Carbohydrate Research最新文献

{"title":"Photo-induced glycosylation using edible polyphenol ellagic acid","authors":"Hidenari Shigeta,&nbsp;Satomi Goi,&nbsp;Daisuke Takahashi,&nbsp;Kazunobu Toshima","doi":"10.1016/j.carres.2025.109461","DOIUrl":"10.1016/j.carres.2025.109461","url":null,"abstract":"<div><div>Photo-induced glycosylation reactions of trichloroacetoimidate donors with alcohol acceptors were investigated under visible light (470 nm) irradiation using the edible polyphenol, ellagic acid. We found, for the first time, that these glycosylations proceeded smoothly under mild reaction conditions, and the corresponding glycosides were obtained in high yields. Furthermore, this glycosylation method was applicable to a wide range of trichloroacetimidate donors and alcohol acceptors, and showed high chemoselectivity over glycosyl phosphate, fluoride, glycal, thioglycoside, and (<em>N</em>-phenyl)trifluoroacetimidate.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109461"},"PeriodicalIF":2.4,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143678964","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":"Structural studies on the O-polysaccharide of Vreelandella alkaliphila strain B521","authors":"Elena N. Sigida ,&nbsp;Maxim S. Kokoulin ,&nbsp;Vlada S. Belova ,&nbsp;Marina S. Kuzina ,&nbsp;Natalya S. Velichko ,&nbsp;Vyacheslav S. Grinev ,&nbsp;Yuliya P. Fedonenko","doi":"10.1016/j.carres.2025.109462","DOIUrl":"10.1016/j.carres.2025.109462","url":null,"abstract":"<div><div>Lipopolysaccharide was obtained by hot aqueous-phenol extraction from <em>Vreelandella alkaliphila</em> B521, a moderately halophilic gram-negative bacterium isolated from mud of Lake Botkul, Volgograd Region, Russia. The O-polysaccharide (OPS) was released by mild acid hydrolysis of the lipopolysaccharide and was structurally characterized by chemical analyses and by 1D and 2D NMR spectroscopy. The following structure of the OPS trisaccharide repeating unit was identified: →4)-α-<span>l</span>-Gul<em>p</em>NAcA-(1 → 4)-α-<span>l</span>-Gul<em>p</em>NAcA-(1 → 6)-α-<span>d</span>-Glc<em>p</em>NAc-(1→</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109462"},"PeriodicalIF":2.4,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644438","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":"Ganglioside analog synthesis via late-stage sialylation and fatty acid introduction","authors":"Maina Takahashi ,&nbsp;Naoko Komura ,&nbsp;Hide-Nori Tanaka ,&nbsp;Akihiro Imamura ,&nbsp;Hideharu Ishida ,&nbsp;Hiromune Ando","doi":"10.1016/j.carres.2025.109460","DOIUrl":"10.1016/j.carres.2025.109460","url":null,"abstract":"<div><div>Gangliosides are sialylated glycosphingolipids comprising various chemical forms of glycans and ceramides. They perform various biological functions in cell plasma membranes. Differences in the sialic acid forms (Neu5Ac and Neu5Gc) and ceramide species (lengths and degrees of unsaturation) result in variations in ganglioside's functions, even though their core glycan structures are common. However, ganglioside research requires considerable effort due to complications in their chemical synthesis. Further, a facile supply of ganglioside samples with variations in substructures is required for comprehensive research. We recently reported a chemical synthesis method for gangliosides <em>via</em> the late-stage sialylation of oligosaccharyl ceramide acceptors. Based on this method, we developed a synthetic method <em>via</em> late-stage incorporation of sialic acids and fatty acids. An oligosaccharyl sphingosine acceptor was efficiently sialylated using a minimally protected design to enhance the reactivity of the acceptor hydroxyl group. Subsequently, the azide group at the sphingosine C2 position was reduced for fatty acid incorporation. Further several steps of Neu C5-modification (<em>N</em>-Ac or <em>N</em>-Gc), global deprotection, and fluorescent dye incorporation enabled neolacto-series ganglioside (sialyl-neolactotetraosylceramide, Neu nLc₄Cer) probe synthesis. These results indicate the applicability of this method for the systematic synthesis of ganglioside analogs with modifications to the sialic acid or lipid structure.