Description
This alkaloid was isolated by Renz from Mimosia pudica L. and also from
Leucaena glauca Benth. It is laevorotatory with [α]
22D - 21 ° (H20) and yields a
blue, crystalline copper salt. On heating the chloride under pressure, a sublimate
is formed which has been shown, by comparison with a synthetic specimen, to
be N-methyl-3-hydroxypyrid-4-one, m.p. 224°C. The alkaloid is toxic and in
horses produces loss of hair when administered in large doses.
Chemical Properties
light tan to pink crystalline powder
Uses
L-Mimosine from
Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).
Definition
ChEBI: An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein
plant amino acid isolated from Mimosa pudica.
General Description
L-mimosine [β-N (3-hydroxy-4-pyridone)-α-amino propionic acid] is a non-protein amino acid and is a vital component of tropical legumes, such as
Leucaena glauca and other legumes belonging to
Mimosa spp. Structurally L-mimosine resembles dihydroxyphenylalanine except 3,4-dihydroxy-phenyl ring replaced by 3-hydroxy-4-pyridone ring.
Biochem/physiol Actions
L-Mimosine is a plant amino acid and potential inhibitor of the cell cycle giving rise to growth arrest in G1-phase. It is an iron chelator that inhibits DNA replication in mammalian cells. L-Mimosine has been shown to promote apoptosis in xenotransplanted human pancreatic cancer. L-Mimosine stabilizes hypoxia inducible factor 1 (HIF-1) and stimulates the expression of B-cell translocation gene 2 (Btg2) and N-myc downstream regulated gene 1 (Ndrg1) at the transcriptional level, which reduce cell proliferation of prostate carcinoma cells in vitro. L-Mimosine stabilizes HIF-1 through the inhibition of prolyl hydroxylases (PHDs) which target HIF-1 through degradation. The mechanism of inhibition is likely through the chelation of Fe2+ bound to the active site of PHD which is required for enzymatic activity. Mimosine inhibits cell cycle progression via iron chelation in MDA-MB-453 human breast cancer cells. Mimosine, hinder folate metabolism in cell-specific manner.
References
Renz., Zeit. physiol. Chem., 244, 153 (1936)
Nienburg, Taubock., ibid, 250,80 (1937)
Kostermanns., Rec. trav. Chim. Pays-Bas, 65, 319 (1946)
Kostermann., ibid, 66,93 (1947)
