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Anthocyanins: Antioxidant Capacity and Health Effects

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A special issue of Antioxidants (ISSN 2076-3921). This special issue belongs to the section "Natural and Synthetic Antioxidants".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 18881

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Prof. Dr. Agustín G. Asuero

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Department of Analytical Chemistry, University of Seville, 41012 Sevilla, Spain
Interests: natural antioxidants; chemometrics; solution chemistry
Special Issues, Collections and Topics in MDPI journals

Dr. Noelia Tena

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Guest Editor

Department of Analytical Chemistry, University of Seville, 41012 Sevilla, Spain
Interests: analytical chemistry; food chemistry; food safety and quality; oxidation stability; sensory assessment; spectroscopic techniques; chemometrics
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Interest in natural bioactive compounds has been increasing in recent years. Their beneficial health implications act as a lure for consumers and producers, leading to increased demand. In the particular case of anthocyanins or other colored antioxidants, they are not only in demand for their antioxidant properties but also for their usefulness as natural dyes—a dual function that is currently highly appreciated. This Special Issue has been created with the intention of compiling the most up-to-date information on the state of the art of these compounds by providing a broad overview of: (i) The different extraction sources, giving special relevance to the extraction of agricultural and food waste and byproducts, for example, grape and winery wastes; (ii) The different extraction methods, their extractive capacity, and the impact on the antioxidant activity of the extracts, also paying attention to nonconventional and sustainable green techniques and to deeply biocompatible natural eutectic solvents; (iii) The physicochemical and biochemical characterization of the extracted compounds in addition to innovative technological processes that may affect bioavailability and biological effects; (iv) Studies on the antioxidant capacity of these compounds as investigated from different perspectives—individually and in mixtures, in different matrices, in vivo and in vitro; (v) Studies on the synergy and competition between bioactive compounds and their kinetics of action; (vi) Studies demonstrating the beneficial effect of these value-added products on health, primarily their high anti-aging activities; (vii) Co-pigmentation and encapsulation to achieve stabilization of anthocyanins; (viii) The search for markers of food quality and authenticity with the help of chemometric methods. Findings in these fields will play an important role in life sciences, especially in age-related diseases. Following studies over the past decades, these plant chameleons—or anthocyanins, as baptized by Tswett, the inventor of chromatography—can seem partly mythical or magical considering their effects on health.

Dr. Agustín G. Asuero
Dr. Noelia Tena
Guest Editors

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Keywords

antioxidant capacity
anthocyanins
natural antioxidant
modern assisted extraction methods
bioavailability
biological effect
extraction efficiency
co-pigmentation
encapsulation
age-related diseases

Published Papers (8 papers)

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Research

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16 pages, 3259 KiB

Open AccessArticle

When Cannabis sativa L. Turns Purple: Biosynthesis and Accumulation of Anthocyanins

by Laura Bassolino, Flavia Fulvio, Chiara Pastore, Federica Pasini, Tullia Gallina Toschi, Ilaria Filippetti and Roberta Paris

Antioxidants 2023, 12(7), 1393; https://doi.org/10.3390/antiox12071393 - 06 Jul 2023

Cited by 1 | Viewed by 4297

Abstract

Environmental cues elicit anthocyanin synthesis in plant vegetative and reproductive tissues. Their accumulation in different organs accounts for their diverse biological functions, mainly related to their antioxidant properties, and it depends on a temporally and spatially regulated mechanism controlled by the action of a well-known multi-transcription factor complex. Despite the highly recognizable value of Cannabis sativa L. as a natural biorefinery of phytochemicals, very little information is known on anthocyanin pigmentation in this species. In this work, a targeted quantification of anthocyanins via HPLC-MS/MS, combined with the transcriptional profile via RT-qPCR of genes encoding for structural and decorating enzymes and regulatory transcription factors in different C. sativa tissues, help gain insights into the anthocyanin pathway in this species. To the best of our knowledge, this is the first report on the identification of cyanidin-3-rutinoside (keracyanin) as the major anthocyanin in C. sativa vegetative and floral tissues. Keracyanin amounts were higher than in small berries, suggesting that Cannabis biomass is a valuable source of colored antioxidants to be exploited in diverse applications. Furthermore, a gene putatively encoding for an anthocyanin DTX35 type transporter and CsTTG1 were identified in silico and their transcriptional levels were assessed via RT-qPCR. The results allow us to provide the first model of anthocyanin regulation in C. sativa, opening a new research scenario in this species for both breeding purposes and phytochemical exploitation. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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29 pages, 19067 KiB

