Balsam poplar and black poplar (Populus balsamifera L. and Populus nigra L.) buds that grow in Lithuania are the primary source of propolis, therefore it is proper to evaluate and compare the composition of these raw plant materials and propolis quantitatively and qualitatively. Propolis and balsamic poplar bud extract are dominated by p-coumaric acid and black poplar-caffeic acid. Antioxidant activity was evaluated by DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric-reducing antioxidant power) and CUPRAC (cupric reducing antioxidant capacity) methods and all extracts showed antioxidant activity, and obtained results correlated with the obtained amounts of phenolic compounds and flavonoids in the extracts. Studies of antimicrobial activity have shown that all extracts have a growth inhibitory effect against Staphylococcus aureus and Candida albicans, but the extract of balsam poplar buds showed the most significant effect of such kind. Considering the results of the research, it can be stated that balsam poplar buds cultured in Lithuania are the primary raw material of propolis, which is rich in phenolic compounds with antioxidant properties and is a promising raw material for pharmaceutical purposes.

The balsam poplar (Populus balsamifera L.) buds that grow in Lithuania are a polyphenol-rich plant material with a chemical composition close to that of propolis. In order to potentially adapt the extracts of this plant’s raw material for therapeutic purposes, it is important to carry out detailed studies on the chemical composition and biological activity of balsam poplar buds. An important step is to evaluate the yield of polyphenols by different extraction methods and using different solvents. According to our research, extracts of balsam poplar buds collected in Lithuania are dominated by p-coumaric (496.9–13,291.2 µg/g), cinnamic acid (32.9–11,788.5 µg/g), pinobanksin (34.9–1775.5 µg/g) and salicin (215.3–1190.7 µg/g). The antioxidant activity of poplar buds was evaluated by the ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), DPPH (2,2-diphenyl-1-picrylhydrazyl) and FRAP (ferric-reducing antioxidant power) methods, all extracts showed antioxidant activity and the obtained results correlated with the obtained amounts of total phenolic compounds in the extracts (ABTS r = 0.974; DPPH r = 0.986; FRAP r = 0.955, p < 0.01). Studies of antimicrobial activity have shown that ethanolic extracts have an antimicrobal activity effect against Staphylococcus aureus, Enterococcus faecalis and Escherichia coli. The extracts showed a better antimicrobal activity against gram-positive bacteria.

Balsam poplar buds are a raw material with a high content of polyphenols. Various polyphenols are known for their anti-inflammatory and antioxidant properties. In this study, an aqueous extract of balsam poplar buds was prepared in order to use environmentally friendly and non-aggressive solvents. The aqueous extract was lyophilized, and a 1% aqueous solution of lyophilized balsam poplar buds extract (L1) was prepared. L1 solution was used as a source of polyphenols for the production of ophthalmic in situ gels, so as to develop a product featuring antioxidant properties. Poloxamer 407 (P407) and hydroxypropyl methylcellulose (HPMC) were selected as gelling agents for the in situ gels. In order to select the formulations with the best conditions of use, formulations of different polymer concentrations (P407—10%, 12%, 15%; HPMC—0.5%, 0.75%) were prepared, choosing the same amount of the active polyphenol source L1. The physicochemical properties, rheological parameters, stability, and irritant effect on the rabbit corneal cell line (SIRC) were evaluated. Formulations in which P407 and HMPC concentrations were 10/0.75% and 12%/0.75% reached a gelation point close to the ocular surface temperature; the gels remained stable for 30 days and did not cause an irritant effect on the SIRC cell line.

Caffeic acid is a widely distributed phenolic acid. It is described in the scientific literature that caffeic acid has poor solubility. The aim of this study was to improve the solubility of caffeic acid for better dissolution kinetics when administered orally. During the study, oral capsules of different compositions were modeled. The results of the disintegration test revealed that the excipients affected the disintegration time of the capsules. The excipient hypromellose prolonged the disintegration time and dissolution time of caffeic acid. The dissolution kinetics of caffeic acid from capsules depend on the chosen excipients. P407 was more effective compared to other excipients and positively affected the dissolution kinetics of caffeic acid compared to other excipients. When the capsule contained 25 mg of β-cyclodextrin, 85% of the caffeic acid was released after 60 min. When the capsule contained 25–50 mg poloxamer 407, more than 85.0% of the caffeic acid was released from capsules after 30 min. The research results showed that in order to improve the dissolution kinetics of caffeic acid, one of the important steps is to improve its solubility.

The growing interest in polyphenols of natural origin and their plant sources encourages the study of their chemical composition and biological activity. Propolis is widely used as a source of phenolic compounds. The aim of this study is to evaluate and compare the chemical composition, antioxidant activity and sun protection factor (SPF) of the ethanolic extracts of the poplar buds, birch buds and pine buds of propolis plant precursors collected in Lithuania. The IC50 concentration of the extracts was evaluated using DPPH and ABTS methods. Extracts of poplar buds, birch buds and propolis showed a lower IC50 concentration by ABTS and DPPH methods compared with pine buds extracts. Poplar buds and propolis extracts showed the highest SPF value, while birch and pine buds extracts showed a lower SPF value. High-performance liquid chromatography (HPLC) analysis results showed that phenolic acids, such as p-coumaric acid and cinnamic acid, and flavonoids, such as pinobanksin and pinocembrin, were identified in all the tested extracts. Salicin has been identified only in poplar buds extracts. The results of antioxidant activity showed that propolis poplar and birch buds are a promising source of biologically active polyphenols.

In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (N-Boc-azetidin-3-ylidene)acetate was obtained from (N-Boc)azetidin-3-one by the DBU-catalysed Horner–Wadsworth–Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (N-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki–Miyaura cross-coupling from the corresponding brominated pyrazole–azetidine hybrid with boronic acids. The structures of the novel heterocyclic compounds were confirmed via ¹H-, ¹³C-, ¹⁵N-, and ¹⁹F-NMR spectroscopy, as well as HRMS investigations.