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Special Issue "Anthocyanins"

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (31 May 2017).

Special Issue Editors

Prof. Dr. Nuno Mateus
E-Mail Website
Guest Editor
REQUIMTE/LAQV, Chemistry and Biochemistry Department, Faculty of Sciences University of Porto, Rua do Campo Alegre, s/n, 4169-007 Porto, Portugal
Interests: food chemistry; biochemistry; food polyphenols; red wine chemistry; industrial wastes recycling
Dr. Iva Fernandes
E-Mail Website
Guest Editor
REQUIMTE/LAQV, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, 4169-007, Porto, Portugal
Interests: The bioavailability, biological activity and metabolism of polyphenols and their putative applications as nutraceuticals. Anthocyanin derivatives for technological applications in the cosmetic industry and for topical photodynamic therapy.
Special Issues and Collections in MDPI journals

Special Issue Information

Dear Colleagues,

Anthocyanins are plant pigments that are widespread in nature. They play relevant roles in plant proliferation and physiology and plant defense mechanisms, and are responsible for the color of fruits and vegetables. Over the last few decades, a large number of novel anthocyanin structures have been identified, both in natural sources and processed products. In addition to the optimization of extraction or purification processes of anthocyanin pigments from plant sources, evidence regarding their benefits in human health has accumulated. Furthermore, processes of anthocyanin absorption and biotransformation in the human organism have started to be ascertained. There may be several novel uses of these natural dyes or derivative pigments. These advances in anthocyanin research will be the main focus of the International Journal of Molecular Sciences Special Issue. Authors are invited to submit manuscripts, where aspects related to anthocyanins applications in different areas like agricultural and food chemistry, nutrition, biomedicine, nanomaterials or cosmetics, are explored.

Dr. Nuno Mateus
Dr. Iva Fernandes
Guest Editors

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Keywords

  • Anthocyanins
  • bioavailability
  • biological activity
  • disease prevention
  • protein interaction
  • biomarkers

Published Papers (15 papers)

