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Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives

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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 (31 May 2023) | Viewed by 41012

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Dr. Matej Sova

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Faculty of Pharmacy, University of Ljubljana, Askerceva 7, 1000 Ljubljana, Slovenia
Interests: drug discovery; medicinal chemistry; organic synthesis; enzyme inhibitors; immunomodulators; antimicrobials; anticancer agents; antioxidants; cinnamic acid derivatives
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Dear Colleagues,

I am pleased to invite you to submit an original research article, a review paper, or a communication to this Special Issue of Molecules on the chemistry, biology, and pharmacology of natural phenolic compounds and their synthetic derivatives.

Natural (poly)phenolic compounds have attracted much interest in the scientific community due to their diverse biological activities and been acknowledged to have antioxidant, anti-inflammatory, anticarcinogenic, antimicrobial, antihypertensive, antidiabetic, cardio-protective, hepato-protective, and many other activities. Thus, these compounds possess significant potential in the prevention and treatment of numerous diseases as well as a relevant role in the maintenance of human health. To date, numerous synthetic derivatives of natural phenolic compounds have been prepared to obtain or enhance a selected biological activity and improve their pharmacokinetic properties. Due to the pharmaceutical and nutraceutical significance of natural and synthetic phenolic compounds, the aim of this Special Issue is to present a collection of the most recent contributions regarding their chemistry, biology, and pharmacology with emphasis on novel findings describing their key in vitro and in vivo health-beneficial effects.

You may choose our Joint Special Issue in Chemistry.

Dr. Matej Sova
Guest Editor

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Keywords

(poly)phenols
bioactive compounds
flavonoids
phenolic acids
secondary metabolites
pharmacological properties
mechanism of action
health effects
synthesis

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Related Special Issue

Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives in Chemistry

Published Papers (9 papers)

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Research

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12 pages, 2116 KiB

Open AccessArticle

Quinone Pool, a Key Target of Plant Flavonoids Inhibiting Gram-Positive Bacteria

by Li Zhang, Yu Yan, Jianping Zhu, Xuexue Xia, Ganjun Yuan, Shimin Li, Beibei Deng and Xinrong Luo

Molecules 2023, 28(13), 4972; https://doi.org/10.3390/molecules28134972 - 24 Jun 2023

Cited by 5 | Viewed by 1651

Abstract

Plant flavonoids have attracted increasing attention as new antimicrobial agents or adjuvants. In our previous work, it was confirmed that the cell membrane is the major site of plant flavonoids acting on the Gram-positive bacteria, which likely involves the inhibition of the respiratory chain. Inspired by the similar structural and antioxidant characters of plant flavonoids to hydro-menaquinone (MKH₂), we deduced that the quinone pool is probably a key target of plant flavonoids inhibiting Gram-positive bacteria. To verify this, twelve plant flavonoids with six structural subtypes were preliminarily selected, and their minimum inhibitory concentrations (MICs) against Gram-positive bacteria were predicted from the antimicrobial quantitative relationship of plant flavonoids to Gram-positive bacteria. The results showed they have different antimicrobial activities. After their MICs against Staphylococcus aureus were determined using the broth microdilution method, nine compounds with MICs ranging from 2 to 4096 μg/mL or more than 1024 μg/mL were eventually selected, and then their MICs against S. aureus were determined interfered with different concentrations of menaquinone−4 (MK−4) and the MKs extracted from S. aureus. The results showed that the greater the antibacterial activities of plant flavonoids were, the more greatly their antibacterial activities decreased along with the increase in the interfering concentrations of MK−4 (from 2 to 256 μg/mL) and the MK extract (from 4 to 512 μg/mL), while those with the MICs equal to or more than 512 μg/mL decreased a little or remained unchanged. In particular, under the interference of MK−4 (256 μg/mL) and the MK extract (512 μg/mL), the MICs of α-mangostin, a compound with the greatest inhibitory activity to S. aureus out of these twelve plant flavonoids, increased by 16 times and 8 to 16 times, respectively. Based on the above, it was proposed that the quinone pool is a key target of plant flavonoids inhibiting Gram-positive bacteria, and which likely involves multiple mechanisms including some enzyme and non-enzyme inhibitions. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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27 pages, 12604 KiB

Open AccessArticle

Dracocephalum jacutense Peschkova from Yakutia: Extraction and Mass Spectrometric Characterization of 128 Chemical Compounds

by Zhanna M. Okhlopkova, Mayya P. Razgonova, Zoya G. Rozhina, Polina S. Egorova and Kirill S. Golokhvast

Molecules 2023, 28(11), 4402; https://doi.org/10.3390/molecules28114402 - 28 May 2023

