Article

Concentrations of Anthocyanins in Common Foods in the United States and Estimation of Normal Consumption

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Abstract

Anthocyanins (ACNs) are water-soluble plant pigments that have important functions in plant physiology as well as possible health effects. Over 100 common foods were screened for ACNs, and 24 of them were found to contain ACNs. Concentrations of total ACNs varied considerably from 0.7 to 1480 mg/100 g of fresh weight in gooseberry ('Careless' variety) and chokeberry, respectively. Not only does the concentration vary, but the specific anthocyanins present in foods are also quite different. Only six common aglycones, delphinidin, cyanidin, petunidin, pelargonidin, peonidin, and malvidin, were found in all of these foods. However, their sugar moieties and acylation patterns varied from food to food. Results from this study will add to the available data for the USDA Nutrient Database of flavonoids. On the basis of the concentration data and updated food intake data from NHANES 2001-2002, the daily intake of ACNs is estimated to be 12.5 mg/day/person in the United States. Of the different aglycones, cyanidin, delphinidin, and malvidin were estimated to contribute 45, 21, and 15%, respectively, of the total ACN intake. Nonacylated contributed 77% compared to 23% from acylated ACNs.

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... ACNs are present in large quantities in red/blue fruits and vegetables, and their amount in plants varies significantly between species, depending on the cultivar or variety, growing region, climate, farming practices, harvesting period, ripening, seasonal variability, processing and storage, temperature, and light exposure. ACN levels in berries range from about 100 to roughly 700 mg/100 g of fresh product [44,45], with elderberries and chokeberries having the greatest amounts at up to 1.4-1.8 g/100 g. ...
... Purple corn, cherries, plums, pomegranates, eggplant, wine, grapes, and red/purple vegetables such as black carrots, red cabbage, and purple cauliflower are other excellent sources of ACNs [44,45]. These foods can have concentrations of as little as a few milligrams to as much as 200-300 mg/100 g of product. ...
... It has been estimated that the daily consumption of ACNs in the US is about 12.5 mg/day [45], whereas in Europe the mean intake ranges from 19 to 65 mg/day for males and from 18 to 44 mg/day for women [54]. However, estimating the daily intake of ACNs is difficult and imprecise, mostly because there is insufficient data on the quantities of ACNs in food. ...
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Anthocyanins are widespread and biologically active water-soluble phenolic pigments responsible for a wide range of vivid colours, from red (acidic conditions) to purplish blue (basic conditions), present in fruits, vegetables, and coloured grains. The pigments’ stability and colours are influenced mainly by pH but also by structure, temperature, and light. The colour-stabilizing mechanisms of plants are determined by inter- and intramolecular co-pigmentation and metal complexation, driven by van der Waals, π–π stacking, hydrogen bonding, and metal-ligand interactions. This group of flavonoids is well-known to have potent anti-inflammatory and antioxidant effects, which explains the biological effects associated with them. Therefore, this review provides an overview of the role of anthocyanins as natural colorants, showing they are less harmful than conventional colorants, with several technological potential applications in different industrial fields, namely in the textile and food industries, as well as in the development of photosensitizers for dye-sensitized solar cells, as new photosensitizers in photodynamic therapy, pharmaceuticals, and in the cosmetic industry, mainly on the formulation of skin care formulations, sunscreen filters, nail colorants, skin & hair cleansing products, amongst others. In addition, we will unveil some of the latest studies about the health benefits of anthocyanins, mainly focusing on the protection against the most prevalent human diseases mediated by oxidative stress, namely cardiovascular and neurodegenerative diseases, cancer, and diabetes. The contribution of anthocyanins to visual health is also very relevant and will be briefly explored.
... Anthocyanins are one of the major sources of color which provide the purple reddish hue to purple corn. Anthocyanin content in purple corn ranges from 6.8mg/g fresh weight to 82.3 mg/g fresh weight depending on the section analyzed (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006;Li et al., 2008). This content was higher than most of the known anthocyanin-rich plants based on fresh weight such as blueberries (1.3 to 3.8 mg/g) (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006), strawberries (0.21±0.03 mg/g) (Wang and Lin, 2000; Wu et al., 2006), red cabbage (3.22±0.41 ...
... Anthocyanin content in purple corn ranges from 6.8mg/g fresh weight to 82.3 mg/g fresh weight depending on the section analyzed (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006;Li et al., 2008). This content was higher than most of the known anthocyanin-rich plants based on fresh weight such as blueberries (1.3 to 3.8 mg/g) (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006), strawberries (0.21±0.03 mg/g) (Wang and Lin, 2000; Wu et al., 2006), red cabbage (3.22±0.41 mg/g) (Ahmadiani et al., 2014;Wu et al., 2006), eggplants (8.57 ...
... Anthocyanin content in purple corn ranges from 6.8mg/g fresh weight to 82.3 mg/g fresh weight depending on the section analyzed (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006;Li et al., 2008). This content was higher than most of the known anthocyanin-rich plants based on fresh weight such as blueberries (1.3 to 3.8 mg/g) (Cevallos-Casals and Cisneros-Zevallos, 2003;Wu et al., 2006), strawberries (0.21±0.03 mg/g) (Wang and Lin, 2000; Wu et al., 2006), red cabbage (3.22±0.41 mg/g) (Ahmadiani et al., 2014;Wu et al., 2006), eggplants (8.57 ...
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La creciente demanda de los consumidores de alimentos más nutritivos, ingredientes de origen natural y etiquetas más limpias está empujando a las industrias de alimentos y cosméticos a pasar del uso de colorantes artificiales a alternativas de origen natural. En este contexto, la industria busca continuamente fuentes de colorantes más estables, con especial interés en las fuentes vegetales. La vibrante biodiversidad que se encuentra en el Perú representa una emocionante oportunidad económica. En esta revisión, destacamos cultivos peruanos seleccionados con excelente potencial para su uso como fuentes de colorantes para aplicaciones industriales, con algunas fuentes que se estudian ampliamente y otras que reciben atención en años más recientes. El maíz morado, un cultivo nativo de la región de los Andes, es una rica fuente de pigmentos con gran estabilidad y una larga historia de uso en diferentes aplicaciones alrededor del mundo. Las papas de pulpa coloreada, cultivos andinos subutilizados, pueden expresar diferentes colores debido a sus perfiles de pigmentos variados. Sauco, la baya del saúco peruana, tiene una fuerte actividad antioxidante y un perfil de pigmento único que le da su característico color negro-púrpura. Las especies de Berberis, una clase diversa de arbustos con bayas altamente pigmentadas, se pueden usar directamente como aditivos de color sin necesidad de procedimientos de extracción. Huito, una fruta poco estudiada originaria del Amazonas es naturalmente incolora, pero puede volverse azul cuando se expone al oxígeno o a los aminoácidos y puede expresar diferentes tonalidades según la fuente del grupo de aminas primarias. En general, el maíz morado, las papas de pulpa coloreada, el sauco, las especies de Berberis y el huito son fuentes peruanas prometedoras de colorantes naturales para aplicaciones alimentarias y cosméticas debido a su versatilidad, estabilidad y atractivas características de color.
... According to the OECD Food Consumption Statistics for 1955-1971 and reported by Kühnau (1976) the average daily intake of ACNs was estimated to be as high as 185-215 mg/day/person (USA data), for winter and summer, respectively. However, Wu et al. (2006) estimated that the overall intake was 12.5 mg/day/person (USA data) (Table 1). This huge difference of total ACN daily intake estimation must result from different food intake data and not due to the ACN food content itself. ...
... Based on this previous study, the ACN monoglycosides contributed to 73.1% of total ACN daily intake, whereas diglycosides and triglycosides contributed only with 17.3 and 9.6%, respectively. Table 1 shows the estimation of daily consumption of ACN from several food sources according to the National Health and Nutrition Examination Survey (NHANES 2001(NHANES −2002 and reported by Wu et al. (2006). Nevertheless, methodological differences in extracting and analysing the target compounds, as well as nutritional, social and cultural differences of the populations, may also explain the wide range of ACN consumption estimated in different studies. ...
Chapter
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Since ancient times, human beings have consumed plants, and different cultures have found many health benefits from them. These have been attributed to the magical powers that plants possess or to the divine intervention of gods. However, since the advent of science and research, it has been found that these curative benefits come from a high content of secondary metabolites such as anthocyanins, flavonoids, terpenes, and phenols, among many other compounds, whose biological and pharmacological activity has been proven. Various African, Asian, and pre-Columbian cultures, among others, have understood the healing powers of many plants from ancestral knowledge. In this chapter, we present a brief description report about the use of the anthocyanin content of some fruits, flowers, barks, and herbs. The applications of these plants in traditional medicine and some scientific research that support the traditional uses is also presented.
... While various anthocyanins are present in many common berries, blackcurrants have been shown to be a particularly good source of anthocyanins [33], a type of flavonoid responsible for the red/purple color of many berries. Anthocyanins have been shown to improve blood glucose control and other risk factors associated with MetS [34]. ...
... Furthermore, studies should look to use commercially available juices and extracts when conducting trials, as these are reflective of what is applicable for the consumer. Most of the studies evaluating the effects of blackcurrant anthocyanins on biomarkers of MetS have used blackcurrants and blackcurrant extracts from New Zealand, which have reported higher anthocyanin levels [71] than non-New Zealand fruit/juice [33]. It is speculative to suggest that New Zealand blackcurrant could be more beneficial in managing MetS and its risk factors, but more research on this possibility in well-designed RCTs is required. ...
... The phenolic range is from 114 to 1056 mg/100FW. Anthocyanins are the main cyanidin derivatives which are rutinose, xylose, and glucose attached at C3. [53] Cranberry also consists of phenolic contents like hydroxycinnamic and hydroxybenzoic acids [54,55] and much lower contents of o-hydroxybenzoic acids, 2,4-dihydroxybenzoic, p-hydroxybenzoic. The main contents of hydroxycinnamic acids present in cranberry are sinapic, p-coumaric, ferulic acids and caffeic acid. ...
... There is a chance of variation in this approach seems to affect the health properties and bioavailability of anthocyanins. [53] Ellagitannins Ellagitannins are distinctive aggregates of hexahydroxydiphenic and gallic acid in combination with glucose, available with an extensive variety of chemical structures, for example, monomers (such as ellagic acid glycosides), oligomers (such as sanguiin H-6, the common ellagitannins present in the strawberry) and multiplex polymers. A combination of ellagitannins and gallotannins is known as hydrolyzable tannins, and ellagic acid is produced as a result of hydrolysis, except ellagic acid other metabolites can also be synthesized. ...
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In millennia, berries have captured great attention owing to their broad spectrum of functional as well as therapeutic activities, which is due to presence of their bioactive compounds. All edible forms of berries show important nutritional properties leading to their therapeutic potential and are considered as safe functional foods. Recently, various researches for further exploration of berries concerning nutritional and bioactive profiles as well as potential health benefits are on the way. This review highlights the latest research on bioactive compounds of all edible forms of berries and their related nutritional activities in humans and animals against different diseases. The current article revealed that berries have an array of bioactive moieties including phenolics, anthocyanins and ellagitannins with strong antioxidant potential contributing to their anti-cancer, anti-diabetic, anti-inflammatory and cardio-protective roles. The demand and consumption trend is increasing day by day, due to their therapeutic effects as mentioned above.
... However, the highest losses reaching even 80% were recorded for anthocyanins, converted to cyanidin 3-glucoside (Nelson F1 cultivar after cooking). These compounds are very soluble in water (Wu et al., 2006) so it should be expected that their losses will be higher for thermal operations carried out in the presence of water (cooking, blanching) and at increased water activity (freezing), which is confirmed by the obtained results. ...
... To this should be added that the estimated exposure of the European population to anthocyanins from the regular diet is very low (at the mean about 0.1 mg/kg bw/day for adults and 0.3 mg/ kg bw/day for children) (EFSA, 2013). The daily intake of anthocyanins is estimated to be 12.5 mg/day/person in the United States (Wu et al., 2006). On the other hand, the consumption of 160 mg of anthocyanins twice a day for 1 to 2 months showed no adverse health effects, revealing that in most individuals anthocyanins are well-tolerated (He and Giusti, 2010). ...
... The total anthocyanin concentration of the developed line 'Tim1' at eating stage (23 DAP) in this current research (140.51 mg/100 g FW) (Fig. 4a) was significantly higher (P < 0.05) than anthocyanin found in other crops, for example, coloured strawberries (60 mg/100 g FW) 29 , red plums (30.1 mg/100 g FW) 30 , and red currants (12.8 mg/100 g FW) 31 , in which anthocyanin concentrations were not as high as in the purple-pericarp super-sweetcorn line, 'Tim1' . ...
