Two new eudesman-4α-ol epoxides from the stem essential oil of Laggera pterodonta from Côte d'Ivoire

Nat Prod Res. 2020 Oct;34(19):2765-2771. doi: 10.1080/14786419.2019.1586701. Epub 2019 Mar 25.

Abstract

The investigation of the stem essential oil of Laggera pterodonta (DC.) Sch. Bip. ex Oliv. (Asteraceae) from Côte d'Ivoire was carried out, using a combination of chromatographic (GC-RI, CC, pc-GC) and spectroscopic (GC-MS, 13C NMR) techniques. This study led to the identification of fifty constituents of which two new natural compounds 7β,11β-epoxy-eudesman-4α-ol and 7α,11α-epoxy-eudesman-4α-ol. Their structures were elucidated by 1 D and 2 D NMR spectroscopy after pc-GC purifying. Finally, 98.9% of the whole composition of the oil was identified with a high amount of 2,5-dimethoxy-p-cymene (78.9%). The other significant components were α-humulene (6.2%), (E)-β-caryophyllene (1.7%), thymyl methyl oxide (1.7%), α-phellandrene (1.5%), p-cymene (1.2%), (3αH,4βH,6αH,1αMe)-1,6-epoxy-3-hydroxycarvotanacetone angelic acid ester (1.1%) and 10-epi-γ-eudesmol (1.0%).

Keywords: 2,5-dimethoxy-p-cymene; Côte d’Ivoire; Laggera pterodonta; eudesman-4α-ol epoxide; stem oil.

MeSH terms

  • Asteraceae / chemistry*
  • Cote d'Ivoire
  • Cyclohexane Monoterpenes / analysis
  • Cymenes / analysis
  • Epoxy Compounds / chemistry
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Monocyclic Sesquiterpenes / analysis
  • Oils, Volatile / chemistry*
  • Plant Stems / chemistry*
  • Polycyclic Sesquiterpenes / analysis
  • Sesquiterpenes, Eudesmane / analysis
  • Stereoisomerism

Substances

  • Cyclohexane Monoterpenes
  • Cymenes
  • Epoxy Compounds
  • Monocyclic Sesquiterpenes
  • Oils, Volatile
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes, Eudesmane
  • gamma-eudesmol
  • 4-cymene
  • alpha phellandrene
  • humulene
  • caryophyllene