ARS | Publication request: ISOLATION AND PURIFICATION OF NITRILES AND ISOTHIOCYANATES, PRODUCTS OF GLUCOSINOLATE DEGRADATION

Submitted to: Phytochemical Society of North America Meeting and Newsletter
Publication Type: Abstract
Publication Acceptance Date: August 13, 2003
Publication Date: N/A

Technical Abstract: The crucifer family, Brassicaceae, is an economically important family for its many food crops. Crucifers are characterized by the presence of a group of secondary compounds called glucosinolates, which with their degradation products are primarily responsible for the characteristic aromas and flavors of crucifers. Glucosinolate degradation products include substituted isothiocyanates, nitriles, thiocyanates, epithionitriles and oxazolidinethiones, which vary depending on the plant species studied, side-chain substitution, cell pH and cell iron concentration. Many of these degradation products have biological activity ranging from insect attractants to suspected human health benefits, but are not commercially available. We have developed methods for isolation and purification of several of these degradation products, including the isothiocyanates erucin, iberin, cheirolin, hesperin, and lesquerellin (as well as most of the corresponding nitriles) using seed from several different genera within the Brassicaceae as the source of parent glucosinolates. By manipulating seed source, reaction conditions (e.g. temperature, pH) and through solvent partitioning, relatively pure (>95%) compounds can be isolated without necessitating any chromatographic separation.