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PubMedDate not supplied

Test for decreased serotonin/tryptophan metabolite ratios in abstinent alcoholics.

A segment of the population has a defect in the metabolism of tryptophan that causes a lowered concentration of serotonin in the central nervous system and indicates a predisposition towards chronic alcoholism. The metabolic defect in tryptophan metabolism is in the pathway between tryptophan and 5-hydroxyindoleacetic acid (5-HIAA) but not in the other pathways of tryptophan metabolism. A test using HPLC with amperometric detection was developed to detect the presence of an impaired serotonin metabolic pathway and therefore indicate a predisposition towards chronic alcoholism. The test used a ratio between 5-HIAA and two metabolites (indoleacetic acid and anthranilic acid) from the other pathways of tryptophan metabolism to indicate the presence or absence of an impaired serotonin metabolic pathway while correcting for variations in the concentration of urine.

Adult↗

PubMed1967

Studies with tryptophan metabolites in vitro. Kynurenine metabolism in liver homogenates of normal and Schistosoma mansoni-infested mice.

The conversion of kynurenine into kynurenic acid and anthranilic acid in both normal and Schistosoma mansoni-infested mouse liver was investigated. It was found that in the S. mansoni-infested mouse liver there is probably a deficiency of pyridoxal phosphate that resulted in an inhibition of kynurenine transaminase and a low production of kynurenic acid. Deoxypyridoxine and its phosphorylated derivative inhibited kynurenine transaminase in the normal liver in a pattern qualitatively similar to that observed with infested liver. The lowered concentration of pyridoxal phosphate in the infested liver is discussed in view of the possibility of two combined mechanisms: (a) an antimetabolite being secreted by the infesting worms or present in its eggs that partially inhibited the phosphorylation of pyridoxal, and (b) concentration of pyridoxal phosphate by the worms, resulting in a lowered concentration of the cofactor in the host tissue.

Animals↗

PubMed1968

Studies with tryptophan metabolites in vitro. Kynurenine metabolism in kidneys of mice infested with Schistosoma mansoni.

The conversion in vitro of kynurenine into kynurenic acid and anthranilic acid in both normal kidneys and those obtained from mice infested with Schistosoma mansoni was investigated. Normal mouse kidneys seem to possess an excess of functional pyridoxal phosphate over those obtained from infested mice. Kynureninase and kynurenine transaminase in the latter kidneys are more easily inhibited by deoxypyridoxal phosphate and tartar emetic, indicating low stores of active pyridoxal phosphate. The possible implication of these findings in relation to the role of the kidneys in producing abnormal patterns of tryptophan metabolism and possibly contributing to the production of bladder tumours in bilharzial patients is discussed.

Animals↗

PubMed1987

Epithelial chloride channel. Development of inhibitory ligands.

Chloride channels are present in the majority of epithelial cells, where they mediate absorption or secretion of NaCl. Although the absorptive and secretory channels are well characterized in terms of their electrophysiological behavior, there is a lack of pharmacological ligands that can aid us in further functional and eventually molecular characterization. To obtain such ligands, we prepared membrane vesicles from bovine kidney cortex and apical membrane vesicles from trachea and found that they contain a chloride transport process that is electrically conductive. This conductance was reduced by preincubating the vesicles in media containing ATP or ATP-gamma-S, but not beta-methylene ATP, which suggests that the membranes contain a kinase that can close the channels. We then screened compounds derived from three classes: indanyloxyacetic acid (IAA), anthranilic acid (AA), and ethacrynic acid. We identified potent inhibitors from the IAA and the AA series. We tritiated IAA-94 and measured binding of this ligand to the kidney cortex membrane vesicles and found a high-affinity binding site whose dissociation constant (0.6 microM) was similar to the inhibition constant (1 microM). There was a good correlation between the inhibitory potency of several IAA derivatives and their efficacy in displacing [3H]IAA-94 from its binding site. Further, other chloride channel inhibitors, including AA derivatives, ethacrynic acid, bumetanide, and DIDS, also displaced the ligand from its binding site. A similar conductance was found in apical membrane vesicles from bovine trachea that was also inhibited by IAA-94 and AA-130B, but the inhibitory effects of these compounds were weaker than their effects on the renal cortex channel. The two drugs were also less potent in displacing [3H]IAA-94 from the tracheal binding site.