Article
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The existence of purple-pericarp super-sweetcorn based on the supersweet mutation, shrunken2 ( sh2 ), has not been previously reported, due to its extremely tight genetic linkage to a non-functional anthocyanin biosynthesis gene, anthocyaninless1 ( a1 ). Generally, pericarp-pigmented starchy purple corn contains significantly higher anthocyanin. The development of purple-pericarp super-sweetcorn is dependent on breaking the a1–sh2 tight genetic linkage, which occurs at a very low frequency of < 1 in 1000 meiotic crossovers. Here, to develop purple-pericarp super-sweetcorn, an initial cross between a male purple-pericarp maize, ‘Costa Rica’ ( A1Sh2.A1Sh2 ) and a female white shrunken2 super-sweetcorn, ‘Tims-white’ ( a1sh2.a1sh2 ), was conducted. Subsequent self-pollination based on purple-pericarp-shrunken kernels identified a small frequency (0.08%) of initial heterozygous F3 segregants ( A1a1.sh2sh2 ) producing a fully sh2 cob with a purple-pericarp phenotype, enabled by breaking the close genetic linkage between the a1 and sh2 genes. Resulting rounds of self-pollination generated a F6 homozygous purple-pericarp super-sweetcorn ( A1A1.sh2sh2 ) line, ‘Tim1’. Genome sequencing revealed a recombination break between the a1 and yz1 genes of the a1–yz1-x1–sh2 multigenic interval. The novel purple-pericarp super-sweetcorn produced a similar concentration of anthocyanin and sugar as in its purple-pericarp maize and white super-sweetcorn parents, respectively, potentially adding a broader range of health benefits than currently exists with standard yellow/white sweetcorn.
... Red cabbage is a rich source of anthocyanins, has a long shelf-life, and its extract is easy to prepare making red cabbage a sustainable and potential material for smart packaging [14,28]. The anthocyanin profile of red cabbage is very complex, more than 20 anthocyanin pigments can be identified [14,29,30], which is due to the glycosylation of the cyanidin with two different sugars and acylation with different aromatic acids [31]. The main anthocyanin found to be cyanidin-3-O-diglucoside-5-O-glucoside, which can be mono-or diacylated with the presenting sinapic, ferulic, caffeic and p-coumaric acids [14]. ...
Article
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Color-based time-temperature indicators (TTIs) can show the time and temperature changes of an environment with a visually recognizable color change. Made from natural dyes, these TTIs are simple, inexpensive and sustainable. In this study, cellulose-based TTI labels were prepared with red cabbage extract of pH2, pH7 and pH9 to determine how pH alter the response of the labels to time and temperature changes. This study also aimed to determine the relationship between color change and time at different temperatures. The color responses of the labels were followed spectrophotometrically by measuring the CIE Lab color coordinates and by giving the total color difference at 4 °C, 23 °C, 40 °C, 80 and 100 °C after increments of time. The best fitting linear or nonlinear regression models of the CIE Lab coordinates, total color difference and time data as a function of temperature were also determined. The labels prepared with red cabbage extract at different pH behaved differently. Opposite to expectations, the acidic, pink colored labels did not have the highest color stability. Our finding was, that the label prepared with the acidic red cabbage extract is the most suitable as time-temperature label for indicating long-term temperature storage and the label prepared with the neutral red cabbage extract is the most suitable as time-temperature label for indicating short-term storage by color change. According to the results the color changes of the labels are predictable with the fitted models with a correlation coefficient between 0.96 and 1.
... Anthocyanidins are sugar-free anthocyanins with an aromatic A ring bound to a heterocyclic C ring with oxygen. The C ring is linked to a third aromatic ring B via a carboncarbon bond [77]. The absence of a ketone group at position 4 on the C ring distinguishes anthocyanidins from flavonols and flavanones. ...
Article
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Flavonoids, a group of natural compounds with phenolic structure, are becoming popular as alternative medicines obtained from plants. These compounds are reported to have various pharmacological properties, including attenuation of inflammatory responses in multiple health issues. Epilepsy is a disorder of the central nervous system implicated with the activation of the inflamma-tory cascade in the brain. The aim of the present study was to summarize the role of various neu-roinflammatory mediators in the onset and progression of epilepsy, and, thereafter, to discuss the flavonoids and their classes, including their biological properties. Further, we highlighted the modulation of anti-inflammatory responses achieved by these substances in different forms of epilepsy, as evident from preclinical studies executed on multiple epilepsy models. Overall, the review summarizes the available evidence of the anti-inflammatory potential of various flavonoids in epilepsy.
... We found that cyanidin-3-O-beta-glucopyranoside (cyanidin 3glucoside, C3G) and its congener malvidin 3-glucoside (M3G) (but not peonidin 3-glucoside, P3G) are the only molecules that inhibit the uptake of BR in the female rat liver. Both belong to the anthocyanin family (a subclass of flavonoids) and are found in red berries, black rice, and red wine, among others [10]. Both are competitive inhibitors [11] of bilitranslocase (TCDB 2.A.65.1.1), ...
Article
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One of the organ-specific functions of the liver is the excretion of bilirubin into the bile. Membrane transport of bilirubin from the blood to the liver is not only an orphan function, because there is no link to the protein/gene units that perform this function, but also a poorly characterised function. The aim of this study was to investigate the pharmacology of bilirubin uptake in the liver of the female Wistar rat to improve basic knowledge in this neglected area of liver physiology. We treated isolated perfused livers of female rats with repeated single-pass, albumin-free bilirubin boli. We monitored both bilirubin and bilirubin glucuronide in perfusion effluent with a bio-fluorometric assay. We tested the ability of nine molecules known as substrates or inhibitors of sinusoidal membrane transporters to inhibit hepatic uptake of bilirubin. We found that cyanidin 3-glucoside and malvidin 3-glucoside were the only molecules that inhibited bilirubin uptake. These dietary anthocyanins resemble bromosulfophthalein (BSP), a substrate of several sinusoidal membrane transporters. The SLCO-specific substrates estradiol-17 beta-glucuronide, pravastatin, and taurocholate inhibited only bilirubin glucuronide uptake. Cyanidin 3-glucoside and taurocholate acted at physiological concentrations. The SLC22-specific substrates indomethacin and ketoprofen were inactive. We demonstrated the existence of a bilirubin-glucuronide transporter inhibited by bilirubin, a fact reported only once in the literature. The data suggest that bilirubin and bilirubin glucuronide are transported to the liver via pharmacologically distinct membrane transport pathways. Some dietary anthocyanins may physiologically modulate the uptake of bilirubin into the liver.
... Anthocyanins are water-soluble pigments that provide red, blue, and violet hues to eggplants, blueberries, purple corn, and geraniums, among others. [1], [2]. These chemical compounds that biosynthesize plants perform non-essential functions in them. ...
Article
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Radish (Raphanus sativus L. var Crimson Gigant) contains significant quantities of glycosylated anthocyanins, it can be used as natural food colorants due to their high stability. These pigments have therapeutic and pharmacological characteristics that are associated to antioxidant activity. Furthermore, the pigments of radish are important for nutritional and medicinal uses, for all the benefits that they provide to human health. The objective of this research was to extract anthocyanins from the shell of radish in pure form, evaluate its antioxidant activity in vitro and then use it as a food coloring in natural yogurt. For sample extraction, the radish shell was separated by finely cutting it from the body of the radish, it was macerated with an acidified solution of methanol-water and evaporated by 80%. The extract was absorbed with an ion exchange resin, subsequently the anthocyanins were released in an acidified solution, finally the extracts were purified by reverse phase column chromatography. 14 fractions were obtained and were monitored by thin layer chromatography, afterwards antioxidant activity was evaluated by methods such as DPPH, ABTS and TBARS. A stable cherry powder was obtained, which was used as a yogurt colorant and was very well accepted by the judges.
... It has the advantages of drought resistance, vigorous growth, and easy reproduction [2,3]. The fruits are rich in nutrients such as sugars, vitamin C, vitamin E, polyphenols, and flavonoids [4,5] and have extremely high nutritional and medicinal value, including antibacterial, anti-inflammatory, antioxidant and antiaging effects [6,7]. These fruits are widely used in medical and health care fields with good prospects for further applications. ...
Article
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As an emerging third-generation fruit, blackberry has high nutritional value and is rich in polyphenols, flavonoids and anthocyanins. Flavonoid biosynthesis and metabolism is a popular research topic, but no related details have been reported for blackberry. Based on previous transcriptome data from this research group, two blackberry flavonol synthase genes were identified in this study, and the encoded proteins were subjected to bioinformatics analysis. RuFLS1 and RuFLS2 are both hydrophobic acidic proteins belonging to the 2OG-Fe(II) dioxygenase superfamily. RuFLS2 was expressed at 27.93-fold higher levels than RuFLS1 in red–purple fruit by RNA-seq analysis. Therefore, RuFLS2-overexpressing tobacco was selected for functional exploration. The identification of metabolites from transgenic tobacco showed significantly increased contents of flavonoids, such as apigenin 7-glucoside, kaempferol 3-O-rutinoside, astragalin, and quercitrin. The high expression of RuFLS2 also upregulated the expression levels of NtF3H and NtFLS in transgenic tobacco. The results indicate that RuFLS2 is an important functional gene regulating flavonoid biosynthesis and provides an important reference for revealing the molecular mechanism of flavonoid accumulation in blackberry fruit.
... The content of malvidin-based anthocyanins in blueberries is much higher than those of petunidin-, delphinidin-, or cyanidinbased anthocyanins (Wang et al., 2008). Of the secondary plant metabolites found in blueberries, the anthocyanins have received the most attention (Gao and Mazza, 1994;Wu et al., 2006); although flavonols (predominantly quercetin derivatives), phenolic acids (caffeic, chlorogenic, pcoumaric and ferulic acid) and proanthocyanidins are also present (Moyer et al., 2002;Taruscio et al., 2004). In addition to anthocyanins, blueberries are also one of the richest sources of chlorogenic acid, quercetin, kaempferol, myricetin, procyanidins, catechin, epicatechin, resveratrol, and vitamin C with antioxidant activity. ...
Thesis
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Abstract Berries are highly valued crops due to their unique flavour, texture, colour and phytochemicals. They are rich in phenolic compounds which have been recognized as having beneficial health effects in humans. Phenolic compounds are present in the free, soluble ester and insoluble-bound forms; these were extracted using four different solvents {methanol–acetone–water (7:7:6, v/v/v), acetone-water (80: 20, v/v), methanol-water (70: 30, v/v), and water}. The insoluble-bound phenolics were procured after alkaline hydrolysis and subsequent extraction into diethyl ether-ethyl acetate. Phenolic extracts of each fraction were separately assayed for their antioxidant activity using several methods, namely oxygen radical absorbance capacity (ORAC), the reducing power capacity, as well as iron (II) chelation capacity, among others. There were significant differences in the total content of phenolics, flavonoids, and anthocyanins between blackberry, black raspberry, and blueberry seed meals. The bound phenolics contributed the highest proportion to the total contents of different classes of phenolics. Furthermore, blackberry seed meals had higher total antioxidant activity compared with black raspberry and blueberry seed meals in all assays employed. High-performance liquid chromatography−diode array detection−electrospray ionization multistage mass spectrometry (HPLC-DAD-ESI-MSn) was used to identify and quantify the phenolic compounds. Hydroxybenzoic and hydroxycinnamic acids, anthocyanins, flavonols, flavan-3-ols, and proanthocyanidins were identified and quantified in the aforementioned fractions. Extracts were found to contain various levels of phenolic compounds that were specific to each berry seed meal type.
... This is confirmed by the reports in common berries including blue honeysuckle, grape, haskap and sweet cherry [3,[48][49][50], where 3-monoglycosyl-anthocyanins are the primary anthocyanins, and 3,5-diglycosylanthocyanins are present only in a small proportion. The most common naturally occurring anthocyanidins are cyanidin (Cy, 50%), Dp (12%), Pn (12%), pelargonidin (Pg, 12%), Mv (7%) and Pt (7%) ( Figure 1A) [47], and Pt is rarely present in berries [51]. However, Pt is the major component of black goji anthocyanidins, followed by Mv and Dp, with average contents of 5.71, 0.47 and 0.29 mg/g DW, respectively [1]. ...
Article
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Lycium ruthenicum is a therapeutic plant and its fruits (black goji) are commonly used as a traditional Chinese medicine. This review comprehensively discusses the recent research developments of black goji anthocyanins (BGAs), including chemical compositions, biosynthesis, color properties and health benefits. Among the 39 identified BGAs, most are 3,5-diglycoside derivatives of petunidin (>95%) with an individual anthocyanin [petunidin 3-O-rutinoside (trans-p-coumaroyl)-5-O-glucoside], accounting for 80% of the total BGAs. Due to their unique anthocyanin profile, BGAs possess various health benefits, including antioxidant activities, α-glucosidase inhibiting activity, alleviating insulin resistance, improving mitochondrial function, anti-inflammatory effects, etc., and therefore have the potential to treat a range of chronic diseases, such as type 2 diabetes mellitus, memory disorders, stroke, colitis, atherosclerosis, cardiovascular and cerebrovascular diseases. In addition, BGAs exhibit a pH-dependent “red-purple-blue” pattern of color change and thus could be used as natural colorants and to prepare smart food packaging materials. This review is valuable for broad applications of BGAs as promising natural colorants, functional foods and potential herbal medicines.
... However, Zamora-Ros et al. [50] reported that the daily intake of anthocyanins in Europe ranges from 19.3 to 64.88 mg in men and from 18.73 to 44.08 mg in women. In contrast, in the United States of America (USA), daily consumption ranges from 180-215 mg [51]. Among anthocyanin-rich sources, in Europe, apples, berries, grapes, and pears (50%), and red wine (21%) are the main contributors to daily anthocyanin intake, while in the USA, berries, wine, grapes, and bananas (20,16,11, and 11%, respectively) are the main sources [52]. ...
