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PubMed2003

[Conjugation reactions of ciprofibrate with human and laboratory animals].

An open problem of the lipid lowering agent ciprofibrate (rac-2-[4-(2,2-dichlorocyclopropyl)-phenoxy]-2-methylpropanoic acid, CAS 52214-84-3) is its metabolism concerning the conjugation with amino acids and glucuronic acid. It could be solved by syntheses of the needed reference compounds--unknown up to now--and administration of ciprofibrate to volunteers and rats. Unexpectedly the conjugation compounds with amino acids are stable in vitro and in metabolism. There was no evidence for any conjugation reaction with amino acids by investigating samples of urine and faeces. On the contrary the urine of humans contains 90-97% of beta-O-acylglucuronide, whereas rat urine shows only 10% of the calculated amount.

Amino Acids↗
PubMed1997

Bacteroides J-37, a human intestinal bacterium, produces alpha-glucuronidase.

beta-Glucuronidases of mammalian tissues metabolized glycyrrhizin (18 beta-glycyrrhetinic acid, beta-D-glucuronyl alpha-D-glucuronic acid, GL) to glycyrrhetinic acid (GA) via 18 beta-glycyrrhetinic acid alpha-D-glucuronic acid (GAMG); they hydrolyzed beta-glucuronic acid conjugates better than alpha-glucuronic acid conjugates. However, human intestinal bacteria directly metabolized GL to GA, and minorly to GA via GAMG. Bacteroides J-37, isolated from human intestinal bacteria, transformed GL or GAMG to GA, but not baicalin; it produced alpha-glucuroniase, which hydrolyzed the alpha-linkage of glucuronic acid conjugates. alpha-Glucuronidase of Bacteroides J-37 hydrolyzed alpha-glucuronic acid conjugates better than beta-glucuronic acid conjugates. beta-Glucuronidase from E. coli, a human intestinal bacterium, hydrolyzed baicalin to baicalein, but did not transform GL.

Animals↗
PubMed1975

[Urinary excretion of glucuronic and hippuric acids in rats ingesting heated linseed oil].

Nutritionally harmful substances are formed when edible vegetable oils are heated (cyclization, polymerization of unsaturated fatty acids, ...). How are these substances metabolized in animals? This work is a first attempt to experiment if these altered fatty acids or their metabolites are excreted as conjugated compounds in the urine. Weaning rats (weighing 45 g) were divided into 3 groups of 9 animals each. They received balanced diets containing 10 p. 100 by weight of lipids. In the first group, the dietary of lipids was linseed oil which had been heated for 12 hours at 275 degrees C under nitrogen (group HC275); in the second group, the linseed oil had been heated 100 hours at 200 degrees C in presence of air (group HC200). These two groups of animals were fed ad libitum. The control group (group HF) was fed a diet containing fresh linseed oil and its food consumption was restricted to the quantity eated by the HC275 group (pair feeding). Urines were collected daily from the 8th to the 15th day of experiment and pooled for each rat. Hippuric acid and glucuronic acid contents were determined in these urines. During this period the hippuric acid excretion in HC275 and HC200 groups is twice as high as in HF group (32, 35 and 17 mumoles respectively). On the other hand urinary excretion of glucoronic acid is 8 times higher in HC275 and 3 times in HC200 than in HF (2214, 739 and 269 mumoles respectively). Hippuric acid excretion is very small as compared to that of glucuronic acid. Therefore it seems that most of the compounds formed during heating of the oil or their metabolites are excreted as glucoronic acid conjugates.

Air↗
PubMed1989

The interaction of xylosyltransferase and glucuronyltransferase involved in glucuronoxylan synthesis in pea (Pisum sativum) epicotyls.

A particulate enzyme preparation from etiolated pea (Pisum sativum) epicotyls was found to incorporate xylose from UDP-D-xylose into beta-(1----4)-xylan. The ability of this xylan to act as an acceptor for incorporation of [14C]glucuronic acid from UDP-D-[14C]glucuronic acid in a subsequent incubation was very limited, even though glucuronic acid incorporation was greatly prolonged when UDP-D-xylose was present in the same incubation as UDP-D-[14C]glucuronic acid. This indicated that glucuronic acid could not be added to preformed xylan. However, the presence of UDP-D-glucuronic acid inhibited incorporation of [14C]xylose from UDP-D-[14C]xylose into beta-(1----4)-xylan, and neither S-adenosylmethionine nor acetyl-CoA stimulated either the xylosyltransferase or the glucuronyltransferase.

