Synthesis and Structure–Activity Relations in Allylsulfide and Isothiocyanate Compounds From Garlic and Broccoli Against In Vitro Cancer Cell Growth
2016
Kaschula, Catherine H. | Hunter, Roger
The edible plants garlic (Allium sativum) and broccoli (Brassica olevacea) are rich in sulfur-containing compounds that are reported to offer protection against a number of diseases, including cancer. These compounds have a sulfide, polysulfide, thiosulfinate, or isothiocyanate functional group that is proposed to be the bioactive pharmacophore. Specific bioactive compounds commonly studied from garlic and broccoli includes allicin, ajoene, diallyl trisulfide, sulforaphane, and phenyl isothiocyanate. Herein we review the biosynthesis of these compounds in the plant as well as current synthetic approaches to these compounds and their derivatives in the laboratory. Both allylsulfides and isothiocyanates are electrophilic, able to react with cysteine sulfhydryl groups in peptides or proteins to form mixed disulfides and dithiocarbamates, respectively, in which the resultant lowering of glutathione levels and posttranslational modification of specific protein targets is proposed to trigger a number of biological outcomes. Herein we also summarize the current understanding behind the synthesis, chemistry, and protein targets of allylsulfides and isothiocyanates and their derivatives in cancer cells.
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