Fructose Molecules Research Articles

Influence of Genotype and Environment on Wheat Grain Fructan Content

Fructans are naturally occurring plant polymers composed of fructose molecules. Approximately 15% of flowering plant species contain fructans, including wheat (Triticum aestivum L.). Fructans serve as carbon stores in plants and exhibit potentially beneficial effects on human health. The main objectives of this study were to examine the effects of genotype and environment on winter wheat grain fructan content and to assess the feasibility of using genomic selection for grain fructan content. Total grain fructan content was determined for 288 winter wheat genotypes grown across 2 yr at three locations each year. Observed variation in wheat grain fructan content was significantly influenced by genotype, environment, and genotype × environment interactions. The high genetic correlation, small impact of genotype × environment interactions on genomic predictability, and lack of significant hits in a genome‐wide association study suggest that genomic selection is a suitable tool in breeding for wheat grain fructan content. The results of this study will be useful for implementing recurrent genomic selection in winter wheat and guiding future decisions regarding breeding methodologies for total fructan content in wheat. This study provides a deeper understanding of the effects of genotype, environment, and genotype × environment interaction on fructan content, which will have implications for breeders seeking to develop nutritionally improved, climate‐resilient wheat cultivars.

Small Molecular Weight Aldose (d-Glucose) and Basic Amino Acids (l-Lysine, l-Arginine) Increase the Occurrence of PAHs in Grilled Pork Sausages.

(1) Background: Amino acids and carbohydrates are widely used as additives in the food industry. These compounds have been proven to be an influencing factor in the production of chemical carcinogenic compounds polycyclic aromatic hydrocarbons (PAHs). However, the effect of the properties of the amino acids and carbohydrates on the production of PAHs is still little known. (2) Methods: We added different (i) R groups (the R group represents an aldehyde group in a glucose molecule or a ketone group in a fructose molecule); (ii) molecular weight carbohydrates; (iii) polarities, and (iv) acid-base amino acids to pork sausages. The effects of the molecular properties of carbohydrates and amino acids on the formation of PAHs in grilled pork sausages were investigated. (3) Results: The results showed that a grilled sausage with aldehyde-based d-glucose was capable of producing more PAHs than a sausage with keto-based d-fructose. A higher PAH content was determined in the grilled pork sausage when the smaller molecular weight, d-glucose, was added compared with the sausage where the larger molecular weight, 4-(α-d-glucosido)-d-glucose and cellulose were added. The addition of basic amino acids (l-lysine, l-arginine) was capable of producing more PAHs compared with the addition of acidic amino acids (l-glutamic acid, l-aspartate). When amino acid containing a benzene ring was added, a smaller volume of PAHs was produced compared with the addition of other amino acids. (4) Conclusions: Our study suggests that systematic consideration of molecule properties is necessary when using food additives (amino acids and carbohydrates) for food processing.

In situ synthesis of sulfur-doped graphene quantum dots decorated carbon nanoparticles hybrid as metal-free electrocatalyst for oxygen reduction reaction

In this study, we have successfully prepared in-situ synthesis of sulfur-doped graphene quantum dots decorated carbon nanoparticles (S-GQDs/CNPs) hybrid from low-cost fructose and H2SO4 by the hydrothermal method. Fructose molecules are dehydrated by concentrated sulfuric acid, then formed honeycomb carbon matrix including sulfate radical in the hydrothermal process, while H2SO4 catalyses the reaction and offers sulfur atom for the carbon material. The result of transmission electron microscopy (TEM) demonstrates that a lot of in-situ grown S-GQDs are decorated on carbon nanoparticles by π–π stacking in the hydrothermal process, advantages of both GQDs and carbon nanoparticles combined, which facilitates the electron transfer between S-GQDs and carbon nanoparticles. X-ray photoelectron spectroscopy (XPS) and Fourier Transform Infrared (FT-IR) spectra show the presence of –C–S–C– bonds and the absence of oxygen-containing groups in S-GQDs/CNPs hybrid. As expected, the electrochemical data of S-GQDs/CNPs hybrid indicate that the layer by layer modified method can inhibit the occurrence of a two-electron pathway and cause a four-electron pathway for ORR. Moreover, the resulting S-GQDs/CNPs hybrid has a better methanol tolerance and long-term durability than commercial 20% Pt/C.

