%) than flavonols, flavan-3-ols and phenolic acids (∼10%). A biphasic reaction was observed between DPPH• radicals and phenols, with ‘fast’ and ‘slow’ scavenging rates which might be important in the biological activity of these fruits. Sour cherries and blackberries which stand out with the highest total phenol content (1416 and 1040 mg kg−1) had also the strongest antioxidant activity (EC50 = 807 and 672 g of fruit per gram of DPPH) and can be considered as good source of dietary phenols.
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Dietary freeze-dried black raspberries inhibit tumor induction by N-nitrosomethylbenzylamine in the rat esophagus, but the constituents responsible for this chemopreventive activity have not been identified. We fractionated freeze-dried black raspberries and used mouse epidermal JB6 Cl 41 cells stably transfected with either a nuclear factor kappa B (NFkappaB)- or an activator protein 1 (AP-1)-luciferase reporter, and treated with racemic anti-benzo[a]pyrene-7,8-diol-9,10-epoxide (BPDE), to assess the inhibitory effects of the fractions. The ethanol and water extracts of the freeze-dried black raspberries had inhibitory activity and these extracts were fractionated by HPLC to give several bioactive fractions. Further HPLC analysis yielded multiple subfractions, some of which inhibited BPDE-induced NFkappaB activity. Major constituents of the most active subfractions were identified by their spectral properties and in comparison with standards as cyanidin-3-O-glucoside, cyanidin 3-O-(2(G)-xylosylrutinoside) and cyanidin 3-O-rutinoside. Analysis of freeze-dried black raspberries indicated that these three components comprised approximately 3.4% of the material by dry weight. Consistent with these results, standard cyanidin-3-O-glucoside and cyanidin chloride were also good inhibitors of BPDE-induced NFkappaB activity. The results of this study demonstrate that cyanidin glycosides of freeze-dried black raspberries are bioactive compounds which could account for at least some of the chemopreventive activity observed in animal models.
Article
Anthocyanin and colour stability of red raspberry jams made from two different varieties (‘Zeva’ and ‘Heritage’) were analysed during 6 months, stored at three temperatures (20, 30 and 37°C). Also the influence of freezing the fruit, previously to jam manufacture, was evaluated. Different anthocyanin composition was detected for both cultivars and while ‘Zeva’ fruit had a higher total anthocyanin content, Heritage variety produced jams with a higher redness hue. The development of browning was directly related to storage temperature but not to thawing or the variety of fruit used. © 1998 Society of Chemical Industry.
Article
The capabilities of mass spectrometry for microscale determination of anthocyanins were investigated using high-performance liquid chromatography electrospray ionization mass spectrometry (LC-ESI/ MS) and tandem mass spectrometry (MS-MS). Four anthocyanins [cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-(2(G)-xylosylrutinoside) and cyanidin 3-rutinoside] were characterized in black raspberry samples by LC-ESI/MS-MS using both positive and negative ion analyses. Quantification of anthocyanins was conducted using ESI/MS-MS with selected reaction monitoring (SRM). Linear responses of several anthocyanins were determined during MS-MS analyses. Detection limits as low as 1 femtomol for most anthocyanins were obtained during ESI/MS-MS. Compared with other quantitative procedures such as high-performance liquid chromatography (HPLC) and ultraviolet/visible spectrophotometry, the current method provides an improved sensitive, specific technique for direct determination of intact anthocyanins. The developed methodology was successfully applied to analysis of trace levels of anthocyanins in human plasma and epithelial cells.
Article
Rubus occidentalis is a black-fruited raspberry originating from North America. Its popularity and demand has been growing over the years, as studies outline its high anthocyanin and ellagitannin content and significance for human health. Interaction between chemical composition and pharmacological activity, mechanisms of action at cellular and molecular levels are all active areas of study. The vast majority of research concerning black raspberries is focused on chemoprevention and anticancer effects. This review summarizes the data on chemical composition and anticancer activity of black raspberry fruits throughout the years.
