Carbohydrate Research最新文献

{"title":"Synthesis and antioxidant evaluation of coumarin-functionalised chitosan: A potent, non-toxic free radical scavenging compound.","authors":"Siyu Zhu, Qin Miao, Qiuhong Chen, Liguang Tian, Fang Dong, Zhanyong Guo, Qing Li","doi":"10.1016/j.carres.2024.109311","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109311","url":null,"abstract":"<p><p>In the present study, we designed to link the coumarin molecule to chitosan via a triazole group and synthesized chitosan-coumarin derivatives, which were further quaternized in one step in order to further improve their solubility to obtain a second series of chitosan-coumarin ammonium salt derivatives. The structures of these chitosan derivatives were verified by FT-IR and ¹H NMR. They were tested for their antioxidant activities. The experimental results showed that the derivatives had excellent free radical scavenging ability. The introduction of the coumarin moiety significantly improved the antioxidant activity, and the scavenging capacity was much higher than that of the chitosan feedstock in all three antioxidant tests. Overall, the scavenging capacity of chitosan-coumarin ammonium salt derivatives was slightly higher than that of chitosan-coumarin derivatives, with the highest scavenging rates in all three tests. Compound 8B scavenged 98.74 % (0.01 mg/mL) of superoxide anion radicals, compound 8D scavenged 95.5 % (0.3 mg/mL) of DPPH radicals and compound 8A scavenged 92.97 % (0.2 mg/mL) of hydroxyl radicals. Toxicity assays used L929 cells demonstrated that there was no significant toxicity of the derivatives. The results indicated that the chitosan derivatives described herein were safe and non-toxic and have good antioxidant activity.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109311"},"PeriodicalIF":2.4,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142791033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Recent trends in the separation and analysis of chitooligomers.","authors":"Lucie Petrásková, Pavla Bojarová","doi":"10.1016/j.carres.2024.109337","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109337","url":null,"abstract":"<p><p>Chitosan is a widely used linear biopolymer composed mainly of glucosamine and to a lesser extent of N-acetylglucosamine units. Many biological activities of chitosan are attributed to its shorter oligomeric chains, which consist of chitosan prepared either by enzyme activity (lysozyme, bacterial chitinase) or chemically by acid-catalyzed hydrolysis (e.g. in the stomach). However, these processes always result in a mixture of shorter chitooligosaccharides with varying degrees of acetylation whereas for relevant results of biological studies it is necessary to work with a precisely defined material. In this review, we provide an overview and comparison of analytical methods leading to the determination of the degree of polymerization (DP), the degree of acetylation (DA), the fraction of acetylation (FA) and the acetylation patterns (PA) of chitooligosaccharide chains and of the current state of knowledge on chitooligosaccharide separation. This review aims to present the most promising routes to well-defined low molecular weight chitosan with low dispersity.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109337"},"PeriodicalIF":2.4,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142790975","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A review on the biological activities and the nutraceutical potential of chitooligosaccharides.","authors":"Makyson R S Leal, Luiza R A Lima, Natalie E R Rodrigues, Paulo A G Soares, Maria G Carneiro-da-Cunha, Priscilla B S Albuquerque","doi":"10.1016/j.carres.2024.109336","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109336","url":null,"abstract":"<p><p>Chitooligosaccharides (CHOS) or chitosan oligosaccharides (COS) are oligomers mainly composed of d-glucosamine (GlcN) units and structured in a positively charged, basic, amino molecule obtained from the degradation of chitin/chitosan through physical, chemical, or enzymatic methods. CHOS display physicochemical properties attractive to applications from the food to the biomedical field, such as non-toxicity to humans, high water solubility, low viscosity, biocompatibility, and biodegradability. These properties also allow CHOS to exert important biological activities, for example, antioxidant, antimicrobial, anti-inflammatory, immunomodulatory, antitumor, and hypocholesterolemic ones, besides to exhibit applications in food systems, technological, and nutraceutical potential. Therefore, this study summarized the synthesis and chemical structure, biological functions, and mechanisms of action of CHOS; with this, we aimed to contribute to the knowledge about the application of CHOS from the food to the biomedical industries.