Carbohydrate Research最新文献

{"title":"A review on the biological activities and the nutraceutical potential of chitooligosaccharides","authors":"Makyson R.S. Leal ,&nbsp;Luiza R.A. Lima ,&nbsp;Natalie E.R. Rodrigues ,&nbsp;Paulo A.G. Soares ,&nbsp;Maria G. Carneiro-da-Cunha ,&nbsp;Priscilla B.S. Albuquerque","doi":"10.1016/j.carres.2024.109336","DOIUrl":"10.1016/j.carres.2024.109336","url":null,"abstract":"<div><div>Chitooligosaccharides (CHOS) or chitosan oligosaccharides (COS) are oligomers mainly composed of <span>d</span>-glucosamine (GlcN) units and structured in a positively charged, basic, amino molecule obtained from the degradation of chitin/chitosan through physical, chemical, or enzymatic methods. CHOS display physicochemical properties attractive to applications from the food to the biomedical field, such as non-toxicity to humans, high water solubility, low viscosity, biocompatibility, and biodegradability. These properties also allow CHOS to exert important biological activities, for example, antioxidant, antimicrobial, anti-inflammatory, immunomodulatory, antitumor, and hypocholesterolemic ones, besides to exhibit applications in food systems, technological, and nutraceutical potential. Therefore, this study summarized the synthesis and chemical structure, biological functions, and mechanisms of action of CHOS; with this, we aimed to contribute to the knowledge about the application of CHOS from the food to the biomedical industries.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109336"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142784213","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 ,&nbsp;Gayathiri Gunasangkaran ,&nbsp;Harshini Swaminathan ,&nbsp;Peter Linus Kilambo ,&nbsp;Anjali K. Ravi ,&nbsp;Vijaya Anand Arumugam ,&nbsp;Velayuthaprabhu Shanmugam ,&nbsp;Marie Arockianathan Pushpam ,&nbsp;Ashokkumar Kaliyaperumal ,&nbsp;Gurusaravanan Packiaraj","doi":"10.1016/j.carres.2024.109344","DOIUrl":"10.1016/j.carres.2024.109344","url":null,"abstract":"<div><div>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 <em>Nyctanthes arbor-tristis</em> 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. <em>In vitro</em> 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. <em>In vivo</em> acute toxicity assessments of Nat-CSNPs on <em>Danio rerio</em> 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 <em>Danio rerio</em>, Nat-CSNPs are considered a promising novel anti-cancer drug for breast and ovarian cancer treatment.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109344"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","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":"Highly efficient esterification of waxy maize starch in choline chloride/acetic acid acidic deep eutectic solvent system","authors":"Kexuan Sun ,&nbsp;Jie Yi ,&nbsp;Rui Dai ,&nbsp;Hui Chen","doi":"10.1016/j.carres.2024.109345","DOIUrl":"10.1016/j.carres.2024.109345","url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109345"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","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}

{"title":"Sialylation reactions: Expanding the C-5 effect to phosphate leaving groups","authors":"Anupama Das ,&nbsp;Shay Adio ,&nbsp;Jeremy Brincken ,&nbsp;Alexei V. Demchenko ,&nbsp;Cristina De Meo","doi":"10.1016/j.carres.2024.109353","DOIUrl":"10.1016/j.carres.2024.109353","url":null,"abstract":"<div><div>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 <em>N</em>-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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109353"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","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":"2A,6A−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,&nbsp;Mikael Bols","doi":"10.1016/j.carres.2024.109354","DOIUrl":"10.1016/j.carres.2024.109354","url":null,"abstract":"<div><div>During a synthesis of the well-known and useful building block 6^A−F-hexa-O-<em>tert</em>-butyldimethylsilyl α-cyclodextrin (<strong>2</strong>) by silylation of α-cyclodextrin (<strong>1</strong>) we isolated as a byproduct the oversilylated 2^A,6^A−F-hepta-O-<em>tert</em>-butyldimethylsilyl α-cyclodextrin (<strong>3</strong>) 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 <strong>3</strong> 