mugineic acid
Identification
| Name | mugineic acid |
| CAS Number | 69199-37-7 |
| FDA UNII | KR256JY76I |
| Molecular Formula | C12 H20 N2 O8 |
| Molecular Weight | 320.29900000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for mugineic acid usage levels up to | not for fragrance use. |
| Recommendation for mugineic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
1-
azetidinebutanoic acid, 2-carboxyl-alpha-((3-carboxy-3-hydroxypropyl)amino)-beta-hydroxy-, (2S-(1(alphaR*(R*),betaR*),2R*))-
(2S)-1-[(2S,3S)-3-
carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-2-hydroxypropyl]azetidine-2-carboxylic acid
N-(3-(3-
carboxypropylamino)-2-hydroxy-3-carboxypropyl)azetidine-2-carboxylic acid
PubMed:
[Bioinorganic Chemistry of Iron].
PubMed:
The iron-chelate transporter OsYSL9 plays a role in iron distribution in developing rice grains.
PubMed:
Characterisation of the nicotianamine aminotransferase and deoxymugineic acid synthase genes essential to Strategy II iron uptake in bread wheat (Triticum aestivum L.).
PubMed:
Diurnal Changes in Transcript and Metabolite Levels during the Iron Deficiency Response of Rice.
PubMed:
Comparison on cellular mechanisms of iron and cadmium accumulation in rice: prospects for cultivating Fe-rich but Cd-free rice.
PubMed:
Identification and molecular characterization of the nicotianamine synthase gene family in bread wheat.
PubMed:
Mugineic acid, active ingredient of wheat grass: an oral novel hexadentate iron chelator in iron overloaded diseases.
PubMed:
Evolutionary analysis of iron (Fe) acquisition system in Marchantia polymorpha.
PubMed:
Transcriptomic analyses of maize ys1 and ys3 mutants reveal maize iron homeostasis.
PubMed:
The Phytosiderophore Efflux Transporter TOM2 Is Involved in Metal Transport in Rice.
PubMed:
Iron deficiency responses in rice roots.
PubMed:
Synthesis of [13C4]-labeled 2'-deoxymugineic acid.
PubMed:
Rice nicotianamine synthase localizes to particular vesicles for proper function.
PubMed:
Iron biofortification of rice using different transgenic approaches.
PubMed:
Rice genes involved in phytosiderophore biosynthesis are synchronously regulated during the early stages of iron deficiency in roots.
PubMed:
Nicotianamine synthase 2 localizes to the vesicles of iron-deficient rice roots, and its mutation in the YXXÏ or LL motif causes the disruption of vesicle formation or movement in rice.
PubMed:
Iron-biofortification in rice by the introduction of three barley genes participated in mugineic acid biosynthesis with soybean ferritin gene.
PubMed:
Characterizing the crucial components of iron homeostasis in the maize mutants ys1 and ys3.
PubMed:
A sensitive LC-ESI-Q-TOF-MS method reveals novel phytosiderophores and phytosiderophore-iron complexes in barley.
PubMed:
OsYSL16 plays a role in the allocation of iron.
PubMed:
Getting a sense for signals: regulation of the plant iron deficiency response.
PubMed:
Analysis of iron-phytosiderophore complexes in soil related samples: LC-ESI-MS/MS versus CE-MS.
PubMed:
OsYSL6 is involved in the detoxification of excess manganese in rice.
PubMed:
A novel barley yellow stripe 1-like transporter (HvYSL2) localized to the root endodermis transports metal-phytosiderophore complexes.
PubMed:
The binding of aluminum to mugineic acid and related compounds as studied by potentiometric titration.
PubMed:
Isolation and characterization of a barley yellow stripe-like gene, HvYSL5.
PubMed:
Mugineic acid derivatives as molecular probes for the mechanistic elucidation of iron acquisition in barley.
PubMed:
Recent insights into iron homeostasis and their application in graminaceous crops.
PubMed:
Successful reproduction requires the function of Arabidopsis Yellow Stripe-Like1 and Yellow Stripe-Like3 metal-nicotianamine transporters in both vegetative and reproductive structures.
PubMed:
Toward mechanistic elucidation of iron acquisition in barley: efficient synthesis of mugineic acids and their transport activities.
PubMed:
Complexation of metals by phytosiderophores revealed by CE-ESI-MS and CE-ICP-MS.
PubMed:
Time course analysis of gene expression over 24 hours in Fe-deficient barley roots.
PubMed:
Rice OsYSL15 is an iron-regulated iron(III)-deoxymugineic acid transporter expressed in the roots and is essential for iron uptake in early growth of the seedlings.
PubMed:
Investigation of ascorbate-mediated iron release from ferric phytosiderophores in the presence of nicotianamine.
PubMed:
Deoxymugineic acid increases Zn translocation in Zn-deficient rice plants.
PubMed:
Identification and localisation of the rice nicotianamine aminotransferase gene OsNAAT1 expression suggests the site of phytosiderophore synthesis in rice.
PubMed:
Isotopomer-based metabolomic analysis by NMR and mass spectrometry.
PubMed:
Mutation in nicotianamine aminotransferase stimulated the Fe(II) acquisition system and led to iron accumulation in rice.
