Ionic thiocyanate (SCN-) production from 4-hydroxybenzyl glucosinolate contained in Sinapis alba seed meal

Abstract

Meal produced from Sinapis alba seed by crushing to remove oil contains a glucosinolate that when hydrolyzed produces phytotoxic allelochemicals; however, the responsible compounds and pathways for their production have not been elucidated. S. alba seed meal and partially purified extracts containing 4-hydroxybenzyl glucosinolate were included in experiments to identify and monitor enzymatically released products using GC-MS and HPLC-MS. The initial product, 4-hydroxybenzyl isothiocyanate, was unstable in aqueous media, showing a half-life of 321 min at pH 3.0, decreasing to 6 min at pH 6.5. More alkaline pH values decrease the stability of 4-hydroxybenzyl isothiocyanate by promoting the formation of a proposed quinone that hydrolyzes to SCN-. Measurement of SCN- showed stoichiometric release from S. alba meal at 48 h when buffered at pH values as low as 4.0, demonstrating that SCN - production in soil is not only probable but likely responsible for observed phytoxicity of the meal. © 2005 American Chemical Society.