Acetyl Coenzyme A↗
PubMed1976

Bilirubin conjugates in bile of man, rat and dog. Semi-quantitative analysis of bile composition by thin-layer chromatography.

1. Conjugated bile pigments, separated in two fractions by semi-quantitative t.l.c. performed on silicic acid with phenol/water as the developing solvent, were treated with diazotized ethyl anthranilate. Resulting dipyrrylazo derivatives were analysed by quantitative t.l.c. 2. The tentative structure elucidation of tetrapyrrolic bilirubin conjugates and semi-quantitative evaluation of rat bile, post-obstructive human bile and dog bile composition is presented. 3. Homogeneous and mixed hexuronic acid diesters of bilirubin containing glucuronic acid constitute 51% of the total conjugates in normal rat bile, 45% of those in human post-obstructive bile and 38% of those in obstructed rat biles. 4. Monoconjugated bilirubin amounts to 33% of total conjugated bile pigments in normal rat bile, and 17 and 14% in post-obstructive hepatic human bile and gall-bladder bile of dog respectively. After loading with unconjugated bilirubin a greater amount of monoconjugates (56%) occur in the rat bile, whereas bilirubin diglucuronide excretion is decreased (34%). 5. In gall-bladder bile of normal dog, 40% of glucose-containing diconjugates, 32% of homogeneous and/or mixed hexuronic acid (mainly glucuronic acid) diesters of bilirubin and 14% of xylose-containing diconjugates are estimated. 6. Increased amounts of bilirubin conjugates, including some with unidentified uronic acid groups, were observed in cholestatic rat biles and quantities of conjugates with glucuronic acid were decreased.

Animals↗
PubMed1987

Characterization of structural component of cell walls of alkalophilic strain of Bacillus sp. C-125. Preparation of poly(gamma-L-glutamate) from cell wall component.

The cell wall of an alkalophilic strain of Bacillus sp. C-125 is composed of A1 gamma-peptidoglycan, a teichuronic acid and an unknown acidic polymer composed of glutamic acid and glucuronic acid, of which the molar ratio is approx. 4-5:1. Poly(gamma-L-glutamate) was prepared from the acidic polymer by removal of almost all of the glucuronic residues with trifluoromethanesulphonic acid treatment and purified chromatographically. The Mr of the polyglutamate preparation was estimated to be 14,000 by gel chromatography, or 43,000 on the basis of the content of N-terminal acid residues. The acidic polymer found in the cell wall of the organism was concluded to be a polyglutamate substituted with (oligo)glucuronic acid residues or a complex composed of two kinds of polymers (polyglutamate and polyglucuronate).

Bacillus↗
PubMed2005

Characterisation of natural polysaccharides (plant gums) used as binding media for artistic and historic works by capillary zone electrophoresis.

The monosaccharide constituents of plant gums were separated by capillary electrophoresis at pH 12.1 and detected with indirect UV absorbance. The plant gums investigated were gum arabic, gum acacia, gum tragacanth, cherry gum and locust bean gum (carob gum). The monosaccharides obtained after hydrolysis with 2M trifluoroacetic acid and lyophilisation of the hydrolysate were arabinose, galactose, mannose, rhamnose, xylose, fucose, and glucose, and the two sugar acids galacturonic and glucuronic acid, in accordance with the literature. They were separated in a background electrolyte consisting of NaOH to adjust the pH, 20 mM 2,6-pyridinedicarboxylic acid as chromophore for detection and 0.5 mM cetyltrimethylammonium bromide as additive to reverse the electroosmotic flow. Based on their electropherograms, the plant gums could be identified by their typical composition (depicted in a decision scheme) as follows: a peak of glucuronic acid, together with that of rhamnose, is indicative for gum arabic. Peaks of galacturonic acid and fucose point to gum tragacanth. Locust bean gum shows a major peak for mannose (with the concomitant galactose peak in ratio 4-1), whereas a glucuronic acid and a mannose peak together with a prominent arabinose peak indicates cherry gum. The method was applied to identify the plant gums in samples like watercolours and in several paint layers like gum tempera or those with egg white or drying oils as additives. Artificial aging experiments of thin layers of gum arabic on paper or glass carried out with UV-A radiation (366 nm) did not result in changes of the saccharide patterns, in contrast to the simultaneously conducted aging of a drying oil layer.