Article
This study compared the antioxidant effects of two kinds of black raspberry extract, obtained from fruits of Rubus coreanus and Rubus occidentalis, which can be found in Korea. The fruits of R. coreanus and R. occidentalis were each extracted with 0%, 25%, 50%, 75%, and 100% ethanol (EtOH). Among the extracts of these two varieties, 50% EtOH extract of R. occidentalis showed the highest contents of total polyphenols (46.96±2.78 mg/g) and flavonoid compounds (11.77±0.81 mg/g). The 50% EtOH extract of R. occidentalis showed the highest antioxidant activity (84.77±0.97%) in terms of DPPH radical scavenging activity. On the contrary, 25% EtOH extract of R. occidentalis showed the best antioxidant activity (29.65±2.41%) in terms of ABTS radical scavenging activity. In the results of ferric reducing antioxidant power (FRAP) assay, 50% EtOH extract of R. occidentalis showed the highest antioxidant activity (0.49±0.02%). In the cytotoxicity test stimulated with H2O2, the extracts of 75% and 100% EtOH from R. occidentalis showed the highest cell viability (93.54±3.37% and 97.19±0.74%, respectively). According to our results, extracts of R. occidentalis showed higher antioxidant activities than extracts of R. coreanus. Especially, total polyphenol and flavonoid contents of R. occidentalis showed the highest significant correlation with FRAP by Pearson's correlation (P=0.005 and P=0.013, respectively). © 2014, Korean Society of Food Science and Nutrition. All rights reserved.
Article
Raspberries are rich in phenolic phytochemicals. To study the health benefits of raspberries, four fresh raspberry varieties (Heritage, Kiwigold, Goldie, and Anne) were evaluated for total antioxidant and antiproliferative activities. The total amount of phenolics and flavonoids for each of the four raspberry varieties was determined. The Heritage raspberry variety had the highest total phenolic content (512.7 +/- 4.7 mg/100 g of raspberry) of the varieties measured followed by Kiwigold (451.1 +/- 4.5 mg/100 g of raspberry), Goldie (427.5 +/- 7.5 mg/100 g of raspberry), and Anne (359.2 +/- 3.4 mg/100 g of raspberry). Similarly, the Heritage raspberry variety contained the highest total flavonoids (103.4 +/- 2.0 mg/100 g of raspberry) of the varieties tested, followed by Kiwigold (87.3 +/- 1.8 mg/100 g of raspberry), Goldie (84.2 +/- 1.8 mg/100 g of raspberry), and Anne (63.5 +/- 0.7 mg/100 g of raspberry). The color of the raspberry juice correlated well to the total phenolic, flavonoid, and anthocyanin contents of the raspberry. Heritage had the highest a/b ratio and the darkest colored juice, and the Anne variety showed the lowest phytochemical content and the palest color. Heritage raspberry variety had the highest total antioxidant activity, followed by Kiwigold and Goldie, and the Anne raspberry variety had the lowest antioxidant activity of the varieties tested. The proliferation of HepG(2) human liver cancer cells was significantly inhibited in a dose-dependent manner after exposure to the raspberry extracts. The extract equivalent to 50 mg of Goldie, Heritage, and Kiwigold fruit inhibited the proliferation of those cells by 89.4 +/- 0.1, 88 +/- 0.2, and 87.6 +/- 1.0%, respectively. Anne had the lowest antiproliferative activity of the varieties measured but still exhibited a significant inhibition of 70.3 +/- 1.2% with an extract equivalent to 50 mg of fruit. The antioxidant activity of the raspberry was directly related to the total amount of phenolics and flavonoids found in the raspberry (p < 0.01). No relationship was found between antiproliferative activity and the total amount of phenolics/flavonoids found in the same raspberry (p > 0.05).
Article
Colour and chemical composition of fruits of 10 red raspberry genotypes grown in Nordic climate during three harvest seasons were studied. The main phenolic compounds in the fruits were ellagitannins and anthocyanins, contributing 57% and 42% to the quantified phenolic compounds, respectively. Cyanidin-3-sophoroside was the most abundant anthocyanin (61%). All quality parameters were significantly affected by genotype. The genotypes could be categorised into three groups. 'Veten' and 'RU984 06038' were characterised by high concentrations of flavonoids, i.e., anthocyanins and quercetin glycosides, and dark red colour. 'Octavia', 'Glen Magna', 'RU004 03067', 'Glen Ample' and 'RU974 07002' were characterised by light colour, high titratable acids and low flavonoid concentrations. 'Malling Hestia', 'RU024 01003' and 'RU004 04095' had high content of dry matter, soluble solids, ascorbic acid and ellagic acid containing compounds, in addition to high hue and chroma values. All quality parameters, except ascorbic acid and lambertianin C, varied significantly between harvest seasons. The lowest seasonal variation in fruit quality was observed in 'RU024 01003' and 'Glen Ample' and the highest 'RU004 03067' and 'Glen Magna'.
