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 cultivatio...

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Autores principales:	Min-Ji Ryu, Prima F. Hillman, Jihye Lee, Sunghoon Hwang, Eun-Young Lee, Sun-Shin Cha, Inho Yang, Dong-Chan Oh, Sang-Jip Nam, William Fenical
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	chlorinated meroterpenoid merochlorins G−J dihydronaphthalenedione precursor ECD DP4 antibacterial Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/f04e7cc959324d0fbb6a156ac03522de
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spelling	oai:doaj.org-article:f04e7cc959324d0fbb6a156ac03522de2021-11-25T18:12:51ZAntibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.10.3390/md191106181660-3397https://doaj.org/article/f04e7cc959324d0fbb6a156ac03522de2021-10-01T00:00:00Zhttps://www.mdpi.com/1660-3397/19/11/618https://doaj.org/toc/1660-3397Four new chlorinated meroterpenoids, merochlorins G−J (<b>1</b>−<b>4</b>), and <b>10</b>, a dihydronaphthalenedione precursor, along with known merochlorins A (<b>5</b>) and C−F (<b>6</b>−<b>9</b>), were obtained from cultivation of the bacterium strain <i>Streptomyces</i> sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds <b>1</b>−<b>4</b> and <b>10</b> were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds <b>1</b>−<b>4</b> 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 <b>1</b>−<b>4</b> to those of previously reported possible enantiomer models and DP4 calculations. Compound <b>3</b> displayed strong antibacterial activities against <i>Bacillus subtilis</i>, <i>Kocuria rhizophila</i>, and <i>Staphylococcus aureus</i>, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound <b>1</b> exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range.Min-Ji RyuPrima F. HillmanJihye LeeSunghoon HwangEun-Young LeeSun-Shin ChaInho YangDong-Chan OhSang-Jip NamWilliam FenicalMDPI AGarticlechlorinated meroterpenoidmerochlorins G−Jdihydronaphthalenedione precursorECDDP4antibacterialBiology (General)QH301-705.5ENMarine Drugs, Vol 19, Iss 618, p 618 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	chlorinated meroterpenoid merochlorins G−J dihydronaphthalenedione precursor ECD DP4 antibacterial Biology (General) QH301-705.5
spellingShingle	chlorinated meroterpenoid merochlorins G−J dihydronaphthalenedione precursor ECD DP4 antibacterial Biology (General) QH301-705.5 Min-Ji Ryu Prima F. Hillman Jihye Lee Sunghoon Hwang Eun-Young Lee Sun-Shin Cha Inho Yang Dong-Chan Oh Sang-Jip Nam William Fenical Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
description	Four new chlorinated meroterpenoids, merochlorins G−J (<b>1</b>−<b>4</b>), and <b>10</b>, a dihydronaphthalenedione precursor, along with known merochlorins A (<b>5</b>) and C−F (<b>6</b>−<b>9</b>), were obtained from cultivation of the bacterium strain <i>Streptomyces</i> sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds <b>1</b>−<b>4</b> and <b>10</b> were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds <b>1</b>−<b>4</b> 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 <b>1</b>−<b>4</b> to those of previously reported possible enantiomer models and DP4 calculations. Compound <b>3</b> displayed strong antibacterial activities against <i>Bacillus subtilis</i>, <i>Kocuria rhizophila</i>, and <i>Staphylococcus aureus</i>, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound <b>1</b> exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range.
format	article
author	Min-Ji Ryu Prima F. Hillman Jihye Lee Sunghoon Hwang Eun-Young Lee Sun-Shin Cha Inho Yang Dong-Chan Oh Sang-Jip Nam William Fenical
author_facet	Min-Ji Ryu Prima F. Hillman Jihye Lee Sunghoon Hwang Eun-Young Lee Sun-Shin Cha Inho Yang Dong-Chan Oh Sang-Jip Nam William Fenical
author_sort	Min-Ji Ryu
title	Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
title_short	Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
title_full	Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
title_fullStr	Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
title_full_unstemmed	Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.
title_sort	antibacterial meroterpenoids, merochlorins g–j from the marine bacterium <i>streptomyces</i> sp.
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f04e7cc959324d0fbb6a156ac03522de
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Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.

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