Differential growth inhibitory effects of highly oxygenated guaianolides isolated from the middle eastern indigenous plant Achillea falcata in HCT-116 colorectal cancer cells

Molecules

Volumn 18, Issue 7, 2013, Pages 8275-8288

  Tohme, Rita ^a   Al Aaraj, Lamis ^a   Ghaddar, Tarek ^a   Gali Muhtasib, Hala ^a   Saliba, Najat A ^a   Darwiche, Nadine ^a  

^a AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

Author keywords

Achillea falcata; Bioassay guided fractionation; Colorectal cancer cells; Guaianolides; Sesquiterpene lactones; Structure activity relationship

Indexed keywords

ANTINEOPLASTIC AGENT; PLANT EXTRACT; SESQUITERPENE;

ACHILLEA; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; HCT116 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; MEDICINAL PLANT; METABOLISM; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; ARTICLE; CELL STRAIN HCT116; DRUG EFFECT;

ACHILLEA; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; HCT116 CELLS; HUMANS; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANTS, MEDICINAL; SESQUITERPENES, GUAIANE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84880815027     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18078275     Document Type: Article

References (51)

1. Koehn, F.E.; Carter, G.T. The evolving role of natural products in drug discovery. Nat. Rev. Drug Discov. 2005, 4, 206-220.
2. Wink, M. Biochemistry of Plant Secondary Metabolism; Sheffield Academic Press: Sheffield, England, 1999; Volume 2.
3. Ghantous, A.; Gali-Muhtasib, H.; Vuorela, H.; Saliba, N.A.; Darwiche, N. What made sesquiterpene lactones reach cancer clinical trials? Drug Discov. Today 2010, 15, 668-678.
4. Ghantous, A.; Nasser, N.; Saab, I.; Darwiche, N.; Saliba, N.A. Structure-activity relationship of seco-tanapartholides isolated from Achillea falcata for inhibition of HaCaT cell growth. Eur. J. Med. Chem. 2009, 44, 3794-3797.
5. Merfort, I. Perspectives on sesquiterpene lactones in inflammation and cancer. Curr. Drug Targets 2011, 12, 1560-1573.
6. Kreuger, M.R.; Grootjans, S.; Biavatti, M.W.; Vandenabeele, P.; D'Herde, K. Sesquiterpene lactones as drugs with multiple targets in cancer treatment: Focus on parthenolide. Anti-Cancer Drug. 2012, 23, 883-896.
7. Kupchan, S.M.; Fessler, D.C.; Eakin, M.A.; Giacobbe, T.J. Reactions of alpha methylene lactone tumor inhibitors with model biological nucelophiles. Science 1970, 168, 376-378.
8. Saikali, M.; Ghantous, A.; Halawi, R.; Talhouk, S.N.; Saliba, N.A.; Darwiche, N. Sesquiterpene lactones isolated from indigenous middle eastern plants inhibit tumor promoter-induced transformation of JB6 cells. BMC Complem. Altern. M. 2012, 12, 89.
9. Salla, M.; Fakhoury, I.; Saliba, N.; Darwiche, N.; Gali-Muhtasib, H. Synergistic anticancer activities of the plant-derived sesquiterpene lactones salograviolide A and iso-seco-tanapartholide. J. Nat. Med. 2013, 468-479.
10. Adib, S.M.; Daniel, J. National cancer registry: Cancer in lebanon 2003; Republic of Lebanon Ministry of Public Health and World Health Organization: Beirut, Lebanon, 2003.
11. Siegel, R.; Naishadham, D.; Jemal, A. Cancer statistics, 2013. CA: Cancer J. Clin. 2013, 63, 11-30.
12. W.H.O. International Agency for Research on Cancer. Available online: http://www.iarc.fr/en/media-centre/iarcnews/2010/globocan2008.php (accessed on 28 April 2013).
13. Ikediobi, O.N.; Davies, H.; Bignell, G.; Edkins, S.; Stevens, C.; O'Meara, S.; Santarius, T.; Avis, T.; Barthorpe, S.; Brackenbury, L.; et al. Mutation analysis of 24 known cancer genes in the NCI-60 cell line set. Mol. Cancer Ther. 2006, 5, 2606-2612.
