[3-METHOXY-4-HYDROXYMANDELIC ACID (VANILLYL-MANDELIC) AND 3-METHOXY-4-HYDROXYPHENYLACETIC ACID (HOMOVANILLIC) IN SYMPATHOADRENAL SYNDROMES].
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Adrenal Gland Neoplasms↗
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Characteristics of transposon insertion mutants of mandelic acid-utilizing Pseudomonas putida strain A10L.
A soil isolate, Pseudomonas putida strain A10L that utilizes mandelate via the mandelate pathway was mutagenized by transposon Tn5-Mob insertion and mutant 168 lacking mandelate racemase (MR) and a mutant 254 lacking benzoylformate decarboxylase (BFDC) were obtained. Expression of (S)-mandelate dehydrogenase (MDH), BFDC, NAD(+)-dependent benzaldehyde dehydrogenase (BDH) and NADP(+)-dependent BDH in the MR-lacking mutant was not affected by the insertion, and it was inducible similarly to the wild type strain. On the other hand, expression of MR and MDH in the BFDC-lacking mutant was low and constitutive, and NAD(+)- and NADP(+)-dependent BDHs were produced at a rather high level under non-induced conditions by the mutant. Genes for MR (mdlA), MDH (mdlB), and BFDC (mdlC) were indicated to be organized in an operon in the order of mdlCBA. Optical resolution to obtain (R)-mandelate, a useful synthon for pharmaceuticals, was shown to be performed with the MR-lacking mutant.
Aldehyde Oxidoreductases↗
Effect of oestradiol-17 beta on the metabolism of noradrenaline in brain slices of ovariectomized rats.
Ovariectomized rats received a single injection of 10 microgram oestradiol-17 beta 3-benzoate; 90 min or 19 h after injection, slices of various brain areas were prepared and incubated with tritiated noradrenaline for 30 min. Methylated and non-methylated metabolites of tritiated noradrenaline were determined after chromatographic separation. Nineteen h after administration of oestradiol-17 beta 3-benzoate, the formation of normetanephrine, 3-methoxy 4-hydroxy phenylglycol and 3-methoxy 4-hydroxy mandelic acid was decreased (P less than 0.05) in hypothalamic tissue, whereas that of 3,4-dihydroxy mandelic acid was increased (P less than 0.001). In thalamus tissue a decrease or normetanephrine (P less than 0.005) and an increase of 3,4-dihydroxy mandelic acid (P less than 0.001) were also observed. No conclusive results were obtained with hypophyseal tissue. The present findings suggest that oestrogens reduce the methylation of noradrenaline, probably through a competitive inhibition of the catechol-O-methyl-transferase by 2-hydroxylated oestrogens.
Animals↗
Nitrilase from Pseudomonas fluorescens EBC191: cloning and heterologous expression of the gene and biochemical characterization of the recombinant enzyme.
The gene encoding an enantioselective arylacetonitrilase was identified on a 3.8 kb DNA fragment from the genomic DNA of Pseudomonas fluorescens EBC191. The gene was isolated, sequenced and cloned into the L-rhamnose-inducible expression vector pJOE2775. The nitrilase was produced in large quantities and purified as a histidine-tagged enzyme from crude extracts of L-rhamnose-induced cells of Escherichia coli JM109. The purified nitrilase was significantly stabilized during storage by the addition of 1 M ammonium sulfate. The temperature optimum (50 degrees C), pH optimum (pH 6.5), and specific activity of the recombinant nitrilase were similar to those of the native enzyme from P. fluorescens EBC191. The enzyme hydrolysed various phenylacetonitriles with different substituents in the 2-position and also heterocyclic and bicyclic arylacetonitriles to the corresponding carboxylic acids. The conversion of most arylacetonitriles was accompanied by the formation of different amounts of amides as by-products. The relative amounts of amides formed from different nitriles increased with an increasing negative inductive effect of the substituent in the 2-position. The acids and amides that were formed from chiral nitriles demonstrated in most cases opposite enantiomeric excesses. Thus mandelonitrile was converted by the nitrilase preferentially to R-mandelic acid and S-mandelic acid amide. The nitrilase gene is physically linked in the genome of P. fluorescens with genes encoding the degradative pathway for mandelic acid. This might suggest a natural function of the nitrilase in the degradation of mandelonitrile or similar naturally occurring hydroxynitriles.
