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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↗
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↗
PubMed1991

[Excretion of vanillic acid and homovanillic acid and tissue distribution of catecholamines and their metabolites in mice with various levels of pigmentation].

Studies concerning metabolism of catecholamines in mice differing with respect to the degree of pigmentation were based on determination of daily excretion of vanillylmandelic and homovanillic acid and tissue content of epinephrine, norepinephrine, dopamine and their methoxy derivatives. It was found that pigmented mice excrete more homovanillic acid, the metabolite of dopamine, than do albinotic mice. Tissue studies have shown that the brain of albinotic mice contains more dopamine and kidneys more epinephrine, norepinephrine and their methoxy derivatives than the respective organs of the pigmented mice. The probable reasons of differences in the rate of inactivation of catecholamines in albinotic and pigmented mice have been discussed.

Animals↗
PubMed1979

A gas chromatographic-mass spectrometric assay for nine hydroxyphenolic acids in uremic serum.

A mass fragmentographic method for the determination of m-hydroxybenzoic acid, p-hydroxybenzoic acid, o-hydroxyphenylacetic acid, m-hydroxyphenylacetic acid, p-hydroxyphenylacetic acid, vanillic acid, p-hydroxymandelic acid, homovanillic acid and vanilmandelic acid in uremic serum is described. The hydroxyphenolic acids were extracted from one ml of serum ultrafiltrate. After trimethylsilylation, the extract was analyzed by a gas chromatograph-mass spectrometer. Concentrations of nine hydroxyphenolic acids are higher in uremic serum. In particular, p-hydroxybenzoic acid and p-hydroxyphenylacetic acid are markedly increased in uremic serum. The influence of hemodialysis on the hydroxyphenolic acids was studied by quantitating the acids before and after hemodialysis.

Female↗
PubMed1975

[On the phenolic acids of vegetables. IV. Hydroxycinnamic acids and hydroxybenzoic acids of vegetables and potatoes (author's transl)].

Lettuce, endive and chicory exclusively, cornsalad and sweet fennel almost exclusively contain caffeic acid derivatives beside traces of ferulic acid. Parsley exclusively and spinach almost exclusively show p-coumaric acid derivatives. Compared to root, fruit and seed vegetables the contents of phenolic acids in green leaves are considerably high. Rhubarb is the only vegetable, which contains gallic acid (chief phenolic acid) beside hydroxycinnamic, protocatechuic and vanillic acid derivatives. Furthermore hydroxybenzoic acid derivatives (salicylic, gentisic and vanillic acid) occur in cornsalad, sweet fennel, parsley and spinach in small concentrations; cornsalad shows p-hydroxybenzoic acid (ca. 20 mg/kg). Onions (Allium cepa) contain almost only protocatechuic acid beside small amounts of p-hydroxybenzoic and vanillic acid. In the outer dry coloured skins protocatechuic acid reaches concentrations up to 2% of plant material; the internal pulpy tissues show lower concentrations (ca. 20 mg/kg). On the contrary to the bulbs the green leaves of onions like chive and leek contain almost exclusively compounds of ferulic and p-coumaric acid. Garlic even shows a different phenolic acid pattern of skins and internal tissues. The caffeic acid derivatives of potatoes are mainly localized to a 1--2 mm thick outer layer. The different localization of phenolic acids in the different parts of vegetable plants is discussed.

Caffeic Acids↗
PubMed1975

[V. The phenolics of strawberries and their changes during development and ripeness of the fruits (author's transl)].

16 strawberry varieties contained ca. 10--70 mg (+)-catechin per kg freshweight, frequently up to 10 mg (-)-epicatechin, seldom (+)-gallocatechin and never (-)-epigallocatechin. The phenolic contents after hydrolysis were up to ca. 10 mg caffeic acid, ca. 10--15 mg p-coumaric acid, ca. 10--35 mg 4-hydroxybenzoic acid, up to 6 mg protocatechuic acid and ca. 10--40 mg gallic acid per 1000 g freshweight. From "Senga Sengana" ca. 10 mg/kg methyl gallate and ellagic acid were isolated. Salicylic acid, gentisic acid and vanillic acid were found in traces (1 mg/kg). The concentrations of all the examined phenolic acids, relating to the whole fruit (mg per fruit) increased, and, relating to fresh weight (mg per kg) decreased during the growth of the fruits with exception of 4-hydroxybenzoic acid. This acid appeared only in a relatively late stage of the fruit. The changes in catechins were similar. In the ripe fruit the catechin level was reduced a little.

Benzopyrans↗
PubMedDate not supplied

Degradation of non-phenolic beta-o-4 lignin substructure model compounds by Acinetobacter sp.

Acinetobacter sp. utilized non-phenolic beta-o-4-model compounds, 2-methoxy-4-formylphenoxyacetic acid and veratrylglycerol-beta-guaiacyl ether (VGE) as sole carbon source. Vanillin, vanillic acid, protocatechuic acid and catechol were detected in the 2-methoxy-4-formylphenoxyacetic acid amended culture. Veratryl alcohol, veratraldehyde, veratric acid, vanillic acid, protocatechuic acid, catechol and guaiacol were identified from veratrylglycerol-beta-guaiacyl ether culture. Acinetobacter sp. produced catechol 1,2-dioxygenase and protocatechuate 3,4-dioxygenase that cleaved catechol and protocatechuic acid, respectively.

