Antimicrobial Lavandulylated Flavonoids from a Sponge-Derived Streptomyces sp. G248 in East Vietnam Sea

Mar Drugs. 2019 Sep 10;17(9):529. doi: 10.3390/md17090529.

Abstract

Three new lavandulylated flavonoids, (2S,2''S)-6-lavandulyl-7,4'-dimethoxy-5,2'-dihydroxylflavanone (1), (2S,2''S)-6-lavandulyl-5,7,2',4'-tetrahydroxylflavanone (2), and (2''S)-5'-lavandulyl-2'-methoxy-2,4,4',6'-tetrahydroxylchalcone (3), along with seven known compounds 4-10 were isolated from culture broth of Streptomyces sp. G248. Their structures were established by spectroscopic data analysis, including 1D and 2D nuclear magnetic resonance (NMR), and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configurations of 1-3 were resolved by comparison of their experimental and calculated electronic circular dichroism spectra. Compounds 1-3 exhibited remarkable antimicrobial activity. Whereas, two known compounds 4 and 5 exhibited inhibitory activity against Mycobacterium tuberculosis H37Rv with minimum inhibitory concentration (MIC) values of 6.0 µg/mL and 11.1 µg/mL, respectively.

Keywords: Streptomyces; actinomycete; anti-microbial; anti-tuberculosis; cytotoxicity; flavonoid.

MeSH terms

  • Animals
  • Antibiotics, Antitubercular / chemistry
  • Antibiotics, Antitubercular / isolation & purification
  • Antibiotics, Antitubercular / pharmacology*
  • Cell Line, Tumor
  • Circular Dichroism
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects
  • Porifera / microbiology*
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / chemistry*
  • Vietnam

Substances

  • Antibiotics, Antitubercular
  • Flavonoids