Carnosine

Chembox new
Reference= [ [http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C9625 Carnosine] at Sigma-Aldrich]
ImageFile=Carnosine.pngImageSize=200px
IUPACName=(2"S")-2- [(3-Amino-1-oxopropyl)amino] -3-(3"H"-imidazol-4-yl)propanoic acid
OtherNames=β-Alanyl-L-histidine
Section1= Chembox Identifiers
CASNo=305-84-0
PubChem=439224
SMILES=C1=C(NC=N1)CC(C(=O)O)NC(=O)CCN
Section2= Chembox Properties
Formula=C₉H₁₄N₄O₃
MolarMass=226.23
Appearance=Crystalline solid
Density=
MeltingPt=253 °C (decomposition)
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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. [cite journal |journal= J Child Neurol |year=2002 |volume=17 |issue=11 |pages=833–7 |title= Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders |author= Chez MG, Buchanan CP, Aimonovitch MC "et al." |doi=10.1177/08830738020170111501 |pmid=12585724] 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. [cite journal |journal= Ment Retard Dev Disabil Res Rev |year=2005 |volume=11 |issue=2 |pages=131–42 |title= Novel treatments for autistic spectrum disorders |author= Levy SE, Hyman SL |doi=10.1002/mrdd.20062 |pmid=15977319] Supplemental carnosine may increase corticosterone levels, which can explain the hyperactivity sometimes seen in high doses.Fact|date=August 2007 Researchers in Britain [cite journal |author=Aruoma OI, Laughton MJ, Halliwell B |title=Carnosine, homocarnosine and anserine: could they act as antioxidants in vivo? |journal=Biochem. J. |volume=264 |issue=3 |pages=863–9 |year=1989 |pmid=2559719 |doi=] , South Korea [cite journal |author=Choi SY, Kwon HY, Kwon OB, Kang JH |title=Hydrogen peroxide-mediated Cu,Zn-superoxide dismutase fragmentation: protection by carnosine, homocarnosine and anserine |journal=Biochim. Biophys. Acta |volume=1472 |issue=3 |pages=651–7 |year=1999 |pmid=10564779 |doi=] , Russia [cite journal |author=Klebanov GI, Teselkin YuO, Babenkova IV, "et al" |title=Effect of carnosine and its components on free-radical reactions |journal=Membr Cell Biol |volume=12 |issue=1 |pages=89–99 |year=1998 |pmid=9829262 |doi=] [cite journal |author=Babizhayev MA, Seguin MC, Gueyne J, Evstigneeva RP, Ageyeva EA, Zheltukhina GA |title=L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities |journal=Biochem. J. |volume=304 ( Pt 2) |issue= |pages=509–16 |year=1994 |pmid=7998987 |doi=] and other countries [cite journal |author=Chan KM, Decker EA |title=Endogenous skeletal muscle antioxidants |journal=Crit Rev Food Sci Nutr |volume=34 |issue=4 |pages=403–26 |year=1994 |pmid=7945896 |doi=] [cite journal |author=Kohen R, Yamamoto Y, Cundy KC, Ames BN |title=Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=85 |issue=9 |pages=3175–9 |year=1988 |pmid=3362866|doi=10.1073/pnas.85.9.3175] 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 [cite journal |author=Reddy VP, Garrett MR, Perry G, Smith MA |title=Carnosine: a versatile antioxidant and antiglycating agent |journal=Sci Aging Knowledge Environ |volume=2005 |issue=18 |pages=pe12 |year=2005 |pmid=15872311 |doi=10.1126/sageke.2005.18.pe12] [ cite journal |author=Rashid I, van Reyk DM, Davies MJ |title=Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro |journal=FEBS Lett. |volume=581 |issue=5 |pages=1067–70 |year=2007 |pmid=17316626 |doi=10.1016/j.febslet.2007.01.082] and it can chelate divalent metal ions. Chronic glycolysis is suspected to accelerate aging. [cite journal |author=Hipkiss AR |title=Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works? |journal=Ann. N. Y. Acad. Sci. |volume=1067 |issue= |pages=361–8 |year=2006 |pmid=16804012 |doi=10.1196/annals.1354.051]

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. [ [http://www.rcophth.ac.uk/scientific/publications Statement on N-acetyl-carnosine eye drops] , Royal College of Ophthamologists]

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. [cite journal |author=Janssen B, Hohenadel D, Brinkkoetter P, "et al" |title=Carnosine as a protective factor in diabetic nephropathy: association with a leucine repeat of the carnosinase gene CNDP1 |journal=Diabetes |volume=54 |issue=8 |pages=2320–7 |year=2005 |pmid=16046297|doi=10.2337/diabetes.54.8.2320]

ee also

* Carnosinemia
* Anserine
* Homocarnosine

References