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Anthocyanins: Extraction, Purification and Applications

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Colorants".

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 30363

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Dr. Ana Fernandes

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REQUIMTE/LAQV, Faculdade de Ciências da Universidade do Porto, Rua do Campo 6 Alegre, 689, 4169-007 Porto, Portugal
Interests: agro-food residues and wastes; anthocyanins; functional food; polysaccharides
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Special Issue Information

Dear Colleagues,

Anthocyanins are key molecules in several research topics, from food quality and nutrition, to health, cosmetic, textile, packaging, or sensors research fields. The great interest that has been given to these natural compounds is mainly generated by their color diversity, spanning practically the whole visible spectrum and by the wide range of biological activities described either for individual or mixture of anthocyanins. Anthocyanins’ chemistry and stability is influenced by two main routes, supramolecular and metamorphose chemistry. All these have crucial implications on anthocyanins functions, from their color and sensorial features, to their physicochemical state, antioxidant properties, transport mechanisms in biological systems, bioavailability, metabolism, and implication for disease alleviation pathways.

This Special Issue is dedicated to the most recent advances on the extraction, purification, and innovative applications of plant anthocyanins, specially focused on the chemical and biological features of these molecules. Furthermore, articles addressing the interactions that occur within plant-based food products, namely with polysaccharides, proteins, and fibers (physically or covalently linked), relating to anthocyanins functions in food and health benefits, are also in the scope of this Molecules Special Issue.

Dr. Ana Fernandes
Guest Editor

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Keywords

anthocyanins
food quality
nutrition
biological activities
antioxidant properties
extraction
plant food products

Published Papers (11 papers)

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Research

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14 pages, 1947 KiB

Open AccessArticle

Stability and Antiproliferative Activity of Malvidin-Based Non-Oxonium Derivative (Oxovitisin A) Compared with Precursor Anthocyanins and Pyranoanthocyanins

by Muci Wu, Yan Ma, Ao Li, Jingyi Wang, Jingren He and Rui Zhang

Molecules 2022, 27(15), 5030; https://doi.org/10.3390/molecules27155030 - 7 Aug 2022

Cited by 3 | Viewed by 1664

Abstract

Oxovitisins are a unique group of anthocyanin derivatives with a non-oxonium nature and α-pyranone (lactone) D ring on the structure. In this study, oxovitisin A was synthesized through the micro-oxidative reaction of carboxypyranomalvidin-3-O-glucoside (vitisin A) with water, and its thermostability, pH, and SO₂ color stability were studied compared with its two precursors, malvidin-3-O-glucoside (Mv3glc) and vitisin A, as well as methylpyrano-malvidin-3-O-glucoside (Me-py). Results showed that oxovitisin A exhibited the highest stabilities, which were inseparably related to its noncharged structure and the additional carbonyl group on the D ring. Moreover, the antiproliferative capacity of oxovitisin A was comparatively evaluated against two human gastrointestinal cancer cell lines. Interestingly, oxovitisin A presented the strongest antiproliferative ability on MKN-28 (IC₅₀ = 538.42 ± 50.06 μM) and Caco-2 cells (IC₅₀ = 434.85 ± 11.87 μM) compared with two other pyranoanthocyanins. Therefore, we conclude that oxovitisin A as a highly stable anthocyanin derivative still exhibits a satisfactory antiproliferative ability. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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19 pages, 39467 KiB

Open AccessArticle

Optimization of a Sustainable Protocol for the Extraction of Anthocyanins as Textile Dyes from Plant Materials

by Elisa Gecchele, Stefano Negri, Anna Cauzzi, Anna Cuccurullo, Mauro Commisso, Alessia Patrucco, Anastasia Anceschi, Giorgio Zaffani and Linda Avesani

Molecules 2021, 26(22), 6775; https://doi.org/10.3390/molecules26226775 - 9 Nov 2021