The interaction of low-energy electrons with fructose molecules

Using a hypocycloidal electronic spectrometer, the interactions of low energy electrons (0–8.50 eV) with fructose molecules, namely, electron scattering and dissociative attachment, are studied. The results of these studies showed that the fragmentation of fructose molecules occurs effectively even at an electron energy close to zero. In the total electron-scattering cross section by molecules, resonance features (at energies ~3.10 and ~5.00 eV) were first observed near the formation thresholds of light ion fragments OH– and H–. The correlation of the features observed in the cross sections of electron scattering and dissociative attachment is analyzed.

Fast probing of glucose and fructose in plant tissues via plasmonic affinity sandwich assay with molecularly-imprinted extraction microprobes

Determination of specific target compounds in agriculture food and natural plant products is essential for many purposes; however, it is often challenging due to the complexity of the sample matrices. Herein we present a new approach called plasmonic affinity sandwich assay for the facile and rapid probing of glucose and fructose in plant tissues. The approach mainly relies on molecularly imprinted plasmonic extraction microprobes, which were prepared on gold-coated acupuncture needles via boronate affinity controllable oriented surface imprinting with the target monosaccharide as the template molecules. An extraction microprobe was inserted into plant tissues under investigation, which allowed for the specific extraction of glucose or fructose from the tissues. The glucose or fructose molecules extracted on the microprobe were labeled with boronic acid-functionalized Raman-active silver nanoparticles, and thus affinity sandwich complexes were formed on the microprobes. After excess Raman nanotags were washed away, the microprobe was subjected to Raman detection. Upon being irradiated with a laser beam, surface plasmon on the gold-coated microprobes was generated, which further produced plasmon-enhanced Raman scattering of the silver-based nanotags and thereby provided sensitive detection. Apple fruits, which contain abundant glucose and fructose, were used as a model of plant tissues. The approach exhibited high specificity, good sensitivity (limit of detection, 1 μg mL−1), and fast speed (the whole procedure required only 20 min). The spatial distribution profiles of glucose and fructose within an apple were investigated by the developed approach.

The mechanism for cleavage of three typical glucosidic bonds induced by hydroxyl free radical

A novel mechanism for cleavage of three typical α(1→2), α(1→4) and β(1→4) glucosidic bonds induced by hydroxyl free radical was examined with DFT theory at B3LYP/6–31+G(d,p) level using PCM water solvent model. It was found that the hydrogen abstraction from the CH bonds outside the saccharide rings could induce the hydrogen transfer from the hydroxyl at the radical carbon to the oxygen atom of saccharide ring with the mediation of water, which led to the opening of saccharide ring and the breakage of glucosidic bonds. Alternatively, the hydrogen in COH outside the saccharide ring of maltose and sucrose could also transfer to the adjacent glucosidic oxygen atom with a water molecule mediation to make glucosidic bond break directly. Based on this study, it can be well explained the experimental results that the oxidation of some oligosaccharides with hydroxyl free radicals can produce molecules of glucose, fructose and other monosaccharides.

An Analysis of the Composition, Health Benefits, and Future Market Potential of the Jerusalem Artichoke in Canada

