An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods

Phytochemistry

Volumn 70, Issue 10, 2009, Pages 1315-1320

  Areche, Carlos ^a   San Martín, Aurelio ^a   Rovirosa, Juana ^a   Soto Delgado, Jorge ^a   Contreras, Renato ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

Dictyotaceae; GIAO DFT; Meroditerpenoids; Seaweeds; Stypopodium flabelliforme; Stypotriol

Indexed keywords

DITERPENE; STYPOTRIOL; TERPENE;

ARTICLE; BIOLOGY; BROWN ALGA; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALGAE, BROWN; COMPUTATIONAL BIOLOGY; DITERPENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; TERPENES;

DICTYOTACEAE; PHAEOPHYCEAE; STYPOPODIUM;

EID: 69249155762     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.07.017     Document Type: Article

References (32)

1. Abad A., Agulló C., Arnó M., Cuñat A.C., Meseguer B., and Zaragozá R.J. An efficient stereoselective synthesis of stypodiol and epistypodiol. J. Org. Chem. 63 (1998) 5100-5106
2. Barone V., Cossi M., and Tomasi J. Geometry optimization of molecular structures in solution by the polarizable continuum model. J. Comput. Chem. 19 (1998) 404-417
3. 13C-chemical shifts. Tetrahedron 59 (2003) 9555-9562
4. Braddock D.C., and Rzepa H.S. Structural reassignment of obtusallenes V, VI, and VII by GIAO-based density functional prediction. J. Nat. Prod. 71 (2008) 728-730
5. Chini M.G., Riccio R., and Bifulco G. DFT/NMR integrated approach: a valid support to the total synthesis of chiral molecules. Magn. Reson. Chem. 46 (2008) 962-968
6. Da-Silva G.V.J., and Cunha-Neto A. Calculated NMR as a tool for structural elucidation of jungianol and mutisianthol. Tetrahedron 61 (2005) 7763-7767
7. Depix M.S., Martinez J., Santibañez F., Rovirosa J., San-Martin A., and 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. 187 (1998) 191-199
8. Dictionary of Natural Products on CD-ROM, 2007. Chapman and Hall/CRC, Boca Raton, Florida, USA.
9. Dorta E., Cueto M., Brito I., and Darias J. New terpenoids from the brown alga Stypopodium zonale. J. Nat. Prod. 65 (2002) 1727-1730
10. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Inc., Wallingford, CT
11. Gerwick W.H., and Fenical W. Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss. J. Org. Chem. 46 (1981) 22-27
12. Gerwick W., and Fenical W. Phenolic lipids from related marine algae of the order dictyotales. Phytochemistry 21 (1982) 633-637
13. Gerwick W.H., Fenical W., and Norris J.N. Chemical variation in the tropical seaweed Stypopodium zonale (dictyotaceae). Phytochemistry 24 (1985) 1279-1283
14. Gil B., Ferrandiz M.L., Sanz M.J., Terencio M.C., Ubeda A., Rovirosa J., San-Martin A., Alcaraz M.J., and Paya M. Inhibition of inflammatory responses by epitaondiol and other marine natural products. Life Sci. 57 (1995) PL25-PL30
15. Gonzalez A.G., Alvarez M.A., Martin J.D., Norte M., Perez C., and Rovirosa J. Diterpenoids of mixed biogenesis in phaeophyta biogenetic-type interconversions. Tetrahedron 38 (1982) 719-728
16. Hay M.E. Marine chemical ecology: what is known and what is next?. J. Exp. Mar. Biol. Ecol. 200 (1996) 103-134
17. Hehre W.J., Radom L., Schleyer P.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
18. Ianora A., Boersma M., Casotti R., Fontana A., Harder J., Hoffmann F., Pavia H., Potin P., Poulet S., and Toth G. New trends in marine chemical ecology. Estuaries and Coasts 29 (2006) 531-551
19. Inoue S., Saito K., Kato K., Nozaki S., and Sato K. Selective synthesis of monomethyltocols via n-allylnickel complexes. JCS Perkin I (1974) 2097-2101
20. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37 (1988) 785-789
21. Mori J., Iwashima M., Wakasugi H., Saito H., Matsunaga T., Ogasawara M., Takahashi S., Suzuki H., and Hayashi T. New plastoquinones isolated from the brown alga, Sargassum micracanthun. Chem. Pharm. Bull. 53 (2005) 1159-1163
22. Numata A., Kanbara S., Takahashi C., Fujiki R., Yoneda M., Usami Y., and Fujita E. A cytotoxic principle of the brown alga Sargassum tortile and structures of chromenes. Phytochemistry 31 (1992) 1209-1213
23. Rovirosa J., Sepulveda M., Quezada E., and San-Martin A. Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives. Phytochemistry 31 (1992) 2679-2681
24. Rovirosa J., Darias J., Quezada E., and San-Martin A. A new diterpenoid from the alga Stypopodium flabelliforme. Bol. Soc. Chil. Quim. 39 (1994) 219-221
25. Sabry O.M.M., Andrews S., McPhail K.L., Goeger D.E., Yokochi A., LePage K.T., Murray T.F., and Gerwick W.H. Neurotoxic meroditerpenoids from the tropical marine brown alga Stypopodium flabelliforme. J. Nat. Prod. 68 (2005) 1022-1030
26. Sanchez-Ferrando F., and San-Martin A. Epitaondiol: the first polycyclic meroditerpenoid containing two fused six-membered rings forced into the twist-boat conformation. J. Org. Chem. 60 (1995) 1475-1478
27. Seo Y., Park K.E., Kim Y.A., Lee H.J., Yoo J.S., Ahn J.W., and Lee B.J. Isolation of tetraprenyltoluquinols from the brown alga Sargassum thunbergii. Chem. Pharm. Bull. 54 (2006) 1730-1733
28. Soares A.R., Teixeira V.L., Pereira R.C., and Villaca R. Variation on diterpene production by the brazilian alga Stypopodium zonale (Dictyotales, Phaeophyta). Biochem. Syst. Ecol. 31 (2003) 1347-1350
29. Tomasi J., and Persico M. Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem. Rev. 94 (1994) 2027-2094
30. Tziveleka L.A., Abatis D., Paulus K., Bauer R., Vagias C., and Roussis V. Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation. Chem. Biodivers. 2 (2005) 901-909
31. Wessels M., König G.M., and Wright A.D. A new tyrosine kinase inhibitor from the marine brown alga Stypopodium zonale. J. Nat. Prod. 62 (1999) 927-930
32. Wolinski K., Hilton J.F., and Pulay P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 112 (1990) 8251-8260