Emma M. Dangerfield , Michael A. Meijlink , Alex A. Hunt-Painter , Seyed A. Nasseri , Stephen G. Withers , Bridget L. Stocker , Mattie S.M. Timmer
{"title":"Synthesis and glycosidase inhibition of 3,4,5-trihydroxypiperidines using a one-pot amination-cyclisation cascade reaction","authors":"Emma M. Dangerfield , Michael A. Meijlink , Alex A. Hunt-Painter , Seyed A. Nasseri , Stephen G. Withers , Bridget L. Stocker , Mattie S.M. Timmer","doi":"10.1016/j.carres.2024.109198","DOIUrl":"10.1016/j.carres.2024.109198","url":null,"abstract":"<div><p>Trihydroxypiperidines are a therapeutically valuable class of iminosugar. We applied a one-pot amination-cyclisation cascade reaction to synthesise 3,4,5-trihydroxypiperidine stereoisomers in three steps from commercially available pentoses and in excellent overall yields. Using our methodology, the yields of the syntheses of <strong><em>meso</em>-1</strong>, <strong><em>meso</em>-2</strong> and <strong>3L</strong> are the highest reported to date. The synthetic methodology was readily extended to the three-step synthesis of <em>N</em>-alkyl derivatives by replacing the ammonia nitrogen source with a primary amine. The trihydroxypiperidines and <em>N</em>-alkyl analogues were screened for enzyme inhibitory activity using Fabrazyme (Fabry disease), GCase (Gaucher's disease), <em>Agrobacterium</em> sp. β-glucosidase, and <em>Escherichia coli</em> β-galactosidase. <em>N</em>-Phenylethyl 3,4,5-trihydroxypiperidine (<em>N</em>-phenylethyl-1-(3<em>R</em>,4<em>R</em>,5<em>S</em>)-piperidine-3,4,5-triol) showed good inhibitory activity of Fabrazyme (<em>K</em><sub>i</sub> = 46 μM). This activity was abolished when the <em>N</em>-phenylethyl group was removed or replaced with a non-aromatic alkyl chain.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"543 ","pages":"Article 109198"},"PeriodicalIF":2.4,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0008621524001770/pdfft?md5=d0a10f2048fed1a52bbd104f83b6ed34&pid=1-s2.0-S0008621524001770-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141598535","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}
Monica Denise R , Nagarajan Usharani , Natarajan Saravanan , Swarna V. Kanth
{"title":"In vitro and in silico approach towards antimicrobial and antioxidant behaviour of water-soluble chitosan dialdehyde biopolymers","authors":"Monica Denise R , Nagarajan Usharani , Natarajan Saravanan , Swarna V. Kanth","doi":"10.1016/j.carres.2024.109192","DOIUrl":"10.1016/j.carres.2024.109192","url":null,"abstract":"<div><p>Chitosan dialdehyde (ChDA) was prepared from a three-step process initiated by thermal organic acid hydrolysis, periodate oxidization, and precipitation from native chitosan (NCh). The developed ChDA resulted in an aldehydic content of about 82 % with increased solubility (89 %) and maximum yield (97 %). The functional alteration of the aldehydic (-CHO) group in ChDA was established using vibrational stretching at 1744 cm<sup>−1</sup>. The increase in the zone of inhibition of ChDA compared to NCh has confirmed the inherent antimicrobial effect against bacterial and fungal species. ChDA showed better antioxidant activity of about 97.4 % (DPPH) and 31.1 % (ABTS) compared to NCh, measuring 45.3 % (DPPH) and 15.9 % (ABTS), respectively. The novel <em>insilico</em> predictions of the ChDA's biocidal activity were confirmed through molecular docking studies. The amino acid moiety such as ARG 110 (A), ASN 206 (A), SER 208 (A), THR 117 (B), ASN 118 (B), and LYS 198 (B) residues of 7B53 peptide from <em>E. coli</em> represents the binding pockets responsible for interaction with aldehyde group of ChDA. Whereas PHE 115 (E), ALA 127 (H), TYR 119 (C), GLN 125 (H), ASN 175 (E), ARG 116 (E), LYS 101 (H), and LYS 129 (H) of 1IYL A peptide from <em>Candida albicans</em> makes possible for binding with ChDA. Hence, the synergistic effect of ChDA as a biocidal compound is found to be plausible in the drug delivery system for therapeutic applications.