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PubMed1986

Quantification of 2-keto-3-deoxyoctonate in (lipo)polysaccharides by methanolytic release, trifluoroacetylation and capillary gas chromatography.

Several conditions of acidic anhydrous methanolysis were examined to optimize the release and minimize the degradation of unphosphorylated 2-keto-3-deoxy-D-manno-octonic acid (KDO) from bacterial lipopolysaccharides and polysaccharides. The reaction was monitored by capillary gas chromatography after derivatization by trifluoroacetic anhydride. The best results were obtained by use of 2 M hydrochloric acid at 60 degrees C for 2 h. Under these conditions a single KDO component appeared, and KDO was quantitatively released from all model compounds except when glycosidically linked to hexosamines. For quantitative cleavage of this linkage a reaction time of 6 h was required at 60 degrees C, giving rise to 5-10% of secondary KDO products. The KDO detection limit was about 250 pmol (50 ng) and the molar response was the same as for glucose. The KDO derivative gave a mass spectrometric fragmentation pattern consistent with a pyranosidic methylketoside methyl ester structure. Differentiation of KDO linkage types could be obtained by determination of the rates of KDO release by mild methanolysis.

Chemical Phenomena↗
PubMed1986

Simultaneous determination of N-acetylglucosamine, N-acetylgalactosamine, N-acetylglucosaminitol and N-acetylgalactosaminitol by gas-liquid chromatography.

A gas-liquid chromatographic procedure is described which will concomitantly separate and quantitate N-acetylglucosamine, N-acetylgalactosamine, N-acetylglucosaminitol and N-acetylgalactosaminitol in a single analytical run. The hexosamines, as their O-methyloximes, and the hexosaminitols can be separated as either their per-O-acetylated or per-O-trimethylsilylated derivatives. This method is particularly useful with samples that possess both N-acetylhexosaminitols and N-acetylhexosamines as are seen with N-linked oligosaccharides that are cleaved from glycoproteins by alkaline borohydride treatment. This procedure demonstrates a range of acceptable linearity of 1-1000 nmoles for each type of amino sugar.

Acetylgalactosamine↗
PubMed2000

Analysis of glycosaminoglycan monosaccharides by capillary electrophoresis using indirect laser-induced fluorescence detection.

Two methods for monosaccharide analysis by capillary electrophoresis (CE) using counterelectroosmotic and coelectroosmotic modes with indirect laser-induced fluorescence detection were optimised and compared. A mixture of seven glycosaminoglycan-derived hexoses was separated in alkaline fluorescein-based electrolytes and detected in both counterelectroosmotic and coelectroosmotic conditions. The fluorescein concentration and pH of the background electrolyte, and the influence of the reversal of electroosmotic flow by addition of hexadimethrine bromide on the separation were studied. Coelectroosmotic CE conditions provided better resolution and limits of detection. A 10(-6) M fluorescein solution at pH 12.25 containing 0.0005% (w/v) hexadimethrine bromide was used as background electrolyte. Quality parameters such as run-to-run, day-to-day precision and limits of detection were calculated, and better figures of merit were obtained for the coelectrooosmotic conditions than for the counterelectroosmotic mode. The coelectroosmotic method was applied to the quantitation of the hexosamine contents in glycosaminoglycans after acid hydrolysis. The method proved to be suitable for the determination of dermatan sulfate in heparin down to 2% (w/w).

Electrophoresis, Capillary↗
PubMed1998

Glucosamine infusion in rats mimics the beta-cell dysfunction of non-insulin-dependent diabetes mellitus.

