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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6950519 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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