Chemical investigation on Pseudoceratina purpurea collected from Banyuwangi Indonesia

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


Chemical investigation on marine sponge Pseudoceratina purpurea collected from Banyuwangi, 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 cytotoxicity activity on mouse lymphoma cell line L5178Y.

Isolation procedure was performed by using different chromatography techniques. NMR spectroscopy and mass spectrometry methods were used to identify the compounds chemical structures. Cytotoxicity of the isolates was tested on mouse lymphoma cell line L5178Y by using the microculture tetrazolium (MTT) assay.

This study yielded five known tyrosine-derived alkaloids, two of which, aplysamine-2 (1) and aeroplysinin-1 (2) showed growth inhibition of mouse lymphoma cell line L5178Y with IC50 value of 1.7 mg/mL and 0.57 mg/mL, respectively.

Key words: Pseudoceratina purpurea, sponge, alkaloids.

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Andersen, R.J., and Faulkner, D.J., 1973, A novel antibiotic from a sponge of the genus Verongia, Tetrahedron Lett., 14, 1175-1178.

Amir, I., A, 2005, Comparison of sponge fauna of exposed and sheltered reef flats in eastern Indonesia, Mar. Res. Indonesia, 28, 1-12, cit Calcinai, Barbara; Bavestrello, Giorgio; and Cerrano, Carlo, 1992, Zoological Studies, 44(1): 5-18.

Bergquist, P.R., and Cook, S.C., In: Hooper, J.N.A., and Van Soest, R.W.M. (Eds.), 2002, Systema Porifera: A guide to the classification of sponges, Kluwer Academic/Plenum, New York, 1081, 1086-1088.

Calcinai, B., Bavestrello, G., and Cerrano, C., 2005, Excavating sponge species from the Indo- Pacific ocean, Zoological Studies, 44(1): 5-18.

Capon, R.J., and Macleod, J.K., 1987, Two epimeric dibromo nitriles from the Australian sponge Aplysina laevis, Aust. J. Chem., 40(2), 341-346.

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.

Cimino, G., de Rosa, S., de Stefano, S., Spinella, A., and Sodano, G., 1984, The zoochrome of the sponge Verongia aerophoba (“Uranidine”), Tetrahedron Lett., 25 (27), 2925 – 2928.

D’Ambrosio, M.D., Guerriero, A., and Pietra, F., 168. 1984, Novel, racemic or nearly-racemic antibacterial bromo- and chloroquinols and g-lactams of the verongiaquinol and the cavernicolin type from the marine sponge Aplysina (= Verongia) cavernicola, Helv. Chim. Acta, 67,1484-1492.

D’Ambrosio, M., Guerriero, A., Traldi, P., and Pietra, F., 1982, Cavernicolin-1 and Cavernicolin-2, Two epimeric dibromolactams from the Mediterranean sponge Aplysina (Verongia) cavernicola, Tetrahedron Lett., 23(42), 4403-4406.

Ebel, R., Brenzinger, M., Kunze, A., Gross, H.J., and Proksch, P., 1997, Wound activation of protoxins in marine sponge Apysina aerophoba, J. Chem. Ecol., 23, 1451-1462.

Fattorusso, E., Minale, L., and Sodano, G., 1970, Aeroplysinin-1, a new bromo-compound from Aplysina aerophoba, Chem. Communs., 751-752.

Fulmor, W., Van Lear, G.E, Morton, G.O., and Mills, R.D., 1970, Isolation and absolute configuration of the aeroplysinin 1 enantiomorphic pair from Ianthella ardis, Tetrahedron Lett., 52, 4551-4552.

Kijjoa, A., Bessa, J., Wattanadilok, R., Sawangwong, P., Nascimento, M.S.J., Pedro, M., Silva, A.M.S., Eaton, G., Van Soest, R.W., and Herz, W., 2005, Dibromotyrosine derivatives, a maleimide, aplysamine-2 and other constituents of the marine sponge Pseudoceratina purpurea, Z. Naturforsch., 60b, 904 – 908.

Kossuga, M.H., MacMillan, J.B., Rogers, E.W., Molinski, T.F., Nascimento, G.G.F., Rocha, R.M., and Berlinck, R.G.S., 2004, 2S,3R)-2-Aminododecan-3-ol, a new antifungal agent from the ascidian Clavelina oblonga, J. Nat. Prod., 67, 1879-1881.

