Praziquantel (PZQ) is a biopharmaceutical classification system (BCS) class II anthelmintic drug characterized by poor solubility and a bitter taste, both of which can be addressed by inclusion complexation with cyclodextrins (CD). In this work, a comprehensive investigation of praziquantel/cyclodextrin (PZQ/CD) complexes was conducted by means of UV–vis spectroscopy, spectrofluorimetry, NMR spectroscopy, liquid chromatography-high-resolution mass spectrometry (LC-HRMS/MS), and molecular modeling. Phase solubility studies revealed that among four CDs tested, the randomly methylated β-CD (RMβCD) and the sulfobutylether sodium salt β-CD (SBEβCD) resulted in the highest increase in PZQ solubility (approximately 16-fold). The formation of 1:1 inclusion complexes was confirmed by HRMS, NMR, and molecular modeling. Both cyclohexane and the central pyrazino ring, as well as an aromatic part of PZQ are included in the CD central cavity through several different binding modes, which exist simultaneously. Furthermore, the influence of CDs on PZQ stability was investigated in solution (HCl, NaOH, H₂O₂) and in the solid state (accelerated degradation, photostability) by ultra-high-performance liquid chromatography–diode array detection–tandem mass spectrometry (UPLC-DAD/MS). CD complexation promoted new degradation pathways of the drug. In addition to three already known PZQ degradants, seven new degradation products were identified (m/z 148, 215, 217, 301, 327, 343, and 378) and their structures were proposed based on HRMS/MS data. Solid complexes were prepared by mechanochemical activation, a solvent-free and ecologically acceptable method.

Health-oriented preferences, a demand for innovative food concepts, and technological advances have greatly influenced changes in the food industry and led to remarkable development of the functional food market. Incorporating herbal extracts as a rich source of bioactive compounds (BC) could be an effective solution to meet the high demand of consumers in terms of expanding the high-quality range of functional foods. The aim of this study is the valorization of the bioactive potential of T. montanum L., an understudied Mediterranean plant species, and the in-depth elucidation of a polyphenolic profile with a UHPLC-HR MS/MS and NMR analysis. The total phenolic content (TPC) and antioxidant capacity (AC) were determined on heat-assisted (HAE), microwave-assisted (MAE) and subcritical water (SWE) extracts. In terms of antioxidant capacity, SWE extracts showed the most notable potential (ABTS: 0.402–0.547 mmol eq Trolox g⁻¹ dw, DPPH: 0.336–0.427 mmol eq Trolox g⁻¹ dw). 12 phenolic compounds were identified in the samples of T. montanum from six microlocations in Croatia, including nine phenylethanoid glycosides (PGs) with total yields of 30.36–68.06 mg g⁻¹ dw and 25.88–58.88 mg g⁻¹ dw in HAE and MAE extracts, respectively. Echinacoside, teupolioside, stachysoside A, and poliumoside were the most abundant compounds HAE and MAE extracts, making T. montanum an emerging source of PGs.

Beta-blockers are chiral compounds with enantiomers that have different bioactivity, which means that while one is active, the other can be inactive or even harmful. Due to their high consumption and incomplete degradation in waste water, they may reach surface waters and affect aquatic organisms. To address this issue we developed a chromatographic method suitable for determining beta-blocker enantiomers in surface waters. It was tested on five beta-blockers (acebutolol, atenolol, bisoprolol, labetalol and metoprolol) and validated on bisoprolol enantiomers. Good enantioseparation of all analysed beta-blockers was achieved on the Chirobiotic V column with the mobile phase composed of methanol/acetic acid/triethylamine (100/0.20/0.15 v/v/v) at a flow rate of 0.5 mL/min and column temperature of 45 °C. Method proved to be linear in the concentration range from 0.075 µg/mL to 5 µg/mL, and showed good recovery. The limits of bisoprolol enantiomer detection were 0.025 µg/mL and 0.026 µg/mL and of quantification 0.075 µg/mL and 0.075 µg/mL. Despite its limitations, it seems to be a promising method for bisoprolol enantiomer analysis in surface water samples. Further research could focus on waste water analysis, where enantiomer concentrations may be high. Furthermore, transferring the method to a more sensitive one such as liquid chromatography coupled with tandem mass spectrometry and using ammonium acetate as the mobile phase additive instead of acetic acid and triethylamine would perhaps yield much lower limits of detection and quantification.