Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria

Nikolay Vasilev, Rainer Ebel, RuAngelie Edrada-Ebel, Elizabeth Fuss, Wilhelm. A. Alfermann, Illana Ionkova, Ana Petrova, Miriam Repplinger, Thomas. J. Schmidt

Research output: Contribution to journalArticle

22 Citations (Scopus)

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.
LanguageEnglish
Pages273-280
Number of pages7
JournalPlanta Medica
Volume74
Issue number3
DOIs
Publication statusPublished - 2008

Fingerprint

Flax
Bulgaria
Lignans
High Pressure Liquid Chromatography
Podophyllotoxin
Oxygenation
Glucosides
Phylogeny
Glycosides
Sequence Analysis
Esters
Derivatives

Keywords

  • aryltetralin lignan
  • HPLC-ESI/MS
  • HPLC-UV/DAD
  • linum L.
  • linaceae
  • chemical and molecular systematics

Cite this

Vasilev, N., Ebel, R., Edrada-Ebel, R., Fuss, E., Alfermann, W. A., Ionkova, I., ... Schmidt, T. J. (2008). Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria. Planta Medica, 74(3), 273-280. https://doi.org/10.1055/s-2008-1034298
Vasilev, Nikolay ; Ebel, Rainer ; Edrada-Ebel, RuAngelie ; Fuss, Elizabeth ; Alfermann, Wilhelm. A. ; Ionkova, Illana ; Petrova, Ana ; Repplinger, Miriam ; Schmidt, Thomas. J. / Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria. In: Planta Medica. 2008 ; Vol. 74, No. 3. pp. 273-280.
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Vasilev, N, Ebel, R, Edrada-Ebel, R, Fuss, E, Alfermann, WA, Ionkova, I, Petrova, A, Repplinger, M & Schmidt, TJ 2008, 'Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria' Planta Medica, vol. 74, no. 3, pp. 273-280. https://doi.org/10.1055/s-2008-1034298

Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria. / Vasilev, Nikolay; Ebel, Rainer; Edrada-Ebel, RuAngelie; Fuss, Elizabeth; Alfermann, Wilhelm. A.; Ionkova, Illana; Petrova, Ana; Repplinger, Miriam; Schmidt, Thomas. J.

In: Planta Medica, Vol. 74, No. 3, 2008, p. 273-280.

Research output: Contribution to journalArticle

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T1 - Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria

AU - Vasilev, Nikolay

AU - Ebel, Rainer

AU - Edrada-Ebel, RuAngelie

AU - Fuss, Elizabeth

AU - Alfermann, Wilhelm. A.

AU - Ionkova, Illana

AU - Petrova, Ana

AU - Repplinger, Miriam

AU - Schmidt, Thomas. J.

PY - 2008

Y1 - 2008

N2 - 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.

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KW - aryltetralin lignan

KW - HPLC-ESI/MS

KW - HPLC-UV/DAD

KW - linum L.

KW - linaceae

KW - chemical and molecular systematics

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UR - http://dx.doi.org/10.1055/s-2008-1034298

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