Anserine (β-alanyl-''3''-methylhistidine) is a
dipeptide
A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiological ...
containing
β-alanine and
3-methylhistidine.
Anserine is a derivative of
carnosine
Carnosine (''beta''-alanyl-L-histidine) is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues. Carnosine was discovered by Russian chemist Vladimir Gulevich.
Ca ...
, 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
Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...
, 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
Skeletal muscle (commonly referred to as muscle) is one of the three types of vertebrate muscle tissue, the others being cardiac muscle and smooth muscle. They are part of the somatic nervous system, voluntary muscular system and typically are a ...
and
brain
The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...
of
mammal
A mammal () is a vertebrate animal of the Class (biology), class Mammalia (). Mammals are characterised by the presence of milk-producing mammary glands for feeding their young, a broad neocortex region of the brain, fur or hair, and three ...
s and birds.
Anserine is also found in human kidney.
The
pKa
In chemistry, an acid dissociation constant (also known as acidity constant, or acid-ionization constant; denoted ) is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction
:H ...
of the
imidazole
Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole.
Many natural products, ...
ring of
histidine
Histidine (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an Amine, α-amino group (which is in the protonated –NH3+ form under Physiological condition, biological conditions), a carboxylic ...
, 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.
[
]
See also
* Carnosine
Carnosine (''beta''-alanyl-L-histidine) is a dipeptide molecule, made up of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues. Carnosine was discovered by Russian chemist Vladimir Gulevich.
Ca ...
References
{{reflist
Dipeptides