Carbohydrate Research最新文献

{"title":"Synthesis of branched heterooligosaccharides related to Aspergillus galactomannan containing short Galf side chains.","authors":"Darya A Rastrepaeva, Dmitry A Argunov, Ilya A Puchkin, Dmitry V Yashunsky, Vadim B Krylov, Nikolay E Nifantiev","doi":"10.1016/j.carres.2024.109360","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109360","url":null,"abstract":"<p><p>The members of a widespread Aspergillus fungi genus cause various diseases including the invasive aspergillosis with high morbidity and mortality rates, especially for immunosuppressed patients. One of the main carbohydrate structures on the surface of their cell wall is the galactomannan (GM) which is used in diagnostic kits for the detection of specific types of aspergillosis. However, limited specificity of currently available test systems urges the need for their further improvement. Herein we report the first synthesis of branched heterosaccharides related to GM and containing α-(1→2)-/α-(1→6)-linked tetramannoside backbone chain bearing one galactofuranoside unit or its β-(1→5)-linked dimer. The preparation of conjugates of the obtained spacered oligosaccharides with BSA is also performed to produce tools for the assessment the specificity of anti-Aspergillus immune response and to select antibodies suitable for the development of novel diagnostic kits that may discriminate distinct types of aspergillosis.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109360"},"PeriodicalIF":2.4,"publicationDate":"2024-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142881438","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":"Advances in structural modification of fucoidans, ulvans, and carrageenans to improve their biological functions for potential therapeutic application.","authors":"Sara El Asri, Reda Ben Mrid, Zakia Zouaoui, Zoulfa Roussi, Abdelhamid Ennoury, Mohamed Nhiri, Fatiha Chibi","doi":"10.1016/j.carres.2024.109358","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109358","url":null,"abstract":"<p><p>Marine sulfated polysaccharides constitute a class of bioactive polymers commonly found in cell walls of macroalgae. Among these macromolecular substances, fucoidans, ulvans, and carrageenans have attracted considerable attention providing interesting therapeutic properties affected by a combination of various structural factors, such as sulfation pattern, molecular weight, monosaccharide composition, and glycosidic linkages. Remarkably, chemical modification, enzymatic hydrolysis and crosslinking are promising approaches for developing the application of these polysaccharides through enhancement and/or addition of new biological properties. This paper reviews the recent advances on these structure modification methods on fucoidans, ulvans, and carrageenans. The physical, chemical and biological properties influenced by the addition of functional groups are also discussed. In addition, an overview of specific enzymes selectively producing oligosaccharides with improved bioactivities as well as ionic and covalent cross-linking strategies are provided. These targeted methods have the potential to develop novel compounds with outstanding biodegradability and biocompatibility, along with low toxicity suitable for diverse applications in biomedical fields, including drug delivery.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109358"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142881434","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":"Unveiling cyclodextrin conjugation as multidentate excipients: An exploratory journey across industries.","authors":"Roshani Gandhi, Nishant Chopade, Prashant K Deshmukh, Rahul G Ingle, Minal Harde, Sameer Lakade, Mahesh P More, Rahul S Tade, Mahesh S Bhadane","doi":"10.1016/j.carres.2024.109357","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109357","url":null,"abstract":"<p><p>The discovery of branched molecules like dextrin by Schardinger in 1903 marked the inception of cyclodextrin (CD) utilization, catalyzing its journey from laboratory experimentation to widespread commercialization within the pharmaceutical industry. CD, a cyclic oligosaccharide containing glucopyranose units, acts as a versatile guest molecule, forming inclusion complexes (ICs) with various host molecules. Computational studies have become instrumental in elucidating the intricate interactions between β-CD and guest molecules, enabling the prediction of binding energy, forces, affinity, and complex stability. The computational approach has established robust correlations with experimental outcomes, enhancing our understanding of CD-mediated complexation phenomena. This comprehensive review delves into the CD based Inclusion complex (CDIC) formation and a myriad of components, including drug molecules, amino acids, vitamins, and volatile oils. These complexes find applications across diverse industries, ranging from pharmaceuticals to nutraceuticals, food, fragrance, and beyond. In the pharmaceutical realm, β- CDICs offer innovative solutions for enhancing drug solubility, stability, and bioavailability, thus overcoming formulation challenges associated with poorly water-soluble drugs. Furthermore, the versatility of CDs extends beyond pharmaceuticals, with applications in the encapsulation of phytoactive compounds in nutraceuticals and the enhancing flavor, aroma in food and fragrance industries. This review underscores the pivotal role of CDs conjugation in modern drug delivery systems, emphasizing the importance of interdisciplinary approaches that integrate computational modeling with experimental validation. As the pharmaceutical landscape continues to evolve, CDs-based formulations stand poised to drive innovation and address the ever-growing demand for efficacious and patient-friendly drug delivery solutions.