Anti-cancer potential of sesquiterpene lactones: Bioactivity and molecular mechanisms

Current Medicinal Chemistry - Anti-Cancer Agents

Volumn 5, Issue 3, 2005, Pages 239-249

  Zhang, Siyuan ^a   Won, Yen Kim ^a   Ong, Choon Nam ^a   Shen, Han Ming ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Anti cancer; Anti inflammatory; Apoptosis; NF B; Sesquiterpene lactones; Thiols

Indexed keywords

ANTINEOPLASTIC AGENT; APOPTOTIC PROTEASE ACTIVATING FACTOR 1; ARCTIGENIN; ARCTIIN; ARTEMINOLIDE; CALCIUM; CASPASE 8; CASPASE 9; COSTUNOLIDE; DNA; ESTROGEN; GLUTATHIONE SYNTHASE; HELENALIN; I KAPPA B KINASE INHIBITOR; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE 1; PACLITAXEL; PARTHENOLIDE; PROTEIN BAX; PROTEIN BCL 2; PROTEIN BCL XL; PROTEIN BID; PROTEIN FARNESYLTRANSFERASE; RNA; SECOND MITOCHONDRIAL ACTIVATOR OF CASPASE; SESQUITERPENE LACTONE DERIVATIVE; STRESS ACTIVATED PROTEIN KINASE INHIBITOR; THIOL PROTEINASE; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR RELATED APOPTOSIS INDUCING LIGAND; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BINDING AFFINITY; CANCER CHEMOTHERAPY; CANCER INHIBITION; CANCER PREVENTION; CARCINOGENESIS; CELL CYCLE; CELL DIFFERENTIATION; CELL PROLIFERATION; DRUG BINDING; ENZYME INHIBITION; ESTROGEN SYNTHESIS; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATORY DISEASE; MEDICINAL PLANT; METASTASIS; METASTASIS INHIBITION; NONHUMAN; OXIDATION REDUCTION STATE; OXIDATIVE STRESS; PROTEIN EXPRESSION; REVIEW; SENSITIZATION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; HUMANS; LACTONES; MOLECULAR STRUCTURE; NEOPLASMS; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 18444367100     PISSN: 15680118     EISSN: None     Source Type: Journal    
DOI: 10.2174/1568011053765976     Document Type: Review

References (116)

1. Heinrich, M.; Robles, M.; West, J.E.; Ortiz de Montellano, B.R.; Rodriguez, E. Annu. Rev. Pharmacol. Toxicol., 1998, 38, 539.
2. Heywood, V.H.; Harborne, J.B.; Turner, B.L. The biology and chemistry of the compositae, vols I and II, Academic press: New York, 1977.
3. Merfort, I. J. Chromatography A. 2002, 967, 115.
4. Lee, K.H.; Hall, I.H.; Mar, E.C.; Starnes, C.O.; EIGebaly, S.A.; Waddell, T.G.; HADGRAFT, R.I.; Ruffner, C.G.; Weidner, I. Science, 1977, 196, 533.
5. Wen, J.; You, K.R.; Lee, S.Y.; Song, C.H.; Kim, D.G. J. Biol. Chem., 2002, 277, 38954.
6. Zhang, S.; Ong, C.N.; Shen, H.M. Cancer Lett., 2004, 208, 143.
7. Kupchan, S.M.; Eakin, M.A.; Thomas, A.M. J. Med. Chem., 1971, 14, 1147.
8. Lee, K.H.; Huang, E.S.; Piantadosi, C.; Pagano, J.S.; Geissman,T.A. Cancer Res., 1971, 31, 1649.
9. Lee, K.H.; Meck, R.; Piantadosi, C.; Huang, E.S. J. Med. Chem., 1973, 16, 299.
10. Hall, I.H.; Lee, K.H.; Starnes, C.O.; Eigebaly, S.A.; Ibuka, T.; Wu, Y.S.; Kimura, T.; Haruna, M. J. Pharm. Sci., 1978, 67, 1235.
11. Beekman, A.C.; Woerdenbag, H.J.; van Uden, W.; Pras, N.; Konings, A.W.; Wikstrom, H.V.; Schmidt, T.J. J. Nat. Prod., 1997, 60, 252.
