{"title":"Photocatalyst-free light-promoted carbohydrate synthesis and modification","authors":"Jing Wang , Fan Zhou , Yuping Xu , Lei Zhang","doi":"10.1016/j.carres.2024.109304","DOIUrl":"10.1016/j.carres.2024.109304","url":null,"abstract":"<div><div>Photoredox catalysis has recently emerged as a powerful approach for preparing oligosaccharides because it uses mild conditions, is compatible with partially or completely unprotected carbohydrate substrates, and exhibits impressive regio‐ and stereo‐selectivity and high functional group tolerance. However, most catalytic photoredox reactions require an external photocatalyst (organic dye or expensive transition-metal complex) to deliver key glycosyl radicals. Several photocatalyst-free photocatalytic reactions that avoid the use of expensive metal salts or organic-dye additives have received significant attention. In this review, we highlight the most recent developments in photocatalyst-free light-promoted carbohydrate synthesis and modification, which is expected to inspire broad interest in further innovations in the green synthesis of saccharides.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"546 ","pages":"Article 109304"},"PeriodicalIF":2.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142615338","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":"Entropy-enthalpy compensation in the methyl 5-thio-α-d-galactopyranoside–Jacalin interaction","authors":"Daniil Ahiadorme , David Crich","doi":"10.1016/j.carres.2024.109305","DOIUrl":"10.1016/j.carres.2024.109305","url":null,"abstract":"<div><div>Methyl 5-thio-α-<span>d</span>-galactopyranoside was synthesized and found to have a more favorable enthalpy of binding to Jacalin than methyl α-<span>d</span>-galactopyranoside, which is attributed to the greater magnitude of sulfur-π over oxygen-π interactions. This increase in enthalpy, however, was offset by a less favorable entropy of binding, arising from the need to constrain the more flexible thiosugar, thereby highlighting the complexities inherent in the design of effective sugar mimetics.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"547 ","pages":"Article 109305"},"PeriodicalIF":2.4,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142692722","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}
Ming Ma , Fengdie Yan , Jing Jing , Kunyan Chen , Peng Wang , Changguo Wang , Qianfeng Chen
{"title":"Structure analysis and immunomodulatory activity of novel oligosaccharide from Nicotiana tabacum roots","authors":"Ming Ma , Fengdie Yan , Jing Jing , Kunyan Chen , Peng Wang , Changguo Wang , Qianfeng Chen","doi":"10.1016/j.carres.2024.109303","DOIUrl":"10.1016/j.carres.2024.109303","url":null,"abstract":"<div><div>A novel oligosaccharide (NTRP60-W-2) with an average molecular weight of 1377 Da was isolated and purified from <em>Nicotiana tabacum</em> roots. Its structural characteristics and immunomodulatory properties were investigated. Structural analysis revealed that NTRP60-W-2 was composed exclusively of glucose, featuring →1)-α-D-Glc<em>p</em>-(6→ backbone. Immunological assays demonstrated that NTRP60-W-2 significantly enhanced cell viability, nitric oxide production and cytokine secretion (IL-6 and TNF-α) in RAW264.7 cells. These findings provide a foundation for further exploration of <em>Nicotiana tabacum</em> carbohydrates and their potential biological activities.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109303"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142567592","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":"Synthetic strategy for polyhydroxylated indolizidine iminosugar from sugar-derived HWE precursor","authors":"Nagaraja Ingaladal , Ravi S. Lankalapalli","doi":"10.1016/j.carres.2024.109302","DOIUrl":"10.1016/j.carres.2024.109302","url":null,"abstract":"<div><div>The diversity of polyhydroxylated indolizidine (PI) iminosugars is ever-expanding due to the wide range of methods developed and substrate choice during synthesis. This study used an HWE precursor derived from <span>d</span>-glucose to extend the chain length at the C1 position. A double reductive amination and dihydroxylation of the resulting olefin, followed by intramolecular cyclization, enabled the successful synthesis of a new PI. In addition, the precursor intermediate for Mitsunobu reaction was utilized in synthesis of a new iminononulol.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109302"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578931","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}
Maxim S. Kokoulin , Vlada S. Belova , Lyudmila A. Romanenko
{"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 , Vlada S. Belova , 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 <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, including <sup>1</sup>H,<sup>1</sup>H COSY, <sup>1</sup>H,<sup>1</sup>H TOCSY, <sup>1</sup>H,<sup>1</sup>H ROESY and <sup>1</sup>H,<sup>13</sup>C HSQC, and <sup>1</sup>H,<sup>13</sup>C 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, Yongtai Wang, Yimo Feng, Xiangling Zhu, 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 (H<sub>4</sub>PMo<sub>11</sub>VO<sub>40</sub>·2H<sub>2</sub>O) 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 , 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}
Ziyu Jiang , Yi Xu , Liu Yang , Xing Huang , Jun Bao
{"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 , Yi Xu , Liu Yang , Xing Huang , 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}
Xuerong Luo , Lingyu Zhao , Imran Mahmood Khan , Lin Yue , Yin Zhang , Zhouping Wang
{"title":"Chitosan-curcumin conjugate prepared by one-step free radical grafting: Characterization, and functional evaluation","authors":"Xuerong Luo , Lingyu Zhao , Imran Mahmood Khan , Lin Yue , Yin Zhang , 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 , Ling-Ling Ding , Yan-Yan Chen , 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}