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BioMed Research International
Volume 2014 (2014), Article ID 752941, 14 pages
http://dx.doi.org/10.1155/2014/752941
Research Article

Antiproliferative Activity of the Isofuranonaphthoquinone Isolated from Bulbine frutescens against Jurkat T Cells

1School of Pharmacy, College of Health Sciences, University of Zimbabwe, Mount Pleasant, Harare, Zimbabwe
2The African Academy of Sciences, P.O. Box 24916, Nairobi, Kenya
3Biomolecular Interactions Analyses Group, Department of Biochemistry, University of Zimbabwe, P.O. Box MP 167, Mount Pleasant, Harare, Zimbabwe

Received 30 April 2013; Revised 19 August 2013; Accepted 29 October 2013; Published 16 January 2014

Academic Editor: Ajit S. Narang

Copyright © 2014 Penelope Tambama et al. 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.

Linked References

  1. B. A. J. Ponder, “Cancer genetics,” Nature, vol. 411, no. 6835, pp. 336–341, 2001. View at Publisher · View at Google Scholar · View at Scopus
  2. P. Duesberg, R. Li, A. Fabarius, and R. Hehlmann, “The chromosomal basis of cancer,” Cellular Oncology, vol. 27, no. 5-6, pp. 293–318, 2005. View at Scopus
  3. J. D. Martinez, M. T. Parker, K. E. Fultz, et al., “Molecular biology of cancer,” Journal of Clinical Oncology, vol. 20, pp. 325–334, 2003.
  4. S. Mukanganyama, S. Dumbura, and L. Mampuru, “Antiproliferative effects of plant extracts from Zimbabwean medicinal plants against human Leukemia cell lines,” The African Journal of Plant Science and Biotechnology, vol. 6, pp. 14–20, 2012.
  5. K. C. Mouli, T. Vijaya, and S. D. Rao, “Phytoresources as potential therapeutic agents for cancer treatment and prevention,” Journal of Global Pharma Technology, vol. 1, pp. 4–18, 2009.
  6. R. Pinar, “To investigate knowledge of Turkish people about cancer,” Cancer Agenda, vol. 2, pp. 66–73, 1998.
  7. “NCI International Portfolio: Addressing the Global Challenge of Cancer,” National Cancer Institute, Bethesda, Md , USA, 2006, http://cgch.lshtm.ac.uk/tobacco/nci-international-portfolio.pdf.
  8. E. Chokunonga, M. Z. Borok, Z. M. Chirenje, et al., “Pattern of cancer in Zimbabwe,” Zimbabwe National Cancer Registry for 2006 Annual Report, 2010.
  9. D. C. Whiteman and A. C. Green, “Melanoma and sun exposure: where are we now?” International Journal of Dermatology, vol. 38, no. 7, pp. 481–489, 1999. View at Publisher · View at Google Scholar · View at Scopus
  10. R. Goldman, L. Enewold, E. Pellizzari et al., “Smoking increases carcinogenic polycyclic aromatic hydrocarbons in human lung tissue,” Cancer Research, vol. 61, no. 17, pp. 6367–6371, 2001. View at Scopus
  11. M. A. Knowles and P. J. Selby, Introduction to the Cellular and Molecular Biology of Cancer, Oxford University Press, 4th edition, 2007.
  12. L. P. Bignold, B. L. Coghlan, and H. P. Jersmann, “Cancer morphology, carcinogenesis and genetic instability: a background,” EXS, vol. 96, pp. 1–24, 2006. View at Scopus
  13. R. K. Oldham, “Biologicals and biological response modifiers: fourth modality of cancer treatment,” Cancer Treatment Reports, vol. 68, no. 1, pp. 221–232, 1984. View at Scopus
  14. M. M. Gottesman, “Mechanisms of cancer drug resistance,” Annual Review of Medicine, vol. 53, pp. 615–627, 2002. View at Publisher · View at Google Scholar · View at Scopus
  15. N. Noda and H. Wakasugi, “Cancer and oxidative stress,” Japanese Medical Association Journal, vol. 44, pp. 535–539, 2001.
  16. K. N. Agbafor and N. Nwachukwu, “Phytochemical analysis and antioxidant property of leaf extracts of vitex doniana and Mucuna pruriens,” Biochemistry Research International, vol. 2011, Article ID 459839, 4 pages, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. J. M. Mates, C. Perez-Gomez, and I. Nunez de Castro, “Antioxidant enzymes and human diseases,” Clinical Biochemistry, vol. 32, pp. 595–603, 1999.
