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3 pages, 184 KiB

Open AccessEditorial

Anthocyanins: The Infinite Properties of These Incredible Compounds

by Pasquale Crupi

Molecules 2023, 28(4), 1812; https://doi.org/10.3390/molecules28041812 - 15 Feb 2023

Cited by 1 | Viewed by 1446

Abstract

Anthocyanins are acknowledged for their great heterogeneity of colors, from orange to blue hues in the visible spectrum [...] Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

Research

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15 pages, 2637 KiB

Open AccessFeature PaperArticle

Functionalization of 7-Hydroxy-pyranoflavylium: Synthesis of New Dyes with Extended Chromatic Stability

by Ana Rita Pereira, Victor de Freitas, Nuno Mateus and Joana Oliveira

Molecules 2022, 27(21), 7351; https://doi.org/10.3390/molecules27217351 - 29 Oct 2022

Cited by 4 | Viewed by 1565

Abstract

This work reports the functionalization of pyranoflavyliums pigment using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride coupling chemistry. Four cinnamic acids were used to establish an ester bond with the hydroxyl group of the pyranoflavylium, namely 4-dimethylamino-, 4-amino-, 4-bromo-, and trans-cinnamic acids. The experimental condition, namely the molar [...] Read more.

This work reports the functionalization of pyranoflavyliums pigment using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride coupling chemistry. Four cinnamic acids were used to establish an ester bond with the hydroxyl group of the pyranoflavylium, namely 4-dimethylamino-, 4-amino-, 4-bromo-, and trans-cinnamic acids. The experimental condition, namely the molar ratios, solvent, and reaction time, were adjusted to obtain higher reaction yields in a reduced period. Excellent reaction yields of 68%, 85%, 94%, and 99% were achieved for 4-amino, trans-, 4-bromo, and 4-dimethylamino pyranoflavylium cinnamates, respectively. The structure of the functionalized pigments was fully clarified using one-dimensional (1H) and two-dimensional (COSY, HSQC, and HMBC) NMR experiments and HRSM analysis. Regardless of the type of functionalization, the UV-Visible spectrum showed a bathochromic shift (red region) on the maximum absorption wavelength and the absence of acid-base reactions throughout a broad pH range in comparison to the pyranoflavylium precursor. This work offers a valuable environmentally friendly, quick, and straightforward alternative to flavylium compounds’ challenging and labor-intensive functionalization, resulting in novel dyes with higher stability and dissimilar chromatic features. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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13 pages, 1178 KiB

Open AccessArticle

Evaluation of the Chemical Composition, Bioactive Substance, Gas Production, and Rumen Fermentation Parameters of Four Types of Distiller’s Grains

by Qi Lu, Qingyuan Luo, Jiaxuan Li, Xu Wang, Chao Ban, Jixiao Qin, Yayuan Tian, Xingzhou Tian and Xiang Chen

Molecules 2022, 27(18), 6134; https://doi.org/10.3390/molecules27186134 - 19 Sep 2022

Cited by 9 | Viewed by 2332

Abstract

Distiller’s grain is rich in natural active ingredients and can be used as an excellent antioxidant feed for goats. The current study aimed to assess the feeding value of four different types of distiller’s grains with an in vitro gas production trial. The [...] Read more.

Distiller’s grain is rich in natural active ingredients and can be used as an excellent antioxidant feed for goats. The current study aimed to assess the feeding value of four different types of distiller’s grains with an in vitro gas production trial. The chemical composition, total phenols, total anthocyanins, dry matter degradability, methane, hydrogen, and rumen fermentation parameters were evaluated. The results indicated that red distiller’s grain and glutinous rice distiller’s grain had higher (p < 0.05) levels of crude protein than the other two types. There were significantly (p < 0.05) higher concentrations of dry matter, ether extract, hemicellulose, and total carbohydrate in corn distiller’s grain than in the other three types of distiller’s grain. In addition, red distiller’s grain showed a higher (p < 0.05) gas production rate constant (c) and ruminal outflow rate, as well as higher (p < 0.05) concentrations of total phenol, total anthocyanins and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity, than the other three types of distiller’s grains. In contrast, red distiller’s grain displayed the lowest (p < 0.05) immediately soluble fraction (a) and half the time of maximum gas production relative to the other samples. In particular, the levels of methane (%) in white distiller’s grain and glutinous rice distiller’s grain were greater (p < 0.05) than that in red distiller’s grain. Moreover, the ammonia nitrogen content in red distiller’s grain was greater (p < 0.05) than that in white distiller’s grain and corn distiller’s grain. In contrast, red distiller’s grain exhibited a lower (p < 0.05) level of ruminal fluid acetic acid relative to that found in white distiller’s grain and corn distiller’s grain. Taken together, the results showed that red distiller’s grain and glutinous rice distiller’s grain could be used as protein feed, red distiller’s grain had higher levels of total phenols and total anthocyanins and a high DPPH scavenging activity; corn distiller’s grain might be considered as an alternative energy source feed, and white distiller’s grain exhibited higher total gas production. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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18 pages, 3654 KiB

