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At least 19 recordsLinked to original sources
PubMed1979

Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma.

We report quantitative data on beta-glucuronidase- and sulfatase-hydrolyzable conjugates of homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid in the urine of 20 apparently normal and healthy control persons and of three patients with neuroblastoma. We used organic solvent extraction and capillary gas chromatography. There was considerable person-to-person variation in the conjugation percentages calculated. Mean conjugated percentages of the four compounds for 16 normal healthy persons 2.5--40 years of age were, respectively, 12%, 33%, 14%, and 35%. For newborns and patients with neuroblastoma, these percentages were somewhat different. Increased amounts of vanillic acid were found in the urine of the patients with neuroblastoma, but results of a small metabolic study in rats suggest that this increase most probably is of dietary origin.

3,4-Dihydroxyphenylacetic Acid↗
PubMed2000

Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13.

From a ferulic-acid-degrading Pseudomonas fluorescens strain (BF13), we have isolated a transposon mutant, which retained the ability to bioconvert ferulic acid into vanillic acid but lost the ability to further degrade the latter acid. The mutant, BF13-97, was very stable, and therefore it was suitable to be used as a biocatalyst for the preparative synthesis of vanillic acid from ferulic acid. By use of resting cells we determined the effect on the bioconversion rate of several parameters, such as the addition of nutritional factors, the concentration of the biomass, and the carbon source on which the biomass was grown. The optimal yield of vanillic acid was obtained with cells pregrown on M9 medium containing p-coumaric acid (0.1% [wt/vol]) as a sole carbon source and yeast extract (0.001% [wt/vol]) as a source of nutritional factors. Under these conditions, 1 mg (wet weight) of biomass produced 0.23 mg of vanillic acid per h. The genomic region of BF13-97 flanking the transposon's site of insertion was cloned and sequenced revealing two open reading frames of 1,062 (vanA) and 954 (vanB) bp, respectively. The van genes are organized in a cluster and encode the subunits of the vanillate-O-demethylase, which catalyzes the first step of the vanillate catabolism. Amino acid sequences deduced from vanA and vanB genes were shown to have high identity with known VanAs and VanBs from Pseudomonas and Acinetobacter spp. Highly conserved regions known to exist in class IA oxygenases were also found in the vanillate-O-demethylase components from P. fluorescens BF13. The terminal oxygenase VanA is characterized by a conserved Rieske-type [2Fe-2S](R) ligand center. The reductase VanB contains a plant-type ferredoxin [2Fe-2S](Fd), flavin mononucleotide, and NAD-ribose binding domains which are located in its C-terminal and N-terminal halves, respectively. Transfer of wild-type vanAB genes to BF13-97 complemented this mutant, which recovered its ability to grow on either vanillic or ferulic acid.

Base Sequence↗
PubMed1993

Mechanisms of ferulic acid conversions to vanillic acid and guaiacol by Rhodotorula rubra.

Resting cells of Rhodotorula rubra converted transferulic acid (1) to vanillic acid (2), then to guaiacol (3) and protocatechuic acid (4), under aerobic conditions. In an argon atmosphere, R. rubra transformed ferulic acid to vanillic acid and 4-hydroxy-3-methoxystyrene (5). Metabolites were isolated by solid-phase extraction and characterized by mass spectrometry, 1H, and 13C-nuclear magnetic resonance spectroscopy (NMR). The biotransformation of ferulic acid to vanillic acid by R. rubra cell-free extracts required CoA, ATP, and NAD+. Mass spectrometry and 13C-NMR were used to demonstrate the incorporation of oxygen from H2(18)O during the conversion of ferulic acid to vanillic acid. The results suggest a parallel between this bioconversion reaction and the beta-oxidation of fatty acids. Proton-carbon correlation NMR spectroscopy was used to demonstrate the specific incorporation of deuterium from D2O into guaiacol obtained from vanillic acid. The incorporation of deuterium implicates the involvement of a quinoid vanillic acid tautomer as an intermediate in the decarboxylation reaction.

Cell-Free System↗
PubMed1999

Characterization of a vanillic acid non-oxidative decarboxylation gene cluster from Streptomyces sp. D7.

