Karakin
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| Names | |
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| IUPAC name
[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5,6-bis(3-nitropropanoyloxy)oxan-2-yl]methyl 3-nitropropanoate | |
| Other names
1,2,6-tri-(3-nitropropanoyl)-β-D-glucopyranose | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| Properties | |
| C15H21N3O15 | |
| Molar mass | 483.34 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Karakin is a toxic glucoside found in several plants, principally in the berries of the New Zealand native tree Karaka (Corynocarpus laevigatus), though it has also been identified in other plants such as Corynocarpus similis, Coronilla varia, Lotus pedunculatus, and Heteropterys umbellata.[1][2][3] Karakin is the glucoside of 3-nitropropionic acid and can produce severe toxicity when consumed by humans, with symptoms including vomiting, diarrhea, muscle weakness, paralysis, confusion and convulsions. Karaka berries can however be consumed safely by some native New Zealand birds such as Kereru, and were traditionally eaten by Māori after an extensive preparation process to remove the toxin.[4][5][6][7]
References
[edit]- ↑ Hutchins RF, Sutherland OR, Gnanasunderam C, Greenfield WJ, Williams EM, Wright HJ. Toxicity of nitro compounds from Lotus pedunculatus to grass grub (Costelytra zealandica) (Coleoptera: Scarabaeidae). J Chem Ecol. 1984 Jan;10(1):81-93. doi:10.1007/BF00987645 PMID 24318230
- ↑ Cabalion P, Poisson J. Corynocarpus similis Hemsley, plante alimentaire et toxique de Vanuatu (ex-Nouvelles-Hebrides) [Corynocarpus similis Hemsley, dietary and toxic plant of Vanuatu (formerly New Hebrides)]. J Ethnopharmacol. 1987 Nov;21(2):189-91. doi:10.1016/0378-8741(87)90130-9 PMID 3501820
- ↑ Mannochio-Russo H, Nunes WDG, Almeida RF, Albernaz LC, Espindola LS, Bolzani VS. Old Meets New: Mass Spectrometry-Based Untargeted Metabolomics Reveals Unusual Larvicidal Nitropropanoyl Glycosides from the Leaves of Heteropterys umbellata. J Nat Prod. 2023 Mar 24;86(3):621-632. doi:10.1021/acs.jnatprod.2c00788 PMID 36848642
- ↑ Shaw SD, Billing T. Karaka (Corynocarpus laevigatus) toxicosis in North Island brown kiwi (Apteryx mantelli). Vet Clin North Am Exot Anim Pract. 2006 Sep;9(3):545-9. doi:10.1016/j.cvex.2006.05.014 PMID 16931372
- ↑ MacAskill JJ, Manley-Harris M, Field RJ. Quantification of nitropropanoyl glucosides in karaka nuts before and after treatment. Food Chem. 2015 May 15;175:543-8. doi:10.1016/j.foodchem.2014.12.022 PMID 25577118
- ↑ Watson DJ, Evans A, Blockman M, Wiesner L. Detection of karakin poisoning using a targeted mass spectrometric workflow. S Afr Med J. 2022 Dec 1;112(12):901-903. doi:10.7196/SAMJ.2022.v112i12.16667 PMID 36472319
- ↑ McAlpine, Kate G.; Cory, Sally; Cox, Bart Te Manihera; McLeod (Taranaki Whānui), Terese; Rapson, Gillian; Roskruge (Te Ātiawa, Ngāti Tama), Nick Rahiri; Shepherd, Lara D. (5 September 2024). "Karaka (Corynocarpus laevigatus): native taonga (treasure) or environmental weed?". New Zealand Journal of Botany. 63 (5). Informa UK Limited: 887–912. doi:10.1080/0028825x.2024.2388751. ISSN 0028-825X.
