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