Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and Aphicidal Activity Evaluation

J Org Chem. 2019 Sep 6;84(17):10757-10763. doi: 10.1021/acs.joc.9b01212. Epub 2019 Aug 19.

Abstract

A new dimeric eudesmane sesquiterpenoid with an unreported 6/6/5/6/6 fused carbon skeleton, echingridimer A (1), and five monomers (2-6), including two new compounds (2 and 3), were isolated from the roots of Echinops grijsii. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses and confirmed by X-ray crystallography or electronic circular dichroism spectra. Compound 1 represents the first example of a 3,15'-linked Michael-type adduct of two eudesmanes, which feature a unique 1-oxaspiro[4.5]decan moiety. The plausible biogenetic pathway for 1-6 was briefly discussed. The oxaspiro dimer (1) not only showed stronger aphicidal activity than closely related monomeric compounds (2-6) and the commercial aphicide pymetrozine but also exhibited remarkable insecticide activity against a broad range of aphids, thus could be used as a potential biobased insecticide to suppress aphids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aphids*
  • Asteraceae / chemistry*
  • Dimerization*
  • Insecticides / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Sesquiterpenes / chemistry*

Substances

  • Insecticides
  • Sesquiterpenes