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Cytotoxic Activities of Flavonoids from Centaurea Scoparia

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Cytotoxic Activities of Flavonoids from Centaurea Scoparia Hindawi Publishing Corporation e Scientific World Journal Volume 2014, Article ID 274207, 7 pages http://dx.doi.org/10.1155/2014/274207 Research Article Cytotoxic Activities of Flavonoids from Centaurea scoparia Sayed A. Ahmed and Emadeldin M. Kamel Chemistry Department, Faculty of Science, Beni Suef University, Salah Salem Street, P.O. Box 62514, Beni Suef 62514, Egypt Correspondence should be addressed to Sayed A. Ahmed; [email protected] Received 17 January 2014; Accepted 22 May 2014; Published 11 June 2014 Academic Editor: Diego Savoia Copyright © 2014 S. A. Ahmed and E. M. Kamel. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Phytochemical studies on the ethanolic extract of the aerial parts of Centaurea scoparia ledtotheisolationof two new flavonoids, 3 ,4 -dihydroxy-(3 ,4 -dihydro-3 -hydroxy-4 -acetoxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)-flavone-3-O-- D-glucopyranoside (1)and3,3,4 -trihydroxy-(3 ,4 -dihydro-3 ,4 -dihydroxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)-flavone (2), along with eight known flavonoids isolated for the first time from this plant, cynaroside (3), Apigetrin (4), centaureidin (5), oroxylin A(6), 5,7-dihydroxy-3 ,4 ,5 -trimethoxyflavone (7), atalantoflavone (8), 5-hydroxy-3 ,4 ,8-trimethoxy-2 ,2 -dimethylpyrano (5 ,6 :6,7)-flavone (9), and 3 ,4 ,5,8-tetramethoxy-2 ,2 -dimethylpyrano (5 ,6 :6,7)-flavone (10). The structures of the isolated compounds were elucidated by means of spectroscopic tools including 1D and 2D NMR, UV,IR, and mass spectroscopy. Cytotoxic activities of the isolated compounds were evaluated against human cervical carcinoma HeLa, human hepatocellular carcinoma HepG2, and human breast carcinoma MCF-7. Compound 2 was the most potent cytotoxic agent against HeLa cells with an IC50 0.079 M. 1. Introduction and led to the isolation of two new hydropyranoflavones(1,2), two known flavonoid glycosides(3,4), three known flavonoid The genus Centaurea belongs to the family Asteraceae and aglycones (5–7), and three known pyranoflavones (8–10). contains several hundreds of species of herbaceous thistle which are mainly distributed north of the equator, mostly in the Middle East and Western Asia [1]. Many of the Centaurea 2. Experimental species have been utilized in traditional medicine for the 1 13 2.1. General. H(500MHz)and C(125MHz)NMRwere treatment of cancer [2], microbial infections [3, 4]andas stimulant, tonic [5, 6], antidiabetic [7–9], diuretic [7], and recorded in DMSO- 6 onaBrukerAV-500NMRspectrome- terusingTMSasinternalstandard.Chemicalshifts()are antirheumatic [10, 11]. C. scoparia is an annual or biannual herb growing in Sinai, Egypt [11]. Previous phytochemical expressed in ppm and coupling constants ( ) are reported screening showed that C. scoparia contains phenolic com- in Hz. Optical rotations were measured with Perkin-Elmer pounds including luteolin, apigenin, hispidulin, cirsimar- 341 polarimeter. UV data were obtained from Shimadzu itin, salvigenin, (-)-matairesinol, (-)-arctigenin, vanillin, and UV-vis 160i spectrophotometer. HREIMS and EIMS mass omega-hydroxypropioguaiacone [12]. Also, C. scoparia con- spectroscopic analysis was measured on a Finnigan MAT tains chlorinated and nonchlorinated guaianolides including TSQ 700 mass spectrometer. IR spectra were recorded on KBr diain, janerin, cynaropicrin, deacylcynaropicrin [13, 14], and pellets on a Shimadzu FTIR-8400 instrument. other sesquiterpenes lactones [15, 16]. In our research on phe- nolic constituents and biological activities of folk medicinal 2.2. Plant Material. The aerial parts of C. scoparia were col- plants, we have found that the ethanolic extract of the aerial lected from the Eastern desert close to Beni Suef governorate parts C. scoparia exhibited a potent cytotoxic activity against onApril2011.Identificationoftheplantwasconfirmedby human cancer cell lines. So a phytochemical fractionation the Department of flora, Agricultural Museum, Ministry of for the ethanolic extract of C. scoparia has been performed Agriculture and Herbarium of the Department of Botany, 2 The Scientific World Journal Faculty of Science, Cairo University. Voucher specimen was carcinoma cells). Cells were grown or maintained upon ∘ kept in Herbarium, National Research Center, Giza, Egypt. arrival at 37 C in a humidified incubator with 5% CO2 and 95% atmosphere as recommended by ATCC. All media were supplemented with penicillin (100 U/mL), streptomycin 2.3. Extraction and Isolation. The dried and powdered aerial (100 g/mL), and 10% heat-inactivated fetal bovine serum parts of C. scoparia (5 kg) were extracted at room temperature (FBS). with 70% EtOH (10 L × 4 times). The solvent in the combined extracts was removed under reduced pressure