Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium <i>Streptomyces</i> sp.

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 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
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ECD
DP4
Acceso en línea:https://doaj.org/article/f04e7cc959324d0fbb6a156ac03522de
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Sumario: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.