Selenoneine

Edit links
From Wikipedia, the free encyclopedia
The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.
Selenoneine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C9H15N3O2Se/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
    Key: MTIQLELFQVCRSW-ZETCQYMHSA-N
  • selenol tautomer: InChI=1S/C9H14N3O2Se/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H-,10,11,13,14)/t7-/m0/s1
    Key: FONQTPPQNMLDTP-ZETCQYMHSA-N
  • C[N+](C)(C)[C@@H](Cc1c[nH][c](=[Se])[nH]1)C([O-])=O
  • selenol tautomer: C[N+](C)(C)[C@@H](CC1=CN=C(N1)[Se])C(=O)[O-]
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).

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; Hossain, Md. Anwar; Yabu, Takeshi; Touhata, Ken (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. Bibcode:2013MarBt..15..559Y. doi:10.1007/s10126-013-9508-1. PMC 3742965. PMID 23709046. S2CID 7805355.
  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. PMC 2881734. 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. Bibcode:2019Chmsp.229..549A. doi:10.1016/j.chemosphere.2019.04.191. hdl:20.500.11794/38377. ISSN 0045-6535. PMID 31100626.
  4. ^ a b c El Hanafi, Khouloud; Pedrero, Zoyne; Ouerdane, Laurent; Marchán Moreno, Claudia; Queipo-Abad, Silvia; Bueno, Maite; Pannier, Florence; Corns, Warren T.; Cherel, Yves; Bustamante, Paco; Amouroux, David (1 March 2022). "First Time Identification of Selenoneine in Seabirds and Its Potential Role in Mercury Detoxification" (PDF). Environmental Science & Technology. 56 (5): 3288–3298. Bibcode:2022EnST...56.3288E. doi:10.1021/acs.est.1c04966. PMID 35170956. S2CID 246865626.
  5. ^ a b 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. S2CID 31792266.
  6. ^ Kim, Se-Kwon (21 January 2015). Springer Handbook of Marine Biotechnology. Springer. p. 1063. ISBN 978-3-642-53971-8.
  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. Bibcode:2022Natur.610..199K. doi:10.1038/s41586-022-05174-2. PMID 36071162. S2CID 252120205.
  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. PMC 3844148. 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. Bibcode:2019EnInt.127..243L. doi:10.1016/j.envint.2018.11.077. hdl:20.500.11794/38343. 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. S2CID 231702745.
  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. S2CID 42340594.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Selenoneine&oldid=1218503059"