Carnosine

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Not to be confused with carnitine.
Carnosine[1]
Carnosine-2D-skeletal.png
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 YesY
ChEBI CHEBI:57485 YesY
ChEMBL ChEMBL242948 YesY
ChemSpider 388363 YesY
4559
Jmol-3D images Image
Image
KEGG C00386 YesY
PubChem 439224
UNII 8HO6PVN24W YesY
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).
 YesY verify (what isYesY/N?)
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. 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. 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[edit]

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[edit]

Atherosclerosis and aging[edit]

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[edit]

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[edit]

References[edit]

  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. ^ 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. 
  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.