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Special Issue "Advances in Anthocyanin Research 2018"

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

Deadline for manuscript submissions: 30 June 2018

Special Issue Editors

Guest Editor
Prof. Dr. M. Monica Giusti

Department of Food Science and Technology, The Ohio State University, Columbus, OH 43210, USA
Website | E-Mail
Interests: functional foods, phytonutrients, natural colorants; chemistry and functionality of flavonoids, with emphasis on anthocyanins as food colorants and functional foods and other phenolic compounds, such as isoflavones and proanthocyanidins
Guest Editor
Dr. Gregory T. Sigurdson

Department of Food Science and Technology, The Ohio State University, Columbus, OH 43210, USA
Website | E-Mail
Interests: naturally derived pigments; anthocyanins and polyphenolics; chemistry affecting color expression; color quality, analytical methods; application in foods and other matrices as colorants or bioactives; health promoting properties

Special Issue Information

Dear Colleagues,

Interest and research on anthocyanin-based pigments has been increasing considerably in recent years. PubMed shows an almost exponential growth curve in the number of anthocyanins publications, having increased from 55 (in 1996) to 264 (in 2006) and to 892 (in 2016). Anthocyanins have long been identified as important pigments responsible for many flower, fruit, and vegetable colorations, producing a complex variety of hues ranging from yellow–red–purple–blue. More recently, colorants are being studied, not only for their biochemical roles in plants, but also for their applications in human products and contributions to health. Works on anthocyanins, specifically, as well as epidemiological findings, further indicate these plant produced pigments to be beneficial in the reduction of chronic inflammatory diseases, such as type 2 diabetes and cardiovascular disease. Considerable advances in the identification, analysis, application, and biological activities of anthocyanins have been made in recent years. However, the pigments exhibit diverse natural chemistry. Currently, more than 700 unique anthocyanin structures have been identified in nature, and many more in processed foods, each generally having distinctive reactivity and colorimetric properties. Therefore, authors are invited to submit manuscripts to this Molecules Special Issue, “Advances in Anthocyanin Research 2018”, in which all aspects related to anthocyanin chemistry, such as composition, degradative reactions, biosynthesis; applications in agricultural, cosmetic, and food chemistry; use as natural colorants; and aspects or mechanisms of nutrition or reducing the risks of chronic diseases will be discussed.

Prof. Dr. M. Monica Giusti
Dr. Gregory T. Sigurdson
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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 monthly 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 1800 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
  • Natural colorants
  • Botanical aspects
  • Color quality of foods, drugs, and cosmetics
  • Anthocyanin chemistry and application
  • Anthocyanin absorption and metabolism
  • Anthocyanin Bioactivity and functionality
  • Anthocyanin’s role in the reduction of chronic diseases

Published Papers (10 papers)

