Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis
Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C(15) acetogenin medium-ring ethers. Here, we described the isolation of three new C(15) acetogenins (3–5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. Thes...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793053/ https://www.ncbi.nlm.nih.gov/pubmed/29286293 http://dx.doi.org/10.3390/md16010005 |
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author | Morales-Amador, Adrián de Vera, Caterina R. Márquez-Fernández, Olivia Hernández Daranas, Antonio Padrón, José M. Fernández, José J. Souto, María L. Norte, Manuel |
author_facet | Morales-Amador, Adrián de Vera, Caterina R. Márquez-Fernández, Olivia Hernández Daranas, Antonio Padrón, José M. Fernández, José J. Souto, María L. Norte, Manuel |
author_sort | Morales-Amador, Adrián |
collection | PubMed |
description | Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C(15) acetogenin medium-ring ethers. Here, we described the isolation of three new C(15) acetogenins (3–5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives (3–4). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J-based configuration analysis and DFT (Density Functional Theory) calculations. Their antiproliferative activity against six human solid tumor cell lines was evaluated. |
format | Online Article Text |
id | pubmed-5793053 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-57930532018-02-06 Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis Morales-Amador, Adrián de Vera, Caterina R. Márquez-Fernández, Olivia Hernández Daranas, Antonio Padrón, José M. Fernández, José J. Souto, María L. Norte, Manuel Mar Drugs Article Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C(15) acetogenin medium-ring ethers. Here, we described the isolation of three new C(15) acetogenins (3–5), and one truncated derivative (6) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives (3–4). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J-based configuration analysis and DFT (Density Functional Theory) calculations. Their antiproliferative activity against six human solid tumor cell lines was evaluated. MDPI 2017-12-29 /pmc/articles/PMC5793053/ /pubmed/29286293 http://dx.doi.org/10.3390/md16010005 Text en © 2017 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 Morales-Amador, Adrián de Vera, Caterina R. Márquez-Fernández, Olivia Hernández Daranas, Antonio Padrón, José M. Fernández, José J. Souto, María L. Norte, Manuel Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title | Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title_full | Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title_fullStr | Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title_full_unstemmed | Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title_short | Pinnatifidenyne-Derived Ethynyl Oxirane Acetogenins from Laurencia viridis |
title_sort | pinnatifidenyne-derived ethynyl oxirane acetogenins from laurencia viridis |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5793053/ https://www.ncbi.nlm.nih.gov/pubmed/29286293 http://dx.doi.org/10.3390/md16010005 |
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