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Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.

Chemical investigation of a halophilic actinomycete strain belonging to the genus Nocardiopsis inhabiting a hypersaline saltern led to the discovery of new 18-membered macrolides with nitrile functionality, borrelidins C–E (1–3), along with a previously reported borrelidin (4). The planar structures...

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Autores principales: Kim, Jungwoo, Shin, Daniel, Kim, Seong-Hwan, Park, Wanki, Shin, Yoonho, Kim, Won Kyung, Lee, Sang Kook, Oh, Ki-Bong, Shin, Jongheon, Oh, Dong-Chan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5484116/
https://www.ncbi.nlm.nih.gov/pubmed/28587270
http://dx.doi.org/10.3390/md15060166
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author Kim, Jungwoo
Shin, Daniel
Kim, Seong-Hwan
Park, Wanki
Shin, Yoonho
Kim, Won Kyung
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
author_facet Kim, Jungwoo
Shin, Daniel
Kim, Seong-Hwan
Park, Wanki
Shin, Yoonho
Kim, Won Kyung
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
author_sort Kim, Jungwoo
collection PubMed
description Chemical investigation of a halophilic actinomycete strain belonging to the genus Nocardiopsis inhabiting a hypersaline saltern led to the discovery of new 18-membered macrolides with nitrile functionality, borrelidins C–E (1–3), along with a previously reported borrelidin (4). The planar structures of borrelidins C–E, which are new members of the rare borrelidin class of antibiotics, were elucidated by NMR, mass, IR, and UV spectroscopic analyses. The configurations of borrelidines C–E were determined by the interpretation of ROESY NMR spectra, J-based configuration analysis, a modified Mosher’s method, and CD spectroscopic analysis. Borrelidins C and D displayed inhibitory activity, particularly against the Gram-negative pathogen Salmonella enterica, and moderate cytotoxicity against the SNU638 and K562 carcinoma cell lines.
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spelling pubmed-54841162017-06-29 Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp. Kim, Jungwoo Shin, Daniel Kim, Seong-Hwan Park, Wanki Shin, Yoonho Kim, Won Kyung Lee, Sang Kook Oh, Ki-Bong Shin, Jongheon Oh, Dong-Chan Mar Drugs Article Chemical investigation of a halophilic actinomycete strain belonging to the genus Nocardiopsis inhabiting a hypersaline saltern led to the discovery of new 18-membered macrolides with nitrile functionality, borrelidins C–E (1–3), along with a previously reported borrelidin (4). The planar structures of borrelidins C–E, which are new members of the rare borrelidin class of antibiotics, were elucidated by NMR, mass, IR, and UV spectroscopic analyses. The configurations of borrelidines C–E were determined by the interpretation of ROESY NMR spectra, J-based configuration analysis, a modified Mosher’s method, and CD spectroscopic analysis. Borrelidins C and D displayed inhibitory activity, particularly against the Gram-negative pathogen Salmonella enterica, and moderate cytotoxicity against the SNU638 and K562 carcinoma cell lines. MDPI 2017-06-06 /pmc/articles/PMC5484116/ /pubmed/28587270 http://dx.doi.org/10.3390/md15060166 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
Kim, Jungwoo
Shin, Daniel
Kim, Seong-Hwan
Park, Wanki
Shin, Yoonho
Kim, Won Kyung
Lee, Sang Kook
Oh, Ki-Bong
Shin, Jongheon
Oh, Dong-Chan
Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title_full Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title_fullStr Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title_full_unstemmed Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title_short Borrelidins C–E: New Antibacterial Macrolides from a Saltern-Derived Halophilic Nocardiopsis sp.
title_sort borrelidins c–e: new antibacterial macrolides from a saltern-derived halophilic nocardiopsis sp.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5484116/
https://www.ncbi.nlm.nih.gov/pubmed/28587270
http://dx.doi.org/10.3390/md15060166
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