Chemistry:Selenoneine

From HandWiki
Selenoneine
Selenoneine.png
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
Properties
C9H14N3O2Se
Molar mass 275.201 g·mol−1
Related compounds
Related compounds
 Selenocysteine; Ergothioneine; Histidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Selenoneine is a selenium containing ergothioneine derivative where the selenium (Se) atom replaces a sulfur atom. It can be systematically named as (2-selenyl-Nα,Nα,Nα-trimethyl-L-histidine or 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate).

It is found in the blood of bluefin tuna,[1][2] and other sea dwelling animals like turtles, mackerel, beluga,[3] and giant petrels.[4] It is an antioxidant,[5] combining with reactive oxygen species and boosting the action of GPx1.[6]

Selenoneine is produced by microorganisms using enzymes that form a selenium-carbon bond.[7] Humans that eat fish have selenoneine in their blood. About half of selenium is in the form of selenoneine.[8] [9] Selenoneine inhibits angiotensin-converting enzyme.[10] In vertebrates, selenoneine is transported into cells using OCTN1.[4] Selenoneine reacts with methyl mercury to form a mercury tetraselenoate complex, which degrades to tiemannite, a mercury selenide. This is a mechanism used to detoxify mercury in marine vertebrates.[4] A related derivative, Se-methylselenoneine is found in lesser quantities in mackerel, sardine and tuna.[11]

In air selenoneine is easily oxidised to a dimer containing a diselenide bond (Se-Se).[5]

References

  1. ↑ Yamashita, Michiaki; Yamashita, Yumiko; Suzuki, Tamami; Kani, Yoko; Mizusawa, Nanami; Imamura, Shintaro; Takemoto, Kenji; Hara, Tatsuro et al. (October 2013). "Selenoneine, a Novel Selenium-Containing Compound, Mediates Detoxification Mechanisms against Methylmercury Accumulation and Toxicity in Zebrafish Embryo". Marine Biotechnology 15 (5): 559–570. doi:10.1007/s10126-013-9508-1. PMID 23709046. 
  2. ↑ Yamashita, Yumiko; Yamashita, Michiaki (June 2010). "Identification of a Novel Selenium-containing Compound, Selenoneine, as the Predominant Chemical Form of Organic Selenium in the Blood of Bluefin Tuna". Journal of Biological Chemistry 285 (24): 18134–18138. doi:10.1074/jbc.C110.106377. PMID 20388714. 
  3. ↑ Achouba, Adel; Dumas, Pierre; Ouellet, Nathalie; Little, Matthew; Lemire, Mélanie; Ayotte, Pierre (2019-08-01). "Selenoneine is a major selenium species in beluga skin and red blood cells of Inuit from Nunavik". Chemosphere 229: 549–558. doi:10.1016/j.chemosphere.2019.04.191. ISSN 0045-6535. PMID 31100626. 
  4. ↑ 4.0 4.1 4.2 El Hanafi, Khouloud; Pedrero, Zoyne; Ouerdane, Laurent; Marchán Moreno, Claudia; Queipo-Abad, Silvia; Bueno, Maite; Pannier, Florence; Corns, Warren T. et al. (1 March 2022). "First Time Identification of Selenoneine in Seabirds and Its Potential Role in Mercury Detoxification". Environmental Science & Technology 56 (5): 3288–3298. doi:10.1021/acs.est.1c04966. PMID 35170956. https://hal-univ-pau.archives-ouvertes.fr/hal-03591549/file/Manuscript.pdf. 
  5. ↑ 5.0 5.1 Gammelgaard, Bente; Jackson, Matthew I.; Gabel-Jensen, Charlotte (February 2011). "Surveying selenium speciation from soil to cell—forms and transformations". Analytical and Bioanalytical Chemistry 399 (5): 1743–1763. doi:10.1007/s00216-010-4212-8. PMID 20953781. https://pubag.nal.usda.gov/download/58220/pdf. 
  6. ↑ Kim, Se-Kwon (21 January 2015) (in en). Springer Handbook of Marine Biotechnology. Springer. p. 1063. ISBN 978-3-642-53971-8. https://books.google.com/books?id=Z-tVBgAAQBAJ&pg=PA1063. 
  7. ↑ Kayrouz, Chase M.; Huang, Jonathan; Hauser, Nicole; Seyedsayamdost, Mohammad R. (7 September 2022). "Biosynthesis of selenium-containing small molecules in diverse microorganisms". Nature 610 (7930): 199–204. doi:10.1038/s41586-022-05174-2. PMID 36071162. 
  8. ↑ Yamashita, Michiaki; Yamashita, Yumiko; Ando, Tetsuo; Wakamiya, Junji; Akiba, Suminori (December 2013). "Identification and Determination of Selenoneine, 2-Selenyl-N α , N α , N α -Trimethyl-l-Histidine, as the Major Organic Selenium in Blood Cells in a Fish-Eating Population on Remote Japanese Islands". Biological Trace Element Research 156 (1–3): 36–44. doi:10.1007/s12011-013-9846-x. PMID 24197605. 
  9. ↑ Little, Matthew; Achouba, Adel; Dumas, Pierre; Ouellet, Nathalie; Ayotte, Pierre; Lemire, Mélanie (2019-06-01). "Determinants of selenoneine concentration in red blood cells of Inuit from Nunavik (Northern Québec, Canada)". Environment International 127: 243–252. doi:10.1016/j.envint.2018.11.077. ISSN 0160-4120. PMID 30928848. 
  10. ↑ Gröber, Uwe; Holick, Michael F. (2021). "The coronavirus disease (COVID-19) – A supportive approach with selected micronutrients". Int J Vitam Nutr Res 92 (1): 13–34. doi:10.1024/0300-9831/a000693. PMID 33487035. 
  11. ↑ Kroepfl, Nina; Jensen, Kenneth B.; Francesconi, Kevin A.; Kuehnelt, Doris (October 2015). "Human excretory products of selenium are natural constituents of marine fish muscle". Analytical and Bioanalytical Chemistry 407 (25): 7713–7719. doi:10.1007/s00216-015-8936-3. PMID 26253229. 



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