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J Nat Prod. 2010 Apr 23;73(4):613-9. doi: 10.1021/np900758d.

Enzymatic kinetic resolution of silybin diastereoisomers.

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Istituto di Chimica del Riconoscimento Molecolare, CNR, Via Mario Bianco 9, I-20131 Milano, Italy.


In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transesterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.

[Indexed for MEDLINE]

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