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HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)
Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6025042/ https://www.ncbi.nlm.nih.gov/pubmed/29849004 http://dx.doi.org/10.3390/md16060189 |
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author | Buedenbender, Larissa Robertson, Luke P. Lucantoni, Leonardo Avery, Vicky M. Kurtböke, D. İpek Carroll, Anthony R. |
author_facet | Buedenbender, Larissa Robertson, Luke P. Lucantoni, Leonardo Avery, Vicky M. Kurtböke, D. İpek Carroll, Anthony R. |
author_sort | Buedenbender, Larissa |
collection | PubMed |
description | Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1–2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility. |
format | Online Article Text |
id | pubmed-6025042 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-60250422018-07-09 HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) Buedenbender, Larissa Robertson, Luke P. Lucantoni, Leonardo Avery, Vicky M. Kurtböke, D. İpek Carroll, Anthony R. Mar Drugs Article Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1–2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility. MDPI 2018-05-30 /pmc/articles/PMC6025042/ /pubmed/29849004 http://dx.doi.org/10.3390/md16060189 Text en © 2018 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 Buedenbender, Larissa Robertson, Luke P. Lucantoni, Leonardo Avery, Vicky M. Kurtböke, D. İpek Carroll, Anthony R. HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title_full | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title_fullStr | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title_full_unstemmed | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title_short | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
title_sort | hsqc-tocsy fingerprinting-directed discovery of antiplasmodial polyketides from the marine ascidian-derived streptomyces sp. (usc-16018) |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6025042/ https://www.ncbi.nlm.nih.gov/pubmed/29849004 http://dx.doi.org/10.3390/md16060189 |
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