Sustained hyperglycemia can cause peripheral insulin resistance and pancreatic beta-cell dysfunction and has been termed glucose toxicity or glucose-induced desensitization. Glucosamine, a product of glucose flux through the hexosamine biosynthetic pathway (HBP), causes insulin resistance in peripheral tissues and has been shown to cause abnormal glucose-insulin secretion coupling, and thus has been implicated in the pathogenesis of glucose toxicity. Here, we investigate whether glucosamine-induced insulin secretory dysfunction is specific to glucose or also extends to nonglucose secretagogues such as arginine. Two groups of 12 weight-matched Sprague-Dawley rats underwent hyperglycemic clamp studies (steady-state blood glucose, approximately 220 mg x dL(-1)) during infusion of normal saline or glucosamine 3.5 mg x kg(-1) x min(-1) over a 100-minute period. Insulin levels were measured at baseline and between 90 and 100 minutes. One hundred minutes into the hyperglycemic clamp, subgroups of seven rats each (saline- and glucosamine-infused rats) received a bolus of arginine (100 mg x kg(-1)) while the glucose infusion rate was unaltered. Glucose and insulin levels were measured at 1, 3, 5, 10, 15, and 30 minutes after the arginine bolus. Both groups had similar fasting glucose and insulin levels. At steady state (60 to 100 minutes), glucose levels were almost identical in both groups (223.58+/-3.94 v 224.58+/-4.34 mg x dL(-1)), but the glucose infusion rate (26.55+/-1.60 v 8.83+/-1.35 mg x kg(-1) x min(-1), P < .0001) and insulin level (41.36+/-6.47 v 18.04+/-2.95 mU x mL(-1), P < .0001) were markedly reduced in animals receiving glucosamine. Peak insulin levels 1 minute after the arginine bolus were lower in rats infused with glucosamine versus saline (274.00+/-30.38 v 176.25+/-20.12 microU x ml(-1), P=.0319). Total insulin secretion in response to arginine was significantly lower in the glucosamine group as determined by the area under the curve (1,268.09+/-142.27 v 706.77+/-84.79 microU x mL(-1) x min, P=.0054). In conclusion, glucosamine causes severe impairment in glucose-induced insulin secretion. Further, glucosamine-induced beta-cell secretory dysfunction extends to nonglycemic stimuli like arginine. This pattern of insulin secretory dysfunction is similar to that observed in patients with non-insulin-dependent diabetes mellitus (NIDDM). These data suggest that glucosamine may participate in the pathogenesis of glucose toxicity at the level of the beta cell in NIDDM patients.

Animals↗
PubMed1999

Differential effects of troglitazone and D-chiroinositol on glucosamine-induced insulin resistance in vivo in rats.

Troglitazone and D-chiroinositol have been shown to exert antidiabetic effects by either potentiating or mimicking insulin action. We studied whether pretreatment with these compounds can prevent the deleterious effects of glucosamine on insulin action that may play an important role in hyperglycemia-induced insulin resistance. Normal Wistar rats were pretreated with troglitazone (100 mg/kg/d), D-chiroinositol (100 mg/kg/d), or placebo (saline) for 7 days. Glucosamine (50 micromol/kg/min) was then infused for 210 minutes, and a euglycemic glucose clamp was performed during the last 120 minutes. Pretreatment with troglitazone or D-chiroinositol had no effect on fasting plasma glucose or insulin or basal hepatic glucose output (HGO). Under the euglycemic-hyperinsulinemic (956+/-93 pmol/L) clamp condition, HGO in glucosamine-infused placebo-treated rats was not suppressed, but instead was increased over the basal level, indicative of hepatic insulin resistance. In contrast, HGO failed to increase during glucosamine infusion in rats pretreated with troglitazone but was not normally suppressed. This may indicate a partial improvement in the hepatic insulin resistance. D-Chiroinositol pretreatment had no effect on the glucosamine-induced increase in HGO. The glucose disposal rate (GDR) was 25% lower in rats infused with glucosamine versus saline-infused rats (25.5+/-2.5 v 34.1+/-2.0 mg/kg/min), indicative of peripheral insulin resistance. Pretreatment with D-chiroinositol (34.5+/-2.3 mg/kg/min) prevented the glucosamine-induced decrease in the GDR, indicating an improvement in peripheral insulin resistance. Troglitazone (25.2+/-3.3 mg/kg/min) was without effect. In conclusion, (1) in normal control rats, glucosamine infusion induced hepatic and peripheral insulin resistance; (2) D-chiroinositol, but not troglitazone, pretreatment prevented glucosamine-induced peripheral insulin resistance; and (3) troglitazone, but not D-chiroinositol, partially blocked the glucosamine-induced hepatic insulin resistance. D-Chiroinositol may provide a novel pharmacological approach to hexosamine-induced peripheral insulin resistance.

