Twenty species of Salvia, naturally grown or cultivated in Poland, are investigated by headspace gas chromatography-mass spectrometry analysis. The main components of the volatile fraction of Salvia species are identified as alpha-pinene, camphene, beta-pinene, thujol, camphor, beta-chamigrene, and cadina-3,9-diene. There are also the compounds that can be considered as chemotaxonomic markers, namely beta-myrcene for Salvia lavadulifolia, beta-phelandrene for Salvia verticillata, tau-terpinene for Salvia stepposa, and isocaryophyllene and caryophyllene for Salvia officinalis. Certain compounds (such as o-cymene present in Salvia canariensis and Salvia stepposa; beta-trans-ocymene present in Salvia lavadulifolia, Salvia sclarea, and Salvia amplexicaulis; thujenone present in Salvia staminea, Salvia atropatana, Salvia jurisicii, and Salvia officinalis; and thujone present in Salvia azurea, Salvia lavandulifolia, Salvia hians, and Salvia triloba) can constitute chemotaxonomic advice for the aforementioned species. Also, the lack of certain compounds otherwise common in the individual sage species can be considered as chemotaxonomic advice (e.g., Salvia sclarea has no alpha-pinene and beta-pinene; Salvia lavadulifolia lacks camphene; Salvia triloba lacks beta-pinene and camphene; and Salvia officinalis lacks beta-chamigrene, thujol, and cadina-3,9-diene).

In our earlier studies, we demonstrated an ability of selected enantiomeric profen drugs (e.g., S-(+)-ibuprofen, S-(+)-naproxen, and S-(+)-and R-(−)-flurbiprofen) and one amino acid (i.e., L--phenylalanine) to undergo oscillatory transenantiomerization when dissolved in simple, low molecular weight solvents (e.g., water, ethanol, dichloromethane, acetonitrile, etc.) and stored for a longer period of time at ambient temperature or in a refrigerator. Experimental evidence of this process originates from a number of analytical techniques, with thin layer chromatography (TLC) and polarimetry among the best performing ones. There are two common structural features of all these compounds, namely: (i) they are 2-arylpropionic acids (2-APAs), and (ii) their chirality center is located on the -carbon atom of the respective molecules. It has also been established that the basic and the amphiprotic environment catalyzes the oscillatory transenantiomerization of the investigated compounds, while the acidic environment tends to hamper this process. Moreover, it has been established that all the aforementioned compounds can organize molecules present in the solution in such a manner as to produce the density anisotropy of the liquids considered. Model explanation of the oscillatory transenantiomerization of profens and L--phenylalanine was also developed as a starting point, adapting an earlier established oscillator known as Templator. The new model comprises two linked Templators. The quintessence of the Templator model adapted to the demands of the oscillatory transenantiomerization of profens and amino acids was based on an assumption Correspondence: Teresa Kowalska, 2007that the H-bonded 2-APA dimer is a template, able to generate the new dimers having the same steric configuration of their respective monomeric units. From our earlier studies, it clearly comes out that in spite of common traits of the oscillatory transenantiomerization of the selected profens and L--phenylalanine, the dynamics of this process can significantly differ from one compound to another, due to their differentiated molecular structure and, hence, to the different electron density distribution. Thus, in this study, we investigated the ability of L-tyrosine (another 2-APA and the amino acid regarded as essential for the humans) to undergo oscillatory transenantiomerization. Solubility of L-tyrosine in the amphiprotic binary mixture (70% aqueous ethanol solution) widely used in our earlier studies proved too low to use it as a solvent in the present investigation. Instead, we traced the behavior of L-tyrosine when stored for over one week in the following mixed solvents: ethanol-1M NaOH (7:3, v/v) and ethanol-1M HCl (7:3, v/v). The results of our experiments clearly confirm the ability of L-tyrosine to undergo the oscillatory transenantiomerization, similar to that of the previously studied profens and L--phenylalanine, although the individual dynamics of the oscillatory transenantiomerization with this particular enantiomer is also evident and disc...

Fingerprints developed in the experiments proved useful for the analysis of complex extracts of the different Salvia species.

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Salvia (sage) is the largest plant genus in the family Lamiaceae, embracing ca. 900 species. There is a growing interest in investigating chemical contents of different Salvia species, as some of them have been reported to exhibit a wide spectrum of biological activity. In this paper, conjugated (i.e., binary) chromatographic fingerprints have been introduced for the twenty Salvia species that are grown and cultivated in Poland. Apart from videoscans traditionally used for a comparison of the high-performance thin-layer chromatography fingerprints, digital scanning profiles and images obtained with use of the image processing program have also been employed. It is the first time that binary chromatographic fingerprints are used for the investigation of chemical contents of the Salvia species. The proposed procedure is rapid when compared with the similar ones presented in the literature, and moreover, it is easy to handle. The proposed method offers a possibility to discern the investigated species. It can be applied not only for chemotaxonomic purposes but also for finding new plant species that can be used as medical herbs (as it has been proposed, with S. triloba having a similar profile to S. officinalis). Validation of the method reveals that it is specific, reproducible, precise, and robust.