Carbohydrate Research最新文献

This study aimed at optimizing process protocols for development of low glycemic index (GI) rice flour (LGIRF) by employing enzymatic hydrolysis method using central composite rotatable design (CCRD). LGIRF was evaluated for pasting, farinographic, spectroscopic and microbiological attributes. Independent variables for optimization included concentrations of α-amylase (0.02–0.12 %), glucoamylase (0.02–0.24 %), as well as the incubation temperature (55–80°C). Resistant starch (RS), glycemic index (GI) and glycemic load (GL) were investigated as response variables. The optimum conditions for development of LGIRF with better quality were- α-amylase concentration of 0.040 %, glucoamylase concentration of 0.070 % and an incubation temperature of 60 °C. The results of mineral analysis revealed significantly (p < 0.05) lower levels of boron, potassium, zinc, phosphorus, magnesium, and manganese in LGIRF, while iron and copper were significantly higher. The viscosity profile as evident from pasting profile and farinographic characteristics of LGIRF were significantly (p < 0.05) lower than native rice flour. ¹H NMR and ¹³C NMR spectroscopic studies showed an increase in flexible starch segments and a decrease in amorphous portion of starch LGIRF, along with chemical shift alterations in carbons 1 and 4. Free fatty acids and total plate count were significantly (p < 0.05) higher in LGIRF although was within limits.

The most common precursors to synthetic glycoproteins are reducing end glycosyl amines. To afford these amines, a carbohydrate is reacted with an excess of an ammonia source to yield the β-anomer, exclusively, in a reaction known as the Kochetkov amination. Although this process is the state-of-the-art method to synthesize non-functionalized, β-amino (βA) glycans, misconceptions surrounding the stability of these amines has limited their use in subsequent reactions. Here, we investigated the stability of seven amino sugars in the neutral, acidic, and basic conditions they would be subject to in common reactions using amines. In neutral and basic conditions, the amino sugars proved relatively stable with the fastest time to 50% hydrolysis being four days for only one carbohydrate. However, acidic conditions promoted rapid hydrolysis, with all amino sugars reaching over 97% hydrolysis within 2 h. Finally, we performed a bioconjugation using fluorescein isothiocyanate and βA-difucosyllactose, revealing sufficient stability of the amino product for a successful subsequent reaction.

The conformational study of carbohydrates is critical to understand the molecular recognition mechanisms underlying their biological functions. Moreover, the systematic study of their conformational patterns can unlock useful tools to design optimized glycomimetics and drug candidates. Using nuclear magnetic resonance, we studied the interglycosidic rotamer equilibria of ester-protected and deprotected alkyl O-rutinosides (α-L-Rha(1,6)β-D-GlcOR). In the protected series, the equilibrium about the C5–C6 bond distributes among the three possible rotamers gg, gt, and tg, being gt the predominant conformer. In these series, the flexibility about C5–C6 shows a marked dependency on the aglycone's structure, where the increase on the aglycone's volume leads to a progressive increment on the tg contributions at the expense of gt, with gg remaining practically constant along the series. The removal of the protective groups results in rutinosides displaying an equilibrium equally distributed between gg and gt with no tg contributions regardless of the aglycone's structure.

An efficient synthetic strategy has been developed to achieve a pyruvic acid acetal containing tetrasaccharide repeating unit corresponding to the K82 capsular polysaccharide of Acinetobacter baumannii LUH5534 strain in very good yield. The synthetic scheme involves the use of suitably functionalized monosaccharide thioglycosides as glycosyl donors and a combination of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) as thiophilic glycosylation activator to furnish satisfactory yield of the products with appropriate stereochemistry at the glycosidic linkages. Incorporation of the (R)-pyruvic acid acetal in the d-galactose moiety was achieved in very good yield by the treatment of the diol derivative with methyl 2,2-bis(p-methylphenylthio)propionate in the presence of a combination of NIS and triflic acid.

The escalation of heavy metal pollutants in soils and effluents, driven by industrialization and human activities, poses significant environmental and health risks. Conventional remediation methods are often costly and ineffective, prompting a shift towards sustainable alternatives such as biological treatments. Natural biosorbents, including microbial cells and their byproducts, have emerged as promising solutions. One such approach involves leveraging exopolysaccharides (EPS), complex high-molecular-weight biopolymers synthesized by microbes under environmental stress conditions. EPS are intricate organic macromolecules comprising proteins, polysaccharides, uronic acids, humic compounds, and lipids, either located within microbial cells or secreted into their surroundings. Their anionic functional groups enable efficient electrostatic binding of cationic heavy metals, making EPS effective biosorbents for soil remediation. This review thoroughly explores the pivotal role of bacterial EPS in the removal of heavy metals, focusing on EPS biosynthesis mechanisms, the dynamics of interaction with heavy metals, and case studies that illustrate their effectiveness in practical remediation strategies. By highlighting these aspects, the review underscores the innovation and practical implications of EPS-based bioremediation technologies, demonstrating their potential to address critical environmental challenges effectively while paving the way for sustainable environmental management practices. Key findings reveal that EPS exhibit robust metal-binding capacities, facilitated by their anionic functional groups, thereby offering a promising solution for mitigating metal pollution in diverse environmental matrices.

