title: Metabolomics approach to chemical diversity of the Mediterranean marine sponge Agelas oroides.
abstract: The Mediterranean marine sponge Agelas oroides is known to contain a large quantity of oroidin, a deterrent, antifouling and antibiofilm pyrrole-2-aminoimidazole. In contrast with other tropical specimens, the chemical composition of Mediterranean Agelas oroides is surprisingly relatively poor in other related metabolites. In the course of finding novel marine natural products, LC-MS based metabolomics study of the Mediterranean Agelas oroides, however, revealed that next to the major compound oroidin, the sponge contains in fact a great diversity of known pyrrole-imidazole alkaloids in minute amounts. Here, we describe identification of 13 known oroidin class alkaloids along with one new monobromoagelaspongin (24). Five betaines and one amine were also identified from the aqueous fraction. One of those compounds (-)-equinobetaine B (30) was found to be an enantiomer of the known natural product (+)-equinobetaine B.
authors.affiliation: a LBCM, IUEM , University of Bretagne-Sud , Lorient , France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Sauleau
authors.affiliation: b Institut de Chimie des Substances Naturelles, CNRS UPR 2301 , University Paris-Sud, Université Paris-Saclay , Gif-sur-Yvette , France.
authors.forename: Céline
authors.initials: C
authors.lastname: Moriou
authors.affiliation: b Institut de Chimie des Substances Naturelles, CNRS UPR 2301 , University Paris-Sud, Université Paris-Saclay , Gif-sur-Yvette , France.
authors.forename: Ali
authors.initials: A
authors.lastname: Al Mourabit
mesh_terms: D047230:Agelas / Q000737:chemistry*; D000470:Alkaloids / Q000032:analysis / Q000737:chemistry; D000818:Animals; D001688:Biological Products / Q000032:analysis; D007093:Imidazoles / Q000032:analysis; D055432:Metabolomics / Q000379:methods*; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000032:analysis
chemical_list: D000470:Alkaloids; D001688:Biological Products; D007093:Imidazoles; D011758:Pyrroles; C552324:pyrrole-2-aminoimidazole; C029899:imidazole; C077209:oroidin
keywords: Agelas oroides; Agelasidae, pyrrole-2-aminoimidazole; monobromoagelaspongin, (−)-equinobetaine B