12. Schmidt, T.J. Bioorg. Med. Chem., 1997, 5, 645.
13. Rungeler, P.; Castro, V.; Mora, G.; Goren, N.; Vichnewski, W.; Pahl, H.L.; Merfort, I.; Schmidt, T.J. Bioorg. Med. Chem., 1999, 7, 2343.
14. Siedle, B.; Garcia-Pineres, A.J.; Murillo, R.; Schulte-Monting, J.; Castro, V.; Rungeler, P.; Klaas, C.A.; Da Costa, F.B.; Kisiel, W.; Merfort, I. J. Med. Chem., 2004, 47, 6042.
15. Dirsch, V.M.; Stuppner, H.; Ellmerer-Muller, E.P.; Voilmar, A.M. Bioorg. Med. Chem., 2000, 8, 2747.
16. Evan, G.I.; Vousden, K.H. Nature, 2001, 411, 342.
17. Carnero, A. Br. J. Cancer, 2002, 87, 129.
18. Cho, J.Y.; Kim, A,R.; Jung, J.H.; Chun, T.; Rhee, M.H.; Yoo, E.S. Eur. J. Pharmacol., 2004, 492, 85.
19. Tsiftsoglou, A.S.; Pappas, I.S.; Vizirianakis, I.S. Pharmacol. Ther., 2003, 100, 257.
20. Choi, J.H.; Seo, B.R.; Seo, S.H.; Lee, K.T.; Park, J.H.; Park, H.J.; Choi, J.W.; Itoh, Y.; Miyamoto, K. Arch. Pharm. Res., 2002, 25, 480.
21. Kang, S.N.; Kim, S.H.; Chung, S.W.; Lee, M.H.; Kim, H.J.; Kim,T.S. Br. J. Pharmacol., 2002, 135, 1235.
22. Kim, S.H.; Kang, S.N.; Kim, H.J.; Kim, T.S. Biochem. Pharmacol., 2002, 64, 1233.
23. Kim, S.H.; Kim, T.S. Planta Med., 2002, 68, 886.
24. Hengartner, M.O. Nature, 2000, 407, 770.
25. Kaufmann, S.H.; Hengartner, M.O. Trends Cell Biol., 2001, 11, 526.
26. Sartorius, U.; Schmitz, I.; Krammer, P.H. Chembiochem., 2001, 2, 20.
27. Kaufmann, S.H.; Earnshaw, W.C. Exp. Cell Res., 2000, 256, 42.
28. Choi, J.H.; Ha, J.; Park, J.H.; Lee, J.Y.; Lee, Y.S.; Park, H.J.; Choi, J.W.; Masuda, Y.; Nakaya, K.; Lee, K.T. Jpn. J. Cancer Res., 2002, 93, 1327.
29. Dirsch, V.M.; Stuppner, H.; Vollmar, A.M. Cancer Res., 2001, 61, 5817.
30. Lee, M.G.; Lee, K.T.; Chi, S.G.; Park, J.H. Biol. Pharm. Bull., 2001, 24, 303.
31. Zhang, S.; Ong, C.N.; Shen, H.M. Cancer Lett., 2004, 211, 175.
32. Rao, R.V.; Castro-Obregon, S.; Frankowski, H.; Schuler, M.; Stoka, V.; del Rio, G.; Bredesen, D.E.; Ellerby, H.M. J. Biol. Chem., 2002, 277, 21836.
33. Pozarowski, P.; Halicka, D.H.; Darzynkiewicz, Z. Cytometry, 2003, 54A, 118.
34. Patel, N.M.; Nozaki, S.; Shortle, N.H.; Bhat-Nakshatri, P.; Newton, T.R.; Rice, S.; Gelfanov, V.; Boswell, S.H.; Goulet, R.J., Jr.; Sledge, G.W., Jr.; Nakshatri, H. Oncogene, 2000, 19, 4159.
