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Merck

M0253

Sigma-Aldrich

L-Mimosine from Koa hoale seeds

≥98%

Sinónimos:

(S)-α-Amino-β-[1-(3-hydroxy-4-oxopyridine)]propionic acid, Leucenol

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About This Item

Fórmula empírica (notación de Hill):
C8H10N2O4
Número de CAS:
Peso molecular:
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

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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.[1]

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).[2]

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.[3] It is an iron chelator that inhibits DNA replication in mammalian cells.[4] L-Mimosine has been shown to promote apoptosis in xenotransplanted human pancreatic cancer.[5] 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.[3] 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.[6] Mimosine, hinder folate metabolism in cell-specific manner.[4]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Li-Chuan Chung et al.
American journal of physiology. Cell physiology, 302(4), C676-C685 (2011-11-26)
L-Mimosine, an iron chelator and a prolyl 4-hydroxylase inhibitor, blocks many cancer cells at the late G1 phase. B-cell translocation gene 2 (Btg2) regulates the G1/S transition phases of the cell cycle. N-myc downstream regulated gene 1 (Ndrg1) is a
Tian-Xia Jiang et al.
Theranostics, 11(3), 1458-1472 (2021-01-05)
The epigenetic inheritance relies on stability of histone marks, but various diseases, including aging-related disorders, are usually associated with alterations of histone marks. Whether and how the proteasome is responsible for maintaining the histone marks during transcription and aging remain
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
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
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)

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