Trained Immunity is defined as a biological process normally induced by exogenous or endogenous insults that triggers epigenetic and metabolic reprogramming events associated with long-term adaptation of innate immune cells. This trained phenotype confers enhanced responsiveness to subsequent triggers, resulting in an innate immune “memory” effect. Trained Immunity, in the past decade, has revealed important benefits for host defense and homeostasis, but can also induce potentially harmful outcomes associated with chronic inflammatory disorders or autoimmune diseases. Interestingly, evidence suggest that the “trainers” prompting trained immunity are frequently glycans structures. In fact, the exposure of different types of glycans at the surface of pathogens is a key driver of the training phenotype, leading to the reprogramming of innate immune cells through the recognition of those glycan-triggers by a variety of glycan-binding proteins (GBPs) expressed by the immune cells. β-glucan or mannose-enriched structures in Candida albicans are some of the examples that highlight the potential of glycans in trained immunity, both in homeostasis and in disease. In this review, we will discuss the relevance of glycans exposed by pathogens in establishing key immunological hubs with glycan-recognizing receptors expressed in immune cells, highlighting how this glycan-GBP network can impact trained immunity. Finally, we discuss the power of glycans and GBPs as potential targets in trained immunity, envisioning potential therapeutic applications.

Punica granatum L., commonly known as pomegranate, is native to Afghanistan and Iran, and today widely cultivated all over the world. Pomegranate polysaccharides are one of the most important bioactive components of P. granatum, which have a wide range of beneficial biological activities, such as anticancer, immunostimulatory, hepatoprotection, anti-psoriasis and antioxidation. Hot water extraction is currently the most commonly used method to isolate pomegranate polysaccharides. The structural characteristics of pomegranate polysaccharides have been extensively investigated through various advanced modern analytical techniques. This review focuses on the extraction, purification, structural characteristics, biological activities and structure-activity relationships of polysaccharides from Punica granatum. The aim of this article is to comprehensively and systematically summarize recent information of polysaccharides from Punica granatum and to serve as a basis for further research and development as therapeutic agents and functional foods.

Sugars are vital biomolecules widely found in nature, playing an indispensable role in a plethora of biological processes. Similarly, coumarins are heterocycles with an effective pharmacophore skeleton, making them crucial in drug design and development. Coupling carbohydrate moieties to the small biologically active molecules creates a vast library of glycoconjugates with impressive structural diversity. The potential of coumarin glycosides is being extensively explored due to their broad spectrum of applications, including antibacterial, anticancer, and anticoagulant properties, etc. This review highlights various chemical methodologies for synthesizing diverse coumarin glycohybrids with distinct linkages and explores their immense biological potential, making a significant contribution to the field of organic synthesis.

Five novel imidazole-functionalized chitosan derivatives 3a-3e were synthesized via addition reactions of chitosan with imidazole derivatives. The partial incorporation of imidazole moiety in chitosan were confirmed by FTIR, UV, ¹H NMR, XRD, SEM and GPC. Meanwhile, the antifungal activity against three common plant pathogenic fungi: Phytophthora nicotianae (P. nicotianae), Fusarium graminearum (F. graminearum) and Rhizoctonia solani (R. solani), was assayed in vitro at 0.5 and 1.0 mg/mL by hyphal measurement, and the introduction of imidazole group can influence the antifungal activity. At 0.5 mg/mL, 3e inhibited P. nicotianae growth by 42 % and had an inhibitory index against R. solani of 50 %. Derivative 3e was more effective than unmodified chitosan whose antifungal index was 17 % against P. nicotianae and 22 % against R. solani. To our surprise, at 1.0 mg/mL, the inhibition rate of 3e against R. solani can reach 99 %, while the inhibition rate of chitosan is only 38 %. These results indicated that some imidazole chitosan derivatives with enhanced antifungal activities could serve as potential biomaterial for antifungal application.

We designed metabolically engineered non-pathogenic strains of Escherichia coli to produce unsulfated chondroitin with and without chondroitin lyase to produce the chondroitin polymer or its related oligosaccharides. Chondroitin was synthesized using chondroitin synthase KfoC and chondroitin was degraded using Pl35, a chondroitin lyase from Pedobacter heparinus. Pl35 behaved as a true endo-enzyme generating a large panel of oligosaccharides ranging from trimers to 18-mers instead of the di- and tetramers obtained with most chondroitin lyases. Two series of oligosaccharides were characterized, sharing an unsaturated uronic acid (4-deoxy-α-L-threo-hex-4-enepyranosyluronic acid, △UA) residue at their non-reducing end. The major “even-numbered” series was characterized by a terminal reducing N-acetylgalactosaminyl residue. The minor “odd-numbered” series oligosaccharides carried a terminal reducing glucuronic acid residue instead.

Cultures were conducted in fed-batch conditions, and led to the production of up to 10 g L⁻¹ chondroitin or chondroitin oligosaccharides.

All products were purified and fully characterized using NMR and mass spectrometry analyses.

This is the first report of the microbial production of large chondro-oligosaccharides.