Novel cassane and cleistanthane diterpenes from Myrospermum frutescens: absolute stereochemistry of the cassane diterpene series

J Nat Prod. 2004 Oct;67(10):1711-5. doi: 10.1021/np049890c.

Abstract

Four new diterpenes (1-4) were isolated from the leaves of Myrospermum frutescens as minor constituents. Chagresnol (1), 6beta,18-diacetoxycassan-13,15-diene (2), and chagreslactone (3) possess cassane skeletons, while chagresnone (4) exhibits a cleistanthane skeleton. Molecular structures and their relative stereochemistries were elucidated using NMR spectroscopy in combination with UV, IR, and MS spectral data. Although compound 2 was previously reported as a synthetic product, we report its first isolation as a natural product. Derivative products (10-13) were obtained to test their activities against Chagas's disease. In addition, the absolute stereochemistry of the previously isolated cassane diterpene 5 from M. frutescens is presented.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Chagas Disease / drug therapy*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Fabaceae / chemistry*
  • Mass Spectrometry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Structure-Activity Relationship
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification*
  • Trypanocidal Agents / pharmacology

Substances

  • Diterpenes
  • Trypanocidal Agents