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109336"},"PeriodicalIF":2.4,"publicationDate":"2024-11-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142784213","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans","authors":"Zuchao Ma ,&nbsp;Harry E. Ensley ,&nbsp;Douglas W. Lowman ,&nbsp;Michael D. Kruppa ,&nbsp;David L. Williams","doi":"10.1016/j.carres.2024.109325","DOIUrl":"10.1016/j.carres.2024.109325","url":null,"abstract":"<div><div>Fungal mannans are located on the exterior of the fungal cell wall, where they interact with the environment and, ultimately, the human host. Mannans play a major role in shaping the innate immune response to fungal pathogens. Understanding the phosphodiester linkage and mannosyl repeat units in the acid-labile portion of mannans is crucial for comprehending their structure/activity relationships and for development of anti-fungal vaccines and immunomodulators. The phosphodiester linkages connect the acid-stable and acid-labile portions of the mannan polymer. Phosphate groups are attached to positions 4 and/or 6 of mannosyl repeat units in the acid-stable portion and to position 1 of mannosyl repeat units in the acid-labile portion. This review focuses on the synthesis of phosphodiester linkages as an approach to the development of mannan glycomimetics, which are based on natural product fungal mannans. Development of successful synthetic strategies for the phosphodiester linkages may enable the production of mannan glycomimetics that elicit anti-fungal immune responses against existing and emerging fungal pathogens, such as <em>Candida albicans</em> and <em>Candida auris</em>.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109325"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142722419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical extension and glycodendrimer formation of the matriglycan decasaccharide, -(3Xylα1-3GlcAβ1)5- and its affinity for laminin","authors":"Kota Kotera ,&nbsp;Ren Miyamoto ,&nbsp;Gakuto Mochizuki ,&nbsp;Takahiro Tamura ,&nbsp;Noriyoshi Manabe ,&nbsp;Yoshiki Yamaguchi ,&nbsp;Jun-ichi Tamura","doi":"10.1016/j.carres.2024.109328","DOIUrl":"10.1016/j.carres.2024.109328","url":null,"abstract":"<div><div>Muscle tissue is stabilized by the strong interaction between laminin and matriglycan. Matriglycan is a polysaccharide composed of the repeating disaccharide, -3Xylα1-3GlcAβ1-, and is a pivotal part of the core M3 <em>O</em>-mannosyl glycan. Patients with muscular dystrophy cannot synthesize matriglycan or the core M3 <em>O</em>-mannosyl glycan due to a defect in or the lack of glycosyltransferases owing to glycan synthesis. Therefore, a supply of matriglycan may be a powerful tool for reconstructing muscle tissue in these patients. We herein report the synthesis of a matriglycan-repeating decasaccharide and a dendrimer comprising three branches of the decasaccharide. The glycan was regio- and stereoselectively synthesized by the stepwise addition of the corresponding disaccharide unit. The immobilized decasaccharide and glycodendrimer bound to laminin-G-like domains 4 and 5 of laminin-α2. The dissociation constants of the decasaccharide and dendrimer obtained from bio-layer interferometry were estimated to be 4.4 × 10⁻⁸ M and 6.8 × 10⁻⁸ M, respectively, showing higher affinity than those of a matriglycan-repeating hexasaccharide (1.6 × 10⁻⁷ M) and the dendrimer (1.8 × 10⁻⁷ M).</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109328"},"PeriodicalIF":2.4,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702510","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of a heptasaccharide N-glycan comprising two mannose-6-phosphate residues","authors":"Nozomi Ishii ,&nbsp;Andrea Mascherpa ,&nbsp;Antony J. Fairbanks","doi":"10.1016/j.carres.2024.109327","DOIUrl":"10.1016/j.carres.2024.109327","url":null,"abstract":"<div><div>A deprotected biantennary high mannose heptasaccharide <em>N</em>-glycan comprising two mannose-6-phosphate residues was synthesised as a putative ligand for the mannose 6-phosphate receptors, using a convergent [3 + 4] glycosylation strategy.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109327"},"PeriodicalIF":2.