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Biomolecules
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Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives
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Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives

A special issue of Biomolecules (ISSN 2218-273X). This special issue belongs to the section "Enzymology".

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 17224

Special Issue Editors

Prof. Dr. Ewa Białecka-Florjańczyk

E-Mail Website
Guest Editor
Department of Chemistry, Institute of Food Sciences, Warsaw University of Life Sciences-SGGW, Warsaw, Poland
Interests: biocatalysis; whole-cell catalysis; phenolic antioxidants
Dr. Bartłomiej Zieniuk

E-Mail Website
Guest Editor
Department of Chemistry, Institute of Food Sciences, Warsaw University of Life Sciences, Warsaw, Poland
Interests: lipase-catalyzed ester synthesis; lipophilization; enzymatic (trans)esterification; whole-cell modification of phenolic compounds; microbiology; yarrowia lipolytica; lipases biosynthesis; antimicrobial and antioxidant activities of phenolic compounds; microbial enzymes
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phenolic compounds are a large group of secondary metabolites of various chemical structures, widespread mainly in plants and fungi, ranging from 5,000 to 8,000 different chemical structures. The common part of these substances is the presence of an aromatic ring with a hydroxyl substituent. Phenolic compounds include flavonoids, phenolic acids, stilbenes and lignans as well as phenolic terpenes, alkylphenols, curcuminoids, coumarins or phenolic derivatives of aldehydes, ketones and alcohols. These substances are present in large amounts in herbs and cereals, berries, as well as in coffee, tea, beer and red wine. They influence the modulation of plant growth and reproduction, defense mechanisms against microorganisms and the interaction between plants. Great interest in these compounds is related to their significant antioxidant and antibacterial potential, which translates into their therapeutic effects as well as practical, biological and pharmacological importance.

Despite so many biological activities of phenolic compounds and the interest in them not only from the scientific world these substances also have some disadvantages. Unfortunately, phenolic compounds suffer from low solubility in organic/aqueous environments, hence their application is often limited. One of the ways to change the solubility and biological properties of chemical compounds is their modification using biotechnological methods, such as biocatalysis or biotransformation.

Potential topics include, but are not limited to:

  • whole-cell modification of phenolic compounds
  • lipase-catalyzed ester synthesis
  • enzymatic (trans)esterification
  • enzymatic synthesis of lipophilic antioxidants and antimicrobials
  • enzymatic lipophilization of phenolic extracts
  • lipids modification

Prof. Dr. Ewa Białecka-Florjańczyk
Dr. Bartłomiej Zieniuk
Guest Editors

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. Biomolecules is an international peer-reviewed open access monthly 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

  • biocatalysis
  • biotransformation
  • enzyme-catalyzed reactions
  • whole-cell catalysis
  • green chemistry
  • enzymes
  • phenolic compounds
  • polyphenols
  • lipases
  • lipophilization
  • enzymatic synthesis
  • esterification
  • transesterification

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Published Papers (5 papers)

