New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties |
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Authors: | Zarrelli Armando Sgambato Alessandro Petito Valentina De Napoli Lorenzo Previtera Lucio Di Fabio Giovanni |
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Affiliation: | a Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli ‘Federico II’, Complesso Universitario di Monte S. Angelo, via Cintia 4, 80126 Napoli, Italy b Centro di Ricerche Oncologiche ‘Giovanni XXIII’ - Istituto di Patologia Generale, Università Cattolica, Largo Francesco Vito 1, 00168 Roma, Italy |
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Abstract: | Silybin is the major flavonolignan of silymarin and it displays a plethora of biological effects, generally ascribed to its antioxidant properties. Herein we shall describe an efficient synthetic strategy to obtain a variety of new and more water-soluble silybin and 2,3-dehydrosilybin (DHS) derivatives in which the 23-hydroxyl group was converted to a sulfate, phosphodiester, or amine group, using a solution-phase approach. Furthermore a new and efficient method for the preparation of DHS from silybin was developed and optimised.The antioxidant properties of the new compounds were evaluated in a cellular model in vivo and they displayed an antioxidant activity comparable to or higher than silybin and DHS, being able to prevent H2O2-induced generation of intracellular reactive oxygen species (ROS). Most of the derivatives also displayed a better hydrophilicity while retaining the biological activities of silybin and they might broaden the in vivo applications of this class of natural compounds. |
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Keywords: | Flavonolignans Silybin Dehydrosilybin Antioxidants DCFH-DA assay |
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