This article presents an overview of the Jerusalem artichoke and its potential uses in consumer food products. Jerusalem artichoke, native to North America, is characterized by its sunflower-like appearance and carbohydrate-rich tubers. For centuries, Jerusalem artichoke tubers were a food source for Aboriginal Canadians and early European settlers. Today, Jerusalem artichoke is used to obtain inulin for addition into food products. Inulin is a polysaccharide that provides several health benefits when consumed. Due to its unique structure of fructose and glucose molecules, inulin is indigestible by the human digestive system. Its benefits are realized when it enters the large intestine and is fermented by microorganisms. This process stimulates prebiotic and dietary fibre effects that improve the growth of beneficial bacteria and promote greater digestive health. Additionally, inulin can act as a sugar or fat substitute in foods, and even facilitates the absorption of minerals in the large intestine. Currently, the use of Jerusalem artichoke inulin in commercial food products is limited. However, trends focusing on healthy living and supporting local industry indicate that Canadian consumers will positively view products made with Canadian-grown Jerusalem artichoke. The advantage that Jerusalem artichoke has over other inulin-rich products is that it can grow on poor land and is also more resistant to extreme weather conditions relative to corn and/or sugar beet; this is significant in the Canadian context. Given these trends and supplementary market data, the potential market size for Jerusalem artichoke-enriched products has been determined. Additionally, prices of currently available inulin-enriched products have been used as guidelines to determine total market potential. Market potential for baked goods, particularly muffins, was found to be $CAD 8,721,788 while market potential for beverages, namely soda, was found to be $CAD 11,707,098. These numbers, though imperfect, indicate that there is strong potential for Jerusalem artichoke-enriched products to be marketed to Canadian consumers.

Functional Effects of Prebiotic Fructans in Colon Cancer and Calcium Metabolism in Animal Models.

Inulin-type fructans are polymers of fructose molecules and are known for their capacity to enhance absorption of calcium and magnesium, to modulate gut microbiota and energy metabolism, and to improve glycemia. We evaluated and compared the effects of Chicory inulin “Synergy 1®” and inulin from Mexican agave “Metlin®” in two experimental models of colon cancer and bone calcium metabolism in mice and rats. Inulins inhibited the development of dextran sulfate sodium-induced colitis and colon cancer in mice; these fructans reduced the concentration of tumor necrosis factor alpha and prevented the formation of intestinal polyps, villous atrophy, and lymphoid hyperplasia. On the other hand, inulin treatments significantly increased bone densitometry (femur and vertebra) in ovariectomized rats without altering the concentration of many serum biochemical parameters and urinary parameters. Histopathology results were compared between different experimental groups. There were no apparent histological changes in rats treated with inulins and a mixture of inulins-isoflavones. Our results showed that inulin-type fructans have health-promoting properties related to enhanced calcium absorption, potential anticancer properties, and anti-inflammatory effects. The use of inulin as a prebiotic can improve health and prevent development of chronic diseases such as cancer and osteoporosis.

An Alteration in the Cecal Microbiota Composition by Feeding of 1-Kestose Results in a Marked Increase in the Cecal Butyrate Content in Rats.

Functional food ingredients, including prebiotics, have been ardently developed for improving the intestinal environment. Fructooligosaccarides (FOS), including fructans, are the well researched and commercialized prebiotics. However, to our knowledge, few studies have been conducted on the physiological effects of each component of FOS as prebiotics. 1-Kestose, a component of FOS, is composed of one glucose and two fructose molecules, and is considered as a key prebiotic component in short-chain FOS. In the present study, we examined the effects of dietary 1-kestose using 0.5–5% 1-kestose diets on cecal microbiota composition and cecal contents of short-chain fatty acids and lactate in rats. The findings indicate that dietary 1-kestose induced cecal hypertrophy and alterations in the cecal microbiota composition, including a marked increase in the cell number of Bifidobacterium spp. These alterations were associated with significant increases in acetate and lactate, and a marked increase in butyrate in cecal contents. Furthermore, dietary 1-kestose induced a significant decrease in serum insulin concentration in rats fed 2.5–5% 1-kestose diet. These findings suggest a potential of 1-kestose to be a prebiotic for improving the metabolism of the host.

Synthesis and characterization of functionalized alumina catalysts with thiol and sulfonic groups and their performance in producing 5-hydroxymethylfurfural from fructose