  18. T. B. Kryston, A. B. Georgiev, P. Pissis, and A. G. Georgakilas, “Role of oxidative stress and DNA damage in human carcinogenesis,” Mutation Research, vol. 711, no. 1-2, pp. 193–201, 2011. View at Publisher · View at Google Scholar · View at Scopus
  19. T. Shinya, K. Okamoto, J. Yodoi, and H. Hiai, “Persistent oxidative stress in cancer,” Federation of European Biochemical Societies Letters, vol. 358, pp. 1–3, 1995.
  20. A.-P. Arrigo, “Gene expression and the thiol redox state,” Free Radical Biology and Medicine, vol. 27, no. 9-10, pp. 936–944, 1999. View at Publisher · View at Google Scholar · View at Scopus
  21. H. E. Poulsen, H. Prieme, and S. Loft, “Role of oxidative DNA damage in cancer initiation and promotion,” European Journal of Cancer Prevention, vol. 7, no. 1, pp. 9–16, 1998. View at Scopus
  22. S. Loft and H. E. Poulsen, “Cancer risk and oxidative DNA damage in man,” Journal of Molecular Medicine, vol. 74, no. 6, pp. 297–312, 1996. View at Publisher · View at Google Scholar · View at Scopus
  23. K. C. Mouli, T. Vijaya, and S. D. Rao, “Phytoresources as potential therapeutic agents for cancer treatment and prevention,” Journal of Global Pharma Technology, vol. 1, pp. 4–18, 2009.
  24. Z. Saify, N. Mushtaq, F. Noor, et al., “Role of Quinone moiety as antitumor agents: a review,” Pakistan Journal of Pharmaceutical Science, vol. 12, pp. 21–31, 1999.
  25. R. R. Kitagawa, W. Vilegas, I. Z. Carlos, and M. S. G. Raddi, “Antitumor and immunomodulatory effects of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin,” Brazilian Journal of Pharmacognosy, vol. 21, no. 6, pp. 1084–1088, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. L. H. Hartwell and M. B. Kastan, “Cell cycle control and cancer,” Science, vol. 266, no. 5192, pp. 1821–1828, 1994. View at Scopus
  27. R. R. T. Majinda, B. M. Abegaz, M. Bezabih et al., “Recent results from natural product research at the University of Botswana,” Pure and Applied Chemistry, vol. 73, no. 7, pp. 1197–1208, 2001. View at Scopus
  28. B. E. van Wyk, A. Yenesew, and E. Dagne, “Chemotaxonomic significance of anthraquinones in the roots of Asphodeloideae (Asphodelaceae),” Biochemical Systematics and Ecology, vol. 23, no. 3, pp. 277–281, 1995. View at Publisher · View at Google Scholar · View at Scopus
  29. B. M. Abegaz, M. Bezabih, T. Msuta et al., “Gaboroquinones A and B and 4′-O-demethylknipholone-4′-O-α-D-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens,” Journal of Natural Products, vol. 65, no. 8, pp. 1117–1121, 2002. View at Publisher · View at Google Scholar · View at Scopus
  30. K. Rajandeep, K. Karan, and K. Harpreet, “Plants as a source of anticancer agents,” Journal of Natural Products and Plant Resources, vol. 1, pp. 119–124, 2011.
  31. A. D. Kinghorn, J. Esperanza, E. J. C. de Blanco et al., “Discovery of anticancer agents of diverse natural origin,” Pure and Applied Chemistry, vol. 81, no. 6, pp. 1051–1063, 2009. View at Publisher · View at Google Scholar · View at Scopus
  32. G. M. Cragg and D. J. Newman, “Plants as a source of anti-cancer agents,” Journal of Ethnopharmacology, vol. 100, no. 1-2, pp. 72–79, 2005. View at Publisher · View at Google Scholar · View at Scopus
  33. S. Mukanganyama, M. Bezabih, M. Robert et al., “The evaluation of novel natural products as inhibitors of human glutathione transferase P1-1,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 26, no. 4, pp. 460–467, 2011. View at Publisher · View at Google Scholar · View at Scopus
  34. B. Mannervik, “Five decades with glutathione and the GSTome,” The Journal of Biological Chemistry, vol. 287, no. 9, pp. 6072–6083, 2012. View at Publisher · View at Google Scholar · View at Scopus