Open AccessArticle

Antioxidant Properties Mediate Nephroprotective and Hepatoprotective Activity of Essential Oil and Hydro-Alcoholic Extract of the High-Altitude Plant Skimmia anquetilia

by Neha Kukreti, Havagiray R. Chitme, Vinay K. Varshney, Basel A. Abdel-Wahab, Masood Medleri Khateeb and Mohammed Shafiuddin Habeeb

Antioxidants 2023, 12(6), 1167; https://doi.org/10.3390/antiox12061167 - 28 May 2023

Cited by 4 | Viewed by 1937

Abstract

There are many high-altitude plants such as Skimmia anquetilia that are unexplored for their possible medicinal values. The present study was conducted to examine the antioxidant activities of Skimmia anquetilia (SA) using in vitro and in vivo models. The SA hydro-alcoholic extracts were investigated using LC-MS for their chemical constituents. The essential oil and hydro-alcoholic extracts of SA were evaluated for pharmacological properties. The antioxidant properties were evaluated using in vitro DPPH, reducing power, cupric reducing antioxidant power, and metal chelating assays. The anti-hemolytic activity was carried out using a human blood sample. The in vivo antioxidant activities were evaluated using CCL₄-induced hepatotoxicity and nephrotoxicity assay. The in vivo evaluation included histopathological examination, tissue biochemical evaluation such as the kidney function test, catalase activity, reduced glutathione activity, and lipid peroxidation estimation. The phytochemical investigation showed that the hydro-alcoholic extract contains multiple important active constituents such as L-carnosine, acacetin, linoleic acid, leucylleucyl tyrosine, esculin sesquihydrate, etc., similar to the components of SA essential oil reported in a previous study. The high amount of total phenolic content (TPC) and total flavonoid content (TFC) reflect (p < 0.001) a high level of reducing power, cupric reducing, and metal chelating properties. This significantly (p < 0.001) inhibited enlargement of the liver, with a significant reduction in ALT (p < 0.01) and AST (p < 0.001). Highly significant improvement in the functioning of the kidney was noted using the blood urea and creatinine (p < 0.001) levels. Tissue-based activities showed a major rise in catalase, reduced glutathione, and reduced lipid peroxidation activities. We conclude from this study that the occurrence of a high quantity of flavonoid and phenolic contents had strong antioxidant properties, leading to hepatoprotective and nephroprotective activity. Further active constituent-specific activities should be evaluated. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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19 pages, 1933 KiB

Open AccessArticle

Optimization of a Microwave Assisted Extraction Method for Maximum Flavonols and Antioxidant Activity of Onion Extracts

by Ana V. González-de-Peredo, Mercedes Vázquez-Espinosa, Estrella Espada-Bellido, Marta Ferreiro-González, Gerardo F. Barbero, Miguel Palma and Ceferino Carrera

Antioxidants 2022, 11(12), 2393; https://doi.org/10.3390/antiox11122393 - 02 Dec 2022

Cited by 5 | Viewed by 2056

Abstract

Nowadays, consumers demand bioactive foods that have the potential to limit the risk of suffering from several medical conditions. Onions present these desirable capabilities owing to its high content in antioxidant bioactive compounds. This work has used a Box–Behnken design with a response surface methodology to determine the best conditions in which to extract the polyphenols that are found in onions. Two extraction methods—one for the extraction of total flavonols and another one intended to obtain extracts with the highest possible antioxidant activity—have been developed and optimized. The following factors have been studied: temperature, %methanol in water, solvent pH, and sample–solvent volumetric ratio. The optimal conditions for the extraction of flavonols were 93.8% methanol in water, pH 2, 50 °C extraction temperature and 0.2:17.9 g:mL sample–solvent ratio. The best antioxidant activity levels were registered when using 74.2% methanol in water, pH 2, 99.9 °C extraction temperature and 0.2:18.2 g:mL sample–solvent ratio. Both optimized methods used short extraction times, and presented good precision levels and successful results when used with an assortment of onion varieties. According to total flavonols and antioxidant activity data, with 7.557 ± 0.3261 and 12.08 ± 0.0379 mg g⁻¹, respectively, the developed methods achieved comparable or even superior results to those obtained by other authors. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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20 pages, 4961 KiB

Open AccessArticle

Balance of Macrophage Activation by a Complex Coacervate-Based Adhesive Drug Carrier Facilitates Diabetic Wound Healing

by Ching-Shuen Wang, Shen-Dean Luo, Shihai Jia, Wilfred Wu, Shwu-Fen Chang, Sheng-Wei Feng, Chieh-Hsiang Yang, Jiann-Her Lin and Yinshen Wee

Antioxidants 2022, 11(12), 2351; https://doi.org/10.3390/antiox11122351 - 28 Nov 2022

