Carbohydrate Research最新文献

{"title":"Regioselective deacetylation of peracetylated glycosides with a cleavable aglycone","authors":"Alexander A. Abramov ,&nbsp;Anastasia G. Fefelova ,&nbsp;Andrey Shatskiy ,&nbsp;Markus D. Kärkäs ,&nbsp;Elena V. Stepanova","doi":"10.1016/j.carres.2025.109626","DOIUrl":"10.1016/j.carres.2025.109626","url":null,"abstract":"<div><div>Partially acetylated carbohydrates are integral to several biological functions and serve as synthetic intermediates for accessing complex glycoconjugates and oligosaccharides; however, their chemical synthesis remains highly challenging. Herein, we describe a straightforward protocol for the synthesis of monoacetylated sugars through acid-catalyzed regioselective deacetylation of readily accessible peracetylated glycosides featuring a cleavable aglycone (4-methoxyphenyl). The protocol proved effective for β-1,2-trans and α-1,2-cis-configured peracetylated pyranosides and its utility was demonstrated by large-scale synthesis, optimization for continuous flow, and application towards oligosaccharide synthesis.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109626"},"PeriodicalIF":2.5,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144763820","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":"Polysaccharides from mushrooms Russula: a review on extraction, structural features, bioactivities, structure-activity relationships and applications","authors":"Prasenjit Maity ,&nbsp;Ipsita Kumar Sen","doi":"10.1016/j.carres.2025.109625","DOIUrl":"10.1016/j.carres.2025.109625","url":null,"abstract":"<div><div>For centuries, worldwide-distributed <em>Russula</em> mushrooms are used as food and traditional medicine due to their characteristic flavor, good nutritional and precious medicinal value. Polysaccharides are the main active and significant components present in <em>Russula</em> mushrooms and show inclusive biological properties such as immunomodulatory, hepatoprotective, antitumor, anti-inflammatory, antioxidant, antibacterial and so on. This article highlights the several extraction methods in terms of alkali extraction, acid extraction, ultrasonic-assisted extraction, hot water extraction, and microwave-assisted extraction for the isolation of polysaccharides from <em>Russula</em> mushrooms. It also discusses how the structural features of <em>Russula</em> polysaccharides, such as monosaccharide composition, backbone structure, molecular weight, chemical modifications, mode of linkage, and degree of branching are highly related to their biological activities. This article systematically summarized the different extraction approaches, structural features, biological activities and applications of <em>Russula</em> polysaccharides. These will provide a valuable insight for improving the future research, progress, and utilization of <em>Russula</em> polysaccharides.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109625"},"PeriodicalIF":2.5,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144757858","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":"Glycosidic acids with α-glucosidase inhibitory activity as the alkaline hydrolysis products of resin glycoside fractions from Convolvulus tricolor and Ipomoea biflora","authors":"Bo-Yi Fan ,&nbsp;Su-Peng Guo ,&nbsp;Xin Lan ,&nbsp;Jin-Ping Gu ,&nbsp;Yu-Xin Li ,&nbsp;Rui Fan ,&nbsp;Min Yang ,&nbsp;Guang-Tong Chen ,&nbsp;Wen-Li Wang ,&nbsp;Xiao-Lin Liao ,&nbsp;Jia-Lie Luo","doi":"10.1016/j.carres.2025.109624","DOIUrl":"10.1016/j.carres.2025.109624","url":null,"abstract":"<div><div>Alkaline hydrolysis of the resin glycoside fractions of <em>Convolvulus tricolor</em> and <em>Ipomoea biflora</em> yielded three glycosidic acids (<strong>1</strong>–<strong>3</strong>). Contrilic acid A (<strong>1</strong>), a hexasaccharide glycosidic acid with a 3<em>S</em>,11<em>S</em>-dihydroxytetradecanoic acid as the aglycone, was isolated from <em>Convolvulus tricolor</em>, while a tetrasaccharide ipomofic acid A (<strong>2</strong>) and pentasaccharide operculinic acid A (<strong>3</strong>) were obtained from <em>Ipomoea biflora</em>, and were identified to possess a 11<em>S</em>-hydroxyhexadecanoic acid as the aglycone. Their structures were thoroughly established by the spectroscopic data and chemical evidences. Compounds <strong>1</strong> and <strong>2</strong> are previously undescribed compounds, and compound <strong>3</strong> exhibited potent <em>α</em>-glucosidase inhibitory activity with an IC₅₀ value of 78.32 μM. The molecular docking analysis indicated that compound <strong>3</strong> could bind within the active pocket of the <em>α</em>-glucosidase through the hydrogen bonding and hydrophobic contacts. Taken together, our results expanded the structural diversity of resin glycosides and provided promising candidates in the search for treatment of diabetes mellitus.