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PubMed1978

[Behavior of various blood constituents (glucose, fructose, insulin, lactate, pyruvate, free fatty acids, inorganic phosphate) and half-life of monosaccharides in the plasma after i.v. infusion of glucose, fructose, galactose and invert sugar solutions in ruminants. 2. Studies in cattle].

Monosaccharides were intravenously injected to eight adult heads of cattle, between 380 kg and 670 kg in live weight, to study, in the context of stress endurance, the half-life values of the sugars as well as monosaccharide effects upon concentrations of various blood components. The fructose concentration in the blood plasma went up temporarily following the infusion of glucose solution. Fructose infusion usually caused only little rise of the glucose concentration in blood plasma, with hypoglycaemia occurring quite often towards the end of an experimental period. The half-life values of sugar in blood plasma were between twelve and 29 and those of fructose between ten and 17 minutes. The rate of fructose conversion was higher than that of glucose conversion, but values were identical in some cases. The pyruvate concentration in the blood and the insulin level in blood plasma went up in response to infusion of monosaccharide solutions. Urine excretion of monosaccharides following invert sugar infusion was less than half of that in response to glucose infusion.

Animals↗

PubMed1997

Lactose, oligosaccharide and monosaccharide content of milk from mothers delivering preterm newborns over the first month of lactation.

BACKGROUND: Monosaccharide, lactose and oligosaccharide content of milk from mothers delivering prematurely (PT milk) was studied to evaluate whether changes occur during lactation, as observed in milk from mothers delivering at term (T milk). METHODS: To study a homogeneous population, women having the most common phenotype (secretory both Lewis and A, B, or H phenotype) were selected. Milk samples from 26 mothers who delivered between the 27th and 35th week of gestation were collected at the 4th, 10th, and 30th post-partum days. Monosaccharides, lactose and oligosaccharides were measured by high-pressure liquid chromatography. RESULTS: Lactose concentration increased significantly (p < 0.05) from 52.81 +/- 8.2 g/L on day 4 to 69.24 +/- 9.36 g/L on day 30. During the same period of time oligosaccharide content decreased significantly (p < 0.05) from 25.61 +/- 5.19 g/L to 15.83 +/- 6.05 g/L. Monosaccharides did not show statistically significant variations. CONCLUSIONS: Our results indicate that PT milk contains in addition to lactose, a substantial amount of oligosaccharides and a lower percentage of monosaccharides. Compared to T milk, in the colostral phase PT milk presents significantly lower lactose concentration (p < 0.0001); on the contrary its oligosaccharide content is significantly higher (p < 0.0001). The physiological role of human milk carbohydrates in view of the peculiar needs of the preterm newborn is also discussed.

Female↗

PubMed1995

Determination of the affinity constants of concanavalin A for monosaccharides by fluorescence affinity probe capillary electrophoresis.

Dissociation constants between a legume lectin, concanavalin A (Con A), and unlabeled neutral monosaccharides were determined by affinity probe capillary electrophoresis (APCE). An affinity probe was synthesized by coupling Lissamine rhodamine B and p-amino-phenyl-alpha-D-mannopyranoside, with glutathione as a negatively charged linker. Electrophoresis of the affinity probe was carried out at neutral pH in a fused silica capillary coated with succinylpolylysine on its inner surface, using laser-induced fluorescence detection. In the presence of Con A, the mobility of the affinity probe decreased and this decrement was analyzed as a function of the concentration of Con A. In the presence of a mixture of Con A and an unlabeled monosaccharide, APCE can thus measure the concentration of Con A unoccupied by the unlabeled monosaccharide, and this allows the determination of the dissociation constant of the Con A-monosaccharide complex. The method should be useful for the analysis of a wide range of molecular interactions on a microscale.

Concanavalin A↗

PubMed2003

Cell activation by monosaccharide lipid A analogues utilizing Toll-like receptor 4.

