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Polyphenols and Their Transformation Products: Properties and Mechanism of Action

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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: 20 February 2025 | Viewed by 11546

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Special Issue Editors

Dr. Yuri Shatalin

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Guest Editor

Institute of Theoretical and Experimental Biophysics, Russian Academy of Sciences, 142290 Pushchino, Russia
Interests: natural compounds; cell death; oxidative stress; natural compound analogs; structure-activity relationship

Prof. Dr. Konstantin Belosludtsev

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Guest Editor

Institute of Theoretical and Experimental Biophysics, Russian Academy of Sciences, Institutskaya 3, 142290 Pushchino, Russia
Interests: mitochondria; biophysics; diabetes mellitus; myopathy; mitochondrial Ca²⁺ transport; permeability transition pore; oxidative stress; reactive oxygen species; lipids; membrane proteins; liposomes
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Dear Colleagues,

Polyphenols are secondary metabolites in plants. These compounds are found in plant-based foods and beverages and are an integral part of our diet. The consumption of polyphenols or their sources may be associated with a reduced risk of a number of diseases, including cardiovascular, neurodegenerative and other diseases. These compounds exhibit a variety of biological activities, including antioxidant, anti-inﬂammatory, antidiabetic, antibacterial and anticarcinogenic activities. During the storage, processing and digestion, polyphenols undergo various modifications. In particular, they interact with compounds present in food, are metabolized by the microbiota of the gastrointestinal tract and/or transform inside the cells. As a result, a wide range of transformation products of polyphenols are formed. The properties of these compounds and their impact on health remain largely unknown.

This Special Issue focuses on the mechanisms underlying the effects of polyphenols on human health, with special attention to their transformation products. We welcome comprehensive reviews and original research papers.

Potential topics include, but are not limited to:

Transformation products of polyphenols formed in real foods and in vivo;
Properties of polyphenols and their transformation products;
Biological activity of polyphenols and their products;
Potential cytotoxic effects of these compounds;
Mechanisms underlying the effects of polyphenols and their products;
Future perspective of these compounds in medicine.

Dr. Yuri Shatalin
Prof. Dr. Konstantin Belosludtsev
Guest Editors

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Keywords

polyphenols
transformation products
Biological activity
cytotoxic effects
mechanism of action
health effect

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Published Papers (7 papers)

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Research

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44 pages, 20348 KiB

Open AccessArticle

Testing Green Tea Extract and Ammonium Salts as Stimulants of Physical Performance in a Forced Swimming Rat Experimental Model

by Ekaterina A. Korf, Artem V. Novozhilov, Igor V. Mindukshev, Andrey S. Glotov, Igor V. Kudryavtsev, Ekaterina V. Baidyuk, Irina A. Dobrylko, Natalia G. Voitenko, Polina A. Voronina, Samarmar Habeeb, Afrah Ghanem, Natalia S. Osinovskaya, Maria K. Serebryakova, Denis V. Krivorotov, Richard O. Jenkins and Nikolay V. Goncharov

Int. J. Mol. Sci. 2024, 25(19), 10438; https://doi.org/10.3390/ijms251910438 - 27 Sep 2024

