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PubMed1999

Determination of the oxygen-18/oxygen-16 isotope ratios of sugar, citric acid and water from single strength orange juice.

The ratio of the stable isotopes of oxygen (18O/16O) has been measured in the sugar, citric acid and water from authentic single strength orange juices, originating from a number of different countries. The sugars and citric acid were recovered from the juices and their 18O/16O ratios were determined by pyrolysis/continuous flow-isotope ratio mass spectrometry (Py/CF-IRMS). The 18O/16O ratio of the fruit juice water was determined by the carbon dioxide/water equilibration method. The delta 18O/1000 values of 45 different sugars ranged from +29.1 to +38.8/1000 and 15 citric acids ranged from +18.9 to +25.4/1000. The delta 18O/1000 value of the water present in the same samples ranged from -2.1 to +7.8/1000. A correlation was evident between the delta 18O/1000 values of the sugar, citric acid and water from the juices. This information can be used to improve the assessment of the authenticity of commercial 'freshly squeezed' orange juices. The detection of the presence of reconstituted orange juice concentrate in 'freshly squeezed' orange juices was improved by 37% using regression analysis of the combined water and sugar delta 18O/1000 ratios when compared to the use of delta 18O/1000 ratios of fruit juice water alone.

Beverages↗
PubMed1987

Effect of sugar fatty acid esters on rumen fermentation in vitro.

1. The effect of sugar fatty acid esters (SFEs; currently used as food additives for human consumption) on rumen volatile fatty acids (VFA) and gas production was studied with sheep rumen contents in vitro. 2. Some SFEs having monoester contents of more than 70% increased the molar proportion of propionate in conjunction with reduction in the acetate:propionate ratio when the individual SFE was added to rumen contents in a final concentration of 4 g/l. Laurate sugar ester was the most potent propionate enhancer and rumen gas depressor, the effective dose being as low as 1 g/l in a final concentration. Fatty acid esters other than SFEs had little, if any, effect on rumen VFA production and their molar proportions. 3. Approximately 50% of laurate sugar ester was hydrolysed by in vitro incubation with rumen fluid for 2 h. The addition of fatty acids and sucrose was also effective in the alterations of rumen VFA and gas production. However, the effect of SFEs on in vitro rumen fermentation was significantly greater than that of their constituent fatty acids or sucrose, or both. Accordingly, the effect appeared to be ascribed to the complex action of SFE itself and to its constituents, free fatty acids and sucrose. 4. SFEs, at the level of 4 g/l, reduced substantially the froth formation (ingesta volume increase) and seemed to be effective for the prevention of bloat.

Animals↗
PubMed1986

[Organic acids of various kinds of vegetables. IV. Changes in the acids and sugar in tomatoes, sweet peppers and cucumbers during development and ripening].

Concentrations of organic acids and sugars in tomatoes and sweet peppers change notably during ripening. The concentration of malic acid decreases while that of citric acid increases considerably and in redripe fruits clearly exceeds the content of malic acid. Several maxima and minima in acid concentrations occur during development. Both species show constant proportions of citric and isocitric acid (200:1 and 30:1 respectively). In sweet pepper, quinic and ascorbic acid can be found in noticeably higher amounts than in tomatoes. Additionally, succinic acid was detected in tomatoes and fumaric and shikimic acid in sweet pepper. Glucose and fructose, in approximately equal amounts, are the main sugar components; their concentrations are increased during ripening, especially in sweet peppers. The leaves of tomatoes and sweet pepper contain more malic acid and less citric acid than redripe fruits, though here as well citric acid predominates. There is considerably less glucose and fructose present in the leaves of sweet pepper than in the fruits while sucrose is increased. Sucrose is the main sugar component in the leaves. Compared to tomatoes and sweet peppers, egg-plants contain more amounts. - Potatoes contain citric, malic, quinic, succinic, fumaric, and soluble oxalic acid (in order of decreasing amounts). - In cucumbers malic acid notably exceeds citric acid. Both acids hardly change in concentration during ripening. Sugar content decreases during ripening.

Acids↗
PubMed2003

Turkish Tombul hazelnut (Corylus avellana L.). 1. Compositional characteristics.