Art↗
PubMed1998

Ion-spray mass spectrometry for identification of the nonreducing terminal sugar of glycosaminoglycan.

Various oligosaccharides from hyaluronic acid, which have glucuronic acid or N- acetylglucosamine at the nonreducing terminal, were prepared by digestion with a combination of testicular hyaluronidase and beta-glucuronidase. These oligo saccharides were analyzed by negative-mode ion-spray mass spectrometry (MS) with an atmospheric pressure ion source. Introduction of collisionally activated dissociation tandem mass spectrometry (CAD-MS/MS) produced ions derived from cleavage of the glycosidic bonds, allowing the structure to be analyzed. The CAD-MS/MS spectrum showed an intense and characteristic fragment ion at m/z 193 for oligosaccharides having glucuronic acid at the nonreducing terminal. On the other hand, this ion was not observed in the spectra of oligosaccharides having N- acetylglucosamine at the nonreducing terminal. Therefore, the fragmentation pattern revealed by CAD-MS/MS provides useful information for distinguishing glucuronic acid and N- acetylglucosamine at the nonreducing terminal of oligosaccharides derived from hyaluronic acid and other glycosaminoglycans. This ion-spray CAD-MS/MS technique was also applied successfully to the characterization of glycosaminoglycans reconstructed by glycotechnology.

Animals↗
PubMed1976

Dermatan sulfate-chondroitin sulfate copolymers from ambilical cord. Isolation and characterization.

Dermatan sulfate-chondroitin sulfate copolymers have been isolated from human umbilical cord as a major galactosaminoglycan component of this tissue. The galactosaminoglycan fraction was obtained from this tissue by papain [EC 3.4.22.2] digestion followed by precipitation with cetylpyridinium chloride in a yield of 700 mg per 100 g of dry tissue. Ethanol fractionation resolved 4-5 subfractions differing in relative content of L-iduronic acid and D-glucuronic acid. No galactosaminoglycan containing either solely L-iduronic acid or D-glucuronic acid was obtained. The copolymeric structure of the material in each subfraction was demonstrated by analysis of oligosaccharide fragments obtained by chondroitinase-AC [EC 4.2.2.5] digestion. All the polymers contained repeating disaccharide units, D-glucuronosyl-N-acetylgalactosamine, D-glucuronosyl-N-acetylgalactosamine 4-sulfate, D-glucuronosyl-N-acetyl-galactosamine 6-sulfate, and L-iduronosyl-N-acetylgalactosamine 4-sulfate, of which D-glucuronosyl-N-acetylgalactosamine 6-sulfate and L-iduronosyl-N-acetylgalactosamine 4-sulfate were predominant. Both iduronic acid- and glucuronic acid-containing units were arranged in clusters. The presence of a considerable amount of nonsulfated disaccharide units was noted. The copolymers show extensive polydispersity in electrophoresis on cellulose acetate and gel chromatography on Sephadex G-200.

Amino Acids↗
PubMed2000

Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures.

UDP-glucuronate: baicalein 7-O-glucuronosyltransferase (UBGAT) catalyzes the transfer of glucuronic acid from UDP-glucuronic acid to the 7-OH of baicalein. UBGAT was purified from cultured cells of Scutellaria baicalensis Georgi (Lamiaceae). It was purified 95-fold using various chromatography and chromatofocusing procedures to apparent homogeneity. The Mr was estimated to be 110 kDa by gel filtration chromatography with a 52 kDa subunit by SDS-PAGE. The isoelectric point was pH 4.8. UBGAT was specific to UDP-glucuronic acid as a sugar donor and flavones with substitution ortho- to the 7-OH group such its baicalein (6-OH), scutellarein (6-OH) and wogonin (8-OMe).

Chromatography, Gel↗
PubMed1991

Sialic acid storage diseases. A multiple lysosomal transport defect for acidic monosaccharides.

