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Bioactive Phenolic and Polyphenolic Compounds, Volume III

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

Deadline for manuscript submissions: 31 December 2025 | Viewed by 16001

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Dr. Cristina Forzato

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Department of Chemical and Pharmaceutical Sciences, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy
Interests: food chemistry; natural products; plant extracts; antioxidants; polyphenols; liquid chromatography; nuclear magnetic resonance; mass spectrometry; organic synthesis; sensors
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Dear Colleagues,

The plant kingdom is one of the richest reservoirs of organic compounds of different structures, called secondary metabolites, which are quite always unique for each species. Among the thousands of secondary metabolites present in plants, phenolic compounds are one of the wider classes synthetized. To this class of compounds belong those that possess one phenol ring, such as phenolic acids and phenolic alcohols, or more than one phenol ring, which are named polyphenols. They are considered excellent antioxidants and are related to the diminishment of risks of important chronic diseases. In addition, industrial agri-food wastes can be still rich in polyphenols and their recovery through different extraction techniques would help to reduce the environmental impact of these wastes. At the same time, they could have potential applications in the food, cosmetic, and pharmaceutical industries, contributing to the circular bio-economy.

Different extraction techniques can be used for the recovery of polyphenols and more efficient unconventional extraction techniques are also applied such as microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE), pulse-elec. Field extraction (PEFE), etc.

This Special Issue aims to collect original research articles and reviews dealing with the identification, extraction and quantification of bioactive phenolic and polyphenolic compounds in food and natural products. Papers focused on new analytical methodologies and sensor development for bioactive polyphenol identification will also be considered, as well as papers on new extraction techniques and biological activity studies.

I look forward to receiving your contributions.

Prof. Dr. Cristina Forzato
Guest Editor

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Keywords

food chemistry
natural products
antioxidants
polyphenols
chromatography
spectroscopy
mass spectrometry
extraction
biological activity
sensors

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Related Special Issues

Bioactive Phenolic and Polyphenolic Compounds in Molecules (35 articles)
Bioactive Phenolic and Polyphenolic Compounds-2nd Edition in Molecules (27 articles)

Published Papers (11 papers)

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Research

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19 pages, 2419 KiB

Open AccessArticle

Promiscuity in Polyphenol–Protein Interactions—Monitoring Protein Conformational Change upon Polyphenol–Protein Binding by Nano-Differential Fluorimetry (Nano-DSF)

by Dorothea Schmidt, Amelie Wohlers and Nikolai Kuhnert

Molecules 2025, 30(4), 965; https://doi.org/10.3390/molecules30040965 - 19 Feb 2025

Viewed by 467

Abstract

In this article, we introduce nano-differential fluorimetry (nano-DSF) as an analytical technique that is suitable for investigating polyphenol–protein interactions in solution. Nano-DSF monitors conformational changes in proteins induced by external agents upon interaction at the molecular level. We demonstrate the suitability of this technique to qualitatively monitor an interaction between selected dietary polyphenols and selected proteins including BSA, ovalbumin, amylase, pepsin, trypsin, mucin and ACE-1. Protein conformational changes induced by dietary polyphenols can be investigated. As a major advantage, measurements are carried out at a high dilution, avoiding the precipitation of polyphenol–protein complexes, allowing the rapid and efficient acquisition of quantitative and qualitative binding data. From this concentration, quantitative binding data could be obtained from the fluorescence response curve in line with published values for the association constants. We demonstrate that qualitative interactions can also be established for real food extracts such as cocoa, tea or coffee containing mixtures of dietary polyphenols. Most importantly, we demonstrate that polyphenols of very different structural classes interact with the same protein target. Conversely, multiple protein targets show an affinity to a series of structurally diverse polyphenols, therefore suggesting a dual level of promiscuity with respect to the protein target and polyphenol structure. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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15 pages, 2205 KiB

Open AccessArticle

Agathisflavone Inhibits Viability and Modulates the Expression of miR-125b, miR-155, IL-6, and Arginase in Glioblastoma Cells and Microglia/Macrophage Activation

by Karina Costa da Silva, Irlã Santos Lima, Cleonice Creusa dos Santos, Carolina Kymie Vasques Nonaka, Bruno Solano de Freitas Souza, Jorge Mauricio David, Henning Ulrich, Ravena Pereira do Nascimento, Maria de Fátima Dias Costa, Balbino Lino dos Santos and Silvia Lima Costa