Article
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Anthocyanins are among the best-known phenolic compounds and possess remarkable biological activities, including antioxidant, anti-inflammatory, anticancer, and antidiabetic effects. Despite their therapeutic benefits, they are not widely used as health-promoting agents due to their instability, low absorption, and, thus, low bioavailability and rapid metabolism in the human body. Recent research suggests that the application of nanotechnology could increase their solubility and/or bioavailability, and thus their biological potential. Therefore, in this review, we have provided, for the first time, a comprehensive overview of in vitro and in vivo studies on nanocarriers used as delivery systems of anthocyanins, and their aglycones, i.e., anthocyanidins alone or combined with conventional drugs in the treatment or management of chronic diseases.
... Data of vitamin C content reported by a Delva & Schneider (2013), b Mezadri et al. (2008), d Mieszczakowska-Frąc et al. (2021) Data of -carotene content reported by b Mezadri et al. (2018), e Kandlakunta et al. (2008), f Kha et al. (2013), g Elvira-Torales et al. (2019) Data of anthocyanin content reported by a Delva & Schneide (2013), b Mezadri et al. (2008), h Wu et al. (2006). Data of antioxidant activity reported by a Delva & Schneider (2013) By-products of fruits were picked up from peels, seeds, and unused flesh that were generated by different steps of the industrial process. ...
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Various studies have evaluated that acerola fruit is one of the best natural sources of vitamin- C. Besides that, the fruits also contain a high level of phenolic and carotenoids. The result tested in vitro performed that acerola extract can be antioxidative, anti-inflammatory, antihyperglycemic, antitumor antigenotoxic and hepatoprotective activity. The techniques such as pasteurization, fermentation, extraction, drying, encapsulation can diversify acerola products.
... However, Zamora-Ros et al. [50] reported that the daily intake of anthocyanins in Europe ranges from 19 in women. In contrast, in the United States of America (USA), daily consumption ranges from 180-215 mg [51]. Among anthocyanin-rich sources, in Europe, apples, berries, grapes, and pears (50%), and red wine (21%) are the main contributors to daily anthocyanin intake, while in the USA, berries, wine, grapes, and bananas (20, 16, 11, and 11%, respectively) are the main sources [52]. ...
Preprint
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Anthocyanins are among the best-known phenolic compounds and possess remarkable biological activities, including antioxidant, anti-inflammatory, anticancer, and antidiabetic effects. Despite their therapeutic benefits, they are not widely used as health-promoting agents due to their insta-bility, low absorption, and thus, low bioavailability and rapid metabolism in the human body. Recent research suggests that the application of nanotechnology could increase their solubility and/or bioavailability, and thus, their biological potential. Therefore, in this review, we decided to provide, for the first time, a comprehensive overview of in vitro and in vivo studies on nanocarriers used as delivery systems of anthocyanins, and their aglycones, i.e., anthocyanidins alone or com-bined with conventional drugs to the treatment or management of chronic diseases.
... They play crucial roles in plants via enhancing their survivability as free radical scavengers and light filters besides their contribution to pollination and seed dispersal as attractants for insects [19][20][21]. They are also important components of the human diet with a daily intake of 12.5 mg in the United States [22] and 19.8-64.9 mg in men and 18.4-44.1 mg in women in Europe [23]. ...
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Tea is the first most popular beverage worldwide and is available in several selections such as black (fully oxidized), Oolong (partially oxidized) and green (non-oxidized), in addition to purple tea, an emerging variety derived from the same tea plant (Camellia sinensis). This study investigated purple tea leaves (non-oxidized) and flakes (water extractable) to thoroughly identify their composition of anthocyanins and catechins and to study the effect of a water extraction process on their compositional properties in comparison with green tea. Anthocyanin and catechin compounds were separated and quantified using UPLC, and their identity was confirmed using LC-MS/MS in positive and negative ionization modes. Delphinidin was the principal anthocyaninidin in purple tea, while cyanidin came in second. The major anthocyanin pigments in purple tea were delphinidin-coumaroyl-hexoside followed by delphinidin-3-galactoside and cyanidin-coumaroyl-hexoside. The water extraction process resulted in substantial reductions in anthocyanins in purple tea flakes. There were no anthocyanin compounds detected in green tea samples. Both purple and green tea types were rich in catechins, with green tea containing higher concentrations than purple tea. The main catechin in purple or green tea was epigallocatechin gallate (EGCG) followed by either epicatechin gallate (ECG) or epigallocatechin (EGC), subject to tea type. The extraction process increased the concentration of catechins in both purple and green tea flakes. The results suggest that purple tea holds promise in making healthy brews, natural colorants and antioxidants and/or functional ingredients for beverages, cosmetics and healthcare industries due to its high content of anthocyanins and catechins.
... The results indicate that the extraction HCl/ethanol (1:99 v/v) constitutes a suitable method for obtaining these bioactives; it is even 50% more efficient than ATPE, a method that is typically used for its selectivity [25,26]. Other commercially recognized berries such as elderberry (Sambucus nigra) and chokeberry (Aronia spp.) presented values of 1375 and 1480 mg C3G eq./100 g FW, respectively [27]. On the basis of our results, it is possible to consider that H. macrocarpa berries are an important source of anthocyanins. ...
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This study investigated the effect of different storage temperatures (35-55 °C) on the bio-active substances and antioxidant properties of Hyeronima macrocarpa berries loaded on nanocellu-lose. NC was extracted from banana pseudo-stems and presented an interesting surface and poros-ity properties. The acidified ethanol extract showed better anthocyanin extraction (1317 mg C3G eq./100 g FW) and was used for the preparation of the powdered product, which presented an intense and uniform magenta color, with CIELAB parameters of L* = 59.16, a* = 35.61, and b* = 7.08. The powder exhibited significant stability at storage temperatures of 35 and 45 °C, in which there was no significant loss of anthocyanins or a decrease in antioxidant capacity. In addition, the color was stable for up to 4 months without adding any preservative agent. The anthocyanin-rich extract of H. macrocarpa reached an estimated shelf-life of 315 days (stored at 35 °C), as a result of the im-pregnation process between the extract and NC, with the ability to protect the bioactives from degradation , due to NC surface properties.
... These compounds are generally recognized as safe, due to the long history of use and consumption of foods rich in flavonoids. The total daily intake of flavonoids in Europe is estimated to be around 428 ± 49 mg, with 136 ± 14 mg being monomeric [135,139], while flavonoid-rich beverages and vegetables can reach 1,000 mg/day of flavonoids [135,140]. ...
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Some fruits and vegetables, rich in bioactive compounds such as polyphenols, flavonoids, and anthocyanins, may inhibit platelet activation pathways and therefore reduce the risk of suffering from CVD when consumed regularly. Aristotelia chilensis Stuntz (Maqui) is a shrub or tree native to Chile with outstanding antioxidant activity, associated with its high content in anthocyanins, polyphenols, and flavonoids. Previous studies reveal different pharmacological properties for this berry, but its cardioprotective potential has been little studied. Despite having an abundant composition, and being rich in bioactive products with an antiplatelet role, there are few studies linking this berry with antiplatelet activity. This review summarizes and discusses relevant information on the cardioprotective potential of Maqui, based on its composition of bioactive compounds, mainly as a nutraceutical antiplatelet agent. Articles published between 2000 and 2022 in the following bibliographic databases were selected: PubMed, ScienceDirect, and Google Scholar. Our search revealed that Maqui is a promising cardiovascular target since extracts from this berry have direct effects on the reduction in cardiovascular risk factors (glucose index, obesity, diabetes, among others). Although studies on antiplatelet activity in this fruit are recent, its rich chemical composition clearly shows that the presence of chemical compounds (anthocyanins, flavonoids, phenolic acids, among others) with high antiplatelet potential can provide this berry with antiplatelet properties. These bioactive compounds have antiplatelet effects with multiple targets in the platelet, particularly, they have been related to the inhibition of thromboxane, thrombin, ADP, and GPVI receptors, or through the pathways by which these receptors stimulate platelet aggregation. Detailed studies are needed to clarify this gap in the literature, as well as to specifically evaluate the mechanism of action of Maqui extracts, due to the presence of phenolic compounds.
... Recent observations revealed that consumption of polyphenol-rich fruits can affect the bileacidome [13,14]. Blueberries are highly concentrated in anthocyanins, a type of polyphenol that give the characteristic colors of the berries [15] and are known to influence the microbiome [16,17]. Based on these observations, we hypothesized that the consumption of blueberry extracts may have significant impacts on the fecal bileacidome. ...
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Cholesterol-derived bile acids (BAs) affect numerous physiological functions such as glucose homeostasis, lipid metabolism and absorption, intestinal inflammation and immunity, as well as intestinal microbiota diversity. Diet influences the composition of the BA pool. In the present study, we analyzed the impact of a dietary supplementation with a freeze-dried blueberry powder (BBP) on the fecal BA pool composition. The diet of 11 men and 13 women at risk of metabolic syndrome was supplemented with 50 g/day of BBP for 8 weeks, and feces were harvested before (pre) and after (post) BBP consumption. BAs were profiled using liquid chromatography coupled with tandem mass spectrometry. No significant changes in total BAs were detected when comparing pre- vs. post-BBP consumption samples. However, post-BBP consumption samples exhibited significant accumulations of glycine-conjugated BAs (p = 0.04), glycochenodeoxycholic (p = 0.01), and glycoursodeoxycholic (p = 0.01) acids, as well as a significant reduction (p = 0.03) in the secondary BA levels compared with pre-BBP feces. In conclusion, the fecal bileacidome is significantly altered after the consumption of BBP for 8 weeks. While additional studies are needed to fully understand the underlying mechanisms and physiological implications of these changes, our data suggest that the consumption of blueberries can modulate toxic BA elimination.
... Raspberries, blackberries, strawberries and blueberries contain from 20-690 mg/100 g serving, while even higher amounts are in elderberry and chokeberry (410-1800 mg/100 g serving [165,166]. Amounts in a 100 g serving of other fruits and vegetables include red cabbage (322 mg), red onion (49 mg), red grape (27 mg), apple (12 mg), peach (5 mg) and red bean (7 mg) [167]. Purple potato contains up to 16 mg per gram dry weight [168]. ...
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Many environmental stresses cause an increase in reactive oxygen species in plants and alter their nutritional value. Plants respond to many stresses by producing increased amounts of compounds with antioxidant properties including vitamins, phenylpropanoids and carotenoids. Such compounds have wide-ranging health-promoting effects in humans that are partly due to their antioxidant function because oxidative stress underlies many human diseases. Some of these compounds have complex interactions with the gut, promoting gut health and changing the gut microbiome, whereas the gut influences the bioavailability of the ingested compounds and may metabolize them into products with different effects on health than the original compound. Substantial efforts have been made to increase the nutritional value of crops through breeding or transgenic approaches, but comparatively little effort has been directed towards increasing nutritional value through crop management and environment, which may present another approach to enhance the nutritional quality.
... The results of a systematic review showed that vitamin C, a drug candidate with antioxidant capacity, has the ability to prevent the occurrence of UTI, and anthocyanins can inhibit ROS to treat UTI caused by K.pneumoniae and P.aeruginosa (157,158). Among the anthocyanin extracts of all plants, blueberry is an excellent candidate because of its very rich anthocyanin content (159,160). We conclude that reducing the content of ROS through the use of antioxidant drugs is a promising intervention for bladder infection. ...
Article
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Urinary tract infection (UTI) caused by uropathogens is the most common infectious disease and significantly affects all aspects of the quality of life of the patients. However, uropathogens are increasingly becoming antibiotic-resistant, which threatens the only effective treatment option available-antibiotic, resulting in higher medical costs, prolonged hospital stays, and increased mortality. Currently, people are turning their attention to the immune responses, hoping to find effective immunotherapeutic interventions which can be alternatives to the overuse of antibiotic drugs. Bladder infections are caused by the main nine uropathogens and the bladder executes different immune responses depending on the type of uropathogens. It is essential to understand the immune responses to diverse uropathogens in bladder infection for guiding the design and development of immunotherapeutic interventions. This review firstly sorts out and comparatively analyzes the immune responses to the main nine uropathogens in bladder infection, and summarizes their similarities and differences. Based on these immune responses, we innovatively propose that different microbial bladder infections should adopt corresponding immunomodulatory interventions, and the same immunomodulatory intervention can also be applied to diverse microbial infections if they share the same effective therapeutic targets.
... In the case of blueberries, studies have shown that their consumption induces positive effects on cognitive, vascular, and gluco-regulatory functions (Krikorian et al., 2010;Whyte et al., 2018;Kalt et al., 2020). Blueberries are among the fruits with the highest content of anthocyanins, pigments from the flavonoids family, which have antioxidant properties (Wu et al., 2006;Kalt et al., 2020). These health benefits may explain why the global demand for blueberries is increasing worldwide (Brazelton, 2013). ...