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109624"},"PeriodicalIF":2.5,"publicationDate":"2025-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721550","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":"Corrigendum to \"Dual-crosslinked Cirsiumsetosum polysaccharide/quaternary chitosan self-healing hydrogel promotes wound healing\" [Carbohydrate Research 556 2025 109616].","authors":"Li Ma, Liyuan Lu, Xiaoliang Zhao, Qingsong Zhou, Li Luo, Doudou Ma, Wenya Wang, Weijie Zhang","doi":"10.1016/j.carres.2025.109623","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109623","url":null,"abstract":"","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":" ","pages":"109623"},"PeriodicalIF":2.4,"publicationDate":"2025-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144717601","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":"Capsular Polysaccharide of Acinetobacter baumannii MRSN 31196 (a KL1 Variant Strain) and its Degradation by a Recombinant Depolymerase from Bacteriophage vB_AbaP_B5","authors":"Evguenii Vinogradov ,&nbsp;Lillian Zou ,&nbsp;Jacek Stupak ,&nbsp;Yuliya Martynova ,&nbsp;Melanie Arbour ,&nbsp;Frank St Michael ,&nbsp;Dean Williams ,&nbsp;Greg Beaudoin ,&nbsp;Jianjun Li ,&nbsp;Wangxue Chen ,&nbsp;Wei Zou ,&nbsp;Danielle L. Peters","doi":"10.1016/j.carres.2025.109621","DOIUrl":"10.1016/j.carres.2025.109621","url":null,"abstract":"<div><div><em>Acinetobacter baumannii</em> MRSN 31196 was assigned as KL1, but has now been reassigned as KL1-v as new polymerase <em>wzy</em> and acetyl transferase (<em>atr25</em>) genes are discovered outside of its gene locus due to horizontal gene transfer. Its capsular polysaccharide (CPS), namely K1v, was isolated by a standard water-phenol extraction and an aqueous base extraction. K1v is degradable by a recombinant phage depolymerase B5 which is known to hydrolyze <em>A. baumannii</em> K9 CPS. The structure of oligosaccharides obtained were determined by NMR and mass spectroscopic analysis. The results showed that the K1v structure is closely related to K1 CPS, with the same sugar composition and linkages except β-QuiNAcNR-(<em>1–3</em>)-GlcNAc in K1v replaced β-QuiNAcNR-(<em>1–4</em>)-GlcNAc in K1, due to an altered Wzy. However, the <em>atr25</em> gene is likely silenced, or the transferase activity is inhibited, as K1v is not O-acetylated. We also found that the N-acetyl and N-3-hydroxybutyryl (HBu) substitutions (R) in QuiNAcNR has approximately a 1:1 ratio. The mass spectroscopic analysis provided evidence that structural blocks with consecutive QuiNAcNAc or QuiNAcNHBu are present in the polysaccharide. The K1v CPS structure has the following trisaccharide repeating unit.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109621"},"PeriodicalIF":2.5,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144724501","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":"Design, synthesis, and in-silico studies of hydrazide-hydrazone linked coumarin glycoconjugates with possible antiproliferative activity","authors":"Ravendra Kumar ,&nbsp;Deepanshi Chauhan ,&nbsp;Vinay Kumar Singh ,&nbsp;Ambuj Kumar Kushwaha ,&nbsp;Divya Kushwaha","doi":"10.1016/j.carres.2025.109620","DOIUrl":"10.1016/j.carres.2025.109620","url":null,"abstract":"<div><div>Coumarins, known for their broad-spectrum bioactivity, continue to serve as versatile scaffolds in drug design and development. Given the recent advancements in coumarin-based anticancer therapeutics, the design of novel coumarin derivatives has garnered significant attention for the development of multifunctional drug candidates. In this study, we designed and synthesized a series of novel hydrazide-hydrazone anchored coumarin-glycohybrids (<strong>1–8</strong>) using acetyl-protected β-C-glycopyranosyl propanone (<strong>11a</strong> and <strong>11b</strong>) as starting materials. The glycosyl ketones were first converted into the corresponding hydrazones of cyanoacetohydrazide (<strong>13a</strong> and <strong>13b</strong>) <em>via</em> reaction with cyanoacetohydrazide. Subsequent Knoevenagel condensation of <strong>13a</strong> and <strong>13b</strong> with salicylaldehyde derivatives, followed by hydrolysis, yielded the target