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Research of Phenolic Compounds from Natural Source

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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: closed (30 November 2023) | Viewed by 25961

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Dr. Ye Tian

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Guest Editor

Food Sciences, Department of Life Technologies, University of Turku, FI-20014 Turku, Finland
Interests: mass spectrometry; liquid chromatography; food chemistry; plant secondary metabolites; bioactivity of phenolic compounds; valorization of agro-industrial side streams

Prof. Dr. Baoru Yang

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Guest Editor

Food Sciences, Department of Life Technologies, University of Turku, FI-20014 Turku, Finland
Interests: biochemistry and chemistry of lipids; chemistry and bioactivities of polyphenols; impact of growth environment on northern food crops; quality and health effects of food; food metabolomics

Dr. Oskar Laaksonen

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Guest Editor

Food Sciences, Department of Life Technologies, University of Turku, FI-20014 Turku, Finland
Interests: sensory qualities of food; sensory-active compounds in foods; taste and astringency; phenolic compounds
Special Issues, Collections and Topics in MDPI journals

Dr. Ying Zhou

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Guest Editor

Food Sciences, Department of Life Technologies, University of Turku, FI-20014 Turku, Finland
Interests: environmental science; waste management; food technology and nutrition; food chemistry; chromatographic technology

Special Issue Information

Dear Colleagures,

Phenolic compounds have attracted great attention in recent decades due to their remarkable properties in promoting human health. These compounds are a large group of phytochemicals which present ubiquitously in nature primarily as the secondary metabolites of plants. To date, thousands of phenolic compounds have been characterized from different natural sources, showing a large diversity in chemical structure. Extensive research has revealed that phenolic profiles in plants vary among plant species and organs. In terms of dietary plants, the level of phenolics is also highly associated with cultivars, cultivation approaches, growing seasons, and processing methods. Variations in phenolic profile inevitably lead to noticeable changes in the health-beneficial functions of plants, which will further affect their application in medicine or human foods.

This Special Issue aims to explore new natural sources of phenolic compounds and improve knowledge on the health benefits of phenolics, the impacts of phenolics on human foods, and the key factors influencing phenolic composition. The topics of the Special Issue include, but are not limited to:

Phenolic compounds from new natural sources (e.g. new cultivars/varieties of plants, agro-industrial side streams);
Health-promoting functions of naturally sourced phenolic compounds;
Influences of phenolic compounds on sensory properties of foods;
Effects of phenolic compounds on food safety;
Impacts of plant genotypes on phenolic composition;
Impacts of climate change on phenolic composition;
Variations in phenolic profiles during the growing stage of plants;
Effects of cultivation approach on phenolic composition in plants;
Effects of processing or storage methods on phenolic composition in plants.

Research or review articles are both welcomed. For research articles, a precise determination of phenolic compounds is required. We expect articles that provide detailed information of phenolic composition in study materials (by using both chromatographic and mass spectrometric approaches) and a clear association between phenolic compounds and their bioactivities. Studies measuring only 1) total phenolic content, 2) total contents of certain groups of phenolic compounds, or 3) in vitro bioactivity of study materials with colorimetric methods will not be considered. Review articles should focus on the recently published literature (from the previous 5 years) and provide a comprehensive assessment of published material to extend and give new insights into past research.

Dr. Ye Tian
Prof. Dr. Baoru Yang
Dr. Oskar Laaksonen
Dr. Ying Zhou
Guest Editors

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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. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

phenolic compounds
natural sources
health-beneficial functions
sensorial property of foods
food safety
genotypes
growing stage
cultivation
storage
food processing

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Published Papers (11 papers)

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Research

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19 pages, 3418 KiB

Open AccessArticle

Plant-Derived Phenolic Acids Limit the Pathogenesis of Salmonella Typhimurium and Protect Intestinal Epithelial Cells during Their Interactions

by Zabdiel Alvarado-Martinez, Zajeba Tabashsum, Arpita Aditya, Katherine Hshieh, Grace Suh, Matthew Wall, Aaron Scriba, George Sellers, Christa Canagarajah, Sarika Kapadia and Debabrata Biswas

Molecules 2024, 29(6), 1364; https://doi.org/10.3390/molecules29061364 - 19 Mar 2024

