Pub Date : 2024-12-17DOI: 10.1016/j.carres.2024.109359
Juan Song, Guangzhong Tu, Yue Liu, Si Liu, Yuting Zhang, Wenxi Yang, Xu Pang, Xiaojuan Chen, Haizhen Liang, Jie Zhang, Baiping Ma
A heptasaccharide was isolated from an active fraction of Trillium tschonoskii using HILIC and high-temperature PGC chromatography methods. UHPLC-Q/TOF-MS analysis gave this oligosaccharide a degree of polymerization (DP) of 7 and MS/MS showed that it has a six-carbon aldehyde glucan structure with the possible chain 1 → 4 connected. The structure was determined by series 1D and 2D NMR in two solvents D2O and DMSO‑d6. Using 1H resonances of the -OH groups as the starting point and HSQC-TOCSY on the covalent structure definition for structural elucidation allowed this heptasaccharide to be uncovered. This heptasaccharide was elucidated as maltoheptaose via complete assignment of 1H and 13C with jigsaw H-C-OH pieces produced by HSQC-TOCSY at increasing mixing time. The significance of identifying maltoheptaose in Trillium tschonoskii indicates the high potential of -OH introducing strategy for other oligosaccharides' structural determination with relatively higher DP.
{"title":"Hydroxyl groups introducing NMR strategy for structural elucidation of a heptasaccharide isolated from Trillium tschonoskii.","authors":"Juan Song, Guangzhong Tu, Yue Liu, Si Liu, Yuting Zhang, Wenxi Yang, Xu Pang, Xiaojuan Chen, Haizhen Liang, Jie Zhang, Baiping Ma","doi":"10.1016/j.carres.2024.109359","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109359","url":null,"abstract":"<p><p>A heptasaccharide was isolated from an active fraction of Trillium tschonoskii using HILIC and high-temperature PGC chromatography methods. UHPLC-Q/TOF-MS analysis gave this oligosaccharide a degree of polymerization (DP) of 7 and MS/MS showed that it has a six-carbon aldehyde glucan structure with the possible chain 1 → 4 connected. The structure was determined by series 1D and 2D NMR in two solvents D<sub>2</sub>O and DMSO‑d<sub>6</sub>. Using <sup>1</sup>H resonances of the -OH groups as the starting point and HSQC-TOCSY on the covalent structure definition for structural elucidation allowed this heptasaccharide to be uncovered. This heptasaccharide was elucidated as maltoheptaose via complete assignment of <sup>1</sup>H and <sup>13</sup>C with jigsaw H-C-OH pieces produced by HSQC-TOCSY at increasing mixing time. The significance of identifying maltoheptaose in Trillium tschonoskii indicates the high potential of -OH introducing strategy for other oligosaccharides' structural determination with relatively higher DP.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109359"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142876341","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}
Pub Date : 2024-11-22DOI: 10.1016/j.carres.2024.109325
Zuchao Ma , Harry E. Ensley , Douglas W. Lowman , Michael D. Kruppa , David L. Williams
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 Candida albicans and Candida auris.
{"title":"Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans","authors":"Zuchao Ma , Harry E. Ensley , Douglas W. Lowman , Michael D. Kruppa , 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}
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 O-mannosyl glycan. Patients with muscular dystrophy cannot synthesize matriglycan or the core M3 O-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).
{"title":"Chemical extension and glycodendrimer formation of the matriglycan decasaccharide, -(3Xylα1-3GlcAβ1)5- and its affinity for laminin","authors":"Kota Kotera , Ren Miyamoto , Gakuto Mochizuki , Takahiro Tamura , Noriyoshi Manabe , Yoshiki Yamaguchi , 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<sup>−8</sup> M and 6.8 × 10<sup>−8</sup> M, respectively, showing higher affinity than those of a matriglycan-repeating hexasaccharide (1.6 × 10<sup>−7</sup> M) and the dendrimer (1.8 × 10<sup>−7</sup> 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}
Pub Date : 2024-11-20DOI: 10.1016/j.carres.2024.109327
Nozomi Ishii , Andrea Mascherpa , Antony J. Fairbanks
A deprotected biantennary high mannose heptasaccharide N-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.