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Thermal pruning was a common pruning method in the past but has progressively been replaced by mechanical pruning for economic reasons. Both practices are known to enhance and maintain high yields; however, thermal pruning was documented to have an additional sanitation effect by reducing weeds and fungal diseases outbreaks. Nevertheless, there is no clear consensus on the optimal fire intensity required to observe these outcomes. Furthermore, fire is known to alter the soil microbiome as it impacts the soil organic layer and chemistry. Thus far, no study has investigated into the effect of thermal pruning intensity on the wild blueberry microbiome in agricultural settings. This project aimed to document the effects of four gradual thermal pruning intensities on the wild blueberry performance, weeds, diseases, as well as the rhizosphere fungal and bacterial communities. A field trial was conducted using a block design where agronomic variables were documented throughout the 2-year growing period. MiSeq amplicon sequencing was used to determine the diversity as well as the structure of the bacterial and fungal communities. Overall, yield, fruit ripeness, and several other agronomical variables were not significantly impacted by the burning treatments. Soil phosphorus was the only parameter with a significant albeit temporary change (1 month after thermal pruning) for soil chemistry. Our results also showed that bacterial and fungal communities did not significantly change between burning treatments. The fungal community was dominated by ericoid mycorrhizal fungi, while the bacterial community was mainly composed of Acidobacteriales, Isosphaerales, Frankiales, and Rhizobiales. However, burning at high intensities temporarily reduced Septoria leaf spot disease in the season following thermal pruning. According to our study, thermal pruning has a limited short-term influence on the wild blueberry ecosystem but may have a potential impact on pests (notably Septoria infection), which should be explored in future studies to determine the burning frequency necessary to control this disease.
... Compared to black chokeberry fruits, apples have a low anthocyanin content, that, depending on the cultivar, may vary in the range of 1.3-12.3 mg/100 g [35]. In adition, anthocyanins are present in apples mainly in the skin; therefore, they are partially removed during juice processing. ...
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Black chokeberries are a valuable source of anthocyanins and other phenolic compounds, but they are underutilized due to their unpalatable astringent taste. The aim of this study was to determine the potential of using black chokeberry juice as a health-promoting ingredient in apple juice with a view to develop a new functional food product and to increase the dietary consumption of bioactive compounds. Mixed juices were prepared from apple (A) juice and black chokeberry (BC) juice at 95:5 (ABC5), 90:10 (ABC10), 85:15 (ABC15), and 80:20 (ABC20) volumetric ratios. Comparative studies on the effect of heat treatment (90 °C, 10 min) and storage (four months, 20 °C) on the physicochemical and antioxidant properties of apple, black chokeberry, and mixed juices were carried out. The soluble solids content, titratable acidity, total phenolic, total anthocyanin and ascorbic acid content, and antioxidant activity increased while the total soluble solids/titratable acidity ratio decreased with increasing addition levels of BC juice. Mixing A juice with BC juice at 95:5 and 90:10 volumetric ratios improved the color and enhanced the palatability and general acceptability of the juice. The percentage losses of anthocyanins and polyphenols registered after heat treatment and storage increased with increasing addition levels of BC juice.
... Natural dietary sources are dark and red, such as berries as well as vegetables [3]. Daily anthocyanins intake is estimated to range between 12.5 mg/d and 65 mg/d in the U.S. and Europe [4,5]. Currently, they are an upcoming topic as nutraceuticals and as experimental approaches that suggest that intake decreases oxidative stress, blood pressure, cholesterol, and inflammation markers, thus resulting in vaso-and neuroprotection [6][7][8]. ...
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Oxidative stress and inflammation play a pivotal role in the development of cardiovascular diseases, an ever-growing worldwide problem. As a non-pharmacological approach, diet, especially a flavonoid-rich diet, showed promising results in the reduction of cardiovascular diseases and alleviation of their symptoms. In this study, in vitro systems based on human microvascular endothelial cells (hmvEC) and human umbilical cord endothelial cells (HUVEC) were established to determine the effect of Healthberry 865® (HB) and ten of its relating single anthocyanins on oxidative stress. Furthermore, five metabolites were used in order to examine the effect of anthocyanin’s most common breakdown molecules. The results showed an effect of HB in both models after 24 h, as well as most of its single anthocyanins. Cyanidin-rutinoside, peonidin-galactoside, and petunidin-glucoside had a model-specific effect. For the metabolites, phloroglucinaldeyhde (PGA) showed an effect in both models, while vanillic acid (VA) only had an effect in HUVEC. When combined, a combination of several anthocyanins did not have a cumulative effect, except for combining glucosides in hmvEC. The combination of PGA and VA even revealed an inhibitive behavior. Overall, the study demonstrates the antioxidative effect of HB and several of its single anthocyanins and metabolites, which are partially model specific, and coincides with animal studies.
... 1101/2022 The total anthocyanin concentration of the developed line 'Tim1' at eating stage (23 DAP) found in this current research (140.51 mg/100g FW) (Fig 5a) was significantly higher than anthocyanin found in other crops, for example, coloured strawberries (60 mg/100g FW) (Aaby et al., 2012), red plums (30.1 mg/100g FW) (Proteggente et al., 2002), and red currants (12.8 mg/100g FW) (Wu et al., 2006), in which anthocyanins were not as high as in the purple-pericarp super-sweetcorn line, 'Tim1'. ...
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The existence of purple-pericarp super-sweetcorn based on the most common supersweet mutation, shrunken2 (sh2), has not been previously reported, partly due to its extremely tight genetic linkage to a non-functional anthocyanin biosynthesis gene, anthocyaninless1 (a1). Generally, both aleurone- and pericarp-pigmented purple corn is starchy, the latter of which contains significantly higher anthocyanin compared to the former. The development of purple-pericarp super-sweetcorn is dependent on breaking the a1-sh2 tight genetic linkage, which occurs at a very low frequency of <1 in 1000 meiotic crossovers. Here, to develop purple-pericarp super-sweetcorn, an initial cross between a male purple-pericarp maize (purple-round seed), Costa Rica (A1Sh2.A1Sh2) and a female white shrunken2 super-sweetcorn (white-shrunken seed), Tims-white (a1sh2.a1sh2), was conducted. Subsequent self-pollination based on purple-pericarp-shrunken kernels identified a small frequency (0.08%) of initial heterozygous F3 segregants (A1a1.sh2sh2) producing a fully sh2 cob with a purple-pericarp phenotype, enabled by breaking the close genetic linkage between the a1 and sh2 genes. Resulting rounds of self-pollination generated a F6 homozygous purple-pericarp super-sweetcorn (A1A1.sh2sh2) line, Tim1. Genome sequencing revealed a recombination break between the a1 and yz1 genes of the a1-yz1-x1-sh2 multigenic interval, with the sequence pattern of Tim1 similar to the Costa Rica parent, and after the linkage break, similar to the Tims-white parent. The novel purple-pericarp super-sweetcorn produced a similar concentration of anthocyanin and sugar as in its purple-pericarp maize and white super-sweetcorn parents, respectively, potentially adding a broader range of health benefits than currently exists with standard yellow/white sweetcorn.
... However, anthocyanins in fruits are primarily present as glycosides or acylated glycosides. Berries such as blueberries, blackberries, raspberries, cranberries, and grapes show anthocyanin contents between 21 and 390 mg per 100 g fresh weight [16] with peonidin and cyanidin being the major anthocyanins in grapes and berries, respectively [17]. It is well known, that due to their structural polyphenolic characteristics, anthocyanins exhibit a high antioxidative potential, e.g., because of their capability for donating electrons [18], scavenging ROS [19,20], preventing ROS-induced oxidative damage or influencing antioxidative enzyme expression [21,22]. ...
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Cancer mortality is mainly due to metastasis. Therefore, searching for new therapeutic agents suppressing cancer cell migration is crucial. Data from human studies regarding effects of anthocyanins on cancer progression, however, are scarce and it is unclear whether physiological concentrations of anthocyanins and their metabolites reduce cancer cell migration in vivo. In addition, interactions with chemotherapeutics like 5-fluorouracil (5-FU) are largely unknown. Thus, we combined a placebo-controlled, double-blinded, cross-over study with in vitro migration studies of colon cancer cell lines to examine the anti-migratory effects of plasma-isolated anthocyanins and their metabolites (PAM). Healthy volunteers (n = 35) daily consumed 0.33 L of an anthocyanin-rich grape/bilberry juice and an anthocyanin-depleted placebo juice for 28 days. PAM were isolated before and after intervention by solid-phase extraction. HT-29 and Caco-2 cells were incubated with PAM in a Boyden chamber. Migration of HT-29 cells was significantly inhibited by PAM from juice but not from placebo. In contrast, Caco-2 migration was not affected. Co-incubation with 5-FU and pooled PAM from volunteers (n = 10), which most effectively inhibited HT-29 migration, further reduced HT-29 migration in comparison to 5-FU alone. Therefore, PAM at physiological concentrations impairs colon cancer cell migration and may support the effectiveness of chemotherapeutics.
... The content of anthocyanins in purple eggplant is higher than that in white and green eggplant (Tian et al., 2019), and 2.34 and 7.08 times higher than those in grapes and red onions, respectively (Wu et al., 2006). Recently, deeper research into eggplant anthocyanins has been reported, including functional characterization of eggplant TFs (Xi et al., 2021;He et al., 2021;Moglia et al., 2021) and expression of genes related to eggplant anthocyanin biosynthesis . ...
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Fruit color is an important commercial characteristic of eggplant (Solanum melongena L.), which affects both the profits of growers and consumer choice. Two eggplant inbred lines were discovered: “Z,” which is a light purple color under the fruit calyx, with purple on the fruit apex; and “L,” fruits of which are green under the calyx and at the apex. To determine the molecular mechanisms underlying the effect of fruit peel color under the calyx on that at the fruit apex, we conducted a combined transcriptomic and metabolomic analyses of the Z and L inbred eggplant lines. Transcriptome analysis of peel samples from three fruit regions (under the calyx, the apex, and the middle surface) of each line was conducted by RNA sequencing, and generated a total of 791,512,404 clean reads from 18 samples (three biological replicates). Differentially expressed genes (DEGs; n = 424) were identified in comparisons of peel samples from the three sites of L line fruits. Gene ontology analysis showed that “catalytic activity” was extremely significantly enriched. Further, DEGs (n = 8) were enriched in the Kyoto Encyclopedia of Genes and Genomes pathway “flavonoid biosynthesis.” Levels of CHI, LDOX, F3′5′H, and dihydroflavonol reductase were higher in the Z line than the L line. In addition, metabolome analysis showed that, 10 differentially accumulated metabolites were detected between peel samples from the apex of L and Z line fruit. The most significant DAM was delphinidin-3-O-rutinoside (Z line content, 34.89 μg/g vs. L line content 0.01 μg/g). Combined transcriptomic and metabolomic analyses indicated that DFR and F3′5′H were closely related to content of the metabolites, cyanidin and delphinidin, and that some downstream metabolites differed significantly between the L and Z lines. Content levels of delphinidin-3-O-rutinoside, delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, and cyanidin-3-O-rutinoside were markedly down-regulated in the L line. Altogether, increased CHI levels could up-regulate the downstream genes, LDOX, F3′5′H, and DFR, which further lead to increasing the content of delphindin. Thus, the uniform purple color was presented at the apex of fruits in Z plants. These findings not only identify key candidate genes, but will also improve understanding of the genetics and the efficiency of breeding for eggplant fruit color.
... It is evident that the ACs are known to vary in their number and position of hydroxyl and methoxy1 groups regarding their basic antioxidant skeleton, the identified number and position at which sugars are attached (Wu et al. 2006). Some common foods that are high in ACs include cherries, strawberries, raspberries, blackberries, blackcurrants, blueberries, and grapes, and the concentration of ACs varies widely between fruit. ...
Chapter
There is increasing attention on anthocyanins (ACs) and carotenoids as significant sources of antioxidants with biological activity regarding human health. However, the roles of these compounds in human health depend on their availability in food, extraction methods, and stability. The results of this chapter indicate the structures, extraction and analytical methods, stability, bioavailability, biological activity, and finally commercial utilization of ACs and carotenoids. The effect of these compounds in the food industry is significantly attributed. Finally, with their high-level content of antioxidants, these bioactive compounds can be very attractive in biotechnology, used as fortified and natural additives to foods delivering special benefits in both health and the wider economy.KeywordsAnthocyaninCarotenoidsFruitsBioavailabilityBiologicalProduction
... Anthocyanin concentrations are sometimes reported in the form of aglycones, after hydrolysis reaction, to reduce the complexity of structural biological differences. However, the variety of anthocyanin forms present in a sample will have different responses, different potential health benefits, and different bioavailabilities (Wu, Beecher et al., 2006). Further, it is well known that anthocyanin hydrolysis contributes to the hydrolysis of proanthocyanidins (a class of polyphenols) resulting in aglycones exaggerating the concentration of aglycones present in the food (Prior and Gu, 2005). ...
Article
It is well known that changes in the anthocyanin content occur during fruit/vegetable development. However, the anthocyanin content variation due to various analytical methods has not been established in the literature. Therefore, in this study, the individual and the total anthocyanin content of the 64 Australian foods have been determined using liquid chromatography (LC-MS, LC-UV) and spectrophotometry methods. Anthocyanin-rich foods were systematically selected and extracted using an optimized ultrasound-assisted extraction method and the total anthocyanin content of the foods was measured using various molar absorptivity values. A comparison of the anthocyanin content between methods demonstrated that the anthocyanin in the same foods showed different degrees of quantification. In general, there was no specific pattern for the anthocyanin type present in similar foods. The comprehensive data with both the total and the individual anthocyanidin-3-glucoside concentration will aid in understanding the functional properties in future research for determining anthocyanin composition.
