Cargando…
Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp.
Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (6−9), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures...
Autores principales: | , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8624273/ https://www.ncbi.nlm.nih.gov/pubmed/34822489 http://dx.doi.org/10.3390/md19110618 |
_version_ | 1784606133618475008 |
---|---|
author | Ryu, Min-Ji Hillman, Prima F. Lee, Jihye Hwang, Sunghoon Lee, Eun-Young Cha, Sun-Shin Yang, Inho Oh, Dong-Chan Nam, Sang-Jip Fenical, William |
author_facet | Ryu, Min-Ji Hillman, Prima F. Lee, Jihye Hwang, Sunghoon Lee, Eun-Young Cha, Sun-Shin Yang, Inho Oh, Dong-Chan Nam, Sang-Jip Fenical, William |
author_sort | Ryu, Min-Ji |
collection | PubMed |
description | Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (6−9), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds 1−4 and 10 were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds 1−4 were determined via analysis of nuclear Overhauser effect (NOE) spectroscopic data, after which their absolute configurations were established by comparing the experimental electronic circular dichroism (ECD) spectra of compounds 1−4 to those of previously reported possible enantiomer models and DP4 calculations. Compound 3 displayed strong antibacterial activities against Bacillus subtilis, Kocuria rhizophila, and Staphylococcus aureus, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound 1 exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range. |
format | Online Article Text |
id | pubmed-8624273 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-86242732021-11-27 Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. Ryu, Min-Ji Hillman, Prima F. Lee, Jihye Hwang, Sunghoon Lee, Eun-Young Cha, Sun-Shin Yang, Inho Oh, Dong-Chan Nam, Sang-Jip Fenical, William Mar Drugs Article Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (6−9), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds 1−4 and 10 were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds 1−4 were determined via analysis of nuclear Overhauser effect (NOE) spectroscopic data, after which their absolute configurations were established by comparing the experimental electronic circular dichroism (ECD) spectra of compounds 1−4 to those of previously reported possible enantiomer models and DP4 calculations. Compound 3 displayed strong antibacterial activities against Bacillus subtilis, Kocuria rhizophila, and Staphylococcus aureus, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound 1 exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range. MDPI 2021-10-30 /pmc/articles/PMC8624273/ /pubmed/34822489 http://dx.doi.org/10.3390/md19110618 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Ryu, Min-Ji Hillman, Prima F. Lee, Jihye Hwang, Sunghoon Lee, Eun-Young Cha, Sun-Shin Yang, Inho Oh, Dong-Chan Nam, Sang-Jip Fenical, William Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title | Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title_full | Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title_fullStr | Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title_full_unstemmed | Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title_short | Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp. |
title_sort | antibacterial meroterpenoids, merochlorins g–j from the marine bacterium streptomyces sp. |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8624273/ https://www.ncbi.nlm.nih.gov/pubmed/34822489 http://dx.doi.org/10.3390/md19110618 |
work_keys_str_mv | AT ryuminji antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT hillmanprimaf antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT leejihye antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT hwangsunghoon antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT leeeunyoung antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT chasunshin antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT yanginho antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT ohdongchan antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT namsangjip antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp AT fenicalwilliam antibacterialmeroterpenoidsmerochlorinsgjfromthemarinebacteriumstreptomycessp |