Large-scale separation of silybin diastereoisomers using lipases

• Published in: Process Biochemistry
• Main Authors: Gažák, R. (Radek), Marhol, P. (Petr), Purchartová, K. (Kateřina), Monti, D., Biedermann, D. (David), Riva, S., Cvak, L., Křen, V. (Vladimír)
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2010
• Subjects: Silybin A; silymarin; silibinin; Antarc*; Antarctica
• Online Access: https://doi.org/10.1016/j.procbio.2010.06.019; http://hdl.handle.net/11104/0188740

The flavonolignan silybin (1), isolated from the seeds of milk thistle (Silybum marianum), occurs in nature as an equimolar mixture of two diastereoisomers, silybin A and silybin B, that exhibit different biological activities. The preparative production of optically pure silybin A and B in a diastereoisomeric purity greater than 95 percent was accomplished using immobilized Candida antarctica lipase B (Novozym 435) in a combination of two reactions: regioselective acetylation of a natural silybin mixture (1) and subsequent stereoselective alcoholysis of the resulting 23-O-acetylsilybin (2). Several grams of the optically pure substances can be produced within one week using this new, robust and scalable process, which is selective, mild and high-yielding