Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
6.7
4.6
Journals
Molecules
Special Issues
From Natural Polyphenols to Synthetic Bioactive Analogues
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

From Natural Polyphenols to Synthetic Bioactive Analogues

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

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 20463

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Corrado Tringali

E-Mail Website1 Website2
Guest Editor
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, I-95125 Catania, Italy
Interests: synthesis of natural-derived polyphenols; low environmental impact reagents and enzymes; isolation and identification of bioactive compounds; extraction and fractionation of biological material from natural sources

Special Issue Information

Dear Colleagues,

In recent years, phenolic compounds from plant sources, commonly referred to as ‘plant polyphenols’, have been the subject of an impressive number of research studies, to a large extent focused on the healthy properties attributed to diet polyphenols, including antioxidant, anti-inflammatory, antineoplastic, antidiabetic, neuroprotective, and other biological activities. Additionally, phenolic compounds isolated from toxic plants and showing cytotoxic or antiproliferative activity have been intensively investigated in view of a possible exploitation of their anticancer properties. In parallel, many research groups have focused their work on obtaining synthetic or semisynthetic analogues of these molecules, with the aim of enhancing their biological activity and possibly improving their metabolic stability and bioavailability, as a first step towards the discovery of new chemotherapeutics agents. The preparation of libraries of analogues derived from natural polyphenols may also contribute to a better understanding of the molecular mechanisms of action of the most promising compounds through structure-activity relationship (SAR) studies. Finally, synthetic compounds inspired to a natural scaffold may also show new and unexpected biological properties.

Thus, this Special Issue aims to highlight the most recent results both in the field of natural polyphenols and in that of their synthetic bioactive analogues. Original articles, as well as reviews, regarding studies on analogues of flavonoids, stilbenoids, curcuminoids, lignans, neolignans and polyphenol-derived compounds are welcome.

Prof. Dr. Corrado Tringali
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Polyphenols
  • Organic synthesis
  • Medicinal chemistry
  • Molecular modeling
  • Structure–activity relationship (SAR)
  • Biological activity
  • Bioinspired compounds
  • Antiproliferative
  • Anti-inflammatory
  • Neuroprotective

Published Papers (6 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Editorial

Jump to: Research, Review

3 pages, 165 KiB  
Editorial
Special Issue: From Natural Polyphenols to Synthetic Bioactive Analogues
by Corrado Tringali
Molecules 2020, 25(12), 2772; https://doi.org/10.3390/molecules25122772 - 16 Jun 2020
Cited by 4 | Viewed by 1579
Abstract
In recent years, phenolic compounds from plant sources, commonly referred to as ‘plant polyphenols’, have been the subject of an impressive number of research studies, to a large extent focused on the healthy properties attributed to diet polyphenols, including antioxidant, anti-inflammatory, antineoplastic, antidiabetic, [...] Read more.
In recent years, phenolic compounds from plant sources, commonly referred to as ‘plant polyphenols’, have been the subject of an impressive number of research studies, to a large extent focused on the healthy properties attributed to diet polyphenols, including antioxidant, anti-inflammatory, antineoplastic, antidiabetic, neuroprotective, and other biological activities [...] Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)

Research

Jump to: Editorial, Review

17 pages, 2560 KiB  
Article
Synthesis of Bisphenol Neolignans Inspired by Honokiol as Antiproliferative Agents
by Nunzio Cardullo, Vincenza Barresi, Vera Muccilli, Giorgia Spampinato, Morgana D’Amico, Daniele Filippo Condorelli and Corrado Tringali
Molecules 2020, 25(3), 733; https://doi.org/10.3390/molecules25030733 - 07 Feb 2020
Cited by 14 | Viewed by 3838
Abstract
Honokiol (2) is a natural bisphenol neolignan showing a variety of biological properties, including antitumor activity. Some studies pointed out 2 as a potential anticancer agent in view of its antiproliferative and pro-apoptotic activity towards tumor cells. As a further contribution to these [...] Read more.
Honokiol (2) is a natural bisphenol neolignan showing a variety of biological properties, including antitumor activity. Some studies pointed out 2 as a potential anticancer agent in view of its antiproliferative and pro-apoptotic activity towards tumor cells. As a further contribution to these studies, we report here the synthesis of a small library of bisphenol neolignans inspired by honokiol and the evaluation of their antiproliferative activity. The natural lead was hence subjected to simple chemical modifications to obtain the derivatives 3–9; further neolignans (12a-c, 13a-c, 14a-c, and 15a) were synthesized employing the Suzuki–Miyaura reaction, thus obtaining bisphenols with a substitution pattern different from honokiol. These compounds and the natural lead were subjected to antiproliferative assay towards HCT-116, HT-29, and PC3 tumor cell lines. Six of the neolignans show GI50 values lower than those of 2 towards all cell lines. Compounds 14a, 14c, and 15a are the most effective antiproliferative agents, with GI50 in the range of 3.6–19.1 µM, in some cases it is lower than those of the anticancer drug 5-fluorouracil. Flow cytometry experiments performed on these neolignans showed that the inhibition of proliferation is mainly due to an apoptotic process. These results indicate that the structural modification of honokiol may open the way to obtaining antitumor neolignans more potent than the natural lead. Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)
►▼ Show Figures