The quality of Tombul (Round) hazelnut, grown in the Giresun province of Turkey, was determined by measuring proximate composition, minerals, vitamins, dietary fiber, amino acids, and taste active components (free amino acids, sugars, and organic acids). Fat was the predominant component in Tombul hazelnut (approximately 61%). The major minerals were potassium, phosphorus, calcium, magnesium, and selenium. Hazelnut was also found to serve as an excellent source of vitamin E (24 mg/100 g) and a good source of water soluble (B complex) vitamins and dietary fiber. The major amino acids were glutamic acid, arginine, and aspartic acid. The three nonessential amino acids and the essential amino acids contributed 44.9 and 30.9% to the total amino acids present, respectively, while lysine and tryptophan were the limiting amino acids in Tombul hazelnut. Twenty-one free amino acids, six sugars, and six organic acids were positively identified; among these, arginine, sucrose, and malic acid predominated, respectively. These taste active components may play a significant role in the taste and flavor characteristics of hazelnut. Thus, the present results suggest that Tombul hazelnut serves as a good source of vital nutrients and taste active components.

Amino Acids↗
PubMed1985

Potassium movements associated with amino acid and sugar transport in enterocytes isolated from rabbit jejunum.

Active transport of amino acids and the sugar, alpha-methyl-D-glucoside (alpha-MG) caused an increase in the rate of K efflux from isolated rabbit enterocytes. These effects were inhibited by apamin (5 X 10(-7) M), quinidine (10(-3) M), Ba (5 X 10(-3) M) and trifluoperazine (5 X 10(-5) M) but not by the loop diuretic furosemide (10(-4) M). None of these drugs affected the basal rate of K efflux. The stimulatory effects of amino acids or alpha-MG on K efflux are too great to be explained in terms of an increase in the electrical driving force across the plasma membrane of these cells and a change in membrane permeability is envisaged. An apparent Ca-dependent K permeability in isolated enterocytes can be demonstrated using the Ca ionophore A23187. The effect of the ionophore on K efflux is abolished by apamin or Ba. It is proposed that Ca-dependent K channels mediate the sugar and amino acid induced increases of K efflux. Under control conditions there is a decrease in intracellular K concentration during accumulation of alanine or alpha-MG. Ba by itself does not alter K concentration but it did produce a marked increase when used in conjunction with alanine or alpha-MG. The accumulation of alpha-MG was inhibited in the presence of Ba. This is consistent with an interference with the driving force for sugar accumulation. It is suggested that the increase in K permeability described has a role in both maintaining ion homoeostasis during Na-coupled transport and contributing to the driving force for sugar and amino acid absorption.

Amino Acids↗
PubMed1988

A micromethod for the estimation of oligosaccharides containing glycosidically linked sialic acid or hexoses, or both, in glycoproteins.

The peeling reaction, the process by which oligosaccharides are degraded in alkali, was used as the basis for an assay to provide structural information about glycosidically linked oligosaccharides in glycoproteins. Glycoproteins were treated with 0.05 M NaOH at 50 degrees to induce release, and subsequent degradation ("peeling"), of glycosidically linked, but not of N-glycosydically linked, oligosaccharides. Among the degradation products generated from O-linked chains were three 3-deoxy sugar acids whose formation was correlated with certain structural features of the oligosaccharides. N-Acetylneuraminic acid was released from terminal positions in the oligosaccharides, and iso- and meta-saccharinic acids were derived from the degradation of 4-O- and 3-O-substituted hexoses, respectively. All of these sugar acids were detected colorimetrically by periodate oxidation and reaction of the product with 2-thiobarbituric acid. The ability of the method to generate 3-deoxy sugar acids was tested in 8 alkali-treated glycoproteins. 3-Deoxy sugar acids were detected only in those glycoproteins whose glycosidically linked carbohydrates contained N-acetylneuraminic acid, or 3-O- or 4-O-substituted hexoses, or both. As little as 0.12 microgram of 3-deoxy sugar acid produced from 5 micrograms of human chorionic gonadotropin was sufficient for detection. This method is novel in its ability to distinguish sialylation of glycosidically linked carbohydrates. Furthermore, it combines the specificity of beta-elimination with the sensitivity of the 2-thiobarbituric acid assay in targeting degradation products of the peeling reaction as candidates for an assay method.

