o:3257 Sekundarni metaboliti odabranih vrsta roda Bupleurum L. (Apiaceae): izolovanje, identifikacija i biološka aktivnost Secondary metabolites of selected taxa of the genus bupleurum L. (apiaceae): isolation, identification and biological activity : doctoral dissertation sr In this doctoral dissertation, a phytochemical study of the secondary metabolites of selected species of the genus Bupleurum L. (Apiaceae) was undertaken with the goals of isolating, identifying and evaluating the biological activity of the less-polar metabolites. The study encompassed a detailed chemical investigation of diethyl-ether extracts of B. praealtum, B. veronense, B. falcatum and B. sibthorpianum, as well as the essential oils of B. praealtum and B. affine. Using dry-flash chromatography, GC–MS analysis and NMR spectroscopy, sixteen new compounds were isolated and structurally characterized. These include a large cohort of polyunsaturated metabolites—a hydrocarbon, several esters, a γ-butyrolactone and a macrolide—together with one lignan and one phloroglucinol derivative. In the extract of B. praealtum, four new polyunsaturated esters, a new polyunsaturated γ-butyrolactone and one new lignan, 7-oxoarctin, were identified. From B. veronense, a new macrolide (homodihydrofalcarinolide), a polyunsaturated veronaester and a phloroglucinol derivative were obtained. In B. falcatum and B. sibthorpianum, three new polyunsaturated aliphatic esters and one new polyunsaturated hydrocarbon were detected. The essential oils of B. praealtum and B. affine were analyzed by GC–MS, revealing a total of 230 constituents. Sesquiterpene hydrocarbons predominated in both oils, while the oil of B. affine was also notable for a high content of alkanes. For the first time, perillyl 2-methyl-butanoate (its identity confirmed by synthesis) was detected, along with two new natural acetate esters—4-decyl acetate and 4-undecyl acetate. Selected compounds were assayed against primary rat immune cells (macrophages and splenocytes). They displayed concentration-dependent, bidirectional activity with marked immunomodulatory selectivity. These findings broaden current knowledge of the chemical diversity within Bupleurum, underscoring its taxonomic and pharmacological potential. Biografija: list. 251.Bibliografija: list. 174-188. Datum odbrane: 12.11.2025. Organic chemistry and biochemistry, organic synthesis 91552100 186248969 91552101 8823 2026-04-07T17:55:32.053Z 45 no 46 Milica, 1992- Nešić 103527945 2025 63 mentor Niko, 1981- Radulović 8429415 2025 63 član komisije Irena, 1990- Raca 16265063 2025 63 član komisije Marija S., 1985- Genčić 72061961 2025 63 član komisije Milan S., 1980- Dekić 69160201 2025 257 listova 14481280 http://phaidrani.ni.ac.rs/o:3257 no yes 12 2026-04-07T17:55:32.320Z 70 Bupleurum, ekstrakt, etarsko ulje, polinezasićeni estri, lignani, makrolid, floroglucinol, spinska simulacija, NMR, GC-MS, hromatografija, Mosher-ovi estri Bupleurum, extract, essential oil, polyunsaturated esters, lignans, macrolide, phloroglucinol, spin simulation, NMR, GC-MS, chromatography, Mosher’s esters (582.794.1:577.13):(54.061+615.322)(043.3)577.121:582.321.2(043.3) P 003; P 004; P 390; P 300 1738 18A07 18A0703 2025