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Nutrition is one of the most important factors determining human health. Enrichment of food products with minerals, antioxidant compounds, and vitamins are relevant today. In this work, dry orange peel was used to enrich a fermented drink based on kvass wort with phenolic compounds and vitamin C. The following indicators were determined: the content of vitamin C, the amount of phenolic compounds and anthocyanins, the antioxidant activity of orange peel dried to a moisture content of 18%. The drink fermentation lasted 12 hours at 30 °C. Secondary fermentation was carried out for 48 hours. At this stage, orange peel was added in the amount of 10 g/l. During the experiment, the concentration of dry matter content, the acidity of the medium, and the content of ethyl alcohol were measured. Organoleptic indicators were determined during the tasting of the finished product. In the finished drink, the content of ethyl alcohol was 0.98%. It was found that the finished drink with peel contains 4 times more phenolic compounds and 1.5 times more vitamin C.
Chapter
Due to the fact that vegetables are the only cheapest source of nutrients, vitamins, and minerals, hence they are a crucial part of the human diet. They provide good remunerative to the growers as they fetch more money from market. The effects of climate change, such as global warming, modifications to seasonal and monsoon patterns, and biotic and abiotic variables, are also having an impact on these crops, just like they do on other crops. Crop failures, low yields, declining quality, and an increase in pest and disease issues are frequent under climate change-related conditions, which make unprofitable to cultivate vegetables. Because of many physiological and enzymatic processes depend on temperature, they will be significantly impacted. The two most significant effects of temperature rise on vegetable cultivation are drought and salt. Crop yields may improve as a result of increased CO2 fertilisation; however, this positive effect decreases after certain point. Greenhouse gases produced by human activity, such as CO2, CH4, and CFCs, are a major factor in global warming, while sulphate and nitrogen dioxides weaken the ozone layer and allow dangerous UV rays to enter the atmosphere. These climate change effects also have severe impact on the prevalence of pests and diseases, as well as on the nutritional value (vitamins, minerals, proteins, etc.) and aesthetics of vegetable crops. Iron and zinc levels, as well as the amount of protein in vegetable crops, were dramatically lowered by higher CO2 levels. In the end, the quality and volume of global vegetable output are falling due to climate change.KeywordsVegetablesClimate changeGreenhouse gassesNutritional value
Chapter
There is a diverse array of berries found wild in tropical, temperate and arid ecosystems or cultivated in both field and control environments across the globe. It is evident berry genetics, species, growth environment, cultivation techniques, postharvest management practices, packaging and processing affect the nutritional and functional properties of berries. The level and composition of functional and nutritional compounds in berries are primarily responsible for their health promotive properties. In particular, anthocyanins and flavonoids are shown to be very effective in managing, treating and reducing CVD risks in humans; and the effects are even more pronounced when combined with personalized nutrition or diets and physical activities. Globally, there is a steady increase in CVD incidences and associated deaths. There is a need for interventive strategies to reduce these CVD incidences and associated deaths. Personalized nutrition and diets containing increase levels or consumption of fresh berries, berry-based functional foods, nutritional products, or nutraceuticals could be an effective long-term strategy to reduce CVD disease risks, as well as improve population health globally.
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Black raspberries (BRB) are rich in anthocyanins with purported anti-inflammatory properties. However, it is not known whether dietary supplementation would ameliorate Western-diet enhanced gut inflammation and colon tumorigenesis. We employed a mouse model of colitis-associated colorectal cancer (CAC) to determine the effects of dietary supplementation with 5 to 10% (w/w) whole, freeze-dried BRB in male C57BL/6J mice fed either a standard healthy diet (AIN93G) or the total Western diet (TWD). In a pilot study, BRB suppressed colitis and colon tumorigenesis while also shifting the composition of the fecal microbiome in favor of taxa with purported health benefits, including Bifidobacterium pseudolongum. In a follow-up experiment using a 2 ´ 2 factorial design with AIN and TWD basal diets with and without 10% (w/w) BRB, supplementation with BRB reduced tumor multiplicity and increased colon length, irrespective of the basal diet, but it did not apparently affect colitis symptoms, colon inflammation or mucosal injury based on histopathological findings. However, BRB intake increased alpha diversity, altered beta diversity and changed the relative abundance of Erysipelotrichaceae, Bifidobacteriaceae, Streptococcaceae, Rikenellaceae, Ruminococcaceae and Akkermansiaceae, among others, of the fecal microbiome. Notably, changes in microbiome profiles were inconsistent with respect to the basal diet consumed. Overall, these studies provide equivocal evidence for in vivo anti-inflammatory effects of BRB on colitis and colon tumorigenesis; yet, BRB supplementation led to dynamic changes in the fecal microbiome composition over the course of disease development.
Article
BACKGROUND: Black medic is used as a pasture, cover, siderate, anti-erosion culture for fixing embankments along roads, on mining dumps and for phytoremediation. Mono-, bi- and polycarpic forms are distinguished within the species, differing in the number of fruitions during the plant life cycle. The presence of polymorphism of morphological features and features of ontogenesis suggests the presence of differences in biochemical parameters in the selected groups. AIM: The aim of the study was to study the polymorphism of biochemical parameters of various life forms of black medic. MATERIALS AND METHODS: The material for the study was 20 accessions of black medic of various origins from groups of mono-, bi- and polycarpic plants of the VIR collection. For the study, a freshly harvested green mass of plants was used. The assessment was carried out according to the following biochemical parameters: the content of dry matter, protein, sugars, ascorbic acid, total acidity, chlorophylls, carotenoids, carotenes, -carotene, anthocyanins. Statistical processing of the results included calculation of the main parameters of variation, analysis of variance and discriminant analysis. RESULTS: The nutritional value of black medic was characterized by the content of crude protein and sugars. The range of protein variability ranged from 11,94 to 19,69 mg / 100 g of raw matter, sugars from 0,44 to 2,67%. Differences in the sugar content of plants of different groups were revealed. The content of ascorbic acid was the highest in five varieties from the polycarpic plant group presented in the study in comparison with wild-growing accessions and the monocarpic Bereginya variety. Monocarpics are distinguished by the content of anthocyanin (19,5 1,41 mg / 100 g); no significant differences were found in the content of other pigments. CONCLUSIONS: The results of in-depth biochemical analysis of accessions from the collection of plant genetic resources demonstrate the high variability of biologically active substances in the green mass of plants and will significantly improve the choice of the initial material for selection for forage usage.
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The effects of drying air temperatures (50, 60, 70 and 80°C) and velocities (0.5, 0.8, 1.2 m.s − 1 ) used for the convective drying of chokeberry on fruit quality were quantified. The drying air temperature rise shortened the drying time from 2660 min at 50 o C to 185 min at 80 o C. Drying time was 220 min at the drying air velocity of 1.2 m.s − 1 . An increase in the temperature from 50 to 80°C and the air velocity from 0.5 m·s − 1 to 1.2 m·s − 1 enhanced fruit color quality index. All the drying treatments enriched the biochemical fruit content. 70°C and the air velocity between 0.5 m.s − 1 and 1.2 m.s − 1 achieved the highest antioxidant activity, total anthocyanin content and total phenolic content.
Article
BACKGROUND: Lingonberry (Vaccinium vitis-idaea L.), as an important natural and wild plant resource in the world, has high economic and nutritional values. Many researchers have focused on the effect of antioxidant and enzyme inhibitors. OBJECTIVE: The present study aimed to evaluate the active ingredients, in vitro antioxidant and enzyme-inhibitory activity from different parts (root, stem, leaf, and fruit) of wild lingonberry. METHODS: The active ingredients of lingonberry were determined by ultra-performance liquid chromatography-triple quadrupole-mass spectrometry (UPLC-TQ-MS/MS). Antioxidant activities were measured by DPPH, ABTS, FRAP and CUPRAC assays. Principal component analysis (PCA) and agglomerated hierarchical clustering (AHC) were used to analyze the relationship between active ingredients, antioxidant and enzyme-inhibitory activity. RESULTS: Phenolic compounds were significantly higher in leaf and stem. The enzyme inhibitory of the extracts varied observably according to the plant parts. Fruit had the highest acetylcholinesterase (317.67 mg GALAEs/g) and butyrylcholinesterase (346.04 mg GALAEs/g) inhibitory activity, while leaf had the most potent activity on α-amylase (256.59 mg ACAEs/g), α-glucosidase (186.70 mg ACAEs/g) and tyrosinase (42.87 mg KAEs/g). Tyrosinase had strong correlation and similarity with phenolic acids and flavonoids in the correlation analysis and PCA. CONCLUSIONS: 29 active ingredients were detected, including phenolic acids, flavonoids, anthocyanins, and triterpenes. Lingonberry sample to inhibit the activity of tyrosinase was associated with five flavonoids (kaempferol-3-O-galactoside, kaempferol-3-O-β-D-glucosyl (1 ⟶ 2) galactoside, biorobin,,quercetin 3-O-glucoside-7-O-rhamnoside, rutinum) and phenolic acid content (arbutin). These results suggested that the lingonberry could be used as a promising natural resource for functional food and medicinal development.
Article
Among plant pigments, anthocyanins are one of the most important. However, there are great difficulties related to applying appropriate techniques able to identify molecules with similar structures (suchlike anthocyanins) and simultaneously estimate their variety and concentration within fruit matrices. Therefore, several methods have been evaluated to achieve the best workflows for anthocyanin analysis. For the first time, this review article presents the current findings on analytical procedures for anthocyanin investigation based on the robust liquid chromatography coupled to mass spectrometry (LC-MS) workflow. Anthocyanins extraction, LC-MS analytical instrumentation, and chemometric strategies that converge to the better performance of such workflow are herein presented. By means of this metabolomics platform, it is possible to obtain the most accurate identification of phenolic compounds, such as anthocyanins. This is a crucial step since these compounds are related to the sensory qualities of food, such as color, flavor, and aroma.
Article
Objective: Anthocyanins are polyphenols which are promising chemopreventive agents, which stand out for their anti-inflammatory properties, with specific modulatory actions on the immune system. Additionally, with regard to the immune system, a group of cells identified as mesenchymal stem cells (MSCs) have been attracting attention, mainly due to their capacity to migrate to sites of inflammation and produce potent immunomodulatory effects. Considering the ability of these cells to act on the immune system, as well as the properties of anthocyanins, especially delphinidin in modulating the immune system, this work aimed to investigate the effects of delphinidin in influencing some immunoregulatory properties of MSCs. Methods: MSCs were cultivated in the presence of delphinidin 3-O-β-D-glycoside and cell viability, the cell cycle and the production of soluble factors (IL-1β, IL-6, IL-10, TGF-β, PGE2 and NO) were evaluated, as well as the expression of the transcription factors NFκB and STAT3. Additionally, the effects of conditioned media from MSCs on macrophage activation were assessed. Results: Delphinidin at 50 µM does not affect cell viability, also showing that delphinidin in association with lipopolysaccharide was able to induce MSC proliferation. Additionally, delphinidin modulated the MSC immune response, showing increased levels of anti-inflammatory cytokines such as IL-10 and TGF-β as well as lower expression of NFκB. Furthermore, conditioned media from MSCs inhibited macrophage metabolism, reducing the production of IL-1β, IL-12 and TNF-α and increasing IL-10. Conclusions: Overall, this work showed that delphinidin is able to modify the immunomodulatory properties of MSCs, increasing the IL-10 production by macrophages.
Article
Anthocyanins can prevent and ameliorate type 2 diabetes mellitus (T2DM), but its mechanism of action has not been fully established. IKK/NF-κB and JAK/Stat pathways have multiple effects, triggering T2DM. Liver abnormalities in individuals with T2DM are detrimental to glycemic control. We determined whether anthocyanins could improve the liver of individuals with T2DM using IKK/NF-κB and JAK/Stat. We established a T2DM mouse model using a high-fat diet and streptozotocin and then performed Aronia melanocarpa anthocyanin extracts' (AMAEs') administration for 5 weeks. AMAEs improved blood glucose and hyperinsulinemia of T2DM mice. In the liver of AMAE-administered T2DM mice, ROS, IKKβ/NF-κB p65, and JAK2/Stat3/5B signalings were down-regulated, thereby reducing the suppressor of cytokine signaling 3 (SOCS3), iNOS, and inflammatory mediators. AMAE-improved hyperinsulinemia also down-regulated SOCS3 by decreasing p-Stat5B in hepatocytes. AMAEs enhanced glucose uptake and conversion and decreased hepatocyte enlargement and inflammatory cells in the liver of T2DM mice. These indicated that AMAEs could alleviate oxidative stress, insulin resistance, inflammation, and tissue damage in the liver of T2DM mice through inhibiting NF-κB p65 and Stat3/5B.
Article
Anthocyanins, have received the attention of the scientific community due to their antioxidant, antimetastatic, and cancer-inhibitory properties. The aim of this review is to comprehensively summarize the possible mechanisms by which anthocyanins exhibit anticarcinogenic properties in breast cancer (BC) cell lines and animal models. Anthocyanins inhibit proinflammatory, signal transducer and activator of transcription 3 (STAT3) and nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) pathways and increase the activities of detoxification enzymes. In addition, downregulation of metalloproteinases (MMPs) by anthocyanins inhibits tumor invasion and metastatic processes in experimental systems. Anthocyanins mediate anticancer and angiogenic effects by modifying multiple receptor families. Furthermore, inhibition of cell cycle upstream polo-like kinase (Plk) signaling, the chromosomal replication checkpoint and ataxia telangiectasia mutated (ATM) signaling may contribute to the anticarcinogenic effects of anthocyanins. Finally, anthocyanins induce mitochondrial-mediated apoptosis and downregulate the PI3K/AKT/mTOR pathway. In conclusion, anthocyanins have been shown to exert potential antitumor effects against breast carcinogenesis in vitro and in vivo, providing insights into the use of anthocyanins as a natural chemopreventive intervention in BC.