Lipid A is the bioactive centre of lipopolysaccharide (LPS), and its properties exhibit various endotoxic and biological effects toward host cells. We examined whether Toll-like receptors (TLRs) are mediated by the signals from various synthetic acylated derivatives of d-glucosamine monophosphate. All test synthetic monosaccharide lipid A analogues similar to acylated beta-(1-6)-d-glucosamine disaccharide bisphosphates, such as Escherichia coli-type lipid A (compound 506) and its precursor (compound 406), clearly induced nuclear factor (NF)-kappaB activation in Ba/F3 cells expressing murine TLR4 and its accessory protein MD-2 (Ba/mTLR4/mMD-2), but no induction was found in those expressing murine TLR2 (Ba/mTLR2). Compound 411, the non-reducing sugar moiety of compound 506, exhibited interleukin-8 (IL-8) and tumour necrosis factor-alpha (TNF-alpha)-producing activities in human peripheral blood mononuclear cells (PBMC), whereas compound 401, the reducing moiety of compounds 506 and 406, and Gifu lipid A-46 (GLA-46), the non-reducing moiety of compound 406, induced no production of IL-8 and TNF-alpha, which was similar to the findings for compound 406. Among the synthetic triacylated monosaccharide lipid A analogues, some compounds with three tetradecanoyl (C14) groups or that included a dodecanoyl (C12) group were more active toward murine and human cells than were other analogues with a decanoyl (C10) or hexadecanoyl (C16) group. Furthermore, IL-8 production in PBMC stimulated with the active monosaccharide lipid A analogues as well as compound 506 was clearly inhibited by the monoclonal antibody to human TLR4. These findings suggest that monosaccharide lipid A analogues similar to disaccharide lipid As are capable of activating both murine and human cells through TLR4.

Animals↗

PubMed2004

UDP-sugar pyrophosphorylase with broad substrate specificity toward various monosaccharide 1-phosphates from pea sprouts.

UDP-sugars, activated forms of monosaccharides, are synthesized through de novo and salvage pathways and serve as substrates for the synthesis of polysaccharides, glycolipids, and glycoproteins in higher plants. A UDP-sugar pyrophosphorylase, designated PsUSP, was purified about 1,200-fold from pea (Pisum sativum L.) sprouts by conventional chromatography. The apparent molecular mass of the purified PsUSP was 67,000 Da. The enzyme catalyzed the formation of UDP-Glc, UDP-Gal, UDP-glucuronic acid, UDP-l-arabinose, and UDP-xylose from respective monosaccharide 1-phosphates in the presence of UTP as a co-substrate, indicating that the enzyme has broad substrate specificity toward monosaccharide 1-phosphates. Maximum activity of the enzyme occurred at pH 6.5-7.5, and at 45 degrees C in the presence of 2 mm Mg(2+). The apparent K(m) values for Glc 1-phosphate and l-arabinose 1-phosphate were 0.34 and 0.96 mm, respectively. PsUSP cDNA was cloned by reverse transcriptase-PCR. PsUSP appears to encode a protein with a molecular mass of 66,040 Da (600 amino acids) and possesses a uridine-binding site, which has also been found in a human UDP-N-acetylhexosamine pyrophosphorylase. Phylogenetic analysis revealed that PsUSP can be categorized in a group together with homologues from Arabidopsis and rice, which is distinct from the UDP-Glc and UDP-N-acetylhexosamine pyrophosphorylase groups. Recombinant PsUSP expressed in Escherichia coli catalyzed the formation of UDP-sugars from monosaccharide 1-phosphates and UTP with efficiency similar to that of the native enzyme. These results indicate that the enzyme is a novel type of UDP-sugar pyrophosphorylase, which catalyzes the formation of various UDP-sugars at the end of salvage pathways in higher plants.

Amino Acid Sequence↗

PubMed1998

Analysis of Monosaccharides Derivatized with 2-aminoacridone by Capillary Electrophoresis.

A new method for simultaneous analysis of 11 monosaccharides with reducing ends derivatized with 2-aminoacridone (AMAC) by the capillary electrophoresis in 300 mmol/L borate, pH 10.5 or 100 mmol/L disodium tetraborate and a pH 10.5 buffer was described. The chemical derivatization was performed at 45 degrees for 5 h, and then the derivatized monosaccharides were separated by capillary electrophoresis and detected at 264 nm. The chemical derivatization limit was 10 &mgr;mol/L. Concentration and mass detection limits of 0.6 &mgr;mol/L and 17 fmol, respectively, could be achieved. The linear correlation coefficients between the quotient of each integrated peak area divided by retention time and the concentration of monosaccharide were all greater than 0.992 (n=6) for the 11 monosaccharides in concentration ranging from 5 to 25 &mgr;mol/L. The relationship between the electrophoretic mobility of the derivatives and the structure of sugar moieties was discussed. The carbohydrate components of several glycoproteins were also by the method described above.

