Vanillactic Acid Research Articles

Conjugated versus "free" acidic metabolites of catecholamines in random urine samples: significance for the diagnosis of neuroblastoma.

Random urine samples were obtained from 31 patients with neuroblastoma (newborn to 8 yr of age) and from 100 children without this tumor (newborn to 10 yr). The urine samples were studied for the presence of sulfate and glucuronide conjugates of homovanillic (HVA), dihydroxyphenylacetic, vanilmandelic, and vanillactic acids. The urinary concentrations of these acids were determined by capillary gas-chromatography before and after enzymatic treatment with glucuronidase and sulfatase. Concentrations of the "free" fraction and "total" urinary content of these acids were determined using the results from untreated and treated urines respectively. Age-related reference values were established for children without neuroblastoma. Fractions of the total content of urinary HVA (18-39%) and dihydroxyphenylacetic acid (36-66%) were excreted as glucuronides and/or sulfates by the control group, with the highest conjugated fractions found in the urine of young infants (0-3 months). Vanilmandelic was excreted mainly as "free" acid (unconjugated), whereas vanillactic acid was undetectable in almost all control samples. Patients with neuroblastoma also excreted a fraction of these acids as glucuronide and/or sulfate conjugates, (25% of urinary HVA, 39% of dihydroxyphenylacetic acid and 45% of vanillactic acid) whereas vanilmandelic acid was excreted only as "free" in controls. Determination of "total" rather than "free" urinary HVA was diagnostic in one neuroblastoma patient with borderline "free" HVA levels, whereas determination of "free" or "total" dihydroxyphenylacetic acid and vanillactic acid did not improve the diagnostic sensitivity in the cases examined. We conclude that it may be clinically useful to determine "total" urinary HVA in patients with borderline "free" HVA levels who are suspected of having neuroblastoma.

Data processing of urine chromatograms for the clinical management of melanoma

A data processing system for the analysis of melanoma urine chromatograms is described. The system operates on a MODCOMP IV computer and processes in three distinct stages the chromatographic data that has been logged and stored on nine-track magnetic tape. While the initial data reduction stage uses standard programming techniques for peak-area computations, the other stages involve novel graphical displays that provide an overview not only of the clinical data, but also of the operation of the chromatography system itself. Among other results, the data processing provides clear evidence that vanillactic acid is a urinary melanogen.

Initial Urinary Catecholamine Metabolite Concentrations and Prognosis in Neuroblastoma

Initial urinary catecholamine metabolite and amino acid excretion patterns were examined in 54 children with neuroblastoma. The relationships between prognosis and age at diagnosis, stage of disease, primary site, and histologic grade of tumor were similar in this population to those found in previous studies, but only age and stage were found to be independent prognostic variables. Prognosis in disseminated disease was found to correlate directly with the urinary vanilmandelic acid (VMA)/homovanillic acid (HVA) ratio but not with the absolute levels of HVA. The presence of the dopa metabolite, vanillactic acid, as well as increased amounts of cystathionine and/or low levels of VMA indicated poor prognosis. These results are consistent with the hypothesis that biochemically primitive neuroblastomas deficient in dopamine beta-hydroxylase are move virulent than their mature analogues which produce epinephrine, norepinephrine, and their metabolites.

Deuteration of catecholamines, catecholamine metabolites and tryptophan metabolites

AbstractThe preparation of some deuterium labelled catecholamines, catecholamine metabolites and tryptophan metabolites is described. Simple exchange reactions in DC1/D20 solution or reductions with Li Al D4 were used. The deuterium labelled compounds prepared are suitable for use as internal standards for quantitative mass‐fragmentographic analysis of their unlabelled analogs in biological material. Mass spectra of trimethylsilyl and trimethylsilyl‐N‐trifluoroacetyl derivatives of 2,5,6‐trideutero vanillactic acid, 1,1‐dideutero‐1‐hydroxy‐2 (2,5,6‐trideutero catechol)‐ethane, 2,5,6‐trideutero epinephrine, 2,5,6‐trideutero normetanephrine and hexadeutero indole‐3‐acetic acid are given together with those of their natural occurring analogs.

Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography.

We describe a mass-fragmentographic method for determination in urine of the following metabolites of L-3,4-dihydroxyphenylalanine and dopamine: vanillactic acid, 3,4-dihydroxyphenylacetic acid, 3-methoxy-4-hydroxyphenylethanol, and 3,4-dihydroxyphenylethanol. Deuterated analogs were used as internal standards. The method is fast, reproducible, sensitive, and selective, and does not require the use of time-consuming clean-up procedures. Normal excretion values in terms of creatinine, expressed as a function of age, as well as values obtained for patients with neurogenic tumors, a patient during therapy with L-3,4-dihydroxyphenylalanine, and a patient receiving dopamine are presented and discussed.

Gas chromatographic determination of urinary vanilglycolic acid, vanilglycol, vanilacetic acid and vanillactic acid — Chemical parameters for the diagnosis of neurogenic tumours and the evaluation of their treatment

A gas Chromatographic method is described for the determination of urinary vanilglycolic acid, vanilglycol, vanilacetic acid and vanillactic acid as their trimethylsilyl derivatives. These metabolites are chemical parameters for the diagnosis of neurogenic tumours. Their determination is especially recommended in order to evaluate the effect of the therapy. Results in normals and controls are given. Data in a number of selected patients with neuroblastoma, ganglioneuroma and phaeochromocytoma are presented and discussed.