Cited by 1 | Viewed by 1097

Abstract

The incidence of gastrointestinal illness attributable to Salmonella enterica serovar Typhimurium (ST) remains a concern for public health worldwide, as it can progress into systemic infections mediated by the type-three secretion system (T3SS), which allows for adherence and invasion to intestinal epithelial cells. The current study evaluates the ability of gallic acid (GA), protocatechuic acid (PA), and vanillic acid (VA) to impair the adhesion and invasion abilities of ST to a human epithelial (INT-407) cell monolayer while also assessing their cytotoxicity. GA, PA, and VA inhibited detectable ST growth at specific concentrations but showed cytotoxicity against INT-407 cells (>20% reduction in viability) after 3 h of treatments. Adjusting the pH of the solutions had a neutralizing effect on cytotoxicity, though it did reduce their antimicrobial potency. Adhesion of ST was reduced significantly when the cells were treated with 4.0 mg/mL of VA, whereas invasion was reduced in all treatments, with GA requiring the lowest concentration (0.5 mg/mL). Relative gene expression of virulence genes after treatment with GA showed downregulation in the T3SS regulator and effector hilA and sipA, respectively. These findings suggest further use of phenolic acids in reducing the activity of key virulence factors critical during ST infection. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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16 pages, 3106 KiB

Open AccessArticle

Chemical Composition, and Antioxidant and Antimicrobial Activity of Oregano Essential Oil

by Magdalena Walasek-Janusz, Agnieszka Grzegorczyk, Anna Malm, Renata Nurzyńska-Wierdak and Daniel Zalewski

Molecules 2024, 29(2), 435; https://doi.org/10.3390/molecules29020435 - 16 Jan 2024

Cited by 7 | Viewed by 3388

Abstract

Antimicrobial resistance (AMR) is a global public health problem, and the rapid rise in AMR is attributed to the inappropriate and/or overuse of antibiotics. Therefore, alternative antimicrobial agents, including those of natural origin, are being sought for the development of new drugs. The purpose of our study was to analyze the chemical composition, and antimicrobial and antioxidant activities of four oregano essential oils (OEOs) from Poland, Europe, Turkey and the USA. The antimicrobial activity (AMA) was evaluated using 23 strains, including Gram-positive bacteria, Gram-negative bacteria and Candida species. The antioxidant activity (AA) of essential oils (EOs) was determined by the DPPH method. The main component of the EOs tested was carvacrol (76.64–85.70%). The highest amount of this compound was determined in the Polish OEO. The OEOs we tested showed antimicrobial resistance, which was especially strong against fungi (MIC = 0.06–0.25 mg/mL⁻¹). These products also showed high AA (71.42–80.44%). OEOs high in carvacrol should be the subject of further research as potential antimicrobial and antioxidant agents. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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20 pages, 2340 KiB

Open AccessArticle

Exploring Antioxidant and α-Glucosidase Inhibitory Activities in Mulberry Leaves (Morus alba L.) across Growth Stages: A Comprehensive Metabolomic Analysis with Chemometrics

by Wenjie Li, Shenghui Hao, Hengyang Li, Qi An, Lina Yang, Bing Guo, Zijing Xue, Yongli Liu, Long Guo, Yuguang Zheng and Dan Zhang

Molecules 2024, 29(1), 171; https://doi.org/10.3390/molecules29010171 - 27 Dec 2023

Viewed by 1877

Abstract

Metabolic product accumulation exhibited variations among mulberry (Morus alba L.) leaves (MLs) at distinct growth stages, and this assessment was conducted using a combination of analytical techniques including high-performance liquid chromatography (HPLC), gas chromatography–mass spectrometry (GC-MS), and liquid chromatography–mass spectrometry (LC-MS). Multivariate analysis was applied to the data, and the findings were correlated with antioxidant activity and α-glucosidase inhibitory effects in vitro. Statistical analyses divided the 27 batches of MLs at different growth stages into three distinct groups. In vitro assays for antioxidant activity and α-glucosidase inhibition revealed that IC₅₀ values were highest at the Y23 stage, which corresponds to the ‘Frost Descends’ solar term. In summary, the results of this study indicate that MLs at different growth stages throughout the year can be categorized into three primary growth stages using traditional Chinese solar terms as reference points, based on the observed variations in metabolite content. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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13 pages, 2276 KiB

Open AccessArticle

Stevia Polyphenols, Their Antimicrobial and Anti-Inflammatory Properties, and Inhibitory Effect on Digestive Enzymes

by Khaing Zar Myint, Zhuoyu Zhou, Qiandai Shi, Junming Chen, Xinyu Dong and Yongmei Xia

Molecules 2023, 28(22), 7572; https://doi.org/10.3390/molecules28227572 - 13 Nov 2023

