Carbohydrate Research最新文献

{"title":"Effect of bacterial dissociation on lipopolysaccharide structure: A study of O-polysaccharide from the marine bacterium Pseudoalteromonas agarivorans KMM 232 (O-form)","authors":"Maxim S. Kokoulin ,&nbsp;Vlada S. Belova ,&nbsp;Lyudmila A. Romanenko","doi":"10.1016/j.carres.2024.109300","DOIUrl":"10.1016/j.carres.2024.109300","url":null,"abstract":"<div><div>The lipopolysaccharide (LPS) was obtained from a bacterium <em>Pseudoalteromonas agarivorans</em> KMM 232 (O-form) isolated from a seawater sample collected at a depth of 500 m. The O-polysaccharide (OPS) was isolated by mild acid degradation of the LPS and studied by chemical methods along with 1D and 2D ¹H and ¹³C NMR spectroscopy, including ¹H,¹H COSY, ¹H,¹H TOCSY, ¹H,¹H ROESY and ¹H,¹³C HSQC, and ¹H,¹³C HMBC experiments. The following new structure of the OPS from <em>P. agarivorans</em> KMM 232 (O-form) containing 2-acetamido-2-deoxy-<span>d</span>-glucose (D-GlcNAc), <span>d</span>-glucose (D-Glc), <span>d</span>-glucuronic acid (D-GlcA), 4,6-<em>O</em>-[(<em>R</em>)-1-carboxyethylidene]-<span>d</span>-galactose [D-Gal<em>p</em>4,6 (<em>R</em>-Pyr)] and two residues of <span>d</span>-galactose (D-Gal) was established:</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109300"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142543871","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":"Sustainable production of organic acids from chitin biomass catalyzed by Keggin-type heteropolyacid under hydrothermal condition","authors":"Yulong Chang,&nbsp;Yongtai Wang,&nbsp;Yimo Feng,&nbsp;Xiangling Zhu,&nbsp;Hongjun Zang","doi":"10.1016/j.carres.2024.109299","DOIUrl":"10.1016/j.carres.2024.109299","url":null,"abstract":"<div><div>The “shell biorefinery,” which valorizes the shell waste chitin into fine chemicals, has developed rapidly in recent years. Herein, we present a novel base-free heteropolyacid-catalyzed oxidation method for the transformation of chitin biomass into organic acid. After a series of optimization experiments, a 5.93 % yield of formic acid and 25.09 % yield of acetic acid were achieved in the presence of 0.5 equivalent of Mo–V–P heteropolyacids (H₄PMo₁₁VO₄₀·2H₂O) and air at 180 °C under hydrothermal conditions for 4 h. Meanwhile, we have demonstrated that the Keggin-type heteropolyacid catalysts are capable of efficiently converting microcrystalline chitin into organic acids. The synthesized heteropolyacids are well characterized with FT-IR, XRD, ICP-AES, and TGA. The possible reaction pathway was speculated accordingly. This method offers several advantages, including readily available raw materials, simple operation, and relatively higher yield.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109299"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142543873","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":"Modeling conformational changes in alginic acid oligomers induced by external forces","authors":"Agnieszka Brzyska ,&nbsp;Wojciech Płaziński","doi":"10.1016/j.carres.2024.109294","DOIUrl":"10.1016/j.carres.2024.109294","url":null,"abstract":"<div><div>In this study, the mechanism and nature of mechanical force-induced conformational transitions of alginate oligomers with different ratios of β-<span>d</span>-mannuronic acid (M unit) and α-<span>l</span>-guluronic acid (G unit) units were investigated. The influence of the type of glycosidic linkage in either homo- or heterooligomers on the nature of conformational transitions was also considered. For this purpose, two different theoretical methods were used: quantum mechanics (QM) at the DFT level with the EGO (Enforced Geometry Optimization) approach previously tested also for other saccharide systems, and molecular dynamics (MD) simulations within hybrid interaction potentials, which take into account both the ab initio (QM) level of theory and classical molecular mechanics (MM) force fields. This allowed to characterize in detail the structural and energetic properties of the conformational transition occurring upon the influence of external, mechanical forces (e.g. ring conformations at the path of ring-inversion process as well as the energies corresponding to initial, final and intermediate states). The results indicate qualitatively various responses against the applied force, depending on the G:M ratio, which have their source in differing topologies of glycosidic linkage in either G or M units. This is of potential relevance for determining the content of naturally heterogeneous alginate chains by the AFM experimental studies. The effects of explicit solvent and non-zero temperature are not of primarily importance in the context of determined stretching properties.