Animals↗

PubMed1980

Inhibition of Aspergillus growth and aflatoxin release by derivatives of benzoic acid.

A study was conducted to determine the effects of o-nitrobenzoate, p-aminobenzoate, benzocaine (ethyl aminobenzoate), ethyl benzoate, methyl benzoate, salicylic acid (o-hydroxybenzoate), trans-cinnamic acid (beta-phenylacrylic acid), trans-cinnamaldehyde (3-phenylpropenal), ferulic acid (p-hydroxy-3-methoxycinnamic acid), aspirin (o-acetoxy benzoic acid), and anthranilic acid (o-aminobenzoic acid) upon growth and aflatoxin release in Aspergillus flavus NRRL 3145 and A. parasiticus NRRL 3240. A chemically defined medium was supplemented with various concentrations of these compounds and inoculated with spores, and the developing cultures were incubated for 4, 6, and 8 days at 27 degree C in a mechanical shaker. At the beginning of day 8 of incubation, aflatoxins were extracted from cell-free filtrates, separated by thin-layer chromatography, and quantitated by ultraviolet spectrophotometry. The structure of these aromatic compounds appeared to be critically related to their effects on mycelial growth and aflatoxin release. At concentrations of 2.5 and 5.0 mg per 25 ml of medium, methyl benzoate and ethyl benzoate were the most effective in reducing both mycelial growth and aflatoxin release by A. flavus and A. parasiticus. Inhibition of mycelial growth and aflatoxin release by various concentrations of the above-named aromatic compounds may indicate the possibility of their use as fungicides.

Acrolein↗

PubMed1988

Nutritional requirements of Methanomicrobium mobile.

A defined medium was developed for Methanomicrobium mobile BP. M. mobile required acetate for growth; the optimal concentration was 30 mM. Other requirements and their optimal concentrations included isobutyrate (0.65 mM), isovalerate (0.73 mM), and 2-methylbutyrate (1.5 mM). The appropriate branched-chain amino acids did not substitute for these branched-chain fatty acids. M. mobile required tryptophan at an optimal concentration of 24 microM. Indole substituted for tryptophan, but the possible precursor compounds shikimic acid and anthranilic acid and the degradation compound skatole did not. Vitamin requirements and their optimal concentrations included pyridoxine (0.49 microM), thiamine (0.15 microM), biotin (0.04 microM), and vitamin B12 (0.04 microM); p-aminobenzoic acid (0.18 microM) was required for optimal growth, but folic acid did not replace p-aminobenzoic acid. M. mobile required an unidentified growth factor found in ruminal fluid or extracts of Methanobacterium thermoautotrophicum for growth. M. mobile has a complex nutrition compared with that of other methanogens, but not an unusual nutrition in the context of organisms from the ruminal ecosystem.

Acetates↗

PubMed1962

Tryptophan synthetase levels in Escherichia coli, Shigella dysenteriae, and transduction hybrids.

Eisenstein, Richard B. (Western Reserve University, Cleveland, Ohio) and Charles Yanofsky. Tryptophan synthetase levels in Escherichia coli, Shigella dysenteriae, and transduction hybrids. J. Bacteriol. 83:193-204. 1962-Shigella dysenteriae and Escherichia coli, strains K-12 and B, were found to produce low levels of tryptophan synthetase, although some hybrids, formed by the introduction of the gene cluster concerned with tryptophan synthesis from S. dysenteriae into E. coli, produced high levels of this enzyme system. A revertant obtained from a tryptophan-requiring mutant also formed high levels of tryptophan synthetase. The gene or genes responsible for high enzyme production in these strains was shown to be linked to the cluster of genes concerned with tryptophan synthesis. The cause of high enzyme production was investigated. Various lines of evidence, including stimulation of growth by tryptophan precursors, sensitivity to inhibition by 5-methyltryptophan, absence of accumulation of tryptophan, and repression of enzyme formation by anthranilic acid and tryptophan, suggested that high enzyme production in the strains examined results from a partial block in the tryptophan pathway and not from resistance to repression by tryptophan. The conversion of shikimic acid-5-phosphate to anthranilic acid appears to be the partially blocked reaction in the strains studied.

