Studies on the sesquiterpene lactones from Laurus novocanariensis lead to the clarification of the structures of 1-epi-tatridin B and its epimer tatridin B

Phytochemistry. 2018 Sep;153:48-52. doi: 10.1016/j.phytochem.2018.05.014. Epub 2018 Jun 1.

Abstract

The germacranolide 1-epi-tatridin B has been isolated from the aerial parts of Laurus novocanariensis. We have observed that the identification of this lactone and its epimer tetradin B in the scientific literature is confusing and contradictory. We have therefore studied this issue clarifying errors and contributing to the structural elucidation of other related products. Moreover, we have isolated from this plant a lactone with an 1,5-ether bridge, previously obtained from Austrolabium candidum. We have now named it austroliolide, reassigned its 13C NMR spectrum and compared its structure with that of badgerin. In addition, we have also isolated from L. novocanariensis the known germacranolides artemorin, costunolide, tatridin A, tulirinol and verlotorin, the eudesmanolides β-cyclopyrethrosin, 1β-hydroxy-arbusculin A, magnoliaolide and reynosin, and the guaianolide dehydrocostus lactone.

Keywords: 1-Epi-Tatridin B; Austroliolide; Chiliophyllin; Lauraceae; Laurus novocanariensis; Sesquiterpene lactones.

MeSH terms

  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Laurus / chemistry*
  • Molecular Conformation
  • Plant Components, Aerial / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Stereoisomerism

Substances

  • Lactones
  • Sesquiterpenes
  • tatridin B