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109294"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142543872","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":"Bile acid conjugated chitosan nanoparticles promote the proliferation and epithelial-mesenchymal transition of hepatocellular carcinoma by regulating the PI3K/Akt/mTOR pathway","authors":"Ziyu Jiang ,&nbsp;Yi Xu ,&nbsp;Liu Yang ,&nbsp;Xing Huang ,&nbsp;Jun Bao","doi":"10.1016/j.carres.2024.109296","DOIUrl":"10.1016/j.carres.2024.109296","url":null,"abstract":"<div><div>Bile acids have been known to play significant roles at certain physiological levels in gastrointestinal metabolism. Yet, they are known to be carcinogenic and aid in tumor progression in most cases, although the roles remain uncertain. Hence, we tested the cytotoxic potential of cholic acid (CA) loaded chitosan nanoparticles (CNPs) on Hep3B cells. The physicochemical properties of the CNPs synthesized with CA load (CA-CNPs) were determined using standard techniques such as ultraviolet–visible spectrophotometry (UV–Vis), fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), dynamic light scattering (DLS) and transmission electron microscopy (TEM). The characteristic peak for chitosan nanoparticles were observed for plain CNPs (pCNPs) and CA-CNPs at around 300 nm as per UV–Vis analysis. FTIR analysis indicated the possible trapping of CA onto CNPs as certain peaks were retained and some peaks were shifted. XRD analysis determined that the peaks representing CA and pCNPs were collectively obtained in CA-CNPs. As per DLS analysis, the particle size, PDI and ζ-potential of the CA-CNPs were 259 nm, 0.284 and 30.4 mV. Further, the CA-CNPs were non-cytotoxic on Hep3B cells at the maximum tested concentration of 500 μg/mL. The viability at 500 μg/mL of CA-CNPs was two-fold higher than 500 μg/mL of pCNPs. Also, the pCNPs were not hemolytic and therefore could not have played a role in the increase of viability after treatment with CA-CNPs, which indicates that CA posed a major role in increased viability of Hep3B cells. As per quantitative PCR (qPCR), the upregulated gene expressions of PI3K, Akt, mTORC2, cMyc, Fibronectin, hVPS34, Slug and ZEB1 and the downregulated expression of the tumor suppressor PTEN indicates that PI3K/Akt/mTOR pathway mediated the induction of epithelial-to-mesenchymal transition (EMT) in response to CA-CNPs treatment on Hep3B cells.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109296"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142543870","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":"Chitosan-curcumin conjugate prepared by one-step free radical grafting: Characterization, and functional evaluation","authors":"Xuerong Luo ,&nbsp;Lingyu Zhao ,&nbsp;Imran Mahmood Khan ,&nbsp;Lin Yue ,&nbsp;Yin Zhang ,&nbsp;Zhouping Wang","doi":"10.1016/j.carres.2024.109297","DOIUrl":"10.1016/j.carres.2024.109297","url":null,"abstract":"<div><div>Curcumin (Cur) is a naturally hydrophobic polyphenol, and it has a wide range of physiological functions. But the practical application of Cur is constrained by its low water solubility and poor stability. To improve these deficiencies of Cur, a novel Cur derivative (CS-Cur) was prepared by grafting chitosan (CS) with Cur through a one-step reaction of a free radical-mediated redox system. A series of characterizations provided evidence that the grafting of CS with Cur was successful. The obtained CS-Cur showed lower crystallinity and thermal properties than CS and Cur. After grafting, the water solubility of CS-Cur was found to be 9.76 ± 2.45 g/L and greatly improved. Meanwhile, the CS-Cur showed good photothermal stability, antioxidant activity, and photodynamic antibacterial activity in an aqueous solution, and it had good <em>in vitro</em> biosafety. This provides an idea for the design and synthesis of novel highly water-soluble Cur derivatives and also improves the practical application of Cur in aqueous systems.