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109192"},"PeriodicalIF":2.4,"publicationDate":"2024-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141466337","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":"Fatty acid-modified chitosan and nanoencapsulation of essential oils: A snapshot of applications","authors":"Rukayat Abiola Abdulsalam, Oluwatosin Ademola Ijabadeniyi, Saheed Sabiu","doi":"10.1016/j.carres.2024.109196","DOIUrl":"10.1016/j.carres.2024.109196","url":null,"abstract":"<div><p>Chitosan (CS) and its modification with fatty acid (FA) in addition to the nanoencapsulation with essential oils (EOs) have emerged as promising approaches with diverse applications, particularly in food and fruit preservation. This review aims to curate data on the prospects of CS modified with FA as nanostructures, serving as carriers for EOs and its application in the preservation of fruits. A narrative review with no restricted period was used for the general overview of CS and strategies for its modification with FA. Report on CS modified with FA and nanoencapsulation with EO and their applications were appraised. The prospects of CS modified with FA and EO nanoencapsulation in food and fruit preservation were outlined. Most chitosan-fatty acid (CS-FA) studies have found relevance in water, medical and pharmaceutical industries, with few studies on food preservation. CS-FA formulation with EOs shows substantial potential in preserving fruits and will significantly impact the food industry in the future by extending the shelf life of fruits and reducing food waste.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109196"},"PeriodicalIF":2.4,"publicationDate":"2024-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141466336","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":"Inhibitory effect of organogermanium compound 3-(trihydroxygermyl)propanoic acid on fructose-induced glycation of amino compounds","authors":"Mika Masaki , Yasuhiro Shimada , Tomoya Takeda , Hisashi Aso , Takashi Nakamura","doi":"10.1016/j.carres.2024.109191","DOIUrl":"10.1016/j.carres.2024.109191","url":null,"abstract":"<div><p>3-(Trihydroxygermyl)propanoic acid (THGP), a hydrolysate of poly-<em>trans</em>-[(2-carboxyethyl)germasesquioxane] (Ge-132, also known as repagermanium), can inhibit glycation between glucose/ribose and amino compounds. In addition, THGP may inhibit glycation by inhibiting reactions that occur after Amadori rearrangement and inducing the reversible solubilization of AGEs. In this study, we first investigated the effects and mechanisms on the glycation of fructose and amino compounds by THGP, as a greater reactivity was obtained with fructose than with glucose. Unlike other anti-glycation materials, THGP can form a complex with fructose, the initial compound of glycation. THGP also inhibited the production of AGEs and suppressed the reduction of fructose in a reaction between fructose and arginine. These results indicate that THGP forms a complex with cyclic fructose possessing a <em>cis</em>-diol structure at a reducing end, and that it suppresses the ring-opening of fructose and the progress of the initial glycation reaction. We next tried to evaluate the suppressive effect of glucosyl hesperidin (GHes) and THGP on the reaction of glycation between fructose and collagen. Both compounds effectively reduced the production of AGEs individually, and the combination of them led to a synergistic suppression. Therefore, through combination with other antiglycation materials, THGP may cooperatively exhibit glycation-inhibitory effects and be able to suppress the AGE production.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109191"},"PeriodicalIF":2.4,"publicationDate":"2024-06-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0008621524001708/pdfft?md5=3f95b17af9e647ff45b57edbee114222&pid=1-s2.0-S0008621524001708-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141466338","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":"Isolation and characterization of feruloylated oligosaccharides from Phyllostachys acuta and in vitro antioxidant activity","authors":"Xiaohong Yu, Hengyuan Cao, Xiaochen Liu, Jinbin Liu, Yongmei Lyu, Dujun Wang, Ming Wei","doi":"10.1016/j.carres.2024.109193","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109193","url":null,"abstract":"<div><p>Feruloylated oligosaccharides (FOs) generated by decomposing plant hemicellulose, offer a wide range of potential applications in both the food and biomedical areas. As a graminaceous plant, bamboo is rich in hemicellulose. However, the structural composition and activity studies of FOs from it were rarely reported. In this study, FOs from <em>Phyllostachys acuta</em> (pFOs) obtained by enzymatic hydrolysis were isolated by AmberliteXAD-2 