Article
Black raspberry seed extract and its tannin fraction were characterized and their antioxidant and anti-inflammatory activities were compared to grape seed extract and its tannin fraction. Tannin fraction of black raspberry seed extract was mostly composed of ellagitannins including pedunculagin, sanguiin H6 and H10 isomers and galloyl-bis-HHDP glucose isomer, while that of grape seed extract was composed of proanthocyanidins including proanthocyanidin dimers, trimers, tetramers, pentamers, their monogallates and hexamers. Antioxidant activities of the tannin fraction of black raspberry seed extract, measured by polyphenol content, FRAP, DPPH and ABTS assays, were significantly higher than those of grape seed extract. Anti-inflammatory activity of the tannin fraction of black raspberry seed extract, measured by NO assay, was also significantly higher than that of grape seed extract. The results indicate that black raspberry seeds have potential benefits as a source of natural antioxidant and anti-inflammatory agents comparable to grape seeds. Practical ApplicationsBlack raspberry and grape fruits are widely consumed in various ways including wine, juice or raw fruits. Many byproducts, including seeds and wine pomace, are an attractive source of functional compounds. Our results show that the tannins extracted from the seeds have potential antioxidant and anti-inflammatory activities. Thus, these results may help increase utilization of byproducts to make dietary supplements. This may also reduce the waste products generated by the industry and provide additional profit to farmers and manufacturers.
Article
Epithelial to mesenchymal transition (EMT) has been considered essential for cancer metastasis, a multistep complicated process including local invasion, intravasation, extravasation, and proliferation at distant sites. Herein we provided molecular evidence associated with the antimetastatic effect of Rubus idaeus L. extracts (RIE) by showing a nearly complete inhibition on the invasion (p < 0.001) of highly metastatic A549 cells via reduced activities of matrix metalloproteinase-2 (MMP-2) and urokinasetype plasminogen activator (u-PA). We performed Western blot to find that RIE could induce up-regulation of epithelial marker such as E-cadherin and α-catenin and inhibit the mesenchymal markers such as N-cadherin, fibronectin, snail-1, and vimentin. Selective snail-1 inhibition by snail-1-specific-siRNA also showed increased E-cadherin expression in A549 cells suggesting a possible involvement of snail-1 inhibition in RIE-caused increase in E-cadherin level. RIE also inhibited p-FAK, p-paxillin and AP-1 by Western blot analysis, indicating the anti-EMT effect of RIE in human lung carcinoma. Importantly, an in vivo BALB/c nude mice xenograft model showed that RIE treatment reduced tumor growth by oral gavage, and RIE represent promising candidates for future phytochemical-based mechanistic pathway-targeted cancer prevention strategies.
Article
Red raspberry (Rubus idaeus L.) is an economically important berry crop that contains numerous phenolic compounds with potential health benefits. It is known that the content of phenolics is affected by processing factors, but limited information is available on the influence of cultural factors or genotype. To clarify this issue, phenolic compounds were analysed from a diverse range of raspberry cultivars grown under northern European conditions, in Finland.The content of phenolic compounds varied widely and significantly between cultivars. The quercetin content ranged from 0.32 (yellow cultivar) to 1.55mg/100g fresh weight (fw) (cv. Balder). The ellagic acid content varied from 38 (cv. Gatineau and cv. Nova) to 118mg/100g fw (cv. Ville). The total anthocyanin content varied from close to 0 (yellow cultivars) to 51mg/100g fw (cv. Gatineau). The content of total phenolics varied from 192 (cv. Gatineau) to 359mg/100g fw (cv. Ville). In addition, environment had a significant effect on the content of quercetin. Thus, breeding material should be evaluated for their potential health benefits over several regions in northern raspberry breeding.
Article
Here we attempt to clarify contemporary scientific findings of Rubus fruit phenolics, focusing mainly on published peer-reviewed work from the last 6 years. Our review focuses on research papers that identified phenolics of Rubus fruit, although other edible parts of Rubus plants (i.e. leaves, roots) also contain phenolics. With an increased awareness given to the potential health benefits of consuming berries high in phenolics, efforts have been directed at enhancing Rubus fruit quality and colour (through plant selection, harvesting, storage, etc.) for processors and consumers alike. Assessment of any progress requires knowing the state of the starting material, so effective research into Rubus phenolics relies upon the accurate identification of the components in Rubus fruit in the initial investigations. We have summarised these reports into three sections: anthocyanins, phenolic monomers other than anthocyanins, and phenolic polymers. More work is needed in identification and quantification, and further opportunities remain for deciphering and clarifying existing phenolic information for Rubus fruit.
Article
Anthocyanin and colour stability of red raspberry jams made from two different varieties (‘Zeva’ and ‘Heritage’) were analysed during 6 months, stored at three temperatures (20, 30 and 37°C). Also the influence of freezing the fruit, previously to jam manufacture, was evaluated. Different anthocyanin composition was detected for both cultivars and while ‘Zeva’ fruit had a higher total anthocyanin content, Heritage variety produced jams with a higher redness hue. The development of browning was directly related to storage temperature but not to thawing or the variety of fruit used. © 1998 Society of Chemical Industry.
