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Carnosine

 
(′kär·nə′sēn)

(biochemistry) C9H14N4O3 A colorless, crystalline dipeptide occurring in the muscle tissue of vertebrates.


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Food and Nutrition: carnosine
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A dipeptide, β-alanyl-histidine, found in the muscle of most animals. Its function is not known.

Veterinary Dictionary: carnosine
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A dipeptide composed of beta-alanine and histidine, found in skeletal muscle of vertebrates.

Wikipedia: Carnosine
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Carnosine[1]
Carnosine.png
IUPAC name
Other names β-Alanyl-L-histidine
Identifiers
CAS number 305-84-0 Yes check.svgY
PubChem 439224
SMILES
InChI
InChI key CQOVPNPJLQNMDC-UHFFFAOYAL
ChemSpider ID 9001
Properties
Molecular formula C9H14N4O3
Molar mass 226.23
Appearance Crystalline solid
Melting point

253 °C (decomposition)

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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.

Researchers in Britain[2], South Korea[3], Russia[4][5] and other countries[6][7] 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[8][9] and it can chelate divalent metal ions. Chronic glycolysis is suspected to accelerate aging.[10] Carnosine was found to inhibit diabetic nephropathy by protecting the podocytes and mesangial cells.[11] Because of its antioxidant, antiglycator and metal chelator properties, carnosine supplements have been proposed as a general anti-aging therapy. [12]

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.[13] However, claims that carnosine confers these and other posited ophthamological benefits are, as of yet, insufficiently supported for endorsement by the mainstream medical community; Britain's Royal College of Ophthamologists, for instance, has asserted that neither safety nor efficacy has been sufficiently demonstrated to recommend carnosine's use as a topical treatment for cataracts.[14]

A small 2002 study reported that carnosine improved on a measure of socialization and receptive vocabulary in children with autism.[15] 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.[16] Supplemental carnosine may increase corticosterone levels, which can explain the hyperactivity sometimes seen in high doses.[citation needed]

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

See also

References

  1. ^ Carnosine at Sigma-Aldrich
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Klebanov, Gi; Teselkin, Yuo; Babenkova, Iv; Lyubitsky, Ob; Rebrova, Oyu; Boldyrev, Aa; Vladimirov, Yua (1998). "Effect of carnosine and its components on free-radical reactions." (Free full text). Membrane & cell biology 12 (1): 89–99. ISSN 1023-6597. PMID 9829262. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+71-00-1. 
  5. ^ 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. 
  6. ^ Chan KM, Decker EA (1994). "Endogenous skeletal muscle antioxidants". Crit Rev Food Sci Nutr 34 (4): 403–26. PMID 7945896. 
  7. ^ 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:10.1073/pnas.85.9.3175. PMID 3362866. 
  8. ^ Reddy VP, Garrett MR, Perry G, Smith MA (2005). "Carnosine: a versatile antioxidant and antiglycating agent". Sci Aging Knowledge Environ 2005 (18): pe12. doi:10.1126/sageke.2005.18.pe12. PMID 15872311. 
  9. ^ 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:10.1016/j.febslet.2007.01.082. PMID 17316626. 
  10. ^ Hipkiss AR (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Ann. N. Y. Acad. Sci. 1067: 361–8. doi:10.1196/annals.1354.051. PMID 16804012. 
  11. ^ Janssen, B. (2005). "Carnosine as a Protective Factor in Diabetic Nephropathy: Association With a Leucine Repeat of the Carnosinase Gene CNDP1". Diabetes 54: 2320. doi:10.2337/diabetes.54.8.2320. PMID 16046297. 
  12. ^ http://www.antiaging-systems.com/extract/kyriazis.htm
  13. ^ http://pubs.acs.org/doi/abs/10.1021/bi900343n "Protective Effects of L- and D-Carnosine on α-Crystallin Amyloid Fibril Formation: Implications for Cataract Disease", Francesco Attanasio, et al., Biochemistry, 2009, 48 (27), pp 6522–6531 (July 28, 2009)
  14. ^ Statement on N-acetyl-carnosine eye drops, Royal College of Ophthamologists
  15. ^ 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. 
  16. ^ 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. 

 
 
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Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved.  Read more
Food and Nutrition. A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.  Read more
Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
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