European Journal of Chemistry

The cytotoxic activity of Linum grandiflorum leaves

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Magdy Mostafa Desoky Mohammed
Ming Chen
Lin Zhai
Nabaweya Ali Ibrahim


The CHCl3 and MeOH fractions of the leaves of Linum grandiflorum, showed cytotoxic activity against EL4 (Murine Leukemia) cell line with IC50 = 60 and 250 mg/mL respectively. Bioassay guided fractionation and isolation (BGFI) of the MeOH fraction resulted in the isolation of two new cytotoxic compounds 1 [luteolin 7-O-α-D-(6```-E-feruloyl)glucopyranosyl (1→2)-β-D-glucopyranoside] and 6 [2-[(3`-isopropoxy-O-β-D-glucopyranosyl)oxy]-2-methylbutane nitrile] against EL4 with IC50 = 0.2 and 0.3 mM/mL respectively, together with 2 [luteolin 7-O-β-D-glucopyranoside], 3 [vicenin-1], 4 [vicenin-2], 5 [vicenin-3], 7 [linamarin], 8 [lotaustralin], 9 [neolinustatin], and  10 [butan-2-O-β-D-glucopyranoside] which showed cytotoxicity against EL4 with IC50 = 0.2, 0.9, 0.8, 0.9, 0.4, 0.4, 0.2, 0.4 mM/mL respectively. BGFI of the CHCl3 fraction revealed the isolation of three cytotoxic aryltetrahydronaphthalene-type lignans identified as 11 [podophyllotoxin], 12 [deoxypodophylotoxin] and 13 [5-methoxypodophyllotoxin] against EL4 with IC50 = 0.2, 0.09 and 0.2 mM/mL respectively. The isolated compounds were structurally elucidated using 1D, 2D NMR, HR-ESI-MS, and HR-MALDI-MS techniques.


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Mohammed, M. M. D.; Chen, M.; Zhai, L.; Ibrahim, N. A. The Cytotoxic Activity of Linum Grandiflorum Leaves. Eur. J. Chem. 2010, 1, 110-114.

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[1]. Sang, K. L.; Kyung, A. N.; Yoen, H. H. Planta Med. 2003, 69, 21−25.

[2]. Bown D. Encyclopedia of Herbs and their Uses. Dorling Kindersley, London, 1995.

[3]. Hartwell J. L. Plants Used Against Cancer. A Survey. Quarterman Publication Inc., USA, 1982. p. 350.

[4]. Nielsen, S. E.; Freese, R.; Cornett, C.; Dragsted, L. O. Anal. Chem. 2000, 72, 1503−1509.

[5]. Hakkinen, S.; Auriola, S. J. Chromatog. A 1998, 829, 91−100.

[6]. Es-Safi, N. E.; Krhoas, L.; Einhorn, J.; Ducrot, P. H. Int. J. Mass Spectrom. 2005, 247, 93−100.

[7]. Ma, Y. L.; Vedernikova, I.; Van Den Heuvel, H.; Claeys, M. J. Am. Soc. Mass Spectom. 2000, 11, 136−144.

[8]. Mabry T. J.; Markham K. R.; Thomas M. B. The Systematic Identification of Flavonoids. Springer, Berlin, 1970.

[9]. Vistica, D.T.; Skehan, P.; Scudiero, D.; Monks, A.; Pittman, A.; Boyd, M.R. Cancer Res. 1991, 51, 2515−2520.

[10]. Rubinstein, L.V.; Paull, K.D.; Shoemaker, R.H.; Simon, R. M.; Tosini, S.; Skehan, P.; Scudiero, D.A.; Monks, A.; Boyd, M.R. Cancer Res. 1989, 30, 607−613.

[11]. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; Mcmahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. J. Natl. Cancer Inst. 1990, 82, 1107–1112.

[12]. Seikel, M. K.; Chow, J. H. S.; Feldman, L. Phytochemistry 1966, 5, 439−455.

