Chemical investigation on Indonesian marine sponge Mycale phyllophila

Triana Hertiani; Ru Angelie Edrada; Rob W.M. Van Soest; Sudarsono .; Werner E.G. Muller; Peter Proksch

doi:10.14499/indonesianjpharm0iss0pp104-111

Chemical investigation on Indonesian marine sponge Mycale phyllophila

Triana Hertiani, Ru Angelie Edrada, Rob W.M. Van Soest, Sudarsono ., Werner E.G. Muller, Peter Proksch

Abstract

Chemical investigation on marine sponge Mycale phyllophila collected from Bali, Indonesia has been performed. This study was aimed to isolate and to identify structures of the sponge secondary metabolites as well as to test their cytotoxic activity on mouse lymphoma cell line L5178Y.

The sponge extract was fractionated by liquid-liquid partition followed with a vacuum liquid chromatography method. Structure elucidation was performed on the basis of extensive spectroscopic analysis involving one and two dimensional NMR spectroscopy as well as mass spectrometry. Cytotoxicity was tested on mouse lymphoma cell line L5178Y by using the microculture tetrazolium (MTT) assay. This study found a mixture of 5-pentadecyl-1H-pyrrole-2-carbaldehyde and (6’E)-5-(6’pentadecenyl)-1H-pyrrole-2-carbaldehyde as major constituents of the sponge extract. Those compounds were expected to be the active constituent to show growth inhibition of mouse lymphoma cell line (L5178Y) in vitro.

Key words : Mycale phyllophila, cytotoxic agent, NMR spectroscopy.

Full Text:

IJPSeptember2009_104-111

References

Carmichael, J., DeGraff, W.G., Gazdar, A.F., Minna, J.D., and Mitchell, J.B., 1987, Evaluation of Tetrazolium-based semi automated colorimetric assay: Assessment of radio sensitivity, Cancer Res., 47, 943-946.

Corriero, G., Madaio, A., Mayol, L., Piccialli, V., and Sica, D., 1989, Rotalin A and B, two novel diterpene metabolites from the encrusting sponge Mycale rotalis, Tetrahedron, 45, 277-288.

Fusetani, N., Sugawara, T., Matsunaga, S., and Hirota, H., 1991, Bioactive marine metabolites. Part 35. Cytotoxic metabolites of the marine sponge Mycale adhaerens Lambe, J. Org. Chem., 56 (16), 4971-4974.

Fusetani, N., Yasumuro, K., Matsunaga, S., and Hashimoto, K., 1989, Mycalolides A-C, hybrid macrolides of ulapualides and halichondramide, from a sponge of the genus mycale, Tetrahedron Lett., 30(21), 2809-2812.

Giordano, F., Mayol, L., Notaro, G., Piccialli, V., and Sica, D., 1990, Structure and absolute configuration of two new polybrominated C16 acetogenins from the sponge Mycale rotalis, J. Chem. Soc. Chem. Commun., 22, 1559-1561.

Jones, R.A., and Bean, G.P., 1977, The chemistry of pyrroles, Academic Press, New York.

Kato,Y., Fusetani, N., Matsunaga, S., and Hashimoto, K., 1985, Bioactive marine metabolites IX. Mycalisines A and B, novel nucleosides which inhibit cell division of fertilized starfish eggs, from the marine sponge Mycale sp. Tetrahedron Lett., 26(29), 3483-3486.

Ortega, Maria J.; Zubia, Eva; Sánchez, M. Carmen; Salvá, Javier; and Carballo, J. Luis, 2004, Structure and cytotoxicity of new metabolites from the sponge Mycale Cecilia, Tetrahedron, 60(11), 2517 – 2524.

Ortega, M.J., Zubia, E., Carballo, J.L., and Salvá, 1997, New cytotoxic metabolites from the sponge Mycale micracanthoxea, Tetrahedron, 53(1), 331 – 340.

Perry, N.B., Blunt, W.J., Munro, M.H.G., and Thompson, A.M., 1990, Antiviral and antitumor agents from a New Zealand sponge, Mycale sp. 2. Structures and conformations of mycalamides A and B, J. Org. Chem., 55(1), 223-227.

Reddy, G. Bala Show; and Dhananjaya, N., 2000, Chemical investigations of Mycale mytilorum and a study on toxicity and anti diabetic activity of 5- octadecylpyrrole-2-carboxaldehyde, Bioorg. Med. Chem., 8(1), 27–36.

Stierle, D.B., and Faulkner, D.J., 1980, Metabolites of the marine sponge Laxosuberites sp., J. Org. Chem., 45(24), 4980-4982.

Venkatesham, U., Rao, M.R., and Venkateswarlu, Y., 2000, New 5-alkylpyrrole-2- carboxaldehyde derivatives from the sponge Mycale tenuisiculata, J. Nat. Prod., 63(9) 1318-1320.

DOI: http://dx.doi.org/10.14499/indonesianjpharm0iss0pp104-111