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"549 ","pages":"109357"},"PeriodicalIF":2.4,"publicationDate":"2024-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142871485","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":"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 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.</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}

{"title":"2^A,6^A-F-Hepta-O-tert-butyldimethylsilyl α-cyclodextrin - A carbohydrate undecaol with all OH groups visible in NMR indicative of a partially disrupted hydrogen bond network.","authors":"Morten Lang Zimmermann, Mikael Bols","doi":"10.1016/j.carres.2024.109354","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109354","url":null,"abstract":"<p><p>During a synthesis of the well-known and useful building block 6^A-F-hexa-O-tert-butyldimethylsilyl α-cyclodextrin (2) by silylation of α-cyclodextrin (1) we isolated as a byproduct the oversilylated 2^A,6^A-F-hepta-O-tert-butyldimethylsilyl α-cyclodextrin (3) where one 2-OH group has also been silylated. This unsymmetrical new compound has a remarkable ¹H NMR spectrum in CDCl₃ where all 11 alcohol groups are visible. We have analyzed the spectrum of 3 using 1D and 2D 800 MHz NMR and are able to assign all the 11 alcohol protons. The remarkable chemical shifts of these protons are interpreted as being due to a partial disruption of an otherwise efficient hydrogen bond network.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109354"},"PeriodicalIF":2.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833905","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":"Sialylation reactions: Expanding the C-5 effect to phosphate leaving groups.","authors":"Anupama Das, Shay Adio, Jeremy Brincken, Alexei V Demchenko, Cristina De Meo","doi":"10.1016/j.carres.2024.109353","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109353","url":null,"abstract":"<p><p>With the expanding use of phosphates as leaving groups in sialylations, little remains known about the C-5 effect towards their reactivity and stereoselectivity in the presence of a range of acceptors, and in different solvents. Herein we report the comparison between sialyl phosphate donors bearing N-acetyloxazolidinone and trifluoroacetamido functionalities at C-5. Excellent results and complete stereoselectivity were observed in several sialylations, but the outcome was influenced by the nature of the solvent and/or glycosyl acceptor.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109353"},"PeriodicalIF":2.4,"publicationDate":"2024-12-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142863407","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":"Transglycosylation behavior of Mucor hiemalis endo-β-N-acetylglucosaminidase to β-cyclodextrin derivatives with multivalent glucose moieties for synthesizing cyclodextrin-based oligosaccharide clusters.","authors":"Yusuke Tomabechi, Yoshiki Oda, Kenji Yamamoto, Takashi Yamanoi","doi":"10.1016/j.carres.2024.109352","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109352","url":null,"abstract":"<p><p>We investigated the transglycosylation reaction of two types of oligosaccharide acceptors, i.e., β-cyclodextrin (CD) derivatives 1 and 2 conjugated with multiple glucose (Glc) units, catalyzed by endo-β-N-acetyl-glucosaminidase from Mucor hiemalis (Endo-M) using the oligosaccharide donor sialoglycopeptide (SGP). The acceptor specificity of the enzyme transglycosylation of 1 and 2 having seven Glc moieties within small nanoscale spatial regions on the β-CDs was investigated on the basis of the effect of the molar ratios of SGP to acceptors 1 or 2 with different spatial configurations on the transglycosylation behavior. The formation of the corresponding CD-based oligosaccharide clusters from Endo-M was also evaluated.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109352"},"PeriodicalIF":2.4,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142869398","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":"Analysing the apoptotic potential of green synthesized Nyctanthes arbor-tristis chitosan nanoparticles in MDA-MB-231 and SKOV3 cell lines.","authors":"Saradhadevi Muthukrishnan, Gayathiri Gunasangkaran, Harshini Swaminathan, Peter Linus Kilambo, Anjali K Ravi, Vijaya Anand Arumugam, Velayuthaprabhu Shanmugam, Marie Arockianathan Pushpam, Ashokkumar Kaliyaperumal, Gurusaravanan Packiaraj","doi":"10.1016/j.carres.2024.109344","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109344","url":null,"abstract":"<p><p>Gynecological tumors are highly aggressive cancers in women, often treated with conventional treatments that can cause significant side effects. This study focuses on the preparation of chitosan nanoparticles from Nyctanthes arbor-tristis leaves, which possess anti-tumor properties, to address and overcome these issues. The successfully