Graphical abstract

19 pages, 1516 KiB  
Article
Multicomponent Synthesis of Polyphenols and Their In Vitro Evaluation as Potential β-Amyloid Aggregation Inhibitors
by Denise Galante, Luca Banfi, Giulia Baruzzo, Andrea Basso, Cristina D’Arrigo, Dario Lunaccio, Lisa Moni, Renata Riva and Chiara Lambruschini
Molecules 2019, 24(14), 2636; https://doi.org/10.3390/molecules24142636 - 19 Jul 2019
Cited by 8 | Viewed by 3466
Abstract
While plant polyphenols possess a variety of biological properties, exploration of chemical diversity around them is still problematic. Here, an example of application of the Ugi multicomponent reaction to the combinatorial assembly of artificial, yet “natural-like”, polyphenols is presented. The synthesized compounds represent [...] Read more.
While plant polyphenols possess a variety of biological properties, exploration of chemical diversity around them is still problematic. Here, an example of application of the Ugi multicomponent reaction to the combinatorial assembly of artificial, yet “natural-like”, polyphenols is presented. The synthesized compounds represent a second-generation library directed to the inhibition of β-amyloid protein aggregation. Chiral enantiopure compounds, and polyphenol-β-lactam hybrids have been prepared too. The biochemical assays have highlighted the importance of the key pharmacophores in these compounds. A lead for inhibition of aggregation of truncated protein AβpE3-42 was selected. Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)
►▼ Show Figures

Graphical abstract

15 pages, 872 KiB  
Article
Isorhamnetin, Hispidulin, and Cirsimaritin Identified in Tamarix ramosissima Barks from Southern Xinjiang and Their Antioxidant and Antimicrobial Activities
by Xiaopu Ren, Yingjie Bao, Yuxia Zhu, Shixin Liu, Zengqi Peng, Yawei Zhang and Guanghong Zhou
Molecules 2019, 24(3), 390; https://doi.org/10.3390/molecules24030390 - 22 Jan 2019
Cited by 37 | Viewed by 3832
Abstract
As a natural potential resource, Tamarix ramosissima has been widely used as barbecue skewers for a good taste and unique flavor. The polyphenolics in the branch bark play a key role in the quality improvement. The purposes of the present work were to [...] Read more.
As a natural potential resource, Tamarix ramosissima has been widely used as barbecue skewers for a good taste and unique flavor. The polyphenolics in the branch bark play a key role in the quality improvement. The purposes of the present work were to explore the polyphenolic composition of T. ramosissima bark extract and assess their potential antioxidant and antimicrobial activities. Hispidulin and cirsimaritin from T. ramosissima bark extract were first identified in the Tamarix genus reported with UPLC-MS analysis. Isorhamnetin (36.91 μg/mg extract), hispidulin (28.79 μg/mg extract) and cirsimaritin (13.35 μg/mg extract) are rich in the bark extract. The extract exhibited promising antioxidant activity with IC50 values of 117.05 μg/mL for 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 151.57 μg/mL for hydroxyl radical scavenging activities, as well as excellent reducing power with an EC50 of 93.77 μg/mL. The bark extract showed appreciable antibacterial properties against foodborne pathogens. Listeria monocytogenes was the most sensitive microorganism with the lowest minimum inhibitory concentration (MIC) value of 5 mg/mL and minimum bactericidal concentration (MBC) value of 10 mg/mL followed by S. castellani and S. aureus among the tested bacteria. The T. ramosissima bark extract showed significantly stronger inhibitory activity against Gram-positive than Gram-negative bacteria. Nevertheless, this extract failed to show any activity against tested fungi. Overall, these results suggested that T. ramosissima shows potential in improving food quality due to its highly efficacious antioxidant and antibacterial properties. Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)
►▼ Show Figures