and C18 SPE columns. Then, pFOs were qualitatively and quantitatively analyzed by UPLC-ESI-MS/MS after labeled by 3-Amino-9-ethyl-carbazole (AEC), and the chemical antioxidant activity of pFOs and effects of pFOs on H<sub>2</sub>O<sub>2</sub>-induced oxidative damage were investigated. Finally, 14 of pFOs isomers were distinguished and identified, of which 10 did not contain hexoses and 4 did, and the three most abundant pFO structures were <strong>12</strong> (Iso 7, F1A1X2H2-AEC, 29.04 %), <strong>11</strong> (Iso 6, F1A1X1H2-AEC, 17.96 %), and <strong>4</strong> (Iso 3-1, F1A1X3-AEC, 15.57 %). The results of antioxidant studies showed that pFOs possessed certain reducing power, scavenging DPPH radicals, scavenging superoxide anion radicals, and scavenging hydroxyl radicals. Among them, the ability to clear DPPH radicals was particularly significant. pFOs significantly reduced the viability of RAW264.7 cells after H<sub>2</sub>O<sub>2</sub> induction, whereas pFOs had a significant protective effect (p < 0.001). pFOs increased the viability of T-AOC and SOD enzymes in oxidatively damaged cells, as well as had a significant inhibition effect on ROS elevation (p < 0.001). This study lays the foundation for the structural analysis and antioxidant activity evaluation of bamboo-derived feruloyl oligosaccharides for their application in food and pharmaceutical fields.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109193"},"PeriodicalIF":2.4,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141438775","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}
Andreja Jakas , Ramya Ayyalasomayajula , Mare Cudic
{"title":"Amadori and Heyns rearrangement products of bioactive peptides as potential new ligands of galectin-3","authors":"Andreja Jakas , Ramya Ayyalasomayajula , Mare Cudic","doi":"10.1016/j.carres.2024.109195","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109195","url":null,"abstract":"<div><p>Non-enzymatic cascade reactions between amines and reducing sugars are known as Maillard reaction. The late phase of these reactions consists of advanced glycation end products (AGEs), which have been implicated in the pathogenesis of numerous human diseases. Recent evidence suggests that galectin-3 acts as a receptor for AGEs and some early products of the Maillard reaction. The early phase of the Maillard reaction, which consists of 1-amino-1-deoxyketoses (Amadori compounds) and 2-amino-2-deoxyaldoses (Heyns compounds), was the subject of our study. The binding interactions between galectin-3 and the Amadori and Heyns compounds of leucine-enkephalin (YGGFL), leucine-enkephalin methyl ester (YGGFL-OMe), truncated enkephalin (YGG and Y) and tetrapeptide (LSKL) were measured using the AlphaScreen competitive binding assay. The affinity of galectin-3 for Amadori and Heyns compounds depends on both the sugar moiety and the amino acid sequence of the model compounds. The best results were obtained with Leu-enkephalin derivatives of Amadori (IC<sub>50</sub> = 6.06 μm) and Heyns (IC<sub>50</sub> = 8.6 μm) compound, respectively.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109195"},"PeriodicalIF":2.4,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141434805","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}
Lin Wang , Yu Pang , Zhongwen Su , Meihua Xin , Mingchun Li , Yangfan Mao
{"title":"Synthesis of N-isonicotinic sulfonate chitosan and its antibiofilm activity against E. coli and S. aureus","authors":"Lin Wang , Yu Pang , Zhongwen Su , Meihua Xin , Mingchun Li , Yangfan Mao","doi":"10.1016/j.carres.2024.109194","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109194","url":null,"abstract":"<div><p><em>N</em>-(sodium 2-hydroxypropylsulfonate) chitosan (HSCS), <em>N</em>-sulfonate chitosan (SCS) and <em>N</em>-isonicotinic sulfonate chitosan (ISCS) were prepared. The structures of the prepared chitosan derivatives were characterized by nuclear magnetic resonance (<sup>1</sup>H NMR) spectroscopy, Fourier transform infrared (FTIR) spectroscopy, ultraviolet–visible (UV–vis) spectroscopy and elemental analysis (EA). Antibacterial and antibiofilm activities of these chitosan derivatives were evaluated <em>in vitro</em>. The minimum inhibitory concentration (MIC) of HSCS and SCS against <em>Escherichia coli</em> (<em>E. coli</em>) and <em>Staphylococcus aureus</em> (<em>S. aureus</em>) were 0.625 mg/mL and 0.156 mg/mL, respectively. ISCS exhibited MIC values of 0.313 mg/mL and 0.078 mg/mL against <em>E. coli</em> and <em>S. aureus</em>, respectively. ISCS demonstrated superior antibacterial and antibiofilm properties compared to SCS and HSCS. These findings suggest that the incorporation of a pyridine structure into sulfonate chitosan enhances its antibacterial and antibiofilm activities, and the prepared ISCS has a promising application prospect for controlling the reproduction of microorganisms in the field of food packaging.