Two novel inclusion complexes of colon cancer chemopreventers, Auraptene and 4'-Geranyloxyferulic acid
In recent years we have demonstrated that two prenyloxyphenylpropanoids, namely the geranyloxycoumarin auraptene, widespread in edible fruits of plants belonging to the genus Citrus, and 4'-geranyloxyferulic acid, extracted from the Australian shrub Acronychia baueri Schott (Rutaceae), exert valuable effects as dietary feeding colon cancer chemopreventive agents.1 The same was seen for the well known iNOS inhibitor N-nitro-L-arginine methyl ester (L-NAME).2 As a continuation of our studies about physico-chemical and pharmacological properties of cyclodextrin-inclusion compounds of prenyloxyphenylpropanoids, we describe herein the synthesis and structural characterization of complexes between auraptene, 4'-geranyloxyferulic acid, each coupled to L-NAME, and β-cyclodextrin to be used as novel prodrugs of the title cancer chemopreventers.
1. Tanaka, T.; de Azevedo M.B.; Durán, N.; Alderete, J.B.; Epifano, F.; Genovese, S.; Tanaka, M.; Tanaka, T.; Curini, M. Int. J. Cancer, 2010, 126, 830, 2. Yu, L.B.; Dong, X.S.; Sun, W.Z.; Zhao, D.L.; Yang, Y. World J. Gastroenterol. 2005, 11, 6385.