Cited by 3 | Viewed by 1961

Abstract

Dracocephalum jacutense Peschkova is a rare and endangered species of the genus Dracocephalum of the Lamiaceae family. The species was first described in 1997 and listed in the Red Data Book of Yakutia. Significant differences in the multicomponent composition of extracts from D. jacutense collected in the natural environment and successfully introduced in the Botanical Garden of Yakutsk were identified by a team of authors earlier in a large study. In this work, we studied the chemical composition of the leaves, stem, and inflorescences of D. jacutense using the tandem mass spectrometry method. Only three cenopopulations of D. jacutense were found by us in the territory of the early habitat—in the vicinity of the village of Sangar, Kobyaysky district of Yakutia. The aboveground phytomass of the plant was collected, processed and dried as separate parts of the plant: inflorescences, stem and leaves. Firstly, a total of 128 compounds, 70% of which are polyphenols, were tentatively identified in extracts of D. jacutense. These polyphenol compounds were classified as 32 flavones, 12 flavonols, 6 flavan-3-ols, 7 flavanones, 17 phenolic acids, 2 lignans, 1 dihydrochalcone, 4 coumarins, and 8 anthocyanidins. Other chemical groups were presented as carotenoids, omega-3-fatty acids, omega-5-fatty acids, amino acids, purines, alkaloids, and sterols. The inflorescences are the richest in polyphenols (73 polyphenolic compounds were identified), while 33 and 22 polyphenols were found in the leaves and stems, respectively. A high level of identity for polyphenolic compounds in different parts of the plant is noted for flavanones (80%), followed by flavonols (25%), phenolic acids (15%), and flavones (13%). Furthermore, 78 compounds were identified for the first time in representatives of the genus Dracocephalum, including 50 polyphenolic compounds and 28 compounds of other chemical groups. The obtained results testify to the unique composition of polyphenolic compounds in different parts of D. jacutense. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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14 pages, 2327 KiB

Open AccessArticle

Autohydrolysis Application on Vine Shoots and Grape Stalks to Obtain Extracts Enriched in Xylo-Oligosaccharides and Phenolic Compounds

by Graziana Difonzo, Marica Troilo, Michele Casiello, Lucia D’Accolti and Francesco Caponio

Molecules 2023, 28(9), 3760; https://doi.org/10.3390/molecules28093760 - 27 Apr 2023

Cited by 1 | Viewed by 1540

Abstract

Agronomic practices and the winemaking process lead to the production of considerable quantities of waste and by-products. These are often considered waste with negative effects on environmental sustainability. However, vine shoots and grape stalks can be reused, representing a potential source of xylo-oligosaccharides and polyphenols. In this context, the purpose of this work was to obtain enriched extracts using three different autohydrolysis treatments with (i) H₂O, (ii) H₂O:EtOH, and (iii) H₂O:Amberlyst. The obtained extracts were characterized by their xylo-oligosaccharide and polyphenol profiles using LC-MS techniques. The use of ethanol during autohydrolysis allowed for greater extraction of xylan-class compounds, especially in vine shoot samples, while an increase in antioxidant activity (128.04 and 425.66 µmol TE/g for ABTS and DPPH, respectively) and in total phenol content (90.92 mg GAE/g) was obtained for grape stalks. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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18 pages, 3883 KiB

Open AccessArticle

Lipase-Catalyzed Synthesis, Antioxidant Activity, Antimicrobial Properties and Molecular Docking Studies of Butyl Dihydrocaffeate

by Bartłomiej Zieniuk, Chimaobi James Ononamadu, Karina Jasińska, Katarzyna Wierzchowska and Agata Fabiszewska

Molecules 2022, 27(15), 5024; https://doi.org/10.3390/molecules27155024 - 7 Aug 2022

Cited by 4 | Viewed by 2553

Abstract

Green chemistry approaches, such as lipase-catalyzed esterification, are promising methods for obtaining valuable chemical compounds. In the case of the use of lipases, unlike in aqueous environments, the processes of the ester bond formations are encountered in organic solvents. The aim of the current research was to carry out the lipase-catalyzed synthesis of an ester of dihydrocaffeic acid. The synthesized compound was then evaluated for antioxidant and antimicrobial activities. However, the vast majority of its antioxidant activity was retained, which was demonstrated by means of DPPH· (2,2-diphenyl-1-picrylhydrazyl) and CUPRAC (cupric ion reducing antioxidant capacity) methods. Regarding its antimicrobial properties, the antifungal activity against Rhizopus oryzae is worth mentioning. The minimum inhibitory and fungicidal concentrations were 1 and 2 mM, respectively. The high antifungal activity prompted the use of molecular docking studies to verify potential protein targets for butyl ester of dihydrocaffeic ester. In the case of one fungal protein, namely 14-α sterol demethylase B, it was observed that the ester had comparable binding energy to the triazole medication, isavuconazole, but the interacted amino acid residues were different. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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9 pages, 1957 KiB

