Global InformationNodularin information
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Cyclo[(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl-(2Z)-2-(methylamino)-2-butenoyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl]
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Chemical formula
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C41H60N8O10 |
| Molar mass | 824.977 g·mol−1 |
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H300, H310, H315, H317, H319, H330, H335 |
Precautionary statements
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P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Nodularins are potent toxins produced by the cyanobacterium Nodularia spumigena,[1] among others.[2] This aquatic, photosynthetic cyanobacterium forms visible colonies that present as algal blooms in brackish water bodies throughout the world.[3] The late summer blooms of Nodularia spumigena are among the largest cyanobacterial mass occurrences in the world. Cyanobacteria are composed of many toxic substances, most notably of microcystins and nodularins: the two are not easily differentiated. A significant homology of structure and function exists between the two, and microcystins have been studied in greater detail. Because of this, facts from microcystins are often extended to nodularins.[4]
Nodularin-R is the predominant toxin variant, though 10 variants of nodularin have been discovered to date. Nodularins are cyclic nonribosomal pentapeptides and contain several unusual non-proteinogenic amino acids such as N-methyl-didehydroaminobutyric acid and the β-amino acid ADDA. These compounds are relatively stable compounds: light, temperature, and microwaves do little to degrade the compounds.[5]
Nodularins are often attributed to gastroenteritis, allergic irritation reactions, and liver diseases.[6] Nodularin-R is most notorious as a potent hepatotoxin that may cause serious damage to the liver of humans and other animals. The WHO drinking water concentration limit for nodularins (extended from microcystins-LR) is 1.5 ug /L.[7]
- ^ Sivonen K, Kononen K, Carmichael WW, Dahlem AM, Rinehart KL, Kiviranta J, Niemela SI (1989). "Occurrence of the hepatotoxic cyanobacterium Nodularia spumigena in the Baltic Sea and structure of the toxin". Appl. Environ. Microbiol. 55 (8): 1990–5. Bibcode:1989ApEnM..55.1990S. doi:10.1128/aem.55.8.1990-1995.1989. PMC 202992. PMID 2506812.
- ^ Gehringer, Michelle M; Adler, Lewis; Roberts, Alexandra A; Moffitt, Michelle C; Mihali, Troco K; Mills, Toby J T; Fieker, Claus; Neilan, Brett A (October 2012). "Nodularin, a cyanobacterial toxin, is synthesized in planta by symbiotic Nostoc sp". The ISME Journal. 6 (10): 1834–1847. doi:10.1038/ismej.2012.25. PMC 3446798. PMID 22456448.
- ^ Chen, Yun; Shen, Danfeng; Fang, Danjun (21 October 2013). "Nodularins in Poisoning". Clinica Chimica Acta. 425: 18–29. doi:10.1016/j.cca.2013.07.005. PMID 23872223.
- ^ Chen, Yun; Shen, Danfeng; Fang, Danjun (21 October 2013). "Nodularins in Poisoning". Clinica Chimica Acta. 425: 18–29. doi:10.1016/j.cca.2013.07.005. PMID 23872223.
- ^ Chen, Yun; Shen, Danfeng; Fang, Danjun (21 October 2013). "Nodularins in Poisoning". Clinica Chimica Acta. 425: 18–29. doi:10.1016/j.cca.2013.07.005. PMID 23872223.
- ^ Dawson, R. M. (1998). "The Toxicology of Microcystins". Toxicon. 36 (7): 953–962. doi:10.1016/S0041-0101(97)00102-5. PMID 9690788.
- ^ "Nodularin". Substances of Biological Interest, Bacterial Toxin, Natural Toxin. SelfDecode. Retrieved 30 April 2017.