Carbohydrate-binding specificity of concanavalin lectin from Canavalia spp.

The carbohydrate-binding specificity of lectins from the four accessions of Canavalia seeds (C. ensiformis (ConA), C. cathartica (ConC), C. gladiata (ConG) and C. rosea (ConM) was studied by hemagglutination inhibition assay using monosaccharides, disaccharides and sugar derivatives. Canavalia seed extracts subjected to ammonium sulphate precipitation and the fraction with higher specific activity were analysed for carbohydrate-binding specificity and its mitogenic potential. All four lectins exhibited similar carbohydrate-binding specificity in agglutination inhibition which is in line with docking experiments. Dmannose and D-maltose were highly specific than other sugars. The results of computational method revealed differences in the affinity towards various carbohydrates. Mitogenic activity of all four lectins in human lymphocytes showed varied mitotic index. Among the four lectins studied, binding affinity to mannose and proliferation index was in the order ConG>ConA>ConM>ConC accounting to the efficacy of biological functions of highly similar analogues.

Metabolite Profiling and Anti-Aging Activity of Rice Koji Fermented with Aspergillus oryzae and Aspergillus cristatus: A Comparative Study

Rice koji, used as a starter for maximizing fermentation benefits, produces versatile end products depending on the inoculum microbes used. Here, we performed metabolite profiling to compare rice koji fermented with two important filamentous fungus, Aspergillus oryzae and A. cristatus, during 8 days. The multivariate analyses showed distinct patterns of primary and secondary metabolites in the two kojis. The rice koji fermented with A. oryzae (RAO) showed increased α-glucosidase activity and higher contents of sugar derivatives than the one fermented with A. cristatus (RAC). RAC showed enhanced β-glucosidase activity and increased contents of flavonoids and lysophospholipids, compared to RAO. Overall, at the final fermentation stage (8 days), the antioxidant activities and anti-aging effects were higher in RAC than in RAO, corresponding to the increased metabolites such as flavonoids and auroglaucin derivatives in RAC. This comparative metabolomic approach can be applied in production optimization and quality control analyses of koji products.

Selenium-Containing Polysaccharides—Structural Diversity, Biosynthesis, Chemical Modifications and Biological Activity

Selenosugars are a group of sugar derivatives of great structural diversity (e.g., molar masses, selenium oxidation state, and selenium binding), obtained as a result of biosynthesis, chemical modification of natural compounds, or chemical synthesis. Seleno-monosaccharides and disaccharides are known to be non-toxic products of the natural metabolism of selenium compounds in mammals. In the case of the selenium-containing polysaccharides of natural origin, their formation is also postulated as a form of detoxification of excess selenium in microorganisms, mushroom, and plants. The valency of selenium in selenium-containing polysaccharides can be: 0 (encapsulated nano-selenium), IV (selenites of polysaccharides), or II (selenoglycosides or selenium built into the sugar ring to replace oxygen). The great interest in Se-polysaccharides results from the expected synergy between selenium and polysaccharides. Several plant- and mushroom-derived polysaccharides are potent macromolecules with antitumor, immunomodulatory, antioxidant, and other biological properties. Selenium, a trace element of fundamental importance to human health, has been shown to possess several analogous functions. The mechanism by which selenium exerts anticancer and immunomodulatory activity differs from that of polysaccharide fractions, but a similar pharmacological effect suggests a possible synergy of these two agents. Various functions of Se-polysaccharides have been explored, including antitumor, immune-enhancement, antioxidant, antidiabetic, anti-inflammatory, hepatoprotective, and neuroprotective activities. Due to being non-toxic or much less toxic than inorganic selenium compounds, Se-polysaccharides are potential dietary supplements that could be used, e.g., in chemoprevention.

Fructose separation from sorghum syrup by using HPLC approach: a review

Liquid sugar available today is usually the result of dissolving granulated sugar using hot water. Sorghum syrup can be obtained from the concentrate without involving crystallization, centrifugation, sieving and drying and dissolving processes. However, the sorghum syrup produced from the concentrate still containing complex sugar components such as sucrose, sugar, fructose and others. This review was examined the separation of fructose from sorghum syrup using the HPLC approach. Compared with artificial sweeteners or sugar derivative products such as dextrose, maltodextrin, sorbitol, saccharin, sucralose, and xylitol, sorghum syrup still has lower economic value. The manufacture of these sugar derivatives generally uses chemical processes such as chlorination of sucralose, hydrogenation of xylitol or enzymatic processes and fermentation of fructose. Chemical processes in general can pose a danger to consumer health, while enzymatic and biological processes require high operational costs and complex processes of enzyme and cell separation such corn fructose production. Chromatography is a technology for separating complex mixtures such as sorghum concentrates to obtain separate components, such as fructose syrup and byproducts. On a laboratory scale, sugar fractionation or fructose purification is generally carried out using High Performance Liquid Chromatography (HPLC) with the Carbopac ion exchange column as the stationary phase and ultrapure water as the mobile phase. The industrial scale fractionation in the food sector is still applied to palm oil processing. This is a great opportunity to conduct research related to the components of sorghum concentrates using chromatography column fractionation technology to obtain pure fructose with greater process efficiency and economics.

Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering

The inverse electron-demand Diels-Alder (IEDDA or DAinv) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering (MGE). MGE is a versatile tool to introduce unnatural sugar derivatives that are modified with a chemical reporter group into cellular glycans. The IEDDA reaction can then be used to modify the chemical reporter group allowing, for instance, the visualization or isolation of glycoconjugates. During the last years, many different sugar derivatives as well as reporter groups have been published. These probes are summarized, and their chemical and biological properties are discussed. Furthermore, we discuss examples of MGE and subsequent IEDDA reaction that highlight its suitability for application within living systems.

Oxidative Stress-Induced Alteration of Plant Central Metabolism

Oxidative stress is an integral component of various stress conditions in plants, and this fact largely determines the substantial overlap in physiological and molecular responses to biotic and abiotic environmental challenges. In this review, we discuss the alterations in central metabolism occurring in plants experiencing oxidative stress. To focus on the changes in metabolite profile associated with oxidative stress per se, we primarily analyzed the information generated in the studies based on the exogenous application of agents, inducing oxidative stress, and the analysis of mutants displaying altered oxidative stress response. Despite of the significant variation in oxidative stress responses among different plant species and tissues, the dynamic and transient character of stress-induced changes in metabolites, and the strong dependence of metabolic responses on the intensity of stress, specific characteristic changes in sugars, sugar derivatives, tricarboxylic acid cycle metabolites, and amino acids, associated with adaptation to oxidative stress have been detected. The presented analysis of the available data demonstrates the oxidative stress-induced redistribution of metabolic fluxes targeted at the enhancement of plant stress tolerance through the prevention of ROS accumulation, maintenance of the biosynthesis of indispensable metabolites, and production of protective compounds. This analysis provides a theoretical basis for the selection/generation of plants with improved tolerance to oxidative stress and the development of metabolic markers applicable in research and routine agricultural practice.

Silane- and peroxide-free hydrogen atom transfer hydrogenation using ascorbic acid and cobalt-photoredox dual catalysis

Hydrogen atom transfer (HAT) hydrogenation has recently emerged as an indispensable method for the chemoselective reduction of unactivated alkenes. However, the hitherto reported systems basically require stoichiometric amounts of silanes and peroxides, which prevents wider applications, especially with respect to sustainability and safety concerns. Herein, we report a silane- and peroxide-free HAT hydrogenation using a combined cobalt/photoredox catalysis and ascorbic acid (vitamin C) as a sole stoichiometric reactant. A cobalt salophen complex is identified as the optimal cocatalyst for this environmentally benign HAT hydrogenation in aqueous media, which exhibits high functional-group tolerance. In addition to its applicability in the late-stage hydrogenation of amino-acid derivatives and drug molecules, this method offers unique advantage in direct transformation of unprotected sugar derivatives and allows the HAT hydrogenation of unprotected C-glycoside in higher yield compared to previously reported HAT hydrogenation protocols. The proposed mechanism is supported by experimental and theoretical studies.

Influence of L-lactate and low glucose concentrations on the metabolism and the toxin formation of Clostridioides difficile

The virulence of Clostridioides difficile (formerly Clostridium difficile) is mainly caused by its two toxins A and B. Their formation is significantly regulated by metabolic processes. Here we investigated the influence of various sugars (glucose, fructose, mannose, trehalose), sugar derivatives (mannitol and xylitol) and L-lactate on toxin synthesis. Fructose, mannose, trehalose, mannitol and xylitol in the growth medium resulted in an up to 2.2-fold increase of secreted toxin. Low glucose concentration of 2 g/L increased the toxin concentration 1.4-fold compared to growth without glucose, while high glucose concentrations in the growth medium (5 and 10 g/L) led to up to 6.6-fold decrease in toxin formation. Transcriptomic and metabolic investigation of the low glucose effect pointed towards an inactive CcpA and Rex regulatory system. L-lactate (500 mg/L) significantly reduced extracellular toxin formation. Transcriptome analyses of the later process revealed the induction of the lactose utilization operon encoding lactate racemase (larA), electron confurcating lactate dehydrogenase (CDIF630erm_01321) and the corresponding electron transfer flavoprotein (etfAB). Metabolome analyses revealed L-lactate consumption and the formation of pyruvate. The involved electron confurcation process might be responsible for the also observed reduction of the NAD+/NADH ratio which in turn is apparently linked to reduced toxin release from the cell.