Journal Article↗

PubMed1981

Anomeric specificity of the monosaccharide carrier in yeasts and yeast-like organisms.

The anomeric specificity of monosaccharide uptake was investigated in 42 species of yeasts and related mycelium-forming fungi. Differences in the uptake of anomers were determined by the following methods. (1) Shift of anomeric equilibrium in the outer medium caused by preferential uptake of one of the anomeric forms was monitored polarimetrically as induced mutarotation. (2) The uptake of 14C-D-glucose by cells was examined after addition of freshly prepared solutions of alpha- or beta-D-glucose. Most of the organisms examined display the Saccharomyces-type preference for the alpha-anomers of glucose and xylose which is caused by the higher affinity of the monosaccharide carrier for the alpha-pyranose configuration. The following genera show this type of preference (the number of species is given in parenthesis): Saccharomyces (5), Schizosaccharomyces (1), Endomycopsis (2), Eremascus (1), Endomyces (1), Pichia (1), Hansenula (1), Debaryomyces (2), Lipomyces (1), Willia (1), Nematospora (1), Kluyveromyces (2), Candida (5), Torulopsis (5), Cryptococcus (1). No anomeric specificity was shown by the following genera: Nadsonia (1), Dipodascus (2), Rhodotorula (5), Sporobolomyces (2), Bullera (1), Rhodosporidium (1). A parallel investigation of the concentration dependence of glucose uptake indicates that most yeasts possess a constitutive monosaccharide carrier characterized by the following features: a high maximum rate of uptake, a relatively low affinity, and preference for alpha-anomers. Besides this carrier the majority of these microorganisms possess a glucose-transporting carrier with a higher affinity and a lower capacity.

Biological Transport, Active↗

PubMed1997

Novel monosaccharides as potent inhibitors of cell proliferation.

The effects of several novel monosaccharides upon thymidine incorporation into both normal and tumour cells were investigated. The monosaccharide 2-deoxy-3-[1-(R)-(ethoxycarbonyl)ethyl]- alpha-D-allo-pyranose had the most inhibitory effect on proliferation, with the (S)-enantiomer having less inhibitory effects. The chiral centre at carbon-7 was found to be an important part of the molecule, as 2-deoxy-3-[methoxycarbonyl methyl]-alpha-D-allo-pyranose had greatly decreased anti-proliferative properties in comparison with the parent compound. In addition, the 2-deoxy structure at carbon-2 was also found to be important, as 3-[1-(S)-(ethoxycarbonyl)ethyl]-alpha-D-allo-hexopyranose had greatly decreased inhibitory properties in comparison with the parent compound. The results indicate that these novel monosaccharides possess potent anti-proliferative properties, related to their chiral carbon-7 and 2-deoxy carbon-2 structure and suggest that further substitutions of the functional group at carbon-7 may improve these properties and possibly produce inhibitor selectivity for tumour cells in preference to normal cells.

Animals↗

PubMed2001

A hydrogen-bonding receptor that binds cationic monosaccharides with high affinity in methanol.

