The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland’s group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.
The purpose of this work was to study the behavior of (1-3)(1-4)- β -D-glucan in pressurized hot water. For this purpose, solid β -glucan (450 kDa) was put in water and heated at different temperatures (120, 150, and 170°C) for different times (5 to 360 minutes). At 120°C it was found that the highest soluble β -glucan concentration was measured after 60 minutes; at 150 and 170°C optimal times were 45 and 20 minutes, respectively. The maximum amount of β -glucan dissolved in each of the optimal conditions was 1.5, 2.2, and 2.0 g/L, respectively. Under those conditions an important reduction was observed in the molecular weight: at 120°C and 60 min it was 63 kDa; at 150°C and 45 min it was reduced down to 8 kDa; and at 170°C and 20 min it was only 7 kDa. Besides this reduction in the MW some hydrolysis products, such as glucose and HMF, were observed. These results revealed the convenience of using PHW to dissolve β -glucans since the operation times, compared to the conventional process (55°C, 3 h), were reduced despite the fact that the MW was significantly reduced once the β -glucan was dissolved; therefore, PHW can be used to extract β -glucans from barley under controlled conditions in order to prevent severe degradation.
Five products of N-(6-carboxyl cyclohex-3-ene carbonyl) chitosan as antimicrobial agents were prepared by reaction of chitosan with tetrahydrophthalic anhydride (THPA) at different degrees of substitution (DS). The antimicrobial activity was evaluated against four plant bacteria and eight fungi. The results proved that the inhibitory property and water solubility of the synthesized chitosan derivatives, with increase of the DS, exhibited a remarkable improvement over chitosan. The product with a DS of 0.40 was the most active one with MIC of 510, 735, 240, and 385 mg/L against Erwinia carotovora, Ralstonia solanacearum, Rhodococcus fascians, and Rhizobium radiobacter, respectively, and also in mycelial growth inhibition against Alternaria alternata (EC50 = 683 mg/L), Botrytis cinerea (EC50 = 774 mg/L), Botryodiplodia theobromae (EC50 = 501 mg/L), Fusarium oxysporum (EC50 = 500 mg/L), F. solani (EC50 = 260 mg/L), Penicillium digitatum (EC50 = 417 mg/L), Phytophthora infestans (EC50 = 298 mg/L), and Sclerotinia sclerotiorum (EC50 = 763 mg/L). These compounds based on a biodegradable and biocompatible chitosan could be used as potentially antimicrobial agents in crop protection instead of hazardous synthetic pesticides.
Since the bleaching process is one of the most important environmental pollutant stages in the pulp and paper industry, here, the total chlorine-free (TCF) bleaching of poplar kraft pulp by applying Oxone and peroxide under alkaline conditions has been investigated. The pulp samples were bleached in two stages of Oxone (OX) treatment using an AOX1OX2sequence (A: acid pretreatment), and then the treated pulps were bleached by peroxide (P) to achieve target brightness (about 80%). The influence of various reaction parameters such as alkali charge, temperature, reaction time, and bleaching agent dosage was optimized. The final achieved brightness was more than 78%. Accelerated aging experiments showed more stability in brightness for the Oxone treated pulp, because alkali Oxone bleaching stops thermal degradation. Similarly, the AOX1OX2P bleaching sequence was found to be effective in regaining some strength that had been lost during acidification of the pulp. Improvement in pulp strength made with acid treatment was achieved along with significant amount of lignin removal and it demonstrates the feasibility of Oxone in TCF bleaching. Furthermore, other results indicated the feasibility of Oxone bleaching as an environmentally favorable alternative TCF bleaching sequence, compared with elemental chlorine-free bleaching approaches and also other TCF bleaching sequences.
Since the bleaching process is one of the most important environmental pollutant stages in the pulp and paper industry, here, the total chlorine-free (TCF) bleaching of poplar kraft pulp by applying Oxone and peroxide under alkaline conditions has been investigated. The pulp samples were bleached in two stages of Oxone (O X ) treatment using an AO X1 O X2 sequence (A: acid pretreatment), and then the treated pulps were bleached by peroxide (P) to achieve target brightness (about 80%). The influence of various reaction parameters such as alkali charge, temperature, reaction time, and bleaching agent dosage was optimized. The final achieved brightness was more than 78%. Accelerated aging experiments showed more stability in brightness for the Oxone treated pulp, because alkali Oxone bleaching stops thermal degradation. Similarly, the AO X1 O X2 P bleaching sequence was found to be effective in regaining some strength that had been lost during acidification of the pulp. Improvement in pulp strength made with acid treatment was achieved along with significant amount of lignin removal and it demonstrates the feasibility of Oxone in TCF bleaching. Furthermore, other results indicated the feasibility of Oxone bleaching as an environmentally favorable alternative TCF bleaching sequence, compared with elemental chlorine-free bleaching approaches and also other TCF bleaching sequences.
