Caramboxin

Last updated
Caramboxin
Caramboxin.svg
Names
IUPAC name
2-Carboxy-3-hydroxy-5-methoxy-L-phenylalanine
Systematic IUPAC name
2-[(2S)-2-Amino-2-carboxyethyl]-6-hydroxy-4-methoxybenzoic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C11H13NO6/c1-18-6-2-5(3-7(12)10(14)15)9(11(16)17)8(13)4-6/h2,4,7,13H,3,12H2,1H3,(H,14,15)(H,16,17)/t7-/m0/s1
    Key: DYJIDGJHOLTGBO-ZETCQYMHSA-N
  • OC(=O)c1c(O)cc(OC)cc1C[C@H](N)C(=O)O
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).

Caramboxin (CBX) is a toxin found in star fruit (Averrhoa carambola). [1] [2] Individuals with some types of kidney disease are susceptible to adverse neurological effects including intoxication, seizures and even death after eating star fruit. [3] Caramboxin has been identified as the neurotoxin responsible for these effects. Caramboxin is a non-proteinogenic amino acid that stimulates the glutamate receptors in neurons. Its chemical structure is similar to the amino acid phenylalanine. Caramboxin is an agonist of both NMDA and AMPA glutamatergic ionotropic receptors with potent excitatory, convulsant, and neurodegenerative properties. [2]

A possible interaction between caramboxin and oxalic acid in starfruit can lead to both neurotoxic and nephrotoxic effects. Consuming large amounts of starfruit or its juice on an empty stomach is not recommended, even for individuals with normal kidney function. [4]

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<span class="mw-page-title-main">Carambola</span> Fruit

Carambola, also known as star fruit, is the fruit of Averrhoa carambola, a species of tree native to tropical Southeast Asia. The edible fruit has distinctive ridges running down its sides. When cut in cross-section, it resembles a star, giving it the name of star fruit. The entire fruit is edible, usually raw, and may be cooked or made into relishes, preserves, garnish, and juices. It is commonly consumed in Southeast Asia, South Asia, the South Pacific, Micronesia, parts of East Asia, the United States, parts of Latin America, and the Caribbean. The tree is cultivated throughout tropical areas of the world.

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<i>Averrhoa carambola</i> Species of tree

Averrhoa carambola is a species of tree in the family Oxalidaceae native to tropical Southeast Asia; it has a number of common names, including carambola, star fruit and five-corner. It is a small tree or shrub that grows 5 to 12 m tall, with rose to red-purple flowers. The flowers are small and bell-shaped, with five petals that have whitish edges. The flowers are often produced year round under tropical conditions. The tree is cultivated in tropical and semitropical regions for its edible fruits.

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References

  1. "Star fruit's chemical curse". Chemical & Engineering News : 28. December 2, 2013.
  2. 1 2 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.
  3. 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.
  4. 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.