Carnosine

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Carnosine[1]
Carnosine-2D-skeletal.png
Identifiers
CAS number 305-84-0 YesY
PubChem 439224
ChemSpider 388363 YesY
UNII 8HO6PVN24W YesY
KEGG C00386 YesY
ChEBI CHEBI:57485 YesY
ChEMBL CHEMBL242948 YesY
Jmol-3D images Image 1
Image 2
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 are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/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 can oppose glycation[10][11] and it can chelate divalent metal ions. Chronic glycolysis is suspected to accelerate aging.[12] Carnosine was found to inhibit diabetic nephropathy by protecting the podocytes and mesangial cells.[13]

Carnosine containing products are also used in topical preparations to reduce wrinkles on the skin.[14]

Some studies have detected beneficial effects of N-acetylcarnosine 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.[15] However, claims that carnosine confers these and other posited ophthalmological benefits are, as yet, insufficiently supported for endorsement by the mainstream medical community; Britain's Royal College of Ophthalmologists, for instance, has asserted that neither safety nor efficacy has been sufficiently demonstrated to recommend carnosine's use as a topical treatment for cataracts.[16]

A small 2002 study reported that carnosine improved socialization and receptive vocabulary in children with autism.[17] 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.[18] In animal models, supplemental carnosine can increase corticosterone levels, which may explain the hyperactivity sometimes seen in high doses.[19] However, the aforementioned study used carnosine injected into chicks intracerebroventricularly, and a raise in corticosterone levels has not yet been found in humans.

In animal models carnosine has been shown to retard cancer growth[20] and protect against alcohol-induced oxidative stress[21] as well as ethanol-induced chronic liver damage.[22] Carnosine is also neuroprotective against permanent poor oxygen supply to brain in mice.[23]

Carnosine can increase the Hayflick limit in human fibroblasts,[24] as well as appearing to reduce the telomere shortening rate.[25] This could potentially favor the growth of certain cancers that thrive due to telomere preservation.[14] Carnosine is also considered as a geroprotector.

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.[26]

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. ^ 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. 
  11. ^ 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. 
  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. 
  13. ^ Janssen, B.; Hohenadel, D.; Brinkkoetter, P.; Peters, V.; Rind, N.; Fischer, C.; Rychlik, I.; Cerna, M. et al. (2005). "Carnosine as a Protective Factor in Diabetic Nephropathy: Association with a Leucine Repeat of the Carnosinase Gene CNDP1". Diabetes 54 (8): 2320–7. doi:10.2337/diabetes.54.8.2320. PMID 16046297. 
  14. ^ a b Schwarz, E; Guest, P C; Rahmoune, H; Wang, L; Levin, Y; Ingudomnukul, E; Ruta, L; Kent, L et al. (2010). "Sex-specific serum biomarker patterns in adults with Asperger's syndrome". Molecular Psychiatry 16 (12): 1213–20. doi:10.1038/mp.2010.102. PMID 20877284. 
  15. ^ Attanasio, Francesco; Cataldo, Sebastiano; Fisichella, Salvatore; Nicoletti, Silvia; Nicoletti, Vincenzo Giuseppe; Pignataro, Bruno; Savarino, Anna; Rizzarelli, Enrico (2009). "Protective Effects of l- and d-Carnosine on α-Crystallin Amyloid Fibril Formation: Implications for Cataract Disease". Biochemistry 48 (27): 6522–31. doi:10.1021/bi900343n. PMID 19441807. 
  16. ^ Amoaku, Winfried (August 6, 2008). "N-Acetyl Carnosine for Cataracts". Royal College of Ophthalmologists. 
  17. ^ Chez, M. G.; Buchanan, C. P.; Aimonovitch, M. C.; Becker, M.; Schaefer, K.; Black, C.; Komen, J. (2002). "Double-Blind, Placebo-Controlled Study of L-Carnosine Supplementation in Children with Autistic Spectrum Disorders". Journal of Child Neurology 17 (11): 833–7. doi:10.1177/08830738020170111501. PMID 12585724. 
  18. ^ Levy, Susan E.; Hyman, Susan L. (2005). "Novel treatments for autistic spectrum disorders". Mental Retardation and Developmental Disabilities Research Reviews 11 (2): 131–42. doi:10.1002/mrdd.20062. PMID 15977319. 
  19. ^ Tomonaga, Shozo; Tachibana, Tetsuya; Takagi, Tomo; Saito, Ei-Suke; Zhang, Rong; Denbow, D.Michael; Furuse, Mitsuhiro (2004). "Effect of central administration of carnosine and its constituents on behaviors in chicks". Brain Research Bulletin 63 (1): 75–82. doi:10.1016/j.brainresbull.2004.01.002. PMID 15121241. 
  20. ^ Renner, Christof; Zemitzsch, Nadine; Fuchs, Beate; Geiger, Kathrin D; Hermes, Matthias; Hengstler, Jan; Gebhardt, Rolf; Meixensberger, Jürgen; Gaunitz, Frank (2010). "Carnosine retards tumor growth in vivo in an NIH3T3-HER2/neu mouse model". Molecular Cancer 9: 2. doi:10.1186/1476-4598-9-2. PMC 2818694. PMID 20053283. 
  21. ^ Ozel Turkcu, Ummuhani; Bilgihan, Ayşe; Biberoglu, Gursel; Mertoglu Caglar, Oznur (2010). "Carnosine supplementation protects rat brain tissue against ethanol-induced oxidative stress". Molecular and Cellular Biochemistry 339 (1–2): 55–61. doi:10.1007/s11010-009-0369-x. PMID 20047045. 
  22. ^ Liu, Wen-hu; Liu, Te-Chung; Yin, Mei-Chin (2008). "Beneficial effects of histidine and carnosine on ethanol-induced chronic liver injury". Food and Chemical Toxicology 46 (5): 1503–9. doi:10.1016/j.fct.2007.12.013. PMID 18222027. 
  23. ^ Min, Jiangyong; Senut, Marie-Claude; Rajanikant, Krishnamurthy; Greenberg, Eric; Bandagi, Ram; Zemke, Daniel; Mousa, Ahmad; Kassab, Mounzer et al. (2008). "Differential neuroprotective effects of carnosine, anserine, andN-acetyl carnosine against permanent focal ischemia". Journal of Neuroscience Research 86 (13): 2984–91. doi:10.1002/jnr.21744. PMC 2805719. PMID 18543335. 
  24. ^ 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. 
  25. ^ 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. 
  26. ^ 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.