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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"Article 109354"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"The preparation, physicochemical characterization and antibacterial activity of Pectin/Zinc Alginate composite film","authors":"Chang Liu ,&nbsp;Ning Li ,&nbsp;Li Niu ,&nbsp;Xu Li ,&nbsp;Jacko Feng ,&nbsp;Zhiming Liu","doi":"10.1016/j.carres.2025.109412","DOIUrl":"10.1016/j.carres.2025.109412","url":null,"abstract":"<div><div>Pectin and sodium alginate (SA) were mixed to form composite films using the casting method. Antibacterial packaging films (pectin/ZA) were obtained by a simple ion exchange method with a pectin/SA blend film. The effect of Zn²⁺ on the pectin/SA blend in terms of structural, morphological, thermal, physical, and mechanical properties, as well as antibacterial activity, was investigated in detail. The FT-IR, XRD, and XPS results indicated that Zn²⁺ was successfully introduced into the pectin/SA blend film. Additionally, SEM images exhibited the uniform incorporation of Zn²⁺ into the pectin/SA blend film. Moreover, the blend film of pectin and alginate improved its thermal properties, mechanical properties, and water resistance compared to the pure pectin film. Furthermore, the pectin/ZA blend film had significant antimicrobial activity against <em>S. aureus</em> and <em>E. coli</em>, revealing its potential application in food packaging.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109412"},"PeriodicalIF":2.4,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143167492","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: An overview of its properties, solubility, functional technologies, food and health applications","authors":"Great Iruoghene Edo ,&nbsp;Winifred Ndudi ,&nbsp;Ali B.M. Ali ,&nbsp;Emad Yousif ,&nbsp;Khalid Zainulabdeen ,&nbsp;Patrick Othuke Akpoghelie ,&nbsp;Endurance Fegor Isoje ,&nbsp;Ufuoma Augustina Igbuku ,&nbsp;Rapheal Ajiri Opiti ,&nbsp;Arthur Efeoghene Athan Essaghah ,&nbsp;Dina S. Ahmed ,&nbsp;Huzaifa Umar ,&nbsp;Ahmed A. Alamiery","doi":"10.1016/j.carres.2025.109409","DOIUrl":"10.1016/j.carres.2025.109409","url":null,"abstract":"<div><div>The properties and potential applications of chitosan have attracted a lot of interest; each year, the number of publications and patents based on this polymer increases. A significant obstacle to the application of chitosan is its limited solubility in basic and neutral solutions. The fact that chitosan is a series of molecules with variations in size, content, and monomer distribution rather than a single polymer with a well-defined structure and a natural origin is another significant barrier. Some of the claimed biological qualities are distinct, and these characteristics have a fundamental effect on the polymer's technological and biological performance. The poor solubility of the polymer can be improved by chitosan chemistry, and in this assessment, we discuss the changes made to make chitosan more soluble and its possible uses. We concentrate on a few of the primary biological characteristics of chitosan and how they relate to the physicochemical characteristics of the polymer. The use of chitosan in the environmentally friendly manufacture of metallic nanoparticles as well as its usage as a booster for biocatalysts are two further applications of polymers that are linked to green processes that we revisit. This study also presents information about utilizing chitosan's technological advantages.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109409"},"PeriodicalIF":2.4,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143073974","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":"Odorless synthesis of thioglycosides using isothiouronium salts","authors":"Lanrong Tang ,&nbsp;Jie Zhang ,&nbsp;Tianyun Guo,&nbsp;Xiaolei Wang,&nbsp;Jian Liu","doi":"10.1016/j.carres.2025.109408","DOIUrl":"10.1016/j.carres.2025.109408","url":null,"abstract":"<div><div>A practical and efficient method for the synthesis of thioglycosides has been developed using readily available isothiouronium salts as masked S-glycosylation reagents. Under optimized conditions, per-acetylated glycoside bromides were robustly converted into thioglycosides in moderate to good yields with exclusive stereoselectivity. By employing an increased dosage of TMG(1,1,3,3-tetramethylguanidine), a one-pot <em>S</em>-glycosylation–deacetylation process was achieved, affording deprotected thioglycosides in high yields. The methodology was successfully applied to a variety of monosaccharide substrates and demonstrated scalability to gram-scale reactions while maintaining efficiency. This approach represents an environmentally friendly alternative to conventional thioglycoside synthesis methods, overcoming the challenges of unpleasant odor and the limited availability of traditional thiol reagents.