L-BMAA (BioDeep_00001868318)

Main id: BioDeep_00000003102

 


代谢物信息卡片


(S)-2-AMINO-3-(METHYLAMINO)PROPANOIC ACID

化学式: C4H10N2O2 (118.0742)
中文名称: L-Β-(N-甲基氨基)丙氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CNCC(C(=O)O)N
InChI: InChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)/t3-/m0/s1

描述信息

A non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens is replaced by a methylamino group. A non-proteinogenic amino acid produced by cyanobacteria, it is a neurotoxin that has been postulated as a possible cause of neurodegenerative disorders of aging such as Alzheimers disease, amyotrophic lateral sclerosis, and the amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS-PDC) syndrome of Guam.
D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists

同义名列表

4 个代谢物同义名

(S)-2-AMINO-3-(METHYLAMINO)PROPANOIC ACID; beta-N-Methylamino-L-alanine; L-BMAA; 3-Methylamino-L-alanine



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 14 CASP1, CASP3, CAT, GFAP, GLUL, GRM5, HPGDS, HTT, MAPT, NPPA, SLC9A1, SOD1, SQSTM1, TARDBP
Peripheral membrane protein 1 MAPT
Endosome membrane 1 HTT
Endoplasmic reticulum membrane 1 SLC8A3
Cytoplasmic vesicle, autophagosome 1 SQSTM1
Nucleus 9 CASP3, CRISP1, GLUL, GRM1, HTT, MAPT, SOD1, SQSTM1, TARDBP
autophagosome 2 HTT, SQSTM1
cytosol 11 CASP1, CASP3, CAT, GFAP, GLUL, HPGDS, HTT, MAPT, SLC7A5, SOD1, SQSTM1
dendrite 5 GRM1, GRM5, HTT, MAPT, SLC8A3
nucleoplasm 7 CASP3, HPGDS, HTT, SLC9A1, SOD1, SQSTM1, TARDBP
Cell membrane 11 CASP1, GLUL, GRID1, GRM1, GRM5, HTT, MAPT, SLC1A5, SLC7A5, SLC8A3, SLC9A1
Lipid-anchor 1 GLUL
Cytoplasmic side 1 MAPT
lamellipodium 1 SLC9A1
Cell projection, axon 1 MAPT
Multi-pass membrane protein 8 GRID1, GRM1, GRM5, HTT, SLC1A5, SLC7A5, SLC8A3, SLC9A1
Synapse 2 HTT, SLC8A3
cell junction 1 SLC8A3
cell surface 1 SLC9A1
dendritic shaft 1 GRM5
glutamatergic synapse 5 CASP3, GRID1, GRM1, GRM5, SQSTM1
Golgi apparatus 1 HTT
growth cone 1 MAPT
lysosomal membrane 1 SLC7A5
neuromuscular junction 1 SLC8A3
neuronal cell body 5 CASP3, GRM5, MAPT, SLC8A3, SOD1
postsynapse 2 GRM5, SLC8A3
presynaptic membrane 1 HTT
sarcolemma 1 SLC8A3
Cytoplasm, cytosol 3 GLUL, MAPT, SQSTM1
Lysosome 1 SQSTM1
plasma membrane 11 CASP1, GLUL, GRID1, GRM1, GRM5, HTT, MAPT, SLC1A5, SLC7A5, SLC8A3, SLC9A1
Membrane 6 CAT, GRM5, SLC1A5, SLC7A5, SLC8A3, SLC9A1
apical plasma membrane 2 SLC7A5, SLC9A1
axon 3 HTT, MAPT, SLC8A3
basolateral plasma membrane 2 SLC7A5, SLC9A1
extracellular exosome 8 CAT, GLUL, GRID1, SLC1A5, SLC7A5, SLC9A1, SOD1, SQSTM1
Lysosome membrane 1 SLC7A5
endoplasmic reticulum 3 GLUL, HTT, SQSTM1
extracellular space 3 CRISP1, NPPA, SOD1
perinuclear region of cytoplasm 3 HTT, SLC8A3, SLC9A1
Schaffer collateral - CA1 synapse 2 GRM1, GRM5
intercalated disc 1 SLC9A1
mitochondrion 7 CAT, GLUL, MAPT, SLC9A1, SOD1, SQSTM1, TARDBP
protein-containing complex 5 CASP1, CAT, HTT, NPPA, SOD1
intracellular membrane-bounded organelle 4 CAT, HPGDS, SLC7A5, SQSTM1
postsynaptic density 2 CASP3, SLC8A3
Secreted 2 MAPT, NPPA
extracellular region 5 CAT, CRISP1, MAPT, NPPA, SOD1
Mitochondrion outer membrane 1 SLC8A3
mitochondrial outer membrane 1 SLC8A3
astrocyte end-foot 1 GFAP
mitochondrial matrix 2 CAT, SOD1
anchoring junction 1 SLC8A3
dendritic spine 3 GRM5, MAPT, SLC8A3
T-tubule 1 SLC9A1
perikaryon 2 NPPA, SLC8A3
cytoplasmic vesicle 2 SOD1, SQSTM1
microtubule cytoskeleton 1 MAPT
nucleolus 1 CASP1
axon cytoplasm 2 MAPT, SOD1
sarcoplasm 1 SLC8A3
P-body 1 SQSTM1
Early endosome 1 HTT
postsynaptic membrane 2 GRID1, HTT
Apical cell membrane 1 SLC7A5
Cell membrane, sarcolemma 1 SLC8A3
Cytoplasm, perinuclear region 1 SLC8A3
Membrane raft 3 HTT, MAPT, SLC9A1
Cell junction, focal adhesion 1 HTT
Cytoplasm, cytoskeleton 1 MAPT
focal adhesion 3 CAT, HTT, SLC9A1
