Cytotoxic Bagremycins from Mangrove-Derived Streptomyces sp. Q22

J Nat Prod. 2017 May 26;80(5):1450-1456. doi: 10.1021/acs.jnatprod.6b01136. Epub 2017 May 15.

Abstract

New bagremycins C-E (3-5) and bagrelactone A (6), together with known bagremycins A (1) and B (2), 4-hydroxystyrene (7), and 4-hydroxystyrene 4-O-α-d-galactopyranoside (8), were isolated from a mangrove-derived actinomycete, Streptomyces sp. Q22. Structures of these new compounds were elucidated based on their NMR and HRESIMS spectroscopic data as well as chemical degradation. Bagremycin C (3) is a unique analogue with an N-acetyl-(S)-cysteine moiety, while bagrelactone A (6) represents the first example of this type of bagremycin-derived macrolide. Bagremycin C (3) was active against four glioma cell lines, with IC50 values in the range from 2.2 to 6.4 μM, induced apoptosis in human glioma U87MG cells in a dose- and time-dependent manner, and arrested the U87MG cell cycle at the G0/G1 phase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinobacteria / chemistry*
  • Aminobenzoates / chemistry
  • Aminobenzoates / pharmacology*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Glioma / chemistry
  • Glioma / drug therapy*
  • Humans
  • Inhibitory Concentration 50
  • Macrolides / chemistry
  • Macrolides / pharmacology*
  • Molecular Structure
  • Phenols / chemistry*
  • Streptomyces / chemistry*

Substances

  • Aminobenzoates
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Macrolides
  • Phenols
  • bagremycin A
  • bagremycin B
  • bagremycin C
  • 4-vinylphenol