Skip to main content
SpringerLink
Log in

Deamination of 3-hydroxykynurenine in bovine lenses: a possible mechanism of cataract formation in general

  • Laboratory Investigation
  • Published:
Graefe's Archive for Clinical and Experimental Ophthalmology Aims and scope Submit manuscript

Abstract

• Background: 3-Hydroxykynurenine, a metabolite of tryptophan, acts as UV filter in the human lens. In this study, we looked for this substance and its metabolites in young and old bovine lenses, because of their possible role in the formation of cataract. • Methods: The substances were detected by HPLC analysis. The fluorescent substance formed from 3-hydroxykynurenine was characterized by thin-layer chromatography followed by reaction with ninhydrin, UV and fluorescence spectrum analysis, and atom bombardment for molecular mass determination. The kynurenine aminotransferase activity was determined by the method of Tobes. • Results: 3-Hydroxykynurenine was detected at concentrations of 0.07, 0.19, and 1.14 μg/g of tissue in the bovine iris/ciliary body, retina, and transparent bovine lenses respectively. 3-Hydroxykynurenine was deaminated in old bovine eyes but not in calf eyes. In old eyes, kynurenine aminotransferase activity was 2.7, 3.5, and 9.6 μmol/g of tissue per h in retina, iris/ciliary body, and lens respectively. • Conclusion: The deamination of 3-hydroxykynurenine resulted in the formation of a fluorescent substance which was identified as oxidized xanthurenic acid. This substance, accumulating in the bovine lens and interacting with lens proteins, could induce cataract formation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bessems GJH, Keizer E, Wallensak J, Hoenders HJ (1987) Non-tryptophan fluorescence of crystallins from normal and cataractous lenses. Invest Ophthalmol Vis Sci 28:1157–1163

    Google Scholar 

  2. Borkman RF, Tassin JD, Lerman S (1981) The rates of photodestruction of tryptophan residues in human and bovine ocular lens proteins. Exp Eye Res 32:747–754

    Google Scholar 

  3. Christen S, Peterhans E, Stocker R (1990) Antioxidant activities of some tryptophan metabolites: possible implication of inflammatory diseases. Proc Natl Acad Sci USA 87:2506–2510

    Google Scholar 

  4. Dillon J (1980) The anaerobic photolysis of tryptophan-containing peptides. Photochem Photobiol 32:37–39

    Google Scholar 

  5. Garcia-Castineiras S, Dillon J, Spector A (1978) Non-tryptophan fluorescence associated with human lens protein: apparent complexity and isolation of bityrosine and anthranilic acid. Exp Eye Res 26:461–476

    Google Scholar 

  6. Harding JJ (1991) Radiation cataract. In: Harding JJ (ed) Cataract. Biochemistry, epidemiology and pharmacology. Chapman and Hall, London, pp 147–155

    Google Scholar 

  7. Harding JJ, Crabe MJC (1984) The lens: development, proteins, metabolism and cataract. In: Davson H (ed) The eye, vol IB. Academic Press, London, pp 207–492

    Google Scholar 

  8. Heyningen R van (1971) Fluorescent glucoside in the human lens. Nature 230:393–394

    Google Scholar 

  9. Heyningen R van (1973) Photo-oxidation of lens proteins by sunlight in the presence of fluorescent derivatives of kynurenine, isolated from the human lens. Exp Eye Res17:137–147

    Google Scholar 

  10. Heyningen R van (1973) Assay of the fluorescent glucosides in the human lens. Exp Eye Res 15:121–126

    Google Scholar 

  11. Horowitz J (1992) α-Crystallin can function as a molecular chaperone. Proc Natl Acad Sci USA 89:10449–10453

    Google Scholar 

  12. Ichijima H, Iwata S (1987) Changes of lens crystallins photosensitized with tryptophan metabolites. Ophthalmic Res 19:157–163

    Google Scholar 

  13. Krishna CM, Uppuluri S, Riesz P, Zigler Jr JS, Balasubramanian D (1991) The study of the photodynamic efficiencies of some eye lens constituents. Photochem Photobiol 54:1–8

    Google Scholar 

  14. Kurzel BR, Wolbarsht M, Yamanashi BS, Staton G W, Borkman RF (1973) Tryptophan excited states and cataracts in the human lens. Nature 241:132–133

    Google Scholar 

  15. Lerman S, Borkman R (1976) Spectroscopic evaluation and classification of normal, aging, and cataractous lens. Ophthalmic Res 8:335–353

    Google Scholar 

  16. Lerman S, Borkman R (1978) Photoacoustic, fluorescence and light transmission spectra of normal, aging, and cataractous lenses. Ophthalmic Res 10:168–176

    Google Scholar 

  17. Luthra M, Balasubramanian D (1992) 3-Hydroxykynurenine and 3-hydroxyanthranilic acid may act as endogenous antioxidant in the eye lens. Exp Eye Res 55:641–643