Molecules 2025, 30(1), 158; https://doi.org/10.3390/molecules30010158 - 3 Jan 2025

Viewed by 1024

Abstract

Glioblastomas (GBM) are malignant tumours with poor prognosis. Treatment involves chemotherapy and/or radiotherapy; however, there is currently no standard treatment for recurrence, and prognosis remains unfavourable. Inflammatory mediators and microRNAs (miRNAs) influence the aggressiveness of GBM, being involved in the communication with the cells of the tumour parenchyma, including microglia/macrophages, and maintaining an immunosuppressive microenvironment. Hence, the modulation of miRNAs and inflammatory factors may improve GBM treatments. In this study, we investigated the effects of agathisflavone, a biflavonoid purified from Cenostigma pyramidale (Tul.), on the growth and migration of GBM cells, on the expression of inflammatory cytokines and microRNAs, as well on the response of microglia. Agathisflavone (5–30 μM) induced a dose- and time-dependent reduction in the viability of both human GL-15 and rat C6 cells, as determined by the MTT test, and reduced cell migration, as determined by cell scratch assay. RT-qPCR analysis revealed that agathisflavone (5 μM) down-regulated the expression of miR-125b and miR-155 in the secretome derived from GL-15 cells, which was associated with upregulation of the mRNA expression of IL-6 and arginase-1 immunoregulatory factors. Exposure of human microglia/macrophage to the secretome from GL-15 GMB cells modulated proliferation and morphology, effects that were modulated by agathisflavone treatment. These results demonstrate the effect of flavonoids on the growth of GBM cells, which impacts cells in the microenvironment and can be considered for preclinical studies for adjuvant treatments. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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16 pages, 2622 KiB

Open AccessArticle

The Influence of Basal Medium on Polyphenol Accumulation in Shoot Cultures of Clerodendrum trichotomum and Clerodendrum colebrookianum

by Jan Gomulski, Marta Krzemińska, Magdalena Jochymek, Anna K. Kiss and Izabela Grzegorczyk-Karolak

Molecules 2024, 29(24), 5983; https://doi.org/10.3390/molecules29245983 - 19 Dec 2024

Viewed by 751

Abstract

Plants of the Clerodendrum genus, known for their rich phytochemical profiles, are used in traditional Chinese, Korean, Japanese, and Indian medicine to treat various ailments, including inflammation, hypertension, diabetes, hyperlipidemia, and cancer. Due to the limited natural availability of these plants, there is a growing interest in utilizing in vitro culture techniques to produce their bioactive compounds sustainably. In this study, the effects are compared of Murashige and Skoog (MS), Woody Plant medium (WP), Gamborg B5 (B5), and Schenk and Hildebrandt (SH) basal media on growth, biomass accumulation, and polyphenolic compound production in shoot cultures of Clerodendrum colebrookianum and Clerodendrum trichotomum. The composition of the culture medium significantly influenced the growth and metabolic profiles of both species. C. trichotomum exhibited the highest proliferation potential on WP and SH media, while C. colebrookianum was similar on WP, SH, and B5 media (multiplication factor of about 20). Dry weight accumulation was highest in C. trichotomum grown on SH medium (0.292 g/culture), while C. colebrookianum achieved a comparable biomass on SH and WP media (0.240 g/culture and 0.228 g/culture, respectively). The chemical analysis showed similar secondary metabolite profiles between the two Clerodendrum species with phenylethanoids such as acteoside being the predominant bioactive compounds in hydromethanolic extracts. WP medium was the most favorable for polyphenol accumulation in C. colebrookianum (64.5 mg/g DW), while the SH medium yielded the highest total polyphenol content in C. trichotomum (36.6 mg/g DW). In this study, the importance is underscored of basal medium selection in optimizing the in vitro production of bioactive polyphenolic compounds in Clerodendrum species, providing a foundation for the sustainable and scalable production of these pharmacologically significant metabolites. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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14 pages, 2046 KiB

Open AccessArticle

Effect of Ag⁺ and Cd²⁺ Elicitation on Polyphenol Production in Shoot Culture of Dracocephalum ruyschiana L.

by Izabela Weremczuk-Jeżyna, Jan Gomulski, Anna K. Kiss and Izabela Grzegorczyk-Karolak

Molecules 2024, 29(22), 5263; https://doi.org/10.3390/molecules29225263 - 7 Nov 2024

