Summary
In addition to the main catabolic routes of tryptophan (Trp), there exist minor and less thoroughly investigated pathways; one of these leads to indolylacrylic acid (IAcrA). IAcrA is a plant growth hormone, whereas its biological role in animals is still obscure, as is the way and site where it is formed in the organism. A two-stage production is likely: Intestinal microorganisms catabolize Trp to indole derivatives which are then absorbed and converted to IAcrA and its glycine conjugate, indolylacryloylglyeine (IAcrGly). Our finding of IAcrGly in the urine of proven germ-free piglets points to the possibility that Trp can be converted to IAcrA without the intervention of intestinal microorganisms. Seasonal and age variations, influence of light and connection with photodermatoses have been reported. Besides other pathological conditions the differences in IAcrGly excretion relative to normal controls were especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Binazzi M, Calandra P (1975) Tryptophan metabolism in skin diseases. Acta Vitamin Enzymol (Milano) 29: 161–163
Gautheret RJ, Raoul Y (1949) Recherches sur Faction conjugé de Facide indol-acrylique et de tryptophane sur les cultures de tissues de Carottes et Topinambour. Bull Soc Ch im Biol 31: 1635–1638
Hofinger M, Monseur X, Pais M, Jarreau FX (1975) Futher confirmation of the presence of indolylacrylic acid in lentil seedlings and identification of hypaphorine as its precursor. Phytochem 14: 475–477
Kimmig J, Sticherling W, Tschesche R, Urbach HG (1958) N-/(beta-)Indolyl-(3)acryloyl/-glycin. Isolierung aus Harn and Synthese. Z Physiol Chem 311: 234–238
Mandel L, Talafantová M, Trebichovský I, Trávníček J, Koukal M (1985) Selective decontamination, induced colonisation resistance and connected immunological changes in piglets. Folia Mierobiol 30: 312–318
Mandell AJ, Rubin RT (1965) Indolylacroyl glycine excretion in man. Life Sci 4: 1657–1664
Marklová E, Hais IM (1972) A method for the estimation of indolylacryloylglycine in urine. Clin Chim Acta 40: 455–460
Marklová E, Hais IM (1978a) Urinary excretion of indolyl-3-acryloylglycine throughout the year and under the influence of UV irradiation. Sbor věd Prací LF UK v Hradci Králové 21 5: 515–520
Marklová E, Hais IM (1978b) Age variations of indolyl-3-acryloylglycine excretion in healthy children. Sbor věd Prací LF UK v Hradci Králové 21 5: 521–525
Marklová E, Fojtásková A (1996) HPLC profiling of indolylacryloylglycine and its possible precursors in body fluids. J Chromatogr A 730: 133–137
Marklová E, Malina L, Hais IM (1975) Urinary excretion of indolyl-acryloylglycine in some skin affections. Clin Chim Acta 64: 273–280
Marklová E, Mandel L, Jebavý L, Sobotka L, Hais IM (1986a) Metabolism of indolylacrylic acid. 1. Hypaphorine. II. Effect of the diet on indolylacryloylglycine excretion in urine. 111. Effect of intestinal microbes on excretion of indolylacryloylglycine in urine. Sbor ved Pracf LF UK v Hradci Králove [Suppl] 29/4–5: 435–455
Marklová E, Lichý J, Nesvadba Z, Hais IM (1986b) Urinary excretion of indolyl-3acryloylglycine in Duchenne type muscular dystrophy. Sbor věd Prací LF UK v Hradci Králové 21 5: 527–531
Marklová E, Hak J, Pařízek J, Morávek P (1992) Urinary excretion of some metabolites of tryptophan in malignant diseases. Sbor věd Prací LF UK v Hradci Králové 35 3: 275–279
Marklová E, Klein L, Hais IM (1993) Urinary excretion of indolylacryloylglycine, indolylacetic acid and 5-hydroxyindolylacetic acid in burn patients. Sbor věd Prací LF UK v Hradci Králové [Suppl] 36/4–5: 299–303
Marklová E, Fojtášková A, Makovičková H (1996) HPLC methods for determination of tryptophan and its metabolites. Chem Listy 90 9: 732–733
Monboisse JC, PierreLee P, Bisker A, Pailler V, Randoux A, Borel JP (1982) Quantitation of the urinary methylhistidine isomers by a combination of thin-layer and fluorimetric techniques. J Chromatogr 233: 355–360
Sergeeva TI, Zharova EI, Raushenbach MO (1979) Development of spontaneous leukemias induced by 3-indoleacrylic acid in a highly-leucemic mouse strain AKR Probl Gematol Pereliv Krovi 24: 44–45
Smith HG, Smith WRD, Jepson JB (1968) Interconversion of indolic acids by bacteria and rat tissue. Possible relevance to Hartnup disorder. Clin Sci 34: 333–342
Tompsett SL (1997) The determination in urine of some metabolites of tryptophan — kynurenine, anthranilic acid and 3-hydroxyanthranilic acid — and reference to the presence of o-aminophenol in urine. Clin Chim Acta 4: 414–419
Udenfriend S, Titus E, Weissbach H (1955) The identification of 5-hydroxy-3-indoleacetic acid in normal urine and a method for its assay. J Biol Chem 216: 499–505
Weisbach H, King W, Sjoerdsma A, Udenfriend S (1997) Formation of indole-3-acetic acid and tryptamine in animals. A method for estimation of indole-3-acetic acid in tissues. J Biol Chem 234: 81–86
Wiskemann A, Kimmig J (1963) Photodermatosen durch Arzneistoffe and endogene Sensibilisatoren. Internist 4: 509–513
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Marklová, E. Where does indolylacrylic acid come from. Amino Acids 17, 401–413 (1999). https://doi.org/10.1007/BF01361665
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01361665