35. Nakshatri, H.; Rice, S.E.; Bhat-Nakshatri, P. Oncogene, 2004, (in press).
36. Zhang, S.; Lin, Z.N.; Yang, C.F.; Shi, X.; Ong, C.N.; Shen, H.M. Carcinogenesis, 2004, (in press).
37. Kucharczak, J.; Simmons, M.J.; Fan, Y.; Gelinas, C. Oncogene, 2003, 22, 8961.
38. Schutze, S.; Wiegmann, K.; Machleidt, T.; Kronke, M. Immunobiology, 1995, 193, 193.
39. Bussemakers, M.J.; Schalken, J.A. World J. Urol., 1996, 14, 151.
40. Melotti, P.; Nicolis, E.; Tamanini, A.; Rolfini, R.; Pavirani, A.; Cabrini, G. Gene Ther., 2001, 8, 1436.
41. Schnyder, B.; Schnyder-Candrian, S.; Panski, A.; Bommel, H.; Heim, M.; Duschl, A.; Moser, R. Biochem. Biophys. Res. Commun., 2002, 292, 841.
42. Jeong, S.J.; Itokawa, T.; Shibuya, M.; Kuwano, M.; Ono, M.; Higuchi, R.; Miyamoto, T. Cancer Lett., 2002, 187, 129.
43. Dhawan, S.; Singh, S.; Aggarwal, B.B. Eur. J. Immunol., 1997, 27, 2172.
44. Chen, C.C.; Manning, A.M. Agents Actions Suppl, 1995, 47, 135.
45. Coussens, L.M.; Werb, Z. Nature, 2002, 420, 860.
46. Coussens, L.M.; Werb, Z. J. Exp. Med., 2001, 193, F23.
47. Mazor, R.L.; Menendez, I.Y.; Ryan, M.A.; Fiedler, M.A.; Wong, H.R. Cytokine, 2000, 12, 239.
48. Whan, H.J.; Gon, L.B.; Kee, K.Y.; Woo, Y.J.; Kyoung, J.H.; Hong, S.; Young, L.H.; Ro, L.K.; Woo, L.H. Br. J. Pharmacol., 2001, 133, 503.
49. Lee, H.J.; Kim, N.Y.; Jang, M.K.; Son, H.J.; Kim, K.M.; Sohn, D.H.; Lee, S.H.; Ryu, J.H. Planta Med., 1999, 65, 104.
50. Kang, B.Y.; Chung, S.W.; Kim, T.S. Immunol. Lett., 2001, 77, 159.
51. Li-Weber, M.; Giaisi, M.; Baumann, S.; Treiber, M.K.; Krammer, P.H. Cell Death. Differ., 2002, 9, 1256.
52. Sobota, R.; Szwed, M.; Kasza, A.; Bugno, M.; Kordula, T. Biochem. Biophys. Res. Commun., 2000, 267, 329.
53. Fukuda, K.; Akao, S.; Ohno, Y.; Yamashita, K.; Fujiwara, H. Cancer Lett., 2001, 164, 7.
54. Kim, E.J.; Jin, H.K.; Kim, Y.K.; Lee, H.Y.; Lee, S.Y.; Lee, K.R.; Zee, O.P.; Han, J.W.; Lee, H.W. Biochem. Pharmacol., 2001, 61, 903.
55. Cho, J.Y.; Baik, K.U.; Jung, J.H.; Park, M.H. Eur. J. Pharmacol., 2000, 398, 399.
56. Dubois, R.N.; Abramson, S.B.; Crofford, L.; Gupta, R.A.; Simon, L.S.; Van De Putte, L.B.; Lipsky, P.E. FASEB J., 1998, 12, 1063.
57. Gupta, R.A.; Dubois, R.N. Nat. Rev. Cancer, 2001, 1, 11.
58. Hehner, S.P.; Heinrich, M.; Bork, P.M.; Vogt, M.; Rafter, F.; Lehmann, V.; Schulze-Osthoff, K.; Droge, W.; Schmitz, M.L. J. Biol. Chem., 1998, 273, 1288.
