Carbohydrate Research最新文献

{"title":"Antimicrobial biodegradable packaging films from phosphorylated starch: A sustainable solution for plastic waste","authors":"Neeru Devi ,&nbsp;Shayoraj ,&nbsp;Geeta ,&nbsp;Shivani ,&nbsp;Simran Ahuja ,&nbsp;Santosh Kumar Dubey ,&nbsp;Sanjay Sharma ,&nbsp;Satish Kumar","doi":"10.1016/j.carres.2025.109404","DOIUrl":"10.1016/j.carres.2025.109404","url":null,"abstract":"<div><div>This study focused on developing biodegradable packaging films based on starch as an alternative to non-biodegradable such as petroleum-derived synthetic polymers. To improve its physicochemical properties, potato starch was chemically modified through phosphorylation. Starch phosphorylation was carried out using cyclic 1,3-propanediol phosphoryl chloride (CPPC), produced phosphorylated starch (PS), and analyzed using Fourier transform infrared (FT-IR), X-ray diffraction (XRD), Nuclear magnetic resonance (NMR), and Thermogravimetric analysis (TGA). The thermal stability of PS increased to 292 °C due to the formation of starch phosphate ester in comparison to pure starch (281 °C). Moreover, using glycerol as a plasticizer, the solvent casting method was employed to synthesize the PS/PVA biofilms. The synthesized biofilms (PPS) were further characterized using FT-IR, TGA, Mechanical testing, and Scanning electron microscopy (SEM). The result indicated that blend films have higher tensile strength (41.61 MPa) and elongation at break (240 %) than pure PVA film (29.84 MPa, 102 %). The soil burial study showed that the biodegradation of PPS blend films increased to 63.79 %. Nevertheless, the blend film showed decreased solubility, water absorption, water vapor transmission rate, and moisture content with PS, while its surface hydrophobicity increased from 61.2° to 95.6°. PPS blends have stronger antibacterial activity against <em>S. aureus</em> than <em>E. coli.</em> Accordingly, the prepared PPS III biofilm was further used for brown bread packaging. Compared to LDPE packaging, the bread wrapped in PPS III blend film exhibited enhanced visual appearance and extended shelf-life. The novelty of our work lies in the modification of starch using CPPC, which was further used to fabricate biodegradable films. Therefore, the developed biofilm may be a reference for additional research and can potentially replace synthetic, non-degradable polymer-based films in the packaging industry.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109404"},"PeriodicalIF":2.4,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063608","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 ,&nbsp;Edileuza Marcelo Vieira ,&nbsp;Jemmyson Romário de Jesus ,&nbsp;Cláudio Carvalho Santana Júnior ,&nbsp;José Adão Carvalho Nascimento Júnior ,&nbsp;Ana Maria Santos Oliveira ,&nbsp;Adriano Antunes de Souza Araújo ,&nbsp;Laurent Picot ,&nbsp;Izabel Almeida Alves ,&nbsp;Mairim Russo Serafini","doi":"10.1016/j.carres.2025.109406","DOIUrl":"10.1016/j.carres.2025.109406","url":null,"abstract":"<div><div>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 <em>in vitro</em> 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. <em>In vivo</em> toxicity assay was performed using <em>Tenebrio molitor</em> 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 <em>S. aureus</em> ATCC 25923.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 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 ,&nbsp;Michele Verboni ,&nbsp;Serena Benedetti ,&nbsp;Daniele Paderni ,&nbsp;Carla Carfagna ,&nbsp;Andrea Duranti ,&nbsp;Simone Lucarini","doi":"10.1016/j.carres.2025.109405","DOIUrl":"10.1016/j.carres.2025.109405","url":null,"abstract":"<div><div>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 (<strong>4a-g</strong>), ribose (<strong>4h</strong>) and lactose (<strong>4i</strong>) starting from the respective acetals <strong>3</strong>. The latter were obtained through oxidative alkoxycarbonylation of olefins. For all compounds <strong>3</strong> and <strong>4</strong>, 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 <em>ad hoc</em> synthesized compound <strong>3k</strong>, featuring a 4-methoxy substituent on the phenyl ring and a 1,2-<em>O</em>-isopropylidene ribose moiety, provided the most promising results for a possible use as a sunscreen. Indeed, its Sun Protection Factor (SPF), calculated <em>in vitro</em>, was higher with respect to that of ethylhexyl methoxycinnamate (EHMC), which is already utilized in sun care products. Moreover, <strong>3k</strong> 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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Glycans of parasitic nematodes – from glycomes to novel diagnostic tools and vaccines","authors":"Shi Yan","doi":"10.1016/j.carres.2025.109407","DOIUrl":"10.1016/j.carres.2025.109407","url":null,"abstract":"<div><div>Nematodes, commonly known as roundworms, are among the most prevalent and diverse multicellular organisms on Earth, belonging to the large phylum <em>Nematoda</em>. In addition to free-living species, many nematodes are parasitic, infecting plants, animals, and humans. Nematodes possess a wide array of genes responsible for carbohydrate metabolism and glycosylation. The glycosylation processes in parasitic nematodes often result in unique glycan modifications that are not present in their hosts. These distinct glycans can be highly immunogenic to mammalian hosts and play significant immunoregulatory roles during infection. This mini-review article summarises the glycosylation capabilities and characteristics of parasitic nematodes based on glycomic data. It also highlights recent research advances that explore the biological significance of nematode glycans and their potential for diagnostic and vaccine applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109407"},"PeriodicalIF":2.4,"publicationDate":"2025-01-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063642","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":"Efficient synthesis of coumarin based triazole linked O-glycoconjugates as new bio-active glycohybrids","authors":"Sunil Sharma,&nbsp;Ram Sagar","doi":"10.1016/j.carres.2025.109395","DOIUrl":"10.1016/j.carres.2025.109395","url":null,"abstract":"<div><div>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 <em>O</em>-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 <em>O</em>-glycoconjugates as new glycohybrids were designed and efficiently synthesized in very good isolated yields, using <span>d</span>-glucose, <span>d</span>-galactose, <span>d</span>-mannose, <span>d</span>-arabinose, 3,4,6-tri-<em>O</em>-acetyl-D-glucal, 3,4,6-tri-<em>O</em>-acetyl-D-galactal and 3,4-di-<em>O</em>-acetyl-D-arabinal derived 1-<em>O</em>-propargylated glycosides, reacting with various 4-azidocoumarins under click-chemistry reaction conditions. The prepared new coumarin-based <em>O</em>-glycoconjugates as glycohybrids were found to possess anticancer activity against MCF-7 breast cancer cell lines at micromolar concentration.