Aminohydrolases↗
Disturbances in psychological functions of workers occupationally exposed to styrene.
The relationship between long-term occupational styrene exposure and disturbances in psychological functions was studied. The exposed group consisted of 98 male workers exposed to styrene in the manufacture of polyester plastic products, and the comparison group comprised 43 concrete reinforcement workers. The duration of exposure in years and the mean mandelic acid concentration in urine (five determinations during 5 weeks before the clinical examination) and the cumulative dose of exposure were used as the indicators of exposure. The psychological functions studied were intelligence, visuomotor speed, visuomotor accuracy, memory, vigilance, and psychomotor performance. Some personality test variables were also included. In a group comparison two variables (visuomotor inaccuracy and poor psychomotor performance) out of 20 showed statistically significant differences and characterized the styrene exposed group. These findings were confirmed when workers with low and high styrene exposure were compared. One variable measuring visuomotor speed and another measuring visual memory were related to the duration of exposure (R = 0.28, p less than 0.05). In a multiple regression analysis disturbances in visuomotor accuracy, poor psychomotor performance, and lowered vigilance proved to have some connection with a high mandelic acid concentration (R = 0.49, p less than 0.01). In addition workers with disturbances in visuomotor accuracy and slight disturbances in virumotor speed had higher mandelic acid concentrations when compared with those workers without any deterioration. The results indicate that disturbances in visuomotor accuracy and, to a lesser degree, in psychomotor performance are the main findings measured by test methods used in this study and related to one indicator of styrene exposure, mandelic acid concentration. The psychological methods used revealed subclinical symptoms related to exposure, and they should aid in making group diagnoses, e.g., when additional information is needed for the determination of the threshold limit value. The deterioration found in visuomotor accuracy could be related to lowered safety in work and traffic.
Adolescent↗
Asymmetric environments in encapsulation complexes.
Symmetrical, self-assembled capsules capable of surrounding two guests offer a new approach to enantioselection through coencapsulation: when one guest is chiral, the space remaining is also chiral. This notion is explored within a cylindrical capsule. The dimensions of the capsule select appropriately sized combinations of guests, the shape of the capsule prevents tumbling of rigid molecules, and the chemical surface of the capsule orients polar functions within. Chiral carboxylic acids such as mandelic acid and alpha-Br-butyric acid are identified as promising compounds for this purpose, but diastereoselection is modest (<25% de).
Butyrates↗
Phenylalanine metabolism in uremic and normal man.
The metabolism of phenylalanine and tyrosine was evaluated in six normal men, five chronically uremic men, and three men undergoing maintenance hemodialysis. Phenylalanine, tyrosine, and 13 acidic metabolites of those amino acids were measured in plasma postabsorptively and in plasma and urine after a phenylalanine load of 100 mg/kg. In addition, five normal subjects and five dialysis patients ingested L-[14C]-phenylalanine (uniformly labeled) with the load. In uremic and dialysis patients, plasma phenylalanine rose higher and fell more gradually after the load, and tyrosine rose more slowly. The 24-hr urinary concentrations of phenylalanine and tyrosine were similar in the three groups. At 24 hr, cumulative expiration of 14CO2 was 20.2% in the dialysis patients and 28.4% in the normal subjects. Plasma phenylalanine levels and 14CO2 expiration varied with protein intake in normal subjects. In uremic and dialysis patients, plasma phenyllactic acid, p-hydroxyphenylacetic acid, and p-hydroxybenzoic acid were elevated, the last one markedly so. Moreover, plasma phenylpyruvic acid (PPA) and mandelic acid were detected only in dialysis patients. After the phenylalanine load, plasma conjugated phenylacetic acid rose in uremic patients, and PPA increased transiently in some dialysis patients. In urine of dialysis patients, concentrations of benzoic acid and conjugated o-hydroxyphenylacetic acid were decreased, and PPA was sometimes increased. The data suggest a mild impairment in the hydroxylation of phenylalanine which does not result in marked changes in plasma or in urinary metabolites after a phenylalanine load.