Viewed by 1023

Abstract

Abiotic elicitation with heavy metals has demonstrated considerable potential to stimulate the production of industrially important secondary metabolites in plant in vitro cultures. The present study investigates the effect of exogenous silver nitrate and cadmium chloride supplementation on flavonoid and phenolic acid production, as well as other indicators of oxidative stress, in shoot cultures of Dracocephalum ruyschiana L. Owing to the presence of bioactive polyphenolic compounds, this Mongolian medicinal plant is traditionally used as an anti-inflammatory, antibacterial and antipyretic agent. The shoots were cultured for three weeks, and then, cadmium (Cd²⁺) and silver (Ag⁺) ions (50 or 100 µM) were added to the medium. The maximum proliferation rate was observed in the presence of 100 µM Ag⁺ (almost 5), the highest chlorophyll content in the presence of 100 µM Cd²⁺ (0.6 mg/g FW) and the highest biomass was observed with both these treatments (73.4–75.7 g FW and 7.53–7.72 g DW). UPLC-PDA-ESI-MS analysis revealed four phenolic acids and five flavonoid derivatives in the hydromethanolic extract of D. ruyschiana shoots. All treatments stimulated the production of rosmarinic acid (RA), which was the dominant compound in the analyzed culture; the highest level of RA, i.e., about three times higher than the control, was noted in shoots exposed to 50 µM Cd²⁺ (14.72 mg/g DW), whereas the level of most flavonoids in the culture increased most significantly when exposed to Cd²⁺ at a concentration of 100 µM. Moreover, the shoots grown in the presence of 100 µM Cd²⁺ exhibited significantly higher antioxidant potential in comparison to the control. Our findings indicate that heavy metals are able to stimulate phenolic compound biosynthesis in Dracocephalum shoots without any negative impact on their growth. These results could be of significant importance for the medical, nutraceutical and agronomic industries. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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16 pages, 1791 KiB

Open AccessArticle

Extraction of Bioactive Phenolics from Various Anthocyanin-Rich Plant Materials and Comparison of Their Heat Stability

by Yanli Yu, Syyu Shiau, Weichen Pan and Yvette Yang

Molecules 2024, 29(22), 5256; https://doi.org/10.3390/molecules29225256 - 6 Nov 2024

Viewed by 1309

Abstract

Butterfly pea flower (BPF), roselle calyx (RC), and grape skin (GS) are rich in bioactive phenolics with health benefits. Due to its simplicity, safety, and environmental friendliness, this study used water as a solvent to explore different extraction conditions in these plant materials and compared the heat stability of anthocyanins in the aqueous extracts. To maximize the total anthocyanins and polyphenols in the aqueous extracts, the powders of BPF, GS, and RC should be extracted for 30 min at 90 °C; 30 min and 120 min at 90 °C; and 30 min and 60 min at 60 °C, respectively. Among the tested plant materials, the content of total anthocyanins was RC > GS > BPF, while the total phenolic content was GS > BPF > RC. Anthocyanins of the aqueous extracts underwent rapid thermal degradation at high temperatures and high pH values. The thermal stability of anthocyanins in the materials was in the order: BPF > GS > RC. This is likely related to the types and structures of the anthocyanins such as the degree of acylation and glycosylation. The study demonstrates that hot water extraction is efficient and practical for these materials, yielding extracts suitable for food and nutraceutical applications. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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14 pages, 4052 KiB

Open AccessArticle

Anti-Inflammatory Effects of the Combined Treatment of Resveratrol- and Protopanaxadiol-Enriched Rice Seed Extract on Lipopolysaccharide-Stimulated RAW264.7 Cells

by Chaiwat Monmai and So-Hyeon Baek

Molecules 2024, 29(18), 4343; https://doi.org/10.3390/molecules29184343 - 13 Sep 2024

