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Scientific article
English

Investigation of Symphytum cordatum alkaloids by liquid–liquid partitioning, thin-layer chromatography and liquid chromatography–ion-trap mass spectrometry

Contributors

Mroczek, T.; Ndjoko Ioset, Karine; Glowniak, K.; Mietkiewicz-Capala, A.; Hostettmann, Kurt

Published in

Analytica chimica acta, vol. 566, no. 2, p. 157-166

Publication date

2006

Abstract

From the alkalised crude extract of Symphytum cordatum (L.) W.K. roots, pyrrolizidine alkaloids (PAs) were extracted as free tertiary bases and polar N-oxides in a merely one-step liquid-liquid partitioning (LLP) in separation funnel and subsequently pre-fractionated by preparative multiple-development (MD) thin-layer chromatography (TLC) on silica gel plates. In this way three alkaloid fractions of different polarities and retention on silica gel plates were obtained as: the most polar N-oxides of the highest retention, the tertiary bases of medium retention, and diesterified N-oxides of the lowest retention. The former fraction was reduced into free bases by sodium hydrosulfite and purified by LLP on Extrelut-NT3 cartridge. It was further analysed together with the two other fractions by high-performance liquid chromatography (HPLC)-ion-trap mass spectrometry with atmospheric pressure chemical ionization (APCl) interface on XTerra C-18 column using a gradient elution. Based on MSn spectra, 18 various alkaloids have been tentatively determined for the first time in this plant as the following types of structure: echimidine-N-oxide (three diasteroisomers), 7-sarracinyl-9-viridifloryiretronecine (two diasteroisomers), echimidine (two diasteroisomers), lycopsamine (two diasteroisomers), dihydroechinatine-N-oxide, dihydroheliospathuline-N-oxide, lycopsamine-N-oxide (three diasteroisomers), 7-acetyllycopsamine-N-oxide, symphytine-N-oxide (two diasteroisomers) and 2 '',3 ''-epoxyechiui-nine-N-oxide. (c) 2006 Elsevier B.V. All rights reserved.

Keywords

  • SOLID-PHASE EXTRACTION
  • PYRROLIZIDINE ALKALOIDS
  • GAS-CHROMATOGRAPHY
  • OFFICINALE L
  • FREE BASES
  • N-OXIDES
  • HPLC-MS
  • RADIX
  • SPECTROSCOPY
  • METABOLITES

UNIGE affiliation entities

Citation (ISO format)

MROCZEK, T. et al. Investigation of Symphytum cordatum alkaloids by liquid–liquid partitioning, thin-layer chromatography and liquid chromatography–ion-trap mass spectrometry. In: Analytica chimica acta, 2006, vol. 566, n° 2, p. 157–166. doi: 10.1016/j.aca.2006.03.016

Main files (1)

Article (Published version)

Identifiers

Additional URL for this publication

http://linkinghub.elsevier.com/retrieve/pii/S0003267006005435

Journal ISSN

0003-2670
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Technical informations

Creation

10/08/2010 11:14:00

First validation

10/08/2010 11:14:00

Update

14/03/2023 16:01:59

Status update

14/03/2023 16:01:59

Last indexation

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