Animals↗
PubMed1983

Lectins in the unicellular Tetrahymena. II. Impact of nutrition and sugar treatment on anti-lectin binding.

Tetrahymena pyriformis GL cells showed partly intracytoplasmic, partly intramembraneous accumulation of lectin-like proteins in conditions of starvation, as demonstrated cytochemically by reaction with antibodies to pea, lens, bean, Datura, and snail lectin. The lectins binding to simple sugars tended to accumulate in the membrane, whereas those capable of interacting with hexosamines in the cytoplasm. While the fluorescence pattern of lectin localization was generally homogeneous in normally nourished cells, it assumed a variegated appearance in starved cells, owing to patching of the membrane, and spot-like accumulation of lectins in the cytoplasm, presumably within membranes of endocytosed vesicles. Snail lectin was an exception, since its distribution remained homogeneous also in conditions of starvation.

Animals↗
PubMed1983

Ultrastructural localization of complex carbohydrates present in the sublingual gland of rabbits.

Stainings with dialized iron (DI), high-iron diamine-thiocarbohydrazide-silver proteinate HID-TCH-SP), tannic acid-uranylacetate (TA-U), tannic acid-ferric chloride (TA-F), and periodate-thiocarbohydrazide-silver proteinate (PA-TCH-SP) were applied to samples of sublingual glands of rabbits. Comparing the results obtained with what had been previously demonstrated biochemically, it is possible to assert that the faintly electron-opaque, granules of the cells of the preterminal tracts contain sulphated glycoconjugates because of the presence of sulphated hexosamines and hexoses, acid glycoconjugates because of the presence of sialic acid and uronic acids, and neutral glycoconjugates because of the presence of hexoses.

Animals↗
PubMedDate not supplied

Some structural studies on the galactose-containing polysaccharide from bovine placenta.

Polysaccharides were extracted from 8-month-old placenta with aqueous HgCl2. The protein-free material was purified by selective precipitation with Cetavlon in the presence of sodium borate at pH 8.5 and was homogeneous on molecular-sieve chromatography, electrophoresis, and on treatment with Concanavalin A. The preparation contained galactose and glucose as principal monosaccharides with 5 per cent of hexosamines. Methylation studies suggested that D-gluco and D-galactopyranosyl units may be constituents of glucan and galactan respectively which form a molecular aggregate that does not dissociate during the fractionation procedures. After treatment of the fraction with beta-amylase, the proportion of glucose in the polysaccharide diminished, indicating the presence of (1-->4)-linked alpha-D-glucopyranosyl residues. Also, when the fraction was treated with a crude protease having glucosidase activity a residual alpha-D-galactopyranan was isolated and found to contain non-reducing end-groups (30.0 per cent), 3-O-(39.5 per cent) and 3,6-di-O-substituted (30.5 per cent) units. The structure of the galactan was not modified according to methylation data, on removal of the glucosyl component. The polysaccharide fraction (pH 8.5 Cetavlon), isolated from bovine placenta, thus contains a glycogen-like material associated with a galactan as molecular aggregate. This galactan has not been previously recognized in bovine placenta and its occurrence in this organ supports the hypothesis that galactose-containing polysaccharides are involved in foetal development.

Animals↗
PubMed2002

Glucosamine-6-phosphate synthase--the multi-facets enzyme.

L-Glutamine: D-fructose-6-phosphate amidotransferase, known under trivial name of glucosamine-6-phosphate synthase, as the only member of the amidotransferase subfamily of enzymes, does not display any ammonia-dependent activity. This enzyme, catalysing the first committed step in a pathway leading to the eventual formation of uridine 5'-diphospho-N-acetyl-D-glucosamine (UDP-GlcNAc), is an important point of metabolic control in biosynthesis of amino sugar-containing macromolecules. The molecular mechanism of reaction catalysed by GlcN-6-P synthase is complex and involves both amino transfer and sugar isomerisation. Substantial alterations to the enzyme structure and properties have been detected in different neoplastic tissues. GlcN-6-P synthase is inflicted in phenomenon of hexosamine-induced insulin resistance in diabetes. Finally, this enzyme has been proposed as a promising target in antifungal chemotherapy. Most of these issues, especially their molecular aspects, have been extensively studied in recent years. This article provides a comprehensive overview of the present knowledge on this multi-facets enzyme.