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109408"},"PeriodicalIF":2.4,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143350156","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 multigram synthesis of 1,4:3,6-Dianhydro-α-D-glucopyranose by chemical synthesis methods: Development and scale-up study of synthetic routes","authors":"Zhi-Fei Chen ,&nbsp;Jia-Ming Zhao ,&nbsp;Hao-Liang Li ,&nbsp;Hao-Yang Chen ,&nbsp;Gao-Lei Xi ,&nbsp;Liu-Ke Zhang ,&nbsp;Qing-Fu Wang ,&nbsp;Qiu-Ling Wang ,&nbsp;Yong-Zhen Zhao ,&nbsp;Kai Yang","doi":"10.1016/j.carres.2025.109402","DOIUrl":"10.1016/j.carres.2025.109402","url":null,"abstract":"<div><div>A reliable chemical synthesis method for the preparation of 1,4:3,6-dianhydro-α-D-glucopyranose (DGP) has been developed on the first time, with an overall four-step yield of 20 % on a 200g scale. The method for 2-OH regioselective benzylation protection of Methyl α-<span>d</span>-glucopyranoside was systematically optimized, providing a more scalable and cost-effective approach. The 3,6-anhydro pyranose intermediate was obtained through a two-step one-pot process. It has been confirmed that 2-OH protection enhanced the ring stability of 3,6-anhydro pyranose and also found that the conformation of 3,6-anhydro pyranose indeed promoted the construction of 1,4-ether bonds. Overall, this work facilitated further application research of DGP in the fields of chemical synthesis, medicinal chemistry, and food chemistry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"551 ","pages":"Article 109402"},"PeriodicalIF":2.4,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143350155","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":"Recombinant expression and characterization of an α-galactosidase from Thermoclostridium stercorarium subsp. thermolacticum DSM 2910 and its application in the hydrolysis of raffinose","authors":"Lin Ge ,&nbsp;Ruobing Jia ,&nbsp;Yingying Liu ,&nbsp;Lingling Zhan","doi":"10.1016/j.carres.2025.109410","DOIUrl":"10.1016/j.carres.2025.109410","url":null,"abstract":"<div><div>Soybean contains anti-nutritional factor raffinose oligosaccharide (RFOs), which can cause flatulence, gastrointestinal dysfunction and low feed utilization rate. However, α-galactosidase can hydrolyze raffinose oligosaccharides (RFOs). Therefore, in this study, a novel α-galactosidase from <em>Thermoclostridium stercorarium subsp. thermolacticum</em> DSM 2910 (TstGal) which can hydrolyze raffinose was cloned, expressed, purified, and characterized. The gene fragment size is 2208 bp, and the enzyme TstGal consists of 736 amino acids. Under the optimum culture conditions, the maximum enzyme activity of the target protein TstGal was 23.8 U/mL. The enzyme was purified 11.3-fold by Ni-NTA agarose resin with an overall recovery of 51.4 % and specific activity of 9.0 U/mg, and its relative molecular weight was about 85 kDa. The optimal temperature of TstGal was 70 °C, and it exhibited excellent thermal stability at 60 °C. Furthermore, The TstGal had the highest activity at pH 6.5 and good pH stability at pH 5.0–7.5. Besides, the enzyme has a good sugar tolerance to galactose and sucrose. In addition, K⁺ and Fe²⁺ could significantly enhance the enzyme activity at a concentration of 5 mM. The values of K_M, V_max, k_cat, and k_cat/K_M for <em>p</em>NPGal were found to be 0.507 mM, 13.979 U/mg, 19.735 s⁻¹, and 38.895 s⁻¹mM⁻¹, respectively. Under the optimum conditions, the maximum hydrolysis rate of raffinose by TstGal reached 99.8 %, which shows that the enzyme had potential application value in food and feed industry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109410"},"PeriodicalIF":2.4,"publicationDate":"2025-01-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143073977","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}