microtubule 2 CASP1, MAPT
axolemma 1 MAPT
GABA-ergic synapse 1 GRID1
Peroxisome 2 CAT, SOD1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Cell projection, dendritic spine 1 SLC8A3
Nucleus, PML body 1 SQSTM1
PML body 1 SQSTM1
mitochondrial intermembrane space 1 SOD1
collagen-containing extracellular matrix 1 NPPA
intermediate filament 1 GFAP
nuclear speck 2 MAPT, TARDBP
NLRP3 inflammasome complex 1 CASP1
Postsynaptic cell membrane 2 GRID1, GRM1
dendrite cytoplasm 1 SOD1
Cytoplasm, myofibril, sarcomere 1 SQSTM1
Late endosome 2 HTT, SQSTM1
sarcomere 1 SQSTM1
Cell projection, neuron projection 1 HTT
neuron projection 2 HTT, MAPT
chromatin 1 TARDBP
cell projection 2 GFAP, NPPA
centriole 1 HTT
cytoplasmic ribonucleoprotein granule 1 MAPT
sperm midpiece 1 SQSTM1
Basolateral cell membrane 1 SLC9A1
microvillus membrane 1 SLC7A5
Endomembrane system 1 HTT
phagophore assembly site 1 SQSTM1
Cytoplasmic vesicle membrane 1 HTT
Cell projection, dendrite 2 MAPT, SLC8A3
Melanosome 1 SLC1A5
Cytoplasm, Stress granule 1 TARDBP
cytoplasmic stress granule 1 TARDBP
cell body 3 GFAP, GLUL, MAPT
intermediate filament cytoskeleton 1 GFAP
basal plasma membrane 2 SLC1A5, SLC7A5
Microsome 1 GLUL
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
axon terminus 1 SLC8A3
postsynaptic density membrane 3 GRID1, GRM1, GRM5
aggresome 1 SQSTM1
AIM2 inflammasome complex 1 CASP1
perichromatin fibrils 1 TARDBP
external side of apical plasma membrane 1 SLC7A5
death-inducing signaling complex 1 CASP3
canonical inflammasome complex 1 CASP1
intracellular non-membrane-bounded organelle 2 SQSTM1, TARDBP
Lewy body 1 SQSTM1
postsynaptic cytosol 1 HTT
somatodendritic compartment 1 MAPT
Preautophagosomal structure 1 SQSTM1
nuclear periphery 1 MAPT
presynaptic cytosol 1 HTT
astrocyte projection 1 GRM5
cytoplasmic side of lysosomal membrane 1 GFAP
glial cell projection 2 GLUL, MAPT
[Long-acting natriuretic peptide]: Secreted 1 NPPA
[Vessel dilator]: Secreted 1 NPPA
[Kaliuretic peptide]: Secreted 1 NPPA
[Urodilatin]: Secreted 1 NPPA
[Atrial natriuretic peptide]: Secreted 1 NPPA
[Atriopeptin-3]: Secreted 1 NPPA
Cytoplasm, sarcoplasm 1 SLC8A3
Autolysosome 1 SQSTM1
catalase complex 1 CAT
inclusion body 2 HTT, SQSTM1
neurofibrillary tangle 1 MAPT
amino acid transport complex 1 SLC7A5
main axon 1 MAPT
tubulin complex 1 MAPT
cation-transporting ATPase complex 1 SLC9A1
serotonergic synapse 1 HTT
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
[Huntingtin]: Cytoplasm 1 HTT
[Huntingtin, myristoylated N-terminal fragment]: Cytoplasmic vesicle, autophagosome 1 HTT
interchromatin granule 1 TARDBP
G protein-coupled receptor dimeric complex 1 GRM1
G protein-coupled receptor homodimeric complex 1 GRM1
amphisome 1 SQSTM1


文献列表

  • Sea-Yong Kim, Ulla Rasmussen, Sara Rydberg. Impact of the neurotoxin β-N-methylamino-L-alanine on the diatom Thalassiosira pseudonana using metabolomics. Marine pollution bulletin. 2024 May; 202(?):116299. doi: 10.1016/j.marpolbul.2024.116299. [PMID: 38581736]
  • Pankajini Bal, Geetgovind Sinam, Chandrasekharan Yahavi, Sheelendra Pratap Singh, Satyanarayan Jena, Aditya Bhushan Pant, Saroj Kanta Barik. A UPLC-MS/MS method for quantification of β-N-methylamino-L-alanine (BMAA) in Cycas sphaerica roxb. and its use in validating efficacy of a traditional BMAA removal method. Toxicon : official journal of the International Society on Toxinology. 2024 Feb; 238(?):107566. doi: 10.1016/j.toxicon.2023.107566. [PMID: 38151204]
  • Sea-Yong Kim, Ulla Rasmussen, Sara Rydberg. Effect and function of β-N-methylamino-L-alanine in the diatom Phaeodactylum tricornutum. The Science of the total environment. 2022 Jul; 830(?):154778. doi: 10.1016/j.scitotenv.2022.154778. [PMID: 35341850]
