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 bromopy...
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2014
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v77_n5_p1170_PatinoC http://hdl.handle.net/20.500.12110/paper_01633864_v77_n5_p1170_PatinoC |
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paper:paper_01633864_v77_n5_p1170_PatinoC2023-06-08T15:14:19Z Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum Puricelli, Lydia Inés Palermo, Jorge Alejandro 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 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. Fil:Puricelli, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Palermo, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v77_n5_p1170_PatinoC http://hdl.handle.net/20.500.12110/paper_01633864_v77_n5_p1170_PatinoC |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Puricelli, Lydia Inés Palermo, Jorge Alejandro Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| topic_facet |
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 |
| description |
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. |
| author |
Puricelli, Lydia Inés Palermo, Jorge Alejandro |
| author_facet |
Puricelli, Lydia Inés Palermo, Jorge Alejandro |
| author_sort |
Puricelli, Lydia Inés |
| title |
Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| title_short |
Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| title_full |
Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| title_fullStr |
Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| title_full_unstemmed |
Bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| title_sort |
bromopyrrole alkaloids isolated from the patagonian bryozoan aspidostoma giganteum |
| publishDate |
2014 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01633864_v77_n5_p1170_PatinoC http://hdl.handle.net/20.500.12110/paper_01633864_v77_n5_p1170_PatinoC |
| work_keys_str_mv |
AT puricellilydiaines bromopyrrolealkaloidsisolatedfromthepatagonianbryozoanaspidostomagiganteum AT palermojorgealejandro bromopyrrolealkaloidsisolatedfromthepatagonianbryozoanaspidostomagiganteum |
| _version_ |
1768543747078881280 |