Glycoproteins↗
PubMed2000

Gustatory responsiveness to food-associated sugars and acids in pigtail macaques, Macaca nemestrina.

Taste-preference thresholds for five food-associated sugars and acids, respectively, as well as relative sweet-taste preferences were assessed in six pigtail macaques using two-bottle choice tests of brief duration (1 min). In experiment 1, the animals were found to significantly prefer concentrations as low as 10 mM maltose and sucrose, 20 mM fructose and glucose, and 30 mM lactose over tap water. In experiment 2, the monkeys were given a choice between all binary combinations of the same five saccharides presented in equimolar concentrations of 50, 100, 200, and 400 mM. Preferences for individual sugars were stable across the concentrations tested and indicate the following order of relative effectiveness: maltose>sucrose>glucose> or =fructose> or =lactose. In experiment 3, Macaca nemestrina was found to significantly discriminate concentrations as low as 5 mM malic acid, 10 mM ascorbic acid, 20 mM citric acid and acetic acid, and 0.5 mM tannic acid from the alternative stimulus. With the latter substance, the monkeys rejected all suprathreshold concentrations tested, whereas with the former four substances, the animals showed an inverted U-shaped function of preference. The results showed pigtail macaques to be the first primate species tested so far whose taste-preference threshold for maltose is as low as that for sucrose, and which - similar to rodents - prefers maltose over equimolar concentrations of sucrose and other saccharides. Further, unlike most other primates, pigtail macaques do not generally reject acidic tastants but show a substance- and concentration-dependent change in their behavioral response that may range from rejection to preference. The results support the assumption that the gustatory responsiveness of M. nemestrina to food-associated sugars and acidic tastants might reflect an evolutionary adaptation to its dietary habits.

Acetic Acid↗
PubMed2003

Microwave-mediated analysis for sugar, fatty acid, and sphingoid compositions of glycosphingolipids.

For chemical characterization of glycosphingolipids, it is necessary to determine the chemical compositions of three constituents, i.e., sugars, fatty acids, and sphingoids. A new rapid analytical method is described using a one-pot reaction in a household microwave oven, producing sugars, fatty acids, and especially sphingoids free of by-products, from a single aliquot of a biological sample. Glycosphingolipids were hydrolyzed by microwave exposure with 0.1 M NaOH/CH(3)OH for 2 min followed by 1 M HCl/CH(3)OH for 45 s. The alkaline methanolysis step produced intermediate lysoglycosphingolipids virtually free of by-products such as the O-methyl ethers usually seen. The fatty acid methyl esters were extracted with n-hexane, and other reaction products were dried, taken up in aqueous alkaline methanol, and shaken with chloroform. Sphingoids partitioned into the organic phase under these conditions, whereas the sugar portion that partitioned into the aqueous phase was re-N-acetylated and remethanolyzed for 30 s by microwave exposure. Analysis of the profiles of glycosphingolipid constituents obtained using the microwave oven method showed that they were quantitatively and qualitatively comparable to those obtained by time-consuming conventional methods, which require reaction for several hours. Analysis of the three constituents, including analysis by gas chromatography, may be obtained within 1 day using the method described here.

Acetylation↗
PubMed2002

Sugar amino acids and their uses in designing bioactive molecules.

In search of new molecular entities for discovering new drugs and materials, organic chemists are looking for innovative approaches that try to imitate nature in assembling quickly large number of distinct and diverse molecular structures from 'nature-like' and yet unnatural designer building blocks using combinatorial approach. The main objective in developing such libraries is to mimic the diversities displayed in structures and properties of natural products. The unnatural building blocks used in these assemblies are carefully designed to manifest the structural diversities of the monomeric units used by nature like amino acids, carbohydrates and nucleosides to build its arsenal. Compounds made of such unnatural building blocks are also expected to be more stable toward proteolytic cleavage in physiological systems than their natural counterparts. Sugar amino acids constitute an important class of such polyfunctional scaffolds where the carboxyl, amino and hydroxyl termini provide an excellent opportunity to organic chemists to create structural diversities akin to nature's molecular arsenal. Recent advances in the area of combinatorial chemistry give an unprecedented technological support for rapid compilations of sugar amino acid-based libraries exploiting the diversities of carbohydrate molecules and well-developed solid-phase peptide synthesis methods. This review describes the development of sugar amino acids as a novel class of peptidomimetic building blocks and their applications in creating large number of structurally diverse peptide-based molecules many of which display interesting three-dimensional structures as well as useful biological properties.