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Research

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Article
Radical Scavenging and Anti-Inflammatory Activities of Representative Anthocyanin Groupings from Pigment-Rich Fruits and Vegetables
Int. J. Mol. Sci. 2018, 19(1), 169; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms19010169 - 06 Jan 2018
Cited by 45 | Viewed by 4723
Abstract
Anthocyanins, the naturally occurring pigments responsible for most red to blue colours of flowers, fruits and vegetables, have also attracted interest because of their potential health effects. With the aim of contributing to major insights into their structure–activity relationship (SAR), we have evaluated [...] Read more.
Anthocyanins, the naturally occurring pigments responsible for most red to blue colours of flowers, fruits and vegetables, have also attracted interest because of their potential health effects. With the aim of contributing to major insights into their structure–activity relationship (SAR), we have evaluated the radical scavenging and biological activities of selected purified anthocyanin samples (PASs) from various anthocyanin-rich plant materials: two fruits (mahaleb cherry and blackcurrant) and two vegetables (black carrot and “Sun Black” tomato), differing in anthocyanin content (ranging from 4.9 to 38.5 mg/g DW) and molecular structure of the predominant anthocyanins. PASs from the abovementioned plant materials have been evaluated for their antioxidant capacity using Trolox Equivalent Antioxidant Capacity (TEAC) and Oxygen Radical Absorbance Capacity (ORAC) assays. In human endothelial cells, we analysed the anti-inflammatory activity of different PASs by measuring their effects on the expression of endothelial adhesion molecules VCAM-1 and ICAM-1. We demonstrated that all the different PASs showed biological activity. They exhibited antioxidant capacity of different magnitude, higher for samples containing non-acylated anthocyanins (typical for fruits) compared to samples containing more complex anthocyanins acylated with cinnamic acid derivatives (typical for vegetables), even though this order was slightly reversed when ORAC assay values were expressed on a molar basis. Concordantly, PASs containing non-acylated anthocyanins reduced the expression of endothelial inflammatory antigens more than samples with aromatic acylated anthocyanins, suggesting the potential beneficial effect of structurally diverse anthocyanins in cardiovascular protection. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Identification of Light-Independent Anthocyanin Biosynthesis Mutants Induced by Ethyl Methane Sulfonate in Turnip “Tsuda” (Brassica rapa)
Int. J. Mol. Sci. 2017, 18(7), 1288; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18071288 - 22 Jun 2017
Cited by 7 | Viewed by 3066
Abstract
The epidermis of swollen storage roots in purple cultivars of turnip “Tsuda” (Brassica rapa) accumulates anthocyanin in a light-dependent manner, especially in response to UV-A light, of which the mechanism is unclear. In this study, we mutagenized 15,000 seeds by 0.5% [...] Read more.
The epidermis of swollen storage roots in purple cultivars of turnip “Tsuda” (Brassica rapa) accumulates anthocyanin in a light-dependent manner, especially in response to UV-A light, of which the mechanism is unclear. In this study, we mutagenized 15,000 seeds by 0.5% (v/v) ethyl methane sulfonate (EMS) and obtained 14 mutants with abnormal anthocyanin production in their epidermis of swollen storage roots. These mutants were classified into two groups: the red mutants with constitutive anthocyanin accumulation in their epidermis of storage roots even in underground parts in darkness and the white mutants without anthocyanin accumulation in the epidermis of storage roots in aboveground parts exposed to sunlight. Test cross analysis demonstrated that w9, w68, w204, r15, r21, r30 and r57 contained different mutations responsible for their phenotypic variations. Further genetic analysis of four target mutants (w9, w68, w204 and r15) indicated that each of them was controlled by a different recessive gene. Intriguingly, the expression profiles of anthocyanin biosynthesis genes, including structural and regulatory genes, coincided with their anthocyanin levels in the epidermis of storage roots in the four target mutants. We proposed that potential genes responsible for the mutations should be upstream factors of the anthocyanin biosynthesis pathway in turnips, which provided resources to further investigate the mechanisms of light-induced anthocyanin accumulation. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Antiproliferative and Apoptotic Potential of Cyanidin-Based Anthocyanins on Melanoma Cells
Int. J. Mol. Sci. 2017, 18(5), 949; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18050949 - 30 Apr 2017
Cited by 11 | Viewed by 2175
Abstract
Elderberries are known for their high anthocyanins content, which have been shown to possess anti-proliferative and anti-cancer effects. Anthocyanins enriched extract (AEE) was obtained from elderberries and was characterized by LC/DAD/ESI-MS analysis. Five cyanidin-based anthocyanins were identified, among which Cy-3-O-samb was [...] Read more.
