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Anthocyanins

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

Deadline for manuscript submissions: closed (30 September 2014) | Viewed by 167696

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editors

Prof. Dr. Ronald E. Wrolstad

E-Mail Website
Guest Editor
Department of Food Science and Technology, Wiegand Hall, Oregon State University, OR 97331-6602, USA
Interests: anthocyanins and polyphenolics; color quality, analytical methods; natural colorants; fruit juice authenciticy
Dr. M. Monica Giusti

E-Mail Website
Guest Editor
Department of Food Science and Technology, The Ohio State University, Columbus, OH 43210, USA
Interests: chemistry of polyphenols; anthocyanins; phytochemicals; analytical chemistry
Special Issues, Collections and Topics in MDPI journals
Dr. Wilhelmina Kalt

E-Mail Website
Guest Editor
Agriculture and Agri-Food Canada
Interests: anthocyanins; berries; blueberries; bioavailability; bioactivity; flavonoids; health

Special Issue Information

Dear Colleagues,

Research articles on anthocyanin pigments have escalated dramatically in the last 20 years. While PubMed shows 230 anthocyanin publications in the decade from 1982 through 1991, there were 753 from 1992 through 2001, and 3,043 from 2002 through 2011. Anthocyanin pigments have long intrigued scientists, and earlier investigations documented the dynamic nature of their chemistry and their role in the color quality of foods, particularly wine because of its high economic value. Historically, botanists have investigated these pigments in chemotaxonomic and horticultural research to understand the role of anthocyanins in the color quality of flowers and in fruit ripening. More recently, the widely-publicized “French Paradox” made the public aware of the epidemiological evidence that the French, despite a diet high in saturated fats, had a lower than predicted rate of coronary heart disease compared to people in several Western countries with similar risk factors. It was suggested that the consumption of flavonoid-rich foods including anthocyanins that are abundant in red wine and other fruit-based foods might account at least in part for the phenomena. These findings have stimulated an explosion of investigations on various phytochemicals, their bioactivities and their possible role in human health. As part of an early working hypothesis it was suggested that the antioxidant properties of plant food phytochemicals could be a positive predictor of possible health benefits. Numerous investigations revealed that there was a high correlation specifically between the anthocyanin content of some vegetables, fruits and especially berries and their antioxidant activity in vitro. However, determining the in vivo significance of anthocyanin antioxidant activity in human health has been more difficult since studies have shown that anthocyanins are poorly absorbed and rapidly cleared from the body. Notwithstanding there remains abundant in vivo evidence from closely-controlled animal studies, and an increasing amount of human clinical evidence that anthocyanins do indeed provide beneficial health effects. Complementary mechanistic studies have shown that anthocyanins can affect a variety of physiological processes in a beneficial manner. Most encouraging perhaps is recent epidemiological evidence indicating that anthocyanins specifically are associated with a reduced risk of both cardiac events and type 2 diabetes in free-living human populations.

Research articles covering all aspects of anthocyanin chemistry, such as composition, degradative reactions, biosynthesis, their use as natural colorants, and the possible mechanisms for reducing the risks of chronic diseases are welcomed for inclusion in the Special Issue of Molecules.

Prof. Dr. Ronald E Wrolstad
Dr. Monica Giusti
Dr. Wilhelmina Kalt
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.


Keywords

  • anthocyanin pigments
  • color quality of foods
  • natural colorants
  • anthocyanin absorption and metabolism
  • mechanisms for reducing risk of chronic diseases

Published Papers (20 papers)

