The absolute configuration of ecklonialactones A, B, and E, novel oxylipins from brown algae of the genera Ecklonia and Egregia

J Nat Prod. 1994 Jan;57(1):171-4. doi: 10.1021/np50103a028.

Abstract

Ecklonialactones A, B, and E, previously isolated from the brown alga Ecklonia stolonifera, have been isolated from the Oregon phaeophyte Egregia menziesii. The structure and relative stereochemistry of ecklonialactone E were independently determined by various nmr techniques. The absolute stereochemistry of ecklonialactone A was deduced by cd analysis of a dibenzoate derivative, which indicated it possessed a 11S, 12R, 13S, 15R, 16S stereochemistry. Similar 1H- and 13C-nmr data and optical rotations for all of the ecklonialactones indicate that B and E have the same stereochemistry as A at comparable stereocenters.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bridged Bicyclo Compounds / chemistry*
  • Bridged Bicyclo Compounds / isolation & purification
  • Crystallography, X-Ray
  • Lactones / chemistry*
  • Lactones / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Phaeophyceae / chemistry*

Substances

  • Bridged Bicyclo Compounds
  • Lactones
  • ecklonialactone A
  • ecklonialactone B
  • ecklonialactone E