Amino Acid Sequence↗
PubMed1998

Isolation, properties and N-terminal amino acid sequence of a factor V activator from Vipera lebetina (Levantine viper) snake venom.

A factor V activator (VLFVA) was separated from Vipera lebetina venom by gel filtration on Sephadex G-100 superfine, followed by chromatography on CM-cellulose and on heparin-agarose. This enzyme (VLFVA) with a molecular mass of 28.4 kDa, as determined by matrix assisted laser desorption ionization time-of-flight mass spectrometry, is a single-chain glycoprotein containing seven residues of neutral sugars, seven residues of hexosamines and three residues of neuraminic acid per molecule. The treatment with N-glycosidase F lowered the molecular mass approximately 6%. The N-terminal sequencing of VLFVA up to the 30th residue evidenced a high homology with Vipera russelli factor V activator RVV-Vgamma (90% identity). Aside from factor V, no other protein substrate for VLFVA has yet been identified. VLFVA hydrolyzes several synthetic arginine ester substrates, such as benzoylarginine ethyl ester (BAEE), tosylarginine methyl ester (TAME) and amide substrates such as Pro-Phe-Arg-MCA. The arginine ester hydrolase activity of the enzyme is markedly lower than that of the crude venom. The ability of VLFVA to activate factor V and its activity to BAEE and TAME were inhibited by the serine proteinase inhibitor, diisopropylfluorophosphate. VLFVA is thermostable protein, heating for 20 min at 70 degrees C does not alter the arginine esterase activity of the enzyme.

Amino Acid Sequence↗
PubMed1999

Purification and characterisation of a minor low-sulphated dermatan sulphate-proteoglycan from ray skin.

A minor low-sulphated dermatan sulphate proteoglycan was isolated from ray skin by extraction with 2% sodium dodecyl sulphate, followed with ion-exchange chromatography, gel chromatography and density gradient centrifugation. The proteoglycan with a relative molecular mass (Mr) ranging from 70 to 120 kDa is composed of about two dermatan sulphate chains (Mr 33 kDa) bound on a protein core of Mr 27 kDa, and oligosaccharides consisting of uronic acids, hexosamines and neutral sugars. The major amino acids of the protein core were glycine (corresponding to about one-fourth of the total amino acids), serine, threonine, glutamic acid/glutamine, leucine and cysteine, together amounting to 56% of the total. The isolated proteoglycan does not interact with hyaluronic acid and does not form self-aggregates. Dermatan sulphate was rich in iduronic acid (62% of total uronic acid) and composed of non-sulphated (44%), and mono-sulphated disaccharides bearing esterified sulphate groups at positions C-4 (53%) or C-6 (3%) of the N-acetyl galactosamine. HPLC analysis of a pure preparation of dermatan sulphate, showed the presence of galactose and glucose possibly as branches on the dermatan sulphate chain.

Amino Acids↗
PubMed2003

The effect of nerve growth factor on the early responses during the process of wound healing.

In this study, we investigated the role of nerve growth factor (NGF)-incorporated collagen on wound healing in rats. Full-thickness excision wounds were made on the back of female rats weighing about 150-160 g. Topical application of NGF-incorporated collagen, at a concentration of 1 microg/1.2 mg collagen/cm(2), once a day, for 10 days resulted in complete healing of wounds on the 15th day. The concentrations of collagen, hexosamine and uronic acid in the granulation tissue were determined. The NGF-incorporated collagen-treated rats required shorter duration for the healing with an increased rate of wound contraction. Histological and electron microscopical evaluations were also performed, which reveal the activation of fibroblasts and endoplasmic reticulum and therefore increased level of collagen synthesis due to NGF application. These results clearly indicate that the topical application of NGF-incorporated collagen enhanced the rate of healing of excision wounds.