{"title":"Synthesis of a heptasaccharide N-glycan comprising two mannose-6-phosphate residues","authors":"Nozomi Ishii , Andrea Mascherpa , 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}
Pub Date : 2024-11-20DOI: 10.1016/j.carres.2024.109326
Yasemin Tantan , Özlem Kaplan , Kevser Bal , Sema Şentürk , Emine Büşra Eker Fidan , Sibel Çelik , Kamber Demir , Mehmet Koray Gök
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 (nLMWChiTri), which exhibit suitable properties for gene transfer studies, were evaluated regarding pDNA complexation ability, cytotoxicity and in vitro 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 nLMWChiTri 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.
{"title":"Tricine-modified chitosan as a strategy for enhancing hydrophilicity and gene delivery","authors":"Yasemin Tantan , Özlem Kaplan , Kevser Bal , Sema Şentürk , Emine Büşra Eker Fidan , Sibel Çelik , Kamber Demir , 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<sub>Tri</sub>), 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<sub>Tri</sub> 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}
Pub Date : 2024-11-19DOI: 10.1016/j.carres.2024.109324
Andrea Iovine , Andrei V. Filatov , Anastasiya A. Kasimova , Nowshin S. Sharar , Stephanie J. Ambrose , Andrey S. Dmitrenok , Mikhail M. Shneider , Anna M. Shpirt , Andrei V. Perepelov , Yuriy A. Knirel , Ruth M. Hall , Cristina De Castro , Johanna J. Kenyon
Capsular polysaccharide (CPS), a heteropolymeric carbohydrate structure present on the cell surface of most isolates of the bacterial pathogen Acinetobacter baumannii, is a major virulence determinant. Here, the CPS produced by A. baumannii 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-Glcp), galactose (d-Galp), N-acetyl-galactosamine (d-GalpNAc), and 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic acid (5,7-di-N-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 psaA-F genes in KL58, which are responsible for Pse5Ac7Ac synthesis. 4-O-acetylation of Pse5Ac7Ac was traced to an acetyltransferase, Atr44, 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-N-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.
{"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 , Andrei V. Filatov , Anastasiya A. Kasimova , Nowshin S. Sharar , Stephanie J. Ambrose , Andrey S. Dmitrenok , Mikhail M. Shneider , Anna M. Shpirt , Andrei V. Perepelov , Yuriy A. Knirel , Ruth M. Hall , Cristina De Castro , 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 <sup>1</sup>H and <sup>13</sup>C 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}
Pub Date : 2024-11-17DOI: 10.1016/j.carres.2024.109323
Juliana S.M. Tondolo , Gilson Zeni , Guilherme L. Sassaki , Janio M. Santurio , Erico S. Loreto
This study aimed to evaluate the impact of carboxymethylation on the structural and functional properties of β-glucan derived from the pathogenic oomycete Pythium insidiosum. 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 in vitro 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.
{"title":"Carboxymethylation of β-Glucan from Pythium insidiosum: Structural characterization and preliminary adsorption evaluation of DON and T2 toxin","authors":"Juliana S.M. Tondolo , Gilson Zeni , Guilherme L. Sassaki , Janio M. Santurio , 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 <sup>13</sup>C and <sup>1</sup>H 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}
Pub Date : 2024-11-15DOI: 10.1016/j.carres.2024.109322
Rafael da Silva Prudêncio , Antonio Kleiton de Sousa , Denise Mayara Melo Silva , Jayro dos Santos Ferreira , Danyela Maria Leal Rocha , Viviane Pinheiro Alves de Almeida , João Janilson da Silva Sousa , Stefany Guimarães Sousa , Tino Marcos Lino da Silva , André dos Santos Carvalho , José Simião da Cruz Júnior , Even Herlany Pereira Alves , Daniel Fernando Pereira Vasconcelos , Roosevelt D.S. Bezerra , Flaviane de França Dourado , Aline Lima de Oliveira , Wanessa Feliz Cabral , José Roberto de Souza de Almeida Leite , Durcilene Alves da Silva , Elias Borges do Nascimento Junior , André Luiz dos Reis Barbosa
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 Gracilaria domingensis (SP-GD) are agarans, primarily composed of residues of β-d-galactopyranose 6-sulfate and 3,6-anhydro-α-l-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 G. domingensis 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.
