Antitumor effects of two novel naturally occurring terpene quinones isolated from the mediterranean ascidian Aplidium conicum

Journal of Medicinal Chemistry

Volumn 48, Issue 9, 2005, Pages 3410-3416

  Aiello, Anna ^a   Fattorusso, Ernesto ^a   Luciano, Paolo ^a   Macho, Antonio ^b   Menna, Marialuisa ^a   Muñoz, Eduardo ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF CÓRDOBA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; NATURAL PRODUCT; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; TERPENE DERIVATIVE; THIAPLIDIAQUINONE A; THIAPLIDIAQUINONE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APLIDIUM CONICUM; APOPTOSIS; ARTICLE; ASCIDIACEA; CANCER CELL DESTRUCTION; CELL TRANSPORT; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG TRANSPORT; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; MEMBRANE POTENTIAL; MITOCHONDRION; PRENYLATION; SEASHORE; SOUTHERN EUROPE; STRUCTURE ACTIVITY RELATION; T CELL LYMPHOMA;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZOQUINONES; HUMANS; JURKAT CELLS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE POTENTIALS; MITOCHONDRIA; REACTIVE OXYGEN SPECIES; TERPENES; THIAZINES; UROCHORDATA;

EID: 18244384224     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0489915     Document Type: Article

References (33)