Article
Anthocyanin composition of black raspberry (Rubus occidentalis) was studied using high-performance liquid chromatography coupled to photodiode array (PDA) detection and electrospray ionization mass spectrometry (LC-ESI/MS) and tandem mass spectrometry (MS/MS). Pelargonidin 3-rutinoside was isolated and identified in black raspberries using HPLC, UV–Vis spectroscopy, MS, and NMR spectroscopy. No pelargonidin derivative had been previously found in Rubus occidentalis. In addition, the presence and identities of four previously reported anthocyanins (cyanidin 3-glucoside, cyanidin 3-sambubioside, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside) were confirmed by HPLC/MS and MS/MS analyses.
Article
Black raspberry (Rubus occidentalis L.) has long been recognized as a rich source of anthocy-anins. Despite renewed interest in this crop for its potential health benefits, the range of variation in anthocyanin content and other phenolic compounds has not been well exam-ined. Here we present anthocyanin concentration and profiles, as well as total phenolics, in the fruit of 26 black raspberry seedling populations (190 samples over two growing seasons) derived from cultivated and wild parents. There was more than a twofold difference in total anthocyanin concentration between the lowest and highest pigmented populations (ranging from 244.8 to 541.3 mg 100 mL À1). The relative amounts of the two major anthocy-anins (cyanidin-3-rutinoside and cyanidin-3-xylosylrutinoside) in black raspberry fruit were significantly different. The range of total phenolics found was much lower (206.7– 330.4 mg 100 mL À1). This information will provide a valuable baseline for researchers interested in studying the health effects of these compounds, product developers in the nutraceutical market, and breeders interested in developing new cultivars with improved fruit chemistry traits. Published by Elsevier Ltd.
Article
 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.
Article
The purpose of the study was to determine polyphenols, anthocyanins and ascorbic acid in the extracts of black raspberry fruits and wine, along with their anti-oxidant, anti-proliferative and anti-inflammatory activities. Black raspberry fruits without or with seeds crushed were blended in 60% ethanol (FE and FES, respectively) or in water (FW and FWS, respectively). Black raspberry wine without or with seeds crushed (W and WS, respectively) were prepared. Polyphenol content was the highest in the FES (8.25 mg/g fruit). Generally the ethanol extracts with seeds crushed showed higher anti-oxidant activities with the lowest DPPH IC50 (130 μg/ml (freeze-dried extract/reaction solution)) for the FES and the lowest ABTS IC50 (198 μg/ml) for the WS. Cell viabilities were reduced by 13–70% when treated with 100 μg/ml (freeze-dried extract/medium) for HT-29 cells and 1000 μg/ml for LNCaP cells. The FES most actively suppressed nitric oxide production in LPS-stimulated RAW264.7 cells (p < 0.05). Superoxide dismutase and glutathione peroxidase activities treated with the extracts were higher than the control (p < 0.05).
Article
The raspberry (Rubus idaeus L.) is an economically important berry crop that contains many phenolic compounds with potential health benefits. In this study, important pomological features, including nutrient content and antioxidant properties, of a domesticated and 3 wild (Yayla, Yavuzlar, and Yedigöl) raspberry fruits were evaluated. Also, the amount of total phenolics and flavonoids in lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were calculated as gallic acid equivalents (GAEs) and quercetin equivalents (QE). The highest phenolic compounds were found in wild Yayla ecotype (26.66 ± 3.26 GAE/mg extract). Whilst, the highest flavonoids were determined in wild Yedigöl ecotype (6.09 ± 1.21 QA/mg extract). The antioxidant activity of lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were investigated as trolox equivalents using different in vitro assays including DPPH(•), ABTS(•+), DMPD(•+), and O(•-)(2) radical scavenging activities, H(2)O(2) scavenging activity, ferric (Fe(3+)) and cupric ions (Cu(2+)) reducing abilities, ferrous ions (Fe(2+)) chelating activity. In addition, quantitative amounts of caffeic acid, ferulic acid, syringic acid, ellagic acid, quercetin, α-tocopherol, pyrogallol, p-hydroxybenzoic acid, vanillin, p-coumaric acid, gallic acid, and ascorbic acid in lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were detected by high-performance liquid chromatography and tandem mass spectrometry (LC-MS-MS). The results clearly show that p-coumaric acid is the main phenolic acid responsible for the antioxidant and radical scavenging activity of lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits.