59. Hwang, D.; Fischer, N.H.; Jang, B.C.; Tak, H.; Kim, J.K.; Lee, W. Biochem. Biophys. Res. Commun., 1996, 226, 810.
60. Pugh, W.J.; Sambo, K. J. Pharm. Pharmacol., 1988, 40, 743.
61. Mew, D.; Balza, F.; Towers, G.H.; Levy, J.G. Planta Med., 1982, 45, 23.
62. Abramowski, Z.; Towers, G.H.N. Biochem. Syst. Ecol., 1985, 365.
63. Marco, J.A.; Barbera, O. In Studies in Natural Products Chemistry. Elsevier: Amsterdam, 1990.
64. Robles, M.; Aregullin, M.; West, J.; Rodriguez, E. Planta Med., 1995, 61, 199.
65. Tan, R.X.; Tang, H.Q.; Hu, J.; Shuai, B. Phytochemistry, 1998, 49, 157.
66. Lee, S.H.; Kim, H.K.; Seo, J.M.; Kang, H.M.; Kim, J.H.; Son, K.H.; Lee, H.; Kwon, B.M.; Shin, J.; Seo, Y. J. Org. Chem., 2002, 67, 7670.
67. Lee, S.H.; Lee, M.Y.; Kang, H.M.; Han, D.C.; Son, K.H.; Yang, D.C.; Sung, N.D.; Lee, C.W.; Kim, H.M.; Kwon, B,M. Bioorg. Med. Chem., 2003, 11, 4545.
68. Hladon, B.; Drozdz, B.; Holub, M.; Bobkiewicz, T. Arch. Immunol. Ther. Exp. (Warsz), 1975, 23, 845.
69. Woerdenbag, H.J.; Lemstra, W.; Hendriks, H.; Malingre, T.M.; Konings, A.W. Planta Med., 1987, 53, 318.
70. Takasaki, M.; Konoshima, T.; Komatsu, K.; Tokuda, H.; Nishino, H. Cancer Lett., 2000, 158, 53.
71. Knight D.W. Nat. Prod. Rep., 1995, 12, 271.
72. Won, Y.K.; Ong, C.N.; Shi, X.L.; Shen, H.M. Carcinogenesis, 2004, 25, 1449.
73. Mori, H.; Kawamori, T.; Tanaka, T.; Ohnishi, M.; Yamahara, J. Cancer Lett., 1994, 83, 171.
74. Ohnishi, M.; Yoshimi, N.; Kawamori, T.; Ino, N.; Hirose, Y.; Tanaka, T.; Yamahara, J.; Miyata, H.; Mori, H. Jpn. J. Cancer Res., 1997, 88, 111.
75. Packer, L. Biothiols, Part A and Part B, Academic Press:San Diego, 1995.
76. Deneke, S.M. Curr. Top. Cell Regul., 2000, 36, 151.
77. Paget, M.S.; Buttner, M.J. Annu. Rev. Genet., 2003, 37, 91.
78. Sen, C.K. Curr. Top. Cell Regul., 2000, 36, 1.
79. Arrick, B.A.; Nathan, C.F.; Cohn, Z.A. J. Clin. Invest, 1983, 71, 258.
80. Merrill, J.C.; Kim, H.L.; Safe, S.; Murray, C.A.; Hayes, M.A. J. Toxicol. Environ. Health, 1988, 23, 159.
81. Robles, M.; Wang, N.; Kim, R.; Choi, B.H. J. Neurosci. Res., 1997, 47, 90.
82. Schmidt, T.J.; Lyss, G.; Pahl, H.L.; Merfort, I. Bioorg. Med. Chem., 1999, 7, 2849.
83. Garcia-Pineres, A.J.; Castro, V.; Mora, G.; Schmidt, T.J.; Strunck, E.; Pahl, H.L.; Merfort, I. J. Biol. Chem., 2001, 276, 39713.