[13]. Harborne J. B. The Flavonoids in Advances in Research since 1986. Chapman & Hall, New York, 1994.

[14]. Cecil, R. S. Jr.; David, W.; Roger, W.; Miller, I. S. P.; Oscar, E. O. J. Org. Chem. 1980, 45, 507−510.

[15]. Cable, J.; Nocke, H. Australian J. Chem. 1975, 28, 2737−2739.

[16]. Mohammed M. M. D. Phytochemical and Biological Studies on Linum grandiflorum (Linaceae) and Ixora undulata (Rubiaceae) Growing in Egypt. Doctoral Thesis, Menoufia University, Egypt, 2008.

[17]. Ayres, D. C.; Loike, J. D. Chemistry and Pharmacology of Natural Products. Lignans: Chemistry, Biological, and Clinical Properties. Cambridge University Press, Cambridge, 1990. p. 138.

[18]. Day, P. M.; Harborne, J. B. Plant Phenolics. (Vol. 1). In Methods in Plant Biochemistry. Academic Press, London, 1989.

[19]. David, N.; Michael, P. W. The Nuclear Overhauser Effect in Structural and Conformational Analysis. Wiley-VCH Publishers INC., New York, 1989 & 2000.

[20]. Es-Safi, N. E.; Krhoas, L.; Einhorn, J.; Ducrot, P-H. Int. J. Mass Spectrom. 2005, 247, 93−100.

[21]. Cuyckens, F.; Rozenberg, R.; Hoffmann, E-D, Claeys, M. J. Mass Spectrom. 2001, 36, 1203−1210.

[22]. Ma, Y. L.; Cuyckens, F.; Van Den Heuvel, H.; Claeys, M. Phytochem. Anal. 2001, 12, 159−165.

[23]. Cuyckens, F.; Shahat, A. A.; Van den Heuvel, H.; Abdel-Shafeek, K. A.; El-Messiry, M. M.; Seif El-Nasr, M. M.; Pieters, L.; Vlietinck, A. J.; Claeys, M. Eur. J. Mass Spectrom. 2003, 9, 409−420.

[24]. Bylka, W.; Franski, R.; Stobiecki, M. J. Mass Spectrom. 2002, 37, 648−650.

[25]. Mohammed, M. M. D.; Christensen, L. P.; Ibrahim, N. A.; Awad, N. E.; Zeid, I. F.; Pedersen, E. B. Nat. Prod. Res. 2009, 23(5), 489−497.

[26]. Suolina, E. M.; Buchsbaum, R. N.; Racker, E. Cancer Res. 1975, 35, 1865−1872.

[27]. Hirano, T.; Gotoh, M.; Oka, K. Life Sci. 1994, 55, 1061−1069.

[28]. Giuseppe, G.; Peter, J. O. Free Radical Biol. & Med. 2004, 37, 287–303.

[29]. Lopez-Lazaro, M.; Martin-Cordero, C.; Cortes, F.; Pinero, J.; Ayuso, M. J. Z. Naturforch. (Section C) 2000, 55, 40−43.

[30]. Wu, J. H.; Wang, X. H.; Yi, Y. H.; Lee, K. H. Bioorg. Med. Chem. Lett. 2003, 13, 1813−1815.

[31]. Norman R. F. J. Pharmaceut. Sci. 1966, 55, 225−276.

[32]. Raphael I. Selected Topics in the Chemistry of Scientific Research. World Scientific Publishing Co. Pte. Ltd., Singapore, 2008. p. 471.

[33]. Gordon, M. C.; David, G. I. K.; David, J. N. Anticancer Agents from Natural Products. CRC Press Taylor & Francis Group, Boca Raton FL., 2005.

[34]. Kalwinskyl, D. K.; Look, A. T.; Ducore, J.; Fridland, A. Cancer Res. 1983, 43, 1592−1597.

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