Skip to main content
Log in

Carnosine and its (S)-Trolox™ derivative protect animals against oxidative stress

  • Original Article
  • Published:
Amino Acids Aims and scope Submit manuscript

Abstract

The novel synthetic derivative of carnosine, (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carbonyl-β-alanyl-l-histidine (S-Trolox™-Carnosine, STC) increases the resistance of rats to experimental acute hypobaric hypoxia (AHH) thus protecting brain from the oxidative damage. This effect is accompanied by better preservation of the acquired skills in Morris water maze possibly by increasing efficiency of the brain antioxidant system. In addition, STC caused an increase in life span of both male and female fruit fly Drosophila melanogaster whereas carnosine increased life span only in male fruit flies. The results indicate that development of the drug based on STC could be beneficial in neurology and gerontology.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Aldini G, Orioli M, Rossoni G, Savi F, Braidotti P, Vistoli G, Yeum KJ, Negrisoli G, Carini M (2011) The carbonyl scavenger carnosine ameliorates dyslipidaemia and renal function in Zucker obese rats. J Cell Mol Med 15(6):1339–1354

    Article  PubMed  CAS  Google Scholar 

  • Aruoma O, Laughton M, Halliwell B (1989) Carnosine, homocarnosine and anserine: could they act as antioxidants in vivo? Biochem J 264:863–869

    PubMed  CAS  Google Scholar 

  • Biegel A, Knütter I, Hartrodt B, Gebauer S, Theis S, Luckner P, Kottra G, Rastetter M, Zebisch K, Thondorf I, Daniel H, Neubert K, Brandsch M (2006) The renal type H+/peptide symporter PEPT2: structure-affinity relationships. Amino Acids 31(2):137–156

    Article  PubMed  CAS  Google Scholar 

  • Boldyrev AA (1993) Does carnosine possess direct antioxidant activity? Int J Biochem 25:1101–1107

    Article  PubMed  CAS  Google Scholar 

  • Boldyrev AA (2003) Significance of reactive oxygen species for neuronal function. In: Tomasi A et al (eds) Free radicals, NO, and Inflammation: molecular, biochemical and clinical aspects. IOS Press, The Netherlands, pp 153–169

  • Boldyrev A (2005) Protection of proteins from oxidative stress: a new illusion or a novel strategy? Ann N Y Acad Sci 1057:193–205

    Article  PubMed  CAS  Google Scholar 

  • Boldyrev A (2006) Carnosine and protection of cells and tissues against oxidative stress, NovaPubl., NY

  • Boldyrev AA, Dupin AM, Bunin AYa, Babizhaev MA, Severin SE (1987) The antioxidative properties of carnosine, a natural histidine containing dipeptide. Biochem Int 15:1105–1113

    PubMed  CAS  Google Scholar 

  • Boldyrev AA, Stvolinsky SL, Tyulina OV, Koshelev VB, Hori N, Carpenter D (1997) Biochemical and physiological evidence that carnosine is an endogenous neuroprotector against free radicals. Cell Mol Neurobiol 17(2):259–271

    Article  PubMed  CAS  Google Scholar 

  • Boldyrev A, Song R, Lawrence D, Carpenter DO (1999) Carnosine protects against excitotoxic cell death independently of effects on reactive oxygen species. Neuroscience 94:571–577

    Article  PubMed  CAS  Google Scholar 

  • Boldyrev A, Stvolinsky S, Fedorova T, Suslina Z (2010) Carnosine as a natural antioxidant and geroprotector: from molecular mechanisms to clinical trials. Rejuv Res 13(2–3):156–158

    Article  CAS  Google Scholar 

  • Dobrota D, Fedorova T, Stepanova M, Babusikova E, Statelova D, Tatarkova Z, Stvolinsky S, Boldyrev A (2010) Oxidative stress, induced in rat brain by a combination of 3-nitropropionic acid and global ischemia. J Clin Exp Med 3:144–152

    CAS  Google Scholar 

  • Feldman LA, Shapiro ML, Nalbantoglu J (2010) A novel, rapidly acquired and persistent spatial memory task that induces immediate early gene expression. Behav Brain Funct 6:35–46

    Article  PubMed  Google Scholar 

  • Gallant S, Kukley M, Stvolinsky S, Bulygina E, Boldyrev A (2000) Effect of carnosine on rats under experimental brain ischemia. Tohoku J Exp Med 191:85–99

    Article  PubMed  CAS  Google Scholar 

  • Gupta S, Sharma SS (2006) Neuroprotective effects of Trolox™ in global cerebral ischemia in gerbils. Biol Pharm Bull 29:957–961

    Article  PubMed  CAS  Google Scholar 

  • Hipkiss A (2009) Carnosine and its possible roles in nutrition and health. Adv Food Nutr Res 57:87–154

