Page last updated: 2024-12-10
nicotianamine
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Description
nicotianamine: an angiotensin I-converting enzyme inhibitor from soy sauce [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
(S,S,S)-nicotianamine : The (S,S,S)-stereoisomer of nicotianamine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 9882882 |
| CHEMBL ID | 3581907 |
| CHEBI ID | 17721 |
| SCHEMBL ID | 542007 |
| MeSH ID | M0220723 |
Synonyms (21)
| Synonym |
|---|
| unii-2ogx6yhq1f |
| 2ogx6yhq1f , |
| 1-azetidinebutanoic acid, alpha-((3-amino-3-carboxypropyl)amino)-2-carboxy-, (2s-(1(alphar*(r*)),2r*))- |
| (2s)-1-[(3s)-3-{[(3s)-3-amino-3-carboxypropyl]amino}-3-carboxypropyl]azetidine-2-carboxylic acid |
| CHEBI:17721 |
| (s,s,s)-nicotianamine |
| 34441-14-0 |
| nicotianamine |
| C05324 |
| 044DBB66-112B-48B2-8A19-380C1C452CB2 |
| SCHEMBL542007 |
| bdbm50090921 |
| CHEMBL3581907 , |
| DTXSID8037677 |
| AKOS030242342 |
| J-019609 |
| Q11324211 |
| 1-azetidinebutanoic acid, alpha-((3-amino-3-carboxypropyl)amino)-2-car boxy-, (2s-(1(alphar*(r*)),2r*))- |
| (2s)-1-[(3s)-3-[[(3s)-3-amino-3-carboxypropyl]amino]-3-carboxypropyl]azetidine-2-carboxylic acid |
| [2s-[1[alphar*(r*)],2r*]]-alpha-[(3-amino-3-carboxypropyl)amino]-2-carboxy- 1-azetidinebutanoic acid |
| (alphas,2s)-alpha-[[(3s)-3-amino-3-carboxypropyl]amino]-2-carboxy-1-azetidinebutanoic acid |
Research Excerpts
Bioavailability
Nicotianamine (NA) is a natural chelator of Fe, zinc (Zn) and other metals in higher plants. NA-chelated Fe is highly bioavailable in vitro.
| Excerpt | Reference | Relevance |
|---|---|---|
| " Bioavailability of Fe from the high NA grain, as measured by ferritin synthesis in an in vitro Caco-2 cell model that simulates the human digestive system, was twice as much as that of the control line." | ( Nicotianamine, a novel enhancer of rice iron bioavailability to humans. Ai, C; Bei, X; Cheng, Z; Glahn, RP; Jiang, X; Lei, XG; Miller, DD; Shou, H; Welch, RM; Zheng, L; Zheng, Y, 2010) | 0.36 |
| "The metal chelator nicotianamine promotes the bioavailability of Fe and reduces cellular Fe toxicity." | ( Nicotianamine functions in the Phloem-based transport of iron to sink organs, in pollen development and pollen tube growth in Arabidopsis. Abadía, J; Bauer, P; Fink-Straube, C; Rellán-Álvarez, R; Schuler, M, 2012) | 0.38 |
| " However, phytate is only part of the answer to the multifaceted bioavailability question, albeit an important one." | ( Zn and Fe biofortification: the right chemical environment for human bioavailability. Clemens, S, 2014) | 0.4 |
| "Iron bioavailability in unleavened white and wholegrain bread made from two commercial wheat varieties was assessed by measuring ferritin production in Caco-2 cells." | ( Iron bioavailability in two commercial cultivars of wheat: comparison between wholegrain and white flour and the effects of nicotianamine and 2'-deoxymugineic acid on iron uptake into Caco-2 cells. Eagling, T; Fairweather-Tait, SJ; Shewry, PR; Wawer, AA; Zhao, FJ, 2014) | 0.4 |
| " Biofortification is a micronutrient intervention aimed at increasing the density and bioavailability of essential vitamins and minerals in staple crops; Fe biofortification of wheat has proved challenging." | ( Metabolic engineering of bread wheat improves grain iron concentration and bioavailability. Beasley, JT; Bonneau, JP; Callahan, DL; Glahn, RP; Johnson, AAT; Lombi, E; Moreno-Moyano, LT; Sánchez-Palacios, JT; Tako, E, 2019) | 0.51 |
| " Nicotianamine (NA) is a natural chelator of Fe, zinc (Zn) and other metals in higher plants and NA-chelated Fe is highly bioavailable in vitro." | ( Nicotianamine-chelated iron positively affects iron status, intestinal morphology and microbial populations in vivo (Gallus gallus). Beasley, JT; Bonneau, JP; Glahn, RP; Johnson, AAT; Kolba, N; Koren, O; Ozeri, L; Tako, E, 2020) | 0.56 |
| " It is unclear how important plant-derived chelators, such as nicotianamine (NA), an organic small molecule that is ubiquitous in crops, vegetables, and various other foods, contribute to iron bioavailability in mammals." | ( Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine. Morimoto, S; Murata, Y; Namba, K; Sakamoto, N; Watanabe, T; Yoshida, M, ) | 0.13 |