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794 KiB  
Article
Distinctive Anthocyanin Accumulation Responses to Temperature and Natural UV Radiation of Two Field-Grown Vitis vinifera L. Cultivars
by Ana Fernandes de Oliveira, Luca Mercenaro, Alessandra Del Caro, Luca Pretti and Giovanni Nieddu
Molecules 2015, 20(2), 2061-2080; https://doi.org/10.3390/molecules20022061 - 27 Jan 2015
Cited by 47 | Viewed by 6790
Abstract
The responses of two red grape varieties, Bovale Grande (syn. Carignan) and Cannonau (syn. Grenache), to temperature and natural UV radiation were studied in a three-years field experiment conducted in Sardinia (Italy), under Mediterranean climate conditions. Vines were covered with plastic films with [...] Read more.
The responses of two red grape varieties, Bovale Grande (syn. Carignan) and Cannonau (syn. Grenache), to temperature and natural UV radiation were studied in a three-years field experiment conducted in Sardinia (Italy), under Mediterranean climate conditions. Vines were covered with plastic films with different transmittances to UV radiation and compared to uncovered controls. Light intensity and spectral composition at the fruit zone were monitored and berry skin temperature was recorded from veraison. Total skin anthocyanin content (TSA) and composition indicated positive but inconsistent effects of natural UV light. Elevated temperatures induced alterations to a greater extent, decreasing TSA and increasing the degree of derivatives acylation. In Cannonau total soluble solids increases were not followed by increasing TSA as in Bovale Grande, due to both lower phenolic potential and higher sensitivity to permanence of high temperatures. Multi linear regression analysis tested the effects of different ranges of temperature as source of variation on anthocyanin accumulation patterns. To estimate the thermal time for anthocyanin accumulation, the use of normal heat hours model had benefit from the addition of predictor variables that take into account the permanence of high (>35 °C) and low (<15 °C and <17 °C) temperatures during ripening. Full article
(This article belongs to the Special Issue Anthocyanins)
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2008 KiB  
Article
Decreasing pH Results in a Reduction of Anthocyanin Coprecipitation during Cold Stabilization of Purple Grape Juice
by David C. Manns, Passaporn Siricururatana, Olga I. Padilla-Zakour and Gavin L. Sacks
Molecules 2015, 20(1), 556-572; https://doi.org/10.3390/molecules20010556 - 05 Jan 2015
Cited by 4 | Viewed by 7113
Abstract
Anthocyanin pigments in grape juice can coprecipitate with potassium bitartrate (KHT) crystals during cold stabilization, but factors that reduce these adsorptive losses are not well understood. We hypothesized that coprecipitation on a % w/w basis should be decreased at lower pH. In initial [...] Read more.
Anthocyanin pigments in grape juice can coprecipitate with potassium bitartrate (KHT) crystals during cold stabilization, but factors that reduce these adsorptive losses are not well understood. We hypothesized that coprecipitation on a % w/w basis should be decreased at lower pH. In initial experiments, model juice solutions containing an anthocyanin monoglucoside extract and varying pH values were subjected to cold-storage to induce KHT crystallization, and anthocyanins in the resulting precipitant were characterized by HPLC. The pH of the model juice was directly correlated with the % w/w concentration of anthocyanins in the KHT crystals, with a maximum observed at pH 3.40 (0.20% w/w) and a minimum at pH 2.35 (0.01% w/w). A pH dependency was also observed for anthocyanin-KHT coprecipitation in purple Concord grape juice, although the effect was smaller. Coprecipitation was significantly greater for anthocyanin monoglucosides and acylated anthocyanins as compared to anthocyanin diglucosides at pH > 3.05, but coprecipitation of mono- and acylated forms declined more sharply at lower pH values. Full article
(This article belongs to the Special Issue Anthocyanins)
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1140 KiB  
Article
A New Solid Phase Extraction for the Determination of Anthocyanins in Grapes
by Marta Ferreiro-González, Ceferino Carrera, Ana Ruiz-Rodríguez, Gerardo F. Barbero, Jesús Ayuso, Miguel Palma and Carmelo G. Barroso
Molecules 2014, 19(12), 21398-21410; https://doi.org/10.3390/molecules191221398 - 19 Dec 2014
Cited by 19 | Viewed by 7086
Abstract
A method for the concentration and cleaning of red grape extracts prior to the determination of anthocyanins by UPLC-DAD has been developed. This method is of special interest in the determination of phenolic maturity as it allows the analysis of the anthocyanins present [...] Read more.
A method for the concentration and cleaning of red grape extracts prior to the determination of anthocyanins by UPLC-DAD has been developed. This method is of special interest in the determination of phenolic maturity as it allows the analysis of the anthocyanins present in grapes. Several different SPE cartridges were assessed, including both C-18- and vinylbenzene-based cartridges. C-18-based cartridges presented a very low retention for the glucosylated anthocyanidins while vinylbenzene-based cartridges showed excellent retention for these compounds. The optimized method involves the initial conditioning of the cartridge using 10 mL of methanol and 10 mL of water, followed by loading of up to 100 mL of red grape extract. Ten mL of water was used in the washing step and anthocyanins were subsequently eluted using 1.5 mL of acidified methanol at pH 2. This method simplifies the determination of individual anthocyanins as, on the one hand, it cleans the sample of interference and, on the other hand, it increases the concentration to up to 25:1.5. The developed method has been validated with a range of different grapes and it has also been tested as a means of determining the different anthocyanins in grapes with different levels of maturity. Full article
