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PubMed2000

The use of the 2-aminobenzoic acid tag for oligosaccharide gel electrophoresis.

Gel electrophoresis of fluorophore labeled saccharides provides a rapid and reliable method to screen enzymatic and/or chemical treatments of polysaccharides and glycoconjugates, as well as a sensitive and efficient microscale method to separate and purify oligosaccharides for further analysis. A simple and inexpensive method of derivatization and analysis using 2-aminobenzoic acid (anthranilic acid, AA) is described and applied to the extracellular polysaccharide released by the desiccation tolerant cyanobacterium Nostoc commune DRH-1. The results of these analyses suggest a possible protective functionality of two pendent groups, as well as a potential relationship between these groups and the desiccation tolerance of the organism.

Carbohydrate Sequence↗

PubMed1995

Pentafluorobenzylation method for quantification of acidic tryptophan metabolites using electron capture negative ion mass spectrometry.

An improved pentafluorobenzylation method was developed for derivatization of L-tryptophan and its acidic metabolites (L-kynurenine, kynurenic acid, anthranilic acid, xanthurenic acid, 3-hydroxyanthranilic acid, picolinic acid, quinolinic acid) present at trace levels in aqueous samples. This method employs lyophilization of aqueous samples in the presence of excess tetrabutylammonium hydrogen sulfate, followed by base-catalyzed anhydrous pentafluorobenzylation. A comparison with other published methods shows the advantage of this modification for the derivatization of kynurenine metabolites. The derivatives were analyzed by gas chromatography/electron capture negative ion mass spectrometry (GC/ECNI-MS) or liquid chromatography/particle beam/ECNI-MS (LC/ECNI-MS). The detection limits for injected standards are in the femtogram range by GC/ECNI-MS and in the low picogram range by LC/ECNI-MS. GC/ECNIMS is 3.6 (xanthurenic acid) to 66 (quinolinic acid) times more sensitive than LC/ECNI-MS. The simultaneous determination of two neuroactive metabolites, quinolinic and kynurenic acids, in culture medium is presented. The minimum measurable concentrations of these metabolites in 100 microL of culture medium are 0.11 nM for quinolinic acid and 0.21 nM for kynurenic acid.

Fluorobenzenes↗

PubMed1968

Tryptophan Biosynthesis in Cell Cultures of Nicotiana tabacum.

Some of the general features of the pathway for l-tryptophan biosynthesis in cell cultures of Nicotiana tabccum var. Wisc. 38 have been investigated. The results of both isotope competition and direct-labeling experiments show that shikimic acid, anthranilic acid, indoleglycerol phosphate, and indole can serve as precursors to l-tryptophan in these cells, indicating that, in terms of its biochemical intermediates, the pathway is similar to that described for the bacteria and fungi.

Journal Article↗

PubMed2002

Tryptophan metabolism via the kynurenine pathway in experimental chronic renal failure.

BACKGROUND: Kidneys are involved in tryptophan (TRP) metabolism in two ways. They eliminate TRP derivatives on the one hand, and they produce several enzymes taking part in TRP metabolism mainly via the kynurenine pathway on the other. The aim of the present study was to examine the time-course of changes in the peripheral kynurenine products degradation during experimental chronic renal failure in rats. METHODS: Tryptophan, kynurenine, 3-hydroxykynurenine, kynurenic acid, xanthurenic acid, anthranilic acid and quinolinic acid were determined in plasma using high-performance liquid chromatography technique with UV, fluorescence and electrochemical detection. RESULTS: A decreased TRP level and significant increase in kynurenine pathway metabolite concentrations in plasma of uremic rats were found. CONCLUSIONS: Substantial disturbances in the peripheral kynurenic pathway were observed in experimental chronic renal failure. They may contribute to several symptoms of uremia.

Animals↗

PubMed1986

Renal toxicity of non-steroidal anti-inflammatory drugs.