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109460"},"PeriodicalIF":2.4,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679014","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":"Noncovalent interactions: An emerging focal point in stereoselective catalytic carbohydrate synthesis","authors":"Hao Guo ,&nbsp;Charles C.J. Loh","doi":"10.1016/j.carres.2025.109458","DOIUrl":"10.1016/j.carres.2025.109458","url":null,"abstract":"<div><div>The incorporation of frontier synthetic concepts into stereoselective carbohydrate synthesis is gaining significant traction. In the last five years, there are increasing reports documenting that the consideration of weak non-covalent interactions (NCIs) constitutes a vital factor in steering the anomeric and site-selectivity, as well as in activating difficult glycosylations. In light of blossoming developments on this front, we present a brief overview of recent case studies that involve the harnessing of hydrogen bonding (HB), halogen bonding (XB), chalcogen bonding (ChB) and π-interactions. These NCIs represent a considerable palette of classical/non-classical weak interactions that is of current interest to the broad synthesis community. Significantly, a close mechanistic analysis often revealed that NCIs were instrumental in dictating the final stereoselectivity outcome of many glycosylation pathways. We are optimistic that by expanding the focal point from purely glycosyl substrate modifications towards tweaking catalytic NCIs at the supramolecular level of chemical glycosylations, this emerging concept offers new levers of stereoselectivity control beyond classical stereoelectronic and steric considerations.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109458"},"PeriodicalIF":2.4,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143679015","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":"Chitosan-based fluorescent nanocarriers: A novel drug delivery strategy for oral squamous cell carcinoma therapy","authors":"Gang Zhu ,&nbsp;Qiang Ruan ,&nbsp;Zhonghui Tian ,&nbsp;Fengxia Liu ,&nbsp;Luyan Guo ,&nbsp;Zhongrui Zhang","doi":"10.1016/j.carres.2025.109459","DOIUrl":"10.1016/j.carres.2025.109459","url":null,"abstract":"<div><div>Oral squamous cell carcinoma (OSCC) accounts for over 90 % of all oral cancers, underscoring the urgent need for effective treatment strategies to improve patient survival. Grape seed polyphenols (GSP), a naturally occurring plant-derived compound, have shown promise as a therapeutic agent for OSCC. However, their clinical application is limited by poor solubility and instability. To address these challenges, coordination polymers (CPs) were employed as drug carriers, enhancing GSP's solubility, bioavailability, and controlled release. In this study, compound 1 (CP1) was synthesized and incorporated with GSP (CP1@1@GSP), significantly improving drug encapsulation efficiency (over 50 %) and drug loading (16 %), ensuring more effective drug delivery. Despite these advantages, concerns about metal ion release and potential immune responses necessitate further safety evaluation. To mitigate these risks, chitosan (CS), a biocompatible and low-toxicity natural polymer, was introduced. The development of pyrene-modified chitosan-based hollow nanoparticles (Pyrene-CS@CP1@1@GSP) facilitated both drug delivery and fluorescence-based real-time tracking. Characterization using scanning electron microscopy (SEM) and dynamic light scattering (DLS) confirmed the uniform spherical morphology of the nanoparticles, with an average size of approximately 150 nm, stable dispersion, a low polydispersity index (PDI), and excellent self-assembly properties. Further functional evaluation revealed that Pyrene-CS@CP1@1@GSP effectively modulates glycolysis in OSCC cells. Treatment significantly inhibited OSCC cell proliferation in a dose-dependent manner, with glucose levels in the cell supernatant increasing significantly (p &lt; 0.05), indicating reduced glucose uptake by cancer cells. Simultaneously, lactic acid levels decreased (p &lt; 0.05), suggesting suppression of glycolytic activity. Additionally, fluorescence quenching and subsequent restoration of pyrene fluorescence during drug release enabled real-time tracking of drug distribution. These findings demonstrate that Pyrene-CS@CP1@1@GSP enhances the bioavailability and stability of GSP while effectively regulating glycolysis, thereby influencing OSCC progression. This study presents a promising strategy for targeted OSCC therapy, offering both improved treatment efficacy and real-time drug release monitoring, with potential applications in future clinical settings.