A dicarboxylate host (1) binds cationic monosaccharides such as D-glucosamine HCl (2), D-galactosamine-HCl (3), and D-mannosamine-HCl (4) with high affinity (K1 = 8.0 x 10(4)-2.0 x 10(5) M(-1)) in methanol. In circular dichroism (CD) spectroscopy a positive exciton-coupling band was observed near 290 nm; this indicates that the saccharides are recognized by multiple point interactions. Since the corresponding neutral monosaccharides are not significantly bound, one may conclude that complex formation is primarily due to the electrostatic interaction between NH3+ in the guest and one carboxylate in the host and secondarily due to hydrogen-bonding interactions of OH groups with the other carboxylate and/or nitrogen bases. Molar ratio plots and Job plots indicate that host 1 and cationic monosaccharide guests form CD-active, pseudo-cyclic 1:1 complexes at low guest concentration followed by the formation of CD-silent, acyclic 1:2 1-saccharide complexes at high guest concentration. The possible binding modes are discussed in detail on the basis of molecular mechanics calculations and chemical shift changes in 1H NMR spectra. The results of competition experiments with several cationic reference compounds bearing fewer OH groups than 2-4 are consistent with the proposed binding model. Thus, the present study is a rare example of saccharide recognition in a protic solvent, where in general, hydrogen-bonding interactions are rarely useful because of strong solvation energy. These are apparently the strongest saccharide complexes involving noncovalent interactions between host and guest. We believe that the findings are significant as a milestone toward development of new saccharide recognition systems ultimately useful in aqueous solution.

Carrier Proteins↗

PubMed1998

Separation of 1-phenyl-3-methyl-5-pyrazolone derivatives of monosaccharides by capillary electrochromatography.

1-Phenyl-3-methyl-5-pyrazolone (PMP) derivatives of component monosaccharides in glycoproteins (fucose, galactose, mannose, N-acetylgalactosamine and N-acetylglucosamine) and epimeric aldopentoses (arabinose, lyxose, ribose and xylose) were well separated from each other by capillary electrochromatography on a Hypersil ODS column with a mixture of 50 mM N-(2-hydroxyethyl)piperazine-2'-(2-ethanesulfonic acid) buffer, pH 6.0 to approximately 6.3, and acetonitrile (2.2:1 v/v) as eluent. The elution of these compounds showed relatively strong dependence on the pH and concentration of the buffer salts contained in the eluent, as compared to the elution by pressure-driven high-performance liquid chromatography (HPLC) on the same stationary phase, but separation of PMP-monosaccharides was better than that by HPLC. Retention times of PMP-monosaccharides were highly reproducible with a relative standard deviation (RSD) of approximately 0.6%, and quantification with an RSD less than 5% could be achieved using 3-O-methylglucose as an internal standard.

Antipyrine↗

PubMed2006

Chiral resolution of monosaccharides as 1-phenyl-3-methyl-5-pyrazolone derivatives by ligand-exchange CE using borate anion as a central ion of the chiral selector.

Six reducing monosaccharides (mannose, galactose, fucose, glucose, xylose, and arabinose) were derivatized with 1-phenyl-3-methyl-5-pyrazolone (PMP) and chiral resolution of these racemic PMP-monosaccharides was studied by ligand-exchange CE using borate anion as a central ion of the chiral selector and (S)-3-amino-1,2-propanediol (SAP) as a chiral selector ligand. PMP-mannose, PMP-galactose and PMP-fucose were successfully enantioseparated. Lowering the capillary temperature increased the resolution of PMP-mannose system, but decreased that of PMP-galactose and PMP-fucose systems. Whereas the maximum resolution was obtained at pH 8.9 in the PMP-mannose system, resolution increased gradually with pH in the PMP-galactose and PMP-fucose systems. Expecting the formation of the ternary borate complexes with SAP and PMP-monosaccharide in the CE experiments, the optimized structures of the borate diastereomers were obtained by semiempirical molecular orbital calculations to discuss the structural difference of the diastereomers in connection with the enantioseparation behaviors.

Anions↗

PubMed1988

Effects of fusarenon-X and T-2 toxin on intestinal absorption of monosaccharide in rats.