  35. S. A. Terlouw, R. Masereeuw, P. H. H. van den Broek, S. Notenboom, and F. G. M. Russel, “Role of multidrug resistance protein 2 (MRP2) in glutathione-bimane efflux from Caco-2 and rat renal proximal tubule cells,” British Journal of Pharmacology, vol. 134, no. 5, pp. 931–938, 2001. View at Scopus
  36. S. Mohammad, “Anticancer agents from medicinal plants,” Bangladesh Journal of Pharmacology, vol. 2, pp. 35–41, 2006.
  37. K. Zandi, S. Tajbakhsh, I. Nabipour et al., “In vitro antitumor activity of gracilaria corticata (a red alga) against jurkat and molt-4 human cancer cell lines,” African Journal of Biotechnology, vol. 9, no. 40, pp. 6787–6790, 2010. View at Scopus
  38. M. A. Moosavi, R. Yazdanparast, and M. H. Sanati, “The cytotoxic and anti-proliferative effects of 3-hydrogenkwadaphnin in K562 and Jurkat cells is reduced by guanosine,” Journal of Biochemistry and Molecular Biology, vol. 38, no. 4, pp. 391–398, 2005. View at Scopus
  39. S. Syeda, S. Sandhya, K. R. Vinod, et al., “Pharmacognostic studies on the leaf of ventilago mederaspatana,” International Journal of Pharmaceutical and Clinical Research, vol. 2, pp. 51–53, 2010.
  40. B. Chittethu Amrutha, S. Sathianarayanan, A. Nair, et al., “Preliminary phytochemical screening and cytotoxicity activity of ethanolic extract of Ventilago madraspatana against human breast cancer,” International Journal of Pharmacology, vol. 5, pp. 75–78, 2011.
  41. P. J. Thornalley, M. D'Arcy Doherty, M. T. Smith, J. V. Bannistera, and G. M. Cohen, “The formation of active oxygen species following activation of 1-naphthol, 1,2- and 1,4-naphthoquinone by rat liver microsomes,” Chemico-Biological Interactions, vol. 48, no. 2, pp. 195–206, 1984. View at Publisher · View at Google Scholar · View at Scopus
  42. A. Begleiter, “Cytocidal action of the quinone group and its relationship to antitumor activity,” Cancer Research, vol. 43, no. 2, pp. 481–484, 1983. View at Scopus
  43. R. R. Kitagawa, W. Vilegas, I. Z. Carlos, and M. S. G. Raddi, “Antitumor and immunomodulatory effects of the naphthoquinone 5-methoxy-3,4-dehydroxanthomegnin,” Brazilian Journal of Pharmacognosy, vol. 21, no. 6, pp. 1084–1088, 2011. View at Publisher · View at Google Scholar · View at Scopus
  44. J. Verrax, R. Beck, N. Dejeans et al., “Redox-active quinones and ascorbate: an innovative cancer therapy that exploits the vulnerability of cancer cells to oxidative stress,” Anti-Cancer Agents in Medicinal Chemistry, vol. 11, no. 2, pp. 213–221, 2011. View at Scopus
  45. A. Prasad and N. Rao, “Erythrocyte glutathione system and plasma protein oxidation in thyroid dysfunction,” Pharmacie Globale International Journal of Comprehensive Pharmacy, vol. 3, pp. 1–4, 2012.
  46. A. L. Ortega, S. Mena, and J. M. Estrela, “Glutathione in cancer cell death,” Cancers, vol. 3, no. 1, pp. 1285–1310, 2011. View at Publisher · View at Google Scholar · View at Scopus
  47. V. R. Tandon, S. Sharma, A. Mahajan, et al., “Oxidative stress: a novel strategy in cancer treatment,” JK Science, New Horizons, vol. 7, pp. 1–3, 2005.
  48. D. Trachootham, J. Alexandre, and P. Huang, “Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach?” Nature Reviews Drug Discovery, vol. 8, no. 7, pp. 579–591, 2009. View at Publisher · View at Google Scholar · View at Scopus
  49. L. G. Nicolson and R. Settineri, “Lipid replacement therapy: a functional food approach with new formulations for reducing cellular oxidative damage, cancer-associated fatigue and the adverse effects of cancer therapy,” Functional Foods in Health and Disease, vol. 4, pp. 135–160, 2011.
  50. I. Dalle-Donne, D. Giustarini, R. Colombo, R. Rossi, and A. Milzani, “Protein carbonylation in human diseases,” Trends in Molecular Medicine, vol. 9, no. 4, pp. 169–176, 2003. View at Publisher · View at Google Scholar · View at Scopus