(This article belongs to the Special Issue Anthocyanins)
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1585 KiB  
Article
Obtaining Ready-to-Eat Blue Corn Expanded Snacks with Anthocyanins Using an Extrusion Process and Response Surface Methodology
by Anayansi Escalante-Aburto, Benjamín Ramírez-Wong, Patricia Isabel Torres-Chávez, Jaime López-Cervantes, Juan De Dios Figueroa-Cárdenas, Jesús Manuel Barrón-Hoyos, Ignacio Morales-Rosas, Néstor Ponce-García and Roberto Gutiérrez-Dorado
Molecules 2014, 19(12), 21066-21084; https://doi.org/10.3390/molecules191221066 - 15 Dec 2014
Cited by 15 | Viewed by 6090
Abstract
Extrusion is an alternative technology for the production of nixtamalized products. The aim of this study was to obtain an expanded nixtamalized snack with whole blue corn and using the extrusion process, to preserve the highest possible total anthocyanin content, intense blue/purple coloration [...] Read more.
Extrusion is an alternative technology for the production of nixtamalized products. The aim of this study was to obtain an expanded nixtamalized snack with whole blue corn and using the extrusion process, to preserve the highest possible total anthocyanin content, intense blue/purple coloration (color b) and the highest expansion index. A central composite experimental design was used. The extrusion process factors were: feed moisture (FM, 15%–23%), calcium hydroxide concentration (CHC, 0%–0.25%) and final extruder temperature (T, 110–150 °C). The chemical and physical properties evaluated in the extrudates were moisture content (MC, %), total anthocyanins (TA, mg·kg−1), pH, color (L, a, b) and expansion index (EI). ANOVA and surface response methodology were applied to evaluate the effects of the extrusion factors. FM and T significantly affected the response variables. An optimization step was performed by overlaying three contour plots to predict the best combination region. The extrudates were obtained under the following optimum factors: FM (%) = 16.94, CHC (%) = 0.095 and T (°C) = 141.89. The predicted extrusion processing factors were highly accurate, yielding an expanded nixtamalized snack with 158.87 mg·kg−1 TA (estimated: 160 mg·kg−1), an EI of 3.19 (estimated: 2.66), and color parameter b of −0.44 (estimated: 0.10). Full article
(This article belongs to the Special Issue Anthocyanins)
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885 KiB  
Article
Stability of Anthocyanins from Red Grape Skins under Pressurized Liquid Extraction and Ultrasound-Assisted Extraction Conditions
by Ali Liazid, Gerardo F. Barbero, Latifa Azaroual, Miguel Palma and Carmelo G. Barroso
Molecules 2014, 19(12), 21034-21043; https://doi.org/10.3390/molecules191221034 - 15 Dec 2014
Cited by 24 | Viewed by 6053
Abstract
The stability of anthocyanins from grape skins after applying different extraction techniques has been determined. The following compounds, previously extracted from real samples, were assessed: delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, peonidin 3-glucoside, malvidin 3-glucoside, peonidin 3-acetylglucoside, malvidin 3-acetylglucoside, malvidin 3-caffeoylglucoside, petunidin 3- [...] Read more.
The stability of anthocyanins from grape skins after applying different extraction techniques has been determined. The following compounds, previously extracted from real samples, were assessed: delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, peonidin 3-glucoside, malvidin 3-glucoside, peonidin 3-acetylglucoside, malvidin 3-acetylglucoside, malvidin 3-caffeoylglucoside, petunidin 3-p-coumaroylglucoside and malvidin 3-p-coumaroylglucoside (trans). The techniques used were ultrasound-assisted extraction and pressurized liquid extraction. In ultrasound-assisted extraction, temperatures up to 75 °C can be applied without degradation of the aforementioned compounds. In pressurized liquid extraction the anthocyanins were found to be stable up to 100 °C. The relative stabilities of both the glycosidic and acylated forms were evaluated. Acylated derivatives were more stable than non-acylated forms. The differences between the two groups of compounds became more marked on working at higher temperatures and on using extraction techniques with higher levels of oxygen in the extraction media. Full article
(This article belongs to the Special Issue Anthocyanins)
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909 KiB  
Article
Chemically Synthesized Glycosides of Hydroxylated Flavylium Ions as Suitable Models of Anthocyanins: Binding to Iron Ions and Human Serum Albumin, Antioxidant Activity in Model Gastric Conditions
by Sheiraz Al Bittar, Nathalie Mora, Michèle Loonis and Olivier Dangles
Molecules 2014, 19(12), 20709-20730; https://doi.org/10.3390/molecules191220709 - 11 Dec 2014
Cited by 15 | Viewed by 7496
Abstract
Polyhydroxylated flavylium ions, such as 3',4',7-trihydroxyflavylium chloride (P1) and its more water-soluble 7-O-β-d-glucopyranoside (P2), are readily accessible by chemical synthesis and suitable models of natural anthocyanins in terms of color and species distribution in aqueous solution. Owing to their catechol B-ring, [...] Read more.
Polyhydroxylated flavylium ions, such as 3',4',7-trihydroxyflavylium chloride (P1) and its more water-soluble 7-O-β-d-glucopyranoside (P2), are readily accessible by chemical synthesis and suitable models of natural anthocyanins in terms of color and species distribution in aqueous solution. Owing to their catechol B-ring, they rapidly bind FeIII, weakly interact with FeII and promote its autoxidation to FeIII. Both pigments inhibit heme-induced lipid peroxidation in mildly acidic conditions (a model of postprandial oxidative stress in the stomach), the colorless (chalcone) forms being more potent than the colored forms. Finally, P1 and P2 are moderate ligands of human serum albumin (HSA), their likely carrier in the blood circulation, with chalcones having a higher affinity for HSA than the corresponding colored forms. Full article
(This article belongs to the Special Issue Anthocyanins)
