A bioinspired look at the glucosinolate metabolic pathway. Structural insights into the reaction of benzyl isothiocyanate and d-glucosamine

Through a well-established enzymatic transformation glucosinolates release reactive isothiocyanates that can undergo further metabolic pathways affording a plethora of reactive metabolites. This study explores in detail the reaction of benzyl isothiocyanate, which possesses antitumor activity as alkylating agent, with d-glucosamine, commonly employed in oral treatments against osteoarthritis and inflammation. Structures of the resulting products and their evolution have been assessed and compared with those involving d-glucose, reported previously. Chemical results suggest that clinical treatments with d-glucosamine could reduce the beneficial effects associated with diets based on glucosinolate-rich foods.

All products and reaction mechanism of BITC (an inhibitor of carcinogenesis from glucosinolate hydrolysis) with d-glucosamine (an anti-inflammatory agent) have been characterized.