Structures of eremophilane-type sesquiterpene glucosides, alticolosides A-G, from the Far Eastern endemic Ligularia alticola Worosch

Phytochemistry. 2015 Mar:111:169-76. doi: 10.1016/j.phytochem.2014.11.003. Epub 2014 Dec 3.

Abstract

Seven eremophilane-type sesquiterpene glucosides, alticolosides A-G, have been isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae) along with two known compounds, monoterpenoid glycoside (4S)-α-terpineol 8-O-β-D-glucopyranoside and norditerpenoid glycoside 7(8)-dihydro-β-ionone 3-O-β-D-glucopyranoside. Alticoloside D was identified with the earlier known 8-O-(β-D-glucopyranosyl)-2-oxo-eremophila-1(10),8,11-triene, but the stereostructure of the latter was revised on the basis of ROESY and CD data. All the glycosides are derivatives of new eremophilane-type aglycones, differing from known eremophilanes in details of planar and/or stereo structures except for the aglycone of alticoloside E.

Keywords: Alticolosides; Ligularia alticola; NMR; Sesquiterpene eremophilane-type glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asteraceae / chemistry*
  • Diterpenes / chemistry
  • Glucosides / chemistry
  • Glucosides / isolation & purification*
  • Molecular Structure
  • Monoterpenes / chemistry
  • Monoterpenes / isolation & purification
  • Norisoprenoids / chemistry
  • Norisoprenoids / isolation & purification
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*

Substances

  • Diterpenes
  • Glucosides
  • Monoterpenes
  • Norisoprenoids
  • Sesquiterpenes
  • beta-ionone