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905 KiB  
Article
The Regulation of Anthocyanin Synthesis in the Wheat Pericarp
by Olesya Y. Shoeva, Elena I. Gordeeva and Elena K. Khlestkina
Molecules 2014, 19(12), 20266-20279; https://doi.org/10.3390/molecules191220266 - 04 Dec 2014
Cited by 56 | Viewed by 7785
Abstract
Bread wheat producing grain in which the pericarp is purple is considered to be a useful source of dietary anthocyanins. The trait is under the control of the Pp-1 homoealleles (mapping to each of the group 7 chromosomes) and Pp3 (on chromosome 2A). [...] Read more.
Bread wheat producing grain in which the pericarp is purple is considered to be a useful source of dietary anthocyanins. The trait is under the control of the Pp-1 homoealleles (mapping to each of the group 7 chromosomes) and Pp3 (on chromosome 2A). Here, TaMyc1 was identified as a likely candidate for Pp3. The gene encodes a MYC-like transcription factor. In genotypes carrying the dominant Pp3 allele, TaMyc1 was strongly transcribed in the pericarp and, although at a lower level, also in the coleoptile, culm and leaf. The gene was located to chromosome 2A. Three further copies were identified, one mapping to the same chromosome arm as TaMyc1 and the other two mapping to the two other group 2 chromosomes; however none of these extra copies were transcribed in the pericarp. Analysis of the effect of the presence of combinations of Pp3 and Pp-1 genotype on the transcription behavior of TaMyc1 showed that the dominant allele Pp-D1 suppressed the transcription of TaMyc1. Full article
(This article belongs to the Special Issue Anthocyanins)
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604 KiB  
Article
Composition and Antioxidant Activity of the Anthocyanins of the Fruit of Berberis heteropoda Schrenk
by Li-Li Sun, Wan Gao, Meng-Meng Zhang, Cheng Li, Ai-Guo Wang, Ya-Lun Su and Teng-Fei Ji
Molecules 2014, 19(11), 19078-19096; https://doi.org/10.3390/molecules191119078 - 19 Nov 2014
Cited by 22 | Viewed by 8086
Abstract
In present study, the anthocyanin composition and content of the fruit of B. heteropoda Schrenk were determined for the first time. The total anthocyanins were extracted from the fruit of B. heteropoda Schrenk using 0.5% HCl in 80% methanol and were then purified [...] Read more.
In present study, the anthocyanin composition and content of the fruit of B. heteropoda Schrenk were determined for the first time. The total anthocyanins were extracted from the fruit of B. heteropoda Schrenk using 0.5% HCl in 80% methanol and were then purified using an AB-8 macroporous resin column. The purified anthocyanin extract (PAE) was evaluated by high-performance liquid chromatography with a diode array detector (HPLC-DAD) and HPLC-high resolution-electrospray ionization-mass spectrometry (HPLC-HR-ESI-MS) under the same experimental conditions. The results revealed the presence of seven different anthocyanins. The major anthocyanins purified by preparative HPLC were confirmed to be delphinidin-3-O-glucopyranoside (30.3%), cyanidin-3-O-glucopyranoside (33.5%), petunidin-3-Ο-glucopyranoside (10.5%), peonidin-3-O-glucopyranoside (8.5%) and malvidin-3-O-glucopyranoside (13.8%) using HPLC-HR-ESI-MS and NMR spectroscopy. The total anthocyanin content was 2036.6 ± 2.2 mg/100 g of the fresh weight of B. heteropoda Schrenk fruit. In terms of its total reducing capacity assay, DPPH radical-scavenging activity assay, ferric-reducing antioxidant power (FRAP) assay and ABTS radical cation-scavenging activity assay, the PAE also showed potent antioxidant activity. The results are valuable for illuminating anthocyanins composition of B. heteropoda Schrenk and for further utilising them as a promising anthocyanin pigment source. This research enriched the chemical information of B. heteropoda Schrenk. Full article
(This article belongs to the Special Issue Anthocyanins)
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3864 KiB  
Article
Support for a Photoprotective Function of Winter Leaf Reddening in Nitrogen-Deficient Individuals of Lonicera japonica
by Kaylyn L. Carpenter, Timothy S. Keidel, Melissa C. Pihl and Nicole M. Hughes
Molecules 2014, 19(11), 17810-17828; https://doi.org/10.3390/molecules191117810 - 03 Nov 2014
Cited by 18 | Viewed by 5882
Abstract
Plants growing in high-light environments during winter often exhibit leaf reddening due to synthesis of anthocyanin pigments, which are thought to alleviate photooxidative stress associated with low-temperature photoinhibition through light attenuation and/or antioxidant activity. Seasonal high-light stress can be further exacerbated by a [...] Read more.
Plants growing in high-light environments during winter often exhibit leaf reddening due to synthesis of anthocyanin pigments, which are thought to alleviate photooxidative stress associated with low-temperature photoinhibition through light attenuation and/or antioxidant activity. Seasonal high-light stress can be further exacerbated by a limited photosynthetic capacity, such as nitrogen-deficiency. In the present study, we test the following hypotheses using three populations of the semi-evergreen vine Lonicera japonica: (1) nitrogen deficiency corresponds with reduced photosynthetic capacity; (2) individuals with reduced photosynthetic capacity synthesize anthocyanin pigments in leaves during winter; and (3) anthocyanin pigments help alleviate high-light stress by attenuating green light. All populations featured co-occurring winter-green and winter-red leafed individuals on fully-exposed (high-light), south-facing slopes in the Piedmont of North Carolina, USA. Consistent with our hypotheses, red leaves consistently exhibited significantly lower foliar nitrogen than green leaves, as well as lower total chlorophyll, quantum yield efficiency, carboxylation efficiency, and photosynthesis at saturating irradiance (Asat). Light-response curves measured using ambient sunlight versus red-blue LED (i.e., lacking green wavelengths) demonstrated significantly reduced quantum yield efficiency and a higher light compensation point under sunlight relative to red-blue LED in red leaves, but not in green leaves, consistent with a (green) light-attenuating function of anthocyanin pigments. These results are consistent with the hypothesis that intraspecific anthocyanin synthesis corresponds with nitrogen deficiency and reduced photosynthetic capacity within populations, and support a light-attenuating function of anthocyanin pigments. Full article