Elderberries are known for their high anthocyanins content, which have been shown to possess anti-proliferative and anti-cancer effects. Anthocyanins enriched extract (AEE) was obtained from elderberries and was characterized by LC/DAD/ESI-MS analysis. Five cyanidin-based anthocyanins were identified, among which Cy-3-O-samb was the major compound (51%). The total anthocyanins content of AEE was 495 mg Cy-3-O-samb/100 g FW. AEE inhibited proliferation of metastatic B16-F10 murine melanoma cells, in a concentration-dependent manner, with an IC50 of 264.3 μg/mL. LDH (lactate dehydrogenase), as a marker of membrane integrity, increased 74% in B16-F10 cells treated with 250 μg/mL AEE, compared to control. It was observed that apoptosis is the mechanism of melanoma cell death after AEE treatment, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. These results indicate that elderberry-derived anthocyanins might be utilized in future applications as topical adjuvant in skin cancer therapy. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Delphinidin Reduces Glucose Uptake in Mice Jejunal Tissue and Human Intestinal Cells Lines through FFA1/GPR40
Int. J. Mol. Sci. 2017, 18(4), 750; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18040750 - 05 Apr 2017
Cited by 22 | Viewed by 2603
Abstract
Anthocyanins are pigments with antihyperglycemic properties, and they are potential candidates for developing functional foods for the therapy or prevention of Diabetes mellitus type 2 (DM2). The mechanism of these beneficial effects of anthocyanins are, however, hard to explain, given their very low [...] Read more.
Anthocyanins are pigments with antihyperglycemic properties, and they are potential candidates for developing functional foods for the therapy or prevention of Diabetes mellitus type 2 (DM2). The mechanism of these beneficial effects of anthocyanins are, however, hard to explain, given their very low bioavailability due to poor intestinal absorption. We propose that free fatty acid receptor 1 (FFA1, also named GPR40), is involved in an inhibitory effect of the anthocyanidin delphinidin over intestinal glucose absorption. We show the direct effects of delphinidin on the intestine using jejunum samples from RF/J mice, and the human intestinal cell lines HT-29, Caco-2, and NCM460. By the use of specific pharmacological antagonists, we determined that delphinidin inhibits glucose absorption in both mouse jejunum and a human enterocytic cell line in a FFA1-dependent manner. Delphinidin also affects the function of sodium-glucose cotransporter 1 (SGLT1). Intracellular signaling after FFA1 activation involved cAMP increase and cytosolic Ca2+ oscillations originated from intracellular Ca2+ stores and were followed by store-operated Ca2+ entry. Taken together, our results suggest a new GPR-40 mediated local mechanism of action for delphinidin over intestinal cells that may in part explain its antidiabetic effect. These findings are promising for the search for new prevention and pharmacological treatment strategies for DM2 management. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
A New Chemical Pathway Yielding A-Type Vitisins in Red Wines
Int. J. Mol. Sci. 2017, 18(4), 762; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18040762 - 04 Apr 2017
Cited by 8 | Viewed by 2135
Abstract
A new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. [...] Read more.
A new chemical pathway yielding A-type vitisins in red wines is proposed herein from the reaction between anthocyanins and oxaloacetic acid (OAA). This new chemical path is thought to occur in the first stages of the wine production even during the fermentation process. This is due to the revealed high reactivity of OAA with anthocyanins compared with the already known precursor (pyruvic acid, PA). In model solutions at wine pH (3.5), when malvidin-3-O-glucoside (mv-3-glc) is in contact with OAA and PA a decrease in the OAA concentration is observed along with the formation of A-type vitisin. Moreover, part of the OAA is also chemically converted into PA in model solutions. The reaction yields were also determined for OAA and PA using different mv-3-glc:organic acid molar ratios (1:0.5, 1:1, 1:5, 1:10; 1:50, and 1:100) and these values were always higher for OAA when compared to PA, even at the lowest molar ratio (1:0.5). The reaction yields were higher at pH 2.6 in comparison to pH 1.5 and 3.5, being less affected at pH 3.5 for OAA. These results support the idea that OAA can be at the origin of A-type vitisins in the first stages of wine production and PA in the subsequent ageing process. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Characterization of Active Anthocyanin Degradation in the Petals of Rosa chinensis and Brunfelsia calycina Reveals the Effect of Gallated Catechins on Pigment Maintenance
Int. J. Mol. Sci. 2017, 18(4), 699; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18040699 - 25 Mar 2017
Cited by 11 | Viewed by 3209
Abstract
Anthocyanin degradation decreases ornamental or nutritional values of horticultural products. To investigate factors that may influence colour change in flower development, anthocyanin degradation was compared between the flowers of Brunfelsia calycina and Rosa chinensis, which show rapid and slow degradation, respectively. In-gel [...] Read more.