  • Tiziana Petrozziello, Francesca Boscia, Valentina Tedeschi, Anna Pannaccione, Valeria de Rosa, Angela Corvino, Beatrice Severino, Lucio Annunziato, Agnese Secondo. Na+/Ca2+ exchanger isoform 1 takes part to the Ca2+-related prosurvival pathway of SOD1 in primary motor neurons exposed to beta-methylamino-L-alanine. Cell communication and signaling : CCS. 2022 01; 20(1):8. doi: 10.1186/s12964-021-00813-z. [PMID: 35022040]
  • Kate Samardzic, Joel R Steele, Jake P Violi, Anne Colville, Simon M Mitrovic, Kenneth J Rodgers. Toxicity and bioaccumulation of two non-protein amino acids synthesised by cyanobacteria, β-N-Methylamino-L-alanine (BMAA) and 2,4-diaminobutyric acid (DAB), on a crop plant. Ecotoxicology and environmental safety. 2021 Jan; 208(?):111515. doi: 10.1016/j.ecoenv.2020.111515. [PMID: 33099142]
  • Sea-Yong Kim, Sara Rydberg. Transfer of the Neurotoxin β-N-methylamino-l-alanine (BMAA) in the Agro-Aqua Cycle. Marine drugs. 2020 May; 18(5):. doi: 10.3390/md18050244. [PMID: 32384637]
  • Nadezda Zguna, Agnes M L Karlson, Leopold L Ilag, Andrius Garbaras, Elena Gorokhova. Insufficient evidence for BMAA transfer in the pelagic and benthic food webs in the Baltic Sea. Scientific reports. 2019 07; 9(1):10406. doi: 10.1038/s41598-019-46815-3. [PMID: 31320701]
  • Saki Okamoto, Shigeyuki Esumi, Kayoko Hamaguchi-Hamada, Shun Hamada. β-N-methylamino-L-alanine (BMAA) suppresses cell cycle progression of non-neuronal cells. Scientific reports. 2018 12; 8(1):17995. doi: 10.1038/s41598-018-36418-9. [PMID: 30573743]
  • Alexandra A Popova, Tatiana A Semashko, Natalia V Kostina, Ulla Rasmussen, Vadim M Govorun, Olga A Koksharova. The Cyanotoxin BMAA Induces Heterocyst Specific Gene Expression in Anabaena sp. PCC 7120 under Repressive Conditions. Toxins. 2018 Nov; 10(11):. doi: 10.3390/toxins10110478. [PMID: 30453523]
  • Paula Pierozan, Marie Andersson, Ingvar Brandt, Oskar Karlsson. The environmental neurotoxin β-N-methylamino-L-alanine inhibits melatonin synthesis in primary pinealocytes and a rat model. Journal of pineal research. 2018 Aug; 65(1):e12488. doi: 10.1111/jpi.12488. [PMID: 29528516]
  • Alexandra A Popova, Ulla Rasmussen, Tatiana A Semashko, Vadim M Govorun, Olga A Koksharova. Stress effects of cyanotoxin β-methylamino-L-alanine (BMAA) on cyanobacterial heterocyst formation and functionality. Environmental microbiology reports. 2018 06; 10(3):369-377. doi: 10.1111/1758-2229.12647. [PMID: 29624906]
  • Deepak Bhandari, Brett A Bowman, Anish B Patel, David M Chambers, Víctor R De Jesús, Benjamin C Blount. UPLC-ESI-MS/MS method for the quantitative measurement of aliphatic diamines, trimethylamine N-oxide, and β-methylamino-l-alanine in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Apr; 1083(?):86-92. doi: 10.1016/j.jchromb.2018.02.043. [PMID: 29524697]
  • Valeska Contardo-Jara, Torsten Schwanemann, Maranda Esterhuizen-Londt, Stephan Pflugmacher. Protein association of β-N-methylamino-L-alanine in Triticum aestivum via irrigation. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2018 Apr; 35(4):731-739. doi: 10.1080/19440049.2018.1427283. [PMID: 29324084]
  • Oddvar Myhre, Dag Marcus Eide, Synne Kleiven, Hans Christian Utkilen, Tim Hofer. Repeated five-day administration of L-BMAA, microcystin-LR, or as mixture, in adult C57BL/6 mice - lack of adverse cognitive effects. Scientific reports. 2018 02; 8(1):2308. doi: 10.1038/s41598-018-20327-y. [PMID: 29396538]
  • Suramya Waidyanatha, Kristen Ryan, J Michael Sanders, Jacob D McDonald, Christopher J Wegerski, Melanie Doyle-Eisle, C Edwin Garner. Disposition of β-N-methylamino-l-alanine (L-BMAA), a neurotoxin, in rodents following a single or repeated oral exposure. Toxicology and applied pharmacology. 2018 01; 339(?):151-160. doi: 10.1016/j.taap.2017.12.008. [PMID: 29248465]
