Indolyl-3-acryloylglycine explained

Indolyl-3-acryloylglycine, also known as trans-indolyl-3-acryloylglycine, or IAG for short, is a compound consisting of an indole group attached to an acrylic acid moiety, which is in turn attached to a glycine molecule. This compound has been shown to isomerize when exposed to light.[1] It is likely a metabolic intermediate in the biosynthesis of tryptophan,[2] and is synthesized from tryptophan via indolepropionic acid and indoleacrylicacid (IAcrA). It is also likely that IAcrA is converted into IAG in the gut wall.[3] It may also be produced by certain elements of the mammalian gut microbiota by phenylalanine ammonia-lyase.[4] Identifiable in the urine by high-performance liquid chromatography, it may be a biomarker for autism spectrum disorders, as demonstrated by the research of Paul Shattock[5] [6] [7] and other researchers from Australia.[8] These researchers have reported that urinary levels of IAG are much higher in autistic children than in controls; however, other researchers have found no association between IAG concentrations in the urine and autism.[9] Its excretion in the urine may also be changed in Hartnup disease and celiac disease,[10] as well as photodermatosis, muscular dystrophy, and liver cirrhosis.[11]

Notes and References

  1. 10.1016/S0378-4347(98)00153-4 . Mills . M. J. . Savery . D. . Shattock . P. E. . Rapid analysis of low levels of indolyl-3-acryloylglycine in human urine by high-performance liquid chromatography . Journal of Chromatography B . 712 . 1–2 . 51–58 . 1998 . 9698228.
  2. Marklová. E.. 1999. Where does indolylacrylic acid come from. Amino Acids. 17. 4. 401–413. 10.1007/BF01361665. 10707769.
  3. The Role of Tryptophan in Autism and Related Disorders . Shattock, Paul . The Nutrition Practitioner . Summer 2006.
  4. Clayton . T. A. . Metabolic differences underlying two distinct rat urinary phenotypes, a suggested role for gut microbial metabolism of phenylalanine and a possible connection to autism . 10.1016/j.febslet.2012.01.049 . FEBS Letters . 586 . 7 . 956–961 . 2012 . 22306194. free .
  5. Anderson . R. J. . Bendell . D. J. . Garnett . I. . Groundwater . P. W. . Lough . W. J. . Mills . M. J. . Savery . D. . Shattock . P. E. G. . 10.1211/0022357021778349 . Identification of indolyl-3-acryloylglycine in the urine of people with autism . Journal of Pharmacy and Pharmacology . 54 . 2 . 295–298 . 2002 . 11858215. free .
  6. Bull . G. . Shattock . P. . Whiteley . P. . Anderson . R. . Groundwater . P. W. . Lough . J. W. . Lees . G. . Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders . Medical Science Monitor . 9 . 10 . CR422–CR425 . 2003 . 14523330.
  7. Whiteley . P. . Mrpharms . P. S. . 10.1080/13590840310001641996 . What Makes Trans‐indolyl‐3‐acryloylglycine Identified by High‐performance Liquid Chromatography Relevant to Pervasive Developmental Disorders? . Journal of Nutritional and Environmental Medicine . 13 . 4 . 231 . 2003 .
  8. Wang . L. . Angley . M. T. . Gerber . J. P. . Young . R. L. . Abarno . D. V. . McKinnon . R. A. . Sorich . M. J. . 10.3109/13547500903183962 . Is urinary indolyl-3-acryloylglycine a biomarker for autism with gastrointestinal symptoms? . Biomarkers . 14 . 8 . 596–603 . 2009 . 19697973 .
  9. 10.1017/S0012162205000344 . Wright . B. . Brzozowski . A. M. . Calvert . E. . Farnworth . H. . Goodall . D. M. . Holbrook . I. . Imrie . G. . Jordan . J. . Kelly . A. . Miles . J. . Smith . R. . Town . J. . Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder? . Developmental Medicine & Child Neurology . 47 . 3 . 190–192 . 2005 . 15739724.
  10. Keszthelyi . D. . Troost . F. J. . Masclee . A. A. M. . 10.1111/j.1365-2982.2009.01370.x . Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function . Neurogastroenterology & Motility . 21 . 12 . 1239–1249 . 2009 . 19650771.
  11. 10.1016/0021-9673(95)00943-4 . Marklová . E. . Fojtásková . A. . High-performance liquid chromatographic profiling of indolylacryloylglycine and its possible precursors in body fluids . Journal of Chromatography A . 730 . 1–2 . 133–137 . 1996 . 8680585.

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