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Patiño C, L.P.; Muniain, C.; Knott, M.E.; Puricelli, L.; Palermo, J.A. "Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum" (2014) Journal of Natural Products. 77(5):1170-1178
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Abstract:

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. © 2014 The American Chemical Society and American Society of Pharmacognosy.

Registro:

Documento: Artículo
Título:Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum
Autor:Patiño C, L.P.; Muniain, C.; Knott, M.E.; Puricelli, L.; Palermo, J.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, (1428), Buenos Aires, Argentina
Laboratorio de Ecología Química y Biodiversidad Acuática, Instituto de Investigación e Ingeniería Ambiental, Universidad de San Martín, Peatonal Belgrano 3563, (1650)-San-Martín-Buenos-Aires, Argentina
Research Area, Angel H. Roffo Institute of Oncology, University of Buenos Aires, Avenida San Martín 5481, (C1417DTB), Buenos Aires, Argentina
Palabras clave:alkaloid; aspidazide a; aspidostomide a; aspidostomide b; aspidostomide c; aspidostomide d; aspidostomide e; aspidostomide f; aspidostomide g; aspidostomide h; carboxylic acid; lactam derivative; piperazine derivative; pyrrole derivative; tryptophan derivative; tyrosine derivative; unclassified drug; article; aspidostoma giganteum; Bryozoa; carbon nuclear magnetic resonance; chemical phenomena; chemical transformation; cytotoxicity; drug isolation; drug structure; human; human cell; invertebrate; methylation; proton nuclear magnetic resonance; renal cell carcinoma cell line; Agelas; Alkaloids; Animals; Carboxylic Acids; Humans; Hydrocarbons, Brominated; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pyrroles
Año:2014
Volumen:77
Número:5
Página de inicio:1170
Página de fin:1178
DOI: http://dx.doi.org/10.1021/np500012y
Título revista:Journal of Natural Products
Título revista abreviado:J. Nat. Prod.
ISSN:01633864
CODEN:JNPRD
CAS:tyrosine derivative, 42406-77-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v77_n5_p1170_PatinoC

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Citas:

---------- APA ----------
Patiño C, L.P., Muniain, C., Knott, M.E., Puricelli, L. & Palermo, J.A. (2014) . Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum. Journal of Natural Products, 77(5), 1170-1178.
http://dx.doi.org/10.1021/np500012y
---------- CHICAGO ----------
Patiño C, L.P., Muniain, C., Knott, M.E., Puricelli, L., Palermo, J.A. "Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum" . Journal of Natural Products 77, no. 5 (2014) : 1170-1178.
http://dx.doi.org/10.1021/np500012y
---------- MLA ----------
Patiño C, L.P., Muniain, C., Knott, M.E., Puricelli, L., Palermo, J.A. "Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum" . Journal of Natural Products, vol. 77, no. 5, 2014, pp. 1170-1178.
http://dx.doi.org/10.1021/np500012y
---------- VANCOUVER ----------
Patiño C, L.P., Muniain, C., Knott, M.E., Puricelli, L., Palermo, J.A. Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum. J. Nat. Prod. 2014;77(5):1170-1178.
http://dx.doi.org/10.1021/np500012y