Abstract
The genus Schizanthus (Solanaceae) comprises 12 accepted species primarily endemic to Chile. It is characterized by the presence of numerous tropane alkaloids found as ester derivatives of isomeric acids like angelic, senecioic, or tiglic, as well as mesaconic, itaconic, and citraconic acids, leading to numerous positional and configurational isomers. Up to now 50 alkaloids with these esters have been isolated and most of them are fully characterized. Analytical methods and techniques engaged during the investigation of this class of compounds, as well as their identification capabilities, are discussed. In several cases the absolute configuration is also well established, and some alkaloids are reported as biologically active. This review summarizes updated information on the distribution, botanical characteristics, phytochemical, and pharmacological knowledges of this genus up to mid-2018.
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Abbreviations
- AC:
-
Absolute configuration
- BA:
-
6-Benzylaminopurine
- CE:
-
Capillary electrophoresis
- COSY:
-
Correlation spectroscopy
- Da:
-
Dalton
- DFT:
-
Density functional theory
- ECD:
-
Electronic circular dichroism
- EI:
-
Electron impact
- FID:
-
Flame ionization detector
- FTIR:
-
Fourier transform infrared
- GC:
-
Gas chromatography
- HMBC:
-
Heteronuclear multiple bond correlation
- HPLC:
-
High performance liquid chromatography
- HPTLC:
-
High performance thin-layer chromatography
- HRESIMS:
-
High-resolution electrospray ionization mass spectrometry
- HSQC:
-
Heteronuclear single-quantum correlation
- IR:
-
Infrared
- ITMS:
-
Ion trap mass spectrometry
- IUPAC:
-
International union of pure and applied chemistry
- LLE:
-
Liquid–liquid extraction
- MEKC:
-
Micellar electrokinetic chromatography
- MS:
-
Mass spectrometry
- MW:
-
Molecular weight
- NACE:
-
Non aqueous capillary electrophoresis
- NOESY:
-
Nuclear Overhauser effect spectroscopy
- NMR:
-
Nuclear magnetic resonance
- PGC:
-
Porous graphitic carbon
- NAA:
-
1-Naphthaleneacetic acid
- NPD:
-
Nitrogen phosphorus detector
- SPE:
-
Solid phase extraction
- TDDFT:
-
Time dependent density functional theory
- TLC:
-
Thin-layer chromatography
- TOFMS:
-
Time-of-flight mass spectrometry
- UHPLC:
-
Ultra-high performance liquid chromatography
- UV:
-
Ultraviolet
- VCD:
-
Vibrational circular dichroism
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Acknowledgements
The authors want to thank Dr José San Martin, Departamento de Botanica, Universidad de Talca (Chile) for the identification of the plant material.
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Christen, P., Cretton, S., Humam, M. et al. Chemistry and biological activity of alkaloids from the genus Schizanthus. Phytochem Rev 19, 615–641 (2020). https://doi.org/10.1007/s11101-018-9598-5
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DOI: https://doi.org/10.1007/s11101-018-9598-5