Enzymes↗

PubMed1968

Itoic acid synthesis in Bacillus subtilis.

Under conditions of iron deficiency, strains of Bacillus subtilis produced 2,3-dihydroxybenzoic acid (DHB), 2,3-dihydroxybenzolyglycine (DHBG), or both of these compounds. DHB(G) production [production of DHB(G) refers to the production of DHB, or DHBG, or both] was proportional to the amount of iron present and occurred logarithmically, paralleling growth. Supplementation of media with more than 150 mug of iron per liter at zero-time inhibited DHB accumulation completely. In the presence of DHB, lower levels of iron inhibited DHB(G) production, so that the actual inhibitor of synthesis may involve the Fe(3+):[DHB(G)](3) complex. The strains producing DHBG also produced coproporphyrin III during iron-deficient growth, whereas a strain producing DHB did not produce coproporphyrin III under these conditions. Accumulation of DHB(G) was influenced by the levels of aromatic amino acids and anthranilic acid in the medium. In vivo experiments with strain B-1471 demonstrated that DHB was coupled to added glycine to form DHBG. Metabolism of DHB(G) was observed in two of the strains studied.

Bacillus subtilis↗

PubMed1968

Alteration of tryptophan-mediated regulation in Neurospora crassa by indoleglycerol phosphate.

The accumulation of imidazoleglycerol phosphate during growth of Neurospora crassa in the presence of 3-amino-1,2,4-triazole was found to cause derepression of tryptophan synthetase and to inhibit the induction of kynureninase. Accumulation of indoleglycerol phosphate in response to growth in the presence of indole acrylic acid or anthranilic acid was also accompanied by derepressed synthesis of tryptophan synthetase. Enzyme synthesis in mutants (his-7 and trp-4) unable to form these intermediates was not altered under similar conditions. The rate of formation of tryptophan synthetase and kynureninase was found to differ in the presence of tryptophan and indole.

Enzyme Induction↗

PubMed1985

3-Hydroxykynurenine, 3-hydroxyanthranilic acid, and o-aminophenol inhibit leucine-stimulated insulin release from rat pancreatic islets.

Individual islets were isolated from rat pancreas to study the effects of tryptophan and its metabolites on leucine-stimulated release of insulin. 3-Hydroxykynurenine, 3-hydroxyanthranilic acid, and o-aminophenol were inhibitors at concentrations below 10 mM whereas tryptophan, kynurenine, kynurenic acid, xanthurenic acid, and anthranilic acid were ineffective inhibitors at concentrations up to 10 mM. A structure-activity analysis of these metabolites demonstrated that vicinal aromatic hydroxy and amino groups with their concomitant electron donating properties are required for inhibition of insulin release. Inhibition of islet insulin release by the three kynurenine metabolites may be involved in the depressed insulin levels found in vitamin B6-deficient rats by other workers.

3-Hydroxyanthranilic Acid↗

PubMedDate not supplied

Clinical, biochemical and histochemical studies on infants with Acrodermatitis enteropathica chronica.

7 infants diseased with Acrodermatitis enteropathica and 10 normal controls were included in this study. The values of anthranilic acid glucuronide, 6- aminohippuric, anthranilic acid, N-acetyl Kneurine, Kneurine and 30 H Kneurenine, were estimated in mg/24 hours urine, both basal and after tryptophane load. In addition, histopathological and histochemical studies for lactase, succinic dehydrogenase, alkaline phosphatase, acid phosphatase, and alpha-non-specific esterases activities were done for the intestinal mucosal biopsies. All the previous investigations were then repeated after two months treatment with 500 mg/day diiodohydroxyquinoline. The tryptophan metabolites were significantly low in the diseased infants, both basal and after tryptophan load. Moreover, the intestinal enzymes activities were altered. After 2 months treatment with diiodohydroxyquinoline the diseased infants became clinically improved, tryphtophan metabolites became normal, but the activities of the intestinal enzymes were not altered. The biochemical and histochemical findings were discussed, giving the possibility of competitive inhibition of the diiodohydroxyquinolines and the by-product 8 OH Quinololic acid resulting in more degradation of Kneurine and 3 OH Kneurenine to nicotinamide adenine dinucleotide.

