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Anthocyanins: Naturally occuring fruit pigments with functional properties
Abstract and Figures
Anthocyanin is a water-soluble pigment existing in plants, and has various health benefits to humans. As far as that goes, the number and location of the hydroxyl groups of the parent nucleus have significant effects on the anthocyanin activities. This review summarizes anthocyanin content in fruits, the importance of anthocyanin in relation to human health, some aspects of anthocyanin biochemistry and their bioavailability, the distribution in some fruits, the biosynthetic pathway, different extraction, separation and purification methods, and also identification methods. Beneficial effects of anthocyanin pigments are
reported in the scientific literature and these compounds are nowadays recognized as potentially therapeutic. The lack of antioxidant defense mechanisms in humans is associated with the cardiovascular and coronary artery diseases, cancer and
diabetes, besides others.
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... Caffeoylated anthocyanin, malonylated anthocyanin, acrylated anthocyanin, and coumaroylated anthocyanin can be further categorized as the acylated form of anthocyanins. Both color and hue of anthocyanins are affected by hydroxylation, glycosylation, methylation, and acylation pattern of the phenyl constituent of the anthocyanidins, and the color varies from orange-red (cyanidin, pelargonidin) to purple and pink-magenta (petunidin, delphinidin, malvidin, and peonidin) (da Costa et al., 2000;Iversen, 1996;Keppler and Humpf, 2005;Khoo et al., 2017;Lo Piero, 2015 Figure 2. Anthocyanidins relevance to human diet -general structure, distribution, and metabolic products (Leong et al., 2018;Turturică et al., 2015) It is currently thought that six anthocyanins are relevant to the human diet ( Figure 2). Their distribution in fruits and vegetables are 50% cyanidin, 12% delphinidin, 12% pelargonidin, 12% peonidin, 7% malvidin, and 7% petunidin (Leong et al., 2018;Turturică et al., 2015). ...
... Both color and hue of anthocyanins are affected by hydroxylation, glycosylation, methylation, and acylation pattern of the phenyl constituent of the anthocyanidins, and the color varies from orange-red (cyanidin, pelargonidin) to purple and pink-magenta (petunidin, delphinidin, malvidin, and peonidin) (da Costa et al., 2000;Iversen, 1996;Keppler and Humpf, 2005;Khoo et al., 2017;Lo Piero, 2015 Figure 2. Anthocyanidins relevance to human diet -general structure, distribution, and metabolic products (Leong et al., 2018;Turturică et al., 2015) It is currently thought that six anthocyanins are relevant to the human diet ( Figure 2). Their distribution in fruits and vegetables are 50% cyanidin, 12% delphinidin, 12% pelargonidin, 12% peonidin, 7% malvidin, and 7% petunidin (Leong et al., 2018;Turturică et al., 2015). ...
Anthocyanins are flavonoid containing polyphenolic phytochemicals. They are widely present in plants and accounts for different color shades displayed by the plant organs. A broad range of health-revitalizing effects is attributed to anthocyanins, constituting a vital part of the human diet. They are also accountable for ameliorating the detrimental effects of various lifestyle diseases, including cancer, cardiovascular disorders, neurological disorders, etc. These beneficial impacts highly depend on the bioavailability of anthocyanins, governed by their absorption and metabolism in the human body. The primary goal of this review is to summarize the latest anthocyanin knowledge while focusing on the chemistry, pharmacokinetics, and various biological advantages with anti-cancer, neuroprotective, antidiabetic, antioxidant, cardiovascular protective, vision improvement, antiviral, and antimicrobial effects.
... The stability of ACNs is closely related to pH, temperature, light, presence of solvents and oxygen, and other factors such as the type of pigment or copigments present but also the chemical structure and the presence of hydroxyl and methoxyl groups (Castañeda-Ovando et al., 2009;Turturicȃ et al., 2015). The characteristic coloration of ACNs depends on the pH of the solution. ...
... ACNs are extracted as a raw blend, with large amounts of unwanted products such as sugars, acids, amino acids, and proteins, so it is necessary to purify them. The purification of ACNs can be performed with various methods including C18 cartridges previously activated with methanol, followed by water or 0.01% aqueous HCl or 3% formic acid or with chromatographic methods, including thin layer chromatography, high fast counter-current chromatography, high performance liquid chromatography, cellulose column reverse phase chromatography, and ion pair chromatography, as well as gas chromatography (Turturicȃ et al., 2015). In the last years, new unconventional ultrasound-based extraction methods have been studied. ...