  • Laura Louise Scott, Simoné Downing, Timothy Grant Downing. The Evaluation of BMAA Inhalation as a Potential Exposure Route Using a rat Model. Neurotoxicity research. 2018 Jan; 33(1):6-14. doi: 10.1007/s12640-017-9742-9. [PMID: 28470568]
  • Upasana Roy, Laura Conklin, Jürgen Schiller, Jörg Matysik, John P Berry, A Alia. Metabolic profiling of zebrafish (Danio rerio) embryos by NMR spectroscopy reveals multifaceted toxicity of β-methylamino-L-alanine (BMAA). Scientific reports. 2017 12; 7(1):17305. doi: 10.1038/s41598-017-17409-8. [PMID: 29230019]
  • J S Metcalf, Doug Lobner, Sandra Anne Banack, Gregory A Cox, Peter B Nunn, Peter B Wyatt, Paul Alan Cox. Analysis of BMAA enantiomers in cycads, cyanobacteria, and mammals: in vivo formation and toxicity of D-BMAA. Amino acids. 2017 08; 49(8):1427-1439. doi: 10.1007/s00726-017-2445-y. [PMID: 28620737]
  • Oskar Karlsson, Wojciech Michno, Yusuf Ransome, Jörg Hanrieder. MALDI imaging delineates hippocampal glycosphingolipid changes associated with neurotoxin induced proteopathy following neonatal BMAA exposure. Biochimica et biophysica acta. Proteins and proteomics. 2017 Jul; 1865(7):740-746. doi: 10.1016/j.bbapap.2016.12.004. [PMID: 27956354]
  • L Bláhová, J Kohoutek, E Kadlecová, L Kozáková, L Bláha. Assessment of non-derivatized β-N-methylamino-l-alanine (BMAA) neurotoxin in free form in urine of patients with nonspecific neurological symptoms. Toxicon : official journal of the International Society on Toxinology. 2017 Jul; 133(?):48-57. doi: 10.1016/j.toxicon.2017.04.011. [PMID: 28428069]
  • Sandra Lage, Linnea Ström, Anna Godhe, Sara Rydberg. The effect of exogenous β-N-methylamino-l-alanine (BMAA) on the diatoms Phaeodactylum tricornutum and Thalassiosira weissflogii. Harmful algae. 2016 Sep; 58(?):85-92. doi: 10.1016/j.hal.2016.08.005. [PMID: 28073463]
  • Paul Alan Cox, David A Davis, Deborah C Mash, James S Metcalf, Sandra Anne Banack. Dietary exposure to an environmental toxin triggers neurofibrillary tangles and amyloid deposits in the brain. Proceedings. Biological sciences. 2016 Jan; 283(1823):. doi: 10.1098/rspb.2015.2397. [PMID: 26791617]
  • Sandra Lage, Alfred Burian, Ulla Rasmussen, Pedro Reis Costa, Heléne Annadotter, Anna Godhe, Sara Rydberg. BMAA extraction of cyanobacteria samples: which method to choose?. Environmental science and pollution research international. 2016 Jan; 23(1):338-50. doi: 10.1007/s11356-015-5266-0. [PMID: 26304815]
  • Daniel G Beach, Elliott S Kerrin, Michael A Quilliam. Selective quantitation of the neurotoxin BMAA by use of hydrophilic-interaction liquid chromatography-differential mobility spectrometry-tandem mass spectrometry (HILIC-DMS-MS/MS). Analytical and bioanalytical chemistry. 2015 Nov; 407(28):8397-409. doi: 10.1007/s00216-015-9012-8. [PMID: 26396078]
  • Simoné Downing, Maranda Esterhuizen-Londt, Timothy Grant Downing. β-N-methylamino-L-alanine (BMAA) metabolism in the aquatic macrophyte Ceratophyllum demersum. Ecotoxicology and environmental safety. 2015 Oct; 120(?):88-92. doi: 10.1016/j.ecoenv.2015.05.022. [PMID: 26036420]
  • L Berntzon, L O Ronnevi, B Bergman, J Eriksson. Detection of BMAA in the human central nervous system. Neuroscience. 2015 Apr; 292(?):137-47. doi: 10.1016/j.neuroscience.2015.02.032. [PMID: 25725357]
  • Emma Muñoz-Sáez, Estefanía de Munck García, Rosa María Arahuetes Portero, Francisca Vicente, Francisco Javier Ortiz-López, Juan Cantizani, Begoña Gómez Miguel. Neuroprotective role of sphingosine-1-phosphate in L-BMAA treated neuroblastoma cells (SH-SY5Y). Neuroscience letters. 2015 Apr; 593(?):83-9. doi: 10.1016/j.neulet.2015.03.010. [PMID: 25769802]