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Research

Open AccessArticle Roselle Anthocyanins: Antioxidant Properties and Stability to Heat and pH
Molecules 2018, 23(6), 1357; https://doi.org/10.3390/molecules23061357
Received: 1 May 2018 / Revised: 30 May 2018 / Accepted: 31 May 2018 / Published: 5 June 2018
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Abstract
Roselle is rich in anthocyanins and is traditionally used to prepare a bright red beverage by decoction. However, heat treatment and different pH environments are often encountered during food processing, and these factors are often detrimental to anthocyanins. Therefore, it is very important
[...] Read more.
Roselle is rich in anthocyanins and is traditionally used to prepare a bright red beverage by decoction. However, heat treatment and different pH environments are often encountered during food processing, and these factors are often detrimental to anthocyanins. Therefore, it is very important to understand the influence of pH and heat treatment on anthocyanins for the application of roselle. This study determined the antioxidant properties of roselle extract, explored changes in the color and anthocyanin content in different pH environments, and evaluated the thermal stability of roselle anthocyanins using kinetic equations. The results showed that the roselle extract is rich in anthocyanins and has good antioxidant capacity (DPPH IC50 = 4.06 mg/mL, ABTS IC50 = 3.7 mg/mL). The anthocyanins themselves exhibited a certain degree of heat resistance and good color stability in an acidic environment. In contrast, they degraded very quickly and exhibited significant changes in color in a low-acid environment. The activation energy (Ea) ranges of the anthocyanins in the acidic and low-acid environments were quite different at 55.8–95.7 and 31.4–74.9 kJ/mol, respectively. Thus, it can be concluded that roselle anthocyanins are susceptible to heat treatment in a low-acid environment, affecting their quality and appearance; however, they can serve as a good source of functional ingredients and color in an acidic environment. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Vermicompost Supplementation Improves the Stability of Bioactive Anthocyanin and Phenolic Compounds in Clinacanthus nutans Lindau
Molecules 2018, 23(6), 1345; https://doi.org/10.3390/molecules23061345
Received: 25 April 2018 / Revised: 26 May 2018 / Accepted: 30 May 2018 / Published: 4 June 2018
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Abstract
This project studied the effect of vermicompost application on the composition of bioactive anthocyanin and phenolic compounds, and the antioxidant activity of Clinacanthus nutans. The correlation between the bioactive constituents and antioxidant capacity was also evaluated. In this project, a field study
[...] Read more.
This project studied the effect of vermicompost application on the composition of bioactive anthocyanin and phenolic compounds, and the antioxidant activity of Clinacanthus nutans. The correlation between the bioactive constituents and antioxidant capacity was also evaluated. In this project, a field study was conducted using a randomized complete block design (RCBD) with four treatment groups, including control plants (CC), plants supplied with chemical fertilizer (CF), plants supplied with vermicompost (VC), and plants supplied with mixed fertilizer (MF). The leaves of C. nutans from all treatment groups were harvested, subjected to solvent extraction, and used for quantification of total anthocyanin content (TAC), total phenolic content (TPC), and total flavonoid content (TFC). The initial antioxidant activity of the extracts was evaluated using 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays, as well as after two and four weeks of storage at −20 °C and 4 °C. Data analysis showed that CC plants contained the highest TAC (2180.14 ± 338.43 µg/g dry weight) and TFC (276.25 ± 3.09 mg QE/g dry weight). On the other hand, CF plants showed the highest TPC (181.53 ± 35.58 mg GAE/g dry weight). Moreover, we found that CC plants had the highest antioxidant potential against DPPH radicals whereas MF plants showed the lowest antioxidant potential. After four weeks of extract storage at −20 °C and 4 °C, the TPC, TFC, TAC, and antioxidant potential of the extracts decreased. Extracts from VC showed the lowest percentage of total phenolic and total flavonoid loss after extract storage at −20 °C and 4 °C compared with other plant extracts. At this juncture, it could be deduced that the application of vermicompost had little effect on the expression of phenolics, flavonoids, or anthocyanin in C. nutans. However, the extract from plants treated with vermicompost (VC and MF) showed better stability compared with CC and CF after extract storage at different temperatures. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle The Microencapsulation of Maqui (Aristotelia chilensis (Mol.) Stuntz) Juice by Spray-Drying and Freeze-Drying Produces Powders with Similar Anthocyanin Stability and Bioaccessibility
Molecules 2018, 23(5), 1227; https://doi.org/10.3390/molecules23051227
Received: 31 March 2018 / Revised: 16 May 2018 / Accepted: 16 May 2018 / Published: 20 May 2018
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Abstract
The microencapsulation of maqui juice by spray-drying and freeze-drying was studied as a strategy to protect anthocyanins in new food formulations in order to improve the anthocyanin retention before consumption and the bioaccessibility. It is well known that the encapsulation method affects both