Non-steroidal anti-inflammatory drugs represent the most heavily prescribed and used class of drugs in human medicine. Most are derivatives of either salicylates, propionic acid, indoleacetic acid, anthranilic acid, pyrazolone, or oxicams. They depress the synthesis of prostaglandins from arachidonic acid by reversible inhibition of the enzyme cyclooxygenase. In the kidney, prostaglandins PGE2 and PGI2 modulate the vasoconstrictor effects of angiotensin II, norepinephrine, and vasopressin. In the presence of volume contraction, anesthesia, or disease states associated with high levels of these hormones, prostaglandins regulate glomerular filtration, vascular resistance, and renin secretion. They additionally influence urine volume and sodium content. In man, a syndrome of analgesic abuse that has been identified worldwide occurs more frequently in females than males and can result in severe renal damage, most notably renal papillary necrosis. Most common laboratory animals are relatively resistant to developing the renal lesion associated with NSAIDs unless high doses are given over long periods of time and some withholding of water is introduced into the protocol. Diuresis with 5% dextrose and water is protective. Studies of paracetamol and salicylate have demonstrated that these compounds concentrate in the papillary tip of the kidney at concentrations of 4 to 13 times the plasma levels in dogs and rabbits, respectively. Renal papillary necrosis has been described in horses on maintenance doses of phenylbutazone where dehydration or reduced water consumption has occurred. The lesion can be reproduced experimentally if water is withheld during a portion of the dosing interval. An increased incidence of uroepithelial tumors have been reported in patients with a history of analgesic abuse.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗

PubMed2026

Metabolic pathways linked to sarcopenia in the Bushehr Elderly Health Program: kynurenine, nicotinamide, B-vitamins, and sulfur amino acids.

BACKGROUND: Sarcopenia, characterized by the loss of muscle mass and function, is a common condition in the elderly, associated with increased morbidity and mortality. Metabolic pathways, including the kynurenine, nicotinamide, B-vitamins, and sulfur amino acid pathways, may play a significant role in the development and progression of sarcopenia. This study investigates the relationship between metabolic pathways and sarcopenia, aiming to identify potential therapeutic targets. METHOD: Four hundred participants over 60 years were randomly selected from the second stage of the Bushehr Elderly Health Program (BEH). Frozen plasma samples were used to measure metabolomics. We used factor analysis and logistic regression analysis to determine the kynurenine-tryptophan metabolites associated with sarcopenia and its components. RESULT: Study participants included 89 sarcopenic subjects aged 72.92 ± 7.32 years and 307 non-sarcopenic subjects aged 68.12 ± 5.56 years. In full model adjustment, factor 3, which included methionine, tryptophan, 3-hydroxyanthranilic acid, picolinic acid, and xanthurenic acid, was associated with 38.3% lower risk of sarcopenia (OR = 0.617 [95%CI = 0.436–0.875]); Factor 6, which included methylmalonic acid and total homocysteine, was associated with a 33.7% increased risk of sarcopenia (OR = 1.337 [95%CI = 1.031–1.735]); and factor 7, consisting of nicotinamide, were related to a 25.2% lower risk of developing sarcopenia (OR = 0.748 [95%CI = 0.571–0.979]). Additionally, factor 1, which included quinolinic acid, kynurenine, 3-hydroxykynurenine, neopterin, kynurenic acid, anthranilic acid, cystathionine, and total cysteine, was linked to a 49.2% higher risk of low muscle strength, while factors 3 and 7 were associated with approximately a 24% decrease in risk of low muscle strength. Factors 5, consisting of serine and glycine, and factor 7 were related to 43% and 27.7% lower risk of low skeletal muscle index, respectively. While factor 6 was related to a 32.8% higher risk of low skeletal muscle index. Factor 1 was also related to a 32.9% higher risk of low walking speed, while factor 3 was related to a 28.5% lower risk of low walking speed. CONCLUSION: Specific metabolites from the kynurenine, nicotinamide, B-vitamin, and sulfur amino acid pathways are significantly associated with sarcopenia and its key parameters, such as muscle strength, skeletal muscle index, and walking speed. These findings suggest that metabolic profiling could offer valuable insights for early detection and targeted interventions for sarcopenia in elderly populations.

Humans↗

PubMed1990

Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp.

