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Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis
The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A seq...
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/PMC6154597/ https://www.ncbi.nlm.nih.gov/pubmed/28333106 http://dx.doi.org/10.3390/molecules22040513 |
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author | Dziwornu, Godwin A. Caira, Mino R. de la Mare, Jo-Anne Edkins, Adrienne L. Bolton, John J. Beukes, Denzil R. Sunassee, Suthananda N. |
author_facet | Dziwornu, Godwin A. Caira, Mino R. de la Mare, Jo-Anne Edkins, Adrienne L. Bolton, John J. Beukes, Denzil R. Sunassee, Suthananda N. |
author_sort | Dziwornu, Godwin A. |
collection | PubMed |
description | The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A sequence of column chromatography, preparative TLC and normal phase HPLC resulted in the isolation of eleven compounds comprising three labdane-type diterpenes (1–3), four polyether triterpenes (4–7), three cholestane-type ecdysteroids (8–10) and a glycolipid (11). Compounds 1–3, 5–8 and 10 have not previously been reported, while compound 9 is reported here for the first time from a natural source and the known compound 11 isolated for the first time from the genus Laurencia. The structural elucidation and the relative configuration assignments of the compounds were accomplished by extensive use of 1D- and 2D-NMR, HR-ESI-MS, UV and IR spectroscopic techniques, while the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis. All compounds were evaluated against the MDA-MB-231 breast and HeLa cervical cancer cell lines. Compound 2 exhibited low micromolar antiproliferative activity (IC(50) = 9.3 µM) against the triple negative breast carcinoma and compound 7 was similarly active (IC(50) = 8.8 µM) against the cervical cancer cell line. |
format | Online Article Text |
id | pubmed-6154597 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61545972018-11-13 Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis Dziwornu, Godwin A. Caira, Mino R. de la Mare, Jo-Anne Edkins, Adrienne L. Bolton, John J. Beukes, Denzil R. Sunassee, Suthananda N. Molecules Article The marine red algae of the genus Laurencia have been widely studied for their structurally diverse and biologically active secondary metabolites. We report here the natural product investigation of the organic extract of a newly identified South African endemic species, Laurencia alfredensis. A sequence of column chromatography, preparative TLC and normal phase HPLC resulted in the isolation of eleven compounds comprising three labdane-type diterpenes (1–3), four polyether triterpenes (4–7), three cholestane-type ecdysteroids (8–10) and a glycolipid (11). Compounds 1–3, 5–8 and 10 have not previously been reported, while compound 9 is reported here for the first time from a natural source and the known compound 11 isolated for the first time from the genus Laurencia. The structural elucidation and the relative configuration assignments of the compounds were accomplished by extensive use of 1D- and 2D-NMR, HR-ESI-MS, UV and IR spectroscopic techniques, while the absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis. All compounds were evaluated against the MDA-MB-231 breast and HeLa cervical cancer cell lines. Compound 2 exhibited low micromolar antiproliferative activity (IC(50) = 9.3 µM) against the triple negative breast carcinoma and compound 7 was similarly active (IC(50) = 8.8 µM) against the cervical cancer cell line. MDPI 2017-03-23 /pmc/articles/PMC6154597/ /pubmed/28333106 http://dx.doi.org/10.3390/molecules22040513 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 Dziwornu, Godwin A. Caira, Mino R. de la Mare, Jo-Anne Edkins, Adrienne L. Bolton, John J. Beukes, Denzil R. Sunassee, Suthananda N. Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title | Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title_full | Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title_fullStr | Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title_full_unstemmed | Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title_short | Isolation, Characterization and Antiproliferative Activity of New Metabolites from the South African Endemic Red Algal Species Laurencia alfredensis |
title_sort | isolation, characterization and antiproliferative activity of new metabolites from the south african endemic red algal species laurencia alfredensis |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154597/ https://www.ncbi.nlm.nih.gov/pubmed/28333106 http://dx.doi.org/10.3390/molecules22040513 |
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