Cited by 7 | Viewed by 2550

Abstract

Anthocyanins are the largest group of polyphenolic pigments in the plant kingdom. These non-toxic, water-soluble compounds are responsible for the pink, red, purple, violet, and blue colors of fruits, vegetables, and flowers. Anthocyanins are widely used in the production of food, cosmetic and textile products, in the latter case to replace synthetic dyes with natural and sustainable alternatives. Here, we describe an environmentally benign method for the extraction of anthocyanins from red chicory and their characterization by HPLC-DAD and UPLC-MS. The protocol does not require hazardous solvents or chemicals and relies on a simple and scalable procedure that can be applied to red chicory waste streams for anthocyanin extraction. The extracted anthocyanins were characterized for stability over time and for their textile dyeing properties, achieving good values for washing fastness and, as expected, a pink-to-green color change that is reversible and can therefore be exploited in the fashion industry. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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14 pages, 1940 KiB

Open AccessFeature PaperArticle

Anti-Inflammatory and Anti-Diabetic Effect of Black Soybean Anthocyanins: Data from a Dual Cooperative Cellular System

by Jin-Nam Kim, Sung Nim Han and Hye-Kyeong Kim

Molecules 2021, 26(11), 3363; https://doi.org/10.3390/molecules26113363 - 2 Jun 2021

Cited by 11 | Viewed by 2911

Abstract

Obesity is characterized by elevated infiltration of macrophages into adipose tissue, leading to the development of insulin resistance. The black soybean seed coat is a rich source of anthocyanins with antioxidative and anti-inflammatory activities. This study investigated the effects of black soybean anthocyanin extract (BSAn) on obesity-induced oxidative stress, the inflammatory response, and insulin resistance in a coculture system of hypertrophied 3T3-L1 adipocytes and RAW264 macrophages. Coculture of adipocytes with macrophages increased the production of reactive oxygen species and inflammatory mediators and cytokines (NO, MCP-1, PGE₂, TNFα, and IL-6) and the release of free fatty acids but reduced anti-inflammatory adiponectin secretion. BSAn treatment (12.5, 25, 50, and 100 μg/mL) alleviated the coculture-induced changes (p < 0.001) and inhibited coculture-induced activation of JNK and ERK signaling (p < 0.01). BSAn also blocked the migration of RAW264.7 macrophages toward 3T3-L1 adipocytes. In addition, treatment with BSAn increased PPARγ expression and glucose uptake in response to insulin in hypertrophied 3T3-L1 adipocyte and RAW264.7 macrophage coculture (p < 0.01). These results demonstrate that BSAn attenuates inflammatory responses and improves adipocyte metabolic function in the coculture of hypertrophied 3T3-L1 adipocytes and RAW264.7 macrophages, suggesting the effectiveness of BSAn for obesity-induced insulin resistance. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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14 pages, 2063 KiB

Open AccessArticle

Optimization of an Ultrasound-Assisted Extraction Method for the Analysis of Major Anthocyanin Content in Erica australis Flowers

by Ceferino Carrera, María José Aliaño-González, Jaime Rodríguez-López, Marta Ferreiro-González, Fernando Ojeda-Copete, Gerardo F. Barbero and Miguel Palma

Molecules 2021, 26(10), 2884; https://doi.org/10.3390/molecules26102884 - 13 May 2021

Cited by 7 | Viewed by 2249

Abstract

Erica australis plants have been used in infusions and folk medicine for years for its diuretic and antiseptic properties and even for the treatment of infections. In addition, a recently published thorough study on this species has demonstrated its antioxidant, antibiotic, anti-inflammatory, anticarcinogenic and even antitumoral activities. These properties have been associated with the high content of anthocyanins in E. australis leaves and flowers. The aim of the present research is to optimize an ultrasound-assisted extraction methodology for the recovery of the anthocyanins present in E. australis flowers. For that purpose, a Box Behnken design with response surface methodology was employed, and the influence of four variables at different values was determined: namely, the composition of the extraction solvents (0–50% MeOH in water), the pH level of those solvents (3–7), the extraction temperature (10–70 °C), and the sample:solvent ratio (0.5 g:10 mL–0.5 g:20 mL). UHPLC-UV-vis has been employed to quantify the two major anthocyanins detected in the samples. The extraction optimum conditions for 0.5 g samples were: 20 mL of solvent (50% MeOH:H₂O) at 5 pH, with a 15 min extraction time at 70 °C. A precision study was performed and the intra-day and inter-day relative standard deviations (RSDs) obtained were 3.31% and 3.52%, respectively. The developed methodology has been successfully applied to other Erica species to validate the suitability of the method for anthocyanin extraction. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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18 pages, 1237 KiB