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A healthy gut provides the perfect habitat for trillions of bacteria, called the intestinal microbiota, which is greatly responsive to the long-term diet; it exists in a symbiotic relationship with the host and provides circulating metabolites, hormones, and cytokines necessary for human metabolism. The gut–heart axis is a novel emerging concept based on the accumulating evidence that a perturbed gut microbiota, called dysbiosis, plays a role as a risk factor in the pathogenesis of cardiovascular disease. Consequently, recovery of the gut microbiota composition and function could represent a potential new avenue for improving patient outcomes. Despite their low absorption, preclinical evidence indicates that polyphenols and their metabolites are transformed by intestinal bacteria and halt detrimental microbes’ colonization in the host. Moreover, their metabolites are potentially effective in human health due to antioxidant, anti-inflammatory, and anti-cancer effects. The aim of this review is to provide an overview of the causal role of gut dysbiosis in the pathogenesis of atherosclerosis, hypertension, and heart failure; to discuss the beneficial effects of polyphenols on the intestinal microbiota, and to hypothesize polyphenols or their derivatives as an opportunity to prevent and treat cardiovascular diseases by shaping gut eubiosis.
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The health benefits of anthocyanins are compromised by their chemical instability and susceptibility to external stress. Researchers found that the interaction between anthocyanins and macromolecular components such as proteins and polysaccharides substantially determines the stability of anthocyanins during food processing and storage. The topic thus has attracted much attention in recent years. This review underlines the new insights gained in our current study of physical and chemical properties and functional properties in complex food systems. It examines the interaction between anthocyanins and food proteins or polysaccharides by focusing on the “structure–stability” relationship. Furthermore, multispectral and molecular computing simulations are used as the chief instruments to explore the interaction's mechanism. During processing and storage, the stability of anthocyanins is generally influenced by the adverse characteristics of food and beverage, including temperature, light, oxygen, enzymes, pH. While the action modes and types between protein/polysaccharide and anthocyanins mainly depend on their structures, the noncovalent interaction between them is the key intermolecular force that increases the stability of anthocyanins. Our goal is to provide the latest understanding of the stability of anthocyanins under food processing conditions and further improve their utilization in food industries. Practical Application: This review provides support for the steady‐state protection of active substances.
Book
The term “reactive oxygen species” (ROS) refers to a group of reactive molecules and free radicals produced by molecular oxygen. In recent decades, there has been great interest in the role of ROS in various diseases. From basic science research to clinical trials, biomedical scientists have made rapid progress toward a better understanding of ROS-metabolizing systems and their role in health and diseases. This book includes sixteen chapters that address topics such as the history of ROS, its role in autoimmunity, neurodegeneration, and aging, and recent advances in various antioxidants and their therapeutic potential.
Article
Solanum melongena is a widely consumed vegetable crop comprising health-benefiting phenolic compounds. It has a complex network of biosynthetic enzymes involved in synthesizing nutraceuticals, including anthocyanins. The present study was conducted to investigate the activities of key enzymes involved in biosynthesis and accumulation of anthocyanins in developing genotypes, such as phenylalanine ammonia lyase (PAL), tyrosine ammonia lyase (TAL), and anthocyanidin synthase (ANS). As inadequate information is available in this context, fruit and leaf tissues were analyzed for enzyme activities and anthocyanin accumulation. The study included characterization of extracted anthocyanin followed by expression studies for gateway enzyme (ANS) involved in anthocyanin biosynthesis. Delphinidin was a major anthocyanidin present in fruit tissues (1.46–110.49 mg/100 g) of S. melongena. Anthocyanin accumulation is backed up by the correlation between biochemical analysis and expression studies. The study has shown variation for PAL, TAL and ANS enzymes in different tissues at developmental stages. Enzyme activities had a strong positive correlation with anthocyanin biosynthesis.
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Androgen is a kind of steroid hormone that plays a vital role in reproductive system and homeostasis of the body. Disrupted androgen balance serves as the causal contributor to a series of physiological disorders and even diseases. Flavonoids, as an extremely frequent family of natural polyphenols, exist widely in plants and foods and have received great attention when considering their inevitable consumption and estrogen-like effects. Mounting evidence illustrates that flavonoids have a propensity to interfere with androgen synthesis and metabolism, and also have a designated improvement effect on androgen disorders. Therefore, flavonoids were divided into six subclasses based on the structural feature in this paper, and the literature about their effects on androgens published in the past ten years was summarized. It could be concluded that flavonoids have the potential to regulate androgen levels and biological effects, mainly by interfering with the hypothalamic-pituitary-gonadal axis, androgen synthesis and metabolism, androgen binding with its receptors and membrane receptors, and antioxidant effects. The faced challenges about androgen regulation by flavonoids masterly include target mechanism exploration, individual heterogeneity, food matrixes interaction, and lack of clinical study. This review also provides a scientific basis for nutritional intervention using flavonoids to improve androgen disorder symptoms.
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Anthocyanins are water-soluble flavonoids, in nature found in flowers, fruits and some vegetables such as red radish, red cabbage and red onion. Due to its characteristics as a natural colorant and its bioactive properties, the food, pharmaceutical and cosmetic industries have focused their interest on them. To quantify these compounds, some spectrophotometric and chromatographic techniques exist, its use, however, is in disadvantage because of the long execution times and high cost of the reagents. Therefore, the aim of the present work was to evaluate the validation parameters of a spectrophotometric microassay based on the pH differential method to quantify the total monomeric anthocyanins content of red cabbage. The validation of the method by microassay was carried out evaluating the selectivity, specificity, linearity, limits of detection and quantification, precision, robustness and applicability. The results of selectivity and specificity showed that only total monomeric anthocyanins can be identified with the validated method. Which proved to be linear (r² = 0.9999), precise (RSD < 7.5%), applicable in varied vegetables and robust by not presenting significant difference between the extract with different pH, as well as in the evaluations carried out with the buffers distinct to those established in the official method. The official method and the modified showed a similar content 7.08 ± 0.81 and 6.42 ± 0.41 mg EC3G g− 1 respectively. Results confirmed that the modified method is acceptable to identify and quantify total monomeric anthocyanins.
Article
Anthocyanins, which are the labile flavonoid pigments widely distributed in many fruits, vegetables, cereal grains, and flowers, are receiving intensive interest for their potential health benefits. Proteins are important food components from abundant sources and present high binding affinity for small dietary compounds, e.g., anthocyanins. Protein-anthocyanin interactions might occur during food processing, ingestion, digestion, and bioutilization, leading to significant changes in the structure and properties of proteins and anthocyanins. Current knowledge of protein-anthocyanin interactions and their contributions to functions and bioactivities of anthocyanin-containing foods were reviewed. Binding characterization of dietary protein-anthocyanins complexes is outlined. Advances in understanding the structure-affinity relationship of dietary protein-anthocyanin interaction are critically discussed. The associated properties of protein-anthocyanin complexes are considered in an evaluation of functional and nutritional values.
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The absorption and metabolism of anthocyanins (ACN) in humans was studied in four elderly women given 12 g elderberry extract (EBX) (720 mg total ACN), and six elderly women given 189 g lowbush blueberry (BB) (690 mg total ACN). The two major ACN in EBX, cyanidin-3-glucoside and cyanidin-3-sambubioside, as well as four metabolites: 1) peonidin 3-glucoside, 2) peonidin 3-sambubioside, 3) peonidin monoglucuronide, and 4) cyanidin-3-glucoside monoglucuronide were identified in urine within 4 h of consumption using HPLC-MS/MS with diode-array detector detection and retention time. Total EBX ACN excretion was 554 +/- 90 microg (mean +/- SD, n = 4) (0.077% of intake/4 h, wt/wt). In 5 of 6 women fed BB, urine samples contained ACN, which were identified as the original forms based upon comparisons to the BB food sample, which contained 24 ACN, 22 of which were identified by HPLC-MS/MS. Reasonable correlations between BB and urine proportions of the different ACN were obtained except for ACN arabinosides. Total urinary excretion during the first 6 h was 23.2 +/- 10.9 microg (mean +/- SD, n = 5) (0.004% of intake/6 h, wt/wt). Plasma ACN levels were below detection limits using 2 mL plasma in women that consumed BB. This study demonstrates for the first time that in vivo methylation of cyanidin to peonidin and glucuronide conjugate formation occurs after people consume ACN and demonstrates the low absorption and excretion of ACN compared with other flavonoids.
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Anthocyanins are a group of naturally occuring phenolic compounds related to the coloring of plants, flowers and fruits. These pigments are important as quality indicators, as chemotaxonomic markers and for their antioxidant activities. Here, we have investigated the therapeutic efficacy of anthocyanins contained in blackberry extract (cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents) in an experimental model of lung inflammation induced by carrageenan in rats. Injection of carrageenan into the pleural cavity elicited an acute inflammatory response characterized by fluid accumulation which contained a large number of neutrophils as well as an infiltration of polymorphonuclear leukocytes in lung tissues and subsequent lipid peroxidation, and increased production of nitrite/nitrate (NOx) and prostaglandin E2 (PGE2). All parameters of inflammation were attenuated in a dose-dependent manner by anthocyanins (10, 30 mg kg(-1) 30 min before carrageenan). Furthermore, carrageenan induced an upregulation of the adhesion molecule ICAM-1, nitrotyrosine and poly (ADP-ribose) synthetase (PARS) as determined by immunohistochemical analysis of lung tissues. The degree of staining was lowered by anthocyanins treatment. Thus, the anthocyanins contained in the blackberry extract exert multiple protective effects in carrageenan-induced pleurisy.
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Anthocyanin-rich extracts, potent antioxidants and commercially available food coloring agents, have been reported to inhibit growth of various cancer cell lines. We investigated the effect of semipurified anthocyanin-rich extract from fruits of Aronia meloncarpa, on normal colon and colon cancer cell lines. A 24-h exposure to 50 mg monomeric anthocyanin/ml of Aronia extract resulted in 60% growth inhibition of human HT-29 colon cancer cells. The treated cells showed a blockage at G1/G0 and G2/M phases of the cell cycle. The cell cycle arrest coincided with an increased expression of the p21WAF1 and p27KIP1 genes and decreased expression of cyclin A and B genes. Prolonged exposure to the extract resulted in no further change in the cell number, indicating a cytostatic inhibition of cell growth. NCM460 normal colon cells demonstrated <10% growth inhibition at the highest concentration of 50 mg/ml extract. A 35% decrease in the cyclooxygenase-2 gene expression was observed within 24 h of exposure of HT-29 cells but did not translate into decreased protein levels or protein activity. These results support the need for further research to identify the specific component(s) in this extract that suppress cancer cell growth and the genes affected by these natural compounds.
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Cyanidin and its glycosides belong to the anthocyanins, a widespread class of water-soluble plant compounds that are responsible for the brilliant color (red, orange, blue) of fruits and flowers. They are widely ingested by humans as it has been estimated a daily intake around 180 mg, mainly deriving from fruits and red wines. This paper reviews the literature on the biological activities, absorption and metabolism of cyanidins, with emphasis to the antioxidant, antimutagenic and other protective activities ascribed to these compounds. Their role in contrasting development of cancer and other pathologies is also reviewed. It is concluded that a great deal of work is still necessary to i) definitively clarify the metabolism of cyanidins in human beings; ii) assess the dietary burden and variations within and between populations; iii) evaluate the relationship between cyanidin glycosides-rich food consumption and incidence of given pathologies. The amount of work to be performed is even more significant when considering a possible therapeutic use of cyanidin glycosides-based drugs. With this aim, information on absorption, distribution, metabolism and excretion of cyanidin-glycosides administered by main possible routes are largely insufficient. However, consisting findings allow looking at cyanidins as dietary compounds with a potential beneficial role for human health.
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Proanthocyanidins (PAs) have been shown to have potential health benefits. However, no data exist concerning their dietary intake. Therefore, PAs in common and infant foods from the U.S. were analyzed. On the bases of our data and those from the USDA's Continuing Survey of Food Intakes by Individuals (CSFII) of 1994-1996, the mean daily intake of PAs in the U.S. population (>2 y old) was estimated to be 57.7 mg/person. Monomers, dimers, trimers, and those above trimers contribute 7.1, 11.2, 7.8, and 73.9% of total PAs, respectively. The major sources of PAs in the American diet are apples (32.0%), followed by chocolate (17.9%) and grapes (17.8%). The 2- to 5-y-old age group (68.2 mg/person) and men >60 y old (70.8 mg/person) consume more PAs daily than other groups because they consume more fruit. The daily intake of PAs for 4- to 6-mo-old and 6- to 10-mo-old infants was estimated to be 1.3 mg and 26.9 mg, respectively, based on the recommendations of the American Academy of Pediatrics. This study supports the concept that PAs account for a major fraction of the total flavonoids ingested in Western diets.