A defective efflux of free sialic acid from the lysosomal compartment has been found in the clinically heterogeneous group of sialic acid storage disorders. Using radiolabeled sialic acid (NeuAc) as a substrate, we have recently detected and characterized a proton-driven carrier for sialic acid in the lysosomal membrane from rat liver. This carrier also recognizes and transports other acidic monosaccharides, among which are uronic acids. If no alternative routes of glucuronic acid transport exist, the disposal of uronic acids can be affected in the sialic acid storage disorders. In this study we excluded the existence of more than one acidic monosaccharide carrier by measuring uptake kinetics of labeled glucuronic acid [( 3H]GlcAc) in rat lysosomal membrane vesicles. [3H]GlcAc uptake was carrier-mediated with an affinity constant of transport (Kt) of 0.3 mM and the transport could be cis-inhibited or trans-stimulated to the same extent by sialic acid or glucuronic acid. Human lysosomal membrane vesicles isolated from cultured fibroblasts showed the existence of a similar proton-driven transporter with the same properties as the rat liver system (Kt of [3H]GlcAc uptake 0.28 mM). Uptake studies with [3H]NeuAc and [3H]GlcAc in resealed lysosome membrane vesicles from cultured fibroblasts of patients with different clinical presentation of sialic acid storage showed defective carrier-mediated transport for both sugars. Further evidence that the defective transport of acidic sugars represents the primary genetic defect in sialic acid storage diseases was provided by the observation of reduced, half-normal transport rates in lymphoblast-derived lysosomal membrane vesicles from five unrelated obligate heterozygotes. This study reports the first observation of a human lysosomal transport defect for multiple physiological compounds.

Animals↗
PubMed1983

Evidence for an active site arginine in UDP-glucuronyltransferase.

2,3-Butanedione inactivates the pure form of UDP-glucuronyltransferase used in these experiments (GT2P) (EC 2.4.1.17) purified from pig liver microsomes. The kinetics of the reaction indicates that 2,3-butanedione reacts with two amino acids that affect activity. A rapid, partial inactivation is followed by a slower rate of inactivation that leads eventually to completely inactive enzyme. UDP-glucuronic acid and glucuronic acid, as compared with UDP, are effective as protectors against the slow, secondary phase of inactivation; no ligand tested protected against the rapid phase of inactivation. The lipid environment of GT2P was a determinant of the pseudo-first order rate constant for the slow phase of inactivation, but did not affect the rate of the rapid phase of inactivation. The data suggest that GT2P contains an active site arginine that interacts with the -COO- at C-6 of the glucuronic acid moiety of UDP-glucuronic acid.

Amino Acids↗
PubMed2004

Structure of a hydroxyproline (Hyp)-arabinogalactan polysaccharide from repetitive Ala-Hyp expressed in transgenic Nicotiana tabacum.

A synthetic gene encoding the fusion protein (Ala-Hyp)(51)-enhanced green fluorescent protein expressed in Nicotiana tabacum cells produced a fusion glycoprotein with all proline residues hydroxylated and substituted with an arabinogalactan polysaccharide. Alkaline hydrolysis of the fusion glycoprotein yielded a population of hydroxyproline (Hyp)-arabinogalactan polysaccharides ranging in size from 13 to 26 saccharide residues/Hyp, with a median size of 15-17 residues. We isolated a 15-residue Hyp-arabinogalactan for structure determination by sugar analyses and one- and two-dimensional nuclear magnetic resonance techniques that provided the assignment of proton and carbon signals of a small polysaccharide O-linked to the hydroxyl group of Hyp. The polysaccharide consisted of a 1,3-linked beta-D-Galp backbone with a single 1,6-linked beta-D-Galp "kink." The backbone had two side chains of Galp substituted at position 3 with an arabinose di- or trisaccharide and at position 6 with glucuronic acid or rhamnosyl glucuronic acid. Energy-minimized space-filling molecular models showed hydrogen bonding within polysaccharides attached to repetitive Ala-Hyp and also between polysaccharides and the peptide backbone. Polysaccharides distorted the peptide Ramachandran angles consistent with the circular dichroic spectra of isolated (Ala-Hyp)(51) and its reversion to a polyproline II-like helix after deglycosylation. This first complete structure of a Hyp-arabinogalactan polysaccharide shows that computer-based molecular modeling of Hyp-rich glycoproteins is now feasible and supports the suggestion that small repetitive subunits comprise larger arabinogalactan polysaccharides.

