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Planta Med 2008; 74(3): 273-280
DOI: 10.1055/s-2008-1034298
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Metabolic Profiling of Lignan Variability in Linum species of Section Syllinum native to Bulgaria

Nikolay Vasilev1 , Rainer Ebel2 , RuAngelie Edrada3 , Elisabeth Fuss4 , A. Wilhelm Alfermann5 , Iliana Ionkova1 , Ana Petrova6 , Miriam Repplinger7 , Thomas J. Schmidt8
  • 1Faculty of Pharmacy, Medical University of Sofia, Sofia, Bulgaria
  • 2Department of Chemistry, University of Aberdeen, Aberdeen, Scotland, UK
  • 3Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Düsseldorf, Germany
  • 4Interfakultäres Institut für Biochemie, Eberhard-Karls-Universität Tübingen, Tübingen, Germany
  • 5Institut für Entwicklungs- und Molekularbiologie der Pflanzen, Heinrich-Heine-Universität Düsseldorf, Düsseldorf, Germany
  • 6Institute of Botany, Bulgarian Academy of Sciences, Sofia, Bulgaria
  • 7Institut für Spezielle Botanik und Botanischer Garten, Johannes Gutenberg-Universität Mainz, Mainz, Germany
  • 8Institut für Pharmazeutische Biologie und Phytochemie, Westfälische Wilhelms-Universität Münster, Münster, Germany
Further Information

Publication History

Received: July 12, 2007 Revised: January 4, 2008

Accepted: January 8, 2008

Publication Date:
08 February 2008 (online)

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Abstract

Lignans in eighteen samples of Linum species (L. tauricum ssp. tauricum, serbicum, bulgaricum and linearifolium; L. elegans; L. flavum ssp. sparsiflorum, L. capitatum var. laxiflorum), all members of the section Syllinum occurring in Bulgaria, were analysed by HPLC-ESI/MS and HPLC-UV/DAD. The ESI/MS fragmentation pathways recently established for aryltetralin lignans are now extended to ester and glycoside derivatives. In total, 22 different lignans, mainly of the aryltetralin type, were identified. 6-Methoxypodophyllotoxin and its glucoside were present as major constituents in all samples. Differences between the investigated taxa were observed especially with respect to the accumulation of 6-deoxy-7-hydroxy-aryltetralins such as podophyllotoxin and of 6-hydroxy-7-deoxy-aryltetralin lignans of the peltatin type. The distribution of aryltetralin lignans with different oxygenation patterns in the various samples, and correlations between the chemical data and the molecular phylogeny based on an analysis of ITS sequences of the investigated species are discussed.

Key words

Aryltetralin lignan - HPLC-ESI/MS - HPLC-UV/DAD - Linum L. - Linaceae - chemical and molecular systematics

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Prof. Dr. Thomas J. Schmidt

Institut für Pharmazeutische Biologie und Phytochemie

Westfälische Wilhelms-Universität Münster

Hittorfstraße 56

48149 Münster

Germany

Phone: +49-251-83-33378

Fax: +49-251-83-38341

Email: thomschm@uni-muenster.de

    www.thieme-connect.de/ejournals/toc/plantamedica