epiglucan and ferulic-acid

Ferulic acid (FA) is an effective chemopreventive and therapeutic agent for colorectal cancer. However, FA cannot stably reach the colon through human digestive system, and it can be grafted into oligosaccharides to improve its digestion stability. Therefore, in this study, different degrees of substitution of feruloylated oat β-glucan (FA-OβG) were prepared by grafting FA onto water soluble oat β-glucan. FA grafting changed the crystallinity and surface morphology of OβG, and the thermal stability of the FA-OβG improved. As the DS increased, the antioxidant activity of FA-OβG increased, and FA-OβG III with DS of 0.184 showed the same antioxidant activities compared to the equal amount of free FA. The FA-OβG showed higher stability under gastrointestinal and colonic conditions than free FA. Furthermore, the FA-OβG conjugates exhibited good in vitro anticancer activity against human colorectal cancer cells, while FA-OβG III showed better anticancer activity than an equal amount of free FA.

Topics: Adult; Antineoplastic Agents, Phytogenic; Antioxidants; Benzothiazoles; beta-Glucans; Biphenyl Compounds; Cell Proliferation; Colon; Coumaric Acids; Feces; Female; Fermentation; Gastric Juice; HCT116 Cells; Humans; Intestinal Secretions; Male; Picrates; Sulfonic Acids; Surface Properties; Young Adult

A biopolymer-polyphenol conjugate-stabilized oil-in-water emulsion system was established to improve the chemical stability and bioaccessibility of β-carotene (BC). In this study, the emulsifying properties and contribution of a ferulic acid-grafted curdlan conjugate (Cur-D-g-FA) to the chemical stability of BC were investigated. Results showed that the emulsification ability of emulsions stabilized by Cur-D-g-FA remarkably increased with an increasing concentration from 0.05% to 0.8% (w/v) along with decreasing average droplet sizes, negatively charged zeta potentials, and uniform size distributions. The emulsions stabilized by 0.8% Cur-D-g-FA exhibited pronounced shear thinning and solid-like elastic properties as well as satisfactory oxidation stability. The emulsions stabilized by 0.8% Cur-D-g-FA had excellent ability to improve the chemical stability of BC when exposed to different environmental stresses and resulted in the favorable bioaccessibility of BC in vitro. The results prove that Cur-D-g-FA as a promising stabilizer has great potential to protect liposoluble nutrients in food-grade emulsion-delivery systems.

Topics: beta Carotene; beta-Glucans; Biological Availability; Corn Oil; Coumaric Acids; Emulsifying Agents; Emulsions; Food Storage; Hydrogen-Ion Concentration; Osmolar Concentration; Oxidation-Reduction

Grafting copolymerization of phenolic acids onto polysaccharides is an important strategy to improve their biological activities. In this study, ferulic acid (FA)-grafted carboxylic curdlan conjugates, namely, Cur-8-g-FA, Cur-24-g-FA, and Cur-48-g-FA, were synthesized by free radical-induced grafting. Results showed that FA was covalently grafted onto carboxylic curdlans via ester bonds. The grafting ratios of Cur-8-g-FA, Cur-24-g-FA, and Cur-48-g-FA were 223.03 ± 12.63, 115.63 ± 5.96, and 152.30 ± 4.57 mg FA/g, respectively, which were related with the carboxylate contents, molecular weights, and chain conformations of carboxylic curdlans. Compared with carboxylic curdlans, the FA-grafted carboxylic curdlan conjugates had lower thermal stability, molecular weight, and rheological property and looser surface morphology but had more prominent antioxidant benefits in vitro, which were proportional to their grafting ratios. Moreover, good storage stability against chemical degradation was exhibited by the β-carotene in Pickering emulsions stabilized by Cur-8-g-FA with a high grafting ratio and molecular weight.