Open AccessArticle

Application of Crude Pomace Powder of Chokeberry, Bilberry, and Elderberry as a Coloring Foodstuff

by Nicole Jasmin Nemetz, Andreas Schieber and Fabian Weber

Molecules 2021, 26(9), 2689; https://doi.org/10.3390/molecules26092689 - 4 May 2021

Cited by 13 | Viewed by 2501

Abstract

Berry pomace, rich in polyphenols, especially anthocyanins, accumulates during the production of red juices. Pomace from chokeberry (Aronia melanocarpa Michx.), bilberry (Vaccinium myrtillus L.), and elderberry (Sambucus nigra L.) represent good sources of coloring foodstuffs. Pomace powders (PP) were prepared by milling the seedless fractions of the three dried berry pomaces (50 °C, 8 h). Techno-functional properties of the powders such as particle size distribution, bulk density, sedimentation velocity, and swelling capacity were determined to evaluate the powders for possible food applications. Total anthocyanin content was quantified by UHPLC-DAD before and during a storage experiment to monitor the degradation of anthocyanins in the PP and in a yogurt model application. The high content of phenolic compounds and the still intact cell structure ensured high stability of anthocyanins over 28 days of storage. In the model application, color saturation was stable over the whole storage time of 14 days. Regarding the techno-functional properties, only a few differences between the three PP were observed. The particle size of elderberry PP was larger, resulting in lowest bulk density (0.45 g/mL), high cold-water solubility (16.42%), and a swelling capacity of 10.16 mL/g dw. Sedimentation velocity of the three PP was fast (0.02 mL/min) due to cluster formation of the particles caused by electrostatic and hydrophobic properties. Compared to other high-intensity coloring foodstuffs, the use of PP, showing acceptable color stability with potential health-promoting effects, represents a wide applicability in different food applications and especially in products with a longer shelf-life. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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8 pages, 1040 KiB

Open AccessArticle

Functional Characterization of an Anthocyanin Dimalonyltransferase in Maize

by Michael Paulsmeyer and John Juvik

Molecules 2021, 26(7), 2020; https://doi.org/10.3390/molecules26072020 - 1 Apr 2021

Cited by 9 | Viewed by 2399

Abstract

Anthocyanins are pigments with appealing hues that are currently being used as sources of natural colorants. The interaction of acylation on the stability of anthocyanin molecules has long been known. Maize is an abundant source of malonylglucoside and dimalonylglucoside anthocyanins. The enzyme Aat1 is an anthocyanin acyltransferase known to synthesize the majority of acylated anthocyanins in maize. In this paper, we characterize the substrate specificity and reaction kinetics of Aat1. It was found that Aat1 has anthocyanin 3-O-glucoside dimalonyltransferase activity and is only the second enzyme of this type characterized to this date. Our results indicate that Aat1 can utilize malonyl-CoA; succinyl-CoA and every anthocyanin 3-O-glucoside tested. Results of this study provide insight into the structure–function relations of dimalonyltransferases and give a unique insight into the activity of monocot anthocyanin acyltransferases. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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14 pages, 3240 KiB

Open AccessArticle

Extracts of Digested Berries Increase the Survival of Saccharomyces cerevisiae during H₂O₂ Induced Oxidative Stress

by Gabriel Oliveira, Nataša Radovanovic, Maria Cecilia do Nascimento Nunes, Rikard Fristedt, Marie Alminger and Thomas Andlid

