Planta Med 2008; 74 - PG71
DOI: 10.1055/s-0028-1084823

Biosynthesis of bromopyrrole alkaloids in Agelas oroides

N Cachet 1, OP Thomas 1, A Al-Mourabit 2, F Oberhänsli 3, JL Teyssié 3, R Jeffree 3
  • 1LCMBA, UMR 6001 CNRS-Université de Nice-Sophia Antipolis, Faculté des Sciences, Parc Valrose 06108 Nice Cedex 02, France
  • 2ICSN CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
  • 3Radioecology Laboratory, IAEA Marine Environment Laboratories, 4 Quai Antoine 1er, Monaco, MC, 98000, Monaco

Marine sponges are a source of a great diversity of secondary metabolites presumably used for protection against predators, overgrowing space competitors, invading microorganisms, etc[1].

Bromopyrrole alkaloids are a large bioactive family of secondary metabolites especially found in the sponge families Agelasidae and Axinellidae [2] where oroidin is considered as a key precursor of the elaboration of polycyclic C11N5 pyrrole-2-aminoimidazole derivatives [3].

The common Mediterranean sponge Agelas oroides was chosen as our model species for its wide distribution but also due to the high and almost exclusive production of oroidin by this organism.

The first step of our biosynthetic studies is the confirmation of the origin of oroidin where arginine and proline are proposed as precursors using radiolabelled ex situ experiments.4

The following steps are the understanding of the overall biosynthetic pathway of oroidin and its kinetic accumulation in order to optimize the condition of production. The main purpose of these studies is to understand when, why and how oroidin is produced by Agelas oroides.

References:

1. Pawlik J.R. (1993) Chem Rev, 93: 1911–1922

2. Braekman et al (1992) Biochem. Syst. Ecol., 20: 417–431.

3. Fattorusso et al (1996) Tetrahedron Lett., 37: 3587–3590.

4. Al-Mourabit et al (2006) Org. Lett., 8: 2421–2424.