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Advances in Pharmacological Sciences
Volume 2014, Article ID 847574, 8 pages
http://dx.doi.org/10.1155/2014/847574
Research Article

Comparative Evaluation of Cytotoxic and Apoptogenic Effects of Several Coumarins on Human Cancer Cell Lines: Osthole Induces Apoptosis in p53-Deficient H1299 Cells

1Novel Drug Delivery Research Center, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah 6734667149, Iran
2Department of Pharmacognosy and Biotechnology, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah 6734667149, Iran
3Students Research Committee, School of Pharmacy, Kermanshah University of Medical Sciences, Kermanshah 6734667149, Iran
4Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah 6734667149, Iran

Received 25 June 2014; Accepted 12 August 2014; Published 3 September 2014

Academic Editor: Ismail Laher

Copyright © 2014 Yalda Shokoohinia 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. H. Itokawa, S. L. Morris-Natschke, T. Akiyama, and K.-H. Lee, “Plant-derived natural product research aimed at new drug discovery,” Journal of Natural Medicines, vol. 62, no. 3, pp. 263–280, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. K. N. Venugopala, V. Rashmi, and B. Odhav, “Review on natural coumarin lead compounds for their pharmacological activity,” BioMed Research International, vol. 2013, Article ID 963248, 14 pages, 2013. View at Publisher · View at Google Scholar · View at Scopus
  3. K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, and D. N. Nicolaides, “Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities,” Current Pharmaceutical Design, vol. 10, no. 30, pp. 3813–3833, 2004. View at Publisher · View at Google Scholar · View at Scopus
  4. A. Ghannadi, K. Fattahian, Y. Shokoohinia, M. Behbahani, and A. Shahnoush, “Anti-viral evaluation of sesquiterpene coumarins from Ferula assa-foetida against HSV-1,” Iranian Journal of Pharmaceutical Research, vol. 13, pp. 523–530, 2014. View at Google Scholar
  5. T. Ojala, S. Remes, P. Haansuu et al., “Antimicrobial activity of some coumarin containing herbal plants growing in Finland,” Journal of Ethnopharmacology, vol. 73, no. 1-2, pp. 299–305, 2000. View at Publisher · View at Google Scholar · View at Scopus
  6. I. Kostova, “Synthetic and natural coumarins as cytotoxic agents,” Current Medicinal Chemistry—Anti-Cancer Agents, vol. 5, no. 1, pp. 29–46, 2005. View at Publisher · View at Google Scholar · View at Scopus
  7. S. W. Yoo, J. S. Kim, S. S. Kang et al., “Constituents of the fruits and leaves of Euodia daniellii,” Archives of Pharmacal Research, vol. 25, pp. 824–830, 2002. View at Publisher · View at Google Scholar
  8. S. S. Bhattacharyya, S. Paul, A. de et al., “Poly (lactide-co-glycolide) acid nanoencapsulation of a synthetic coumarin: cytotoxicity and bio-distribution in mice, in cancer cell line and interaction with calf thymus DNA as target,” Toxicology and Applied Pharmacology, vol. 253, no. 3, pp. 270–281, 2011. View at Publisher · View at Google Scholar · View at Scopus
  9. P.-C. Liao, S.-C. Chien, C.-L. Ho et al., “Osthole regulates inflammatory mediator expression through modulating NF-κB, mitogen-activated protein kinases, protein kinase C, and reactive oxygen species,” Journal of Agricultural and Food Chemistry, vol. 58, no. 19, pp. 10445–10451, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. E. Shin, C. Lee, S. H. Sung, Y. C. Kim, B. Y. Hwang, and M. K. Lee, “Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells,” Journal of Natural Medicines, vol. 65, no. 2, pp. 370–374, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. T. Murata, M. Itoigawa, C. Ito et al., “Induction of apoptosis in human leukaemia HL-60 cells by furanone-coumarins from Murraya siamensis,” Journal of Pharmacy and Pharmacology, vol. 60, no. 3, pp. 385–389, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. S. E. Sajjadi, H. Zeinvand, and Y. Shokoohinia, “Isolation and identification of osthol from the fruits and essential oil composition of the leaves of Prangos asperula Boiss,” Research in Pharmaceutical Sciences, vol. 4, no. 1, pp. 19–23, 2009. View at Google Scholar · View at Scopus