Koulman, A., Proksch, P., Ebel., R., Beekman, A., van Uden, W., Konings, A.W.T., Pedersen, J.A., Pras, N., and Woerdenbag, H.J., 1996, Cytotoxicity and mode of action of aeroplysinin 1 and a related dienone from the sponge Aplysina aerophoba, J. Nat. Prod., 59, 591-594.

Kreuter, M.H., Leake, R.E., Rinaldi, F., Müller-Klieser, W., Maidhof, A., Müller, W.E.G., Schröder, H.C., 1990, Comp. Biochem. Physiol., 97B, 151-158.

Kreuter, M.H., Bernd, A., Holzmann, H., Müller-Klieser, W., Maidhof, A., Weissmann, N., Kljajic, E., Batel, R., Schröder, H.C., and Müller, W.E.G., 1989, Z. Naturforsch., 44c, 680-688.

Minale, L., Cimino, G., DeStefano, S., and Sodano, G., 1976, Fortschr. Chem. Org. Naturst., 33, 1-72.

Norte, M., Rodriguez, M.L., Fernández, J.J., Eguron, L., and Estrada, D.M., 1988, Aplysinadiene and (R,R) 5 (3,5-dibromo-4-[(2-oxo-5-oxazolidinyl)] methoxyphenyl)-2-oxazolidinone, two novel metabolites from Aplysina aerophoba. Synthesis of aplysinadiene, Tetrahedron, 44(15), 4973-4980.

Ortlepp, S., Dissertation, 2007, Heinrich-Heine Universität, Düsseldorf.

Rogers, E.W., de Oliveira, M.F., Berlinck, R.G.S., König, G.M., and Molinski, T.F., 2005, Stereochemical heterogeneity in Verongid sponge metabolites. Absolute stereochemistry of (+)-fistularin-3 and (+)-11-epi-fistularin-3 by microscale LCMSMarfey’s analysis, J. Nat. Prod., 68, 891-896.

Simmons, T. Luke; Andrianasolo, Eric; McPhail, Kerry, Flatt, Patricia; and Gerwick, William, 2005, Marine natural products as anticancer drugs, Mol. Cancer Ther., 4(2) 333-342.

Smith, R.M., 2005, Understanding mass spectra: a basic approach, Wiley-Interscience, New Jersey.

Tabudravu, J.N.; and Jaspars M., 2002, Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp., J. Nat. Prod., 65, 1798 – 1801.

Teeyapant, R., Woerdenbag, H.J., Kreis, P., Hacker, J., Wray, V., Witte, L., and Proksch, P., 1993, Antibiotic and cytotoxic of brominated compounds from the marine sponge Verongia aerophoba, Z. Naturforsch., 48c, 939-945.

Thompson, J.E., Barrow, K.D., and Faulkner, D.J., 1983, Localization of two brominated metabolites, aerothionin and homoaerothionin, in spherulous cells of the marine sponge Aplysina fistularis, Acta Zool., 64, 199-210.

Thoms, C., Ebel, R., and Proksch, P., 2006, Activated chemical defense in Aplysina sponges revisited, J. Chem. Ecol., 32(1), 97-123.

Thoms, C., Wolff, M., Padmakumar, K., Ebel., R., and Proksch, P., 2004, Chemical defense of Mediterranean sponges Aplysina cavernicola and Aplysina aerophoba, Z. Naturforsch., 59c, 113-122.

Thoms, C., Ebel, R., Hentschel, U., and Proksch, P., 2003, Sequestration of dietary alkaloids by the spongivorous marine mollusc Tylodina perversa, Z. Naturforsch., 58c, 426-432.

Turon, X., Becerro, M.A., and Uriz, M.J., 2000, Distribution of brominated compounds within the sponge Aplysina aerophoba: Coupling of X-ray microanalyses with cryofixation techniques, Cell Tissue Res., 301, 311-322.

Van Soest, R.W.M., 1989, The Indonesian sponge fauna: a status report, Netherlands Journal of Sea Research, 23(2), 223 – 230.

Weiss, B., Ebel, R., Elbrächter, M., Kirchner, M., and Proksch, P., 1996, Defense metabolites from the marine sponge Verongia aerophoba, Biochem. Syst. Ecol., 24, 1-12.

Xynas, R., and Capon, R., Aust. J. Chem., 1989, 42, 1427-1433.

Yagi, H., Matsunaga, S., and Fusetani, N., Tetrahedron, 1993, 49, 3749-3754.



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