Dereplication of Bromotyrosine-derived Metabolites by LC-PDA-MS and Analysis of the Chemical Profile of 14 Aplysina Sponge Specimens from the Brazilian Coastline

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Contents Vol 63(6)

doi:10.1071/CH09616

Dereplication of Bromotyrosine-derived Metabolites by LC-PDA-MS and Analysis of the Chemical Profile of 14 Aplysina Sponge Specimens from the Brazilian Coastline*

Michelli M. Silva ^A, Juliana Bergamasco ^A, Simone P. Lira ^A ^B, Norberto P. Lopes ^C, Eduardo Hajdu ^D, Solange Peixinho ^E, Roberto G. S. Berlinck ^A ^F

^A Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, São Carlos, SP, Brazil.
^B Departamento de Ciências Exatas, LCE, Escola Superior ‘Luiz de Queiroz’, Universidade de São Paulo, Pavilhão de Engenharia, Av. Pádua Dias, 11, CP 9, CEP 13418-900, Piracicaba, SP, Brazil.
^C Departamento de Física e Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café - S/N, Monte Alegre, CEP 14049-000, Ribeirão Preto, SP, Brazil.
^D Museu Nacional, Universidade Federal do Rio de Janeiro, Quinta da Boa Vista, s/n, 20940-040, Rio de Janeiro, RJ, Brazil.
^E Instituto de Biologia, Universidade Federal da Bahia, Salvador, BA, Brazil.
^F Corresponding author. Email: rgsberlinck@iqsc.usp.br





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Australian Journal of Chemistry 63(6) 886–894 http://dx.doi.org/10.1071/CH09616
Submitted: 29 November 2009 Accepted: 11 March 2010 Published online: 11 June 2010

Abstract

In order to investigate the chemical profile of 14 specimens of Aplysina spp. marine sponges, we have developed a method based on LC-PDA-MS for the detection of bromotyrosine-derived metabolites. The method enabled the dereplication of three distinct chemotypes of bromotyrosine-derived compounds based on UV absorptions, which were further refined by electrospray ionization-mass spectrometry analysis of the brominated quasi-molecular ion clusters. This procedure led to either a single compound assignment, or a maximum of two possible isobaric compounds. The dereplication study indicated that the chemical profile of the 14 specimens of Aplysina spp. analyzed presented practically the same dibromotyrosine-derived compounds. The results obtained suggested a possible biogenetic pathway for the formation of dibromotyrosine-derived compounds of wide occurrence in Verongida sponges.

^* Dedicated to Professor Ernesto Fattorusso, University of Naples ‘Federico II’, for his outstanding contributions to the chemistry of marine organisms.