Carnosine

Not to be confused with carnitine.
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
305-84-0 Yes
ChEBI CHEBI:57485 Yes
ChEMBL ChEMBL242948 Yes
ChemSpider 388363 Yes
Jmol-3D images Image
Image
KEGG C00386 Yes
PubChem 439224
UNII 8HO6PVN24W Yes
Properties
Molecular formula
 C9H14N4O3
Molar mass 226.23 g·mol−1
Appearance Crystalline solid
Melting point 253 °C (487 °F; 526 K) (decomposition)
Except where noted otherwise, data is 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) is a dipeptide 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 V.Gulevich.[2] Researchers in Britain,[3] South Korea,[4] Russia[5][6] and other countries[7][8][9] 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.

Like carnitine, carnosine is composed of the root word carn, meaning flesh, alluding to its prevalence in animal protein. A vegetarian (especially vegan) diet is deficient in adequate carnosine, compared to levels found in a standard diet.[10]

Carnosine can chelate divalent metal ions.[11]

Carnosine can increase the Hayflick limit in human fibroblasts,[12] as well as appearing to reduce the telomere shortening rate.[13] Carnosine is also considered as a geroprotector.[14]

Biochemistry

In humans, postprandial blood plasma levels of carnosine is zero within several hours of red meat consumption, implying that carnosine is rapidly metabolized considering the slow digestion of animal protein.[15] This denotes a significantly short-lived impact when carnosine is taken in the form of a dietary supplement, though the latent cascade of effects from supplementing carnosine may still prove beneficial.

Physiological effects

Atherosclerosis and aging

Carnosine acts as an antiglycating agent, reducing the rate of formation of advanced glycation end-products (AGEs) (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.[16]), and ultimately reducing development of atherosclerotic plaque build-up.[11][17][18] Chronic glycolysis is speculated to accelerate aging, making carnosine a candidate for therapeutic potential.[19]

Unreviewed studies & claims

The Professor Wang et al. clinical trial study called 'Use of carnosine as a natural anti-senescence drug for human beings' was carried out on 96 patients with cataracts of varying degrees of severity, which showed a success rate of 80% in advanced senile cataracts, and 100% in patients with mild to moderate cataracts, over the 6 months trial period.[20]

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. doi:10.1002/cber.19000330275.
  3. ↑ Aruoma, OI; Laughton, MJ; Halliwell, B (1989). "Carnosine, homocarnosine and anserine: Could they act as antioxidants in vivo?". The Biochemical journal 264 (3): 863–9. PMC 1133665. PMID 2559719.
  4. ↑ Choi, Soo Young; Kwon, Hyeok Yil; Kwon, Oh Bin; Kang, Jung Hoon (1999). "Hydrogen peroxide-mediated Cu,Zn-superoxide dismutase fragmentation: Protection by carnosine, homocarnosine and anserine". Biochimica et Biophysica Acta (BBA) - General Subjects 1472 (3): 651. doi:10.1016/S0304-4165(99)00189-0.
  5. ↑ 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". Membrane & cell biology 12 (1): 89–99. PMID 9829262.
  6. ↑ 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". The Biochemical journal 304 (2): 509–16. PMC 1137521. PMID 7998987.
  7. ↑ A. Karton, R. J. O’Reilly, D. I. Pattison, M. J. Davies and L. Radom (2012). "Computational design of effective, bioinspired HOCl antioxidants: The role of intramolecular Cl+ and H+ shifts". Journal of the American Chemical Society 134 (46): 19240–5. doi:10.1021/ja309273n. PMID 23148773.
  8. ↑ Chan, Kin M.; Decker, Eric A.; Feustman, Cameron (1994). "Endogenous skeletal muscle antioxidants". Critical Reviews in Food Science and Nutrition 34 (4): 403–26. doi:10.1080/10408399409527669. PMID 7945896.
  9. ↑ Kohen, R.; Yamamoto, Y.; Cundy, K. C.; Ames, B. N. (1988). "Antioxidant Activity of Carnosine, Homocarnosine, and Anserine Present in Muscle and Brain". Proceedings of the National Academy of Sciences 85 (9): 3175. doi:10.1073/pnas.85.9.3175.
  10. ↑ 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.
  11. ↑ 11.0 11.1 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
  15. ↑ Park, Y. J.; Volpe, S. L.; Decker, E. A. (2005). "Quantitation of carnosine in humans plasma after dietary consumption of beef". Journal of Agricultural and Food Chemistry 53 (12): 4736–9. doi:10.1021/jf047934h. PMID 15941308.
  16. ↑ 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 (12): Suppl 1:3–27. doi:10.3109/10715762.2013.815348. PMID 10946212.
  17. ↑ 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.
  18. ↑ 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.
  19. ↑ 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.
  20. ↑ Wang, AM; Ma, C; Xie, ZH; Shen, F (2000). "Use of carnosine as a natural anti-senescence drug for human beings". Biochemistry. Biokhimiia 65 (7): 869–71. PMID 10951108.