Anserine

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title: "Anserine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["dipeptides"] topic_path: "general/dipeptides" source: "https://en.wikipedia.org/wiki/Anserine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443392191 | ImageFile = Anserine.svg | ImageSize = 220px | SystematicName = (2S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid | OtherNames = beta-Alanyl-3-methyl-L-histidine | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 100482 | KEGG_Ref = | KEGG = C01262 | InChI = 1/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1 | InChIKey = MYYIAHXIVFADCU-QMMMGPOBBJ | ChEMBL_Ref = | ChEMBL = 448301 | StdInChI_Ref = | StdInChI = 1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = MYYIAHXIVFADCU-QMMMGPOBSA-N | CASNo_Ref = | CASNo=584-85-0 | UNII_Ref = | UNII = HDQ4N37UGV | PubChem=112072 | ChEBI_Ref = | ChEBI = 18323 | SMILES = O=C(O)C@@HCc1cncn1C | Section2 = {{Chembox Properties | Formula = C10H16N4O3 | MolarMass = 240.25904 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine. Anserine is a derivative of carnosine, which has been methylated.

Anserine has biological activities similar to those of carnosine, including buffering activity, antioxidant properties, metal ion chelation, and anti-aggregation effects. Both anserine and carnosine chelate copper. Because of its methylation, anserine is more stable in serum and resistant to degradation than carnosine. Compared with carnosine, anserine have a higher antioxidant capacity.

Anserine can be found in the skeletal muscle and brain of mammals and birds. Anserine is also found in human kidney.

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04.

Biosynthesis

Anserine can be synthesized through methylation of carnosine, by carnosine N-methyltransferase (CARNMT1).

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. In another high-fat diet model, anserine treatment exhibited hypolipidemic and anti-obesity effects by inhibiting p-NF-κB p65 expression.

Metal binding

Both anserine and carnosine bind copper and other transition metals. Chelation of transition metals is one mechanism for their antioxidant activity.

References

References

  1. (2012). "Biochemistry". Cengage Learning.
  2. (2016-09-01). "Carnosine and anserine homeostasis in skeletal muscle and heart is controlled by β-alanine transamination". The Journal of Physiology.
  3. (Oct 2013). "Physiology and pathophysiology of carnosine". Physiological Reviews.
  4. (January 2019). "Development and validation of a sensitive LC-MS/MS assay for the quantification of anserine in human plasma and urine and its application to pharmacokinetic study". Amino Acids.
  5. (Sep 2018). "Protective Actions of Anserine Under Diabetic Conditions". International Journal of Molecular Sciences.
  6. (2015). "Intrinsic carnosine metabolism in the human kidney". Amino Acids.
  7. Wu, Guoyao. (March 2020). "Important roles of dietary taurine, creatine, carnosine, anserine and 4-hydroxyproline in human nutrition and health". Amino Acids.
  8. (October 2017). "Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AβPPswe/PSEN1dE9 Alzheimer's-model mice". Scientific Reports.
  9. (Jun 2023). "Carnosinase-1 Knock-Out Reduces Kidney Fibrosis in Type-1 Diabetic Mice on High Fat Diet". Antioxidants.
  10. (Mar 2024). "Hypolipidemic and Anti-Obesity Effect of Anserine on Mice Orally Administered with High-Fat Diet via Regulating SREBP-1, NLRP3, and UCP-1". Molecular Nutrition & Food Research.
  11. (1991). "The SOD like activity of copper:carnosine, copper:anserine and copper:homocarnosine complexes". Free Radical Research Communications.
  12. (1994). "Endogenous skeletal muscle antioxidants". Critical Reviews in Food Science and Nutrition.

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dipeptides