In continuation of phytochemical investigations of plants of the Dipsacaceae family growing in the Republic of Azerbaidzhan [1, 2], we studied flowers of Scabiosa caucasica M.B. for flavonoid and triterpenoid content. Air-dried flowers (2 kg) collected during full flowering at the end of July 2006 near the village Slavyanka of Kedabek region of the Republic of Azerbaidzhan were extracted with ethanol (95%, 2×). The combined extracts were evaporated to 250 mL and left at room temperature. The resulting white precipitate was filtered off after a day.The filtrate was evaporated to 100 mL and diluted with water (300 mL). The resulting aqueous solution was treated successively with a mixture of ethylacetate and petroleum ether (1:1), ethylacetate, and n-butanol.Recrystallization of the aforementioned white precipitate from ethanol gave oleanolic acid, C 30 H 48 O 3 , mp 303-305°C, [α] D 20 -79 ± 2° (c 1.02, pyridine:methanol, 1:1) [2]. The extract obtained using ethylacetate:petroleum ether was evaporated and recrystallized from chloroform:ethanol to afford apigenin (1), C 15 H 10 O 5 , mp 343-345°C. IR spectrum (KBr, ν max , cm −1 ): 3300 (OH), 1655 (C=O), 1645, 1550 (C 6 H 5 ). UV spectrum (MeOH, λ max , nm): 270, 340 [3].1: R = R 1 = R 2 = R 3 = H 2: R = β-D-Glcp, R 1 = R 2 = H, R 3 = OH 3: R = β-D-Glcp, R 1 = R 3 = OH, R 2 = H 4: R = α-L-Arap(1→6)-β-D-Glcp, R 1 = H, R 2 = CH 3 , R 3 = OHThe ethylacetate extract was evaporated to dryness. The solid was dissolved in water (100 mL). The aqueous solution was shaken with ethylacetate (150 mL) and left for a day. The crystals that formed between the phases were separated and recrystallized from ethanol to afford cinaroside (2), C 21 H 20 O 11 ·2H 2 O, mp 270-272°C, [α] D 20 -48 ± 2° (c 0.5, formamide). UV spectrum (MeOH, λ max , nm): 256, 268, 350 (no change upon adding sodium acetate) [1]. The aqueous phase was evaporated to dryness. The solid was recrystallized from ethanol to afford quercimeritrin (3), C 21 H 20 O 12 , mp 245-247°C, [α] D 20 -52 ± 2° (c 0.5, methanol). IR spectrum (KBr, ν max , cm −1 ): 3480-3300,

We have continued research on chemical components from representatives of the family Dipsacaceae Lindl. (teasel) [1, 2], one species of which, Cephalaria grossheimii Bobr., is endemic to Azerbaidzhan [3]. According to Cherepanov [4], this species is synonymous with C. kotschyi Boiss et Hoh. However, this contradicts the literature on the phytochemistry of these plants. Thus, roots of C. kotschyi contained the alkaloids gentianine, gentianadine, and gentianaine [5] whereas alkaloids were not observed in those of C. grossheimii.Flowers of C. kotschyi contained the flavonoids kaempferol, hyperoside, quercimeritrin, cinaroside, cephaside, and cephacoside [2]. The flavonoid composition of C. grossheimii has not been studied.Therefore, we studied the flavonoid composition of C. grossheimii flowers. Flowers of this plant contained oleanolic acid in addition to apigenin, hyperoside, quercimeritrin, cinaroside, and palustroside. It can be seen that the flavonoid composition of flowers differed significantly for the two compared plants. The recent literature is consistent with this [6,7].Dry flowers of C. grossheimii (2 kg) that were collected near Rozgov, Lerik Region, Republic of Azerbaidzhan, during full flowering (beginning of July 2007) were extracted with ethanol (96%, 1:8) for 1 d. The extract was decanted. The extraction was repeated two more times using a fresh portion of ethanol (1:6) each time. The extracts were combined and evaporated in a rotary evaporator (fraction 1). The processed raw material was extracted a fourth time with ethanol (80%, 1:8) for 1 d. The extract was filtered and evaporated to a watery residue (fraction 2).Fraction 1 was treated with water (300 mL), shaken, and extracted successively with CHCl 3 , EtOAc:hexane, and EtOAc.Purification of the CHCl 3 extract over Al 2 O 3 and recrystallization afforded oleanolic acid, C 30 H 18 O 3 , mp 305-306°C (EtOH), [ ] α D 20 +79 ± 2° (c 1.2, MeOH). The crystals were white; soluble in alcohols, CHCl 3 , and Py; and insoluble in H 2 O. The EtOAc:hexane extract was evaporated. Recrystallization from aqueous EtOH gave apigenin, C 15 H 10 O 5 , mp 342-343°C. The crystals were light-yellow, soluble in alcohols, and insoluble in H 2 O.The EtOAc extract was dried over Na 2 SO 4 and evaporated to dryness. The solid was dissolved in MeOH (50 mL) and left at room temperature for 2 d. The resulting crystals were filtered off and recrystallized from MeOH to afford hyperoside, C 21 H 20 O 12 , mp 230-232°C. UV spectrum (λ max , MeOH, nm): 361, 305 sh, 277; +AlCl 3 : 434, 342 sh, 275. Light-yellow crystalline powder, soluble in alcohols and DMF, insoluble in CHCl 3 . Acid hydrolysis produced quercetin (64%) and D-galactose.The mother liquor was evaporated to dryness. Recrystallization of the solid from acetone afforded quercimeritrin, C 21 H 20 O 12 , mp 250-252°C, [ ] α D 20 −58 ± 2° (c 0.3, Py:MeOH). UV spectrum (λ max , MeOH, nm): 370, 256; +CH 3 COONa: 350, 256. Acid hydrolysis produced quercetin (65%) and D-glucose. The acetone solution was evaporated to drynes...

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