Frondoplysins A and B, Unprecedented Terpene-Alkaloid Bioconjugates from Dysidea frondosa

Org Lett. 2019 Aug 16;21(16):6190-6193. doi: 10.1021/acs.orglett.9b01754. Epub 2019 Jun 27.

Abstract

The chemical investigation of the marine sponge Dysidea frondosa discovered a pair of unprecedented bioconjugates that are composed of a meroterpene and an unusual psammaplysin alkaloid. The structures of frondoplysins A (1) and B (2) were characterized by analysis of HRMS and NMR data coupled with single-crystal X-ray diffraction. Frondoplysin A was found to be a potent inhibitor targeting protein-tyrosine phosphatase 1B (PTP1B) with an IC50 value of 0.39 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Alkaloids / toxicity
  • Animals
  • Animals, Genetically Modified
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Crystallography, X-Ray
  • Dysidea / chemistry*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
  • Zebrafish / genetics

Substances

  • Alkaloids
  • Antioxidants
  • Enzyme Inhibitors
  • PTPN1 protein, human
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1