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Research

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20 pages, 2947 KiB  
Article
From Hamamelitannin Synthesis to the Study of Enzymatic Acylations of D-Hamamelose
by Mária Mastihubová and Vladimír Mastihuba
Biomolecules 2023, 13(3), 519; https://doi.org/10.3390/biom13030519 - 12 Mar 2023
Cited by 1 | Viewed by 2130
Abstract
The bioactive natural substance, hamamelitannin, was effectively synthesized in two ways. The chemical acylation of 2,3-O-isopropylidene-α,β-D-hamamelofuranose promoted by Bu2SnO using 3,4,5-tri-O-acetylgalloyl chloride, followed by the deprotection provided hamamelitannin in 79%. Pilot enzymatic benzoylation of D-hamamelose using vinyl [...] Read more.
The bioactive natural substance, hamamelitannin, was effectively synthesized in two ways. The chemical acylation of 2,3-O-isopropylidene-α,β-D-hamamelofuranose promoted by Bu2SnO using 3,4,5-tri-O-acetylgalloyl chloride, followed by the deprotection provided hamamelitannin in 79%. Pilot enzymatic benzoylation of D-hamamelose using vinyl benzoate (4 equiv.) and Lipozyme TL IM as a biocatalyst in t-butyl methyl ether (t-BuMeO) gave mainly benzoylated furanoses (89%), of which tribenzoates reached (52%). Enzymatic galloylation of 2,3-O-isopropylidene-α,β-D-hamamelofuranose with vinyl gallate under the catalysis of Lipozyme TL IM in t-butyl alcohol (t-BuOH) or t-BuMeO provided only the 5-O-galloylated product. The reaction in t-BuMeO proceeded in a shorter reaction time (61 h) and higher yield (82%). The more hydrophobic vinyl 3,4,5-tri-O-acetylgallate in the same reactions gave large amounts of acetylated products. Vinyl gallate and triacetylgallate in the enzymatic acylation of D-hamamelose with Lipozyme TL IM in t-BuMeO yielded 2′,5-diacylated hamamelofuranoses in a yield below 20%. The use of other vinyl gallates hydrophobized by methylation or benzylation provided 2′,5-diacylated hamamelofuranoses in good yields (65–84%). The reaction with silylated vinyl gallate did not proceed. The best results were obtained with vinyl 2,3,5-tri-O-benzyl gallate, and the only product, 2′,5-diacylated hamamelofuranoside precipitated from the reaction mixture (84% in 96 h). After debenzylation, hamamelitannin was obtained an 82% yield from hamamelose in two steps. This synthesis is preparatively undemanding and opens the way to multigram preparations of bioactive hamamelitannin and its analogues. Full article
(This article belongs to the Special Issue Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives)
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22 pages, 5889 KiB  
Article
Development of a Multi-Enzymatic Approach for the Modification of Biopolymers with Ferulic Acid
by Archontoula Giannakopoulou, Georgia Tsapara, Anastassios N. Troganis, Panagiota Koralli, Christos L. Chochos, Angeliki C. Polydera, Petros Katapodis, Nektaria-Marianthi Barkoula and Haralambos Stamatis
Biomolecules 2022, 12(7), 992; https://doi.org/10.3390/biom12070992 - 17 Jul 2022
Cited by 3 | Viewed by 3499
Abstract
A series of polymers, including chitosan (CS), carboxymethylcellulose (CMC) and a chitosan–gelatin (CS–GEL) hybrid polymer, were functionalized with ferulic acid (FA) derived from the enzymatic treatment of arabinoxylan through the synergistic action of two enzymes, namely, xylanase and feruloyl esterase. Subsequently, the ferulic [...] Read more.
A series of polymers, including chitosan (CS), carboxymethylcellulose (CMC) and a chitosan–gelatin (CS–GEL) hybrid polymer, were functionalized with ferulic acid (FA) derived from the enzymatic treatment of arabinoxylan through the synergistic action of two enzymes, namely, xylanase and feruloyl esterase. Subsequently, the ferulic acid served as the substrate for laccase from Agaricus bisporus (AbL) in order to enzymatically functionalize the above-mentioned polymers. The successful grafting of the oxidized ferulic acid products onto the different polymers was confirmed through ultraviolet–visible (UV–Vis) spectroscopy, attenuated total reflectance (ATR) spectroscopy, scanning electron microscopy (SEM) and nuclear magnetic resonance (NMR) spectroscopy. Additionally, an enhancement of the antioxidant properties of the functionalized polymers was observed according to the DDPH and ABTS protocols. Finally, the modified polymers exhibited strong antimicrobial activity against bacterial populations of Escherichia coli BL21DE3 strain, suggesting their potential application in pharmaceutical, cosmeceutical and food industries. Full article
(This article belongs to the Special Issue Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives)
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Review

