Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, Prague 4, CZ 14220, Czech Republic.
Nat Prod Rep. 2022 Jun 22;39(6):1264-1281. doi: 10.1039/d2np00013j.
Covering: 2015 up to 2022 (Feb)Silymarin, an extract of milk thistle () fruits, has been used in various medicinal applications since ancient times. A major component of silymarin is the flavonolignan silybin and its relatives isosilybin, silychristin, silydianin, 2,3-dehydrosilybin, and some others. Except for silydianin, they occur in nature as two stereomers. This review focuses on recent developments in chemistry, biosynthesis, modern advanced analytical methods, and transformations of flavonolignans specifically reflecting their chirality. Recently described chemotypes of , but also the newest findings regarding the pharmacokinetics, hepatoprotective, antiviral, neuroprotective, and cardioprotective activity, modulation of endocrine functions, modulation of multidrug resistance, and safety of flavonolignans are discussed. A growing number of studies show that the respective diastereomers of flavonolignans have significantly different activities in anisotropic biological systems. Moreover, it is now clear that flavonolignans do not act as antioxidants , but as specific ligands of biological targets and therefore their chirality is crucial. Many controversies often arise, mainly due to the non-standard composition of this phytopreparation, the use of various undefined mixtures, the misattribution of silymarin silybin, and also the failure to consider the chemistry of the respective components of silymarin.
2015 年至 2022 年（2 月）水飞蓟素，一种从奶蓟草（）果实中提取的物质，自古以来就在各种药用应用中使用。水飞蓟素的主要成分是黄酮木脂素水飞蓟宾及其类似物水飞蓟宾、水飞蓟宁、水飞蓟丁、2,3-脱水水飞蓟宾等。除了水飞蓟丁，它们在自然界中以两种立体异构体的形式存在。本文综述了黄酮木脂素化学、生物合成、现代先进分析方法以及转化的最新进展，特别反映了它们的手性。最近描述的水飞蓟素化学型，以及关于黄酮木脂素的药代动力学、肝保护、抗病毒、神经保护和心脏保护活性、内分泌功能调节、多药耐药性调节以及安全性的最新发现也进行了讨论。越来越多的研究表明，黄酮木脂素的各自非对映异构体在手性生物系统中具有明显不同的活性。此外，现在很清楚，黄酮木脂素不是作为抗氧化剂，而是作为生物靶标的特定配体，因此它们的手性至关重要。经常出现许多争议，主要是由于这种植物制剂的成分不标准，使用各种未定义的混合物，对水飞蓟素的水飞蓟宾的错误归因，以及未能考虑水飞蓟素的各个成分的化学性质。