Acrodermatitis↗

PubMed1992

Biosynthesis of glyantrypine by Aspergillus clavatus.

The biosynthesis of glyantrypine from radiolabelled amino acid precursors has been shown experimentally to involve anthranilic acid, tryptophan and glycine. Low values for percentage incorporation of radiolabel into glyantrypine were partly influenced by a complex array of other novel alkaloids shown by the radiolabelling experiments to be related to glyantrypine. Interpretation of radiolabel incorporation from [14C-carboxyl]-anthranilic acid into microbial metabolites seen to contain an anthranilyl moiety in various biosynthetic arrangements is discussed. The possibility of diversion of anthranilic acid from the kynurenine pathway to glyantrypine biosynthesis is recognised.

Alkaloids↗

PubMed1981

Tolfenamic acid. Detection and structure of urinary metabolites.

N-(2-Methyl-3-chlorophenyl)anthranilic acid (tolfenamic acid) and its metabolites in serum and urine were analyzed by a reversed-phase ion-pair HPLC method. The major metabolites were N-(2-methyl-3-chloro-4-hydroxyphenyl)anthranilic acid, and one of the minor metabolites was N-(2-formyl-3-chlorophenyl)anthranilic acid, i.e., products resulting from hydroxylation in either the methyl group or the methylchlorophenyl group of tolfenamic acid, and further oxidation of the hydroxymethyl group to a formyl group.

Adult↗

PubMed1976

Tryptophan biosynthesis in Coprinus lagopus: a genetic analysis of mutants.

Thirty-one tryptophan-requiring mutants of Coprinus lagopus have been assigned by genetic and complementation analyses to four loci designated trp-I, trp-2, trp-3 and trp-4. The trp-1 and trp-3 loci were located in group III and trp-2 in group G of the linkage map. The trp-4 locus showed no linkage to the other trp loci or to markers in three additional linkage groups tested. From auxanographic tests and a study of accumulated biosynthetic intermediates, the enzymes controlled by each locus have been provisionally assigned. The trp-2 and trp-3 loci both appear necessary for anthranilate synthetase activity since mutants accumulated no intermediates. Only the trp-3 mutant could utilize anthranilic acid, therefore the trp-2 locus must also be involved in a subsequent step in the pathway. The trp-4 mutants utilized indole and accumulated anthranilic acid, and hence this locus is involved in the conversion of anthranilic acid to indoleglycerol phosphate. The trp-1 mutants utilized only tryptophan and accumulated indoleglycerol phosphophate and anthranilic acid. They are therefore blocked in the final steps of the pathway catalysed by tryptophan synthetase.

Agaricales↗

PubMed1979

Absorption, distribution and metabolism of propyl anthranilate.

Analysis of the gut contents of rats killed at intervals after dosage with propyl anthranilate or anthranilic acid suggested that both acid and ester were absorbed rapidly; the chief site of absorption was the stomach. Not more than a trace of the ester was hydrolysed in the stomach but of the dosed ester detected in the small intestine (less than 7%) a considerable proportion, increasing with time after dosing was present as anthranilic acid. Measurement of the level of radioactivity in the blood after administration of 14C-labelled propan-1-ol, propyl anthranilate or anthranilic acid showed that the alcohol was absorbed more rapidly than either the ester or acid. Unchanged propyl anthranilate was readily detected in the blood of rats dosed with the ester and some unhydrolysed ester was excreted in the urine. The level of radioactivity of the organs of rats 2 h and 4 h after administration of the 14C-labelled compounds was measured. Velocity constants for the excretion of 14CO2 by rats dosed with 14C-labelled propyl anthranilate were significantly lower than those found for rats dosed with [14C]propan-1-ol indicating a limiting step in the metabolism of the propyl moiety of the ester which did not occur in the metabolism of propan-1-ol. The urinary metabolites of anthranilic acid excreted by rabbits and rats dosed with the acid were qualitatively the same as those excreted by these species after dosing with propyl anthanilate; some quantitative differences were however, observed.

