Sesquiterpene Lactones with Astrodaucane Skeleton from Astrodaucus orientalis

Planta Med. 2023 Feb;89(2):134-139. doi: 10.1055/a-1822-1486. Epub 2022 Apr 9.

Abstract

Four sesquiterpene lactones, astrodaucanolide A - D (1: -4: ) with unique structures, toghether with two known phenylpropanoid esters (5: and 6: ) were isolated from a flower extract of Astrodaucus orientalis. The structures were established by 1D and 2D NMR spectroscopy and high-resolution mass spectrometry (HRESIMS), and the absolute configuration of 1: -4: was determined by electronic circular dichroism (ECD). Compounds 1: -4: novel architecture represents a new class of sesquiterpenes with new skeleton. A putative biosynthetic pathway for their scaffold is proposed with a germacryl cation as the precursor. The suggested biosynthesis pathway is similar to that of eudesmane sesquiterpenes with a different direction of protonation which then leads to the new skeleton, named astrodaucane by the 1,2-methyl migration.

MeSH terms

  • Lactones / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes, Eudesmane* / chemistry
  • Skeleton

Substances

  • Sesquiterpenes, Eudesmane
  • Lactones
  • Sesquiterpenes