Aromatic acids, Urinary

The prediction of retention times in a given eluent from log P has been proposed for aromatic hydrocarbons.19 The log A values of phenols21 and nitrogen-containing compounds22 were also related to their logP, and the calculated log P was used for the qualitative analysis of urinary aromatic acids, i.e. for the identification of metabolites in urine from the differences of log P in reversed-phase liquid chromatography.23,24... 

H17. Homing, M. G., Knox, K. L., Dalgleish, C. E., and Horning, E. C., Gas-liquid chromatographic study and estimation of several urinary aromatic acids. Anal. Biochem. 17, 244-257 (1966). 

Williams and Sweeley (1964) have given methods for the chromatographic separation of many urinary aromatic acids and have discussed diagnostic applications to (1) secreting tumors, e.g., malignant carcinoid, pheochromocytoma, and neuroblastoma, and (2) inborn errors of metabolism, e.g., tyrosinosis, phenylketonuria, Hartnup disease (involves aminoaciduria), and other inherited diseases. These authors referred to the use of infrared spectroscopy for verification of the identity of fractions of volatile organic anesthetics in blood. Chlorpromazine, pentobarbitone, and amphetamine, are examples of pharmacological substances that have been separated (Scott, 1966). 

Spectrometry for the Diagnosis and Study of Metabolic Disorders. Screening and Identification of Urinary Aromatic Acids... 

Gas-Liquid Chromatography of the Urinary Aromatic Acids Especially, 03-Phenylaliphatic Acids Having Hydroxy or Methoxy Group in Aromatic Ring... 

Analysis of Urinary Aromatic Acids by Gas Chromatography Joint Mtg., Am. Assoc, of Clin. Chemists and Am. Assoc, of Sciences, December 1960 cf. Abstr. Clin. Chem. 7 306 (1961)... 

Determination of Urinary Aromatic Acids by Gas Chromatography. Results from Healthy Infants and from Patients with Phenylketonuria Z. Klin. Chem. Klin. Biochem. 9(5) 402-404 (1971) CA 76 1526g... 

Sweeley, C.C. and Williams, C.M. (1961), Microanalytical determination of urinary aromatic acids by gas chromatography. Anal. Biochem., 2,83. 

Williams, C.M. (1962), Gas chromatography of urinary aromatic acids. Anal Biochem., 4,423. 

Inoue, O., Seiji, K., Kudo, S., Jin, C., Cai S.-X., Liu, S.-J., Watanabe, T., Nakatsuka, H. Ikeda, M. (1995) Urinary phenylglyoxylic acid excretion after exposure to ethylbenzene among solvent-exposed Chinese workers. Int. J. occup. environ. Health, 1, 1-8 Johnstone, R.A.W., Quan, P.M. Carmthers, W. (1962) Composition of cigarette smoke some low-boiling components. Nature, 195, 1267-1269 Jonsson, A., Persson, K.A. Grigoriadis, V (1985) Measurement of some low molecular-weight oxygenated aromatic and chlorinated hydrocarbons in ambient air and in vehicle emissions. Environ, int., 11, 383-392... 

Some inborn errors of metabolism can be characterized by excessive urinary excretion of aromatic acid metabolites. These acids are distinct from the vanillyl acids discussed in a previous section. Phenylketonuria, alkaptonuria, and tyrosinosis can be diagnosed by determination of the aromatic acid metabolites. Aromatic acid profiles are characteristic of specific metabolic defects, and can be used to confirm diagnoses obtained from amino acid and other studies. Quantification of the individual aromatic acid gives information as to the fate of ingested amino acid in diseases such as phenylketonuria, where there is a block in the metabolic pathway involving the particular amino acid. 

The abnormalities in the urinary excretion of aromatic acids during phenylketonuria have been recently reviewed (S25) and will only be summarized here. 

The existence of a multiple specific enzymatic deficiency during phenylketonuria has been suggested by Boscott and Bickel (B26) to explain the abnormal excretion of aromatic acids other than phenyl-pyruvic acid, phenyllactic acid, and phenylacetylglutamine, as well as that of indolic acids. Jervis (J3) has, however, stated very recently that it is not necessary to postulate such a multiple enzymatic deficiency, since the complete biochemical urinary picture of phenylketonuria (including the presence of phenyl, hydroxyphenyl, and indolyl compounds) can be obtained temporarily in normal individuals following ingestion of large amounts of phenylalanine. 

Martin AK. The origin or urinary aromatic compounds excreted by ruminants. II. The metabolism of phenolic cinnamic acids to benzoic acid. Br J Nutr 1982 47 155-164. 

Indahl SR, Scheline RR. Quinic acid aromatization in the rat urinary hippuric acid and catechol excretion following the singular or repeated administration of quinic... 

MARTIN A.K. 1982a. The origin of urinary aromatic compounds excreted by ruminants 1. The metabolism of quinic, cyclohexanecarboxylic and non-phenolic aromatic acids to benzoic acid. British Journal of Nutrition, 47, 139-154. 

Decarboxylation of histidine to histamine is catalyzed by a broad-specificity aromatic L-amino acid decarboxylase that also catalyzes the decarboxylation of dopa, 5-hy-droxytryptophan, phenylalanine, tyrosine, and tryptophan. a-Methyl amino acids, which inhibit decarboxylase activity, find appfication as antihypertensive agents. Histidine compounds present in the human body include ergothioneine, carnosine, and dietary anserine (Figure 31-2). Urinary levels of 3-methylhistidine are unusually low in patients with Wilson s disease. 

A mammal may emit many volatile compounds. Humans, for instance, give off hundreds of volatiles, many of them chemically identified (Ellin etal., 1974). The volatiles include many classes of compound such as acids (gerbil), ketones, lactones, sulfides (golden hamster), phenolics (beaver, elephant), acetates (mouse), terpenes (elephant), butyrate esters (tamarins), among others. The human samples mentioned before contained hydrocarbons, unsaturated hydrocarbons, alcohols, acids, ketones, aldehydes, esters, nitriles, aromatics, heterocyclics, sulfur compounds, ethers, and halogenated hydrocarbons. Sulfur compounds are found in carnivores, such as foxes, coyotes, or mustelids. The major volatile compound in urine of female coyotes, Canis latrans, is methyl 3-methylhut-3-enyl sulfide, which accounts for at least 50% of all urinary volatiles (Schultz etal, 1988). 

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