Separation of Rosmarinic Acid Enantiomers by Three Different Chromatographic Methods (HPLC, CE, GC) and the Determination of Rosmarinic Acid inHedera helix L.

Abstract

Three methods employing high performance liquid chromatography (HPLC), capillary electrophoresis (CE), and gas chromatography (GC) were developed for the separation of enantiomers of rosmarinic acid (RA). Chiral resolution of underivatized RA was achieved on a chiral AGP® HPLC column and by micellar electrokinetic capillary chromatography (MECC). Alternatively, after derivatization, the resulting diastereomeric 3,4-di-hydroxyphenyllactic acid (-)-menthyl esters were separated by non-chiral GC. These methods allow reliable and rapid determination of the enantiomeric ratio of RA samples. RA obtained from vegetative material of Hedera helix L. (Araliaceae) was determined to be (R)-(+)-RA. In contrast to published data, the optical rotation value of rosmarinic acid was found to be +106°.