Anti-proliferative activity of meroditerpenoids isolated from the brown alga Stypopodium flabelliforme against several cancer cell lines

Marine Drugs

Volumn 9, Issue 5, 2011, Pages 852-862

  Pereira, David M ^a   Cheel, Jose ^b,c   Areche, Carlos ^d   San Martin, Aurelio ^d   Rovirosa, Juana ^d   Silva, Luis R ^a   Valentao, Patricia ^a   Andrade, Paula B ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^c CPN Sro ^*  (Czech Republic)

^d UNIVERSITY OF CHILE   (Chile)

Author keywords

Anti proliferative; Antimicrobial; Meroditerpenoids; Stypopodium flabelliforme

Indexed keywords

14 KETOSTYPODIOL DIACETATE; ALGAL EXTRACT; ANTIBIOTIC AGENT; ANTIMITOTIC AGENT; DITERPENOID; EPITAONDIOL; EPITAONDIOL DIACETATE; EPITAONDIOL MONOACETATE; MERODITERPENOID DERIVATIVE; STYPODIOL; STYPOTRIOL TRIACETATE; UNCLASSIFIED DRUG; VINCRISTINE;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BROWN ALGA; CANCER CELL CULTURE; CELL STRAIN CACO 2; CHINESE HAMSTER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG ISOLATION; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; ENTEROCOCCUS FAECALIS; FIBROBLAST; HUMAN; HUMAN CELL; MACROPHAGE; MAST CELL LEUKEMIA; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; MITOSIS INHIBITION; MOUSE; NEUROBLASTOMA CELL; NONHUMAN; PROTEUS MIRABILIS; RAT; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; STYPOPODIUM FLABELLIFORME;

ALGAE; BACILLUS CEREUS; CRICETULUS GRISEUS; ENTEROCOCCUS FAECALIS; MICROCOCCUS LUTEUS; MURINAE; PHAEOPHYCEAE; PROTEUS MIRABILIS; RATTUS; SALMONELLA TYPHIMURIUM; STAPHYLOCOCCUS AUREUS; STYPOPODIUM;

EID: 79957636202     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md9050852     Document Type: Article

References (26)

1. Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007, 70, 461-477. (Pubitemid 46595760)
2. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2006, 23, 26-78.
3. Huang, H.L.; Wu, S.L.; Liao, H.F.; Jiang, C.M.; Huang, R.L.; Chen, Y.Y.; Yang, Y.C.; Chen, Y.J. Induction of apoptosis by three marine algae through generation of reactive oxygen species in human leukemic cell lines. J. Agric. Food Chem. 2005, 53, 1776-1781.
4. Numata, A.; Kanbara, S.; Takahashi, C.; Fujiki, R.; Yoneda, M.; Fujita, E.; Nabeshima, Y. Cytotoxic activity of marine algae and a cytotoxic principle of the brown alga Sargassum tortile. Chem. Pharm. Bull. (Tokyo) 1991, 39, 2129-2131.
5. Fenical, W.; Paul, V.J. Antimicrobial and cytotoxic terpenoids from tropical green algae of the family Udoteaceae. Hydrobiologia 1984, 116-117, 135-140.
6. Itoh, H.; Noda, H.; Amano, H.; Zhuaug, C.; Mizuno, T.; Ito, H. Antitumor activity and immunological properties of marine algal polysaccharides, especially fucoidan, prepared from Sargassum thunbergii of Phaeophyceae. Anticancer Res. 1993, 13, 2045-2052. (Pubitemid 24036324)
7. Jang, K.H.; Lee, B.H.; Choi, B.W.; Lee, H.S.; Shin, J. Chromenes from the brown alga Sargassum siliquastrum. J. Nat. Prod. 2005, 68, 716-723. (Pubitemid 40825282)
8. Soares, A.R.; Abrantes, J.L.; Souza, T.M.L.; Fontes, C.F.L.; Pereira, R.C.; Frugulhetti, I.C.D.P.P.; Teixeira, V.L. In vitro antiviral effect of meroditerpenes isolated from the Brazilian seaweed Stypopodium zonale (Dictyotales). Planta Med. 2007, 73, 1221-1224. (Pubitemid 47572362)
9. Martinez, J.L.; Sepulveda, S.P.; Rovirosa, J.; San Martin, A. Efectos en aorta y auricula aisladas de rata de diacetil epitaondiol, diterpenoide del alga Stypopodium flabelliforme. An. Asoc. Quim. Argent. 1997, 85, 69-75. (Pubitemid 127800159)
10. Gil, B.; Ferrándiz, M.L.; Sanz, M.J.; Terencio, M.C.; Ubeda, A.; Rovirosa, J.; San-Martin, A.; Alcaraz, M.J.; Payá, M. Inhibition of inflammatory responses by epitaondiol and other marine natural products. Life Sci. 1995, 57, 25-30.
11. Rovirosa, J.; San-Martin, A. Antimicrobial activity of the brown alga Stypopodium flabelliforme constituents. Fitoterapia 1997, 68, 473-475. (Pubitemid 27505059)
12. Vichai, V.; Kirtikara, K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. Protoc. 2006, 1, 1112-1116.
13. Sabry, O.M.M.; Andrews, S.; McPhail, K.L.; Goeger, D.E.; Yokochi, A.; LePage, K.T.; Murray, T.F.; Gerwick, W.H. Neurotoxic meroditerpenoids from the tropical marine brown alga Stypopodium flabelliforme. J. Nat. Prod. 2005, 68, 1022-1030. (Pubitemid 41151756)
14. Cheng, W.T.; Guo, Z.X.; Lin, C.A.; Lin, M.Y.; Tung, L.C.; Fang, K. Oxidative stress promotes autophagic cell death in human neuroblastoma cells with ectopic transfer of mitochondrial PPP2R2B (B 2). BMC Cell Biol. 2009, 10, 91.
15. Gimenez-Xavier, P.; Francisco, R.; Santidrian, A.F.; Gil, J.; Ambrosio, S. Effects of dopamine on LC3-II activation as a marker of autophagy in a neuroblastoma cell model. Neurotoxicology 2009, 30, 658-665.
16. Depix, M.S.; Martínez, J.; Santibañez, F.; Rovirosa, J.; Martín, A.S.; Maccioni, R.B. The compound 14-keto stypodiol diacetate from the algae Stypopodium flabelliforme inhibits microtubules and cell proliferation in DU-145 human prostatic cells. Mol. Cell. Biochem. 1998, 187, 191-199. (Pubitemid 28454290)
17. Gibbons, S. Anti-staphylococcal plant natural products. Nat. Prod. Rep. 2004, 21, 263-277. (Pubitemid 38527319)
18. Rios, J.L.; Recio, M.C. Medicinal plants and antimicrobial activity. J. Ethnopharmacol. 2005, 100, 80-84. (Pubitemid 41073526)
19. Areche, C.; San-Martín, A.; Rovirosa, J.; Soto-Delgado, J.; Contreras, R. An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods. Phytochemistry 2009, 70, 1315-1320.
20. Rovirosa, J.; Darias, J.; Quezada, E.; Sanmartin, A. A New diterpenoid from the alga Stypopodium flabelliforme. Bol. Soc. Chil. Quim. 1994, 39, 219-221.
21. Rovirosa, J.; Sepulveda, M.; Quezada, E.; San-Martin, A. Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives. Phytochemistry 1992, 31, 2679-2681.
22. Gerwick, W.H.; Fenical, W. Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) papenfuss. J. Org. Chem. 1981, 46, 22-27.
23. Houghton, P.; Fang, R.; Techatanawat, I.; Steventon, G.; Hylands, P.J.; Lee, C.C. The sulphorhodamine (SRB) assay and other approaches to testing plant extracts and derived compounds for activities related to reputed anticancer activity. Methods 2007, 42, 377-387. (Pubitemid 46860387)
24. Ferreres, F.; Pereira, D.M.; Gil-Izquierdo, A.; Valentao, P.; Botelho, J.; Mouga, T.; Andrade, P.B. HPLC-PAD-atmospheric pressure chemical ionization-MS metabolite profiling of cytotoxic carotenoids from the echinoderm Marthasterias glacialis (spiny sea-star). J. Sep. Sci. 2010, 33, 2250-2257.
25. Zgoda, J.R.; Porter, J.R. A convenient microdilution method for screening natural products against bacteria and fungi. Pharm. Biol. 2001, 39, 221-225. (Pubitemid 32881533)
26. Kuete, V.; Ngameni, B.; Simo, C.C.F.; Tankeu, R.K.; Ngadjui, B.T.; Meyer, J.J.M.; Lall, N.; Kuiate, J.R. Antimicrobial activity of the crude extracts and compounds from Ficus chlamydocarpa and Ficus cordata (Moraceae). J. Ethnopharmacol. 2008, 120, 17-24.