Cited by 1 | Viewed by 2845

Abstract

Polyphenols from stevia leaves (PPSs) are abundant byproducts from steviol glycoside production, which have been often studied as raw extracts from stevia extracts for their bioactivities. Herein, the PPSs rich in isochlorogenic acids were studied for their antimicrobial and anti-inflammatory properties, as well as their inhibitory effects on digestive enzymes. The PPSs presented stronger antibacterial activity against E. coli, S. aureus, P. aeruginosa, and B. subtilis than their antifungal activity against M. furfur and A. niger. Meanwhile, the PPSs inhibited four cancer cells by more than 60% based on their viability, in a dose-dependent manner. The PPSs presented similar IC₅₀ values on the inhibition of digestive enzyme activities compared to epigallocatechin gallate (EGCG), but had weaker anti-inflammatory activity. Therefore, PPSs could be a potential natural alternative to antimicrobial agents. This is the first report on the bioactivity of polyphenols from stevia rebaudiana (Bertoni) leaves excluding flavonoids, and will be of benefit for understanding the role of PPSs and their application. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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19 pages, 5072 KiB

Open AccessArticle

Mass Spectrometric Fingerprint Mapping Reveals Species-Specific Differences in Plant Polyphenols and Related Bioactivities

by Suvi Vanhakylä and Juha-Pekka Salminen

Molecules 2023, 28(17), 6388; https://doi.org/10.3390/molecules28176388 - 31 Aug 2023

Cited by 2 | Viewed by 1424

Abstract

Plant species show large variation in the composition and content of their tannins and other polyphenols. These large metabolites are not easy to measure accurately, but they are important factors for species bioactivity and chemotaxonomy. Here, we used an automated group-specific UHPLC-DAD-MS/MS tool to detect and quantify eight most common polyphenol groups in 31 chemically diverse plant species representing many types of growth forms and evolutionary ages. Ten replicate plants were used for each species and two polyphenol-related bioactivities, i.e., protein precipitation capacity and oxidative activity were measured in all samples as well. By the help of a novel 2D fingerprint mapping tool we were able to visualize the qualitative and quantitative differences between the species in hydrolysable tannins (galloyl and hexahydroxydiphenoyl derivatives), proanthocyanidins (procyanidins and prodelphinidins), flavonols (kaempferol, quercetin and myricetin derivatives) and quinic acid derivatives together with the two bioactivities. The highest oxidative activities were found with species containing ellagitannins (e.g., Quercus robur, Geranium sylvaticum, Lythrum salicaria and Chamaenerion angustifolium) or prodelphinidin-rich proanthocyanidins (e.g., Ribes alpinum, Salix phylicifolia and Lysimachia vulgaris). The best species with high protein precipitation capacity were rich in gallotannins (Acer platanoides and Paeonia lactiflora) or oligomeric ellagitannins (e.g., Comarum palustre, Lythrum salicaria and Chamaenerion angustifolium). These types of tools could prove their use in many types of screening experiments and might reveal even unusually active polyphenol types directly from the crude plant extracts. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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20 pages, 4274 KiB

Open AccessArticle

Seasonal Variation in Plant Polyphenols and Related Bioactivities across Three Years in Ten Tree Species as Visualized by Mass Spectrometric Fingerprint Mapping

by Suvi Vanhakylä and Juha-Pekka Salminen

Molecules 2023, 28(16), 6093; https://doi.org/10.3390/molecules28166093 - 16 Aug 2023

Cited by 1 | Viewed by 1230

Abstract

The currently changing climates and environments place plants under many types of stresses that affect both their survival and levels of chemical defenses. The gradual induction of defenses in stressed plant populations could be monitored on a yearly basis unless a seasonal and yearly variation in natural defense levels obscures such monitoring schemes. Here, we studied the stability of the species-specific polyphenol composition and content of 10 tree species over three growing seasons using five replicate trees per species. We specifically measured hydrolyzable tannins (galloyl and hexahydroxydiphenoyl derivatives), proanthocyanidins (procyanidins and prodelphinidins), flavonols (kaempferol, quercetin and kaempferol derivatives) and quinic acid derivatives with the group-specific UHPLC-DAD-MS/MS tool, together with two bioactivities, the protein precipitation capacity and oxidative activity. With the help of a fingerprint mapping tool, we found out that species differed a lot in their seasonal and between-year variation in polyphenols and that the variation was also partially specific to compound groups. Especially ellagitannins tended to have declining seasonal patterns while the opposite was true for proanthocyanidins. Some of the species showed minimal variation in all measured variables, while others showed even induced levels of certain polyphenol groups during the 3-year study. For every species, we found either species-specific baseline levels in qualitative and quantitative polyphenol chemistry or the compound groups with the most plasticity in their production. The used tools could thus form a good combination for future studies attempting to monitor the overall changes in polyphenol chemistry due to various biotic or abiotic stress factors in plant populations or in more controlled environments. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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12 pages, 4130 KiB