Administration, Topical↗
PubMed2000

Organic compounds in the extrapalial fluid and haemolymph of Anodonta cygnea (L.) with emphasis on the seasonal biomineralization process.

Bivalve mollusks, such as the freshwater mussel Anodonta cygnea, show seasonal changes in calcification. This cycle of calcification must either be a cause or a consequence for seasonal fluctuations in the organic composition of the animal's fluids, haemolymph and extrapallial fluid, the liquid media for biomineralization. We monitored the fluids of A. cygnea, throughout a 1-year cycle, for the presence of organic constituents, known to be important for biomineralization, such as proteins, glycosaminoglycans (GAGs) and hexosamines. Proteins were subjected to further study, namely through the total amino acid determination and fraction separation by agarose gel electrophoresis. GAG levels were fairly constant throughout the year, with a maximum concentration in July and a minimum in January, a feature also detected for glucosamine, although with higher fluctuations. Proteins showed highly increased concentrations during June and July, both in total amounts and individual fractions. All fractions showed similar trends throughout the year, with lowest general levels in October, the starting month of a period when some fractions were not detectable at all. All fractions ended this low period in May, when a sometimes-important increase could be detected. As to the total amino acid composition of the fluids, the general trend followed that of proteins, except for ornithine (Orn), a non-proteic amino acid. The overall fluctuations detected in the biological fluids of A. cygnea suggest that the main variation related to the calcification cycle must be quantitative, since no different compounds appear in specific periods, to achieve also specific results.

Amino Acids↗
PubMed2003

Effect of naturally occurring allyl and phenyl isothiocyanates in the inhibition of experimental pulmonary metastasis induced by B16F-10 melanoma cells.

The effect of naturally occurring allyl and phenyl isothiocyanates in the inhibition of B16F-10 melanoma cells-induced metastasis has been studied in C57BL/6 mice. The two compounds were administered by three different modalities. Simultaneous administration of the compounds with tumour induction was found to produce significant reduction in the lung tumour nodule formation; of the two compounds studied, allyl isothiocyanate have shown to be more effective and it produced 93% inhibition of tumour nodules while phenyl isothiocyanate has an inhibition of 77.3%. Prophylactic administration also produces considerable effect but no effect was observed by their administration after the tumour development. Lung collagen hydroxyproline, lung uronic acid, lung hexosamine content, serum sialic acid and serum GGT levels were also estimated and the enhanced levels of these parameters in the control animals were found to be reduced by the simultaneous administration of these isothiocyanates; these data were also correlated with the inhibition of lung tumour nodules produced and the increase in life span of the animals.

Animals↗
PubMed2003

Extracellular polymeric substances responsible for bacterial adhesion onto solid surface.

The influence of extracellular polymeric substances (EPS) on bacterial cell adhesion onto solid surfaces was investigated using 27 heterotrophic bacterial strains isolated from a wastewater treatment reactor. Cell adhesion onto glass beads was carried out by the packed-bed method and the results were discussed in terms of the amount of each EPS component produced and cell surface characteristics such as zeta potential and hydrophobicity. Protein and polysaccharides accounted for 75-89% of the EPS composition, indicating that they are the major EPS components. Among the polysaccharides, the amounts of hexose, hexosamine and ketose were relatively high in EPS-rich strains. For EPS-poor strains, the efficiency of cell adhesion onto glass beads increased as the absolute values of zeta potential decreased, suggesting that electrostatic interaction suppresses cell adhesion efficiency. On the other hand, the amounts of hexose and pentose exhibited good correlations with cell adhesiveness for EPS-rich strains, indicating that polymeric interaction due to the EPS covering on the cell surface promoted cell adhesion. It was concluded that, if the EPS amount is relatively small, cell adhesion onto solid surfaces is inhibited by electrostatic interaction, and if it is relatively large, cell adhesion is enhanced by polymeric interaction.

Bacteria↗
PubMed2000

Cloning and characterization of mouse glutamine:fructose-6-phosphate amidotransferase 2 gene promoter.

