Carnosine

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Not to be confused with carnitine.
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.

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 was found to inhibit diabetic nephropathy by protecting the podocytes and mesangial cells.[12]

Carnosine-containing products are also used in topical preparations to reduce wrinkles on the skin.[13]

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.[14] 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.[15]

A small 2002 study reported that carnosine improved socialization and receptive vocabulary in children with autism.[16] 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.[17] In animal models, supplemental carnosine can increase corticosterone levels, which may explain the hyperactivity sometimes seen in high doses.[18] However, the aforementioned study used carnosine injected into chicks intracerebroventricularly, and a rise in corticosterone levels has not yet been found in humans.

In animal models carnosine has been shown to retard cancer growth[19] and protect against alcohol-induced oxidative stress[20] as well as ethanol-induced chronic liver damage.[21] Carnosine is also neuroprotective against permanent poor oxygen supply to brain in mice.[22]

Carnosine can increase the Hayflick limit in human fibroblasts,[23] as well as appearing to reduce the telomere shortening rate.[24] This could potentially favor the growth of certain cancers that thrive due to telomere preservation.[13] Carnosine is also considered as a geroprotector.

Biochemistry[edit]

In humans, postprandial blood plasma levels of carnosine is zero within several hours of red meat consumption, inferring that carnosine is rapidly metabolized considering the slow digestion of animal protein.[25] 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[edit]

Carnosine acts as an antiglycating agent, reducing the rate of formation of advanced glycation end-products (AGEs), and ultimately reducing development of atherosclerotic plaque build-up.[11][26][27] Chronic glycolysis is speculated to accelerate aging, making carnosine a candidate for therapeutic potential.[28]

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.[29]


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.  edit
  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. ^ 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. 
  13. ^ 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. 
  14. ^ 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. 
  15. ^ Amoaku, Winfried (August 6, 2008). "N-Acetyl Carnosine for Cataracts". Royal College of Ophthalmologists. 
  16. ^ 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. 
  17. ^ 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. 
  18. ^ 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. 
  19. ^ 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. 
  20. ^ 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. 
  21. ^ 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. 
  22. ^ 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. 
  23. ^ 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. 
  24. ^ 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. 
  25. ^ 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.  edit
  26. ^ 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. 
  27. ^ 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.  edit
  28. ^ 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. 
  29. ^ 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.