Structural and spectroscopic characteristics of two new dibenzylbutane type lignans from Taxus baccata L.

Erdemoglu N., Sener B., Ozcan Y., Ide S.

JOURNAL OF MOLECULAR STRUCTURE, vol.655, no.3, pp.459-466, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 655 Issue: 3
  • Publication Date: 2003
  • Doi Number: 10.1016/s0022-2860(03)00359-4
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.459-466
  • Keywords: Taxus baccata, lignans, isolariciresinol, spectral data, molecular mechanic calculations, NEEDLES
  • Hacettepe University Affiliated: Yes


Chromatographic separation of chloroform extracts of the heartwood of Taxus baccata L. has yielded two new dibenzylbutane type lignans, together with a known lignan. Their structures were established as 3'-demethylisolariciresinol-9'-hydroxy isopropylether (1) and 3-demethylisolariciresinol (2) and isolariciresinol (3) on the basis of 1D- and 2D-NMR spectroscopic analysis. Compounds 1 and 2 were identified as new lignans of isolariciresinol derivatives. Compound 1 is the first lignan with a hydroxyisopropyl group at C-9'. Molecular mechanic calculations of these compounds were carried out by using MM3 program. Furthermore, the conformations of these three compounds were computed with the semi-empirical molecular orbital methods AM1 and PM3 by using X-ray crystal structure results of similar compounds. So, three-dimensional, the most probable structure of these compounds were obtained, compared and discussed. (C) 2003 Elsevier B.V. All rights reserved.