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Selenoneine

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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

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  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.
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