    Google Scholar 

  18. Malina HZ, Martin XD (1993) Indoleamine 2,3-dioxygenase activity in aqueous humor, iris/ciliary body, and retina of bovine eye. Graefe's Arch Clin Exp Ophthalmol 231:482–486

    Google Scholar 

  19. Malina HZ, Martin XD (1993) Activity of indoleamine 2,3-dioxygenase in human lens. Invest Ophthalmol Vis Sci 34 [Suppl]: 291

    Google Scholar 

  20. Martin XD, Malina HZ (1993) Indoleamine 2,3-dioxygenase activity in human iris/ciliary body and retina. Invest Ophthalmol Vis Sci 34 [Suppl]: 1284

    Google Scholar 

  21. Martin XD, Brennan MC, Lichter PR (1988) Serotonin in human aqueous humor. Ophthalmology 95:1221–1226

    Google Scholar 

  22. Ohnishi T, Hirata F, Hayaishi O (1977) Indoleamine 2,3-dioxygenase. Potassium superoxide as substrate. J Biol Chem 252:4643–4647

    Google Scholar 

  23. Satoh K, Bando M, Nakajima A (1973) Fluorescence in human lens. Exp Eye Res 16:167–172

    Google Scholar 

  24. Stutchbury GM, Truscott RJW (1993) The modification of proteins by 3-hydroxykynurenine. Exp Eye Res 57:149–155

    Google Scholar 

  25. Tobes MC (1987) Kynurenine-oxoglutarate aminotransferase from rat kidney. Methods Enzymol 142:217–224

    Google Scholar 

  26. Tomoda A, Yoneyama Y, Yamaguchi T, Shirao E, Kawasaki K (1990) Mechanism of coloration of human lenses induced by near-ultraviolet-photo-oxidized 3-hydroxykynurenine. Ophthalmic Res 22:152–159

    Google Scholar 

  27. Truscott RJW, Martin F (1989) The reaction of proteins with 3-hydroxyanthranilic acid as a possible model for senile nuclear cataract in man. Exp Eye Res 49:927–940

    Google Scholar 

  28. Truscott RJW, Faull K, Augusteyn RC (1977) The identification of anthranilic acid in proteolytic digest of cataractous lens proteins. Ophthalmic Res 9:263–268

    Google Scholar 

  29. Truscott RJW, Carver JA, Thorpe A, Douglas RH (1992) Identification of 3-hydroxykynurenine as the lens pigment in the gourami Trichogaster trichopterus. Exp Eye Res 54:1015–1017

    Google Scholar 

  30. Wood AM, Truscott RJ (1993) UV filters in human lenses: tryptophan catabolism. Exp Eye Res 56:317–325

    Google Scholar 

  31. Yamazaki F, Kuroiwa T, Takikawa O, Kido R (1985) Human indolylamine 2,3-dioxygenase. Its tissue distribution and characterization of placental enzyme. Biochem J 230:635–638

    Google Scholar 

  32. Yu NT, Cai MZ, Ho DJ, Kuck JFR (1988) Automated laser scanning-microbeam fluorescence/Raman image analysis of human lens with multi-channel detection: evidence for metabolic production of a green fluorophor. Proc Natl Acad Sci USA 85:103–106

    Google Scholar 

  33. Zigman S (1971) Eye lens color: formation and function. Science 171:807–809

    Google Scholar 

  34. Zigman S, Paxhia T (1988) The nature and properties of squirrel lens yellow pigment. Exp Eye Res 47:819–824

    Google Scholar 

  35. Zigman S, Groff J, Yulo T (1977) Enhancement of the non-tryptophan fluorescence of human lens proteins after near-UV light exposure. Photochem Photobiol 26:505–509

    Google Scholar 

  36. Zigman S, Paxhia T, McDaniel T, Lou ME, Yu NT (1991) Effect of chronic near-ultraviolet radiation on the gray squirrel lens in vivo. Invest Ophthalmol Vis Sci 32:1723–1732

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire d'Ophtalmologie Expérimentale, Institut Universitaire de Pathologie, 25, rue du Bugnon, CH-1005, Lausanne, Switzerland

    Xavier Daniel Martin

  2. Department of Ophthalmology, University of Zurich, Frauenklinikstrasse 24, CH-8091, Zürich, Switzerland

    Halina Zofia Malina

Authors
  1. Halina Zofia Malina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xavier Daniel Martin
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Malina, H.Z., Martin, X.D. Deamination of 3-hydroxykynurenine in bovine lenses: a possible mechanism of cataract formation in general. Graefe's Arch Clin Exp Ophthalmol 233, 38–44 (1995). https://doi.org/10.1007/BF00177784

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00177784

Keywords

Search

Navigation