Bromopyrrole alkaloids isolated from the Patagonian bryozoan Aspidostoma giganteum.
Nine new bromopyrrole alkaloids, aspidostomides A-H and aspidazide A (1-9), were isolated from the Patagonian bryozoan Aspidostoma giganteum. Aspidostomides A-H have dibromotyrosine- or bromotryptophan-derived moieties forming either linear amides or pyrroloketopiperazine-type lactams with a bromopyrrole carboxylic acid as a common structural motif. On the other hand, aspidazide A is a rare asymmetric acyl azide formed by an N-N link of two different pyrroloketopiperazine lactams and is the first isolated compound of this class from marine invertebrates. This work is the first report of secondary metabolites isolated from a bryozoan from the Patagonian region. The structures of compounds 1-9 were elucidated by spectroscopic methods and chemical transformations. One of these compounds, aspidostomide E (5), was moderately active against the 786-O renal carcinoma cell line.
UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires , Ciudad Universitaria, Pabellón 2 (1428), Buenos Aires, Argentina.
Laura P
LP
Patiño C
Claudia
C
Muniain
Maria Elena
ME
Knott
Lydia
L
Puricelli
Jorge A
JA
Palermo
D047230:Agelas / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D002264:Carboxylic Acids; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011758:Pyrroles / Q000737:chemistry
D000470:Alkaloids; D002264:Carboxylic Acids; D006842:Hydrocarbons, Brominated; D011758:Pyrroles; C000591887:aspidostomide E