[...] Read more.
The microencapsulation of maqui juice by spray-drying and freeze-drying was studied as a strategy to protect anthocyanins in new food formulations in order to improve the anthocyanin retention before consumption and the bioaccessibility. It is well known that the encapsulation method affects both the shape and size of powders, being assumed that undefined forms of freeze-drying powders might affect their stability due to the high permeability to oxygen. The objective of this study was to compare the microencapsulation of maqui juice by spray-drying and freeze-drying, evaluating the stability of specific anthocyanins in yogurt and after in vitro digestion. Results indicated that most relevant differences between spray-drying and freeze-drying powders were the morphology and particle size that affect their solubility (70.4–59.5%) when they were reconstituted in water. Nevertheless these differences did not affect the stability of anthocyanins as other research have proposed. Both encapsulation methods generated powders with a high stability of 3-O-monoglycosylated anthocyanins in yogurt (half-life values of 75–69 days for delphinidin-3-sambubioside). Furthermore, no significant differences in the bioaccessibility of anthocyanins between maqui juice powders (44.1–43.8%) were found. In conclusion, the microencapsulation of maqui juice by freeze-drying is as effective as spray-drying to produce new value-added food formulations with stable anthocyanins. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Anthocyanin Composition and Content in Rye Plants with Different Grain Color
Molecules 2018, 23(4), 948; https://doi.org/10.3390/molecules23040948
Received: 29 March 2018 / Revised: 17 April 2018 / Accepted: 17 April 2018 / Published: 19 April 2018
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Abstract
The color of grain in cereals is determined mainly by anthocyanin pigments. A large level of genetic diversity for anthocyanin content and composition in the grain of different species was observed. In rye, recessive mutations in six genes (vi1...vi6) lead to the absence
[...] Read more.
The color of grain in cereals is determined mainly by anthocyanin pigments. A large level of genetic diversity for anthocyanin content and composition in the grain of different species was observed. In rye, recessive mutations in six genes (vi1...vi6) lead to the absence of anthocyanins in all parts of the plant. Moreover, dominant genes of anthocyanin synthesis in aleurone (gene C) and pericarp (gene Vs) also affect the color of the grain. Reverse phase high-performance liquid chromatography and mass spectrometry were used to study anthocyanins in 24 rye samples. A lack of anthocyanins in the lines with yellow and brown grain was determined. Delphinidin rutinoside and cyanidin rutinoside were found in the green-seeded lines. Six samples with violet grains significantly varied in terms of anthocyanin composition and content. However, the main aglycone was cyanidin or peonidin in all of them. Monosaccharide glucose and disaccharide rutinose served as the glycoside units. Violet-seeded accession forms differ in the ratio of the main anthocyanins and the range of their acylated derivatives. The acyl groups were presented mainly by radicals of malonic and sinapic acids. For the colored forms, a profile of the revealed anthocyanins with the indication of their contents was given. The obtained results are discussed in connection to similar data in rice, barley, and wheat, which will provide a perspective for future investigations. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessCommunication Cardiovascular Mechanisms of Action of Anthocyanins May Be Associated with the Impact of Microbial Metabolites on Heme Oxygenase-1 in Vascular Smooth Muscle Cells
Molecules 2018, 23(4), 898; https://doi.org/10.3390/molecules23040898
Received: 22 March 2018 / Revised: 6 April 2018 / Accepted: 11 April 2018 / Published: 13 April 2018
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Abstract
Anthocyanins are reported to have cardio-protective effects, although their mechanisms of action remain elusive. We aimed to explore the effects of microbial metabolites common to anthocyanins and other flavonoids on vascular smooth muscle heme oxygenase-1 (HO-1) expression. Thirteen phenolic metabolites identified by previous
[...] Read more.
Anthocyanins are reported to have cardio-protective effects, although their mechanisms of action remain elusive. We aimed to explore the effects of microbial metabolites common to anthocyanins and other flavonoids on vascular smooth muscle heme oxygenase-1 (HO-1) expression. Thirteen phenolic metabolites identified by previous anthocyanin human feeding studies, as well as 28 unique mixtures of metabolites and their known precursor structures were explored for their activity on HO-1 protein expression in rat aortic smooth muscle cells (RASMCs). No phenolic metabolites were active when treated in isolation; however, five mixtures of phenolic metabolites significantly increased HO-1 protein expression (127.4–116.6%, p ≤ 0.03). The present study demonstrates that phenolic metabolites of anthocyanins differentially affect HO-1 activity, often having additive, synergistic or nullifying effects. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessFeature PaperArticle Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins
Molecules 2018, 23(4), 744; https://doi.org/10.3390/molecules23040744
Received: 27 February 2018 / Revised: 18 March 2018 / Accepted: 21 March 2018 / Published: 23 March 2018
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Abstract
Juices colored by anthocyanins experience color loss related to fortification with ascorbic acid (AA), thought to be the result of condensation at Carbon-4 of anthocyanins. To further understand this mechanism, pyranoanthocyanins, having a fourth-ring covalently occupying Carbon-4, were synthesized to compare its reactivity
[...] Read more.
Juices colored by anthocyanins experience color loss related to fortification with ascorbic acid (AA), thought to be the result of condensation at Carbon-4 of anthocyanins. To further understand this mechanism, pyranoanthocyanins, having a fourth-ring covalently occupying Carbon-4, were synthesized to compare its reactivity with AA against that of anthocyanins. Pyranoanthocyanins were synthesized by combining chokeberry anthocyanins with pyruvic acid. AA (250–1000 mg/L) was added to either chokeberry extract, cyanidin-3-galactoside, or 5-Carboxypyranocyanidin-3-galactoside. Samples were stored in the dark for 5 days at 25 °C and spectra (380–700 nm), color (CIE-L*c*h*), and composition changes (HPLC-MS/MS) were monitored. Extensive bleaching occurred for cyanidin-3-galactoside and chokeberry colored solutions, with a decrease in half-lives from 22.8 to 0.3 days for Cyanidin-3-galactoside when 1000 mg/L AA was added. 5-Carboxypyranocyanidin-3-galactoside solution better maintained color with limited loss in absorbance, due to the formation of colored degradation products (λvis-max = 477 to 487 nm), and half-life decrease from 40.8 to 2.7 days, an 8–13-fold improvement compared to anthocyanins. This suggested alternative sites of reactivity with AA. Carbon-4 may be the preferred site for AA-pigment interactions, but it was not the only location. With Carbon-4 blocked, 5-Carboxypyranocyanidin-3-galactoside reacted with AA to form new pigments and reduce bleaching. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Cis–Trans Configuration of Coumaric Acid Acylation Affects the Spectral and Colorimetric Properties of Anthocyanins
Molecules 2018, 23(3), 598; https://doi.org/10.3390/molecules23030598
Received: 2 February 2018 / Revised: 23 February 2018 / Accepted: 4 March 2018 / Published: 7 March 2018
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Abstract
The color expression of anthocyanins can be affected by a variety of environmental factors and structural characteristics. Anthocyanin acylation (type and number of acids) is known to be key, but the influence of acyl isomers (with unique stereochemistries) remains to be explored. The
[...] Read more.
The color expression of anthocyanins can be affected by a variety of environmental factors and structural characteristics. Anthocyanin acylation (type and number of acids) is known to be key, but the influence of acyl isomers (with unique stereochemistries) remains to be explored. The objective of this study was to investigate the effects of cis–trans configuration of the acylating group on the spectral and colorimetric properties of anthocyanins. Petunidin-3-rutinoside-5-glucoside (Pt-3-rut-5-glu) and Delphinidin-3-rutinoside-5-glucoside (Dp-3-rut-5-glu) and their cis and trans coumaroylated derivatives were isolated from black goji and eggplant, diluted in pH 1–9 buffers, and analyzed spectrophotometrically (380–700 nm) and colorimetrically (CIELAB) during 72 h of storage (25 °C, dark). The stereochemistry of the acylating group strongly impacted the spectra, color, and stability of the Dp and Pt anthocyanins. Cis acylated pigments exhibited the greatest λmax in all pH, as much as 66 nm greater than their trans counterparts, showing bluer hues. Cis acylation seemed to reduce hydration across pH, increasing color intensity, while trans acylation generally improved color retention over time. Dp-3-cis-p-cou-rut-5-glu exhibited blue hues even in pH 5 (C*ab = 10, hab = 256°) where anthocyanins are typically colorless. Cis or trans double bond configurations of the acylating group affected anthocyanin spectral and stability properties. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Exogenous 24-Epibrassinolide Interacts with Light to Regulate Anthocyanin and Proanthocyanidin Biosynthesis in Cabernet Sauvignon (Vitis vinifera L.)
Received: 2 November 2017 / Revised: 28 December 2017 / Accepted: 29 December 2017 / Published: 9 January 2018
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Abstract
Anthocyanins and proanthocyanidins (PAs) are crucial factors that affect the quality of grapes and the making of wine, which were stimulated by various stimuli and environment factors (sugar, hormones, light, and temperature). The aim of the study was to investigate the influence of
[...] Read more.
