Carnosine
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2008-06-21T14:36:10Z
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{{Chembox new
|Reference=<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C9625 Carnosine] at [[Sigma-Aldrich]]</ref>
|ImageFile=Carnosine.png
|ImageSize=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=C<sub>9</sub>H<sub>14</sub>N<sub>4</sub>O<sub>3</sub>
| 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]] [[biological tissue|tissue]]s.
A small 2002 study reported that carnosine improved on a measure of socialization and receptive vocabulary in children with [[autism]].<ref>{{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}}</ref> 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.<ref>{{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}}</ref> Supplemental carnosine may increase [[corticosterone]] levels, which can explain the [[hyperactivity]] sometimes seen in high doses.{{Fact|date=August 2007}} Researchers in Britain<ref>{{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=}}</ref>, South Korea<ref>{{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=}}</ref>, Russia<ref>{{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=}}</ref><ref>{{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=}}</ref> and other countries<ref>{{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=}}</ref><ref>{{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}}</ref> 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]]<ref>{{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}}</ref><ref> {{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}}</ref> and it can [[chelate]] [[valency (chemistry)|divalent]] metal ions. Chronic glycolysis is suspected to accelerate aging.<ref>{{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}}</ref>
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.<ref>[http://www.rcophth.ac.uk/scientific/publications Statement on N-acetyl-carnosine eye drops], [[Royal College of Ophthamologists]]</ref>
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.<ref>{{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}}</ref>
==See also==
* [[Carnosinemia]]
* [[Anserine]]
* [[Homocarnosine]]
==References==
{{reflist|2}}
{{Neuropeptides}}
[[Category:Biomolecules]]
[[Category:Peptides]]
[[es:Carnosina]]
[[de:Carnosin]]
[[fr:Carnosine]]
[[ja:カルノシン]]
[[pl:Karnozyna]]
[[fi:Karnosiini]]