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

Flavotoxin A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Bongkrekic+acid
Properties
C28H38O7
Molar mass 486.61 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 more deadly than other mitochondrial poisons 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 the soybean and coconut-based product known as tempe bongkrèk, which is banned in Indonesia.[4]

It is highly toxic because of its effect on the ATP/ADP translocation mechanism. It shuts this system down, preventing ATP from leaving the mitochondria and providing energy to the rest of the cell.[5]

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. PMID 10435074. doi:10.1080/026520399284217. 
  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. ^ 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. 
  4. ^ 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. ISBN 978-1-4398-5334-4. doi:10.1201/b11876-10. 
  5. ^ Toxicants Occurring Naturally in Foods. National Academy of Sciences. 1973. p. 472.