Anthocyanin degradation decreases ornamental or nutritional values of horticultural products. To investigate factors that may influence colour change in flower development, anthocyanin degradation was compared between the flowers of Brunfelsia calycina and Rosa chinensis, which show rapid and slow degradation, respectively. In-gel activity assays, high performance liquid chromatography (HPLC) analysis of tannins, enzyme kinetics measurement and immune-detection of anthocyanin degradation related-perioxidases (PODs) were carried out for the comparison. Rose petals possessed significantly lower anthocyanin degradation-related POD activities than Brunfelsia petals, which may be related to the high tannin contents. Epicatechin gallate (ECG) and gallocatechin gallate (GCG) were detected in rose as 161.3 ± 12.34 and 273.56 ± 41.23 μg/g FW (Fresh Weight) respectively, while not detected in Brunfelsia. ECG and GCG inhibited the activities of the Brunfelsia POD with half maximal inhibitory concentrations (IC50s) as 21.5 and 29.7 μM respectively, and increased the colour intensities of the anthocyanins. Catechin and epicatechin did not inhibit the POD activity, while serving as POD substrates, with Km (the Michaelis constant) as 0.48 and 1.23 mM. Similar protein levels of the anthocyanin degradation-related 40-kDa PODs were detected in Brunfelsia and rose. In summary, high amount of tannins, particularly ECG and GCG, in red rose petals may inhibit the degradation-related enzymes, leading to the maintenance of anthocyanins in vivo. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Tentative Characterization of Polyphenolic Compounds in the Male Flowers of Phoenix dactylifera by Liquid Chromatography Coupled with Mass Spectrometry and DFT
Int. J. Mol. Sci. 2017, 18(3), 512; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18030512 - 02 Mar 2017
Cited by 44 | Viewed by 3201
Abstract
Phoenix dacylifera is an ancient palm species rich in (poly)phenols. These phenolic compounds were tentatively identified by using liquid chromatography coupled with ion spray mass spectrometry in tandem mode (LC/MS/MS) with negative ion detection. Negative identification of the compounds was based on their [...] Read more.
Phoenix dacylifera is an ancient palm species rich in (poly)phenols. These phenolic compounds were tentatively identified by using liquid chromatography coupled with ion spray mass spectrometry in tandem mode (LC/MS/MS) with negative ion detection. Negative identification of the compounds was based on their retention times and mass spectra in full scan mode (MS), and in different MS/MS modes. For the first time, complete hypothesis, and routs for both p-coumaroylshikimic acids (CoSA) and caffeoylshikimic acids (CSA) were suggested and confirmed by Density Fonctional Theory (DFT) study. Notably, of the 53 compounds characterized, 19 hydroxycinnamates derivatives were tentativelycharacterized in male flowers of date palm and 15 of them were recorded for the first time. In addition, five organic acids, six B-type proanthocyanidins, two anthocyanidin and 21 flavonoid derivatives have been tentatively characterized. Identification of B-type proanthocyanidins were based on the diagnostic ions resulting from heterocyclic ring fission (HRF) and retro-Diels-Alder (RDA) reaction of flavan-3-ol provided information on the hydroxylation pattern and the type of inter-flavan bond proanthocyanidins. The sequence of proanthocyanidins was detected through ions extracted from quinone methide (QM) cleavage of the inter-flavan bond. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Time, Concentration, and pH-Dependent Transport and Uptake of Anthocyanins in a Human Gastric Epithelial (NCI-N87) Cell Line
Int. J. Mol. Sci. 2017, 18(2), 446; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18020446 - 18 Feb 2017
Cited by 13 | Viewed by 2678
Abstract
Anthocyanins are the largest class of water soluble plant pigments and a common part of the human diet. They may have many potential health benefits, including antioxidant, anti-inflammatory, anti-cancer, and cardioprotective activities. However, anthocyanin metabolism is not well understood. Studies suggest that anthocyanins [...] Read more.
Anthocyanins are the largest class of water soluble plant pigments and a common part of the human diet. They may have many potential health benefits, including antioxidant, anti-inflammatory, anti-cancer, and cardioprotective activities. However, anthocyanin metabolism is not well understood. Studies suggest that anthocyanins absorption may occur in the stomach, in which the acidic pH favors anthocyanin stability. A gastric epithelial cell line (NCI-N87) has been used to study the behavior of anthocyanins at a pH range of 3.0–7.4. This work examines the effects of time (0–3 h), concentration (50–1500 µM), and pH (3.0, 5.0, 7.4) on the transport and uptake of anthocyanins using NCI-N87 cells. Anthocyanins were transported from the apical to basolateral side of NCI-N87 cells in time and dose dependent manners. Over the treatment time of 3 h the rate of transport increased, especially with higher anthocyanin concentrations. The non-linear rate of transport may suggest an active mechanism for the transport of anthocyanins across the NCI-N87 monolayer. At apical pH 3.0, higher anthocyanin transport was observed compared to pH 5.0 and 7.4. Reduced transport of anthocyanins was found to occur at apical pH 5.0. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Synthesis of 8-Aryl-O-methylcyanidins and Their Usage for Dye-Sensitized Solar Cell Devices
Int. J. Mol. Sci. 2017, 18(2), 427; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18020427 - 16 Feb 2017
Cited by 4 | Viewed by 2120
Abstract
Anthocyanins as natural pigments are colorful and environmentally compatible dyes for dye-sensitized solar cells (DSSCs). To increase the efficiency, we designed and synthesized unnatural O-methylflavonols and O-methylcyanidins that possess an aryl group at the 8-position. We synthesized per-O-methylquercetin [...] Read more.
