Disease relevance of Vanillic acid

• Doubly recombinant resting E. coli cells efficiently reduce vanillic acid to vanillin [1].
• 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 [2].
• Cloning and sequencing of Pseudomonas genes encoding vanillate demethylase [3].
• Whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus [4].
• An Acinetobacter sp. genetic screen was used to probe structure-function relationships in vanillate demethylase, a two-component monooxygenase [5].

High impact information on Vanillic acid

• Several dietary plant micronutrients that inhibit carcinogenesis, including indole-3-carbinol, indole-3-carboxaldehyde, ferulic acid, vanillic acid, and epigallocatechin-3-gallate, were effective inhibitors of the activity of catalase oxidase [6].
• 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 [7].
• The incorporation of deuterium implicates the involvement of a quinoid vanillic acid tautomer as an intermediate in the decarboxylation reaction [7].
• The biotransformation of ferulic acid to vanillic acid by R. rubra cell-free extracts required CoA, ATP, and NAD+ [7].
• These enzymes are involved in the catabolism of tryptophan and vanillate, the biodegradation of hydroxylbenzoates, and the thymidine salvage pathways in certain organisms [8].

Chemical compound and disease context of Vanillic acid

• 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 [9].
• The 4-oxalomesaconate hydratase gene, involved in the protocatechuate 4,5-cleavage pathway, is essential to vanillate and syringate degradation in Sphingomonas paucimobilis SYK-6 [10].
• Formaldehyde fixation contributes to detoxification for growth of a nonmethylotroph, Burkholderia cepacia TM1, on vanillic acid [11].
• Purified Nocardia carboxylic acid reductase, an ATP and NADPH-dependent enzyme, quantitatively reduced vanillic acid to vanillin [12].
• 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 [13].

Biological context of Vanillic acid

• For this study, we isolated a 4.7-kb SmaI fragment that conferred on Escherichia coli the activity required for the conversion of vanillate to PCA [14].
• Under these conditions, 1 mg (wet weight) of biomass produced 0.23 mg of vanillic acid per h [9].
• Analysis of the genome context, operon arrangement, and regulation of the PhaK-like porin OpdK indicated that it might be involved in vanillate uptake [15].
• Thirty-four thermophilic Bacillus sp. strains were isolated from decayed wood bark and a hot spring water sample based on their ability to degrade vanillic acid under thermophilic conditions [16].
• Disruption of ligH resulted in the same phenotype as DC-49; its cell extract, however, was found to be able to convert vanillate and syringate in the presence of H(4)folate [17].

Anatomical context of Vanillic acid

• 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 [18].
• Only vanillic acid was detected in the intracellular fraction of protoplasts [19].
• In addition, vanillic acid was found in the ester-bound fraction and protocatechuic acid in the cell-wall bound fraction of elicited tissue [20].
• The addition of carbonylcyanide m-chlorophenylhydrazone, which dissipates the pH gradient across the plasma membrane, inhibited the uptake of either vanillin or vanillic acid into the cell [19].
• Direct exposure of spermatozoa to vanillic acid at doses 25-100 mg% did not significantly affect their motility, percent acrosome reaction or fertilizing ability [21].

Associations of Vanillic acid with other chemical compounds

• We mix 1 mL of urine sample with 2 mL of Tris buffer containing vanillic acid as internal standard (IS) and percolate this through a preconditioned ion-exchange column [22].
• Guaiacoxyacetic acid, 2-(o-methoxyphenoxy)ethanol, vanillic acid, and vanillin were detected as degradation products of veratrylglycerol-beta-guaiacyl ether by thin-layer chromatography, gas chromatography, and gas chromatography-mass spectrometry [23].
• Microbial catabolism of vanillate: decarboxylation to guaiacol [24].
• 1,2,4-Trihydroxybenzene (THB) is an intermediate in the Phanerochaete chrysosporium degradation of vanillate and aromatic pollutants [25].
• Intracellular quinone reduction in Sporotrichum pulverulentum by a NAD(P)H:quinone oxidoreductase: possible role in vanillic acid catabolism [26].

Gene context of Vanillic acid

• An Acinetobacter strain with a knockout mutation in vanR constitutively converted vanillate to protocatechuate [27].
• The QR activity in cultures of P. chrysosporium increased following the addition of 2-dimethoxybenzoquinone, vanillic acid, or several other aromatic compounds [28].
• Second, a 2.4A structure of CL complexed with the inhibitor vanillate shows the flaps partly opened relative to their product-bound positions [29].
• The amino acid sequence of the enzyme is similar to those of 4-hydroxybenzoate decarboxylase of Clostridium hydroxybenzoicum (53% identity), VdcC protein (vanillate decarboxylase) of Streptomyces sp. strain D7 (72%) and 3-octaprenyl-4-hydroxybenzoate decarboxylase of Escherichia coli (28%) [30].
• The concentrations (mmol/mol creatinine) of VMA, DOPAC, HVA, 5-HIAA and VA in the first-morning urine from healthy subjects increased from 7 days after birth to 1 year and then decreased to adult levels at 13 years of age [31].

Analytical, diagnostic and therapeutic context of Vanillic acid

• D. escambiense did not dehalogenate any of the compounds dehalogenated by the coculture, nor dit it O-demethoxylate 5CV or vanillate [32].
• PCR mutagenesis of vanAB, followed by selection for strains unable to metabolize vanillate, yielded mutant organisms in which vanillate metabolism is more strongly inhibited by the vanillate analogs [5].
• 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 [13].
• Mass balance modeling of vanillin production from vanillic acid by cultures of the fungus Pycnoporus cinnabarinus in bioreactors [33].
• We applied coulometric detection (three electrochemical electrodes in series) to quantitate vanillic acid and isovanillic acid using reversed-phase HPLC [34].

References