Selenoneine

Last updated
Selenoneine
Selenoneine.png
Names
IUPAC name
(2-selenyl-Nα,Nα,Nα-trimethyl-L-histidine or 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • 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 (SEN) is a selenium-containing ergothioneine derivative where the selenium (Se) atom replaces a sulfur atom. It is made by microorganisms and is concentrated by vertebrates higher up in the food chain. It is mainly found in marine environments. [1]

Contents

Occurrence

Selenoneine is made by microorganisms and concentrated by vertebrates, mainly marine vertebrates, into their bodies. In vertebrates, selenoneine is transported into cells using OCTN1. [1]

It is found in the blood of bluefin tuna, [2] [3] and other sea-dwelling animals like turtles, mackerel, beluga, [4] and giant petrels. [1] It is found in seabirds. [1]

Humans that eat fish have selenoneine in their blood. In populations that eat a lot of fish (Japanese remote islanders and Inuit), about half of selenium found in their blood is in the form of selenoneine. [5] [6]

Function

It is an antioxidant with the ability to react with reactive oxygen species. [7] It also boosts the action of GPx1. [8]

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. [1]

Selenoneine inhibits angiotensin-converting enzyme. [9]

Biosynthesis

Selenoneine is produced by microorganisms using enzymes that form a selenium-carbon bond. [10] Specifically it can be made when the biosynthetic machinery for ergothioneine uses selenocysteine instead of cysteine. [11]

It can also be made using a specialized biosynthetic cluster senABC in bacteria, where senA is homologous to the hercynine oxygenase egtB in ergothioneine biosynthesis and senC is homologous to the selenophosphate synthetase selD. senA combines hercynine and a selenosugar together. The hercynine is made by egtD, a gene from the ergothioneine pathway. The selenosugar is made by senB using a UDP-sugar and a selenophosphate ion made by senC. [12] The crystal structures of selA and senB were solved in 2024. [13]

Derivatives

A related derivative, Se-methylselenoneine (MeSEN) is found in lesser quantities in mackerel, sardine and tuna. MeSEN is the major metabolized form of SEN in mammals, [14] being mainly excreted in urine. SEN's metabolism stands in contrast with other dietary sources of selenium such as selenite, SeMet, and SeCys, which are instead metabolized to selenide and then excreted as a selenosugar or as trimethylselenonium. [15]

In air selenoneine is easily oxidised to a dimer containing a diselenide bond (Se–Se). [7]

References

  1. 1 2 3 4 5 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.
  2. ↑ 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.
  3. ↑ 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. Bibcode:2010JBiCh.28518134Y. doi: 10.1074/jbc.C110.106377 . PMC   2881734 . PMID   20388714.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. 1 2 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. Archived from the original on 2022-09-09. Retrieved 2022-09-09.
  8. ↑ Kim, Se-Kwon (21 January 2015). Springer Handbook of Marine Biotechnology. Springer. p. 1063. ISBN   978-3-642-53971-8.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ Pluskal T, Ueno M, Yanagida M (2014). "Genetic and metabolomic dissection of the ergothioneine and selenoneine biosynthetic pathway in the fission yeast, S. pombe, and construction of an overproduction system". PLOS ONE. 9 (5) e97774. Bibcode:2014PLoSO...997774P. doi: 10.1371/journal.pone.0097774 . PMC   4020840 . PMID   24828577.
  12. ↑ Kayrouz, CM; Huang, J; Hauser, N; Seyedsayamdost, MR (October 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.
  13. ↑ Xu, S; Zhao, J; Liu, X; Yang, X; Xu, Z; Gao, Y; Ma, Y; Yang, H (30 June 2024). "Structures of SenB and SenA enzymes from Variovorax paradoxus provide insights into carbon-selenium bond formation in selenoneine biosynthesis". Heliyon. 10 (12) e32888. Bibcode:2024Heliy..1032888X. doi: 10.1016/j.heliyon.2024.e32888 . PMC   11237966 . PMID   38994077.
  14. ↑ 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. Bibcode:2015ABiCh.407.7713K. doi:10.1007/s00216-015-8936-3. PMID   26253229. S2CID   42340594.
  15. ↑ Seko, Takuya; Yamashita, Yumiko; Yamashita, Michiaki (2025). "Overview of the biochemistry and biology of selenoneine". Metallomics Research. 5. doi:10.11299/metallomicsresearch.MR202414.
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