Inhibition Effect of Carnosine on Protein Oxidation and Saccharification
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The effects of carnosine (beta-alanyl-L-histidine) and anserine (beta-alanyl-1-methyl-L-histidine) on ascorbate-dependent lipid peroxidation in frog skeletal muscle sarcoplasmic reticulum were studied. It was found that the dipeptides (10-50 mM) cause a 25-90% inhibition of ascorbate-dependent lipid peroxidation and decrease the reaction rate and the amount of end products. The nature of lipid peroxidation primary products in the presence of the dipeptides changes which can be evidenced from changes in their spectral properties. Unlike other known natural antioxidants, skeletal muscle dipeptides do not only inhibit lipid peroxidation but also decrease the level of accumulated lipid peroxidation products. Histidine and beta-alanine, similar to imidazole, glycyl-glycine, arginyl-phenyl alanine and alpha-alanyl-D-histidine do not inhibit lipid peroxidation. At the same time, the carnosine stereoisomer D-carnosine which does not exist in nature exhibits a far greater inhibiting effect as compared to its natural counterpart. It is assumed that the skeletal muscle dipeptides carnosine and anserine are highly effective as natural antioxidants.
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Anserine
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Monosaccharide
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The authors studied the protective action of carnosine on sarcoplasmic reticulum (SR) membranes from frog skeletal muscles destroyed by ascorbic acid-dependent lipid peroxidation (LPO). It was demonstrated that addition of carnosine to the incubation medium at a concentration of 25 mM sharply decelerated inactivation of Ca-ATPase of SR membranes, maintaining at the same time the coupling of hydrolysing and transport functions of the Ca-pump. When given at the same concentration carnosine inhibited the accumulation of LPO products reacting with 2-thiobarbituric acid. This effect of carnosine was followed by its utilization.
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Thiobarbituric acid
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Carnosine, homocarnosine, and anserine are present in high concentrations in the muscle and brain of many animals and humans. However, their exact function is not clear. The antioxidant activity of these compounds has been examined by testing their peroxyl radical-trapping ability at physiological concentrations. Carnosine, homocarnosine, anserine, and other histidine derivatives all showed antioxidant activity. All of these compounds showing peroxyl radical-trapping activity were also electrochemically active as reducing agents in cyclic voltammetric measurements. Furthermore, carnosine inhibited the oxidative hydroxylation of deoxyguanosine induced by ascorbic acid and copper ions. Other roles of carnosine, such as chelation of metal ions, quenching of singlet oxygen, and binding of hydroperoxides, are also discussed. The data suggest a role for these histidine-related compounds as endogenous antioxidants in brain and muscle.
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Anserine
Hydroxylation
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Carnosine is a dipeptide(β-Ala-L-His)found in skeletal muscle and brain tissue of vertebrates.To determine the correlation between its structure and antioxidant properties,carnosine,β-alanine and L-histidine were analyzed.The scavenging ability on DPPH radical and the inhibitory effect on BSA oxidation were tested.The results illustrated that carnosine significantly scavenged DPPH radical(P0.01);histidine had much weaker ability than carnosine but alanine had no role on DPPH.Carnosine significantly decreased the protein carbonyl formation(P0.01);alanine showed low inhibitory effect among the compounds,but the effects of histidine as the concentration of 10,20,50mmol·L-1 were better than carnosine.
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Alanine
Anserine
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Abstract The antioxidant effects of carnosine on lipids and nonlipids, including liposomes, carbohydrates, and proteins, were investigated. Carnosine exhibited a remarkable antioxidant effect in liposome and deoxyribose model systems. Carnosine at high amounts (50 mg/mL) was effective in protecting protein against oxidation. The correlation coefficients between reducing ability and the inhibition of liposome, albumin, and deoxyribose oxidation were r =0.92, 0.83, and 0.41, respectively. Carnosine exhibited metal‐binding ability and scavenging ability for hydroxyl radicals generated by photolysis of H 2 O 2 with UV light. The correlation coefficients between hydroxyl radical scavenging and the inhibitory effect on deoxyribose, liposome, and albumin oxidative damage were r =0.97, 0.60, and 0.29, respectively. These properties may explain how carnosine protects lipids and non‐lipids against oxidative damage.
Deoxyribose
Carnosine
Hydroxyl radical
Lipid Oxidation
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The activity of carnosine as a quencher for superoxide anion radical and ·OH radical was evaluated in the auto-oxidation of pyrogallol system and deoxyribose degradation system respectively,and the inhibitory effect of carnosine on lipid peroxidation was determined in different systems including that red blood cell was induced by H_2O_2、UV and liver homogate was induced by CCl_4.The results show that carnosine can quench the superoxide anion radical at a low concentration(1mmol/L) and the ability decreased with a high concentration,carnosine scavenged ·OH radical in a dose-dependent manner and protected the deoxyribose from oxidative damage,carnosine inhibited the peroxidation in RBC and greatly decreased the content of lipid peroxidation products in liver homogate.
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Deoxyribose
Pyrogallol
Hydroxyl radical
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The antioxidant activity of carnosine, a β‐alanine‐histidine dipeptide found in skeletal muscle, was investigated. Carnosine (25 mM) inhibited the catalysis of lipid oxidation by iron, hemoglobin, lipoxidase and singlet oxygen from 35–96% suggesting that the antioxidant mechanism of carnosine is not solely due to metal chelation. Heating the carnosine at 100°C for 15 min had no effect on its ability to inhibit these lipid oxidation catalysts, and the activity of carnosine was not affected over the pH range of 5.1–7.1. Studies using tocopherol‐containing liposomes suggest that carnosine and tocopherol do not act synergistically to inhibit lipid oxidation. These data indicate that carnosine has excellent potential for use as a natural antioxidant in processed foods.
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Lipid Oxidation
Anserine
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