PURIFICATION OF THE OMEGA-(METHYLSULFINYL)ALKYL GLUCOSINOLATE HYDROLYSIS PRODUCTS - 1-ISOTHIOCYANATO-3-(METHYLSULFINYL)PROPANE, 1-ISOTHIOCYANATO-4-(METHYLSULFINYL)BUTANE, 4-(METHYLSULFINYL)BUTANENITRILE, AND 5-(METHYLSULFINYL)PENTANENITRILE FROM BROCCOLI AND LESQUERELLA-FENDLERI

The purification of the omega-(methylsulfinyl)alkyl glucosinolate hydrolysis products 1-isothiocyanato-3-(methylsulfinyl)propane (IMSP), 1-isothiocyanato-4-(methylsulfinyl)butane (IMSB), 4-(methylsulfinyl)-butanenitrile (MSBN), and 5-(methylsulfinyl)pentanenitrile (MSPN) from the seeds of broccoli and Lesquerella fendleri (Gray) S. Watson is described. The procedure uses solvent extraction of autolyzed defatted seed meals, followed by purification of the hydrolysis products using gel filtration chromatography and reversed-phase high-performance liquid chromatography (HPLC). Purity and confirmation of the compounds were monitored and verified using gas chromatography with flame ionization detection (GC-FID), thin-layer chromatography (TLC), gas chromatography-mass spectroscopy (GC-MS), and nuclear magnetic resonance (NMR). The techniques are useful for the preparative-scale isolation of structurally related glucosinolate hydrolysis products arising from omega-(methylsulfinyl)alkyl glucosinolates and should facilitate more extensive studies into the biological effects of these naturally occurring compounds.