Article
Ellagitannins from red raspberries (Rubus idaeus) and cloudberries (Rubus chamaemorus) were isolated by using column chromatography and preparative HPLC. The berry phenolic isolates consisted of 80% (cloudberry) and of 60% (raspberry) of ellagitannins, with raspberries also containing anthocyanins. The main ellagitannins of both raspberries and cloudberries were identified by ESI-MS to consist of the dimeric sanguiin H-6 and the trimeric lambertianin C. Monomeric ellagitannins such as casuarictin in raspberries and pedunculagin in cloudberries were also found. The antioxidant activity of the berry phenolic isolate, ellagitannin isolate (mixture), ellagitannin main fraction (dimer and trimer), and ellagic acid was studied in bulk and emulsified methyl linoleate, in human low-density lipoprotein in vitro, and the radical scavenging activity was studied in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. Cloudberry and red raspberry ellagitannins were highly effective as radical scavengers. Berry ellagitannins also showed significant antioxidant activity toward oxidation of both human LDL and methyl linoleate emulsions. However, only weak or moderate antioxidant activity was exhibited by ellagitannins toward oxidation of bulk oil. Thus, ellagitannins contribute significantly to the antioxidant capacity of cloudberries and red raspberries in lipoprotein and lipid emulsion environments, the latter being more relevant for food applications.
Article
Raspberry flavonoid compounds have significant antioxidant activities, and regular consumption may help prevent and/or moderate chronic diseases. Targeted metabolite profiling is useful to identify compounds contributing to these antioxidant properties and health benefits and for tailored breeding for functional foods. In this study, metabolomic variation was determined among three fall-fruiting red raspberry cultivars ('Autumn Britten', 'Caroline', 'Nantahala') grown at three North Carolina locations differing in elevation and average day/night temperatures. 'Nantahala' was specifically bred for the mountainous regions of the southern United States. Ten flavonoid compounds were detected by liquid chromatography-time-of-flight-mass spectrometry (LC-TOF-MS). Of those, cyanidin-3-glucoside, cyanidin-3-sophoroside, cyanidin-3-rutinoside, cyanidin-3-sambubioside, and quercetin-3-glucoside were quantified against external standards. Variation in flavonoid composition was primarily attributed to genotype and associated with night temperature and hours exposed to temperatures over 29 °C. 'Nantahala' had particularly high levels of cyanidin-3-sambubioside, indicative of its purple raspberry lineage. Quercetin-3-glucoside levels increased the most with elevated temperatures.
Article
The red raspberry ( Rubus idaeus ) fruit contains bioactive polyphenols including anthocyanins and ellagitannins with reported anti-inflammatory properties. This study sought to investigate the cartilage-protecting and anti-inflammatory effects of a polyphenolic-enriched red raspberry extract (RRE; standardized to total polyphenol, anthocyanin, and ellagitannin contents) using (1) an in vitro bovine nasal explant cell culture model and (2) an in vivo adjuvant-induced arthritis rat model. RRE contained 20% total polyphenols (as gallic acid equivalents), 5% anthocyanins (as cyanidin-3-glucoside equivalents), and 9.25% ellagitannins (as ellagic acid equivalents). In the in vitro studies, bovine nasal explants were stimulated with 10 ng/mL IL-1β to induce the release of proteoglycan and type II collagen. On treatment with RRE (50 μg/mL), there was a decrease in the rate of degradation of both proteoglycan and type II collagen. In the in vivo antigen-induced arthritis rat model, animals were gavaged daily with RRE (at doses of 30 and 120 mg/kg, respectively) for 30 days after adjuvant injection (750 μg of Mycobacterium tuberculosis suspension in squalene). At the higher dose, animals treated with RRE had a lower incidence and severity of arthritis compared to control animals. Also, histological analyses revealed significant inhibition of inflammation, pannus formation, cartilage damage, and bone resorption by RRE. This study suggests that red raspberry polyphenols may afford cartilage protection and/or modulate the onset and severity of arthritis.
Article
Black raspberries have been shown to inhibit multiple stages of oral, esophageal, and colon cancer. The objective of this study was to evaluate how black raspberry extract variability conditioned by horticultural factors affected the antiproliferative activity of 75 black raspberry extracts using an in vitro colon cancer cell model. HT-29 cells grown in 96-well plates were treated with freeze-dried extracts at 0.6 and 1.2 mg of extract/mL of medium. Percent cell growth inhibition for each concentration of the extracts was determined using the sulforhodamine B assay. All extracts significantly inhibited the growth of HT-29 colon cancer cells in a dose-dependent manner. Cell proliferation was significantly influenced by cultivar, production site, and stage of maturity. The lack of correlation between growth inhibition and extract total phenolic and total monomeric anthocyanin assays suggested horticultural parameters influence bioactivity in a complex manner.