Carbon↗
PubMed1988

Digestibility of pentose sugars and uronic acids and their effect on chick weight gain and caecal size.

1. In the first experiment D-xylose, L-arabinose, D-galacturonic and D-glucuronic acids were fed ad libitum to young chicks for 2 weeks at 200 g/kg of diet and weight gains and food consumption were recorded. 2. L-arabinose and D-xylose did not depress food consumption in the first week but prolonged feeding caused food consumption to decrease and weight gain to be adversely affected. 3. D-galacturonic acid and D-glucuronic acid caused severe growth retardation as early as the first week of feeding, primarily because of voluntary starvation. 4. Apparent metabolisable energy values for the diets were obtained when chicks were 19 to 21 d of age and were 14.04 +/- 0.52, 12.03 +/- 0.61, 11.77 +/- 1.21, 11.68 +/- 0.34 and 11.66 +/- 0.45 KJ/g for the basal diet with glucose, xylose, arabinose, galacturonic and glucuronic acids respectively. 5. True metabolisable energy values for the diets were obtained from adult cockerels and were 15.07 +/- 0.16, 13.45 +/- 0.16, 13.12 +/- 0.37, 12.29 +/- 0.26 and 12.69 +/- 0.23 KJ/g for basal diet with glucose, xylose, arabinose, galacturonic and glucuronic acids respectively. 6. In the second experiment D-galactose, D-xylose, L-arabinose, D-galacturonic and D-glucuronic acid were fed ad libitum to young chicks for 3 weeks at 50 g/kg of diet and weight gains and food consumption were recorded. 7. Chicks grew and ate well on all diets. 8. The digestibilities of sugars and uronic acids were obtained by measurement of these constituents in diets and digesta using titanium dioxide as a marker. The digestibilities were 1.000 +/- 0.0, 0.997 +/- 0.002, 0.936 +/- 0.041, 0.628 +/- 0.103, 0.588 +/- 0.059, and 0.645 +/- 0.089 for D-glucose, D-galactose, D-xylose, L-arabinose, D-galacturonic and D-glucuronic acids respectively. 9. Both at 200 and 50 g/kg dietary inclusion there was noticeable caecal fermentation from L-arabinose, D-galacturonic and D-glucuronic acid. Only at 200 g/kg dietary inclusion did D-xylose produce significant evidence of caecal fermentation.

Animals↗
PubMed1996

Description of a new polymer-secreting bacterium from a deep-sea hydrothermal vent, Alteromonas macleodii subsp. fijiensis, and preliminary characterization of the polymer.

A deep-sea, aerobic, mesophilic, heterotrophic bacterium was isolated from fluid collected near an active hydrothermal vent. On the basis of phenotypic and phylogenetic analyses and DNA-DNA relatedness, strain ST716 could be assigned to the species Alteromonas macleodii as a new subspecies. This bacterium secreted an unusual high-molecular-weight polysaccharide in the presence of glucose in batch cultures. The viscosity of this exopolysaccharide is of the same order of magnitude as that of xanthan, another bacterial polysaccharide of industrial interest. This polysaccharide, produced during the stationary phase, contained glucose, mannose, pyruvated mannose, and galactose along with galacturonic acid and glucuronic acid.

Base Composition↗
PubMed1982

Uridine diphosphate-glucuronic acid-independent conversion of bilirubin monoglucuronides to diglucuronide in presence of plasma membranes from rat liver is nonenzymic.