Amino Acids↗
PubMed1966

Effect of amino acids on sugar absorption.

1. Sacs of everted mid-small intestine of the hamster have been used to study the effect of amino acids on sugar absorption.2. The sugars employed were D-glucose, D-galactose, 3-O-methyl-D-glucose, D-fucose, L-glucose, alpha-glucoheptose, L-fucose, D-mannose and L-sorbose. The amino acids were L- and D-histidine, L- and D-methionine, L- and D-alanine, L- and D-valine, L- and D-glutamic acid, L-leucine, L-proline, L-ornithine and L-aspartic acid.3. Actively absorbed amino acids considerably inhibit the transport of actively absorbed sugars. The results give support for the view that D-histidine and L-glucose are actively transferred. Passively absorbed amino acids and sugars are not involved.4. As L-glutamic and L-aspartic acids in the mucosal fluid have no inhibitory effect on D-glucose absorption, although mucosal fluid L-alanine is quite potent, the step at which the latter exerts its inhibitory action must be before that at which the intracellular transamination of L-glutamic and L-aspartic acids occurs. It would seem likely, therefore, that L-alanine interferes with the process by which epithelial cells capture and concentrate sugars at the luminal border.5. More than one active transfer system may exist for D-glucose.6. The influence of actively absorbed L-amino acids on D-glucose active transport seems to be in some way related to the efficiency with which the amino acids are themselves concentrated.7. Inhibition of D-glucose active absorption by an amino acid may be a simple test of an amino acid's participation in an active transport system.

Alanine↗
PubMed2005

Sugar amino acids in designing new molecules.

Emulating the basic principles followed by nature to build its vast repertoire of biomolecules, organic chemists are developing many novel multifunctional building blocks and using them to create 'nature-like' and yet unnatural organic molecules. Sugar amino acids constitute an important class of such polyfunctional scaffolds where the carboxyl, amino and hydroxyl termini provide an excellent opportunity to organic chemists to create structural diversities akin to Nature's molecular arsenal. This article describes some of our works on various sugar amino acids and many other related building blocks, like furan amino acids, pyrrole amino acids etc. used in wide-ranging peptidomimetic studies.

Amino Acids↗
PubMed2003

Synthesis of new sugar amino acid derivatives of D-glucosamine.

The synthesis of several new sugar amino acid derivatives of 2-acetamido-2-deoxy-D-glucose, bearing a C-glycosyl functionality as building blocks for the design and synthesis of natural glycoconjugates mimetics, is described. These compounds were prepared from the readily accessible per-benzylated amino C-allyl glucopyranosyl compounds, with TMSOTf/Ac(2)O-mediated selective acetolysis of the 6-O-benzyl group as the key step.

Acetylglucosamine↗
PubMed2003

Solid-phase synthesis of cyclic RGD-furanoid sugar amino acid peptides as integrin inhibitors.

The solid-phase synthesis of cyclic RGD peptides containing either one or two furanoid sugar amino acids (SAAs) is reported. Using a cyclization-cleavage approach five peptides were successfully assembled and consecutively tested on their ability to bind to the integrin receptors alpha(v)beta(3) and alpha(IIb)beta(3). The cyclic tetrapeptide c[RGD-SAA] (1) showed the most promising activity in an inhibition assay with an IC(50) of 1.49 microM for the alpha(v)beta(3) receptor and 384 nM for the alpha(IIb)beta(3) receptor.

Binding, Competitive↗
PubMed2005

Further studies on a mixture of fatty acids from sugar cane (Saccharum officinarum) wax oil in animal models of hypersensitivity.

