Flavonoids from Cephalaria grossheimii

Abstract

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...

Extracts from Cephalaria Uralensis (Murray) Roem. & Schult. and Cephalaria Gigantea (Ledeb.) Bobrov as Potential Agents for Treatment of Acne Vulgaris: Chemical Characterization and In Vitro Biological Evaluation

“…This compound was confirmed in Cephalaria grossheumii Bobr. species [26]. Compounds 21, 24 and 28 were identified as apigenin derivatives.…”

“…335 for apigenin derivatives (21, 24, 28), and ca. 350 for luteolin and quercetin glycosides (22,23,26). Compound 26 showed deprotonated ion at m/z = 463.…”

Phytochemical and Biological Investigations on Cephalaria anatolica

“…IR spectra were obtained on an ATI Mattson Genesis Series Fourier transform infrared spectrophotometer. NMR experiments were performed on Varian AS 400 MHz and Varian ASP 600 MHz instruments in DMSO-d 6 . All chemical shifts were given in ppm units with reference to tetramethylsilane (TMS) as an internal standard and the coupling constant (J) were in Hz.…”

“…This wide range of usages has led to investigations on different Cephalaria species. Many chemical identification studies have been reported that this genus contains triterpenoid saponins, flavonoids, alkaloids, furofuranic lignans and iridoids [5][6][7][8][9][10][11][12][13]. According to these literatures, it is also known that these compounds have different activities including antimicrobial, hemolytic, hypolipidemic, immunomodulating and cytotoxic [7-8, 11-12, 14].…”

Antimicrobially Active Hederagenin Glycosides from Cephalaria elmaliensis

“…In light of all of this knowledge, we decided to investigate the glycosidic compounds in Cephalaria elmaliensis (Dipsacaceae). Previous phytochemical investigations on different Cephalaria species have reported a number of triterpene saponins, iridoids, flavonoids, alkaloids, lignans, and their glycosidic compounds [4][5][6][7][8][9][10][11][12][13][14][15]. Triterpene saponins are the major examples of these types of substances [4][5][6][7][8][9][10][11].…”