Xylarianaphthol-1, a novel dinaphthofuran derivative, activates p21 promoter in a p53-independent manner

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3389-91. doi: 10.1016/j.bmcl.2014.05.083. Epub 2014 Jun 4.

Abstract

Xylarianaphthol-1, a novel dinaphthofuran derivative, was isolated from a marine sponge-derived fungus of order Xylariales on the guidance of a bioassay using the transfected human osteosarcoma MG63 cells (MG63(luc+)). The chemical structure of xylarianaphthol-1 was determined from the (1)H and (13)C NMR analysis and was further confirmed by the total synthesis. Xylarianaphthol-1 activated p21 promoter stably transfected in MG63 cells dose-dependently. Expression of p21 protein in the wild-type MG63 cells was also increased by xylarianaphthol-1 treatment.

Keywords: Dinaphthofuran; Marine natural product; Structure elucidation; Total synthesis; Xylarianaphthol-1; p21 promoter activator.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemistry
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology*
  • Cell Line, Tumor
  • Cyclin-Dependent Kinase Inhibitor p21 / genetics
  • Cyclin-Dependent Kinase Inhibitor p21 / metabolism*
  • Dose-Response Relationship, Drug
  • Humans
  • Structure-Activity Relationship
  • Tumor Suppressor Protein p53 / metabolism*
  • Xylariales / chemistry
  • Xylariales / metabolism

Substances

  • Benzofurans
  • Cyclin-Dependent Kinase Inhibitor p21
  • Tumor Suppressor Protein p53
  • xylarianaphthol-1