Open AccessArticle

Anti-Inflammatory Activity of an In Vitro Digested Anthocyanin-Rich Extract on Intestinal Epithelial Cells Exposed to TNF-α

by Antonio Speciale, Romina Bashllari, Claudia Muscarà, Maria Sofia Molonia, Antonella Saija, Shikha Saha, Peter J. Wilde and Francesco Cimino

Molecules 2022, 27(17), 5368; https://doi.org/10.3390/molecules27175368 - 23 Aug 2022

Cited by 13 | Viewed by 2598

Abstract

Background: The consumption of foods rich in anthocyanins (ACN) have been associated with beneficial properties in chronic inflammatory disorders such as intestinal bowel diseases (IBD). These effects were attributed not only to a direct antioxidant mechanism but also to the modulation of cell [...] Read more.

Background: The consumption of foods rich in anthocyanins (ACN) have been associated with beneficial properties in chronic inflammatory disorders such as intestinal bowel diseases (IBD). These effects were attributed not only to a direct antioxidant mechanism but also to the modulation of cell redox-dependent signaling. However, ACN bioavailability is low for their poor stability in the digestive tract, so ACN gastrointestinal digestion should be considered. Methods: To have a more realistic knowledge of the effects of ACN, we performed an in vitro simulated gastrointestinal digestion of an ACN-rich purified and standardized bilberry and blackcurrant extract (BBE), followed by an evaluation of ACN composition modification (HPLC-DAD and pH differential method) and antioxidant activity (FRAP assay). Then, we studied the effects of BBE gastrointestinal extract on Caco-2 exposed to TNF-α. Results: The results confirmed the high instability of ACN in the mild alkaline environment of the small intestine (17% recovery index). However, the digested BBE maintained part of its bioactivity. Additionally, BBE gastrointestinal extract inhibited the TNF-α-induced NF-κB pathway in Caco-2 and activated the Nrf2 pathway. Conclusions: Although ACN stability is affected by gastrointestinal digestion, the anti-inflammatory and antioxidant activity of digested extracts were confirmed; thus, the loss of ACN can probably be counterweighed by their metabolites. Then, ACN introduced by diet or food supplements could represent an approach for IBD prevention. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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Review

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64 pages, 1855 KiB

Open AccessReview

Advances in the Chemistry, Analysis and Adulteration of Anthocyanin Rich-Berries and Fruits: 2000–2022

by Bharathi Avula, Kumar Katragunta, Ahmed G. Osman, Zulfiqar Ali, Sebastian John Adams, Amar G. Chittiboyina and Ikhlas A. Khan

Molecules 2023, 28(2), 560; https://doi.org/10.3390/molecules28020560 - 5 Jan 2023

Cited by 21 | Viewed by 4177

Abstract

Anthocyanins are reported to exhibit a wide variety of remedial qualities against many human disorders, including antioxidative stress, anti-inflammatory activity, amelioration of cardiovascular diseases, improvement of cognitive decline, and are touted to protect against neurodegenerative disorders. Anthocyanins are water soluble naturally occurring polyphenols [...] Read more.

Anthocyanins are reported to exhibit a wide variety of remedial qualities against many human disorders, including antioxidative stress, anti-inflammatory activity, amelioration of cardiovascular diseases, improvement of cognitive decline, and are touted to protect against neurodegenerative disorders. Anthocyanins are water soluble naturally occurring polyphenols containing sugar moiety and are found abundantly in colored fruits/berries. Various chromatographic (HPLC/HPTLC) and spectroscopic (IR, NMR) techniques as standalone or in hyphenated forms such as LC-MS/LC-NMR are routinely used to gauge the chemical composition and ensure the overall quality of anthocyanins in berries, fruits, and finished products. The major emphasis of the current review is to compile and disseminate various analytical methodologies on characterization, quantification, and chemical profiling of the whole array of anthocyanins in berries, and fruits within the last two decades. In addition, the factors affecting the stability of anthocyanins, including pH, light exposure, solvents, metal ions, and the presence of other substances, such as enzymes and proteins, were addressed. Several sources of anthocyanins, including berries and fruit with their botanical identity and respective yields of anthocyanins, were covered. In addition to chemical characterization, economically motivated adulteration of anthocyanin-rich fruits and berries due to increasing consumer demand will also be the subject of discussion. Finally, the health benefits and the medicinal utilities of anthocyanins were briefly discussed. A literature search was performed using electronic databases from PubMed, Science Direct, SciFinder, and Google Scholar, and the search was conducted covering the period from January 2000 to November 2022. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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14 pages, 667 KiB

Open AccessReview

Potential Benefits of Anthocyanins in Chronic Disorders of the Central Nervous System

by Sunil K. Panchal and Lindsay Brown

Molecules 2023, 28(1), 80; https://doi.org/10.3390/molecules28010080 - 22 Dec 2022

Cited by 6 | Viewed by 3773

Abstract

Anthocyanins have been shown to be effective in chronic diseases because of their antioxidant and anti-inflammatory effects together with changes in the gut microbiota and modulation of neuropeptides such as insulin-like growth factor-1. This review will examine whether these mechanisms may be effective [...] Read more.