Acetates↗
A note on individual differences in the urinary excretion of optical enantiomers of styrene metabolites and of styrene-derived mercapturic acids in humans.
Urine samples from 20 male workers in the polyester industry exposed by inhalation to styrene concentrations ranging from 29 to 41 ppm were investigated. Excretion products of styrene metabolism, mandelic acid and mercapturic acids, were purified from the urine over an extraction column packed with Porapak Q, with subsequent ether elution. The optical enantiomers R- and S-mandelic acid were then determined by thin layer chromatography (TLC) using chiral plate material and selective staining with vanadium pentoxide. Quantitative analysis of these compounds was performed using commercial reference substances. Styrene-specific mercapturic acids were analyzed by a modified TLC method, using synthesized reference substances. The concentration of racemic mandelic acid in the individual urine samples ranged from 80 to 1610 mg/l, and the ratio of the R- and S-enantiomers ranged from 0.7 to 2.2. These individual variations are not explained by differences in individual styrene exposure levels, or by differences in the concentration of the urine samples (in relation to creatinine excretion). Styrene-specific mercapturic acids were detected in the urine of only 1 of the 20 workers, at a concentration much lower than expected from previous investigations by others in humans and laboratory animals, in which less specific analytical methods had been used. The results point to marked interindividual differences in metabolism of styrene, probably related to enzyme polymorphisms.
Acetylcysteine↗
Reversed-phase ion-pair partition chromatography of phenylacetic, mandelic and pyridinecarboxylic acid derivatives.
Phenylacetic, mandelic and pyridinecarboxylic acids of physiological interest have been separated by ion-pair partition chromatography with 1-pentanol as stationary phase and tetrabutylammonium as counter ion in the aqueous mobile phase. The stability of the chromatographic system is very high and the support is spontaneously re-coated with stationary phase. Untreated plasma samples can be injected in relatively large volumes without serious loss of separating efficiency. A venting system was found efficiently to reduce disturbing early peaks on injection of biological samples.
Buffers↗
Application of preferential crystallization to resolve racemic compounds in a hybrid process.
The application of preferential crystallization is at present limited to conglomerate forming systems, which cover only a minor part of chiral substances. In this paper, a hybrid process is proposed that extends the applicability of the preferential crystallization principle to the more common racemic compound forming systems. It comprises a preliminary (e.g., chromatographic) enantiomeric enrichment step and preferential crystallization to finally produce the desired pure enantiomer(s). The applicability of preferential crystallization to racemic compounds is demonstrated on the example of mandelic acid as a model system. Direct monitoring of the separation progress is performed using combined online polarimetry and online density measurements. A cyclic crystallization process, which provides alternating the pure mandelic acid enantiomer and the racemic compound, is feasible and allows the resolution of rac-mandelic acid as part of the proposed hybrid approach.
Crystallization↗
Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers.
Factory surveys were conducted in the second half of work weeks on 360 solvent workers (202 men and 158 women) and 281 controls in China. Monitoring personal exposures showed that ethylbenzene exposure was low (geometric mean 1.8 ppm) and was accompanied by coexposure to toluene (1.5 ppm) and three xylene isomers (6.7 ppm). Urine samples collected at the end of the eight-hour shift were analyzed for phenylglyoxylic and mandelic acids by high-pressure liquid chromatography at 257 nm. Despite the low level of the exposures, a significant correlation was observed between ethylbenzene exposure and urinary phenylglyoxylic acid, with high (0.6-0.7) correlation coefficients, suggesting that urinary phenylglyoxylic acid is a good marker of occupational exposure to ethylbenzene. Mandelic acid also correlated with ethylbenzene exposure, but with much smaller coefficients (0.2), possibly because the method employed was more sensitive to phenylglyoxylic acid than to mandelic acid.
Journal Article↗
A functionally diverse enzyme superfamily that abstracts the alpha protons of carboxylic acids.