5-Hydroxymethylfurfural (HMF) has been identified as a potential candidate for biofuels and a high-potential intermediate chemical compound. The obtention of HMF from fructose is efficiently carried out using acid catalysts. In this work, a new catalyst of alumina synthesized by sol-gel as support was bifunctionalized with thiol (SH) and sulfonic (SO3−) groups by the grafting method and compared with other supports, i.e., synthesized boehmite and commercial alumina. The 3-mercaptopropyl-trimethoxysilane was utilized as a source of the thiol group to promote fructose tautomerization to its furanose form. The sulfonic group was obtained from 1,3-propanesultone, which carries out the dehydration of the fructose molecule. The prepared bifunctionalized catalysts were tested in the fructose dehydration reaction. The functional groups were identified through Fourier transform infrared spectroscopy (FTIR) as the primary characterization. The type of acid site was identified by Fourier transform infrared spectroscopy (–pyridine (FTIR-py)) and quantified by temperature-programmed desorption of ammonia (TPD-NH3). The molecular structures of thiol and the sulfonic groups anchored on the supports were resolved by nuclear magnetic resonance with cross-polarization (CP) and magic angle spinning (MAS) (CP-MAS-NMR). The bifunctionalized catalyst of alumina synthesized by sol-gel, being a very competitive material, reached a 55% selectivity to HMF at a 72% conversion at 453K.

Spontaneous Capture of Carbohydrate Guests through Folding and Zipping of Self‐Assembled Ribbons

AbstractOne of the great challenges in molecular self‐assembly is how to confer self‐folding and closing characteristics on flat two‐dimensional structures in response to external triggers. Herein, we report a planar ribbon assembly that folds into closed tubules in response to fructose. The ribbons, ≈28 nm wide and 3.5 nm thick, consist of 8 laterally‐associated elementary fibrils in which disc‐shaped macrocycle amphiphiles are stacked along their axis. Upon addition of fructose, these flat structures spontaneously fold into closed tubules, with an outer diameter of ≈8 nm, through zipping of the two sides of the ribbons. Notably, the folding and then zipping of the flat ribbons is accompanied by spontaneous capture of the fructose molecules inside the tubular cavities.

Spontaneous Capture of Carbohydrate Guests through Folding and Zipping of Self-Assembled Ribbons.

One of the great challenges in molecular self-assembly is how to confer self-folding and closing characteristics on flat two-dimensional structures in response to external triggers. Herein, we report a planar ribbon assembly that folds into closed tubules in response to fructose. The ribbons, ≈28 nm wide and 3.5 nm thick, consist of 8 laterally-associated elementary fibrils in which disc-shaped macrocycle amphiphiles are stacked along their axis. Upon addition of fructose, these flat structures spontaneously fold into closed tubules, with an outer diameter of ≈8 nm, through zipping of the two sides of the ribbons. Notably, the folding and then zipping of the flat ribbons is accompanied by spontaneous capture of the fructose molecules inside the tubular cavities.

Dielectric study on temperature–concentration superposition of liquid to glass in fructose–water mixtures

Broadband dielectric measurements of fructose–water mixtures with various fructose concentrations, Cf (wt.%), in the range of 5–94.6wt.% were carried out in the frequency range of 2mHz–50GHz at 25 and 0°C, to clarify the dynamics of water and fructose molecules in the mixtures from liquid to glass states as a function of Cf. For the mixtures with Cf below 45wt.%, a single relaxation process originating from the reorientational motion of water, i.e., ν relaxation, was observed. In contrast, in the mixtures with Cf above 45wt.%, in addition to the ν relaxation, α relaxation resulting from the cooperative motion of two components appears at a lower frequency than that of the ν relaxation. The temperature dependences of the relaxation time and strength of the α and ν relaxations are governed by the deviation from the glass transition temperature. Similarly, the concentration dependences of the relaxation time and strength are governed by the deviation from the glass transition concentration, which was defined as the concentration at which the relaxation time is 100s. This means that the temperature–concentration superposition appears to be valid for the ν and α relaxations.

Preparation of Inulin from Dahlia Tubers

Inulin is polysaccharide chains comprised primarily of linked fructose molecules that are bifidogenic. Inulin-type prebiotics are used as functional food ingredients in beverages, yogurts, biscuits, and spreads; they are also used as dietary supplements. The objective of this study was to increase the yield of inulin by improving the inulin extraction from dahlia tubers. Inulin was isolated from fresh and chips of dahlia tubers. The dahlia tubers was blanched, sliced and blended by adding the hot water in ratio 1:1. inulin extract was evaporated and precipitated by 95% ethanol for 24hours in a room temperature. Inulin was separated and dried at 50°C for 24hours. Results showed that the best ratio of inulin extract and ethanol is 1: 2 and the highest yield of inulin powder was produced from inulin extract of 30.0% brix. Moreover, the yield of inulin which refer to fresh dahlia tubers is between 6.0 - 9.5% w/w.