{"title":"Structural characterization of a sulfated polysaccharide from Gracilaria domingensis and potential anti-inflammatory and antinociceptive effects","authors":"Rafael da Silva Prudêncio , Antonio Kleiton de Sousa , Denise Mayara Melo Silva , Jayro dos Santos Ferreira , Danyela Maria Leal Rocha , Viviane Pinheiro Alves de Almeida , João Janilson da Silva Sousa , Stefany Guimarães Sousa , Tino Marcos Lino da Silva , André dos Santos Carvalho , José Simião da Cruz Júnior , Even Herlany Pereira Alves , Daniel Fernando Pereira Vasconcelos , Roosevelt D.S. Bezerra , Flaviane de França Dourado , Aline Lima de Oliveira , Wanessa Feliz Cabral , José Roberto de Souza de Almeida Leite , Durcilene Alves da Silva , Elias Borges do Nascimento Junior , 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}
Pub Date : 2024-11-13DOI: 10.1016/j.carres.2024.109301
Sunny Kumar, Zeel Bhatia, Sriram Seshadri
Chitosan was formulated into a microsphere and comprehensively characterized and evaluated for its anti-inflammatory potential and anti-diabetic properties against the high sugar fat diet-induced diabetic animals. The diabetic model was induced through feeding with a high-sugar fat diet. Metformin, a standard antidiabetic drug, and CMS (chitosan microspheres) were administered orally for 90 days as reversal strategies. Upon completion of the study, the following parameters, such as serum biochemistry, cytokine analysis, tissue histology, liver miRNA sequencing, and Shotgun metagenomics studies from stool samples, were performed. SEM images of the microsphere indicated a smooth morphology, while FTIR and DSC respectively, confirmed the presence of functional groups of chitosan and the thermal stability of the formulation. Following HSFD induction, all the parameters analyzed were altered compared to the control group. In both reversal groups, serum biochemical parameters were restored, which was at par with the control. A significant increase in the anti-inflammatory cytokine IL-10, and a remarkable reduction in TNF-α and MCP-1 inflammatory cytokines were observed in both reversal groups. Tissue histology indicated improvements in low-grade inflammation, induced in the diabetic group. miR-203 was upregulated in the CMS-treated group, while miR-103 was downregulated. The study further delved into the impact on gut microbiota and KEGG. Major phyla i.e., Bacteroidetes, Cyanobacteria, Firmicutes, Proteobacteria, and Verrucomicrobia showed restoration, while upregulation of DNA polymerase zeta in T2D showed reversal after the treatment. The formulation showed reversal at par with metformin and also confirms its anti-diabetic and anti-inflammatory activities of CMS, with microfloral and miR regulatory functions.
{"title":"Formulated chitosan microspheres remodelled the altered gut microbiota and liver miRNA in diet-induced Type-2 diabetic rats","authors":"Sunny Kumar, Zeel Bhatia, Sriram Seshadri","doi":"10.1016/j.carres.2024.109301","DOIUrl":"10.1016/j.carres.2024.109301","url":null,"abstract":"<div><div>Chitosan was formulated into a microsphere and comprehensively characterized and evaluated for its anti-inflammatory potential and anti-diabetic properties against the high sugar fat diet-induced diabetic animals. The diabetic model was induced through feeding with a high-sugar fat diet. Metformin, a standard antidiabetic drug, and CMS (chitosan microspheres) were administered orally for 90 days as reversal strategies. Upon completion of the study, the following parameters, such as serum biochemistry, cytokine analysis, tissue histology, liver miRNA sequencing, and Shotgun metagenomics studies from stool samples, were performed. SEM images of the microsphere indicated a smooth morphology, while FTIR and DSC respectively, confirmed the presence of functional groups of chitosan and the thermal stability of the formulation. Following HSFD induction, all the parameters analyzed were altered compared to the control group. In both reversal groups, serum biochemical parameters were restored, which was at par with the control. A significant increase in the anti-inflammatory cytokine IL-10, and a remarkable reduction in TNF-α and MCP-1 inflammatory cytokines were observed in both reversal groups. Tissue histology indicated improvements in low-grade inflammation, induced in the diabetic group. miR-203 was upregulated in the CMS-treated group, while miR-103 was downregulated. The study further delved into the impact on gut microbiota and KEGG. Major phyla i.e., <em>Bacteroidetes</em>, <em>Cyanobacteria</em>, <em>Firmicutes</em>, <em>Proteobacteria</em>, and <em>Verrucomicrobia</em> showed restoration, while upregulation of DNA polymerase zeta in T2D showed reversal after the treatment. The formulation showed reversal at par with metformin and also confirms its anti-diabetic and anti-inflammatory activities of CMS, with microfloral and miR regulatory functions.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109301"},"PeriodicalIF":2.4,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702508","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}
