Carbohydrate Research最新文献

{"title":"Synthesis and antioxidant evaluation of coumarin-functionalised chitosan: A potent, non-toxic free radical scavenging compound.","authors":"Siyu Zhu, Qin Miao, Qiuhong Chen, Liguang Tian, Fang Dong, Zhanyong Guo, Qing Li","doi":"10.1016/j.carres.2024.109311","DOIUrl":"10.1016/j.carres.2024.109311","url":null,"abstract":"<p><p>In the present study, we designed to link the coumarin molecule to chitosan via a triazole group and synthesized chitosan-coumarin derivatives, which were further quaternized in one step in order to further improve their solubility to obtain a second series of chitosan-coumarin ammonium salt derivatives. The structures of these chitosan derivatives were verified by FT-IR and ¹H NMR. They were tested for their antioxidant activities. The experimental results showed that the derivatives had excellent free radical scavenging ability. The introduction of the coumarin moiety significantly improved the antioxidant activity, and the scavenging capacity was much higher than that of the chitosan feedstock in all three antioxidant tests. Overall, the scavenging capacity of chitosan-coumarin ammonium salt derivatives was slightly higher than that of chitosan-coumarin derivatives, with the highest scavenging rates in all three tests. Compound 8B scavenged 98.74 % (0.01 mg/mL) of superoxide anion radicals, compound 8D scavenged 95.5 % (0.3 mg/mL) of DPPH radicals and compound 8A scavenged 92.97 % (0.2 mg/mL) of hydroxyl radicals. Toxicity assays used L929 cells demonstrated that there was no significant toxicity of the derivatives. The results indicated that the chitosan derivatives described herein were safe and non-toxic and have good antioxidant activity.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"548 ","pages":"109311"},"PeriodicalIF":2.4,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142791033","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":"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":"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, Jie Yi, Rui Dai, Hui Chen","doi":"10.1016/j.carres.2024.109345","DOIUrl":"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":"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":"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":"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":"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":"","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":"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":"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":"Development and characterization of farnesol complexed in β- and hydroxypropyl-β-cyclodextrin and their antibacterial activity.","authors":"Anamaria Mendonça Santos, Edileuza Marcelo Vieira, Jemmyson Romário de Jesus, Cláudio Carvalho Santana Júnior, José Adão Carvalho Nascimento Júnior, Ana Maria Santos Oliveira, Adriano Antunes de Souza Araújo, Laurent Picot, Izabel Almeida Alves, Mairim Russo Serafini","doi":"10.1016/j.carres.2025.109406","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109406","url":null,"abstract":"<p><p>Farnesol (FAR) belongs to terpenes group and is a sesquiterpene alcohol and a hydrophobic compound, which can be extracted from natural sources or obtained by organic chemical or biological synthesis. Recent advances in the field of nanotechnology allow the drawbacks of low drug solubility, which can improve the drug therapeutic index. Therefore, this study aimed to prepare the FAR inclusion complexes with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) through freeze-drying method, proposing their physicochemical characterization, comparing their toxicity, and evaluating their in vitro antibacterial activity. Initially, physical mixture and freeze-dried inclusion complexes of FAR/β-CD and FAR/HP-β-CD were obtained in the molar ratio (1:1). The samples were characterized by DSC, TG/DTG, FTIR, PXRD, SEM, pH_PZC, and the complexation efficiency were performed by HPLC. In vivo toxicity assay was performed using Tenebrio molitor larvae to determine the LD50 and toxic dose of the samples. Also, it was proposed that the evaluation of the fluorescence suppression of Bovine Serum Albumin and the antibacterial activity. The complexation of FAR was evidenced with β-CD and HP-β-CD by the characterization techniques analyzed. The complexation efficiency of FAR/β-CD and FAR/HP-β-CD were 73,53 % and 74.12 %, respectively. The inclusion complexes demonstrated a reduction in toxicity, as evidenced by lower toxic and LD50 doses compared to the free FAR. The inclusion complexes induced conformational changes in BSA, suggesting that they reached the subdomains containing tryptophan residues. In terms of antibacterial activity, FAR/β-CD and FAR/HP-β-CD did not exhibit significant MIC results compared to free FAR, except for FAR/HP-β-CD against S. aureus ATCC 25923.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109406"},"PeriodicalIF":2.4,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045662","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":"New cinnamic acid sugar esters as potential UVB filters: Synthesis, cytotoxicity, and physicochemical properties.","authors":"Diego Olivieri, Michele Verboni, Serena Benedetti, Daniele Paderni, Carla Carfagna, Andrea Duranti, Simone Lucarini","doi":"10.1016/j.carres.2025.109405","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109405","url":null,"abstract":"<p><p>Cinnamic Acid Sugar Ester Derivatives (CASEDs) are a class of natural compounds that exhibit several interesting biological activities. However, to date, no examples of their use in sunscreen formulations have been reported. Here, we describe the synthesis of a series of novel cinnamic acid esters of glucose (4a-g), ribose (4h) and lactose (4i) starting from the respective acetals 3. The latter were obtained through oxidative alkoxycarbonylation of olefins. For all compounds 3 and 4, UV-Vis spectra were recorded and lipophilicity (i.e., clogP) and cytotoxicity were evaluated. All but one of the synthesized compounds were found to be non-cytotoxic at the concentrations tested and, as expected, absorption spectra depended only on the substituents on the aromatic ring. Finally, the ad hoc synthesized compound 3k, featuring a 4-methoxy substituent on the phenyl ring and a 1,2-O-isopropylidene ribose moiety, provided the most promising results for a possible use as a sunscreen. Indeed, its Sun Protection Factor (SPF), calculated in vitro, was higher with respect to that of ethylhexyl methoxycinnamate (EHMC), which is already utilized in sun care products. Moreover, 3k showed greater antioxidant properties than EHMC, effectively protecting keratinocytes against H₂O₂-induced oxidative damage. At the same time, it showed no cytotoxic effects and preserved cellular metabolic activity and protein content. Based on these results, we believe that CASEDs could find valid applications in the skincare and cosmetics sectors.