Anthocyanins have been shown to be effective in chronic diseases because of their antioxidant and anti-inflammatory effects together with changes in the gut microbiota and modulation of neuropeptides such as insulin-like growth factor-1. This review will examine whether these mechanisms may be effective to moderate the symptoms of disorders of the central nervous system in humans, including schizophrenia, Parkinson’s disease, Alzheimer’s disease, autism spectrum disorder, depression, anxiety, attention-deficit hyperactivity disorder and epilepsy. Thus, anthocyanins from fruits and berries should be considered as complementary interventions to improve these chronic disorders. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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29 pages, 2015 KiB

Open AccessReview

Maize Flavonoid Biosynthesis, Regulation, and Human Health Relevance: A Review

by Héctor A. Peniche-Pavía, Tereso J. Guzmán, Jesús M. Magaña-Cerino, Carmen M. Gurrola-Díaz and Axel Tiessen

Molecules 2022, 27(16), 5166; https://doi.org/10.3390/molecules27165166 - 13 Aug 2022

Cited by 21 | Viewed by 4089

Abstract

Maize is one of the most important crops for human and animal consumption and contains a chemical arsenal essential for survival: flavonoids. Moreover, flavonoids are well known for their beneficial effects on human health. In this review, we decided to organize the information [...] Read more.

Maize is one of the most important crops for human and animal consumption and contains a chemical arsenal essential for survival: flavonoids. Moreover, flavonoids are well known for their beneficial effects on human health. In this review, we decided to organize the information about maize flavonoids into three sections. In the first section, we include updated information about the enzymatic pathway of maize flavonoids. We describe a total of twenty-one genes for the flavonoid pathway of maize. The first three genes participate in the general phenylpropanoid pathway. Four genes are common biosynthetic early genes for flavonoids, and fourteen are specific genes for the flavonoid subgroups, the anthocyanins, and flavone C-glycosides. The second section explains the tissue accumulation and regulation of flavonoids by environmental factors affecting the expression of the MYB-bHLH-WD40 (MBW) transcriptional complex. The study of transcription factors of the MBW complex is fundamental for understanding how the flavonoid profiles generate a palette of colors in the plant tissues. Finally, we also include an update of the biological activities of C3G, the major maize anthocyanin, including anticancer, antidiabetic, and antioxidant effects, among others. This review intends to disclose and integrate the existing knowledge regarding maize flavonoid pigmentation and its relevance in the human health sector. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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17 pages, 5252 KiB

Open AccessReview

Anthocyanin Pigments: Beyond Aesthetics

by Bindhu Alappat and Jayaraj Alappat

Molecules 2020, 25(23), 5500; https://doi.org/10.3390/molecules25235500 - 24 Nov 2020

Cited by 195 | Viewed by 21712

Abstract

Anthocyanins are polyphenol compounds that render various hues of pink, red, purple, and blue in flowers, vegetables, and fruits. Anthocyanins also play significant roles in plant propagation, ecophysiology, and plant defense mechanisms. Structurally, anthocyanins are anthocyanidins modified by sugars and acyl acids. Anthocyanin [...] Read more.

Anthocyanins are polyphenol compounds that render various hues of pink, red, purple, and blue in flowers, vegetables, and fruits. Anthocyanins also play significant roles in plant propagation, ecophysiology, and plant defense mechanisms. Structurally, anthocyanins are anthocyanidins modified by sugars and acyl acids. Anthocyanin colors are susceptible to pH, light, temperatures, and metal ions. The stability of anthocyanins is controlled by various factors, including inter and intramolecular complexations. Chromatographic and spectrometric methods have been extensively used for the extraction, isolation, and identification of anthocyanins. Anthocyanins play a major role in the pharmaceutical; nutraceutical; and food coloring, flavoring, and preserving industries. Research in these areas has not satisfied the urge for natural and sustainable colors and supplemental products. The lability of anthocyanins under various formulated conditions is the primary reason for this delay. New gene editing technologies to modify anthocyanin structures in vivo and the structural modification of anthocyanin via semi-synthetic methods offer new opportunities in this area. This review focusses on the biogenetics of anthocyanins; their colors, structural modifications, and stability; their various applications in human health and welfare; and advances in the field. Full article

(This article belongs to the Special Issue Anthocyanins: The Infinite Properties of These Incredible Compounds)

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