Bongkrek acid

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Bongkrek acid
Bongkrekic acid.svg
Names
IUPAC name
20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
Other names
Bongkrekic acid
Bonqkrekik acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Bongkrekic+acid
Properties
C28H38O7
Molar mass 486.605 g·mol−1
Melting point 50 to 60 °C (122 to 140 °F; 323 to 333 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Bongkrek acid (also known as bongkrekic acid[1]) is a respiratory toxin produced in fermented coconut contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans.[2][3][4] it has been implicated in deaths resulting from eating coconut-based product known as tempe bongkrèk, which is banned in Indonesia.[5] It was also responsible for 75 deaths and over 200 hospitalizations due to contaminated beer in a Mozambique funeral.[6]

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.[7] 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[8].

References[edit]

  1. ^ Garcia, R. A.; Hotchkiss, J. H.; Steinkraus, K. H. (1999). "The Effect of Lipids on Bongkrekic (Bongkrek) Acid Toxin Production by Burkholderia cocovenenans in Coconut Media". Food Additives and Contaminants. 16 (2): 63–69. doi:10.1080/026520399284217. PMID 10435074.
  2. ^ Henderson, P. J. F.; Lardy, H. A. (1970). "Bongkrekic Acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria" (PDF). Journal of Biological Chemistry. 245 (6): 1319–1326. PMID 4245638.
  3. ^ Henderson, P. J. F.; Lardy, H. A. (1970). "Bongkrekic Acid: An Inhibitor of Adenine Nucleotide Translocase of Mitochondria" (PDF). Journal of Biological Chemistry. 245 (6): 1319–1326. PMID 4245638.
  4. ^ De Bruijn, J.; Frost, D. J.; Nugteren, D. H.; Gaudemer, A.; Lijmbach, G. W. M.; Cox, H. C.; Berends, W. (1973). "Structure of Bongkrekic Acid". Tetrahedron. 29 (11): 1541–1547. doi:10.1016/S0040-4020(01)83395-0.
  5. ^ Bhavbhuti M. Mehta, Afaf Kamal-Eldin and Robert Z. Iwanski, ed. (2012). Chapter 9. Fermented Cereal and Legume Products. Fermentation: Effects on Food Properties. CRC Press. doi:10.1201/b11876-10. ISBN 978-1-4398-5334-4.
  6. ^ "Mozambique: Mass Poisoning Caused By Bacterial Contamination". allafrica.com. 4 November 2015. Retrieved 7 February 2016.
  7. ^ Toxicants Occurring Naturally in Foods. National Academy of Sciences. 1973. p. 472.
  8. ^ Ruprecht, Jonathan J.; King, Martin S.; Zögg, Thomas; Aleksandrova, Antoniya A.; Pardon, Els; Crichton, Paul G.; Steyaert, Jan; Kunji, Edmund R.S. (2019). "The Molecular Mechanism of Transport by the Mitochondrial ADP/ATP Carrier". Cell. 176 (3): 435–447.e15. doi:10.1016/j.cell.2018.11.025. ISSN 0092-8674. PMC 6349463. PMID 30611538.