Quinaldine catabolism was investigated with the bacterial strain Arthrobacter sp., which is able to grow aerobically in a mineral salt medium with quinaldine as sole source of carbon, nitrogen and energy. The following degradation products of quinaldine were isolated from the culture fluid and identified: 1H-4-oxoquinaldine, N-acetylisatic acid, N-acetylanthranilic acid, anthranilic acid, 3-hydroxy-N-acetylanthranilic acid and catechol. 3-Hydroxy-N-acetylanthranilic acid was not further metabolized by this organism. A degradation pathway is proposed.

Arthrobacter↗

PubMed1990

Microbial metabolism of quinoline and related compounds. V. Degradation of 1H-4-oxoquinoline by Pseudomonas putida 33/1.

A bacterial strain was isolated with the ability to use 1H-4-oxoquinoline as the sole source of carbon, nitrogen and energy. On the basis of its physiological properties, this isolate was classified as Pseudomonas putida. 1H-3-Hydroxy-4-oxoquinoline, N-formylanthranilic acid, anthranilic acid and catechol were identified as intermediates in the degradation pathway. The latter was further degraded by ortho-cleavage. The enzymatic conversion of 1H-4-oxoquinoline into 1H-3-hydroxy-4-oxoquinoline requires oxygen and NADH. Experiments with 18O2 showed that the oxygen consumed in this enzymatic reaction is derived from the atmosphere.

Aerobiosis↗

PubMed1979

The functional roles of cytochrome P-450 mediated systems: present knowledge and future areas of investigations.

Research in recent years has considerably enhanced our understanding of the membrane-bound cytochrome P-450-catalyzed biotransformations in organisms. A remarkable similarity has become apparent between diversified animal groups with respect to the components and functional roles of the cytochrome P-450 systems. For example, the steroidal hormone metabolism role for this cytochrome in mammals was recently extended to insect species. In addition, this cytochrome functions importantly in mammalian species for the metabolism of a variety of other endogenous substrates such as bile acids, anthranilic acid, fatty acids, bilirubin and heme, indoles, amines, and purines. Regarding the exogenous role, the system has been known to convert toxic lipophilic substances such as drugs and insecticides to more hydrophilic metabolites which can be easily eliminated by the water-based excretory system in organisms. This detoxication ability apparently arose in organisms, particularly the herbivores, in response to the need to detoxify plant-defensive toxins such as tannins, phenols, quinones, alkaloids, steroids, lecithins, and lignins. The interface between plants and insects is enormous, and therefore it appears probable that cytochrome P-450 will one day be shown to be important in the conversion/utilization of other plant secondary substances, e.g., synthesis of cholesterol from phytosterols, and sex pheromones from olefins, terpenes, and alkaloids.

Biotransformation↗

PubMed2001

Kynurenine and its metabolites in the rat with experimental renal insufficiency.

In uremia a great number of the endogenous metabolites that are ordinarily excreted in urine accumulate in the blood. Among these are the products of KYN degradation. In the present study we evaluated the peripheral KYN metabolism in the various stages of the rat experimental chronic renal insufficiency. Our results showed significant disturbances in peripheral kynurenic pathway, which resulted in the significant decrease of TRP plasma level and augmentation of concentration of its metabolites. The high concentrations of 3-hydroxykynurenine, xanthurenic acid, kynurenic acid, anthranilic acid and quinolinic acid positively correlated with degree of the renal insufficiency. Talking into account the biological properties of KYN metabolites, their accumulation in the blood, may be at least partially, responsible for severity of uremia as well as for uremic symptoms such as neuropathy, increased susceptibility to infections, hypertension, lipid disturbances and anemia.

Animals↗

PubMed1986

Evidence for the existence of high affinity binding sites for indomethacin on human blood platelets.

Using human blood-washed platelets and [3H]indomethacin, we demonstrated the presence of saturable, time- and temperature-dependent high affinity binding sites for non-steroidal anti-inflammatory drugs. The observed Kd value for indomethacin was 5 nM. Structural specificity of the non-steroidal anti-inflammatory drug site was studied with arylacetic acids, anthranilic acids, and compounds from other chemical families. Arylacetic acid drugs had affinities which were similar to the affinity of indomethacin. Affinity differences among the other drugs may be related to the presence or absence of the lipophilic substituent on the central ring. As expected, anti-inflammatory pyrrazole derivatives, aspirin, bucloxic acid, cortisol, nordihydroguaiaretic acid, and the chemotactic peptide formyl-Met-Leu-Phe were not recognized by the indomethacin binding site.