  13. S. E. Sajjadi, Y. Shokoohinia, and S. Hemmati, “Isolation and identification of furanocoumarins and a phenylpropanoid from the acetone extract and identification of volatile constituents from the essential oil of Peucedanum pastinacifolium,” Chemistry of Natural Compounds, pp. 1–4, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. A. Ghahreman, Flora of Iran, Research Institute of Forests and Rangelands Publication, Tehran, Iran, 1986.
  15. N. Kafash-Farkhad, M. Asadi-Samani, and M. Rafieian-Kopaei, “A review on phytochemistry and pharmacological effects of Prangos ferulacea (L.) Lindl,” Life Science Journal, vol. 10, no. 8, pp. 360–367, 2013. View at Google Scholar · View at Scopus
  16. H. Sadraei, Y. Shokoohinia, S. E. Sajjadi, and B. Ghadirian, “Antispasmodic effect of osthole and prangos ferulacea extract on rat uterus smooth muscle motility,” Research in Pharmaceutical Sciences, vol. 7, no. 3, pp. 141–149, 2012. View at Google Scholar · View at Scopus
  17. H. Sadraei, Y. Shokoohinia, S. E. Sajjadi, and M. Mozafari, “Antispasmodic effects of Prangos ferulacea acetone extract and its main component osthole on ileum contraction,” Research in Pharmaceutical Sciences, vol. 8, no. 2, pp. 137–144, 2013. View at Google Scholar · View at Scopus
  18. Y. Shokoohinia, S. E. Sajjadi, S. Gholamzadeh, A. Fattahi, and M. Behbahani, “Antiviral and cytotoxic evaluation of coumarins from Prangos ferulacea (L.) Lindl,” Pharmaceutical Biology, 2014. View at Publisher · View at Google Scholar
  19. A. Z. Abyshev, “Coumarin composition of the roots, stems, and fruit of Prangos lophoptera,” Chemistry of Natural Compounds, vol. 10, no. 6, pp. 731–733, 1976. View at Publisher · View at Google Scholar · View at Scopus
  20. O. Rakotoarison, I. Rabenau, A. Lobstein et al., “Vasorelaxing properties and bio-guided fractionation of Cedrelopsis grevei,” Planta Medica, vol. 69, no. 2, pp. 179–181, 2003. View at Publisher · View at Google Scholar · View at Scopus
  21. L. Xie, Y. Takeuchi, L. M. Cosentino, and K.-H. Lee, “Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3′R,4′R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents,” Journal of Medicinal Chemistry, vol. 42, no. 14, pp. 2662–2672, 1999. View at Publisher · View at Google Scholar · View at Scopus
  22. L. Xie, Y. Takeuchi, L. M. Cosentino, and K.-H. Lee, “Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3′R,4′R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents,” Journal of Medicinal Chemistry, vol. 42, no. 14, pp. 2662–2672, 1999. View at Publisher · View at Google Scholar · View at Scopus
  23. G. W. Ivie, “Linear furocoumarins (psoralens) from the seed of Texas Ammi majus L. (Bishop's weed),” Journal of Agricultural and Food Chemistry, vol. 26, no. 6, pp. 1394–1403, 1978. View at Publisher · View at Google Scholar · View at Scopus
  24. R. Liu, A. Li, and A. Sun, “Preparative isolation and purification of coumarins from Angelica dahurica (Fisch. ex Hoffm) Benth, et Hook. f (Chinese traditional medicinal herb) by high-speed counter-current chromatography,” Journal of Chromatography A, vol. 1052, no. 1-2, pp. 223–227, 2004. View at Publisher · View at Google Scholar · View at Scopus
  25. M. E. Kaighn, K. S. Narayan, Y. Ohnuki, J. F. Lechner, and L. W. Jones, “Establishment and characterization of a human prostatic carcinoma cell line (PC-3),” Investigative Urology, vol. 17, no. 1, pp. 16–23, 1979. View at Google Scholar · View at Scopus
  26. R. C. Seeger, S. A. Rayner, A. Banerjee et al., “Morphology, growth, chromosomal pattern, and fibrinolytic activity of two new human neuroblastoma cell lines,” Cancer Research, vol. 37, no. 5, pp. 1364–1371, 1977. View at Google Scholar · View at Scopus
  27. H. L. Mao, P. S. Liu, J. F. Zheng et al., “Transfection of Smac/DIABLO sensitizes drug-resistant tumor cells to TRAIL or paclitaxel-induced apoptosis in vitro,” Pharmacological Research, vol. 56, no. 6, pp. 483–492, 2007. View at Publisher · View at Google Scholar · View at Scopus
