Asid bongkrek

Asid bongkrek
Nama
	Nama IUPAC 20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
	Nama lain Asid bongkrekik
Pengecam
No. Pendaftaran CAS	11076-19-0 ;
Imej model 3D Jmol	Imej berinteraktif; Imej berinteraktif;
ChEBI	CHEBI:77742 ;
ChemSpider	4938689 (2E,4E,8E,10E,14E,18E,20E) ; 4529223 (2E,4Z,8Z,10E,14E,18E,20Z) ; 23764 (6R,17S) ; 2329 () ;
MeSH	Bongkrekic+acid
PubChem CID	25463 (6R,17S); 2423 ();
UNII	L7V4I673D2 ;
CompTox Dashboard (EPA)	DTXSID00894840 ;
	InChI 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) Key: SHCXABJSXUACKU-UHFFFAOYSA-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;
	SMILES 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;
Sifat
Formula kimia	C28H38O7
Jisim molar	486.61 g·mol−1
Takat lebur	50 hingga 60 °C (122 hingga 140 °F; 323 hingga 333 K)
	Kecuali jika dinyatakan sebaliknya, data diberikan untuk bahan-bahan dalam keadaan piawainya (pada 25 °C [77 °F], 100 kPa).
	pengesahan (apa yang perlu: /?)
	Rujukan kotak info

Asid bongkrek (juga dikenali sebagai asid bongkrekik^[1]) ialah toksin pernafasan yang terhasil dalam kelapa ditapai atau jagung tercemar oleh bakterium Burkholderia gladioli pathovar cocovenenans.^[2]^[3]^[4]

Ia amat toksik kerana sebatian tersebut merencat translokase ADP/ATP, juga dipanggil pembawa ADP/ATP mitokondria, mencegah ATP daripada meninggalkan mitokondria memberi tenaga metabolik ke keseluruhan sel yang tinggal.^[5] Struktur asid bongkrek yang terikat dengan translokase ADP/ATP telah dilarutkan pada tahun 2019, menunjukkan ia mengikat dengan tapak pengikatan substrat, mencegah ATP dalam matriks mitokondria daripada pengikatan.^[6]

Ia terbabit dalam kematian akibat makan keluaran berasaskan kelapa yang dikenali sebagai tempe bongkrèk, yang diharamkan di Indonesia.^[7] Ia juga bertanggungjawab atas 75 kematian dan lebih 200 orang dimasukkan ke hospital disebabkan bir tercemar di majlis pengebumian Mozambique. Pada bulan Oktober 2020, sembilan ahli keluarga di China mati selepas makan mi jagung tercemar dengan asid tersebut.^[8]

Rujukan

^ 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.
^ 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.
^ 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.
^ 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.
^ Toxicants Occurring Naturally in Foods. National Academy of Sciences. 1973. m/s. 472.
^ 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.
^ Bhavbhuti M. Mehta, Afaf Kamal-Eldin and Robert Z. Iwanski, penyunting (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.
^ Majumder, Bhaswati Guha (20 October 2020). "Deadly Breakfast: 9 Family Members Die After Eating Homemade Noodles in China". www.ibtimes.sg (dalam bahasa Inggeris). Dicapai pada 24 October 2020.

[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.

[pjf-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] 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. m/s. 472.

[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, penyunting (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 (dalam bahasa Inggeris). Dicapai pada 24 October 2020.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]