Innovative Approaches to Modify Polyphenols

A special issue of Molbank (ISSN 1422-8599).

Deadline for manuscript submissions: closed (30 April 2022) | Viewed by 8390

Special Issue Editors


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Guest Editor
Department of Pharmacy, Health, and Nutritional Sciences, University of Calabria Via Pietro Bucci, 87036 Arcavacata di Rende, CS, Italy
Interests: synthesis of heterocyclic compounds; chemotherapeutics; antioxidants; food-derived bioactive molecules; medicinal chemistry
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Assistant Guest Editor
Department of Chemistry, University of Milan, Via Golgi 19, 20133 Milan, Italy
Interests: medicinal chemistry; organic chemistry; chemical biology; new antibacterial small molecules; new antiviral small molecules
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Special Issue Information

Dear Colleagues,

Polyphenols are highly interesting natural products that can become innovative tools for pharmaceutical/cosmetic/nutraceutical research. This Special Issue aims to focus on chemistry approaches that try to achieve sustainability at the molecular level. Examples include the amelioration of extraction methods and chemical modifications to improve the solubility, bioavailability, shelf-life, and stability of polyphenols.

Dr. Francesca Aiello
Guest Editor

Dr. Gabriele Carullo
Dr. Sarah Mazzotta
Assistant Guest Editors

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Keywords

  • enzymatic reactions
  • waste prevention
  • renewable feedstocks
  • safer solvents
  • catalysis

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Published Papers (3 papers)

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Research

12 pages, 1628 KiB  
Communication
2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate: Synthesis, In Silico Analysis and In Vitro Pharmacological Evaluation
by Antonella Brizzi, Alfonso Trezza, Ottavia Spiga, Samuele Maramai, Francesco Scorzelli, Simona Saponara and Fabio Fusi
Molbank 2021, 2021(3), M1258; https://doi.org/10.3390/M1258 - 23 Jul 2021
Cited by 1 | Viewed by 2406
Abstract
Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, [...] Read more.
Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, and vasorelaxant. The aim of the present work was the combination of the two molecules in a single chemical entity, conceivably endowed with more efficacious vasorelaxant activity. Preliminary in silico studies herein described suggested that the new hybrid compound bound spontaneously and with high affinity on the KCa1.1 channel. Thus, the synthesis of the 3′-ferulic ester derivative of quercetin was achieved and its structure confirmed by 1H- and 13C-NMR spectra, HSQC and HMBC experiments, mass spectrometry, and elementary analysis. The effect of the new hybrid compound on vascular KCa1.1 and CaV1.2 channels revealed a partial loss of the stimulatory activity that characterizes the parent compound quercetin. Therefore, further studies are necessary to identify a better strategy to improve the vascular properties of this flavonoid. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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4 pages, 471 KiB  
Short Note
7-Docosahexaenoyl-Quercetin
by Sarah Mazzotta, Gabriele Carullo, Fabio Sciubba, Maria Enrica Di Cocco and Francesca Aiello
Molbank 2021, 2021(2), M1203; https://doi.org/10.3390/M1203 - 15 Apr 2021
Cited by 2 | Viewed by 2204
Abstract
Fatty acids and polyphenols represent different classes of pharmacologically active molecules. Hybrid derivatives of these compounds are interesting therapeutic tools. They could be obtained using enzymatic approaches, which allow regioselective derivatizations. In this short note, the pancreatic porcine lipase was employed to mediate [...] Read more.
Fatty acids and polyphenols represent different classes of pharmacologically active molecules. Hybrid derivatives of these compounds are interesting therapeutic tools. They could be obtained using enzymatic approaches, which allow regioselective derivatizations. In this short note, the pancreatic porcine lipase was employed to mediate the regioselective synthesis of 7-docosahexaenoyl-quercetin was described. The C-7 regioisomer formation was confirmed by 1H-NMR experiment. Generally, in this approach the alcoholic OH- was preferred when present. Nevertheless, in this case, it was demonstrated that the hindrance of the acyl group is a variable to obtain a good regioselectivity in C-7 position, employing only one-step reaction. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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8 pages, 1538 KiB  
Short Note
(Z)-5-(3′,4′-Bis(benzyloxy)benzylidene)furan-2(5H)-one
by Angelica Artasensi, Giovanna Baron, Giulio Vistoli, Giancarlo Aldini and Laura Fumagalli
Molbank 2021, 2021(1), M1193; https://doi.org/10.3390/M1193 - 28 Feb 2021
Cited by 4 | Viewed by 2806
Abstract
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some [...] Read more.
Over the years secondary metabolites have been considered as lead molecules both in their natural form and as templates for medicinal chemistry. Some secondary metabolites such as polyphenols and flavan-3-ols exert beneficial effects after a modification by the microbiota. Synthetic precursors of some of these modified compounds, in turn, carried a γ-alkylidenebutenolide moiety which characterizes a large class of bioactive natural products endowed with a wide range of biological activities. For these reasons stereoselective preparation of γ-alkylidenebutenolide continues to be an important issue for organic chemists. Our objective is to synthetize the novel compound (Z)-5-(3′,4′-bis(benzyloxy)benzylidene)furan-2(5H)-one in a stereocontrolled-one-pot reaction. The product was obtained in good yield. Furthermore, the theoretical investigation of the transition states suggests a new procedure to achieve Z-isomer of β-unsubstituted γ-alkylidenebutenolide. Full article
(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)
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