Chemical constituents from the roots of Cephalaria kotschyi

Abstract

Cephalaria kotschyi Boiss. et Hoh. (Dipsacaceae) is an endemic plant of the Caucasus region growing in Azerbaijan. Earlier phytochemical studies reported the isolation of triterpene saponins, flavonoids, and gentianine type alkaloids from the roots and flowers of C. kotschyi [1][2][3][4][5][6][7]. In our previous study we described the isolation of the iridoid glycosides loganin and gentiopicroside from the roots of this plant [8].Herein we report, together with the gentiopicroside and loganin described previously, the isolation of three iridoid and secoiridoid glycosides: loganic acid [9], swertiamarin [10], and cantleyoside [11]; two furofuranic lignans: prinsepiol glycoside [12] and 8-hydroxypinoresinol-4c-O-E-D-glucoside [13]; and two triterpene saponins: giganteoside Jc [14] and dipsacoside B [15], from an investigation of the chemical constituents of the roots of C. kotschyi. The plant was collected in the Lerik region of Azerbaijan in September 2005. A voucher specimen (C 8131005) was deposited at the herbarium of the Botanical Institute, Academy of Science, Azerbaijan.Air-dried roots (100 g) were extracted by percolation at room temperature with MeOH (1 L for 24 h), and the obtained solution was concentrated under vacuum. The MeOH extract (5 g) was submitted to flash column chromatography on polyamide MN SC 6 Macherey Nagel® (70 Pm), using a step gradient of H 2 O-MeOH of 90:10, 50:50, and 0:100, to give 3 main fractions (F1-F3). Fraction F1 was further purified by low-pressure liquid chromatography on Prepamatic Chromatospac 10 (Jobin Yvon) with Lichroprep RP18 Merck® (25-40 Pm). A step gradient of H 2 O-MeOH and 0:100, 1 L for each) allowed us to obtain 20 fractions, Sp1-Sp20. Fractions Sp2, Sp5, Sp7, Sp9, and Sp16 afforded respectively loganic acid (18 mg), swertiamarin (73 mg), gentiopicroside (250 mg), loganin (75 mg), and cantleyoside (230 mg). Purification of fractions Sp12 and Sp13 by means of preparative high-performance liquid chromatography on a Symmetry C18 column (5 Pm, 250 u 4.6, waters®), using H 2 O-MeOH (75:25), yielded prinsepiol glycoside (20 mg) and 8-hydroxypinoresinol glycoside (18 mg) respectively. Fraction F2 (1 g) was fractionated by silica gel CC using CH 2 Cl 2 -MeOH-H 2 O (50:16:3) and (30:13:3) successively as eluent to give dipsacoside B (30 mg) and giganteoside Jc (30 mg). The structural elucidations of the obtained compounds were performed by spectroscopic analysis, including 2D NMR data, and confirmed by comparison with the previously reported data. NMR spectra were recorded in CD 3 OD (G ppm) on a Bruker DRX 500 spectrometer operating at 500.13 MHz and 125.13 MHz.All the isolated compounds, except loganin and gentiopicroside, have been reported for the first time from C. kotschyi. The iridoid glycosides loganin, loganic acid, and cantleyoside of Cephalaria and other genus of the Dipsacaceae family [16][17][18][19][20] have been previously reported. These compounds are used as chemosystematic markers for plants of the Dipsacaceae family. The secoiridoid swertiamarin has b...

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

“…Compounds 3 and 4 showed deprotonated ion as m / z = 375 with UV-Vis maximum at 231 nm. Based on comparison with chemical standard compound 3 was identified as loganic acid, which was previously confirmed in Cephalaria kotshyi [ 46 ]. Compound 4 was described as loganic acid isomer due to the same molecular weight and identical fragmentation pattern ( Table 1 ).…”

“…After the comparison with chemical standard, 15 was identified as loganin. Loganin was previously confirmed in Cephalaria elaziginesis , Cephalaria kotschyi and Cephalaria isaurica [ 27 , 46 , 48 ]. Compounds 8 , 16 – 20 and 29 were tentatively classified as other iridoids based on UV-Vis maxima observed at ca.…”

“…Compounds 3 and 4 showed deprotonated ion as m/z = 375 with UV-Vis maximum at 231 nm. Based on comparison with chemical standard compound 3 was identified as loganic acid, which was previously confirmed in Cephalaria kotshyi [46]. Compound 4 was described as loganic acid isomer due to the same molecular weight and identical fragmentation pattern (Table 1) The quantitative evaluation of the major compounds detected in the analyzed extracts was performed based on the calibration curves of different compounds: luteolin for the quantification of flavonoid derivatives, aucubin for iridoids, chlorogenic acid for phenolic acids and unidentified compounds.…”

Phytochemical and Biological Investigations on Cephalaria anatolica

“…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].…”