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. 2022 Nov 25;27(23):8217.
doi: 10.3390/molecules27238217.

A GC-MS Protocol for the Identification of Polycyclic Aromatic Alkaloids from Annonaceae

Ilya A P Jourjine  1 , Carolin Bauernschmidt  1 , Christoph Müller  1 , Franz Bracher  1
Affiliations

A GC-MS Protocol for the Identification of Polycyclic Aromatic Alkaloids from Annonaceae

Ilya A P Jourjine et al. Molecules. .

Abstract

The Annonaceae are an old family of flowering plants belonging to the order Magnoliales, distributed mainly in tropical regions. Numerous Annonaceae species find ethnobotanical use for curing a broad range of diseases, among them cancer and infections by diverse pathogens. Hence, bioactive natural products from Annonaceae have received considerable interest in drug development. Beyond cytotoxic acetogenins, unique aporphine-derived polycyclic aromatic alkaloids are characteristic constituents of Annonaceae. Among them are unique tri- and tetracyclic aromatic alkaloids like azafluorenones, diazafluoranthenes, azaanthracenes, and azaoxoaporphines. The complex substitution pattern of these alkaloids represents a major challenge in structure elucidation of isolated natural products. Based on a broad spectrum of alkaloids available from our previous work, we present a GC-MS protocol for the identification of over 20 polycyclic aromatic alkaloids from Annonaceae. This collection of data will contribute to the future identification of the metabolite patterns of extracts from Annonaceae as an important source of novel bioactive secondary metabolites.

Keywords: Annonaceae; alkaloids; azafluorenones; azaoxoaporphines; diazafluoranthenes; gas chromatography; mass spectrometry; oxoaporphines.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Postulated biosynthesis of azaoxoaporphines (e.g., sampangine, (5)), diazafluoranthenes (e.g., eupolauridine, (6)), azaanthraquinones (e.g., cleistopholine, (9)), and azafluorenones (e.g., onychine, (10)) starting from aporphinoid precursors.
Figure 2
Figure 2
Structures of the alkaloids (and synthetic analogues) analyzed in this investigation.
Figure 3
Figure 3
Total ion chromatogram of the compounds 3–25; 3 O,O-dimethylannocherine A, 4 lysicamine, 5 sampangine, 6 eupolauridine, 7 eupolauridine mono-N-oxide, 8 eupolauridine di-N-oxide, 9 cleistopholine, 10 onychine, 11 ursuline, 12 isoursuline, 13 6-methoxyonychine, 14 darienine, 15 polyfothine, 16 5,6,7,8-tetramethoxyonychine, 17 7-hydroxy-5,8-dimethoxyonychine, 18 7-methoxyonychine, 19 muniranine, 20 5,6-dimethoxyonychine, 21 3-methoxyonychine, 22 5,8-dimethoxyonychine, 23 5,7,8-trimethoxyonychine, 24 polynemoraline C, 25 annomontine; * impurities. Due to the individual volatility and thermal stability of the compounds, different concentrations were used in order to obtain a chromatogram visualizing the chromatographic behavior of all analytes (3 100 µg/mL, 4–6 20 µg/mL, 7, 8 50 µg/mL, 9–25 and IS 20 µg/mL.
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