at temperature ∘ not exceeding 40 Ctilldrynesstogiveacruderesidue 2.5. Cytotoxicity Assay. Cytotoxicity was quantitatively eval- (275 g) which was successively partitioned with hexane (1 L × uated by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetra- 3 times), ethyl acetate (1 L × 3 times), and -butanol (1 L × 3 zolium bromide (MTT) method as previously described [17]. The cells were seeded in 96-well plate at a cell concentration times) to give three extracts hexane (70 g), ethyl acetate (50 g), 4 and -butanol (75 g). The ethyl acetate extract was subjected of 1 × 10 cells per well in 100 Lofgrowthmediumthen × treated with various concentrations of test compounds and to fractionation on a column (150 4cm)containing600gm ∘ of polyamide 6S. Gradient elution started with water followed incubatedinahumidified5%CO2 atmosphere at 37 Cfor by H2O/EtOH mixtures of decreasing polarities (10 : 0, 9 : 1, 72 h. After the incubation, 10 L of 5 mg/mL MTT was added 8 : 2, 7 : 3, 6 : 4, 5 : 5, 4 : 6, 3 : 7, 2 : 8, 1 : 9, and 0 : 10). The to each well and incubated for another 4 h. After removal of bands migrated along the column were observed under UV the supernatant, formazan crystals were dissolved in 100 L light during elution process to control the fractionation DMSO and the optical density values were measured at processaspossible.Atotalof44fractionswerecollected 570 nm with a microplate reader. Deguelin was used as the and combined into 12 main fractions (E1–E12) according positive control. to their TLC behavior. These fractions were dried under ≈ ∘ Vacou 40 C and subjected to detailed investigations by 3. Results and Discussion TDPC and TLC. Phytochemical investigation of fractions E1andE2revealedthepresenceoftraceamountsofphe- A phytochemical investigation of the ethyl acetate extract of nolic compounds and majority of free sugars, which were C. scoparia aerial parts led to the isolation of two new (1-2) detected by comparative paper chromatography. Fraction E3 and eight known (3–10) flavonoids isolated for the first time (1.7 g) was applied to a polyamide column (35 × 2.5 cm) from this plant (Figure 1). The structures of the new com- using EtOH/H2Omixture(1:1)asaneluenttogivefour pounds 3 ,4 -dihydroxy-(3 ,4 -dihydro-3 -hydroxy-4 - subfractions (E3-1, E3-2, E3-3, and E3-4). Subfractions E3- acetoxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)-flavone-3-O-- 2 and E3-3 were combined and purified on Sephadex LH- D-gulcopyranoside (1) and 3,3 ,4 -trihydroxy-(3 ,4 -dihy- 20 (30 × 1.5 cm) column and eluted with MeOH/H2O(1:1) dro-3 ,4 -dihydroxy)-2 ,2 -dimethylpyrano-(5 ,6 :7,8)- to give the purified compounds 1 (25 mg) and 2 (32 mg). flavone2 ( ) were elucidated by means of spectroscopic tools Fraction E4 (1.5 g) was chromatographed on Sephadex LH- andtheknowncompoundswereidentifiedascynaroside(3) 20 column eluted by EtOH to give two major subfractions [18], Apigetrin (4)[19], centaureidin (5)[20, 21], oroxylin (E4-1 and E4-2). Subfraction E4-1 was further purified by A(6)[22, 23], 5,7-dihydroxy-3 ,4 ,5 -trimethoxyflavone ODS CC eluted with a gradient MeOH/H2Osolventsystem (7)[24, 25], atalantoflavone (8)[26], 5-hydroxy-3 ,4 ,8- (from 5 : 5 to 9 : 1) to yield compound 3 (21 mg). Subfraction trimethoxy-2 ,2 -dimethylpyrano (5 ,6 :6,7)-flavone (9) E4-2 was further purified on Sephadex LH-20 column eluted [27, 28], and 3 ,4 ,5,8-tetramethoxy-2 ,2 -dimethylpyrano by MeOH to give compound 4 (19 mg). Fraction E8 (1.8 g) (5 ,6 :6,7)-flavone (10)[27, 28]. was rechromatographed on polyamide column (35 × 2.5 cm) Compound 1 was obtained as a pale yellow amorphous using EtOH/H2O (8 : 2) to afford three major subfractions powder. The UV spectrum showed maxima at 258 and (E8-1, E8-2, and E8-3), and these subfractions were purified 335 nm, suggesting a flavone moiety [28]. The IR spectrum −1 on Sephadex LH-20 columns using MeOH as an eluent to displayed strong bands for OH (3371 cm )andconjugated 5 6 7 −1 yield the purified compounds (27 mg), (17 mg), and carbonyl (1691 cm ). The HREIMS mass spectrum revealed 8 9 10 + (24 mg). Compounds (14 mg), (22 mg), and (18 mg) a [M + H] ion at / 590.5124 corresponding to the were obtained from fraction E9 (750 mg) after application to 1 13 molecular formula C28H30O14.The Hand CNMR Sephadex LH-20 columns using MeOH/H2O(9.5:0.5)asan spectrum of 1 (Table 1), recorded in DMSO-6,showeda eluent to yield three major successive subfractions (E9-1, E9- downfield conjugated carbonyl C 178.2 (C-4) and displayed a 2, and E9-3). Subfraction E9-1 was purified on Sephadex LH- =8.9 8 pair of aromatic protons at H 7. 5 1 a n d 6 . 9 5 ( 1 H , , Hz 20 columns using MeOH as an eluent to afford compound . each). The values of 8.9 Hz indicated an ortho-coupling, Subfractions E9-2 and E9-3 were further purified by ODS CC hence diagnostic for protons at positions C-5 and C-6, using MeOH/H2O (8 : 2) to yield compounds 9 and 10.
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