The third generation of glycoconjugated azo dyes (GADs) was prepared linking monoazo dyes to 6-amino-6-deoxy-d-galactose or 6′amino-6′-deoxylactose through mixed amido-ester connections. The complementary conjugation reactions were studied using the succinyl derivative of either the acetal protected aminosugar or the azo dye. Target “naturalized” GADs were obtained after acid hydrolysis of the acetal protecting groups present on the sugar moiety.
Chitin and chitosan, valuable marine biopolymers, recovered from shrimp waste, are an abundant by-product of the shrimp processing industry in Vietnam, at an estimated 200000 metric tons per year. The obtained chitin and chitosan are characterized by their purity and functional properties. The polymers show good quality with low residual ash and protein content (<1%). The antioxidant potency of chitosan is evaluated by several different in vitro systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, total reducing power, and inhibition of lipid peroxidation. The DPPH free radical scavenging, total reducing power, and lipid peroxidation inhibition activities of chitosan at varying concentration (0.125 to 1.0 mg/mL) range from 3.7 to 16.8%, 0.05 to 0.15, and 1.7 to 15.1%, respectively. This study demonstrates that chitin and chitosan, of good quality and having characteristics compatible with a broad range of applications, can be prepared from white shrimp waste.
A commercial apple pectin was sequentially digested with the cloned enzymes endopolygalacturonase, galactanase, arabinofuranosidase, xylogalacturonase, and rhamnogalacturonan hydrolase. The rhamnogalacturonan hydrolase-generated oligosaccharides were separated by ultrafiltration, anion exchange, and size-exclusion chromatography. Fractions from the ion exchange chromatography were pooled, lyophilized, and screened by MALDI-TOF MS. An oligosaccharide (RGP14P3) was identified and its structure, α -D-Gal p A-(1→2)- α -L-Rha p -(1→4)- α -D-Gal p A-(1→2)- α -L-Rha p -(1→4)- α -D-Gal p A, determined by 1D and 2D NMR spectrometry. This oligosaccharide probably represents a direct connection between homogalacturonan and rhamnogalacturonan in pectin. Alternatively, it could indicate that the nonreducing end of rhamnogalacturonan starts with a galacturonic acid residue.
The complex mixture studied, a hydrolyzed soy protein (HSP), κ -carrageenan ( κ C), and an hydroxypropyl methylcellulose (HPMC), could be used as a foaming agent under refrigeration or heating conditions because of the presence of one polysaccharide (HPMC) that gels on heating and another ( κ C) that gels on cooling. The objective of this work was to study the role of these polysaccharides on foaming properties by whipping methods at heating conditions. For this purpose, response surface methodology was used to optimize the mixed product in foamed food systems. The obtained results showed that the combination of E4M, κ C, and HSP is an adequate strategy to generate good foam capacity and stability at heating conditions. The huge stability increase of foams at heating conditions was ascribed to combined effect of polysaccharides: gelling property of E4M and the viscozieng character imparted by κ C to continuous phase of foaming.
The PI/UV system ((4-trimethyl ammonium methyl) benzophenone chloride/UV) was used to synthesize carboxymethyl starch- (CMS-) stabilized silver nanoparticles (AgNPs). AgNPs so prepared had round shape morphology with size of 1–7 nm. The prepared AgNPs were utilized to impart antibacterial finishing for cotton fabrics. The PI/UV system was further utilized to fix AgNPs onto cotton fabrics by photocrosslinking of AgNPs-CMS composite onto cotton fabrics to impart durable antibacterial properties. Effect of irradiation time and incorporating N, N-methylene diacrylamide (MDA) in different concentrations on antibacterial performance before and after repeated washing cycles was studied. S. aureus and E. coli were used to evaluate the antibacterial performance of finished fabrics. The antibacterial performance was directly proportional to the irradiation time and concentration of MDA but inversely proportional to the number of washing cycles. The inhibition zone of S. aureus and E. coli is the same although they are different in the cell wall structure and mode of action due to the nanosize structure formed.