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41 pages, 2973 KiB  
Review
Dihydrocaffeic Acid—Is It the Less Known but Equally Valuable Phenolic Acid?
by Bartłomiej Zieniuk
Biomolecules 2023, 13(5), 859; https://doi.org/10.3390/biom13050859 - 18 May 2023
Cited by 4 | Viewed by 2908
Abstract
Dihydrocaffeic acid (DHCA) is a phenolic acid bearing a catechol ring and three-carbon side chain. Despite its being found in minor amounts in numerous plants and fungi of different origins, it has attracted the interest of various research groups in many fields of [...] Read more.
Dihydrocaffeic acid (DHCA) is a phenolic acid bearing a catechol ring and three-carbon side chain. Despite its being found in minor amounts in numerous plants and fungi of different origins, it has attracted the interest of various research groups in many fields of science, from food to biomedical applications. The review article presented herein aims to show a wider audience the health benefits and therapeutic, industrial, and nutritional potential of dihydrocaffeic acid, by sheddinglight on its occurrence, biosynthesis, bioavailability, and metabolism. The scientific literature describes at least 70 different derivatives of dihydrocaffeic acid, both those occurring naturally and those obtained via chemical and enzymatic methods. Among the most frequently used enzymes that were applied for the modification of the parent DHCA structure, there are lipases that allow for obtaining esters and phenolidips, tyrosinases used for the formation of the catechol ring, and laccases to functionalize this phenolic acid. In many studies, both in vitro and in vivo, the protective effect of DHCA and its derivatives on cells subjected to oxidative stress and inflammation were acknowledged. Full article
(This article belongs to the Special Issue Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives)
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25 pages, 9999 KiB  
Review
Bio-Based Valorization of Lignin-Derived Phenolic Compounds: A Review
by Ludmila Martínková, Michal Grulich, Miroslav Pátek, Barbora Křístková and Margit Winkler
Biomolecules 2023, 13(5), 717; https://doi.org/10.3390/biom13050717 - 22 Apr 2023
Cited by 21 | Viewed by 4554
Abstract
Lignins are the most abundant biopolymers that consist of aromatic units. Lignins are obtained by fractionation of lignocellulose in the form of “technical lignins”. The depolymerization (conversion) of lignin and the treatment of depolymerized lignin are challenging processes due to the complexity and [...] Read more.
Lignins are the most abundant biopolymers that consist of aromatic units. Lignins are obtained by fractionation of lignocellulose in the form of “technical lignins”. The depolymerization (conversion) of lignin and the treatment of depolymerized lignin are challenging processes due to the complexity and resistance of lignins. Progress toward mild work-up of lignins has been discussed in numerous reviews. The next step in the valorization of lignin is the conversion of lignin-based monomers, which are limited in number, into a wider range of bulk and fine chemicals. These reactions may need chemicals, catalysts, solvents, or energy from fossil resources. This is counterintuitive to green, sustainable chemistry. Therefore, in this review, we focus on biocatalyzed reactions of lignin monomers, e.g., vanillin, vanillic acid, syringaldehyde, guaiacols, (iso)eugenol, ferulic acid, p-coumaric acid, and alkylphenols. For each monomer, its production from lignin or lignocellulose is summarized, and, mainly, its biotransformations that provide useful chemicals are discussed. The technological maturity of these processes is characterized based on, e.g., scale, volumetric productivities, or isolated yields. The biocatalyzed reactions are compared with their chemically catalyzed counterparts if the latter are available. Full article
(This article belongs to the Special Issue Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives)
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19 pages, 1215 KiB  
Review
Phenolipids, Amphipilic Phenolic Antioxidants with Modified Properties and Their Spectrum of Applications in Development: A Review
by Silvia Ivonne Arzola-Rodríguez, Laila-Nayzzel Muñoz-Castellanos, César López-Camarillo and Erika Salas
Biomolecules 2022, 12(12), 1897; https://doi.org/10.3390/biom12121897 - 17 Dec 2022
Cited by 15 | Viewed by 3072
Abstract
Polyphenols, as secondary metabolites from plants, possess a natural antioxidant capacity and biological activities attributed to their chemical and structural characteristics. Due to their mostly polar character, polyphenols present a low solubility in less polar environments or hydrophobic matrices. However, in order to [...] Read more.
Polyphenols, as secondary metabolites from plants, possess a natural antioxidant capacity and biological activities attributed to their chemical and structural characteristics. Due to their mostly polar character, polyphenols present a low solubility in less polar environments or hydrophobic matrices. However, in order to make polyphenols able to incorporate in oils and fats, a transformation strategy is necessary. For the above, the functionalization of polyphenols through chemical or enzymatic lipophilization has allowed the synthesis of phenolipids. These are amphipilic molecules that preserve the natural phenolic core to which an aliphatic motif is attached by esterification or transesterification reactions. The length of the aliphatic chain in phenolipids allows them to interact with different systems (such as emulsions, oily molecules, micelles and cellular membranes), which would favor their use in processed foods, as vehicles for drugs, antimicrobial agents, antioxidants in the cosmetic industry and even in the treatment of degenerative diseases related to oxidative stress Full article
(This article belongs to the Special Issue Recent Advances in the Enzymatic Synthesis of Phenolic Compounds Derivatives)
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