Sulforaphane nitrile

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. 

Sulforaphane nitrile (R(CN)-N=C = S) Pro-inflammatory protein synthesis blockage (For many inhibitors of NFKB-mediated iNOS COX expression see Tables 7.3 8.1) From Glucoraphanin Induces GST, NADPH quinone reductase [indirect AO] 14.4B... 

Chiang WCK, Pusateri DJ, Leitz REA. Gas chromatography/mass spectrometry method for the determination of sulforaphane and sulforaphane nitrile in broccoli. J Agric Food Chem 1998 46 1018-1021. 

Matusheski NV, Wallig MA, Juvik JA, Klein BP, Kushad MM, Jeffery EH. Preparative HPLC method for the purification of sulforaphane and sulforaphane nitrile from Brassica oleracea. J Agric Food Chem 2001 49 1867-1872. 

GSL aglycones may yield a nitrile rather than an ITC under certain conditions, like a low pH and the presence of a protein similar to the epithiospecifier protein (ESP) that has been characterized in B. napus and Arabidopsis thaliana (Lambrix etal 2001 Matusheski etal 2004 Neugart et al. 2012). The production of nitriles as opposed to ITC impacts negatively on the anticancer potential of these vegetables. It appears that ITCs are more potent inducers compared to allyl nitriles and their activity is expressed in a wider range of tissues (Tanii etal. 2005). However, few works have studied the chemopreventive effect of GSL-derived nitriles. Among the known cruciferous nitriles, the most studied are nitrile crambene, sulforaphane nitrile, and allyl nitrile. 

Basten, G.P., Bao, Y. and Williamson, G. (2002) Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGTIAI) and glutathione transferase (GSTAl) in cultured cells. Carcinogenesis, 23, 1399-1404. 

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. 

---