Molecules 2021, 26(4), 1057; https://doi.org/10.3390/molecules26041057 - 18 Feb 2021

Cited by 5 | Viewed by 2018

Abstract

Many studies suggest anthocyanins may prevent the development of several diseases. However, anthocyanin bioactivity against cellular stress is not fully understood. This study aimed to evaluate the protective effect of berry anthocyanins on stressed cells using Saccharomyces cerevisiae. The impact of in vitro gastrointestinal digestion on anthocyanin profiles was also assessed. Bilberry and blackcurrant had higher anthocyanin levels than raspberry and strawberry, but digestion reduced the detected anthocyanins by approximately 90%. Yeast cells with and without digested or nondigested anthocyanin extracts were exposed to H₂O₂ and examined for survival. In the presence of anthocyanins, particularly from digested strawberry, a significant increase in cell survival was observed, suggesting that the type and levels of anthocyanins are important factors, but they also need to undergo gastrointestinal (GI) structural modifications to induce cell defence. Results also showed that cells need to be exposed to anthocyanins before the stress was applied, suggesting induction of a cellular defence system by anthocyanins or their derivatives rather than by a direct antioxidative effect on H₂O₂. Overall, data showed that exposure of severely stressed yeast cells to digested berry extracts improved cell survival. The findings also showed the importance of considering gastrointestinal digestion when evaluating anthocyanins’ biological activity. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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20 pages, 3980 KiB

Open AccessArticle

Ultrasound-Assisted Deep Eutectic Solvent Extraction of Anthocyanins from Blueberry Wine Residues: Optimization, Identification, and HepG2 Antitumor Activity

by Hongkun Xue, Jiaqi Tan, Qian Li, Jintian Tang and Xu Cai

Molecules 2020, 25(22), 5456; https://doi.org/10.3390/molecules25225456 - 20 Nov 2020

Cited by 19 | Viewed by 2844

Abstract

Blueberry wine residues produced during the wine-brewing process contain abundant anthocyanins and other bioactive compounds. To extract anthocyanins from blueberry wine residues more efficiently, a novel procedure of ultrasound-assisted deep eutectic solvent extraction (UADESE) was proposed in this work. The extraction process was optimized by response surface methodology coupled with genetic algorithm. The optimum extraction parameters to achieve the highest yield of anthocyanins (9.32 ± 0.08 mg/g) from blueberry wine residues by UADESE were obtained at water content of 29%, ultrasonic power of 380 W, extraction temperature of 55 °C, and extraction time of 40 min. The AB-8 macroporous resin combined with Sephadex LH-20 techniques was used to purify the crude extract (CE) obtained under optimum extraction conditions and analyze the anthocyanins composition by HPLC-ESI-MS/MS. The cyanidin-3-rutinoside with purity of 92.81% was obtained. The HepG2 antitumor activity of CE was better than that of the purified anthocyanins component. Moreover, CE could increase the intracellular reactive oxygen species levels and the apoptosis, and arrest HepG2 cells in the S phases. These findings provided an effective and feasible method for anthocyanins extraction, and reduced the environmental burden of this waste. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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11 pages, 1247 KiB

Open AccessArticle

Carbohydrate Hydrolase-Inhibitory Activity of Juice-Based Phenolic Extracts in Correlation to Their Anthocyanin/Copigment Profile

by Kirsten Berger, Johanna Josefine Ostberg-Potthoff, Tamara Bakuradze, Peter Winterhalter and Elke Richling

Molecules 2020, 25(22), 5224; https://doi.org/10.3390/molecules25225224 - 10 Nov 2020