In order to delineate the effects of Fusarenon-X (FX) and T-2 toxin (T-2) on intestinal absorption of monosaccharide, jejunal absorption in vivo and uptake in vitro of 3-0-methyl glucose (m-glucose) and L-glucose were studied in rats. Jejunal absorption in vivo was assessed by determining the rate of appearance of the sugars in plasma of the mesenteric vein draining the jejunal segment, which was perfused with the medium containing radiolabelled m-glucose or L-glucose. Jejunal uptake in vitro was assessed by determining the m-glucose or L-glucose uptake by the everted jejunum taken from toxin-treated rats. m-Glucose absorption was reduced 1 or 3 h after either toxin was injected into the jejunal lumen. A reduction of m-glucose absorption was also noted after intravenous injection of the toxins, although the timing and magnitude of the reduction were slightly different from those seen after the luminal injection. These results suggest that both toxins impair the jejunal function relating to monosaccharide absorption in the early stages of intoxication. The reduction in m-glucose absorption was associated with a reduction in L-glucose absorption and unchanged or increased uptake of L-glucose. The active transport component, which was indicated by the difference between absorption or uptake of the two sugars, was also reduced in association with the reduction of m-glucose absorption. These results suggest that the toxins cause specific damage in the active transport system for monosaccharides on the one hand, and impairment of their diffusional movement from the epithelial layer to the mesenteric vein on the other.

3-O-Methylglucose↗

PubMed1988

The effect of monosaccharides on in situ hepatic trapping of Candida albicans.

The initial clearance of Candida albicans in situ by hepatic tissue was investigated using the isolated perfused mouse liver model in combination with various monosaccharides. When 10(6) yeasts were infused into untreated ICR mouse livers, approximately 61 +/- 2% (mean + SEM) were recovered from the liver and 13 +/- 2% in the effluent for a total recovery of 74 +/- 2%. This suggests that 26 +/- 2% of the infused yeasts were eliminated within the liver and that a total of 87 +/- 1% were trapped (% in the liver + % killed) by the liver. In contrast, when either D-mannose or alpha-methyl-D-mannoside, but not glucose, sucrose, lactose or mannitol, were added to perfusion media (1% w/v) the ability of hepatic tissue to trap C. albicans decreased, in a dose-dependent manner, with increasing concentrations of monosaccharide. Decreased trapping was due to the interaction of these monosaccharides with hepatic tissue and not directly with yeasts. The data suggest that one component of in situ hepatic clearance of C. albicans was the binding of mannose containing structures on the surface of yeasts, most probably by hepatic mannose receptors.

Animals↗

PubMed1975

A Na+-independent, phloretin-sensitive monosaccharide transport system in isolated intestinal epithelial cells.

A monosaccharide transport system in addition to the active Na+-dependent system characteristic of the brush border surface of vertebrate intestinal tissue has been identified in isolated chick intestinal epithelial cells. The newly described system differs in several characteristics from the Na+-dependent process, including function in the absence of Na+; a high sensitivity to phloretin, relative insensitivity to phlorizin; different substrate specificity; and a very high KT and Vmax. The system apparently functions only in a facilitated diffusion manner so that it serves to move monosaccharide across the cell membrane down its chemical gradient. An appreciable fraction of total sugar efflux occurs via the Na+-independent carrier from cells which have accumulated sugar to a steady state. Phloretin selectively blocks this efflux so that a normal steady-state sugar gradient of seven- to eightfold is transformed to a new steady-state gradient which is greater than 14-fold. Locus of the new system is tentatively ascribed to the serosal cell surface where it would serve for monosaccharide transfer between enterocyte and lamina propria of the villus.

Animals↗

PubMed1998

Effects of the polyacetate esters of nutrient and nonnutrient monosaccharides on 45calcium efflux and insulin release from perifused rat pancreatic islets.

CONCLUSION: The polyacetate esters of selected nonnutrient monosaccharides represent potential tools for either stimulation of insulin release in noninsulin-dependent diabetes or inhibition of insulin secretion in hyperinsulinemic syndromes. BACKGROUND: The polyacetate esters of several monosaccharides were recently shown to display greater nutritional value or biological efficiency than the corresponding unesterified carbohydrates. METHODS: The effects of seven polyacetate esters of monosaccharides, all tested at a 1.7-mM concentration, on both 45Ca efflux and insulin release were investigated in prelabeled rat pancreatic islets perifused in the presence of 10.0 mM succinic acid dimethyl ester. RESULTS: Both alpha-D-glucose penta-acetate and, to a lesser extent, beta-L-glucose penta-acetate stimulated insulin release. Inversely, alpha-D-galactose penta-acetate, but not beta-D-galactose penta-acetate inhibited insulin secretion evoked by succinic acid dimethyl ester. Esters of carbohydrates which are inhibitors of D-glucose metabolism, such as D-mannoheptulose hexa-acetate and the two anomers of 2-deoxy-D-glucose tetra-acetate also enhanced insulin output, with a preference for the alpha-anomer of 2-deoxy-D-glucose tetra-acetate. Only those esters with positive insulinotropic action augmented 45Ca efflux from the prelabeled islets.