84. Page, J.D.; Chaney, S.G.; Hall, I.H.; Lee, K.H.; Holbrook, D.J. Biochim. Biophys. Acta, 1987, 926, 186.
85. Hall, I.H.; Lee, K.H.; Williams, W.L., Jr.; Kimura, T.; Hirayama,T. J. Pharm. Sci., 1980, 69, 294.
86. Hall, I.H.; Lee, K.H.; Imakura, Y.; Sims, D. J. Pharm. Sci., 1983, 72, 1008.
87. Grippo, A.A.; Hall, I.H.; Kiyokawa, H.; Muraoka, O.; Shen, Y.C.; Lee, K.H. Drug Des Discov., 1992, 8, 191.
88. Hall, I.H.; Williams, W.L., Jr.; Grippo, A.A.; Lee, K.H.; Holbrook,D.J.; Chaney, S.G. Anticancer Res., 1988, 8, 33.
89. Duszenko, M.; Balla, H.; Mecke, D. Biochim. Biophys. Acta, 1982, 714, 344.
90. Davis, W., Jr.; Ronai, Z.; Tew, K.D. J. Pharmacol. Exp. Ther., 2001, 296, 1.
91. Halliwell, B. Am. J. Med., 1991, 91, 14S.
92. Karin, M.; Lin, A. Nat. Immunol., 2002, 3, 221.
93. Karin, M.; Yamamoto, Y.; Wang, Q.M. Nat. Rev. Drug Discov., 2004, 3, 17.
94. Bork, P.M.; Schmitz, M.L.; Kuhnt, M.; Escher, C.; Heinrich, M. FEBS Lett., 1997, 402, 85.
95. Hehner, S.P.; Hofmann, T.G.; Droge, W.; Schmitz, M.L. J. Immunol., 1999, 163, 5617.
96. Koo, T.H.; Lee, J.H.; Park, Y.J.; Hong, Y.S.; Kim, H.S.; Kim, K.W.; Lee, J.J. Planta Med., 2001, 67, 103.
97. Lyss, G.; Schmidt T.J.; Merfort, I.; Pahl, H.L. Biol. Chem., 1997, 378, 951.
98. Kwok, B.H.; Koh, B.; Ndubuisi, M.I.; Elofsson, M.; Crews, C.M. Chem. Biol., 2001, 8, 759.
99. Garcia-Pineres, A.J.; Lindenmeyer, M.T.; Merfort, I. Life Sci., 2004, 75, 841.
100. Seger, R.; Krebs, E.G. FASEB J., 1995, 9, 726.
101. Kyriakis, J.M. Biochem. Soc. Symp., 1999, 64, 29.
102. Fiebich, B.L.; Lieb, K.; Engels, S.; Heinrich, M. J. Neuroimmunol., 2002, 132, 18.
103. Kang, J.S.; Yoon, Y.D.; Lee, K.H.; Park, S.K.; Kim, H.M. Biochem. Biophys. Res. Commun., 2004, 313, 171.
104. Lotem, J.; Kama, R.; Sachs, L. Proc. Natl. Acad. Sci. U. S. A, 1999, 96, 12016.
105. Sasco, A.J.; Kaaks, R.; Little, R.E. Expert. Rev. Anticancer Ther., 2003, 3, 546.
106. Buzdar, A.U. Clin. Breast Cancer, 2003, 4 Suppl 2, S84.
107. Blanco, J.G.; Gil, R.R.; Alvarez, C.I.; Patrito, L.C.; Genti-Raimondi, S.; Flury, A. FEBS Lett., 1997, 409, 396.
108. Blanco, J.G.; Gil, R.R.; Bocco, J.L.; Meragelman, T.L.; Genti-Raimondi, S.; Flury, A. J. Pharmacol. Exp. Ther., 2001, 297, 1099.
109. Chen, H.C.; Chou, C.K.; Lee, S.D.; Wang, J.C.; Yeh, S.F. Antiviral Res., 1995, 27, 99.
110. Park, H.J.; Kwon, S.H.; Han, Y.N.; Choi, J.W.; Miyamoto, K.; Lee,S.H.; Lee, K.T. Arch. Pharm. Res., 2001, 24, 342.
111. Bocca, C.; Gabriel, L.; Bozzo, F.; Miglietta, A. Chem. Biol. Interact., 2004, 147, 79.
112. Ross, J.J.; Arnason, J.T.; Birnboim, H.C. Planta Med., 1999, 65, 126.
113. Hall, I.H.; Grippo, A.A.; Lee, K.H.; Chaney, S.G.; Holbrook, D.J. Pharm. Res., 1987, 4, 509.
114. Williams, W.L., Jr.; Hall, I.H.; Grippo, A.A.; Oswald, C.B.; Lee,K.H.; Holbrook, D.J.; Chaney, S.G. J. Pharm. Sci., 1988, 77, 178.
115. Hausott, B.; Greger, H.; Marian, B. J. Cancer Res. Clin. Oncol., 2003, 129, 569.
116. Baguley, B.C. Lancet Oncol., 2003, 4, 141.