Chemistry:Dinogunellin
Dinogunellins are unusual toxic phospholipids found in the roe of some fishes, and is one of the best studied ichthyotoxin.[1] These phospholipids could be found as a complex with non-toxic proteins like in the cabezon toxin or in the lipostichaerin.[2][3]
Occurrence
Dinogunellins were detected in the mature roe of four fishes: the cabezon or marbled sculpin Scorpaenichthys marmoratus, [2] the blennies Stichaeus grigorjewi [1][3] and Stichaeus nozawae, [4] and the killifish Fundulus heteroclitus. [4]
The presence of dinogunellins has been discarded in the roe of the carp Cyprinus carpio, the sculpin Hemitripterus villosus, the blenny Lumpenus fowleri,[4] and the lamprey Lapetra japonica.[5]
Structure
Dinogunellins are unusual phospholipids having a nucleotide instead of the typical glycerol in their structure. They consist of an adenine nucleotide, with a 2-aminosuccinimide attached to the phosphorus moiety and a fatty acid attached to the oxygen from either the C2' or the C3' of the sugar moiety.[1] The fatty acid chain could be either the eicosapentaenoic acid (Dinogunellin-A and Dinogunellin-B) or the stearidonic acid (Dinogunellin-C and Dinogunellin-D).[1] In consequence, Dinogunellin-A and Dinogunellin-B have the same molecular formula (C34H49N8O9P) and molecular weight (744.8 g/mol), an so do Dinogunellin-C and Dinogunellin-D (C32H47N8O9P; 718.7 g/mol).
Pharmacology
When intraperitoneally administered to mice, dinogunellins have a mean lethal dose (LD50) of 25 mg/kg.[3] Dinogunellins are also orally toxic to mice and guinea pigs and has also deleterious effects on humans.[6] A few hours after ingestion, humans develop abrupt onset diaphoresis, chills, abdominal pain and cramping, with nausea and vomiting followed by voluminous, non-bloody diarrhea.[7]
Analysis made on the cabezon toxin showed that its effects start 12 hours after administration and is characterized by several signs such as diarrhea, nasal discharge, and death.[8] In addition, cabezon toxin showed cytotoxicity on fibroblast in culture.[8][9] Besides, toxin administration causes an increase in white cell number, but with a decrease in lymphocytes associated with the observation of spleen necrosis. [9]
References
- ↑ 1.0 1.1 1.2 1.3 "Dinogunellins A-D: Putative ichthyootoxic phospholipids of northern blenny Stichaeus grigorjewi eggs". Pure and Applied Chemistry 81 (6): 1001–1008. 2009-05-05. doi:10.1351/PAC-CON-08-08-28. ISSN 1365-3075. https://www.degruyter.com/view/journals/pac/81/6/article-p1001.xml.
- ↑ 2.0 2.1 "Occurrence of a toxic phospholipid in cabezon roe". Toxicon 14 (2): 141–3. 1976. doi:10.1016/0041-0101(76)90105-7. PMID 1273860.
- ↑ 3.0 3.1 3.2 "Properties of a toxic phospholipid in the northern blenny roe". Toxicon 12 (3): 231–6. May 1974. doi:10.1016/0041-0101(74)90063-4. PMID 4458104.
- ↑ 4.0 4.1 4.2 Kamiya H, Hatano M, and Hashimoto Y. 1997. Screening of Icthyootoxin. Bulletin of the Japanese Society of Scientific Fisheries. 43(12):1461-1465.
- ↑ "Purification and Properties of a Proteinaceous Toxin Newly Found in the Roe of Lamprey Lampetra japonica". Fisheries Science 63 (1): 142–146. 1997. doi:10.2331/fishsci.63.142. https://www.jstage.jst.go.jp/article/fishsci1994/63/1/63_1_142/_article.
- ↑ "Toxicity of the roe of the cabezon, Scorpaenichthys marmoratus.". Calif Fish Game 37: 195. 1951.
- ↑ "Acute human toxicity after the ingestion of cabezon, Scorpaenichthys marmoratus, roe". Clinical Toxicology 52 (7): 820. August 2014. doi:10.3109/15563650.2014.933232. PMID 25089726.
- ↑ 8.0 8.1 "Toxins from eggs of fishes and Amphibia". Journal of Agricultural and Food Chemistry 17 (3): 417–424. May 1969. doi:10.1021/jf60163a043.
- ↑ 9.0 9.1 "Toxic effects produced by extracts of eggs of the cabezon Scorpaenichthys marmoratus". Toxicon 8 (1): 55–61. May 1970. doi:10.1016/0041-0101(70)90174-1. PMID 5465747.
External links
- Dinogunellin A (Pubchem)
- Dinogunellin B (Pubchem)
- Dinogunellin C (Pubchem)
- Dinogunellin D (Pubchem)
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