Cited by 4 | Viewed by 1790

Abstract

Uncontrolled and sustained inflammation disrupts the wound-healing process and produces excessive reactive oxygen species, resulting in chronic or impaired wound closure. Natural antioxidants such as plant-based extracts and natural polysaccharides have a long history in wound care. However, they are hard to apply to wound beds due to high levels of exudate or anatomical sites to which securing a dressing is difficult. Therefore, we developed a complex coacervate-based drug carrier with underwater adhesive properties that circumvents these challenges by enabling wet adhesion and controlling inflammatory responses. This resulted in significantly accelerated wound healing through balancing the pro- and anti-inflammatory responses in macrophages. In brief, we designed a complex coacervate-based drug carrier (ADC) comprising oligochitosan and inositol hexaphosphate to entrap and release antioxidant proanthocyanins (PA) in a sustained way. The results from in vitro experiments demonstrated that ADC is able to reduce LPS-stimulated pro-inflammatory responses in macrophages. The ability of ADC to reduce LPS-stimulated pro-inflammatory responses in macrophages is even more promising when ADC is encapsulated with PA (ADC-PA). Our results indicate that ADC-PA is able to polarize macrophages into an M2 tissue-healing phenotype via up-regulation of anti-inflammatory and resolution of inflammatory responses. Treatment with ADC-PA around the wound beds fine-tunes the balance between the numbers of inducible nitric oxide synthase-positive (iNOS+) and mannose receptor-negative (CD206-) M1 and iNOS-CD206+ M2 macrophages in the wound microenvironment compared to controls. Achieving such a balance between the numbers of iNOS+CD206- M1 and iNOS-CD206+ M2 macrophages in the wound microenvironment has led to significantly improved wound closure in mouse models of diabetes, which exhibit severe impairments in wound healing. Together, our results demonstrate for the first time the use of a complex coacervate-based drug delivery system to promote timely resolution of the inflammatory responses for diabetic wound healing by fine-tuning the functions of macrophages. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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24 pages, 8228 KiB

Open AccessArticle

Hot-Melt Extrusion Enhances Antioxidant Effects of Mulberry on Probiotics and Pathogenic Microorganisms

by Eun Ji Go, Byeong Ryeol Ryu, Gyeong Ju Gim, Ha Yeon Lee, Han Sol You, Hyun Bok Kim, Hyun Tai Lee, Ji Young Lee, Man Sop Shim, Jong-Suep Baek and Jung Dae Lim

Antioxidants 2022, 11(11), 2301; https://doi.org/10.3390/antiox11112301 - 21 Nov 2022

Cited by 3 | Viewed by 2109

Abstract

Mulberry is a rich source of anthocyanins (ACNs) known to possess biological activities. However, these ACNs are unstable in high pH, heat, and aqueous environments with a low bioavailability. In this study, a colloidal dispersion was prepared by hot melt extrusion with proper excipients. In this process, a hydrophilic polymer matrix was used to confirm the stability of the compound in high pH, high temperature, and aqueous media. It was confirmed that the particle size and the polydispersity index value were reduced, thereby improving the solubility. In vitro release studies revealed that the extrudate had a sustained release compared to a non-extruded product. As a result of measuring changes of intestinal microorganisms (Lacticaseibacillus rhamnosus, Pediococcus pentosaceus, Escherichia coli, Enterococcus faecalis, and Staphylococcus aureus), contents of probiotics were found to be increased whereas contents of pathogenic microorganisms were decreased. Thus, hot-melt extrusion could enhance the stability of ACN with prolonged release. The processed formulation exhibited probiotic properties and antimicrobial activities against pathogenic intestinal microflora. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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30 pages, 5758 KiB

Open AccessArticle

Metabolite Profiling Analysis and the Correlation with Biological Activity of Betalain-Rich Portulaca grandiflora Hook. Extracts

by Aneta Spórna-Kucab, Anna Tekieli, Agnieszka Grzegorczyk, Łukasz Świątek, Barbara Rajtar, Krystyna Skalicka-Woźniak, Karolina Starzak, Boris Nemzer, Zbigniew Pietrzkowski and Sławomir Wybraniec

Antioxidants 2022, 11(9), 1654; https://doi.org/10.3390/antiox11091654 - 25 Aug 2022