Article
The separation of anthocyanins present in the fruits of 11 varieties of red raspberries (Rubus idaeus L.) was performed by high performance liquid chromatography (HPLC) with a diode-array detector and evaporative light scattering detection (ELSD). The ELSD parameters--drift tube temperature, nebulising gas flow rate and gain value--were optimised to get the best detection and identification of the anthocyanins. The varieties Heritage and Willamette had the simplest anthocyanin sets consisting of only two predominant anthocyanins--cyanidin-3-O-sophoroside (1) and cyanidin-3-O-glucoside (3), while in the other varieties two other predominant compounds were also present, cyanidin-3-O-rutinoside (4) and cyanidin-3-O-(2(G)-O-glucosylrutinoside) (2). Moreover, using ELSD, simultaneous analysis of anthocyanins and sanguiin H-6 (5), an ellagitannin, was performed. The contents of anthocyanins and sanguiin H-6 (5) were estimated by HPLC with ultraviolet-visible (UV-vis) light detection. The determined concentrations of anthocyanins varied from 76.22 to 277.06 mg per 100 g of dry weight (d.w.). The content of sanguiin H-6 (5) was in the range from 135.04 to 547.48 mg per 100 g of d.w.
Article
A process was developed to ascertain the bioactive components of black raspberry (Rubus occidentalis L.) fruit extracts by relating chemical constituents determined by high-field nuclear magnetic resonance (NMR) spectroscopy to biological responses using partial least-squares regression analysis. To validate our approach, we outlined relationships between phenolic signals in NMR spectra and chemical data for total monomeric anthocyanin (TMA) content and antioxidant capacity by the ferric-reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays. Anthocyanins, cyanidin 3-O-rutinoside (Cy 3-rut), cyanidin 3-O-(2(G))-xylosylrutinoside (Cy 3-xylrut), and cyanidin 3-O-glucoside (Cy 3-glc), were significant contributors to the variability in assay results, with the two most important NMR bins corresponding to the methyl peaks in Cy 3-rut (6''') and/or Cy 3-xylrut (6(IV)). Many statistically important bins were common among assay models, but differences in structure-activity relationships resulted in changes in bin ranking. The specificity of these results supported the application of the process to investigate relationships among health-beneficial natural products and potential biological activity.
Article
Dietary guidelines around the world recommend the increased consumption of fruits and vegetables as good sources of antioxidant phytochemicals for the prevention of chronic diseases. Red raspberries are a common and important fruit in the Western diet due to their content of essential nutrients and beneficial phytochemicals. Anthocyanins and ellagitannins are polyphenolic compounds and the major antioxidant phytochemicals present in raspberries. Whereas individual phytochemical constituents of raspberries have been studied for their biological activities, human intervention studies using whole berries are lacking in the literature. The nutritional and phytochemical compositions of red raspberries and their absorption, metabolism, and biological activity are reviewed. Finally, future directions of research are also identified.
Article
Consumption of raspberries promotes human health through intake of pharmaceutically active antioxidants, including cyanidin and pelargonidin anthocyanins; products of flavonoid metabolism and also pigments conferring colour to fruit. Raspberry anthocyanin contents could be enhanced for nutritional health and quality benefits utilising DNA polymorphisms in modern marker assisted breeding. The objective was to elucidate factors determining anthocyanin production in these fruits. HPLC quantified eight anthocyanin cyanidin and pelargonidin glycosides: -3-sophoroside, -3-glucoside, -3-rutinoside and -3-glucosylrutinoside across two seasons and two environments in progeny from a cross between two Rubus subspecies, Rubus idaeus (cv. Glen Moy)xRubus strigosus (cv. Latham). Significant seasonal variation was detected across pigments less for different growing environments within seasons. Eight antioxidants mapped to the same chromosome region on linkage group (LG) 1, across both years and from fruits grown in field and under protected cultivation. Seven antioxidants also mapped to a region on LG 4 across years and for both growing sites. A chalcone synthase (PKS 1) gene sequence mapped to LG 7 but did not underlie the anthocyanin quantitative traits loci (QTL) identified. Other candidate genes including basic-helix-loop-helix (bHLH), NAM/CUC2-like protein and bZIP transcription factor underlying the mapped anthocyanins were identified.
