Carnosine: Difference between revisions

| verifiedrevid = 443505972

|Reference=<ref>{{cite web |url=http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/C9625 |title=C9625 L-Carnosine ~99%, crystalline |publisher=[[Sigma-Aldrich]]}}</ref>

| ImageFile= Carnosine-2D-skeletal.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

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| CASNo=305-84-0

| PubChem=439224

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 57485

| SMILES = O=C(O)C(NC(=O)CCN)Cc1cncn1

|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 should not be confused with [[Carnitine]]''.

'''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.

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=[[The Biochemical Journal]] |volume=264 |issue=3 |pages=863–9 |year=1989 |month=December |pmid=2559719 |pmc=1133665}}</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=Biochimica et Biophysica Acta |volume=1472 |issue=3 |pages=651–7 |year=1999 |month=November |pmid=10564779 |doi=10.1016/S0304-4165(99)00189-0}}</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=[[Membrane & Cell Biology]] |volume=12 |issue=1 |pages=89–99 |year=1998 |pmid=9829262}}</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=The Biochemical Journal |volume=304 |issue=2 |pages=509–16 |year=1994 |month=December |pmid=7998987 |pmc=1137521}}</ref> and other countries<ref>{{cite journal |author=Chan KM, Decker EA |title=Endogenous skeletal muscle antioxidants |journal=[[Critical Reviews in Food Science and Nutrition]] |volume=34 |issue=4 |pages=403–26 |year=1994 |pmid=7945896 |doi=10.1080/10408399409527669}}</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=[[Proceedings of the National Academy of Sciences of the United States of America]] |volume=85 |issue=9 |pages=3175–9 |year=1988 |month=May |pmid=3362866 |pmc=280166 |doi=10.1073/pnas.85.9.3175}}</ref> have 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]].

Carnosine can oppose [[glycation]]<ref>{{cite journal |author=Reddy VP, Garrett MR, Perry G, Smith MA |title=Carnosine: a versatile antioxidant and antiglycating agent |journal=[[Science of Aging Knowledge Environment]] |volume=2005 |issue=18 |pages=pe12 |year=2005 |month=May |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 Letters]] |volume=581 |issue=5 |pages=1067–70 |year=2007 |month=March |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=[[Annals of the New York Academy of Sciences]] |volume=1067 |issue= |pages=361–8 |year=2006 |month=May |pmid=16804012 |doi=10.1196/annals.1354.051}}</ref> 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 (journal)|Diabetes]] |volume=54 |issue=8 |pages=2320–7 |year=2005 |month=August |pmid=16046297 |doi=10.2337/diabetes.54.8.2320}}</ref> Because of its antioxidant, antiglycator and metal chelator properties, carnosine supplements have been proposed as a general [[anti-aging]] therapy.<ref>http://www.antiaging-systems.com/extract/kyriazis.htm</ref>

Carnosine containing products are also used in topical preparations to reduce wrinkles on the skin.<ref>http://www.ncbi.nlm.nih.gov/pubmed/19735523 J Cosmet Dermatol. 2009 Sep;8(3):228-33. Efficacy of anti-aging products for periorbital wrinkles as measured by 3-D imaging</ref>

Some studies have detected beneficial effects of N-[[acetyl-carnosine]] in preventing and treating cataracts of the eyes; in one of these, carnosine was found to reduce cloudiness in rat lenses that were exposed to guanidine to cause cataracts.<ref>{{cite journal |author=Attanasio F, Cataldo S, Fisichella S, ''et al.'' |title=Protective effects of L- and D-carnosine on alpha-crystallin amyloid fibril formation: implications for cataract disease |journal=[[Biochemistry (journal)|Biochemistry]] |volume=48 |issue=27 |pages=6522–31 |year=2009 |month=July |pmid=19441807 |doi=10.1021/bi900343n}}</ref> However, claims that carnosine confers these and other posited ophthalmological benefits are, as of yet, insufficiently supported for endorsement by the mainstream medical community; Britain's Royal College of Ophthalmologists, for instance, has asserted that neither safety nor efficacy has been sufficiently demonstrated to recommend carnosine's use as a topical treatment for cataracts.<ref>{{cite web |url=http://www.rcophth.ac.uk/docs/publications/published-guidelines/N_ACETYL-CARNOSINE_FOR_CATARACTS.pdf |title=N-Acetyl Carnosine for Cataracts |first=Winfried |last=Amoaku |publisher=Royal College of Ophthalmologists |date=August 6, 2008}}</ref>