Cited by 12 | Viewed by 2284

Abstract

Red fruits and their juices are rich sources of polyphenols, especially anthocyanins. Some studies have shown that such polyphenols can inhibit enzymes of the carbohydrate metabolism, such as α-amylase and α-glucosidase, that indirectly regulate blood sugar levels. The presented study examined the in vitro inhibitory activity against α-amylase and α-glucosidase of various phenolic extracts prepared from direct juices, concentrates, and purees of nine different berries which differ in their anthocyanin and copigment profile. Generally, the extracts with the highest phenolic content—aronia (67.7 ± 3.2 g GAE/100 g; cyanidin 3-galactoside; chlorogenic acid), pomegranate (65.7 ± 7.9 g GAE/100 g; cyanidin 3,5-diglucoside; punicalin), and red grape (59.6 ± 2.5 g GAE/100 g; malvidin 3-glucoside; quercetin 3-glucuronide)—showed also one of the highest inhibitory activities against α-amylase (326.9 ± 75.8 μg/mL; 789.7 ± 220.9 μg/mL; 646.1 ± 81.8 μg/mL) and α-glucosidase (115.6 ± 32.5 μg/mL; 127.8 ± 20.1 μg/mL; 160.6 ± 68.4 μg/mL) and, partially, were even more potent inhibitors than acarbose (441 ± 30 μg/mL; 1439 ± 85 μg/mL). Additionally, the investigation of single anthocyanins and glycosylated flavonoids demonstrated a structure- and size-dependent inhibitory activity. In the future in vivo studies are envisaged. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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Review

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24 pages, 1736 KiB

Open AccessReview

Alternative Extraction and Downstream Purification Processes for Anthocyanins

by Ana N. Nunes, Alexandra Borges, Ana A. Matias, Maria Rosário Bronze and Joana Oliveira

Molecules 2022, 27(2), 368; https://doi.org/10.3390/molecules27020368 - 7 Jan 2022

Cited by 18 | Viewed by 3289

Abstract

Anthocyanins are natural pigments displaying different attractive colors ranging from red, violet, to blue. These pigments present health benefits that increased their use in food, nutraceuticals, and the cosmetic industry. However, anthocyanins are mainly extracted through conventional methods that are time-consuming and involve the use of organic solvents. Moreover, the chemical diversity of the obtained complex extracts make the downstream purification step challenging. Therefore, the growing demand of these high-value pigments has stimulated the interest in designing new, safe, cost-effective, and tunable strategies for their extraction and purification. The current review focuses on the potential application of compressed fluid-based (such as subcritical and supercritical fluid extraction and pressurized liquid extraction) and deep eutectic solvents-based extraction methods for the recovery of anthocyanins. In addition, an updated review of the application of counter-current chromatography for anthocyanins purification is provided as a faster and cost-effective alternative to preparative-scale HPLC. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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17 pages, 359 KiB

Open AccessReview

Anthocyanins, Microbiome and Health Benefits in Aging

by Rachel Hair, Junichi R. Sakaki and Ock K. Chun

Molecules 2021, 26(3), 537; https://doi.org/10.3390/molecules26030537 - 21 Jan 2021

Cited by 46 | Viewed by 4712

Abstract

The percentage of individuals over the age of 60 is projected to reach 22% by 2050; chronic diseases associated with aging can present challenges for these individuals. Anthocyanins and the gut microbiome have each been studied as independent influencers of health. Both these factors have shown to have a positive effect on cardiovascular and bone health in individuals, as well as on the prevention or treatment of certain forms of cancers. Anthocyanins have shown to modulate the composition of the gut microbiome and may have overlapping mechanisms in the prevention and treatment of cardiovascular disease, cancer, neurodegenerative disorders and aging-associated bone loss. These health outcomes are responsible for the hospitalization and deaths of millions of Americans every year and they cost the United States billions of dollars each year to maintain, prevent and treat. Alternative methods of treatment and prevention are desired since conventional methods (surgical and pharmacological methods, physical therapy, etc.) can be costly and have significant side effects; evidence suggests that anthocyanins and the gut microbiome may be potential avenues for this. This review evaluates the findings of existing literature on the role of anthocyanins and the gut microbiome on health and their potential as a natural therapeutic agent or a target organ to provide an alternative to the conventional methods of disease prevention and treatment. Full article

(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)

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