L- carnosine

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Structural formula
Structure of Carnosine
General
Surname L- carnosine
other names
  • β- alanyl- L- histidine
  • ( S ) -2- (3-Aminopropanoylamino) -3- (3 H -imidazol-4-yl) propanoic acid
  • CARNOSINE ( INCI )
Molecular formula C 9 H 14 N 4 O 3
Brief description

colorless crystals

External identifiers / databases
CAS number
EC number 206-169-9
ECHA InfoCard 100.005.610
PubChem 439224
ChemSpider 388363
DrugBank DB11695
Wikidata Q413822
properties
Molar mass 226.23 g mol −1
Physical state

firmly

Melting point

260 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 14,930 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carnosine ( β- alanyl- L- histidine) is a dipeptide composed of the amino acids β-alanine and L - histidine .

Carnosine was first isolated in 1900 by Vladimir Gulevich and his student Amiradzibi, and Gulevich also found the correct structural formula in 1907.

description

Carnosine is found in increased concentrations in human muscle and brain tissue . In birds, the methyl derivative anserine is found instead .

A clinical study has shown that carnosine can be an effective dietary supplement for people with autism . It affects areas of the brain that are responsible for hearing, language, movement and socialization. However, carnosine can cause corticosterone levels to rise. This explains the hyperactivity observed when high doses are administered.

The reaction of carnosine with ROS ( reactive oxygen species ) was tested. It can scavenge these as well as α-β-unsaturated aldehydes , which are formed during the peroxidation of fatty acids in the cell membrane during oxidative stress. It can chelate various metal ions and prevent glycation .

However, some studies regarding the beneficial effect of N- acetylcarnosine on cataracts have not yet been reviewed. Britain's Royal College of Ophthalmologists stated that neither safety nor efficacy has been sufficiently demonstrated to justify its use.

literature

  • Shozo Tomonagaa, Tetsuya Tachibanaa, Tomo Takagia, Ei-Suke Saitoa, Rong Zhanga, D. Michael Denbowb, Mitsuhiro Furusea: Effect of central administration of carnosine and its constituents on behaviors in chicks. In: Brain research bulletin. Vol. 63, No. 1, March 2004, pp. 75-82, PMID 15121241 , doi : 10.1016 / j.brainresbull.2004.01.002 .

Web links

Individual evidence

  1. ↑ entry to CARNOSINE in CosIng database of the European Commission, accessed on 20 April 2020th
  2. ↑ L-Carnosine data sheet from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
  3. ↑ a b Entry on L-carnosine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ a b Data sheet L-Carnosine, ~ 99%, crystalline from Sigma-Aldrich , accessed on February 12, 2013 ( PDF ).
  5. ↑ Wladimir Sergejewitsch Gulewitsch , S. Amiradžibi: About carnosine, a new organic base of meat extract . In: Reports of the German Chemical Society . 33, No. 2, 1900, p. 1902. doi : 10.1002 / cber.19000330275 .
  6. ↑ Gulevich, Amiradzibi, Z. f. Physiol. Chemie, Volume 30, 1900, p. 565
  7. ↑ Anatoly Bezkorovainy: Carnosine, carnitine, and Vladimir Gulevich . In: J. Chem. Education , Vol. 51, 1974, pp. 652-654. doi : 10.1021 / ed051p652 .
  8. ↑ Michael G. Chez, Cathleen P. Buchanan, Mary C. Aimonovitch, Marina Becker, Karla Schaefer, Carter Black, Jamie Komen: Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders. In: Journal of child neurology. Vol. 17, No. 11, November 2002, pp. 833-837, PMID 12585724 , doi : 10.1177 / 08830738020170111501 .
  9. ↑ OI Aruoma, MJ Laughton, B Halliwell: Carnosine, homocarnosine and anserine: Could They act as antioxidants in vivo? . In: The Biochemical journal . 264, No. 3, 1989, pp. 863-9. PMID 2559719 . PMC 1133665 (free full text).
  10. ↑ Soo Young Choi, Hyeok Yil Kwon, Oh Bin Kwon, Jung Hoon Kang: Hydrogen peroxide-mediated Cu, Zn-superoxide dismutase fragmentation: Protection by carnosine, homocarnosine and anserine . In: Biochimica et Biophysica Acta (BBA) - General Subjects . 1472, No. 3, 1999, p. 651. doi : 10.1016 / S0304-4165 (99) 00189-0 .
  11. ↑ GI Klebanov, YuO Teselkin, IV Babenkova, OB Lyubitsky, OYu Rebrova, AA Boldyrev, YuA Vladimirov: Effect of carnosine and its components on free-radical reactions . In: Membrane & cell biology . 12, No. 1, 1998, pp. 89-99. PMID 9829262 .
  12. ↑ MA Babizhayev, MC Seguin, J Gueyne, RP Evstigneeva, EA Ageyeva, GA Zheltukhina: L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid -peroxidase activities . In: The Biochemical journal . 304, No. 2, 1994, pp. 509-16. PMID 7998987 . PMC 1137521 (free full text).
  13. ^ A. Karton, RJ O'Reilly, DI Pattison, MJ Davies and L. Radom: Computational design of effective, bioinspired HOCl antioxidants: The role of intramolecular Cl + and H + shifts. . In: Journal of the American Chemical Society . 2012. doi : 10.1021 / ja309273n .
  14. ↑ Kin M. Chan, Eric A. Decker, Cameron Feustman: Endogenous skeletal muscle antioxidants . In: Critical Reviews in Food Science and Nutrition . 34, No. 4, 1994, pp. 403-26. doi : 10.1080 / 10408399409527669 . PMID 7945896 .
  15. ^ R. Kohen: Antioxidant Activity of Carnosine, Homocarnosine, and Anserine Present in Muscle and Brain . In: Proceedings of the National Academy of Sciences . 85, No. 9, 1988, p. 3175. doi : 10.1073 / pnas.85.9.3175 .
  16. ↑ VP Reddy, MR Garrett, G Perry, MA Smith: Carnosine: A Versatile Antioxidant and Antiglycating Agent . In: Science of Aging Knowledge Environment . 2005, No. 18, 2005, p. Pe12. doi : 10.1126 / sageke.2005.18.pe12 . PMID 15872311 .
  17. ↑ Imran Rashid, David M. Van Reyk, Michael J. Davies: Carnosine and its constituents inhibit glycation of low-density lipoproteins that promotes foam cell formation in vitro . In: FEBS Letters . 581, No. 5, 2007, pp. 1067-1070. doi : 10.1016 / j.febslet.2007.01.082 . PMID 17316626 .