Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
7584864 | Food Chemistry | 2018 | 9 Pages |
Abstract
Rocket is rich in glucosinolates and valued for its hot and spicy taste. Here we report the structure elucidation, bioactivity, and stability of the mainly formed glucosinolate hydrolysis product, namely sativin, which was formerly thought to be 4-mercaptobutyl isothiocyanate. However, by NMR characterization we revealed that sativin is in fact 1,3-thiazepane-2-thione, a tautomer of 4-mercaptobutyl isothiocyanate with 7-membered ring structure and so far unknown. This finding was further substantiated by conformation sampling using molecular modeling and total enthalpy calculation with density functional theory. During aqueous heat treatment sativin in general was quite stable, while the isothiocyanates erucin and sulforaphane were labile, having half-lives of 132â¯min and 56â¯min (pH 5, 100â¯Â°C), respectively. Moreover, using a WST-1 assay, we found that sativin did not reduce cell viability of HepG2 cells in a range of 0.3-30â¯ÂµM, and, therefore, exhibited no cytotoxic effects in this cell line.
Related Topics
Physical Sciences and Engineering
Chemistry
Analytical Chemistry
Authors
Jana Fechner, Martin Kaufmann, Corinna Herz, Daniela Eisenschmidt, Evelyn Lamy, Lothar W. Kroh, Franziska S. Hanschen,