2007Planta MedicaRequires access

Identification of alkaloids from fumariaceous plants

Ann Meyer, K Relius, Peter Imming

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Abstract

The majority of alkaloids from fumariaceous plants belong to protopine, protoberberine, phthalideisoquinoline, spirobenzylisoquinoline and aporphine alkaloids [1]. Protopine, protoberberine and aporphine alkaloids were assigned by GC-MS. Even constitutional isomers could be separated by GC and showed little but distinct variation of MS spectra. Although the molecular peak of phthalideisoquinoline alkaloids is missing in regular EI-MS, it appears with ESI-MS. Their distinctive EI-MS spectra contribute to structure elucidation as their fragmentation is quite characteristic [2]. The NMR spectra reveal aromatic substitution patterns and conformational preferences. We present results from an analytical study of various alkaloids from fumariaceous plants covering their GC-MS, TLC, UV and NMR data with an emphasis on spectral details that enable assignment to an isoquinoline alkaloid subclass. References: [1] Suau, R. et al. (2002) Phytochem Anal 13: 363–7. [2] Wickens, J. R. et al. (2006) Rapid Commun Mass Spectrom 20: 473–480.

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The majority of alkaloids from fumariaceous plants belong to protopine, protoberberine, phthalideisoquinoline, spirobenzylisoquinoline and aporphine alkaloids [1]. Protopine, protoberberine and aporphine alkaloids were assigned by GC-MS. Even constitutional isomers could be separated by GC and showed little but distinct variation of MS spectra. Although the molecular peak of phthalideisoquinoline alkaloids is missing in regular EI-MS, it appears with ESI-MS. Their distinctive EI-MS spectra contribute to structure elucidation as their fragmentation is quite characteristic [2]. The NMR spectra reveal aromatic substitution patterns and conformational preferences. We present results from an analytical study of various alkaloids from fumariaceous plants covering their GC-MS, TLC, UV and NMR data with an emphasis on spectral details that enable assignment to an isoquinoline alkaloid subclass. References: [1] Suau, R. et al. (2002) Phytochem Anal 13: 363–7. [2] Wickens, J. R. et al. (2006) Rapid Commun Mass Spectrom 20: 473–480.

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Available abstract

The majority of alkaloids from fumariaceous plants belong to protopine, protoberberine, phthalideisoquinoline, spirobenzylisoquinoline and aporphine alkaloids [1]. Protopine, protoberberine and aporphine alkaloids were assigned by GC-MS. Even constitutional isomers could be separated by GC and showed little but distinct variation of MS spectra. Although the molecular peak of phthalideisoquinoline alkaloids is missing in regular EI-MS, it appears with ESI-MS. Their distinctive EI-MS spectra contribute to structure elucidation as their fragmentation is quite characteristic [2]. The NMR spectra reveal aromatic substitution patterns and conformational preferences. We present results from an analytical study of various alkaloids from fumariaceous plants covering their GC-MS, TLC, UV and NMR data with an emphasis on spectral details that enable assignment to an isoquinoline alkaloid subclass. References: [1] Suau, R. et al. (2002) Phytochem Anal 13: 363–7. [2] Wickens, J. R. et al. (2006) Rapid Commun Mass Spectrom 20: 473–480.

Key concepts: Protopine, Aporphine, Alkaloid, Stereochemistry, Chemistry, Traditional medicine, Medicine

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