A mixture of fatty acids obtained from sugar cane wax oil, the main components of which are palmitic, oleic, linoleic and linolenic acids, was evaluated topically in two experimental models of hypersensitivity: the ear swelling response to ovalbumin in sensitized mice (ED50 edema: 0.63 +/- 0.06 mg/ear, ED50 myeloperoxidase: 0.56 +/- 0.04 mg/ear, ED50 degranulated cells: 0.70 +/- 0,08 mg/ear) and oxazolone-induced contact hypersensitivity in mice (ED50 edema: 1.63 +/- 0.26 mg/ear, ED50 myeloperoxidase: 1.50 +/- 0.28 mg/ear, ED50 degranulated cells: 1.69 +/- 0.08 mg/ear). Also, the effect of this mixture was studied on the chemotaxis induced by fmlp (ED50: 25 +/- 3 microg/mL). The mixture showed anti-inflammatory activity in both in vivo models of allergy and in the chemotaxis test. Therefore, these results provide evidence about the potential usefulness of the mixture of fatty acids from sugar cane wax oil in cutaneous inflammatory and allergic disorders.

Animals↗
PubMed1997

Fast separation of underivatized carbohydrates by coelectroosmotic capillary electrophoresis.

A method for the rapid quantitative analysis of underivatized acidic sugars, monosaccharides and disaccharides using coelectroosmotic capillary electrophoresis was developed. Indirect UV detection at 254 nm using sorbate as background electrolyte was employed for monitoring the analytes. A highly alkaline pH value of the electrolyte system was chosen in order to achieve an electrophoretic mobility of the saccharides towards the anode. A dynamic reversal of the electroosmotic flow and, by this means, a codirectional movement of the negatively charged analytes and the electroosmotic flow is accomplished by employing a polycationic surfactant (hexadimethrine bromide), which is added to the background electrolyte. To further improve the resolution of specific carbohydrates, acetone is used as organic modifier. A practical application of the developed method for the fast determination of fructose, glucose, and sucrose in various soft drinks is provided.

Acetone↗
PubMed2004

Physicochemical characterization of a new pineapple hybrid (FLHORAN41 Cv.).

The physicochemical characteristics (pH, total and soluble solids, and titratable acidity), sugars, organic acids, carotenoids, anthocyanins, volatile compounds, and cell wall polysaccharides of a new pineapple hybrid (FLHORAN41 cultivar) were measured throughout maturation and compared with the Smooth Cayenne cv. At full maturity, the FLHORAN41 cv. has a higher titratable acidity and soluble solids content than the Smooth Cayenne cv. The golden yellow flesh and red-orange to scarlet shell of ripe FLHORAN41 cv. fruits are due to carotenoid and anthocyanin levels that are, respectively, 2.5 and 1.5 times higher than those of the flesh and shell of the ripe Smooth Cayenne cv., respectively. During maturation of the FLHORAN41 cv., there was an increase in all classes of aroma compounds (mainly terpene hydrocarbons and esters), although their relative proportions were similar in both cultivars at full maturity. Cell wall polysaccharides undergo little change during maturation.

Ananas↗
PubMed2004

Analysis of transport activity of Arabidopsis sugar alcohol permease homolog AtPLT5.

The transporters responsible for sugar uptake into non-photosynthetic sink tissues in plants, such as roots and flowers, have not been fully identified and analyzed. Plants encode around 100 putative sugar transporters within the major facilitator superfamily, yet only a few have been studied. Here we report the analysis of a sugar alcohol permease homolog (AtPLT5, At3g18830) from Arabidopsis. A wide range of sugars including hexoses, pentoses, tetroses, a sugar acid, and sugar alcohols but not disaccharides induced inward currents in oocytes expressing AtPLT5. AtPLT5 expression also resulted in 14C-labeled substrate uptake in oocytes, indicating that AtPLT5 encodes an ion-coupled uptake transporter. K(0.5) values for glucose and sorbitol were highly dependent on external pH. Expression of AtPLT5 was found primarily in sink tissues: in the elongation zone of roots, in the inflorescence stem, and several floral structures, especially in the floral abscission zone. Expression was induced by mechanical wounding and insect feeding. Analysis of transport properties and expression in Arabidopsis indicate that AtPLT5 functions to transport a wide range of sugars into specific sink tissues in the plant.

Animals↗