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Bioactive Phenolics and Polyphenols 2022

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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 (15 January 2023) | Viewed by 26852

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Prof. Dr. Davide Barreca

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Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, 98168 Messina, Italy
Interests: plant biochemistry; isolation and identification of polyphenols; evaluation of biological potentials of polyphenols on isolate cells in culture; identification of molecular mechanisms of antioxidants action
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Special Issue Information

Dear Colleagues,

This Special Issue, "Bioactive Phenolics and Polyphenols 2021", which is the third volume of our previous Special Issue "Bioactive Phenolics and Polyphenols 2018" (https://www.mdpi.com/journal/ijms/special_issues/bioactive_phenolics), will cover a selection of recent research topics and current review articles in the field of bioactive phenolics and polyphenols. Experimental papers, up-to-date review articles, and commentaries are all welcome.

The scientific interest in plant phenolics as chemopreventive and therapeutic agents against chronic and degenerative diseases has been increasing since the late 1990s, when the French paradox was associated with the high intake of polyphenols present in red wine. Since then, research advances include their biosynthesis, biological activities, purification, and chemical characterization in different plant species. Furthermore, research on the stability of phenolics in food processing techniques and storage is an area of major interest.

Contributions to this Special Issue may cover all aspects of phenolics and polyphenols including not only their chemical characterization on different plant species and methods for their extraction, purification, and quantification, but also elucidation of their mechanism of action; development of innovative methods for the evaluation of their bioactivity in vitro and in vivo; evaluation of their stability to thermal and non-thermal food processing techniques; elicitation of plant phenolic biosynthesis pathway; and effect of postharvest handling on the phenolic profiles of plant foods. Papers regarding the development of food products and dietary supplements enriched with plant phenolics will be also taken into consideration.

Prof. Dr. Davide Barreca
Guest Editor

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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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

phenolic metabolism
biological activities
stability to food processing
elicitation
methods of analysis
dietary supplements
nutraceutical ingredients
non-thermal processing
extraction and purification

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Published Papers (8 papers)

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14 pages, 1789 KiB

Open AccessArticle

A Comparative Study of Binding Interactions between Proteins and Flavonoids in Angelica Keiskei: Stability, α-Glucosidase Inhibition and Interaction Mechanisms

by Rui Wang, Lanlan Tu, Daodong Pan, Xinchang Gao, Lihui Du, Zhendong Cai, Jinhong Wu and Yali Dang

Int. J. Mol. Sci. 2023, 24(7), 6582; https://doi.org/10.3390/ijms24076582 - 1 Apr 2023

Cited by 3 | Viewed by 2231

Abstract

Flavonoids are easily destroyed and their activity lost during gastrointestinal digestion. Protein-based nanocomplexes, a delivery system that promotes nutrient stability and bioactivity, have received increasing attention in recent years. This study investigated the stability, inhibitory activity against α-glucosidase and interaction mechanisms of protein-based nanocomplexes combining whey protein isolate (WPI), soybean protein isolate (SPI) and bovine serum albumin (BSA) with flavonoids (F) from A. keiskei using spectrophotometry, fluorescence spectra and molecular docking approaches. The results show that the flavonoid content of WPI-F (23.17 ± 0.86 mg/g) was higher than those of SPI-F (19.41 ± 0.56 mg/g) and BSA-F (20.15 ± 0.62 mg/g) after simulated digestion in vitro. Furthermore, the inhibition rate of WPI-F (23.63 ± 0.02%) against α-glucosidase was also better than those of SPI-F (18.56 ± 0.02%) and BSA-F (21.62 ± 0.02%). The inhibition rate of WPI-F increased to nearly double that of F alone (12.43 ± 0.02%) (p < 0.05). Molecular docking results indicated that the protein-flavonoids (P-F) binding occurs primarily through hydrophobic forces, hydrogen bonds and ionic bonds. Thermodynamic analysis (ΔH > 0, ΔS > 0) indicated that the P-F interactions are predominantly hydrophobic forces. In addition, the absolute value of ΔG for WPI-F is greater (−30.22 ± 2.69 kJ mol⁻¹), indicating that WPI-F releases more heat energy when synthesized and is more conducive to combination. This paper serves as a valuable reference for the stability and bioactivity of flavonoids from A. keiskei. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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16 pages, 7810 KiB

