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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, and other sea dwelling animals like turtles, mackerel, Beluga whale, and . It is an antioxidant, combining with reactive oxygen species and boosting the action of GPx1.
Selenoneine is produced by microorganisms using enzymes that form a selenium-carbon bond. Humans that eat fish have selenoneine in their blood. About half of selenium is in the form of selenoneine. Selenoneine inhibits angiotensin-converting enzyme. In vertebrates, selenoneine is transported into cells using OCTN1. 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. A related derivative, Se-methylselenoneine is found in lesser quantities in mackerel, sardine and tuna.
In air selenoneine is easily oxidised to a dimer containing a diselenide bond (Se-Se).
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