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109297"},"PeriodicalIF":2.4,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142521075","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":"Exploring the therapeutic potential of polysaccharide from Portulaca oleracea L.: A review of phytochemistry and immunomodulatory effect","authors":"Hai-Xin Liu ,&nbsp;Ling-Ling Ding ,&nbsp;Yan-Yan Chen ,&nbsp;Shi-Yuan Wen","doi":"10.1016/j.carres.2024.109298","DOIUrl":"10.1016/j.carres.2024.109298","url":null,"abstract":"<div><div><em>Portulaca oleracea</em> L., a plant with both edible and medicinal properties, is traditionally valued for its diuretic, antipyretic, antiseptic, antispasmodic, and anthelmintic functions in folk medicine. <em>P</em>. <em>oleracea</em> polysaccharide (POP), a pivotal bioactive component, has various biological activities. Notably, their immunomodulatory capabilities have emerged as a significant area of research. The extraction, purification, monosaccharide composition, structure characterization, and biological activity of POP have been extensively investigated to identify the active components and to clarify their pharmacological actions and underlying molecular mechanisms. It aims to delineate the pharmacological mechanisms and molecular pathways associated with these polysaccharides, thereby underscoring their therapeutic promise and nutritional significance. Furthermore, the review critically examines the current research landscape of POP, identifying gaps and proposing innovative perspectives to enrich the scientific discourse surrounding these bioactive compounds.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109298"},"PeriodicalIF":2.4,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532063","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 the pentasaccharide repeating unit with a conjugation-ready linker corresponding to the O-antigenic polysaccharide of Acinetobacter junii strain 65","authors":"Aniket Majhi,&nbsp;Samim Sahaji,&nbsp;Anup Kumar Misra","doi":"10.1016/j.carres.2024.109295","DOIUrl":"10.1016/j.carres.2024.109295","url":null,"abstract":"<div><div>A straightforward synthesis of the pentasaccharide with a readily available linker arm corresponding to the <em>O</em>-antigenic polysaccharide of <em>Acinetobacter junii</em> strain 65 has been achieved in good yield. The synthesis has been carried out using thioglycosides as glycosyl donor in the presence of a combination of <em>N</em>-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) as thiophilic activator. The yields of the glycosylation steps were very good with satisfactory stereochemistry at the glycosidic linkages. The pentasaccharide derivative has also been obtained using a one-pot iterative glycosylation strategy.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109295"},"PeriodicalIF":2.4,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142495632","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":"Trehalulose: Exploring its benefits, biosynthesis, and enhanced production techniques","authors":"Yogaletchumy Seevanathan ,&nbsp;Norhasnida Zawawi ,&nbsp;Abu Bakar Salleh ,&nbsp;Siti Nurbaya Oslan ,&nbsp;Nur Suhanawati Ashaari ,&nbsp;Amir Syahir Amir Hamzah ,&nbsp;Suriana Sabri","doi":"10.1016/j.carres.2024.109293","DOIUrl":"10.1016/j.carres.2024.109293","url":null,"abstract":"<div><div>The increasing concern over sugar-related health issues has sparked research interest in seeking alternatives to sucrose. Trehalulose, a beneficial structural isomer of sucrose, is a non-cariogenic sugar with a low glycemic and insulinemic index. Besides its potential as a sugar substitute, trehalulose exhibits high antioxidant properties, making it attractive for various industrial applications. Despite its numerous advantages and potential application in various sectors, the industrial adoption of trehalulose has yet to be established due to lack of studies on its characteristics and practical uses. This review aims to provide a comprehensive overview of the properties of trehalulose, emphasizing its health benefits. The industrial prospects of trehalulose as sweetener and reducing agent, particularly in food and beverages pharmaceutical, and cosmeceutical sectors, are explored. Additionally, the review delves into the sources of trehalulose and the diverse organisms capable of producing trehalulose. The biosynthesis of this sugar primarily involves an enzyme-mediated process. Thus, these enzymes' properties, mechanisms, and the heterologous expression of genes associated with trehalulose production are explored. The strategies discussed in this review can be improved and applied to establish trehalulose bio-factories for efficient synthesis of trehalulose in the future. With further research and development, trehalulose holds promise as a valuable component across various industries.