Sulforaphane bioactivity

Biocatalytic access to both antipodal sulfoxides was exploited in total syntheses of bioactive compounds, which is outlined in some representative examples. Biooxidation of functionalized dialkyl sulfides was utilized in the direct synthesis of both enantiomers of sulforaphane and some analogs in low to good yields and stereoselectivities (Scheme 9.27) [206]. This natural product originates from broccoli and represents a potent inducer of detoxification enzymes in mammalian metabolism it might be related to anticarcinogenic properties of plants from the cruciform family. All four possible stereoisomers of methionine (R = Me) and ethionine sulfoxides... 

MATUSHESKL N.V., JEFFERY, E.H., Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile., J. Agric. Food Chem., 2001,49,5743-5749. 

Recently, it has been found that, in addition to its detoxification function and its function as a biomarker for up-regulation of other phase II enzymes, up-regulation of quinone reductase by monofunctional inducers may play a role in the stabilization of p53, the protein product of a tumor suppressor gene, which induces growth arrest and apoptosis. Sulforaphane has also been shown to mediate growth arrest and induce cell cycle arrest and apoptosis in many cancer cell lines, including those of human prostate, colon, and T-cell leukemia origin. - The exact mechanisms, and whether all the bioactivities of sulforaphane involve the ARE, are not yet understood. 

Keck, A.S., Qiao, Q., and Jeffery, E.H., Food matrix effects on the bioactivity of broccoli-derived sulforaphane in liver and colon of F344 rats, J. Agric. Food Chem., 51, 3320-3327, 2003. 

Keck, A.S., Staack, R., and Jeffery, E.H., The cruciferous nitrile crambene has bioactivity similar to sulforaphane when administered to Fischer 344 rats but is far less potent in cell culture, Nutr. Cancer, 42, 233-240, 2002. 

The use of GSLs and their derivatives in functional food products and pharmaceuticals may provide additional routes for the exploitation of these attractive natural plant products. In the last few years, pharmaceutical forms (pills, powders, capsules, vials, etc.) containing GSLs as food bioactive compounds (especially broccoli extracts that provide sulforaphane and other phytochemicals) have appeared in the market. Among them it is possible to find capsules with sulforaphane, with indole-3-carbinol and capsules made from a cruciferous mix. 

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