Extraction and separation of pinosylvins by Centrifugal Partition Chromatography

Pinosylvins are stilbenoid toxins available in the heartwood and knots of Pinaceae, protecting them from microbiological attacks [1]. Extraction of pinosylvins can be easily realized from chopped knots, a less expensive byproduct of wood production, by well-known extraction techniques using non-chlorinated solvents. However chromatographic separation is needed to separation pinosylvin from methyl-ethers and other impurities. Our goal of research was to find an economic method for production of pure pinosylvin for further studies, alternative to former flash chromatographic techniques [2].

Centrifugal Partition Chromatography Chromatography (CPC) is a special chromatographic technique where both stationary and mobile phase are liquid, and the stationary phase is immobilized by a strong centrifugal force. The main advantage is the cost-effectiveness, since it does not need any expensive and bulky solid stationary phase, and both quantity and quality requirements for solvents are less decreased contrast to standard liquid chromatographic techniques.

We screened various combination of non-chlorinated solvents for a scalable and economic separation of pinosylvins by CPC. A few suitable systems, where partition coefficients and selectivity were in a good range were screened on an Armen SCPC-250 laboratory scale CPC. The most suitable systems were scaled up in 20x size to a RotaChrom pilot CPC, to check possibility of later industrial production.

It was found that combinations of n-pentane, n-hexane, cyclohexane, n-heptane as alkane, acetone, isopropanol as intermediate solvent and water, as other combinations, provide suitable systems for scalable production. The exact system choice depends only on solvent availability, price, ICH residual solvent regulation, and other industrial parameters.

References:

[1] Lee SK, Lee HJ, Min HY, Park EJ, Lee KM, Ahn YH, Cho YJ, Pyee JH. Antibacterial and antifungal activity of pinosylvin, a constituent of pine. Fitoterapia 2005; 76: 258 – 260

[2] Poljansek I, Oven P, Vek V, Willför S, Raitanen JE. Extraction and isolation of pinosylvins from pine wood residue. 21th International Symposium on Separation Science, Poster 11, Ljubljana, Slovenie, 2015