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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 |
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Published in | Phytochemical analysis. 2006, vol. 17, no. 2, p. 78-86 | |
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 | |
Identifiers | DOI: 10.1002/pca.889 PMID: 16634283 | |
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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 https://archive-ouverte.unige.ch/unige:6716 |