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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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
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