Cembrane diterpenoids from the soft coral Sarcophyton trocheliophorum Marenzeller as a new class of PTP1B inhibitors

Bioorg Med Chem. 2013 Sep 1;21(17):5076-80. doi: 10.1016/j.bmc.2013.06.043. Epub 2013 Jun 27.

Abstract

A detailed investigation of the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller yielded, along with six known terpenes (6-11), the new sarcophytonolides N-R (1-5), whose structures have been elucidated by detailed spectroscopic analysis. Sarcophytonolides N-R are mono- or bicyclic cembranoids characterized by the presence of three/four double bonds and oxidized methyl groups. Some of the isolated compounds showed significant inhibitory activity against human protein tyrosine phosphatase 1B (PTP1B) enzyme, a key target for the treatment of type-II diabetes and obesity, and some preliminary structure-activity relationships have been drawn. This is the first report on the anti-PTP1B activity of cembrane diterpenoids.

Keywords: Cembrane; Marinde diterpenoids; PTP1B inhibition; Sarcophyton trocheliophorum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / metabolism
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / metabolism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Protein Binding
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • Enzyme Inhibitors
  • cembrane
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1