| 词条 | Bongkrek acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 459981098 | ImageFile = Bongkrekic acid.svg | ImageSize = 250px | IUPACName = 20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid | OtherNames = Bongkrekic acid Bonqkrekik acid |Section1={{Chembox Identifiers | InChI = 1/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1 | InChIKey = SHCXABJSXUACKU-WUTQZGRKBG | SMILES1 = O=C(O)\\C(=C\\C=C(\\C)[C@H](OC)C/C=C\\C=C\\CC/C=C/C[C@@H](/C=C/C(=C\\C(=O)O)CC(=O)O)C)C | InChI1 = 1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/b8-6+,11-9+,12-10-,18-15+,22-16-,23-17+,24-19+/t21-,25+/m0/s1 | InChIKey1 = SHCXABJSXUACKU-WUTQZGRKSA-N | CASNo = 11076-19-0 | CASNo_Ref = {{cascite|changed|??}} | PubChem = 25463 | PubChem_Comment = (6R,17S) | PubChem1 = 2423 | PubChem1_Comment = () | ChemSpiderID = 4938689 | ChemSpiderID_Comment = (2E,4E,8E,10E,14E,18E,20E) | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 4529223 | ChemSpiderID1_Comment = (2E,4Z,8Z,10E,14E,18E,20Z) | ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID2 = 23764 | ChemSpiderID2_Comment = (6R,17S) | ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID3 = 2329 | ChemSpiderID3_Comment = () | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 77742 | MeSHName = Bongkrekic+acid | SMILES = COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C(O)=O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = SHCXABJSXUACKU-UHFFFAOYSA-N}} |Section2={{Chembox Properties | C=28 | H=38 | O=7 | MolarMass = | Appearance = | Density = | MeltingPtC = 50 to 60 | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | EUClass = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | RPhrases = | SPhrases = | RSPhrases = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }}Bongkrek acid (also known as bongkrekic acid[1]) is a respiratory toxin more deadly than other mitochondrial poisons such as cyanide or 2,4-dinitrophenol.[2] There was some dispute regarding the actual structure of bongkrek acid, but this was resolved in 1973, which explains different structures appearing in the literature prior to this date.[3] It is produced in fermented coconut contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans. In particular, it has been implicated in deaths resulting from eating coconut-based product known as tempe bongkrèk, which is banned in Indonesia.[4] It was also responsible for 75 deaths and over 200 hospitalizations due to contamined beer in a Mozambique funeral.[5] It is highly toxic because the compound inhibits the ADP/ATP translocase, also called the mitochondrial ADP/ATP carrier, preventing ATP from leaving the mitochondria to provide metabolic energy to the rest of the cell.[6] The structure of bongkrekic acid bound to ADP/ATP translocase was solved in 2019, demonstrating that it binds to the substrate binding site, preventing ATP in the mitochondrial matrix from binding[7]. References1. ^{{cite journal | last1 = Garcia | first1 = R. A. | last2 = Hotchkiss | first2 = J. H. | last3 = Steinkraus | first3 = K. H. | title = The Effect of Lipids on Bongkrekic (Bongkrek) Acid Toxin Production by Burkholderia cocovenenans in Coconut Media | journal = Food Additives and Contaminants | year = 1999 | volume = 16 | issue = 2 | pages = 63–69 | pmid = 10435074 | doi = 10.1080/026520399284217 }} 2. ^{{cite journal | last = Henderson | first = P. J. F. | last2 = Lardy | first2 = H. A. | title = Bongkrekic Acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria | journal = Journal of Biological Chemistry | year = 1970 | volume = 245 | issue = 6 | pages = 1319–1326 | pmid = 4245638 | url = http://www.jbc.org/content/245/6/1319.full.pdf | format = pdf }} 3. ^{{cite journal | last = De Bruijn | first = J. | last2 = Frost | first2 = D. J. | last3 = Nugteren | first3 = D. H. | last4 = Gaudemer | first4 = A. | last5 = Lijmbach | first5 = G. W. M. | last6 = Cox | first6 = H. C. |last7 = Berends | first7 = W. | title = Structure of Bongkrekic Acid | journal = Tetrahedron | year = 1973 | volume = 29 | issue = 11 | pages = 1541–1547 | doi = 10.1016/S0040-4020(01)83395-0 }} 4. ^{{cite book | title = Chapter 9. Fermented Cereal and Legume Products| work = Fermentation: Effects on Food Properties | editor = Bhavbhuti M. Mehta, Afaf Kamal-Eldin and Robert Z. Iwanski | publisher = CRC Press | date = 2012 | isbn = 978-1-4398-5334-4 | doi = 10.1201/b11876-10}} 5. ^{{cite news|url=http://allafrica.com/stories/201511050128.html|title=Mozambique: Mass Poisoning Caused By Bacterial Contamination|date=4 November 2015|accessdate=7 February 2016|website=allafrica.com}} 6. ^{{Cite book | title = Toxicants Occurring Naturally in Foods | publisher = National Academy of Sciences | date = 1973 | page = 472 }} 7. ^{{Cite journal|last=Ruprecht|first=Jonathan J.|last2=King|first2=Martin S.|last3=Zögg|first3=Thomas|last4=Aleksandrova|first4=Antoniya A.|last5=Pardon|first5=Els|last6=Crichton|first6=Paul G.|last7=Steyaert|first7=Jan|last8=Kunji|first8=Edmund R.S.|date=2019|title=The Molecular Mechanism of Transport by the Mitochondrial ADP/ATP Carrier|url=https://doi.org/10.1016/j.cell.2018.11.025|journal=Cell|volume=176|issue=3|pages=435–447.e15|doi=10.1016/j.cell.2018.11.025|issn=0092-8674|via=}} 6 : Toxicology|Carboxylic acids|Alkene derivatives|Ethers|ADP/ATP translocase inhibitors|Bacterial toxins |
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