  • Sandra Lage, Heléne Annadotter, Ulla Rasmussen, Sara Rydberg. Biotransfer of β-N-methylamino-L-alanine (BMAA) in a eutrophicated freshwater lake. Marine drugs. 2015 Mar; 13(3):1185-201. doi: 10.3390/md13031185. [PMID: 25738330]
  • Bruce C McGorum, R Scott Pirie, Laura Glendinning, Gerry McLachlan, James S Metcalf, Sandra A Banack, Paul A Cox, Geoffrey A Codd. Grazing livestock are exposed to terrestrial cyanobacteria. Veterinary research. 2015 Feb; 46(?):16. doi: 10.1186/s13567-015-0143-x. [PMID: 25828258]
  • E Rivadeneyra-Domínguez, J F Rodríguez-Landa. Cycads and their association with certain neurodegenerative diseases. Neurologia (Barcelona, Spain). 2014 Nov; 29(9):517-22. doi: 10.1016/j.nrl.2013.03.005. [PMID: 23725821]
  • Hong Z Yin, Stephen Yu, Cheng-I Hsu, Joe Liu, Allan Acab, Richard Wu, Anna Tao, Benjamin J Chiang, John H Weiss. Intrathecal infusion of BMAA induces selective motor neuron damage and astrogliosis in the ventral horn of the spinal cord. Experimental neurology. 2014 Nov; 261(?):1-9. doi: 10.1016/j.expneurol.2014.06.003. [PMID: 24918341]
  • Kiyo Mondo, W Broc Glover, Susan J Murch, Guangliang Liu, Yong Cai, David A Davis, Deborah C Mash. Environmental neurotoxins β-N-methylamino-l-alanine (BMAA) and mercury in shark cartilage dietary supplements. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Aug; 70(?):26-32. doi: 10.1016/j.fct.2014.04.015. [PMID: 24755394]
  • Sandra Lage, Pedro Reis Costa, Teresa Moita, Johan Eriksson, Ulla Rasmussen, Sara Jonasson Rydberg. BMAA in shellfish from two Portuguese transitional water bodies suggests the marine dinoflagellate Gymnodinium catenatum as a potential BMAA source. Aquatic toxicology (Amsterdam, Netherlands). 2014 Jul; 152(?):131-8. doi: 10.1016/j.aquatox.2014.03.029. [PMID: 24747603]
  • Audrey Combes, Saïda El Abdellaoui, Jérome Vial, Emmeline Lagrange, Valérie Pichon. Development of an analytical procedure for quantifying the underivatized neurotoxin β-N-methylamino-L-alanine in brain tissues. Analytical and bioanalytical chemistry. 2014 Jul; 406(19):4627-36. doi: 10.1007/s00216-014-7872-y. [PMID: 24858470]
  • Valeska Contardo-Jara, Torsten Schwanemann, Stephan Pflugmacher. Uptake of a cyanotoxin, β-N-methylamino-L-alanine, by wheat (Triticum aestivum). Ecotoxicology and environmental safety. 2014 Jun; 104(?):127-31. doi: 10.1016/j.ecoenv.2014.01.039. [PMID: 24675440]
  • Maitham Ahmed Al-Sammak, Kyle D Hoagland, David Cassada, Daniel D Snow. Co-occurrence of the cyanotoxins BMAA, DABA and anatoxin-a in Nebraska reservoirs, fish, and aquatic plants. Toxins. 2014 Jan; 6(2):488-508. doi: 10.3390/toxins6020488. [PMID: 24476710]
  • Liying Jiang, Johan Eriksson, Sandra Lage, Sara Jonasson, Shiva Shams, Martin Mehine, Leopold L Ilag, Ulla Rasmussen. Diatoms: a novel source for the neurotoxin BMAA in aquatic environments. PloS one. 2014; 9(1):e84578. doi: 10.1371/journal.pone.0084578. [PMID: 24392143]
  • Maitham Ahmed Al-Sammak, Kyle D Hoagland, Daniel D Snow, David Cassada. Methods for simultaneous detection of the cyanotoxins BMAA, DABA, and anatoxin-a in environmental samples. Toxicon : official journal of the International Society on Toxinology. 2013 Dec; 76(?):316-25. doi: 10.1016/j.toxicon.2013.10.015. [PMID: 24140919]
  • Glen E Kisby, Holly Moore, Peter S Spencer. Animal models of brain maldevelopment induced by cycad plant genotoxins. Birth defects research. Part C, Embryo today : reviews. 2013 Dec; 99(4):247-55. doi: 10.1002/bdrc.21052. [PMID: 24339036]
  • Mikael K R Engskog, Oskar Karlsson, Jakob Haglöf, Albert Elmsjö, Eva Brittebo, Torbjörn Arvidsson, Curt Pettersson. The cyanobacterial amino acid β-N-methylamino-l-alanine perturbs the intermediary metabolism in neonatal rats. Toxicology. 2013 Oct; 312(?):6-11. doi: 10.1016/j.tox.2013.07.010. [PMID: 23886855]
