European Journal of Chemistry

The cytotoxic activity of Linum grandiflorum leaves



Main Article Content

Magdy Mostafa Desoky Mohammed
Ming Chen
Lin Zhai
Nabaweya Ali Ibrahim

Abstract

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.

1_2_110_114_800


icon graph This Abstract was viewed 2359 times | icon graph Article PDF downloaded 1922 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Sang, K. L.; Kyung, A. N.; Yoen, H. H. Planta Med. 2003, 69, 21−25.
doi:10.1055/s-2003-37021
PMid:12567274

[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.
doi:10.1021/ac991296y
PMid:10763246

[5]. Hakkinen, S.; Auriola, S. J. Chromatog. A 1998, 829, 91−100.
doi:10.1016/S0021-9673(98)00756-0

[6]. Es-Safi, N. E.; Krhoas, L.; Einhorn, J.; Ducrot, P. H. Int. J. Mass Spectrom. 2005, 247, 93−100.
doi:10.1016/j.ijms.2005.10.002

[7]. Ma, Y. L.; Vedernikova, I.; Van Den Heuvel, H.; Claeys, M. J. Am. Soc. Mass Spectom. 2000, 11, 136−144.
doi:10.1016/S1044-0305(99)00133-6

[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.
PMid:2021931

[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.
doi:10.1093/jnci/82.13.1107

[12]. Seikel, M. K.; Chow, J. H. S.; Feldman, L. Phytochemistry 1966, 5, 439−455.
doi:10.1016/S0031-9422(00)82158-5

[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.
doi:10.1021/jo01291a027

[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.
doi:10.1016/j.ijms.2005.10.002

[21]. Cuyckens, F.; Rozenberg, R.; Hoffmann, E-D, Claeys, M. J. Mass Spectrom. 2001, 36, 1203−1210.
doi:10.1002/jms.224
PMid:11747116

[22]. Ma, Y. L.; Cuyckens, F.; Van Den Heuvel, H.; Claeys, M. Phytochem. Anal. 2001, 12, 159−165.
doi:10.1002/pca.573
PMid:11705020

[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.
doi:10.1255/ejms.559
PMid:12939492

[24]. Bylka, W.; Franski, R.; Stobiecki, M. J. Mass Spectrom. 2002, 37, 648−650.
doi:10.1002/jms.313
PMid:12112748

[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.
doi:10.1080/14786410802364168
PMid:19296395

[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.
doi:10.1016/0024-3205(94)00641-5

[28]. Giuseppe, G.; Peter, J. O. Free Radical Biol. & Med. 2004, 37, 287–303.
doi:10.1016/j.freeradbiomed.2004.04.034
PMid:15223063

[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.
doi:10.1016/S0960-894X(03)00197-5

[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.

Supporting Agencies

Danish Institute of Agricultural Sciences, Research Center Aarslev, Denmark and University of Southern Denmark, Odense, Denmark
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).