(This article belongs to the Special Issue Anthocyanins)
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997 KiB  
Article
Effect of Standardized Cranberry Extract on the Activity and Expression of Selected Biotransformation Enzymes in Rat Liver and Intestine
by Hana Bártíková, Iva Boušová, Pavla Jedličková, Kateřina Lněničková, Lenka Skálová and Barbora Szotáková
Molecules 2014, 19(9), 14948-14960; https://doi.org/10.3390/molecules190914948 - 18 Sep 2014
Cited by 9 | Viewed by 7843
Abstract
The use of dietary supplements containing cranberry extract is a common way to prevent urinary tract infections. As consumption of these supplements containing a mixture of concentrated anthocyanins and proanthocyanidins has increased, interest in their possible interactions with drug-metabolizing enzymes has grown. In [...] Read more.
The use of dietary supplements containing cranberry extract is a common way to prevent urinary tract infections. As consumption of these supplements containing a mixture of concentrated anthocyanins and proanthocyanidins has increased, interest in their possible interactions with drug-metabolizing enzymes has grown. In this in vivo study, rats were treated with a standardized cranberry extract (CystiCran®) obtained from Vaccinium macrocarpon in two dosage schemes (14 days, 0.5 mg of proanthocyanidins/kg/day; 1 day, 1.5 mg of proanthocyanidins/kg/day). The aim of this study was to evaluate the effect of anthocyanins and proanthocyanidins contained in this extract on the activity and expression of intestinal and hepatic biotransformation enzymes: cytochrome P450 (CYP1A1, CYP1A2, CYP2B and CYP3A), carbonyl reductase 1 (CBR1), glutathione-S-transferase (GST) and UDP-glucuronosyl transferase (UGT). Administration of cranberry extract led to moderate increases in the activities of hepatic CYP3A (by 34%), CYP1A1 (by 38%), UGT (by 40%), CBR1 (by 17%) and GST (by 13%), while activities of these enzymes in the small intestine were unchanged. No changes in the relative amounts of these proteins were found. Taken together, the interactions of cranberry extract with simultaneously administered drugs seem not to be serious. Full article
(This article belongs to the Special Issue Anthocyanins)
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4566 KiB  
Article
Simple Rain-Shelter Cultivation Prolongs Accumulation Period of Anthocyanins in Wine Grape Berries
by Xiao-Xi Li, Fei He, Jun Wang, Zheng Li and Qiu-Hong Pan
Molecules 2014, 19(9), 14843-14861; https://doi.org/10.3390/molecules190914843 - 17 Sep 2014
Cited by 30 | Viewed by 7292
Abstract
Simple rain-shelter cultivation is normally applied during the grape growth season in continental monsoon climates aiming to reduce the occurrence of diseases caused by excessive rainfall. However, whether or not this cultivation practice affects the composition and concentration of phenolic compounds in wine [...] Read more.
Simple rain-shelter cultivation is normally applied during the grape growth season in continental monsoon climates aiming to reduce the occurrence of diseases caused by excessive rainfall. However, whether or not this cultivation practice affects the composition and concentration of phenolic compounds in wine grapes remains unclear. The objective of this study was to investigate the effect of rain-shelter cultivation on the accumulation of anthocyanins in wine grapes (Vitis vinifera L. Cabernet Sauvignon) grown in eastern China. The results showed that rain-shelter cultivation, compared with the open-field, extended the period of rapid accumulation of sugar, increased the soluble solid content in the grape berries, and delayed the senescence of the green leaves at harvest. The concentrations of most anthocyanins were significantly enhanced in the rain-shelter cultivated grapes, and their content increases were closely correlated with the accumulation of sugar. However, the compositions of anthocyanins in the berries were not altered. Correspondingly, the expressions of VvF3'H, VvF3'5'H, and VvUFGT were greatly up-regulated and this rising trend appeared to continue until berry maturation. These results suggested that rain-shelter cultivation might help to improve the quality of wine grape berries by prolonging the life of functional leaves and hence increasing the assimilation products. Full article
(This article belongs to the Special Issue Anthocyanins)
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2048 KiB  
Article
Effects of Climatic Conditions and Soil Properties on Cabernet Sauvignon Berry Growth and Anthocyanin Profiles
by Guo Cheng, Yan-Nan He, Tai-Xin Yue, Jun Wang and Zhen-Wen Zhang
Molecules 2014, 19(9), 13683-13703; https://doi.org/10.3390/molecules190913683 - 02 Sep 2014
Cited by 97 | Viewed by 8396
Abstract
Climatic conditions and soil type have significant influence on grape ripening and wine quality. The reported study was conducted in two “Cabernet Sauvignon (Vitis vinifera L.V)” vineyards located in Xinjiang, a semiarid wine-producing region of China during two vintages (2011 and 2012). [...] Read more.