Viewed by 862

Abstract

The study of drugs of natural origin that increase endurance and/or accelerate recovery is an integral part of sports medicine and physiology. In this paper, decaffeinated green tea extract (GTE) and two ammonium salts—chloride (ACL) and carbonate (ACR)—were tested individually and in combination with GTE as stimulants of physical performance in a forced swimming rat experimental model. The determined parameters can be divided into seven blocks: functional (swimming duration); biochemistry of blood plasma; biochemistry of erythrocytes; hematology; immunology; gene expression of slow- and fast-twitch muscles (m. soleus, SOL, and m. extensor digitorum longus, EDL, respectively); and morphometric indicators of slow- and fast-twitch muscles. Regarding the negative control (intact animals), the maximum number of changes in all blocks of indicators was recorded in the GTE + ACR group, whose animals showed the maximum functional result and minimum lactate values on the last day of the experiment. Next, in terms of the number of changes, were the groups ACR, ACL, GTE + ACL, GTE and NaCl (positive control). In general, the number of identified adaptive changes was proportional to the functional state of the animals of the corresponding groups, in terms of the duration of the swimming load in the last four days of the experiment. However, not only the total number but also the qualitative composition of the identified changes is of interest. The results of a comparative analysis suggest that, in the model of forced swimming we developed, GTE promotes restoration of the body and moderate mobilization of the immune system, while small doses of ammonium salts, especially ammonium carbonate, contribute to an increase in physical performance, which is associated with satisfactory restoration of skeletal muscles and the entire body. The combined use of GTE with ammonium salts does not give a clearly positive effect. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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31 pages, 4064 KiB

Open AccessArticle

Genus Ribes: Ribes aureum, Ribes pauciflorum, Ribes triste, and Ribes dikuscha—Comparative Mass Spectrometric Study of Polyphenolic Composition and Other Bioactive Constituents

by Mayya P. Razgonova, Muhammad Amjad Nawaz, Andrey S. Sabitov and Kirill S. Golokhvast

Int. J. Mol. Sci. 2024, 25(18), 10085; https://doi.org/10.3390/ijms251810085 - 19 Sep 2024

Viewed by 737

Abstract

This study presents the metabolomic profiles of the four Ribes species (Ribes pauciflorum Turcz., Ribes triste Pall., Ribes dicuscha Fisch., and Ribes aureum Purch.). The plant material was collected during two expeditions in the Russian Far East. Tandem mass spectrometry was used to detect target analytes. A total of 205 bioactive compounds (155 compounds from polyphenol group and 50 compounds from other chemical groups) were tentatively identified from the berries and extracts of the four Ribes species. For the first time, 29 chemical constituents from the polyphenol group were tentatively identified in the genus Ribes. The newly identified polyphenols include flavones, flavonols, flavan-3-ols, lignans, coumarins, stilbenes, and others. The other newly detected compounds in Ribes species are the naphthoquinone group (1,8-dihydroxy-anthraquinone, 1,3,6,8-tetrahydroxy-9(10H)-anthracenone, 8,8′-dihydroxy-2,2′-binaphthalene-1,1′,4,4′-tetrone, etc.), polyhydroxycarboxylic acids, omega-3 fatty acids (stearidonic acid, linolenic acid), and others. Our results imply that Ribes species are rich in polyphenols, especially flavanols, anthocyanins, flavones, and flavan-3-ols. These results indicate the utility of Ribes species for the health and pharmaceutical industry. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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17 pages, 7719 KiB

Open AccessArticle

UHPLC-DAD/ESI-TOF-MS Phytochemical Characterization and Evaluation of the Impact of Eleutherococcus senticosus Fruit Intractum on Biochemical, Hepatological, and Blood Parameters in Balb/c Mice

by Filip Graczyk, Jakub Gębalski, Dorota Sulejczak, Milena Małkowska, Magdalena Wójciak, Dorota Gawenda-Kempczyńska, Elżbieta Piskorska, Krystian Krolik, Maciej Markiewicz, Aneta Kondrzycka-Dąda, Wiktoria Lepianka, Grzegorz Borowski, Marcin Feldo, Robert Verporte and Daniel Załuski

Int. J. Mol. Sci. 2024, 25(17), 9295; https://doi.org/10.3390/ijms25179295 - 27 Aug 2024