Topics: Antioxidants; beta Carotene; beta-Glucans; Carboxylic Acids; Coumaric Acids; Emulsions; Free Radicals; Hydroxybenzoates; Molecular Weight

The interaction behavior between food bio-macromolecules is the key point to develop the novel functional food ingredients. Effects of high pressure (HP) or microwave treatment (MW) on the physicochemical properties and microstructures of soy protein hydrolysates (SH)/β-glucan/ferulic acid complexes (S-G-F) were investigated. The results showed that both HP and MW treatment significantly reduced the S-G-F complex particle size and fluorescence intensity along with the improved thermal stability and antioxidant activity but did not affect the zeta potential and the crystal structure. HP treatment changed the conformation of SH by increasing the β-sheet content and decreasing the unordered structure, while MW treatment induce the increase in random coils content and the decreased in the α-helix content of SH. Accordingly, compared with MW treatment, HP treatment could result in the formation of a more compact structure with the uniform distribution through the stronger hydrogen bonding and hydrophobic interaction between components. This work revealed the interaction behaviors of food multi-component self-assembled nanoscale aggregation under high-technology in the food processing, which could provide a new direction for the development of antioxidant food ingredients by effectively utilizing the interaction between food components.

Topics: Antioxidants; beta-Glucans; Coumaric Acids; Food Handling; Food Technology; Hydrophobic and Hydrophilic Interactions; Microwaves; Particle Size; Pressure; Protein Conformation, alpha-Helical; Protein Conformation, beta-Strand; Protein Hydrolysates; Soybean Proteins; X-Ray Diffraction

In this study, water-soluble curdlan products (Cur and Cur-D) were prepared by an alkali-neutralization treatment process, after which ferulic acid (FA)-grafted Cur conjugates (Cur-g-FA and Cur-D-g-FA) were fabricated in the presence and absence of salt by adopting an approach involving free-radicals generated by the ascorbic acid/hydrogen peroxide redox pair under an inert atmosphere. Results showed that FA was successfully grafted onto the C-6 and C-4 positions of the Cur chains through covalent linkages and that the presence of salt exerted minor influences on the grafting ratios and structural characterizations of the products. Cur-g-FA and Cur-D-g-FA showed decreased crystallinity, thermal stability, and rheological properties, as well as a distinct surface morphology, when compared with those of native Cur. However, Cur-g-FA and Cur-D-g-FA also exhibited remarkably enhanced free-radical scavenging ability and antioxidant capacity in vitro. These results indicate that FA-grafted Cur conjugates have great potential application in the field of functional foods.

Topics: Antioxidants; Ascorbic Acid; beta-Glucans; Coumaric Acids; Free Radicals; Hydrogen Peroxide; Oxidation-Reduction; Rheology; Solubility; Surface Properties; Water

Rye bran and aleurone, wheat bran and aleurone, and oat bran and cell wall concentrate were compared in their in vitro gut fermentation patterns of individual phenolic acids and short-chain fatty acids, preceded by enzymatic in vitro digestion mimicking small intestinal events. The formation of phenolic metabolites was the most pronounced from the wheat aleurone fraction. Phenylpropionic acids, presumably derived from ferulic acid (FA), were the major phenyl metabolites formed from all bran preparations. The processed rye, wheat, and oat bran fractions contained more water-extractable dietary fiber (DF) and had smaller particle sizes and were thus more easily fermentable than the corresponding brans. Rye aleurone and bran had the highest fermentation rate and extent probably due to high fructan and water-extractable arabinoxylan content. Oat samples also had a high content of water-extractable DF, β-glucan, but their fermentation rate was lower. Enzymatic digestion prior to in vitro colon fermentation changed the structure of oat cell walls as visualized by microscopy and increased the particle size, which is suggested to have retarded the fermentability of oat samples. Wheat bran was the most slowly fermentable among the studied samples, presumably due to the high proportion of water-unextractable DF. The in vitro digestion reduced the fructan content of wheat samples, thus also decreasing their fermentability. Among the studied short-chain fatty acids, acetate dominated the profiles. The highest and lowest production of propionate was from the oat and wheat samples, respectively. Interestingly, wheat aleurone generated similar amounts of butyrate as the rye fractions even without rapid gas production.

