Carnosine

Carnosine[1]
Names
IUPAC name
(2S)-2-[(3-Amino-1-oxopropyl)amino]-3-(3H-imidazol-4-yl)propanoic acid
Other names
β-Alanyl-L-histidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.610
KEGG
UNII
Properties
C9H14N4O3
Molar mass 226.24 g·mol−1
Appearance Crystalline solid
Melting point 253 °C (487 °F; 526 K) (decomposition)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carnosine (beta-alanyl-L-histidine), featuring the characteristic imidazole-ring, is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues.

Carnosine and carnitine were discovered by Russian chemist Vladimir Gulevich.[2] It 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 also buffers pH in muscle cells, and acts as a neurotransmitter in the brain. It is also a zwitterion, a neutral molecule with a positive and negative end.

Like carnitine, carnosine is composed of the root word carn, meaning "flesh", alluding to its prevalence in animal protein.[3] A vegetarian (especially vegan) diet provides less carnosine, compared to levels found in a diet including meat.[4]

Carnosine can chelate divalent metal ions.[5]

Carnosine can increase the Hayflick limit in human fibroblasts,[6] as well as appearing to reduce the telomere shortening rate.[7] It is also considered as a geroprotector.[8]

Physiological effects

Atherosclerosis and aging

Carnosine acts as an antiglycating agent, reducing the rate of formation of advanced glycation end-products (substances that can be a factor in the development or worsening of many degenerative diseases, such as diabetes, atherosclerosis, chronic renal failure, and Alzheimer's disease[9]), and ultimately reducing development of atherosclerotic plaque build-up.[5][10][11] Chronic glycolysis is speculated to accelerate aging, making carnosine a candidate for therapeutic potential.[12]

See also

References

  1. ↑ "C9625 L-Carnosine ~99%, crystalline". Sigma-Aldrich.
  2. ↑ Gulewitsch, Wl.; Amiradžibi, S. (1900). "Ueber das Carnosin, eine neue organische Base des Fleischextractes". Berichte der deutschen chemischen Gesellschaft. 33 (2): 1902–1903. doi:10.1002/cber.19000330275.
  3. ↑ Hipkiss, A. R. (2006). "Does chronic glycolysis accelerate aging? Could this explain how dietary restriction works?". Annals of the New York Academy of Sciences. 1067: 361–8. doi:10.1196/annals.1354.051. PMID 16804012.
  4. ↑ Alan R. Hipkiss (2009). "Chapter 3: Carnosine and Its Possible Roles in Nutrition and Health". Advances in Food and Nutrition Research.
  5. 1 2 Reddy, V. P.; Garrett, MR; Perry, G; Smith, MA (2005). "Carnosine: A Versatile Antioxidant and Antiglycating Agent". Science of Aging Knowledge Environment. 2005 (18): pe12. doi:10.1126/sageke.2005.18.pe12. PMID 15872311.
  6. ↑ McFarland, G; Holliday, R (1994). "Retardation of the Senescence of Cultured Human Diploid Fibroblasts by Carnosine". Experimental Cell Research. 212 (2): 167–75. doi:10.1006/excr.1994.1132. PMID 8187813.
  7. ↑ Shao, Lan; Li, Qing-Huan; Tan, Zheng (2004). "L-Carnosine reduces telomere damage and shortening rate in cultured normal fibroblasts". Biochemical and Biophysical Research Communications. 324 (2): 931–6. doi:10.1016/j.bbrc.2004.09.136. PMID 15474517.
  8. ↑ Boldyrev, A. A.; Stvolinsky, S. L.; Fedorova, T. N.; Suslina, Z. A. (2010). "Carnosine as a natural antioxidant and geroprotector: From molecular mechanisms to clinical trials". Rejuvenation Research. 13 (2–3): 156–8. doi:10.1089/rej.2009.0923. PMID 20017611.
  9. ↑ Vistoli, G; De Maddis, D; Cipak, A; Zarkovic, N; Carini, M; Aldini, G (Aug 2013). "Advanced glycoxidation and lipoxidation end products (AGEs and ALEs): an overview of their mechanisms of formation". Free Radic Res. 47: Suppl 1:3–27. doi:10.3109/10715762.2013.815348. PMID 23767955.
  10. ↑ Rashid, Imran; Van Reyk, David M.; Davies, Michael J. (2007). "Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro". FEBS Letters. 581 (5): 1067–70. doi:10.1016/j.febslet.2007.01.082. PMID 17316626.
  11. ↑ Hipkiss, A. R. (2005). "Glycation, ageing and carnosine: Are carnivorous diets beneficial?". Mechanisms of Ageing and Development. 126 (10): 1034–9. doi:10.1016/j.mad.2005.05.002. PMID 15955546.
  12. ↑ Hipkiss, A. R. (2006). "Does Chronic Glycolysis Accelerate Aging? Could This Explain How Dietary Restriction Works?". Annals of the New York Academy of Sciences. 1067: 361–8. doi:10.1196/annals.1354.051. PMID 16804012.
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