| " Here we describe multi-location confined field trial (CFT) evaluation of a low-copy transgenic CE-OsNAS2 wheat event (CE-1) over 3 years and demonstrate higher concentrations of NA, DMA, Fe, and Zn in CE-1 wholemeal flour, white flour, and white bread and higher Fe bioavailability in CE-1 white flour relative to a null segregant (NS) control." | ( Multi-year field evaluation of nicotianamine biofortified bread wheat. Appels, R; Beasley, JT; Bonneau, JP; Callahan, DL; Glahn, RP; Howell, KS; Johnson, AAT; Moreno-Moyano, LT; Tako, E; Taylor, J, 2022) | 0.72 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " The analysis of dose-response and time-course Ni treatments have revealed that the exposure to Ni triggers the accumulation of NA in the roots." | ( Root-to-shoot long-distance circulation of nicotianamine and nicotianamine-nickel chelates in the metal hyperaccumulator Thlaspi caerulescens. Briat, JF; Czernic, P; Gendre, D; Lebrun, M; Lobinski, R; Mari, S; Ouerdane, L; Pianelli, K, 2006) | 0.33 |
| " The grass Deschampsia cespitosa was dosed with either Ni or Cd or pulsed with exogenous ABA." | ( Chelator profiling in Deschampsia cespitosa (L.) Beauv. Reveals a Ni reaction, which is distinct from the ABA and cytokinin associated response to Cd. Coates, KE; Emery, RJ; Galer, AL; Hayward, AR; Hutchinson, TC, 2013) | 0.39 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Roles (3)
| Role | Description |
|---|---|
| chelator | A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. |
| EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor | An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Drug Classes (2)
| Class | Description |
|---|---|
| nicotianamine | |
| amino acid zwitterion | The zwitterionic form of an amino acid having a negatively charged carboxyl group and a positively charged amino group. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Pathways (4)
| Pathway | Proteins | Compounds |
|---|---|---|
| AtMetExpress overview | 0 | 109 |
| Response to iron deficiency | 10 | 17 |
| Mugineic acid biosynthesis | 2 | 14 |
| Iron uptake and transport in root vascular system | 8 | 5 |
Protein Targets (1)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Angiotensin-converting enzyme | Homo sapiens (human) | IC50 (µMol) | 18.7000 | 0.0001 | 0.5336 | 10.0000 | AID1228660 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (56)
Molecular Functions (16)
Ceullar Components (10)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular space | Angiotensin-converting enzyme | Homo sapiens (human) |
| extracellular region | Angiotensin-converting enzyme | Homo sapiens (human) |
| extracellular space | Angiotensin-converting enzyme | Homo sapiens (human) |
| lysosome | Angiotensin-converting enzyme | Homo sapiens (human) |
| endosome | Angiotensin-converting enzyme | Homo sapiens (human) |
| plasma membrane | Angiotensin-converting enzyme | Homo sapiens (human) |
| external side of plasma membrane | Angiotensin-converting enzyme | Homo sapiens (human) |
| basal plasma membrane | Angiotensin-converting enzyme | Homo sapiens (human) |
| brush border membrane | Angiotensin-converting enzyme | Homo sapiens (human) |
| extracellular exosome | Angiotensin-converting enzyme | Homo sapiens (human) |
| sperm midpiece | Angiotensin-converting enzyme | Homo sapiens (human) |
| plasma membrane | Angiotensin-converting enzyme | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (1)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1228660 | Inhibition of ACE (unknown origin) using 3-Hydroxybutylyl-Gly-Gly-Gly substrate assessed as reduction in 3-Hyroxybutylic acid generation incubated for 1 hr by colorimetric assay | 2015 | Journal of natural products, May-22, Volume: 78, Issue:5 | Top-down Targeted Metabolomics Reveals a Sulfur-Containing Metabolite with Inhibitory Activity against Angiotensin-Converting Enzyme in Asparagus officinalis. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (114)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 4 (3.51) | 18.2507 |
| 2000's | 35 (30.70) | 29.6817 |
| 2010's | 64 (56.14) | 24.3611 |
| 2020's | 11 (9.65) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 14 (12.07%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 102 (87.93%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||