compounds (<strong>1</strong>–<strong>8</strong>). The synthesized compounds were structurally characterized using spectroscopic techniques, including ¹H and ¹³C NMR, FT-IR, and mass spectrometry. The binding interactions of the synthesized glycohybrids were investigated through molecular docking studies targeting key cancer-related kinases, including EGFR, VEGFR-2, and CDK2. Docking results demonstrated strong binding affinities in compounds, particularly towards EGFR and CDK2 proteins, when compared with their known inhibitors. Molecular dynamics (MD) simulation studies predicted stable binding for the selected compounds <strong>7</strong> and <strong>5</strong> within the binding pocket of EGFR and VEGFR-2, respectively. Furthermore, computational evaluations of drug-likeness indicated that all synthesized compounds possess favourable pharmacokinetic profiles.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109620"},"PeriodicalIF":2.4,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144686129","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":"The influence of protective groups in sialyl halides on their reactivity and selectivity in glycosylation reactions: implications for the mechanism of sialylation","authors":"Zarina Z. Mamirgova,&nbsp;Alexander I. Zinin,&nbsp;Leonid O. Kononov","doi":"10.1016/j.carres.2025.109617","DOIUrl":"10.1016/j.carres.2025.109617","url":null,"abstract":"<div><div>In this study, a comparative analysis of the reactivity of known and novel sialyl donors bearing various protective and leaving groups (sialyl chlorides and sialyl bromides) was conducted through their reactions with methanol and isopropyl alcohol in the absence of added promoter. NMR analysis of the reaction mixtures following solvolysis provided clear insights into the variations in reactivity and selectivity as a function of the nature of the protective and leaving groups present in the sialyl halide molecules.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109617"},"PeriodicalIF":2.5,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144721551","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":"Psyllium husk, carbohydrate polymer based novel plug-in capsule device for pulsatile release from meloxicam-β-cyclodextrin-pectin ternary complex","authors":"Rajesh S. Jagtap ,&nbsp;Sneha R. Jagtap ,&nbsp;Sandeep D. Chavan ,&nbsp;Vikram R. Shinde ,&nbsp;Sanjeevani R. Desai ,&nbsp;Sandhyarani R. Sagavkar ,&nbsp;Atul S. Alkunte","doi":"10.1016/j.carres.2025.109614","DOIUrl":"10.1016/j.carres.2025.109614","url":null,"abstract":"<div><div>Chronomodulated diseases demonstrate circadian fluctuations. Conventional dosage forms are inadequate for mitigating these ailments; instead, time-scheduled drug release is necessary for pharmacological efficacy. The current investigation aims to develop natural, carbohydrate polymer-based novel plug-in capsule, pulsatile drug delivery system with engineered specificity of meloxicam with low aqueous solubility. β-CD is employed to boost solubility by forming solid ternary inclusion complexes where natural polymers, viz., pectin and agar, act as ternary agents. Plug-in capsule device is prepared using formaldehyde-treated capsule bodies and optimized by 3²full factorial design by considering concentrations of HPMC-E15 (<span><math><mrow><msub><mi>X</mi><mn>1</mn></msub></mrow></math></span>) and psyllium husk (<span><math><mrow><msub><mi>X</mi><mn>2</mn></msub></mrow></math></span>) as independent variables and lag time <span><math><mrow><mrow><mo>(</mo><msub><mi>Y</mi><mn>1</mn></msub><mo>)</mo></mrow><mtext>,</mtext></mrow></math></span> time required to release 80 % drug <span><math><mrow><mo>(</mo><msub><mi>Y</mi><mn>2</mn></msub><mo>)</mo></mrow></math></span>, release of drug at 6 h, (<span><math><mrow><msub><mi>Y</mi><mn>3</mn></msub></mrow></math></span>) as responses. Dissolution order was ternary complex (pectin 60.21 %) &gt; ternary complex (agar 53.64 %) &gt; binary complex (41.56 %) &gt; pure drug (18.87 %). Batch F6, demonstrated a significant lag time of 6.15 ± 0.07 h followed by maximum drug release (85.21 % at 60 min) from its ternary complex containing β-CD and pectin. <span><math><mrow><msub><mi>X</mi><mn>1</mn></msub></mrow></math></span> and <span><math><mrow><msub><mi>X</mi><mn>2</mn></msub></mrow></math></span> demonstrates significant positive effects on <span><math><mrow><msub><mi>Y</mi><mn>1</mn></msub></mrow></math></span> and <span><math><mrow><msub><mi>Y</mi><mn>2</mn></msub></mrow></math></span> but decrease in <span><math><mrow><msub><mi>Y</mi><mn>3</mn></msub></mrow></math></span>. Thus, developed formulation serves as remedy for early morning pain with stiffness that rheumatoid arthritis patients experience, as it follows circadian pattern. Simultaneously, it maximizes drug delivery and achieves desired therapeutic effect, thus eliminating risk of early morning pain.