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Sisymbrium officinale (L.) Scop: glucosinolate profile and synthesis of isopropyl isothiocyanate

Hedge mustard (Sisymbrium officinale (L.) Scop.), a plant from Brassicaceae family, was collected in Split and in the Krka River area during May 2019. The aim of the study was to isolate and identify glucosinolates (GSLs) and their breakdown products. Different isolation methods have been applied in this work: hydrodistillation in the modified Clevenger apparatus, autolysis, and microwave-assisted distillation and microwave hydrodiffusion and gravity. GC-MS analysis of the volatile isolates indicated that the most abundant volatile product was isopropyl isothiocyanate (ITC), originated from glucoputranjivin degradation. GSLs were also identified and quantified by their desulfo counterparts using HPLC-DAD analysis in different plant parts (root, stem, leaf, flower). Three GSLs were identified in all plant parts: glucoputranjivin (0.68-16.00 µmol/g DW), 4-hydroxyglucobrassicin (0.04-2.73 µmol/g DW) and glucobrassicin (0.24- 6.40 µmol/g DW). Furthermore, glucosinalbin, 4- methoxyglucobrassicin and neoglucobrassicin were also identified in the roots. In order to investigate biological properties (cytotoxic and antiviral), isopropyl ITC was synthesized by one-pot synthesis by reaction of isopropyl amine with CS2 in aqueous K2CO3 solution affording the dithiocarbamate intermediate, which was further desulfurized by adding cyanuric acid at 0 °C to provide the corresponding ITC. After purification with petroleum ether, the ITC was confirmed by GC-MS and spectroscopic techniques.

Sisymbrium officinale ; glucosinolates ; isopropyl isothiocyanate ; synthesis ; antiviral activity ; cytotoxic activity

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