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We present the specific cooperative effect of a semisynthetic glycopeptide antibiotic teicoplanin and chiral ionic liquids containing the (1 R,2 S,5 R)-(-)-menthol moiety on the chiral recognition of enantiomers of mandelic acid, vanilmandelic acid, and phenyllactic acid. Experiments were performed chromatographically on an Astec Chirobiotic T chiral stationary phase applying the mobile phase with the addition of the chiral ionic liquids. The stereoselective binding of enantiomers to teicoplanin in presence of new chiral ionic liquids were evaluated applying thermodynamic measurements and the docking simulations. Both the experimental and theoretical methods revealed that the chiral recognition of enantiomers in the presence of new chiral ionic liquids was enthalpy driven. The changes of the teicoplanin conformation occurring upon binding of the chiral ionic liquids are responsible for the differences in the standard changes in Gibbs energy (Δ G0) values obtained for complexes formed by the R and S enantiomers and teicoplanin. Docking simulations revealed the steric adjustment between the chiral ionic liquids cyclohexane ring (chair conformation) and the β- d-glucosamine ring of teicoplanin and additionally hydrophobic interactions between the decanoic aliphatic chain of teicoplanin and the alkyl group of the tested salts. The obtained terpene derivatives can be considered as 'structural task-specific ionic liquids' responsible for enhancing the chiral resolution in synergistic systems with two chiral selectors. [ABSTRACT FROM AUTHOR]

Terpenes—a diverse group of secondary metabolites—constitute the largest class of natural products abundant in almost every plant species. The properties of concrete terpenes and essential oils have been intensively studied due to their widespread use in the pharmaceutical, food and cosmetics industries. Despite the popularity of these aromatic compounds, their derivatives, terpenoids, are still not comprehensively characterized despite exhibiting potent bioactive properties. This review aims to assess the anticancer properties of selected monoterpenes including carvone, carvacrol, perillyl alcohol, perillaldehyde, limonene, menthol and their derivatives while also evaluating potential applications as novel anticancer treatments. Special attention is paid to functional groups that improve the bioactivity of monoterpene molecules. This review also covers the therapeutic potential of deep eutectic solvents that contain monoterpene substances. Taken together, the literature supports the use of monoterpene derivatives in the development of new alternatives for disease treatment and prevention. [ABSTRACT FROM AUTHOR]

A comprehensive physico-chemical characterization of the chiral ionic liquids of a 3-alkyl-1-[(1 R ,2 S ,5 R )-(–)-menthoxymethyl]imidazolium bis(trifluoromethylsulfonyl)imides homologous series with a linear alkyl substituent ranging from the methyl up to the dodecyl group was carried out experimentally to investigate the way in which the measured thermophysical properties were influenced by the alkyl chain length on the cation. Refractive index, density, speed of sound, and isobaric heat capacity were measured as a function of temperature at atmospheric pressure and analyzed by methods based on mathematical gnostics. A robust linear regression along a gnostic influence function was used to optimize parameters of the relationships used in this work and to estimate the changing nanosegregation in the studied ionic liquid series by finding the Critical Alkyl Length Size (CALS) from heat capacity data. In addition, we propose the use of the marginal analysis to assess the quality of the measured data as an alternative to the estimate of the measurement uncertainty. [ABSTRACT FROM AUTHOR]