Cited by 6 | Viewed by 2423

Abstract

The aim of the study was to evaluate the possible correlation between the bioactivity and the phytochemical profile of four betalain-rich extracts from Portulaca grandiflora Hook. The HPLC-DAD-ESI-MS analysis indicated the presence of 19 betaxanthins and two betacyanins. The highest concentrations of betaxanthins (982 mg/100 g DE) and betacyanins (650 mg/100 g DE) were noticed in orange and purple flowers extracts, respectively. The HPLC-DAD-ESI-HRMS/MS analyses revealed the presence of a total of 71 compounds. Fifteen new betaxanthins and fifty other metabolites were identified for the first time. The antioxidant activity of the studied flower extracts increased in the sequence of yellow < orange < purple < red (0.066–0.176 mM TE/g DE). Betalains showed less effect on the antioxidant activity of extracts than other metabolites did. Extracts from yellow and orange flowers were more active against Gram-positive bacteria (MIC = 4–16 mg/L), whereas extracts from red and purple flowers were slightly more active against Gram-negative bacteria (MIC = 16–32 mg/L). All the extracts showed the same activity against yeasts (MIC = 32 mg/L). Betaxanthins were active against Gram-positive bacteria, whereas betacyanins were active against Gram-negative bacteria. Remaining metabolites also exhibited antimicrobial activities. The cytotoxicity assessment showed that the P. grandiflora extracts were non-toxic to normal VERO cells. No significant antiviral activity towards Human Herpesvirus type 1 was observed (62 µg/mL). Among the tested varieties, the purple one showed anticancer selectivity towards colon carcinoma cells (RKO). Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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11 pages, 1634 KiB

Open AccessArticle

Regulation of Anthocyanin Biosynthesis by Drought and UV-B Radiation in Wild Tomato (Solanum peruvianum) Fruit

by Gerardo Tapia, Monserrat Castro, Carlos Gaete-Eastman and Carlos R. Figueroa

Antioxidants 2022, 11(9), 1639; https://doi.org/10.3390/antiox11091639 - 24 Aug 2022

Cited by 5 | Viewed by 2124

Abstract

Anthocyanins are plant pigments derived from the phenylpropanoid pathway which are produced in many different species, contributing to defense against stresses by their antioxidant properties. Cultivated tomatoes cannot synthesize flavonoids; however, wild tomatoes such as Solanum chilense and Solanum lycopersicoides have anthocyanin pigmented skin. Other wild tomato species such as Solanum peruvianum have been poorly studied concerning anthocyanin accumulation in the fruit. This research is the first to address the regulation of anthocyanin biosynthesis mediated by drought stress and light radiation in S. peruvianum fruit. Transcript accumulation of SpAN2, encoding for a key MYB type transcription factor for the regulation of anthocyanin biosynthesis, was induced in the fruit of plants exposed to drought treatment. In addition, fruit peel accumulates a greater anthocyanin content in water deficit-treated plants. The expression of SpAN2 was also regulated according to sunlight exposure, reaching a higher expression during maximal daily UV radiation and under controlled UV-B treatments. Similar results were observed for the expression of the late flavonoid biosynthetic gene dihydroflavonol 4-reductase (SpDFR). These results suggest that SpAN2 and SpDFR are involved in anthocyanin biosynthesis under drought stress and UV radiation in S. peruvianum. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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Review

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14 pages, 1883 KiB

Open AccessReview

Effect of HHP and UHPH High-Pressure Techniques on the Extraction and Stability of Grape and Other Fruit Anthocyanins

by Antonio Morata, Juan Manuel del Fresno, Mohsen Gavahian, Buenaventura Guamis, Felipe Palomero and Carmen López

Antioxidants 2023, 12(9), 1746; https://doi.org/10.3390/antiox12091746 - 10 Sep 2023

Cited by 1 | Viewed by 1259

Abstract

The use of high-pressure technologies is a hot topic in food science because of the potential for a gentle process in which spoilage and pathogenic microorganisms can be eliminated; these technologies also have effects on the extraction, preservation, and modification of some constituents. Whole grapes or bunches can be processed by High Hydrostatic Pressure (HHP), which causes poration of the skin cell walls and rapid diffusion of the anthocyanins into the pulp and seeds in a short treatment time (2–10 min), improving maceration. Grape juice with colloidal skin particles of less than 500 µm processed by Ultra-High Pressure Homogenization (UHPH) is nano-fragmented with high anthocyanin release. Anthocyanins can be rapidly extracted from skins using HHP and cell fragments using UHPH, releasing them and facilitating their diffusion into the liquid quickly. HHP and UHPH techniques are gentle and protective of sensitive molecules such as phenols, terpenes, and vitamins. Both techniques are non-thermal technologies with mild temperatures and residence times. Moreover, UHPH produces an intense inactivation of oxidative enzymes (PPOs), thus preserving the antioxidant activity of grape juices. Both technologies can be applied to juices or concentrates; in addition, HHP can be applied to grapes or bunches. This review provides detailed information on the main features of these novel techniques, their current status in anthocyanin extraction, and their effects on stability and process sustainability. Full article

(This article belongs to the Special Issue Anthocyanins: Antioxidant Capacity and Health Effects)

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