Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4–18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified o...

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Autores principales: Göthel, Qun, Sirirak, Thanchanok, Köck, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685874/
https://www.ncbi.nlm.nih.gov/pubmed/26734082
http://dx.doi.org/10.3762/bjoc.11.254
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author Göthel, Qun
Sirirak, Thanchanok
Köck, Matthias
author_facet Göthel, Qun
Sirirak, Thanchanok
Köck, Matthias
author_sort Göthel, Qun
collection PubMed
description Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4–18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The (13)C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells.
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spelling pubmed-46858742016-01-05 Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa Göthel, Qun Sirirak, Thanchanok Köck, Matthias Beilstein J Org Chem Full Research Paper Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4–18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The (13)C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells. Beilstein-Institut 2015-11-26 /pmc/articles/PMC4685874/ /pubmed/26734082 http://dx.doi.org/10.3762/bjoc.11.254 Text en Copyright © 2015, Göthel et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Göthel, Qun
Sirirak, Thanchanok
Köck, Matthias
Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title_full Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title_fullStr Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title_full_unstemmed Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title_short Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
title_sort bromotyrosine-derived alkaloids from the caribbean sponge aplysina lacunosa
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685874/
https://www.ncbi.nlm.nih.gov/pubmed/26734082
http://dx.doi.org/10.3762/bjoc.11.254
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