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Chalcones: Biosynthesis, Functions, and Biological Implications
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Chalcones: Biosynthesis, Functions, and Biological Implications

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Biochemistry".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 6467

Special Issue Editor

Prof. Dr. Pál Perjési

E-Mail Website
Guest Editor
Institute of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Pécs, Rókus Str. 2, H-7624 Pécs, Hungary
Interests: organic chemistry; medicinal chemistry; chemical biology; bioorganic chemistry; molecular toxicology; glutathione; redox homeostasis, oxidative stress; reactive oxygen species; antioxidants; chemoprevention; chalcones; flavonoids; cyclic chalcone analogs; glutathione conjugation
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural and synthetic chalcones display various biological effects, including antibacterial, antiprotozoal, antimalarial, anti-inflammatory activities, cytotoxicity towards cancer cell lines, antiproliferative, and antitumor-promoting activities. The chalcone scaffold is one of the natural privileged structures with a geometry suitable for decoration with side chains, such that the resulting products interact with different target proteins. This Special Issue aims to summarize up-to-date data on isolation, synthesis, structural characterization, as well biological and industrial applications of natural and synthetic chalcones and chalcone derivatives.

Search for new natural chalcones and synthesis of their synthetic analogs are of continuous scientific interest. The number of recognized biological effects of the compounds and their mechanism of action continuously increases. Most of their biological effects are associated either with their noncovalent interactions with or covalent modification of the nucleophilic sites of cellular macromolecules. Furthermore, using chalcones as potential optical material is still a matter of interest. Nonlinear optical crystals are used in many different nonlinear parametric applications.

Accordingly, this Special Issue, "Chalcones: Biosynthesis, Functions and Biological Implications", aims to publish original research and review articles that explore the above potential topics.

Prof. Dr. Pál Perjési
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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. 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

  • Chalcones
  • Flavonoids
  • Synthesis
  • Biosynthesis
  • Stereochemistry
  • Physico-chemical characterization
  • Bioavailability
  • Biotransformations
  • Biological activities
  • Cytoprotection
  • Chemoprevention
  • Noncovalent interactions
  • Nucleophylic additions
  • Electronic spectra
  • Nonlinear optical materials

Published Papers (5 papers)

