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 H 2O 2-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.
New C-23 modified of silybin and 2,3-dehydrosilybin: Synthesis and preliminary evaluation of antioxidant properties / Zarrelli, Armando; Sgambato, Alessandro; Petito, Valentina; DE NAPOLI, Lorenzo; Previtera, Lucio; DI FABIO, Giovanni. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - 21:15(2011), pp. 4389-4392. [10.1016/j.bmcl.2011.06.049]
New C-23 modified of silybin and 2,3-dehydrosilybin: Synthesis and preliminary evaluation of antioxidant properties
ZARRELLI, ARMANDO;DE NAPOLI, LORENZO;PREVITERA, LUCIO;DI FABIO, GIOVANNI
2011
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 H 2O 2-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.File | Dimensione | Formato | |
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2-2011. BMCL 4389-4392. Silibine modificate.pdf
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