β-アラニル-L-ヒスチジン

解説カルノシン，ジペプチドの一つ，いろいろな動物の筋肉中に存在する．ガチョウ，ハトではアンセリンが，ヘビではオフィジンがかわりになっている．L-ヒスチジンとカルボベンゾキシβ-アラニンから合成できる．分解点246～250 ℃．＋24.1°(水)．生体中の役割は明確でないが，筋収縮，神経伝達，糖の代謝などに関与していると考えられる．強いpH緩衝性，抗酸化性，膜安定性を示す．

用途生体内アミノ酸分析の指標、生理活性の研究。

説明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.

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

使用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.

使用用途カルノシンは、抗酸化作用、緩衝作用、抗疲労作用など多くの効果が期待できます。しかし、体内のカルノシンは加齢に伴って減少していきます。ですから、カルノシンを摂取することで、運動力の維持、活性酸素を抑えての疲労回復やアンチエイジング効果が期待できます。カルノシンは、鶏肉、牛肉、豚肉から多く摂取できます。また、サプリメントでも摂取できます。 カルノシンは、肉製品の褐色化を抑制します。また、銅イオンによるアスコルビン酸の酸化を阻害します。そのため、カルノシンとアスコルビン酸を肉製品に添加すると、品質を保ち、色調の安定に効果的です。

純化方法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.]

定義本品は、次の化学式で表されるジペプチドである。

定義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.