Selaginpulvilins A-D, new phosphodiesterase-4 inhibitors with an unprecedented skeleton from Selaginella pulvinata

Org Lett. 2014 Jan 3;16(1):282-5. doi: 10.1021/ol403282f. Epub 2013 Dec 12.

Abstract

Selaginpulvilins A-D (1-4), four new phenols with an unprecedented 9,9-diphenyl-1-(phenylethynyl)-9H-fluorene skeleton, together with four known selaginellins (5-8) were isolated from Selaginella pulvinata. Their structures were elucidated by spectroscopic analysis and chemical correlation. The structure of 1 was confirmed by single-crystal X-ray diffraction. Compounds 1-8 exhibited remarkable inhibitory activities (IC50 values in the range of 0.11-5.13 μM) against phosphodiesterase-4 (PDE4), a drug target for the treatment of asthma and chronic obstructive pulmonary disease.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / pharmacology*
  • Crystallography, X-Ray
  • Cyclic Nucleotide Phosphodiesterases, Type 4 / metabolism*
  • Dose-Response Relationship, Drug
  • Fluorenes / chemistry*
  • Fluorenes / pharmacology*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Phosphodiesterase 4 Inhibitors / chemistry
  • Phosphodiesterase 4 Inhibitors / isolation & purification
  • Phosphodiesterase 4 Inhibitors / pharmacology*
  • Selaginellaceae / chemistry*
  • Structure-Activity Relationship

Substances

  • 9,9-diphenyl-1-(phenylethynyl)-9H-fluorene
  • Biological Products
  • Fluorenes
  • Phosphodiesterase 4 Inhibitors
  • Cyclic Nucleotide Phosphodiesterases, Type 4