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109405"},"PeriodicalIF":2.4,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143051803","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":"Efficient synthesis of coumarin based triazole linked O-glycoconjugates as new bio-active glycohybrids.","authors":"Sunil Sharma, Ram Sagar","doi":"10.1016/j.carres.2025.109395","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109395","url":null,"abstract":"<p><p>Glycohybrids are biologically significant molecules with variety of biological functions and are found as structural motifs in numerous natural products. Here, we report the synthesis of various new coumarin-based O-glycoconjugates as glycohybrids that are chirally enriched and bridged by 1,2,3-triazoles ring system. The1,2,3-triazoles bridging was done via CuAAC click-chemistry. Click chemistry offers several advantages, including high chemo- and regioselectivity, mild reaction conditions, easy purification, and compatibility with multiple functional groups. Two series of O-glycoconjugates as new glycohybrids were designed and efficiently synthesized in very good isolated yields, using d-glucose, d-galactose, d-mannose, d-arabinose, 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal and 3,4-di-O-acetyl-D-arabinal derived 1-O-propargylated glycosides, reacting with various 4-azidocoumarins under click-chemistry reaction conditions. The prepared new coumarin-based O-glycoconjugates as glycohybrids were found to possess anticancer activity against MCF-7 breast cancer cell lines at micromolar concentration.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109395"},"PeriodicalIF":2.4,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045663","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":"Chloramphenicol glycoside derivative: A way to overcome its antimicrobial resistance and toxicity.","authors":"Mariusz Dziadas, Natalia Pachura, Anna Duda-Madej, Mateusz Garbicz, Tomasz Gębarowski, Alicia Dominguez-Martin, Magdalena Rowińska-Żyrek","doi":"10.1016/j.carres.2025.109387","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109387","url":null,"abstract":"<p><p>Triggered by the urgent need to tackle the global crisis of multidrug-resistant bacterial infections, in this work, we present a way to overcome chloramphenicol resistance by introducing modifications based on the glycosylation of its hydroxyl groups. The synthesized derivatives demonstrate complete resistance to the action of recombinant chloramphenicol acetyltransferase (CAT) from Escherichia coli and efficacy against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli ESBL, and Pseudomonas aeruginosa ATCC 27853. Glycosylation gives chloramphenicol an additional advantage - the stable glycosidic form is less toxic to human dermal fibroblasts and has significantly better water solubility than non-glycosylated chloramphenicol. Using a specific glycosidase, chloramphenicol can be almost immediately released from the stable prodrug at the site of polybacterial infections.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109387"},"PeriodicalIF":2.4,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143037008","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":"Cassava starch extraction with a polygalacturonase from a wild yeast strain with disintegration activity on plant tissues.","authors":"Silvana A Maidana, Ana Paula Butiuk, Luis Alberto Brumovsky, María Alicia Martos","doi":"10.1016/j.carres.2025.109386","DOIUrl":"https://doi.org/10.1016/j.carres.2025.109386","url":null,"abstract":"<p><p>The objective of the present study was to optimize an enzymatic starch extraction process from cassava roots using a polyglacturonase (PGase) from a wild yeast strain (Wickerhanomyces anomalus). The supernatant of W. anomalus culture, with PGase activity, was used as source of enzyme (enzymatic extract, EE). The cassava starch extractions with the EE were done at lab scale and the effects of several factors were studied by using statistical designs. Chemical and functional properties of the starch obtained (enzymatic starch, ES) and those of a commercial starch (CS), were determined. The highest extraction yield was obtained using processed cassava tissues, a solid-liquid ratio of 3:6, EE with an enzyme dosage of 15 EU mL^-1, at 40 °C for 5 h. Proximal analysis of the ES did not show significant differences with the CS. Swelling power and water solubility of ES increased with the temperature up to 70 °C (1.97 gg^-1) and 90 °C (4.27 % w/w), respectively, similar to those of CS. Viscoamylographic profiles of ES showed a pasting temperature of 63.5 °C, a viscosity peak of 422 BU, an stability of the pasta during cooking of 202 BU and a retrograde trend of 98 BU. These values were slightly different compared to those of CS. Clarity assays determined that ES paste is considered a clear or transparent paste. Microscopic evaluation of the ES grains revealed that they were intact without any mechanical damage. The production of cassava starch by enzyme technology seems to be an interesting alternative to the traditional method of extraction by mechanical means, resulting in a novel biotechnological process.</p>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"109386"},"PeriodicalIF":2.4,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027845","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}