Unprecedented diterpenoids as a PTP1B inhibitor from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller

Org Lett. 2013 Jan 18;15(2):274-7. doi: 10.1021/ol303110d. Epub 2012 Dec 28.

Abstract

Methyl sarcotroates A and B (3 and 4), two unprecedented diterpenoids possessing a tetradecahydrocyclopenta[3',4']cyclobuta[1',2':4,5]cyclonona[1,2-b]oxirene ring system, along with their probable biogenetic precursor, sarcophytonolide M (1), were isolated from the Hainan soft coral Sarcophyton trocheliophorum. Their structures were elucidated by detailed spectroscopic analysis, and the absolute configuration of compound 3 was determined by TDDFT ECD calculations. Compound 4 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), being similar to that of positive control oleanolic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleanolic Acid / pharmacology
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*

Substances

  • Diterpenes
  • methyl sarcotroate A
  • methyl sarcotroate B
  • Oleanolic Acid
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1