Climatic conditions and soil type have significant influence on grape ripening and wine quality. The reported study was conducted in two “Cabernet Sauvignon (Vitis vinifera L.V)” vineyards located in Xinjiang, a semiarid wine-producing region of China during two vintages (2011 and 2012). The results indicate that soil and climate affected berry growth and anthocyanin profiles. These two localities were within a distance of 5 km from each other and had soils of different physical and chemical composition. For each vineyard, the differences of anthocyanin concentrations, and parameters concerning berry growth and composition between the two years could be explained by different climatic conditions. Soil effect was studied by investigation of differences in berry composition and anthocyanin profiles between the two vineyards in the same year, which could be explained mainly by the different soil properties, vine water and nitrogen status. Specifically, the soils with less water and organic matter produced looser clusters, heavier berry skins and higher TSS, which contributed to the excellent performance of grapes. Compared with 2011, the increases in anthocyanin concentrations for each vineyard in 2012 could be attributed to smaller number of extreme temperature (>35 °C) days and rainfall, lower vine water status and N level. The explanation for higher anthocyanin concentrations in grape skins from the soils with less water and organic matter could be the vine status differences, lighter berry weight and heavier skin weight at harvest. In particular, grapes from the soils with less water and organic matter had higher levels of 3′5′-substituded, O-methylated and acylated anthocyanins, which represented a positive characteristic conferring more stable pigmentation to the corresponding wine in the future. The present work clarifies the effects of climate and soil on berry growth and anthocyanin profiles, thus providing guidance for production of high-quality wine grapes in different regions. Full article
(This article belongs to the Special Issue Anthocyanins)
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1490 KiB  
Article
Anti-Inflammatory Effect of the Blueberry Anthocyanins Malvidin-3-Glucoside and Malvidin-3-Galactoside in Endothelial Cells
by Wu-Yang Huang, Ya-Mei Liu, Jian Wang, Xing-Na Wang and Chun-Yang Li
Molecules 2014, 19(8), 12827-12841; https://doi.org/10.3390/molecules190812827 - 21 Aug 2014
Cited by 108 | Viewed by 13306
Abstract
Blueberry fruits have a wide range of health benefits because of their abundant anthocyanins, which are natural antioxidants. The purpose of this study was to investigate the inhibitory effect of blueberry’s two main anthocyanins (malvidin-3-glucoside and malvidin-3-galactoside) on inflammatory response in endothelial cells. [...] Read more.
Blueberry fruits have a wide range of health benefits because of their abundant anthocyanins, which are natural antioxidants. The purpose of this study was to investigate the inhibitory effect of blueberry’s two main anthocyanins (malvidin-3-glucoside and malvidin-3-galactoside) on inflammatory response in endothelial cells. These two malvidin glycosides could inhibit tumor necrosis factor-alpha (TNF-α) induced increases of monocyte chemotactic protein-1 (MCP-1), intercellular adhesion molecule-1 (ICAM-1), and vascular cell adhesion molecule-1 (VCAM-1) production both in the protein and mRNA levels in a concentration-dependent manner. Mv-3-glc at the concentration of 1 μM could inhibit 35.9% increased MCP-1, 54.4% ICAM-1, and 44.7% VCAM-1 protein in supernatant, as well as 9.88% MCP-1 and 48.6% ICAM-1 mRNA expression (p < 0.05). In addition, they could decrease IκBα degradation (Mv-3-glc, Mv-3-gal, and their mixture at the concentration of 50 μM had the inhibition rate of 84.8%, 75.3%, and 43.2%, respectively, p < 0.01) and block the nuclear translocation of p65, which suggested their anti-inflammation mechanism was mediated by the nuclear factor-kappa B (NF-κB) pathway. In general malvidin-3-glucoside had better anti-inflammatory effect than malvidin-3-galactoside. These results indicated that blueberry is good resource of anti-inflammatory anthocyanins, which can be promising molecules for the development of nutraceuticals to prevent chronic inflammation in many diseases. Full article
(This article belongs to the Special Issue Anthocyanins)
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1229 KiB  
Article
Anthocyanin Characterization, Total Phenolic Quantification and Antioxidant Features of Some Chilean Edible Berry Extracts
by Anghel Brito, Carlos Areche, Beatriz Sepúlveda, Edward J. Kennelly and Mario J. Simirgiotis
Molecules 2014, 19(8), 10936-10955; https://doi.org/10.3390/molecules190810936 - 28 Jul 2014
Cited by 110 | Viewed by 11158
Abstract
The anthocyanin composition and HPLC fingerprints of six small berries endemic of the VIII region of Chile were investigated using high resolution mass analysis for the first time (HR-ToF-ESI-MS). The antioxidant features of the six endemic species were compared, including a variety of [...] Read more.
The anthocyanin composition and HPLC fingerprints of six small berries endemic of the VIII region of Chile were investigated using high resolution mass analysis for the first time (HR-ToF-ESI-MS). The antioxidant features of the six endemic species were compared, including a variety of blueberries which is one of the most commercially significant berry crops in Chile. The anthocyanin fingerprints obtained for the fruits were compared and correlated with the antioxidant features measured by the bleaching of the DPPH radical, the ferric reducing antioxidant power (FRAP), the superoxide anion scavenging activity assay (SA), and total content of phenolics, flavonoids and anthocyanins measured by spectroscopic methods. Thirty one anthocyanins were identified, and the major ones were quantified by HPLC-DAD, mostly branched 3-O-glycosides of delphinidin, cyanidin, petunidin, peonidin and malvidin. Three phenolic acids (feruloylquinic acid, chlorogenic acid, and neochlorogenic acid) and five flavonols (hyperoside, isoquercitrin, quercetin, rutin, myricetin and isorhamnetin) were also identified. Calafate fruits showed the highest antioxidant activity (2.33 ± 0.21 μg/mL in the DPPH assay), followed by blueberry (3.32 ± 0.18 μg/mL), and arrayán (5.88 ± 0.21), respectively. Full article
(This article belongs to the Special Issue Anthocyanins)
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Graphical abstract