Viewed by 829

Abstract

Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. (ES) has gained popularity for its adaptogenic, immunostimulant, and anti-inflammatory properties. Because of overexploitation of the roots, the species is considered to be endangered and has been put on the Red List in some countries (e.g., the Republic of Korea). Therefore, the fruits of E. senticosus might be explored as a new sustainable source of compounds with adaptogenic activity. This study aimed to assess the chemical composition and the safety profile (hepatotoxicity, blood morphology, biochemical parameters of blood plasma) of E. senticosus fruit intractum in Balb/c mice after oral administration of 750 and 1500 mg/kg b.w. UHPLC analysis coupled with DAD and MS detectors was used to quantify the metabolites. For the first time, oleanolic and ursolic acids were quantified in the intractum (16.01 ± 1.3 and 2.21 ± 0.17 µg/g of oleanolic and ursolic acids, respectively). Regarding polyphenols, chlorogenic acid (0.92 mg/g of dried extract), caffeic acid (0.43 mg/g), dicaffeoylquinic acids (in total: 1.27 mg/g), and an unidentified caffeic acid ester (0.81 mg/g) were identified. The results in Balb/c mice revealed that the intractum does not cause significant variations in red blood cells parameters. In turn, a significant decrease in the total number of leukocytes was observed (5.8 × 10³ µL), with a percentage increase in lymphocytes among the groups (80.2, 81.8, and 82.6). The ability of the intractum to decrease alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels may indicate its anti-inflammatory activity. Our observations justify that the fruits of E. senticosus are safe in the doses used and do not cause significant changes in the activity of the liver enzymes or in blood parameters. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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14 pages, 3239 KiB

Open AccessArticle

Comparative Analysis of Fluorescence Emission in Myricetin, Kaempferol, and Quercetin Powders and Solutions

by Alexandra Deriabina, Tatiana Prutskij, Hector Daniel Morales Ochoa, Eduardo Gonzalez Jimenez and Sergei Deriabin

Int. J. Mol. Sci. 2024, 25(5), 2558; https://doi.org/10.3390/ijms25052558 - 22 Feb 2024

Cited by 1 | Viewed by 1088

Abstract

Myricetin is a flavonol with high antioxidant properties. In this research, the fluorescence emission of myricetin powder and its solutions in different solvents were measured and analyzed by comparing with the results of calculations. Comparison of the calculated and measured characteristic wavelengths allowed the identification of all the spectral features in the fluorescence spectra of myricetin powder and solutions with different concentrations. The computation was based on modeling the process of the excited state intermolecular proton transfer, which predicts the formation of tautomeric forms of the flavonol molecule. Characteristic emission wavelengths were obtained using TDDFT/M06-2X/6-31++G(d,p). To understand the influence of the hydroxyl groups in the B-ring of the flavonol molecule on the emission spectrum, we also compared the fluorescence spectra of myricetin with those of kaempferol and quercetin. Moreover, based on the analysis of the changes in the shape of the FL spectra with the concentration of the solution, a criterion for the complete dissolution of the flavonol powders was established, which is important for bioavailability of flavonoids. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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10 pages, 5721 KiB

Open AccessCommunication

Identification of One O-Methyltransferase Gene Involved in Methylated Flavonoid Biosynthesis Related to the UV-B Irradiation Response in Euphorbia lathyris

by Wanli Zhao, Long Huang, Shu Xu, Junzhi Wu, Fan Wang, Pirui Li, Linwei Li, Mei Tian, Xu Feng and Yu Chen

Int. J. Mol. Sci. 2024, 25(2), 782; https://doi.org/10.3390/ijms25020782 - 8 Jan 2024

