A series of new steroidal mono- and bis(thiosemicarbazones) (2a–e and 3a–e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a–e and 5a–e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono- and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a–e and 5a–e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.

The composition and content of individual phenolic compounds in various fruit wines and overall antioxidant properties of these fruit wines were studied. Phenolic compounds were separated by reverse phase (RP) HPLC techniques, and their content was determined by means of mass spectrometer (MS) with triple quadrupole (TQ) analyser, which recorded specific precursor-product transitions. Antioxidant activity was monitored by the following spectrophotometric methods: DPPH, FRAP and Folin-Ciocalteu assay, respectively. Four types of berries (raspberry, blackberry, chokeberry and blueberry), one type of pome (apple) and one type of stone fruit (cherries) were used for the production of fruit wines. Corresponding fruit wines were produced by microvinification with or without adding sugar into the must before fermentation. Increase in alcohol level was responsible for the increased content of phenolic compounds in fruit wine due to improved extraction conditions. Produced fruit wines were preserved by adding SO2 which interferes with the determination of antioxidant activity of phenolic compounds. In this case, the development of a correlation method based on FRAP assay was introduced. Fruit wines are a rich source of substances which show beneficial effects on human health. Depending on the fruit type, different antioxidant compounds were predominant in wine samples.

The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (E)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5μM to 14.9μM), eight on HeLa cells (IC50 values ranging from 8.9μM to 15.1μM) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7μM to 25.6μM) than cisplatin (21.5μM) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.

Metal chelation to bioactive small molecules is a well-established strategy to enhance the biological activity of the resulting complexes. Among the widely explored structural motifs, the combination of prominent metal centers with naturally inspired derivatives has attracted considerable attention. One such promising platform is the flavone scaffold, derived from flavonoids and studied since ancient times. Flavones are plant-derived compounds known for their diverse biological activities and health benefits. They exhibit significant structural variability, primarily through backbone modifications such as hydroxylation. Importantly, coordination of metal ions to hydroxylated flavone cores often improves their natural bioactivities, including anticancer and antimicrobial effects. In this review, we summarize transition metal complexes incorporating hydroxyflavone (OH–F) ligands reported over the past 15 years. We provide a concise overview of synthetic approaches and structural characterization, with a particular emphasis on coordination modes (e.g., maltol-type, acetylacetonate-type, catechol-type, and others). Furthermore, we discuss biological evaluation results, especially anticancer and antimicrobial studies, to highlight the therapeutic potential of these complexes. Finally, we suggest directions for the future development of metal-based agents bearing hydroxyflavone moieties through several critical points in terms of the accuracy, reproducibility, and relevance of biological studies involving metal-based compounds.