The genetics of non-oxidative decarboxylation of aromatic acids are poorly understood in both prokaryotes and eukaryotes. Although such reactions have been observed in numerous micro-organisms acting on a variety of substrates, the genes encoding enzymes responsible for these processes have not, to our knowledge, been reported in the literature. Here, the isolation of a streptomycete from soil (Streptomyces sp. D7) which efficiently converts 4-hydroxy-3-methoxybenzoic acid (vanillic acid) to 2-methoxyphenol (guaiacol) is described. Protein two-dimensional gel analysis revealed that several proteins were synthesized in response to vanillic acid. One of these was characterized by partial amino-terminal sequencing, leading to the cloning of a gene cluster from a genomic DNA lambda phage library, consisting of three ORFs, vdcB (602 bp), vdcC (1424 bp) and vdcD (239 bp). Protein sequence comparisons suggest that the product of vdcB (201 aa) is similar to phenylacrylate decarboxylase of yeast; the putative products of vdcC (475 aa) and vdcD (80 aa) are similar to hypothetical proteins of unknown function from various micro-organisms, and are found in a similar cluster in Bacillus subtilis. Northern blot analysis revealed the synthesis of a 2.5 kb mRNA transcript in vanillic-acid-induced cells, suggesting that the cluster is under the control of a single inducible promoter. Expression of the entire vdc gene cluster in Streptomyces lividans 1326 as a heterologous host resulted in that strain acquiring the ability to decarboxylate vanillic acid to guaiacol non-oxidatively. Both Streptomyces sp. strain D7 and recombinant S. lividans 1326 expressing the vdc gene cluster do not, however, decarboxylate structurally similar aromatic acids, suggesting that the system is specific for vanillic acid. This catabolic system may be useful as a component for pathway engineering research focused towards the production of valuable chemicals from forestry and agricultural by-products.

Amino Acid Sequence↗
PubMed1981

Streptomyces setonii: catabolism of vanillic acid via guaiacol and catechol.

Streptomyces setonii (strain 75Vi2) was grown at 45 degrees C in liquid media containing simple aromatic compounds as principal carbon sources. Thin-layer chromatography, UV spectrophotometry, and gas chromatography were used to show that S. setonii converted benzoic acid, guaiacol, and vanillic acid to catechol; p-hydroxybenzoic acid to protocatechuic acid; and m-hydroxybenzoic acid to gentisic acid. Presence of the ring-cleavage enzymes catechol 1,2-dioxygenase, protocatechuate 3,4-dioxygenase, and gentisate 2,3-dioxygenase was shown both by O2 uptake in ring-cleavage reactions catalyzed by cell-free extracts and by changes in UV spectra that indicated the presence of specific ring-cleavage products. A unique feature of this strain was its catabolism of vanillic acid by of guaiacol and catechol, using a pathway that had not been confirmed previously.

Benzoates↗
PubMed1976

On the occurence of vanillic acid in human brain and cerebrospinal fluid.

3-methoxy-4-hydroxyphenylbenzoic (vanillic) acid was previously shown to be one of the endogenous metabolites of adrenaline and noradrenaline. Using thin-layer chromatographic methods for identification and quantification of phenolic acids and phenolic alcohols, the authors identified vanillic acid in different regions of the human brain. The concentration of vanillic acid in the cerebrospinal fluid was also determined and compared to the concentration of 3-methoxy-4-hydroxyphenylethylene glycol. The identification of VA in the human brain suggests that the vanillic acid of the cerebrospinal fluid originates, at least in part, from the catecholamines in the brain. The authors discuss other possible origins of vanillic acid besides the noradrenaline catabolism of dopamine. As the concentration of vanillic acid in the cerebrospinal fluid was found to be greater than the concentration of 3-methoxy-4-hydroxyphenylethylene glycol, it might be important for clinical biological studies to measure vanillic acid in the cerebrospinal fluid as well as the other alcoholic and acid catabolites of the catecholamines.

Brain Chemistry↗
PubMed2002

Isolation from a shea cake digester of a tannin-tolerant Escherichia coli strain decarboxylating p-hydroxybenzoic and vanillic acids.

A facultatively anaerobic, mesophilic, Gram-negative, non-motile, non-sporulated bacterium, designated strain C2, was isolated from an anaerobic digester fed with shea cake rich in tannins and aromatic compounds and previously inoculated with anaerobic sludge from the pit of a slaughterhouse, after enrichment on tannic acid. The straight rods occurred singly or in pairs. Strain C2 fermented numerous carbohydrates (fructose, galactose, glucose, lactose, mannose, maltose, melibiose, raffinose, rhamnose, ribose, saccharose, sorbitol, trehalose, and xylose) and peptides (Biotrypcase, Casamino acids, and yeast extract), producing acid and gas, and had a G + C content of 51.6 +/- 0.1 mol %. Strain C2 was very closely related to Escherichia coli (= DSM 30083(T)) phylogenetically (similarity of 99%), genotypically (DNA homology of 79%), and phenotypically. The isolate tolerated tannic acid (hydrolyzable tannin) and decarboxylated by non-oxidative decarboxylation only p-hydroxybenzoic and vanillic acids to their corresponding phenol and guaicol, under anaerobic and aerobic conditions without further degradation. Adding glucose increased growth and the rate of conversion. High concentrations of p-hydroxybenzoic acid or vanillic acid inhibited growth, and decarboxylation could not occur completely, suggesting phenol toxicity. In contrast, the type strain of E. coli cannot metabolize p-hydroxybenzoic and vanillic acids, anaerobically or aerobically, with or without glucose added.

Aerobiosis↗