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| | L-MIMOSINE Basic information |
| Product Name: | L-MIMOSINE | | Synonyms: | L-LEUCININE;L(-)-MIMOSINE;L-MIMOSINE;BETA-[N-(3-HYDROXY-4-PYRIDONE)]-ALPHA-AMINOPROPIONIC ACID;LEUCENOL;ALPHA-AMINO-BETA-[N-(3-HYDROXY-4-PYRIDONE)]-PROPIONIC ACID;MIMOSINE;(S)-ALPHA-AMINO-BETA-(1-[3-HYDROXY-4-OXOPYRIDINE])PROPIONIC ACID | | CAS: | 500-44-7 | | MF: | C8H10N2O4 | | MW: | 198.18 | | EINECS: | 207-905-1 | | Product Categories: | Inhibitors;Alkaloids | | Mol File: | 500-44-7.mol |  |
| | L-MIMOSINE Chemical Properties |
| Melting point | 224-228 °C | | Boiling point | 335.48°C (rough estimate) | | density | 1.3764 (rough estimate) | | refractive index | 1.6180 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Water (Slightly, Heated, Sonicated) | | form | Pink to brown powder. | | pka | 2.06±0.10(Predicted) | | color | White to Off-White | | Merck | 13,6221 | | InChIKey | WZNJWVWKTVETCG-YFKPBYRVSA-N | | LogP | -1.080 (est) | | CAS DataBase Reference | 500-44-7(CAS DataBase Reference) | | EPA Substance Registry System | Mimosine (500-44-7) |
| | L-MIMOSINE Usage And Synthesis |
| 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) |
| | L-MIMOSINE Preparation Products And Raw materials |
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