Anthocyanins as natural pigments are colorful and environmentally compatible dyes for dye-sensitized solar cells (DSSCs). To increase the efficiency, we designed and synthesized unnatural O-methylflavonols and O-methylcyanidins that possess an aryl group at the 8-position. We synthesized per-O-methylquercetin from quercetin, then using selective demethylation prepared various O-methylquercetins. Using the Suzuki-Miyaura coupling reaction, 8-arylation of per-O-methylquercetin was achieved. Using a LiAlH4 reduction or Clemmensen reduction, these flavonols were transformed to the corresponding cyanidin derivatives in satisfactory yields. Using these dyes, we fabricated DSSCs, and their efficiency was investigated. The efficiency of tetra-O-methylflavonol was 0.31%. However, the introduction of the 8-aryl residue increased the efficiency to 1.04%. In comparison to these flavonols, O-methylcyanidins exhibited a lower efficiency of 0.05% to 0.52%. The introduction of the 8-aryl group into the cyanidin derivatives did not result in a remarkable increase in the efficiency. These phenomena may be due to the poor fit of the HOMO-LUMO level of the dyes to the TiO2 conduction band. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Metabolic Effects of Berries with Structurally Diverse Anthocyanins
Int. J. Mol. Sci. 2017, 18(2), 422; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18020422 - 15 Feb 2017
Cited by 62 | Viewed by 5638
Abstract
Overconsumption of energy dense foods and sedentary lifestyle are considered as major causes of obesity-associated insulin resistance and abnormal glucose metabolism. Results from both cohort studies and randomized trials suggested that anthocyanins from berries may lower metabolic risks, however these reports are equivocal. [...] Read more.
Overconsumption of energy dense foods and sedentary lifestyle are considered as major causes of obesity-associated insulin resistance and abnormal glucose metabolism. Results from both cohort studies and randomized trials suggested that anthocyanins from berries may lower metabolic risks, however these reports are equivocal. The present study was designed to examine effects of six berries with structurally diverse anthocyanin profiles (normalized to 400 µg/g total anthocyanin content) on development of metabolic risk factors in the C57BL/6 mouse model of polygenic obesity. Diets supplemented with blackberry (mono-glycosylated cyanidins), black raspberry (acylated mono-glycosylated cyanidins), blackcurrant (mono- and di-glycosylated cyanidins and delphinidins), maqui berry (di-glycosylated delphinidins), Concord grape (acylated mono-glycosylated delphinidins and petunidins), and blueberry (mono-glycosylated delphinidins, malvidins, and petunidins) showed a prominent discrepancy between biological activities of delphinidin/malvidin-versus cyanidin-type anthocyanins that could be explained by differences in their structure and metabolism in the gut. Consumption of berries also resulted in a strong shift in the gastrointestinal bacterial communities towards obligate anaerobes that correlated with decrease in the gastrointestinal luminal oxygen and oxidative stress. Further work is needed to understand mechanisms that lead to nearly anoxic conditions in the gut lumens, including the relative contributions of host, diet and/or microbial oxidative activity, and their implication to human health. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Transcriptome Analysis Identifies Key Candidate Genes Mediating Purple Ovary Coloration in Asiatic Hybrid Lilies
Int. J. Mol. Sci. 2016, 17(11), 1881; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms17111881 - 20 Nov 2016
Cited by 7 | Viewed by 3225
Abstract
Lily tepals have a short lifespan. Once the tepals senesce, the ornamental value of the flower is lost. Some cultivars have attractive purple ovaries and fruits which greatly enhance the ornamental value of Asiatic hybrid lilies. However, little is known about the molecular [...] Read more.
Lily tepals have a short lifespan. Once the tepals senesce, the ornamental value of the flower is lost. Some cultivars have attractive purple ovaries and fruits which greatly enhance the ornamental value of Asiatic hybrid lilies. However, little is known about the molecular mechanisms of anthocyanin biosynthesis in Asiatic hybrid lily ovaries. To investigate the transcriptional network that governs purple ovary coloration in Asiatic hybrid lilies, we obtained transcriptome data from green ovaries (S1) and purple ovaries (S2) of Asiatic “Tiny Padhye”. Comparative transcriptome analysis revealed 4228 differentially expressed genes. Differential expression analysis revealed that ten unigenes including four CHS genes, one CHI gene, one F3H gene, one F3′H gene, one DFR gene, one UFGT gene, and one 3RT gene were significantly up-regulated in purple ovaries. One MYB gene, LhMYB12-Lat, was identified as a key transcription factor determining the distribution of anthocyanins in Asiatic hybrid lily ovaries. Further qPCR results showed unigenes related to anthocyanin biosynthesis were highly expressed in purple ovaries of three purple-ovaried Asiatic hybrid lilies at stages 2 and 3, while they showed an extremely low level of expression in ovaries of three green-ovaried Asiatic hybrid lilies during all developmental stages. In addition, shading treatment significantly decreased pigment accumulation by suppressing the expression of several unigenes related to anthocyanin biosynthesis in ovaries of Asiatic “Tiny Padhye”. Lastly, a total of 15,048 Simple Sequence Repeats (SSRs) were identified in 13,710 sequences, and primer pairs for SSRs were designed. The results could further our understanding of the molecular mechanisms of anthocyanin biosynthesis in Asiatic hybrid lily ovaries. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions
Int. J. Mol. Sci. 2016, 17(11), 1842; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms17111842 - 05 Nov 2016
Cited by 19 | Viewed by 2737
Abstract