TWO ROUTES HAVE BEEN PROPOSED FOR CONVERSION OF BILIRUBIN MONOGLUCURONIDE TO THE DIGLUCURONIDE: glucuronyl transfer (a) from UDP-glucuronic acid to bilirubin monoglucuronide, catalyzed by a microsomal UDP-glucuronyltransferase, and (b) from one molecule of bilirubin monoglucuronide to another (transglucuronidation), catalyzed by an enzyme present in liver plasma membranes. The evidence regarding the role of the latter enzyme for in vivo formation of bilirubin diglucuronide is conflicting. We therefore decided to reexamine the transglucuronidation reaction in plasma membranes and to study the conversion of bilirubin monoglucuronide to diglucuronide in vivo. Purified bilirubin monoglucuronide was incubated with homogenates and plasma membrane-enriched fractions from liver of Wistar and Gunn rats. Stoichiometric formation of bilirubin and bilirubin diglucuronide out of 2 mol of bilirubin monoglucuronide was paralleled by an increase of the IIIalpha- and XIIIalpha-isomers of the bilirubin aglycone, thus showing that dipyrrole exchange, not transglucuronidation, is the underlying mechanism. Complete inhibition by ascorbic acid probably reflects intermediate formation of free radicals of dipyrrolic moieties. The reaction was nonenzymic because it proceeded independently of the protein concentration and heat denaturation of the plasma membranes did not result in decreased conversion rates. Collectively, these findings show spontaneous, nonenzymic dipyrrole exchange when bilirubin monoglucuronide is incubated in the presence of rat liver plasma membranes. Because bilirubin glucuronides present in biological fluids contain exclusively the bilirubin-IXalpha aglycone, formation of the diglucuronide from the monoglucuronide by dipyrrole exchange does not occur in vivo. Rapid excretion of unchanged bilirubin monoglucuronide in Gunn rat bile after injection of the pigment provides confirmatory evidence for the absence of a UDP-glucuronic acid-independent process.

Animals↗
PubMed1991

Nucleotide sequence and expression of the algE gene involved in alginate biosynthesis by Pseudomonas aeruginosa.

Alginate (Alg), a random polymer of mannuronic acid and glucuronic acid residues, is synthesized and secreted by Pseudomonas aeruginosa primarily during its infection of the lungs of cystic fibrosis patients. The molecular biology and biochemistry of the enzymatic steps leading to the production of the Alg precursor GDP-mannuronic acid have been elucidated, but the mechanism of polymer formation and export of Alg are not understood. We report the nucleotide sequence of a 2.4-kb DNA fragment containing the algE gene, previously designated alg76, encoding the AlgE protein (Mr 54,361) that is believed to be involved in these late steps of Alg biosynthesis. Expression of algE appears to occur from its own promoter. The promoter region contains several direct and inverted repeat sequences and shares structural similarity with promoters of several other alg genes from P. aeruginosa. In addition, the AlgE protein was overproduced from the tac promoter in P. aeruginosa. N-terminal amino acid sequence analysis showed that the polypeptide contains a signal peptide which is cleaved to form the mature protein during AlgE export from the cell cytoplasm.

Alginates↗
PubMed1982

The discovery of a lipid-linked glucuronide and its synthesis by chicken liver.

Upon incubation with uridine diphosphate-[14C]glucuronic acid, membrane fractions from adult and phenobarbital-induced embryonic liver synthesize a single glucuronide, which is soluble in chloroform:methanol (2:1). The compound is completely hydrolyzed and glucuronic acid released by either mild acid or beta-glucuronidase, whereas mild base hydrolysis results in a mixture of glucuronic acid and glucuronic acid-1,2-cyclic phosphate. These data and the behavior of the lipid-linked glucuronide on DEAE-cellulose chromatography indicate that the compound contains a monophosphate diester of glucuronic acid, which is beta-linked to a lipid. The synthesis of the lipid-linked glucuronide in uninduced normal embryonic liver is very low (5-15 pmol product/mg/5 min) at all developmental ages up to hatching, but the introduction of phenobarbital into the air space of a 9-10-day-old embryo causes a premature increase of activity (75-150 pmol products/mg/5 min) within 7 days. The glucuronyltransferase in adult and induced embryonic liver has a Km for UDPGlcUA of 0.17 x 10(-3) M and a broad pH optimum between pH 6 and 7. Glucuronic acid is released from the lipid-linked glucuronide by a beta-glucuronidase in liver that is active at neutral pH and is not inhibited by saccharolactone. This glycosidase activity appears, therefore, to be distinct from the previously characterized lysosomal beta-glucuronidase. Fractionation of adult chicken liver membranes by differential centrifugation indicates that over 70% of the glucuronyltransferase is associated with the nuclear and mitochondrial fractions. The endogenous beta-glucuronidase capable of hydrolyzing the lipid-linked glucuronide was not separated from the glucuronyl-transferase activity during fractionation. The data available suggests that the lipid-linked glucuronide is involved directly in the generation of free glucuronic acid for further metabolism.

Animals↗