A small 2002 study reported that carnosine improved socialization and receptive vocabulary in children with [[autism]].<ref>{{cite journal |author=Chez MG, Buchanan CP, Aimonovitch MC, ''et al.'' |title=Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders |journal=[[Journal of Child Neurology]] |volume=17 |issue=11 |pages=833–7 |year=2002 |month=November |pmid=12585724 |doi=10.1177/08830738020170111501}}</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 |author=Levy SE, Hyman SL |title=Novel treatments for autistic spectrum disorders |journal=[[Mental Retardation and Developmental Disabilities Research Reviews]] |volume=11 |issue=2 |pages=131–42 |year=2005 |pmid=15977319 |doi=10.1002/mrdd.20062}}</ref> In animal models, supplemental carnosine can increase [[corticosterone]] levels, which may explain the [[hyperactivity]] sometimes seen in high doses.<ref>{{cite web |url=http://www.sciencedirect.com/science/article/B6SYT-4BP9PC3-1/2/bc6bfe64185c28814fb02b218a8cfa16 |title=Effect of central administration of carnosine and its constituents on behaviors in chicks |first=Shozu, et al. |last= Tomonaga |publisher=Royal College of Ophthalmologists |date=August 6, 2008}}</ref> However, the aforementioned study used carnosine injected into chicks intracerebroventricularly, and a raise in corticosterone levels has not yet been found in humans.

In animal models carnosine has been shown to retard cancer growth<ref>{{cite journal |author=Renner C, Zemitzsch N, Fuchs B, ''et al.'' |title=Carnosine retards tumor growth in vivo in an NIH3T3-HER2/neu mouse model |journal=[[Molecular Cancer]] |volume=9 |issue= |pages=2 |year=2010 |pmid=20053283 |pmc=2818694 |doi=10.1186/1476-4598-9-2}}</ref> and protect against alcohol-induced oxidative stress<ref>{{cite journal |author=Ozel Turkcu U, Bilgihan A, Biberoglu G, Mertoglu Caglar O |title=Carnosine supplementation protects rat brain tissue against ethanol-induced oxidative stress |journal=[[Molecular and Cellular Biochemistry]] |volume= 339|issue= 1-2|pages= 55–61|year=2010 |month=January |pmid=20047045 |doi=10.1007/s11010-009-0369-x}}</ref> as well as ethanol-induced chronic liver damage.<ref>{{cite journal |author=Liu WH, Liu TC, Yin MC |title=Beneficial effects of histidine and carnosine on ethanol-induced chronic liver injury |journal=[[Food and Chemical Toxicology]] |volume=46 |issue=5 |pages=1503–9 |year=2008 |month=May |pmid=18222027 |doi=10.1016/j.fct.2007.12.013}}</ref> Carnosine is also neuroprotective against permanent cerebral ischemia in mice.<ref>{{cite journal |author=Min J, Senut MC, Rajanikant K, ''et al.'' |title=Differential neuroprotective effects of carnosine, anserine, and N-acetyl carnosine against permanent focal ischemia |journal=[[Journal of Neuroscience Research]] |volume=86 |issue=13 |pages=2984–91 |year=2008 |month=October |pmid=18543335 |pmc=2805719 |doi=10.1002/jnr.21744}}</ref>

Carnosine can increase the [[Hayflick limit]] in human [[fibroblasts]],<ref>{{cite journal |author=McFarlan GA. |coauthors=Holliday R. |title=Retardation of the senescence of cultured human fibroblasts by carnosine |journal=Exp. Cell Res. |volume=212 |issue=2 |pages=167–175 |year=1994 |pmid=8187813 |doi=10.1006/excr.1994.1132}}</ref> as well as appearing to reduce the telomere shortening rate.<ref>{{cite journal |author=Shao L |coauthors=Li QH, Tan Z |title=L-carnosine reduces telomere damage and shortening rate in cultured normal fibroblasts. |journal= Biochem Biophys Res Commun. |year=2004 |volume=324 |issue=2 |pages=931–936 |pmid=15474517 |doi=10.1016/j.bbrc.2004.09.136}}</ref> This could potentially favor the growth of certain cancers that thrive due to telomere preservation.<ref>http://www.ncbi.nlm.nih.gov/pubmed/11327115 Telomerase activation, cellular immortalization and cancer, Ann Med. 2001 Mar;33(2):123-9</ref>

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

* [[Carnosinemia]]

* [[Anserine]]

* [[Homocarnosine]]

* [[Acetyl-carnosine]]

[[Category:Biomolecules]]

[[de:Carnosin]]

[[es:Carnosina]]

[[fr:Carnosine]]

[[ja:カルノシン]]

[[pl:Karnozyna]]

[[ru:Карнозин]]

[[fi:Karnosiini]]