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Research

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13 pages, 2456 KiB  
Article
Protein Modelling Highlighted Key Catalytic Sites Involved in Position-Specific Glycosylation of Isoflavonoids
by Moon Sajid and Parwinder Kaur
Int. J. Mol. Sci. 2023, 24(15), 12356; https://doi.org/10.3390/ijms241512356 - 02 Aug 2023
Viewed by 998
Abstract
Uridine diphosphate glycosyltransferases (UGTs) are known for promiscuity towards sugar acceptors, a valuable characteristic for host plants but not desirable for heterologous biosynthesis. UGTs characterized for the O-glycosylation of isoflavonoids have shown a variable efficiency, substrate preference, and OH site specificity. Thus, 22 [...] Read more.
Uridine diphosphate glycosyltransferases (UGTs) are known for promiscuity towards sugar acceptors, a valuable characteristic for host plants but not desirable for heterologous biosynthesis. UGTs characterized for the O-glycosylation of isoflavonoids have shown a variable efficiency, substrate preference, and OH site specificity. Thus, 22 UGTs with reported isoflavonoid O-glycosylation activity were analyzed and ranked for OH site specificity and catalysis efficiency. Multiple-sequence alignment (MSA) showed a 33.2% pairwise identity and 4.5% identical sites among selected UGTs. MSA and phylogenetic analysis highlighted a comparatively higher amino acid substitution rate in the N-terminal domain that likely led to a higher specificity for isoflavonoids. Based on the docking score, OH site specificity, and physical and chemical features of active sites, selected UGTs were divided into three groups. A significantly high pairwise identity (67.4%) and identical sites (31.7%) were seen for group 1 UGTs. The structural and chemical composition of active sites highlighted key amino acids that likely define substrate preference, OH site specificity, and glycosylation efficiency towards selected (iso)flavonoids. In conclusion, physical and chemical parameters of active sites likely control the position-specific glycosylation of isoflavonoids. The present study will help the heterologous biosynthesis of glycosylated isoflavonoids and protein engineering efforts to improve the substrate and site specificity of UGTs. Full article
(This article belongs to the Special Issue Chalcones: Biosynthesis, Functions, and Biological Implications)
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22 pages, 6556 KiB  
Article
The Effects of 2′-Hydroxy-3,6′-Dimethoxychalcone on Melanogenesis and Inflammation
by Sungmin Bae and Chang-Gu Hyun
Int. J. Mol. Sci. 2023, 24(12), 10393; https://doi.org/10.3390/ijms241210393 - 20 Jun 2023
Viewed by 1163
Abstract
In this study, we demonstrated that 2′-hydroxy-3,6′-dimethoxychalcone (3,6′-DMC) alleviated α-MSH-induced melanogenesis and lipopolysaccharides (LPS)-induced inflammation in mouse B16F10 and RAW 264.7 cells. In vitro analysis results showed that the melanin content and intracellular tyrosinase activity were [...] Read more.
In this study, we demonstrated that 2′-hydroxy-3,6′-dimethoxychalcone (3,6′-DMC) alleviated α-MSH-induced melanogenesis and lipopolysaccharides (LPS)-induced inflammation in mouse B16F10 and RAW 264.7 cells. In vitro analysis results showed that the melanin content and intracellular tyrosinase activity were significantly decreased by 3,6′-DMC, without cytotoxicity, via decreases in tyrosinase and the tyrosinase-related protein 1 (TRP-1) and TRP-2 melanogenic proteins, as well as the downregulation of microphthalmia-associated transcription factor (MITF) expression through the upregulation of the phosphorylation of extracellular-signal-regulated kinase (ERK), phosphoinositide 3-kinase (PI3K)/Akt, and glycogen synthase kinase-3β (GSK-3β)/catenin, and downregulation of the phosphorylation of p38, c-Jun N-terminal kinase (JNK), and protein kinase A (PKA). Furthermore, we investigated the effect of 3,6′-DMC on macrophage RAW264.7 cells with LPS stimulation. 3,6′-DMC significantly inhibited LPS-stimulated nitric oxide production. 3,6′-DMC also suppressed the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 on the protein level. In addition, 3,6′-DMC decreased the production of the tumor necrosis factor-α and interleukin-6. Successively, our mechanistic studies revealed that 3,6′-DMC also suppressed the LPS-induced phosphorylation of the inhibitor of IκBα, p38MAPK, ERK, and JNK. The Western blot assay results showed that 3,6′-DMC suppresses LPS-induced p65 translocation from cytosol to the nucleus. Finally, the topical applicability of 3,6′-DMC was tested through primary skin irritation, and it was found that 3,6′-DMC, at 5 and 10 μM concentrations, did not cause any adverse effects. Therefore, 3,6′-DMC may provide a potential candidate for preventing and treating melanogenic and inflammatory skin diseases. Full article
(This article belongs to the Special Issue Chalcones: Biosynthesis, Functions, and Biological Implications)
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17 pages, 4436 KiB  
Article
(E)-2-Benzylidenecyclanones: Part XVIII Study the Possible Link between Glutathione Reactivity and Cancer Cell Cytotoxic Effects of Some Cyclic Chalcone Analogs A Comparison of the Reactivity of the Open-Chain and the Seven-Membered Homologs
by Fatemeh Kenari, Szilárd Molnár, Igor D. Borges, Hamilton B. Napolitano and Pál Perjési
Int. J. Mol. Sci. 2023, 24(10), 8557; https://doi.org/10.3390/ijms24108557 - 10 May 2023
Cited by 2 | Viewed by 1499
Abstract
Non-enzymatic thiol addition into the α,β-unsaturated carbonyl system is associated with several biological effects. In vivo, the reactions can form small-molecule thiol (e.g., glutathione) or protein thiol adducts. The reaction of two synthetic (4′-methyl- and 4′-methoxy substituted) cyclic chalcone analogs with reduced glutathione [...] Read more.
Non-enzymatic thiol addition into the α,β-unsaturated carbonyl system is associated with several biological effects. In vivo, the reactions can form small-molecule thiol (e.g., glutathione) or protein thiol adducts. The reaction of two synthetic (4′-methyl- and 4′-methoxy substituted) cyclic chalcone analogs with reduced glutathione (GSH) and N-acetylcysteine (NAC) was studied by (high-pressure liquid chromatography-ultraviolet spectroscopy) HPLC-UV method. The selected compounds displayed in vitro cancer cell cytotoxicity (IC50) of different orders of magnitude. The structure of the formed adducts was confirmed by (high-pressure liquid chromatography-mass spectrometry) HPLC-MS. The incubations were performed under three different pH conditions (pH 3.2/3.7, 6.3/6.8, and 8.0/7.4). The chalcones intrinsically reacted with both thiols under all incubation conditions. The initial rates and compositions of the final mixtures depended on the substitution and the pH. The frontier molecular orbitals and the Fukui function were carried out to investigate the effects on open-chain and seven-membered cyclic analogs. Furthermore, machine learning protocols were used to provide more insights into physicochemical properties and to support the different thiol-reactivity. HPLC analysis indicated diastereoselectivity of the reactions. The observed reactivities do not directly relate to the different in vitro cancer cell cytotoxicity of the compounds. Full article
(This article belongs to the Special Issue Chalcones: Biosynthesis, Functions, and Biological Implications)
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Review

