Anserine
Chemical compound
From Wikipedia, the free encyclopedia
Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine.[1] Anserine is a derivative of carnosine, which has been methylated.[2]
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| Names | |
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| Systematic IUPAC name
(2S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid | |
| Other names
beta-Alanyl-3-methyl-L-histidine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.679 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H16N4O3 | |
| Molar mass | 240.25904 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anserine has biological activities similar to those of carnosine, including buffering activity, antioxidant properties, metal ion chelation, and anti-aggregation effects.[3] Both anserine and carnosine chelate copper.[4] Because of its methylation, anserine is more stable in serum and resistant to degradation than carnosine.[5] Compared with carnosine, anserine have a higher antioxidant capacity.[6]
Anserine can be found in the skeletal muscle and brain of mammals and birds.[2] Anserine is also found in human kidney.[7]
The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04.[8][9]
Biosynthesis
Anserine can be synthesized through methylation of carnosine, by carnosine N-methyltransferase (CARNMT1).[3]
Anti-inflammatory effects
High concentration of anserine reduced interstitial inflammation and alleviated Kidney Fibrosis in Type-1 diabetic mice with Carnosinase-1 knock-out on high fat diet.[10] In another high-fat diet model, anserine treatment exhibited hypolipidemic and anti-obesity effects by inhibiting p-NF-κB p65 expression.[11]