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Tricine-modified chitosan as a strategy for enhancing hydrophilicity and gene delivery","authors":"Yasemin Tantan ,&nbsp;Özlem Kaplan ,&nbsp;Kevser Bal ,&nbsp;Sema Şentürk ,&nbsp;Emine Büşra Eker Fidan ,&nbsp;Sibel Çelik ,&nbsp;Kamber Demir ,&nbsp;Mehmet Koray Gök","doi":"10.1016/j.carres.2024.109326","DOIUrl":"10.1016/j.carres.2024.109326","url":null,"abstract":"<div><div>In this study, we investigated the effect of chitosan modification with tricine on transfection efficiency by preserving its ability to form complexes with plasmid DNA (pDNA) and increasing its hydrophilicity. The inherent limitations of chitosan, such as poor solubility at physiological pH, insufficient cellular uptake, and strong ionic interactions with pDNA, typically result in low transfection efficiency. To overcome these challenges, Tricine, a hydrophilic molecule containing a secondary amine group, was conjugated to chitosan. Chitosan of three different molecular weights (low, medium, and high) was modified with tricine. Structural characterization of the modified chitosan was conducted using Fourier Transformed Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR) analyses. The effects of tricine modification were assessed in terms of hydrophilicity/hydrophobicity, proton buffering capacity, particle size, PDI and zeta potential. Tricine modified low molecular weight chitosan nanoparticles (nLMWChi_Tri), which exhibit suitable properties for gene transfer studies, were evaluated regarding pDNA complexation ability, cytotoxicity and <em>in vitro</em> transfection efficiency. The results demonstrated that tricine modification enhanced the gene transfer potential of chitosan, making it competitive with the commercial transfection agent Lipofectamine™ 2000 and offering a promising strategy for non-viral gene therapy applications. Furthermore, the biocompatibility and biodegradability of chitosan, combined with the improved hydrophilicity provided by tricine, makes nLMWChi_Tri a safer and more sustainable option for repeated use in gene delivery, overcoming the major limitations associated with other synthetic vectors such as Lipofectamine™ 2000.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109326"},"PeriodicalIF":2.4,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142695292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structure of the K58 capsular polysaccharide produced by Acinetobacter baumannii isolate MRSN 31468 includes Pse5Ac7Ac that is 4-O-acetylated by a phage-encoded acetyltransferase","authors":"Andrea Iovine ,&nbsp;Andrei V. Filatov ,&nbsp;Anastasiya A. Kasimova ,&nbsp;Nowshin S. Sharar ,&nbsp;Stephanie J. Ambrose ,&nbsp;Andrey S. Dmitrenok ,&nbsp;Mikhail M. Shneider ,&nbsp;Anna M. Shpirt ,&nbsp;Andrei V. Perepelov ,&nbsp;Yuriy A. Knirel ,&nbsp;Ruth M. Hall ,&nbsp;Cristina De Castro ,&nbsp;Johanna J. Kenyon","doi":"10.1016/j.carres.2024.109324","DOIUrl":"10.1016/j.carres.2024.109324","url":null,"abstract":"<div><div>Capsular polysaccharide (CPS), a heteropolymeric carbohydrate structure present on the cell surface of most isolates of the bacterial pathogen <em>Acinetobacter baumannii</em>, is a major virulence determinant<em>.</em> Here, the CPS produced by <em>A. baumannii</em> MRSN 31468, which carries the KL58 CPS biosynthesis locus, was studied by sugar analysis, one- and two-dimensional ¹H and ¹³C NMR spectroscopy. The structure was found to consist of a repeating tetrasaccharide K-unit that includes glucose (d-Glc<em>p</em>), galactose (d-Gal<em>p</em>), <em>N</em>-acetyl-galactosamine (d-Gal<em>p</em>NAc), and 5,7-diacetamido-3,5,7,9-tetradeoxy-<span>l</span>-<em>glycero</em>-<span>l</span>-<em>manno</em>-non-2-ulosonic acid (5,7-di-<em>N</em>-acetylpseudaminic acid; Pse5Ac7Ac). The CPS has a branched repeating unit with the disaccharide →3)-β-d-Glc-(1→3)-β-d-GalNAc-(1→ as the mainchain and O-6 of the Glc unit substituted with the disaccharide β-Pse5Ac7Ac-(2→6)-α-d-Gal, and Pse5Ac7Ac is partially acetylated at O-4. The presence of Pse5Ac7Ac in the K58 structure is consistent with the presence of <em>psaA-F</em> genes in KL58, which are responsible for Pse5Ac7Ac synthesis. 4-O-acetylation of Pse5Ac7Ac was traced to an acetyltransferase, Atr44<em>,</em> which was found to be closely related to Atr29 that similarly decorates Pse5Ac7Ac with 4OAc in the K46-type CPS. Atr44 like Atr29 is encoded by a gene found in a prophage. The K58 CPS produced by MRSN 31468 did not include the 8-epimer of Pse5Ac7Ac (5,7-di-<em>N</em>-acetyl-8-epipseudaminic acid; 8ePse5Ac7Ac) found in the closely related CPS from BAL062 that also carries KL58. Hence, the gene(s) for conversion of Pse5Ac7Ac to 8ePse5Ac7Ac must lie elsewhere.