L-карнозин

Описание

L-Carnosine is a dipeptide composed of β-alanine and L-histidine that has been found in rat olfactory bulb, skeletal muscle, brain, kidney, and spleen tissues, as well as human skeletal muscle, and has diverse biological activities. It is a metal chelator that forms complexes with copper, cobalt, nickel, cadmium, or zinc. Dietary administration of L-carnosine (60 mg/kg per day) reduces plasma levels of advanced glycation end products (AGEs) in diabetic rats. It reduces brain edema, blood-brain barrier disruption, microglial activation, and neuronal apoptosis in a rat model of intracerebral hemorrhage when administered at a dose of 1,000 mg/kg. L-Carnosine (250, 500, and 1,000 mg/kg, i.p.) reduces hepatic protein carbonylation and necrosis in a rat model of cirrhosis induced by bile duct ligation. It also reduces lung myeloperoxidase (MPO) activity, production of reactive oxygen species (ROS), and TNF-α and IL-6 levels, as well as alveolar hemorrhage, interstitial edema, and pulmonary leukocyte infiltration in a mouse model of LPS-induced lung injury.

Химические свойства

white to off-white crystalline.

История

Carnosine, a dipeptide composed of beta-alanine and L-histidine, was first identified in beef extracts by Russian chemists Gulewitch and Amiradzibi in 1900.

Использование

L-Carnosine is a naturally-occurring histidine-containing compound and the biological role of this dipeptide is to act as cytosolic buffering agents. Other roles ascribed to L-Carnosine include action s as neurotransmitters, modulation of enzymic activities and chelation of heavy metals. Studies indicate an ability to boost the immunological functions. In cosmetics, it has anti-aging and skin-conditioning applications.

Определение

ChEBI: Carnosine is a dipeptide that is the N-(beta-alanyl) derivative of L-histidine. It has a role as an anticonvulsant, an antioxidant, an antineoplastic agent, a human metabolite, a Daphnia magna metabolite, a mouse metabolite, a neuroprotective agent and a geroprotector. It is a conjugate acid of a carnosinate. It is a tautomer of a carnosine zwitterion.

Побочные эффекты

L-carnosine is generally considered safe when taken by mouth for short periods of time or when used by adults on the skin. However, there can be rare side effects, including rash, itchiness, dry mouth, changes in appetite, feelings of tiredness or vivid dreams. Rare but severe possible zinc carnosine side effects include decreased white blood cells, disorder of the digestive system and sideroblastic anemia. Less severe side effects may include stomach cramps, indigestion and nausea.

Профиль безопасности

Mildly toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

Методы очистки

Likely impurities are histidine and β-alanine. Crystallise L-carnosine from water by adding EtOH in excess. Recrystallise it from aqueous EtOH by slow addition of EtOH to a strong aqueous solution of the dipeptide. Its solubility in H2O is 33.3% at 25o. [Vinick & Jung J Org Chem 48 392 1983, Turner J Am Chem Soc 75 2388 1953, Sifford & du Vigneaud J Biol Chem 108 753 1935, Beilstein 25 H 516, 25 I 717, 25 II 408.]

использованная литература

1. P. J. Quinn, A. A. Boldyrev, V. E. Formazuyk, Carnosine: Its properties, functions and potential therapeutic applications, Molecular Aspects of Medicine, 1992, vol. 13, pp. 379-444 DOI:10.1016/0098-2997(92)90006-L
2. https://www.webmd.com/vitamins/ai/ingredientmono-1038/carnosine
3. G. M. Halpern, Zinc-Carnosine: Nature’s Safe and Effective Remedy for Ulcers, 2005, ISBN-10 0757002749
4. l-Carnosine, a Substrate of Carnosinase-1, Influences Glucose Metabolism DOI:10.2337/db07-0177
5. L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities. DOI:10.1042/BJ3040509
6. Boldyrev, A.A., Aldini, G., and Derave, W. Physiology and pathophysiology of carnosine. Physiol. Rev. 93(4), 1803-1845 (2013). DOI:10.1152/physrev.00039.2012
7. Ghodsi, R., and Kheirouri, S. Carnosine and advanced glycation end products: A systematic review. Amino Acids 50(9), 1177-1186 (2018). DOI:10.1007/s00726-018-2592-9
8. Tanaka, K.I., Sugizaki, T., Kanada, Y., et al. Preventive effects of carnosine on lipopolysaccharide-induced lung injury. Sci. Rep. 7:42813, (2017). DOI:10.1038/srep42813