14. Yoshioka, H.; Mabry, T.J.; Irwin, M.A.; Geissman, T.A.; Samek, Z. The geminal coupling and paramagnetic shift of exomethylene protons in the α, β'-unsaturated γ-lactone group of sesquiterpene lactones containing c8-α-hydroxyl groups. Tetrahedron 1971, 27, 3317-3322.
15. Irwin, M.A.; Geissman, T.A. Rupicolin-A and -B, rupin-A and -B, and cumambrin-B oxide from Artemisia tripartita ssp. Rupicola. Phytochemistry 1973, 12, 863-869.
16. Jakupovic, J.; Boeker, R.; Grenz, M.; Paredes, L.; Bohlmann, F.; El-Din, A.S. Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry 1988, 27, 1135-1140.
17. Kelsey, R.G.; Shafizadeh, F.; Campbell, J.A.; Craig, A.C.; Campana, C.F.; Craig, R.E.R. Canin from Artemisia cana Pursh ssp. cana. Crystal structure and identification of chrysartemin A. J. Org. Chem. 1983, 48, 125-127.
18. Milosavjević, S.; Macura, S.; Stefanović, M. Sesquiterpene lactones from Achillea crithmifolia. J. Nat. Prod. 1994, 57, 64-67.
19. Öksüz, S. Sesquiterpenoids and other constituents from Tanacetum cilicium. Phytochemistry 1990, 29, 887-890.
20. Romo, J.; Romo de Vivar, A.; Treviño, R.; Joseph-Nathan, P.; Díaz, E. Constituents of Artemisia and Chrysanthemum species-the structures of chrysartemins A and B. Phytochemistry 1970, 9, 1615-1621.
21. Jakupovic, J.; Tan, R.X.; Bohlmann, F.; Boldt, P.E.; Jia, Z.J. Sesquiterpene lactones from Artemisia ludoviciana. Phytochemistry 1991, 30, 1573-1577.
22. Yusupov, M.I.; Kasymov, S.Z.; Sidyakin, G.P.; Rakhmankulov, U. Sesquiterpene lactones from Ajania fastigiata. Chem. Nat. Compd. 1979, 15, 579-580.
23. Yusupov, M.I.; Mallabaev, A.; Sidyakin, G.P. The lactones of Achillea biebersteinii. Chem. Nat. Compd. 1976, 12, 396-397.
24. Milosavjević, S.; Aljančić, I.; Macura, S.; Milinkovic, D.; Stefanović, M. Sesquiterpene lactones from Achillea crithmifolia. Phytochemistry 1991, 30, 3464-3466.
25. Todorova, M.; Vogler, B.; Tsankova, E. Terpenoids from Achillea setacea. Zeitschrift fuer Naturforschung, C: J. Biosciences 2000, 55, 840-842.
26. Ghavami, G.; Sardari, S.; Shokrgozar, M.A. Anticancerous potentials of Achillea species against selected cell lines. J. Med. Plants Res. 2010, 4, 2411-2417.
27. Zakirov, S.K.; Kasymov, S.Z.; Abdusamatov, A.; Sidyakin, G.P. Canin and chrysartemin A from Artemesia aschurbajevii. Chem. Nat. Compd. 1985, 21, 542-542.
28. Ohno, N.; Gershenzon, J.; Roane, C.; Mabry, T.J. 11, 13- dehydrodesacetylmatricarin and other sesquiterpene lactones from Artemisia ludoviciana var. Ludoviciana and the identity of artecanin and chyrsartemin B. Phytochemistry 1980, 19, 103-106.
29. Ruiz-Cancino, A.; Cano, A.E.; Delgado, G. Sesquiterpene lactones and flavonoids from Artemisia ludoviciana ssp. Mexicana. Phytochemistry 1993, 33, 1113-1115.
30. Osawa, T.; Suzuki, A.; Tamura, S. Isolation of chrysartemins A and B as rooting cofactors in Chrysanthemum morifolium. Agric. Biol. Chem. 1971, 35, 1966-1972.
31. Bruno, M.; Herz, W. Guaianolides and other constituents of Achillea ligustica. Phytochemistry 1988, 27, 1871-1872.
32. Mallabaev, A.; Rakhmankulov, U.; Sidyakin, G.P. Lactones of Achillea santolina. Chem. Nat. Compd. 1978, 14, 457-457.
33. Tarasov, V.A.; Abdullaev, N.D.; Kasymov, S.Z.; Sidyakin, G.P. Chrysartemin B- a sesquiterpene lactone from Handelia trichophylla. Chem. Nat. Compd. 1976, 12, 601-602.
