Anserine

Anserine (β‑N‑π‑carboxyethylhistidine) is a naturally occurring imidazole dipeptide composed of β‑alanine and 1‑methylhistidine.

• Source: Found primarily in the skeletal muscle and brain of birds and fish.
• Function: Acts as a potent antioxidant and metal‑chelating agent.
• Use: Commonly used as a dietary supplement to support cognitive health and mitigate oxidative stress.

• Type: A dipeptide (β‑alanine‑1‑methyl‑histidine).
• Molecular Formula: C₈H₁₅N₅O₃
• Molecular Weight: 219.24 g·mol⁻¹
• IUPAC Name: N‑β‑alanine‑1‑methyl‑L‑histidine
• Structure: Consists of a β‑alanine (NH₂‑CH₂‑CH₂‑COOH) linked via an amide bond to a 1‑methyl‑histidine residue, giving the characteristic imidazole ring with a methyl group at the N1 position.
• Charge: Zwitterionic at physiological pH.
• pKa: ≈ 7.2, which confers its buffering capacity.
• Solubility: Highly soluble in water (≈30 g/L at 25 °C).
• Stability: Stable under neutral pH.
• Hydrolysis: Susceptible to enzymatic hydrolysis by dipeptidases, which can be mitigated by encapsulation or co-administration with carnosine.

• Source: Predominantly extracted from the skeletal muscle of poultry (especially chicken breast) and certain fish (e.g., tuna, mackerel).
• Content: Can constitute up to 2 % of the total protein content.
• Production: Commercial production often utilizes enzymatic hydrolysis of meat protein followed by solid‑phase extraction and high‑performance liquid chromatography (HPLC) purification to achieve >95 % purity.
• Synthetic Route: Synthetic routes involve stepwise coupling of β‑alanine with protected 1‑methyl‑histidine, but this is less common due to cost.
• Supplement Quality: Quality‑controlled supplements should specify “≥ 95 % anserine, minimal contaminants, GMP‑certified” and provide a certificate of analysis (COA) confirming absence of heavy metals, microbial contamination, and accurate labeling.
• Bioavailability: Formulations may use micro-encapsulation or co-delivery with a small amount of carnosine to exploit shared intestinal transporters.