1. Powis, G.; Free radical formation by antitumor quinones Free. Radic. Biol. Med. 1989, 6, 63-101.
2. Moore, H. W.; Czerniak, R.; Hamdam, A. Natural quinones as quinone methide precursoi-ideas in rational drug design Drugs Exp. Clin. Res. 1986, 12, 475-494.
3. Nohl, H.; Jordan, W.; Youngman, R. J. Quinones in biology: functions in electron transfer and oxygen activation Adv. Free Radic. Biol. Med. 1986, 2, 211-279.
4. Schmitz, F. J.; Bloor, S. J. Xesto-and Halenaquinone derivatives from a sponge, Adocia sp., from Truk Lagoon J. Org. Chem. 1988, 53, 3922-3925.
5. Alvi, K. A.; Rodriguez, J.; Diaz, M. C.; Moretti, R.; Wilhelm, R. S.; Lee, R. H.; Slate, D. L.; Crews, P. Protein tyrosine kinase inhibitory properties of panar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis. J. Org. Chem. 1993, 58, 4871-4880.
6. Inbaraj, J. J.; Gandhisan, E.; Murugesan, E. Cytotoxicity and superoxide anion generation by some naturally occurring quinones Free Radic. Biol. Med. 1999, 26, 1072-1078.
7. Benchekroun, M. N.; Myers, C. E.; Sinha, B. K. Free radical formation by ansamycin benzoquinone in human breast tumor cells: implication for cytotoxicity and resistance Free Radic. Biol. Med. 1994, 17, 191-200.
8. Huang, P.; Feng, L.; Oldham, E. A.; Keating, M. J.; Plunkett, W. Superoxide dismutase as a target for the selective killing of cancer cells. Nature (London) 2000, 407, 390-395.
9. Faulkner, D. J. Marine Natural Reports. Nat Prod. Rep. 2002, 19, 1-48; and previous reviews of this series.
10. Fenical, W. Geranyl hydroquinone, a cancer protective agent from the Tunicate Aplidium species. Food-Drugs Sea, Proc. Conf. 4th 1976, 4, 388-394.
11. Fu, X.; Hossain, M. B.; van der Helm, D.; Schmitz, F. J. Longithorone A: unprecedented dimeric prenylated quinone from the tunicate. Aplydium longithorax. J. Am. Chem. Soc. 1994, 116, 12125-12126; this reference has been corrected in J. Am. Chem. Soc. 1995, 117, 9381.
12. Fu, X.; Hossain, M. B.; van der Helm, D.; Schmitz, F. J. Longithorone A: unprecedented dimeric prenylated quinone from the tunicate. Aplydium longithorax. J. Am. Chem. Soc. 1994, 116, 12125-12126; this reference has been corrected in J. Am. Chem. Soc. 1995, 117, 9381.
13. Fu, X.; Hossain, M. B.; Schmitz, F. J.; van der Helm, D. Longithorones, unique prenylated para- and metacyclophane type quinones from the tunicate. Aplydium longithorax. J. Org. Chem. Soc. 1897, 62, 3810-3819.
14. Davis, R. A.; Carroll, A. R.; Quinn, R. J. Longithorones J and K, two new cyclofarnesylated quinine derived metabolites from the Australian tunicate. Aplydium longithorax. J. Nat. Prod., 1999, 62, 158-160.
15. Fu, X.; Ferreira, L. G.; Schmitz, F. J. Longithorols A and B, novel prenylated paracyclophane- and metacyclophane-tipe hydroquinones from the tunicate. Aplydiurn longithorax. J. Nat. Prod. 1999, 62, 1306-1310.
16. Davis, R. A.; Carroll, A. R.; Quinn, R. J. Longithorols C-E. Three new macrocyclic sesquiterpene hydroquinone metabolites from the Australian tunicate. Aplydium longithorax J. Nat. Prod., 1999, 62, 1405-1409.
17. Aiello, A.; Fattorusso, E.; Luciano, P.; Menna, M.; Esposito, G.; Iuvone, T.; Pala, D. Conicaquinones A and B, two novel cytotoxic terpene quinones from the Mediterranean ascidian. Aplidium conicum. Eur. J. Org. Chem. 2003, 898-900.
18. Smith, M. T. Quinones as mutagens, carcinogens and anticancer agents: introduction and overview. J. Toxico. Environ. Health 1985, 16, 665-672.
19. de Tinguy-Moreaud, E.; Pourquier, P.; Montaudon, D.; Robert, J. Relationships between DNA damage and growth inhibition induced by topoisomerase II-interfering drugs in doxorubicin-sensitive and -resistant rat glioblastoma cells. Anticancer Res. 1994, 14, 99-103.
20. Macho, A.; Sancho, R.; Minassi, A.; Appendino, G.; Lawen, A.; Muñoz, E. Involvement of reactive oxygen species in capsaicinoid-induced apoptosis in transformed cells. Free Radic. Res. 2003, 37, 611-9.
21. Macho, A.; Lucena, C.; Calzado, M. A.; Blanco, M.; Donnay, I.; Appendino, G.; Muñoz, E. Phorboid 20-homovanillates induce apoptosis through a VR1-independent mechanism. Chem Biol. 2000, 7, 483-92.
22. Macho, A.; Blazquez, M. V.; Navas, P.; Muñoz, E. Induction of apoptosis by vanilloid compounds does not require de novo gene transcription and activator protein 1 activity. Cell Growth Differ. 1998, 9, 277-86.
23. Ly, J. D.; Lawen, A. Transplasma membrane electron transport: Enzymes involved and biological function. Redox Rep. 2003, 8, 3-21.
24. Lawen, A.; Martinus, R. D.; Mcmullen, G. L.; Nagley, P.; Vaillant, F.; Wolvetang, E. J.; Linnane, A. W. The universality of bioenergetic disease: The role of mitochondrial mutation and the putative inter-relationship between mitochondria and plasma membrane NADH oxidoreductase. Mol. Aspects Med. 1994, 15 Suppl, 13-27.
25. Marchetti, P.; Decaudin, D.; Macho, A.; Zamzami, N.; Hirsch, T.; Susin, S. A.; Kroemer, G. Redox regulation of apoptosis: impact of thiol oxidation status on mitochondrial function. Eur. J. Immunol. 1997, 27, 289-96.
26. Costantini, P.; Chernyak, B. V.; Petronilli, V.; Bernardi, P. Modulation of the mitochondrial permeability transition pore by pyridine nucleotides and dithiol oxidation at two separate sites. J. Biol. Chem. 1996, 271, 6746-51.
27. Kim, C.; Crane, F. L.; Faulk, W. P.; Morrẽ, D. J. Purification and characterization of a doxorubicin-inhibited NADH-quinone (NADH-ferricyanide) reductase from rat liver plasma-membranes. J. Biol. Chem. 2002, 277, 16441-16447.
28. Wang, S.; Konorev, E. A.; Kotamraju, S.; Joseph, J.; Kalivendi, S.; Kalyanaraman, B. Doxorubicin induces apoptosis in normal and tumor cells via distinctly different mechanisms, intermediacy of H(2)O(2)- and p53-dependent pathways. J Biol Chem. 2004, 279, 25535-25543.
29. Morré, D. J.; Chueh, P. J.; Lawler, J.; Morré, D. M. The sulfonylurea-inhibited NADH oxidase activity of HeLa cell plasma membranes has properties of a protein disulfide-thiol oxidoreductase with protein disulfide-thiol interchange activity. J. Bioenerg. Biomembr. 1998, 30, 477-487.
30. Morré, D. M.; Lenaz, G.; Morré, D. J. Surface oxidase and oxidative stress propagation in aging. J. Exp. Biol. 2000, 203 Pt 10, 1513-1521.
31. Lenaz, G.; Paolucci, U.; Fato, R.; D'aurelio, M.; Castelli, G. P.; Sgarbi, G.; Biagini, G.; Ragni, L.; Salardi, S.; Cacciari, E. Enhanced activity of the plasma membrane oxidoreductase in circulating lymphocytes from insulin-dependent diabetes mellitus patients. Biochem. Biophys. Res. Commun. 2002, 290, 1589-1592.
32. Mazurek, S.; Boschek, C. B.; Eigenbrodt, E. The role of phosphometabolites in cell proliferation, energy metabolism, and tumor therapy. J. Bioenerg. Biomembr. 1997, 29, 315-330.
33. Larm, J.; Vaillant, F.; Linnane, A.; Lawen, A. Up-regulation of the plasma membrane oxidoreductase as a prerequisite for the viability of human namalwa rho 0 cells. J. Biol. Chem. 1994, 269, 30097-30100.