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Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata

Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as...

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Autores principales: Ragini, Kavita, Piggott, Andrew M., Karuso, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6950519/
https://www.ncbi.nlm.nih.gov/pubmed/31817295
http://dx.doi.org/10.3390/md17120683
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author Ragini, Kavita
Piggott, Andrew M.
Karuso, Peter
author_facet Ragini, Kavita
Piggott, Andrew M.
Karuso, Peter
author_sort Ragini, Kavita
collection PubMed
description Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes.
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spelling pubmed-69505192020-01-16 Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata Ragini, Kavita Piggott, Andrew M. Karuso, Peter Mar Drugs Article Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes. MDPI 2019-12-04 /pmc/articles/PMC6950519/ /pubmed/31817295 http://dx.doi.org/10.3390/md17120683 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ragini, Kavita
Piggott, Andrew M.
Karuso, Peter
Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title_full Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title_fullStr Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title_full_unstemmed Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title_short Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata
title_sort bisindole alkaloids from a new zealand deep-sea marine sponge lamellomorpha strongylata
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6950519/
https://www.ncbi.nlm.nih.gov/pubmed/31817295
http://dx.doi.org/10.3390/md17120683
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