Anthocyanins and proanthocyanidins (PAs) are crucial factors that affect the quality of grapes and the making of wine, which were stimulated by various stimuli and environment factors (sugar, hormones, light, and temperature). The aim of the study was to investigate the influence of exogenous 24-Epibrassinolide (EBR) and light on the mechanism of anthocyanins and PAs accumulation in grape berries. Grape clusters were sprayed with EBR (0.4 mg/L) under light and darkness conditions (EBR + L, EBR + D), or sprayed with deionized water under light and darkness conditions as controls (L, D), at the onset of veraison. A large amount of anthocyanins accumulated in the grape skins and was measured under EBR + L and L treatments, whereas EBR + D and D treatments severely suppressed anthocyanin accumulation. This indicated that EBR treatment could produce overlay effects under light, in comparison to that in dark. Real-time quantitative PCR analysis indicated that EBR application up-regulated the expression of genes (VvCHI1, VvCHS2, VvCHS3, VvDFR, VvLDOX, VvMYBA1) under light conditions. Under darkness conditions, only early biosynthetic genes of anthocyanin biosynthesis responded to EBR. Furthermore, we also analyzed the expression levels of the BR-regulated transcription factor VvBZR1 (Brassinazole-resistant 1) and light-regulated transcription factor VvHY5 (Elongated hypocotyl 5). Our results suggested that EBR and light had synergistic effects on the expression of genes in the anthocyanin biosynthesis pathway. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Phytoestrogenic Activity of Blackcurrant Anthocyanins Is Partially Mediated through Estrogen Receptor Beta
Received: 27 November 2017 / Revised: 22 December 2017 / Accepted: 27 December 2017 / Published: 29 December 2017
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Abstract
Phytoestrogens are plant compounds with estrogenic effects found in many foods. We have previously reported phytoestrogen activity of blackcurrant anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutinoside, delphinidin-3-glucoside, and delphinidin-3-rutinoside) via the estrogen receptor (ER)α. In this study, we investigated the participation of ERβ in the phytoestrogen activity
[...] Read more.
Phytoestrogens are plant compounds with estrogenic effects found in many foods. We have previously reported phytoestrogen activity of blackcurrant anthocyanins (cyanidin-3-glucoside, cyanidin-3-rutinoside, delphinidin-3-glucoside, and delphinidin-3-rutinoside) via the estrogen receptor (ER)α. In this study, we investigated the participation of ERβ in the phytoestrogen activity of these anthocyanins. Blackcurrant anthocyanin induced ERβ-mediated transcriptional activity, and the IC50 of ERβ was lower than that of ERα, indicating that blackcurrant anthocyanins have a higher binding affinity to ERβ. In silico docking analysis of cyanidin and delphinidin, the core portions of the compound that fits within the ligand-binding pocket of ERβ, showed that similarly to 17β-estradiol, hydrogen bonds formed with the ERβ residues Glu305, Arg346, and His475. No fitting placement of glucoside or rutinoside sugar chains within the ligand-binding pocket of ERβ-estradiol complex was detected. However, as the conformation of helices 3 and 12 in ERβ varies depending on the ligand, we suggest that the surrounding structure, including these helices, adopts a conformation capable of accommodating glucoside or rutinoside. Comparison of ERα and ERβ docking structures revealed that the selectivity for ERβ is higher than that for ERα, similar to genistein. These results show that blackcurrant anthocyanins exert phytoestrogen activity via ERβ. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Open AccessArticle Antinociceptive and Antibacterial Properties of Anthocyanins and Flavonols from Fruits of Black and Non-Black Mulberries
Received: 21 November 2017 / Revised: 16 December 2017 / Accepted: 19 December 2017 / Published: 21 December 2017
Cited by 2 | PDF Full-text (3102 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Anthocyanins and flavones are important pigments responsible for the coloration of fruits. Mulberry fruit is rich in anthocyanins and flavonols, which have multiple uses in traditional Chinese medicine. The antinociceptive and antibacterial activities of total flavonoids (TF) from black mulberry (MnTF, TF of
[...] Read more.
Anthocyanins and flavones are important pigments responsible for the coloration of fruits. Mulberry fruit is rich in anthocyanins and flavonols, which have multiple uses in traditional Chinese medicine. The antinociceptive and antibacterial activities of total flavonoids (TF) from black mulberry (MnTF, TF of Morus nigra) and non-black mulberry (MmTF, TF of Morus mongolica; and MazTF, TF of Morus alba ‘Zhenzhubai’) fruits were studied. MnTF was rich in anthocyanins (11.3 mg/g) and flavonols (0.7 mg/g) identified by ultra-performance liquid chromatography–tunable ultraviolet/mass single-quadrupole detection (UPLC–TUV/QDa). Comparatively, MmTF and MazTF had low flavonol contents and MazTF had no anthocyanins. MnTF showed significantly higher antinociceptive and antibacterial activities toward Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus than MmTF and MazTF. MnTF inhibited the expression of interleukin 6 (IL-6), inducible nitric oxide synthase (iNOS), phospho-p65 (p-p65) and phospho-IκBα (p-IκBα), and increased interleukin 10 (IL-10). Additionally, mice tests showed that cyanidin-3-O-glucoside (C3G), rutin (Ru) and isoquercetin (IQ) were the main active ingredients in the antinociceptive process. Stronger antinociceptive effect of MnTF was correlated with its high content of anthocyanins and flavonols and its inhibitory effects on proinflammatory cytokines, iNOS and nuclear factor-κB (NF-κB) pathway-related proteins. Full article
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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