PubMed:
CE of phytosiderophores and related metal species in plants.
PubMed:
A practical synthesis of the phytosiderophore 2'-deoxymugineic acid: a key to the mechanistic study of iron acquisition by graminaceous plants.
PubMed:
[Responses to iron-deficiency stress by graminaceous plants].
PubMed:
The rice bHLH protein OsIRO2 is an essential regulator of the genes involved in Fe uptake under Fe-deficient conditions.
PubMed:
Promoter analysis of iron-deficiency-inducible barley IDS3 gene in Arabidopsis and tobacco plants.
PubMed:
Transporters of ligands for essential metal ions in plants.
PubMed:
The expression of iron homeostasis-related genes during rice germination.
PubMed:
Deoxymugineic Acid synthase: a gene important for fe-acquisition and homeostasis.
PubMed:
Separation and identification of phytosiderophores and their metal complexes in plants by zwitterionic hydrophilic interaction liquid chromatography coupled to electrospray ionization mass spectrometry.
PubMed:
Biosynthesis and secretion of mugineic acid family phytosiderophores in zinc-deficient barley.
PubMed:
Cloning and characterization of deoxymugineic acid synthase genes from graminaceous plants.
PubMed:
Anion exchange liquid chromatography--inductively coupled plasma-mass spectrometry detection of the Co2+, Cu2+, Fe3+ and Ni2+ complexes of mugineic and deoxymugineic acid.
PubMed:
[Study on the structure activity relationship of a phytosiderophore, mugineic acid].
PubMed:
A specific transporter for iron(III)-phytosiderophore in barley roots.
PubMed:
Mg-dechelation activity in radish cotyledons with artificial and native substrates, Mg-chlorophyllin a and chlorophyllide a.
PubMed:
Expression of iron-acquisition-related genes in iron-deficient rice is co-ordinately induced by partially conserved iron-deficiency-responsive elements.
PubMed:
Yellow stripe1. Expanded roles for the maize iron-phytosiderophore transporter.
PubMed:
Three nicotianamine synthase genes isolated from maize are differentially regulated by iron nutritional status.
PubMed:
Speciation of iron coordinated by phytosiderophores by use of HPLC with pulsed amperometric detection and AAS.
PubMed:
cDNA microarray analysis of gene expression during Fe-deficiency stress in barley suggests that polar transport of vesicles is implicated in phytosiderophore secretion in Fe-deficient barley roots.
PubMed:
Real-time [11C]methionine translocation in barley in relation to mugineic acid phytosiderophore biosynthesis.
PubMed:
Determination of phytosiderophores by anion-exchange chromatography with pulsed amperometric detection.
PubMed:
The expression of a barley HvNAS1 nicotianamine synthase gene promoter-gus fusion gene in transgenic tobacco is induced by Fe-deficiency in roots.
PubMed:
In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2'-deoxymugineic acid to mugineic acid in transgenic rice.
PubMed:
Nicotianamine synthase gene expression differs in barley and rice under Fe-deficient conditions.
PubMed:
Two dioxygenase genes, Ids3 and Ids2, from Hordeum vulgare are involved in the biosynthesis of mugineic acid family phytosiderophores.
PubMed:
Hydroxylated phytosiderophore species possess an enhanced chelate stability and affinity for iron(III).
PubMed:
Induced activity of adenine phosphoribosyltransferase (APRT) in iron-deficiency barley roots: a possible role for phytosiderophore production.
PubMed:
A formal asymmetric synthesis of Mugineic acid: an efficient synthetic route through chiral oxazolidinone.
PubMed:
Cloning two genes for nicotianamine aminotransferase, a critical enzyme in iron acquisition (Strategy II) in graminaceous plants.
PubMed:
Cloning of nicotianamine synthase genes, novel genes involved in the biosynthesis of phytosiderophores.
PubMed:
Expression cloning in Fe2+ transport defective yeast of a novel maize MYC transcription factor.
PubMed:
Characterization of Fe(III)-deferoxamine and Mn(II)-pectin as magnetic resonance imaging contrast agents.
PubMed:
Comprehensive analysis of organic ligands in whole root exudates using nuclear magnetic resonance and gas chromatography-mass spectrometry.
PubMed:
Isolation of nicotianamine as a gelatinase inhibitor.
PubMed:
Incorporation of
15
N and
14
C of methionine into the mugineic acid family of phytosiderophores in iron-deficient barley roots.
PubMed:
Two Related Biosynthetic Pathways of Mugineic Acids in Gramineous Plants.
PubMed:
Expression of a gene specific for iron deficiency (Ids3) in the roots of Hordeum vulgare.
PubMed:
Indirect utilization of the phytosiderophore mugineic acid as an iron source to rhizosphere fluorescent Pseudomonas.
PubMed:
Short-term effects of rhizosphere microorganisms on fe uptake from microbial siderophores by maize and oat.
PubMed:
Biosynthesis of Phytosiderophores : In Vitro Biosynthesis of 2'-Deoxymugineic Acid from l-Methionine and Nicotianamine.
PubMed:
Mugineic acid: non-selective enhancement of excitatory amino acid actions on rat central neurones.
PubMed:
Separation and determination of mugineic acid and its analogues by high-performance liquid chromatography.