Acetates↗

PubMed2006

Promoter activity of a putative pollen monosaccharide transporter in Petunia hybrida and characterisation of a transposon insertion mutant.

For the growth of the male reproductive cells of plants, the pollen, the presence of sufficient sucrose or monosaccharides is of vital importance. From Petunia hybrida a pollen-specific putative monosaccharide transporter designated PMT1 (for petunia monosaccharide transporter) has been identified previously. The present work provides an in-depth analysis and characterisation of PMT1 in the context of pollen development with the GUS reporter gene and an insertion mutant. The promoter of the pollen-specific putative PMT1 gene has been isolated by inverse PCR and sequenced. Analysis of plants transformed with the promoter-GUS fusion confirmed the specificity of this gene, belonging to the late pollen-specific expressed genes. GUS activity was detected even after 24 h of in vitro pollen germination, at the pollen tube tip. To elucidate the importance of PMT1 for gametophyte development and fertilisation, we isolated a mutant plant containing a transposon insertion in the PMT1 gene by the dTph1 transposon-tagging PCR-based assay. The PMT1 mutant contained a dTph1 insertion in position 1474 bp of the transcribing part of the gene, before the last two transmembrane-spanning domains. Analysis of the progeny of the heterozygous mutant after selfing revealed no alterations in pollen viability and fertility. Mature pollen grains of a plant homozygous for the transposon insertion were able to germinate in vitro in a medium containing sucrose, glucose, or fructose, which indicates that PMT1 is not essential for pollen survival. Several explanations for these results are discussed in the present work.

Amino Acid Sequence↗

PubMed1984

Detection of the Sanfilippo D syndrome by the use of a radiolabeled monosaccharide sulfate as the substrate for the estimation of N-acetylglucosamine-6-sulfate sulfatase.

N-Acetylglucosamine-6-sulfate sulfatase activity was assayed by incubation of the radiolabeled monosaccharide N-acetylglucosamine [1-14C]6-sulfate (GlcNAc6S) with homogenates of leukocytes and cultured skin fibroblasts and concentrates of urine derived from normal individuals, patients affected with N-acetylglucosamine-6-sulfate sulfatase deficiency (Sanfilippo D syndrome, mucopolysaccharidosis type IIID), and patients affected with other mucopolysaccharidoses. The assay clearly distinguished affected homozygotes from normal controls and other mucopolysaccharidosis types. The level of enzymatic activity toward GlcNAc6S was compared with that toward a sulfated disaccharide and a sulfated trisaccharide prepared from heparin. The disaccharide was desulfated at the same rate as the monosaccharide and the trisaccharide at 30 times that of the monosaccharide. Sulfatase activity toward glucose 6-sulfate and N-acetylmannosamine 6-sulfate was not detected. Sulfatase activity in fibroblast homogenates with GlcNAc6S exhibited a pH optimum at pH 6.5, an apparent Km of 330 mumol/liter, and inhibition by both sulfate and phosphate ions. The use of radiolabeled GlcNAc6S substrate for the assay of N-acetylglucosamine-6-sulfate sulfatase in leukocytes and skin fibroblasts for the routine enzymatic detection of the Sanfilippo D syndrome is recommended.

Cells, Cultured↗

PubMed1976

Stimulation of the gerbil's gustatory receptors by monosaccharides.

The gustatory responses of the Mongolian gerbil were tested with a large number of monosaccharides. Electrophysiological methods were used to record from the chorda tympani nerve. Methyl glycosides which have structural features in common with sucrose are the most effective monosaccharides for eliciting a neural response. Among the monosaccharides tested, efficacy appears to be highest in D-pyranosides having equatorial substituents at the C-2 and C-4 positions and axial substituents at the C-1 position. A C-5 hydroxymethyl group is not required. Similarities in the structural requirements for taste response in the fly and gerbil are discussed.

Animals↗