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Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp.
Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A–C (1–3). The structures of 1–3 were found to be rearranged, multicyclic, angucyclin...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7073551/ https://www.ncbi.nlm.nih.gov/pubmed/32085561 http://dx.doi.org/10.3390/md18020121 |
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author | Bae, Munhyung An, Joon Soo Hong, Seong-Heon Bae, Eun Seo Chung, Beomkoo Kwon, Yun Hong, Suckchang Oh, Ki-Bong Shin, Jongheon Lee, Sang Kook Oh, Dong-Chan |
author_facet | Bae, Munhyung An, Joon Soo Hong, Seong-Heon Bae, Eun Seo Chung, Beomkoo Kwon, Yun Hong, Suckchang Oh, Ki-Bong Shin, Jongheon Lee, Sang Kook Oh, Dong-Chan |
author_sort | Bae, Munhyung |
collection | PubMed |
description | Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A–C (1–3). The structures of 1–3 were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics–based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher’s method. Donghaecyclinones A–C (1–3) displayed cytotoxicity against diverse human cancer cell lines (IC(50): 6.7–9.6 μM for 3). |
format | Online Article Text |
id | pubmed-7073551 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-70735512020-03-20 Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. Bae, Munhyung An, Joon Soo Hong, Seong-Heon Bae, Eun Seo Chung, Beomkoo Kwon, Yun Hong, Suckchang Oh, Ki-Bong Shin, Jongheon Lee, Sang Kook Oh, Dong-Chan Mar Drugs Article Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A–C (1–3). The structures of 1–3 were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics–based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher’s method. Donghaecyclinones A–C (1–3) displayed cytotoxicity against diverse human cancer cell lines (IC(50): 6.7–9.6 μM for 3). MDPI 2020-02-18 /pmc/articles/PMC7073551/ /pubmed/32085561 http://dx.doi.org/10.3390/md18020121 Text en © 2020 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 Bae, Munhyung An, Joon Soo Hong, Seong-Heon Bae, Eun Seo Chung, Beomkoo Kwon, Yun Hong, Suckchang Oh, Ki-Bong Shin, Jongheon Lee, Sang Kook Oh, Dong-Chan Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title | Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title_full | Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title_fullStr | Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title_full_unstemmed | Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title_short | Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp. |
title_sort | donghaecyclinones a–c: new cytotoxic rearranged angucyclinones from a volcanic island-derived marine streptomyces sp. |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7073551/ https://www.ncbi.nlm.nih.gov/pubmed/32085561 http://dx.doi.org/10.3390/md18020121 |
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