Essential oil from herb and rhizome of Peucedanum ostruthium (L. Koch.) ex DC.

Essential oil from herb and rhizome of Peucedanum ostruthium (L.Koch.) ex DC underwent qualitative and quantitative analyses. The content of the oil obtained by hydrodistillation was 0.95% in the herb and 1.25% in the rhizome (per dry weight basis). Gas chromatography (GC) with MS detection and flame ionisation detection showed that the oil from the rhizome contains 39 compounds, of which 29 were identified. Gas chromatography with flame ionisation detection in chiral columns against standard compounds showed the presence of enantiomers of some of the components of the oil. Compounds present in largest quantities are: sabinene (35.2%) of which (+) sabinene accounts for (96.54%) and 4-terpineol (26.6%) of which (+) 4-terpineol accounts for (65.8%). 44 components were found in the herb essential oil, of which 39 compounds were identified. Compounds present in largest quantities were beta-caryophyllene (16.1%) and alpha-humulene (15.8%). The content of sabinene in the herb oil was 4.7%. The following compounds were present in the herb oil only as enantiomers: (+) sabinene (4.7%), (-) limonene (4.4%), (-) beta-pinene (0.4%). A coumarin (osthole) was detected in both essential oils (5.5% in herb oil and 5.1% in rhizome oil).

Comparative study on camphor enantiomers behavior under the conditions of gas-liquid chromatography and reversed-phase high-performance liquid chromatography systems modified with alpha- and beta-cyclodextrins.

The dependence of retention and selectivity parameters of camphor enantiomers on the concentration of alpha- and beta-cyclodextrins were studied under conditions of GLC (matrix solvent: Glycerol, 95 degrees C) and RP-HPLC (matrix solvent: Aqueous methanolic, 20 degrees C). It has been found that beta-cyclodextrin forms complex of 1:1 stoichiometry and does not recognize enantiomers of camphor. In contrast alpha-CD forming complexes of 1:2 stoichiometry appeared to be very efficient chiral selector of (+) and (-)-camphor. Relatively considerable differences have been observed between stability constants determined by GLC and RP-HPLC, what may be explained by the various natures of the matrix solvents and the various temperatures of the measurements. On the contrary, the enantioseparation factor alpha observed at higher concentrations of alpha-cyclodextrin stabilizes on the very similar value alpha+/-(GLC) approximately = alpha-/+(HPLC) approximately = 1.6. Simple theoretical considerations focusing on the differences in the mechanisms of the studied processes have been performed. According to them the enantiomer forming the more stable complex with the cyclodextrin should be eluted from the RP-HPLC column first and GLC column last. This fact has been confirmed experimentally.

Separation ability and stoichiometry of cyclodextrin complexes.

Gas-liquid chromatography has been applied to search relations between selectivity towards isomers and stoichiometry of cyclodextrin complexes. The model tested compounds were: dimethylnaphthalenes and alpha- and beta-pinenes as constitutional isomers; cis/trans decalins, anetholes and isosafroles as diastereomers and as enantiomers (+/-)-alpha-pinenes and (+/-)-camphenes. Experimental retention data are used to confirm a simple theoretical model that allows distinguishing formation of G x CD complexes (1:1) and G x CD2 complexes (1:2). Based on the experimental data, stability constants K were evaluated. It has been found that remarkable selectivity factor alpha may appear both within the range of 1:1 stoichiometry (beta-CD complexes of decalins and of alpha- and beta-pinenes) and 1:2 stoichiometry (alpha-CD complexes with (+/-)-alpha-pinenes and (+/-)-camphenes). Occasionally selectivity arises from a different composition, when one isomer forms a 1:1 stoichiometry complex while another forms a 1:2 complex (dimethylnaphthalenes, cis/trans-anetholes and cis/trans-isosafroles).

Chromatographic studies of the enantiomeric composition of some therapeutic compositions applied in the treatment of liver and kidney diseases.

A gas-liquid chromatographic system with alpha-cyclodextrin in formamide medium (coated on Chromosorb) was used for the separation of enantiomers of alpha-pinene, beta-pinene, limonene and camphene in medicines applied in the therapy of liver and kidney diseases. The drugs under investigation were produced in Poland (Terpichol and Terpinex), in Germany (Rowachol and Rowatinex) and in Slovenia (Uroterp). It was found that, depending on the manufacturer, medicines possessing similar chemical compositions differ considerably from one another regarding the content of enantiomers, mainly those of alpha-pinene.