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109614"},"PeriodicalIF":2.4,"publicationDate":"2025-07-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144680575","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":"Dual-crosslinked cirsiumsetosum polysaccharide/quaternary chitosan self-healing hydrogel promotes wound healing","authors":"Li Ma ,&nbsp;Liyuan Lu ,&nbsp;Xiaoliang Zhao ,&nbsp;Qingsong Zhou ,&nbsp;Li Luo ,&nbsp;Doudou Ma ,&nbsp;Wenya Wang ,&nbsp;Weijie Zhang","doi":"10.1016/j.carres.2025.109616","DOIUrl":"10.1016/j.carres.2025.109616","url":null,"abstract":"<div><div>Hydrogel dressings have attracted considerable attention as essential tools for the treatment of skin wounds. In this study, a physically and chemically double cross-linked self-healing hydrogel (HPOCFe) was developed to promote skin wound healing. Through the dual network hydrogel strategy, the hydrogel not only overcomes the slow formation and recombination of covalent bonds in the chemical crosslinking network, but also overcomes the poor mechanical properties of the physical crosslinking network. The excellent properties of each cross-linking network were preserved, while the self-healing property of the hydrogel was synergistically enhanced. Pyrocatechin (PCA) was grafted onto quaternary chitosan (HACC) to obtain HACC-PCA. Subsequently, oxidized <em>Cirsiumsetosum</em> polysaccharide (OCSP) and FeCl₃ were added to the HACC-PCA solution to prepare HPOCFe hydrogel.The structural and functional properties of the hydrogel were investigated, including morphology, mechanical strength, swelling and degradation behaviour, haemostatic properties, cytotoxicity, antimicrobial activity and wound healing efficacy. The HPOCFe hydrogel exhibited good tissue adhesion, improved compressive strength, excellent self-healing ability, rapid haemostatic ability, low cytotoxicity, promotion of cell migration and strong antimicrobial activity. Importantly, the HPOCFe hydrogel significantly promoted epithelial regeneration, granulation tissue formation, collagen deposition and orientation, angiogenesis and wound contraction in wound healing. In conclusion, the HPOCFe hydrogel can promote wound healing and has broad application prospects as a scaffold in regenerative medicine.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109616"},"PeriodicalIF":2.4,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144655580","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":"Enhancing hydroxytyrosol stability via site-specific glucosylation","authors":"Hiroyuki Ohashi ,&nbsp;Daisuke Koma ,&nbsp;Takashi Ohmoto ,&nbsp;Takao Ohashi ,&nbsp;Yasuharu Satoh ,&nbsp;Ryo Misaki ,&nbsp;Hayato Yamanaka","doi":"10.1016/j.carres.2025.109618","DOIUrl":"10.1016/j.carres.2025.109618","url":null,"abstract":"<div><div>Hydroxytyrosol (HT), a phenolic compound found in olive fruit and oil, has notable biological activity; however, its susceptibility to oxidation limits its application. In plants, HT is naturally glycosylated but the functional relevance of this modification remains unclear. In this study, we investigated the effect of glycosylation positions on HT stability. We successfully synthesized and purified three HT glucoside (HTG) regioisomers using enzymes with position-selective glycosylation activity toward HT. The results revealed that the <em>meta</em>- and <em>para</em>-positions of HT, especially when the <em>para</em>-position is glucosylated, exhibit high stability even under conditions of enhanced catechol oxidation. Glucosylation at specific positions significantly influences the stability of HTGs. Furthermore, HTGs can be converted back to HT via acidic or enzymatic hydrolysis, highlighting its potential as a stable bioactive compound for food- and health-related applications. This study provides valuable insights into the stability mechanism of HTGs and its potential industrial application as a functional material.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"556 ","pages":"Article 109618"},"PeriodicalIF":2.4,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144672463","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}