Use of counter-current chromatography as a selective extractor for the diterpenequinone 7α-hydroxyroyleanone from Tetradenia riparia

A solvent system was developed for selective isolation by high-speed counter-current chromatography (HSCCC) of the benzoquinone 7α-hydroxyroileanone, 1, a bioactive diterpene from a dichloromethane extract of Tetradenia riparia leaves. Several solvent systems were initially studied, including hexane-ethyl acetate-methanol-water in several ratios, hexane-acetone-methanol-water, hexane-ethanol-water and hexane-acetonitrile-methanol, which gave recovery rates for the target compound between 13.4 and 35.9%. The new solvent system hexane-5% aqueous Na2CO3 (1:1) was developed based on the chemical ionization reaction of the benzoquinone hydroxyl group in the basic pH of the carbonate solution, prompted by the extraction procedure used for the extraction of lapachol (a natural naphtoquinone) from a Tabebuia species wood. By using the HSCCC chromatograph as a liquid-liquid extractor with the above mentioned solvent system the recovery rate of 1 increased to 81.8%, affording the quinone with 97% purity.