Antibacterial meroterpenoids, merochlorins g–j from the marine bacterium streptomyces sp.

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

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Abstract

Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaph-thalenedione 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 deter-mined 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.

Original languageEnglish
Article number618
JournalMarine Drugs
Volume19
Issue number11
DOIs
StatePublished - Nov 2021

Keywords

  • Antibacterial
  • Chlorinated meroterpenoid
  • DP4
  • Dihydronaphthalenedione precursor
  • ECD
  • Merochlorins G−J

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