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Scientific article
English

Identification of isomeric tropane alkaloids from Schizanthus grahamii by HPLC-NMR with loop storage and HPLC-UV-MS/SPE-NMR using a cryogenic flow probe

Contributors

Bieri, Stefan; Varesio, Emmanuel; Veuthey, Jean-Luc; Muñoz, Orlando; Tseng, Li-Hong; Braumann, Ulrich; Spraul, Manfred; Christen, Philippe

Published in

Phytochemical analysis, vol. 17, no. 2, p. 78-86

Publication date

2006

Abstract

Two fully automated HPLC-NMR methods are reported and compared for the structure elucidation of four isomeric tropane alkaloids from the stem-bark of an endemic Chilean plant, Schizanthus grahamii Gill. (Solanaceae). The first approach interfaced a conventional HPLC column to NMR by means of a loop storage unit. After elution with a mobile phase consisting of deuterated water and standard protonated organic solvents, the separated analytes were momentarily stored in a loop cassette and then transferred one-at-a-time to the NMR flow probe for measurements. The second strategy combined HPLC with parallel ion-trap MS detection and NMR spectroscopy using an integrated solid-phase extraction (SPE) unit for post-column analyte trapping. The SPE cartridges were dried under a gentle stream of nitrogen and analytes were sequentially eluted and directed to a cryogenically cooled flow-probe with an NMR-friendly solvent. The structures of the four isomeric alkaloids, 3alpha-senecioyloxy-7beta-hydroxytropane, 3alpha-hydroxy-7beta-angeloyloxytropane, 3alpha-hydroxy-7beta-tigloyloxytropane and 3alpha-hydroxy-7beta-senecioyloxytropane, were unambiguously determined by combining NMR assignments with MS data.

Keywords

  • Chromatography, High Pressure Liquid/methods
  • Magnetic Resonance Spectroscopy/methods
  • Molecular Structure
  • Plant Bark/chemistry
  • Plant Stems/chemistry
  • Sensitivity and Specificity
  • Solanaceae/chemistry
  • Spectrophotometry, Ultraviolet/methods
  • Tropanes/analysis/chemistry

UNIGE affiliation entities

Citation (ISO format)

BIERI, Stefan et al. Identification of isomeric tropane alkaloids from Schizanthus grahamii by HPLC-NMR with loop storage and HPLC-UV-MS/SPE-NMR using a cryogenic flow probe. In: Phytochemical analysis, 2006, vol. 17, n° 2, p. 78–86. doi: 10.1002/pca.889

Main files (1)

Article (Published version)

Identifiers

Journal ISSN

0958-0344
614views
1downloads

Technical informations

Creation

27/05/2010 12:03:00

First validation

27/05/2010 12:03:00

Update

14/03/2023 15:29:25

Status update

14/03/2023 15:29:25

Last indexation

29/10/2024 14:57:11
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