Mandelate racemase and muconate lactonizing enzyme are structurally homologous but catalyze different reactions, each initiated by proton abstraction from carbon. The structural similarity to mandelate racemase of a previously unidentified gene product was used to deduce its function as a galactonate dehydratase. In this enzyme superfamily that has evolved to catalyze proton abstraction from carbon, three variations of homologous active site architectures are now represented: lysine and histidine bases in the active site of mandelate racemase, only a lysine base in the active site of muconate lactonizing enzyme, and only a histidine base in the active site of galactonate dehydratase. This discovery supports the hypothesis that new enzymatic activities evolve by recruitment of a protein catalyzing the same type of chemical reaction.
Amino Acid Sequence↗
Impaired colour discrimination among workers exposed to styrene: relevance of a urinary metabolite.
OBJECTIVES: To survey the loss of colour vision among Japanese workers who have been exposed to styrene concentrations currently considered low (about 20 ppm). Also to assess the effects of styrene by examination of the nature of the relation between disorder of colour vision and age, alcohol consumption, and other variables. METHODS: Colour discrimination was examined in 64 male workers exposed to styrene (mean age; 38.0, mean exposed years; 7.0) and in 69 controls (mean age; 38.0). A standardised questionnaire was adopted to collect work history, occupational or non-occupational solvent exposure, alcohol consumption, and drug use. Colour vision was evaluated by the Lanthony desaturated panel D-15 test. The results of the test were expressed as the colour confusion index (CCI). RESULTS: The mean atmospheric styrene concentration was about 20 ppm. The mean urinary concentration of mandelic acid was 0.22 g/l. There was a significant difference in CCI between exposed workers and age matched controls. Colour vision of workers whose concentration of urinary mandelic acid was > or = 0.42 g/l was significantly impaired when compared with workers whose concentration was < 0.42 g/l. Multiple linear regression analysis that controlled confounding variables such as age, alcohol consumption, smoking, and educational attainment showed that the CCI was significantly related to the concentration of urinary mandelic acid. In both exposed workers and controls, the types of defects were mostly blue-yellow loss, although a few subjects showed complex loss. No one showed only red-green loss. CONCLUSIONS: These findings suggest that exposure to moderate styrene concentrations can lead to impairment of colour vision, and that there is a significant correlation with the urinary metabolite of styrene.
Adult↗
Neurophysiological findings among workers occupationally exposed to styrene.
Ninety-six male workers occupationally exposured to styrene in 24 plants producing reinforced polyester plastic products were studied neurophysiologically. The mean age of the subjects was 29.6 +/- 7.4 years, and the duration of the exposure varied from 6 months to 14 years (mean 5.0 years). Mandelic acid concentration in the urine (mean of five values determined during five consecutive weeks) was used as the measure of exposure. The individual means of the mandelic acid concentrations varied from 7 to 4,715 mg/dm3 (median 808 mg/dm3). Neurotoxic effects of styrene exposure upon the central nervous system were revealed by abnormalities in the EEG. The overall prevalence of abnormal EEGs was 24% (23 out of 96), which is higher than that found among a normal population (p less than 0.05). Abnormal EEGs were found in one-third of the subjects with relevant styrene exposure (mandelic acid concentration over 700 mg/dm3), while low-level styrene exposure did not increase the prevalence of normal EEGs above that found in a normal population. Nerve conduction velocity measurements performed on 40 subjects did not reveal any definite relationship between neuropathy and styrene exposure. The EEG examination is useful in the investigation of the neurotoxic effects of styrene. Whenever a possibility exists of excessive styrene exposure or beginning poisoning, the workers should be submitted to an EEG examination.
Adolescent↗
Choice reaction time in workers exposed to styrene vapour.
Behavioural effects of occupational exposure to vapour from styrene-based resin were investigated in 10 female workers with a portable test of choice reaction time. Testing was carried out both at the beginning and end of the day's shift. Uptake and metabolism of styrene were assessed by monitoring post-shift urinary mandelic acid excretion rates. By using these data workers were allocated to three groups reflecting zero, low or high exposure. After exposure slowing of reaction times was found in those with the highest mandelic acid excretion rates, whereas a slight improvement or no change was found in those with low or zero exposure. Subsequent improvements in extraction and ventilation in the workroom were shown to be associated with both decreased mandelic acid excretion and absence of long reaction times in those previously most heavily exposed.