The physicochemical properties of the wine pigments catechyl-pyranomalvidin-3-O-glucoside (PA1) and guaiacyl-pyranomalvidin-3-O-glucoside (PA2) are extensively revisited using ultraviolet (UV)-visible spectroscopy, dynamic light scattering (DLS) and quantum chemistry density functional theory (DFT) calculations. In mildly acidic aqueous solution, each cationic pigment [...] Read more.
The physicochemical properties of the wine pigments catechyl-pyranomalvidin-3-O-glucoside (PA1) and guaiacyl-pyranomalvidin-3-O-glucoside (PA2) are extensively revisited using ultraviolet (UV)-visible spectroscopy, dynamic light scattering (DLS) and quantum chemistry density functional theory (DFT) calculations. In mildly acidic aqueous solution, each cationic pigment undergoes regioselective deprotonation to form a single neutral quinonoid base and water addition appears negligible. Above pH = 4, both PA1 and PA2 become prone to aggregation, which is manifested by the slow build-up of broad absorption bands at longer wavelengths (λ ≥ 600 nm), followed in the case of PA2 by precipitation. Some phenolic copigments are able to inhibit aggregation of pyranoanthocyanins (PAs), although at large copigment/PA molar ratios. Thus, chlorogenic acid can dissociate PA1 aggregates while catechin is inactive. With PA2, both chlorogenic acid and catechin are able to prevent precipitation but not self-association. Calculations confirmed that the noncovalent dimerization of PAs is stronger with the neutral base than with the cation and also stronger than π–π stacking of PAs to chlorogenic acid (copigmentation). For each type of complex, the most stable conformation could be obtained. Finally, PA1 can also bind hard metal ions such as Al3+ and Fe3+ and the corresponding chelates are less prone to self-association. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Analogs of Natural 3-Deoxyanthocyanins: O-Glucosides of the 4′,7-Dihydroxyflavylium Ion and the Deep Influence of Glycosidation on Color
Int. J. Mol. Sci. 2016, 17(10), 1751; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms17101751 - 20 Oct 2016
Cited by 5 | Viewed by 2301
Abstract
3-Deoxyanthocyanidins and their O-β-d-glucosides are natural pigments abundant in black sorghum. O-glycosidation can perturb the acid-base properties of the chromophore and lower its electron density with a large impact on the distribution of colored and colorless forms in aqueous [...] Read more.
3-Deoxyanthocyanidins and their O-β-d-glucosides are natural pigments abundant in black sorghum. O-glycosidation can perturb the acid-base properties of the chromophore and lower its electron density with a large impact on the distribution of colored and colorless forms in aqueous solution. In this work, the influence of O-glycosidation on color is systematically studied from a series of 3-deoxyanthocyanin analogs. The pH- and light-dependent reversible reactions of 7-β-d-glucopyranosyloxy-4′-hydroxyflavylium (P3) and 4′-β-d-glucopyranosyloxy-7-hydroxyflavylium (P5) were completely characterized in mildly acidic solution and compared with the parent aglycone 4′,7-dihydroxyflavylium ion and the O-methylethers of P3 and P5. Except P5, the chalcone forms of the pigments exhibit a high cis-trans isomerization barrier that allows a pseudo-equilibrium involving all species except the trans-chalcone. At equilibrium, only the flavylium cation and trans-chalcone are observed. With all pigments, the colored flavylium ion can be generated by irradiation of the trans-chalcone (photochromism). Glycosidation of C7–OH accelerates hydration and strongly slows down cis-trans isomerization with the pH dependence of the apparent isomerization rate constant shifting from a bell-shaped curve to a sigmoid. The color of P5 is much more stable than that of its regioisomer P3 in near-neutral conditions. Full article
(This article belongs to the Special Issue Anthocyanins)
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Article
Anthocyanin Attenuates Doxorubicin-Induced Cardiomyotoxicity via Estrogen Receptor-α/β and Stabilizes HSF1 to Inhibit the IGF-IIR Apoptotic Pathway
Int. J. Mol. Sci. 2016, 17(9), 1588; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms17091588 - 21 Sep 2016
Cited by 22 | Viewed by 3490
Abstract
Doxorubicin (Dox) is extensively used for chemotherapy in different types of cancer, but its use is limited to because of its cardiotoxicity. Our previous studies found that doxorubicin-induced insulin-like growth factor II receptor (IGF-IIR) accumulation causes cardiomyocytes apoptosis via down-regulation of HSF1 pathway. [...] Read more.
Doxorubicin (Dox) is extensively used for chemotherapy in different types of cancer, but its use is limited to because of its cardiotoxicity. Our previous studies found that doxorubicin-induced insulin-like growth factor II receptor (IGF-IIR) accumulation causes cardiomyocytes apoptosis via down-regulation of HSF1 pathway. In these studies, we demonstrated a new mechanism through which anthocyanin protects cardiomyoblast cells against doxorubicin-induced injury. We found that anthocyanin decreased IGF-IIR expression via estrogen receptors and stabilized heat shock factor 1 (HSF1) to inhibit caspase 3 activation and apoptosis of cardiomyocytes. Therefore, the phytoestrogen from plants has been considered as another potential treatment for heart failure. It has been reported that the natural compound anthocyanin (ACN) has the ability to reduce the risk of cardiovascular disease (CVD). Here, we demonstrated that anthocyanin acts as a cardioprotective drug against doxorubicin-induced heart failure by attenuating cardiac apoptosis via estrogen receptors to stabilize HSF1 expression and down-regulated IGF-IIR-induced cardiomyocyte apoptosis. Full article
(This article belongs to the Special Issue Anthocyanins)
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Review