Animals↗

PubMed2003

Synthesis of some newer derivatives of 2-amino benzoic acid as potent anti-inflammatory and analgesic agents.

Diazotization of N-benzylidene anthranilic acids 1a-1n at pH 9 yielded N-[alpha-(phenylazo) benzylidene] anthranilic acids 2a-2n and at pH 3 yielded N-benzylidene-5-(phenylazo) anthranilic acids 3a-3n. When compounds 3a-3n were treated with thioglycolic/thiolactic acid in the presence of anhydrous ZnCl(2), 2-(4-oxo-2-phenylthiazolidin-3-yl)-5-(phenylazo) benzoic acids 4a-4n were afforded. The newly synthesized compounds were screened for their anti-inflammatory and analgesic activities and were compared with standard drugs, aspirin and phenylbutazone. Out of the compounds studied, the most active compound 4n showed more potent activity than the standard drugs at all doses tested.

Analgesics↗

PubMed1971

Production of substituted L-tryptophans by fermentation.

Claviceps purpurea has been shown to produce extracellular l-tryptophan from indole in stirred fermentors. The substrate specificity of this conversion was investigated by using substituted indoles, anthranilic acid, and 4-chloro-anthranilic acid. Addition of 2-, 4-, 5-, 6-, and 7-methyl indole or 6-chloroindole to C. purpurea C1M produced the corresponding substituted l-tryptophan. In contrast, addition of l-methyl, 6-trifluoromethyl, 6-nitro-, or 4-benzyloxy-substituted indoles, or anthranilic and 4-chloroanthranilic acids did not produce detectable amounts of the corresponding tryptophan.

Ascomycota↗

PubMed2001

Tryptophan catabolism in Brevibacterium linens as a potential cheese flavor adjunct.

Attempts to develop a desirable reduced fat Cheddar cheese are impeded by a propensity for flavor defects such as meaty-brothy, putrid, fecal, and unclean off-flavors in these products. Recent studies suggest aromatic amino acid catabolism of starter, adjunct, and nonstarter lactic acid bacteria significantly impact off-flavor development. The objective of this study was to delineate pathways for catabolism of tryptophan (Trp) in Brevibacterium linens, a cheese flavor adjunct, and to determine the potential for this organism to contribute to this defect. Growth and production of aromatic compounds from Trp by B. linens BL2 were compared in two incubated conditions (laboratory and a cheese-like environment). A chemically defined medium was used to determine the cellular enzymes and metabolites involved in Trp catabolism. Trp was converted to kynurenine, anthranilic acid, and three unknown compounds in laboratory conditions. The accumulation of other unknown compounds in the culture supernatant in laboratory conditions indicated that B. linens BL2 degraded Trp by various routes. Up to 65% of Trp was converted to anthranilic acid via the anthranilic acid pathway. To assess this potential before cheese making, the cells were incubated in cheese-like conditions (15 degrees C, pH 5.2, no sugar source, 4% NaCl). Trp was not utilized by BL2 incubated in this condition. Enzyme studies using cell-free extracts of cells incubated in laboratory conditions and assayed at optimal and nonoptimal enzyme assay conditions revealed Trp transaminase (EC 2.6.1.27) was active before enzymes of the anthranilic acid pathway were detected. The products of Trp transaminase activity were not, however, found in the culture supernatant, indicating these intermediates were not exported nor accumulated by the cells. Enzymes assayed in nonoptimal conditions had considerably lower enzyme activities than found in laboratory incubation conditions. Based on these results, we hypothesize that these enzymes are not likely to be involved in the formation of compounds associated with off-flavors in Cheddar cheese.

Brevibacterium↗