Article
Background Anthocyanins, which are found in high concentrations in fruit and vegetable, may play a beneficial role in retarding or reversing the course of chronic degenerative diseases. However, little is known about the biotransformation and the metabolism of anthocyanins so far. Aim of the study The aim of the study was to investigate possible transformation pathways of anthocyanins by human faecal microflora and by rat liver microsomes as a source of cytochrome P450 enzymes as well as of glucuronyltransferases. Methods Pure anthocyanins, an aqueous extract of red radish as well as the assumed degradation products were incubated with human faecal suspension. The incubation mixtures were purified by solid-phase extraction and analysed by HPLC/DAD/MS and GC/MS. Quantification was done by the external standard method. Furthermore the biotransformation of anthocyanins by incubation with rat liver microsomes in the presence of the cofactor NADPH (as a model for the phase I oxidation) and in the presence of activated glucuronic acid (as a model for the phase II glucuronidation) was investigated. Results Glycosylated and acylated anthocyanins were rapidly degraded by the intestinal microflora after anaerobic incubation with a human faecal suspension. The major stable products of anthocyanin degradation are the corresponding phenolic acids derived from the B-ring of the anthocyanin skeleton. Anthocyanins were not metabolised by cytochrome P450 enzymes, neither hydroxylated nor demethylated. However they were glucuronidated by rat liver microsomes to several products. Conclusions The gut microflora seem to play an important role in the biotransformation of anthocyanins. A rapid degradation could be one major reason for the poor bioavailability of anthocyanins in pharmacokinetic studies described so far in the literature. The formation of phenolic acids as the major stable degradation products gives an important hint to the fate of anthocyanins in vivo
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This text is a comprehensive reference covering the chemistry, physiology, chemotaxonomy, biotechnology and food technology aspects of the anthocyanins. Topics discussed include types of anthocyanins, structural transformations, colour stabilization and intensification factors, biosynthesis and intensification factors, biosynthesis, analysis and functions of anthocyanins. An in-depth review of the literature discussing anthocyanins of fruits, cereals, legumes, roots, tubers, bulbs, cole crops, oilseeds, herbs, spices, and minor crops is included as well.
Article
There is considerable demand for food colorants from natural sources that can serve as alternatives to the use of synthetic dyes due to both legislative action and consumer concerns over the use of synthetic additives. Interest in anthocyanin-rich foods and extracts has intensified because of their possible health benefits. Anthocyanins are potent antioxidants and may be chemoprotective. Optimizing health and performance through the diet is believed to be one of the largest and most lucrative markets in the US, and throughout the world.Findings of acylated anthocyanins with increased stability have shown that these pigments may impart desirable color and stability for commercial food products. Examples of suitable acylated anthocyanin sources may be radishes, red potatoes, red cabbage, black carrots, and purple sweet potatoes. Among these, radishes and red potatoes stand out as potential alternatives for the use of FD&C Red No. 40 (allura red). Maraschino cherries with bright attractive and stable red color were obtained with radish extract. Radish and potato extracts imparted color characteristics to model juices extremely close to those of allura red. Other potential applications for acylated anthocyanins may include other challenging systems such as dairy products. The increased stability of these pigments together with their added value due to potential beneficial effects opens a new window of opportunities for use of these extracts in a variety of food applications.
Article
The National Food and Nutrient Analysis Program (NFNAP) is designed to develop robust estimates of the mean nutrient content of important foods in the food supply and significantly improve the quality of food composition data in the US Department of Agriculture's (USDA) National Nutrient Databank. The program objectives are: (1) evaluation of existing data; (2) identification of Key Foods and nutrients for analysis; (3) development of nationally based sampling plans; (4) analysis of samples; and (5) compilation and calculation of representative food composition data. This paper describes our efforts in development of the sampling plan (objective 3) and presents limited preliminary results. The sampling plan was based on a self-weighting stratified design. First, the U.S. was divided into four regions, then each region was further divided into three implicit strata from which generalized Consolidated Metropolitan Statistical Areas (gCMSAs) were selected. Rural and urban locations were selected within gCMSAs. Commercial supermarket lists were used to select 24 outlets for food pickups; specific brands were selected based on current market share data (pounds consumed). This population-based approach can be applied in the development of other sampling programs for specific ethnic and regional foods. Sampling plans have been developed for margarine, folate-fortified foods (e.g. flours, bread, and pasta), and a number of highly consumed mixed dishes (e.g. pizza and lasagna).
Article
Anthocyanins are natural colorants belonging to the flavonoid family. They are widely distributed among flowers, fruits, and vegetables. Using the automated oxygen radical absorbance capacity (ORAC) assay developed in our laboratory, we determined the antioxidant capacity of 14 anthocyanins including the aglycons delphinidin, cyanindin, pelargonidin, malvidin, peonidin, and their derivatives with different sugar linkages. Among these anthocyanins, kuromanin (cyanidin-3-glucoside) had the highest ORAC activity, which was 3.5 times stronger than Trolox (vitamin E analogue), while pelargonin had the lowest antioxidant activity but was still as potent as Trolox. Different patterns of hydroxylation and glycosylation in anthocyanins appear to modulate their antioxidant properties. Therefore, in addition to their colorful characteristics, anthocyanins possess potent antioxidant properties.
Article
Flavonoids are important dietary constituents owing to their health-promoting properties. As a result, simplified analytic techniques are required for the population of databases with food values so that associations between dietary intake and disease risk/incidence can be established. The current research provides a simplified sample preparation procedure for the accurate estimation of food anthocyanidins, flavones, and flavonols as aglycons. Traditionally, flavonoid aglycons have been formed by acidic hydrolysis. However, some flavonoid aglycons are slowly degraded by acid. A procedure has been developed whereby anthocyanidins and flavonols are deglycosylated with HCl in 50% aqueous methanol and the resulting aglycons subsequently quantified by application of pseudo-first-order kinetics to their degradation. Flavones are also deglycosolated under similar conditions but, at appropriate temperatures, their aglycons are stable in acid, so kinetics were not required for the quantitation of this subclass of flavonoids. Catechins and flavanones were rapidly degraded under the hydrolytic conditions used in these studies.
Article
A method has been established and validated for identification and quantification of individual, as well as total, anthocyanins by HPLC and LC/ES-MS in botanical raw materials used in the herbal supplement industry. The anthocyanins were separated and identified on the basis of their respective M(+) (cation) using LC/ES-MS. Separated anthocyanins were individually calculated against one commercially available anthocyanin external standard (cyanidin-3-glucoside chloride) and expressed as its equivalents. Amounts of each anthocyanin calculated as external standard equivalent were then multiplied by a molecular-weight correction factor to afford their specific quantities. Experimental procedures and use of a molecular-weight correction factors are substantiated and validated using Balaton tart cherry and elderberry as templates. Cyanidin-3-glucoside chloride has been widely used in the botanical industry to calculate total anthocyanins. In our studies on tart cherry and elderberry, its use as external standard followed by use of molecular-weight correction factors should provide relatively accurate results for total anthocyanins, because of the presence of cyanidin as their major anthocyanidin backbone. The method proposed here is simple and has a direct sample preparation procedure without any solid-phase extraction. It enables selection and use of commercially available anthocyanins as external standards for quantification of specific anthocyanins in the sample matrix irrespective of their commercial availability as analytical standards. It can be used as a template and applied for similar quantification in several anthocyanin-containing raw materials for routine quality control procedures, thus providing consistency in analytical testing of botanical raw materials used for manufacturing efficacious and true-to-the-label nutritional supplements.
Article
A high-performance liquid chromatographic (HPLC) method for the determination of anthocyanidins from berries and red wine is described. Delphinidin, cyanidin, petunidin, pelargonidin, peonidin, and malvidin contents of bilberry (Vaccinium myrtillus), black currant (Ribes nigrum), strawberry (Fragaria ananassa cv. Jonsok), and a Cabernet sauvignon (Vitis vinifera) red wine were determined. The aglycon forms of the anthocyanins present in the samples were revealed by acid hydrolysis. A reversed phase analytical column was employed to separate the anthocyanidins before identification by diode array detection. The suitability of the method was tested by determining the recovery (95-102% as aglycons and 69-104% from glycosides) for each anthocyanidin. Method repeatability was tested by charting the total aglycon content of two samples over a period of 14 analyses and determining the coefficients of variation (1.41% for bilberry and 2.56% for in-house reference material). The method developed proved thus to be effective for reliable determination of anthocyanidins from freeze-dried berry samples and red wine. The total anthocyanidin content of the tested samples was as follows: in-house reference material, 447 +/- 8 mg/100 g; strawberry, 23.8 +/- 0.4 mg/100 g; black currant, 135 +/- 3 mg/100 g; bilberry, 360 +/- 3 mg/100 g; and Cabernet sauvignon red wine, 26.1 +/- 0.1 mg/100 mL.
Article
Twelve acylated anthocyanins were isolated from the red radish (Raphanus sativus L.) and their structures were determined by spectroscopic analyses. Six of these were identified as pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-beta-D-glucopyranosyl]-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-caffeoyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), pelargonidin 3-O-[6-O-(E)-p-coumaroyl-2-O-(6-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside), and pelargonidin 3-O-[6-O-(E)-feruloyl-2-O-(2-(E)-feruloyl-beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside).
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
Anthocyanins are phenolic compounds widely distributed in fruits and vegetables. Their consumption has been shown to prevent some chronic diseases. Anthocyanin metabolism, however, is still not fully understood. The aim of this work was to evaluate the bioavailability of anthocyanins in humans consuming a meal containing strawberries and to identify possible metabolites in urine. Six healthy volunteers (three women and three men) consumed a meal containing 200 g strawberries (providing 179 micro mol pelargonidin-3-glucoside). Urine samples were collected before and after the meal and rapidly treated by solid-phase extraction. Identification and quantification of anthocyanin metabolites were carried out by HPLC-ESI-MS-MS and HPLC with UV-visible detection, respectively. In addition to pelargonidin-3-glucoside, five anthocyanin metabolites were identified in urine: three monoglucuronides of pelargonidin, one sulfoconjugate of pelargonidin and pelargonidin itself. Total urinary excretion of strawberry anthocyanin metabolites corresponded to 1.80 +/- 0.29% (mean +/- SEM, n = 6) of pelargonidin-3-glucoside ingested. More than 80% of this excretion was related to a monoglucuronide. Four hours after the meal, more than two-thirds of anthocyanin metabolites had been excreted, although urinary excretion of the metabolites continued until the end of the 24-h experiment. This study demonstrated that anthocyanins were glucuro- and sulfo-conjugated in humans and that the main metabolite of strawberry anthocyanins in human urine was a monoglucuronide of pelargonidin.
Article
Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants. The content of blackberry (Rubus species) juice was investigated by HPLC/ESI/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents in blackberry extract. Here we investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on the endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. In human umbilical vein endothelial cells (HUVEC) in vitro, peroxynitrite caused a significant suppression of mitochondrial respiration (38 +/- 2.1% of control cells), as measured by the mitochondrial-dependent conversion of the dye MTT to formazan. Peroxynitrite caused DNA strand breakage (63 +/- 1.9% single strand vs 3 +/- 0.9% single strand in control cells), as measured by the alkaline unwinding assay, and caused an activation of PARS, as measured by the incorporation of radiolabeled NAD(+) to nuclear proteins. Blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM; 0.028 microM; 0.0085 microM) reduced the peroxynitrite-induced suppression of mitochondrial respiration, DNA damage and PARS activation in HUVECs. Vascular rings exposed to peroxynitrite exhibited reduced endothelium-dependent relaxant responses in response to acetylcholine as well as a vascular contractility dysfunction in response to norepinephrine. The development of this peroxynitrite-induced vascular dysfunction was ameliorated by the blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM;0.028 microM;0.0085 microM). In conclusion our findings clearly demonstrate that blackberry juice containing cyanidin-3-O-glucoside is a scavenger of peroxynitrite and that exert a protective effect against endothelial dysfunction and vascular failure induced by peroxynitrite.
Article
Anthocyanins, which are used as a food coloring, are widely distributed in human diets, suggesting that we ingest large amounts of anthocyanins from plant-based foods. Mice were fed control, cyanidin 3-glucoside-rich purple corn color (PCC), high fat (HF) or HF + PCC diet for 12 wk. Dietary PCC significantly suppressed the HF diet-induced increase in body weight gain, and white and brown adipose tissue weights. Feeding the HF diet markedly induced hypertrophy of the adipocytes in the epididymal white adipose tissue compared with the control group. In contrast, the induction did not occur in the HF + PCC group. The HF diet induced hyperglycemia, hyperinsulinemia and hyperleptinemia. These perturbations were completely normalized in rats fed HF + PCC. An increase in the tumor necrosis factor (TNF)-alpha mRNA level occurred in the HF group and was normalized by dietary PCC. These results suggest that dietary PCC may ameliorate HF diet-induced insulin resistance in mice. PCC suppressed the mRNA levels of enzymes involved in fatty acid and triacylglycerol synthesis and lowered the sterol regulatory element binding protein-1 mRNA level in white adipose tissue. These down-regulations may contribute to triacylglycerol accumulation in white adipose tissue. Our findings provide a biochemical and nutritional basis for the use of PCC or anthocyanins as a functional food factor that may have benefits for the prevention of obesity and diabetes.
