title: New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties.
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(2)O(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.
authors: Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Napoli, Italy.
authors: Armando
authors: A
authors: Zarrelli
authors: Alessandro
authors: A
authors: Sgambato
authors: Valentina
authors: V
authors: Petito
authors: Lorenzo
authors: L
authors: De Napoli
authors: Lucio
authors: L
authors: Previtera
authors: Giovanni
authors: G
authors: Di Fabio
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D051381:Rats; D000077385:Silybin; D012838:Silymarin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000975:Antioxidants; D012838:Silymarin; C515097:dehydrosilybin; D000077385:Silybin