Topics: Avena; beta-Glucans; Butyrates; Cell Wall; Colon; Coumaric Acids; Dietary Fiber; Digestion; Fatty Acids, Volatile; Feces; Fermentation; Humans; Intestine, Small; Metagenome; Phenols; Propionates; Secale; Triticum

The genome of Brachypodium distachyon, also known as purple false brome, was fully sequenced in 2008 largely in response to the demand for a model plant for temperate grasses. A comparative study of the primary cell walls of seedlings of B. distachyon, Hordeum vulgare and Triticum aestivum was carried out. The cell walls of the three species were characterized by similar relative levels of, and developmental changes in, hemicelluloses. The occurrence of (1,3;1,4)-beta-D-glucans was correlated with phases of growth involving cell elongation. Expression profiling of the genes involved in (1,3;1,4)-beta-D-glucan synthesis (cellulose synthase-like F family (CSLF), CSLH and a putative synthase gene CSLJ) did not show a transcriptional regulation that corresponded to the abundance of (1,3;1,4)-beta-D-glucans. CSLF6 transcripts were similarly highly expressed in all three grasses, and were much more abundant than any of the other transcripts. The CSLH transcript was relatively abundant in B. distachyon but almost undetectable in the other species. The deposition of arabinoxylans increased steadily during seedling growth in all three grasses, but they became less substituted and more cross-linked into the wall matrix during cell maturation. Moreover, arabinoxylans in B. distachyon differed from the two other grasses in having a lower degree of arabinose substitution, a higher percentage of ferulic acid in form of dimers and a larger proportion of ester-linked p-coumaric acid.

Topics: Arabinose; beta-Glucans; Cell Wall; Climate; Coumaric Acids; Gene Expression; Gene Expression Regulation, Plant; Genes, Plant; Glucosyltransferases; Plant Proteins; Poaceae; Propionates; Seedlings; Xylans

The present study was conducted to investigate the cell wall properties in two wheat (Triticum aestivum L.) cultivars differing in their sensitivity to Al stress. Seedlings of Al-resistant, Inia66 and Al-sensitive, Kalyansona cultivars were grown in complete nutrient solutions for 4 days and then subjected to treatment solutions containing Al (0, 50 microM) in a 0.5 mM CaCl(2) solution at pH 4.5 for 24 h. Root elongation was inhibited greatly by the Al treatment in the Al-sensitive cultivar compared to the Al-resistant cultivar. The Al-resistant cultivar accumulated less amount of Al in the root apex than in the Al-sensitive cultivar. The contents of pectin and hemicellulose in roots were increased with Al stress, and this increase was more conspicuous in the Al-sensitive cultivar. The molecular mass of hemicellulosic polysaccharides was increased by the Al treatment in the Al-sensitive cultivar. The increase in the content of hemicellulose was attributed to increase in the contents of glucose, arabinose and xylose in neutral sugars. Aluminum treatment increased the contents of ferulic acid and p-coumaric acid especially in the Al-sensitive cultivar by increasing the activity of phenylalanine ammonia lyase (PAL, EC 4.3.1.5). Aluminum treatment markedly decreased the beta-glucanase activity in the Al-sensitive cultivar, but did not exert any effect in the Al-resistant cultivar. These results suggest that the modulation of the activity of beta-glucanase with Al stress may be involved in part in the alteration of the molecular mass of hemicellulosic polysaccharides in the Al-sensitive cultivar. The increase in the molecular mass of hemicellulosic polysaccharides and ferulic acid synthesis in the Al-sensitive cultivar with Al stress may induce the mechanical rigidity of the cell wall and inhibit the elongation of wheat roots.

Topics: Adaptation, Physiological; Aluminum; beta-Glucans; Cell Wall; Coumaric Acids; Hexoses; Pentoses; Plant Roots; Polysaccharides; Propionates; Species Specificity; Triticum