... 20,21 They exist as red in acidic, blue/ purple in basic and green/yellow at higher pH conditions. 22 The advantages of using anthocyanin are its low cost of production, easy preparation, bio-compatibility, production of wide-ranging colour spectrum and high stability at harsh experimental conditions. 23 In the current study, a new media was formulated with the optimized concentrations of NaCl and LiCl. ...
Methicillin resistant Staphylococcus aureus harbouring other virulence factors in food is a serious threat to food safety. Delayed detection of MRSA may lead to fatal consequences due to the challenging treatment methods. To address the issue, early prognosis is prerequisite. We report one step QuEChERS detection method wherein, a media with selective agents such as cefoxitin, cyanidin, lithium chloride and methicillin (CCLM) was formulated for the specific cultivation and detection of MRSA within 5 hours. Direct application of the newly developed method was tested by screening food for MRSA and its comparison with conventional biochemical and molecular characterization. Growth of MRSA in the CCLM media was observed within 4 hours. This highly specific method is sensitive to detect 104 CFU/mL visually and 101 CFU/mL spectrophotometrically. 25% of food samples harboured MRSA which points to an immediate need of consideration by the authorities. The newly designed QuEChERS cyanin based chromogenic detection system is unequivocal with the conventional and molecular method of MRSA detection and can be of great use in diagnostic and in food safety laboratories.
... The activity result of WS-O showed that even without the addition of dye, there was already an antioxidative property in the sample. The smaller difference in the trend before and after incorporation was because each dye reacts differently in different pH and temperature, which also alters their stability after being incorporated into the bioplastic mixture (Turturică et al. 2015;Sigurdson et al. 2017). Each of their IC 50 was determined and presented in Fig. 9b. ...
Pollution caused by petroleum-based plastics, especially single-use food packaging, has become a global problem. In order to offer sustainable alternatives to traditional plastic, it is important to explore the use of new biodegradable plastic materials made from renewable sources. Bioplastics made from seaweed extracts, such as carrageenan and alginate, show promise as viable options. However, these phycocolloids are expensive and require a lengthy extraction process. This report presents the development of bioplastics using the entire biomass of a red seaweed (Kappaphycus sp.). The initial focus of the study was to optimize the concentration of the main ingredients, which included biomass and glycerol (plasticizer agent). The concentration range that was tested included a biomass-to-water ratio of 1:50 to 1:90 and a plasticizer concentration of 1% to 5% (v/v). Subsequently, bioplastics were created by incorporating natural dye extracts from butterfly pea flower (Clitoria ternatea), bougainvillea flower (Bougainvillea glabra), and dragon fruit peel (Hylocereus polyrhizus) using a casting method at the selected optimum concentrations. The resulting bioplastics were then characterized for their physicochemical properties (including shelf-life and biodegradability), and antimicrobial activity using standard methods. The study successfully developed bioplastics with a thickness of less than 100 µm and a moisture content below 40%. Within the tested range, the most optimal concentrations were a biomass-to-water ratio of 1:50 to 1:60 and 1% glycerol, based on factors such as tensile strength (TS), water vapor transmission rate (WVTR), elasticity, appearance, shelf-life, and biodegradability. All of the bioplastics completely degraded during a soil burial test within 13-15 days. The inclusion of brightly coloured plant extracts increased the bioplastics' antioxidant properties by more than 10% in scavenging activity. Furthermore, the dyed bioplastics had a shelf-life that was 20-30% longer. While these biomass bioplastics have lower tensile strength, elasticity, and water vapor permeation rate (<10 MPa, <30 MPa, and >2 g m⁻² h⁻¹, respectively), they show potential for applications where high tensile strength is not required, such as food packaging or wrapping.
... Anthocyanins are water soluble plant pigments and usually present in the form of glycosylated and/or acylated anthocyadinins. Its stability is strongly dependent on the pH of solution because of the ionic nature of its molecular structure having a positive charge at the oxygen atom of the C-ring of basic flavonoid structure called as flavylium (2-phenylchromenylium) ion (Turturicȃ, Oancea & Râpeanu, 2015). The red colored pigments are stable in acidic pH, they would become purple in neutral pH and change to blue in alkaline pH. ...
... The quinonoids are unstable at low pHs. At neutral pH, further deprotonation of quinonoid molecules caused resonance-stabilized quinonoid ions (purple color) (Turturică et al. 2015, Khoo et al. 2017, Mattioli et al. 2020. As the pH increases in alkaline conditions, the yellow chalcone structure appears due to the opening of the main ring of ACY (ring C). Figure 3 shows the structural and color variations of ACY at different pH values. ...