Open AccessArticle

Improving Blueberry Anthocyanins’ Stability Using a Ferritin Nanocarrier

by Wuyang Huang, Xingyu Zhao, Zhi Chai, Daniela D. Herrera-Balandrano, Bin Li, Yiyun Yang, Shan Lu and Zhigang Tu

Molecules 2023, 28(15), 5844; https://doi.org/10.3390/molecules28155844 - 3 Aug 2023

Cited by 7 | Viewed by 2077

Abstract

Blueberries are fruits known for their high level of anthocyanins, which have high nutritional value and several biological properties. However, the chemical instability of anthocyanins is one of the major limitations of their application. The stability of blueberry anthocyanin extracts (BAEs) encapsulated in a ferritin nanocarrier was investigated in this study for several influencing parameters, including pH, temperature, UV–visible light, redox agents, and various metal ions. The outcomes supported the positive role of protein nanoparticles in enhancing the stability of blueberry anthocyanins by demonstrating that the stability of encapsulated BAE nanoparticles with ferritin carriers was significantly higher than that of free BAEs and a mixture of BAEs and ferritin carriers. This study provides an alternative approach for enhancing blueberry anthocyanin stability using ferritin nanocarrier encapsulation. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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18 pages, 1471 KiB

Open AccessArticle

Affinity of Tannins to Cellulose: A Chromatographic Tool for Revealing Structure-Activity Patterns

by Essi Suominen, Santeri Savila, Mimosa Sillanpää, Pia Damlin and Maarit Karonen

Molecules 2023, 28(14), 5370; https://doi.org/10.3390/molecules28145370 - 13 Jul 2023

Cited by 5 | Viewed by 1872

Abstract

Food, feed and beverage processing brings tannins into contact with macromolecules, such as proteins and polysaccharides, leading to different chemical and physical interactions. The interactions of tannins with proteins are well known but less is known about the affinity of tannins to polysaccharides. We used bacterial cellulose from nata de coco as a model compound to investigate how tannins and cellulose interact by adsorption measurements using UPLC-DAD. We also explored how the structure of tannins influences these interactions. The model tannins included nine individual structurally different hydrolysable tannins (HTs) and eight well-defined proanthocyanidin (PA) fractions with different monomeric units, mean degree of polymerization and both A- and B-type linkages. Tannins were found to have both strong and weak interactions with bacterial cellulose, depending on the exact structure of the tannin. For HTs, the main structural features affecting the interactions were the structural flexibility of the HT molecule and the number of free galloyl groups. For PAs, prodelphinidins were found to have a higher affinity to cellulose than procyanidins. Similarly to HTs, the presence of free galloyl groups in galloylated PAs and the flexibility of the PA molecule led to a stronger interaction. Adsorption measurements by UPLC-DAD proved to be a sensitive and rapid tool to evaluate the affinity of tannins to cellulose. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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21 pages, 2571 KiB

Open AccessArticle

Variation in Phenolic Compounds, Antioxidant and Antibacterial Activities of Extracts from Different Plant Organs of Meadowsweet (Filipendula ulmaria (L.) Maxim.)

by Tamara Savina, Valery Lisun, Pavel Feduraev and Liubov Skrypnik

Molecules 2023, 28(8), 3512; https://doi.org/10.3390/molecules28083512 - 16 Apr 2023