  28. O. Porichi, M.-E. Nikolaidou, A. Apostolaki et al., “BCL-2, BAX and P53 expression profiles in endometrial carcinoma as studied by real-time PCR and immunohistochemistry,” Anticancer Research, vol. 29, no. 10, pp. 3977–3982, 2009. View at Google Scholar · View at Scopus
  29. L. Hosseinzadeh, J. Behravan, F. Mosaffa, G. Bahrami, A. R. Bahrami, and G. Karimi, “Effect of curcumin on doxorubicin-induced cytotoxicity in h9c2 cardiomyoblast cells,” Iranian Journal of Basic Medical Sciences, vol. 14, no. 1, pp. 49–56, 2011. View at Google Scholar · View at Scopus
  30. L. Hosseinzadeh, A. Khorand, and A. Aliabadi, “Discovery of 2-phenyl-N-(5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)acetamide derivatives as apoptosis inducers via the caspase pathway with potential anticancer activity,” Archiv der Pharmazie, vol. 346, no. 11, pp. 812–818, 2013. View at Publisher · View at Google Scholar
  31. W. Chen, Z. Zhao, L. Li et al., “Hispolon induces apoptosis in human gastric cancer cells through a ROS-mediated mitochondrial pathway,” Free Radical Biology and Medicine, vol. 45, no. 1, pp. 60–72, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. L. Hosseinzadeh, J. Behravan, F. Mosaffa, G. Bahrami, A. Bahrami, and G. Karimi, “Curcumin potentiates doxorubicin-induced apoptosis in H9c2 cardiac muscle cells through generation of reactive oxygen species,” Food and Chemical Toxicology, vol. 49, no. 5, pp. 1102–1109, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. M. Kawase, H. Sakagami, N. Motohashi et al., “Coumarin derivatives with tumor-specific cytotoxicity and multidrug resistance reversal activity,” In Vivo, vol. 19, no. 4, pp. 705–712, 2005. View at Google Scholar · View at Scopus
  34. L.-L. Yang, M.-C. Wang, L.-G. Chen, and C.-C. Wang, “Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines,” Planta Medica, vol. 69, no. 12, pp. 1091–1095, 2003. View at Publisher · View at Google Scholar · View at Scopus
  35. L. Wu, X. Huang, J. Li, and R. Zhang, “Haibo Hu Recent advances in the multifunction of a natural occurring coumarin: osthole,” Journal of Intercultural Ethnopharmacology, vol. 2, pp. 57–66, 2013. View at Google Scholar
  36. J. H. Kang and D. S. Yim, “Effect of isoimperatorin on the proliferation of prostate cancer cell line DU145 cells,” Biomolecules & Therapeutics, vol. 13, 189, no. 185, 2005. View at Google Scholar
  37. J. S. Lopez-Gonzalez, H. Prado-Garcia, D. Aguilar-Cazares, J. A. Molina-Guarneros, J. Morales-Fuentes, and J. J. Mandoki, “Apoptosis and cell cycle disturbances induced by coumarin and 7-hydroxycoumarin on human lung carcinoma cell lines,” Lung Cancer, vol. 43, no. 3, pp. 275–283, 2004. View at Publisher · View at Google Scholar · View at Scopus
  38. M. E. Riveiro, R. Vazquez, A. Moglioni et al., “Biochemical mechanisms underlying the pro-apoptotic activity of 7,8-dihydroxy-4-methylcoumarin in human leukemic cells,” Biochemical Pharmacology, vol. 75, no. 3, pp. 725–736, 2008. View at Publisher · View at Google Scholar · View at Scopus
  39. M. E. Riveiro, D. Maes, R. Vázquez et al., “Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells,” Bioorganic and Medicinal Chemistry, vol. 17, no. 18, pp. 6547–6559, 2009. View at Publisher · View at Google Scholar · View at Scopus
  40. R. Vázquez, M. E. Riveiro, M. Vermeulen et al., “Structure-anti-leukemic activity relationship study of ortho- dihydroxycoumarins in U-937 cells: Key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action,” Bioorganic and Medicinal Chemistry, vol. 20, no. 18, pp. 5537–5549, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. R. Vázquez, M. E. Riveiro, M. Vermeulen et al., “Toddaculin, a natural coumarin from Toddalia asiatica, induces differentiation and apoptosis in U-937 leukemic cells,” Phytomedicine, vol. 19, no. 8-9, pp. 737–746, 2012. View at Publisher · View at Google Scholar · View at Scopus