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20 pages, 690 KiB  
Review
Natural Chalcones for the Management of Obesity Disease
by Maria Maisto, Adua Marzocchi, Niloufar Keivani, Vincenzo Piccolo, Vincenzo Summa and Gian Carlo Tenore
Int. J. Mol. Sci. 2023, 24(21), 15929; https://doi.org/10.3390/ijms242115929 - 03 Nov 2023
Viewed by 972
Abstract
In the last decade, the incidence of obesity has increased dramatically worldwide, reaching a dangerous pandemic spread. This condition has serious public health implications as it significantly increases the risk of chronic diseases such as type 2 diabetes, fatty liver, hypertension, heart attack, [...] Read more.
In the last decade, the incidence of obesity has increased dramatically worldwide, reaching a dangerous pandemic spread. This condition has serious public health implications as it significantly increases the risk of chronic diseases such as type 2 diabetes, fatty liver, hypertension, heart attack, and stroke. The treatment of obesity is therefore the greatest health challenge of our time. Conventional therapeutic treatment of obesity is based on the use of various synthetic molecules belonging to the class of appetite suppressants, lipase inhibitors, hormones, metabolic regulators, and inhibitors of intestinal peptide receptors. The long-term use of these molecules is generally limited by various side effects and tolerance. For this reason, the search for natural alternatives to treat obesity is a current research goal. This review therefore examined the anti-obesity potential of natural chalcones based on available evidence from in vitro and animal studies. In particular, the results of the main in vitro studies describing the principal molecular therapeutic targets and the mechanism of action of the different chalcones investigated were described. In addition, the results of the most relevant animal studies were reported. Undoubtedly, future clinical studies are urgently needed to confirm and validate the potential of natural chalcones in the clinical prophylaxis of obesity. Full article
(This article belongs to the Special Issue Chalcones: Biosynthesis, Functions, and Biological Implications)
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18 pages, 6616 KiB  
Review
Hydroxy Chalcones and Analogs with Chemopreventive Properties
by Mihail Lucian Birsa and Laura G. Sarbu
Int. J. Mol. Sci. 2023, 24(13), 10667; https://doi.org/10.3390/ijms241310667 - 26 Jun 2023
Cited by 3 | Viewed by 1198
Abstract
The aim of this review is to highlight the chemopreventive properties of hydroxy-substituted natural and synthetic chalcones along with a number of their analogs. These products display various biological activities, and have many applications against various diseases. Antioxidant and anti-inflammatory properties of chalcones [...] Read more.
The aim of this review is to highlight the chemopreventive properties of hydroxy-substituted natural and synthetic chalcones along with a number of their analogs. These products display various biological activities, and have many applications against various diseases. Antioxidant and anti-inflammatory properties of chalcones bearing hydroxy substituents are underlined. The influence of hydroxy substituents located on ring A, B, or both are systematized according to the exhibited biological properties. Full article
(This article belongs to the Special Issue Chalcones: Biosynthesis, Functions, and Biological Implications)
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