New polyether triterpenoids from Laurencia viridis and their biological evaluation

Marine Drugs

Volumn 9, Issue 11, 2011, Pages 2220-2235

  Pacheco, Francisco Cen ^a   Villa Pulgarin, Janny A ^b   Mollinedo, Faustino ^b   Martín, Manuel Norte ^a   Fernández, José Javier ^a   Daranas, Antonio Hernández ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Cytotoxic activity; Laurencia viridis; Polyethers; Squalene

Indexed keywords

1,2 DEHYDROPSEUDODEHYDROTHYRSIFEROL; 1,2 PSEUDODEHYDROTHYRSIFEROL; 22 HYDROXY 15(28) DEHYDROVENUSTATRIOL; DEHYDROTHYRSIFEROL; IUBOL; POLYETHER DERIVATIVE; SECODEHYDROTHYRSIFEROL; TRITERPENOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOGENESIS; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; LAURENCIA; LAURENCIA VIRIDIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; STRUCTURE ANALYSIS;

EID: 82655174093     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md9112220     Document Type: Article

References (19)

1. Cragg, G.M.; Newman, D.J. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007, 70, 461-477. (Pubitemid 46595760)
2. Cragg, G.M.; Grothaus, P.G.; Newman, D.J. Impact of natural products on developing new anti-cancer agents. Chem. Rev. 2009, 109, 3012-3043.
3. Faulkner, D.J. Marine natural products. Nat. Prod. Rep. 2002, 19, 1-48. (Pubitemid 34140331)
4. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2011, 28, 196-268.
5. Fernández, J.J.; Souto, M.L.; Norte, M. Marine polyether triterpenes. Nat. Prod. Rep. 2000, 17, 235-246. (Pubitemid 30390788)
6. Gil-Rodríguez, M.C.; Haroun, R. Laurencia viridis sp. Nov. (Ceramiales, Rhodomelacea) from the macaronesian archipielagos. Bot. Mar. 1992, 35, 227-237.
7. Norte, M.; Fernández, J.J.; Souto, M.L. Evaluation of the cytotoxic activity of polyethers isolated from Laurencia. Bioorg. Med. Chem. 1998, 6, 2237-2243. (Pubitemid 29002918)
8. Souto, M.L.; Manríquez, C.P.; Norte, M.; Leira, F.; Fernández, J.J. The inhibitory effects of squalene-derived triterpenes on protein phosphatase PP2A. Bioorg. Med. Chem. Lett. 2003, 13, 1261-1264. (Pubitemid 36351329)
9. Pec, M.K.; Aguirre, A.; Moser-Thier, K.; Fernández, J.J.; Souto, M.L.; Dorta, J.F.; Díaz-González, F.; Villar, J. Induction of apoptosis in estrogen dependent and independent breast cancer cells by the marine terpenoid dehydrothyrsiferol. Biochem. Pharm. 2003, 65, 1451-1461. (Pubitemid 36555833)
10. Pec, M.K.; Artwohl, M.; Fernández, J.J.; Souto, M.L.; Giraldes, T.; de la Rosa, A.D.; Valenzuela-Fernández, A.; Díaz- González, F. Chemical modulation of VLA integrin affinity in human breast cancer cells. Exp. Cell Res. 2007, 313, 1121-1134. (Pubitemid 46437246)
11. Cen-Pacheco, F.; Villa-Pulgarin, J.A.; Mollinedo, F.; Norte, M.; Daranas, A.; Fernández, J.J. Cytotoxic oxasqualenoids from the red alga Laurencia viridis. Eur. J. Med. Chem. 2011, 46, 3302-3308.
12. Gonzalez, A.G.; Arteaga, J.M.; Fernandez, J.J.; Martín, J.D.; Norte, M.; Ruano, J.Z. Terpenoids of the red alga Laurencia pinnatifida. Tetrahedron 1984, 40, 2751-2755.
13. Dewick, P.M. Secondary Metabolism: The Building Blocks and Construction Mechanisms. In Medicinal Natural Products: A Biosinthetic Approach, 3rd ed.; John Wiley & Sons: Hoboken, NJ, USA, 2009; pp. 7-38.
14. Braddock, D.C. A hypothesis concerning the biosynthesis of the obsutallene family of marine natural products via electrophilic bromination. Org. Lett. 2006, 8, 6055-6058.
15. Souto, M.L.; Manríquez, C.P.; Norte, M.; Fernández, J.J. Novel marine polyethers. Tetrahedron 2002, 58, 8119-8125. (Pubitemid 35284077)
16. Manríquez, C.P.; Souto, M.L.; Gavín, J.A.; Norte, M.; Fernández, J.J. Several new squalene-derived triterpenes from Laurencia. Tetrahedron 2001, 57, 3117-3123. (Pubitemid 32322498)
17. Pec, M.K.; Aguirre, A.; Fernández, J.J.; Souto, M.L.; Dorta, J.; Villar, J. Dehydrothyrsiferol does not modulate multidrug resistance-associated protein 1 resistance: A functional screening system for MRP1 substrates. Int. J. Mol. Med. 2002, 10, 605-608.
18. David-Cordonnier, M.H.; Gajate, C.; Olmea, O.; Laine, W.; de la Iglesia-Vicente, J.; Perez, C.; Cuevas, C.; Otero, G.; Manzanares, I.; Bailly, C.; et al. DNA and non-DNA targets in the mechanism of action of the antitumor drug trabectedin. Chem. Biol. 2005, 12, 1201-1210.
19. Gajate, C.; Santos-Beneit, A.M.; Macho, A.; Lazaro, M.; Hernandez-De Rojas, A.; Modolell, M.; Munoz, E.; Mollinedo, F. Involvement of mitochondria and caspase-3 in ET-18-OCH3-induced apoptosis of human leukemic cells. Int. J. Cancer 2000, 86, 208-218. (Pubitemid 30180816)