A Rapid and Simple Chromatographic Separation of Diastereomers of Silibinin and Their Oxidation to Produce 2,3-Dehydrosilybin Enantiomers in an Optically Pure Form

作者：Di Fabio Giovanni; Romanucci Valeria; Di Marino Cinzia; De Napoli Lorenzo; Zarrelli Armando^*

来源：Planta Medica, 2013, 79(12): 1077-1080.

DOI：10.1055/s-0032-1328703

• prep-RP-HPLC
• flavonolignans
• Silybum marianum
• Asteraceae
• silibinin
• silybin A
• silybin B
• 2
• 3-dehydrosilybin

Silybin A and B were separated from commercial silibinin using the preparative HPLC method. The described method is rapid and effective in obtaining gram-scale amounts of two diastereoisomers with minimal effort. In our approach, silibinin was dissolved in THF (solubility greater than 100 mg/mL), an alternative solvent to H2O or MeOH in which silibinin has a very low solubility (ca 0.05-1.5mg/mL), and then separated into its two components using preparative RP-HPLC. By starting with purified diastereoisomers, it was possible to obtain the two enantiomers of 2,3-dehydrosilybin in good yields and optically pure using an efficient oxidation procedure. All of the purified products were fully characterised using NMR (H-1, C-13), CD, [alpha](D), and ESI MS analyses. The purities of the products, which were evaluated using analytical HPLC, were greater than 98% in all cases.

• 出版日期2013-8