Agelas oroides alkaloids

The pyrrole-imidazole alkaloid taurodispacamide A (486) has been isolated from the Mediterranean sponge Agelas oroides. The structure was established from spectroscopic data. Taurodispacamide A (486) exhibited antihistaminic activity when tested on guinea pig ileum [415]. 

Fattorusso E, Taglialatela-Scafati (2000) Two Novel Pyrrole-Imidazole Alkaloids from the Mediterranean Sponge Agelas oroides. Tetrahedron Lett 41 9917... 

The parent compound of this class is cyclooroidin (38), isolated from the Mediterranean sponge Agelas oroides [40]. Two syntheses of this alkaloid have been proposed [66,67], and one of them, obtaining rac-cyclooroidin by intramolecular cyclization of oroidin formate at 95 °C in protic solvents, could have biomimetic significance [67]. 

Fattorusso, E. and Taglialatela-Scafati, O. (2000) Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides. 

Cyclooroidin (35), from Age las oroides [22], and its analogues agesamide (36) from Agelas sp. [40] and oxocyclostylidol (37) from Stylissa caribica [41] are N1/C9 derivatives (Figme 5). Cyclooroidin (35) could be envisaged as the precursor of the non-imidazole bromopyrrole alkaloids longamides (see below). 

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