Open AccessArticle

Therapeutic Potential of Linearol in Combination with Radiotherapy for the Treatment of Glioblastoma In Vitro

by Vasiliki Zoi, Theodora Papagrigoriou, Olga S. Tsiftsoglou, George A. Alexiou, Maria Giannakopoulou, Eftychia Tzima, Pericles Tsekeris, Anastasia Zikou, Athanasios P. Kyritsis, Diamanto Lazari and Vasiliki Galani

Int. J. Mol. Sci. 2023, 24(4), 3760; https://doi.org/10.3390/ijms24043760 - 13 Feb 2023

Cited by 2 | Viewed by 2169

Abstract

Glioblastoma is one of the most malignant and lethal forms of primary brain tumors in adults. Linearol, a kaurane diterpene isolated from different medicinal plants, including those of the genus Sideritis, has been found to possess significant anti-oxidant, anti-inflammatory and anti-microbial properties. In this study, we aimed to determine whether linearol could exhibit anti-glioma effects when given alone or in combination with radiotherapy in two human glioma cell lines, U87 and T98. Cell viability was examined with the Trypan Blue Exclusion assay, cell cycle distribution was tested with flow cytometry, and the synergistic effects of the combination treatment were analyzed with CompuSyn software. Linearol significantly suppressed cell proliferation and blocked cell cycle at the S phase. Furthermore, pretreatment of T98 cells with increasing linearol concentrations before exposure to 2 Gy irradiation decreased cell viability to a higher extent than linearol or radiation treatment alone, whereas in the U87 cells, an antagonistic relationship was observed between radiation and linearol. Moreover, linearol inhibited cell migration in both tested cell lines. Our results demonstrate for the first time that linearol is a promising anti-glioma agent and further studies are needed to fully understand the underlying mechanism of this effect. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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23 pages, 41134 KiB

Open AccessArticle

Xanthones from Gentianella acuta (Michx.) Hulten Ameliorate Colorectal Carcinoma via the PI3K/Akt/mTOR Signaling Pathway

by Meng-Qi Lu, Jing-Ya Ruan, Hui-Min Li, Ding-Shan Yang, Yan-Xia Liu, Mi-Mi Hao, Hai-Yang Yu, Yi Zhang and Tao Wang

Int. J. Mol. Sci. 2023, 24(3), 2279; https://doi.org/10.3390/ijms24032279 - 23 Jan 2023

Cited by 3 | Viewed by 2227

Abstract

Colorectal carcinoma (CRC) is a kind of malignant tumor closely related to ulcerative colitis. Xanthone derivatives are one of the most promising therapeutic drugs which have been used in phase I/II clinical trials for cancer therapy. Our previous study indicated that the aerial parts of Gentianella acuta Michx. Hulten (GA) was rich in xanthones and showed a good therapeutic effect on ulcerative colitis in mice, suggesting that GA xanthones might have some therapeutic or ameliorative effects on CRC. However, no relevant study has been reported. This study aims to find the effective substances of GA inhibiting CRC and clarify their mechanism. Solvent extraction, column chromatographic separation, and LC-MS analysis were used to characterize the 70% EtOH extract of GA and track xanthones abundant fraction XF. MTT assay was carried out to clarify the activity of GA fractions; the result showed XF to be the main active fraction. LC-MS analysis was executed to characterize XF, 38 xanthones were identified. Network pharmacology prediction, in vitro activity screening, and molecular docking assay were combined to predict the potential mechanism; the PI3K/Akt/mTOR signaling pathway was found to be most important. Western blot assay on the main active xanthones 1,3,5-trihydroxyxanthone (16), 1,3,5,8-tetrahydroxyxanthone (17), 1,5,8-trihydroxy-3-methoxyxanthone (18), and 1,7-dihydroxy-3,8-dimethoxyxanthone (19) was used to verify the above prediction; these xanthones were found to inhibit the PI3K/Akt/mTOR signaling pathway, and 17 played a significant role among them through Western blot assay using PI3K/AKT/mTOR agonist IGF-1. In conclusion, this study demonstrated that GA xanthones were effective compounds of GA inhibiting CRC by regulating PI3K/Akt/mTOR signaling pathway transduction, at least. Importantly, 1,3,5,8-tetrahydroxyxanthone (17), the most abundant active xanthone in GA, might be a candidate drug for CRC. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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17 pages, 2812 KiB

Open AccessArticle

Polysaccharides from European Black Elderberry Extract Enhance Dendritic Cell Mediated T Cell Immune Responses

by Lena Stich, Stephan Plattner, Gordon McDougall, Ceri Austin and Alexander Steinkasserer

Int. J. Mol. Sci. 2022, 23(7), 3949; https://doi.org/10.3390/ijms23073949 - 1 Apr 2022