Open AccessArticle

Phytophenol Dimerization Reaction: From Basic Rules to Diastereoselectivity and Beyond

by Shuqin Liu, Xican Li, Ban Chen, Xiaojian Ouyang, Yulu Xie and Dongfeng Chen

Molecules 2022, 27(15), 4842; https://doi.org/10.3390/molecules27154842 - 28 Jul 2022

Cited by 4 | Viewed by 1878

Abstract

Phytophenol dimerization, which is a radical-mediated coupling reaction, plays a critical role in many fields, including lignin biosynthesis. To understand the reaction, 2,2-diphenyl-1-picrylhydrazyl radical was used to initiate a series of phytophenol dimerization reactions in methanol. The products were identified using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS/MS) analysis in situ. The identified products mainly included biphenols, magnolol, honokiol, gingerol 6,6′-dimers, 3,6-dimethoxylcatechol β,β′ dimer, euphorbetin, bis-eugenol, dehydrodiisoeugenol, trans-ε-viniferin, (+) pinoresinol, and (−) pinoresinol. Structure–function relationship analysis allowed four basic rules to be defined: meta-excluded, C–C bonding domination, ortho-diOH co-activation, and exocyclic C=C involvement. The exocyclic C=C involvement, however, required conjugation with the phenolic core and the para-site of the -OH group, to yield a furan-fused dimer with two chiral centers. Computational chemistry indicated that the entire process was completed via a radical coupling reaction and an intramolecular conjugate addition reaction. Similar results were also found for the horseradish peroxidase (HRP)-catalyzed coniferyl alcohol dimerization, which produced (+) and (−) pinoresinols (but no (−) epipinoresinol), suggesting that the HRP-catalyzed process was essentially an exocyclic C=C-involved phytophenol dimerization reaction. The reaction was highly diastereoselective. This was attributed to the intramolecular reaction, which prohibited Re-attack. The four basic rules and diastereoselectivity can explain and even predict the main products in various chemical and biological events, especially oxidase-catalyzed lignin cyclization. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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14 pages, 7394 KiB

Open AccessArticle

Methoxy-Substituted γ-Oxa-ε-Lactones Derived from Flavanones—Comparison of Their Anti-Tumor Activity In Vitro

by Aleksandra Pawlak, Marta Henklewska, Beatriz Hernández-Suárez, Monika Siepka, Witold Gładkowski, Czesław Wawrzeńczyk, Karolina Motykiewicz-Pers and Bożena Obmińska-Mrukowicz

Molecules 2021, 26(20), 6295; https://doi.org/10.3390/molecules26206295 - 18 Oct 2021

Cited by 2 | Viewed by 1817

Abstract

Background: The study investigated four flavanone-derived γ-oxa-ε-lactones: a parent unsubstituted compound and its three derivatives with the methoxy group in positions 2′, 4′ and 8. Our objective was to find out if the introduction of the methoxy group into the aromatic ring affects in vitro anti-tumor potency of the investigated lactones. Methods: Cytotoxic and pro-apoptotic effects were assessed with cytometric tests with propidium iodide, annexin V, and Western blot techniques. We also investigated potential synergistic potency of the tested lactones and glucocorticoids in canine lymphoma/leukemia cell lines. Results: The tested flavanone-derived lactones showed anti-cancer activity in vitro. Depending on its location, the methoxy group either increased or decreased cytotoxicity of the derivatives as compared with the parent compound. The most potent lactone was the one with the methoxy group at position 4′ of the B ring (compound 3), and the weakest activity was observed when the group was located at C-8 in the A ring. A combination of the lactones with glucocorticoids confirmed their synergy in anti-tumor activity in vitro. Conclusions: Methoxy-substituted flavanone-derived lactones effectively kill canine lymphoma/leukemia cells in vitro and, thanks to their synergistic action with glucocorticoids, may potentially be applied in the treatment of hematopoietic cancers. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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Review

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36 pages, 5632 KiB

Open AccessReview

Role of Phenolic Compounds in Human Disease: Current Knowledge and Future Prospects

by Md. Mominur Rahman, Md. Saidur Rahaman, Md. Rezaul Islam, Firoza Rahman, Faria Mannan Mithi, Taha Alqahtani, Mohannad A. Almikhlafi, Samia Qasem Alghamdi, Abdullah S Alruwaili, Md. Sohel Hossain, Muniruddin Ahmed, Rajib Das, Talha Bin Emran and Md. Sahab Uddin