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109459"},"PeriodicalIF":2.4,"publicationDate":"2025-03-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644437","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":"Design, synthesis, and biological evaluation of novel KRN7000 analogues using 5α-gem-difluorocarba-β-l-arabinopyranose","authors":"Yuanfang Liu ,&nbsp;Chuanfang Zhao ,&nbsp;Jun Liu ,&nbsp;Yuguo Du","doi":"10.1016/j.carres.2025.109457","DOIUrl":"10.1016/j.carres.2025.109457","url":null,"abstract":"<div><div>Two novel KRN7000 analogues, where <span>d</span>-galactopyranosyl residue was replaced by 5α-<em>gem</em>-difluorocarba-β-<span>l</span>-arabinopyranose, were designed based on docking computation and energy decomposition analyses. The target compounds were synthesized employing the key steps of Ferrier's carbocyclic ring closure and <em>gem</em>-difluoride formation with <span>d</span>-galactose as starting material. The <em>in vivo</em> bioassay revealed that the designed glycolipids could stimulate iNKT cells to produce cytokines IFN-<em>γ</em> and IL-4. The introduced hydroxyl groups on glycolipid acyl chain provided extra CD1d substrate affinities, and thus favored to boost Th1-type cytokine secretion. When the ring oxygen was replaced by CF₂ group on sugar unit, its TCR affinities were enhanced in contrast with KRN7000. The <em>in vivo</em> cytokine profiles induced by synthetic glycolipids were initially dominated by the binding ability of CD1/glycolipid, and then adjusted by affinity toward TCR in CD1/<em>α</em>-GalCer/TCR triplex structure. The current results could be helpful in designing of more efficient <em>α</em>-GalCer analogs.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109457"},"PeriodicalIF":2.4,"publicationDate":"2025-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143600604","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":"Isolation and structure elucidation of cell surface polysaccharides from Oenococcus oeni","authors":"Emmanuel Maes ,&nbsp;Irina Sadovskaya ,&nbsp;Nao Yamakawa ,&nbsp;Adeline Goulet ,&nbsp;Claire Le Marrec ,&nbsp;Marie-Pierre Chapot-Chartier","doi":"10.1016/j.carres.2025.109456","DOIUrl":"10.1016/j.carres.2025.109456","url":null,"abstract":"<div><div>The Gram-positive bacterium <em>Oenococcus oeni</em> is a major player in wine malolactic fermentation. In <em>O. oeni</em>, cell wall polysaccharides are considered putative receptors for bacteriophages, virus predators that lead to fermentation failures. In this study, we have developed an efficient stepwise extraction protocol to extract polysaccharides from the cell wall of <em>O. oeni</em> IOEBS277, which were analyzed by methylation, 1D, 2D-NMR spectroscopy, and MALDI-QIT-TOF mass spectrometry. The chemical structures of the two major purified polysaccharides were elucidated<em>.</em> The first one is a heteropolysaccharide with repeating units consisting of a branched hexasaccharide and one glycerol residue, linked by phosphodiester bonds. The second one consists of a →6)-β-Galf-(1→ galactofuranan chain partially substituted on the C-2 hydroxyl with β-Glc<em>p</em>. HR-MAS NMR analysis of intact <em>O. oeni</em> cells indicated that both polysaccharides are exposed to the bacterial surface.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109456"},"PeriodicalIF":2.4,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143669198","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":"Concise first total synthesis of phenylethanoid glycosides parvifloroside A and crassifolioside","authors":"Duc Thinh Khong ,&nbsp;Madhu Babu Tatina ,&nbsp;Zaher M.A. Judeh","doi":"10.1016/j.carres.2025.109455","DOIUrl":"10.1016/j.carres.2025.109455","url":null,"abstract":"<div><div>The first total synthesis of phenylethanoid glycosides parvifloroside A <strong>1</strong> and crassifolioside <strong>2</strong> is disclosed, achieving excellent 31 % and 33 % overall yield, respectively. The synthesis