Cited by 17 | Viewed by 3631

Abstract

Meadowsweet (Filipendula ulmaria (L.) Maxim.) has been widely used in the treatment of various diseases. The pharmacological properties of meadowsweet are derived from the presence of phenolic compounds of a diverse structure in sufficiently large quantities. The purpose of this study was to examine the vertical distribution of individual groups of phenolic compounds (total phenolics, flavonoids, hydroxycinnamic acids, catechins, proanthocyanidins, and tannins) and individual phenolic compounds in meadowsweet and to determine the antioxidant and antibacterial activity of extracts from various meadowsweet organs. It was found that the leaves, flowers, fruits, and roots of meadowsweet are characterized by a high total phenolics content (up to 65 mg g⁻¹). A high content of flavonoids was determined in the upper leaves and flowers (117–167 mg g⁻¹), with high contents of hydroxycinnamic acids in the upper leaves, flowers, and fruits (6.4–7.8 mg g^–1); high contents of catechins and proanthocyanidins in the roots (45.1 and 3.4 mg g^–1, respectively); and high tannin content in the fruits (38.3 mg g^–1). Analysis of extracts by high-performance liquid chromatography (HPLC) showed that the qualitative and quantitative composition of individual phenolic compounds in various parts of the meadowsweet varied greatly. Among the flavonoids identified in meadowsweet, quercetin derivatives dominate, namely quercetin 3-O-rutinoside, quercetin 3-β-d-glucoside, and quercetin 4′-O-glucoside. Quercetin 4′-O-glucoside (spiraeoside) was found only in the flowers and fruits. Catechin was identified in the leaves and roots of meadowsweet. The distribution of phenolic acids across the plant was also uneven. In the upper leaves, a higher content of chlorogenic acid was determined, and in the lower leaves, a higher content of ellagic acid determined. In flowers and fruits, a higher contents of gallic, caftaric, ellagic, and salicylic acids were noted. Ellagic and salicylic acids were also dominant among phenolic acids in the roots. Based on the results of the analysis of antioxidant activity in terms of the ability to utilize the radicals of 2,2-diphenyl-1-picrylhydrazine (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazolino-6-sulfonic acid) (ABTS) and in terms of iron-reducing ability (FRAP), the upper leaves, flowers, and fruits of meadowsweet can be considered plant raw materials suitable to obtain extracts with high antioxidant activity. Extracts of plant fruits and flowers also showed high antibacterial activity against the bacteria Bacillus subtilis and Pseudomonas aeruginosa. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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16 pages, 4797 KiB

Open AccessArticle

Phenolic Compounds from Sonchus arvensis Linn. and Hemerocallis citrina Baroni. Inhibit Sucrose and Stearic Acid Induced Damage in Caenorhabditis elegans

by Qin An, Lei Zhang, Xiyue Qin, Xiong Wang, Wenli Wang, Qingyong Meng and Yali Zhang

Molecules 2023, 28(4), 1707; https://doi.org/10.3390/molecules28041707 - 10 Feb 2023

Viewed by 1822

Abstract

Sonchus arvensis Linn. and Hemerocallis citrina Baroni. have been reported to improve body resistance. However, the underlying mechanism is not clear. In this study, Sonchus arvensis Linn. phenolic compounds (SAP) and Hemerocallis citrina Baroni. phenolic compounds (HCP) were extracted and their protective effects in Caenorhabditis elegans evaluated. SAP and HCP showed considerably different phenolic compositions. In the normal C. elegans model, HCP exhibited better effects in promoting growth than SAP. In the sucrose-incubated C. elegans model, both SAP and HCP showed positive effects against the high-sucrose-induced damage. In the stearic acid-incubated C. elegans model, both SAP and HCP improved lifespan, reproductive ability and growth, while HCP had a more evident effect than SAP on reproductive ability. The TGF-β signaling pathway was confirmed to be involved in the protective effects of SAP and HCP. The antioxidant ability of SAP was also found to be related to skn-1. Our study shows that both SAP and HCP have protective effects against high sucrose- or high stearic acid-induced damage. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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Review

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20 pages, 394 KiB

Open AccessReview

Phenolic Compounds from New Natural Sources—Plant Genotype and Ontogenetic Variation

by Renata Nurzyńska-Wierdak

Molecules 2023, 28(4), 1731; https://doi.org/10.3390/molecules28041731 - 11 Feb 2023

Cited by 30 | Viewed by 3635

Abstract

Phenolic compounds (PCs) are widespread secondary metabolites with potent biological activity. Their sources are mainly plants from cultivated and natural states, providing valuable protective and health-promoting extracts. The wide biological activity of PCs (antioxidant, anti-inflammatory, antimicrobial, antiatherosclerotic, antidiabetic, antiallergic, prebiotic, antimutagenic) means that new sources of PCs are constantly being sought, as exemplified by extracting these compounds from tissue culture or agricultural by-products. Plant phenols show marked qualitative and quantitative variation not only at different genetic levels (between and within species and clones) but also between different physiological and developmental stages. Assessing genetic and seasonal variations in phenolic content and activity allows for selecting the best time to harvest the plant. Learning about the causes of PCs’ variability and putting this knowledge into practice can significantly increase PCs’ yields and extract the most valuable compounds. The health-promoting properties resulting from consuming products rich in plant PCs are undeniable, so it is worth promoting high-phenolic products as a regular diet. This paper presents an overview of different sources of PCs for use as potential therapeutic alternatives. Additionally, factors of variation in the phenolic complex at the genome and ontogeny levels, relevant in practical terms and as a basis for further scientific research, are presented. Full article

(This article belongs to the Special Issue Research of Phenolic Compounds from Natural Source)

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