Cited by 7 | Viewed by 4366

Abstract

European black elderberry (Sambucus nigra L.) is a popular way to treat common colds or influenza infections. Mechanistically, this might be due to a direct antiviral effect or a stimulatory effect on the immune system of the host. Here, we evaluated the modulatory effects of black elderberry derived water extract (EC15) and its polysaccharide enriched fractions (CPS, BOUND, and UNBOUND) in comparison to a conventional alcoholic extract (EE25), regarding the phenotypical and functional properties of dendritic cells (DCs), which are essential cells to induce potent T cell responses. Interestingly, the water extract and its polysaccharide fractions potently induced DC maturation, while the ethanol extract did not. Moreover, the capacity to stimulate T cells by these matured DCs, as assessed using MLR assays, was statistically higher when induced by the water extracted fractions, compared to immature DCs. On the other hand, the ethanol extract EE25 did not induce T cell stimulation. Finally, the cytokine expression profiles of these DC—T cell cocultures were assessed and correlated well with increased T cell stimulation. Also, the expression of inflammatory cytokines, such as IL-6, TNF-α, and IFN-γ was highly increased in the presence of the elderberry water extract EC15, and the polysaccharide enriched CPS, BOUND, and UNBOUND fractions, but not by EE25. Thus, from these data, we conclude that the polysaccharides present in water-derived elderberry fractions induce potent immune-modulatory effects, which represents the basis for a strong immune-mediated response to viruses including influenza. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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29 pages, 3876 KiB

Open AccessArticle

Caffeic Acid/Eu(III) Complexes: Solution Equilibrium Studies, Structure Characterization and Biological Activity

by Żaneta Arciszewska, Sofia Gama, Monika Kalinowska, Grzegorz Świderski, Renata Świsłocka, Ewelina Gołębiewska, Monika Naumowicz, Mateusz Worobiczuk, Adam Cudowski, Anna Pietryczuk, Concetta De Stefano, Demetrio Milea, Włodzimierz Lewandowski and Beata Godlewska-Żyłkiewicz

Int. J. Mol. Sci. 2022, 23(2), 888; https://doi.org/10.3390/ijms23020888 - 14 Jan 2022

Cited by 18 | Viewed by 3768

Abstract

Caffeic acid (CFA) is one of the various natural antioxidants and chemoprotective agents occurring in the human diet. In addition, its metal complexes play fundamental roles in biological systems. Nevertheless, research on the properties of CFA with lanthanide metals is very scarce, and little to no chemical or biological information is known about these particular systems. Most of their properties, including their biological activity and environmental impact, strictly depend on their structure, stability, and solution behaviour. In this work, a multi-analytical-technique approach was used to study these relationships for the Eu(III)/CFA complex. The synthesized metal complex was studied by FT-IR, FT-Raman, elemental, and thermal (TGA) analysis. In order to examine the chemical speciation of the Eu(III)/CFA system in an aqueous solution, several independent potentiometric and spectrophotometric UV-Vis titrations were performed at different M:L (metal:ligand) and pH ratios. The general molecular formula of the synthesized metal complex in the solid state was [Eu(CFA)₃(H₂O)₃]∙2H₂O (M:L ratio 1:3), while in aqueous solution the 1:1 species were observed at the optimum pH of 6 ≤ pH ≤ 10, ([Eu(CFA)] and [Eu(CFA)(OH)]⁻). These results were confirmed by ¹H-NMR experiments and electrospray-ionization mass spectrometry (ESI-MS). To evaluate the interaction of Eu(III)/CFA and CFA alone with cell membranes, electrophoretic mobility assays were used. Various antioxidant tests have shown that Eu(III)/CFA exhibits lower antioxidant activity than the free CFA ligand. In addition, the antimicrobial properties of Eu(III)/CFA and CFA against Escherichia coli, Bacillus subtilis and Candida albicans were investigated by evaluation of the minimum inhibitory concentration (MIC). Eu(III)/CFA shows higher antibacterial activity against bacteria compared to CFA, which can be explained by the highly probable increased lipophilicity of the Eu(III) complex. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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21 pages, 10453 KiB

Open AccessArticle

Screening for the Active Anti-Inflammatory and Antioxidant Polyphenols of Gaultheria procumbens and Their Application for Standardisation: From Identification through Cellular Studies to Quantitative Determination

by Monika Anna Olszewska, Aleksandra Owczarek, Anna Magiera, Sebastian Granica and Piotr Michel

