Antiandrogenic natural Diels--Alder-type adducts from Brosimum rubescens

J Nat Prod. 1997 Oct;60(10):997-1002. doi: 10.1021/np9607215.

Abstract

The isolation and structure elucidation of five novel natural Diels--Alder-type adducts, named palodesangrens A-E (1-5), from the Peruvian folk medicine known as "palo de sangre" (Brosimum rubescens) is described. The structures of the Diels--Alder adducts, consisting of chalcone derivatives and a prenylcoumarin, were elucidated by analysis of spectroscopic data including 2D NMR. Some of these compounds showed potent inhibitory activity towards 5 alpha-dihydrotestosterone (DHT) binding with an androgen receptor to form a DHT-receptor complex that causes androgen-dependent diseases.

MeSH terms

  • 5-alpha Reductase Inhibitors
  • Androgen Antagonists / chemistry
  • Androgen Antagonists / isolation & purification*
  • Androgen Antagonists / pharmacology
  • Androgen Receptor Antagonists
  • Animals
  • Chalcone / analogs & derivatives
  • Chalcone / chemistry
  • Chalcone / isolation & purification*
  • Chalcone / pharmacology
  • Chromatography, High Pressure Liquid
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Male
  • Peru
  • Plant Epidermis / chemistry
  • Plants, Medicinal / chemistry*
  • Rats
  • Rats, Wistar
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • 5-alpha Reductase Inhibitors
  • Androgen Antagonists
  • Androgen Receptor Antagonists
  • Coumarins
  • Chalcone