Article
Raspberries are rich in phenolic phytochemicals. To study the health benefits of raspberries, four fresh raspberry varieties (Heritage, Kiwigold, Goldie, and Anne) were evaluated for total antioxidant and antiproliferative activities. The total amount of phenolics and flavonoids for each of the four raspberry varieties was determined. The Heritage raspberry variety had the highest total phenolic content (512.7 +/- 4.7 mg/100 g of raspberry) of the varieties measured followed by Kiwigold (451.1 +/- 4.5 mg/100 g of raspberry), Goldie (427.5 +/- 7.5 mg/100 g of raspberry), and Anne (359.2 +/- 3.4 mg/100 g of raspberry). Similarly, the Heritage raspberry variety contained the highest total flavonoids (103.4 +/- 2.0 mg/100 g of raspberry) of the varieties tested, followed by Kiwigold (87.3 +/- 1.8 mg/100 g of raspberry), Goldie (84.2 +/- 1.8 mg/100 g of raspberry), and Anne (63.5 +/- 0.7 mg/100 g of raspberry). The color of the raspberry juice correlated well to the total phenolic, flavonoid, and anthocyanin contents of the raspberry. Heritage had the highest a/b ratio and the darkest colored juice, and the Anne variety showed the lowest phytochemical content and the palest color. Heritage raspberry variety had the highest total antioxidant activity, followed by Kiwigold and Goldie, and the Anne raspberry variety had the lowest antioxidant activity of the varieties tested. The proliferation of HepG(2) human liver cancer cells was significantly inhibited in a dose-dependent manner after exposure to the raspberry extracts. The extract equivalent to 50 mg of Goldie, Heritage, and Kiwigold fruit inhibited the proliferation of those cells by 89.4 +/- 0.1, 88 +/- 0.2, and 87.6 +/- 1.0%, respectively. Anne had the lowest antiproliferative activity of the varieties measured but still exhibited a significant inhibition of 70.3+/- 1.2% with an extract equivalent to 50 mg of fruit. The antioxidant activity of the raspberry was directly related to the total amount of phenolics and flavonoids found in the raspberry (p < 0.01). No relationship was found between antiproliferative activity and the total amount of phenolics/flavonoids found in the same raspberry (p > 0.05).
Article
Analysis of extracts of Glen Ample raspberries (Rubus idaeus L.) by gradient, reverse phase HPLC with diode array and tandem mass spectrometry identified eleven anthocyanins, including cyanidin-3-sophoroside, cyanidin-3-(2(G)-glucosylrutinoside), cyanidin-3-glucoside, cyanidin-3-rutinoside, pelargonidin-3-sophoroside, pelargonidin-3-(2(G)-glucosylrutinoside), and pelargonidin-3-glucoside. Significant quantities of an ellagitannin, sanguiin H-6, with an M(r) of 1870 were detected along with lower levels of a second ellagitannin, lambertianin C, which has an M(r) of 2804. Other phenolic compounds that were detected included trace levels of ellagic acid and its sugar conjugates along with one kaempferol- and four quercetin-based flavonol conjugates. Fractionation by preparative HPLC revealed that sanguiin H-6 was a major contributor to the antioxidant capacity of raspberries together with vitamin C and the anthocyanins. Vasodilation activity was restricted to fractions containing lambertianin C and sanguiin H-6.
Article
The antioxidant activity of the six common anthocyanidins, pelargonidin, cyanidin, delphinidin, peonidin, petunidin, and malvidin, and their glycosidic forms was evaluated in three lipid-containing models [human low-density lipoprotein (LDL) and bulk and emulsified methyl linoleate]. In addition, the radical scavenging activity of the compounds against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical was studied. Most anthocyanins and their aglycons acted as strong antioxidants in emulsion and LDL. Many compounds showed an activity comparable to the well-known antioxidants alpha-tocopherol, Trolox, catechin, and quercetin. In bulk methyl linoleate, anthocyanins and anthocyanidins possessed only a weak antioxidant activity or even oxidation-promoting activity. Depending on the anthocyanidin, different glycosylation patterns either enhanced or diminished the antioxidant power. For the most part, the activities of the glycosides and the aglycons did not differ remarkably in emulsion. In LDL the aglycons showed in general higher activities than the glycosides. In bulk oil, to the contrary, the glycosides were more effective than the aglycons.
Article
High-performance liquid chromatography combined with diode array and electrospray ionization mass spectrometric detection was used to study soluble and insoluble forms of phenolic compounds in strawberries, raspberries (red and yellow cultivated and red wild), arctic bramble, and cloudberries. Hydroxycinnamic acids were present as free forms in cloudberries and mainly as sugar esters in the other berries. Quercetin 3-glucuronide was the typical flavonol glycoside in all of the berries studied. The composition of the predominant anthocyanins can be used to distinguish the studied red Rubus species from each other since cyanidin was glycosylated typically with 3-sophorose (56%) in cultivated red raspberry, with 3-sophorose (30%) and 3-glucose (27%) in wild red raspberry, and with 3-rutinose (80%) in arctic bramble. Ellagic acid was present as free and glycosylated forms and as ellagitannins of varying degrees of polymerization. Comparable levels of ellagitannins were obtained by the analysis of soluble ellagitannins as gallic acid equivalents and by the analysis of ellagic acid equivalents released by acid hydrolysis of the extracts.
