Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Napoli, Italy.
Bioorg Med Chem Lett. 2011 Aug 1;21(15):4389-92. doi: 10.1016/j.bmcl.2011.06.049. Epub 2011 Jun 17.
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.
水飞蓟宾是水飞蓟素中的主要黄酮木脂素，具有多种生物学效应，通常归因于其抗氧化特性。本文将描述一种有效的合成策略，以获得各种新的、水溶性更好的水飞蓟宾和 2,3-脱水水飞蓟宾（DHS）衍生物，其中 23-羟基被转化为硫酸盐、磷酸二酯或胺基，采用溶液相方法。此外，还开发并优化了一种从水飞蓟宾制备 DHS 的新方法。在体内细胞模型中评价了新化合物的抗氧化特性，它们显示出与水飞蓟宾和 DHS 相当或更高的抗氧化活性，能够防止 H(2)O(2)诱导的细胞内活性氧（ROS）的产生。大多数衍生物还表现出更好的亲水性，同时保留了水飞蓟宾的生物活性，它们可能拓宽了这类天然化合物的体内应用。