Structurally simple 1-thio-β-D-glucopyranosides were synthesized and tested as potential inhibitors toward several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. Significant selective inhibition was observed for α- and β-glucosidases, while a weak to moderate activation for α- and β-galactosidases.
Kinetics and mechanism of micellar catalyzed N-bromosuccinimide oxidation of dextrose in H 2 SO 4 medium was investigated under pseudo-first-order condition temperature of 40°C. The results of the reactions studied over a wide range of experimental conditions show that NBS shows a first order dependence, fractional order, on dextrose and negative fractional order dependence on sulfuric acid. The determined stoichiometric ratio was 1 : 1 (dextrose : N-bromosuccinimide). The variation of Hg(OAC) 2 and succinimide (reaction product) has insignificant effect on reaction rate. Effects of surfactants, added acrylonitrile, added salts, and solvent composition variation have been studied. The Arrhenius activation energy and other thermodynamic activation parameters are evaluated. The rate law has been derived on the basis of obtained data. A plausible mechanism has been proposed from the results of kinetic studies, reaction stoichiometry, and product analysis. The role of anionic and nonionic micelle was best explained by the Berezin’s model.
In the present work, we have studied the inhibitory effects of aqueous and alcoholic extracts of six Algerian medicinal plants known by their therapeutic virtues against diabetes. The total phenolic compounds content, assayed using Folin-Ciocalteu’s reagent, of the samples ranged from 0.183 mg/g to 43.088 mg/g and from 1.197 mg/g to 7.445 mg/g, expressed as gallic acid equivalent (GAE), for the, respectively, whereas the total flavonoids concentrations, detected using 2% of the aluminium chloride, ranged from 0.41 mg/g to 11.613 mg/g and from 0.0097 mg/g to 1.591 mg/g, expressed as rutin equivalents (RE), for the aqueous and methanolic extracts, respectively. The major plants were found to inhibit enzymatic activities of Aspergillus oryzae-amylase in a concentration dependent manner. The values of the inhibition constants (Ki) have been determined according to the Dixon and Lineweaver-Burk methods. The results showed that the Ki values were less than 55 ppm for the all extracts. A strong inhibition was found in the phenolic extract of Salvia officinalis with a Ki of 8 ppm.
The objective of this work was to determine the effects of high intensity ultrasound application on the foaming properties of soy protein-polysaccharides mixed solutions. To this end, foaming parameters during foam formation were analyzed. The samples were sonicated for 20 min using ultrasonic processor Vibra Cell Sonics, and model VCX 750 at a frequency of 20 kHz and an amplitude of 20%. The foams were produced by a Foamscan instrument. The evolution of the bubble size change in the foam was also determined by a second CCD camera. For all foamed systems, at two pHs 3 and 7, Foam expansion and Relative Foam Conductivity showed a great increase after ultrasonic treatment. Other parameters studied did not show difference. On the other hand, Final Time of Foaming and the Total Gas Volume incorporation for foams formation were correlated with the Relative Foam Conductivity decrease and the Foam Expansion increase when HIUS were applied in every system. Comparative bubble size and shape during the foam formation according to the treatments and pH used confirmed the parameters results.
Guar gum and its derivatives are highly important industrial hydrocolloids as they find applications in various industrial sectors. Guar is a polymer of high molecular weight and its aqueous solutions exhibit unique rheological properties, which has led to its wide acceptance by the industry. In certain industrial applications low molecular weight guar and its derivatives are needed, and conventionally chemical depolymerisation of guar is carried out for this purpose. Radiation processing is a novel and green technology for carrying out depolymerization and can be an ideal substitute for chemical depolymerisation technique. In order to study the effect of radiation on guar derivatives, three types of derivatives have been taken in the present study: carboxymethyl, hydroxyethyl, and methyl guar. The effect of 1–50 KGy radiation dose on the rheological behavior of these derivatives has been studied, and the results have been described in the present paper. The effect on storage and loss modulus with respect to frequency and effect on viscosity with respect to shear rate have been discussed in detail.