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109194"},"PeriodicalIF":3.1,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141422802","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":"Effect of Fenton reaction parameters on the structure and properties of oxidized wheat starch","authors":"Adrien Letoffe , Reza Hosseinpourpia , Valentin Silveira , Stergios Adamopoulos","doi":"10.1016/j.carres.2024.109190","DOIUrl":"https://doi.org/10.1016/j.carres.2024.109190","url":null,"abstract":"<div><p>Wheat starch was oxidized through a Fenton reaction by hydrogen peroxide and Iron II sulfate as a catalyst at various concentrations and reaction duration. The formation of carbonyl and carboxyl groups confirmed the starch oxidation as determined with Fourier-transform infrared (FTIR) spectroscopy. The degree of oxidation was estimated by carbonyl and carboxyl titration. The various oxidized wheat starches presented considerable variations in their oxidation level as a function of the catalyst concentration and oxidative process duration. The effect of the Fenton reaction parameters on the starch macromolecular chains and microstructure was evaluated by X-ray diffraction and amylose content estimation. Significant depolymerization of the starch macromolecules was observed, mainly in the starch amorphous phase, followed by a degradation of the crystalline phase at a higher oxidation level. SEM observations revealed changes in starch structure, which ranged from minor degradation of the starch granules to a more crosslinked morphology.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109190"},"PeriodicalIF":3.1,"publicationDate":"2024-06-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0008621524001691/pdfft?md5=d59f16d593b8dec2aec942e4e1e4cb94&pid=1-s2.0-S0008621524001691-main.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141333135","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":"Inequality relations for NMR-based polymer homoblock analysis and extended application: Reanalysis of historical data on alginates, chitosans, homogalacturonans, and galactomannans","authors":"Xiaohui Xing , Kanglin Xing , Yves S.Y. Hsieh , D. Wade Abbott","doi":"10.1016/j.carres.2024.109189","DOIUrl":"10.1016/j.carres.2024.109189","url":null,"abstract":"<div><p>There has been a long-standing bottleneck in the quantitative analysis of the frequencies of homoblock polyads beyond triads using <sup>1</sup>H and <sup>13</sup>C NMR for linear polysaccharides, primarily because monosaccharides within a long homoblock share similar chemical environments due to identical neighboring units, resulting in indistinct NMR peaks. In this study, through rigorous mathematical induction, inequality relations were established that enabled the calculation of frequency ranges of homoblock polyads from historically reported NMR-derived frequency values of diads and/or triads of alginates, chitosans, homogalacturonans, and galactomannans. The calculated homoblock frequency ranges were then applied to evaluate three chain growth statistical models, including the Bernoulli chain, first-order Markov chain, and second-order Markov chain, for predicting homoblock frequencies in these polysaccharides. Furthermore, based on the mathematically derived inequality relations, a novel 2D array was constructed, enabling the graphical visualization of homoblock features in polysaccharides. It was demonstrated, as a proof of concept, that the novel 2D array, along with a 1D code generated from it, could serve as an effective feature engineering tool for polymer classification using machine learning algorithms.</p></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"542 ","pages":"Article 109189"},"PeriodicalIF":2.4,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141407251","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}