Molecules 2022, 27(1), 233; https://doi.org/10.3390/molecules27010233 - 30 Dec 2021

Cited by 362 | Viewed by 19702

Abstract

Inflammation is a natural protective mechanism that occurs when the body’s tissue homeostatic mechanisms are disrupted by biotic, physical, or chemical agents. The immune response generates pro-inflammatory mediators, but excessive output, such as chronic inflammation, contributes to many persistent diseases. Some phenolic compounds work in tandem with nonsteroidal anti-inflammatory drugs (NSAIDs) to inhibit pro-inflammatory mediators’ activity or gene expression, including cyclooxygenase (COX). Various phenolic compounds can also act on transcription factors, such as nuclear factor-κB (NF-κB) or nuclear factor-erythroid factor 2-related factor 2 (Nrf-2), to up-or downregulate elements within the antioxidant response pathways. Phenolic compounds can inhibit enzymes associated with the development of human diseases and have been used to treat various common human ailments, including hypertension, metabolic problems, incendiary infections, and neurodegenerative diseases. The inhibition of the angiotensin-converting enzyme (ACE) by phenolic compounds has been used to treat hypertension. The inhibition of carbohydrate hydrolyzing enzyme represents a type 2 diabetes mellitus therapy, and cholinesterase inhibition has been applied to treat Alzheimer’s disease (AD). Phenolic compounds have also demonstrated anti-inflammatory properties to treat skin diseases, rheumatoid arthritis, and inflammatory bowel disease. Plant extracts and phenolic compounds exert protective effects against oxidative stress and inflammation caused by airborne particulate matter, in addition to a range of anti-inflammatory, anticancer, anti-aging, antibacterial, and antiviral activities. Dietary polyphenols have been used to prevent and treat allergy-related diseases. The chemical and biological contributions of phenolic compounds to cardiovascular disease have also been described. This review summarizes the recent progress delineating the multifunctional roles of phenolic compounds, including their anti-inflammatory properties and the molecular pathways through which they exert anti-inflammatory effects on metabolic disorders. This study also discusses current issues and potential prospects for the therapeutic application of phenolic compounds to various human diseases. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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17 pages, 1947 KiB

Open AccessReview

Recent Developments in Therapeutic and Nutraceutical Applications of p-Methoxycinnamic Acid from Plant Origin

by Anna Płowuszyńska and Anna Gliszczyńska

Molecules 2021, 26(13), 3827; https://doi.org/10.3390/molecules26133827 - 23 Jun 2021

Cited by 10 | Viewed by 3600

Abstract

The p-methoxycinnamic acid (p-MCA) is one of the most studied phenylpropanoids with high importance not only in the wide spectrum of therapeutic activities but also its potential application for the food industry. This natural compound derived from plants exhibits a wide range of biologically useful properties; therefore, during the last two decades it has been extensively tested for therapeutic and nutraceutical applications. This article presents the natural sources of p-MCA, its metabolism, pharmacokinetic properties, and safety of its application. The possibilities of using this dietary bioactive compound as a nutraceutical agent that may be used as functional food ingredient playing a vital role in the prevention and treatment of many chronic diseases is also discussed. We present the antidiabetic, anticancer, antimicrobial, hepato-, and neuroprotective activities of p-MCA and methods of its lipophilization that have been developed so far to increase its industrial application and bioavailability in the biological systems. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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28 pages, 4507 KiB

Open AccessReview

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

by Vladimir I. Muronetz, Kseniya Barinova, Sofia Kudryavtseva, Maria Medvedeva, Aleksandra Melnikova, Irina Sevostyanova, Pavel Semenyuk, Yulia Stroylova and Matej Sova

Molecules 2020, 25(20), 4647; https://doi.org/10.3390/molecules25204647 - 12 Oct 2020

Cited by 25 | Viewed by 5061

Abstract

This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA derivatives. Then, the results of molecular modeling of HCA derivatives with prion protein as well as with α-synuclein fibrils are summarized, followed by detailed analysis of the experiments on the effect of natural and synthetic HCA derivatives, as well as structurally similar phenylacetic and benzoic acid derivatives, on the pathological transformation of prion protein and α-synuclein. The ability of HCA derivatives to prevent amyloid transformation of some amyloidogenic proteins, and their presence not only in food products but also as natural metabolites in human blood and tissues, makes them promising for the prevention and treatment of neurodegenerative diseases of amyloid nature. Full article

(This article belongs to the Special Issue Chemistry, Biology, and Pharmacology of Natural Phenolic Compounds and Their Synthetic Derivatives)

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