Cited by 1 | Viewed by 1175

Abstract

Flavonoids are ubiquitous polyphenolic compounds that play a vital role in plants’ defense response and medicinal efficacy. UV-B radiation is a vital environmental regulator governing flavonoid biosynthesis in plants. Many plants rapidly biosynthesize flavonoids as a response to UV-B stress conditions. Here, we investigated the effects of flavonoid biosynthesis via UV-B irradiation in Euphorbia lathyris. We found that exposure of the E. lathyris callus to UV-B radiation sharply increased the level of one O-methyltransferase (ElOMT1) transcript and led to the biosynthesis of several methylated flavonoids. The methyltransferase ElOMT1 was expressed heterologously in E. coli, and we tested the catalytic activity of recombinant ElOMT1 with possible substrates, including caffeic acid, baicalin, and luteolin, in vitro. ElOMT1 could efficiently methylate when the hydroxyl groups were contained in the core nucleus of the flavonoid. This molecular characterization identifies a methyltransferase responsible for the chemical modification of the core flavonoid structure through methylation and helps reveal the mechanism of methylated flavonoid biosynthesis in Euphorbiaceae. This study identifies the O-methyltransferase that responds to UV-B irradiation and helps shed light on the mechanism of flavonoid biosynthesis in Euphorbia lathyris. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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22 pages, 3038 KiB

Open AccessArticle

A Comparative Study of the Inhibitory Effect of Some Flavonoids and a Conjugate of Taxifolin with Glyoxylic Acid on the Oxidative Burst of Neutrophils

by Victoria S. Shubina, Victoria I. Kozina and Yuri V. Shatalin

Int. J. Mol. Sci. 2023, 24(20), 15068; https://doi.org/10.3390/ijms242015068 - 11 Oct 2023

Cited by 5 | Viewed by 1438

Abstract

During the storage, processing, and digestion of flavonoid-rich foods and beverages, a condensation of flavonoids with toxic carbonyl compounds occurs. The effect of the resulting products on cells remains largely unknown. The aim of the present study was to evaluate the effects of quercetin, taxifolin, catechin, eriodictyol, hesperetin, naringenin, and a condensation product of taxifolin with glyoxylic acid on the oxidative burst of neutrophils. It was found that the flavonoids and the condensation product inhibited the total production of ROS. Flavonoids decreased both the intra and extracellular ROS production. The condensation product had no effect on intracellular ROS production but effectively inhibited the extracellular production of ROS. Thus, the condensation of flavonoids with toxic carbonyl compounds may lead to the formation of compounds exhibiting potent inhibitory effects on the oxidative burst of neutrophils. The data also suggest that, during these reactions, the influence of a fraction of flavonoids and their polyphenolic derivatives on cellular functions may change. On the whole, the results of the study provide a better understanding of the effects of polyphenols on human health. In addition, these results reveal the structure–activity relationship of these polyphenols and may be useful in a search for new therapeutic agents against diseases associated with oxidative stress. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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Review

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19 pages, 1722 KiB

Open AccessReview

Chemical Constituents of Stinging Nettle (Urtica dioica L.): A Comprehensive Review on Phenolic and Polyphenolic Compounds and Their Bioactivity

by Saša Đurović, Ivan Kojić, Danka Radić, Yulia A. Smyatskaya, Julia G. Bazarnova, Snežana Filip and Tomislav Tosti

Int. J. Mol. Sci. 2024, 25(6), 3430; https://doi.org/10.3390/ijms25063430 - 18 Mar 2024

Cited by 11 | Viewed by 3928

Abstract

Polyphenolic compounds are of great interest in today’s science. Naturally, they occur in plants and other sources in many different forms. Their wide range of biological activity has attracted the attention of the scientific community. One of the sources of phenolic compounds is stinging nettle (Urtica dioica L.), a common plant in almost all parts of the world. A long tradition of utilization and an interesting chemical profile make this plant a fascinating and extensive object of study. The chemical profile also allows this plant to be used as a food and a pigment source in the food, pharmaceutical, and cosmetic industries. Previously conducted studies found phenolic acids and polyphenolic compounds in root, stalk, and stinging nettle leaves. Different extraction techniques were usually used to isolate them from the leaves. Obtained extracts were used to investigate biological activity further or formulate different functional food products. This study aimed to collect all available knowledge about this plant, its chemical composition, and biological activity and to summarize this knowledge with particular attention to polyphenolic compounds and the activity and mechanisms of their actions. Full article

(This article belongs to the Special Issue Polyphenols and Their Transformation Products: Properties and Mechanism of Action)

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