Glucoalyssin is an organic compound belonging to the group of glucosinolates, naturally found in cruciferous vegetables. It is structurally similar to glucoberteroin, which contains a thioether unit in the side chain rather than a sulfoxide unit.
Occurrence.
Glucoalyssin was first isolated in the 1950s from "Alyssum argenteum". It is also present in other species of the genus stonecrop ("Alyssum"), such as "Alyssum montanum" and "Alyssum alyssoides". It generally occurs alongside smaller quantities of glucoberteroin, which is likely also the biosynthesis precursor of glucoalyssin. It is not present as a racemate but in a specific angle of rotation, existing as -(-)-glucoalyssin. In "Degenia velebitica", glucoalyssin coexists with glucoberteroin, primarily concentrated in the stems and leaves, whereas the seeds mainly contain glucoberteroin. A genetic study examined the formation of mustard oil glycosides with aliphatic side chains and their derivatives in "rapeseed" and other "Brassica" species. The study suggests that a specific gene locus determines side-chain length, with methionine chain elongation likely producing glucoiberverine (C3), glucoerucin (C4), and glucoberteroin (C5). These compounds serve as precursors to compounds with sulfoxide or alkene side chains. For C5 side chains, this includes glucoalyssin and glucobrassicanapin.
Properties.
As a mustard oil glycoside, glucoalyssin can release a corresponding isothiocyanate, alyssin.
References.
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