The aim of this research was to investigate the effect of tribomechanical treatments on rheological, thermophysical, and some physical properties of tapioca starch. Samples of tapioca starch were treated using laboratory equipment for tribomechanical micronization and activation (TMA equipment). Before and after the TMA treatment, analysis of the particle size and particle size distribution was carried out, in addition to scanning electron micrography in tapioca starch. Scanning electron micrography showed that tribomechanical processing of tapioca starch resulted in breaking accumulations of starch granules in the form of granules. Pasting parameters have shown that maximal viscosities of model starch suspension have been decreasing after tribomechanical treatment. On the basis of gelatinization curves, it can be concluded that there are changes in the gelatinization point after treatment, and there is decrease in enthalpy of gelatinization for model suspension. After tribomechanical treatment, changes in physical properties of starch suspensions were determined, as well as specific swelling capacity, solubility index, and turbidity of tapioca starch suspensions.
A water soluble polysaccharide and its selective precipitated fractions (F1, F2, and F3) were isolated from hot water extract of fruiting bodies of Agaricus blazei Murril known as Agaricus brasiliensis to evaluate the analgesic activity of the materials in Swiss mice. The isolated material and its fractions were characterized by two-dimensional COSY and HMQC spectra as β -(1→6)- α -(1→4)-glucan-bound-protein polysaccharide constituted mainly by β -(1→6) glucan. The glucan-protein polysaccharide and its fractions were analyzed in relation to the protein, carbohydrate, and mineral elements contents. The analysis of the glucan-protein complex revealed a total carbohydrate content of 36.95% and protein conjugated content of 17.24%. The mineral elements found in larger proportion were K, Na, Ca, P, and Zn. The analgesic activity bioassay of the β -(1→6)- α -(1→4)-glucan bound-protein polysaccharide and its fractions in Swiss mice indicated a significant effect.
Chondroitin sulfate (CS) is a glycosaminoglycan (GAG) side chain of proteoglycans (PGs) which are widely distributed in the extracellular matrix and at cell surface. CS shows a highly structural diversity in not only molecular weight (MW) but sulfonation pattern. CS has been reported to exert anti-inflammatory activity by having effects on cytokine production by helper T cells. In this study, we focused on the structures of CS chains, especially MW of CS, and investigated effect of the different MW of CS on binding affinity with L-selectin and cytokine production by murine splenocytes. Firstly, we fractionated CS by employing gel filtration chromatography and obtained several CS fractions with different MW. Then the interaction between fractionated CS and L-selectin was analyzed by surface plasmon resonance (SPR). Finally, the influence of MW of CS on cytokine production by murine splenocytes was investigated in vitro. The results showed that interferon-gamma production was significantly increased by mouse splenocytes cocultivated with CS. On the contrary, CS inhibited interleukin 5 production by murine splenocytes depending on MW of the cocultivated CS. These results strongly indicate the existence of the optimal molecular size for an anti-inflammatory effect of CS through cytokine production by murine splenocytes.
Polysaccharides present in several seaweeds ( Kappaphycus alvarezii , Calliblepharis jubata , and Chondrus crispus —Gigartinales, Rhodophyta; Gelidium corneum and Pterocladiella capillacea —Gelidiales, Rhodophyta; Laurencia obtusa —Ceramiales, Rhodophyta; Himanthalia elongata , Undaria pinnatifida , Saccorhiza polyschides , Sargassum vulgare , and Padina pavonica —Phaeophyceae, Ochrophyta) are analyzed by spectroscopic techniques. The nature of the polysaccharides (with extraction and without any type of extraction) present in these seaweeds was determined with FTIR-ATR and FT-Raman analysis of extracted phycocolloids and ground dry seaweed.
A series of starch-co-poly(acrylamide) (starch-co-PAAm) hydrogels were synthesized by employing free radical redox polymerization. A novel green approach, Tridax procumbens (TD) leaf extract, was used for reduction of silver ions (Ag + ) into silver nanoparticles in the starch-co-PAAm hydrogel network. The formation of silver nanoparticles was confirmed by UV-visible spectroscopy (UV-Vis), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and X-ray diffraction (X-RD) studies. 22% of weight loss difference between hydrogel and silver nanocomposite hydrogel (SNCH) clearly indicates the formation of silver nanoparticles by TGA. TEM images indicate the successful incorporation of silver nanoparticles ranging from 5 to 10 nm in size and spherical in shape with a narrow size distribution. These developed SNCHs were used to study the antibacterial activity by inhibition zone method against gram-positive and gram-negative bacteria such as Bacillus and Escherichia coli . The results indicated that these SNCHs can be used potentially for biomedical applications.
