Silybin, a secondary metabolite isolated from the seeds of the blessed milk thistle (Silybum marianum) was discovered as the first member of a new family of natural compounds called flavonolignans in 1959. Over the years it has received the research attention of many organic chemists. This research has resulted in a number of semisynthetic derivatives prepared in an effort to modulate and better target the biological activities of silybin or to improve its physical properties, such as its solubility. A fundamental breakthrough in silybin chemistry was the determination of the absolute configurations of silybin A and silybin B, and the development of methods for their separation. This review covers articles dealing with silybin chemistry and also summarizes all the derivatives prepared.

Institute of Microbiology AS CR Centre of Biocatalysis and Biotransformation Vídeňská 1083 Prague 4 CZ 14220 Czech Republic

Selectively Halogenated Flavonolignans-Preparation and Antibacterial Activity

Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

Dual SMO/BRAF Inhibition by Flavonolignans from Silybum marianum †

Simple and Rapid HPLC Separation and Quantification of Flavonoid, Flavonolignans, and 2,3-Dehydroflavonolignans in Silymarin

The Effect of Silymarin Flavonolignans and Their Sulfated Conjugates on Platelet Aggregation and Blood Vessels Ex Vivo

Modulation of Skin Inflammatory Response by Active Components of Silymarin

Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Molecular Defects in Cardiac Myofilament Ca2+-Regulation Due to Cardiomyopathy-Linked Mutations Can Be Reversed by Small Molecules Binding to Troponin

European contribution to the study of ROS: A summary of the findings and prospects for the future from the COST action BM1203 (EU-ROS)

Flavonolignan 2,3-dehydrosilydianin activates Nrf2 and upregulates NAD(P)H:quinone oxidoreductase 1 in Hepa1c1c7 cells

Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties

Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

Flavonolignans As a Novel Class of Sodium Pump Inhibitors

Silibinin and its 2,3-dehydro-derivative inhibit basal cell carcinoma growth via suppression of mitogenic signaling and transcription factors activation

Regioselective alcoholysis of silychristin acetates catalyzed by lipases