Brominated polyunsaturated lipids with protein tyrosine phosphatase-1B inhibitory activity from Chinese marine sponge Xestospongia testudinaria

J Asian Nat Prod Res. 2015;17(8):861-6. doi: 10.1080/10286020.2015.1026334. Epub 2015 Apr 1.

Abstract

A new brominated polyunsaturated lipid, methyl (E,E)-14,14-dibromo-4,6,13-tetradecatrienoate (1), along with three known related analogues (2-4), were isolated from the Et2O-soluble portion of the acetone extract of Chinese marine sponge Xestospongia testudinaria treated with diazomethane. The structure of the new compound was elucidated by detailed spectroscopic analysis and by comparison with literature data. Compound 3 exhibited significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of type II diabetes and obesity, with an IC50 value of 5.30 ± 0.61 μM, when compared to the positive control oleanolic acid (IC50 = 2.39 ± 0.26 μM).

Keywords: PTP1B inhibitory activity; Xestospongia testudinaria; brominated polyunsaturated lipid; sponge.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Diabetes Mellitus, Type 2
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / isolation & purification*
  • Fatty Acids, Unsaturated / pharmacology*
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / isolation & purification*
  • Hydrocarbons, Brominated / pharmacology*
  • Marine Biology
  • Molecular Structure
  • Netherlands
  • Oleanolic Acid / chemistry
  • Porifera / chemistry*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Xestospongia / chemistry*

Substances

  • Fatty Acids, Unsaturated
  • Hydrocarbons, Brominated
  • methyl (E,E)-14,14-dibromo-4,6,13-tetradecatrienoate
  • Oleanolic Acid
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1