Bongkrek acid

Bongkrek acid (also known as bongkrekic acid[1]) is a respiratory toxin produced in fermented coconut or corn contaminated by the bacterium Burkholderia gladioli pathovar cocovenenans.[2][3][4]

Bongkrek acid
Names
Preferred IUPAC name
(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(Carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
Other names
Bongkrekic acid
Bongkrekik acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH Bongkrekic+acid
UNII
  • InChI=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) N
    Key: SHCXABJSXUACKU-UHFFFAOYSA-N N
  • 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
    Key: SHCXABJSXUACKU-WUTQZGRKBG
  • InChI=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
    Key: SHCXABJSXUACKU-WUTQZGRKSA-N
  • COC(CC=CC=CCCC=CCC(C)C=CC(CC(O)=O)=CC(O)=O)C(C)=CC=C(C)C(O)=O
  • 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
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).
N verify (what is YN ?)
Infobox references

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.[5] 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.[6]

It has been implicated in deaths resulting from eating the coconut-based product known as tempe bongkrèk, which is banned in Indonesia.[7] It was also responsible for 75 deaths and over 200 hospitalizations due to contaminated beer in a Mozambique funeral. In October 2020, nine members of a family in China died after eating corn noodles contaminated with the acid.[8]

References
  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. doi:10.1016/S0021-9258(18)63238-7. PMID 4245638. Archived (PDF) from the original on 2020-10-31. Retrieved 2013-01-20.
  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. Anwar, Mehruba; Kasper, Amelia; Steck, Alaina R.; Schier, Joshua G. (June 2017). "Bongkrekic Acid—a Review of a Lesser-Known Mitochondrial Toxin". Journal of Medical Toxicology. 13 (2): 173–179. doi:10.1007/s13181-016-0577-1. ISSN 1556-9039. PMC 5440313. PMID 28105575.
  5. Toxicants Occurring Naturally in Foods. National Academy of Sciences. 1973. p. 472. ISBN 9780309021173.
  6. 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.
  7. 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.
  8. Majumder, Bhaswati Guha (20 October 2020). "Deadly Breakfast: 9 Family Members Die After Eating Homemade Noodles in China". www.ibtimes.sg. Archived from the original on 24 October 2020. Retrieved 24 October 2020.
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