  • Xiaobin Xie, Margaret Basile, Deborah C Mash. Cerebral uptake and protein incorporation of cyanobacterial toxin β-N-methylamino-L-alanine. Neuroreport. 2013 Oct; 24(14):779-84. doi: 10.1097/wnr.0b013e328363fd89. [PMID: 23979257]
  • Lotta Berntzon, Sven Erasmie, Narin Celepli, Johan Eriksson, Ulla Rasmussen, Birgitta Bergman. BMAA inhibits nitrogen fixation in the cyanobacterium Nostoc sp. PCC 7120. Marine drugs. 2013 Aug; 11(8):3091-108. doi: 10.3390/md11083091. [PMID: 23966039]
  • Estefanía de Munck, Emma Muñoz-Sáez, María Teresa Antonio, Javier Pineda, Amparo Herrera, Begoña G Miguel, Rosa María Arahuetes. Effect of β-N-methylamino-L-alanine on oxidative stress of liver and kidney in rat. Environmental toxicology and pharmacology. 2013 Mar; 35(2):193-9. doi: 10.1016/j.etap.2012.12.004. [PMID: 23328118]
  • Valeska Contardo-Jara, Marc Sebastian Funke, Anja Peuthert, Stephan Pflugmacher. β-N-Methylamino-L-alanine exposure alters defense against oxidative stress in aquatic plants Lomariopsis lineata, Fontinalis antipyretica, Riccia fluitans and Taxiphyllum barbieri. Ecotoxicology and environmental safety. 2013 Feb; 88(?):72-8. doi: 10.1016/j.ecoenv.2012.10.026. [PMID: 23177931]
  • Elijah W Stommel, Nicholas C Field, Tracie A Caller. Aerosolization of cyanobacteria as a risk factor for amyotrophic lateral sclerosis. Medical hypotheses. 2013 Feb; 80(2):142-5. doi: 10.1016/j.mehy.2012.11.012. [PMID: 23246360]
  • András Guseo. [The Parkinson puzzle]. Orvosi hetilap. 2012 Dec; 153(52):2060-9. doi: 10.1556/oh.2012.29461. [PMID: 23261994]
  • Steven A Cohen. Analytical techniques for the detection of α-amino-β-methylaminopropionic acid. The Analyst. 2012 May; 137(9):1991-2005. doi: 10.1039/c2an16250d. [PMID: 22421821]
  • Sandra A Banack, Peter B Nunn, Ran Cheng, Walter G Bradley. Washed cycad flour contains β-N-methyl amino-L-alanine and may explain parkinsonism symptoms. Annals of neurology. 2011 Feb; 69(2):423; author reply 423-4. doi: 10.1002/ana.22291. [PMID: 21387387]
  • Thomas E Marler, Laura R Snyder, Christopher A Shaw. Cycas micronesica (Cycadales) plants devoid of endophytic cyanobacteria increase in beta-methylamino-L-alanine. Toxicon : official journal of the International Society on Toxinology. 2010 Sep; 56(4):563-8. doi: 10.1016/j.toxicon.2010.05.015. [PMID: 20570592]
  • Maria Letizia Cucchiaroni, Maria Teresa Viscomi, Giorgio Bernardi, Marco Molinari, Ezia Guatteo, Nicola B Mercuri. Metabotropic glutamate receptor 1 mediates the electrophysiological and toxic actions of the cycad derivative beta-N-Methylamino-L-alanine on substantia nigra pars compacta DAergic neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2010 Apr; 30(15):5176-88. doi: 10.1523/jneurosci.5351-09.2010. [PMID: 20392940]
  • Thomas Krüger, Bettina Mönch, Steven Oppenhäuser, Bernd Luckas. LC-MS/MS determination of the isomeric neurotoxins BMAA (beta-N-methylamino-L-alanine) and DAB (2,4-diaminobutyric acid) in cyanobacteria and seeds of Cycas revoluta and Lathyrus latifolius. Toxicon : official journal of the International Society on Toxinology. 2010 Feb; 55(2-3):547-57. doi: 10.1016/j.toxicon.2009.10.009. [PMID: 19825383]
  • Eric D Brenner, Philip Feinberg, Suzan Runko, Gloria M Coruzzi. A mutation in the Proteosomal Regulatory Particle AAA-ATPase-3 in Arabidopsis impairs the light-specific hypocotyl elongation response elicited by a glutamate receptor agonist, BMAA. Plant molecular biology. 2009 Jul; 70(5):523-33. doi: 10.1007/s11103-009-9489-7. [PMID: 19412571]
  • Donald G Barceloux. Cycad seeds and chronic neurologic disease (Cycas species). Disease-a-month : DM. 2009 Jun; 55(6):353-60. doi: 10.1016/j.disamonth.2009.03.004. [PMID: 19446678]
