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Separation and Purification of (−)Schisandrin B from Schisandrin B Stereoisomers

Ka F. Luk1, Robert Kam M. Ko2, and Ka M. Ng1. (1) Department of Chemical Engineering, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China, (2) Department of Biochemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China

Schisandrin B (Sch B), consisting of a mixture of its stereoisomers, namely (−)Sch B and (±)g-schisandrin, is the most abundant and biologically active dibenzocyclooctadiene lignan present in Fructus Schisandrae (FS). Among the stereoisomers of Sch B in FS, (−)Sch B was found to produce more potent enhancing effect on cellular glutathione and protection against oxidative injury in both cultured cardiomyocytes and hepatocytes. Therefore, it is desirable to recover (−)Sch B in a purified form to achieve the highest bioactivities.

The objective of this study is to develop a process for large-scale separation and purification of (−)Sch B from the Sch B stereoisomeric mixture. To this end, a crystallization-based separation and purification process has been conceptualized. Bench-scale crystallization experiments guided by experimental solid-liquid equilibrium phase diagrams were performed to verify process feasibility. A (−)Sch B product with a purity of 98.5 wt% and a (±)g-schisandrin-enriched product with a purity of 65.0 wt% were obtained. The (−)Sch B product caused a 32% increase in cellular glutathione level and the (±)g-schisandrin-enriched product a 26% increase, indicating a potentially more efficacious pharmaceutical preparation.