421 KiB  
Article
Antioxidant Activity and Acetylcholinesterase Inhibition of Grape Skin Anthocyanin (GSA)
by Mehnaz Pervin, Md. Abul Hasnat, Yoon Mi Lee, Da Hye Kim, Jeong Eun Jo and Beong Ou Lim
Molecules 2014, 19(7), 9403-9418; https://doi.org/10.3390/molecules19079403 - 03 Jul 2014
Cited by 52 | Viewed by 9187
Abstract
We aimed to investigate the antioxidant and acetylcholinesterase inhibitory activities of the anthocyanin rich extract of grape skin. Grape skin anthocyanin (GSA) neutralized free radicals in different test systems, such as 2,-2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays, to form complexes with Fe [...] Read more.
We aimed to investigate the antioxidant and acetylcholinesterase inhibitory activities of the anthocyanin rich extract of grape skin. Grape skin anthocyanin (GSA) neutralized free radicals in different test systems, such as 2,-2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays, to form complexes with Fe2+ preventing 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced erythrocyte hemolysis and oxidative DNA damage. Moreover, GSA decreased reactive oxygen species (ROS) generation in isolated mitochondria thus inhibiting 2',-7'-dichlorofluorescin (DCFH) oxidation. In an in vivo study, female BALB/c mice were administered GSA, at 12.5, 25, and 50 mg per kg per day orally for 30 consecutive days. Herein, we demonstrate that GSA administration significantly elevated the level of antioxidant enzymes in mice sera, livers, and brains. Furthermore, GSA inhibited acetylcholinesterase (AChE) in the in vitro assay with an IC50 value of 363.61 µg/mL. Therefore, GSA could be an excellent source of antioxidants and its inhibition of cholinesterase is of interest with regard to neurodegenerative disorders such as Alzheimer’s disease. Full article
(This article belongs to the Special Issue Anthocyanins)
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277 KiB  
Article
Influence of Temperature and Preserving Agents on the Stability of Cornelian Cherries Anthocyanins
by Bianca Moldovan and Luminiţa David
Molecules 2014, 19(6), 8177-8188; https://doi.org/10.3390/molecules19068177 - 17 Jun 2014
Cited by 42 | Viewed by 7281
Abstract
Cornelian cherry (Cornus mas L.) fruits are known for their significant amounts of anthocyanins which can be used as natural food colorants. The storage stability of anthocyanins from these fruit extracts, at different temperatures (2 °C, 25 °C and 75 °C), [...] Read more.
Cornelian cherry (Cornus mas L.) fruits are known for their significant amounts of anthocyanins which can be used as natural food colorants. The storage stability of anthocyanins from these fruit extracts, at different temperatures (2 °C, 25 °C and 75 °C), pH 3.02, in the presence of two of the most widely employed food preserving agents (sodium benzoate and potassium sorbate) was investigated. The highest stability was exhibited by the anthocyanin extract stored at 2 °C without any added preservative, with half-life and constant rate values of 1443.8 h and 0.48 × 10−3 h−1, respectively. The highest value of the degradation rate constant (82.76 × 10−3/h) was obtained in the case of anthocyanin extract stored at 75 °C without any added preservative. Experimental results indicate that the storage degradation of anthocyanins followed first-order reaction kinetics under each of the investigated conditions. In aqueous solution, the food preservatives used were found to have a slight influence on the anthocyanins’ stability. Full article
(This article belongs to the Special Issue Anthocyanins)
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428 KiB  
Article
Effect of Two Anti-Fungal Treatments (Metrafenone and Boscalid Plus Kresoxim-methyl) Applied to Vines on the Color and Phenol Profile of Different Red Wines
by Noelia Briz-Cid, María Figueiredo-González, Raquel Rial-Otero, Beatriz Cancho-Grande and Jesús Simal-Gándara
Molecules 2014, 19(6), 8093-8111; https://doi.org/10.3390/molecules19068093 - 16 Jun 2014
Cited by 21 | Viewed by 6226
Abstract
The effect of two anti-fungal treatments (metrafenone and boscalid + kresoxim-methyl) on the color and phenolic profile of Tempranillo and Graciano red wines has been studied. To evaluate possible modifications in color and phenolic composition of wines, control and wines elaborated with treated [...] Read more.
The effect of two anti-fungal treatments (metrafenone and boscalid + kresoxim-methyl) on the color and phenolic profile of Tempranillo and Graciano red wines has been studied. To evaluate possible modifications in color and phenolic composition of wines, control and wines elaborated with treated grapes under good agricultural practices were analyzed. Color was assessed by Glories and CIELab parameters. Color changes were observed for treated wines with boscalid + kresoxim-methyl, leading to the production of wines with less color vividness. Phenolic profile was characterized by HPLC analysis. Boscalid + kresoxim-methyl treatment promoted the greatest decrease on the phenolic content in wines. Full article
(This article belongs to the Special Issue Anthocyanins)
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Review

