Manoyl oxide alpha-arabinopyranoside and grindelic acid diterpenoids from Grindelia integrifolia

J Nat Prod. 2001 Oct;64(10):1365-7. doi: 10.1021/np010273n.

Abstract

Two new manoyl oxide-alpha-arabinopyranoside diterpenoids, 15-hydroxy-13-epi-manoyl oxide-14-O-alpha-L-arabinopyranoside (tarapacol-14-O-alpha-L-arabinopyranoside) (1) and 15-acetoxy-13-epi-manoyl oxide-14-O-alpha-L-arabinopyranoside (tarapacol-15-acetate-14-O-alpha-L-arabinopyranoside) (2), as well as a new grindelic acid derivative, 19-hydroxygrindelic acid (3), together with five known diterpenoids (tarapacol, tarapacanol A, grindelic acid, methyl grindeloate, 3beta-hydroxygrindelic acid, 4) were isolated from the aerial parts of Grindelia integrifolia. The structures of 1-3 were elucidated by spectral data analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asteraceae / chemistry*
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Plants, Medicinal / chemistry
  • Spectrophotometry, Infrared
  • Stereoisomerism

Substances

  • 15-acetoxy-13-epi-manoyl oxide-14-O-alpha-L-arabinopyranoside
  • 15-hydroxy-13-epi-manoyl oxide-14-O-arabinopyranoside
  • 19-hydroxygrindelic acid
  • 3-hydroxygrindelic acid
  • Diterpenes
  • Glycosides