Abstract
An exhaustive exploration into the metabolic content of the Mediterranean sponge Axinella-polypoides resulted in the isolation of the new betaine 5 and the new cyclonucleoside 8. The structures of the new metabolites were elucidated by spectroscopic methods assisted by computational methods. The analysis also provided evidence that the sponge does not elaborate pyrrole-imidazole alkaloids (PIAs) but, interestingly, it was shown to contain two already known cyclodipeptides, compounds 9 (verpacamide A) and 10.
Highlights
Diverse natural products found within sponges mediate many of their ecological interactions, including defense against predators and fouling organisms
Specimens of A. polypoides were collected in the bay of Calvi (Corsica, France), they were immediately frozen after collection, and kept at −20 °C until extraction
While highlighting the uncommon chemodiversity of A. polypoides, these results pointed out that the sponge does not elaborate pyrrole-imidazole alkaloids (PIAs). This finding is in agreement with the results of a recent investigation on the chemical defense of A. polypoides and the co-occurring species A. verrrucosa, against microbial fouling and in feeding deterrence of a potential predator [24], activities which are believed to be mediated by PIAs [1,2]
Summary
Diverse natural products found within sponges mediate many of their ecological interactions, including defense against predators and fouling organisms. Drugs 2012, 10 interesting target for chemo-ecological investigations They are a well-known source of pyrrole-imidazole alkaloids (PIAs), which have been found only in the marine environment to date. This family of alkaloids has attracted the attention of natural product chemists because of their structural complexity and pharmacological activity; their role in chemically mediated interactions of Caribbean sponges has been proven [1,2]. IZ208 [18]; the relevant cyclo(L-Arg-L-Pro) stereoisomer, verpacamide A (9), was first reported as a natural metabolite of the sponge Axinella vaceleti along with the analogues verpacamides B–D and these metabolites were considered as possible precursors of PIAs [19]
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