34. Zan, K.; Chen, X.-Q.; Fu, Q.; Zhou, S.-X.; Xiao, M.-T.; Wen, J.; Tu, P.F. Chemical ingredients isolated from the aerial parts of Artemisia anomala. J. Chinese Pharm. Sci. 2010, 19, 95-99.
35. Marco, J.A.; Sanz-cervera, J.F.; Manglano, E.; Sancenon, F.; Rustaiyan, A.; Kardar, M. Sesquiterpene lactones from iranian Artemisia species. Phytochemistry 1993, 34, 1561-1564.
36. Meng, J.C.; Hu, Y.F.; Chen, J.H.; Tan, R.X. Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. Phytochemistry 2001, 58, 1141-1145.
37. Guangrong, H.; Jiaxin, J.; Dehui, D. Antioxidative and antibacterial activity of the methanol extract of Artemisia anomala S. Moore. Afr. J. Biotechnol. 2008, 7, 1335-1338.
38. Wen, J.; Shi, H.; Xu, Z.; Chang, H.; Jia, C.; Zan, K.; Jiang, Y.; Tu, P. Dimeric guaianolides and sesquiterpenoids from Artemisia anomala. J. Nat. Prod. 2010, 73, 67-70.
39. Sun, L.; Shah, F.; Helal, M.A.; Wu, Y.; Pedduri, Y.; Chittiboyina, A.G.; Gut, J.; Rosenthal, P.J.; Avery, M.A. Design, synthesis, and development of novel guaianolide-endoperoxides as potential antimalarial agents. J. Med. Chem. 2010, 53, 7864-7868.
40. Helal, M.A.; Avery, M.A. Combined receptor-based and ligand-based approach to delineate the mode of binding of guaianolide-endoperoxides to PfATP6. Bioorg. Med. Chem. Lett. 2012, 22, 5410-5414.
41. Fischedick, J.T.; Standiford, M.; Johnson, D.A.; De Vos, R.C.H.; Todorović, S.; Banjanac, T.; Verpoorte, R.; Johnson, J.A. Activation of antioxidant response element in mouse primary cortical cultures with sesquiterpene lactones isolated from Tanacetum parthenium. Planta Med. 2012, 78, 1725-1730.
42. Neukirch, H.; Kaneider, N.C.; Wiedermann, C.J.; Guerriero, A.; D'Ambrosio, M. Parthenolide and its photochemically synthesized 1(10)z isomer: Chemical reactivity and structure-activity relationship studies in human leucocyte chemotaxis. Bioorg. Med. Chem. 2003, 11, 1503-1510.
43. Neukirch, H.; Guerriero, A.; D'Ambrosio, M. Transannular cyclization in cyclodecenes: The case study of melampolides. Eur. J. Org. Chem. 2003, 2003, 3969-3975.
44. Dell'Agli, M.; Galli, G.V.; Bosisio, E.; D'Ambrosio, M. Inhibition of NF-κB and metalloproteinase-9 expression and secretion by parthenolide derivatives. Bioorg. Med. Chem. Lett. 2009, 19, 1858-1860.
45. Zhang, Q.; Lu, Y.; Ding, Y.; Zhai, J.; Ji, Q.; Ma, W.; Yang, M.; Fan, H.; Long, J.; Tong, Z.; et al. Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells. J. Med. Chem. 2012, 55, 8757-8769.
46. Kupchan, S.M.; Eakin, M.A.; Thomas, A.M. Tumor inhibitors. 69. Structure-cytotoxicity relations among the sesquiterpene lactones. J. Med. Chem. 1971, 14, 1147-1152.
47. Lee, K.H.; Meck, R.; Piantadosi, C.; Huang, E.S. Antitumor agents. 4. Cytotoxicity and in vivo activity of helenalin esters and related derivatives. J. Med. Chem. 1973, 16, 299-301.
48. Hall, I.H.; Lee, K.H.; Starenes, C.O.; Sumida, Y.; Wu, R.Y.; Waddell, T.G.; Cochran, J.W.; Gerhart, K.G. Anti-inflammatory activity of sesquiterpene lactones and related compounds. J. Pharm. Sci. 1979, 68, 537-542.
49. Fernandes, M.B.; Scotti, M.T.; Ferreira, M.J.P.; Emerenciano, V.P. Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones. Eur. J. Med. Chem. 2008, 43, 2197-2205.
50. Harborne, J.B. Phytochemical Methods: A Guide to Modern Techniques of Plant Analysis; Chapman & Hall: London, UK, 1998.
51. Saliba, N.A.; Dakdouki, S.; Homeidan, F.R.; Kogan, J.; Bouhadir, K.; Talhouk, S.; Talhouk, R. Bio-guided identification of an anti-inflammatory guaianolide from Centaurea ainetensis. Pharm. Biol. 2009, 47, 701-707.