Carnosine
From Wikipedia, the free encyclopedia
| Carnosine[1] | |
|---|---|
 |
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| IUPAC name | (2S)-2-[(3-Amino-1-oxopropyl)amino]-3-(3H-imidazol-4-yl)propanoic acid |
| Other names | β-Alanyl-L-histidine |
| Identifiers | |
| CAS number | [305-84-0] |
| PubChem | |
| SMILES | C1=C(NC=N1)CC(C(=O)O)NC(=O)CCN |
| Properties | |
| Molecular formula | C9H14N4O3 |
| Molar mass | 226.23 |
| Appearance | Crystalline solid |
| Melting point |
253 °C (decomposition) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Carnosine (beta-alanyl-L-histidine) is a dipeptide of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues.
A small 2002 study reported that carnosine improved on a measure of socialization and receptive vocabulary in children with autism.[2] Improvement in this study could have been due to maturation, educational interventions, placebo effect, or other confounds that were not addressed in the study design.[3] Supplemental carnosine may increase corticosterone levels, which can explain the hyperactivity sometimes seen in high doses.[citation needed] Researchers in Britain[4], South Korea[5], Russia[6][7] and other countries[8][9] have also shown that carnosine has a number of antioxidant properties that may be beneficial.
Carnosine has been proven to scavenge reactive oxygen species (ROS) as well as alpha-beta unsaturated aldehydes formed from peroxidation of cell membrane fatty acids during oxidative stress. It can oppose glycation[10][11] and it can chelate divalent metal ions. Chronic glycolysis is suspected to accelerate aging.[12]
While a small number of studies have produced evidence of beneficial effects of N-acetyl carnosine in treating cataracts of the eyes, these and other ophthamological benefits have not been proven. Britain's Royal College of Ophthamologists assert that neither safety nor efficacy has been sufficiently demonstrated to recommend its use as a topical treatment for cataracts.[13]
Typical vegetarian diets are thought to be lacking in carnosine, but whether this has a detrimental effect on vegetarians is controversial.
Carnosine was found to inhibit diabetic nephropathy by protecting the podocytes and mesangial cells.[14]
[edit] See also
- Carnosinemia
- Anserine
- Homocarnosine
[edit] References
- ^ Carnosine at Sigma-Aldrich
- ^ Chez MG, Buchanan CP, Aimonovitch MC et al. (2002). "Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders". J Child Neurol 17 (11): 833–7. doi:. PMID 12585724.
- ^ Levy SE, Hyman SL (2005). "Novel treatments for autistic spectrum disorders". Ment Retard Dev Disabil Res Rev 11 (2): 131–42. doi:. PMID 15977319.
- ^ Aruoma OI, Laughton MJ, Halliwell B (1989). "Carnosine, homocarnosine and anserine: could they act as antioxidants in vivo?". Biochem. J. 264 (3): 863–9. PMID 2559719.
- ^ Choi SY, Kwon HY, Kwon OB, Kang JH (1999). "Hydrogen peroxide-mediated Cu,Zn-superoxide dismutase fragmentation: protection by carnosine, homocarnosine and anserine". Biochim. Biophys. Acta 1472 (3): 651–7. PMID 10564779.
- ^ Klebanov GI, Teselkin YuO, Babenkova IV, et al (1998). "Effect of carnosine and its components on free-radical reactions". Membr Cell Biol 12 (1): 89–99. PMID 9829262.
- ^ Babizhayev MA, Seguin MC, Gueyne J, Evstigneeva RP, Ageyeva EA, Zheltukhina GA (1994). "L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities". Biochem. J. 304 ( Pt 2): 509–16. PMID 7998987.
- ^ Chan KM, Decker EA (1994). "Endogenous skeletal muscle antioxidants". Crit Rev Food Sci Nutr 34 (4): 403–26. PMID 7945896.
- ^ Kohen R, Yamamoto Y, Cundy KC, Ames BN (1988). "Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain". Proc. Natl. Acad. Sci. U.S.A. 85 (9): 3175–9. doi:. PMID 3362866.
- ^ Reddy VP, Garrett MR, Perry G, Smith MA (2005). "Carnosine: a versatile antioxidant and antiglycating agent". Sci Aging Knowledge Environ 2005 (18): pe12. doi:. PMID 15872311.
- ^ Rashid I, van Reyk DM, Davies MJ (2007). "Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro". FEBS Lett. 581 (5): 1067–70. doi:. PMID 17316626.
- ^ Hipkiss AR (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Ann. N. Y. Acad. Sci. 1067: 361–8. doi:. PMID 16804012.
- ^ Statement on N-acetyl-carnosine eye drops, Royal College of Ophthamologists
- ^ Janssen B, Hohenadel D, Brinkkoetter P, et al (2005). "Carnosine as a protective factor in diabetic nephropathy: association with a leucine repeat of the carnosinase gene CNDP1". Diabetes 54 (8): 2320–7. doi:. PMID 16046297.
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