From fructans to difructose dianhydrides.

Fructans are the polymers of fructose molecules, normally having a sucrose unit at what would otherwise be the reducing terminus. Inulin and levan are two basic types of simple fructan, which contain β-(2, 1) and β-(2, 6) fructosyl-fructose linkage, respectively. Fructans not only can serve as soluble dietary fibers for food industry, but also may be biologically converted into high-value products, especially high-fructose syrup and fructo-oligosaccharides. In recent years, much attention has been focused on production of difructose dianhydrides (DFAs) from fructans. DFAs are cyclic disaccharides consisting of two fructose units with formation of two reciprocal glycosidic linkages. They are expected to have promising properties and beneficial effects on human health. DFAs can be produced from fructans by fructan fructotransferases. Inulin fructotransferase (IFTase) (DFA III-forming) and IFTase (DFA I-forming) catalyze the DFA III and DFA I production from inulin, respectively, and levan fructotransferase (LFTase) (DFA IV-forming) catalyzes the production of DFA IV from levan. In this article, the DFA-producing microorganisms are summarized, relevant studies on various DFAs-producing enzymes are reviewed, and especially, the comparisons of the enzymes are presented in detail.

Microbial enzymatic production and applications of short-chain fructooligosaccharides and inulooligosaccharides: recent advances and current perspectives.

The industrial production of short-chain fructooligosaccharides (FOS) and inulooligosaccharides is expanding rapidly due to the pharmaceutical importance of these compounds. These compounds, concisely termed prebiotics, have biofunctional properties and hence health benefits if consumed in recommended dosages. Prebiotics can be produced enzymatically from sucrose elongation or via enzymatic hydrolysis of inulin by exoinulinases and endoinulinases acting alone or synergistically. Exoinulinases cleave the non-reducing β-(2, 1) end of inulin-releasing fructose while endoinulinases act on the internal linkages randomly to release inulotrioses (F3), inulotetraoses (F4) and inulopentaoses (F5) as major products. Fructosyltransferases act by cleaving a sucrose molecule and then transferring the liberated fructose molecule to an acceptor molecule such as sucrose or another oligosaccharide to elongate the short-chain fructooligosaccharide. The FOS produced by the action of fructosyltransferases are 1-kestose (GF2), nystose (GF3) and fructofuranosyl nystose (GF4). The production of high yields of oligosaccharides of specific chain length from simple raw materials such as inulin and sucrose is a technical challenge. This paper critically explores recent research trends in the production and application of short-chain oligosaccharides. Inulin and enzyme sources for the production of prebiotics are discussed. The mechanism of FOS chain elongation and also the health benefits associated with prebiotics consumption are discussed in detail.

The ABC Transporter Encoded at the Pneumococcal Fructooligosaccharide Utilization Locus Determines the Ability To Utilize Long- and Short-Chain Fructooligosaccharides

Streptococcus pneumoniae is an important human pathogen that requires carbohydrates for growth. The significance of carbohydrate acquisition is highlighted by the genome encoding more than 27 predicted carbohydrate transporters. It has long been known that about 60% of pneumococci could utilize the fructooligosaccharide inulin as a carbohydrate source, but the mechanism of utilization was unknown. Here we demonstrate that a predicted sucrose utilization locus is actually a fructooligosaccharide utilization locus and imparts the ability of pneumococci to utilize inulin. Genes in strain TIGR4 predicted to encode an ABC transporter (SP_1796-8) and a β-fructosidase (SP_1795) are required for utilization of several fructooligosaccharides longer than kestose, which consists of two β(2-1)-linked fructose molecules with a terminal α(1-2)-linked glucose molecule. Similar to other characterized pneumococcal carbohydrate utilization transporter family 1 transporters, growth is dependent on the gene encoding the ATPase MsmK. While the majority of pneumococcal strains encode SP_1796-8 at this genomic location, 19% encode an alternative transporter. Although strains encoding either transporter can utilize short-chain fructooligosaccharides for growth, only strains encoding SP_1796-8 can utilize inulin. Exchange of genes encoding the SP_1796-8 transporter for those encoding the alternative transporter resulted in a TIGR4 strain that could utilize short-chain fructooligosaccharide but not inulin. These data demonstrate that the transporter encoded at this locus determines the ability of the bacteria to utilize long-chain fructooligosaccharides and explains the variation in inulin utilization between pneumococcal strains.

