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

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

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Bibliographic Details
Published in:Marine drugs 2017-06, Vol.15 (6), p.166
Main Authors: 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
Format: Article
Language:English
Subjects:
Actinobacteria - chemistry
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
antibacterial
Antibiotics
borrelidin
Cell Line, Tumor
Cell lines
Configurations
Cytotoxicity
Fatty Alcohols - chemistry
Fatty Alcohols - pharmacology
halophilic actinomycetes
Humans
K562 Cells
Macrolides - chemistry
Macrolides - pharmacology
Neoplasms
NMR
Nocardiopsis
Nuclear magnetic resonance
Organic chemistry
Pathogens
Planar structures
Salmonella
Salmonella enterica
Salmonella enterica - drug effects
saltern
Salterns
Spectroscopic analysis
Spectrum Analysis - methods
Toxicity
Tumor cell lines
Ultraviolet radiation
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Summary:Chemical investigation of a halophilic actinomycete strain belonging to the genus inhabiting a hypersaline saltern led to the discovery of new 18-membered macrolides with nitrile functionality, borrelidins C-E ( - ), along with a previously reported borrelidin ( ). 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 , and moderate cytotoxicity against the SNU638 and K562 carcinoma cell lines.
ISSN:1660-3397
1660-3397
DOI:10.3390/md15060166