Article
Antioxidant capacity, as measured by oxygen radical absorbance capacity (ORAC(PE)), total phenolic, total and individual anthocyanins, and proanthocyanidin fraction contents were evaluated in red and white wines from grapes. A comparison in terms of antioxidant capacity is made with nontraditional wines made from highbush blueberry. Blueberries are among fruits that are best recognized for their potential health benefits. In red wines, total oligomeric proanthocyanidin content, including catechins, was substantially higher (177.18 +/- 96.06 mg/L) than that in white wines (8.75 +/- 4.53 mg/L). A relative high correlation in red wines was found between ORAC(PE) values and malvidin compounds (r = 0.75, P < 0.10), and proanthocyanidins (r = 0.87, P < 0.05). In white wines, a significant correlation was found between the trimeric proanthocyanidin fraction and peroxyl radical scavenging values (r = 0.86, P < 0.10). A moderate drink (1 drink per day, about 140 mL) of red wine, or white wine, or wine made from highbush blueberry corresponds to an intake of 2.04 +/- 0.81 mmol of TE, 0.47 +/- 0.15 mmol of TE, and 2.42 +/- 0.88 mmol of TE of ORAC(PE)/day, respectively.
Article
Anthocyanins are naturally occurring compounds that impart color to fruits, vegetables, and plants. They are probably the most important group of visible plant pigments besides chlorophyll. Apart from imparting color to plants, anthocyanins also have an array of health-promoting benefits, as they can protect against a variety of oxidants through a various number of mechanisms. However, anthocyanins have received less attention than other flavonoids, despite this. This article reviews their biological functions and pre-clinical studies, as well as the most recent analytical techniques concerning anthocyanin isolation and identification.
Article
The effects of purple sweet potato anthocyanin (SPA) and Cordyceps mushroom extract (CME) on lipid peroxidation, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and cognitive deficits were examined. Both SPA and CME exhibited DPPH radical scavenging activities with similar potency. In contrast, only SPA was shown to effectively inhibit lipid peroxidation initiated by Fe2+ and ascorbic acid in rat brain homogenates. Furthermore, SPA markedly enhanced cognitive performance, assessed by passive avoidance test in ethanol-treated mice. Combined treatments with SPA and CME did not significantly influence the effects of SPA alone. These results demonstrate that anthocyanin prepared from purple sweet potato exhibits memory enhancing effects, which may be associated with its antioxidant properties.
Article
Both lipophilic and hydrophilic antioxidant capacities were determined using the oxygen radical absorbance capacity (ORAC(FL)) assay with fluorescein as the fluorescent probe and 2,2'-azobis(2-amidinopropane) dihydrochloride as a peroxyl radical generator on over 100 different kinds of foods, including fruits, vegetables, nuts, dried fruits, spices, cereals, infant, and other foods. Most of the foods were collected from four different regions and during two different seasons in U.S. markets. Total phenolics of each sample were also measured using the Folin-Ciocalteu reagent. Hydrophilic ORAC(FL) values (H-ORAC(FL)) ranged from 0.87 to 2641 micromol of Trolox equivalents (TE)/g among all of the foods, whereas lipophilic ORAC(FL) values (L-ORAC(FL)) ranged from 0.07 to 1611 micromol of TE/g. Generally, L-ORAC(FL) values were <10% of the H-ORAC(FL) values except for a very few samples. Total antioxidant capacity was calculated by combining L-ORAC(FL) and H-ORAC(FL). Differences of ORAC(FL) values in fruits and vegetables from different seasons and regions were relatively large for some foods but could not be analyzed in detail because of the sampling scheme. Two different processing methods, cooking and peeling, were used on selected foods to evaluate the impact of processing on ORAC(FL). The data demonstrated that processing can have significant effects on ORAC(FL). Considering all of the foods analyzed, the relationship between TP and H-ORAC(FL) showed a very weak correlation. Total hydrophilic and lipophilic antioxidant capacity intakes were calculated to be 5558 and 166 micromol of TE/day, respectively, on the basis of data from the USDA Continuing Survey of Food Intakes by Individuals (1994-1996).
Article
Weaning pigs (7.9 +/- 1.7 kg) were fed a freeze-dried powder of marionberry (MB) by stomach tube to study the absorption and metabolism of anthocyanins. Four major anthocyanins (ACNs) were found in MB: cyanidin-3-glucoside (Cy-3-glc, 78%), cyanidin-3-rutinoside (Cy-3-rutin, 20%), pelargonidin-3-glucoside (Pg-3-glc, 0.4%), and 1 unknown acylated cyanidin-based ACN (UACy, 1.5%). In the urine, the 4 original ACNs and 11 metabolites were identified and quantified. The main metabolites were glucuronidated and/or methylated forms of the original anthocyanins. Total recovery of the 4 original ACNs plus their related metabolites was 0.087 +/- 0.034% for Cy-3-glc, 0.084 +/- 0.026% for Cy-3-rutin, 0.583 +/- 0.229% for Pg-3-glc and 0.036 +/- 0.011% for UACy (mean +/- SD, n = 3), respectively. For the individual ACNs, the amount of metabolites recovered from Cy-3-rutin was lower than that of the original intact Cy-3-rutin, whereas the amounts of metabolites from Cy-3-glc and Pg-3-glc in the urine were much higher than their original forms. In pig plasma, the 2 original ACNs, Cy-3-glc and Cy-3-rutin, and a trace of 1 metabolite (cyanidin monoglucuronide) were detected. The plasma concentration:dose ratio of Cy-3-rutin was higher than that of Cy-3-glc. Different aglycones and/or sugar moieties may influence the absorption and metabolism of ACNs. Cy-3-glc and Cy-3-rutin had similar apparent excretion rates relative to dose, whereas Pg-3-glc had a much higher total urinary excretion than cyanidin-based anthocyanins. Most of Cy-3-glc and Pg-3-glc were excreted in the form of metabolites, whereas most of the Cy-3-rutin was excreted in its original unmetabolized form. Urinary recovery of the acylated anthocyanin was lower than that of nonacylated anthocyanins.
Article
The aglycons of the most abundant anthocyanins in food, cyanidin (cy) and delphinidin (del), represent potent inhibitors of the epidermal growth factor receptor (EGFR). Structure-activity studies show that the presence of vicinal hydroxy substituents at the phenyl ring at the 2-position (B-ring) is crucial for target interaction. The presence of a single hydroxy group or introduction of methoxy substituents at the B-ring results in a substantial loss of inhibitory properties. However, biological activity is not exclusively limited to compounds bearing vicinal hydroxy groups. A contradictory structure-activity relationship is observed for the inhibition of cAMP-specific phosphodiesterases (PDEs). Of the anthocyanidins tested, malvidin, bearing methoxy substituents in the 3'- and 5'-positions, most effectively inhibited cAMP hydrolysis. The absence of methoxy groups and/or replacement by hydroxy substituents was found to strongly diminish PDE-inhibitory properties. We found that either effective EGFR inhibition or effective PDE inhibition is required to achieve a shut-down of the central mitogen-activated protein kinase (MAPK) pathway, a signaling cascade crucial for the regulation of cell growth. This is consistent with the finding that efficient reduction of cell growth is limited to anthocyanidins that are potent EGFR- or PDE-inhibitors including cy and del or malvidin (mv), respectively. In summary, depending on the substitution pattern at the B-ring, anthocyanidins interfere with different signaling cascades involved in the regulation of cell growth.
Article
Anthocyanins and proanthocyanidins were characterized by HPLC-ESI-MS/MS coupled with a diode array and/or fluorescent detector in seven cultivars of Ribes nigrum (black currant) and Ribes rubrum (red currant, Red Lake), six cultivars of Ribes grossularia (gooseberries), Aronia melanocarpa(chokeberry), and Sambucus nigra (elderberry). Thirty-one different anthocyanins were detected in these berries, but not every anthocyanin was observed in each berry. A number of minor anthocyanins were identified from these berries for the first time. The concentrations of individual anthocyanins in all of the berries were quantified using relevant anthocyanidin 3-glucoside standards. Among the berries studied in this paper and in berries in general, chokeberry has the highest total anthocyanin concentrations [1480 mg/100 g of fresh weight (FW)], whereas the lowest total anthocyanin concentration in the berries studied was found in the gooseberry cv. Careless, which contained only 0.07 mg/100 g of FW. Two cultivars of gooseberries (Marigold and Leveller) did not contain any anthocyanins. Total proanthocyanidin concentrations in the berries studied ranged from 23 to 664 mg/100 g of FW in elderberry and chokeberry, respectively. Procyanidin or prodelphinidin polymers were the predominant components (>65% w/w) in most of the berries. The lipophilic and hydrophilic antioxidant capacities were measured by the oxygen radical absorbance capacity (ORAC(FL)) procedure. The total antioxidant capacity varied from 21 micromol of TE/g of FW in Careless gooseberry to 161 micromol of TE/g of FW in chokeberry. Total phenolics in the berries in general paralleled hydrophilic antioxidant capacity.
Article
Anthocyanins are the chemical components that give the intense color to many fruits and vegetables, such as blueberries, red cabbages and purple sweet potatoes. Epidemiological investigations have indicated that the moderate consumption of anthocyanin products such as red wine or bilberry extract is associated with a lower risk of cardiovascular disease and improvement of visual functions. Recently, there is increasing interesting in the pharmaceutical function of anthocyanins. This review summarizes current knowledge on the various molecular evidences of cancer chemoprevention by anthocyanins. These mechanisms can be subdivided into the following aspects: 1) the antioxidation; 2) the molecular mechanisms involved in anticarcinogenesis; 3) the molecular mechanisms involved in the apoptosis induction of tumor cells. Finally, the bioavailability and structure-activity relationship of anthocyanins are also summarized.
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
Anthocyanins in common foods in the United States, other than fruits and berries, were identified and characterized by high-performance liquid chromatography (HPLC)-electrospray ionization-tandem mass spectrometry coupled with diode array detection. Of all of the 40+ vegetables, nuts, and grains screened, seven vegetables, one nut, and one grain were found to contain anthocyanins; the number of anthocyanins detected varied from two in pistachio nuts to 34 in red radishes. The individual anthocyanins were identified by comparing their mass spectrometric data and retention times with those of standards, published data, and reference food samples. In all of the samples analyzed, except for sorghum, only six common anthocyanidins (delphinidin, cyanidin, pelargonidin, petunidin, peonidin, and malvidin) were found as their glycosides. Anthocyanins in certain vegetables such as red cabbage and red radish were highly conjugated with sugars and acylated groups, and thus, their structures were very complicated. Eight different either aliphatic or aromatic acylated groups (acetoyl, coumaroyl, malonoyl, p-hydroxybenzoyl, feruoyl, caffeoyl, sinapoyl, and oxaloyl) were identified in the anthocyanins. In addition to glucose, six other sugar moieties (galactose, xylose, rhamnose, rutinose, sambubiose, and laminaribiose) were observed. Three varieties of sorghum were found to contain 3-deoxyanthocyanidins and their derivatives as major anthocyanins. A number of new anthocyanins were identified in the foods studied. This paper presents complete HPLC profiles and MS spectrometric data, obtained under the same experimental conditions, for common vegetables, pistachio nuts, and sorghum that contain anthocyanins.
Article
Anthocyanins, which are found in high concentrations in fruit and vegetable, may play a beneficial role in retarding or reversing the course of chronic degenerative diseases. However, little is known about the biotransformation and the metabolism of anthocyanins so far. The aim of the study was to investigate possible transformation pathways of anthocyanins by human faecal microflora and by rat liver microsomes as a source of cytochrome P450 enzymes as well as of glucuronyltransferases. Pure anthocyanins, an aqueous extract of red radish as well as the assumed degradation products were incubated with human faecal suspension. The incubation mixtures were purified by solid-phase extraction and analysed by HPLC/DAD/MS and GC/MS. Quantification was done by the external standard method. Furthermore the biotransformation of anthocyanins by incubation with rat liver microsomes in the presence of the cofactor NADPH (as a model for the phase I oxidation) and in the presence of activated glucuronic acid (as a model for the phase II glucuronidation) was investigated. Glycosylated and acylated anthocyanins were rapidly degraded by the intestinal microflora after anaerobic incubation with a human faecal suspension. The major stable products of anthocyanin degradation are the corresponding phenolic acids derived from the B-ring of the anthocyanin skeleton. Anthocyanins were not metabolised by cytochrome P450 enzymes, neither hydroxylated nor demethylated. However they were glucuronidated by rat liver microsomes to several products. The gut microflora seem to play an important role in the biotransformation of anthocyanins. A rapid degradation could be one major reason for the poor bioavailability of anthocyanins in pharmacokinetic studies described so far in the literature. The formation of phenolic acids as the major stable degradation products gives an important hint to the fate of anthocyanins in vivo.
Article
Anthocyanins are suggested to be responsible for protective effects against cardiovascular diseases and certain forms of cancer. Although previous studies have implicated that intact anthocyanidin glycosides were decreased extensively by interactions in the gastrointestinal tract, only few data are available concerning the metabolism by the intestinal microflora. Using a new in vitro model, we have investigated the microbial deglycosylation and degradation of six anthocyanins exhibiting three different aglycones with mono- or di-beta-D-glycosidic bonds using high-performance liquid chromatography-diode array (HPLC-DAD) and gas chromatography-mass spectrometry (GC-MS) detection. We have found that all anthocyanidin glycosides were hydrolysed by the microflora within 20 min and 2 h of incubation depending on the sugar moiety. Due to the high instability of the liberated aglycones at neutral pH, primary phenolic degradation products were already detected after 20 min of incubation. Further metabolism of the phenolic acids was accompanied by demethylation. Because of their higher chemical and microbial stability, phenolic acids and/or other, not yet identified, anthocyanin metabolites might be mainly responsible for the observed antioxidant activities and other physiological effects in vivo.