Grisemycin, a Bridged Angucyclinone with a Methylsulfinyl Moiety from a Marine-Derived Streptomyces sp

Org Lett. 2016 Mar 18;18(6):1402-5. doi: 10.1021/acs.orglett.6b00332. Epub 2016 Mar 9.

Abstract

Grisemycin (1), the first sulfur angucyclinone with an unusual ether-bridged system, was isolated from a marine-derived Streptomyces griseus strain M268. Its novel, here cage-like, structure was determined by spectroscopic analysis and single-crystal X-ray diffraction. Compound 1 exhibited modestly selective activity against the HL-60 cell line with an IC50 value of 31.54 μM. Futhermore, the absolute stereochemistry of kiamycin (2), an 1,12-epoxybenz[a]anthracene, previously obtained from the same strain, was established by X-ray diffraction analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemical synthesis*
  • Anthraquinones / chemistry
  • Anthraquinones / pharmacology
  • Crystallography, X-Ray
  • HL-60 Cells
  • Hep G2 Cells
  • Humans
  • Lactones / pharmacology
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrroles / pharmacology
  • Streptomyces / chemistry*
  • Streptomyces griseus / chemistry

Substances

  • Anthraquinones
  • Lactones
  • Pyrroles
  • angucyclinone
  • grisemycin
  • kiamycin
  • marizomib