A new germacranolide from Ageratina vernalis

Nat Prod Res. 2022 May;36(9):2254-2262. doi: 10.1080/14786419.2020.1827400. Epub 2020 Oct 1.

Abstract

The aerial parts of Ageratina vernalis provided the new germacranolide 1,10-epoxydeltoidin A (3), together with the known pentacyclic triterpenoid hopane-6α,22-diol (1), and the also known germacranolides deltoidin A (2) and 15-hydroxydeltoidin A (4). In addition, pTsOH catalyzed cyclization of 2 afforded the new guaianolide 5. The absolute configuration of 2, 4, and 5 was assigned by vibrational circular dichroism spectroscopy, while the complete 1H and 13C NMR data assignments of 2-5 followed from 1 D- and 2 D-NMR experiments.

Keywords: Ageratina vernalis; germacranolides; vibrational circular dichroism.

MeSH terms

  • Ageratina* / chemistry
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Sesquiterpenes, Germacrane / chemistry
  • Stereoisomerism

Substances

  • Sesquiterpenes, Germacrane
  • germacranolide