exploited the inherent reactivity differences among the free hydroxyl groups on 4-O-caffeoyl glucopyranoside <strong>3</strong> intermediate, enabling regioselective caffeoylation and rhamnosylation. The key to the synthesis is using chiral 4-pyrrolidinopyridine organocatalyst <strong>6</strong> to achieve the regioselective caffeoylation and migration of acyl groups. Notably, the synthesis avoids the common challenge of <em>E</em>:<em>Z</em> isomerization of the caffeoyl moiety's double bond. Additionally, only a single protection/deprotection step is employed, significantly simplifying the process. This concise approach provides a practical route to these natural products and establishes a versatile strategy for synthesizing a wide array of phenylethanoid glycosides with similar substitution patterns.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109455"},"PeriodicalIF":2.4,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628181","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":"Convergent synthesis of steviol glycosides rebaudioside a and M","authors":"Yuanyuan Li ,&nbsp;Haoru Zhuang ,&nbsp;Xuerui Tao ,&nbsp;Yingguo Liu ,&nbsp;Tianlu Li ,&nbsp;Peng Peng","doi":"10.1016/j.carres.2025.109446","DOIUrl":"10.1016/j.carres.2025.109446","url":null,"abstract":"<div><div>Steviol glycosides, a natural health-focused sweetener, is receiving increasing attention. Herein, an efficient and concise approach for the convergent synthesis of Rebaudioside A and M has been devised. This method features a AuCl₃-<em>t</em>BuCN cooperative catalysis to achieve highly 1, 2-<em>trans</em> stereoselective glycosidation of a C2-branched trisaccharide trichloroacetimidate with tertiary C-13 hydroxy group in steviol aglycone, without relying on neighboring group participation.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109446"},"PeriodicalIF":2.4,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143609367","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":"Tamarind (Tamarindus indica L.) Seed Polysaccharide: A promising biopolymer for drug delivery, wound healing, tissue engineering and beyond","authors":"Madhavi Latha Chinta ,&nbsp;Pradeep Kumar Gandam ,&nbsp;M.V. Sivasankar ,&nbsp;Sreenivasa Rao Parcha","doi":"10.1016/j.carres.2025.109454","DOIUrl":"10.1016/j.carres.2025.109454","url":null,"abstract":"<div><div>Tamarind Seed Polysaccharide (TSP) is a versatile and sustainable biopolymer that has garnered considerable attention for its wide-ranging applications in diverse fields. Derived from the seeds of Tamarindus indica L., TSP offers an eco-friendly alternative to synthetic biopolymers, aligning with the growing demand for natural materials. It is biodegradable, non-toxic, mucoadhesive, antioxidative and anti-inflammatory. TSP has been used extensively in food and pharmaceuticals. Various parts of the tamarind tree have been used in traditional medicine across different cultures around the world, thus TSP has been studied extensively for its impact in treating skin conditions, stubborn wounds and arthritis management. Owing to its non-toxic and healing nature, TSP can be explored as a valuable biomaterial for tissue engineering. This review thoroughly explores TSP's attributes, extraction, and extensive utilization across various sectors, with a main focus on drug delivery, wound healing and tissue engineering. The structure and general properties along with its visco-elastic properties were discussed briefly. The various chemical modifications of TSP which further improve its biodegradability and mucoadhesivity were also discussed. Further, other applications of TSP such as in packaging materials, mineral separation, battery technologies, thermal insulation, cosmetic formulations, agriculture, waste water and land treatments were briefly mentioned to emphasize the versatility of TSP.</div><div>The review also mentions TSP's diverse applications, ranging from mineral separation and battery technologies to thermal insulation and cosmetic formulations, to emphasize its versatility.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"552 ","pages":"Article 109454"},"PeriodicalIF":2.4,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143579907","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}