Graphical abstract

15 pages, 1440 KiB  
Article
Melaleuca styphelioides Sm. Polyphenols Modulate Interferon Gamma/Histamine-Induced Inflammation in Human NCTC 2544 Keratinocytes
by Ferdaous Albouchi, Rosanna Avola, Gianluigi Maria Lo Dico, Vittorio Calabrese, Adriana Carol Eleonora Graziano, Manef Abderrabba and Venera Cardile
Molecules 2018, 23(10), 2526; https://doi.org/10.3390/molecules23102526 - 02 Oct 2018
Cited by 17 | Viewed by 3380
Abstract
Melaleuca styphelioides, known as the prickly-leaf tea tree, contains a variety of bioactive compounds. The purposes of this study were to characterize the polyphenols extracted from Melaleuca styphelioides leaves and assess their potential antioxidant and anti-inflammatory effects. The polyphenol extracts were prepared [...] Read more.
Melaleuca styphelioides, known as the prickly-leaf tea tree, contains a variety of bioactive compounds. The purposes of this study were to characterize the polyphenols extracted from Melaleuca styphelioides leaves and assess their potential antioxidant and anti-inflammatory effects. The polyphenol extracts were prepared by maceration with solvents of increasing polarity. The LC/MS-MS technique was used to identify and quantify the phenolic compounds. An assessment of the radical scavenging activity of all extracts was performed using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonate) (ABTS+), and ferric reducing antioxidant power (FRAP) assays. The anti-inflammatory activity was determined on interferon gamma (IFN-γ)/histamine (H)-stimulated human NCTC 2544 keratinocytes by Western blot and RT-PCR. Compared to other solvents, methanolic extract presented the highest level of phenolic contents. The most frequent phenolic compounds were quercetin, followed by gallic acid and ellagic acid. DPPH, ABTS+, and FRAP assays showed that methanolic extract exhibits strong concentration-dependent antioxidant activity. IFN-γ/H treatment of human NCTC 2544 keratinocytes induced the secretion of high levels of the pro-inflammatory mediator inter-cellular adhesion molecule-1 (ICAM-1), nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and nuclear factor kappa B (NF-κB), which were inhibited by extract. In conclusion, the extract of Melaleuca styphelioides leaves is rich in flavonoids, and presents antioxidant and anti-inflammatory proprieties. It can be proposed as a useful compound to treat inflammatory skin diseases. Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)
►▼ Show Figures

Graphical abstract

Review

Jump to: Editorial, Research

13 pages, 3623 KiB  
Review
Aza- and Azo-Stilbenes: Bio-Isosteric Analogs of Resveratrol
by Gérard Lizard, Norbert Latruffe and Dominique Vervandier-Fasseur
Molecules 2020, 25(3), 605; https://doi.org/10.3390/molecules25030605 - 30 Jan 2020
Cited by 20 | Viewed by 3804
Abstract
Several series of natural polyphenols are described for their biological and therapeutic potential. Natural stilbenoid polyphenols, such as trans-resveratrol, pterostilbene and piceatannol are well-known for their numerous biological activities. However, their moderate bio-availabilities, especially for trans-resveratrol, prompted numerous research groups to investigate innovative [...] Read more.
Several series of natural polyphenols are described for their biological and therapeutic potential. Natural stilbenoid polyphenols, such as trans-resveratrol, pterostilbene and piceatannol are well-known for their numerous biological activities. However, their moderate bio-availabilities, especially for trans-resveratrol, prompted numerous research groups to investigate innovative and relevant synthetic resveratrol derivatives. This review is focused on isosteric resveratrol analogs aza-stilbenes and azo-stilbenes in which the C=C bond between both aromatic rings was replaced with C=N or N=N bonds, respectively. In each series, synthetic ways will be displayed, and structural sights will be highlighted and compared with those of resveratrol. The biological activities of some of these molecules will be presented as well as their potential therapeutic applications. In some cases, structure-activity relationships will be discussed. Full article
(This article belongs to the Special Issue From Natural Polyphenols to Synthetic Bioactive Analogues)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-6
Back to TopTop