    Article  PubMed  CAS  Google Scholar 

  • Iliadi KG, Iliadi NN, Boulianne GL (2009) Regulation of Drosophila life-span: effect of genetic background, sex, mating and social status. Exp Gerontol 44:546–553

    Article  PubMed  Google Scholar 

  • Kang JH (2010) Protective effects of carnosine and homocarnosine on ferritin and hydrogen peroxide-mediated DNA damage. BMB Rep 43(10):683–687

    Article  PubMed  CAS  Google Scholar 

  • Kohen R, Yamamoto Y, Cundy K, Ames BN (1988) Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain. Proc Natl Acad Sci USA 85:3175–3179

    Article  PubMed  CAS  Google Scholar 

  • Koren E, Kohen R, Ginsburg I (2010) Polyphenols enhance total oxidant-scavenging capacities of human blood by binding to red blood cells. Exp Biol Med 235:689–699

    Article  CAS  Google Scholar 

  • Kosolapov VA, Spasov AA, Tibirjkov EV (2009) Antioxidant and membrane protector properties of Trolox™. Exptl Clin Pharmacol 2:47–50

    Google Scholar 

  • Leinsoo T, Abe H, Boldyrev A (2006) Carnosine and related compounds protect double-helices DNA against oxidative injury. J Evol Biochem Physiol 42:453–456

    Article  CAS  Google Scholar 

  • Lints FA, Bourgois M, Delalieux A, Stoll J, Lints CV (1983) Does the female life span exceed that of the male? A study in Drosophila melanogaster. Gerontology 29:336–352

    Article  PubMed  CAS  Google Scholar 

  • Miller DJ, O’Dowd A (2000) Vascular smooth muscle actions of carnosine as its zinc complex are mediated by histamine H(1) and H(2) receptors. Biochemistry (Mosc) 65(7):798–806

    CAS  Google Scholar 

  • Morris R (1984) Developments of a water-maze procedure for studying spatial learning in the rat. J Neurosci Methods 11:47–60

    Article  PubMed  CAS  Google Scholar 

  • Schlesier K, Harwat M, Bőhm V, Bitsch R (2002) Assessment of antioxidant activity by using different in vitro methods. Free Rad Res 36:177–187

    Article  CAS  Google Scholar 

  • Sharma SS, Kaundal RK (2007) Neuroprotective effects of 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox™), an antioxidant in middle cerebral artery occlusion induced focal cerebral ischemia in rats. Neurol Res 29(3):304–309

    Article  PubMed  CAS  Google Scholar 

  • Stvolinsky SL, Kukley ML, Dobrota D, Matejovicova M, Tkac I, Boldyrev AA (1999) Carnosine: an endogeneous neuroprotector in ischemic brain. Cell Molec Neurobiol 19:45–56

    Article  PubMed  CAS  Google Scholar 

  • Stvolinsky SL, Bulygina ER, Fedorova TN, Meguro K, Sato T, Tyulina OV, Abe H, Boldyrev AA (2010a) Biological activity of novel synthetic derivatives of carnosine. Cell Mol Neurobiol 30(3):395–404

    Article  PubMed  CAS  Google Scholar 

  • Stvolinsky S, Antipin M, Meguro K, Sato T, Abe H, Boldyrev A (2010b) Effect of carnosine and its Trolox™-modified derivatives on lifespan of Drosophila melanogaster. Rejuv Res 13(4):453–457

    Article  CAS  Google Scholar 

  • Tanida M, Niijima A, Fukuda Y, Sawai H, Tsuruoka N, Shen J, Yamada S, Kiso Y, Nagai K (2005) Dose-dependent effects of l-carnosine on the renal sympathetic nerve and blood pressure in urethane-anesthetized rats. Am J Physiol Regul Integr Comp Physiol 288(2):R447–R455

    Article  PubMed  CAS  Google Scholar 

  • Yuneva AO, Kramarenko GG, Vetreshchak TV, Gallant S, Boldyrev AA (2002) Effect of carnosine on Drosophila melanogaster life span. Bull Exp Biol Med 133(6):559–661

    Article  Google Scholar 

Download references

Acknowledgments

Supported by RFBR Grants ## 09-04-00505, 10-04-01461, and 11-04-00906.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Boldyrev.

Additional information

To the memory of Steven Gallant, enthusiast in carnosine biochemistry

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stvolinsky, S., Toropova, K., Gordeeva, M. et al. Carnosine and its (S)-Trolox™ derivative protect animals against oxidative stress. Amino Acids 43, 165–170 (2012). https://doi.org/10.1007/s00726-012-1256-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00726-012-1256-4

Keywords

Navigation