... Apart from that, Serna-Saldivar [35] reported that in recent decades, in we consider that purple corn besides being a source of antioxidants, could represent an interesting ingredient for the formulation of gluten-free food products (which can be offered to celiac patients) and, a food with potential use in bakery, where purple corn flour can be used to make products such as gluten-free and eggless muffins, which makes them suitable foods for people allergic to eggs or people of vegan consumption patterns [36]. Likewise, the presence of color in corn opens the outlook for the development of products that are attractive to the eye and simultaneously, due to its anthocyanin content, can promote human health [37]. [22,[24][25]. ...
Background: Anthocyanins (AAs) are natural pigments and bioactive compounds that are of broad interest due to their potential beneficial effects on health. In the market, while some foods, such as berries, provide important amino acid (AA) intakes, there is a growing trend to explore new sources. In Mexico, there is the Mexican Purple Corn, a variant capable to produce AAs in all the organs of the corn ear. We overlook that the preparation of foods and beverages from these raw materials may represent the development of potential functional foods and a means to increase the dietary intake of AAs. Methods: We used spectrophotometry to quantify the total anthocyanins content (TAC) of three foods made from purple kernels, and six beverages prepared from corn husks+corncobs or corn silks. Foods consisted of elote (Mexican street corn or corn on a cob), a snack, and tortillas, while beverages involved what we named functional beverages, infusions, and hot teas. We compared their TAC values and estimated the AAs intake. Results: Foods and beverages exhibited total antioxidant capacities (TACs) ranging from 3.0 mg to 119.5 mg per 100 g of biomass (p ≤ 0.05). Notably, most beverages demonstrated higher TACs than foods. The corn husks+corncobs infusion recorded the highest TAC, succeeded by functional beverages derived from amino acid (AA) extracts of corn husks+corncobs (67.04 and 93.12 mg of TAC per 100 g of biomass, p ≤ 0.05). Among hot teas and infusions, maceration in the latter resulted in a higher AA extraction. For foods, TACs varied from 4.3 to 38.4 mg of TAC per 100 g of biomass, and, similar to beverages, the preparation process influenced TAC. The roasted snack exhibited a higher AA content. Conclusion: Mexican Purple Corn shows promise as a source for foods and beverages rich in amino acids (AAs). This crop represents an option to increase the daily intake of this flavonoid, and to acquire its potential bioactive effects. On a regular day, we can obtain 95 mg of TA from 300 g of purple corn-based foods, and 750 mL of different beverages made from corn husks, corncobs, and corn silks. Keywords: Mexican Purple Corn, anthocyanins, corn husks, corncobs, corn silks, dietary source of anthocyanins.
... Traditionally, solvent extraction is the common method for isolating bioactive compounds, which applies the mechanisms of a solid matrix [111]. The diffusivity and solubility of bioactive compounds from raw materials promote the extraction process [110]. ...
The agriculture and horticulture industries generate many by-products while processing commodities, leading to significant environmental and societal dilemmas. Bioactive compounds obtained from by-products of plants are also known as ingredients in traditional medicines and the food industry due to their potential health benefits for humans as antioxidant, anti-inflammatory, and antimicrobial agents. On the other hand, an extensive array of colorants from natural sources has been scrutinized recently in different sectors to mitigate the negative ecological impacts of synthetic dyes, especially in modern textile manufacturing. Approaching these matters, this paper reviews various chemical compositions of plant secondary metabolites, including flavonoids, tannins, phenolic acids, essential oils, tulipalins, and factors that influence the isolation process. Moreover, the article offers an updated view of the advanced technologies for extraction, focusing on eco-friendly solvents such as water, supercritical carbon dioxide, and deep eutectic solvents. Eventually, a comparison of different extraction methods is highlighted to devise the most appropriate strategy for industries.
Graphical abstract
Rich in antioxidants with a variety of flavones and anthocyanins, passionflower/fruit has been extensively used in food, beverage, medicinal, and natural dyes industries. The individual components present in passionflower are identified by extracting them in methanol, partitioning them between ethyl acetate and aqueous layers, and recording their ESI mass spectrometric data. The steady‐state absorption and fluorescence spectra of the extract in methanol and dimethyl sulfoxide are recorded and the lifetime of the fluorescing species is reported. The pH dependence of the absorption spectrum confirms the presence of the anthocyanins.