Anti-Inflammatory Agents↗

PubMed1982

Investigations on nonsulfonamide Bratton-Marshall-positive compounds in porcine liver.

An unknown Bratton-Marshall-positive compound was observed when liver extracts were screened by a procedure for the simultaneous determination of sulfamethazine and sulfathiazole in swine livers. The unknown has been conclusively identified as o-aminobenzoic acid (anthranilic acid), a tryptophan metabolite, by gas-liquid chromatography-mass spectrometry of swine liver extracts obtained by a modified Tishler procedure for sulfonamide residues in animal tissues.

Animals↗

PubMed1999

Biosynthesis of indole-3-acetic acid in Azospirillum brasilense. Insights from quantum chemistry.

Quantum chemical methods AM1 and PM3 and chromatographic methods were used to qualitatively characterize pathways of bacterial production of indole-3-acetic acid (IAA). The standard free energy changes (delta G(o)'sum) for the synthesis of tryptophan (Trp) from chorismic acid via anthranilic acid and indole were calculated, as were those for several possible pathways for the synthesis of IAA from Trp, namely via indole-3-acetamide (IAM), indole-3-pyruvic acid (IPyA), and indole-3-acetonitrile (IAN). The delta G(o)'sum for Trp synthesis from chorismic acid was -402 (-434) kJ.mol-1 (values in parentheses were calculated by PM3). The delta G(o)'sum for IAA synthesis from Trp were -565 (-548) kJ.mol-1 for the IAN pathway, -481 (-506) kJ.mol-1 for the IAM pathway, and -289 (-306) kJ.mol-1 for the IPyA pathway. By HPLC analysis, the possibility was assessed that indole, anthranilic acid, and Trp might be utilized as precursors for IAA synthesis by Azospirillum brasilense strain Sp 245. The results indicate that there is a high motive force for Trp synthesis from chorismic acid and for IAA synthesis from Trp, and make it unlikely that anthranilic acid and indole act as the precursors to IAA in a Trp-independent pathway.

Azospirillum brasilense↗

PubMed1963

EFFECTS OF CERTAIN AMINO ACIDS ON ANTHRANILATE PRODUCTION IN NEUROSPORA CRASSA.

Soboren, Josephine (University of California, Los Angeles) and Joseph F. Nyc. Effects of certain amino acids on anthranilate production in Neurospora crassa. J. Bacteriol. 85:881-888. 1963.-The level of anthranilic acid produced in cultures of a tryptophanless mutant of Neurospora crassa strain C-83 was closely related to the growth response. A good growth response was attained only on supplements which greatly repressed the level of anthranilate accumulated. The improved growth response of strain C-83 to variable levels of tryptophan and to supplements of the amino acids phenylalanine, tyrosine, leucine, and methionine was correlated with a decreased anthranilate production. The inhibitory effect of these supplements on anthranilate production was ascribed to effects on the mechanisms which regulate the formation of anthranilic acid.

Amino Acids↗

PubMed1995

Catabolism of indole-3-acetic acid and 4- and 5-chloroindole-3-acetic acid in Bradyrhizobium japonicum.

Some strains of Bradyrhizobium japonicum have the ability to catabolize indole-3-acetic acid. Indoleacetic acid (IAA), 4-chloro-IAA (4-Cl-IAA), and 5-Cl-IAA were metabolized to different extents by strains 61A24 and 110. Metabolites were isolated and analyzed by high-performance liquid chromatography and conventional mass spectrometry (MS) methods, including MS-mass spectroscopy, UV spectroscopy, and high-performance liquid chromatography-MS. The identified products indicate a novel metabolic pathway in which IAA is metabolized via dioxindole-3-acetic acid, dioxindole, isatin, and 2-aminophenyl glyoxylic acid (isatinic acid) to anthranilic acid, which is further metabolized. Degradation of 4-Cl-IAA apparently stops at the 4-Cl-dioxindole step in contrast to 5-Cl-IAA which is metabolized to 5-Cl-anthranilic acid.