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 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":"Named reaction in carbohydrate chemistry: A review","authors":"Shakeel Alvi,&nbsp;Rashid Ali","doi":"10.1016/j.carres.2025.109396","DOIUrl":"10.1016/j.carres.2025.109396","url":null,"abstract":"<div><div>Central to the synthetic organic chemist's armoury are the organic/inorganic reagents which are employed to effect a broad range of structural changes. Herein, we report a collection of 29 organic named reactions applicable in the carbohydrate chemistry, arranged in alphabetical order. In this contribution, we have displayed general schemes, examples and probable reaction mechanism for each chemical reaction. This collection should be useful to researchers and students alike.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109396"},"PeriodicalIF":2.4,"publicationDate":"2025-01-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143063745","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 ,&nbsp;Natalia Pachura ,&nbsp;Anna Duda-Madej ,&nbsp;Mateusz Garbicz ,&nbsp;Tomasz Gębarowski ,&nbsp;Alicia Dominguez-Martin ,&nbsp;Magdalena Rowińska-Żyrek","doi":"10.1016/j.carres.2025.109387","DOIUrl":"10.1016/j.carres.2025.109387","url":null,"abstract":"<div><div>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 <em>Escherichia coli</em> and efficacy against methicillin-resistant <em>Staphylococcus aureus</em> (MRSA), <em>Escherichia coli</em> ESBL, and <em>Pseudomonas aeruginosa</em> 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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 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,&nbsp;Ana Paula Butiuk,&nbsp;Luis Alberto Brumovsky,&nbsp;María Alicia Martos","doi":"10.1016/j.carres.2025.109386","DOIUrl":"10.1016/j.carres.2025.109386","url":null,"abstract":"<div><div>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 (<em>Wickerhanomyces anomalus</em>).</div><div>The supernatant of <em>W. anomalus</em> 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.</div><div>The highest extraction yield was obtained using <em>processed</em> 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.</div><div>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.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 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}

{"title":"Antigenicity evaluation of the synthetic trisaccharides related to Plesiomonas shigelloides serotype O51 O-antigen containing an acetamidino group","authors":"Chunjun Qin ,&nbsp;Wei Han ,&nbsp;Guangzong Tian ,&nbsp;Xiaopeng Zou ,&nbsp;Anna Maciejewska ,&nbsp;Jolanta Lukasiewicz ,&nbsp;Peter H. Seeberger ,&nbsp;Jing Hu ,&nbsp;Jian Yin","doi":"10.1016/j.carres.2025.109388","DOIUrl":"10.1016/j.carres.2025.109388","url":null,"abstract":"<div><div>Bacterial surface polysaccharides are widely decorated with diverse rare functional groups. An understanding of the role of these functional groups in immunological activity of the glycans is required for the development of carbohydrate-based treatment against bacterial infectious diseases. Here, the antigenicity evaluation of synthetic trisaccharide <strong>1</strong> related to <em>Plesiomonas shigelloides</em> serotype O51 lipopolysaccharide (LPS) O-antigen and its acetamido derivative <strong>2</strong> was achieved to elucidate the immunological importance of O-antigen structure. The rabbit antisera with high titers of IgG and IgM were collected after immunization with purified <em>P. shigelloides</em> serotype O51 LPS. Glycan microarray screening results showed that both IgG and IgM in rabbit antisera bound specifically to trisaccharides <strong>1</strong> and <strong>2</strong>, indicating that the trisaccharide repeating unit is a key antigenic epitope of <em>P. shigelloides</em> serotype O51 O-antigen, while the acetamidino group has no influence on the antigenicity. This finding provides key information for glycoconjugate vaccine design for <em>P. shigelloides</em> serotype O51.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109388"},"PeriodicalIF":2.4,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000674","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":"Synthesis of 2-hydroxy analogues of castanospermine, 1-epi-castanospermine and their iminooctitols from sugar-derived lactam","authors":"Nagaraja Ingaladal ,&nbsp;Ravi S. Lankalapalli","doi":"10.1016/j.carres.2025.109385","DOIUrl":"10.1016/j.carres.2025.109385","url":null,"abstract":"<div><div>The synthesis of 2-hydroxy analogues of castanospermine from two new iminooctitols via Mitsunobu cyclization is described. The iminooctitols were derived from the dihydroxylation of an allyl alcohol intermediate, obtained by adding vinylmagnesium bromide to the C6-aldehyde of a protected 1-deoxynojirimycin. An orthogonally protected hemiacetal with silyl group at the C6-hydroxy position and remaining as benzyl ethers, synthesized in four steps from <span>d</span>-glucose, served as a building block in the synthesis of the 1-deoxynojirimycin intermediate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"550 ","pages":"Article 109385"},"PeriodicalIF":2.4,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143000685","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}