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; Juliana Bergamasco; Simone P. Lira; Norberto P. Lopes; Eduardo Hajdu; Solange Peixinho; Roberto G. S. Berlinck

doi:10.1071/CH09616

RESEARCH FRONT

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 and Roberto G. S. Berlinck ^A ^F

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 63(6) 886-894 https://doi.org/10.1071/CH09616
Submitted: 29 November 2009 Accepted: 11 March 2010 Published: 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.

Acknowledgements

The authors thank Prof. John Blunt (University of Canterbury, NZ) for help in using MarinLit for dereplication purposes, as well as Katyuscya Veloso and Professor Antonio G. Ferreira (Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, Brazil), for assistance in the NMR analysis. Financial support was provided by the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), grant BIOTA/BIOprospecTA 05/60175–2 to R.G.S.B. and a post-doctoral scholarship (06/60510–9) to S.P.L., as well as by CNPq to N.P.L., E.H., and R.G.S.B.

References

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

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

Abstract

Acknowledgements

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