Air Pollutants, Occupational↗
Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring.
BACKGROUND: Within- and between-worker variance components have seldom been reported for both environmental and biological data collected from the same persons. AIMS: To estimate these variance components and their ratio for air contaminants and urinary metabolites in two different work environments and to predict the attenuation of exposure-response relationships based on these measures. METHODS: Parallel measurements of air and urine were performed among workers exposed to monoterpenes in sawmills (urinary metabolite: verbenol) and styrene in reinforced plastics factories (urinary metabolite: mandelic acid). RESULTS: Among the sawmill workers, variance components of the air and urinary verbenol results were similar; for the reinforced plastics workers the estimated between-worker variance component was greater for styrene in air than mandelic acid in urine. This suggests that attenuation bias would be about equal if air or biological monitoring were employed for monoterpene exposures, but would be greater if urinary mandelic acid were used instead of airborne styrene in an investigation of styrene exposure. CONCLUSIONS: Personal air samplers provide data with similar or superior quality to urinary metabolites as measures of exposure to these monoterpenes in sawmills and styrene in reinforced plastics factories.
Air Pollutants, Occupational↗
Visual dysfunction among styrene-exposed workers.
OBJECTIVES: The present study was undertaken to examine the relation between visual functions and occupational exposure to styrene. METHODS: A total of 128 workers (85% of the total population), from three glass-reinforced plastics plants in Canada, agreed to participate in the study. Environmental and biological measures were made on the day(s) prior to the assessment of near visual acuity (National Optical Visual Chart), chromatic discrimination (Lanthony D-15 desaturated panel), and near contrast sensitivity (Vistech 6000). The analyses were performed on 81 workers with near visual acuity of at least 1 min of arc at 0.5 m. RESULTS: The subjects were relatively young [29 (SD 8) years], with little seniority [5 (SD 4) years]. Styrene exposure for 8 h ranged from 6 to 937 (first quartile 21 mg.m-3, third quartile 303 mg.m-3), depending on the job site. The end-shift concentrations of urinary mandelic acid ranged from nondetectable to 1.90 mmol.mmol creatinine-1. Significant positive relations were found between the internal and external styrene exposure measurements and color vision loss adjusted for age, alcohol consumption, and seniority in a multiple regression analysis. The multiple regression analysis is also showed that the end-shift concentration of urinary mandelic acid was inversely related to contrast sensitivity at 6 and 12 cycles.degree-1. Logistic multiple regression models indicated that the end-shift concentration of urinary mandelic acid was related to the prevalences of blurred vision, tearing, and eye irritation. CONCLUSIONS: These findings suggest that there is a positive relation between styrene exposure and early color and contrast vision dysfunction.
Adult↗
Neurobehavioral effects of acute styrene exposure in fiberglass boatbuilders.
A field investigation of the effects of acute exposure to styrene among fiberglass boatbuilders was performed. Personal samples of styrene in breathing zone air and postshift urinary mandelic acid were collected for 105 workers exposed and not exposed to styrene in 6 fiberglass boatbuilding companies in New England. Three tests from the computerized Neurobehavioral Evaluation System (NES) were performed by the subjects in the morning before exposure to styrene, near midday, and at the end of the work day. Duration of exposure averaged 2.9 years (SD = 4.6), 8-hour TWA styrene exposure averaged 29.9 ppm (SD = 36.2), and urinary mandelic acid averaged 347 mg/g creatinine (SD = 465). Regression analyses indicated a statistically significant relationship between postshift performance on the Symbol-Digit test and both acute styrene exposure and mandelic acid. Other analyses comparing workers exposed to less than 50 ppm and greater than 50 ppm styrene also showed a significant effect on Symbol-Digit performance. All three NES tests showed test-retest correlation coefficients above .80, and ease of use for collection of neurobehavioral data under field conditions was demonstrated.
Adult↗