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109324"},"PeriodicalIF":2.4,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142695285","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Carboxymethylation of β-Glucan from Pythium insidiosum: Structural characterization and preliminary adsorption evaluation of DON and T2 toxin","authors":"Juliana S.M. Tondolo ,&nbsp;Gilson Zeni ,&nbsp;Guilherme L. Sassaki ,&nbsp;Janio M. Santurio ,&nbsp;Erico S. Loreto","doi":"10.1016/j.carres.2024.109323","DOIUrl":"10.1016/j.carres.2024.109323","url":null,"abstract":"<div><div>This study aimed to evaluate the impact of carboxymethylation on the structural and functional properties of β-glucan derived from the pathogenic oomycete <em>Pythium insidiosum</em>. β-Glucan was extracted and subjected to carboxymethylation (CM-glucan), with structural changes analyzed using ¹³C and ¹H NMR spectroscopy. The modified β-glucan's ability to adsorb mycotoxins, specifically deoxynivalenol (DON) and T2 toxin, was assessed through <em>in vitro</em> adsorption assays. Results demonstrated that the adsorption of DON by CM-glucan increased from 0 % to 59.11 %, corresponding to the adsorption of approximately 1.18 μg of DON from the initial concentration (2 μg/mL). Similarly, the adsorption of T2 toxin increased slightly from 0 % to 4.54 %, corresponding to 0.09 μg of T2 toxin adsorbed from the initial concentration (2 μg/mL). These findings underscore the potential of chemical modifications to enhance the functional properties of natural polysaccharides, suggesting future applications in mycotoxin adsorption and other biological properties across various areas.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109323"},"PeriodicalIF":2.4,"publicationDate":"2024-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142686211","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Structural characterization of a sulfated polysaccharide from Gracilaria domingensis and potential anti-inflammatory and antinociceptive effects","authors":"Rafael da Silva Prudêncio ,&nbsp;Antonio Kleiton de Sousa ,&nbsp;Denise Mayara Melo Silva ,&nbsp;Jayro dos Santos Ferreira ,&nbsp;Danyela Maria Leal Rocha ,&nbsp;Viviane Pinheiro Alves de Almeida ,&nbsp;João Janilson da Silva Sousa ,&nbsp;Stefany Guimarães Sousa ,&nbsp;Tino Marcos Lino da Silva ,&nbsp;André dos Santos Carvalho ,&nbsp;José Simião da Cruz Júnior ,&nbsp;Even Herlany Pereira Alves ,&nbsp;Daniel Fernando Pereira Vasconcelos ,&nbsp;Roosevelt D.S. Bezerra ,&nbsp;Flaviane de França Dourado ,&nbsp;Aline Lima de Oliveira ,&nbsp;Wanessa Feliz Cabral ,&nbsp;José Roberto de Souza de Almeida Leite ,&nbsp;Durcilene Alves da Silva ,&nbsp;Elias Borges do Nascimento Junior ,&nbsp;André Luiz dos Reis Barbosa","doi":"10.1016/j.carres.2024.109322","DOIUrl":"10.1016/j.carres.2024.109322","url":null,"abstract":"<div><div>Seaweeds are natural sources of sulfated polysaccharides (SPs), biopolymers with remarkable pharmacological properties, including biological actions capable of attenuating components of the inflammatory process such as edema, cytokines, cell migration and pain. Our results confirm that SPs obtained from <em>Gracilaria domingensis</em> (SP-GD) are agarans, primarily composed of residues of β-<span>d</span>-galactopyranose 6-sulfate and 3,6-anhydro-α-<span>l</span>-galactopyranose. Specifically, SP-GD at a dose of 10 mg/kg was effective in significantly reducing paw edema induced by carrageenan or histamine, serotonin, bradykinin, 48/80 and prostaglandin E2. SP-GD (10 mg/kg) was also able to reduce neutrophil migration and the activity of the myeloperoxidase enzyme in carrageenan-induced peritonitis, as well as conserve glutathione concentration and reduce malondialdehyde levels in the animals' peritoneal fluid. Furthermore, it showed antinociceptive action in the abdominal writhing test induced by acetic acid and in the paw licking test induced by formalin. Thus, the results obtained allow us to infer that SPs extracted from <em>G. domingensis</em> at a dose of 10 mg/kg have anti-inflammatory effects by reducing neutrophil migration and modulating the activity of vasoactive mediators and antinociceptive effects by acting, at least in part, through a peripheral mechanism dependent on the negative modulation of inflammatory mediators.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109322"},"PeriodicalIF":2.4,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646756","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}