  • Reyniel Cruz-Aguado, Christopher A Shaw. The ALS/PDC syndrome of Guam and the cycad hypothesis. Neurology. 2009 Feb; 72(5):474, 476; author reply 475-6. doi: ". [PMID: 19195085]
  • Walter G Bradley, Sandra Anne Banack, Paul Alan Cox. The ALS/PDC syndrome of Guam and the cycad hypothesis. Neurology. 2009 Feb; 72(5):473-4, 476; author reply 475. doi: ". [PMID: 19195084]
  • Peter S Spencer, Valerie Palmer, Glen Kisby. The ALS/PDC syndrome of Guam and the cycad hypothesis. Neurology. 2009 Feb; 72(5):474-6; author reply 475. doi: ". [PMID: 19195086]
  • Peter B Nunn. Three phases of research on beta-N-methylamino-L-alanine (BMAA)--a neurotoxic amino acid. Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases. 2009; 10 Suppl 2(?):26-33. doi: 10.3109/17482960903272975. [PMID: 19929728]
  • Mark M Kushnir, Jonas Bergquist. Beta-methylamino-L-alanine analysis by liquid chromatography tandem mass spectrometry with iTRAQ as the derivative. European journal of mass spectrometry (Chichester, England). 2009; 15(3):439-43. doi: 10.1255/ejms.984. [PMID: 19395779]
  • Vardan T Karamyan, Robert C Speth. Animal models of BMAA neurotoxicity: a critical review. Life sciences. 2008 Jan; 82(5-6):233-46. doi: 10.1016/j.lfs.2007.11.020. [PMID: 18191417]
  • Shyam D Rao, Sandra Anne Banack, Paul Alan Cox, John H Weiss. BMAA selectively injures motor neurons via AMPA/kainate receptor activation. Experimental neurology. 2006 Sep; 201(1):244-52. doi: 10.1016/j.expneurol.2006.04.017. [PMID: 16764863]
  • Paul Alan Cox, Sandra Anne Banack, Susan J Murch. Biomagnification of cyanobacterial neurotoxins and neurodegenerative disease among the Chamorro people of Guam. Proceedings of the National Academy of Sciences of the United States of America. 2003 Nov; 100(23):13380-3. doi: 10.1073/pnas.2235808100. [PMID: 14612559]
  • Eric D Brenner, Dennis W Stevenson, Richard W McCombie, Manpreet S Katari, Stephen A Rudd, Klaus F X Mayer, Peter M Palenchar, Suzan J Runko, Richard W Twigg, Guangwei Dai, Rob A Martienssen, Phillip N Benfey, Gloria M Coruzzi. Expressed sequence tag analysis in Cycas, the most primitive living seed plant. Genome biology. 2003; 4(12):R78. doi: 10.1186/gb-2003-4-12-r78. [PMID: 14659015]
  • Paul Alan Cox, Oliver W Sacks. Cycad neurotoxins, consumption of flying foxes, and ALS-PDC disease in Guam. Neurology. 2002 Mar; 58(6):956-9. doi: 10.1212/wnl.58.6.956. [PMID: 11914415]
  • E D Brenner, N Martinez-Barboza, A P Clark, Q S Liang, D W Stevenson, G M Coruzzi. Arabidopsis mutants resistant to S(+)-beta-methyl-alpha, beta-diaminopropionic acid, a cycad-derived glutamate receptor agonist. Plant physiology. 2000 Dec; 124(4):1615-24. doi: 10.1104/pp.124.4.1615. [PMID: 11115879]
  • H Andersson, E Lindqvist, L Olson. Plant-derived amino acids increase hippocampal BDNF, NGF, c-fos and hsp70 mRNAs. Neuroreport. 1997 May; 8(8):1813-7. doi: 10.1097/00001756-199705260-00005. [PMID: 9223057]
  • D L Eizirik, G E Kisby. Cycad toxin-induced damage of rodent and human pancreatic beta-cells. Biochemical pharmacology. 1995 Jul; 50(3):355-65. doi: 10.1016/0006-2952(95)00150-x. [PMID: 7646537]
  • C Thomsen, E R Mulvihill, B Haldeman, D S Pickering, D R Hampson, P D Suzdak. A pharmacological characterization of the mGluR1 alpha subtype of the metabotropic glutamate receptor expressed in a cloned baby hamster kidney cell line. Brain research. 1993 Aug; 619(1-2):22-8. doi: 10.1016/0006-8993(93)91592-g. [PMID: 7690672]
  • K S Pai, S K Shankar, V Ravindranath. Billion-fold difference in the toxic potencies of two excitatory plant amino acids, L-BOAA and L-BMAA: biochemical and morphological studies using mouse brain slices. Neuroscience research. 1993 Aug; 17(3):241-8. doi: 10.1016/0168-0102(93)90051-q. [PMID: 7901822]
