Available online on www.ijppr.com International Journal of Pharmacognosy and Phytochemical Research 2016; 8(11); 1839-1843 ISSN: 0975-4873 Research Article *Author for Correspondence: sross@olemiss.edu Flavonoids from Leucanthemopsis trifurcatum Leaves and their Cytotoxic Activity Wael M Abdel-Mageed 1,2* , Ahmed A Attia 2 , Muneera S M Al-Saleem 3 , Maged S Abdel- Kader 4 , Krishna Bolla 5 , Samir A Ross 6,7* 1 Pharmacognosy Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia. 2 Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. 3 Chemistry Department, Science College, Princess Noura bint Abdul Rahaman University, Riyadh 11671, Saudi Arabia. 4 Department of Pharmacognosy, College of Pharmacy, Sattam Bin Abdulaziz University, Al-kharj 11942, Saudi Arabia. 5 Department of Microbiology, Kakatiya University, Warangal – 506009 Telangana, India. 6 National Center for Natural Products Research, University of Mississippi, MS 38677, USA. 7 Department of Pharmacognosy, School of Pharmacy, University of Mississippi, MS 38677, USA. Available Online: 15 th November, 2016 ABSTRACT A radical scavenging guided phytochemical study on the leaf of Leucanthemopsis trifurcatum afforded twelve flavonoids (1-12). The structures of the isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. The cytotoxic activity of the isolated compounds was evaluated against human Hela and MCF-7 cell lines. Compound 1 displays the strongest cytotoxic activity with IC50 values of 10.3 (Hela) and 12.2 μ M (MCF-7). Keywords: Leucanthemopsis trifurcatum; Chrysanthemum macrocephalum; Flavonoids; cytotoxicity. INTRODUCTION The genus Leucanthemopsis belongs to the family Asteraceae, with only 6 species widespread mainly in Southwestern Europe, and North Africa 1,2 . Leucanthemopsis trifurcatum (Desf.) Alavi. is a sub-shrub distributed mainly in Tunisia, Morocco, Algeria and Libya and is known by the following synonyms: Chrysanthemum trifurcatum Desf.; Chrysanthemum macrocephalum Viv.; and Pyrethrum trifurcatum (Desf.) Willd 3 . Previous phytochemical reports of the genus Leucanthemopsis revealed the isolation and identification of phloroglucinol derivatives and sesquiterpenoid lactones 1,2,4,5 . To the best of our knowledge, no hits were reported about the chemical constituents of L. trifurcatum which encourage us to investigate its active constituents and potential biological activities. We report here the isolation and identification of 12 flavonoids 1-12 , which were isolated for the first time from this plant. The structures of these compounds were deduced by comparison of their spectral data with those reported in the literature. In our continuous interest to search for drug leads from natural sources, we had the opportunity to work on the leaves of L. trifurcatum to investigate its chemical constituents and their potential biological activities. MATERIALS AND METHODS Apparatus and Chemicals UV spectra were obtained on a Cary 50 spectrophotometer, Varian, Inc. NMR spectra were recorded at 23 °C with a Varian Inova 600 MHz NMR spectrometer. Column chromatography (CC) was performed using a silica gel (Kieselgel 60 Å, 40-63 μM mesh size, Fluorochem, UK). RP-HPLC were carried out using Phenomenex Luna C18 (2) (250 × 4.6 mm) (5 μm) on Shimadzu HPLC-LC-20 AD series binary gradient pump with Shimadzu SPD-M20A detector (Tokyo, Japan). All flash chromatography was performed on Sepacore Flash Chromatography System, Buchi Labortechnik AG, Netherlands. TLC was done using pre-coated silica-gel 60 F254 (0.25 mm, ALUGRAM® SIL G/UV254, Macherey-Nagel, Germany) and RP-18 F254 plates (0.25 mm, Merck, Germany). Plant material The plant was collected at the end of April 2010 from the northeastern region of Libya. The plant material was identified by the members of Plant Taxonomy Department, College of Science, Assiut University. Extraction and isolation 400 g of the air-dried powdered leaves were extracted by maceration (72 h x 3) with 70% EtOH till complete exhaustion (2L x 3). The alcoholic extract was concentrated and the solvent free residue (29 g, 7.3%) was mixed with 500 mL of distilled H2O, and subjected to successive solvent fractionation with n-hexane and chloroform till complete exhaustion in each case to give n- hexane fraction (7.3 g), chloroform fraction (5.5 g), and aqueous fraction (13.8 g). The chloroform fraction was subjected to flash chromatography on silica gel column using CHCl3–MeOH mixtures in a manner of increasing polarities. Thirty-two fractions (20 mL each) were collected and monitored on TLC (silica gel) using CHCl3–