a b s t r a c t Propolis samples from important honey producing locations of Anatolia namely; Bingol (BG), Rize (RZ), Tekirdag (TK) and Van (VN), were evaluated for their antiradical capacities, total phenolic contents and individual phenolic compounds which was recovered by means of pressurized liquid extraction (PLE). Several extraction parameters of PLE such as; temperature, pressure, solvent type, extraction time and cell size were investigated for their effects on the extraction performances. The results showed that, 40 °C, 1500 psi, Ethanol:water:HCl; (70:25:5, v/v/v) containing 0.1% tert-butylhydroquinone (tBHQ) as solvent, three extraction cycles within 15 min, and a cell size of 11 mL was the most favorable PLE oper-ating conditions. Results of the tests performed to designate the success of the polyphenol analysis showed that the recovery was in the range of 97.2% and 99.7%. Major phenolic compounds in all samples were found to be gallocatechin (GCT), catechin (CT), epicat-echin gallate (ECTG), caffeic acid (CA), chlorogenic acid (ChA), and myricetin (Myr). ChA level of BG prop-olis was 4.5, 3 and 23 times higher than that of RZ, TK and VN region, respectively. Antiradical tests showed that all propolis samples have superior antiradical capacities up to 500 mg Trolox equivalent activity per gram of extract.
Anthocyanins belong to a large group of secondary plant metabolites collectively known as flavonoids, a subclass of the polyphenol family. They are a group of very efficient bioactive compounds that are widely distributed in plant food. Anthocyanins occur in all plant tissues, including leaves, stems, roots, flowers, and fruits. Research on phenolic compounds through the last century, from the chemical, biochemical, and biological points of view, has focused mainly on the anthocyanins. Anthocyanins have structures consisting of two aromatic rings linked by three carbons in an oxygenated heterocycle (i.e., a chromane ring bearing a second aromatic ring in position 2). The basic chromophore of anthocyanins is the 7-hydroxyflavilyum ion. Anthocyanin pigments consist of two or three chemical units: an aglycon base or flavylium ring (anthocyanidin), sugars, and possibly acylating groups. Only six of the different anthocyanidins found in nature occur frequently and are of dietary importance: cyanidin, delphinidin, petunidin, peonidin, pelargonidin, and malvidin. Each aglycon may be glycosilated or acylated by different sugars and aromatic or aliphatic acids, yielding over 600 different anthocyanins reported from plants. The sugar moiety is typically attached at the 3-position on the C-ring or the 5-position on the A-ring. The chromophore of eight conjugate double bonds carrying a positive charge on the heterocyclic oxygen ring is responsible for the intensive red-orange to blue-violet color produced by anthocyanins under acidic conditions. Anthocyanins occur in solution as a mixture of different secondary structures: flavylium ion, a quinoidal base, a carbinol base, and a chalcone pseudobase. Self-association, intermolecular, and intramolecular co-pigmentation of anthocyanins leads to the formation of tertiary structures through varying stabilization mechanisms. Anthocyanin composition has been used as a botanical tool for taxonomic classification of plants. In addition, anthocyanin profiles of fruits and vegetables allow detecting adulteration of anthocyanin-based products and are indicators of product quality. Anthocyanins are common components of the human diet, as they are present in many foods, fruits, and vegetables, especially in berries. Moreover, anthocyanins have an antioxidant activity, depending to a large extent upon their chemical structure. Many epidemiological studies have shown the benefits of a diet rich in fruit and vegetables to human health, and for the prevention of various diseases associated with oxidative stress, such as cancer and cardiovascular diseases. Anthocyanin-rich extracts are increasingly attractive to the food industry as natural alternatives to synthetic FD&C dyes and lakes, because of their coloring properties. Anthocyanins are also one of the nine European Union-designated natural color classes. Various adverse effects on health have frequently been attributed to synthetic antioxidants. For these reasons, currently, there is a trend towards relying on antioxidants derived from natural products. Anthocyanins act as antioxidants both in the foodstuffs in which they are found and in the organism after intake of these foods. This review, like the first one of the series, intends to reflect the interdisciplinary nature of the research that is currently carried out in this prolific area.
The aim of this study was to increase extraction rate, yield and quality of products, associating microwave field with extraction of plant's active compounds such as flavonoids and phenolic acids from Cynara scolymus (CS) leaves. Compared to classical hot extraction methods (CE), microwave extraction (MAE) provides higher purities in active compounds while avoiding local overexposure, very important assets for industry. Spectrophotometry was used to separate and quantify flavonoids (FV) and phenolic acids (FA) in herbal extracts of Cynara scolymus.
The microwave-assisted extraction (MAE) system is an efficient technique under the optimal condition in the extraction of bioactive chemical compounds E-and Z-guggolsterone, cinnamaldehyde and tannin from the plants has been investigated. The results show that, this method provides a fast and easy procedure for the extraction compared to the conventional extraction techniques.