Hydration and Aggregation in Mono- and Disaccharide Aqueous Solutions by Gigahertz-to-Terahertz Light Scattering and Molecular Dynamics Simulations

The relaxation properties of hydration water around fructose, glucose, sucrose, and trehalose molecules have been studied by means of extended frequency range depolarized light scattering and molecular dynamics simulations. Evidence is given of hydration dynamics retarded by a factor ξ = 5-6 for all the analyzed solutes. A dynamical hydration shell is defined based on the solute-induced slowing down of water mobility at picosecond time scales. The number of dynamically perturbed water molecules N(h) and its concentration dependence have been determined in glucose and trehalose aqueous solutions up to high solute weight fractions (ca. 45%). For highly dilute solutions, about 3.3 water molecules per sugar hydroxyl group are found to be part of the hydration shell of mono- and disaccharide. For increasing concentrations, a noticeable solute-dependent reduction of hydration number occurs, which has been attributed, in addition to simple statistical shells overlapping, to aggregation of solute molecules. A scaling law based on the number of hydroxyl groups collapses the N(h) concentration dependence of glucose and trehalose into a single master plot, suggesting hydration and aggregation properties independent of the size of the sugar. As a whole, the present results point to the concentration of hydroxyl groups as the parameter guiding both sugar-water and sugar-sugar interactions, without appreciable difference between mono- and disaccharides.

Uric Acid Induces Hepatic Steatosis by Generation of Mitochondrial Oxidative Stress

Uric acid is an independent risk factor in fructose-induced fatty liver, but whether it is a marker or a cause remains unknown. Hepatocytes exposed to uric acid developed mitochondrial dysfunction and increased de novo lipogenesis, and its blockade prevented fructose-induced lipogenesis. Rather than a consequence, uric acid induces fatty liver Hyperuricemic people are more prone to develop fructose-induced fatty liver. Metabolic syndrome represents a collection of abnormalities that includes fatty liver, and it currently affects one-third of the United States population and has become a major health concern worldwide. Fructose intake, primarily from added sugars in soft drinks, can induce fatty liver in animals and is epidemiologically associated with nonalcoholic fatty liver disease in humans. Fructose is considered lipogenic due to its ability to generate triglycerides as a direct consequence of the metabolism of the fructose molecule. Here, we show that fructose also stimulates triglyceride synthesis via a purine-degrading pathway that is triggered from the rapid phosphorylation of fructose by fructokinase. Generated AMP enters into the purine degradation pathway through the activation of AMP deaminase resulting in uric acid production and the generation of mitochondrial oxidants. Mitochondrial oxidative stress results in the inhibition of aconitase in the Krebs cycle, resulting in the accumulation of citrate and the stimulation of ATP citrate lyase and fatty-acid synthase leading to de novo lipogeneis. These studies provide new insights into the pathogenesis of hepatic fat accumulation under normal and diseased states.

O-Glycosidic bond exocyclic cleavage of difructose led by acidic proton migration: Density functional theory calculation study

We investigate proton migrations from (H2O)n (n=1–3) to difructose, α-d-fructofuranose-β-d-fructofuranose-2,3′, using density functional theory. The proton migrations result in O-glycosidic bond cleavage. The highest transition barrier for proton migrations taking place from (H2O)3 to difructose is 11.67kcalmol−1. The barriers are much lower than those for the direct breaking of a covalent bond in a difructose linkage. In addition, an autocatalysis process is also studied. An excess proton can migrate from a fructose molecule to a difructose molecule, leading to O-glycosidic bond cleavage. The transition barrier energy for this proton migration is 5.35kcalmol−1.