Caramboxin
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| IUPAC name
2-Carboxy-3-hydroxy-5-methoxy-L-phenylalanine
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| Systematic IUPAC name
2-[(2S)-2-Amino-2-carboxyethyl]-6-hydroxy-4-methoxybenzoic acid | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C11H13NO6 | |
| Molar mass | 255.226 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Caramboxin (CBX) is a toxin found in star fruit (Averrhoa carambola)[1][2] and the related bilimbi fruit (Averrhoa bilimbi).[3] Individuals with some types of kidney disease are susceptible to adverse neurological effects including intoxication, seizures and even death after eating star fruit[4] and bilimbi fruit.[3] In 2013, caramboxin was identified as the neurotoxin responsible for these effects.[2]
Caramboxin is a non-proteinogenic amino acid, with a chemical structure similar to the amino acid phenylalanine, but with extra hydroxyl, carboxyl and methoxy substituents, making it also a phenol, a benzoic acid, and a phenol ether. Caramboxin stimulates the glutamate receptors in neurons, being an agonist of both NMDA and AMPA glutamatergic ionotropic receptors with potent excitatory, convulsant, and neurodegenerative properties,[2] resulting in symptoms of central nervous system disorder, including mental confusion, seizures, and status epilepticus.[5]
A possible interaction between caramboxin and oxalic acid in starfruit can lead to both neurotoxic and nephrotoxic effects.[6] Consuming large amounts of starfruit or its juice on an empty stomach is not recommended, even for individuals with normal kidney function.[6][7] As caramboxin is water soluble, intense hemodialysis has often been used to improve the outcome for patients.[6]
An enantioselective total synthesis of caramboxin was first published in 2024. It involves a catalytic phase-transfer alkylation of a glycine imine by ethyl acetoacetate.[8]
References
[edit]- ^ "Star fruit's chemical curse". Chemical & Engineering News: 28. December 2, 2013.
- ^ a b c Garcia-Cairasco, Norberto; Moyses-Neto, Miguel; Del Vecchio, Flavio; Oliveira, José A. C; Dos Santos, Francisco L; Castro, Olagide W; Arisi, Gabriel M; Dantas, Márcio; Carolino, Ruither O. G; Coutinho-Netto, Joaquim; Dagostin, Andre L. A; Rodrigues, Marcelo C. A; Leão, Ricardo M; Quintiliano, Samir A. P; Silva, Luiz F; Gobbo-Neto, Leonardo; Lopes, Norberto P (2013). "Elucidating the Neurotoxicity of the Star Fruit". Angewandte Chemie International Edition. 52 (49): 13067–70. doi:10.1002/anie.201305382. PMID 24281890.
- ^ a b Caetano, Camille Pereira; De Sá, Cinara Barros; Faleiros, Bruno Antônio Paixão; Gomes, Marcelo Fonseca Coutinho Fernandes; Pereira, Edna Regina Silva (2017). "Neurotoxicity following the Ingestion of Bilimbi Fruit (Averrhoa bilimbi) in an End-Stage Renal Disease Patient on Hemodialysis". Case Reports in Nephrology and Dialysis. 7 (1): 6–12. doi:10.1159/000454945. PMC 5301110. PMID 28203564.
- ^ Raciti, Christopher; Blanzaco, Melba; Bernstein, Jeffrey (August 2023). "Death associated with ingestion of starfruit (Averrhoa carambola) in a patient with chronic kidney disease". The American Journal of Emergency Medicine. 70: 208.e1–208.e3. doi:10.1016/j.ajem.2023.06.043. PMID 37394384. Retrieved 2 December 2024.
- ^ Yasawardene, Pamodh; Jayarajah, Umesh; De Zoysa, Ishan; Seneviratne, Suranjith L. (November 2020). "Mechanisms of star fruit (Averrhoa carambola) toxicity: A mini-review". Toxicon. 187: 198–202. doi:10.1016/j.toxicon.2020.09.010. PMID 32966829.
- ^ a b c Wong, Koh-Wei; Lansing, Meryl Grace (July 2021). "Case of acute kidney injury due to bilimbi fruit ingestion". BMJ Case Reports. 14 (7): e242325. doi:10.1136/bcr-2021-242325. PMC 8728385. PMID 34301701. Retrieved 2 December 2024.
- ^ Neto, M. M; Silva, G. E; Costa, R. S; Vieira Neto, O. M; Garcia-Cairasco, N; Lopes, N. P; Haendchen, P. F; Silveira, C; Mendes, A. R; Filho, R. R; Dantas, M (2009). "Star fruit: Simultaneous neurotoxic and nephrotoxic effects in people with previously normal renal function". Clinical Kidney Journal. 2 (6): 485–488. doi:10.1093/ndtplus/sfp108. PMC 4421323. PMID 25949386.
- ^ Derrien, Benoit; Leblanc, Karine; Evanno, Laurent; Drège, Emmanuelle (3 May 2024). "Enantioselective Total Synthesis of the Neurotoxin Caramboxin". The Journal of Organic Chemistry. 89 (9): 6489–6493. doi:10.1021/acs.joc.4c00541. PMID 38607991. Retrieved 2 December 2024.