Glutamine:fructose-6-phosphate amidotransferase (GFAT) is the first and rate-limiting enzyme of the hexosamine biosynthesis pathway, which plays an important role in glucose toxicity and cellular insulin resistance. Thus, the mechanisms by which GFAT expression is regulated under physiological and pathological conditions are of interest in connection with diabetes. In this study, we cloned the 5'-flanking region of the mouse GFAT2 gene and characterized its promoter activity. Sequence analysis revealed several putative regulatory elements Sp1, a CCAAT box, AP-1 and AP-2, but no TATA box. Transfection experiments showed that the 5'-flanking region between -2462 to +38 relative to the transcription start site of the GFAT2 gene drives transcription in NIH3T3 cells and that the fragment from -141 to -9 has the highest transcription activity. Reporter assays using deletion and mutant variants suggested that the Sp1 sites at positions -83 to -78 and -22 to -17 both play an important role in the basal promoter activity of the mouse GFAT2 gene. Electrophoretic mobility shift assay showed DNA-protein binding at both Sp1 sites. We also compared the promoter activities of mouse GFAT1 and GFAT2 in several cell lines.

3T3 Cells↗
PubMed2002

Healing potential of Datura alba on burn wounds in albino rats.

Datura alba Nees (Solanaccae) is popular all over the world for its medicinal uses in asthma, muscle spasm, whooping cough, hemorrhoids, skin ulcers, etc. In India, it is widely used traditionally for the relief of rheumatism and other painful affections. Ayurveda and Siddha practitioners use oil based preparations of this plant from ancient days to till date for all types of wounds. Hence, the present study was chosen to evaluate its scientific validity. The alcohol extract of the D. alba leaves were investigated for the evaluation of its healing efficiency on burn wound models in rats. The crude alcohol extract and one of the fractions exhibited antimicrobial effect against all the pathogens studied. A 10% (w/w) formulation of alcoholic extract was topically applied on thermal wounds. Complete wound closure was observed within 12 days in treated rats. The effect produced by the ointment, in terms of wound contracting ability, wound closure time, tissue regeneration at the wound site and histopathological characteristics were significant in treated rats. Collagen, hexosamine and gelatinase expressions were also well correlative with the healing pattern observed. The present study thus provides a scientific rationale for the traditional use of this plant in the management of wounds.

Animals↗
PubMed1999

Biochemical evaluation of antitumor effect of muthu marunthu (a herbal formulation) on experimental fibrosarcoma in rats.

Natural products from plants are rich sources used for treating a number of diseases. Many of the pharmacological principles of the currently used anticancer agents have been initially isolated from plants. Most of the herbal drugs are a mixture of a number of plant ingredients. Their cumulative effect increases the efficacy of the drug in curing the diseases. Muthu Marunthu is a herbal formulation comprising of eight various plant ingredients, and has been claimed to possess antitumor effect. Therefore, attention has been focused on studying the various plant ingredients in the drug as a whole for its antitumor effects. It was observed that the growth rate in rats was normal and there was no change in blood parameters such as glucose, urea, proteins, cholesterol and also in the activities of pathophysiological enzymes such as lactate dehydrogenase (LDH), glutamate oxaloacetate transaminase (GOT), glutamate pyruvate transaminase (GPT), alkaline and acid phosphatase after Muthu Marunthu administration. The tumor weight was found to be reduced in methylcholanthrene induced fibrosarcoma rats after Muthu Marunthu treatment. Elevated levels of glycocomponents of glycoproteins such as hexose, hexosamine, sialic acid and fucose in plasma of fibrosarcoma rats decreased significantly after Muthu Marunthu treatment. The DNA and RNA levels of liver and kidney, which were increased in fibrosarcoma rats, returned to near normal levels after Muthu Marunthu treatment. The vitamins such as A, C and E in plasma were decreased in fibrosarcoma rats but increased significantly after Muthu Marunthu treatment. The altered levels of copper, zinc and selenium in plasma have also been corrected after Muthu Marunthu treatment. These observations clearly suggested the antitumor potency of Muthu Marunthu in experimentally induced fibrosarcoma in rats.

Animals↗