TY - JOUR
T1 - Chemical variability within the marine sponge Aplysina fulva
AU - Nuñez, Cecília V.
AU - de Almeida, Erika V.R.
AU - Granato, Ana Claudia
AU - Marques, Suzi O.
AU - Santos, Kelly O.
AU - Pereira, Fabio R.
AU - Macedo, Mario L.
AU - Ferreira, Antonio G.
AU - Hajdu, Eduardo
AU - Pinheiro, Ulisses S.
AU - Muricy, Guilherme
AU - Peixinho, Solange
AU - Freeman, Christopher J.
AU - Gleason, Daniel F.
AU - Berlinck, Roberto G.S.
PY - 2008/4
Y1 - 2008/4
N2 - Dibromotyrosine-derived metabolites are of common occurrence within marine sponges belonging to the order Verongida. However, previous chemical analysis of crude extracts obtained from samples of the verongid sponge Aplysina fulva collected in Brazil did not provide any dibromotyrosine-derived compounds. In this investigation, five samples of A. fulva from five different locations along the Brazilian coastline and one sample from a temperate reef in the South Atlantic Bight (SAB) (Georgia, USA) were investigated for the presence of bromotyrosine-derived compounds. All six samples collected yielded dibromotyrosine-derived compounds, including a new derivative, named aplysinafulvin, which has been identified by analysis of spectroscopic data. These results confirm previous assumptions that dibromotyrosine-derived metabolites can be considered as chemotaxonomic markers of verongid sponges. The isolation of aplysinafulvin provides additional support for a biogenetic pathway involving an arene oxide intermediate in the biosynthesis of Verongida metabolites. It cannot yet be established if the chemical variability observed among the six samples of A. fulva collected in Brazil and the SAB is the result of different environmental factors, distinct chemical extraction and isolation protocols, or a consequence of hidden genetic diversity within the postulated morphological plasticity of this species.
AB - Dibromotyrosine-derived metabolites are of common occurrence within marine sponges belonging to the order Verongida. However, previous chemical analysis of crude extracts obtained from samples of the verongid sponge Aplysina fulva collected in Brazil did not provide any dibromotyrosine-derived compounds. In this investigation, five samples of A. fulva from five different locations along the Brazilian coastline and one sample from a temperate reef in the South Atlantic Bight (SAB) (Georgia, USA) were investigated for the presence of bromotyrosine-derived compounds. All six samples collected yielded dibromotyrosine-derived compounds, including a new derivative, named aplysinafulvin, which has been identified by analysis of spectroscopic data. These results confirm previous assumptions that dibromotyrosine-derived metabolites can be considered as chemotaxonomic markers of verongid sponges. The isolation of aplysinafulvin provides additional support for a biogenetic pathway involving an arene oxide intermediate in the biosynthesis of Verongida metabolites. It cannot yet be established if the chemical variability observed among the six samples of A. fulva collected in Brazil and the SAB is the result of different environmental factors, distinct chemical extraction and isolation protocols, or a consequence of hidden genetic diversity within the postulated morphological plasticity of this species.
KW - Aplysina fulva
KW - Chemical variability
KW - Chemotaxonomy
KW - Dibromotyrosine
UR - http://www.scopus.com/inward/record.url?scp=40049100830&partnerID=8YFLogxK
U2 - 10.1016/j.bse.2007.09.008
DO - 10.1016/j.bse.2007.09.008
M3 - Article
AN - SCOPUS:40049100830
SN - 0305-1978
VL - 36
SP - 283
EP - 296
JO - Biochemical Systematics and Ecology
JF - Biochemical Systematics and Ecology
IS - 4
ER -