Phytochemical studies of the southern Australian marine alga, Laurencia elata

Phytochemistry

Volumn 72, Issue 16, 2011, Pages 2081-2089

  Dias, Daniel Anthony ^a   Urban, Sylvia ^a  

^a RMIT UNIVERSITY   (Australia)

Author keywords

(3Z) chlorofucin; Antitumour; Antiviral and antimicrobial activities; C 16 terpenes; Cycloelatanene A; Cycloelatanene B; Elatenyne; Laurencia elata; Pacifenol; Rhodomelaceae

Indexed keywords

CYCLOELATANENE A; CYCLOELATANENE B; FURAN DERIVATIVE; PLANT EXTRACT; SESQUITERPENE; SPIRO COMPOUND;

ANIMAL; ARTICLE; AUSTRALIA; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; LAURENCIA; MICROBIOLOGICAL EXAMINATION; MOUSE; NUCLEAR MAGNETIC RESONANCE; TUMOR CELL LINE;

ANIMALS; AUSTRALIA; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FURANS; LAURENCIA; MICE; MICROBIAL SENSITIVITY TESTS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS; SESQUITERPENES; SPIRO COMPOUNDS;

ALGAE; LAURENCIA; LAURENCIA ELATA; RHODOMELACEAE;

EID: 80052941645     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.06.012     Document Type: Article

References (44)