Jump to: Research

907 KiB  
Review
The Encapsulation of Anthocyanins from Berry-Type Fruits. Trends in Foods
by Paz Robert and Carolina Fredes
Molecules 2015, 20(4), 5875-5888; https://doi.org/10.3390/molecules20045875 - 03 Apr 2015
Cited by 90 | Viewed by 10650
Abstract
During the last decade, many berry-type fruits have been recognised as good sources of anthocyanins. Nevertheless, the use of anthocyanins in the development of food colourants and healthy and/or functional ingredients has been limited because of their low stability under given environmental conditions [...] Read more.
During the last decade, many berry-type fruits have been recognised as good sources of anthocyanins. Nevertheless, the use of anthocyanins in the development of food colourants and healthy and/or functional ingredients has been limited because of their low stability under given environmental conditions and interaction with other compounds in the food matrix. This review compiles information about the encapsulation of anthocyanins from twelve different berry-type fruit species as a technology for improving the stability and/or bioavailability of anthocyanins. Encapsulation by spray drying has been the primary method used to encapsulate anthocyanins, and some studies attempt to keep anthocyanin microparticles stable during storage. Nevertheless, more studies are needed to determine the stability of anthocyanin microparticles in food matrices over the product shelf life in the development of food colourants. Studies about encapsulated anthocyanins in simulated gastrointestinal models have primarily been conducted on the release of anthocyanins from microparticles to evaluate their bioavailability. However, adding anthocyanin microparticles to a food vehicle must guarantee the health properties attributed to the specific anthocyanins present in berry-type fruits. Full article
(This article belongs to the Special Issue Anthocyanins)
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594 KiB  
Review
The Role of Acyl-Glucose in Anthocyanin Modifications
by Nobuhiro Sasaki, Yuzo Nishizaki, Yoshihiro Ozeki and Taira Miyahara
Molecules 2014, 19(11), 18747-18766; https://doi.org/10.3390/molecules191118747 - 14 Nov 2014
Cited by 73 | Viewed by 10468
Abstract
Higher plants can produce a wide variety of anthocyanin molecules through modification of the six common anthocyanin aglycons that they present. Thus, hydrophilic anthocyanin molecules can be formed and stabilized by glycosylation and acylation. Two types of glycosyltransferase (GT) and acyltransferase (AT) have [...] Read more.
Higher plants can produce a wide variety of anthocyanin molecules through modification of the six common anthocyanin aglycons that they present. Thus, hydrophilic anthocyanin molecules can be formed and stabilized by glycosylation and acylation. Two types of glycosyltransferase (GT) and acyltransferase (AT) have been identified, namely cytoplasmic GT and AT and vacuolar GT and AT. Cytoplasmic GT and AT utilize UDP-sugar and acyl-CoA as donor molecules, respectively, whereas both vacuolar GT and AT use acyl-glucoses as donor molecules. In carnation plants, vacuolar GT uses aromatic acyl-glucoses as the glucose donor in vivo; independently, vacuolar AT uses malylglucose, an aliphatic acyl-glucose, as the acyl-donor. In delphinium and Arabidopsis, p-hydroxybenzoylglucose and sinapoylglucose are used in vivo as bi-functional donor molecules by vacuolar GT and AT, respectively. The evolution of these enzymes has allowed delphinium and Arabidopsis to utilize unique donor molecules for production of highly modified anthocyanins. Full article
(This article belongs to the Special Issue Anthocyanins)
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625 KiB  
Review
Mistaken Identity: Clarification of Rubus coreanus Miquel (Bokbunja)
by Jungmin Lee, Michael Dossett and Chad E. Finn
Molecules 2014, 19(7), 10524-10533; https://doi.org/10.3390/molecules190710524 - 18 Jul 2014
Cited by 15 | Viewed by 12145
Abstract
In the U.S., there has been a recent surge in Korean black raspberry products available and in the number of reports about this species appearing in the scientific literature. Despite this, the majority of products sold and the work carried out has been [...] Read more.
In the U.S., there has been a recent surge in Korean black raspberry products available and in the number of reports about this species appearing in the scientific literature. Despite this, the majority of products sold and the work carried out has been on Rubus occidentalis L., not R. coreanus Miquel. The importance of accurate recognition of all starting material is multiplied for research downstream, including genetics/genomics, plant breeding, phenolic identification, food processing improvements and pharmacokinetic investigations. An overview of distinguishing characteristics separating R. coreanus from R. occidentalis will be presented. Research conducted on correctly identified fruit will also be summarized to aid future studies that might showcase the unique qualities that bokbunja can offer. Full article
(This article belongs to the Special Issue Anthocyanins)
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