  • D A Butterfield, N C Hall, S J Cross. Effects of beta-(N-methylamino)-L-alanine on cytoskeletal proteins of erythrocyte membranes. Chemical research in toxicology. 1993 Jul; 6(4):417-20. doi: 10.1021/tx00034a004. [PMID: 8397004]
  • C N Allen, P S Spencer, D O Carpenter. Beta-N-methylamino-L-alanine in the presence of bicarbonate is an agonist at non-N-methyl-D-aspartate-type receptors. Neuroscience. 1993 Jun; 54(3):567-74. doi: 10.1016/0306-4522(93)90228-8. [PMID: 7687332]
  • Y C Chang, S J Chiu, K P Kao. beta-N-methylamino-L-alanine (L-BMAA) decreases brain glutamate receptor number and induces behavioral changes in rats. The Chinese journal of physiology. 1993; 36(2):79-84. doi: ". [PMID: 7904554]
  • Q R Smith, H Nagura, Y Takada, M W Duncan. Facilitated transport of the neurotoxin, beta-N-methylamino-L-alanine, across the blood-brain barrier. Journal of neurochemistry. 1992 Apr; 58(4):1330-7. doi: 10.1111/j.1471-4159.1992.tb11346.x. [PMID: 1548467]
  • M W Duncan, S P Markey, B G Weick, P G Pearson, H Ziffer, Y Hu, I J Kopin. 2-Amino-3-(methylamino)propanoic acid (BMAA) bioavailability in the primate. Neurobiology of aging. 1992 Mar; 13(2):333-7. doi: 10.1016/0197-4580(92)90047-2. [PMID: 1522948]
  • G R Stewart, J W Olney, M Pathikonda, W D Snider. Excitotoxicity in the embryonic chick spinal cord. Annals of neurology. 1991 Dec; 30(6):758-66. doi: 10.1002/ana.410300604. [PMID: 1686386]
  • M W Duncan, N E Villacreses, P G Pearson, L Wyatt, S I Rapoport, I J Kopin, S P Markey, Q R Smith. 2-amino-3-(methylamino)-propanoic acid (BMAA) pharmacokinetics and blood-brain barrier permeability in the rat. The Journal of pharmacology and experimental therapeutics. 1991 Jul; 258(1):27-35. doi: . [PMID: 2072299]
  • M D Lewis, I N McQueen, M F Scanlon. Motor neurone disease serum and beta-N-methylamino-L-alanine stimulate thyrotrophin-releasing hormone production by cultured brain cells. Brain research. 1990 Dec; 537(1-2):251-5. doi: 10.1016/0006-8993(90)90365-i. [PMID: 1982241]
  • H Lindström, J Luthman, P Mouton, P Spencer, L Olson. Plant-derived neurotoxic amino acids (beta-N-oxalylamino-L-alanine and beta-N-methylamino-L-alanine): effects on central monoamine neurons. Journal of neurochemistry. 1990 Sep; 55(3):941-9. doi: 10.1111/j.1471-4159.1990.tb04582.x. [PMID: 1974606]
  • J H Weiss, J Y Koh, D W Choi. Neurotoxicity of beta-N-methylamino-L-alanine (BMAA) and beta-N-oxalylamino-L-alanine (BOAA) on cultured cortical neurons. Brain research. 1989 Sep; 497(1):64-71. doi: 10.1016/0006-8993(89)90970-0. [PMID: 2551452]
  • G E Kisby, D N Roy, P S Spencer. Determination of beta-N-methylamino-L-alanine (BMAA) in plant (Cycas circinalis L.) and animal tissue by precolumn derivatization with 9-fluorenylmethyl chloroformate (FMOC) and reversed-phase high-performance liquid chromatography. Journal of neuroscience methods. 1988 Nov; 26(1):45-54. doi: 10.1016/0165-0270(88)90128-8. [PMID: 3199847]
  • L T Kurland. Amyotrophic lateral sclerosis and Parkinson's disease complex on Guam linked to an environmental neurotoxin. Trends in neurosciences. 1988 Feb; 11(2):51-4. doi: 10.1016/0166-2236(88)90163-4. [PMID: 2465598]
  • ". A poison tree. Lancet (London, England). 1987 Oct; 2(8565):947-8. doi: ". [PMID: 2889865]
  • P S Spencer, P B Nunn, J Hugon, A C Ludolph, S M Ross, D N Roy, R C Robertson. Guam amyotrophic lateral sclerosis-parkinsonism-dementia linked to a plant excitant neurotoxin. Science (New York, N.Y.). 1987 Jul; 237(4814):517-22. doi: 10.1126/science.3603037. [PMID: 3603037]
  • P B Nunn, M Seelig, J C Zagoren, P S Spencer. Stereospecific acute neuronotoxicity of 'uncommon' plant amino acids linked to human motor-system diseases. Brain research. 1987 May; 410(2):375-9. doi: 10.1016/0006-8993(87)90342-8. [PMID: 3109690]