ABSTRACT Total anthocyanins from Campbell Early grape peel were extracted by using ultrasonic-assisted extraction technology. The experiments were performed according to a five-level, three-variable central composite rotatable design. The best possible combinations of extraction variables were obtained for the maximum extraction of total anthocyanins from grape peel using response surface methodology. The optimal extraction conditions include 52.35% ethanol, 45.14C temperature and 24.50 min time for the maximum total anthocyanins (6.26 mg/mL). Under these conditions, the experimental total anthocyanins were 6.24 mg/mL of the grape peel extract, which is well matched with the predicted values. PRACTICAL APPLICATION Anthocyanins are functional compounds and natural food colorants, which can replace synthetic colors. Grapes and grape residues are good sources of anthocyanins, and maximum recoveries of these compounds are possible by using optimized extraction processes. In our study, we have optimized the ultrasonic-assisted extraction of anthocyanins from grape peel by using central composite rotatable design and response surface methodology. This extraction method is an inexpensive, because of low instrumental involvement, simple and efficient alternative to conventional extraction techniques. Optimized extraction conditions predicted and validated in our study can be used for improved recovery of anthocyanins from grape peel.
Anthocyanins (AC) are water-soluble natural pigments found in various parts of higher plants. Despite their limited oral bioavailability and very low post-absorption plasma concentrations, the dietary consumption of these pigments has been proposed to be associated with a significant protection against several human pathological conditions, including cardiovascular diseases. Many studies highlighted that some health benefits of AC localize in particular at endothelium level, contributing to vascular homeostasis and also to the control of angiogenesis, inflammation, and platelet aggregation. This review reports and comments on the large existing literature addressing the molecular mechanisms that, beyond the antioxidant properties, may have a significant role in the effects of AC and AC-rich foods on vessel endothelium. Among these, AC have been reported to prevent peroxynitrite-mediated endothelial dysfunction in endothelial cells (ECs), thanks to their capability to modulate the expression and activity of several enzymes involved in NO metabolism. Furthermore, evidence indicates that AC can prevent the expression of adhesion molecules and the adhesion of monocytes to ECs challenged by pro-inflammatory agents. Overall, the activity of AC could be associated with the ability to elicit cell adaptive responses involving the transcription factor Nrf2 by affecting the "nucleophilic tone" of the organism. This review confirms the importance of specific nutritional molecules for human health and suggests new avenues for nutrition-based interventions to reduce the risk of cardiovascular disease in the population.
Agro-industrial byproducts represent a serious environmental problem and the industries producing these residual materials have incurred expenses for their proper disposal and generally increase the pollution due to the high content of organic substances and might represent legal problems. However, the residues such as grape wastes are potential source of phenolic compounds which are widely known for their high antioxidant activity. Bioprocesses such as enzyme technology represent an alternative for production of those bioactive compounds from agro-industrial byproducts. In this study, different types of commercial enzymes such as Celluclast® 1.5 L, Pectinex® Ultra and Novoferm® were used to release phenolic compounds from grape wastes. The hydrolysates were analyzed in their total phenolic compounds and antioxidant activity with Folin–Ciocaletu test and DPPH· radical-scavenging assay, respectively. A good correlation was obtained between antioxidant activity and phenolics released. The highest antioxidant activities registered were 86.8 ± 0.81, 82.9 ± 0.31 and 90 ± 0.37 % at 12 h for Celluclast® 1.5 L, Pectinex® Ultra and Novoferm®, respectively. Novoferm® had the strongest effect on phenolic release from grape waste, followed by Pectinex® Ultra and Celluclast® 1.5 L. High performance liquid chromatography–electrospray–mass spectrometry clearly revealed that the increment of antioxidant activity is associated with the release of O-coumaric acid.
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.
Prevention of E,Z-isomerization of caffeoyl residues of a tri-(E)-caffeoyl anthocyanin, heavenly blue anthocyanin (HBA), and its stability under UV-B irradiation conditions were studied. We isolated four photoproducts from irradiated HBA and their structures were determined to be mono- or di-Z-caffeoyl isomers of HBA and mono-deglucosylated HBA. Under such conditions one caffeoyl residue, the innermost one, never isomerized to the Z-form, suggesting that intramolecular stacking must prevent photoisomerization. In general, anthocyanins are considered to be more stable in strong acidic than neutral aqueous media. However, with UV-B irradiation HBA was most stable in aqueous solution at pH 7.5 and most unstable in acidic methanol solutions. It was found to emit strong fluorescence on excitation with UV-B, possibly resulting from intramolecular association of caffeoyl moieties with the anthocyanidin nucleus. The finding that pigment in petals is more tolerant of UV-irradiation may be rational in the context of the necessity to resist strong solar radiation.