Int. J. Mol. Sci. 2021, 22(21), 11532; https://doi.org/10.3390/ijms222111532 - 26 Oct 2021

Cited by 9 | Viewed by 2731

Abstract

Aerial parts, leaves, and stems of Gaultheria procumbens are polyphenol-rich herbal medicines with anti-inflammatory and antioxidant effects. The present study focused on identifying active markers of the G. procumbens extracts in an integrated approach combining phytochemical and biological capacity tests. The target compounds, representing all classes of Gaultheria polyphenols, were pre-selected by LC-ESI-PDA-MS/MS. For unambiguous identification, the key analytes, including a rare procyanidin trimer (cinnamtannin B-1), miquelianin potassium salt, and two new natural products: quercetin and kaempferol 3-O-β-d-xylopyranosyl-(1→2)-β-d-glucuronopyranosides, were isolated by preparative HPLC and investigated by spectroscopy (HR-ESI-MS, UV-vis, CD, 1D- and 2D-NMR), thiolysis, flame photometry, optical rotation experiments, and absolute configuration studies. The significant contribution of the pre-selected compounds to the biological effects of the extracts was confirmed in vitro: the analytes significantly and in a dose-dependent manner down-regulated the pro-oxidant and pro-inflammatory functions of human neutrophils ex vivo (inhibited the release of reactive oxygen species, IL-1β, TNF-α, and neutrophils elastase, ELA-2), inhibited two key pro-inflammatory enzymes (cyclooxygenase, COX-2, and hyaluronidase), and most of them, except gaultherin, exerted potent direct antioxidant activity (ferric reducing antioxidant power and superoxide anion scavenging capacity). Moreover, cellular safety was confirmed for all compounds by flow cytometry. Eventually, as these mechanisms have been connected to the health benefits of G. procumbens, 11 polyphenols were accepted as active markers, and a simple, accurate, reproducible, and fully validated RP-HPLC-PDA method for standardisation of the target extracts was proposed. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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Review

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14 pages, 1063 KiB

Open AccessReview

Edible Bioactive Film with Curcumin: A Potential “Functional” Packaging?

by Josemar Gonçalves Oliveira Filho and Mariana Buranelo Egea

Int. J. Mol. Sci. 2022, 23(10), 5638; https://doi.org/10.3390/ijms23105638 - 18 May 2022

Cited by 17 | Viewed by 4024

Abstract

Edible packaging has been developed as a biodegradable and non-toxic alternative to traditional petroleum-based food packaging. Biopolymeric edible films, in addition to their passive protective function, may also play a bioactive role as vehicles for bioactive compounds of importance to human health. In recent years, a new generation of edible food packaging has been developed to incorporate ingredients with functional potential that have beneficial effects on consumer health. Curcumin, a bioactive compound widely used as a natural dye obtained from turmeric rhizomes (Curcuma longa L.), has a broad spectrum of beneficial properties for human health, such as anti-inflammatory, anti-hypertensive, antioxidant, anti-cancer, and other activities. To demonstrate these properties, curcumin has been explored as a bioactive agent for the development of bioactive packaging, which can be referred to as functional packaging and used in food. The aim of this review was to describe the current and potential research on the development of functional-edible-films incorporating curcumin for applications such as food packaging. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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19 pages, 1633 KiB

Open AccessReview

Biotechnological Applications and Health-Promoting Properties of Flavonols: An Updated View

by Teresa Gervasi, Antonella Calderaro, Davide Barreca, Ester Tellone, Domenico Trombetta, Silvana Ficarra, Antonella Smeriglio, Giuseppina Mandalari and Giuseppe Gattuso

Int. J. Mol. Sci. 2022, 23(3), 1710; https://doi.org/10.3390/ijms23031710 - 1 Feb 2022

Cited by 30 | Viewed by 3561

Abstract

Flavonols are a subclass of natural flavonoids characterized by a remarkable number of biotechnological applications and health-promoting properties. They attract researchers’ attention due to many epidemiological studies supporting their usage. They are phytochemicals commonly present in our diet, being ubiquitous in the plant kingdom and, in particular, relatively very abundant in fruits and vegetables. All these aspects make flavonols candidates of choice for the valorization of products, based on the presence of a remarkable number of different chemical structures, each one characterized by specific chemical features capable of influencing biological targets inside the living organisms in very different manners. In this review, we analyzed the biochemical and physiological characteristics of flavonols focalizing our attention on the most promising compounds to shed some light on their increasing utilization in biotechnological applications in processing industries, as well as their suitable employment to improve the overall wellness of the humankind. Full article

(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2022)

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