Densitometric determination of catecholamine metabolites and 5-hydroxy-indoleacetic acid after two-dimensional thin-layer chromatography on cellulose

A quantitative two-dimensional chromatographic determination for the catecholamine metabolites vanilglycolic (vanilmandelic) acid, vanilacetic acid, vanillactic acid and vanilglycol is described. The method can also be used for the determination of 5-hydroxy-indoleacetic acid. The analytical procedure consists of the following steps: 1. extraction (after enzymatic hydrolysis when vanilglycol has to be determined); 2. two-dimensional chromatography on thin-layer cellulose; 3. quantitative evaluation of the spots by means of a chromatogram scanner. Standard deviations, recoveries, 24-h excretions in 10 normal adults and results in 10 patient suffering from neurogenic tumors are given. Some of the merits of a multi-component determination of the type described here for the clinical diagnosis of secreting neurogenic and serotonin-producing tumors are discussed.

Dopa and 3- O-methyldopa in cerebrospinal fluid of parkinsonism patients during treatment with oral l-dopa

In a study of dopa metabolism as reflected in the cerebrospinal fluid of parkinsonism patients during l-dopa therapy, it became evident that 3- O-methyldopa is present in these fluids in a concentration eight to ten times that of dopa. This concentration is sufficiently high to cause significant interference in the determination of dopa if appropriate corrections are not made. New fluorimetric methods for the determination of 3- O-methyldopa and dopa in cerebrospinal fluid were devised. The procedure for determination of dopa has the advantage of greater sensitivity than the traditional iodine oxidation method. A thin-layer chromatographic search was made for the metabolites of 3- O-methyldopa, vanilpyruvic acid and vanillactic acid, in cerebrospinal fluid. Neither was found, suggesting that the 3- O-methyldopa in cerebrospinal fluid originates largely from systemic metabolism of dopa rather than from the central nervous system. These findings are discussed in the light of present trends in l-dopa therapy.

Vanillactic acid in the urine of melanoma patients

Arsenic exposure is considered a major environmental threat to human health. It is already known that high-level arsenic exposure has adverse effects on human health. Since the pregnant women are known to be more susceptible to some chemical exposures than ordinary people, the understanding regarding the health effects of low-level arsenic exposure on pregnant women is critical and remains unclear. The aim of this study is to investigate the urinary metabolic changes of pregnant women exposed to low-dose arsenic, and to identify biomarkers from metabolomics analysis. Urine samples of 246 pregnant women were collected in the first trimester of pregnancy and were divided into three groups based on the tertile distribution of urinary arsenic concentrations which were determined using inductively coupled plasma mass spectrometry (ICP-MS). Changes in the metabolite profile were measured using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF MS). Arsenic- related metabolic biomarkers were investigated by comparing the samples of the first and third tertiles of arsenic exposure classifications using a partial least-squares discriminant model (PLS-DA). Nine urine potential biomarkers were putatively identified, including LysoPC (14:0), glutathione, 18-carboxy-dinor-LTE4, 20-COOH-LTE4, cystathionine ketimin, 1-(beta-d-ribofuranosyl)-1,4-dihydronicotinamide, thiocysteine, p-cresol glucuronide and vanillactic acid. The obtained results showed that environmental arsenic exposure, even at low levels, could cause metabolite alterations in pregnant women which might be associated with adverse health outcomes. This is the first report on metabolic changes in pregnant women for arsenic exposure. The findings may be valuable for the arsenic risk assessment for pregnant women.

The vanillactic acid in the urine of melanoma patients

The vanillactic acid in the urine of melanoma patients

Metabolism of aromatic amino acids in collagen diseases. Urinary excretion of metanephrine and normetanephrine, and spontaneous degradation of vanilpyruvic acid

1. 1. Urinary excretion of total metanephrine and normetanephrine was significantly lower in 20 cases of rheumatic fever and relative “collagen diseases”, as compared to 10 normal control cases. 2. 2. Ingestion of l-tryptophan resulted, in 2 out of 3 normal children, in significant increase of the urinary excretion of these compounds ; m 4 out of 6 patients it resulted in significant decrease. The difference between the groups was statistically significant. 3. 3. Synthetic vanilpyruvic acid produced a number of degradation products when its solutions in ether or ethyl acetate were stored in the freezer without exclusion of oxygen, or when freshly prepared solutions were subjected to paper chromatography with an alkaline solvent system. Besides vanillin and homovanillic acid, a substance, accounting for the largest percentage of the degradation products, coincided on the chromatograms with the spot of vanillactic acid.

Metabolism of aromatic amino acids in collagen diseases. urinary excretion of vanillactic acid and dihydroxyphenylalanine

1. (1) Vanillactic acid was newly synthesized, and its chromatographic properties and reactions were investigated and found to be in satisfactory agreement with those of the naturally occurring vanillactic in the urine in rheumatic fever. 2. (2) Increased urinary excretion of DOPA was observed in children suffering from collagen diseases. A relatively simple procedure was devised for the semiquantitative determination of DOPA in the urine. 3. (3) Increased urinary output of an indole compound, probably 3-methoxy-tryptophan, was observed in rheumatic fever. 4. (4) Aspects of the metabolism of aromatic amino acids in rheumatic fever are discussed in relation to these findings.