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109293"},"PeriodicalIF":2.4,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142495642","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":"Chiron approach toward the synthesis of the fused tricyclic core of epi-parvistemonine A","authors":"Esmeralda Marín-Cruz ,&nbsp;Ricardo Tovar-Miranda ,&nbsp;Julio Romero-Ibáñez ,&nbsp;José Alvano Pérez-Bautista ,&nbsp;Alejandro Cordero-Vargas ,&nbsp;Daniel Mendoza-Espinosa ,&nbsp;Rosa L. Meza-León ,&nbsp;Omar Cortezano-Arellano","doi":"10.1016/j.carres.2024.109290","DOIUrl":"10.1016/j.carres.2024.109290","url":null,"abstract":"<div><div>A stereoselective synthesis of fused tricyclic framework of <em>epi</em>-parvistemonine A from D-glucono-δ-lactone is described. The synthetic strategic is based on the stereoselective construction of the 7-membered cyclic skeleton <em>via</em> a cross-metathesis reaction followed by a Michael type cyclization promoted by Tf₂O.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109290"},"PeriodicalIF":2.4,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142458580","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":"Picoplatin (II)-loaded chitosan nanocomposites as effective drug delivery systems: Preparation, mechanistic investigation of BSA/5-GMP/GSH binding and biological evaluations","authors":"Noha M. Ahmed ,&nbsp;Mohamed M. Ibrahim ,&nbsp;Ibrahim M. Elmehasseb ,&nbsp;Shaban Y. Shaban","doi":"10.1016/j.carres.2024.109292","DOIUrl":"10.1016/j.carres.2024.109292","url":null,"abstract":"<div><div>The goal of the current study is to improve the characteristics and bioavailability of the drug picoplatin (PPt) by encapsulating it in chitosan nanoparticles (CS NPs) which allows for the targeted delivery of cytotoxic cargo to cancerous tissue, reducing toxic side effects and raising the therapeutic index. When picoplatin was delivered into the CS, it was able to produce a complex with CS (PPt@CS NPs) that had an appropriate particle size of 275 ± 10 nm, a reasonably low PDI of 0.15 ± 0.05, and high stability (ζ = −22.1 ± 0.3 mV). Since almost all pharmaceuticals work by binding to specific proteins or DNA, the in vitro binding mechanism and affinity of bovine serum albumin (BSA), low molecular building units of nucleic acids (5−GMP), and Glutathione (GSH) (considering that cisplatin resistance could be due to a reaction between cisplatin and GSH) to PPt and PPt@CS NPs were examined using stopped-flow and other spectroscopic approaches. Through two reversible processes, a rapid second-order binding followed by a slower first-order isomerization reaction, and a static quenching mechanism, PPt and PPt@CS NPs bind to BSA with relative reactivity of around (PPt)/(PPt@CS NPs) = 1/2.5. The 5−GMP interaction studies demonstrated that, in addition to changing the binding mechanism, PPt's encapsulation in CS increases its rate of reaction through coordination affinity. PPt interacted with 5-GMP via two reversible processes, a rapid second-order binding to phosphate followed by a slower first−order migration to the N7 of pyrimidine moiety. PPt@CS NPs showed weaker binding to GSH compared to PPt and hence PPt@CS NPs exhibits a lower resistance factor. It was also found that the in vitro drug release of PPt@CS NPs in PBS at pH 7.4 was steady, releasing 30 % of the PPt in just 5 h. Nonetheless, 75 % of the release in a pH 5.4 solution containing 10 mM GSH—a solution that mimics the tumor microenvironment—shows that the PPt@CS NPs system is sensitive to GSH and specifically targets malignant tissue. The encapsulation of PPt in CS complex maintained its anticancer activity, as shown by an in vitro cell-survival assay on HepG2 cancer cell lines and also cleavage efficiency toward the minor groove of pBR322 DNA via the hydrolytic way. These findings collectively suggested that inclusion PPt in CS would be an effective strategy to formulate a novel picoplatin formulation intended for use as targeted anticancer treatment.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109292"},"PeriodicalIF":2.4,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142458582","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}