synthesized nanoparticles were characterized by UV-spectroscopy, DLS, TEM, and FTIR spectroscopy to analyze their physiochemical properties. In vitro studies, including cytotoxicity and scratch wound healing assays, along with staining and qRT-PCR, revealed the nanoparticles' anticancer efficacy against breast and ovarian cancer cells. The formation of Nat-CSNPs showed an absorbance peak at 221 nm, a particle size range of 41-56 nm with a spherical shape, polydispersity, and a positive surface charge. FTIR spectroscopy demonstrated the presence of functional groups associated with the synthesized Nat-CSNPs. It exhibited dose-dependent cytotoxicity, with IC₅₀ values of 62.40 μg/ml for MDA-MB-231 and 44.7 μg/ml for SKOV3 cells. Further assays such as wound healing assay, and DAPI/AO/EtBr staining demonstrated their antiproliferative and apoptotic effects on MDA-MB-231 and SKOV3 cells. Induction of apoptosis by the chitosan-nanoparticle via upregulation of the pro-apoptotic genes (Bax, Cas3, Cas9) and downregulation of antiapoptotic genes (Bcl2) was assessed using qRT-PCR analysis. In vivo acute toxicity assessments of Nat-CSNPs on Danio rerio revealed no significant impact on glucose levels or AST, ALT, and AChE activity, indicating low toxicity. These findings underscore the potent anticancer effects of Nat-CSNPs, particularly inducing apoptosis in MDA-MB-231 and SKOV3 cell lines. While demonstrating low toxicity in Danio rerio, Nat-CSNPs are considered a promising novel anti-cancer drug for breast and ovarian cancer treatment.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109344"},"PeriodicalIF":2.4,"publicationDate":"2024-12-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142794397","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":"Chemically modified chitosan as a functional biomaterial for drug delivery system.","authors":"Devika Sajeev, Aparna Rajesh, R Nethish Kumaar, D Aswin, Rangasamy Jayakumar, Sreeja C Nair","doi":"10.1016/j.carres.2024.109351","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109351","url":null,"abstract":"<p><p>Chitosan is a natural polymer that can degrade in the environment and support green chemistry. It displays superior biocompatibility, easy access, and easy modification due to the reactive amino groups to transform or improve the physical and chemical properties. Chitosan can be chemically modified to enhance its properties, such as water solubility and biological activity. Modified chitosan is the most effective functional biomaterial that can be used to deliver the drugs to the targeted site. With diverse and versatile characteristics, it can be fabricated into various drug delivery systems such as membranes, beads, fibers, microparticles, composites, and scaffolds, for different drug delivery methods. Integrating nanotechnology with modified chitosan enhanced the delivery attributes of antibacterial, antifungal, antiviral, anticancer, anti-inflammatory, protein/peptides, and nucleic acids for intended use toward desired therapeutic outcomes. The review brings out an overview of the research regarding drug delivery systems utilizing modifying chitosan detailing the properties, functionality, and applications.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109351"},"PeriodicalIF":2.4,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142821934","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":"Highly efficient esterification of waxy maize starch in choline chloride/acetic acid acidic deep eutectic solvent system.","authors":"Kexuan Sun, Jie Yi, Rui Dai, Hui Chen","doi":"10.1016/j.carres.2024.109345","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109345","url":null,"abstract":"<p><p>In this study, to address the issue of solvent selection in the chemical modification of starch, a method was developed for the efficient esterification of waxy maize starch (WMS) using an acidic deep eutectic solvent composed of choline chloride and acetic acid (CCHAc-ADES). The impact of different mass fractions of CCHAc-ADES on the degree of substitution and reaction efficiency of lauric acid starch esters was explored. It was found that under the conditions of 70 wt% CCHAc-ADES, starch esters with the highest degree of substitution of 0.161 were successfully prepared, achieving an esterification efficiency of 79.63 %. ¹³C and ¹H nuclear magnetic resonance spectroscopy, X-ray diffraction and gel permeation chromatography revealed that CCHAc-ADES acted within the surface voids of WMS particles without seriously damaging the WMS structure, making it a favorable solvent for chemical modification of WMS. By monitoring changes in the morphology, relative crystallinity, particle size, and hydrophobicity of esterified WMS in CCHAc-ADES, the formation mechanism of lauric acid starch esters was inferred, primarily related to the competitive hydrogen bonding of CCHAc-ADES with WMS. The method proposed in this study allows for the preparation of long-chain fatty acid starch esters without the use of any additional chemicals or enzymes, offering significant guidance for the application of deep eutectic solvents in green synthesis.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109345"},"PeriodicalIF":2.4,"publicationDate":"2024-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142806462","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}