Cited by 2 | Viewed by 1096

Abstract

The overproduction of proinflammatory cytokines triggers a variety of diseases. Protopanaxadiol (PPD) and resveratrol are naturally found in plants such as ginseng and have potential anti-inflammatory properties, and resveratrol- and PPD-enriched rice seeds have been previously successfully generated. Herein, the synergistic anti-inflammatory activities of extracts of these enriched seeds were assessed in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. In comparison with treatment using extract prepared from PPD-producing transgenic rice (DJ-PPD) alone, cotreatment with DJ526 and DJ-PPD (TR_3) markedly enhanced the anti-inflammatory activities at a similar (compared to DJ526) or higher (compared to DJ-PPD) level. Cotreatment with DJ526 and DJ-PPD markedly inhibited the activation of nuclear factor kappa B (NF-κB) and mitogen-activated protein kinase (MAPK) signaling pathways. Thus, DJ526 and DJ-PPD in combination suppressed the expression of phosphorylated (p)-NF-κB p65, p-p38 MAPK, and p-ERK 1/2. Cotreatment with DJ526 and DJ-PPD downregulated the expression of proinflammatory cytokines (IL-1β, IL-6, and TNF-α), LPS receptor (toll-like receptor-4, TLR-4), proinflammatory mediators (nitric oxide and PGE₂), and arachidonic acid pathway critical enzyme (COX-2). These findings demonstrate the synergistic potential anti-inflammatory activities of resveratrol- and PPD-enriched rice seed extract. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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18 pages, 2968 KiB

Open AccessArticle

Improvement of Bioactive Polyphenol Accumulation in Callus of Salvia atropatana Bunge

by Izabela Grzegorczyk-Karolak, Wiktoria Ejsmont, Anna Karolina Kiss, Przemyslaw Tabaka, Wiktoria Starbała and Marta Krzemińska

Molecules 2024, 29(11), 2626; https://doi.org/10.3390/molecules29112626 - 3 Jun 2024

Cited by 4 | Viewed by 1488

Abstract

Callus cultures of the Iranian medicinal plant Salvia atropatana were initiated from three-week-old seedlings on Murashige and Skoog (MS) medium supplemented with α-naphthaleneacetic acid (NAA) and various cytokinins. Although all tested hormonal variants of the medium and explant enabled callus induction, the most promising growth was noted for N-(2-chloro-4-pyridyl)-N′-phenylurea (CPPU)-induced calli. Three lines obtained on this medium (cotyledon line-CL, hypocotyl line—HL, and root line—RL) were preselected for further studies. Phenolic compounds in the callus tissues were identified using UPLC–MS (ultra-performance liquid chromatography–mass spectrometry) and quantified with HPLC (high-performance liquid chromatography). All lines exhibited intensive growth and contained twelve phenolic acid derivatives, with rosmarinic acid predominating. The cotyledon-derived callus line displayed the highest growth index values and polyphenol content; this was exposed to different light-emitting diodes (LED) for improving biomass accumulation and secondary metabolite yield. Under LED treatments, all callus lines exhibited enhanced RA and total phenolic content compared to fluorescent light, with the highest levels observed for white (48.5–50.2 mg/g dry weight) and blue (51.4–53.9 mg/g dry weight) LEDs. The selected callus demonstrated strong antioxidant potential in vitro based on the 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and ferric reducing antioxidant power (FRAP) tests. Our findings confirm that the S. atropatana callus system is suitable for enhanced rosmarinic acid production; the selected optimized culture provide high-quality plant-derived products. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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Review

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32 pages, 6802 KiB

Open AccessReview

p-Coumaroyl Amides from the Plant Kingdom: A Comprehensive Review of Natural Sources, Biosynthesis, and Biological Activities

by Federico Berti, Elena Maria Tamburello and Cristina Forzato

Molecules 2025, 30(6), 1259; https://doi.org/10.3390/molecules30061259 - 11 Mar 2025

Viewed by 552

Abstract

Hydroxycinnamic acids are widely distributed in the plant kingdom, both as free compounds and as conjugates with other molecules, such as amino acids, carbohydrates, alcohols or amines, and polyamines, forming different derivatives, such as amides, esters, thioesters, or ethers. Among the different hydroxycinnamic acids, p-coumaric acid has a high bioavailability and its amide derivatives, also known as phenolamides (PAs) and hydroxycinnamic acid amides (HCAAs), play specific roles in plant development and defense. They are also involved in several biological activities that affect human health. The present review collected data and described secondary and tertiary amides of p-coumaric acids found in plants, from their natural sources to their biosynthesis. The review also described the acyl-transferase mechanisms involved in their formation, their roles in plants, as well as studies of their biological activities in humans. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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32 pages, 2477 KiB

Open AccessReview

Polyphenols and Microbiota Modulation: Insights from Swine and Other Animal Models for Human Therapeutic Strategies

by Andrei Cristian Anghel, Ionelia Țăranu, Alina Orțan, Simona Marcu Spinu, Mihaela Dragoi Cudalbeanu, Petronela Mihaela Rosu and Narcisa Elena Băbeanu

Molecules 2024, 29(24), 6026; https://doi.org/10.3390/molecules29246026 - 20 Dec 2024

