Acetylenic thiophenes from the roots of Escinops ellenbeckii from Ethiopia

Nat Prod Res. 2005 Dec;19(8):755-61. doi: 10.1080/1478641042000301711.

Abstract

The hexane fraction from the roots of Echinops ellenbeckii O. Hoffm. from Ethiopia yielded seven acetylenic thiophenes of which five compounds (1, 3, 4, 6, 7) are reported for the first time in this species: the monothiophenes 5-(penta-1,3-diynyl)-2-(but-3-en-1-ynyl)-thiophene (1), 5-(penta-1,3-diynyl)-2-(4-acetoxy-but-1-ynyl)-thiophene (2), 5-(penta-1,3-diynyl)-2-(3-hydroxy-4-acetoxy-but-1-ynyl)-thiophene (3), 5-(penta-1,3-diynyl)-2-(3,4-diacetoxy-but-1-ynyl)-thiophene (4), 5-(penta-1,3-diynyl)-2-(3-chloro-4-acetoxy-but-1-ynyl)-thiophene (5), 5-(penta-1,3-diynyl)-2-(3,4-epoxy-but-1-ynyl)-thiophene (6) and the dithiophene 5-[(5-acetoxymethyl-2-thienyl)-2-(but-3-en-1-ynyl)]-thiophene (7). Additionally, four fatty acids (C14, C15, C16 and C18), seven fatty acid esters and three long-chain hydrocarbons could be identified. All the structures were elucidated on the basis of spectral data by GC-MS, HRMS and the NMR techniques.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Asteraceae / chemistry*
  • Asteraceae / cytology
  • Asteraceae / physiology
  • Chromatography, Gas
  • Ethiopia
  • Fatty Acids / isolation & purification
  • Gas Chromatography-Mass Spectrometry
  • Plant Roots / chemistry*
  • Plant Roots / cytology
  • Thiophenes / chemistry
  • Thiophenes / isolation & purification*
  • Thiophenes / metabolism

Substances

  • Fatty Acids
  • Thiophenes