Caffeic acid esters and lignans from Piper sanguineispicum

J Nat Prod. 2010 Nov 29;73(11):1884-90. doi: 10.1021/np1005357. Epub 2010 Oct 18.

Abstract

Three new caffeic acid esters (1-3), four new lignans (4-7), and the known compounds (7'S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 1-10 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC(50) 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Caffeic Acids / chemistry
  • Caffeic Acids / isolation & purification*
  • Caffeic Acids / pharmacology
  • Chlorocebus aethiops
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology
  • Dioxolanes / chemistry
  • Dioxolanes / isolation & purification
  • Drug Screening Assays, Antitumor
  • Esters
  • Female
  • Inhibitory Concentration 50
  • Leishmania / drug effects*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Macrophages / drug effects*
  • Mice
  • Nuclear Magnetic Resonance, Biomolecular
  • Peru
  • Piper / chemistry*
  • Plant Leaves / chemistry
  • Vero Cells

Substances

  • (S)-1'-methylbutyl caffeate
  • (S)-1'-methylhexyl caffeate
  • (S)-1'-methyloctyl caffeate
  • Caffeic Acids
  • Cytotoxins
  • Dioxolanes
  • Esters
  • Lignans
  • justiflorinol
  • dihydrocubebin