Acinetobacter↗
PubMed1975

The metabolism of vanillin and isovanillin in the rat.

1. The metabolism of vanillin, isovanillin and the corresponding alcohols and acids in rats was investigated using t.l.c., g.l.c. and combined g.l.c.-mass spectrometry. 2. Oral dosage (100 mg/kg) of the aldehyde resulted in urinary excretion of most metabolites within 24 h, mainly as glucuronide and/or sulphate conjugates although the acids formed were also excreted free and as their glycine conjugates. In 48 h 94% of the dose of vanillin was accounted for as follows (%) : vanillin (7), vanillyl alcohol (19), vanillic acid (47), vanilloylglycine (10), catechol (8), 4-methylcatechol (2), guaiacol (0-5) and 4-methylguaiacol (0-6). Similarly, 89% of the dose of isovanillin was accounted for as follows: isovanillin (19), isovanillyl alcohol (10), isovanillic acid (22), vanillic acid (11), isovanilloylglycine (19), catechol(7) and 4-methylcatechol (1). Protocatechuic acid was also formed from both aldehydes. 3. By means of (a) investigation of biliary metabolites, (b) prevention of biliary excretion, (c) suppression of intestinal bacteria with neomycin sulphate and (d) inhibition of intestinal beta-glucuronidase with saccharo-1,4-lactone, it was found that glucuronides of the aldehydes and their respective alcohol and acid derivatives are excreted in the bile and that the conjugates are metabolized by the intestinal bacteria to toluene derivatives and decarboxylated products.

Administration, Oral↗
PubMed1976

Diazotization of catecholamines and their analogs and metabolites for urinary screening tests: chemical aspects.

Coupling of diazotized p-nitroaniline to catecholamines and their metabolites in urine has been proposed for use in screening for secreting neuroblastoma in childhood. We have coupled diazotized p-nitroaniline to catecholamines, derivatives, and metabolites and examined the reaction products by thin-layer chromatography and physico-chemical methods (ultraviolet spectra, mass spectroscopy, nuclear magnetic resonance). We conclude that during diazotization, products containing a p-hydroxybenzyl alcohol or a p-hydroxybenzoic acid structure (e.g., vanillic acid, vanilmandelic acid, 3-methoxy-4-hydroxyphenyl-ethyleneglycol, metanephrine, normetanephrine, synephrine, and isoproterenol) react with a diazonium cation, with release of their alcohol or acid moiety. Therefore the mentioned qualitative screening methods are very nonspecific. In contrast, thin-layer chromatographic screening methods provide complete separation and unambiguous identification of those metabolites and are to be preferred for use in detecting secreting neuroblastoma in childhood.

Aniline Compounds↗
PubMed1975

[On the phenolic acids of vegetables. II. Hydroxycinnamic acids and hydroxybenzoic acids of fruit and seed vegetables (author's transl)].

Fruits of solanaceae (tomatoes, eggplant, and sweet peppers) almost exclusively contain hydroxycinnamic acid derivatives with caffeic acid dominating. Fruits of cucurbitaceae (cucumbers, melons, pumpkins, and zucchini) are extraordinary, because they show very low concentrations of phenolic acids (up to 10 mg/kg) accumulated in the peels. Peas and broad beans have relatively small contents of phenolic acids too. Their husks show like beans considerable concentrations of hydroxycinnamic acid derivatives with dominating p-coumaric acid. In the group of hydroxybenzoic acids derivatives of salicylic, gentisic and vanillic acid could be determined frequently, but mostly as traces.

Caffeic Acids↗
PubMed1975

[On phenolic acids of vegetables. I. Hydroxycinnamic acids and hydroxybenzoic acids of brassica-species and leaves of other cruciferae (author's transl)].

The contents of phenolic acids in vegetables of the species Brassica almost totally consist of hydroxycinnamic acid compounds. In contrary to other species of vegetables sinapic acid is dominant. Leaves of radish (Rhaphanus sativus var. sativus and var. niger) mainly contain compounds of caffeic and p-coumaric acid; leaves of horse radish show only traces of hydroxycinnamic acids. In the group of hydroxybenzoic acid derivatives traces of salicylic and gentistic acid could be determined in almost all species and frequently vanillic acid. Protocatechnic acid was only identified in red cabbage, especially in the head, syringic acid in gardencress and p-hydroxybenzoic acid in horse radish leaves. No other hydroxybenzoic acids or hydroxycoumarins could be detected.

Caffeic Acids↗
PubMed1978

Microbial catabolism of vanillate: decarboxylation to guaiacol.

A novel catabolic transformation of vanillic acid (4-hydroxy-3-methoxybenzoic acid) by microorganisms is reported. Several strains of Bacillus megaterium and a strain of Streptomyces are shown to convert vanillate to guaiacol (o-methoxyphenol) and CO2 by nonoxidative decarboxylation. Use of a modified most-probable-number procedure shows that numerous soils contain countable numbers (10(1) to 10(2) organisms per g of dry soil) of aerobic sporeformers able to convert vanillate to guaiacol. Conversion of vanillate to guaiacol by the microfloras of most-probable-number replicates was used as the criterion for scoring replicates positive or negative. Guaiacol was detected by thin-layer chromatography. These results indicate that the classic separations of catabolic pathways leading to specific ring-fashion substrates such as protocatechuate and catechol are often interconnectable by single enzymatic transformations, usually a decarboxylation.

Bacillus megaterium↗