M0253
L-Mimosine from Koa hoale seeds
≥98%
Synonym(s):
(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid, Leucenol
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All Photos(4)
About This Item
Empirical Formula (Hill Notation):
C8H10N2O4
CAS Number:
Molecular Weight:
198.18
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77
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Assay
≥98%
SMILES string
N[C@@H](CN1C=CC(=O)C(O)=C1)C(O)=O
InChI
1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)/t5-/m0/s1
InChI key
WZNJWVWKTVETCG-YFKPBYRVSA-N
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.
Application
L-Mimosine from Koa hoale seeds has been used to study its anti-inflammatory effect in chronic inflammatory response (potassium permanganate - induced chronic granuloma).
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Mimosine, a plant-derived amino acid induces apoptosis in human pancreatic cancer xenografts.
Zalatnai A and Bocsi J.
Anticancer Research, 23(5A), 4007-4009 (2003)
H Agis et al.
Journal of periodontal research, 47(2), 165-173 (2011-10-01)
Pharmacological inhibitors of prolyl hydroxylases (PHDs) can induce a proangiogenic response that favors wound healing and bone regeneration. However, the response of periodontal cells to PHD inhibitors is unknown. To determine the effects of PHD inhibitors on periodontal cells, we
Yi Fang et al.
American journal of physiology. Renal physiology, 304(10), F1274-F1282 (2013-03-08)
Treatment with L-mimosine, which activates hypoxia-inducible factor-α (HIF-α), attenuates renal tubulointerstitial injury and improves renal function in a rat remnant kidney model. The miR-29 family of microRNAs directly targets a large number of extracellular matrix genes and reduces renal interstitial
Li-Chuan Chung et al.
Molecular nutrition & food research, 55(11), 1666-1676 (2011-09-22)
Prostate-specific antigen (PSA) is a well-known marker for diagnosing and monitoring prostate cancer. Curcumin, a yellow curry pigment, has been reported to enhance androgen receptor (AR) degradation. We examined the effects of curcumin on increasing PSA expression by hypoxia and
Mimosine is a cell-specific antagonist of folate metabolism.
Oppenheim EW
The Journal of Biological Chemistry, 275(25), 19268-19274 (2000)
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