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Carnosine



Carnosine[1]
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 439224
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

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.

Additional recommended knowledge

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 Australia, Britain, and Russia have also shown that carnosine has a number of antioxidant properties that may be beneficial.[citation needed]

Carnosine has been proven to scavenge radical 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 and it can chelate divalent metal ions.

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 have been sufficiently demonstrated to recommend its use as a topical treatment for cataracts.[4]

Typical vegetarian diets are thought to be lacking in carnosine, but whether this has a detrimental effect on vegetarians is controversial.

Recently, carnosine was found to inhibit diabetic nephropathy by protecting the podocytes and mesangial cells.[citation needed]

See also

  • Anserine

References

  1. ^ Carnosine at Sigma-Aldrich
  2. ^ 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:10.1177/08830738020170111501. PMID 12585724.
  3. ^ Levy SE, Hyman SL (2005). "Novel treatments for autistic spectrum disorders". Ment Retard Dev Disabil Res Rev 11 (2): 131–42. doi:10.1002/mrdd.20062. PMID 15977319.
  4. ^ Statement on N-acetyl-carnosine eye drops, Royal College of Ophthamologists

5. Janssen B, Hohenadel D, Brinkkoetter P et al. Carnosine as a Protective Factor in Diabetic Nephropathy: Association With a Leucine Repeat of the Carnosinase Gene CNDP1. Diabetes. 2005;54(8):2320-7 http://diabetes.diabetesjournals.org/cgi/content/full/54/8/2320

6. Reddy VP, Garrett MR, Perry G, Smith MA. Carnosine: a versatile antioxidant and antiglycating agent. Sci Aging Knowledge Environ. 2005;(18) http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=15872311

7. Hipkiss AR. Would carnosine or a carnivorous diet help suppress aging and associated pathologies? Ann N Y Acad Sci. 2006;1067:369-74 http://www.biovita.fi/suomi/pdf/hipkiss_nyas.pdf

8. Hipkiss AR. Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works? Ann N Y Acad Sci. 2006;1067:361-8

9. Yan H, Harding JJ. Carnosine inhibits modifications and decreased molecular chaperone activity of lens a-crystallin induced by ribose and fructose 6-phosphate. Molecular Vision 2006; 12:205–214 http://www.molvis.org/molvis/v12/a23/

10. Rashid I, van Reyk DM, Davies MJ. Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro. FEBS Lett. 2007;581(5):1067-70 http://newsroom.msu.edu/site/indexer/2881/content.htm

11. Rajanikant GK, Zemke D, Senut MC, et al. Carnosine is neuroprotective against permanent focal cerebral ischemia in mice. Stroke. 2007 Oct


 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Carnosine". A list of authors is available in Wikipedia.
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