Acetophenone derivatives from the roots of Melicope ptelefolia

Fitoterapia. 2019 Jan:132:40-45. doi: 10.1016/j.fitote.2018.11.013. Epub 2018 Nov 27.

Abstract

Five new prenylated acetophenones, melicoptelins A-E (1-5), along with one known congener (6) were isolated from the roots of Melicope ptelefolia. Among them, compounds 2a/2b, 3a/3b, and 4a/4b were obtained as inseparable interconverting mixtures of keto and enol tautomers. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR and HRESIMS. Compouds 2a/2b, 4a/4b and 5 exhibit protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 34.4, 55.2 and 66.6 μM, respectively.

Keywords: Melicope ptelefolia; PTP1B inhibitory activity; Prenylated acetophenones; Tautomers.

MeSH terms

  • Acetophenones / chemistry*
  • Acetophenones / isolation & purification
  • China
  • Molecular Structure
  • Plant Roots / chemistry
  • Prenylation
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Rutaceae / chemistry*

Substances

  • Acetophenones
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1