Pub Date : 2024-11-10DOI: 10.1016/j.carres.2024.109309
Inka Brockhausen, Dylan Falconer, Sara Sara
The mucus layer on epithelial cells is an essential barrier, as well as a nutrient-rich niche for bacteria, forming a dynamic, functional and symbiotic ecosystem and first line of defense against invading pathogens. Particularly bacteria in biofilms are very difficult to eradicate. The extensively O-glycosylated mucins are the main glycoproteins in mucus that interact with microbes. For example, mucins act as adhesion receptors and nutritional substrates for gut bacteria. Mucins also play important roles in immune responses, and they control the composition of the microbiome, primarily due to the abundance of complex O-glycans. In inflammation or infection, the structures of mucin O-glycans can change and thus affect mucin function, impact biofilm formation and the induction of virulence pathways in bacteria. In turn, bacteria can support host cell growth, mucin production and can stimulate changes in the host immune system and responses leading to healthy tissue function. The external polysaccharides of bacteria are critical for controlling adhesion and biofilm formation. It is therefore important to understand the relationships between the mucus layer and microbes, the mechanisms and regulation of the biosynthesis of mucins, of bacterial surface polysaccharides, and adhesins. This knowledge can provide biomarkers, vaccines and help to develop new approaches for improved therapies, including antibiotic treatments.
上皮细胞上的粘液层是一道重要的屏障，也是细菌营养丰富的栖息地，形成了一个动态、功能性和共生的生态系统，是抵御病原体入侵的第一道防线。尤其是生物膜中的细菌很难根除。广泛的 O 型糖基化粘蛋白是粘液中与微生物相互作用的主要糖蛋白。例如，粘蛋白是肠道细菌的粘附受体和营养底物。粘蛋白在免疫反应中也发挥着重要作用，它们还能控制微生物群的组成，这主要归功于大量复杂的 O 型糖。在炎症或感染时，粘蛋白 O 型糖的结构会发生变化，从而影响粘蛋白的功能，影响生物膜的形成和诱导细菌的毒力途径。反过来，细菌又能支持宿主细胞生长、产生粘蛋白，并能刺激宿主免疫系统和反应的变化，从而导致健康的组织功能。细菌的外部多糖对于控制粘附和生物膜的形成至关重要。因此，了解粘液层与微生物之间的关系、粘蛋白、细菌表面多糖和粘附素的生物合成机制和调控非常重要。这些知识可以提供生物标志物和疫苗，并有助于开发改进疗法（包括抗生素疗法）的新方法。
{"title":"Relationships between bacteria and the mucus layer","authors":"Inka Brockhausen, Dylan Falconer, Sara Sara","doi":"10.1016/j.carres.2024.109309","DOIUrl":"10.1016/j.carres.2024.109309","url":null,"abstract":"<div><div>The mucus layer on epithelial cells is an essential barrier, as well as a nutrient-rich niche for bacteria, forming a dynamic, functional and symbiotic ecosystem and first line of defense against invading pathogens. Particularly bacteria in biofilms are very difficult to eradicate. The extensively O-glycosylated mucins are the main glycoproteins in mucus that interact with microbes. For example, mucins act as adhesion receptors and nutritional substrates for gut bacteria. Mucins also play important roles in immune responses, and they control the composition of the microbiome, primarily due to the abundance of complex O-glycans. In inflammation or infection, the structures of mucin O-glycans can change and thus affect mucin function, impact biofilm formation and the induction of virulence pathways in bacteria. In turn, bacteria can support host cell growth, mucin production and can stimulate changes in the host immune system and responses leading to healthy tissue function. The external polysaccharides of bacteria are critical for controlling adhesion and biofilm formation. It is therefore important to understand the relationships between the mucus layer and microbes, the mechanisms and regulation of the biosynthesis of mucins, of bacterial surface polysaccharides, and adhesins. This knowledge can provide biomarkers, vaccines and help to develop new approaches for improved therapies, including antibiotic treatments.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"546 ","pages":"Article 109309"},"PeriodicalIF":2.4,"publicationDate":"2024-11-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142643486","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}
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