LAUSR

In continuation of the search for possible new sources of biologically active compounds, we studied the constituents of flowerheads and roots of Scabiosa georgica Sulak. growing in Azerbaijan [1], which have not previously been adequately studied. Representatives of the genus Scabiosa L. are rich in flavonoids, iridoids, and triterpenoids [2, 3], which stimulated more fundamental research of the chemical constituents of S. georgica growing in Azerbaijan as sources of biologically active compounds. The chemical composition of S. georgica growing in other countries was not found in the literature available to us. Dried and milled flowerheads (1.0 kg) were soaked with EtOH (80%). The extracts were combined, evaporated to a watery residue, and extracted sequentially with hexane, CHCl3, EtOAc–hexane, and EtOAc. The hexane extract afforded steroid 1; the CHCl3 extract, 2; the EtOAc–hexane extract, 3; and the EtOAc extract, 4. Preparative paper chromatography of the mother liquor from the EtOAc extract after isolating 4 yielded flavonoids 5 and 6 [4]. β-Sitosterol (1), C29H50O, mp 138–140°C (aqueous EtOH), [α]D 20 –40° (c 0.3, CHCl3), mp of the acetate 129–131°C (aqueous EtOH). Oleanolic acid (2), C30H48O3, mp 301–302°C (MeOH), [α]D 20 +79 ± 2° (c 1.2, Py–CHCl3), mp of the acetyl derivative 232°C [5]. Luteolin (3), C15H10O6, mp 328–330°C (MeOH), mp of the tetraacetate 224–226°C (CHCl3–hexane). UV spectrum (MeOH, λmax, nm): 356, 260, 275 [6]. Hyperoside (4), C21H20O12, mp 235–236°C (EtOH), [α]D 20 –56° (c 1.2, DMF). UV spectrum (MeOH, λmax, nm): 354, 266, 275 [7, 8]. Cynaroside (5), C21H20O11, mp 234–236°C (aqueous EtOH), [α]D 20 –50° (c 0.45, Py-MeOH) [6, 8]. Quercimeritrin (6), C21H20O12, mp 254–255°C (Me2CO), [α]D 20 –51° (c 0.3, DMF) [6, 9]. Ground dry roots (1.0 kg) were placed into a flask, treated with hexane (4 L), and refluxed on a water bath for 4 h. The solvent was evaporated to a dry solid and recrystallized from aqueous EtOH to afford β-sitosterol (1). The raw material remaining after hexane extraction was extracted with CHCl3 (2×) for 24 h. The extracts were evaporated to a dry solid that was recrystallized from EtOH to afford 2. The raw material remaining after CHCl3 extraction was extracted with EtOH (3×) for 24 h. The extracts were combined, evaporated to a dry solid that was mixed with H2O (250 mL) and extracted sequentially with EtOAc and n-BuOH. The BuOH fraction was evaporated to produce total triterpene saponins consisting of six compounds. The nature of the triterpene saponins (5.0 g total) was established by acid hydrolysis (7% H2SO4, 5 h). The hydrolysate was cooled. The resulting crystals of oleanolic acid (2) were separated. Total alkaloids were obtained from roots of S. georgica (0.5 kg) using the CHCl3 method and were worked up with H2SO4 (5%), made basic with NH4OH (10%), and worked up with CHCl3 to afford total alkaloids (~0.03%). TLC established that the total alkaloids consisted of five compounds (Sorbfil plates, CHCl3–MeOH, 20:1; Dragendorff’s reagent). Alkaloids from representatives of the genus Scabiosa L. were observed for the first time. All isolated compounds were identified using physicochemical properties, IR and UV spectral data, and comparisons with authentic samples.