Article
Anthocyanins were systematically identified and characterized by HPLC-ESI-MS/MS coupled with diode array detection in common fruits from U.S. food markets and other commercial sources. Of the 25 different fruits that were screened, 14 fruits were found to contain anthocyanins; the number of anthocyanins varied from 2 in peaches and nectarines to 31 in Concord grape. The individual anthocyanins were identified by comparing their mass spectral data and retention times with those of standards and published data. In all of the samples analyzed, only 6 common anthocyanidins, delphinidin, cyanidin, pelargonidin, petunidin, peonidin and malvidin, were found. In addition to the well-known major anthocyanins, a number of minor anthocyanins were identified for the first time. Some possible guidelines that help to identify anthocyanins in foods with complex anthocyanin composition were deduced and discussed. For the first time, this paper presents complete anthocyanin HPLC profiles and MS spectral data of common fruits using the same uniform experimental conditions.
Article
Rapeseed, raspberry, and pine bark are promising bioactive sources of plant phenolics selected from among ca. 100 previously screened plant materials for in vitro preclinical evaluation of health related effects. Phenolic extracts and isolated fractions of the selected materials were investigated for antioxidant, antimicrobial, antiinflammatory, and antimutagenic properties as well as for cell permeability. It was shown that rapeseed and pine bark phenolics and raspberry anthocyanins were good or excellent antioxidants toward oxidation of phosphatidylcholine membrane (liposomes), rapeseed oil (crude) phenolics were effective radical scavengers (DPPH test), and both raspberry and pine bark phenolics inhibited LDL oxidation. Rapeseed oil phenolics, principally vinylsyringol, raspberry anthocyanins, and pinoresinol and matairesinol, the principal components of pine bark phenolic isolate, were effective against formation of the proinflammatory mediator, prostaglandin E(2). Raspberry ellagitannins inhibited the growth of Proteus mirabilis and Klebsiella oxytoca. Pine bark and rapeseed had minor effects on the permeability of model drugs in Caco-2 experiments. None of the tested extracts were mutagenic nor toxic to Caco-2 cells or macrophages. Thus, phenolic isolates from rapeseed, raspberry, and pine bark and are safe and bioactive for possible food applications including functional foods intended for health benefit.
Article
In Finland, berries are part of the traditional diet significantly contributing to the intake of flavonoids and other phenolic compounds. Compositional data on phenolic compounds in berries has been rapidly accumulating and included in the national food composition database. Among the different bioactive substances in berries, phenolic compounds including flavonoids, tannins, and phenolic acids have received considerable interest due to their effects in food and health. A great amount of in vitro evidence exists showing that berry phenolics are powerful antioxidants. However, the antioxidant effect of berry phenolics is strongly dependent on the choice of berry raw material, as the antioxidant activity differs between the different phenolic constituents, including anthocyanins, ellagitannins, and proanthocyanidins. In foods, the antioxidant effect is also influenced by the structure of food. Tannin-containing berries exhibit antimicrobial properties against pathogenic bacteria, thus offering many new applications for food industry. Much of the interest in berry phenolics has focused on cranberries and both cultivated and wild blueberries, although also other berries including black currants, cloudberries, lingonberries, and red raspberries possess promising bioactivities that may have relevance to human health. Antioxidant activity of berry phenolics, in addition to other mechanisms, may contribute to human health, but the possible relationship remains yet to be scientifically substantiated.
Article
Plant polyphenolics continue to be the focus of attention with regard to their putative impact on human health. An increasing and ageing human population means that the focus on nutrition and nutritional enhancement or optimisation of our foodstuffs is paramount. Using the raspberry as a model, we have shown how modern metabolic profiling approaches can be used to identify the changes in the level of beneficial polyphenolics in fruit breeding segregating populations and how the level of these components is determined by genetic and/or environmental control. Interestingly, the vitamin C content appeared to be significantly influenced by environment (growth conditions) whilst the content of the polyphenols such as cyanidin, pelargonidin and quercetin glycosides appeared much more tightly regulated, suggesting a rigorous genetic control. Preliminary metabolic profiling showed that the fruit polyphenolic profiles divided into two gross groups segregating on the basis of relative levels of cyanidin-3-sophoroside and cyanidin-3-rutinoside, compounds implicated as conferring human health benefits.