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Carnosine

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.610 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 checkY
    Key: CQOVPNPJLQNMDC-ZETCQYMHSA-N checkY
  • InChI=1/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1
    Key: CQOVPNPJLQNMDC-ZETCQYMHBX
  • O=C(O)C(NC(=O)CCN)Cc1c[nH]cn1
  • c1c(nc[nH]1)C[C@@H](C(=O)O)NC(=O)CCN
Properties
C9H14N4O3
Molar mass 226.236 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).
checkY verify (what is checkY☒N ?)

Carnosine (beta-alanyl-L-histidine) 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] 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. Carnosine 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.[10] A vegetarian (especially vegan) diet provides less carnosine, compared to levels found in a more typical diet including meat.[11]

Carnosine can chelate divalent metal ions.[12]

Carnosine can increase the Hayflick limit in human fibroblasts,[13] as well as appearing to reduce the telomere shortening rate.[14] Carnosine is also considered as a geroprotector.[15]

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.[12][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]

Carnosine and blueberry extract together synergistically improved proliferation of human stem cells in vitro by 83%.[21]

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. ^ 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. doi:10.1042/bj2640863. 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): 651–657. 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. doi:10.1042/bj3040509. PMC 1137521. PMID 7998987.
  7. ^ A. Karton; R. J. O’Reilly; D. I. Pattison; M. J. Davies; 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): 3175–3179. 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. ^ Alan R. Hipkiss (2009). "Chapter 3: Carnosine and Its Possible Roles in Nutrition and Health". Advances in Food and Nutrition Research.
  12. ^ a b 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.
  13. ^ 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.
  14. ^ 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.
  15. ^ 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.
  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: Suppl 1:3–27. doi:10.3109/10715762.2013.815348. PMID 23767955.
  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.
  21. ^ Bickford PC, Tan J, Shytle RD, et al. Nutraceuticals synergistically promote proliferation of human stem cells. Stem Cells Dev. 2006 Feb;15(1):118-23.
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