Chromatography, High Pressure Liquid↗

PubMedDate not supplied

Possible involvement of kynurenamines in the pathogenesis of cataract in diabetic patients.

BACKGROUND: It has been demonstrated that the products of tryptophan degradation, kynurenamines, play an important role in senile cataract formation. However, the involvement of these compounds in the development of diabetic cataract has not been studied. The aim of the present study was to compare the concentration of tryptophan and kynurenamines in the aqueous humor and lenses obtained from non-diabetic and diabetic patients with cataract. MATERIAL AND METHODS: The concentration of tryptophan, kynurenine, 3-hydroxykynurenine, kynurenic acid and anthranilic acid was measured using high-performance liquid chromatography (HPLC) with appropriate detection in aqueous humor and lenses obtained from 38 non-diabetic subjects and 20 patients with type II diabetes in course of surgical cataract extraction. RESULTS: In diabetic patients the concentration of kynurenine, 3-hydroxykynurenine and anthranilic acid in the aqueous humor was increased in comparison with non - diabetic subjects, while the concentration of tryptophan and kynurenic acid was similar in both groups. In the lenses obtained from patients with diabetes accumulation of tryptophan and all of its assayed metabolites was observed. CONCLUSIONS: Concentrations of the products of kynurenine pathway of tryptophan degradation in the aqueous humor and the lenses of diabetic patients are increased. We suggest that these compounds could play an important role in the development of diabetic cataract.

Aqueous Humor↗

PubMed1983

Antagonism of kynurenine-induced seizures by picolinic, kynurenic and xanthurenic acids.

Picolinic, kynurenic, xanthurenic and anthranilic acids are metabolites of L-kynurenine which, when administered intraperitoneally (i.p.) antagonized (in descending order of potency) the seizures induced by intracerebroventricular (i.c.v.) injections of l-kynurenine sulfate in SHR and C57BL/6 mice. Picolinic and anthranilic acids were also effective after oral administration. Picolinic acid completely prevented seizures. Kynurenic acid, when injected i.c.v. prior to l-kynurenine sulfate, appeared to be more effective than after i.p. administration while picolinic and anthranilic acids were less effective. This suggest that the antikynurenine effect of metabolites of kynurenine (kynurenines) is related to different brain structures, i.e. kynurenic acid predominantly affects structures adjacent to ventricles (e.g. hippocampus, caudate nucleus) while picolinic and anthranilic acids act on other brain structures or the periphery. Xanthurenic, kynurenic and picolinic acids merely prolonged the latency of seizures induced by i.c.v. quinolinic acid (another metabolite of kynurenine) or by subcutaneous strychnine sulfate and i.p. pentylenetetrazole, and did not modify seizures induced by i.p. caffeine and thiosemicarbazide. This selective antagonism of the tested kynurenines against kynurenine might be an important anticonvulsant factor in kynurenine-dependent seizures. It is suggested that increased excretion of xanthurenic, kynurenic and picolinic acids in patients with convulsive states may be manifestations of compensatory processes.

Animals↗

PubMed2005

Anthranilic acid-uraemic toxin damaged red cell's membrane.

Normocytic normochromic anaemia is a common syndrome present in patients with chronic renal insufficiency (CRI). Simultaneously in these patients the increase in L-tryptophan (TRP) degradation via kynurenine pathway is observed. On the basis of these observations we tried to examine whether one of the TRP metabolites, anthranilic acid (AA), shows interaction with membranes of erythrocytes and because of that it may contribute to anaemia development. In patients with CRI we have observed changes characteristic for normocytic normochromic anaemia, such as the decrease in erythrocyte count, haemoglobin concentration, haematocrit and the decrease in erythrocyte osmotic resistance as well as the increase in AA concentration in plasma in comparison to healthy subjects. We have also noticed the existence of a positive correlation between anthranilic acid concentration and creatinine and urea concentrations and also negative relationships between anthranilic acid concentration and haematological parameters. Moreover, incubation of healthy erythrocytes with 10 and 100 microM AA caused haemolysis curve movement to the right, which shows decrease in osmotic resistance. In conclusion, the increase in plasma AA concentration might be one of many factors, which damage erythrocyte membrane, and thereby contributes to anaemia development in patients with CRI.

Aged↗