Cited by 1 | Viewed by 1617

Abstract

High consumption of ultra-processed foods, rich in sugar and unhealthy fats, has been linked to the onset of numerous chronic diseases. Consequently, there has been a growing shift towards a fiber-rich diet, abundant in fruits, vegetables, seeds, and nuts, to enhance longevity and quality of life. The primary bioactive components in these plant-based foods are polyphenols, which exert significant effects on modulating the gastrointestinal microbiota through their antioxidant and anti-inflammatory activities. This modulation has preventive effects on neurodegenerative, metabolic, and cardiovascular diseases, and even cancer. The antimicrobial properties of polyphenols against pathogenic bacteria have significantly reduced the need for antibiotics, thereby lowering the risk of antibiotic resistance. This paper advances the field by offering novel insights into the beneficial effects of polyphenols, both directly through the metabolites produced during digestion and indirectly through changes in the host’s gastrointestinal microbiota, uniquely emphasizing swine as a model highly relevant to human health, a topic that, to our knowledge, has not been thoroughly explored in previous reviews. This review also addresses aspects related to both other animal models (mice, rabbits, and rats), and humans, providing guidelines for future research into the benefits of polyphenol consumption. By linking agricultural and biomedical perspectives, it proposes strategies for utilizing these bioactive compounds as therapeutic agents in both veterinary and human health sciences. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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21 pages, 1756 KiB

Open AccessReview

Advances in Extracting Bioactive Compounds from Food and Agricultural Waste and By-Products Using Natural Deep Eutectic Solvents: A Circular Economy Perspective

by Petar Ristivojević, Maja Krstić Ristivojević, Dalibor Stanković and Ilija Cvijetić

Molecules 2024, 29(19), 4717; https://doi.org/10.3390/molecules29194717 - 5 Oct 2024

Cited by 12 | Viewed by 3886

Abstract

Due to the urgent need for a transition to sustainable, zero-waste green technology, the extraction of bioactives from food and agricultural by-products and waste has garnered increasing interest. Traditional extraction techniques often involve using organic solvents, which are associated with environmental and health risks. Natural deep eutectic solvents (NADESs) have emerged as a promising green alternative, offering advantages such as low toxicity, biodegradability, and the ability to dissolve a wide range of biomolecules. This review provides a comprehensive overview of recent trends in the application of NADESs for extracting bioactive compounds from sustainable sources. The review explains the composition and principles of preparation and highlights various applications of NADESs in extracting different classes of bioactive compounds, emphasizing their potential to revolutionize extraction processes. By summarizing the latest advancements and trends, this review aims to support research and industrial applications of NADESs, promoting more sustainable and efficient extraction methods in the food and agricultural sectors. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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13 pages, 1279 KiB

Open AccessReview

The Phytochemical, Quercetin, Attenuates Nociceptive and Pathological Pain: Neurophysiological Mechanisms and Therapeutic Potential

by Mamoru Takeda, Yukito Sashide, Ryou Toyota and Haruka Ito

Molecules 2024, 29(16), 3957; https://doi.org/10.3390/molecules29163957 - 21 Aug 2024

Cited by 4 | Viewed by 1892

Abstract

Although phytochemicals are plant-derived toxins that are primarily produced as a form of defense against insects or microbes, several lines of study have demonstrated that the phytochemical, quercetin, has several beneficial biological actions for human health, including antioxidant and inflammatory effects without side effects. Quercetin is a flavonoid that is widely found in fruits and vegetables. Since recent studies have demonstrated that quercetin can modulate neuronal excitability in the nervous system, including nociceptive sensory transmission via mechanoreceptors and voltage-gated ion channels, and inhibit the cyclooxygenase-2-cascade, it is possible that quercetin could be a complementary alternative medicine candidate; specifically, a therapeutic agent against nociceptive and pathological pain. The focus of this review is to elucidate the neurophysiological mechanisms underlying the modulatory effects of quercetin on nociceptive neuronal activity under nociceptive and pathological conditions, without inducing side effects. Based on the results of our previous research on trigeminal pain, we have confirmed in vivo that the phytochemical, quercetin, demonstrates (i) a local anesthetic effect on nociceptive pain, (ii) a local anesthetic effect on pain related to acute inflammation, and (iii) an anti-inflammatory effect on chronic pain. In addition, we discuss the contribution of quercetin to the relief of nociceptive and inflammatory pain and its potential clinical application. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds, Volume III)

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