Anserine Supplier

Anserine

Catalog No.

S518983

CAS No.

584-85-0

M.F

C10H16N4O3

M. Wt

240.26 g/mol

Availability

In Stock

This item is exclusively intended for research purposes and is not designed for human therapeutic applications or veterinary use.

Content Navigation

• General Information
• Scientific Research Applications
• Description
• Mechanism of Action
• Safety and Hazards
• Chemical Reactions
• Biological Activity
• Synthesis Methods
• Applications
• Similar Compounds
• Specification
• Others
• Reference

General Information

CAS Number

584-85-0

Product Name

Anserine

IUPAC Name

(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid

Molecular Formula

C10H16N4O3

Molecular Weight

240.26 g/mol

InChI

InChI=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

InChI Key

MYYIAHXIVFADCU-QMMMGPOBSA-N

SMILES

CN1C=NC=C1CC(C(=O)O)NC(=O)CCN

solubility

Soluble in DMSO

Synonyms

Anserine, Balanine, Beta Alanyl 3 Methylhistidine, Beta-Alanyl-3-Methylhistidine, Ophidine

Canonical SMILES

CN1C=NC=C1CC(C(=O)O)NC(=O)CCN

Isomeric SMILES

CN1C=NC=C1C[C@@H](C(=O)O)NC(=O)CCN

The exact mass of the compound Anserine is 240.1222 and the complexity rating of the compound is unknown. The solubility of this chemical has been described as Soluble in DMSO. Its Medical Subject Headings (MeSH) category is Chemicals and Drugs Category - Amino Acids, Peptides, and Proteins - Peptides - Oligopeptides - Dipeptides. It belongs to the ontological category of dipeptide in the ChEBI Ontology tree. The storage condition is described as Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Scientific Research Applications

Antioxidant Properties

Anserine exhibits potent antioxidant activity. Studies have shown it can scavenge free radicals, protect cells from oxidative damage, and inhibit lipid peroxidation. This has led researchers to investigate its role in preventing diseases associated with oxidative stress, such as neurodegenerative disorders and cardiovascular diseases.

Neuromodulatory Effects

Anserine is present in high concentrations in the brain and has been shown to modulate various neurological functions. Research suggests it may play a role in learning, memory, and neuroprotection. Studies have investigated its potential benefits in treating neurodegenerative diseases like Alzheimer's disease and Parkinson's disease.

Exercise Performance and Muscle Function

Anserine is found in skeletal muscle and is believed to contribute to muscle buffering capacity and fatigue resistance. Studies have explored its effects on exercise performance and recovery, with some suggesting it may improve endurance and reduce muscle soreness.

Description

Anserine, scientifically known as β-alanyl-N-3-methylhistidine, is a dipeptide formed from the amino acids beta-alanine and 3-methylhistidine. It is a methylated derivative of carnosine, which consists of beta-alanine and L-histidine. Anserine is predominantly found in the skeletal muscles and brains of various mammals and birds, where it plays a significant role in muscle function and neuroprotection. Its structural stability is enhanced by methylation, making it more resistant to degradation compared to carnosine.

Mechanism of Action

Anserine's primary mechanism of action is believed to be related to its buffering capacity in muscle tissue. During exercise, muscles produce lactic acid, leading to a decrease in pH (acidification). Anserine, along with carnosine, acts as a buffer by absorbing protons (H+), thereby helping to maintain muscle pH within a functional range and delaying fatigue.

Additionally, anserine's chelating properties might contribute to its antioxidant activity by scavenging free radicals generated during exercise, potentially reducing oxidative stress in muscle cells. However, further research is needed to fully elucidate the mechanisms of anserine's antioxidant effects.

Safety and Hazards

Anserine is generally considered safe for consumption at recommended doses. However, limited data exists on its potential toxicity in humans. More research is needed to establish a safe upper limit for anserine intake.

Note

This analysis is based on currently available scientific research. As research progresses, our understanding of anserine's properties and mechanisms of action may evolve.

Cited Sources

• Li X, Li Y, Liu X, et al. Carnosine N-methyltransferase from Atlantic cod (Gadus morhua): Molecular cloning, functional characterization and tissue distribution. Comparative Biochemistry and Physiology Part B: Biochemistry and Molecular Biology. 2009;153(3):282-288.

Chemical Reactions

Chemical reactions involving anserine primarily involve its antioxidant properties. It acts as a chelating agent for transition metals such as copper, which helps mitigate oxidative stress by preventing harmful reactions with peroxides. The synthesis of anserine occurs through the methylation of carnosine, catalyzed by the enzyme carnosine-N-methyltransferase, which transfers a methyl group from S-adenosylmethionine to carnosine.

Biological Activity

Anserine exhibits various biological activities that contribute to its physiological roles:

• Antioxidant Properties: Anserine can scavenge free radicals and reduce oxidative damage, particularly during exercise-induced stress. Studies have shown that supplementation with anserine increases the activity of superoxide dismutase, an important antioxidant enzyme.
• Neuroprotective Effects: Research indicates that anserine may improve cognitive function and reduce memory loss in animal models of Alzheimer's disease by decreasing glial inflammatory activity. Human studies also suggest enhanced blood flow in the prefrontal cortex following anserine supplementation.
• Muscle Function: Anserine has been shown to enhance muscle differentiation and contractility, indicating its importance in muscle physiology.

Synthesis Methods

The synthesis of anserine is primarily achieved through enzymatic reactions:

• Formation from Carnosine: Anserine is synthesized by the action of carnosine-N-methyltransferase on carnosine, where a methyl group is added to the nitrogen atom of histidine in carnosine.
• Enzymatic Requirements: The reaction requires S-adenosylmethionine as the methyl donor and occurs in tissues expressing the CARNMT1 gene, particularly in skeletal muscle.

Applications

Anserine has several applications across different fields:

• Nutritional Supplements: Due to its antioxidant properties, anserine is often included in dietary supplements aimed at improving athletic performance and recovery.
• Neuroprotective Agents: Its potential benefits for cognitive health make it a candidate for developing supplements targeting neurodegenerative diseases.
• Food Industry: Anserine levels can be used as indicators in the food industry.