  51. L. Gibellini, M. Pinti, M. Nasi et al., “Interfering with ROS metabolism in cancer cells: the potential role of quercetin,” Cancers, vol. 2, no. 2, pp. 1288–1311, 2010. View at Publisher · View at Google Scholar · View at Scopus
  52. D. Exinger, E. Francoise, M. Bertrand, et al., “Multitargeted antifolate (Pemetrexed): a comprehensive review of its mechanisms of action, recent results and future prospects,” Cancer Therapy, vol. 1, pp. 315–322, 2003.
  53. M. Nishiyama, W. Yamamoto, J.-S. Park et al., “Low-dose cisplatin and 5-fluorouracil in combination can repress increased gene expression of cellular resistance determinants to themselves,” Clinical Cancer Research, vol. 5, no. 9, pp. 2620–2628, 1999. View at Scopus
  54. D. Russo, J. P. Marie, D. C. Zhou et al., “Coexpression of anionic glutathione-S-transferase (GSTπ) and multidrug resistance (mdr1) genes in acute myeloid and lymphoid leukemias,” Leukemia, vol. 8, no. 5, pp. 881–884, 1994. View at Scopus
  55. M. Y. Abdalla, “Glutathione as potential target for cancer therapy,” Jordan Journal of Biological Sciences, vol. 4, pp. 119–124, 2011.
  56. C. Xu, C. Y.-T. Li, and A.-N. T. Kong, “Induction of phase I, II and III drug metabolism/transport by xenobiotics,” Archives of Pharmacal Research, vol. 28, no. 3, pp. 249–268, 2005. View at Scopus
  57. A. S. Morgan, P. J. Ciaccio, K. D. Tew, and L. M. Kauvar, “Isozyme-specific glutathione S-transferase inhibitors potentiate drug sensitivity in cultured human tumor cell lines,” Cancer Chemotherapy and Pharmacology, vol. 37, no. 4, pp. 363–370, 1996. View at Publisher · View at Google Scholar · View at Scopus
  58. R. Hayeshi, F. Chinyanga, S. Chengedza, and S. Mukanganyama, “Inhibition of human glutathione transferases by multidrug resistance chemomodulators in vitro,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 21, no. 5, pp. 581–587, 2006. View at Publisher · View at Google Scholar · View at Scopus
  59. S. Mukanganyama, M. Widersten, Y. S. Naik, B. Mannervik, and J. A. Hasler, “Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance,” International Journal of Cancer, vol. 97, no. 5, pp. 700–705, 2002. View at Publisher · View at Google Scholar · View at Scopus
  60. R. Hayeshi, I. Mutingwende, W. Mavengere, V. Masiyanise, and S. Mukanganyama, “The inhibition of human glutathione S-transferases activity by plant polyphenolic compounds ellagic acid and curcumin,” Food and Chemical Toxicology, vol. 45, no. 2, pp. 286–295, 2007. View at Publisher · View at Google Scholar · View at Scopus
  61. J. J. van Zanden, O. B. Hamman, M. L. P. S. Van Iersel et al., “Inhibition of human glutathione S-transferase P1-1 by the flavonoid quercetin,” Chemico-Biological Interactions, vol. 145, no. 2, pp. 139–148, 2003. View at Publisher · View at Google Scholar · View at Scopus
  62. P. I. Homem de Bittencourt Jr. and R. Curi, “Antiproliferative prostaglandins and the MRP/GS-X pump role in cancer immunosuppression and insight into new strategies in cancer gene therapy,” Biochemical Pharmacology, vol. 62, no. 7, pp. 811–819, 2001. View at Publisher · View at Google Scholar · View at Scopus
  63. T. Ishikawa, J.-J. Bao, Y. Yamane et al., “Coordinated induction of MRP/GS-X pump and γ-glutamylcysteine synthetase by heavy metals in human leukemia cells,” The Journal of Biological Chemistry, vol. 271, no. 25, pp. 14981–14988, 1996. View at Publisher · View at Google Scholar · View at Scopus
  64. S. V. Ambudkar, C. Kimchi-Sarfaty, Z. E. Sauna, and M. M. Gottesman, “P-glycoprotein: from genomics to mechanism,” Oncogene, vol. 22, no. 47, pp. 7468–7485, 2003. View at Publisher · View at Google Scholar · View at Scopus
  65. T. Sugiyama and Y. Sadzuka, “Theanine, a specific glutamate derivative in green tea, reduces the adverse reactions of doxorubicin by changing the glutathione level,” Cancer Letters, vol. 212, no. 2, pp. 177–184, 2004. View at Publisher · View at Google Scholar · View at Scopus