1. V.H. Argandoña, A. San-Martín, and J. Rovirosa Halogenated sesquiterpenes Pacifenol and Pacifenol derivatives on the asphid Schizaphis graminum Phytochemistry 32 1993 1159 1161
2. Z. Aydomu, S. Imre, L. Ersoy, and V. Wray Halogenated secondary metabolites from Laurencia obtusa Nat. Prod. Res. 18 2004 43 49 (Pubitemid 38190209)
3. S. Caccamese, A. Compagnini, and R. Maria Toscano Pacifenol from the Mediterranean red alga Laurencia majuscula J. Nat. Prod. 49 1986 173 174
4. D.A. Dias, J.M. White, and S. Urban Laurencia filiformis: phytochemical profiling by conventional and HPLC-NMR approaches Nat. Prod. Commun. 4 2009 157 172
5. D. Díez, M.G. Núnez, R.F. Moro, W. Lumeras, I.S. Marcos, P. Basabe, and J.G. Urones Enantioselective synthesis of cis-3-oxy-2,2,6,6,- tetrasubstituted tetrahydropyrans Synlett 939 2006 941
6. K.L. Erickson, and P.J. Scheuer Marine Natural Products: Chemical and Biological Perspectives 1983 Academic Press New York pp. 131-257
7. M.E.Y. Francisco, and K.L. Erickson Mailiohydrin, a cytotoxic chamigrene dibromhydrin from a Philippine Laurencia species J. Nat. Prod. 64 2001 790 791 (Pubitemid 32565931)
8. F. Fronczek Redetermination of the absolute configuration of deoxyprepacifenol, from the Mediterranean red alga, Laurencia majuscula Acta Crystallogr., Sect. C 45 1989 1102 1104
9. Y. Gopichand, F.J. Schmitz, J. Shelley, A. Rahman, and D. Van der Helm Marine natural products: halogenated acetylenic ethers from the sea hare Aplysia dactylomela J. Org. Chem. 46 1981 5192 5197
10. Hall, J.G., 1984. Ph.D. Thesis. Latrobe University.
11. J.G. Hall, and J.A. Reiss Elatenyne-a Pyrano[3,2-bpyranyl vinyl acetylene from the red alga Laurencia elata Aust. J. Chem. 39 1986 1401 1409
12. B.M. Howard, G.R. Schulte, and W. Fenical Three new vinyl acetylenes from the marine red alga Laurencia Tetrahedron 36 1980 1747 1751
13. K. In Kyu, M.R. Brennan, and K.L. Erickson Lauroxolanes from the marine alga Laurencia majuscula Tetrahedron 30 1989 1757 1760
14. J. Jongaramruong, A.J. Blackman, B.W. Skelton, and A.H. White Chemical relationships between the sea hare Aplysia parvula and the red seaweed Laurencia filiformis from Tasmania Aust. J. Chem. 55 2002 275 280 (Pubitemid 40000910)
15. 13C NMR assignments of chamigrenes from Aplysia dactilomela Magn. Reson. Chem. 39 2001 147 149
16. H. Kikuchi, T. Suzuki, M. Suzuki, and E. Kurosawa A new chamigrene-type bromo diether from the red alga Laurencia nipponica Yamada Bull. Chem. Soc. Jpn. 58 1985 2437 2438
17. H. Kikuchi, T. Suzuki, E. Kurosawa, and M. Suzuki The structure of notoryne, a halogenated C15 terpenoid with a novel carbon skeleton from the red alga Laurencia nipponica Yamada Bull. Chem. Soc. Jpn. 64 1991 1763 1775
18. J. Kimura, N. Kamada, and Y. Tsujimoto Fourteen chamigrene derivatives from a red alga, Laurencia nidifica Bull. Chem. Soc. Jpn. 72 1999 289 292 (Pubitemid 29091886)
19. G.M. König, and A.D. Wright Laurencia rigida: chemical investigations of its antifouling dichloromethane extract J. Nat. Prod. 60 1997 967 970 (Pubitemid 27469039)
20. Kurata, K., Suzuki, T., Suzuki, M., Kurosawa, E., Furusaki, A., Matsumoto, T., 1983a. Laureacetal-D and -E, two new secochamigrene derivatives from the red alga Laurencia nipponica Yamada. Chem. Lett. 557-560.
21. Kurata, K., Suzuki, T., Suzuki, M., Kurosawa, E., Furusaki, A., Matsumoto, T., 1983b. Laurenical, a novel sesquiterpene α,β- unsaturated aldehyde from the red alga Laurencia nipponica Yamada. Chem. Lett. 299-300.
22. U. Lee, C.M. Park, and J.S. Yun Total synthesis of dactomelynes J. Am. Chem. Soc. 117 1995 8017 8018
23. 15-acetogenins from the marine red alga Laurencia decumbens J. Nat. Prod. 70 2007 1499 1502
24. J. Nai-Yun, L. Xiao-Ming, L. Ke, and W. Bin-Gui Halogenated sesquiterpenes from the marine red alga Laurencia saitoi (Rhodomelaceae) Helv. Chim. Acta 92 2009 1873 1879
25. J. Nai-Yun, L. Xiao-Ming, and W. Bin-Gui Sesquiterpenes from other metabolites from the marine red alga Laurencia composita (Rhodomelaceae) Helv. Chim. Acta 93 2010 2281 2286
26. 15-acetogenins from the marine red alga Laurencia decumens J. Nat. Prod. 73 2010 1192
27. M. Ojika, Y. Shizuri, and K. Yamada A halogenated chamigrane epoxide and six related halogen-containing sesquiterpenes from the red alga Laurencia okamurai Phytochemistry 21 1982 2410 2411
28. A. San-Martín, J. Darias, H. Soto, C. Contreras, J.S. Herrera, and J. Rovirosa A new C15 acetogenin from the marine alga Laurencia claviformis J. Nat. Prod. 10 1997 303 311 (Pubitemid 27487718)
29. H.M. Sheldrake, C. Jamieson, and J.W. Burton The changing faces of halogenated marine natural products: total synthesis of the reported structures of Elatenyne and an enyne from Laurencia majuscula Angew. Chem., Int. Ed. 45 2006 7199 7202 (Pubitemid 44748298)
30. H.M. Sheldrake, C. Jamieson, S.I. Pascu, and J.W. Burton Synthesis of the originally proposed structures of elatenyne and an enyne from Laurencia majuscula Org. Biomol. Chem. 7 2009 238 252
31. J.J. Sims, and W. Fenical Marine natural products III. Johnstonol, an unusual halogenated epoxide from the red alga Laurencia johnstonii Tetrahedron Lett. 3 1972 195 198
32. Sims, J.J., Fenical, W., Wing, R.M., Radlick, P., 1971. Marine natural products. I: Pacifenol, a rare sesquiterpene containing bromine and chlorine from the red alga, Laurencia pacifica. J. Am. Chem. Soc. 3374-3375.
33. 13C NMR calculations: prediction of the stereochemistry of elatenyne J. Org. Chem. 73 2008 4053 4062 (Pubitemid 351812905)
34. Suzuki, T., 1980. Two new sesquiterpene alcohols containing bromine from the marine alga, Laurencia nipponica Yamada. Chem. Lett. 541-542.
35. Suzuki, T., Kurosawa, E., 1979. New bromo acetal from the marine alga, Laurencia nipponica Yamada. Chem. Lett. 301-304.
36. 15-nonterpenoids from the red alga Laurencia venusta Yamada Chem. Lett. 12 1983 779 782
37. M. Suzuki, M. Segawa, T. Suzuki, and E. Kurosawa Structures of two new halochamigrene derivatives from the red alga Laurencia nipponica Yamada Bull. Chem. Soc. Jpn. 58 1985 2435 2436
38. 15 nonterpenoid from Laurencia pannosa Phytochemistry 41 1996 1101 1103
39. M. Suzuki, M. Daitoh, C.S. Vairappan, T. Abe, and M. Masuda Novel halogenated metabolites from the Malaysian Laurencia pannosa J. Nat. Prod. 64 2001 597 602 (Pubitemid 32488675)
40. Y. Usami Recent synthetic studies leading to structural revisions of marine natural products Mar. Drugs 7 2009 314 330
41. C.S. Vairappan, M. Suzuki, T. Ishii, T. Okino, T. Abe, and M. Masuda Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp. Phytochemistry 69 2008 2490 2494
42. S.M. Waraszkiewicz, and K.L. Erickson Halogenated sesquiterpenes from the Hawaiian marine alga Laurencia nidifica: Nidificene and Nidifidiene Tetrahedron Lett. 23 1974 2003 2006
43. K. Watanabe, K. Umeda, and M. Miyakado Isolation and identification of three insecticidal principles from the red alga Laurencia nipponica Yamada Agric. Biol. Chem. 53 1989 2513 2515
44. A.D. Wright, G.M. König, R. De Nys, and O. Sticher Seven new metabolites from the marine red alga Laurencia majuscula J. Nat. Prod. 56 1993 394 401 (Pubitemid 23104352)