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Review
The Effect of High Pressure Techniques on the Stability of Anthocyanins in Fruit and Vegetables
Int. J. Mol. Sci. 2017, 18(2), 277; https://0-doi-org.brum.beds.ac.uk/10.3390/ijms18020277 - 27 Jan 2017
Cited by 52 | Viewed by 3636
Abstract
Anthocyanins are a group of phenolic compounds responsible for red, blue and violet colouration of many fruits, vegetables and flowers. The high content of these pigments is important as it influences directly their health promoting properties as well as the sensory quality of [...] Read more.
Anthocyanins are a group of phenolic compounds responsible for red, blue and violet colouration of many fruits, vegetables and flowers. The high content of these pigments is important as it influences directly their health promoting properties as well as the sensory quality of the product; however they are prone to degradation by, inter alia, elevated temperature and tissue enzymes. The traditional thermal methods of food preservation cause significant losses of these pigments. Thus, novel non-thermal techniques such as high pressure processing, high pressure carbon dioxide and high pressure homogenization are under consideration. In this review, the authors attempted to summarize the current knowledge of the impact of high pressure techniques on the stability of anthocyanins during processing and storage of fruit and vegetable products. Furthermore, the effect of the activity of enzymes involved in the degradation of these compounds has been described. The conclusions including comparisons of pressure-based methods with high temperature preservation techniques were presented. Full article
(This article belongs to the Special Issue Anthocyanins)
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